MY DESCENT INTO CUCKOLDRY PART 1. MY PENIS FAILS TO STAY HARD.
We made contact through a dating service. Our first telephone conversation was exciting and full of promise. We arranged to meet for a coffee and chat over the weekend.
When I first saw her I was very attracted to her, She wore a short black skirt, tights, and a bolero jacket. She had black hair and stunning blue eyes. We got on well and I was taken with her sharp wit and humor. We met again the next weekend at a pub near her house some 40 miles away and I could tell that I was falling for her. I planned on going home (I didn’t want to take her for granted) but she asked me back to stay with her. When we got to her place, we went to bed almost immediately.
At this point, I should tell you that I had split up with my wife due to my unfaithfulness, but harbored a lot of guilt about it and I had subsequently had failed erection problems with several girlfriends. Needless to say, none of them lasted very long. Anyway, I was very aroused and lay on top of her as I slid my penis into her and started to make love. However, after a few minutes, I started to go soft. I was very embarrassed but she reassured me that it was okay and that this had happened to her before and perhaps it was tiredness or drink. I could tell however that she was disappointed and a bit frustrated.
It was lovely to fall asleep holding her. In the morning I was woken by her on top playing with me and she soon had me rock hard. She guided my cock into her moist pussy and it felt glorious. We started to fuck and determined to please her, I concentrated hard on not cumming too soon. We had been fucking for around 10 minutes when I saw her peering out of the window behind my head and then waving. I felt offended as I thought that she should be engrossed in our lovemaking, and I felt my erection begin to subside. “Fucking hell,” she said, “ Don’t tell me you’re one of those limp dicked wimps that can’t satisfy a woman!” and she got off me, gave me a look of contempt, and spat on my now flaccid penis and left the bedroom.
The next thing I heard was the front doorbell and her talking to a man. I resolved to get my clothes on and go. By the time I went downstairs, she had finished talking to the milkman who thought her waving meant she wanted some more milk or something. She asked me where I was going and I told her home. From being an unpleasant swearing spitfire only a few minutes ago, she was now sweetness and light. She said she was sorry and she had been disappointed as she was longing for sex. Anyway, we resolved the situation and spent a pleasant day together. We arranged for her to come to me the next weekend.
Despite my embarrassment the previous weekend, I was looking forward to seeing my new girlfriend, Diane. I’d prepared a meal for her, to impress her with my culinary skills. When she arrived we embraced and settled down with a glass of wine before dinner. ”Listen,” I said “About last time…”
"Shush, don’t worry, I’ve got an idea to help” she interjected, “I’ll tell you later.” We had a pleasant meal after which I tidied the dishes. When I rejoined her in the lounge, she produced a present, I was touched, but when I reached for it she told me “Not yet.” She then proceeded to tell me that she’d confided in a friend of hers called Jane who has ‘problems’ with her partner and had recommended that she buy me the present. “I like you and think we could have a future but if you want to be with me then I want you to trust me and do as I wish, can you do that?” She looked so gorgeous I had to have her as mine, so I agreed. She passed me the gift and I eagerly opened it but was shocked to discover that it was a metal chastity cage. “Before you say anything, Jane told me that having her partner wear a cage stopped him from playing with himself ensuring that he became desperate for her. This, in turn, made her more excited and she says she now has the most mind-blowing sex. I want this for us, and you did promise, so if your word is to be trusted, let me put it on you.”
There was a certain logic to this as I admit, I had been pleasuring myself daily. She proceeded to pull down my jeans and not without some difficulty, managed to ease the cage over my semi-erect cock, deftly aligning the cock cage tongue with the cock ring holes and smoothly locking it on with a small padlock. It felt strange, but Diane acted as though it was perfectly normal. She then told me that as it was my problem she shouldn’t have to ‘do without’ and that she had another present for me to help me satisfy her. I opened the parcel that she handed me to find a double-ended penis gag “I know you probably don’t want a penis-shaped gag in your mouth but it’s just a shape, not an actual penis, and it will help hold it more securely while you pleasure me, yes, I am going to get an orgasm and you are going to give it to me!” She then pushed the shorter penis gag into my mouth, strapped it tightly around my head, and pushed me onto the floor.
She then lubricated the 8” penis dildo and slowly lowered herself onto it. She slid slowly up and down the penis giving grunts and squeals of pleasure. Her smell was intoxicating and I admit my penis was trying to get hard in its new home to the point that it was painful. She then picked up the pace until she was slamming my head into the carpeted floor. I was not remotely comfortable but I desperately wanted her to cum, which she eventually did crying out “Oh, you’re so big and hard Steve, you fucked me so well, Steve!!" Who the hell was Steve? I waited until she dismounted and took the gag out of my mouth.
“Who the hell is Steve?” I asked, “Steve was my last boyfriend how did you know his name?”
“Because you called his name out as you came.”
“Don’t be so silly, I called your name but if you imagine I called out Steve’s name, perhaps I should give you a nickname?“ she replied, “Perhaps I should call you cucky!” She laughed long and loud as if she’d made the funniest joke in the world. “Would you like to taste me?“ she asked, and with that, she pushed the dildo that had been the source of her pleasure into my mouth. Her juices tasted divine and just as I was savoring her juices she added “Of course, if I had been fucking Steve, that means that you would be swallowing both his and my cum from off his penis... hold that thought!”
We made contact through a dating service. Our first telephone conversation was exciting and full of promise. We arranged to meet for a coffee and chat over the weekend.
When I first saw her I was very attracted to her, She wore a short black skirt, tights, and a bolero jacket. She had black hair and stunning blue eyes. We got on well and I was taken with her sharp wit and humor. We met again the next weekend at a pub near her house some 40 miles away and I could tell that I was falling for her. I planned on going home (I didn’t want to take her for granted) but she asked me back to stay with her. When we got to her place, we went to bed almost immediately.
At this point, I should tell you that I had split up with my wife due to my unfaithfulness, but harbored a lot of guilt about it and I had subsequently had failed erection problems with several girlfriends. Needless to say, none of them lasted very long. Anyway, I was very aroused and lay on top of her as I slid my penis into her and started to make love. However, after a few minutes, I started to go soft. I was very embarrassed but she reassured me that it was okay and that this had happened to her before and perhaps it was tiredness or drink. I could tell however that she was disappointed and a bit frustrated.
It was lovely to fall asleep holding her. In the morning I was woken by her on top playing with me and she soon had me rock hard. She guided my cock into her moist pussy and it felt glorious. We started to fuck and determined to please her, I concentrated hard on not cumming too soon. We had been fucking for around 10 minutes when I saw her peering out of the window behind my head and then waving. I felt offended as I thought that she should be engrossed in our lovemaking, and I felt my erection begin to subside. “Fucking hell,” she said, “ Don’t tell me you’re one of those limp dicked wimps that can’t satisfy a woman!” and she got off me, gave me a look of contempt, and spat on my now flaccid penis and left the bedroom.
The next thing I heard was the front doorbell and her talking to a man. I resolved to get my clothes on and go. By the time I went downstairs, she had finished talking to the milkman who thought her waving meant she wanted some more milk or something. She asked me where I was going and I told her home. From being an unpleasant swearing spitfire only a few minutes ago, she was now sweetness and light. She said she was sorry and she had been disappointed as she was longing for sex. Anyway, we resolved the situation and spent a pleasant day together. We arranged for her to come to me the next weekend.
Despite my embarrassment the previous weekend, I was looking forward to seeing my new girlfriend, Diane. I’d prepared a meal for her, to impress her with my culinary skills. When she arrived we embraced and settled down with a glass of wine before dinner. ”Listen,” I said “About last time…”
"Shush, don’t worry, I’ve got an idea to help” she interjected, “I’ll tell you later.” We had a pleasant meal after which I tidied the dishes. When I rejoined her in the lounge, she produced a present, I was touched, but when I reached for it she told me “Not yet.” She then proceeded to tell me that she’d confided in a friend of hers called Jane who has ‘problems’ with her partner and had recommended that she buy me the present. “I like you and think we could have a future but if you want to be with me then I want you to trust me and do as I wish, can you do that?” She looked so gorgeous I had to have her as mine, so I agreed. She passed me the gift and I eagerly opened it but was shocked to discover that it was a metal chastity cage. “Before you say anything, Jane told me that having her partner wear a cage stopped him from playing with himself ensuring that he became desperate for her. This, in turn, made her more excited and she says she now has the most mind-blowing sex. I want this for us, and you did promise, so if your word is to be trusted, let me put it on you.”
There was a certain logic to this as I admit, I had been pleasuring myself daily. She proceeded to pull down my jeans and not without some difficulty, managed to ease the cage over my semi-erect cock, deftly aligning the cock cage tongue with the cock ring holes and smoothly locking it on with a small padlock. It felt strange, but Diane acted as though it was perfectly normal. She then told me that as it was my problem she shouldn’t have to ‘do without’ and that she had another present for me to help me satisfy her. I opened the parcel that she handed me to find a double-ended penis gag “I know you probably don’t want a penis-shaped gag in your mouth but it’s just a shape, not an actual penis, and it will help hold it more securely while you pleasure me, yes, I am going to get an orgasm and you are going to give it to me!” She then pushed the shorter penis gag into my mouth, strapped it tightly around my head, and pushed me onto the floor.
She then lubricated the 8” penis dildo and slowly lowered herself onto it. She slid slowly up and down the penis giving grunts and squeals of pleasure. Her smell was intoxicating and I admit my penis was trying to get hard in its new home to the point that it was painful. She then picked up the pace until she was slamming my head into the carpeted floor. I was not remotely comfortable but I desperately wanted her to cum, which she eventually did crying out “Oh, you’re so big and hard Steve, you fucked me so well, Steve!!" Who the hell was Steve? I waited until she dismounted and took the gag out of my mouth.
“Who the hell is Steve?” I asked, “Steve was my last boyfriend how did you know his name?”
“Because you called his name out as you came.”
“Don’t be so silly, I called your name but if you imagine I called out Steve’s name, perhaps I should give you a nickname?“ she replied, “Perhaps I should call you cucky!” She laughed long and loud as if she’d made the funniest joke in the world. “Would you like to taste me?“ she asked, and with that, she pushed the dildo that had been the source of her pleasure into my mouth. Her juices tasted divine and just as I was savoring her juices she added “Of course, if I had been fucking Steve, that means that you would be swallowing both his and my cum from off his penis... hold that thought!”
My Descent into Cuckoldry Part 2. Chastity and Humiliation.
MY DESCENT INTO CUCKOLDRY CHAPTER 2. CHASTITY AND HUMILIATION.When we went to bed she told me that she’d enjoyed the evening and that I could cuddle up to her if I liked. I went to cradle her, and she slid up and pushed me down cradling my head against her breast. Her softness and her smell were intoxicating, I felt my cock begin to swell in its cage. “Please Diane, unlock the cage and let me feel myself inside you,“ I pleaded.
“Not,” she replied, “Jane told me that you would be desperate, but that I must not give in, and I promised not to." Jane had suggested that I give the keys to her for safekeeping so that I wouldn’t weaken, I thought it was an excellent idea. "You are to wear that cage all week until I see you next weekend. If I discover that you have tried to remove it then I swear that it will be 6 months minimum before I’ll even consider having your pathetically unmanly penis inside my luxurious pussy.” Her rejection seemed only to make my erection harder and it expanded tight against its confining prison and bulged angrily through the bars, inducing considerable pain and making me cry out. “Oh, that’s delightful!“ she said, laughing joyfully “Seeing you suffering for me makes me feel so desirable.“ I don’t understand it, but her firm and controlled manner and her humiliating treatment of me, which should have deterred me, simply made me want her more and more desperately. She was strikingly attractive but could paralyze me with just a witheringly contemptuous look.
Sunday was a very ordinary day. We went for a walk in the country and stopped for brunch and read the papers at a tastefully furbished bistro cafe and talked about ordinary things. On the way back she told me that she enjoyed my company, thought that I was quite good-looking, liked my stability and reliability, and felt that I would suit her need to have a partner who was both respectful of and submissive to women. She then added “I’ve always gone for Alpha males as boyfriends, ones who are well endowed and have stamina and who can satisfy me sexually deep inside, sadly they also want to control me and I don’t want that. I’ve got to be honest and tell you that my fantasy would be to have a supportive and submissive beta like you to love, worship, and cherish me, however, I treat him but also have a manly lover virile Adonis for fulfilling mind-blowing sex. That‘s my ideal but let’s see if we can improve your performance first.” pushing my shoulder playfully and laughing as she blew me a kiss. She then told me that I was to come to her house next Friday and that some of her work colleagues had invited us to a party on Saturday. I was a bit daunted by the thought of a party of people I hadn’t met (I am shy in such situations) and she could sense that I was a bit uncomfortable with it. She said that she would ask her best friend to come for a meal at her house on Friday so that I would know someone other than her at the party the following night, I was touched by her thoughtfulness.
That evening in bed, after she had left to return home, I reflected on my time with her to date, as I played with my cage and wished that I could cum. She had spat on my penis, called me a limp dicked wimp, face fucked me, taunted me with the thought of tasting her and her ex’s cum, had locked me in a chastity cage and when my cock had tried to grow in its cage, had laughed and told me that my pain was ’delightful’ and made her feel ‘desirable' and yet, I could hardly wait to see her again!
My Descent into Cuckoldry Part 3. Diane’s ‘Bestie’s’ Lie Lands Me in Trouble.
MY DESCENT INTO CUCKOLDRY PART 3. DIANE’S ‘BESTIE‘S‘ LIE LANDS ME IN TROUBLE.
Every morning of the next week I was woken by pain from my ‘morning wood’, caused by vivid erotic dreams about Diane. She was different from any other girlfriend I’d had before and she excited me with her unconventional behavior. I dealt with the ‘morning wood‘ pain by thinking of unpleasant things that turned me off. I longed to see her again and the weekend seemed too far in the future. Eventually, Friday arrived and I finished work early to maximize my time with her. When she saw me pull up, she opened the front door, allowed me to kiss her on the cheek, and suggested I take my case upstairs and come down for a drink and to meet her ‘bestie’.
I entered the lounge to find Diane and her friend sitting next to each other on the sofa so I took one of the armchairs opposite. Diane introduced me to her friend and then said, “This is my close friend Jane.” I was taken aback - Jane was the name of her friend who had suggested I wear a chastity cage... was this the same Jane, or did Diane have another friend called Jane? I didn’t know how to react and was embarrassed so didn’t say much. Diane picked up on this saying “In case you’re wondering, this is my dearest friend Jane, who is advising me on how to help you with your problem.” Jane was attractive and quite tall, she looked sporty and quite muscular.
She told me that Diane seemed to be more alive since meeting me and couldn’t stop talking about me. She told me not to be embarrassed about my problem keeping hard, not to fret, and that it would all work out. She was so ‘normal’ about it that she soon put me at ease. She genuinely seemed to like me. We sat down for a lovely meal of lasagna with garlic bread and red wine. There was no more mention of anything embarrassing and I soon felt that I had made a new friend in Jane. We ran out of wine and Diane said she would go to the local shop for another bottle. I offered to go but Diane said that as she knew the way it would be quicker if I stayed and chatted with Jane. I asked Jane what she did and she told me she was a furniture designer. More questions led to me learning that her hobbies included athletics and that she loved horse riding, dance, d..i.y., and ‘inventing things’. “And what does your other half do?”, I asked,
She replied, “Oh, he’s my hubwife." Then Diane returned and topped up our glasses. She then asked what we’d talked about To which Jane replied, “I don’t know how to tell you this, but as soon as you had gone, he asked me to give him a key to his cage. Obviously, I refused and he offered me £100 for it, again I told him no, and then he threatened me - thank goodness, you returned In time!” She broke down in tears!
I couldn’t believe what I heard. None of this was true. I started to protest my innocence but Diane fixed me with a piercing glare that froze me mid-sentence. “You little worm, how dare you to treat Jane like that? Not a word, come with me.” She led me upstairs and told me to take my clothes off, then opened a door from her bedroom into a small empty closet. Wearing only my chastity cage, she put a blindfold over my eyes and told me to hold up my hands. I heard the sound of chains and felt her buckle straps around my wrists and then click! Click! As she locked the straps closed. “I’m going to comfort Jane now. You can think about what you’ve done - I’ll deal with you later!”
This story and each chapter are being added to in small sections as I get an opportunity. Please be patient, keep checking.……and if you want to encourage me, give me some feedback. Thank you.
Every morning of the next week I was woken by pain from my ‘morning wood’, caused by vivid erotic dreams about Diane. She was different from any other girlfriend I’d had before and she excited me with her unconventional behavior. I dealt with the ‘morning wood‘ pain by thinking of unpleasant things that turned me off. I longed to see her again and the weekend seemed too far in the future. Eventually, Friday arrived and I finished work early to maximize my time with her. When she saw me pull up, she opened the front door, allowed me to kiss her on the cheek, and suggested I take my case upstairs and come down for a drink and to meet her ‘bestie’.
I entered the lounge to find Diane and her friend sitting next to each other on the sofa so I took one of the armchairs opposite. Diane introduced me to her friend and then said, “This is my close friend Jane.” I was taken aback - Jane was the name of her friend who had suggested I wear a chastity cage... was this the same Jane, or did Diane have another friend called Jane? I didn’t know how to react and was embarrassed so didn’t say much. Diane picked up on this saying “In case you’re wondering, this is my dearest friend Jane, who is advising me on how to help you with your problem.” Jane was attractive and quite tall, she looked sporty and quite muscular.
She told me that Diane seemed to be more alive since meeting me and couldn’t stop talking about me. She told me not to be embarrassed about my problem keeping hard, not to fret, and that it would all work out. She was so ‘normal’ about it that she soon put me at ease. She genuinely seemed to like me. We sat down for a lovely meal of lasagna with garlic bread and red wine. There was no more mention of anything embarrassing and I soon felt that I had made a new friend in Jane. We ran out of wine and Diane said she would go to the local shop for another bottle. I offered to go but Diane said that as she knew the way it would be quicker if I stayed and chatted with Jane. I asked Jane what she did and she told me she was a furniture designer. More questions led to me learning that her hobbies included athletics and that she loved horse riding, dance, d..i.y., and ‘inventing things’. “And what does your other half do?”, I asked,
She replied, “Oh, he’s my hubwife." Then Diane returned and topped up our glasses. She then asked what we’d talked about To which Jane replied, “I don’t know how to tell you this, but as soon as you had gone, he asked me to give him a key to his cage. Obviously, I refused and he offered me £100 for it, again I told him no, and then he threatened me - thank goodness, you returned In time!” She broke down in tears!
I couldn’t believe what I heard. None of this was true. I started to protest my innocence but Diane fixed me with a piercing glare that froze me mid-sentence. “You little worm, how dare you to treat Jane like that? Not a word, come with me.” She led me upstairs and told me to take my clothes off, then opened a door from her bedroom into a small empty closet. Wearing only my chastity cage, she put a blindfold over my eyes and told me to hold up my hands. I heard the sound of chains and felt her buckle straps around my wrists and then click! Click! As she locked the straps closed. “I’m going to comfort Jane now. You can think about what you’ve done - I’ll deal with you later!”
This story and each chapter are being added to in small sections as I get an opportunity. Please be patient, keep checking.……and if you want to encourage me, give me some feedback. Thank you.
My Descent into Cuckoldry Part 4. Restrained Overnight in the Closet.
MY DESCENT INTO CUCKOLDRY PART 4. RESTRAINED OVERNIGHT IN THE CLOSET.
I could hear their voices from downstairs in the closet, but not what they were saying. I’m guessing that about an hour passed, and then another hour. My arms were aching by now but I had no idea how long I would be left helpless in the closet. Eventually, the door was opened and Diane told me that I had frightened and upset Jane but that she had persuaded Jane not to report me to the police for threatening her on condition that Jane could administer some punishment. Diane also said that if I did not accept punishment, she would let my work and my friends know what I had done and what sort of person I was. This was so unfair but I had no choice and agreed. Jane spoke next “Do you know what ‘Kali‘s teeth’ is?” “No” I replied. She removed my blindfold and held up a hinged steel ring about 2” wide and studded inside with three rows of pointed spikes. It looked threatening. Then Diane grabbed my balls and stretched my sac. Jane deftly clamped the device above my balls and below my caged cock and locked it in place. It hurt - not agony, but more than uncomfortable. She smiled approvingly and told me that Diane had agreed that instead of being uncaged on Saturday, I would wear both cage and Kali’s teeth for a full month and that she would be keeping the keys.
“That look suits you,” Diane said “it's kind of sexy. I bet it would look even sexier underneath a pretty pair of panties.” “You are so right Diane. I would offer mine but I’m afraid they are a bit soiled from the hot sex I had this afternoon!” “He won’t mind that Jane, let’s see what they are like.” Jane reached up under her skirt and pulled off her pink lacy panties. Diane took them from her and held the gusset up in front of my face. I could smell a strong odor of cum and see goo. She rubbed it around my nose and mouth giggling as she did so. “You are a lucky boy, aren’t you? They are gorgeous aren’t they, so pretty, so pink, so feminine.” Then she told me to lift one leg and then the other and slid the panties up into place. Then, with me helpless and humiliated, she and Jane got their phones and each took pictures.
Jane then left and Diane got ready for bed. I asked her to release me. “Oh no. You will spend the night there. It will give you time to reflect on your bad behavior”. With that, she produced a short, fat dildo gag and pushed it into my mouth, strapped it tightly, and locked it in place. ”I can’t have you calling out in the night. I need my beauty sleep,” she told me. Then she held up a pink leather head mask, padded around the ears. Sweet dreams” she said as she pulled it over my head. I could feel her pulling it tightly at the back, and sensed a padlock being clicked into place. My arms were very sore by now. I didn’t know if I would be able to endure the night, but there was no choice…….
MY COCK LOCKED IN KALI’S TEETH RING AND COCK CAGE.
I could hear their voices from downstairs in the closet, but not what they were saying. I’m guessing that about an hour passed, and then another hour. My arms were aching by now but I had no idea how long I would be left helpless in the closet. Eventually, the door was opened and Diane told me that I had frightened and upset Jane but that she had persuaded Jane not to report me to the police for threatening her on condition that Jane could administer some punishment. Diane also said that if I did not accept punishment, she would let my work and my friends know what I had done and what sort of person I was. This was so unfair but I had no choice and agreed. Jane spoke next “Do you know what ‘Kali‘s teeth’ is?” “No” I replied. She removed my blindfold and held up a hinged steel ring about 2” wide and studded inside with three rows of pointed spikes. It looked threatening. Then Diane grabbed my balls and stretched my sac. Jane deftly clamped the device above my balls and below my caged cock and locked it in place. It hurt - not agony, but more than uncomfortable. She smiled approvingly and told me that Diane had agreed that instead of being uncaged on Saturday, I would wear both cage and Kali’s teeth for a full month and that she would be keeping the keys.
“That look suits you,” Diane said “it's kind of sexy. I bet it would look even sexier underneath a pretty pair of panties.” “You are so right Diane. I would offer mine but I’m afraid they are a bit soiled from the hot sex I had this afternoon!” “He won’t mind that Jane, let’s see what they are like.” Jane reached up under her skirt and pulled off her pink lacy panties. Diane took them from her and held the gusset up in front of my face. I could smell a strong odor of cum and see goo. She rubbed it around my nose and mouth giggling as she did so. “You are a lucky boy, aren’t you? They are gorgeous aren’t they, so pretty, so pink, so feminine.” Then she told me to lift one leg and then the other and slid the panties up into place. Then, with me helpless and humiliated, she and Jane got their phones and each took pictures.
Jane then left and Diane got ready for bed. I asked her to release me. “Oh no. You will spend the night there. It will give you time to reflect on your bad behavior”. With that, she produced a short, fat dildo gag and pushed it into my mouth, strapped it tightly, and locked it in place. ”I can’t have you calling out in the night. I need my beauty sleep,” she told me. Then she held up a pink leather head mask, padded around the ears. Sweet dreams” she said as she pulled it over my head. I could feel her pulling it tightly at the back, and sensed a padlock being clicked into place. My arms were very sore by now. I didn’t know if I would be able to endure the night, but there was no choice…….
MY COCK LOCKED IN KALI’S TEETH RING AND COCK CAGE.
My Descent into Cuckoldry Part 5. An Orgasm for Diane/ Dress Shopping.
MY DESCENT INTO CUCKOLDRY PART 5. AN ORGASM FOR DIANE/DRESS SHOPPING
The night in the closet was a nightmare. I was overtired and my arms were in agony. I must have fallen asleep dozens of times only to be cruelly woken by the pain in my arms as they took the weight of my slumping body. I couldn’t see anything, I couldn’t hear anything, I couldn’t call out, and had no idea what time it was or how long it would be until I would be released. Eventually, however, Diane opened the door and removed the hood and the blindfold. She took hold of my cock cage shaking it gently and pushing her fingertips through the gaps. Needless to say, I started to respond and once again my cock strained to grow in its prison until it became first uncomfortable and then painful. She let go and slowly the pain subsided. “I’ve had an awful night sweetie, don’t you feel sorry for me?” she asked, “Next to no sleep as I couldn’t stop thinking of you bravely enduring your ordeal. I was so excited, so turned on, that I kept waking up to play with myself, thinking of all the fun meetings you were bringing me. I must have orgasmed at least 6 times.”
She looked at me coquettishly “you do think that I’m attractive, don’t you?” I nodded yes, “I excite you, don’t I?” Again I nodded. ”Good boy, let’s forget about all the unpleasantness, I’m going to take out that naughty gag and remove those naughty restraints. I’m a bit sticky, I’m going to let you clean me up." Ignoring the pain of my freed body, she led me to her bed, pushed me to my knees on the floor, and lay back, pulling my face into her intimate area. “Lick me gently first to clean me then insert your tongue as deep as you can and move it round and round. Taste me, taste my womanliness, and then you may concentrate on my clit.“ She kept me on my knees for over half an hour, until she came.
She told me that Jane was very sensible in taking the keys as otherwise she would have been tempted to show me some mercy and let me cum. "Can’t you ask Jane for the keys?” I pleaded. “I can’t do that first because she would be very disappointed in me, but chiefly because you promised to accept your punishment, I’ve got to be able to rely on your word.” She then said that as it was going to be a sunny day, we would do a bit of shopping, take a walk and have a coffee.
Anyone looking at us would have simply seen a couple having fun together. She was so attractive that I felt proud to be with her; the kind of attractive that drew glances from other men, and I did notice this happen several times. It made me feel both proud but also a bit jealous. I told her that I needed the toilet, and she said she would meet me in Monsoon. I was quite some time as I had to queue for a cubicle, locked as I was in a cage and spiked ring wearing lacy pink panties. It must have been 20 minutes before I made it to Monsoon. I looked around for her and saw that she was talking to a sales assistant and holding a rather nice dress, it was pink gingham and looked rather like an adult version of a young girl‘s school dress. As I approached I heard the assistant say “I think that you’ve mistakenly picked up the wrong size, that’s an 18 but you look more like a 14 to me.” Diane replied that actually, it wasn’t for her but for a friend. She told her that there was a school-themed party tonight.
“Can my friend try it on?”
“Of course, she can.“
“Oh, I’m afraid you’ve got it wrong,” pointing to me, “This is my friend!” I blushed with embarrassment. The shop assistant was taken aback but said that she thought it would be okay. Diane bustled me into the cubicle. “Put it on then come out and show me.” I didn’t know what to do. I didn’t want to put it on and come out into the shop but I didn’t want a scene with Diane either. I put it on, steeled myself, and walked out of the cubicle. “Give me a twirl.“ I did as I was told, raising smiles and laughter from several other women. “Perfect sweetie, you’ll have the best outfit at the party - go and change, unless you want to wear it now that is?”
I couldn’t wait to get away from the shop, though Diane then took me to Clark’s where at Diane’s insistence, I had to try on Mary Jane style shoes which she said would be perfect, and then into Claire’s where she tried numerous hair clips, bands, and elastics in my hair. I do have quite long hair. She settled on the pink Alice band. “Let‘s have a well-deserved coffee," she said. I wanted to ask about the party being themed. There had been no mention of that and I wanted to protest at having to buy the dress, shoes, and accessories, which cost quite a lot just for a party and why should I go in a girl's outfit? However, I was learning that Diane didn’t like me to question her, or disagree with her, so for now I bit my tongue. I decided I would wait until we got to the coffee shop and pretend that I didn’t remember her telling me that there was a theme to the party.
This story is being added to in small sections, as and when I get the time and the opportunity. Please bear with me, and if you want to encourage me to relate more, then comment and feedback would be welcome. If you would like to have a conversation or ask questions please do.
The night in the closet was a nightmare. I was overtired and my arms were in agony. I must have fallen asleep dozens of times only to be cruelly woken by the pain in my arms as they took the weight of my slumping body. I couldn’t see anything, I couldn’t hear anything, I couldn’t call out, and had no idea what time it was or how long it would be until I would be released. Eventually, however, Diane opened the door and removed the hood and the blindfold. She took hold of my cock cage shaking it gently and pushing her fingertips through the gaps. Needless to say, I started to respond and once again my cock strained to grow in its prison until it became first uncomfortable and then painful. She let go and slowly the pain subsided. “I’ve had an awful night sweetie, don’t you feel sorry for me?” she asked, “Next to no sleep as I couldn’t stop thinking of you bravely enduring your ordeal. I was so excited, so turned on, that I kept waking up to play with myself, thinking of all the fun meetings you were bringing me. I must have orgasmed at least 6 times.”
She looked at me coquettishly “you do think that I’m attractive, don’t you?” I nodded yes, “I excite you, don’t I?” Again I nodded. ”Good boy, let’s forget about all the unpleasantness, I’m going to take out that naughty gag and remove those naughty restraints. I’m a bit sticky, I’m going to let you clean me up." Ignoring the pain of my freed body, she led me to her bed, pushed me to my knees on the floor, and lay back, pulling my face into her intimate area. “Lick me gently first to clean me then insert your tongue as deep as you can and move it round and round. Taste me, taste my womanliness, and then you may concentrate on my clit.“ She kept me on my knees for over half an hour, until she came.
She told me that Jane was very sensible in taking the keys as otherwise she would have been tempted to show me some mercy and let me cum. "Can’t you ask Jane for the keys?” I pleaded. “I can’t do that first because she would be very disappointed in me, but chiefly because you promised to accept your punishment, I’ve got to be able to rely on your word.” She then said that as it was going to be a sunny day, we would do a bit of shopping, take a walk and have a coffee.
Anyone looking at us would have simply seen a couple having fun together. She was so attractive that I felt proud to be with her; the kind of attractive that drew glances from other men, and I did notice this happen several times. It made me feel both proud but also a bit jealous. I told her that I needed the toilet, and she said she would meet me in Monsoon. I was quite some time as I had to queue for a cubicle, locked as I was in a cage and spiked ring wearing lacy pink panties. It must have been 20 minutes before I made it to Monsoon. I looked around for her and saw that she was talking to a sales assistant and holding a rather nice dress, it was pink gingham and looked rather like an adult version of a young girl‘s school dress. As I approached I heard the assistant say “I think that you’ve mistakenly picked up the wrong size, that’s an 18 but you look more like a 14 to me.” Diane replied that actually, it wasn’t for her but for a friend. She told her that there was a school-themed party tonight.
“Can my friend try it on?”
“Of course, she can.“
“Oh, I’m afraid you’ve got it wrong,” pointing to me, “This is my friend!” I blushed with embarrassment. The shop assistant was taken aback but said that she thought it would be okay. Diane bustled me into the cubicle. “Put it on then come out and show me.” I didn’t know what to do. I didn’t want to put it on and come out into the shop but I didn’t want a scene with Diane either. I put it on, steeled myself, and walked out of the cubicle. “Give me a twirl.“ I did as I was told, raising smiles and laughter from several other women. “Perfect sweetie, you’ll have the best outfit at the party - go and change, unless you want to wear it now that is?”
I couldn’t wait to get away from the shop, though Diane then took me to Clark’s where at Diane’s insistence, I had to try on Mary Jane style shoes which she said would be perfect, and then into Claire’s where she tried numerous hair clips, bands, and elastics in my hair. I do have quite long hair. She settled on the pink Alice band. “Let‘s have a well-deserved coffee," she said. I wanted to ask about the party being themed. There had been no mention of that and I wanted to protest at having to buy the dress, shoes, and accessories, which cost quite a lot just for a party and why should I go in a girl's outfit? However, I was learning that Diane didn’t like me to question her, or disagree with her, so for now I bit my tongue. I decided I would wait until we got to the coffee shop and pretend that I didn’t remember her telling me that there was a theme to the party.
This story is being added to in small sections, as and when I get the time and the opportunity. Please bear with me, and if you want to encourage me to relate more, then comment and feedback would be welcome. If you would like to have a conversation or ask questions please do.
My Descent into Cuckoldry Part 6. Coffee Shop Humiliation.
MY DESCENT INTO CUCKOLDRY PART 6. COFFEE SHOP HUMILIATION.
We made our way to a coffee shop at the top of a department store and found ourselves a table, despite it being quite busy. The tables were close to each other which was not ideal as I wanted to talk to Diane about the dress and shoes. Fortunately, we had a partition on one side so only one table to our other side, with two women chatting away, engrossed in their conversation. I felt that if I talked quietly, they wouldn’t overhear. I went to the counter and got some coffee and cake and returned to Diane.
”Diane,” I started “You never said that the party was to be fancy dress. Why do I have to go as a schoolgirl rather than as a boy?”
“I did tell you, obviously you weren’t paying attention, and don’t be so precious - it’s a fancy dress for goodness sake, it’s just for fun, it‘ll be a laugh. Don’t be a spoilsport.”
”But it‘s cost me the best part of £200…..” I began to say. She slapped my face, drawing the attention of the women at the table next to us.
Not attempting to keep her voice down, said “I‘m disappointed by your inability to perform in bed and now you disappoint me further by complaining about the party that I have been looking forward to.” She turned to the women at the next table and taking the photograph of me naked apart from the cock ring and cage, she showed it to them and said “He can’t keep hard for me. I have him locked in this in the vain hope that denial will help improve his performance” They looked at the photo, then at me. I was cringing with embarrassment but also because they might cause an even bigger disturbance by calling for the manager.
As it was, they burst into giggles, one of them said, ”Young lady, you are a very attractive woman, you could have any man you wanted, women don’t have to put up with the things that they used to have to put up with anymore. I applaud you for asserting yourself." She then turned to me and said, “You are a lucky man to have such a gorgeous partner, she’s above your class, if I were you, I wouldn’t push my luck, particularly with your obvious inadequacy in bed that I wouldn’t tolerate.”
“Well, she’s right. You can either stop whinging and come to the party in your new dress, or you can leave now and never see me again.” said Diane “What’s it to be?”
The woman was right, Diane was out of my class. I had lost several girlfriends already and Diane was the most attractive woman I’d ever been with. Nice ordinary girls hadn’t solved my problem. Diane was prepared to tolerate and even help me. Under the stares of Diane and these two women, with my head hung low in embarrassment, I meekly said, “I‘ll wear the dress at the fancy dress party, Diane."
We made our way to a coffee shop at the top of a department store and found ourselves a table, despite it being quite busy. The tables were close to each other which was not ideal as I wanted to talk to Diane about the dress and shoes. Fortunately, we had a partition on one side so only one table to our other side, with two women chatting away, engrossed in their conversation. I felt that if I talked quietly, they wouldn’t overhear. I went to the counter and got some coffee and cake and returned to Diane.
”Diane,” I started “You never said that the party was to be fancy dress. Why do I have to go as a schoolgirl rather than as a boy?”
“I did tell you, obviously you weren’t paying attention, and don’t be so precious - it’s a fancy dress for goodness sake, it’s just for fun, it‘ll be a laugh. Don’t be a spoilsport.”
”But it‘s cost me the best part of £200…..” I began to say. She slapped my face, drawing the attention of the women at the table next to us.
Not attempting to keep her voice down, said “I‘m disappointed by your inability to perform in bed and now you disappoint me further by complaining about the party that I have been looking forward to.” She turned to the women at the next table and taking the photograph of me naked apart from the cock ring and cage, she showed it to them and said “He can’t keep hard for me. I have him locked in this in the vain hope that denial will help improve his performance” They looked at the photo, then at me. I was cringing with embarrassment but also because they might cause an even bigger disturbance by calling for the manager.
As it was, they burst into giggles, one of them said, ”Young lady, you are a very attractive woman, you could have any man you wanted, women don’t have to put up with the things that they used to have to put up with anymore. I applaud you for asserting yourself." She then turned to me and said, “You are a lucky man to have such a gorgeous partner, she’s above your class, if I were you, I wouldn’t push my luck, particularly with your obvious inadequacy in bed that I wouldn’t tolerate.”
“Well, she’s right. You can either stop whinging and come to the party in your new dress, or you can leave now and never see me again.” said Diane “What’s it to be?”
The woman was right, Diane was out of my class. I had lost several girlfriends already and Diane was the most attractive woman I’d ever been with. Nice ordinary girls hadn’t solved my problem. Diane was prepared to tolerate and even help me. Under the stares of Diane and these two women, with my head hung low in embarrassment, I meekly said, “I‘ll wear the dress at the fancy dress party, Diane."
My Descent into Cuckoldry Part 7. At the Party.
MY DESCENT INTO CUCKOLDRY PART 7. AT THE PARTY.
I felt very subdued, slightly numbed. I felt rather like a fly trapped in a Venus flytrap - I couldn’t resist the allure yet the deeper I went into the flytrap, the more trapped I became. Struggling was hard and exhausting, and I knew that my resistance was fading. When we got back to Diane‘s house she told me to have a shower and dry myself in readiness for the party. When I came out of the shower, she was waiting for me in her bedroom where I saw that she had laid out the shopping on the bed. It included a white silky camisole top, but with some padding which she had bought before I met her in Monsoon.
She explained that as I was going as a young pre teenage schoolgirl I would likely have the beginnings of breast development and the padded camisole would emulate it. She told me to hold up my arms and slipped the camisole on me. She then got me to put on the dress and a pair of plain white shin length socks and my new shoes, as the pink lacy panties were dirty, I would have to go without any. Next, she put some very light makeup on my face - I was meant to be a young schoolgirl she said, finally then she put on the elasticated pink Alice band. Standing back and admiring her work she said “Ahhh, you look so sweet. You’ll be the best schoolgirl at the party. I’m going to call you Alice - very suitable for you I think. Now you go downstairs and watch the telly while I prepare my outfit.
It was around an hour later that she came downstairs. I was looking forward to seeing what she was wearing. I hoped that it would be a St. Trinians-style school uniform, which I’d always found rather sexy. When she came into the lounge, I was disappointed because she was wearing a coat. I asked her to let me see her outfit but she told me there was no time and that it would be a surprise for me. She was right, we were running late. I put a coat on which covered my dress but that still left my shoes and ankle socks on display. We got to the party some half an hour late and parked on the street a few houses down. Walking arm-in-arm to the party house and Diane rang the bell. We only had to wait seconds before the door was opened by a man and a woman. “Amanda, Mike - this is Alice,” said Diane. I knew better than to interrupt her. “Say hello Alice.”
They smiled at me and said, ”Hello Alice.” Mike then offered to take our coats. Diane gave me one of her looks and I knew I had no choice, so I took off my coat and gave it to Mike.
“Oh my, oh my,” said Amanda, "Jane told me of your little joke that you were going to play on him, but I didn’t believe that you would manage to pull it off. Alice, you look lovely. I can’t wait to introduce you to the gang!”
I then realized that Amanda and Mike were not in fancy dress. Diane then took her coat off only to reveal that she wasn’t in fancy dress either, just a pair of culottes and a rather revealing black top with lace up detail front. “Come through to the back, everyone is waiting in anticipation,” Diane told me to follow her and we walked into a large room with some 50+ people, none of them in fancy dress. “Hello everyone. I’d like you to give a big cheer and a warm welcome to Alice.” Diane announced, Then she moved from in front of me and there was a collective gasp interspersed with Oohs! and Ahhs! And then everyone burst into laughter. I didn’t know where to put myself and just wanted the ground to swallow me up.
Jane then approached me saying “Alice, you don’t know how pleased I am to see you like this; we must spend some time together soon.” She kissed me on the cheek. Slowly, people went back into their groups and I was left pretty much alone. Diane had moved over to a guy who had been on his own, and was deep in conversation with him. I was so uncomfortable that I withdrew into myself and spent what seemed like forever just standing there like a wallflower. I thought that Diane would rejoin me soon, but by now she was sitting on the man’s lap with her arms around his neck.
I could see a couple of people glancing at me to see how I’d react and overheard one man saying to his partner “What a sissy!” I had to stand there until Jane then took my hand and led me to the center of the room. She then moved behind me, and shouted “Look, everyone!” before I knew it, she pulled up the hem of my dress, exposing my caged cock and my collared ball sack. Hands either side of me grabbed my arms ensuring that I couldn’t pull my dress down and cover myself. There was a cacophony of catcalls, whooping, and laughter until Diane called for hush and said “ As you can see, Alice is in chastity. That’s because her “cock’, or rather her ‘clit’ is useless. " She said, “Alice, this is Steve, my ex - don’t you think he’s manly? I certainly do. His stamina is legendary. He has no problem staying hard for me. I’ve thought of an appropriate full name for you - ‘AliceBanned,‘ because from now on you are banned from having any orgasms. You wearing that Alice Band gave me the idea - an amusing play on words, don’t you think? Jane, please take Alice home and prepare her for the night, as we planned earlier. I was relieved to get out of there, but apprehensive as to exactly what was going to happen to me next……
to be continued
I felt very subdued, slightly numbed. I felt rather like a fly trapped in a Venus flytrap - I couldn’t resist the allure yet the deeper I went into the flytrap, the more trapped I became. Struggling was hard and exhausting, and I knew that my resistance was fading. When we got back to Diane‘s house she told me to have a shower and dry myself in readiness for the party. When I came out of the shower, she was waiting for me in her bedroom where I saw that she had laid out the shopping on the bed. It included a white silky camisole top, but with some padding which she had bought before I met her in Monsoon.
She explained that as I was going as a young pre teenage schoolgirl I would likely have the beginnings of breast development and the padded camisole would emulate it. She told me to hold up my arms and slipped the camisole on me. She then got me to put on the dress and a pair of plain white shin length socks and my new shoes, as the pink lacy panties were dirty, I would have to go without any. Next, she put some very light makeup on my face - I was meant to be a young schoolgirl she said, finally then she put on the elasticated pink Alice band. Standing back and admiring her work she said “Ahhh, you look so sweet. You’ll be the best schoolgirl at the party. I’m going to call you Alice - very suitable for you I think. Now you go downstairs and watch the telly while I prepare my outfit.
It was around an hour later that she came downstairs. I was looking forward to seeing what she was wearing. I hoped that it would be a St. Trinians-style school uniform, which I’d always found rather sexy. When she came into the lounge, I was disappointed because she was wearing a coat. I asked her to let me see her outfit but she told me there was no time and that it would be a surprise for me. She was right, we were running late. I put a coat on which covered my dress but that still left my shoes and ankle socks on display. We got to the party some half an hour late and parked on the street a few houses down. Walking arm-in-arm to the party house and Diane rang the bell. We only had to wait seconds before the door was opened by a man and a woman. “Amanda, Mike - this is Alice,” said Diane. I knew better than to interrupt her. “Say hello Alice.”
They smiled at me and said, ”Hello Alice.” Mike then offered to take our coats. Diane gave me one of her looks and I knew I had no choice, so I took off my coat and gave it to Mike.
“Oh my, oh my,” said Amanda, "Jane told me of your little joke that you were going to play on him, but I didn’t believe that you would manage to pull it off. Alice, you look lovely. I can’t wait to introduce you to the gang!”
I then realized that Amanda and Mike were not in fancy dress. Diane then took her coat off only to reveal that she wasn’t in fancy dress either, just a pair of culottes and a rather revealing black top with lace up detail front. “Come through to the back, everyone is waiting in anticipation,” Diane told me to follow her and we walked into a large room with some 50+ people, none of them in fancy dress. “Hello everyone. I’d like you to give a big cheer and a warm welcome to Alice.” Diane announced, Then she moved from in front of me and there was a collective gasp interspersed with Oohs! and Ahhs! And then everyone burst into laughter. I didn’t know where to put myself and just wanted the ground to swallow me up.
Jane then approached me saying “Alice, you don’t know how pleased I am to see you like this; we must spend some time together soon.” She kissed me on the cheek. Slowly, people went back into their groups and I was left pretty much alone. Diane had moved over to a guy who had been on his own, and was deep in conversation with him. I was so uncomfortable that I withdrew into myself and spent what seemed like forever just standing there like a wallflower. I thought that Diane would rejoin me soon, but by now she was sitting on the man’s lap with her arms around his neck.
I could see a couple of people glancing at me to see how I’d react and overheard one man saying to his partner “What a sissy!” I had to stand there until Jane then took my hand and led me to the center of the room. She then moved behind me, and shouted “Look, everyone!” before I knew it, she pulled up the hem of my dress, exposing my caged cock and my collared ball sack. Hands either side of me grabbed my arms ensuring that I couldn’t pull my dress down and cover myself. There was a cacophony of catcalls, whooping, and laughter until Diane called for hush and said “ As you can see, Alice is in chastity. That’s because her “cock’, or rather her ‘clit’ is useless. " She said, “Alice, this is Steve, my ex - don’t you think he’s manly? I certainly do. His stamina is legendary. He has no problem staying hard for me. I’ve thought of an appropriate full name for you - ‘AliceBanned,‘ because from now on you are banned from having any orgasms. You wearing that Alice Band gave me the idea - an amusing play on words, don’t you think? Jane, please take Alice home and prepare her for the night, as we planned earlier. I was relieved to get out of there, but apprehensive as to exactly what was going to happen to me next……
to be continued
My Descent into Cuckoldry Part 8. My Ordeal in the Cellar.
MY DESCENT INTO CUCKOLDRY PART 8, MY ORDEAL IN THE CELLAR
When Jane pulled up at Diane’s, she told me to get out of the car and follow her into the house. “From now on our training begins in earnest, so in the future, you will always walk behind Diane, me, or indeed any woman in whose charge you may be put. You are not equal, you are inferior to any woman, do you understand?” I nodded meekly, “Good, I have some things to show you.”
We went upstairs into Diane’s bedroom. "I told you when we met that I designed furniture." She then showed me a bedside cabinet. “This I made especially for Diane. Do you see these switches on the side? They control a baby listening device that enables Diane to hear anything from the room in the cellar. She can also turn that off, allow anyone in the cellar to hear any activity in here, and obviously, that too can be turned off if she wants privacy.” She then lifted the top hinged at the rear to reveal a small funnel-shaped basin with an open drain. “This is attached to a flexible pipe that goes into the cellar, but I’ll explain more about that another time, come with me.”
She led me downstairs through a kitchen door and down into a small room in the cellar. There was a wall with a door made of metal bars. She took out a key and unlocked it and went in, indicating that I follow her. She flicked on a light switch to reveal a room of some size. It was filled with several items, all covered with white sheets.
“This is our playroom. All the items under the sheets are of my design. In due course, you will become very familiar with all of them.” She then pulled one of the sheets off to reveal two enormous solid vertical pillars with slots on either side going all the way up, and sunk into both the floor and the ceiling. “Stand between the pillars and hold your hands up.” She picked up a couple of boards with semi-circular holes and slid one in horizontally in front of my wrists and neck, and then the other behind my neck. Pushing them together, she then pushed in heavy squared ‘u’ shaped pieces of metal that held the boards firmly together. She then produced two more boards and slid them on to secure my ankles Similarly. “Do you like my design? The slots enable me to secure you at different heights. I can have you with your feet totally on the floor or up on tiptoes if I wish you to be a little bit less comfortable.” She then pulled up my dress and with a couple of clothes pegs, clipped it up so that my bottom was exposed. “They say that the biggest sex organ in the body is the brain, I want you to think about all that has happened to you since you met Diane, the events of today, the bedside table I’ve shown you in Diane’s bedroom, the device that you’re secured in now and what delights might lie under all the other sheets. Most of all, think about what you are yet to experience once Diane comes home. I’ll leave you to mull it all over and build the anticipation. I’m going upstairs now, but don’t worry, I’ll come back to see you when Diane returns.“ She turned off the light and shut and locked the gate behind her, leaving my mind to run riot. I’d been ordered about, humiliated, and abused by two attractive women. I could have stood up for myself several times, but I’d let it happen. Not only had I not resisted, but I’d also helped them by obeying their demands and orders. I thought of the way I’d treated my ex-wife. I’d mistreated her and hurt her. She’d never deserved it. I knew that my feeble erections were caused by my guilt, and in my heart, I knew that I deserved and needed punishment, and that was perhaps why I was now being so submissive. I was scared by my predicament, yet I was also excited and feeling more alive than I had in a long time.
I have no idea how long it was before I heard footsteps coming in my direction. The gate was unlocked and the light switched on and Diane, Jane, and two other women stood in front of me. The two new women were called Karen and Melanie. ”I need to level with you Alice, I never intended to cure your limp penis problem. I misled you by leading you to believe that Jane cured her partner‘s problem by locking him in chastity. His chastity, like yours, is permanent.
“But Diane, you told me that Jane was now enjoying mind-blowing sex!” I said.
“Oh, I am Alice, but with masculine Alpha boyfriends, not with my sissy hubwife.” Said, Jane.
Jane went on to tell me that they had a small circle of successful women - ‘My‘ Diane, a Staff Nurse, Jane, a furniture designer, Karen, a horse stud farm/stable owner and Melanie, a lawyer - between them they were exceptionally wealthy and didn’t want or need men to support them. At some point in the past, they had all been let down by men and had vowed that they would never marry again, but would just ‘use’ men as and when it suited them, whether that be for sex or domestic service or their amusement. Jane‘s hubwife was, and I was to be, a servant and slave. Karen then added that she had drafted a letter of resignation that I would sign and they would post telling my employers that for health reasons I was leaving their employment immediately. I started to protest, but Karen produced a riding crop and whipped my bare bottom twice causing me to howl in agony.
”Lesson,” She said “ You will only speak when asked to, and you will ALWAYS obey!” Melanie then added to my horror that they knew that I had been unfaithful to my ex-wife and deserved all that would happen to me. Diane said, “I know that you desire my body, but you shall never have it. Karen wanted to geld you but the rest of us disagreed; if we took your balls, you would lose all sex drive, but by leaving you the desire, yet denying you the opportunity, we can have much more fun. Jane showed you around upstairs. I’m now going to join Steve in my bed. The baby monitor will allow you to hear everything, as it will me. I going to love a proper fucking with a real man almost as much as I will love hearing you suffering. Guess what - I’m going to have both! My friends will stay here to help, and Melanie will film it all. As you listen to our lovemaking, they will record your facial expressions, but the best part will be that when Steve slides his big cock into me, Karen will whip you savagely continuously until I cum. Every stroke and every cry of pain I hear will intensify my pleasure and increase the strength of my orgasm!”
Soon the sounds of lovemaking were to be heard through the baby monitor. The foreplay, the sighs, and the kissing made me long jealous of what I couldn’t have. It was lengthy. Jane, Karen, and Melanie were all taunting me, making comments about my inadequacy, and my lack of manliness, and asking me if I thought Diane was enjoying herself. And then the loud groans, satisfied sighs, and cries of ecstasy began. Karen then drew my attention by tapping my bottom with her crop. “Are you ready Alice? And then it began. Swish, and searing pain, then another and another. I couldn’t move or escape the searing pain. Swish, swish, swish. Diane could hear clearly as she called out “Oh, yes Steve, fuck me harder - Karen whip Alice harder. Harder and faster.“ The pain was agonizing and unrelenting until I was on the verge of passing out. Steve had remarkable stamina because his thrusting went on and on and on until I finally heard Diane call out that she was cumming, and Steve said he was cumming too. Simultaneous orgasms. Nobody could have doubted how well Steve had fucked Diane and how much she had enjoyed it. I was so glad that Diane had cum, as it meant that the whipping stopped.
Melanie was still filming my bottom. “We’ve got some great footage girls, but just look at poor Alice’s bum - look at the welts, and Karen’s drawn blood too!“
The girls freed me from the frame and laid me down face up on the floor, the cold floor soothing my burning backside. My head was placed between two pieces of wood and straps secured over my forehead and neck, my arms, wrists, shins, and ankles. These were anchored into the floor and left me with very little movement. My head I couldn’t turn at all. Jane inserted a device into my mouth which held my mouth open. Diane then entered the cellar, hand behind her back. “Alice, that was unbelievable. The sound of the whip, your cries, and your obvious suffering, all added to my pleasure, and all because you wanted me to orgasm so hard. But don’t worry, I believe in giving as well as taking - here’s your reward.” With that, she held out her used condom and lowered it into my restrained mouth. “Can you taste me on it, sweetie? See, I can treat you too! But don’t forget Steve.” And with that she upended the condom and putting her fingers together, she squeezed the contents into my open mouth. Karen and Melanie had their phones out and were taking pictures. “Isn’t that yummy Alice? The texture, is nice and slimy and salty tasting wouldn’t you agree? I want you to swill it around your mouth so you can savor it like a good wine!” I’ve never tasted my cum, any man’s cum before. It disgusted me, but I had no choice. Melanie removed the open-mouth gag and before I could attempt to spit the cum out, pushed the squat penis-shaped gag into my mouth and locked it in place. “It's your choice Alice, you either swallow Steve’s cum or you can savor it all night.” And with that, they all left the cellar laughing, once again leaving me in the darkness with my thoughts.
to be continued
When Jane pulled up at Diane’s, she told me to get out of the car and follow her into the house. “From now on our training begins in earnest, so in the future, you will always walk behind Diane, me, or indeed any woman in whose charge you may be put. You are not equal, you are inferior to any woman, do you understand?” I nodded meekly, “Good, I have some things to show you.”
We went upstairs into Diane’s bedroom. "I told you when we met that I designed furniture." She then showed me a bedside cabinet. “This I made especially for Diane. Do you see these switches on the side? They control a baby listening device that enables Diane to hear anything from the room in the cellar. She can also turn that off, allow anyone in the cellar to hear any activity in here, and obviously, that too can be turned off if she wants privacy.” She then lifted the top hinged at the rear to reveal a small funnel-shaped basin with an open drain. “This is attached to a flexible pipe that goes into the cellar, but I’ll explain more about that another time, come with me.”
She led me downstairs through a kitchen door and down into a small room in the cellar. There was a wall with a door made of metal bars. She took out a key and unlocked it and went in, indicating that I follow her. She flicked on a light switch to reveal a room of some size. It was filled with several items, all covered with white sheets.
“This is our playroom. All the items under the sheets are of my design. In due course, you will become very familiar with all of them.” She then pulled one of the sheets off to reveal two enormous solid vertical pillars with slots on either side going all the way up, and sunk into both the floor and the ceiling. “Stand between the pillars and hold your hands up.” She picked up a couple of boards with semi-circular holes and slid one in horizontally in front of my wrists and neck, and then the other behind my neck. Pushing them together, she then pushed in heavy squared ‘u’ shaped pieces of metal that held the boards firmly together. She then produced two more boards and slid them on to secure my ankles Similarly. “Do you like my design? The slots enable me to secure you at different heights. I can have you with your feet totally on the floor or up on tiptoes if I wish you to be a little bit less comfortable.” She then pulled up my dress and with a couple of clothes pegs, clipped it up so that my bottom was exposed. “They say that the biggest sex organ in the body is the brain, I want you to think about all that has happened to you since you met Diane, the events of today, the bedside table I’ve shown you in Diane’s bedroom, the device that you’re secured in now and what delights might lie under all the other sheets. Most of all, think about what you are yet to experience once Diane comes home. I’ll leave you to mull it all over and build the anticipation. I’m going upstairs now, but don’t worry, I’ll come back to see you when Diane returns.“ She turned off the light and shut and locked the gate behind her, leaving my mind to run riot. I’d been ordered about, humiliated, and abused by two attractive women. I could have stood up for myself several times, but I’d let it happen. Not only had I not resisted, but I’d also helped them by obeying their demands and orders. I thought of the way I’d treated my ex-wife. I’d mistreated her and hurt her. She’d never deserved it. I knew that my feeble erections were caused by my guilt, and in my heart, I knew that I deserved and needed punishment, and that was perhaps why I was now being so submissive. I was scared by my predicament, yet I was also excited and feeling more alive than I had in a long time.
I have no idea how long it was before I heard footsteps coming in my direction. The gate was unlocked and the light switched on and Diane, Jane, and two other women stood in front of me. The two new women were called Karen and Melanie. ”I need to level with you Alice, I never intended to cure your limp penis problem. I misled you by leading you to believe that Jane cured her partner‘s problem by locking him in chastity. His chastity, like yours, is permanent.
“But Diane, you told me that Jane was now enjoying mind-blowing sex!” I said.
“Oh, I am Alice, but with masculine Alpha boyfriends, not with my sissy hubwife.” Said, Jane.
Jane went on to tell me that they had a small circle of successful women - ‘My‘ Diane, a Staff Nurse, Jane, a furniture designer, Karen, a horse stud farm/stable owner and Melanie, a lawyer - between them they were exceptionally wealthy and didn’t want or need men to support them. At some point in the past, they had all been let down by men and had vowed that they would never marry again, but would just ‘use’ men as and when it suited them, whether that be for sex or domestic service or their amusement. Jane‘s hubwife was, and I was to be, a servant and slave. Karen then added that she had drafted a letter of resignation that I would sign and they would post telling my employers that for health reasons I was leaving their employment immediately. I started to protest, but Karen produced a riding crop and whipped my bare bottom twice causing me to howl in agony.
”Lesson,” She said “ You will only speak when asked to, and you will ALWAYS obey!” Melanie then added to my horror that they knew that I had been unfaithful to my ex-wife and deserved all that would happen to me. Diane said, “I know that you desire my body, but you shall never have it. Karen wanted to geld you but the rest of us disagreed; if we took your balls, you would lose all sex drive, but by leaving you the desire, yet denying you the opportunity, we can have much more fun. Jane showed you around upstairs. I’m now going to join Steve in my bed. The baby monitor will allow you to hear everything, as it will me. I going to love a proper fucking with a real man almost as much as I will love hearing you suffering. Guess what - I’m going to have both! My friends will stay here to help, and Melanie will film it all. As you listen to our lovemaking, they will record your facial expressions, but the best part will be that when Steve slides his big cock into me, Karen will whip you savagely continuously until I cum. Every stroke and every cry of pain I hear will intensify my pleasure and increase the strength of my orgasm!”
Soon the sounds of lovemaking were to be heard through the baby monitor. The foreplay, the sighs, and the kissing made me long jealous of what I couldn’t have. It was lengthy. Jane, Karen, and Melanie were all taunting me, making comments about my inadequacy, and my lack of manliness, and asking me if I thought Diane was enjoying herself. And then the loud groans, satisfied sighs, and cries of ecstasy began. Karen then drew my attention by tapping my bottom with her crop. “Are you ready Alice? And then it began. Swish, and searing pain, then another and another. I couldn’t move or escape the searing pain. Swish, swish, swish. Diane could hear clearly as she called out “Oh, yes Steve, fuck me harder - Karen whip Alice harder. Harder and faster.“ The pain was agonizing and unrelenting until I was on the verge of passing out. Steve had remarkable stamina because his thrusting went on and on and on until I finally heard Diane call out that she was cumming, and Steve said he was cumming too. Simultaneous orgasms. Nobody could have doubted how well Steve had fucked Diane and how much she had enjoyed it. I was so glad that Diane had cum, as it meant that the whipping stopped.
Melanie was still filming my bottom. “We’ve got some great footage girls, but just look at poor Alice’s bum - look at the welts, and Karen’s drawn blood too!“
The girls freed me from the frame and laid me down face up on the floor, the cold floor soothing my burning backside. My head was placed between two pieces of wood and straps secured over my forehead and neck, my arms, wrists, shins, and ankles. These were anchored into the floor and left me with very little movement. My head I couldn’t turn at all. Jane inserted a device into my mouth which held my mouth open. Diane then entered the cellar, hand behind her back. “Alice, that was unbelievable. The sound of the whip, your cries, and your obvious suffering, all added to my pleasure, and all because you wanted me to orgasm so hard. But don’t worry, I believe in giving as well as taking - here’s your reward.” With that, she held out her used condom and lowered it into my restrained mouth. “Can you taste me on it, sweetie? See, I can treat you too! But don’t forget Steve.” And with that she upended the condom and putting her fingers together, she squeezed the contents into my open mouth. Karen and Melanie had their phones out and were taking pictures. “Isn’t that yummy Alice? The texture, is nice and slimy and salty tasting wouldn’t you agree? I want you to swill it around your mouth so you can savor it like a good wine!” I’ve never tasted my cum, any man’s cum before. It disgusted me, but I had no choice. Melanie removed the open-mouth gag and before I could attempt to spit the cum out, pushed the squat penis-shaped gag into my mouth and locked it in place. “It's your choice Alice, you either swallow Steve’s cum or you can savor it all night.” And with that, they all left the cellar laughing, once again leaving me in the darkness with my thoughts.
to be continued
My Descent into Cuckoldry Part 9. Karen’s Stables.
MY DESCENT INTO CUCKOLDRY PART 9. KAREN‘S STABLES.
The next day I was told that I was to spend a week with each of the women in rotation, starting with Karen. Sometimes the others would visit to see how my training was going. I was allowed to change into my own clothes, although I did have to wear my camisole and panties underneath. Karen’s place was in the country and quite remote, it took about an hour to reach it. The track from the entrance gateway was so long that the stables weren’t visible until we had driven for several minutes, but as we rounded a small wood, it came into sight. It was a vast homestead comprised of barns, stables, outbuildings, and a farmhouse.
Karen pulled up outside a smaller stable block where a stable girl was unsaddling a 15-hand mare. “When you’ve finished with her Amy, I want you to come to the changing room and help me prep this one.”
Amy didn’t bat an eyelid, “I’ll be with you in a few minutes Karen.”
I followed Karen through a door into a small barn and into a room with toilets, showers, and benches. One wall was equipped with a number of cupboards and lockers. Karen told me to strip and stand against a wall where I saw metal cuffs. “Put your wrists in the cuffs,” she said “I’m going to remove your cage and Kali’s teeth bracelet but you will never ever be out of chastity with your hands-free.” I really wanted a break from the cage and happily obeyed. The cuffs were shut and self-locked. Then Amy arrived and seemed totally unfazed. “Give this beta a good wash down and prepare and fit the belt please Amy. Call me when you’re ready.” she went through another internal door. Amy got a bucket of water and soap and sponged me all over, concentrating on my genitals and bottom. I’d had a ‘horsey’ girlfriend years before. She and her horsey friends all had a no-nonsense way that they used to control creatures much larger and stronger than them, Amy had this same manner. She was probably 17 or 18, and I thought that she might be a softer touch than Karen. She went to a locker and brought a metal belt contraption with a metal strap that hung down, but obviously hinged up to secure to the belt at the front. She opened the belt and fitted it around my waist and locked it shut with a strong-looking padlock. It was only when she lifted up the crotch strap that I saw that it had an integral chastity cage and the cage had spikes in it! I panicked and kept moving from side to side to prevent her from finishing her job. She gave me an angry glare and went through the door that Karen had gone through. Shortly she returned with Karen. “You’ll regret your disobedience, Alice.“ Karen was strong and between her and Amy, they managed to maneuver my cock into the spiked section and locked the strap into place. Surprisingly the cage had a large diameter and the spikes only pressed lightly into my penis. However, it was obvious that any growth would make those spikes dig in much deeper. Going to the cupboards, Karen collected a metal dildo formed by several balls of decreasing sizes. She picked up a jar of Vaseline and rubbed a handful all over the ball shapes and, reaching under my bottom, she pushed the dildo firmly through a hole in the metal strap into my anus, and screwed it tightly into position. Freeing my wrists from the wall cuffs, she immediately secured them again behind my back.
I was led into an area where bales of straw were sitting under a high roof. “Stand on that bale of hay.” I did as I was told. Amy put a rope around my neck and tied it to a hook on the wall before picking up a long whippy cane and positioned herself ready to use it on me. Karen held up a small black box and asked me if I knew what it was. “It looks a bit like a tv remote Karen,” I replied.
“Clever girl, it IS a remote controller, but not for a television.” She pressed a button and suddenly a sharp shock hit me all the way up my anal passage. The dildo wasn’t just a dildo, it was designed to deliver shocks by remote control. “Amy, as Alice disrespected you and despite her already marked bottom, I think three would be in order.” Amy needed no further encouragement and putting all her force behind it, took a large swing and let loose. Searing, agonizing pain followed. If the riding crop had hurt, this was 10 times worse. I howled in pain. Amy walked in front of me and smiled. Returning behind me she took her second swing. I jerked and screamed. Once again she stood in front and gave a smug grin. Back and the third swipe was even worse than the previous ones. Amy returned to the front, kissed her hand a blew me her kiss.
Karen said, “There will be no more disobedience. That butt plug will ensure that. I only had it at half-power. Tomorrow you will visit the stud farm section. Amy, chain her in one of the stalls, one of the dirty ones will do. ”Amy, the controller in hand, had me follow her to the stalls. She looked at a couple, mumbling something about them being clean. The 3rd stall looked as though it hadn’t been cleaned for days, if not weeks.
“Perfect, deliciously fragrant.” She said, ”Come here.”
She picked up a chain that was fastened to the wall and padlocked it to my chastity belt. “You see that large pile of dung in front of you?” I nodded. “Kneel in front of it.” I did as I was told “ Now breathe in, smell it.” I hesitated. I felt the searing pain in my back passage, only worse than before. It took a while to recover. When I did, Amy said, “Next time it will be full power. Now, I want your nose no more than 1 inch away from it.” This time I obeyed immediately. She put her hand on the back of my head and pushed my face deep into the horse muck. ”Just because I’m young, don’t ever, ever think that I‘m an easy touch. I’ll be helping Karen tomorrow do we have some treats in store for you! - sweet dreams.”
ITS DISAPPOINTING WHEN HAVING SPENT TIME ON A STORY THAT, OF THE THOUSANDS WHO HAVE READ IT, SO FEW WRITE A REVIEW, COMMENT OR RATE IT. STILL TO COME WERE ‘THE STUD FARM’, ‘MAID TRAINING’ AND ‘I GET WHAT I DESERVE’, BUT UNLESS I GET MORE FEEDBACK, THEN I’M NOT REALLY MOTIVATED TO CONTINUE.
MY DESCENT INTO CUCKOLDRY CHAPTER 10 - The Stud Farm
“Wake up beta,” said Karen, “You’ve got a busy morning before you get any breakfast." She whipped me with her riding crop, “Stand up you pathetic little weed. You’ve got horse shit all over your face, we’ll need to clean that off.” She led me out of the stall and into the yard. There were iron clasps set into the middle of the yard. “Girls, come and help me” she called to two nearby stable girls. They grabbed me and forced me to the ground, lying on my back, between the clasps. Karen pulled a clasp over my neck and secured it with a padlock while the two girls did the same with clasps by my sides, securing my wrists and then my ankles similarly. One of the girls slipped off her shoes took off her jodhpurs positioned herself above my face and without a word, proceeded to urinate all over my face it was warm and some went into my mouth, leaving a salty taste. The other girl got a cloth and wiped away the residual horse shit. Amy and Karen were both laughing, obviously enjoying my degradation. “You will stay here until your ‘lesson’ in 30 minutes. I want you to reflect on your situation and start to come to terms with the changes in your life, that it is now in our hands and no longer under your control.”
I lay there helpless but at the same time slightly turned on by my predicament. I felt my cock was getting aroused and was beginning to grow slightly. As it swelled I felt the spikes begin to dig in. I wanted to stop this but I couldn’t and as my cock grew the pain worsened until I cried out for help. The pain became agonizing as the spikes pierced through my skin. It was minutes later that Karen came to see what was happening and by the time she arrived, the pain had subsided as my cock shrank. “Lesson number one,” she said, “Erections are not allowed for betas, they are disrespectful to your superiors. You will have to learn this the painful way but don’t worry, by the time your training is finished, you won’t ever be able to get stiff again. Your seed is useless, not fit for breeding. Horses that aren’t thoroughbreds are gelded here. The spiked cage will only remain until I can make an appointment for the vet to castrate you. Now, time for your next lesson.” She called the girls who helped her to unlock the clasps. They took me inside and forced me to my knees then locked my wrists to metal rings behind me, by my feet. Then they produced a hood with a pipe coming out of the mouth opening. The pipe had a funnel attached and the hood had a metal ring at the rear. This hood was put over my head and laced up tightly. Next, a rope was put through the ring at the rear of my head and tightened to another ring set on the floor behind me. This forced me to lean my head backward, “Are you ready for breakfast?” Asked Karen. Suddenly a sharp pain zapped me deep in my arse, it was agonizing. “That’s what will happen if you refuse to swallow your breakfast - here it is; I’m pouring it into the funnel now. Here it comes.” Nothing came and I thought that she was teasing me to see how I would react, but then a gooey thick liquid started flowing into my mouth. I didn’t like the taste one bit, it was quite pungent and revolting and I tried to spit it out, but the pipe that was in my mouth was designed to prevent this. I did however manage to hold it in my mouth and prevent going down my throat. “Ah, ah, ah,” said Karen, and once again my anal passage contorted as a larger electric shock shot up into it. It was intolerable. “You are going to swallow. This lovely thoroughbred horse semen is full of goodness and as there is so much surplus every time we extract it, I don’t want it going to waste. This will be your breakfast every morning. This not only saves me buying your breakfast, but it will also make me money as I will be charging ladies for the fun of feeding you, rather like people feed animals in a petting zoo. Many ladies ride here who have said that they are very excited at the thought - I’ve made bookings and taken deposits already. I will also make you tell me who all your former girlfriends are. You must have been a big disappointment to them, wimp. I bet they’ll pay big money to see you swallow horse semen - who knows, perhaps even more if I invite them to bring their boyfriend's and husband's semen to feed you! Now, SWALLOW or else.” I had no option; I couldn’t bear the pain in my anal passage again, and so I started to swallow. It made me feel nauseous as the thick gooey horse semen slid slowly downwards, coating the walls of my throat as it did so.
I lay there helpless but at the same time slightly turned on by my predicament. I felt my cock was getting aroused and was beginning to grow slightly. As it swelled I felt the spikes begin to dig in. I wanted to stop this but I couldn’t and as my cock grew the pain worsened until I cried out for help. The pain became agonizing as the spikes pierced through my skin. It was minutes later that Karen came to see what was happening and by the time she arrived, the pain had subsided as my cock shrank. “Lesson number one,” she said, “Erections are not allowed for betas, they are disrespectful to your superiors. You will have to learn this the painful way but don’t worry, by the time your training is finished, you won’t ever be able to get stiff again. Your seed is useless, not fit for breeding. Horses that aren’t thoroughbreds are gelded here. The spiked cage will only remain until I can make an appointment for the vet to castrate you. Now, time for your next lesson.” She called the girls who helped her to unlock the clasps. They took me inside and forced me to my knees then locked my wrists to metal rings behind me, by my feet. Then they produced a hood with a pipe coming out of the mouth opening. The pipe had a funnel attached and the hood had a metal ring at the rear. This hood was put over my head and laced up tightly. Next, a rope was put through the ring at the rear of my head and tightened to another ring set on the floor behind me. This forced me to lean my head backward, “Are you ready for breakfast?” Asked Karen. Suddenly a sharp pain zapped me deep in my arse, it was agonizing. “That’s what will happen if you refuse to swallow your breakfast - here it is; I’m pouring it into the funnel now. Here it comes.” Nothing came and I thought that she was teasing me to see how I would react, but then a gooey thick liquid started flowing into my mouth. I didn’t like the taste one bit, it was quite pungent and revolting and I tried to spit it out, but the pipe that was in my mouth was designed to prevent this. I did however manage to hold it in my mouth and prevent going down my throat. “Ah, ah, ah,” said Karen, and once again my anal passage contorted as a larger electric shock shot up into it. It was intolerable. “You are going to swallow. This lovely thoroughbred horse semen is full of goodness and as there is so much surplus every time we extract it, I don’t want it going to waste. This will be your breakfast every morning. This not only saves me buying your breakfast, but it will also make me money as I will be charging ladies for the fun of feeding you, rather like people feed animals in a petting zoo. Many ladies ride here who have said that they are very excited at the thought - I’ve made bookings and taken deposits already. I will also make you tell me who all your former girlfriends are. You must have been a big disappointment to them, wimp. I bet they’ll pay big money to see you swallow horse semen - who knows, perhaps even more if I invite them to bring their boyfriend's and husband's semen to feed you! Now, SWALLOW or else.” I had no option; I couldn’t bear the pain in my anal passage again, and so I started to swallow. It made me feel nauseous as the thick gooey horse semen slid slowly downwards, coating the walls of my throat as it did so.
