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!”
