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.
