My Qualifications to Write About Crossdressing
- 2 years ago
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My Journey Into Crossdressing. free porn video
The following story is 100% true. Only the names have been changed.
About 11 years ago, when I was 28, I met a 40 year old single mum of 2 called Michelle.
We met through a mutual friend. The relationship was purely a sexual relationship. I had just broken up with my girlfriend of 3 years, and she had been single for 7 years after splitting with her violent ex.
The first day we met, we ended up sleeping together. As we lay in bed afterwards, we started talking about what we liked and didn't like in bed.
She told me that she liked to finger a mans anus while she sucked his cock. I wasn't too keen on the idea, but after a couple of drinks I decided to let her do it.
The orgasm I had was unbelievable, and my entire body shook when I came. We had a little rest then she asked if I wanted her to do it again. I immediately said yes, so she started to probe my anus with her fingers once more. I told her to try two fingers, then I wanted three. At that point she stopped what she was doing and sat up on the bed. She looked straight at me. I didn't know what she was thinking of what she was going to say or do next. Then she stood up, walked over to her wardrobe, and brought out a shoebox. She brought it over to the bed and handed it to me. "Look inside" she said, so I did. I was faced with several dildos of different lengths and thicknesses. "Pick one" she said. So I pulled out a 7" dildo that was quite slim. She reach into her bedside table and pulled out a bottle of lube. "Lie down and relax, I think you are going to enjoy this" she said. So I did as she said, then she started to lube up my ass, then she rubbed some lube onto her dildo and started to slowly slide it in and out of my ass. My cock became instantly hard and I started to stroke it. At this point she slapped my hand away from my cock and said "what the fuck do you think you are doing. You're not allowed to touch that until I tell you" so I apologised and placed my hands behind my head. She continued to fuck my arse with the dildo, deeper and deeper, faster and faster. I started to moan with pleasure, then before I knew what I was saying, I was begging her to fuck me. She had awakened my 'Inner Slut'. I was loving every minute of it. I told her to stop. "Why" she said. "Try a bigger one" I replied. So she reached for her biggest dildo, it must've been 12 inches long, and it was thick.
She started to slowly work it into my ass. It hurt, but I soon got used to it. She started to thrust it into me as deep as she could. I was in heaven, I had never thought I would enjoy something so much. Her thrusts got faster and faster. "Stroke your cock" she said, so I did. I must only stroked it a dozen times when I came, my hot cum squirted all over me. My entire body shook with pleasure. Then she pulled her dildo out of my ass, laid beside me and started to feed me my own cum. After she had fed me all my cum, she looked into my eyes and said "I think I'll go shopping tomorrow, I'm going to buy you something that I think you'll like".then we fell asleep in each other's arms.
The following morning, I woke up to find that Michelle had gone shopping. She'd left me a note. The note said 'I won't be too long. Get yourself a bath and have a shave. I'm bringing you back a nice surpise'. I did as she asked. I had a shave and got into the bath. Michelle arrived home while I was still in the bath. She told me to give her a few minutes to get 'everything' ready. So I waited in the bathroom for her to shout me. I walked into the bedroom to find her under the bedclothes. "Pull the covers back" she said, so I did. I was speechless, she was laying there, wearing a big black strap on cock. "That's not all" she said. She pointed to a couple of shopping bags in the corner of the room. "Look inside those, they're for you". So I picked ups the bags and placed them on the bed. I opened the first bag, it contained a Pretty little pink dress and some matching high heels. I looked I the other bag, I had a black bouffant wig, black hold up stockings and the a lipstick that was the brightest shade of red that I had ever seen. I looked at her, she looked back at me. "I'm going to make you my bitch tonight" she said.
And she did.
TO BE CONTINUED.....
About 11 years ago, when I was 28, I met a 40 year old single mum of 2 called Michelle.
We met through a mutual friend. The relationship was purely a sexual relationship. I had just broken up with my girlfriend of 3 years, and she had been single for 7 years after splitting with her violent ex.
The first day we met, we ended up sleeping together. As we lay in bed afterwards, we started talking about what we liked and didn't like in bed.
She told me that she liked to finger a mans anus while she sucked his cock. I wasn't too keen on the idea, but after a couple of drinks I decided to let her do it.
The orgasm I had was unbelievable, and my entire body shook when I came. We had a little rest then she asked if I wanted her to do it again. I immediately said yes, so she started to probe my anus with her fingers once more. I told her to try two fingers, then I wanted three. At that point she stopped what she was doing and sat up on the bed. She looked straight at me. I didn't know what she was thinking of what she was going to say or do next. Then she stood up, walked over to her wardrobe, and brought out a shoebox. She brought it over to the bed and handed it to me. "Look inside" she said, so I did. I was faced with several dildos of different lengths and thicknesses. "Pick one" she said. So I pulled out a 7" dildo that was quite slim. She reach into her bedside table and pulled out a bottle of lube. "Lie down and relax, I think you are going to enjoy this" she said. So I did as she said, then she started to lube up my ass, then she rubbed some lube onto her dildo and started to slowly slide it in and out of my ass. My cock became instantly hard and I started to stroke it. At this point she slapped my hand away from my cock and said "what the fuck do you think you are doing. You're not allowed to touch that until I tell you" so I apologised and placed my hands behind my head. She continued to fuck my arse with the dildo, deeper and deeper, faster and faster. I started to moan with pleasure, then before I knew what I was saying, I was begging her to fuck me. She had awakened my 'Inner Slut'. I was loving every minute of it. I told her to stop. "Why" she said. "Try a bigger one" I replied. So she reached for her biggest dildo, it must've been 12 inches long, and it was thick.
She started to slowly work it into my ass. It hurt, but I soon got used to it. She started to thrust it into me as deep as she could. I was in heaven, I had never thought I would enjoy something so much. Her thrusts got faster and faster. "Stroke your cock" she said, so I did. I must only stroked it a dozen times when I came, my hot cum squirted all over me. My entire body shook with pleasure. Then she pulled her dildo out of my ass, laid beside me and started to feed me my own cum. After she had fed me all my cum, she looked into my eyes and said "I think I'll go shopping tomorrow, I'm going to buy you something that I think you'll like".then we fell asleep in each other's arms.
The following morning, I woke up to find that Michelle had gone shopping. She'd left me a note. The note said 'I won't be too long. Get yourself a bath and have a shave. I'm bringing you back a nice surpise'. I did as she asked. I had a shave and got into the bath. Michelle arrived home while I was still in the bath. She told me to give her a few minutes to get 'everything' ready. So I waited in the bathroom for her to shout me. I walked into the bedroom to find her under the bedclothes. "Pull the covers back" she said, so I did. I was speechless, she was laying there, wearing a big black strap on cock. "That's not all" she said. She pointed to a couple of shopping bags in the corner of the room. "Look inside those, they're for you". So I picked ups the bags and placed them on the bed. I opened the first bag, it contained a Pretty little pink dress and some matching high heels. I looked I the other bag, I had a black bouffant wig, black hold up stockings and the a lipstick that was the brightest shade of red that I had ever seen. I looked at her, she looked back at me. "I'm going to make you my bitch tonight" she said.
And she did.
TO BE CONTINUED.....
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