My First Sissy Crossdresser!
I encountered my first sissy crossdresser one night catching the bus home from work back in November 1981. She was standing on the corner across the street and some drunk guy was all over her fondling, trying to kiss, humping and grinding on her ass. Suddenly I heard, "YOU'RE A FUCKING DUDE!"
He walked away mumbling and cussing and she began to cross the street coming straight to me. Tall brunette, hardly any make up, very cute, white top, shiny black disco pants, slutty heels, painted toe and fingers nails and she smelled great! Maybe is was a pheromone thing with the perfume but it kinda aroused me but I dared not to stare. She got directly in front of me and leaned to the left against the pole shifting her hips to her weight on one leg which was just enough to make her ass jiggle. That's when I looked! She had the ass of a woman, all natural bubble butt.
She looked over her right shoulder and asked me if I had a light. I responded, "No ma'am, I don't smoke." She went, "Hmm, ma'am?" "Did you not hear the drunk guy?" I responded, "I did but its cool because I got a cousin into that dressing up like a girl thing." She formally introduced herself to me as Susan and I told her my name as we shook hands at which time I noticed her bulge. She was untucked and I could clearly (even in low light) make out the unmistakable outline of a possible short penis but very thick head.
She noticed me staring at her bulge and asked me if I liked it. I responded, "I don't know?" She asked me if I'd like to touch it as she guided my hand to it.
Fuck! It was warm and moist and I could feel her precum which had soaked through her panties and disco pants.
I was so turned on that I didn't know what to do and there we were walking back to her apartment about a block away.
Now I'm naked, standing in her bedroom and she's sitting on the bed in what was an awkward moment. She begins to scoot backwards towards the head of the bed saying, "C'mon, whatever happens lets just let it happen." While she's doing this I could not keep my eyes off her short cock with a huge mushroom as it dripped ribbons of precum on her light blue satin bedspread making a glistening trail.
In seconds I was on top of her, spread her legs, cupped her ass and tried to get as much of her cock in my mouth as I could! She squirmed and moaned and within seconds exploded in my mouth and I had no clue what to do so I ate her sperm! By now she's screaming and bucking and I panicked and jumped off the bed while she laid there holding her cock and convulsing. I asked her was she okay and she stammered with a big smile as she tried to catch her breath and said yes..yes..I'm fine. She told me no man had ever sucked her dick before and it caught her off guard and drove her nuts!!
I got back in the bed and we pretty much had foreplay with lots of kissing and stuff. She again exploded within minutes on my thigh. I next ate her asshole like a pussy which lead to another explosion on the bed while she was grinding.
When I finally penetrated her while she was face down and she bucked and squirmed so much that I came deep inside her asspussy within 5 minutes with a huge load that drained my balls. She bucked her hips and milked me for her drop as she blew her final load on the bed, both of us screaming and cussing until we collapsed.
We started laughing and I said, "That was so fucking nasty and hot!" She told me she never had a man make sensual love to her. All they did was fuck her but this was different. I told her this was my first time with her type and all I knew was what I do with a real girl so why should it be different? She agreed.
Every Friday after that I until I left for the military a few months later I made love to my sissy and it kinda fucked with my head. I wasn't gay, I loved pussy but this sissy crossdresser thing was all new to me and really enjoyed making love to her asshole and body.
So I've come to the conclusion that I'm not gay or bi, I'm just FUCKING NASTY and I like my sissies all dressed up and untucked because that was thing that droved me nuts about Susan. She was always hard or semi erect and always untucked.
30 years later my wife and I are fucking and we shared our nastiest sex encounter with each other. When I told her my story it turned her on and we fucked until about 4 in the morning.
One day we plan to add a sissy to our list of sexual plans for the future. For now, we are seeking 2 bisexual bbc, medium build, minimum 8 inches, verbal and versatile, 40's to 50's. No thugs
He walked away mumbling and cussing and she began to cross the street coming straight to me. Tall brunette, hardly any make up, very cute, white top, shiny black disco pants, slutty heels, painted toe and fingers nails and she smelled great! Maybe is was a pheromone thing with the perfume but it kinda aroused me but I dared not to stare. She got directly in front of me and leaned to the left against the pole shifting her hips to her weight on one leg which was just enough to make her ass jiggle. That's when I looked! She had the ass of a woman, all natural bubble butt.
She looked over her right shoulder and asked me if I had a light. I responded, "No ma'am, I don't smoke." She went, "Hmm, ma'am?" "Did you not hear the drunk guy?" I responded, "I did but its cool because I got a cousin into that dressing up like a girl thing." She formally introduced herself to me as Susan and I told her my name as we shook hands at which time I noticed her bulge. She was untucked and I could clearly (even in low light) make out the unmistakable outline of a possible short penis but very thick head.
She noticed me staring at her bulge and asked me if I liked it. I responded, "I don't know?" She asked me if I'd like to touch it as she guided my hand to it.
Fuck! It was warm and moist and I could feel her precum which had soaked through her panties and disco pants.
I was so turned on that I didn't know what to do and there we were walking back to her apartment about a block away.
Now I'm naked, standing in her bedroom and she's sitting on the bed in what was an awkward moment. She begins to scoot backwards towards the head of the bed saying, "C'mon, whatever happens lets just let it happen." While she's doing this I could not keep my eyes off her short cock with a huge mushroom as it dripped ribbons of precum on her light blue satin bedspread making a glistening trail.
In seconds I was on top of her, spread her legs, cupped her ass and tried to get as much of her cock in my mouth as I could! She squirmed and moaned and within seconds exploded in my mouth and I had no clue what to do so I ate her sperm! By now she's screaming and bucking and I panicked and jumped off the bed while she laid there holding her cock and convulsing. I asked her was she okay and she stammered with a big smile as she tried to catch her breath and said yes..yes..I'm fine. She told me no man had ever sucked her dick before and it caught her off guard and drove her nuts!!
I got back in the bed and we pretty much had foreplay with lots of kissing and stuff. She again exploded within minutes on my thigh. I next ate her asshole like a pussy which lead to another explosion on the bed while she was grinding.
When I finally penetrated her while she was face down and she bucked and squirmed so much that I came deep inside her asspussy within 5 minutes with a huge load that drained my balls. She bucked her hips and milked me for her drop as she blew her final load on the bed, both of us screaming and cussing until we collapsed.
We started laughing and I said, "That was so fucking nasty and hot!" She told me she never had a man make sensual love to her. All they did was fuck her but this was different. I told her this was my first time with her type and all I knew was what I do with a real girl so why should it be different? She agreed.
Every Friday after that I until I left for the military a few months later I made love to my sissy and it kinda fucked with my head. I wasn't gay, I loved pussy but this sissy crossdresser thing was all new to me and really enjoyed making love to her asshole and body.
So I've come to the conclusion that I'm not gay or bi, I'm just FUCKING NASTY and I like my sissies all dressed up and untucked because that was thing that droved me nuts about Susan. She was always hard or semi erect and always untucked.
30 years later my wife and I are fucking and we shared our nastiest sex encounter with each other. When I told her my story it turned her on and we fucked until about 4 in the morning.
One day we plan to add a sissy to our list of sexual plans for the future. For now, we are seeking 2 bisexual bbc, medium build, minimum 8 inches, verbal and versatile, 40's to 50's. No thugs
7 years ago
