Sam Cat Role Play
- 1 year ago
- 17
- 0
Switch & Role Play On Halloween free porn video
It was halloween and I knew exactly who I was going to be. I was done with vampires and monsters, plugs and sockets. No, tonight I was going to be the ugliest woman alive. I knew I would never be an even passable woman, and that is what made this all the more fun. I was an attractive man, but one that could never, even remotely be made to look like a woman, so why even try. And that is what my costume would be all about.
I smiled as I looked at myself in the mirror. I had hit most of the tranny stores in Manhattan and even some of them in Brooklyn and Queens in search of heels that would support my weight, tights to fit my thighs, a skirt that was right for my measurements, as well as a wig and makeup for my lips and face. Just enough to have put in an effort without really trying. What was looking back at me was perfect.
I wore a wig that somewhat matched the color of my natural hair, a more natural color lipstick to fit my complexion, and a string of pearls of course. I wasn't after guys, but had heard that women go nuts for a man in a skirt. I was about to put that to a test.
I took a cab to my friend's apartment to somewhat conceal myself from wandering eyes, but alas, when I got out even in the steps to his building I still got heckled by a few couples who catcalled and whistled in mock appreciation. I smiled and nodded at their efforts, which only made it all the better. And yes, it gave me a bit of a thrill to know that people were making the effort, knowing I hadn't.
The doorman nodded at me, hiding his smile, so even the paid help wasn't taking it too seriously. Up the elevator with a couple and the woman asked me what I was supposed to be. I replied "A Cheesy Dame." They both cracked up, telling me I had hit that on the head. When I arrived at the party, everyone turned to look as I entered the door. I cried out, "What does a girl have to do to get a drink around here?"
The people who knew me laughed, the others just stared and shook their heads in mock dismay.
As the evening progressed I got my share of ass pinches and phony come-on lines from couples and single guys introducing themselves, but it wasn't until close to 11 that a woman approached me with a slight slur to her speech, "So what are you supposed to be, a trick or a treat?" Her eyebrow went up in question as she grinned at me over her drink.
She was about as much of a construction worker as I was a lady. Even with her hard hat and tool belt, anyone could see the curves that her T-shirt barely hid. Even with the sleeves rolled up and her fake American eagle tattoo.
"Which would you like me to be?"
The two of us started verbally sparring back and forth. Our words entwined and our bodies followed suit. We began to slide along each other until I realized she was very openly hitting on me. "So this is what it feels like," I asked myself.
She was bold and straight-forward, playing the part of a hard hat all the way through. I was enjoying it and begin to grow a little more shy the tougher she got. I was also getting aroused, but didn't want to look down to see if my bulge was showing beneath my short mid-thigh skirt. I didn't have to wait for long because she smiled at me as she reached out and grabbed my dick, holding it as she slid nearer.
"That's quite a package you've got. Sure you know how to use it?"
Her eyes stared me down as her rough voice showed me who was going to be the boss later on. I almost gulped, not sure if I was really ready for this. I think she knew, my nervousness showed through my smile.
"What do we say we lose this place and head over to my place. I've got some etchings I think you might like..."
I almost laughed at the absurdity of her line but didn't want to break the flow. I felt like I was acting the part and didn't want to let him down, wait, did my brain just say "him"?
When the cab door closed I realized these weren't just roles we were playing, this was going to be the of the direction the night. I could see the cab driver watching us in the mirror, shaking his head as he saw what was going on. He took his hard hat off, reached over and planted a kiss on my lips. His tongue shoved its way past my lips and forced my own tongue back into my mouth. His breath smelled like cigarettes and scotch and I could feel his hand slide up my leg as his finger slid past my cock, straight to where my vagina would have been. Barely lingering to stroke me or fondle my balls, he/she slid her finger to dawdle at my ass.
Not that I'm a twink, but I thought "Oh my God, is this what it's like to be a woman?" I kind of panicked a little until my construction worker for the night backed off a little. "Sorry if I'm moving too fast, we can slow down if you'd like."
I shook my head and said that it was okay, it just kind of took me by surprise.
"Good," was all she said as the cab pulled up in front of a very well appointed apartment building. We went inside and up an elevator to an open floor loft. It must have been 2,500 square feet with very little furniture.
We went through the preliminaries of asked if I wanted a drink and me asking about the etchings. Both of us knowing that was not why we were there.
We went back to sucking face, pulling her t-shirt off over her head as two very large DD breasts fell out. Her tight body gave her the look of an ex-gymnast, broad shoulders, narrow waist, and just slightly wide hips. She grabbed my shirt and lowered the zipper, revealing my shaved legs and a pair of black thigh-highs. My cock was raging as she turned me around, sliding her hand over the fine nylon and following the curve of my hips between my ass cheeks. She spanked me once on either cheek before sitting back in a lounge chair and sliding her jeans wide.
Her left hand traced the outline of what looked like a healthy cock as she said, "I hope you can suck as good as you look." Flipping back between her male/female personalities just about blew my mind when she laughed and pulled out a rubber penis.
"I bought this in a toy store. Something that dykes apparently use when they want to butch it up." She laughed, "The look on your face was priceless though." Pulling her jeans off she looked at me with boozy eyes, "but I was serious about you sucking." She spread her legs as she started massaging an absolutely gorgeous and perfectly trimmed pussy.
"Come on girl, why don't you kick your heels off and make me cum?"
I did my best to look sexy as I removed my heels and rolled my nylons down. I turned over to show her my shaved ass, and yes I shaved it for the party, before sliding a finger down past my cheeks and around my own pucker. She kept massaging herself in slow, sensual circles, inviting me over with an equally slow motion of her other finger.
I gave myself two strokes before kneeling at her pussy and began to taste that salty brine I know and love so well. I played with her labia, feeling her hands hold me there. I moved up to her clit, licking and tonguing it like a kitten at a bowl of milk. I slid down to that oh so velvety and soft space at the base of her sex, before moving even further down to rim her ass. Needless to say her mouth was like a construction worker's. Between moans she was telling me to eat her out, rim her ass, show me what a whore can do, finger my own ass. When I didn't jump on that last one quick enough she got up and went to another room. I sat there wondering what was going on before she walked out with a strap-on, stroking it with lube as if jerking a cock.
"Come on you little whore. Bend over that leather couch over there and spread your cheeks for me. Don't you want some stud breaking you? Isn't that why you dressed up like a little whore and pouted your lips like you wanted to suck a real cock?" She giggled as she told me it was edible lube, "cherry flavor."
There I was naked, lying down on her floor, my body spread out as she fed me her cock. She reached down and stroked me, playing with my balls as her cock slid in and out of my mouth. I was moaning as her finger tips moved from my own cock/clit to my man pussy to my nipples, squeezing and twisting and pinching and pulling them until I was on the verge of cumming. I started begging her to let me cum as if I was a little girl.
"Do you want to cum? Do you want to cum bitch?"
I eagerly begged her to let me. She grabbed my knees and threw them back until the touched my ears, then fucked me Amazon style. She plunged her sopping wet pussy onto my cock as her strap-on bounced with each thrust. All I could do was beg for more. Was that really me I was hearing? Was I one step closer to being the slut I dressed out to be at the start of the evening?
"Oh God Yes!" I heard. "Fuck me harder!" I screamed. "Make me cummmmmmmm." I pleaded.
At some point she lifted up from my cock and on the next thrust, plunged her strap into my waiting ass. My eyes bulged and my mind leapt, but my anus accepted what had just happened as I crossed over and kept begging her for more, only this time as her real-time slut. It blew my mind how quickly and easily it happened, but there I was, on my back, my hands playing with my cock and my nipples as she slid her strap-on into me with loving affection.
She saw it too as her entire body shifted into a king and loving man, smiling between her thrusts, caressing my chin, sliding a finger into my mouth, pulling on my nipples and holding my waist as she slowly and sensually slid in and out of my ass.
"Was this love?" I asked myself? "I'm not a slut, but wow, did this feel good." "Was this me enjoying my own sluttiness?" "But, God did he feel good in me."
I was so torn with what was going on inside of me, but I was loving the results I was feeling.
She would bend down as she thrust in to kiss me and to lick my nipples, before straightening up again as she pulled out to stroke me a few times.
At one point I was non my hands and knees getting fucked up my ass, at another I was on my back as her pussy drenched my face, at another she lay back on her couch as I ate her like a pro feeling the waves of pleasure from the vibrator that was stuck in me. But the best was the moment I was when she was on her side as I lid in and out of her and her hand reached down to gently rub my balls and then to pull my dick out of her and politely slide it into her ass. Her ass was slick with her juices and fit my cock perfectly. She looked over her shoulder, into my eyes and smiled. Her moans turned into deep grunts as our passion turned from her pussy to her ass.
In a few thrusts she reached into her bedside table to pull out a rabbit that she quickly slid into her slit. I quickly felt the vibrations and gyrations of that sex toy as it massaged both of us to climax. Even after cumming we continued our anal fucking. The pleasures were amazing. Hard and wet, slick and orgasmic. She raised her leg to climax, then lowered it to regain herself, raised it again as she came and lowered it to rest. All the while I continued my pumping, flicking her clit, fingering my own ass and playing with my own balls, pinching her nipples and then mine - it was truly a night for two sluts to be our unabashed and honest selves as we gave into ourselves together.
I stayed the night, and in the morning fucked again, until it was time to shower and leave. She had other thoughts in mind. No shower and to walk the walk of shame home to show everyone on the street just how much of a whore I had been last night.
The laughter from the security guards in her building was just the beginning of my shame as I realized I had been turned into one hell of a whore of a girl in just one night by one hell of a man. And yes, I wanted him to do it again, if he would only answer my call...
I smiled as I looked at myself in the mirror. I had hit most of the tranny stores in Manhattan and even some of them in Brooklyn and Queens in search of heels that would support my weight, tights to fit my thighs, a skirt that was right for my measurements, as well as a wig and makeup for my lips and face. Just enough to have put in an effort without really trying. What was looking back at me was perfect.
I wore a wig that somewhat matched the color of my natural hair, a more natural color lipstick to fit my complexion, and a string of pearls of course. I wasn't after guys, but had heard that women go nuts for a man in a skirt. I was about to put that to a test.
I took a cab to my friend's apartment to somewhat conceal myself from wandering eyes, but alas, when I got out even in the steps to his building I still got heckled by a few couples who catcalled and whistled in mock appreciation. I smiled and nodded at their efforts, which only made it all the better. And yes, it gave me a bit of a thrill to know that people were making the effort, knowing I hadn't.
The doorman nodded at me, hiding his smile, so even the paid help wasn't taking it too seriously. Up the elevator with a couple and the woman asked me what I was supposed to be. I replied "A Cheesy Dame." They both cracked up, telling me I had hit that on the head. When I arrived at the party, everyone turned to look as I entered the door. I cried out, "What does a girl have to do to get a drink around here?"
The people who knew me laughed, the others just stared and shook their heads in mock dismay.
As the evening progressed I got my share of ass pinches and phony come-on lines from couples and single guys introducing themselves, but it wasn't until close to 11 that a woman approached me with a slight slur to her speech, "So what are you supposed to be, a trick or a treat?" Her eyebrow went up in question as she grinned at me over her drink.
She was about as much of a construction worker as I was a lady. Even with her hard hat and tool belt, anyone could see the curves that her T-shirt barely hid. Even with the sleeves rolled up and her fake American eagle tattoo.
"Which would you like me to be?"
The two of us started verbally sparring back and forth. Our words entwined and our bodies followed suit. We began to slide along each other until I realized she was very openly hitting on me. "So this is what it feels like," I asked myself.
She was bold and straight-forward, playing the part of a hard hat all the way through. I was enjoying it and begin to grow a little more shy the tougher she got. I was also getting aroused, but didn't want to look down to see if my bulge was showing beneath my short mid-thigh skirt. I didn't have to wait for long because she smiled at me as she reached out and grabbed my dick, holding it as she slid nearer.
"That's quite a package you've got. Sure you know how to use it?"
Her eyes stared me down as her rough voice showed me who was going to be the boss later on. I almost gulped, not sure if I was really ready for this. I think she knew, my nervousness showed through my smile.
"What do we say we lose this place and head over to my place. I've got some etchings I think you might like..."
I almost laughed at the absurdity of her line but didn't want to break the flow. I felt like I was acting the part and didn't want to let him down, wait, did my brain just say "him"?
When the cab door closed I realized these weren't just roles we were playing, this was going to be the of the direction the night. I could see the cab driver watching us in the mirror, shaking his head as he saw what was going on. He took his hard hat off, reached over and planted a kiss on my lips. His tongue shoved its way past my lips and forced my own tongue back into my mouth. His breath smelled like cigarettes and scotch and I could feel his hand slide up my leg as his finger slid past my cock, straight to where my vagina would have been. Barely lingering to stroke me or fondle my balls, he/she slid her finger to dawdle at my ass.
Not that I'm a twink, but I thought "Oh my God, is this what it's like to be a woman?" I kind of panicked a little until my construction worker for the night backed off a little. "Sorry if I'm moving too fast, we can slow down if you'd like."
I shook my head and said that it was okay, it just kind of took me by surprise.
"Good," was all she said as the cab pulled up in front of a very well appointed apartment building. We went inside and up an elevator to an open floor loft. It must have been 2,500 square feet with very little furniture.
We went through the preliminaries of asked if I wanted a drink and me asking about the etchings. Both of us knowing that was not why we were there.
We went back to sucking face, pulling her t-shirt off over her head as two very large DD breasts fell out. Her tight body gave her the look of an ex-gymnast, broad shoulders, narrow waist, and just slightly wide hips. She grabbed my shirt and lowered the zipper, revealing my shaved legs and a pair of black thigh-highs. My cock was raging as she turned me around, sliding her hand over the fine nylon and following the curve of my hips between my ass cheeks. She spanked me once on either cheek before sitting back in a lounge chair and sliding her jeans wide.
Her left hand traced the outline of what looked like a healthy cock as she said, "I hope you can suck as good as you look." Flipping back between her male/female personalities just about blew my mind when she laughed and pulled out a rubber penis.
"I bought this in a toy store. Something that dykes apparently use when they want to butch it up." She laughed, "The look on your face was priceless though." Pulling her jeans off she looked at me with boozy eyes, "but I was serious about you sucking." She spread her legs as she started massaging an absolutely gorgeous and perfectly trimmed pussy.
"Come on girl, why don't you kick your heels off and make me cum?"
I did my best to look sexy as I removed my heels and rolled my nylons down. I turned over to show her my shaved ass, and yes I shaved it for the party, before sliding a finger down past my cheeks and around my own pucker. She kept massaging herself in slow, sensual circles, inviting me over with an equally slow motion of her other finger.
I gave myself two strokes before kneeling at her pussy and began to taste that salty brine I know and love so well. I played with her labia, feeling her hands hold me there. I moved up to her clit, licking and tonguing it like a kitten at a bowl of milk. I slid down to that oh so velvety and soft space at the base of her sex, before moving even further down to rim her ass. Needless to say her mouth was like a construction worker's. Between moans she was telling me to eat her out, rim her ass, show me what a whore can do, finger my own ass. When I didn't jump on that last one quick enough she got up and went to another room. I sat there wondering what was going on before she walked out with a strap-on, stroking it with lube as if jerking a cock.
"Come on you little whore. Bend over that leather couch over there and spread your cheeks for me. Don't you want some stud breaking you? Isn't that why you dressed up like a little whore and pouted your lips like you wanted to suck a real cock?" She giggled as she told me it was edible lube, "cherry flavor."
There I was naked, lying down on her floor, my body spread out as she fed me her cock. She reached down and stroked me, playing with my balls as her cock slid in and out of my mouth. I was moaning as her finger tips moved from my own cock/clit to my man pussy to my nipples, squeezing and twisting and pinching and pulling them until I was on the verge of cumming. I started begging her to let me cum as if I was a little girl.
"Do you want to cum? Do you want to cum bitch?"
I eagerly begged her to let me. She grabbed my knees and threw them back until the touched my ears, then fucked me Amazon style. She plunged her sopping wet pussy onto my cock as her strap-on bounced with each thrust. All I could do was beg for more. Was that really me I was hearing? Was I one step closer to being the slut I dressed out to be at the start of the evening?
"Oh God Yes!" I heard. "Fuck me harder!" I screamed. "Make me cummmmmmmm." I pleaded.
At some point she lifted up from my cock and on the next thrust, plunged her strap into my waiting ass. My eyes bulged and my mind leapt, but my anus accepted what had just happened as I crossed over and kept begging her for more, only this time as her real-time slut. It blew my mind how quickly and easily it happened, but there I was, on my back, my hands playing with my cock and my nipples as she slid her strap-on into me with loving affection.
She saw it too as her entire body shifted into a king and loving man, smiling between her thrusts, caressing my chin, sliding a finger into my mouth, pulling on my nipples and holding my waist as she slowly and sensually slid in and out of my ass.
"Was this love?" I asked myself? "I'm not a slut, but wow, did this feel good." "Was this me enjoying my own sluttiness?" "But, God did he feel good in me."
I was so torn with what was going on inside of me, but I was loving the results I was feeling.
She would bend down as she thrust in to kiss me and to lick my nipples, before straightening up again as she pulled out to stroke me a few times.
At one point I was non my hands and knees getting fucked up my ass, at another I was on my back as her pussy drenched my face, at another she lay back on her couch as I ate her like a pro feeling the waves of pleasure from the vibrator that was stuck in me. But the best was the moment I was when she was on her side as I lid in and out of her and her hand reached down to gently rub my balls and then to pull my dick out of her and politely slide it into her ass. Her ass was slick with her juices and fit my cock perfectly. She looked over her shoulder, into my eyes and smiled. Her moans turned into deep grunts as our passion turned from her pussy to her ass.
In a few thrusts she reached into her bedside table to pull out a rabbit that she quickly slid into her slit. I quickly felt the vibrations and gyrations of that sex toy as it massaged both of us to climax. Even after cumming we continued our anal fucking. The pleasures were amazing. Hard and wet, slick and orgasmic. She raised her leg to climax, then lowered it to regain herself, raised it again as she came and lowered it to rest. All the while I continued my pumping, flicking her clit, fingering my own ass and playing with my own balls, pinching her nipples and then mine - it was truly a night for two sluts to be our unabashed and honest selves as we gave into ourselves together.
I stayed the night, and in the morning fucked again, until it was time to shower and leave. She had other thoughts in mind. No shower and to walk the walk of shame home to show everyone on the street just how much of a whore I had been last night.
The laughter from the security guards in her building was just the beginning of my shame as I realized I had been turned into one hell of a whore of a girl in just one night by one hell of a man. And yes, I wanted him to do it again, if he would only answer my call...
Valentina
- 08.11.2021
- 6
- 0
