I can not believe that this was as long ago as it was. I was in my early 20s. I had not just gone through a bad break up, one that left me broke, jobless, homeless as well as physically injured and scarred. Moved back in with my parents while I looked for a new job and recovered from my injuries (bad car wreck right before the break up that was not my fault as I was the passenger). While I was looking for work, I was also enjoying internet porn (this was in mid 2001). I came across some Shemale porn and I became obsessed with it. I even found myself at gay.com in the shemale chatroom looking for one to experiment with. I met one that lived in the same state that I do, only about 200 miles away. She was hot and suggested that I take some time away from home, and suck off truckers to work my way to see her. Instead we remained in contact here and there and I looked for someone cheaper.
After the new year in early 2002, I moved away to start anew in college. Once I was settled in the dorm I sent her an email (her name was Mona) explaining to her that I had moved closer, still about 100 miles away, but also had a car and free weekends. A month went by and I heard nothing back from her. I wondered if she thought I was stalking her or if she didn't realize that it was a joke and she really wasn't interested in me and that she really wasn't looking at my pics as often as she claimed she had been. Out of the blue one Friday evening she called me up and we made arrangements to meet at her place. I lived in a small dorm room, she had a two bedroom house and she lived alone. Made sense to me to meet her where she lived. She emailed me her address and the next Friday, after a very long week of nerves and excitement, followed by a Friday that seemed to last an eternity, I packed a small bag, jumped into my car and drove to see her.
I pulled into her driveway and was nervous. I had never done anything like this before. I knocked on her door, my heart was pounding. She answered it. She was taller than I was. She had long brown hair, very passable, her tits were Ds and she worn a thin shirt with no bra with her nipples poking through the thin material. She let me in and I looked around, hard and nervous. She apologized for the state of the living room, said that her vacuum cleaner broke. I laughed and said that I came to see her and not her house. We picked out some movies to watch and left to pick up some vodka. Throughout the ride to the store and back she kept rubbing my thigh and flirted with me. It seemed that no one in front of me knew how to drive the speed limit and I'd swear we hit ever light red. I also began to wonder, she was very passable. There was a good ten years between us. Was it possible that she wasn't a shemale but actually a real female?
We got back to her place, she fixed the drinks while I put the movie on, Pulp Fiction. It was the first time I had ever seen that movie. Even now when I watch it I can't help but remember this evening. As the movie started we began to kiss and feel each other up. It wasn't long before we were undressing each other. She got me naked before I got her undressed. As soon as I unzipped her pants I found that she was a shemale and I didn't care. I opened her jeans and there was a pair of panties and the outline of her cock. I pulled both her jeans and panties off at once. I went to kissing her and rubbing her leg with my hand. It was odd when I grabbed her naked dick for the first time. I never really got hard. I softly stroked it, wondering if she could get fully hard, wondering if she could do the stuff I have fantasized about, like taking a load, by force, into my mouth and swallowing it. She asked "Could you go down on me?" I moved, without question, to her crotch. I looked at it. I said "I have never done anything like this before." She said "That doesn't matter, just go for it." And I did.
I had gone down on several women, but she was the first shemale, so this was the first cock I sucked. It was weird. The taste was a flavor I don't know how to describe with the addition of precum. It was both hard and soft. And I bobbed my head up and down, putting my lips right were I had urged my ex to put her lips when sucking me off. She moaned and told me to keep going.
When I finished that I returned to kissing her and she broke the kiss, looked at me, her hand around my dick and said "Honey, I honestly don't know if I can take you." She grabbed a bunch of condoms and lube. She put both the condom on me and lubed me up. She got onto her hands and knees and told me to be gentle. I've fucked a few women in the ass before, one of whom had never done it, so if they could take me I was sure she could. I don't remember much about if it was a challenge or not to get into her, but I do remember it feeling great once I was inside.
She couldn't take me for long periods of time, so we fucked off and on all night. I was either sucking her nipples, cock, kissing her or fucking her ass. If I wasn't doing one of those things, she would rest her head on my lap and smoke a joint with me. One of my favorite memories from that night were those times when she'd roll me onto my back and fuck me with her on top facing me. Her tits bouncing as her dick swayed from side to side or around in circles.
I fucked her and felt the sensation that I was about to cum. I pulled out and got her face and tits. We cleaned up and then everything hit me in a sobering realization. So I panicked, got dressed, lied to her about needing to do school work and left.
It took me a month before I emailed her again. I never saw her again, sadly. Of the shemales that I had the pleasure of fucking, she was my first and hottest, not to mention the most passable. Even girls that I dated after would look up her facebook profile and comment about how good she looked. A friend of mine high fived me when I showed him her facebook page. She and I did talk a few times via email and phone. Every so often I find myself in that city, she, as far as I know, still lives there and I still think about emailing her or contacting her through facebook to let her know that I was in town and if she wouldn't mind meeting with me again.
After the new year in early 2002, I moved away to start anew in college. Once I was settled in the dorm I sent her an email (her name was Mona) explaining to her that I had moved closer, still about 100 miles away, but also had a car and free weekends. A month went by and I heard nothing back from her. I wondered if she thought I was stalking her or if she didn't realize that it was a joke and she really wasn't interested in me and that she really wasn't looking at my pics as often as she claimed she had been. Out of the blue one Friday evening she called me up and we made arrangements to meet at her place. I lived in a small dorm room, she had a two bedroom house and she lived alone. Made sense to me to meet her where she lived. She emailed me her address and the next Friday, after a very long week of nerves and excitement, followed by a Friday that seemed to last an eternity, I packed a small bag, jumped into my car and drove to see her.
I pulled into her driveway and was nervous. I had never done anything like this before. I knocked on her door, my heart was pounding. She answered it. She was taller than I was. She had long brown hair, very passable, her tits were Ds and she worn a thin shirt with no bra with her nipples poking through the thin material. She let me in and I looked around, hard and nervous. She apologized for the state of the living room, said that her vacuum cleaner broke. I laughed and said that I came to see her and not her house. We picked out some movies to watch and left to pick up some vodka. Throughout the ride to the store and back she kept rubbing my thigh and flirted with me. It seemed that no one in front of me knew how to drive the speed limit and I'd swear we hit ever light red. I also began to wonder, she was very passable. There was a good ten years between us. Was it possible that she wasn't a shemale but actually a real female?
We got back to her place, she fixed the drinks while I put the movie on, Pulp Fiction. It was the first time I had ever seen that movie. Even now when I watch it I can't help but remember this evening. As the movie started we began to kiss and feel each other up. It wasn't long before we were undressing each other. She got me naked before I got her undressed. As soon as I unzipped her pants I found that she was a shemale and I didn't care. I opened her jeans and there was a pair of panties and the outline of her cock. I pulled both her jeans and panties off at once. I went to kissing her and rubbing her leg with my hand. It was odd when I grabbed her naked dick for the first time. I never really got hard. I softly stroked it, wondering if she could get fully hard, wondering if she could do the stuff I have fantasized about, like taking a load, by force, into my mouth and swallowing it. She asked "Could you go down on me?" I moved, without question, to her crotch. I looked at it. I said "I have never done anything like this before." She said "That doesn't matter, just go for it." And I did.
I had gone down on several women, but she was the first shemale, so this was the first cock I sucked. It was weird. The taste was a flavor I don't know how to describe with the addition of precum. It was both hard and soft. And I bobbed my head up and down, putting my lips right were I had urged my ex to put her lips when sucking me off. She moaned and told me to keep going.
When I finished that I returned to kissing her and she broke the kiss, looked at me, her hand around my dick and said "Honey, I honestly don't know if I can take you." She grabbed a bunch of condoms and lube. She put both the condom on me and lubed me up. She got onto her hands and knees and told me to be gentle. I've fucked a few women in the ass before, one of whom had never done it, so if they could take me I was sure she could. I don't remember much about if it was a challenge or not to get into her, but I do remember it feeling great once I was inside.
She couldn't take me for long periods of time, so we fucked off and on all night. I was either sucking her nipples, cock, kissing her or fucking her ass. If I wasn't doing one of those things, she would rest her head on my lap and smoke a joint with me. One of my favorite memories from that night were those times when she'd roll me onto my back and fuck me with her on top facing me. Her tits bouncing as her dick swayed from side to side or around in circles.
I fucked her and felt the sensation that I was about to cum. I pulled out and got her face and tits. We cleaned up and then everything hit me in a sobering realization. So I panicked, got dressed, lied to her about needing to do school work and left.
It took me a month before I emailed her again. I never saw her again, sadly. Of the shemales that I had the pleasure of fucking, she was my first and hottest, not to mention the most passable. Even girls that I dated after would look up her facebook profile and comment about how good she looked. A friend of mine high fived me when I showed him her facebook page. She and I did talk a few times via email and phone. Every so often I find myself in that city, she, as far as I know, still lives there and I still think about emailing her or contacting her through facebook to let her know that I was in town and if she wouldn't mind meeting with me again.
