Last year, I broke up with boyfriend and needed to move out of his apartment right away as I wasn't on the lease and couldn't afford to pay half the rent since I am a full-time college student and work 20 hours a week waitressing.
A coworker said that her neighbor's boyfriend had just moved out and the neighbor needed someone to sublet, so I jumped at the chance since it also meant I could carpool with my coworker and save up money to get my own place maybe. Before moving in, I only saw my new roommate for about 15 minutes at the bar when she gave my coworker the keys so I could see the apartment to decide if I wanted it. She warned me that she was going to be away one week so I had only that long to make up my mind. If I liked it, I could move in anytime the week after that and that first week would be rent just in case we didn't mesh.
I moved myself over one morning two Saturday's later. I tried to be quiet because a note said Karen slept days and worked nights.
When I got home from work that night, my roommate was lounging on the sofa in white cotton pj set. Both the neckline of the top and the hem of the bottoms were trimmed with an embroidered lace. It was pretty rather than overly sexy although the top was very low-cut revealing a lot of Karen's tanned breasts.
I'm hardly a prude so once I changed out of my uniform and into silk sleep shorts and a cami, I came out to watch tv, too. While I changed, Karen had made a platter of chips with two types of salsa and an olive spread as well as a pitcher of mojitos. I wasn't hungry, but the drinks were perfect and I had a second one while we chatted. I was a little drunk I guess and the sofa was leather so I slid around a little. when I changed positions. We laughed and I blamed it on the silk against leather. Karen said that's why she only wore cotton sleepwear. I complimented her outfit. She laughed and said that it was to celebrate her new boobs.
I did think that she looked a little different --well bigger, than the first time, but wasn't sure. I said so and Karen said that she had gone up a cup size in implants because she thought it would help her stripping career.
Again, I'm no prude, but I must have looked a bit shocked because Karen said she thought I knew. She pointed to a big poster on the wall showing a woman in g-string grinding against a pole as three hunky looking men knelt at her feet looking up with bare lust.
The woman's hair was elaborately curled and her face was very heavily made-up, but after a few seconds, I could see that it was indeed my roommate. I said "I didn't even notice it. If it was a snake it would have bit me!"
Karen looked funny and asked what else I hadn't noticed. I thought that was a weird question and said so.
Karen bit her lip and said "So you think I'm a beautiful girl."
I've had girls come on to me before and have even kissed a girl friend a few times on a drunken dare. I'd had a third mojito and if I was in bar with a boyfriend egging me on I might have flirted with her, but I'm straight. I said I thought she was beautiful, but that she wasn't my type.
She laughed and asked what was my type.
"I guess from my last couple boyfriends, big dumb jocks. Not really dumb, but just more physical than emotional and yeah, definitely big."
"Big all over?" Karen teased.
Again, I'm not a prude, but I kinda thought it was inappropriate for someone I'd known about an hour at that point. Still I didn't want to make bad feels so I decided that playing along was a good idea. So I winked said "Oh, yeah."
We both laughed. Then Karen stood up and said "What if I told you Melanie that I bet I'm bigger than any of your boyfriends."
I was puzzled. Karen was tall for a woman. I'd noticed that in the bar. Even now I wondered if she was nearly 6 foot. She was well-proportioned for it though. Lean in the belly and hips but with an ass to balance out her implants. I smiled and said she was big, but all the guys I'd dated were at least 6'3" and weighed a solid 180.
"That's not what I mean honey" Karen said and she slid her hand into her pj bottoms and pulled out the biggest dildo I'd ever seen. It was like a third leg and I was shocked for sure. I think I giggled something like "What a big sex toy you've got!"
Then Karen dropped her bottoms and I could see it was attached to her body.
I guess the third mojito was all that kept me from jumping off the couch. She was bigger than all my boyfriends. But more importantly, she was a guy.
Karen picked her pjs back up and said "I guess Sami didn't think to fucking tell you."
I shook my head. But then, my manners caught up to me and I said. "It doesn't matter. I've got plenty of gay friends. It's ok."
Karen smiled, then she looked sad. "I'm not gay. Not really. I guess. I mean, I'm not sure anymore that I'm transgender."
She sat back down and told me her story. How she started having feelings she was in the wrong body when she hit puberty and then got seduced by an older neighbor who figured it would straighten "Kieran" out. Only, it made him more sure he was a she. After high school, she started cross-dressing, got kicked out of the house and had to strip in a gay club to make a living. But her shrink wasn't convinced that Kieran was really Karen because of the lateness of her gender confusion and the fact that Karen didn't really have sexual feelings for any of her boyfriends. She could only perform if she was the top and penetrated the guy. So Karen couldn't have the final surgery.
Meanwhile, she'd split up with her last boyfriend because he caught her looking at porn, regular hetero porn featuring lots of pussies. Karen tried to claim it was research, but her boyfriend said she was really just a screwed up person.
We were both in tears by the end and I went to bed thinking that it would be ok.
Except, I kept thinking about that huge trouser snake. It was so damn big. Even when I was alone at home, I'd stare at Karen's poster trying to figure out how she hid it in her tiny g-strings.
So I asked her to show me.
We'd had a lot to drink that night. It was our habit to wait up for each other with a pitcher of cosmos or mojitos or just rum and coke ready. The we'd drink until 5 AM and talk about our lives.
That night, I got Karen to talk about how much she loves stripping. Then i asked about how she concealed her penis. She explained, but I played dumb and said I was a visual person. She rolled her eyes, but dropped her shorts anyway.
There it was. Not erect and already at least nine inches long. What she did next should have grossed me out, but I was already more interested in other places she could fit it.
I applauded the sight of her tucked away and then asked it it hurt.
She said not really and that it actually was less uncomfortable than fucking her boyfriend's tight ass had been.
I asked if she'd had a woman since the neighbor. She said no, although she thought about it sometimes. At that I noticed that her cock was untucking itself and beginning to be erect.
So I kept her talking about pussy. By the time she finished, it was in full glory with a bit of moisture gleaming at the uncut tip.
She saw me staring and blushed, trying to cover it with her hands. I said it was ok. More than ok and offered myself.
I shed my clothes quickly before Karen could refuse. I was already sopping wet and had myself half-impaled on her monster cock by the time she could ask "Are you sure this is a good idea." My answer was to shove even harder so that she was seated as deep in me as she could go. "Fuck me!" I ordered.
And she did. She rolled me over onto my back, withdrew a little and then slammed home. Splitting me in half the whole time. I had the strange sensation of her balls slapping against my ass as her tits brushed against my lips. I yanked up her t-shirt so that I could clamp my teeth onto her right nipple. My hand came around from behind and grabbed her nut sack. Did I mention my boyfriend broke up with me because I'm rough in bed.
We hurt each other. Karen and I. But through the pain, i had the feeling of that great big dick plowing me, battering my g-spot, invading me like no cock had ever been able to. When I rolled Karen onto her back and started riding her, she went so deep, I though for a second the head of her prick would pop past that last barrier of cervix and enter my womb. The thought was too much for me and I climaxed unexpectedly with a surge so strong that it wrung an orgasm for Karen as well.
And when she withdrew to spray cum all over my chest, the sight of her body with both breasts and an erupting cock was so erotic that I cam again without even being touched.
Karen and I were frequent lovers that year, but then she met an older man who offered to pay for Thai sex reassignment surgery and I never saw her again. It makes me sick to think of that beautiful huge cock cut off. And I'm just glad that before she left, she had herself cast in latex for me.A custom sex toy,I'll cherish forever.
A coworker said that her neighbor's boyfriend had just moved out and the neighbor needed someone to sublet, so I jumped at the chance since it also meant I could carpool with my coworker and save up money to get my own place maybe. Before moving in, I only saw my new roommate for about 15 minutes at the bar when she gave my coworker the keys so I could see the apartment to decide if I wanted it. She warned me that she was going to be away one week so I had only that long to make up my mind. If I liked it, I could move in anytime the week after that and that first week would be rent just in case we didn't mesh.
I moved myself over one morning two Saturday's later. I tried to be quiet because a note said Karen slept days and worked nights.
When I got home from work that night, my roommate was lounging on the sofa in white cotton pj set. Both the neckline of the top and the hem of the bottoms were trimmed with an embroidered lace. It was pretty rather than overly sexy although the top was very low-cut revealing a lot of Karen's tanned breasts.
I'm hardly a prude so once I changed out of my uniform and into silk sleep shorts and a cami, I came out to watch tv, too. While I changed, Karen had made a platter of chips with two types of salsa and an olive spread as well as a pitcher of mojitos. I wasn't hungry, but the drinks were perfect and I had a second one while we chatted. I was a little drunk I guess and the sofa was leather so I slid around a little. when I changed positions. We laughed and I blamed it on the silk against leather. Karen said that's why she only wore cotton sleepwear. I complimented her outfit. She laughed and said that it was to celebrate her new boobs.
I did think that she looked a little different --well bigger, than the first time, but wasn't sure. I said so and Karen said that she had gone up a cup size in implants because she thought it would help her stripping career.
Again, I'm no prude, but I must have looked a bit shocked because Karen said she thought I knew. She pointed to a big poster on the wall showing a woman in g-string grinding against a pole as three hunky looking men knelt at her feet looking up with bare lust.
The woman's hair was elaborately curled and her face was very heavily made-up, but after a few seconds, I could see that it was indeed my roommate. I said "I didn't even notice it. If it was a snake it would have bit me!"
Karen looked funny and asked what else I hadn't noticed. I thought that was a weird question and said so.
Karen bit her lip and said "So you think I'm a beautiful girl."
I've had girls come on to me before and have even kissed a girl friend a few times on a drunken dare. I'd had a third mojito and if I was in bar with a boyfriend egging me on I might have flirted with her, but I'm straight. I said I thought she was beautiful, but that she wasn't my type.
She laughed and asked what was my type.
"I guess from my last couple boyfriends, big dumb jocks. Not really dumb, but just more physical than emotional and yeah, definitely big."
"Big all over?" Karen teased.
Again, I'm not a prude, but I kinda thought it was inappropriate for someone I'd known about an hour at that point. Still I didn't want to make bad feels so I decided that playing along was a good idea. So I winked said "Oh, yeah."
We both laughed. Then Karen stood up and said "What if I told you Melanie that I bet I'm bigger than any of your boyfriends."
I was puzzled. Karen was tall for a woman. I'd noticed that in the bar. Even now I wondered if she was nearly 6 foot. She was well-proportioned for it though. Lean in the belly and hips but with an ass to balance out her implants. I smiled and said she was big, but all the guys I'd dated were at least 6'3" and weighed a solid 180.
"That's not what I mean honey" Karen said and she slid her hand into her pj bottoms and pulled out the biggest dildo I'd ever seen. It was like a third leg and I was shocked for sure. I think I giggled something like "What a big sex toy you've got!"
Then Karen dropped her bottoms and I could see it was attached to her body.
I guess the third mojito was all that kept me from jumping off the couch. She was bigger than all my boyfriends. But more importantly, she was a guy.
Karen picked her pjs back up and said "I guess Sami didn't think to fucking tell you."
I shook my head. But then, my manners caught up to me and I said. "It doesn't matter. I've got plenty of gay friends. It's ok."
Karen smiled, then she looked sad. "I'm not gay. Not really. I guess. I mean, I'm not sure anymore that I'm transgender."
She sat back down and told me her story. How she started having feelings she was in the wrong body when she hit puberty and then got seduced by an older neighbor who figured it would straighten "Kieran" out. Only, it made him more sure he was a she. After high school, she started cross-dressing, got kicked out of the house and had to strip in a gay club to make a living. But her shrink wasn't convinced that Kieran was really Karen because of the lateness of her gender confusion and the fact that Karen didn't really have sexual feelings for any of her boyfriends. She could only perform if she was the top and penetrated the guy. So Karen couldn't have the final surgery.
Meanwhile, she'd split up with her last boyfriend because he caught her looking at porn, regular hetero porn featuring lots of pussies. Karen tried to claim it was research, but her boyfriend said she was really just a screwed up person.
We were both in tears by the end and I went to bed thinking that it would be ok.
Except, I kept thinking about that huge trouser snake. It was so damn big. Even when I was alone at home, I'd stare at Karen's poster trying to figure out how she hid it in her tiny g-strings.
So I asked her to show me.
We'd had a lot to drink that night. It was our habit to wait up for each other with a pitcher of cosmos or mojitos or just rum and coke ready. The we'd drink until 5 AM and talk about our lives.
That night, I got Karen to talk about how much she loves stripping. Then i asked about how she concealed her penis. She explained, but I played dumb and said I was a visual person. She rolled her eyes, but dropped her shorts anyway.
There it was. Not erect and already at least nine inches long. What she did next should have grossed me out, but I was already more interested in other places she could fit it.
I applauded the sight of her tucked away and then asked it it hurt.
She said not really and that it actually was less uncomfortable than fucking her boyfriend's tight ass had been.
I asked if she'd had a woman since the neighbor. She said no, although she thought about it sometimes. At that I noticed that her cock was untucking itself and beginning to be erect.
So I kept her talking about pussy. By the time she finished, it was in full glory with a bit of moisture gleaming at the uncut tip.
She saw me staring and blushed, trying to cover it with her hands. I said it was ok. More than ok and offered myself.
I shed my clothes quickly before Karen could refuse. I was already sopping wet and had myself half-impaled on her monster cock by the time she could ask "Are you sure this is a good idea." My answer was to shove even harder so that she was seated as deep in me as she could go. "Fuck me!" I ordered.
And she did. She rolled me over onto my back, withdrew a little and then slammed home. Splitting me in half the whole time. I had the strange sensation of her balls slapping against my ass as her tits brushed against my lips. I yanked up her t-shirt so that I could clamp my teeth onto her right nipple. My hand came around from behind and grabbed her nut sack. Did I mention my boyfriend broke up with me because I'm rough in bed.
We hurt each other. Karen and I. But through the pain, i had the feeling of that great big dick plowing me, battering my g-spot, invading me like no cock had ever been able to. When I rolled Karen onto her back and started riding her, she went so deep, I though for a second the head of her prick would pop past that last barrier of cervix and enter my womb. The thought was too much for me and I climaxed unexpectedly with a surge so strong that it wrung an orgasm for Karen as well.
And when she withdrew to spray cum all over my chest, the sight of her body with both breasts and an erupting cock was so erotic that I cam again without even being touched.
Karen and I were frequent lovers that year, but then she met an older man who offered to pay for Thai sex reassignment surgery and I never saw her again. It makes me sick to think of that beautiful huge cock cut off. And I'm just glad that before she left, she had herself cast in latex for me.A custom sex toy,I'll cherish forever.
