Chapter 2: The Bar
by AJ ©
After my experiences with my sister Kayla, my sex life changed dramatically. I went from a mild mannered horny guy to this sex hungry creature. The whole first week of college I spent thinking of my younger sister's hot little pussy and how I loved having her muscular legs wrapped around my head. I also couldn't shake that feeling that I got when I swallowed my own cum.
I had moved into one of the dorms set aside for athletes on scholarship. I was rooming with two other guys on the wrestling squad. One of them was a freshman like me, the other guy was a co-captain of the team. My sister Rose would stop by from time to time to 'see me'. Actually she had the hots for my roomie and made no secret to me that she would fuck his eyeballs out given a chance. After a couple of weeks of settling in and getting used to the grind of things I was ready for some fun. My roommate suggested we go to this alternative style bar in the college section of town. So he and I and his brother and another guy they called Tweekie went. I didn't know until much later in the night that Tweekie and my roomates brother were dating! The bar was nice; there was a good mix of people, everything from bikers with huge tattoos to crossdressers! At the bar I saw what I thought was the hottest chick in the joint. She had a nice shapely ass, a slim figure, long brown hair and dress that gave you a hint of how nice her tits were. As I stood staring at her, Tweekie whispered in my ear," He's so bad!" I had no idea that the woman I had been lusting after all night was a man! Or was it? I had to know, so I calmly walked up to the bar and ordered another drink. As I walked away I caught a look down her bra, and there were the cutest looking tits in the world!
While walking away I heard her call out, "I hope you liked them."
I was so embarrassed, the woman had seen me looking at those cute little tits. After another round I was ready to go...I had a urge to take care of and I couldn't drink anymore or I'd be sick. The whole way home I fantasized about that sexy woman, her cute tits, that nice round ass...the way her hair smelled. Damn I needed to get laid.
As Tweekie said good night to all of us, he whispered that the woman I was staring at was 'Carlie" and that she was a regular at the bar. The next night while everyone was at the dorm party I headed out to the bar to find 'Carlie'. Just as I had hoped she was at the bar having a drink and chatting to another sexy woman. I approached rather casually and ordered a beer. She must have recognized my voice because she looked up and said: "What you back for more already?"
"That depends on what else I can get," I said rather cocky. She laughed and told me to sit down. She had obviously been drinking all night, her voice was slurred and her eyes looked heavy. We talked about ourselves and I found out she was 28 and a paralegal working her way through law school... After an hour of conversation, and her hand stroking my thigh, I was ready to go. She suggested that we head to her place because the bar crowd was dying out and she was ready for a more comfortable chair.
When we arrived at her place I was amazed at the sport memorabilia she had around. "You must me a sports fan Carlie, look at all this stuff."
"Well sorta, I was, I just haven't had the time to take it all down, I want to redecorate. But who has the time with a job and school," she called out from the bedroom. "I have changed things in here though, come and see." This was it I thought. My chance to get laid finally and with an older woman to boot. I walked in the bedroom and there was Carlie fighting with the zipper on her dress.
"Allow me," I said.
As I unzipped her dress, she began taking off her bra and letting them both fall to the floor. Then she turned around in nothing but her panties and knelt on the floor. Before I knew it she had my dick in her mouth and was sucking me like I was full of the best tasting wine in the world...I was having trouble standing so she motioned for me to sit on the bed...from that angle I could see her small lips sucking and her tongue caressing my dick. She would stop occasionally to flick the cum on my dick with her tongue...
She asked if I liked what I saw and I said that I'd like it even more if I saw the cum shooting out. That really turned her on and she began sucking me harder and faster....Then I whispered I love to have her share my cum with me. At that moment she grabbed the base of my dick and began jacking me and licking me up and down. As I started to cum I grabbed her head and forced it on my dick. She knew what that meant and in a matter of minutes she was passing the cum from her mouth to mine.
She pushed me back on the bed and began to lick my throbbing dick and my balls...and then my ass! I loved every second of it.
Then Carlie crawled on top of me...only she wasn't facing me. I thought that this meant I was going to be eating her out. But she stopped half way and placed her ass right on my dick, she started bucking against it the whole time I thought she was fingering her self...but she wasn't. She turned around, and there on my chest was a dick. Carlie was really Carl. I was so freaked. She looked at me and said that she was sorry but she was horny and knew that she could only get so far before I noticed. But I was still horny.
"Well, you made me cum, so I guess I owe you the favor," I couldn't believe my ears. I was talking about fucking a she-male!
"Are you sure?"
Carlie slid down my body again, this time to put her dick in me. I wanted it, I wanted to feel what it was like to have a dick inside of me. As she eased her small dick in me, I started sucking on her cute tits. I loved the feeling of her dick in me, after the initial pain, and after her cum started lubricating me.
The feeling was wonderful, her hard cock pumping in me, the look of pleasure on her face, and the thought that soon she'd be cumming in me. It was all driving me even wilder, I began to stroke my hard cock and just as I was about to cum myself I felt a hot stream of Carlie's cum shoot inside my ass. Carlie fell on top of me and began kissing my chest and licking my nipples. Then she rolled off of me and began to stroke my dick again...then she looked at me and with her eyes she guided my dick to her ass. I took that as an invitation to return the favor. As I began to get up Carlie turned over and got on all fours.
"You like it better like this," she said.
I knelt behind her and rubbed my dick against the crack of her ass, each time I passed her asshole she would buck into it. "You are such a tease, go ahead, I want it in me."
I slowly slid my dick into her ass. This was the first time I had anal sex and I already loved it. I loved the tightness of it, and the way it was almost impossible to slip out. I think I may have lasted a full five minutes before I came. Carlie said that is normal for a first timer. After I shot cum in Carlie's ass I was spent. I made an excuse about being locked out of the dorms and gathered my clothes and said thanks for a wonderful evening.
The next time I went to that bar Carlie was no where to be found and no one had seen her. Tweekie had heard that she moved to a more 'friendly environment' in a larger town. I was sorta upset, I wasn't sure if I was ready to explore my new found sexual appetite or if that was a sign of what is was meant to be. But what I found out next was definitely not expected.
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