Like most of my other stories, this one is true. I've changed the names and locations to protect innocent (and guilty) people. You know the routine. This story contains graphic sexual content between a Tg and man. If that grosses you out go elsewhere. Also, if you are under 18 please do not read this story. Instead, check out MTV or something.
The Bartender
Awhile back I had a summer internship in a small city to remain unnamed for reasons that will later be apparent. By day, I did my boring hum-drum work, but by night, I was out enjoying nightlife as much as possible. The city I was in was a rather small and sad example of urban life. Nevertheless, there were several gay bars, and I began to frequent several of them. The one bar, "Studs" (made-up name) was mainly a disco on the weekends, but kind of intimate during the week. Thursdays was Karoke night, that sort of thing.
Anyhow, the next to last night of my stay in the small city, I went to "Studs," intent on having a drink or two. Then I was going straight home to bed. When I got there, the bar was dead. Just a few patrons, a really effeminate guy who the regulars referred to as "cookies," and behind the bar, a tall, but hustling figure. That night, I had on a black dress, fairly high black pumps, black stockings, etc. If you haven't read my other story, I'm early 30s, 5'11, thin and rather exotic looking. Basically I look Hispanic or Italian depending on the time of the month. I attract a lot of attention from men, but generally they are "straight guys." I've found most gay guys have little interest in anything in a skirt: penis or not. That's a shame because often the best looking and nicest guys are 100% gay. They really know how to compliment a girl, but aren't much interested in anything else.
So back to my story. I sat at the bar gathering my usual looks of "is that a man or a woman?" The bartender turned around and looked at me and smiled broadly. "What can I get you Miss?" I ordered a diet coke and rum, all the while checking out the bartender's butt. He had on a pair of jock-type shorts that clung nicely in all of the right places. As it turned out the bartender's name was Jay, and it was his first night on the job. He was a little confused, but "Cookies," was helping him out, showing him where the various beers and liquors were kept. Even though Jay was kind of busy, increasingly so as the night went on, he paid a lot of attention to me. Jay complimented me up and down. He said I was "beautiful." He said he couldn't believe I wasn't a real woman.. In fact, that's what he thought when I first sat down at the bar. He thought I was a lost tourist or something. Of course, I ate all of this up, and smiled back at him as flirtatiously as I knew how.
Because it was getting late, I switched to diet cokes because I was already slightly tipsy after three drinks. (I just can't hold my booze anymore!). Jay slipped me some free diet cokes (remember girls: NEVER drink a calorie) and I tipped him pretty well. We talked when he got the chance. He was from New York, and had worked at bars there. Upon arriving in small city, he had a job at a straight place, but they are even more dead than the gay establishments. So he was lucky enough to get hired at the top gay bar in small city. Jay had been in the military for awhile, and he owned a Jeep Wrangler (I have a Cherokee, sigh...). We seemed destined to be lovers.
Finally, I had to go. It was getting late, and I had a big day at work upcoming. As I bid Jay goodnight, he thanked me for the conversation and the tips. He asked me if I would come back and keep him company the following evening (Thursday). So I said "yes," and left the bar. Out in my Jeep, I began to feel a little affectionate. "Geez, what a nice guy," I thought. Now I was also still a little tipsy and feeling flirty. So I wrote a quick thank-you letter, and kissed it, leaving a lipstick imprint, then I stuck it on Jay's jeep. Giggling, but feeling kind of nice by all of the masculine attention, I headed back to my heinous motel room.
I guess I forgot to describe Jay. Like I said he was from New York, and had a bit of an accent. He was about 6'3 and normal body. Not super muscular, but not fat either: Jay was just a good looking guy. His face has really kind eyes that kind of twinkle, and he has charisma galore. He wore a ball cap as he tended bar (I love jock looking guys!), and he was 35. Purrfect.
The next night, I dressed more provocatively than the night before. I had on a shiny black figure hugging dress and black Mariah Carey rip-of pumps. Because I knew it was going to be dark, I wore slut red lipstick. It suits me well, the red lipstick, but only at night. It's too hard during the day. The thing I like about this particular dress is that it hugs my ass pretty well, and the garment reeks of sex.
When I entered the bar, and sat down, Jay immediately began to compliment me on my outfit. He even noticed my hair was different than the night before (curly instead of straight). All of the sudden "Cookies" came down from the top bar yelling in a loud lisp "oooh honey! I saw your LOVE note. I think your man's gonna fuck you!" Of course, I was instantly embarrassed as was Jay. We ignored "Cookie's" crude remark and continued talking. Jay thanked me for the letter. He said that he couldn't get me out of his mind all night and all day. He said he was really hoping I would show-up. Especially since this was my last night in the small city.
Over the course of the evening, Jay and I talked as much as possible pausing only so he could serve customers. We could talk about anything. One thing I liked about Jay was that he wasn't a braggarts, or crude. He was bright, interesting and well-informed. When I would get up to use the ladies's room, I could feel Jay's eyes on my ass as I walked away from him. Of course, I wiggled it all the more provocatively knowing he was appreciating my assets. I could tell he was smitten, and for my part, I was equally attracted. He asked me how long I could stay out that night, and if I'd be willing to wait until he got off work. With a big smile I said "yeah," and we both smiled the smile of people who know they are going to be intimate.
At about 2pm I went out to my car. I didn't want Jay to have to take any more teasing from or "Cookies,' who seemed jealous (he wanted Jay, not me!). So I sat in my Cherokee fixing my make-up and spraying perfume, etc. Just general feminine maintenance. Cookies left before Jay did, but he ignored me, as he was trying to get with some cute young thing in the parking lot. Finally, Jay was done and he came out. We talked for a second, and decided to go back to my motel room as the only afterhours club was for leather guys. Don't you find it odd that gay people discriminate? Anyway, Jay followed me back to my dive motel room. It was about a 15 minute drive, and I was nervous, but excited.
When we entered the room, Jay confessed some stuff to me. First, he wasn't gay. I kind of wondered about that. First, he had openly flirted with me, and most gay guys do not do that. Second, he just didn't seem as up on gay culture as I would have thought. Third, a cute boy was after him the first night, and he seemed disinterested. So I had been curious: why me? He only said that he was gay because he needed the job. While he felt terrible about having to lie, he also said that he felt that people are people and should be able to work anywhere or do anything regardless of sexuality, etc. So why's the straight guy after me? He said he'd always been curious about someone like me, and when he saw me come into the bar (after he realized that I was a Tgirl), he thought that I was the "girl of his dreams." Romantic stuff, huh? I was certainly hooked! Jay confessed he had never, ever, been with anyone with a penis before, but he found himself so attracted to me that he simply didn't care. By this time we were sitting on my bed talking. My pumps were off and I was still in my skimpy dress and stockings. I don't know how it happened, but suddenly we were kissing passionately. Jay pushed me down on the bed and suddenly I became aware of how strong he was...
While we were kissing, I could feel his erection grinding into my crotch. He laid over me as we kissed each other with abandon. I pushed him off me gently, and pulled down his shorts. His blood engorged penis was a normal, average 6 inches, extremely hard. Reaching into my handy purse sleeve, I put a rubber on his erection, and lowered my mouth to his manhood. I began to suck on his throbbing rod for all I was worth. I let him know through my ministrations how badly I wanted him. It was really cool watching his face contort with pleasure as I caressed his dick with my tongue. Then I could sense he was close to the edge, so I stopped and went over to the night stand. He just laid on his back watching me. It's odd how silent we were. I reached into the drawer and got a tube of KY jelly. I carefully squeezed a small amount into my palm, all the while looking at Jay. I applied some ky to Jay's hard dick, and then a little to my waiting "pussy." Jay just laid there. He said, "Maria, I've never done this even with a female..." He seemed nervous, but anxious to consummate our passion. I told him not to worry that we would both enjoy the ride. In a simple movement, I was impaled on his rod as he lay flat on his back.
Jay moaned his approval and caressed my ass and "tits" while I rode him with abandon. We fucked like that for a few minutes, and then I got off and laid on my stomach with my ass in the air. Jay didn't need a verbal prompt. He shoved into me, groaning with pleasure. That's when he really began to fuck me good. I felt just like a woman who had trapped her man, and was now feeling all of his sexual passion aimed at her. We were fucking so furiously that the bed was actually rocking. Jay was moaning loudly and kissing my neck while he shoved his length deep inside of me. We fucked like that for some time, just enjoying each other's desire. Finally, I felt Jay tense up and he groaned loudly. I knew his penis was spurting a huge load into the rubber lodged deep inside of me. I briskly touched myself and erupted onto the tacky excuse of a comforter with Jay still inside of me. We kind of collapsed in one piece. He was still inside of me. We had finished in the doggie position, and were now kind of spooned together.
Eventually, Jay withdrew his flaccid penis, carefully holding onto the rubber. We then kissed a bit more, and with Jay rubbing his strong hands all over my ass and boobs. But our euphoria had to end. It was late, and I had to be up early: Jay had a 25 mile drive ahead. (I didn't want him to stay as he would have seen razor stubble once my dermablend was off: thank-god my electrolysis is proceeding!) So we exchanged phone numbers. Jay said he would call me, and I thought "right." Even though I felt a strong bond with this man, I knew a relationship wasn't in the cards. He lived far away from me: too far for a serious relationship. As I watched his jeep drive off into the night, I sat thinking about what had just transpired. After stripping off my make-up, I fell asleep in the tacky bed, utterly exhausted, but satisfied..
The prologue is that Jay DID call me. In fact, for about 2 weeks after I got back he continued to call. But finally I didn't return his call. I just figured that it was too far for anything useful to occur. Plus I began working really hard, so I had little time for correspondence. Still, I sometimes think of Jay and wonder if he might have been my husband. Some girl, somewhere has herself a real catch! I just hope it's one of us....