The Girl at the Bar

I returned to the gay bar a few more times, and had some more encounters that broadened my horizons. This story is about my second trip to the bar.

I don't know if it was because it was a Tuesday, or if the party started later, but the bar was pretty empty the next time I went in. I waved hello to the bartender, walked to the back to check out the dance floor - one couple were slow dancing to the music.

I walked back to the bar, sat on a stool, ordered a drink, and chatted a bit with the bartender as he mixed it. Then I sat back and listened to the music, watching the news on the bar's TV. After a while, I went to the bathroom, and upon returning, saw a woman who was just sitting down at the other end of the bar. She was medium height, blonde, and thin. I thought it was odd that a woman would be in this bar, then it struck me that she might be a transwoman. I signaled to the bartender, pointed to my drink, and said "Another for me, and whatever the lady is having." I nodded towards her. The bartender chuckled, and went to take her order. She looked over at me, and smiled. When our drinks came, she motioned for me to come sit near her, so I did.

It took me a minute or two to be sure of it, but she was a he - a very feminine and sexy one. Debbie and I talked for a while while we enjoyed our drinks. She had a smoky, husky, Kathleen Turner voice that seemed to link directly to my cock.

"I wasn't sure if I was ready to dress in public." She told me. "So I came on Tuesday, because it's the slowest night here. What do you think?" She gestured up her body with her hands. "Do I look good?"

"You look sexy, Debbie." I told her. "It took me a minute or two to figure out what you were doing here - at a regular bar I don't think I'd have even noticed." Then with my best poker faced delivery. "You area transwoman, right?"

"No. I'm not." She told me. I blushed and started to apologize. "No, no, you're such an easy target - no, I'm a CD. A cross-dresser. I just dress up sometimes because I like the feeling - I don't live as a woman, and am not transitioning. In fact, I've never been dressed and with a man before." I took a moment to process this. "Hey, I like this song - do you like this song?" She exclaimed, as Roxy Music's "Dance Away" stared playing.

"Would you like to dance?" I asked, holding my hand out, like a gentleman in an old movie.

She tucked herself close into me and I held her as we swayed on the dance floor. Her head was on my shoulder as the song came to an end, and something more up-tempo replaced it. She took my hand and we started back towards our spot at the bar.

"You're sweet." She told me. "You don't think my tits are too small? I don't wear falsies or anything, just put them in a bra - I'm only an A cup."

"No, I actually like small, pert breasts better than large ones - less sag. It was one of the things that my ex and I argued about - she wanted to get implants, I liked her 'itty bitty titties' the way they were."

"You're into women? You're straight? What are you doing here, then?"

"I've mostly been with women, but lately I've been doing a bit of experimenting, trying new things."

"Want to try me?" She asked, leering a bit, and licking her lips sultrily.

"I thought you'd never ask."

It had been overcast when I had entered the bar, now it was raining, which I hadn't been expecting. I held my jacket over Debbie's head, realizing that she had put time into her hair and make-up, and the rain wouldn't help it. "Where to, Deb?" I asked.

"My car is just over there." She pointed across the dark parking lot. We ran over, she dug her keys out of her purse, and jumped in. "Hey, get in!" She called to me, leaning over to unlock the passenger door. I ran around the car and slid in.

"You're all wet." She laughed, and leaned over to kiss me as the rain pounded on the car's roof. She tasted of lipstick, which she wore heavily. I kissed her back, and she surprised me by responding to my attempt to slip the tip of my tongue into her mouth when she aggressively thrust her tongue into my mouth.

We held that first kiss for a long time, both of us running our hands over each other's bodies. We broke the kiss when another car pulled into the lot near us, and the occupants got out. "Your place, or mine?" Debbie asked. We both laughed at the corny line. "I'm just a few miles away, and I don't want to wait any longer to have you." She told me. I shook my head in agreement., and tried to control myself while we drove to her apartment complex. But somehow, we never managed to get inside.

As soon as she parked, she turned and we started kissing again, frantically, passionately, hands on each other's body, I stroked her legs, pushing up her skirt, and admiring the stockings she was wearing. I hadn't had very many experiences with girls in lingerie, so this was an exciting experience.

"You like that?" She asked. "You like my stockings?"

"Yes. They are very sexy."

"Oh, I like you." She arched her back, raising her ass off the seat, so I could flip her skirt higher, and she could show off the garter belt and garters holding the stockings up. I loved the feel of the difference between the fabric of her stockings, her panties, and the smooth skin of her legs. Without making a conscious decision to do so, I bent down to kiss her thighs. "Oh, you're full of surprises!" She gasped out, and caressed the back of my head and neck. I moved to kiss her other thigh, wanting to balance things out, and she wiggled her hips, in response - which placed her panty-clad cock against my cheek.

She rubbed her cock into my cheek. "You comfortable, sweetie? My clit isn't bothering you, is it?"

"No, at least not in a bad way."

"Even better than I hoped." She hummed, "Give my clit some loving, sweetie." I turned my head and started running my lips across her panties, as her cock uncurled form where she had had it hidden. I found a wet spot, and licked her precum from the smooth material of her silky panties. "Oh God, sweetie, that's it!" She reached down and pulled her panties to the side, freeing her cock and allowing me better access.

I may not have been raised to be a gentleman, but I do know that pleasing his lady is a man' s responsibility, so I opened my mouth and slid her hot, sticky cock between my lips, inhaling the musky, sexual aroma of her crotch and precum. She groaned and pulled my head closer into her love nest, pushing her cock into my mouth, then pressing its tip against my throat. I swallowed, swallowed, and swallowed again, hoping to overcome my gage reflex and get all eight inches of Debbie's sweet "clit" to nestle deep into my face. She groaned as her long, thick cock wormed its way deeper into me with each nudge, wiggle, or swallow. I tried to move my head up and down, to bob on her cock, but the back of my head hit the steering wheel after I'd gone up only an inch or so, so I did short bobs, allowing her cockhead to enter and exit my throat as I wrapped my lips around her shaft and twisted my tongue around her meat, grunting out moans of pleasure as I gave myself totally to the task of pleasing this pretty lady and her meaty cock.

"Oh, yeah! Go for it - go for that nut! You want my load, don't you?" I moaned an affirmative response, which she took as an invitation to start fucking my face harder. Her hands pulled on my head, her fingers digging into my scalp as she used my face like a sloppy pussy, driving her cock in and out of my throat. I was having trouble breathing, but enjoying the intensity of the experience. "Take it! Take it! Take my cock you fucking bitch!" She snarled as she raped my mouth. I loved it, her words and aggressive control over me turning me on even more.

"Mmmmmmm! Mmmmmmm! Mmmmmmmffff!" I choked out, trying to let her know how sexy I was finding the whole experience.

"You ready bitch? You ready to eat my load like the greedy slut that you are?" She snarled, thrusting wildly into my mouth, feeding me her wonderful, hot flesh-tube.

"Yefffffff! Yefffffffff! Gfffffffff it to mmmmmmmmmme! I moaned out, my attempts at words humming along her cock as she pounded me harder, ramming my head back into the steering wheel before she finally pulled me down on it, mashing my face into her pubes and pumping me full of her love juices.

"Fuuuuuuuuuck! Take it! Take that load, slut! She cried out in that sexy, throaty voice as she unloaded ropes of her seed directly into my throat. I nursed and suckled on her cock as it pulsed out the last drops of cum, and then slowly softened in my mouth. I took in my surroundings - the stockings and garter belt next to my cheeks and ears, the skirt covering my head , the cock still jammed in my mouth, the sweet taste of the last of Debbie's cum. I stayed there, working her cock like a suckling baby until she finally pulled me off, exhausted.

"Thank you sweetie, that's the most fantastic blowjob I've ever had - you really got into it. I wish my wife had that attitude - maybe I should have you give her lessons." She whispered to me, and raised my head for another passionate kiss. "I guess it's your turn." She said. "I'm not really into this - certainly not like you, but I guess I owe it to you to try." She reached into my jeans, freeing my already throbbing cock. "Wow, that's sticky, did you already cum?" She asked.

"No, but I'm really close." I panted, as she tentatively stroked my cock, running her fingers up and down the shaft. My cock twitched in her hand and I groaned out "Oh hell, here it cooooomes!" As my cock twitched and started spurting my load into her outstretched palm. She stroked me with her other hand, milking all the cum out of me, then looked down at the puddle of warm cum in her hand.

"I think I know somewhere that needs this." She purred, raising her cum filled hand, then cupping it to my lips and pushing it up to my face. "Lick it up, cum slut. I know you love it." And I did.