I was so nervous I was almost sick. For years I'd dreamed of going to a bar that catered to the LGBT community but I'd always come up with an excuse not to, no matter how flimsy it might be. Yes, I'd gone out in public several times, shopping mainly, but also banking, getting gas, and even meeting with other girls like myself.

So far, the only sex I'd indulged in while dressed had been primarily with my hand or a dildo and not with any other human being. To make matters worse, I'd only been involved with three women in my life. At least three that had involved any type of sexual relationship. With all of them, whenever I confessed my love of crossdressing, that had been the end of that.

When I climbed out of bed this morning I knew today would be vastly different. I was horny but not erection horny, it was much deeper than that. I took my time getting dressed, bathing in scented oils, taking time with my nails, carefully applying my makeup, styling my hair, and choosing what to wear. I wanted to look sexy but not desperate, alluring but not out of reach.

Even while I was getting ready I was sure I'd get cold feet before actually going anywhere no matter how badly I wanted to go. Sure, I'd done all my research, knew the bar, where it was, about what it would cost, the music they played, everything but I was positive I'd chicken out even if I made it out of the house. Even so, I continued becoming all the woman I could and when I finished I was very pleased with the outcome.

I wore my red hair stylishly short, short for a woman but a little long for a man. The dangling earrings really pleased me, a curve hugging black dress with thin spaghetti straps holding it up, a strapless bra with my breast forms firmly glued in place, black garter belt and nearly black stockings, and a black thong panty which was tight enough to keep my tucked package in place. This was all topped off with black sandals with three inch heels and sexy ankle straps. I checked and double checked my purse, making certain I had a compact, lipstick, keys, wallet, credit card, cash, and especially condoms. Not that I'd actually be needing the condoms but I carried them just in case I happened to get lucky. Besides, if anyone saw them it made me look more womanly.

Just before dusk I went to my car, a very small, but nice, domestic vehicle which fit my stature like a glove. Did I mention that I'm only five feet five inches? Well, I am, so you can see why I preferred a small vehicle. It was really cute and seemed to fit my female persona like a glove.

Twice, while driving to the bar I nearly lost my resolve and turned around. But for some unknown reason I couldn't. I kept telling myself that I wasn't even in the parking lot, so there was still plenty of time to turn tail and run.

Then I was there and I just sat in my car for several minutes. Could I go inside? Yes, certainly I could. Was I brave enough? I didn't know. Then I saw another girl go inside and immediately recognized her as a man in a dress. I mean, it looked like she just slapped on a dress and a little makeup and then went clubbing. If she had the balls, (no pun intended), to go inside, I certainly could.

More nervous than I'd ever been in my life, I stepped out of my car, picked up my purse, and went to the door. Three men came out as I was about to open the door, already totally wasted.

“Whoa, baby!” the first man out said, looking me up and down.

“Quit that, you animal,” an obviously gay man laughed and took the hand of the man who had spoken. “Sorry, honey.”

“No problem,” I smiled as if that sort of thing happened all the time.

The third man of the trio patted his the nice one's ass and they moved along. I didn't have any doubt where those three were going.

I finally made it into the bar and looked around for a few minutes. I spotted the man in a dress, as I called her, and saw that she was sitting with a man already. Good for her! Making my way to the bar I climbed on a bar stool, crossed my legs as I'd practiced so many times and then ordered a drink. I needed one to bolster my waning courage. Right this minute it was all I could do to keep from running back to my car.

“Here you go dear,” the bartender smiled as he placed my drink in front of me. “I don't think I've seen you in here before.”

“First time.”

“I can understand that. Sometimes it takes a little something extra for the first time.”

“Does it show that badly?”

“Honey, if I said “Boo” you'd be holding onto the ceiling,” he said with a chuckle. “Just relax, we're really pretty friendly around here, especially the regular crowd. By the way, I'm Bobby, the proud owner of this establishment.”

“I'm Karen,” I replied with a smile.

Between his friendly manner and the drink I actually was relaxing.

“Excuse me,” he said and looked down the bar. “Hiya Cassie. The usual?”

“Hi, Bobby. Yes, please,” she responded with a pleasant smile.

While Bobby made her drink she looked at me, extended a well manicured hand and smiled. “I'm Cassie.”

“I'm Karen,” I replied and lightly took her hand.

“Here you go, Cassie,” Bobby said and gave her a drink. “Hey, Cassie, do me a favor and show Karen the ropes, she's new around here.”

“Sure thing. Would you care to join me, Karen?”

“Surely,” I replied, the nervousness still evident in my voice.

“Relax, sweetie, I don't bite. I may suck but I don't bite.”

I giggled at her remark and followed her to a booth.

“Have you been doing this long?”

“Doing?”

“Dressing up and getting out.”

“I've been dressing forever but just started getting out, you know, shopping and stuff, but this is my first time in a bar. You?”

“I'm an old hand at this I guess you could say. I went to my first bar when I was twenty-two and I haven't looked back since,” she giggled.

“The important thing is to know your boundaries. If you're a rookie then you have to make them as you go. You're pretty enough that you'll be hit on by quite a few guys before the night is through, especially since you're a new face. If you don't like them, send them on their way so they'll at least stand a chance of getting laid and if you do, well, there's a motel a block from here.”

I blushed and said, “First time for that as well.”

“Well you certainly picked the right place to get started,” she laughed. “Come on, let's shoot a game of pool. You'd be surprised how bending over to make a shot with a short dress on will attract attention.”

In fact, we shot several games and I know I had shown off my thong quite a few times. At home I had a regulation size table and spent many hours shooting pool by myself.

“Can I play the winner?” a masculine voice asked.

Cassie looked at me and I shrugged.

“Sure, baby,” Cassie smiled.

That was when she started missing all her shots, practically giving me the game.

“Have fun, Karen,” she said after losing and placing her stick back in the rack.

“I'm Dave,” he said, racking the balls.

“Karen,” I smiled before breaking.

I found that I had to miss a few shots to keep the game close and finally scratched on the eight ball.

“Buy you a drink?”

“Okay,” I said and racked the balls for him. I really hadn't expected to be talking with a man in a bar, much less accepting a drink from him but it was nice.

Dave returned with drinks in hand and smiled, “Let's make the game more interesting. Care to place a small wager on the outcome?”

“Okay by me as long as we keep it friendly,” I replied.

“Yes, very friendly,” he replied and gave me his best smile.”How about the winner gets a kiss and can make it as intense as he, or she, wants.”

“A kiss? Okay.”

“Cool,” he laughed. “Get ready to have your tonsils mopped, Karen.”

It hadn't dawned on me that he was talking about that kind of kiss but I'd already agreed to the stakes. Now I faced the possibility of being kissed by a man and I hadn't seen that coming when I left the house today.

I was more than a little nervous but I was also curious. In fact, I was so nervous I only made two balls before the game was over. Not being one to welch on a bet, I stepped closer to him and accepted his kiss. Man, was it ever a kiss! I mean, he pulled me close and sent his tongue deep into my mouth while his hands actually caressed my butt. So many emotions ran through me and revulsion was definitely not one of them.

When he broke the kiss I was shocked to find myself wanting more, so when he asked if I wanted to play again I was more than willing. This time I played more seriously, actually winning the game.

We kissed again with every bit as much intensity as the first time, except I was initiating the kiss.

“I like a girl in a thong,” he whispered after the kiss, “especially a black one.”

That's when I realized that on a few of my shots where I had to stretch out over the table I'd been giving him an excellent view. That fact was both embarrassing and exciting, and it made me wonder if he could tell I wasn't a real female.

“I'll play you for your thong, Karen.

If I win, you take it off and give it to me. If you win, I'll give you a hundred dollars. Either way another kiss is involved.”

“And I keep them on?”

“Of course. Well, for now anyway.”

“My break,” I laughed and gave him the triangle. I didn't notice how loose the rack was until I shot at it and the balls barely moved.

I was doing good until I shot at the eight ball and followed it into the pocket, thereby losing the game.

“Take 'em off, sexy,” he laughed.

“Right here?”

“Sure. I want to watch.”

It took me a minute but I got them down and stepped out of them without showing too much skin. But when he kissed me his hands cupped my naked ass and pulled me close against him letting me feel his swollen member through his clothes. As for me, the kiss combined with his hands on my bare butt was almost too much. What I felt this time couldn't be mistaken for anything except lust. But I had a dilemma. Did he think I was a real woman or had he read me?

As if he were reading my mind, Dave smiled and whispered, “Don't worry, Karen, I know all about what the thong was hiding.”

While his remark was comforting to me it also told me he was wanting more than just a game of pool. Was I willing to go any farther? Part of me screamed no but another part said yes, yes, yes.

Any doubt I may have had about his intentions was answered when he asked, “Would you like to get out of here?”

I didn't think more than a second before replying, “Yes.”

Dave took my hand and lead me outside. He opened the door to his car and I slipped inside and halfway across the seat so that when he got in I was sitting next to him.

“Don't worry about your car, I'll bring you back to it later,” he smiled and pulled out of the parking lot. While he drove Dave placed his hand on the interior of my thigh, letting his fingers lightly caress me.

Fifteen minutes late he pulled into his driveway and killed the engine. Before moving to get out he leaned in and kissed me again, this time his hand moved further under my dress and found my bare dick, teasing me immensely. The fact that I responded to him let him know he had accomplished his goal to make me horny.

“Just so you know, I've never done anything like this,” I said quietly.

“I'll be gentle and you'll love it,” he promised and opened the door.

I followed him out and in sliding across the seat my dress raised a bit too much, revealing myself to him.

“Lovely,” he said and helped me from the car.

It was very dark and I was very horny so I didn't bother smoothing my dress down and instead just followed him to the front door.

Once we were inside he really began kissing me and feeling my ass. His hands spread my cheeks enough that his finger played with my little hole, actually going inside just a little. For my part, I found my hand on his impressive bulge and then I was opening his belt.

As we kissed we moved deeper into the house and left a trail of clothes as we went. His shirt, my shoes, his shoes, my dress, his pants, and finally, as we stepped into the bedroom, his underwear. I got my first look at his very impressive cock and wondered how I could ever hope to take anything as large as that. I mean, damn, even though he wasn't fully hard, he must have been ten inches long and very thick.

Before I knew it we were rolling on his bed and he was between my legs, forcing them wide open, his cock pressing against my belly.

“You're so hot, Karen,” he said and kissed me again.

“I want you so badly,” he groaned.

Had I been the good girl I pretended to be I would have run for the hills. Instead I returned each of his kisses with as much passion as I had in me.

“Make a woman out of me,” I gasped. “Oh, baby, take me to paradise.”

“Are you positive?”

“Yes. Yes.”

“Say it, Karen. Tell me what you want,” he said half teasingly.

“Fuck me! Fuck me, Dave! I need your cock inside me!”

He was already in position and slowly pressed his hard cock against my tiny hole, slowly opening me. He placed my ankles over his shoulders and pushed harder, steadily moving deeper and deeper inside.

“Oooohhhh, you're so big!” I squealed, in no position to stop him even if I wanted. Dave was going to fuck me, of that there was no doubt.

As his cock opened me I felt an incredible amount of pain for a short time and then I felt like I was watching him inch into me.

Then he stopped pushing and I felt his heavy balls against me. He was, as they say, balls deep and I was really beginning to feel good. For the next hour he slowly but steadily stroked his big cock in and out of my hungry asshole.

“Yyyesss! Yyyesss! Oh, baby, fuck me! I need it so badly,” I moaned over and over.

His lips locked over mine just before he started pumping me full of his seed and I could think of nothing in the world that could compare to this glorious feeling. I clung to him and wrapped my legs around his waist, making sure that none of his cum could escape. Of course, when he finally pulled out of me there was a river of cum flowing out of me.

Afterward we lay together for quite a while before he talked me into stripping naked and joining him in his hot tub.

“Damn, you're a fox, Karen,” he smiled as he helped me into the tub.

I sat next to him with his arm over my shoulders, his hand lightly caressing the nipple on that side. It felt very nice and it made the nipple stand up. I learned how to suck his cock while we were in the hot tub and when he filled my mouth with his hot cum I was truly in paradise. Not only was I being treated as a woman both in and out of bed but I was feeling more and more like one.

It was hard for me to believe I'd been so scared of going out in public as Karen. Now I could kick myself for not doing it years ago.

“Have you ever considered getting boobs of your own? Either augmentation or slowly with hormones?”

“Oh yea, I'd love to but I have a real job and I doubt they'd understand,” I replied and giggled.

“It's a wonder you aren't taken for a woman anyway. I mean, except for not having real titties, you look more feminine that some women I know.”

“Thanks,” I said and smiled.

While we sat and enjoyed the hot water bubbling around us I gave some thought on how I might be able to get away with boobs at work. I could always wear loose clothes or a vest or sweater under my suit coat. That could hide my boobs but how about a bra? If I grew my own titties there would be the reality of sagging breasts even if I wore a bra, but with breast augmentation I'd always have perky boobs. Would a sweater hide the bra straps? Would a vest?

If I was found out I knew I'd probably get fired. But if I was accepted then I could gradually transition from suits to dresses. The possible scenarios were endless, some good, some very good, and some were horrible. I grinned because of my thoughts. Yesterday I wouldn't even entertain the possibility of coming out in any way shape or form and now I was actually giving serious thought to fully transitioning. Amazing what a good romp in the sack could do.

I was lost in thought when Dave's lips found mine. His hands roamed over my naked body, feeling my flat breasts and tummy, moving down to my dick, sliding over my legs. No matter where he touched me I felt a tingle surge throughout my body.

My small hand dropped to his lap and I found that he was once again as hard as a rock. We kissed an fondled as we made our way out of the hot tub. Kissed and fondle as we made our way back into the house and to his bedroom. I couldn't believe how badly I wanted to feel him inside me again, to feel him stoking in and out and finally pumping me full of his hot seed again.

“Fuck me, Dave,” I gasped. “Damn, I want you so badly!”

“Just what I was thinking,” he replied pleasantly.

Pushing me back on the bed, Dave placed a pillow under my hips and moved between my open legs. He reached between us and guided his thick shaft to my little hole, pressing against me.

“Fuck me, baby, fuck me hard!”

He pushed and I felt myself open for him. He pushed harder and I opened more. One more push and he slid into me. Dave wasted no time before pulling back and slamming inside. Again and again his thick cock hammered in and out of me. As if moving on their own, my legs crept up and and helped him pound into me harder and harder.

“Yyyesss! Yyyesss! Oooohhhh, yyyesss! Fuck me, baby, fuck me! Oooohhhh damn, it feels so good!”

I have no idea if he fucked me for five minutes or five hours, nor did I care. The feeling of his cock sliding in and out of me was too wonderful. But eventually it happened. I felt him jerk, felt a sudden surge of heat deep inside, then he bucked harder and harder, driving his cock deeper and deeper as he pumped me full of his glorious seed.

When Dave took me back to my car it was a little after four. We'd slept an hour after the last fucking so I wasn't falling asleep. I enjoyed the drive home without the benefit of panties or stockings and I stopped along the way for gasoline and a soft drink. I felt like a real slut when I went into the store knowing that I looked like I'd just gotten out of bed, or at least out of the back seat of some guy's car.