[M]y first [T]ime with a trans woman

So, it was a half-assed sort of bachelor party.

I've been in a few weddings, and the thing is, bachelor parties are off the hook these days. Movies always just have guys go to a strip club or whatever, but nowadays people are getting creative, going on paintballing excursions, hunting trips, indoor skydiving, you know… crazy, awesome, memorable shit.

This was not that. This was not even going to a strip club.

This was going to some bars and getting drunk. I'd flown in from out of town for this, and I was in Chicago – one of the coolest, craziest cities in the world – and I was drinking beers with the fellas, something I could have done for a lot cheaper back home.

The one upside was that one dude in our group had the hookup at this club we were at – friends with the DJ or something – and so we were drinking for free.

It was a decent club, too, I'll say that – expensive, and kinda full of douchebags (we were near Wrigley, the douchebag capitol of Chicago), but it also had good music, cute bartenders, and loads of college-age folks on the dance floor.

And I was uniquely positioned to take in the view. The real best man for the wedding party was a ridiculous alcoholic who could not be persuaded not to drink. He had kids and didn't get out much, so he was kind of making up for lost time with this night. But, even though none of us was driving, I felt a need to keep my head above water a bit, if only to keep an eye on everyone.

Plus, I'd gotten really hammered four nights before and had only recently gotten back onto solid food, so it was honestly difficult for me to even look at a drink. I had a pocketful of 5-hour Energy drinks, and that was forming the basis for most of the drinking I was doing. So, while everybody else was too drunk to see anything any more, I could pretty much openly stare at people and they couldn't catch on. It's like a superpower.

One person on the dance floor clearly stood out – this Asian girl, long hair, with really long legs and a very tight, very short skirt. She smiled at everybody, and danced near the DJ booth, so she was visible most of the time. Periodically, she'd sidle off near the bar to check her makeup in a little Old Style mirror on the wall.

I was glancing at her a bit – not obvious or creeper-y or anything – while I got another round for the guys back at our table, and I heard a guy further down the bar talking about her.

"Oh man," the guy was saying, "I can't stop staring at that girl. I mean, just fucking look at her."

Of course, it was like, 1 in the morning, so the guy really sounded like "Homan, i canshtahp starin' that girl… s'fucking lookiter…" but I don't feel like translating all the drunk talk.

The bartender snorted. Like, legit snorted.

"That chick's a tranny, man," the bartender said.

"…what?" The guy sounded devastated.

"Yeah, I knew a guy who hooked up with her once," he continued, "said she had a bigger dick than he did!"

The dudebro at the bar started getting a lot of shit from his boys at that point, and I carried the drinks back to my table, continuing to glance at this girl out of the corner of my eye.

She was more dressed-up than other girls at the bar; most of them were college students, in jeans or shorts with t-shirts or tank tops. She was in an actual skirt, high heels, a tight top that didn't look cheap.

I was intrigued. More than that, I was bored. These guys at this bachelor party were not particularly interesting drinkers… they mostly sat around the couch, oogling the chicks. It was obvious they were sinking into a comfortable rut for the rest of the evening at this place.

Next time I went to take a leak, I calculated my trajectory across the dance floor so that she'd be in my way. Lightly, I rested my hands on her hips as I passed, saying "Excuse me," with a smile.

When I did, she beamed her thousand-watt grin at me, and definitely looked me up and down.

Next time she went to check her makeup, I "happened" to be standing near the mirror.

"You missed a spot," I said.

"What?" She looked in the mirror, more closely.

"I'm only kidding, you look great," I laughed. She looked relieved. "Only…"

"Only what?" she frowned slightly.

I held out one pointer finger, and gently brushed the tip against her cheek.

"Eyelash," I said, smiling.

There was no eyelash, for the record.

After two or three more moments of mutual eye contact over the next half-hour, I asked her if she was ready to let me buy her a drink.

She was.

Her name was Ana, she said. She came to this particular club almost every weekend.

"Yeah," I said, "I heard some of the staff talking about you."

She looked worried. "What did they say?"

"Oh, nothing really," I said. "But you sounded like just the sort of girl I've been looking for."

She still seemed worried, but a little less so – I was hoping she was picking up that I knew, and was cool with it.

"So what are you doing tonight?" she asked.

"Bachelor party," I said. "Wanna hear a funny story?"

She nodded.

"Okay, see that booth over there? The group of guys who look a couple of years too old for this place?"

"Yes?"

"The one in the black sweater… that's Paul. He's the groom."

She started to say something canned and boring, like "Ohhh, that's nice, when's the wedding" or some shit like that. Her eyes were glazing over with boredom.

"He and I used to fuck," I said.

Her eyes lit up and she snapped back to attention. She looked from me to him surreptitiously. "Really? So is he…"

"Oh, no," I said, "He's marrying a girl. He's not gay, he made that very clear to me when he insisted we stop hanging out."

"So… why are you here?"

"That's the funny part," I said, "His brother's the dude in the ugly-assed Fedora over there. He never really noticed that me and Paul weren't really friends any more, and so he invited me. And he wasn't taking 'no' for an answer, and I couldn't really explain the weirdness… and I figured it was time to put on my big-boy pants and prove that it didn't bother me anymore."

"So," Ana said, "Are you gay?"

"Nah," I said, "I definitely don't mind a good cock every now and then, but… mostly I still date girls."

"Wow," she said, "That's… that's cool."

I thought her eyes lit up a little bit when I said I liked cock.

"I even," I said, in a low, conspiratorial voice, "Dressed up as a girl for him once or twice."

"Really?"

"Yeah," I said, "It was kinda nice. The underwear… it's made out of nicer material than I'm used to, you know?"

We chatted a bit more, for ten, fifteen minutes, and then, Ana dropped the bombshell.

"You know," she said, "I… I have a penis."

"You mean between your legs, right?" I said. "Because if it's in a jar in your purse or something, I'm gonna be a little frightened."

She laughed. "No, I'm… transitioning. I-"

"You're a very pretty girl," I said, "Probably the hottest one in here. Anything else is just details."

---

Back at my hotel room, I found myself staring out the window at the view. I'd been in such a rush when I'd arrived that I hadn't had a chance to realize just what a fantastic deal I'd gotten on this place. Floor-to-ceiling windows with a view of the city… honestly it made me a little dizzy.

The bathroom door opened, and when Ana stepped out, she was naked, except for her shoes.

"Well hello," I said.

Her skin was flawless; hairless, completely devoid of blemishes or razor rash. Whatever method she used worked great. Her cock dangled there, at half-mast, not huge but a decent size, a slightly darker shade than her tanned skin. Her bellybutton was pierced, with a little faux-diamond stud twinkling in the low light of my hotel room.

Her tits were small, but there, ending with perky little points.

"Well," I said, "Aren't I overdressed."

I crossed the room in what felt like one huge step, taking her into my arms and kissing her forcefully, hungrily. She gasped into my mouth, our tongues swirling around each other.

"You are so hot," I said, sucking on her earlobe and kissing my way down her neck. Her cock started to rise up to meet me. Mine, meanwhile, could have cut glass.

I dropped to my knees and took her into my mouth. She moaned, and I started to bob my head up and down, relishing the taste of her.

After a minute or two of that, she pulled me back to my feet and started tearing at my clothes. I spent a few minutes doing the undignified dance of the guy getting laid, kicking my shoes across the room, yanking my shirt over my head, unbuckling my pants.

When my cock sprang free, it was harder than I'd ever seen it, already dripping a thin stream of clear precum on the floor. I was going to have to be super careful, or this would all be over very quickly.

Ana pushed me backwards onto the bed, and started crawling upward towards me. When she reached my face we kissed, her saliva-covered cock rubbing up against mine, grinding on each other.

We made out like teenagers for awhile, my hands taking the occasional field trip to explore her body, her tits, her cock, her ass. We probably did that for half an hour, to be honest, and I felt like I was on the verge of cumming the entire time.

Eventually, she stood, holding up a hand so I wouldn't try to follow her. She went to her purse, and came back with a condom and a bottle of lube.

"Hold still," she said.

Slowly, carefully, she started to unroll the condom onto my cock. She had to do it slowly and carefully or I would've gone off; it was like she was playing 'Operation' with my dick. When that was done, she squirted some lube onto her hand, and reached back behind herself to start applying it to her ass.

That done, she carefully gave me a couple of tugs, slathering lube all over my cock.

She settled onto me slowly, my dick having a surprisingly-hard time sliding in. She was incredibly tight. As she was using her hands to brace herself and guide my cock inside of her, I took advantage of the opportunity to grab hold of her, jerking her off slowly, encouraging what she was doing.

She came to rest, and I was embedded to the hilt in her perfect ass.

She started to bounce up and down then, slowly at first, picking up speed as the lube started to be more evenly-applied. She started to moan louder – so was I, calling out loudly enough that I was starting to get nervous about people complaining to the front desk.

You left the drapes open, I realized, and looked out onto the dazzling cityscape for a moment. All the twinkling lights out there were other rooms, other places where people were awake, and any of them could be looking in at me right now, balls-deep in Ana, jerking her off directly towards my face.

It was an incredibly hot thought.

Suddenly, Ana cried out, louder and higher-pitched than before, and I felt her ass clamp down on me. Her balls spasmed, and I was suddenly hit in the face with a rope of her cum.

That was enough to send me over the edge. Screaming out her name, I erupted, feeling the condom swell as it filled to the brim with my jizz.

She collapsed onto me, a sweaty pile, and slowly I extracted myself from her.

She started to cry a little.

"Sorry," she said, "Sometimes I cry after I cum. It's silly."

"No," I said, "It was wonderful. You were wonderful."

She gave one big, shuddering sigh.

"How long are you in town for?" She asked.

Source: reddit.com/r/gonewildstories/comments/3pp9wq/my_first_time_with_a_trans_woman