Unexpected Sex

bywoman_inside©

My ex-girlfriend hadn't changed since I'd last seen her. She was still slim and, while not exceptionally curvy, definitely with enough curves in the right places. She was also definitely dressed to impress, wearing a yellow summer dress that went well with her shapely, caramel-colored legs and contrasted nicely with her well-brushed jet-black hair, her legs crossed as she was sitting on the bed.

"Hi," I said.

"So you made it," she answered.

"I guess so. You look great."

"Thanks."

I smiled, looking forward to the sex - after all, she had wanted to meet in a hotel room and was sexily dressed. Yet I was a bit overly nervous also, without knowing why.

She took a bag that was next to her and pulled out a bottle and wine glasses.

"Shall we have a drink first? I'm taking medicine so I won't have any alcohol, but I got you some wine."

"Sure, thanks."

I hadn't even finished my first glass of wine when I felt kind of dizzy, and my vision a little blurry. I tried to say something, but my speech was slurred.

She pulled out her phone and made a call.

"Yeah, it's taking effect. I'm ready whenever you are."

There was a knock on the door almost immediately. "Stay here," she said to me. Then she went to get the door. I realized she had put something in my drink, as scared as I was all I could do was to stay where I was, as I'd been told.

I heard her open the door, I heard someone, or maybe two people, walk in. I heard men's voices, but I couldn't hear clearly, and I couldn't make out any words, as if everyone's speech were slurred, which was probably the drug affecting my hearing. I could distinguish a woman's voice, presumably my ex's, and two deeper, male voices. She walked over to me and tapped me on the shoulder.

"Just do whatever I do."

She began to undress. Unable to stop myself, I began doing the same, and soon we were both naked. She then got on all fours on the floor. As if on autopilot, I also got on all fours side by side.

One of the men approached her. He was completely naked - a blond guy, slightly tanned, muscular - and he put his hand on her hips. The tip of his very erect cock grazed against her ass, and he started pushing it in even as she moaned. I felt a pair of strong hands on my own hips. I knew what was going to happen, and I turned my head to at least take a look at the stranger who was going to fuck me.

He was black, very muscular and, judging by his chest, fairly hairy.

I felt the tip of his manhood on my asshole, and closed my eyes. I felt him push, and for a moment I thought he would not go in, but then he did, slowly, very slowly. Firmly, he pushed his thick manhood into me little by little. I had no idea how much more I had to take, I felt I could not take any more yet he pushed deeper into me and, only after what seemed to be forever, I felt his pubic hair against my ass, and knew his manhood had gone in me to the hilt. For a moment he simply held it in place, and grew ever so slightly bigger, sending a spasm of pleasure in me.

Then something broke. No physically, but mentally. It was as if a dam in my mind had broken down, and desires and memories came flooding. I let out a loud moan, and let out tears of joy at what was being done to me. He began thrusting, pulling out slightly and then firmly pushing back in again in a slow but rhythmic motion. With each thrust, memories came flooding back.

I remembered one time when I'd barely hit puberty and I was watching a soccer game with some older boys, and how, as they had no uniforms, one of the teams had played barechested. I remember how I had to put my backpack on my lap to hide my little erection, and how I'd completely lost track of the game while staring at the boys' chests and legs.

I remembered in the showers taking a peek at the other boys, lying to myself, telling myself I was only curious and just wanted to compare myself, when I desperately wanted to touch their cocks. I remembered at a cousin's quinceaños party - I remembered wondering what it would be like to wear an elaborate pink dress like hers.

I remembered one particular time I'd had sex with the woman now being fucked next to me - one time I'd pounded her hard, brutally, and she'd loved it. I didn't dare admit it even to myself then, but I did now: I had fucked her how I wanted to be fucked, and I'd been aroused by imagining myself in her place, that it was me spreading my legs and getting cock.

I remembered one time in my teens when I accidentally walked in on another cousin nursing her baby and how the quick glimpse of her naked breast had seared itself into my mind - I had convinced myself it was desire what I'd felt, but that was a lie - I'd felt envy.

The man fucking me began thrusting harder and faster. I had a vision of myself, undressing as I'd done earlier, but saw myself dressed not in the male clothes I'd been wearing, but in a wedding dress. I saw myself lie on the bed, and the man fucking me in the real world was my husband, and I spread my legs for him. I envisioned him deflowering me even as he thrusted harder and harder. Then he came both in my vision and in reality, and I had a screaming orgasm and everything went blank.

I'm nor sure how long I was unconscious, but when I woke up, I could feel my ass was sore and sticky - it had been no dream. Before I even opened my eyes, I knew my life had changed - not because I'd had sex with a man, but because of what it had made me feel.

"You loved it."

It wasn't a question. My ex-girlfriend, now dressed again, was sitting on the bed. The men were gone.

"It's funny to think you turned out to be more feminine than me."

"Who were they? The men?"

"The one who fucked me is called Mike. The one who fucked you - why do you want to know?"

"Well...."

"You were just a lay to him, you know. He didn't know you were a virgin, either, but he did notice you were tight, he said so, but I guess you were too busy squealing like the bitch you are to notice."

"Why did you do this?"

"You're not complaining, are you? After all, with that drug you can't be made to do anything you really don't want to do. So you wanted to get on all fours and have your brains fucked out, whether you knew it or not."

I paused for a moment. My life would definitely change - I didn't think I'd ever put my cock inside anybody ever again, for starters.

"No, I'm not complaining. Whatever your reasons - thank you."

"After we broke up," she said, "I made some gay friends and through them met all sorts of people - gay, bi, trans. I kind of recognized what you were - I admit part of me just wants to prove you were never a real man, but I also wanted to help you get in touch with yourself. So I enlisted the help of Mike and his partner -they're both bi- and, well, here we are. So there's one last favor I'm going to do for you."

She took a suitcase from underneath the bed.

"This is for you," she said. "Goodbye."

"Goodbye."

She walked out the door. Whatever happened now, I knew she was out of my life.

I opened the suitcase. I smiled nervously.

A couple of hours later, I was putting on a dress. I'd shaved my legs and armpits with the pink razor I found in the suitcase, and I'd put on the matching bra and panties that were underneath it. I put on red nail varnish from the makeup kit in the suitcase. Soon enough I was done dressing up as a woman.

I took out another important item in the suitcase - an LGBT guide for the town. I saw there was a trans and cd-friendly bar just a couple of blocks away - not far to go even in the very high heels I was now wearing. Well, I now knew where I'd be heading next - tonight I'd make sure I got cock again, and this time I would need no drugs to let my need be satisfied.

Report Story

bywoman_inside© 5 comments/ 25442 views/ 9 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartStockcard12, monak4u and 7 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (5 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (5)

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel