[TF][TFM] Experimenting with a couple for the first time…

**I’ll link to my pic in the comments below, for anyone curious**

I learned to pass at a pretty early age. By the time I was out of college I had long, black hair that I could wear in a bun when I presented as a man or styel when I was all dressed up. Being petite and Asian certainly helped. I started frequenting fetish and alternative lifestyle clubs and bars as soon as I legally could. But all my early sexual encounters were with women. I typically dressed with 70s-Bowie flourish, but eventually came out of my shell and started spending most of time in drag.

Eventually I moved on from curious women to people more like me. Other cross dressers, androgynes, and even trasgenders. Anyone who liked to wear silk or satin or lace who liked the way I looked in a skirt. Masculine men didn’t interest me and neither did guys who were just looking to do something out of the ordinary. I always went for women or those who came from a similar point of mind.

It wasn’t until I was out of college and living in a new city when I started to get more adventurous. In 2012 I got my first high paying job and my first place to myself. I immediately filled out my wardrobe with dresses, skirts, lingerie, and heels. If I wasn’t at work or the gym, I was en femme. I got familiar with every club that catered to kink or alternative lifestyles. I joined websites and posted ads on Craig’s List. I had a lot of sex. But it was still the same type of partners–always feminine.

I’d been on Craig’s List for a few months when I met Susan. She was in her late twenties, recently divorced, and just getting into kinkier things. She’d experimented with BDSM, but didn’t really like being with a dom. So instead she’d ended up in a friend’s with benefits relationship with a hipster named Jim. He had pushed her to explore her bi-curious side and she’d met up with a few women, but she always felt disappointed. She just missed cock.

That’s what brought her to my personal ad. I always posted pics when I posted. I didn’t want to get confused with the masculine, hairy guys wearing a pair of panties. Susan found me attractive and wanted to experience the best of both worlds. We exchanged a few emails and agreed to meet up for drinks.

I met her at a suburban bar dressed in a girlie pink dress and flats. Susan was tall and slender with small tits and straight brown hair that she parted in the center. She gave off kind of a hippie vibe and looked overdressed and a little uncomfortable in a little black cocktail dress. Perhaps that’s why it didn’t take that long to get her out of it. Within three hours of meeting I was fucking her doggie style in my apartment. We both kept our heels and stockings on the entire time.

She brought up the idea of a threesome that first night. It was something her man wanted. Of course, he’d been pushing for her with another woman. But she knew he was bi. I didn’t reject it, although I wasn’t really interested either.

I went all out for our next two meetings. We didn’t bother with drinks. She came straight to my place and I’d greet her in a bustier, garter belt, crotchless panties, stockings, and heels. All covered by a little silk robe. She wore lace and satin under her clothes. We played with toys and light bondage. And we also made a video of her riding my cock. When we watched it later she convinced me to let her share it with Jim.

Of course he loved it. She started begging me for a threesome. The sex with Susan so far had been amazing. The thought of adding a new element excited me. It didn’t hurt that Jim was pretty in a Johnny Depp sort of way. I agreed with one stipulation–I wouldn’t receive anal.

I went to Susan’s place for the threesome. I showed up in a silky black dress that buttoned down the front. Beneath it I wore a purple satin bustier, purple satin panties, a black lace garter belt, black stockings, and black heels.

Jim was even more gorgeous in person. He had on tight jeans and a western shirt–probably worn ironically, since he also had a fu manchu despite being a total hipster. He was barefoot when he came to the door.

Susan was sitting on the couch in a loose floral blouse and short denim skirt. She got up and offered to grab me some wine. Instead I wrapped my arm around her neck and pulled her lips to mine. My heart was racing and I was nervous and didn’t want to think about things too long.

We moved to the couch and started making out. Jim didn’t say much. He pulled a chair over and just watched. I pinned Susan down and slid my tongue into her mouth. My cock got rock hard. I ran my hand up her thigh and started rubbing her pussy. She moaned with contentment.

“Slow down,” she finally said.

She pushed me away. I sat up. Susan started unbuttoning my dress. Jim audibly grunted when he saw my sexy purple lingerie. I cock was bulging in my satin panties. I sat on the couch with my dress completely open and Susan slid to the floor. She spread my legs and started kissing her way up my thighs. She licked my cock through my satin panties. Then she slowly pushed the gusset aside and took it out.

I closed my eyes when she started blowing me. I concentrated on not cumming. When I opened them, Jim was behind her on the floor. Her top was unbuttoned and her bra cups pushed down. He was kissing her neck. He unzipped her skirt and it slid off.

Susan got on her hands and knees and kept blowing me. Jim undressed quickly. He had a lean, tight body and a decent cock. Bigger than mine. He pushed it into Susan’s pussy.

We all started moaning. He fucked her while she sucked me. He was going nice and slow. But she was working her was up and down my shaft. I put my hand on the back of her head and pushed with my hips. I fucked her pretty face while Jim drove into her pussy. Finally I exploded. I came in her mouth and she took it all.

The stopped fucking long enough for Susan and I to kiss. Then we moved to the bedroom. Jim got between us in bed. His hard cock was glistening from Susan’s pussy. She started to blow him.

“Kiss me,” he said to me.

I hesistated, but he put his hand behind my head and ran his fingers through my silky black hair. We started to kiss. Already I was getting turned on again.

“Lick my cock, Jennie,” he said.

I didn’t even hesitate. I was still in my lingerie and stockings. Susan was in a lacy black bra and panties. we tooks turns kissing each other and Jim’s cock. I’d never sucked off a “real” man. Just other T-girls.

I went for it. While Susan watched I started blowing her man. He moaned and groaned and kept playing with my hair. I was as agressive as any porn star. I moaned loud and talked dirty. I looked him in the eyes. He grunted when he blew a hot load down my throat.

I was hard again and Susan was the only one who hadn’t cum. I rolled over on my back and she straddled me. I could tell Jim loved the site of the two of us in lingerie as she rode my dick. We fucked long and hard. It was my first time in her without a rubber and she felt incredible. She rubbed her own clit and got herself off twice on top of me. When she rolled off to catch her breath, Jim was ready.

He wrapped his mouth around my shaft and licked tasted Susan’s juices. He got my dick nice and lubed with his tongue.

When he pulled away he rolled on his back and instructed Susan to mount him. We both understood what he was asking.

Susan straddled Jim and put her ass in the air. I spread her cheeks and slid my cock in. And then we slowly moved to Jim’s cock so he could get in her pussy.

I could feel his dick moving inside her. Rubbing mine just centimeters away in her ass. We could barely build a rhythm. Jim and I just took turns jostling Susan around with our two cocks in her. She couldn’t even make audible words. It was insanely hot.

I came first, in her tight little asshole. And when I pulled out she rode Jim hard until she came. And when she rolled away I jerked his lubed cock off until he came again.

Things kind tapered down after that crescendo. I ended up not spending the night. But it wasn’t the last night the three of us spent together.

Source: reddit.com/r/gonewildstories/comments/9a4i9z/tftfm_experimenting_with_a_couple_for_the_first

3 comments on “[TF][TFM] Experimenting with a couple for the first time…

  1. This is a hot story, it makes me wish I wasn’t so much of a burly man, even if I slimmed down, I’d never pass off as anything besides overly manly with my frame. I also wish my fiancee was into transwomen and threesomes, but she isn’t into either which I respect. One of these days I’ll get to writing about my time with a transgirl, but I wish I got to experience it with another woman like this.

    I hope to hear more about the other nights.

Comments are closed.