Seducing Jay at a House Party

Ann seemed pretty happy with the party she threw for her birthday. People were mingling in her garden, talking and laughing while they fought summer's heat with beer. I didn't know many of Ann's friends - in fact, the only face I recognized at the party was her own, but I knew she kept company with mostly single people and any of her gatherings resembled more of a pride parade than a house party. I wasn't with anyone for a long while and honestly, this seemed like a perfect place to hook up with somebody.

She approached me while I was sucking on a nearly empty bottle of beer pretending to take interest in the band that was preparing to start playing. Probably looking as the loneliest guy in the world, her rescue didn't come a moment too early.

"How do you like it?," she asked and without waiting for an answer she put a fresh bottle of bear in my hand and said: "Come on, let me introduce you to someone."

She knew exactly what I was looking for. We often talked about our kinks, and it was no secret to her that I went for both girls and guys. After surveying the crowd for a few seconds, her eyes lit up and she took me by the hand. We were going to meet this gorgeous girl. I only saw her from behind, but she looked to be wearing one of those school-girl uniforms: not-too-high heels, a red short pleated skirt and white shirt, so I could see a bit of her naked back between them. Sexy and inviting, but not slutty.

"Hey, Jay!," Ann tapped her on the shoulder. English isn't my first language, but I was sure Jay would be a guy's name. I could feel my heart skip a beat as I waited for the verdict while Jay turned around.

And Jay did, and I still wasn't sure. Ann politely introduced me, made sure I had a beer for the last time and then leaned over to me and shouted over the band, which by now started playing: "I thought you could try something different. Jay is a great guy!"

I am good at chatting up ladies. I am also fairly social with guys. I figured I should just mix the two and I should be set. Still, I stood there like an idiot just looking at Jay sipping gin and tonic.

He saved the evening: "So, how do you know Ann?"

I started telling him how we met in detail. In fact, probably too much detail, as I could see from the sympathetic smile that came over his face. It was beautiful. For a moment, I stopped to examine it. He was a guy, alright. Not too feminine, but just pretty and smooth enough to be able to pull it off. I would probably fancy him even if he didn't crossdress, but that made him that much more appealing. He was a beautiful mystery to me which I had to resolve.

Realizing that I am getting dumbstruck once more, I quickly got to the point: "Ann is great, yeah. But nevermind how we met. I really like your outfit. You look great in it."

The compliment suited him and he told me something about not doing it too often. This was the first time he was like that in the public. Ann gave him confidence to "come out" as a crossdresser. Alongside a dressing room in her house that he could use, so he didn't have to worry about cab drivers and the general public.

"Well, I think you are amazing," I gave some more compliments and the conversation became relaxed and easy. We talked about everything - we were both 30 at that time and he was working on a Ph.D. Jay liked the same music as I did, or so he said, and I liked the same restaurants as he, or so I said.

Not before long I felt like I had enough courage and beer in me to ask: "So, do you prefer girls or guys?" Many crossdressers aren't gay, and I knew it, but I still felt a little silly for asking it.

He gave that sympathetic smile again: "Well, I've never been with a guy... before."

If there was ever time for mixed signals, this wasn't it. We talked some more and we laughed, and after I said something funny, he touched my waist with his hand. After a few minutes, he just left it there on my waist, so I took the hint and during a short pause in our conversation, I kissed him.

At first, the kiss was gentle, but then I stuck my tongue so far down his mouth I was afraid he would choke. Instead, he wrapped my head in his arms and, as he was a couple of inches shorter than me and the heels didn't help, he stood on his toes. While his hands were all over my shoulders and head, I put mu arm up the back of his white shirt. He just exhaled and pulled away his lips from mine and looked at me from an inch's distance, as if he was trying to read what's in my eyes.

Jokingly, I said we that we should "get a room" before me make somebody uncomfortable. He gave me a dirty look and said: "I think Ann wouldn't mind if we used the changing room".

Holding hands, we briskly walked into the house. Because Jay didn't like the idea of actually making the journey to the party in his schoolgirl outfit, Ann was kind enough to give him her guest room to use as a changing room.

I walked in there first and Jay followed, locking the door behind him. There wasn't much furniture in the room: a small bed, a writing table and a chair.

Still standing, we started kissing again. My hands went for the shirt again, but now I found my way under the skirt. I felt his warm butt cheeks hugging a pair of thongs and I started massaging his ass. He was already rock stiff and he was getting hard - I could tell from him rubbing on my leg.

While I still massaged his ass, getting my fingers just a little bit shy of his hole, I started kissing his neck. He pulled away a little, to give me room, and started unbuttoning his shirt. He stopped when he got halfway down and revealed his hairless chest and a black satin bra.

This made me crazy with excitement. While pressing my lips against his chest, I lifted him from the floor and threw him on the bed. As he was on his back in bed with me kneeling over him, we made a moment's pause and looked into each other's eyes. We were both smiling, anticipating the next thing that would happen.

He was laying in bad comfortably and I slid to the bottom of it. I pulled him, by his legs, to the edge of the bed so I knelt on the floor and slowly spread his legs apart. I started kissing and caressing his thighs and grabbed his panties and pulled them off of him. His cock was ejected from the lace thongs and it stood up straight and hard.

I worked my way up his thighs and then slowly, without touching it with my hands, I put the tip of his cock into mu mouth. Then I started twisting my tongue around it, putting more of it in my mouth a bit by bit. By the time I was fully sucking it, he was groaning, unbuttoning his shirt with one hand while caressing my hair with the other.

I sucked him for several minutes. His skirt was now pulled over my head and I kept his thongs in my hand, every once in a while bringing it to my nose and rubbing it against my face. He seemed to love this and it took him great self control to lift his head and ask me to stop for a moment.

"Do you maybe have some lube? I have a condom," he asked, almost panicked that if we didn't have any lubricant we couldn't go any further.

I produced a bottle of lubricant from my man-purse while he took out a pack of condoms. We got back to our positions - where we left off, but this time, he put a pillow under his ass, so I had easier access.

I sucked his cock a little more and then, while he was still hard and precumming, I took it out of my mouth and worked my way down his balls, putting them in my mouth and kissing the sensitive area between the balls and his asshole.

Finally, I made it to his opening. I was licking around it and I could feel him grabing my hair even harder and pushing my head between his legs. I inserted my tongue as deep into his asshole as I could.

For the first time, he lift his skirt and started stroking his shaft. I kept working my tongue for another couple of moments, while I prepared the lube. I put some on my finger and slowly inserted it into him.

He was moaning and groaning and asking for harder and stronger. I inserted the second finger and the third. He took it all in while he stroked his cock even faster. I was relentless on his asshole and lube was spreading around all over his ass cheeks.

I looked up at him as he exploded. His sperm squirted all over the place, covering his belly and parts of my hair and face. I didn't mind it, I just pulled my fingers out, climbed up the bed and started kissing him on all fours. He kissed me back and then he started kissing my forehead and sucking his cum out of my hair.

Jay got a moment to relax and recover from his ejaculation, while I put on a condom and some more lube over it. He was still on his back, so I started entering him in the missionary position. Fingering and lube helped me get into him very easily and I started pounding. He put another pillow below his back so I had a comfortable position.

At first, he was silent and relaxed, but in a few moments, he started moaning again. He was grabbing me by my chest hair as if to hold on to it, or by my ass, as if to push me in as hard as he can. Sweat from my forehead were dropping on him, but he didn't mind - he even wiped it off.

I was getting very excited and I hugged him and pressed my chest against his. I could feel the bra rubbing against me and it only made me harder. He was getting stiff too and I wish I could give him another ejaculation, but I was nearly done. I whispered into his ear: "I'll cum soon". He asked me if I wanted to do it on his chest.

I pulled out of him, took off the condom and threw it away and a moment later started spraying his chest, his chin and even his mouth. He liked it and licked the sperm from his lips. I was exhausted and happy. I dropped over him like dead weight, but then I pushed back on my elbows so I gave him a little room.

He started pulling his cock again and he put it between my butt cheeks after he felt with his hand where they might be. Then, he squeezed them and started dry humping me. I was still relaxed and enjoyed it - my finger ran over my cum on his chest. I collected some and brought it to his lips - he licked it all off.

Finally, I could feel his hard cock pulsating between my butt cheeks. He ejaculated once again and his warm cum landed on my lower back. I wiped it off with my bear hand and laid next to Jay.

We both breathed slowly. I was facing the ceiling and I could feel his look on my eyes. It felt nice. Jay turned to me, put his hand over my chest and kissed me in the cheek. We stayed in bed for a long while and by the time we got up the cum on our bodies was already cold and brittle. The music was still playing in the garden - people were having fun and nobody seems to have payed any attention to us.

I watched him get dressed as I set on the side of the bed. His kept his skirt and put the panties back on. He changed the shirt, which was drenched in sweat and cum for a clean, blue one, in which he probably came to the party. The outfit still looked hot. He stuffed his jeans, a pair of boxers and regular shoes into a backpack.

He came to me, kissed me on the lips, gently, and turned around to leave. I opened the door as if this were my place. "Ann has my phone number, if you want it," Jay said and left.