Hot Encounters

I joined one of those swinger sites, just out of curiosity. I learned three things right off the bat. The first thing I learned is that there is a lot more men than women on those things. The second, most of the women are so swamped with responses, that they almost never respond back unless you can really catch their eye. The final thing I learned is, most of the guys on there are total sluts, willing to do damn near anything you want them to…which I decided to take advantage of.

I shopped around, and picked my first contact. We’ll call him Joel. Joel lived near me, and was slightly older than myself. He described himself as an ordinary guy, looking for an extraordinary experience. He said he was 5’9, 175 lbs., brown hair and eyes, and clean-shaven. He admitted to a small amount of pudge, due to “desk jockey-itis” as he put it. He didn’t describe himself sexually, or post the obligatory nude shot, which was a bit of a surprise. Seems like that is a requirement for these sites, sometimes.

I emailed him, and we started to chat back and forth. Things moved very slowly at first, as we both worked during the day, and had to be very careful what was said, since who knew might be reading these things. Eventually, we started to chat from home in the evenings, which meant we could be as graphic as we wanted. I quickly learned that he has a bit of a cross-dressing fetish, but had never dressed for a partner. Me being totally into the cross-dressing/transgender scene myself, quickly encouraged him in this. After a few weeks of online chatting, we agreed to meet up for drinks after work one Friday night.

I dressed for work that day with a little extra care, and a nice surprise for him underneath. A couple of years ago, a lady friend bought me several pairs of sexy panties, knowing my preferences, and I pulled one out and slipped into it for that evening. My cock swelled just a little as the red silk slid over it, but I ignored it as best I could. I didn’t want to waste anything for this evening, if things went the way I hoped they would. Besides, I always got a little thrill out of wearing my panties around my coworkers, none of whom knew anything really personal about me.

The day moved much too slowly for me, and I found myself checking the clock constantly. Joel messaged me after lunch and said the same thing. He was nervous, but excited. After that, the day moved a little quicker. At the appointed hour, I closed up my desk, and slipped out the door before my coworkers could make any invitations to join them. As I walked to the bar we were meeting at, I could feel my cock stirring in anticipation of things to come.

I got there first, and grabbed a table towards the back. I sat with facing the door, so I wouldn’t miss him if he came in. Sure enough, a few minutes later, he walked in. I waved him over, and we shook hands. I ordered us a round of drinks, and we settled in to get to know about each other. I told him that I was a bisexual, and very sexually curious. I was always looking for new partners to have fun with, and to try new things.

Joel finally admitted that he’d only been with one other man, but that it had gone on for two years. It was this other man that got him into cross-dressing, and ever since then, he’d been looking for someone who would enjoy his efforts as much as he did. I assured him that I thought he would look fantastic dressed as a lady, and would love to see him that way, if he wanted to. He blushed, but admitted that he wanted to dress for me.

With that, we settled down and did some more chitchatting. My goal was to get Joel relaxed, so that things would be as natural as possible. We eventually ordered dinner, and afterwards, he suggested that we make our way towards his place. That being my whole plan from the start, I of course accepted. We walked casually, but I did notice him casually adjust himself. My thoughts wandered to what he had down there, as it looked like quite a nice package. I was thinking about his cock when I realized he stopped talking.

He was looking at me with a sly grin on his face, and told me I was about to pass his building. I grinned sheepishly, and followed him up the stairs to his apartment, admiring his butt all the way. From where I was, I couldn’t see any trace of a pudge anywhere on him at all. He let us into his place, and offered me another drink. He gave me a quick tour of his apartment, and then excused himself. He said he was going to go “slip into something a little more casual”. I grinned, knowing what he meant.

I was looking out the windows when he returned. I turned to see a stunning creature in a red halter-top, and black micro skirt. He was wearing a black wig, and had made his face up very well. He had on black stockings, and stiletto heels. He was one sexy woman.

I smiled my appreciation, and he shyly smiled back. I walked over to him, and took his chin in my hand. I lifted his face up, and planted a gentle kiss on his lips. I then walked slowly around him, admiring the way he looked from all angles. The skirt made his butt look even sexier than it had on the stairs, and I could tell he was practiced in those heels. I slid my hands over his butt, and he pushed back at me. He turned into me, and we kissed again, this time with much more passion.

His hands moved to the buttons of my shirt, undoing them one by one. He ran his fingers through my chest hair, paying special attention to my nipples, which grew rock hard from the attention. He slipped my shirt down, and ran his hands over my ass. He kissed his way south, flicking my nipples with his tongue, and sucking them just a little. His nimble fingers undid my belt, and then the button of my slacks. He slipped his hands in, and gasped as he felt the silk of my panties. He giggled as he saw what I was wearing, and came back up to kiss me again.

He led me to the bedroom, and laid me down on the bed. He slipped my pants off, and stood back to admire my body, as I had nothing but red panties on. He bent down to me and gave me another kiss. He broke it off, and stepped back from the bed. He turned on some soft jazz, and began a slow seductive striptease for me. He slipped the top off, exposing his smooth chest, and his skimpy push-up bra. He flipped that off, and let it fall. His hips swayed to the rhythm as he slid the zipper of his skirt down, and let the skirt slide slowly to the floor. He was wearing a black thong, and he did have quite a nice package. He turned and showed me his smooth, firm butt, and slipped the panties down, spreading his legs as he did so I could see his balls hanging. He cupped them in his hands, and turned to face me.

His hands ran up his body, and I saw his cock. It was indeed a nice one, had to be at least 7 inches long, and thick. Best of all, he was totally shaven. He reached out, and pulled my panties off of me, making us both naked. I reached for him, and we kissed again. I pulled him on top of me, and our cocks touched. I loved the feel of his smooth skin against mine, as he slipped down my body. I could feel his breath as he neared my cock. He teased me for a long time, running his tongue up and down, flicking my cockhead, but never taking more than just a tiny bit into his mouth. I was moaning, enjoying the treatment, but wanting more. I reached down, and guided my cock into his mouth. He immediately sucked it deep, as if he was waiting for me to do that.

He was a complete pro at cock sucking, doing things most women don’t know how to do. Of course, it stands to reason that a man would know how to make a man feel good, just like women say they can make a woman feel better than any man could. He took my cock all the way down his throat, and teased and fondled my nuts at the same time. I could feel myself building towards release, and apparently, so could he.

He stopped his actions, and got off the bed. He reached into a drawer, and pulled out a bottle of lube. With gentle hands, he spread a nice amount over my cock, and then onto his ass. Without a word being spoken, he straddled my body, and guided my cock to his ass. He was so tight that I started to think it wouldn’t work, when all of a sudden I was in. He lowered himself down, and took my cock all the way. He rode me this way for a while, and then we moved into new positions. I had him stand, and bent him over the side of the bed as I impaled him on my cock. He begged me to be rough on him, so I really pounded my cock into him.

His moans were really getting me hot, and I knew I was close. I asked where did he want me to cum, and he told me to cum on his ass. I gave him one last thrust, and pulled out to explode onto his butt. My cum shot up and landed as high as his shoulder blades, and we collapsed onto the bed. I lay on my back, and Joel brought his rock hard cock to my mouth. He was so ready, that I only had to suck it a few times before he tensed up. He took his cock away, and shot his load all over mine. He covered my dick with his cum, and then licked me clean.

I pulled him up to me, and we kissed again. I loved tasting my own cum on another’s lips. We lay together for a short while, and eventually started up again.

Joel and I spent the weekend together, and I even got him to go out as a woman…

But that’s another story.