Thought I'd write this while it's still fresh in my mind. This happened a week ago.
I was sitting at home, bored, with no plans for the afternoon. It was raining on and off, and the prospect of going anywhere seemed glum. I fired up the computer, thinking to watch some porn movies, read some stories, get hard, and jerk off. As part of the jerking, I checked out the Craigslist ads to see what the perverts were looking for. I went through the M4M section, since sometimes I play with men and the ads might get me hotter. Then I thought, what the hell, let's place an ad for something that I'd like, and see what happens.
I wrote an ad saying, "Older WM wants to lay back on the couch and watch porn while a younger man in panties sucks my cock to completion and swallows my cum." I titled it "Where's my Femme Boy Today?" and posted it. Then I went back to cruising porn, reading incest TG stories, and getting hard. I checked my e-mail periodically to see if I got any answers.
There were a few I wasn't interested in, older guys who just wanted to suck , chubs who wanted me to come to their place. Then, after the ad had been up for an hour, I got a real hit. It was a young man in his 20s who claimed he'd never been with a man, but wanted to explore his submissive side. He said he had panties and a camisole to wear and could be at my place in an hour.
We sent a few e-mails back and forth, and I told him where I lived. He said he'd be there at 7. I showered and dressed in a robe, set up some online video porn of young girls getting fucked in the ass and waited. 7 came and went with no knock on the door. I checked my e-mail one more time, and there was a message saying he was outside in his car and wanted me to show myself. Obviously he was really nervous. I stepped to the door, opened it and looked around, seeing someone sitting in a car, then closed the door. A few seconds later there was a knock, and I let him in.
He was perfect - about 5'8", very slender, a mop of dark hair that could easily be feminine. We sat on the couch and I started a movie. He said he was nervous, this was his first time, could we sit and talk? I said sure, take your time, be comfortable, I'm not going to ask you to do anything you don't want to do.
He explained he had a girlfriend, was in fact engaged, and had been fucking her for 5 years. He had a fantasy about being a submissive sissy that he wanted to explore. I lay back on the end of the couch and opened my robe, nude underneath. We watched the movie for a few minutes and I stroked myself until I was erect. I told him to bmake himself comfortable and do what he wanted. He told me he wanted to try sucking a cock for the first time, and I said I'd be happy to oblige. After looking at my cock for a while, he stood up and began to undress. Under his shirt he wore a plain black camisole. He took off his jeans to reveal white cotton thong panties with little hearts printed on them. His cock was beginning to create a bulge in the panties.
I stood up and joined him, dropping my robe. I knelt down behind him and caressed his naked hairless ass with my hands - it was smooth and perfect. Then he turned around and I felt his cock through the panties. I was stiffening, so I pulled the panties to the side to see. He had shaved completely, having no hair around his cock or butt. His upper body was covered by the camisole, but I could see no hair there either. He was very nervous, asked if I had ever had any STDs. I was recently tested and found completely clean, which I told him. He asked if I minded wearing a condom while he sucked me. I said that would ruin the taste for him, but I was willing if that was what he wanted.
I fell in love with his cock immediately. It was hairless as I said, but it was also slender and getting longer. I asked if I could suck it, and he agreed. I could almost take the whole thing without deepthroating - it was about 5", very slender. I kept thinking it was the perfect size for my ass.
Then he surpised me - he said he didn't think he was ready to suck a cock yet, and asked if I would fuck him instead. I agreed, but said if it was his first time, my cock might hurt - not to brag, but it's over 7" and fairly thick. He said he really wanted it, and if I'd wear a condom he'd be fine. I said okay and went to get a condom and some lube.
When I came back he had removed his panties, and asked how I wanted to do it. I got him on his knees on the couch, and got behind him. I got some of the lube in my hand and greased his hairless little asspussy. I pushed one, then two fingers into him without much resistance. He may have been a virgin to cock, but something had been inside him before. Then I backed off and put a condom on (Trojan Magnum) and lubed my cock. I got behind him - his slender ass was making me incredibly horny. I applied the tip to his hole and began pushing.
Like I said, something had been in there before. He didn't express any pain, and his hole felt like it had been stretched before. I eased in further and further, caressing his ass, and reaching around to caress his balls and cock as I did. Finally I had about 6" inside him, and I knew I couldn't last much longer. As a final precaution, he asked me to pull out before I came (paranoid little bugger). I grabbed his hips and pulled him against me, giving him the last inch or so. Holding his hips tightly, I fucked him hard, pushing as deep as I could get.
After all too few strokes, the situation overcame me and I was ready to cum. I pulled out just before I came, stroking my cock to get al of it out, while he turned and watched.
I told him how good it had been and caressed his hard cock for a minute. I asked him if he wanted to cum, but he wasn't interested. I went off to the bathroom to dispose of the condom.
When I came back, he was stepping into his jeans. In a few seconds, he was ready to go. We talked for a minute. I told him I did this every now and then, and he was welcome to come back any time. He said he had my e-mail address and might be in touch. I told him again he was welcome, and he left.
The next day I dropped an e-mail to his address to say thank you, come again some time. The message bounced, the mailbox had been closed. I hope he gets back in touch. I'd like to buy him some really sexy lingerie and make him my sex toy........