Who was that masked man?
I read the Craigslist ads regularly, sometimes just for amusement, sometimes because there might be something or someone real behind an ad. You never know. I always say that I am open to possibilities.
I don't waste people's time with pointless responses. Generally I use a filter to search ads. Since I am somewhat older, and since many posters are interested only in someone younger than, say, 30, why bother? So my filter is "m4m older" for the city in which I live.
About two weeks ago I ran across an ad from someone who described himself as around 30 but who was interested in meeting an older man. The writer said that he was shaved and sometimes liked to dress in women's underwear. He wanted to meet an older person because he was shy and had never done anything with another guy before.
Yeah, sure. But I decided to write him. So I sent a carefully worded response, expressing my interest and assuring him that I would not be pushy. If he was exploring his interests, then I would be happy to let him go at his own pace.
Well, he wanted me to send him a foto. He had posted a lower body pic with his ad, so I responded in kind. I heard nothing back .
A few days later I re-read the message I had sent him, so I did a follow-up. "Just trolling for dirty photos? Or were you serious about meeting?"
Again no response. But a few days later suddenly there was a message from him, saying he had not really looked at his inbox and he wanted more information from me. First of all he asked for a full body pic. OK, I was able to find a decent mirror and take one with my ipod camera, email it to myself, crop it and save it, and then email it to him.
Well, that was good. Then he wrote that if we were to meet up I had to agree to use latex gloves and condoms for everything.
Now what turns me on about gay sex for me is the heady aroma of a man's cock and the silky smooth texture of the skin around his dick. And don't get me started thinking about how sweet it is to taste a clean rosebud and to inhale deeply the purest essence of manscent. I am not really into exploring the smoothness of latex. Rubber gloves always seem to remind me of washing dishes.
But I am patient. If he gains confidence, then this might lead to something worthwhile. So I wrote back that I would respect his desire for total protection.
Then he mentioned that it would be really nice if I were to buy him some panties. Not expensive ones, just standard stuff from Target or wherever, but he did not want to do it himself because it would create problems if his girlfriend would find them. What size? 7 to 9 he wrote back. Oh, and some knee stockings, too. He would be able to meet up with me the following afternoon.
The next morning, after my workout at the gym, I went shopping at Walmart. Latex gloves. Check. Lube. Check. Condoms. Check. Panties. Check. Check Check. Hmmmm. Looks weird for an older guy with a beard to be buying all that, and I needed some trousers anyway. But the checkout person did not bat an eye. All done with the purchases, I arrived home and sent an email back telling him what I had acquired.
He sounded pleased, asked if I would hand wash and dry the panties beforehand. It made them fit better, he said. I had no basis for disagreeing with him, so went ahead and did that.
As the afternoon began, our message interchange grew more frequent. He wanted me to send him a face picture. He apologized that he was not willing to send me one of him, but it would make him feel more confident if he could see my face.
What the hell? But I have been out to friends and family for years, he is still deeply, deeply closeted, and I remember what it was like before I gained enough courage to be honest with myself and others, so I went ahead.
We were about an hour away from his coming over. Now he wrote that he was very concerned about my seeing his face, so he had a plan. I was to not be able to look at him when he arrived. I should be in another room, with the door closed. He would come in and go straight to the bathroom. I was to leave the panties there. He would change into them and then would emerge, but he would be wearing a ski mask, a baclava, so that I could not see his features.
Suddenly the whole scenario teetered Schrödinger-like between two potential states. This was either very. very weird, or it was very. very kinky. And at the moment, without being able to open the box of the future event and see what it was, it was both and neither at the same time. But my gut told me to go with kinky.
Now I am a pretty vanilla kind of guy. Fisting, scat, cb torture,--all that stuff leaves me cold. Never been one for fetishes. But this was something different. This was just vanilla sex he was after, a hand job and a little fingering, but done in a way to make sure he was totally safe--- hygienic and anonymous. Can I really raise any objection?
When 3:45 came without his arriving, I began to think it was an elaborate scam. But then I noticed two messages from him in my spam folder. Damn. Somehow I had marked one of his messages as spam by mistake. He was asking for my cell number so he could message me.
Well, I had already bought the stuff at Walmart and I had sent him my pics. I was invested, so I followed up with my cell number. Two minutes later came the IM, asking if I had gone into a back room and if it was ok for him to come in.
The guy is real, I thought. This has gone too far for it to be a game. Sure enough, about four minutes later I heard footsteps and then I heard the bathroom door close. I came out to the hallway and asked through the door, "Finding everything ok?'" Yes. I went into the bedroom and dutifully put on a pair of latex examination gloves. About a minute later he stepped out. He was about 6 foot, about 210 pounds I guess, a softish, rounded body. "Zaftig" one might say. He was wearing the black lace panties, a purple t-shirt, his white baclava, and sunglasses. I stepped up to him to feel his body. Nice. Zaftig, like I like them. Then he went back into the bathroom to change into another pair of panties. These were purple, sateen. I liked the feel of them, the smoothness. I could feel them just fine despite the gloves. Then he went back for the last pair, the orange thong. This one disappeared into his crack and I started to get really hot.
"Lie down on the bed," he said, "so you don't see my face". I was puzzled. "Use the pillow. Put it over your eyes." As soon as I complied, he took my hand and guided it to his hole, which he had lubed up.
Oh, it was nice. I wanted to sink my fingers deep inside him, but I knew he would panic at that, so I contented myself with making slow circles and only every now and then dipping my index finger into his well. After about thirty seconds of this I heard him squeeze some lube out of the tube and then he started on my own tool.
Later I determined that he had put on gloves for himself. It certainly didn't matter to me, because I was almost instantly brought to a high point of tension and excitement. I came fast and hard, surprisingly fast and hard. None of that lingering for an hour on a moderately high plateau. This was a jet-assisted launch to the top of the mountain.
A minute later I had recovered. I kept the pillow on my face, even though I was hot and sweaty. I heard him moving and jerking, so I went back to fingering his hole, a bit more forcefully than before. He breathed hard, then was quiet. I just lay there, then I heard him heading back to the bathroom.
I gathered myself and returned to the back room where my computer is. I heard him open the bathroom door. "That was nice", I said. "Thanks for coming." "Ok. Yeah. Bye now." And then he was gone.
A few minutes after he had left, I sent him a text. "Hope you enjoyed it. I sure did." Almost immediately he responded. "Yeah, thanks for the panties and the gloves and stuff."
Will we do this again? There are indications. He asked me to go shopping for a short skirt, something thin, not like jean fabric. Oh, and maybe I could pick up a small toy. I could maybe watch him use it on himself.
In the meantime I am intrigued by my own reaction to these events. The impersonality of it all goes against much of what I think is essential to sex, but I am able to accept our encounter as something mutually beneficial, a transaction that satisfies many of our needs, if not all of them. Intimacy and sharing we do with others. What we did together was not intimacy, it was just pure raw sex. Safe and sanitary and impersonal, but still sex. Nothing wrong with that.