Real Life Adventure of a Cuckoldbystevecraigslist©
This is a true story of a recent adventure. Let me know if you like it at the address in my profile and I will post more.
I met Lydia from a posting on craigslist. I was in the habit of posting a variety of ads every week in the casual sex section, trolling for playmates. Sure, the odds of getting a date out of an ad were low, but what was the cost? And there was something addictive about the unknown, the excitement of new possibilities coming your way.
This ad was straightforward, something to the effect of "Handsome man would like to be your escort to a sex party." It was a basic plea for a woman who wanted to explore the sex party world of San Francisco, but needed a guide. I would escort her, pay any fees, and would expect nothing in return but the chance to get into parties where you needed to be a couple or a single woman. Of course, I hoped for more, but no need to make that explicit. If the chemistry was right, who knew?
Anyway, Lydia responded quickly, and after a bit of flirting on email, she sent me her epic and her number. I called and we arranged for a drink that night, to get to know each other a bit. We agreed to Mecca, a sort of upscale bar, full of beautiful people of mixed sexual orientations.
Well, that drink let to quite a fun evening. What started out as whispering to each in the bar led quickly to passionate kisses and groping, and before too long we headed out to the power exchange for her first foray into a public sexual play space.
Lydia is about 45, blond, large breasts, nice grabbable ass, kind of a slightly fucked out MILF look to her. Sort of slightly slutty soccer mom look. She was recently separated and enjoying exploring her sexual passions.
As for me, well I am a bit of a freak. Married to a sexy woman how I rarely have sex with, I instead have been using public venues to indulge my desires for submission, humiliation, and cuckolding. My wife is not into this kind of play and so I have been looking elsewhere for it for years. I look pretty alpha male, muscular and tall, but inside am pure sissy.
Well, anyway, that night at the power exchange was hot. I probably spent an hour eating Lydia out while groups of guys watched and jerked, and then we invited other men into fuck her. I could tell Lydia, who did not know what I was looking for exactly, was a bit surprised by the submissive role I was taking, and by the fact that I seemed to be getting more pleasure out of kissing her while she fucked others then by trying to fuck her myself. She did seem to enjoy the various guys entering her, and all in all, it was a lot of fun. We parted for the night and agreed to set up a date for another sex party.
Lydia knew of a private party, and after some research, I tracked it down. It was a costumed event, so Lydia went shopping for a sexy corseted gown, and I got myself tricked out in sub gear, all in PVC and leather complete with a collar and dog chain. We agreed to meet for a drink the following Saturday right before the event, to get geared up for the evening and to discuss our wants for the party.
What transpired at that party was a cuckolds fantasy come true, and I sit her the next day typing this, my mind still blown, not knowing if she will ever talk to me again.
So I met Lydia at a bar near where the fetish/sex party was going to happen. She was dressed in a tight rubberized little blue dress, with a cute fringe of feathers. For myself, I was in leather pants and vest (I had a collar and wrist and ankle cuffs that I would put on at the party).
We had a drink and chatted a bit about the party. I slowly felt myself dropping into sub space, and before too long we went to the club. It was a Spring Fling party, with people dressed as fairies and elfs and warlocks and goats and god knows what else. As soon as we were in the door, I put on my collar and leash. Lydia gave me a little smirk, grabbed the leash, and led us on a tour of the rooms.
Things were pretty quiet, but it was clear the back room was where the action would be. There was a bed in the middle of the room, and along the side were lots of benches for sitting, playing, and watching. We sat on a bench, and talked a bit. There was a woman and two guys on the bed opposite us. I began to caress Lydia's legs, our lips met for a kiss, and before long I was on my knees between her legs, her dress up, her panties pushed aside, with my tongue buried in her shaven pussy.
I lapped and lapped, not sure what was going on behind me. Lydia is loud during sex, and she moaned and guided my head. After a bit, my head slid down her legs and I began to lick her shoes. I was on my belly at this point, her sitting above me, and who knows what happening behind me.
After a bit of this Lydia jerked my chain up so I would sit next to her. She led me over to the bed, where the woman was lying on her stomach, rubbing the cock of one of the guys through his jeans, while the other guy was licking her breasts. Lydia immediately began to kiss the girl, and while I kneeled next to the bed began to rub the cock of the other guy through his jeans as well.
Up to this point, while sub, I was not pathetic. I could have joined into the fray her, and been an equal partner for the night. I think Lydia thought I was going to. But no, that was not for me. Instead I bent my head down and began to lick and tongue the asshole of the girl lying on her stomach. She was pretty, petite, youngish, and totally non-plussed by what I was doing. I could have been a fly on the wall for all she cared, as I spent maybe 10 minutes tonguing and sucking on her asshole. Meanwhile, clothes were coming off everyone else, and when I finally stopped (because the girl rolled over and began to get up, without even giving me a glance, Lydia had the cock of one guy out and was rubbing on it.
The girl went away with one of the guys, and Lydia was on her knees on the bed jerking the cock of this guy. I knelt next to her and held her hair and rubber her face, then bent down to suck her shoes some more. Lydia spoke up and asked me to get her a condom. At this point, while she clearly was a bit disgusted with me, I might still have maintained some dignity. But when I came back with the condom, the guy could tell how sub I was, and he asked that I roll the condom on his cock. Lydia giggled, looked at me, and I did so. Then I knelt beside her and took turns with her sucking on his cock.
For Lydia, I don't think this was a big turn on. Rather I think she found it amusing. She would allow me to take a turn now and then, and push the back of my head so he could fuck my face hard. Then she would take the cock back and go about her business. Before too long this progressed and he pushed her too the bed, face first, and entered her. She began to scream, and I knelt in front of her and kissed her while this guy fucked her hard. They fucked for about 15 minutes, during which I kissed her, sucked on her shoes, and got her some water to drink. Eventually the finished (the guy did not cum but sure had fun) and everyone got dressed again.
Lydia led me around some more from room to room, and we chatted with some folks. She tried to treat me like a normal person, but it was clear that she had made some decision about spending the night playing with others. I could feel the difference.
In about an hour, she started chatting with this guy all in latex. I stood about 15 feet away, slowly turning red, as she ignored me and chatted and flirted with him. Eventually she came over and said she was asking about his outfit, and let me into the back room, once again.
This time there was a couple sitting on the bed, facing a grouping of two women and one guy who were on the benches. Lydia walked us over and sat down on the bed next to the couple. I kneeled on the floor next to her. Soon she was necking with the female part of the couple, and I was just kneeling there. One of the women on the bench asked about me, and she said I was a slave, that I liked to lick feet, and that it felt good. With that, I crawled over and began to lick this girls feet.
She was a beautiful young Asian girl, maybe 22 and very petite. I started off licking her shoes, then she kicked them off and before I knew it, I was taking her whole foot into my mouth, kneeling in front of her, holding her leg with my hands as she face fucked me with her foot. The other woman and guy on the bench found this hilarious. I spent a good 30 minutes licking her feet, then her legs, then her shoulders and arms, and finally sucking on her fingers like a good little slut before the threesome decided to get up and leave. When they did so, I turned around to find that Lydia was alone on the bed with this guy, he had his cock out and she was sucking on it.
I crawled back to her and asked her if she would sit on my face so I could eat her while she sucked him. She gave me an annoyed look, said she was busy, and told me "not now." I kneeled and watched. This guy's cock was huge and very hard, and he began really face fucking Lydia. She was loving it, and soon he too threw her down and began fucking her from behind. He fucked her slow and deep, and while doing so starting smacking her ass. I crawled back to her face and tried to kiss her, but she pushed me away. The guy smirked and began telling Lydia to tell him how much she liked his cock. She did, and he told her to say it louder. Soon Lydia was actually screaming at the top of her lungs that she loved his cock and him fucking her. I was so ashamed and turned on.
He kept slowly spanking her ass and fucking her for what felt like hours. It was probably like 30 minutes, then Lydia sent me away to get them cups of water. When I came back, she was lying on her back with him standing above her, plunging his cock into her mouth over and over again. After giving them the water I kneeled at licked her sweet pussy, while he told her what a good slut she was and did she like being gagged by his cock. Her mouth was too full to do much but moan.
Before too much longer she on her back and he was fucking her again, and this time he was not messing around. He powerfucked her for a good 30 minutes, with her screaming the whole time. There were about 20 people watching this, and there I was, kneeling in front of her head, jerking, pathetic. He made me hold her legs up by her ears while fucked her and slapped the insides of her thighs as he turned he out like a little tramp.
She must have come a dozen times. I did not exist to her, until finally he shot in her.
Then she told me to get her coat. She grabbed it and walked out, with me tripping along behind her. She hardly spoke to me as I followed her to her car, and she barely even said goodbye before driving away. I was ashamed, unbelievably turned on, and so horny. I walked home in shame and awe.
It has been almost two weeks since then. Lydia finally has responded too my emails, to tell me she is getting a boob job next week and she would go to another party with me after that. She refuses to talk about that night. Who knows what she thinks of me.