[MM] – A first experience. Not just M&M but kinky too. [Gay] [chastity]

I’ve been a lurker for a while. I was going to post this to another sub but I needed an account that is older. I just needed SOMEONE to see this story.

I’d like to try something outside of my comfort zone today. Throwaway account for obvious reasons. I don’t really want to get into any personal data like how old I am, my name, where I live, etc.

I’ve always thought of myself as kind of curiously bi and experimental. I’ve crossdressed, played with lots of sex toys, all sorts of things. Never with another person though. Only women in my bed and never admitting to this type of stuff.

I’m married and divorced. Single. Had some fun now. A few hookups and random just sexual things that are like bucket list shit. Then, there was this one thing that I can’t get out of my head. I was at a party with a friend. Didn’t know the host but met him that night. Nice guy. He’s married but his wife is out of town on business for two weeks (already gone for half a week).

Party night is Friday night. A lot of people I don’t know (which kind of makes me uncomfortable), loud music, drinking, even some questionable drugs going around that I’m not exactly accustomed to. I’m having fun though. The host is being really nice and friendly to me. The more fucked up I get, the more I realize that he’s a bit touchy but I kind of like it. My one friend leaves soon in an Uber and I stay. I probably don’t really know what I’m doing but just following instructions at this point.

As it gets late, there are a few people crashing here and there on the furniture. The host, his name is Nick btw, grabs me and says that he’s going to show me where I can sleep. He brings me upstairs, into a bedroom, I approach a bed and he’s standing behind me with his hands on my hips as he leans in close to my ear and says, “I’ll be back in five minutes. Put that on.” As I’m looking at lingerie which I guess is his wife’s (before you scoff, he later said he knew I would wear this because he could see the underwear I was already wearing and that it was very feminine. It was.)

He turned around and walked out of the room, closing the door behind him. I was really drunk. I just stripped naked and started putting the clothing on. It was his wife’s stuff and was pretty close to a good fit for me. White thigh highs, white garter, white corset. Once I was done I just sat down on the side of the bed and started wondering what the fuck I was doing.

About 20 minutes later he came back in. Closed the door behind him and was already tossing his shirt on the floor as he approached. He walked over to the closet, got something off the top shelf and then came over to me. Spread my legs and for the first time in my life, someone put a chastity lock on me. He said, “You won’t be using this” as he stood up, dropped his pants and boxers and pushed his cock into my face.

Lots more first for me on this night. First time sucking cock. I think I did well. Certainly the first time being skull fucked. I started noticing how tight the lock was too. My dick really wanted to be hard but just couldn’t. He pushed me back onto the bed, flipped me over onto my stomach, licked his fingers and started fingering my ass to loosen me up. I knew what was coming. His dick wasn’t that much bigger than mine and I had played with my butt at times in my life anyway so I was ready.

So I thought.

He climbed up on my ass and pt just the tip into my tight little virgin hole, and then took my cherry with a big grunt. It fucking hurt so bad. For about 30 seconds. Then it felt so good. Holy shit. He fucked me like that for a while and then flipped me over into missionary and then started making out with me. WOW that unexpected and hot.

Then he just came in my ass. That’s when I realized he wasn’t wearing a condom. We talked about it later and I was better but at the time I was a little freaked. I was also in ecstasy. My legs and arms were wrapped around him, I was screaming his name, begging him to fuck me harder and once I could feel his cum hitting me, I think my eyeballs rolled completely into my skull.
Not that I got to cum though.

Basically I spent the next week and a half at his house worshipping his cock and cum before his wife came back. On the last night we could sleep together in his bed he unlocked me and allowed me to make myself cum while we were having sex. This whole thing was amazing but he’s not available. I feel like I was fishhooked or something into that and while I loved it, I feel bad that he’s married. I want more and more and more of it but I certainly don’t want to be the other “girl” and I don’t know her but I don’t think it’s nice for me to hurt her in that way. Now that I have my head back on straight I can see that.

So apparently I’m looking for a boyfriend that wants me to crossdress and wear a chastity lock. ?Oh…and likes to have sex A LOT.

Source: reddit.com/r/gonewildstories/comments/6211wk/mm_a_first_experience_not_just_mm_but_kinky_too