[M]y casual hookup turned into kinky ro[M]p

This is a true story from around 4 years back. Chose this one to be my first post as I think it qualifies for *gonewild.*

**Intro/backstory:**
I am early 30’s Indian, fit, bi guy with a 6″uncut upward curve cock. Started exploring things with guys from early 20’s. Started with getting my cock sucked, then leave with not much to say but thanks, no favor returned and then feel bad for having to do anything with guys but only until I get the urge to do it again. This repeated and came to a realization that I like getting my cock sucked or fuck men as much as I do with women.

**Story:**
I was browsing CL and came across this post from a guy who lives close by me. The post was not that descriptive and just a casual ‘looking to fuck’ type. It has a face pic (a selfie) and that surprised me as posts like those usually just have dick pics. He looked to be in his 40’s, light stubble, long hair till his shoulders. Not my type from the pic but being close by tempted me to respond. There was not much back and forth and I headed to his place once I got the instructions on getting into his apartment building. I thought it would be a quick cum dump meet..

I got there in less than 10 mins and he opened the door. Pretty much looked the same as in the pic from his post. Talked with an accent and told he is from Russia. We had the awkward small talk and knowing things can proceed, he took off his clothes to reveal a smooth, fully shaven body and not a single hair from his neck down to his toes which I did not expect from his stubble and free flowing long, a bit unkempt hair. Smooth, fem like body is my weakness and brings the wild side out of me.

I instantly knew it is not going to be the usual ‘fuck and leave’ that I do. My mind started racing fast and getting into kinky things to do but we haven’t talked about them or opened up at all. So I know I have to take it slowly and go with the flow of things. To elaborate on that kinky things I just mentioned, I enjoy being dominant in bed but do not call myself a dom as I am the softest guy IRL. But I am open to try things in the bedroom and do not have any hard limits and have done the usual spanking to a bit more raunchy spit on face and slap it with my dick in the middle of getting sucked to giving golden showers, facesitting etc. I may be missing a few but you get the idea.

So I stood there complimenting his smooth body and asked if he wanted to get a massage mentioning that a well kept body like that needs attention. I never massaged a guy till then btw. He okayed and as I took off my clothes, asked him to lay on his stomach with his legs spread out. I got between his legs and sat on my knees. Started with grazing my hands from above the back side of his knees and ran them through his inner thighs and over his sack to getting close to his beautiful asshole but not actually touching it. After doing this a few times, I proceeded to grab a handful of his cheeks with both my hands and gave a good squeeze. I started squeezing them smoothly with a ‘spread the ass out and bring the cheeks in circular motion’ that reveals the asshole in its full glory before closing the cheeks again.

He started to enjoy the attention I am giving to his ass with slight moaning. After doing this for a bit, I brought both my hands to where his butt crack begins and used my right index and middle finger with my left hand pressing down these fingers further to run down his crack to go over his asshole just dropping both my fingers one after another but doing it in a quick motion to start again from the top. He loved it and increased his moans. I gently asked if he likes being spanked and he nodded with an approving ‘yeah’. So I spanked both his cheeks to a resounding echo followed by his moan and the jiggle. He loved it propping his ass up in a wanting more fashion.

I added the spanking to the earlier motion of running my fingers over his asshole. Now that his ass is a bit propped up, I can see his cock hanging and balls that need some action. Without asking him this time, I gripped his balls and cock with my left hand like a cock ring would hold and then spanked his ass with my right hand. Seeing that he loved how tight I held his cock and sack, I flicked his balls with my middle finger after a nice spank. He moaned in pleasure so loud that I got worried about apartment neighbors hearing us. He didnt seem to care and I didn’t care further. I continued spanking his already pink by now ass and flicking his balls.

We both knew by now what we are into and I pulled him close to me grabbing him by his long hair with my right hand while I still choke hold his cock and balls and told him that he will be my slut and do as I say. He obliged with an *Yes sir*. He got on his knees to bend over and I continued spanking and rubbing his balls. Then I asked him if he has toys so I can play with his butt letting him go. He pulled up a bunch of different things like beads, butt plugs, dildos etc and asked me to choose any or all. As he went back to his position, I went with the beads first because I never had a chance to play with those.

I applied some lube on his asshole as I prepped it with my fingers rubbing all over it. Then started inserting the beads one by one as he moans. After having enough of them in, I had him wiggle his butt as I squeezed his cheeks. I started pulling one by one out and it is a sight to see as his hole stretched to let each bead out but close right away.

I looked to pick the big black dildo next but he stopped me to ask if I want to play with his prostate mentioning he can orgasm multiple times with just prostate simulation and not even touch his cock. Now this was news to me. I never knew guys can orgasm this way and I stood there in disbelief. He pulled a glove out and told me he will guide. I put the glove on my right hand and started to prep his hole with lube again, stick a finger in, have it there for a little bit before trying the next one. Ended up having 3 fingers fully in and he asked me to graze my fingers on spongy jello like tissue which I found and stimulating it and he started to continously moan like he is about to pass out. His soft cock started leaking like a fucking tap and I could not believe what I was seeing. We continued this for a good amount of time and I felt him quivering.

I slowly pulled out my fingers telling him I want to fuck as I see his gape. I was so worked up by all the kinky stuff we did and forewarned him that I may cum quick and his smooth ass is to blame. I had the condom on and started to slide my cock in his fingered asshole. It went in so smoothly that it almost felt like cunt. I fucked him for may be less than 30 seconds with few hard pumps grabbing his hips before cumming hard. I collapsed there tired as both of us were a bit sweaty and need a minute to come back to our senses. I apologized for being so quick but he was gracious enough to say it felt amazing.

We both laid there and talked about his long sessions with his gf, his toy collection before jumping in the shower to clean up. We met numerous times after this and I was glad that I responded to the post that day. And it felt good not to open up about everything through the email back and forth before meeting and let things flow. Different toys were explored in our long sessions that ended each time with both of us collapsing.

I hope you guys enjoyed this story. It felt great for me recollecting this and my underwear has a stain from precum. Forgive me for any formatting mistakes.

Source: reddit.com/r/gonewildstories/comments/avrqor/my_casual_hookup_turned_into_kinky_romp