I’ve thought about this experience a number of times over the years and figured I might as well put pen to paper so to speak.
This was a few years ago while I was traveling out of town in southern California on work. I am married.
I had fantasized for some time what it would be like to be with another man. I had watched gay porn once in a while, and at times when I masturbated, I imagined what it would be like to have a cock in my ass. With women, I generally enjoy being more dominant, but there was something about the idea of having a guy holding my hips and fucking me from behind that was such a turn on.
So one evening while I was out of town and at my hotel, I finally worked up the courage to give it a try. This was a big jump for me. I had grown up with religious upbringing. I was married, although, I had been unfaithful before but with women. This was the first time I was going to try something with a guy and felt like a huge step. But I wanted it. I wanted to experience having a cock in my mouth, the feeling of being filled up and fucked. The thought got me so fucking hot, and the time had finally come.
That day, while I was at work, I put a post up online with what I was looking for. I had no idea what I was going to get in response. I got quite a few responses. Most of them were ridiculous one or two line responses. I got a few that were serious and seemed like good prospects, so I started messaging back with them. I finally narrowed it down to one guy. He was Latin and an IT professional that lived in the area. I liked his demeanor and he seemed very calm and level. He repeated back everything I asked for in my post and I could tell he was interested in setting a scene exactly as I wanted.
What I really liked was that he went above and beyond. He knew I’d never been with a guy and knew what challenges I would have, so he had the forethought to suggest he bring some toys to help me get used to having something in my ass before he fucked me. He also said he would bring lot and lots of lube.
We got the whole thing set up and I was confident that he would do everything how I envisioned it.
When I got back to my hotel room, I was a bundle of nerves. I couldn’t believe I was going to go through with this. I knew I was crossing a threshold I couldn’t walk back. Would I like it? Would it change how I viewed my sexuality? One thing I told him I wasn’t ready for was more intimate affection like kissing and cuddling. He was fine with that.
After pacing around my room a million times, I was ready to go through with it. I messaged him and told I was ready for him to come over.
The plan was I would leave the door to the room slightly ajar. I would get into the shower and the plan was that he would let himself in and just discreetly come join me in the shower. I waited about 20 minutes to give him time to get there, and I went and opened the door, putting the lock all the way out to slightly prop it open, turned on the shower, stripped down naked, and got in. I got the soap and washed myself down and got all clean. After being in for a few minutes, I heard the door to the bathroom open and he came in.
He called my name and asked how I was doing. I told him I was well and glad to see him. He didn’t say anything else but got undressed, opened the glass door and stepped into the shower to join me. I just kind of stood there looking at him unsure what to do. He said a few things and we chatted a bit. He asked me if I was ready, and I just shook my head yes.
He reached over and grabbed the bar of soap and walked in closer, grabbed my hand and pulled me in close. He started with the bar of soap and started soaping down my arms and shoulders, then moved to my chest and stomach. He turned me around and soaped up and down my back and neck. As he did so, he pulled me in closer and I could feel his fully erect, hard cock pushing against my ass cheeks.
He then started to soap my ass cheeks. It felt so so good. I got very hard, and as he soaped my ass, he reached around with the other hand and started to stroke my cock with his soapy hand, stopping only to massage and soap my balls with his hands. At some point, he slipped his fingers down the crack of my ass, soaping everything as he went. As he reached around and stroked my cock with one hand, his fingers found my asshole and slowly massaged it from behind. He washed off the soap from his fingers and returned them to my asshole. He kept working and massaging it, and finally he pushed the tip of his finger inside of me.
All of this felt soooo fucking good. I was in heaven feeling my cock being stroked and the beginnings of him pushing a finger inside me a little bit at a time. He kept working my ass, getting his finger deeper inside of me, and I could feel it inside of me. It was a different feeling, but felt amazing. I felt things starting to build and knew if this went much longer I was going to cum. I told him I didn’t want to cum yet, but I wanted him to still keep fingering me. He stopped stroking me but kept his finger inside of me. He started moving his fingers in and out more and I felt my ass getting more used to having it inside. He started finger fucking it faster and faster and it felt very good. I finally asked him to stop and I wanted to try something. He pulled his finger out, which disappointed me as I was enjoying feeling it inside of me.
I turned around and looked down at his hard cock. I told him I wanted to try sucking his cock. I remember him saying “It’s all yours.” I got down on my knees in the shower and moved up close to his cock. I put my hands around it and felt it, feeling the edges with my fingers. This was my first time touching another mans cock and I wanted to really take it in. I felt is balls, gently traced his cock from top to bottom and just explored it with my fingers. Finally, I leaned in close and touched my tongue to the flat smooth skin of the head. I started slowly, kissing and gliding my tongue along the surface. I spent time on the head of his cock and then worked my way down his shaft.
Finally, I moved back to the head and was ready to take it into my mouth. I started kissing it again and slowly wrapped my lips around the head. I pulled is head into my mouth, exploring it with my tongue as I took it in. I slowly went further down, feeling it go all the way in mouth and into my throat. It filled everything in my mouth and part of my throat. I started to gag a bit but managed to get it under control. I put my hand at the base and started to suck his cock in and out of my mouth. Working my way up and down it as it went in and out of mouth. I looked up and heard him moan and could tell he was really starting to enjoy it. I kept going, stroking it with one hand while maneuvering it in and out of my mouth. I loved how smooth it felt in my mouth, I loved the feeling of it filling my mouth, and I loved hearing him moan and move his hips in and out in unison with my sucking motion.
He finally told me the same, that if I kept going, he was going to cum. I wanted him to save it for the main event, so I stopped. I finally stood up, and he put his arms around me and pulled me in closer. I could feel our erect cocks rubbing against each other and could feel the warmth of his body. He finally said, “lets go into the bedroom.” I agreed, and turned off the shower. We got out, he grabbed a towel, and spent time drying me off, very tenderly and slowly. He put his hands all over my ass, squeezing it and feeling it as he dried me down.
We walked into the bedroom and climbed up on the bed, and he told me to lie face down on the bed.
I did as he told me and turned over and put my face on the pillow. He started by massaging my legs and ass. He got down behind me and started to kiss my legs down on my lower thighs. He was kissing and licking my thighs and inner thighs as he spread my legs apart. He kept kissing and licking higher and higher until he came to my ass. He slowly kissed my cheeks and ran his tongue up and down them, lightly biting them as he went. It felt so good. It was very relaxing and I was really enjoying it. Finally he did something that felt like electricity. He started to glide his tongue down the crack of my ass, kissing and licking the inside of my cheeks as he went. My cock was on fire and everything felt amazing. Finally, he focused his attention on my asshole. He started by gently licking and kissing around the edge and became more aggressive, pushing and massaging my asshole with his tongue. My brain was on fire. It was almost too much. He finally pushed his tongue inside my hole a bit and kept kissing and licking and massaging it with his tongue. Just when I thought it couldn’t feel any better, he reached up with a hand and slipped it under my waste and wrapped his fingers around my balls, massaging them while he buried his tongue in my ass, then started to stroke my cock. Since I was lying face down, my cock was caught in between the bed and my body, but he pushed his hand under and stroked and rubbed it while he very firmly attended to my asshole with his tongue.
I was worried I was going to cum and told him to back off a bit on my cock which he did and just kept massaging my ass with his tongue. I laid there forever just enjoying the experience. It felt so amazing and I had never experienced something like this. I was so relaxed and got a little sleepy, and he finally grabbed my hips to pull me up. He asked if I was ready to try the next part and I said I was. He got up and walked over to the dresser and got a bag. He pulled out a dildo and a bottle of lube. He came over and sat on the bed next to me while I was still laying on my stomach.
He grabbed the bottle of lube, poured a generous amount in his hand, and put it on my ass, working it into my asshole with his fingers. I breathed deeply and put my head down while he started to push a finger back inside me again. He started to talk to me more to coach me through the process. He got his full finger inside of me and really started to go deep this time. He pushed up and in as far as his finger would go and I could feel him very deep inside me. It was a feeling of needing to go to the bathroom, but I just let the feeling set in and enjoyed his finger in there as he worked it in and out. Finally, he told me he was going to slowly try the dildo. He applied lube to the dildo, and I could feel him push the head of the dildo against my hole. This was much different than the finger. The head was bigger, and I strained as he slowly tried to push it in. He told me to let him know if it hurt. It kind of did, so he went very slow. It seemed like forever, but he spent a lot of time working the dildo in a bit at a time. Finally he got most of it in. He told me “Ok, I want you to slowly turn over, and take your time moving it in and out yourself and get used to the feeling.” I got up and turned over and put my legs up. He grabbed one of my legs and helped lift it up and I reached under to grab the shaft of the dildo to control it. I could feel it inside of me and experimented moving it in and out and around inside of me.
I did this for a while with his assistance and he encouraged me to take my time and really make sure I was comfortable and to get things loosened up. I really appreciated how slow he took things and coached me through it. We went on like this for a while until I told him I was ready for him to fuck me. He asked if I was sure. He told me he could tell I was very tight and he wanted to make sure I was truly ready. I wanted it.
He said ok and told me to turn back over. I did as I was told, and he slowly pulled the dildo out. He pulled me closer the edge of the bed and he grabbed a condom and put it on. He got the lube and went back to work lubing and working my ass again. I was kind of on my knees a bit, but chest down on the bed. He then put lube on his cock and moved up close behind me and I could feel his cock as he pushed the tip of it between my cheeks. He told me to relax and he pushed my cheeks apart and pushed his cock into my asshole. I could feel the head against my hole as he applied pressure. He slowly and barely pushed the head inside, working it in. He kept going in just a little bit each time, pushing in, and then pulling it back.
He finally grabbed my hips and got right up behind me and started to push his cock inside of me more. I lay there on my stomach, pushing my ass up in the air and spreading my legs as much as I could to give him complete access to my ass. He very slowly pushed his cock in, an inch at a time. There were certainly some points where it was too tight. I strained and caught my breath as I told him to hold on. He was very patient and took his time until I was ready. He would just hold it in place, letting my ass take it in, and open up as it got used to it. This went on for some time as he continued to push his cock inside of me. Finally, he was all the way in. He just stopped there and I took in the feeling. Things were kind of numb from some of the pain, but it also felt good to be filled up. I felt the sensation of the whole thing, being completely submissive on the bed with his hands grabbing my hips, pushed up behind me, his hips pushed into my ass, and cock deep inside.
He finally started to pull it back out, moving out a bit at a time, but then pushing it back in. He kept working my ass, stopping when I needed it, but continued to keep going. Finally we found some rhythm. We managed to finally get to a point where he was truly fucking me, moving in and out. Once we got to this point, he started to let go and really enjoy it. I could hear him moan and knew he was enjoying it as he grabbed my ass tighter and started to really fuck me, pushing in and out. I reached up could feel my cock. It was kind of hard to maintain an erection with his cock in my ass, but I started to stroke my cock to get the erection back until I got hard again as he continued to fuck me.
It didn’t take long, and finally his moans turned into yelling as he came. When he came, he grabbed tight and pushed his cock deep inside as he came into the condom. He kept fucking me while he came and finally came to rest. I collapsed and my knees when out from under me and collapsed down on the back of me, cock still inside. We both lay there quietly while we both took it all in.
He eventually pulled out and took of the condom and grabbed the towel and cleaned off. He looked at me and told me it was my turn. He told me to turn over and lean up on the pillow. I did that, with my back against the pillow and back of the bed and legs spread. He got down on his stomach and kissed my legs for a moment and then grabbed my cock and started to kiss and lick it with his mouth. He finally wrapped his full mouth around it and enveloped it with his mouth. He began to vigorously suck my cock, going up and down it with his mouth. I was really feeling it and leaned back into the headboard and gripped the pillow as he went at it, sucking my cock. It didn’t take much longer and I could feel it build and finally I came harder than I had cum in some time in his mouth. He wrapped his mouth tightly around my cock as I shot my load into his mouth and throat.
I leaned back as I came, feeling his warm mouth all over my cock. He drank it all in, and licked up what was left with his tongue. I was completely spent. He looked up at me and laughed and asked “are you sure you’ve never done this.” I just told him that was amazing and how much I enjoyed it.
The only bad part was he made an advance to cuddle and likely wanted to kiss, but I kind of shied away from that a bit. He asked me if everything was ok, but just said I wasn’t ready for that. I think he was a bit annoyed, but went with it. It really was good. We talked for a bit, and finally he got dressed and thanked me again and left.
I’ve done a few things here and there since then when I’ve been in a threesome with another guy and a girl, but nothing like that experience. I would like to try it again just to make sure I really do enjoy it, and I think if I did it again, I’d be more open to some kissing and other things. Who knows, we will see what the future brings.
Source: reddit.com/r/gonewildstories/comments/ls0uw9/mm_my_first_time_with_another_guy_while_traveling
Very hot!