I was browsing a ” hookup” website. A few days earlier I had created an account, and was practicing navigating the website. My profile read “Wanting to expand my horizon” and I was looking for a man and that I am bi-curious. For some time now, I have been having very strong feelings of having a same sex experience. I came across one profile, that read he would be in town for a few days, and was looking for a same sex hookup.
I asked when he was available. He says “right now” then “no, but seriously I’m at a conference, and I can move my schedule around”. I told him I could go to work a couple hours late, my shift starts at 2:30pm, or take off a couple hours early from work around 9pm. We agreed the 9pm time would be better.I asked if I needed to bring any toys. He said ” surprise me”. This conversation happened on a Saturday.
I go to work Monday, and my job was going to need me for the full eight hour shift, til 11pm. I texted him through my KiK app, ( we had exchanged usernames), that the earliest I could be at his hotel was 11:30. I say to him, “why don’t we plan this for Tuesday, so we could have more time together” He says “yes, more time is better” Then he texted back saying I should come over after work tonight, and then do a back to back on Tuesday. We were both super honey from the anticipation.
I always wondered how nervous I would be in this particular spot. I was surprised.
I was not really nervous at all. I always thought if this situation was happening, that I was “all in”. I texted him when I got to the hotel parking lot, he said he would meet me at the elevators in the hotel lobby.
This is really the only time I felt any nervousness. His room was on the sixth floor. He opened the door, I went in behind him, and walked over to the window commenting on the nice view. He was standing a couple feet behind me. I turned around and he was looking into my eyes. Without hesitation I neared him and put my left hand on his back and my right hand rubbing his chest. He began kissing my neck, our chests or bellies met,( we both have some extra padding) we were licking and kissing our necks and pinching and rubbing nipples. I felt his hand start rubbing my cock. I reached down and felt his stiffening shaft. This is the first time I have every touched male genitals other than mine. His cock was firmer and thicker than mine.
After a few seconds of rubbing each other he planted a kiss on my lips. I had wondered about this earlier, how I would react if this happened. Would I pull back or turn my head. No, our lips met. I was taken by surprise by this. He smiled and said ” you did want to expand your horizon” I agreed, he was correct. The kiss was well place
He was wearing loose shorts and a sport type shirt. I was wearing my work pants and t- shirt. He started pulling up on my shirt from my waist, I raised my arms to help out. He kissed and sucked my nipples. I started removing his shirt, he helped me pull it off. We tossed the shirts on a chair by the window, when I turned back he had already slipped out of his shorts, now he is nude. I followed suit, kicking off my shoes, removing my socks, then my pants. I pull my briefs down slowly.
He is watching me, I find this very erotic. We are in full view of each other. I heard him groan a little. That was a turn on. We again embrace, this time skin to skin. I wrap my arms around his chest under his arms. I slowly slide down til I’m on my knees. I grab his cock, and lower my mouth on the head of his cock. It’s a nice cock, not huge, but I was expecting that because I had seen some photos he sent me. He was bigger than me, and thicker and firmer. This is what I have been craving for, for some time. I wasn’t disappointed.
I tried to run his cock deeper into my mouth. I gagged, he said ” I’ll take that as a compliment”. I actually thought I could take more down my throat, but the gagged reflex would not allow it. I was a bit disappointed by this. I imagined taking it into my throat, but that wasn’t to be. Another thing I imagined was grabbing his ass cheeks and pulling so that his cock would drive into my mouth. He then grabbed my head and started face fucking me. This action felt incredible. I was being used like a fuck toy and I was loving it.
He slowed down, I quickened my bobbing, I really wanted to please him. It worked, he grabbed my head to make me stop. He was at the edge. I licked the tip of his cock hoping to taste his precum. I couldn’t taste it or couldn’t recognize the taste. By now I would have expressed a half teaspoon of precum. I’ve tasted my own, it is very tasty. I wanted to taste him badly. I squeezed from the base of his cock, and was able to “milk” out a small amount, it was as good as mine. Then I raised up off my knees, and he went down on me.
He sucked my cock hard. He would take me down almost all the way then pound his face on my publc bone. This was the only action that night that I really didn’t care for. I grabbed his head and started fucking his face, this felt great and I had to stop. I was reaching the edge. I climbed on his bed, as did he. We laid on our sides in the “69” type position, and slowly began licking and sucking each other. I licked my tongue down his shift, his balls were tight up high, I moved past them and started tonguing his ass. I was rubbing his ass with my fingers a few seconds before, I knew he would like it. He did, he was moving his ass more to my tongue and moaning. I was really enjoying pleasing him. I realized then, that I am submissive, just as I imagined.
This went on for a little while, he was rubbing my ass very well. He then got up and walked around to the other side of the bed near the nightstand. He told me to bring my ass towards him. I complied eagerly. I think he had two dildos and some lubrication in the nightstand, I don’t know, I was turned the opposite way, I’m just guessing. I picked up on this, I do like dildos! I gave my ass to him fully and without hesitation. I spread my legs wide, raised my ass as high as I could, arched my back, and laid my head down on its side like I was listening to the sheets. This is how I hoped it would be.
I wasn’t disappointed. He squeezed out some lube, I could feel it flowing down the crack of my ass til it reached my anus. He was quiet. I knew he was taking great pleasure in this. I wiggled my ass side to side just a little, to let him know I was begging for it. He lubed my anus with his fingers, then inserted one. I moaned softly, hoping he would put another in. Instead he grabbed the smaller of the two dildos, which was roughly the size of the one I play with myself with. He pressed the head of the dildo against my entrance and started applying pressure. I asked him to go slow so my muscles would get accustomed. He said we will go at your pace. I relaxed and started working it past my sphincter. Once it was past he slid it all the way in slowly but without stopping. The feeling was amazing. I took much longer at home. He started pulling it all the way out and sending it back in. My anus was opening and closing fast, my legs started to quiver. He kept this up with a good pace. I could feel the base of the dildo where the balls are and the suction cup is hitting my ass.
He was all the way in, and quickening his pace. It was catching my skin a little, maybe some lube wore off. There was some discomfort but not enough to stop. He stayed quiet. I hadn’t actually seen either dildo very well, as I was facing the opposite way. I was deeply enjoying this. I arched my back as much as I could and kept my head down. My mind started to wonder ( in a good way) like an out of body experience.
He pulled the dildo out, and applied more lube to my ass. He placed the bigger dildo against my ass, and started applying pressure. I could feel the size difference right away. He was working it slowly past my sphincter muscle, again I told him to be very patient with me, but It will go in. I think he was smiling when I said that. “We will go at your pace” he said. I felt some pain, it was a tight fit, just when I felt my muscles relaxed to accept it, he slowly but without stopping sent the large dildo all the way in. He should have been recording my reaction for a good laugh later. I’m sure my eyes went big. My ass muscles felt stretched beyond the limits. I thought my ass was going to split open. I couldn’t take it, and quickly told him to pull it out.
This was basically a stranger, he could have started ramming it in and out, then I would be in a world of hurt. He was kind, and removed it without delay, he also cleaned me up. A true classy gentleman. In a few moments I understood what his goal was. He knew he was going to take my mind to another dimension. He inserted one or two fingers in my ass, hell I couldn’t tell, my ass was stretched proper. With a finger or two, he found my prostate, and started to massage it. I asked him if that is what he was doing, I had never experienced this before. He was sucking my cock at the same time. My mind definitely went to another place, I was in total ecstasy. I was moaning louder, then I lost all control and started bucking wildly. I had an orgasm like never before, the euphoric feeling was absolutely incredible. He consumed my load. Then stopped.
Then he started up again doing the same wonderful thing. I thought to myself, ” what is he doing, I just came, I won’t do that again for at least half a day”. He kept on massaging and sucking me then said “umm, another one” I was in disbelief. I had to ask him if I came again, I really couldn’t feel it much because my whole body was in a total state of bliss. He said I had three orgasms.
I think I asked him to fuck my face. He did kinda straddle me as I took his cock in my mouth. I wanted so much to please him. I felt I was slightly unconscious. I was sucking him and feeling his ass cheeks, then I felt his hot liquid pumping in my mouth. Different than precum, not quite as good to me, but still uniquely tasty. This man knew what the fuck he was doing, and I’m forever grateful.
Imagine my extremely good fortune to have my first same sex experience from a super nice guy, and a real pro. I am truly blessed. We talked for a while, then it was time to go. All of this with a clear head, no drugs or alcohol. I had commented to him that this may be the last time I ever see him. He played that down a bit, saying something like you never know. My birthday is a few days away. I gave him a hug, and told him he gave me my best birthday present ever. Then I left.
I was really looking forward to seeing him Tuesday night. I was still on cloud nine from the night before, but my work needed me for the whole shift. I told him I would try to make it, but I couldn’t, and I felt terrible for it. From what I read in his profile he is only here till Thursday. I was looking forward to possibly seeing him on Wednesday, but things don’t always work out the way we would like them to.
I kept my chin up, and thanked him for the wonderful moment in time we had. I told him I wouldn’t say goodbye, but talk to you later, as I will probably talk to him online.
I drove home Wednesday after work, scrolled through my music player, found Alan Parsons Project, and tapped the song “Don’t Answer Me”. Half way home my emotions got the best of me. I fell apart. I had to pull over in a parking lot for a good cry. I hadn’t cried since my father died eight years ago, and I didn’t cry as much then.
I like to attach music to memories, the lyrics to this song DO NOT correlate to my experience. The vocals and melody fit perfectly for me. I will replay this song from time to time and it will help me keep the memory fresh.
This is not a sad story, I’m not sad, or mad, or hurt, or disappointed, it’s just a trigger for a beautiful emotion. To shed tears is to remember, learn and grow. It tells me I still have a kind heart and soul. Throughout this experience, if I had to do it all over again, I wouldn’t change one thing. I told him I have no regrets. I do have a small one though, I have nobody to tell about my experience in person.
We are both discreet. That is why I have not mentioned names in my writing, I hope “he”…won’t find that impersonal. I am debating sending this to him.
I told myself I knew what I was getting into, but it didn’t matter. How could I feel this strongly in such a short moment of time? I guess because in a way, he was my first. It’s 4:42 am Thursday morning. I have tears running down my face. I’m not ashamed to have feelings, I wanted the experience, and I got much more than I bargained for. I feel I am blessed, and a better person for it. Talk to you later.
This is mostly how I remember the last three days. I’m sure some things were different, (remember, I’m mostly in a state of bliss). I feel more alive now than I have in years. My host does not live too close, about an hour and a half away.
I need to find someone more accessible. I am afraid though. This may be too close for my emotions to handle. Seeing a “hookup” move along to the next, may be too hard on my heart. This is a great part of our country, there are many nice people. I will try. It’s not easy to find a match. I’ve chatted with a few, but it seems like they are there one day, then gone.
This was my experience. This writing is about 98% pure truth. The only reason it is not 100% is that my memory is not so great. I chose not to embellish this story, as I did not want to distort the pure nature of it. In my mind it stands alone and strong just the way it is.