* I dedicated this story Abbie my best friend
* Thanks to maidenrose for editing
I have try to keep in line the best i could with the reality sorry if sometimes is not making sense but that's life!!
*****
I cannot believe what a journey I am about to write. I define myself now as gay or bisexual because I don't know what the future may hold but let me start at the beginning.
I am a 36 year old man, tall and overweight. I have been straight all my life but there are times I found myself immersed in a fantasy about big, nice cocks I have never fantasized about a friend or any other men naked in front of me in the show but 3 or 4 times I was dreaming about big dicks.
Maybe it was curiosity, maybe it was jealousy for having a bigger dick or something I acquired while watching porn.
A year ago, I have tried hooking up online with some guys but I never had the guts to really try to make my fantasy a reality. Even I was not sure about what entails my fantasy, as I know I only like the image of a dick. I never saw myself touching it, sucking it or anything else.
Sometime that year, I find myself in a nice hotel for the weekend. I was single for a few months and I was getting really horny and with nothing much to do, I searched craiglist for classified casual encounters in the area I was on. There were women, and of course a few escorts so I moved on to the men section. It was the beginning of the afternoon and with nothing else to do I scrolled through the different ads displayed. There are the usual ads posted by Tops searching for their bottom, but nothing that really interested me. I could not define myself as a top or bottom, I was not even sure if I wanted to suck cock or be sucked. Something changed inside me at that time, I decided that for once in my life I would take a risk. I decided I would be going to have an adventure. I posted an ad online stating, "Chubby heterosexual looking for first time tonight. I am available today in my hotel room. I don't really know what are my limits but I am liking the idea of playing with another cock, the bigger the better. Send me an email with your response and I will let you know immediately."
I received a few weird replies when an interesting one caught my eye. There was this married guy about the same age as me, i explained to him that I didn't know what I wanted to do but was committed to a handjob atleast. He replied that he didn't want to pressure me but he was an exclusive top and were only looking to get a blowjob while watching the game in front of the tv. I then told him that I was partial to the idea and might change my mind when it happens. We exchanged a couple of messages and he finally told me to take it or leave it. I stepped back and took the time to really think about it and I started to accept the idea of sucking a dick. After I thought about it, I messaged him of my agreement and my enthusiasm to do a great blowjob. Unfortunately, I took too long to reply and he told me that he already went ahead with someone else when he didn't see my reply.
Mixed feelings of frustration and relief warred inside of me, after a while I went for a walk and bought some sushi. It was past 7 pm when I came back. Being a competitive person, being turned down like this at the last minute seemed like a failure to me. I decided to suck a cock tonight and I am not giving up that easily. I went to my computer and start searching for gay sauna, gloryholes, even gay clubs but nothing really gave me that push to go.
At almost 8pm I received an email. An older guy of 45 years old, divorced, mostly gay and really likes chubby guys. I sent him a picture of my chest and he loved it. He in turn sent me a picture of his dick and it was perfect, I didn't really paid any attention to the fact that he was versatile and looking to kiss and cuddle. I was still affected by the earlier incident that after 4 exchange of emails, I gave him my room number. He replied that he will soon be here in half an hour. This is the moment that the shock of what I've done got to me and I felt the stress. I was stressing over the fact that finally, I would be able to give a blowjob, it became an obsession. I jumped into the shower thinking about how should I look, what will I wear when he arrives, that kind of thing. Mulling over the idea of waiting for him in my room naked, or in underwear, or fully clothed. His knock on the door decided things for me and I ended up wearing jeans only.
I opened the door and let him in. As we go closer to the bed, we exchanged a few words and he was talking about how beautiful I look and how hot I was. Finally, he approached me. He took me into his arms and tried to kiss me but this was a big no no for me. I told him this and he understood and started kissing my neck then down to my nipples. I didn't feel a thing except that I wanted a cock. I took off his shirt and we cuddled for a few minutes when I finally got the nerve to touch his dick and lo and behold he was hard, we both were. I stepped back, removed my pants and underwear, and did the same to him. When I saw his beautiful dick, I caressed it and I didn't care where his hands and mouth end up on my body. I was so hungry for his cock that it was not even 5 minutes since he arrived and I am already kneeling in front of him. I touched his cock, smelled it, kissed it and finally, placed it inside my mouth.
Once, twice, thrice I bobbed my head on his dick when he stopped me. He told me to stop as he was close to cumming. That I was turning him on so much. I obeyed him and stood up but I did not know what else to do. Finally I asked him, "Should we take a shower together to help you calm down?" He replied that I can go in and he will follow me inside. I just turned the shower on when he arrived looking at me hungrily. He stood behind me and I felt his dick poke my ass repeatedly and as I was about to turn around he came on my leg. I was so disappointed my erection deflated. I cleaned up my leg while he was touching me everywhere and after that, I went back directly onto the bed. A few minutes later, he joined me on the bed and apologizing, telling me that he came that fast because I was so hot and he was already on edge when he joined me in the shower. Out of nowhere he took a camera and asked me if I will allow him to take a few pictures of my body. I declined but he still insists so I told him that later he could take my picture but without my face.
We start to cuddle again and he tried to kiss me several times but declined each time. His hands were all around me, he started to suck me though I was not even half hard. I asked him to put himself on a kind of 69 position and for the second time that night I have his nice cock in front of me. I took more time to lick his balls but as soon as i put it in my mouth he tried to stop me saying he is about to cum. He tried to stop but he still came all over his chest. He went and got a towel to clean himself up then went back to blow my half erect cock. After I came, he took 3 pictures of my cock covered with my own cum, tasted it then tried to kiss me. I turned my head away and told him it was a great first time for me but that I needed to be alone for a moment. He did not argue and left quickly. As soon as he left I felt a mix of disappointment and pride but mostly pride. I began to laugh about what I had just done. Even if it was quick, I had a weird taste in my mouth so I went to brush my teeth a couple of times and ate my sushi. I fell asleep immediately with a smile on my face. The day after, I was meeting a few friends and I was in a cheery disposition thinking that if only they knew what I had done the night before. For a few months I forgot about this story, I was not feeling any disgust or shame but more of a disappointment to the fact that it brought me no pleasure at all. It was my secret, nobody knows and I don't want to try again.
Until 2 months ago I would never have considered telling anyone about what I've done but one night, I was texting my bestfriend Abbie and it kind of went from there to me telling her about it. I like to play the jock on her especially a sexy one, so I started making a story about a mutual friend that supposedly swapped together. She was really buying it and I started telling her that all of our friends are sex wierdos, even annoying her with some naked pictures of her I found online (It is actually a look alike but I like teasing her with it) and every time it pisses her off. She replies to this by teasing me about a picture of me next to a supposed tranny that I have on a trip in Latin America. The conversation made me remember the guy I was with in that hotel and I decided to tell her about it.
- "Abbie I have something to tell you but promise me first that you won't judge me and that you won't tell anything to anyone."
- "I swear."
- "I think you might kind of know it already but I had an experience with another man. I don't know why I'm telling you this now but I never told it to anyone." I paused after that, I wanted to see her reaction before I started telling her everything and that I was bullshiting about the swapping of our friends.
- "I would have never guessed, but that's okay. Did you really think I would have judged you about that? Are you crazy?"
- "It was just once and it was out of curiosity, I was really drunk." I told her, trying to justify what I did. "Don't tell anyone! Even to Steve!" Steve is Abbie's husband.
- "No don't worry, he's watching CSI." she replied.
- "I am shocked. I don't know where that came from but that made me feel better that I finally shared it to someone. "
- "There is nothing to be ashamed of!"
- "A little bit. I am supposed to be straight!"
- "You are curious and wanted to try, it's better like this then you won't have any regrets."
- "No, but that guy came onto me really hard and I could not resist. He really likes chubby guys, apparently in the gay community that's a thing. Too bad it's not in the hot blonde girls community." I was so nervous but happy at the same time because of her non-violent reaction to my news.
- "You didn't get the big boobs, but that's okay it's not that important."
- "It's something stupid but I could not kiss him. It was more disgusting to me than the rest."
- "When did this happen?"
- "About ten months ago when I went down to Florida."
- "Was he a military?"
