From Straight to Gay

* 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. casino siteleri 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 canlı casino 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?”

– “No, a random guy I met in an online chat, maybe 45 years old.”

– “Good looking?”

– “Divorced, it’s hard to say but he’s tall and well muscled, he loves chubby men. That’s weird how much he loves chubby men like me. I was feeling like Angeline Jolie to his eyes.”

– “More like Brad Pitt.”

– “He told me he only sleeps with big guys.”

– “Hmm, okay then. Brad, I have to go to sleep now. Talk to you tomorrow.” That was the moment I wanted to tell her the two stories were a prank but instead I asked her,

– “Quiz of the day, only one of the two stories is true. Which one?”

– “What two stories?”

– “The one about me and the other about our friends swapping.”

– “Yours is the false one.”

– “Are you sure?”

– “Yes, 100%.”

– “The truth is that our friends never swapped.”

– “Are you kidding me? I can’t believe this. We will talk tomorrow.”

– “Yes I am sure, but thank you for not judging me.”

So it’s like this I start admitting to her or to myself that I was bi. But as you see I didn’t fully told the true story but that came later.

The morning after, I completely freaked out and ended up texting Abbie.

– “Call me asap about what I told you last night, I am freaking out here.”

– “Nothing to worry about, relax! I’ll call you later.” she replied.

Later that day, she called me feeling a bit pissed off at the beginning for not knowing what was true or false. I told her the same story I texted her, she asked if he sucked better than women, I told her no but I told her that I had sucked him also but with a condom. She then asked me if I fucked him so I told her the truth that no, I did not fuck him and the thought of fucking someone in the ass disgusted me even with a woman.

During the following days, I started adding some details then finally told her the whole truth. It took me 2 to 3 weeks to admit my cock fantasy. I even sent her the picture of that man’s dick. I started telling her that what I was feeling was for real, about my disappointment at not having enjoyed sucking his cock so we ended up sharing experience and tips. After a while, I told her that I was over with my gay things and start looking for casual encounters with a girl on tinder. I even started to save some money to go visit an escort. I was sharing everything with Abbie except the fact that maybe I wanted to do it again. Four weeks ago, we started talking again about this experience I had and she told me that she felt that I must have wanted to do it again and that I was just trying to hide it behind all the dates and the escorts.

I didn’t reply until the day after where I admitted that yes, I wanted to meet another guy because the first one did not satisfy me. That I also wanted to go all the way in order to not have any regrets. I don’t want to be passive, I want to kiss, to suck and be fucked. Her answer was simple, “If you feel it, do it.” After that conversation with her, I ordered a small butt plug and some lube online to play with myself. After two weeks of doing this, I know I am ready but I could not find the right person. When the end of that week came, I found someone that seems like a good candidate and I wasmeeting him in a hotel. I texted Abbie,

– “I found the right one. I’m going there now.”

– “Enjoy! Be safe and we’ll talk later.” she replied to me.

As I was driving, I had second thoughts. I was starting to get nervous I decided to text Abbie,

– “Meeting is cancelled tonight. I need to think about it.

– “Why? That too bad.”

Later that night, I texted her that sex have been taking too much space in our discussions and that we should talk about something else for the following weeks.

And that brought me to earlier today when I called her. Two weeks have passed and we talked about life, business and all the other things bestfriends talk about. Tonight though, I was ready to admit to her what I have done in the past two weeks and that it changed me forever.

– “Abbie I have something to tell you.” I started shaking out of nervousness.

– “What? Did you do it?” She didn’t even have to ask what I was talking about.

– “Yes, and my life has changed forever.”

– “What do you mean? How was it? When did it happen?”

– “You remembered 2 weeks ago? When I told you that the guy cancelled on me? He didn’t”

– “Why did you lie?”

– kaçak casino “I don’t know. Maybe I was getting stressed because of the pressure. “

– “So tell me, did you get fucked? Did it hurt?”

– “Yes, and I loved it. Specially the second time.”

– “What? You did it more than once?”

– “Yes, four times in the past 2 weeks. Three times with the same guy and another one last Friday.”

– “I can’t believe you, is that true?”

– “Yes, that’s the truth. My life has changed completely. I think I am gay.”

– “That’s great for you! If that makes you happy, be glad you found it now than never.”

– “Thanks for the support Abbie.”

– “But tell me, how does it feel?”

– “It feels amazing! I’ve never experienced that level of pleasure before. It blows my mind.”

– “I can’t think of anything to say…”

– “Listen, the first time I was nervous and it was good, I mean really good but it’s nothing compared to the second time with that guy.”

– “Not that fast! Tell me everything about that first time, explain to me.”

– “Okay, so it started Friday two weeks ago with this man named Oliver. We met at a motel one hour from here. I arrived before him to prepare myself, taking a hot shower, putting my butt plug in place with lots of lube. As you know, I really wanted to try anal and was really looking forward to enjoy it. When Oliver texted me that he was outside, I removed the plug and hid it then dressed immediately. I went to meet him and he followed me to the room. We talked for a while about random things and then he sat next to me, placed his hand on my cheek and french kissed me.”

– “Wow, that was hot! Did you like kissing him?”

-“It was weird at the beginning but eventually I started getting into it. We kissed like horny teenagers for a while and he started exploring my body. I did the same to him, we removed each others’ top then kissed again. I was still shaking a bit but feeling a bit comfortable in his arms. He suddenly broke the kiss and stood up, told me he was going for a quick shower and that I should get on the bed and make myself comfortable. I undressed, prepared the lube and condoms and waited for him to finish his shower.”

– “Don’t stop! Keep going, we are at the interesting part.”

– “He came out of the bathroom naked, and I stared at his half hard shaven cock, I really wanted to jump on it but my last experience made me control myself. He joined me on the bed and we started kissing again, out naked body rubbing against each other. My hands started playing with his dick while he was more interested at my butt. His hand slid between my ass cheeks and got a first feeling at my ass, he felt that I was prepared and told me how good he is going to take care of me. I felt my face go red and my heart was pumping mad. He made a move that told me he wanted me to blow him, so I did. I took a good look at his dick and went for it.”

– “And you liked it better than the first time?”

“Of course! I really wanted to please this man and now I understand the control that I had on him. I have lost track of time sucking him but then he stopped me, saying we need to save some for the main course and asked me if I was ready. I replied with a yes and he asked me to position myself on all fours. My head was pressed into the pillow, I feel so excited and shy on what was about to happen. I heard the lube open, felt something cold on my ass then one finger slid easily inside me. His other hand was on my balls and cock. The second finger got a bit of a difficulty to push inside but little by little I relaxed and it slid in smoothly. It was a weird feeling when he pulls away his fingers, like I was feeling empty inside, like something was missing. After a couple minutes of finger fucking me, he pulled his fingers away then felt something much bigger poke at the entrance of my ass. He pushed into me slowly, letting me adjust and it was weird, it was hard but also soft like a rock encased in velvet. He was halfway inside and I was feeling a bit of pain, almost making me ask him to stop but managed to keep it quiet. There was a burning feeling so I asked him to use more lube. Little by little the pain disappeared completely and my moans got louder, the pleasure increasing inside me. This time, I’ve felt something different, my prostate was being pegged by his cock and this made me see stars, the pleasure is blinding. He came into the condom before I had a chance to discover more about it.”

– “Shit, you really did it. I’m so happy for you that it went well.”

– “That was a great first time, this guy was gentle and he knew what he was doing.”

– “I cannot believe that I’m hearing those words coming out of your mouth.”

– “That’s not the only thing that came in my mouth that night.”

– “What do you mean that’s not all?”

– “Nothing much, but I might have blown him in the shower while I was masturbating. I might’ve also let him cum in my mouth.”

– “No way! You’re such a slut!”

– “I am not a slut! I didn’t swallow it.” and then were just laughing about that.

We cut the story for that night. I didn’t know what she felt about what I have done but I was really happy to finally share it with someone.

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