Not as Gay as I Thought

Hi all,

Thanks for all the feedback you've left on my stories. Sorry it's been a while since I've posted anything, but this will tell you why.

I know that there are a lot of men like me who, even though they're firmly attracted to women, are still curious about what it could be like with another man. For a few years now I've had a fantasy of having sex with another man, particularly giving blowjobs.

A lot of times when I masturbate, I think about sucking another man's dick. Sometimes I even imagine taking it up the ass, but that's a lot more rare than my blowjob fantasies. Usually I feel guilty when I'm done and think it's crazy.

When I started to write my fantasies on this website it was mostly a way to get all of those dirty ideas out of my head, a catharsis, some might call it. I didn't expect to get the positive comments and emails I ended up getting, and I was happy to see that at least some people share my interest. It actually gave me the courage to go farther and start chatting online with gay men.

To tell you the truth, I quickly found it boring. Most of the guys just wanted to have somebody watching them masturbate, and that doesn't turn me on at all. But there was this one idea that kept taking over my mind and I believed that I was ready to give it a try, so I didn't want to give up so soon. Of course my major issue was discretion, so all the bars, clubs and things like that were out of the equation.

I went online and I tried different websites, posted ads with different pictures of my body, but I didn't find anything interesting. So I finally realized the easiest way-- a certain classified website... I don't know if I can name it here, but most of you will have heard of the "list of Craig", yes?

For my work, I was supposed to travel but I had the possibility of a layover weekend in Florida. For me it was ideal as I was in a city where I knew nobody, I was in a big hotel and I had two days to do what I had to do.

So here begins the story of this first time that might be the last.

I posted the ad on Tuesday night for a Friday night encounter, and the text was more or less this:

"Hi guys,

32 year old guy will be available this friday night at hotel XXX for his first experience.

Really want to suck you and maybe more.

Send me a message with a picture."

I had my own pic, one without my face in it, of course.

I received answers from guys of every age and race, from skinny to chubby. Most of them were more bottom as opposed to top, nothing that interested me. Then on Thursday, I found a message that looked promising.

The guy was in his forties, in shape, with a nice hairy chest. But most importantly, he had a very nice cock; not too long, but thick and really beautiful. I responded to him with interest, and we exchanged numbers to call each other on Friday afternoon.

On Friday, I was having second thoughts. I was really nervous and regretting that I had agreed to meet this guy. I thought about bailing, but in the end I headed to the hotel.

He didn't call me until I was already checked in and I was almost relieved that he had forgotten me. He told me that he was leaving his office and he would be at the hotel in 20 minutes.

I really was considering telling him not to come, but I was at the same time excited by the prospect of sucking this guy after so many years of fantasy. I gave him my room number and told him that I was waiting for him.

I set on my bed and just waited, checking the time every 5 seconds. When he finally knocked on the door I think I was never so close to getting a heart attack as that moment. My legs were shaking, my mouth was dry, my hands damp. I opened the door.

The guy looked pretty much like he did in his picture. He wore a regular business suit, all the better to blend in, and good news! He had a six-pack of beer in hand. I let him make himself comfortable on the couch and we started talking about the weather, the traffic, the usual fascinating subjects. He seemed like a nice guy, I decided as we drank a couple beers. I could almost forget the fact that he was here to have his dick sucked.

Suddenly he clapped his hands together and asked, "Should we start?"

"Yeah, I guess," I answered.

Just as normal as you please, he stood up and started undressing. It felt like I had hardly blinked before he was standing there with nothing on but his briefs. I was in shock, I think. I didn't move one inch during the whole process.

Then he asked me, "Do you want me to remove it, or would you prefer to do it?"

I said, "Whatever you want." At this moment I felt totally lost-- this guy was making it look so natural that it was impossible for me to react. He removed his briefs, and finally I had a good look at his semi-erect cock. It looked just as the picture had promised. He walked closer, stroking himself, and simply presented it to me as I kneeled on the floor.

I stayed frozen for a few more seconds, but then I finally started giving my first blowjob. I have to confess that I was hard as hell, and I really enjoyed the first minutes.

It was like discovering a new toy. I touched, licked, and sucked every inch of his cock and balls, and I even tried to deepthroat. But soon I got bored, taking no pleasure whatsoever. My cock had even gone soft. But I continued trying to do it the best I could, and honestly, I think the guy was happy. My only concern was not letting him come in my mouth, as I wasn't ready for that. But when the guy is holding your head there with both hands, you don't really have a choice in the matter. As soon as he came, I ran to the bathroom and almost puked.

I took a nice long shower, hoping the guy would be gone when I was done. I tied a towel around my waist and went back inside the room. To my surprise he was still there, naked on the bed, watching TV and having a beer.

I remained standing for a while, then decided to move to the couch.

"It was a good first round, no?" he said.

"Yes, thank you."

"Do you want to get room service before round two?"

Fuck. He wasn't ready to leave. It reminded me of the story I wrote about the tranny, except this was real life...

"Let's go for round two. I have some work to do." I was ready to give him another blowjob-- that didn't disgust me, but his lack of interest in me did a little.

I knelt down on the bed in front of and started to masturbate him. His hand pushed my head down after a minute and I began to suck him again. His free hand started to touch my back and my chest, and play with my nipples. I have to confess that my nipples are very sensitive, and I did get some pleasure from it. But I'd reached the conclusion that sucking was really not my thing, and I was hoping that this would be over soon.

But this guy was not ready to let it go. His hand started moving closer to my dick. He said, "My little whore. Come in with me, I want to show you something."

Despite my semi-erect cock, I was now sure of my heterosexuality and that the rest was only fantasy. Good boy that I was, though, I followed the order.

When I moved closer to him, he started to kiss me with a lot of tongue. I didn't really like it, but it wasn't as bad as I would have thought. But when he moved on to kissing my neck, my nipples, and further, I was feeling pretty weird, starting to feel like a woman. For a moment I thought he was going to give me a blowjob; it would have been a benchmark for me. But unfortunately, that was not his goal. His goal was my virgin asshole!

Okay, blowjobs are one thing, assfucking is another. I was having a mini-war in my head. On one hand I liked the idea of being fucked, and on the other hand I was scared of the pain. But when he started playing with my asshole, it wasn't as bad as I expected; the first moments were quite nice, actually. Rather quickly he got 2 fingers inside of me, and there was still no pain. The sensation of being open like that was very nice and I would be lying if I said I didn't like it. Eventually he decided that I was ready to receive him and he made me get in the doggystyle position while he put on a condom and got some lube.

I had, of course, fantasized about being taken like this so by now I really was looking forward to getting fucked. When he placed his cock at my asshole and started to push inside me, I think I screamed like a girl. But I still liked it, receiving him like this, and when he was all in he took a few seconds to let my ass get use of the dimension of his cock.

It was hardly painless, but so far I was enjoying this more than sucking him off, and when he started to move in and out of my tight ass I liked it even more. I have to confess that even though it was not as amazing as I have read in lot of stories, it was a very nice sensation.

After a few minutes he was ready to come so he pulled out of my ass, removed his condom and came all over my back. The guy was so pleased with himself. He gave my ass a big slap and called me a "good bitch".

I really understand why women think we're assholes sometimes.

Once again, I left for the bathroom to take a shower. I was really happy to have realized my fantasy, and I couldn't stop laughing about what I had done. The guy entered the bathroom behind me, fully dressed. He took a leak and as I was getting in the shower, he kissed me and pinched my ass. He told me to call him when I wanted another session. And then, at last, he left.

I slept so well that night, like after a good massage. In the end, I was really happy to have tried this fantasy. I felt more secure now, and I decided that that was the first and last time for me. I was definitely looking forward to having sex with a woman.

If you have the same fantasy and if, like me, you had to try it, I would be interested to know how your experience went.

Thanks for reading.