I was 26 years old, and living in an apartment, just getting my career going after spending time in graduate school. I had always considered myself straight. I was never what you'd calla "babe magnet" and I was never real good at picking up women, but I wouldn't say I was sexually deprived either. Through several one night stands and a few semi-long term girlfriends, I'd say I probably had at least as much sex as the average single male my age.
To make a long story short, I started wondering what it would be like to have sex with a guy. I wasn't attracted to any particular guys, but the idea of gay sex was really starting to turn me on. I had never been homophobic, never disgusted by gay sex like a lot of people. I never really had any interest in it, but it didn't gross me out.
So what does any bi-curious guy do that time, place a personal ad (the internet wasn't that big yet)."Bi-Curious SWM 26 interested in meeting same for talking and maybe more." The ad came with an "800" phone number for the people to reply to, so I didn't have to give out my address or phone number.
The day the newspaper came out with my ad, I couldn't believe what I had done. I said to myself "I can't do this" and decided not to check my messages. But that night I masturbated fantasizing about sucking a guy's dick.
So of course, a few days later I just had to call the number, and my hand was shaking as I dialed the phone. There were about 8 messages, the majority of which were from people who sounded like weirdo's – "Oh, yeah man, I wanna suck your dick and if you're not too bug I'll let you fuck me. Call me, man." Stuff like that. I didn't feel comfortable contacting someone who seemed too into this lifestyle, so I ignored most of the messages.
There was on message that sounded just like me, kind of nervous and curious. "Hi, my name's Anthony. I'm 24, 5'10" about 158 pounds. Average build, I guess. Brown hair. I've been kinda curious about what it's like to be with a guy lately too. If you're interested in talking, call me." His build was a lot like mine, but I was about 15 pounds heavier. Not muscular but not fat either.
Hmmm, this guy at least didn't freak me out. So I called him. He answered! What the hell am I supposed to say? To make a long story short, we were both very awkward in our conversation, but we managed to agree that we were both curious, couldn't imagine ourselves falling "in love" with a guy or being a couple. We both were interested in kissing a guy, and oral sex. We decided to meet that Sunday afternoon (it was the only time he could get away from his girlfriend with no questions asked) at a restaurant near my apartment.
When I hung up, my first thought was "I can't go through with this." My second thought was "I've gotta whack off!" I jerked off thinking about him twice before I fell asleep that night.
So Sunday came. I waited in the lobby of the bar/restaurant. He was 20 minutes late and I figured he chickened out. I was sort of glad, actually. Then a guy walked in, came up to me and asked if I was Bob.
I said "Yes, are you Anthony?"
"Yeah, sorry I'm late" he said "I got a little lost."
"I thought you chickened out," I said. "I almost did."
"Well, the thought did cross my mind."
We both laughed at that and went into the bar and each had a beer. It was obviously not a good place to talk openly so we went back to my apartment. We sat on the couch, I put on the TV and we started talking – again awkwardly. A little talk about our sexual interests, but we mostly made small talk. After about 20 minutes I couldn't take it anymore. If this was going to happen, if I wasn't going to back out, something had to happen soon.
So I looked at him and said "Anthony, do you want to go into my room and fool around or something?" Boy was I smooth!
He took a deep breath, paused and said "Sure. By the way, my name is really Mike. I used Anthony so that if my girlfriend heard the message I could say it was a wrong number." Smart guy I thought.
We went into my bedroom and then stopped, both looking at each other. I wasn't sure what to do – should I get undressed, kiss him or what?
"I'm not really sure how to get started," I said.
"Me either. Maybe we should just lay on the bed and hug each other first."
So, we took our shoes off and laid on the bed next to each other, full clothed. I was looking at the ceiling, he had his eyes closed. I reached over and started stroking his arm. He reached over with his other hand and started stoking my arm too. I quickly started feeling his chest and latched onto a nipple and started rolling it in my hands. He moaned and tuned his head towards me, his eyes still closed. I looked at him and thought to myself, here it goes...and I kissed him!
I placed my lips on his and held them there. He stiffened up for a second then reached behind my head and pulled my face to him and opened his mouth. I immediately met his tongue. Again we were both nervous so not much tongue movement was occurring yet, just touching them to each other. I started tentatively probing with my tongue and he started to respond.
We made out like that for about 5 minutes, the whole time I'm thinking I can't believe I'm doing this. I couldn't believe that I started to get a hard on kissing a guy. This was unreal. Was he hard too?
I stopped playing with his chest and reached between his legs. I ran the palm of my hand over his crotch. He was hard alright! When I touched him there again he moaned. I did too.
I immediately broke the kiss and told him to sit up. He did. I took his shirt off and unbuckled his jeans. I took my shirt of and said "Are you sure you want to go further?" He looked away, but he said "Yes." I started to slide his jeans off and saw he was wearing whit under wear – "tighty whitie's" "Well this guy is definitely not a player I thought.
Since he was just laying on the bed I took my jeans off, and lad next to him. We were both naked. We started to kiss again. I rolled on top of him and we made out some more, grinding our pelvises together lightly.
"Do you want me to go down on you?" I asked him.
He looked me in the eyes and said "Yes!"
I slid down and got a look at his cock for the first time. It was maybe 5 inches long, and thin. I'm about 6" and relatively thick – at least that's what several girls had told me. Thankfully we were both circumcised – I don't think I could have dealt with a foreskin.
