Twenty one years of of bisexual exploration

8 years passed after my first awkward bisexual experience failed to inspire my bisexuality. In that time my wife had a few affairs and we had a child. I had a career that involved a fair amount of traveling and had been at it a few years when the urge started to me again.

Work had taken me to New Jersey and I found myself looking at personals on craigslist my first night at the hotel. To be fair the urge had come a few weeks before on a trip to Washington DC but I wimped out after talking to a few guys. This trip I decided I was on a mission.

The first night I answered a couple ads but nothing really came of the exchanges and I went to bed with the idea that as soon as I got back to my room the next day I would try again. The second night was more of the same.bi did have a couple promising prospects but they didn't pan out and I went to bed frustrated. 

On the third night I decided to post my own ad, after all I was in spitting distance if NYC and there had to be someone interested in taking the virginity of a married business traveler. I wasn't wrong and got a flood of responses, none of which seemed like a fit or planned out. I was about to give up when I got a response from a guy my age (at the time early 30s) his name was Ben and he was gay.

Up until then I had been trying to connect with other bi married guys and hadn't even thought about gay men. He sweet talked me but was clear he wasn't going to get into a long back and forth. I told him I didn't have condoms and he would need to grab some. He sent me a picture of his face, he seemed clean cut and nice, though at the time it was only his cock I was interested in, or so I thought. He told me it would take him about half an hour and I gave him my room number. His last message was "see you soon"

"Oh my God! This is really going to happen" was my first thought and my heart started racing. I had told him my story, about my first time and how I really wanted to experience sucking and being fucked. "I better shower" was my next thought, followed by "I only have 25 minutes"

I turned the shower on and washed my bits thoroughly, making sure to really get my ass clean (at the time I had no real understanding of how to clean up and clean out for a top) and then I put on a nice shirt and dress pants and paced around the room until the knock.

I nervously opened the door "Ben?" I asked "yes, you're Jeff?" He asked "Yes please come in". Until that moment I had really only been thinking about cock, but as this very cute gay men entered my room I found myself attracted to him. "Nice to meet you" he said, followed by "you're even cuter than I expected". Having never been told that by a man made my already racing rate skip a little. "Mind if I wash my hands? I was handling money" he asked and I showed him to the bathroom and then sat nervous on the edge of the bed.

When he came out a minute later I found myself checking him out. He was very good looking, handsome face and a great smile. He was well dressed in a button down shirt, belt and dress pants. He definitely had a much better body than my first partner and I found myself attracted to him immediately.

He sat next to me on the bed, he could tell I was nervous. "Don't be nervous" he said "sorry, it's just been a long time" I muttered and looked at him. He put his hand on my chin and leaned into kiss me. His lips met mine and his tongue danced and teased me. Ten seconds into the kiss and my nervous shyness had been replaced with animal lust.

Unlike my first experience he was making the moves. His hand landed on my bulge as we kissed passionately, shocking me but prompting me to do the same. He was hard and I could tell just from touching his bulge he was much bigger than my first.

He unbuttoned his shirt and then mine. We stood topless kissing as I started to grab at his belt. I moved my kisses to his neck then his firm and sculpted pecs, letting my hands feel his abs "OMG, he is ripped" I screamed to myself. I let my lips explore his body as I pulled at his belt like a kid pulling in the ribbon to a big present on Xmas morning. I pulled the belt loose and undid his pants, letting them fall to the floor. His cock was now bulging in his bikini briefs and I couldn't wait to get it free.

I pulled his briefs down and freed his hard on, it was a nice 7+ inches and was already hard with just a bead of precum on the tip. I admired it and looked up at him admiring his sculpted, muscular body before taking him into my mouth. Immediately I was more turned on than I'd ever been as my lips and tongue met his soft, smooth cock skin. I eagerly bobbed up and down, not able to resist moaning as I felt him grow even more in my mouth. After a few minutes I slid his cock out if my mouth and moaned "I want you" he just smiled and pulled me up for a kiss and then finished stripping me.

"Lay on your stomach" he said and immediately obeyed. Then I felt his hands sliding up my legs, pushing them apart as they moved to my ass and to my pleasant surprise I felt him separate my ass cheeks and his tongue tease my hole. I layed there moaning as his tongue teased my tight hole. "Oh my fucking God that's so good" I wanted as he slid his tongue inside me followed by a finger. A few minutes into him rimming me I was panting and moaning "Oh my god I want you, I want you inside me" and he said "are you ready" and I nodded enthusiastically. He opened the condom wrapper and slid the condom on his throbbing cock as he kissed me, the slight tang of my ass on his kiss.

"You should ride me so you can control it" he said to me and had me straddle him. The excitement and arousal from feeling his cock head press against my hole was quickly replaced with the pain if the reality of a virgin ass being met with a dry condom. I pulled up and tried again, and again and again but my hole wasn't letting him in. "Don't you have lube?" He asked "none" I said "damn, I thought you had lube, I would have brought some...hold on I have an idea" 

He ran to the bathroom and came back with a bottle of shampoo and slathered it on his condom covered cock "let's try it on my back, I trust you" I said as I layed on the edge of the bed and welcomed him between my legs. He lined up to my hole and again it felt amazing as his head met me. But again I was not letting him in "just relax" he said and leaned in to kiss me "push out" he whispered and I did. The head of his head popped past my first ring and quickly popped out with a sting. He tried again he popped in and right back out but this time the sting stayed. The shampoo was burning and we both decided it wasn't going to happen. "I'll suck you if that's ok" I whispered, disappointed but eager to please this sexy man who had been so patient. "It will taste terrible after condom" he responded. "I don't care" I shot back "I want to please you" and I pulled the condom off him and strikes his cock before lowering my head and accepting him in my mouth...he was right, it tasted terrible. 

After a minute of suffering through the tingle of spermicide in my mouth I decided to jerk him off, I was determined to make him cum. I kissed him deeply and nibbled his ear as I stroked him, whispering how I wanted him to cum for me. A minute later he pulled me in for a kiss and I felt his cock start to pulse in my hand and his cum started to onto his stomach, chest and a little bit in my face. After he came I grabbed my own cock and came on myself as we kissed. It wasn't what I was hoping for but it felt great.

Before I opened the door for him, my only interest was in cock itself. By the end of our time together I found myself completely attracted to him. I layed in his arms and we talked for a bit and kissed. I felt his chest and abs and we gave each other pecks like we were old lovers. It was the first time I had that kind of affection from a man and the first time I wanted it. It made me feel different, special, like I was his.

After about 15 minutes he got up and we cleaned up and he got dressed. I slipped on a t-shirt and my boxer briefs and walked him to the door. We shared a passionate kiss followed by a few pecks "If you're in New Jersey again, email me" he said and then he disappeared into the hallway.

I lit a cigarette and sat in the desk chair and sighed "if only he had been my first" unlike the first time when I thought "I never want to do that again" this time I was longing for more, unfortunately it would be a couple of years...