Note: This story explores a bisexual/bi-curious relationship where two friends explore the boundaries of their sexuality.
*
"Here goes nothing," I thought as I clicked submit. I had finally mustered the courage to post an advertisement. For quite a while I had kept my online habits a dirty, little secret. I'd go on chat sites and swap porn links with other guys. It was such a turn on to chat dirty with them about the women in the pictures. We talked about what we would do to them, what made us hard, past sexual experiences. My tastes are fairly diverse when it comes to perversion, from mature to fit to group, my appreciation for women in all shapes, sizes and colors made it easy for me to get on with many of my fellow chatters.
After years of online fun, I was putting up an advertisement on an adult site to find a jerk off buddy in my area. I had been transferred to a new town for work and didn't know anyone there. The anonymity of meeting someone new made me nervous, in a good way. I was excited about the prospect of doing what I've always done online with someone in real life. However, I could not ignore the knots in my stomach.
The following day seemed to crawl by as slow as it could. I was eager to get home and check for responses. I was not even sure what I wanted out of the experience but something about it gave me a raging hard on. When I finally did get home, I signed onto the website where the ad was posted. There were three responses. One was simply, "Hi," another was obviously a spam link for a nude live cam show. The third however, seemed to be more promising.
"Hey, I saw your ad and I thought I'd say hi. I'm from your area and wanted to get to know someone. Perhaps we could chat online a bit and see where things go?"
He included his email address which I assumed was newly created for this purpose. My heart-rate increased. I quickly added the email address to my Yahoo messenger. He was online.
"Hi," I typed after deliberating what to say. "Oh hi. Guessing you got the reply to the ad?"
"Yea, thanks for replying, I was wondering if there was anyone out there," I felt so awkward.
"Haha, yea. I'm used to online chat sites, but never really done the whole ad thing before. I'm actually new in town too. Not that new, a few months. But I don't know very many people here."
"Oh ok, that's cool. Yea, it would be good just to chat online for now. I'm a bit nervous about doing the in-person thing right away."
"Yea man, I totally get you. Same here."
"Nice, that's a relief. What are you into?"
"Almost everything I guess. Big breasts, nice ass, chubby sometimes, mature, Latina, fit...yea pretty much everything except the weird stuff."
"Perfect, me too, got any links?"
"Sure give me a sec."
We began trading links. Usually I'd browse sites and post some of the better pictures I found on a chat site. This time I went to some of my 'favorites' and shared it, hoping to get a feel of my new friend. From what he sent, we were on the same page as far as taste went. The first chat went on for a couple hours and I was content with the results of my ad.
"That was awesome," he said after letting me know he came."Mmm, nice,"
"I'm Chris by the way,"
"Oh, Jon here. Totally forgot about names, lol"
"Ha, yea. Same time tomorrow?"
"Sure."
Falling asleep that night, my mind wandered. I wondered whether I did the right thing giving this stranger my real name. Whether we would ever meet in person, whether we ever should meet in person. Finally, I fell asleep and it didn't matter anymore.
The next day, I kept glancing at people I passed. Anyone could be Chris. It's a fairly large place, he could very well be a half hour away, but still, I kept wondering. That night, sure enough we chatted again. This continued for a few nights. It was basically the same as what I'd do on the chat sites. Share links and chat about them. Then one night Chris seemed ready to push the envelope a bit more.
"What would you do with a guy in person?"
"Not sure, never thought too hard about it, to be honest."
"Would you jerk off in the same room as another guy?"