Names and minor details have been changed to protect the guilty. This happened a few hours ago.
I'm 23 and I'm still ambiguous about my sexuality. I've always been turned on more by guys. Recently I found myself jacking off far too much and not being able to focus on anything else. So I decided to post an ad to find a guy to jack off with.
I knew damn well there are plenty of spammers and perverts on this particular site, but being lonely and desperate I decided to give it a shot. Jack, a 22 year old guy at a local college dorm responded to my ad asking me if I could come over to shower and jack off. This was better than expected: dorms have security officers and I don't have to let strangers in my home.
On the way to the college, I felt nervous as hell and couldn't believe this was happening. It is the same nervous feeling you get when you have to go to the doctor to learn some bad news: you get a tremendous sense of urgency and inevitability. While driving, I thought what the hell am I doing, I can ruin my life and get into so much trouble, yet I knew there was no way back.
Jack met me at the gate and checked me in at the security desk. I was still very nervous and admitted it was my first time. He was bisexual and had messed around with other guys a few times before. We walked to his room and decided to shower first in the communal shower. I went to college, but lived in a dorm with private showers so that was an extra turn on for me. Jack took his shoes and socks off and I kicked off my flip-flops. We gave each other a bear hug. His cock was already hard in his jeans, while I was still soft and nervous. I rubbed my bearded face on his stubble and that felt amazing. His fingers lightly lifted my t-shirt and grazed my back and abs. I began unbuttoning his shirt and he peeled of my t-shirt. His chest was covered by stubble just like his face. I found that extremely arousing and pressed my smooth chest to his. We ran our hands all over our upper bodies and played with each other's nipples.
We hopped on the bed and dry humped in our jeans with our bare chests and feet touching. Jack kept reaching for my crotch but I was still soft. I really wanted to hit the shower at this point to take the edge off. We got off the bed and took off our jeans and underwear. He handed me a towel and we headed to the shower. We decided to pretend we didn't know each other and took separate stalls. We checked out each other's naked bodies in the shower: his cock was mostly soft at this point and so was mine.
After going back to his room, we towelled off and took off the towels. Back on the bed I lay on top of him and our cocks touched. We rolled around like that for a while. He quickly got hard, but I was still soft and thought he was kinda rough on me. I told him to take it slower and he rolled on the side and gently rubbed my body from my neck to my cock and balls and down to my thighs. Jack lightly tickled my ankles and the soles of my feet which started to get me hard. Then he focused on my inner thighs and soon I was harder than ever before. We started jacking each other off. With my free hand I was exploring areas I had never touched on another guy: his hair, his neck, the small of his back, his stubbly chest and nipples, his soft belly. At this point we were jacking each other off quite aggressively.
He told me to stop as he was close. I rolled on top of him again and kissed his neck. I placed his cock in my butt crack and he lightly humped me. I closed my thighs around it and he thrusted rapidly. I then took both of our cocks in my right hand: I've always wanted to frot with another guy. At this point we were both very close. He asked me to make him cum and I obliged. His strong arms hugged me really tightly. At this point I was jacking our cocks furiously. Jack moaned really softly and I felt his load on my hand and between our bellies. This sent me over the edge and I let out a really loud moan, which I rarely do when jacking off by myself. He calmed me down and asked me to stifle my moans as the walls are really thin. I stood up so I was straddling him to behold the cum on our sweaty bodies. We had shot all over the sheets and each other. I hugged him again and we shared the pleasure of the afterglow. He told me he could feel my heart racing against his bare chest.
It was time for me to go and Jack had other plans for the day as well. We wiped the cum and sweat off our bodies and got dressed. He had other plans for the day so we headed to the parking lot. I was in complete disbelief and did not know what to make of what had just happened: it felt like a dream or a nightmare. I never imagined myself doing this. I drove home trying to focus on the road and sat down to write this story still smelling of cum and his cologne.
I have a feeling we both did not fully enjoy our encounter. I was so nervous, it felt like an out of body experience and he was a bit too rushed and rough. While walking to our cars we barely said a word to each other. We have each other's contact information but I have a feeling I will never hear from him again...