Awkward Gay Sexual Encounters
When I was 28 years of age I had gone through 2 bad relationships with women and had not had sexual encounters with men in 4 years since the last time I had sex with Corsica. After having moved across the country, and an extended drought of sexual activity with men I decided it was time to try finding men on man for man chat again. I was still in great shape, at 6 feet tall, and 155 pounds in weight with a 7-inch-thick cut cock that was beginning to be under used.
Sadly, the first 4 guys I met in the gay chats never went anywhere sexually because they were not sure what they were into sexually.
It wasn’t until Dan came to hook up with me that I finally had sex with a guy to end the drought of having gay sex with men. Although having sex with Dan was not very exciting. Dan was 6 feet tall, 180 pounds with an average build. Dan did have a nice ass, and he only liked being fucked, he wasn’t into much else. Sand came over to the House I was living in and didn’t do anything beyond giving me a hand job to get my cock hard before bring his pants down for my to fuck him through the whole he had cut in the back of his underwear so he could be fucked without taking them off, and just pull up hi pants and leave when her was dome being fucked. As boring as the sexual encounter was with Dan, we never got together sexually again after our only sexual encounter that occurred.
A month later I met Greg on the gay chat room, and he said he was into kinky gay sex. Greg told me he loved giving men blowjobs and prostate massages to give men an explosive orgasm from the blowjobs he gives. When Greg came over to my apartment, he came in with a small duffle bag. When I asked Greg what was in the bag he told me it was a thick double ended 20-inch dildo that he likes to use.
When Greg and I were in the bedroom he asked me to take off all my clothes, and to lay comfortably on my back. When I did so Greg told me I looked very sexy and he took his clothes off and crawled into be with me while both of us were naked and Greg rubbed his hands on my chest and asked me if it would be ok for him to finger me while he is giving me a blowjob. When I told Greg I was ok with it he lubed his index finger and put it up my ass to massage my prostate as he gave me head. The prostate massage felt so good that my cock exploded in Greg’s mouth when I came and made my entire body tingle when I came.
After Greg swallowed my cum, he said now it was time for him to use the dildo while giving me a blowjob to make me cum even more if I was ok with it.
I told Greg he could go ahead and he lubed the dildo on both ends, before he slowly slid the dildo up my ass while I was on my back and he started sucking my cock again. As Greg sucked my cock deep, he slowly moved the dildo up and down in my ass until I came deep in Greg’s throat. After Greg swallowed the cum, he told me to roll over and get up onto my knees while the dildo was still in my ass. While doing so Greg got onto his knees and put the other end up the dildo up his ass with our knees touching as he straddled his ass to mine with the dildo up both of our asses as we both moaned until we came onto the bed sheets.
After we finished having sex, I asked Greg why he uses a dildo to fuck rather than using his cock.
Greg told me he likes fucking and being fucked at the same time and the double ended dildo allows him to do so while making it easier to clean up and go afterwards. Greg then said at least he knows that he can’t get any sexual diseases from a dildo as he put the rest of his clothes on and left.
As weird as it left me feeling in the awkward way we had sex, we never got together to have sex again afterward.
The next person I met on the man for man gay chatroom was Emanuel. Emanuel and I chatted with each other online for a few weeks before his got us a motel room to meet and have sex. Emanuel was the first Hispanic guy that I ever had sex with. Emanuel was 6 feet tall, 280 pounds with a large build and big ass and a 7-inch cut and thick cock just as he had described to me when I asked him in the gay chat about his physical stats.
When Emanuel made to room reservation for us he told me that he was going to give me a full body massage that I would never forget and he left me feeling excited when I was left thinking about it as he left to go and check in to our motel room and got back onto the gay chat to let me know he was checked in to the room after he got there so I could take a shower, change clothes and head to the room myself to meet Emanuel.
Much to my surprise, when I got to the motel room and knocked at the door, Emanuel answered the door to let me in while he was already fully naked. When Emanuel opened the door, he gave me a hug and a kiss before he held my hand and led me to the bed after closing the door to the motel room. Emanuel made out with me while helping me to undress until we were both naked when he lifted me into his arms and laid me onto he bed on my back to begin giving me a fully body massage.
Emanuel started by massaging my arms from my hands inward, then my chest and stomach, and my legs from the ankles upward until he got to my cock that he sucked until it was hard when he sat on my cock to take it in his ass all the way to ride until I came deep inside him. After I came deep in his ass Emanuel asked how I enjoyed getting my dick massaged inside him.
When I told him that I truly enjoyed it, Emanuel rolled me over onto my stomach to massage my arms from the wrists inward, then massaging my back from my shoulders to my waist, then my legs from my ankles upward until he got to my ass. When Emanuel got to my ass, he massaged my butt cheeks while eating my asshole to soften it as it became moist when he slowly worked his cock into my ass until it was all the way in. When Emanuel’s cock was fully inside of me he laid on top of me and held my hands with our fingers interlocked as his kissed and tongued my ears while slow fucking me for nearly ten minutes until he came deep inside of my as I enjoyed every minute of and I used my ass muscles to milked every drop of cum out of his cock. After Emanuel came deep inside of my and still had his cock inside my ass he asked me if I enjoyed the deep tissue massage of my guts with his dick in my ass.
I turned my head and said, “Honey, I loved every minute and every inch of it.” I then wiggled my ass with his dick inside of me.
Emanuel said good and his kissed me and said he was going to fuck me to give me another deep anal tissue massage before I showered and left. Emmanuel fucked my slow and deep as he held me close for nearly 10 minutes again before he came deep inside my man pussy again for my ass muscles to milk every last drop for a second time before he rolled me over and we made out for about a half an hour before we both got up and took a shower together to clean up after I began feeling the cum dripping on my leg from the semen inside of me.
After I was dressed when I finished taking a shower, Emanuel and I gave each other a hug and a kiss before I left the room and that was the last time we ever saw each other again. It was a great gay sexual experience that helped make up for the past two men I had sex with that had felt so awkward with both of them.
