First time Anal
So, here goes my story.
I was all straight, except for the one incident at varsity (being drunk and high) where myself and friend wanked each off and kissed. But at 31 years old, i had had a few long term relationships with woman and well a few “not so long” ones.
As with any guy… i found myself watching porn sometimes on-line. But the last year, i was starting to watch gay porn more and more, and well, staring at guys and their build while walking the streets and in the gym. I myself was hard at work getting bigger muscles and toning my stomach to reveal my dissapearing six pack once more.
Gay sex was starting to become an everyday thing, and i even used my gf dildo on my once while she was on a business trip. Very uncomfortable at first, but i managed to get a large part it. At first, it was uncomfortable, a feeling of fullness but almost like having a shit stuck in there. Then it became easier and i started to enjoy it. I used it a few times, but later on went to a sex shop and bought a prostate stimulator. This was even better and then one day, i actually came while playing with myself and my prostate stimulater. It was not a normal orgasm, but instead of 15 seconds, it felt like i came for 2 minutes non stop! I decided it want to try out having anal sex and playing with a guy.
One day – i got onto a sight called manhunt…and well, i created a profile. Obviously hidden pics and so forth, but it wasnt long before i started chatting with a guy, telling him my story and well, how i was curious. And then, well, came my first hookup. I went to his house one early morning (instead of gym) as i was living with my gf at the time, so my place was out. Met him at his door, he walked me in and led me to his bedroom where he sat down. He only had some boxers on, i was in my gym clothes. We started chatting and he touched my leg. I enjoyed in and it wasnt long before he felt my growing cock through my pants. I touched his and he started kissing me. I loved it. We laid down and he stuck his tongue into my mouth, i did the same. Soon his hand was inside my pants, rubbing my cock. I did the same to him. He then took off my shirt, i stood up to take off my shoes and he proceeded to remove his boxers, and laid waiting for me, naked. I removed my pants and laid down again next to him, both of us naked. We kissed and rubbed each others cocks.
He then went between my legs and started sucking my cock. I was on my back, knees up and him inbetween. It was amazing. Him playing with his tongue at my pee hole, then taking all of me in. He then while sucking me, starting rubbing my ass and around my hole, in put his pinky inside. I thought i was going to cum….he stopped and asked if i was okay and i said it hurt a bit, but i liked it. I did tell him about my little experience and that i would like to try anal, but needed time. He then put some lube on his finger and proceeded sucking me and massaging my hole, and with the lube, it became much better…in fact…i enjoyed it very much. He came up and starting kissing me and i tasting something sweet, he told me it was precum. While kissing me, his cock rubbed against my hole and this made me feel hornier.
I then pushed him off me and went on his back and i proceeded to to the same to him. He put a bit of lube on his hole and asked if i would finger him. I tried to put my pinky inside, but he said i should use my index finger, which i did. His backed arched a bit and starting tasting a sweet taste again….i saw precum on his cock as i let his cock slip from my mouth to focus on this ass. The started pinching my nipples, which i enjoyed. He ten pushed me off him and in one swoop turned me around on my back and threw my legs over his shoulders. he started licking my ass…. he then came up and asked if i was okay of he rimmed my ass. Since he already started, and myself enjoying it, i simply said….”mm…just go on, you know what to do”, submitting myself to him. I was sucking and licking at my hole and with his hand, pinching my nipples, hard and soft…i enjoyed the feeling. He took his hands away and starting playing with my cock and balls. One hand then slipped a finger inside me, but this time it was his index finger. I squirmed, it hurt at first, but then it was enjoyable and made it better as he bended his finger and starting playing inside. he started sucking on my balls. I enjoyed it and my hand for some reason squeezed the tube of lube and it messed on my hand and his bed, but i was in ecstacy. He came up and kissed me and grabbed his rock hard cock with my hand. He squirmed a bit and i realised it was with the hand that had lube on it. I apologized, but he stopped me by sticking his tongue in my mouth, we kissed and i jerked his cock. He then looked me in they eyes, smiled and went down again, sucking my cock and playing with his finger in my ass. He again came up, taking his finger out of my ass and looking at me and smiling. I was a bit dissapointed because his finger inside me starting feeling REALLy good, he kissed me again and his cock rubbed against my ass….i sort off moved around, sort of hungry for it. I felt his hand at my ass and the though of having his finger inside me again got me excited. But then i felt him pressing his cock cock against my hole with his hand, his tongue in my mouth and then a hard push and i felt like something was taring inside me, i actually said “ouch”, but then followed it by a a “ooh, that feels good”. IT was painfull but nice…he then put more pressure and i felt him going in deeper. It hurt, but also felt good. I sort of relaxed and suddenly felt him go in much deeper. My cock started feeling very good and i had this feeling of fullness.
he started to thrust and it felt like someone was rubbing my cock, but on the inside. It was amazing! I opened my eyes and saw him, looking me in the eye and smiling. He asked if i was okay and i said it felt amazing. He said i should look at my cock and i saw clear liquid running from it, oozing pre-cum. The feeling of fullness was amazing and i suddenly felt my cock getting really hard and i sort off yelled out “fuck yes” and starting shooting a load that hit my chin…. another shot and yet another as i was cumming. it felt like it would stop and he was in ecstacy. He looked me in they eye, smiled and kissed my chin, licking up my cum, then kissing me. He came up and said “ohh” and he started thrusting faster then stopped, i felt his cock swelling inside me and suddenly felt his cock throbbing and then a warm feeling inside me. He was actually cumming inside of me! He looked me in the eye while cumming and smiled at me, saying how he is enjoying it. After he stopped, he kissed me and then pulled out and stood up.
he said i should come with him, showed me the shower and said we should shower. The cum was dripping down my leg. He opened the water for me and i stepped in, when the water was fine, he walked away and got me a towel. I got out and started to dry myself off and he got in and showered. I got dressed while he got dressed.
Thinking he would offer me a cup of coffee for this early in the morning, we stepped out of the room, he showed me the door, gave me hug and said it was great fuck.
I never heard from him again.