Bottoming with My Mentor

My cock was hard and it rubbed pleasurably against the comforter with the same rhythm as his plunging cock while it slid in and out of my soft moist asshole. I began to realize that we were going at it together for what felt like a long time by this point, and i figured that it was the condom that was keeping him going, so i looked over my shoulder and breathlessly asked him "do you feel like cumming soon?" He had his eyes closed and head tilted back, obviously trying to reach his climax, so I turned back around and let him concentrate. Then I decided that I would help him along by squeezing my asshole around his shaft and sure enough he moaned, then I whispered "cmon, man...give it to me..fuck my ass!!..this feels SO good..fuck me..". Sure enough, he groaned loudly and I felt his body begin to tremble and his hands clamped down my hips in a powerful grip. Then his cock stiffened inside my ass and I knew very well what that meant...

Finally, the air exploded out of his mouth and he yelled out "OH GOODDDDD" while he nestled my ass against his groin as he ground into it. His cock throbbed while buried inside me and I knew he was cumming hard because his breath came in ragged gasps followed by his whole body shuddering. He let go of my hips and planted his hands on the bed on either side of me just to keep himself from falling over on top of me. He was dripping sweat all over my back, and everything smelled like manliness and sweat, which was actually slightly off-putting, probably because I'm used to being stimulated by the smell of a woman, and there is definitely a difference.

Still, the deed was done and there was no turning back, not that I had any regrets to begin with. He regained his composure after a moment and then pulled his hips back and I felt my rectum emptying, followed by my asshole no longer being stretched open for the first time since he first penetrated me. It still felt loose, slippery, and stretched out as I looked over my shoulder at what he was doing. He was staring at my anus which might have been gaping slightly, and I felt cool air against it, so I clenched it closed which it did with a squishy sound. A little bit of fluid ran down my balls when I clenched but I knew it was probably mucus since he was wearing a condom, so it couldn't be cum.

Fred nodded, smiled, and then pulled his condom off and showed it to me. Then it was my turn to nod and smile because there was a huge load of cum in it. I said "wow, that's alot.." and he winked at me and placed it on the night table and rolled onto his side. Then I reached back and touched my anus just to feel it, and it felt soft and dilated. I realized that although I had received during sex, I still needed to climax, so I reached for the lube and pulled out the cushion and rolled onto my back. He looked over at me and told me how amazing that was and how I was a natural at it, then jokingly asked me if I was sure that I wasn't really in the closet.

I didnt answer him and just squeezed some lube onto my hands while he stared at me curiously, then nodded understandingly and said "go ahead, you earned it!" Then he rested his head on one hand and laid there on his side watching me jerk off, commenting on how interesting it was that I used two hands and that he would have to try that one day. Then he asked me if I wanted any "help" but I just shook my head and laid on my back stroking myself until I felt my load gathering in my loins. My cock was rock hard and when I finally came, I felt my tender sphincter pulsate while thick ropes of cum shot out all over my stomach. He chuckled and said "wow, that's a lot!" just like I did, then patted my thigh and thanked me for letting him share such intimate experiences with him.

Then Fred got up off the bed and went to take a piss, saying as he walked to the bathroom that I was welcome to stay as long as I wanted. I said "thanks" and laid there for a minute longer, enjoying the afterglow, before slowly sitting up and attempting to go piss after he came back, but when i stood up, my legs felt wobbly and my ass ached, so i had to walk slowly. He noticed and chuckled saying that I would get used to that and that it would go away soon, that the human anus and rectum were surprisingly elastic. I just nodded in acknowledgment and when I came back after cleaning myself off, I sat down awkwardly on the bed and began to get my clothes on while he just laid there naked on his side watching me.

When I had my shoes on, I turned to him made him swear to keep this between us and never tell anyone. He smiled and nodded and looked genuinely solemn when he swore with his hand in the air. Then he told me to turn off the bedroom light on my way out because he was going to take a nap, so I did as I walked slowly to the front door, acutely aware of the pleasant well earned ache in my butt. When i opened the door, he called out "Thank you again!!" and then it closed.

I slowly walked down the hallway towards the elevator alone, trying not to think about the slippery rawness in my freshly fucked asshole and hoping that none of his neighbors saw or heard us, not that it mattered.

What did matter was his promise to keep this a secret between us, and just the thought of anyone at school or at the hospital finding out was terrifying, but nobody ever did as far as I know. The heterosexual voice of my conscience was trying to make me second guess my decision to surrender myself to Fred, that I was less of a man for allowing him to penetrate me and fuck me in the ass, but I rationalized that I was a grown man and I chose to let it happen...and it actually felt really good.