This is a true story to the best of my recollection. Be gentle, this too is my first time at writing a story. Names have been changed to protect the innocent and guilty.
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I had made it to 48 without a mid-life crisis event. No mistress, sports car, or job self-destruction. But there was a dawning realization that in all likelihood I was half done. There were regrets although by every stretch I had been very successful in life up to this point. And for some reason I focused my regrets on my sex life and what I hadn't done.
I was a 22 year old virgin when I met my wife and she was the only woman I had ever slept with. But had a secret too that I had never told anyone. When I was a shy, naive, and innocent 18 year old I had been borderline molested by a male friend of my grandmothers.
I'm not sure if that's what triggered what transpired but it certainly factored in where my head was.
Thirty Years Earlier
I was staying with her that summer and one of her friends hung around and drank beer on her porch during that summer. George would stay a month at a time in his trailer parked at her place and then go back and captain a fishing boat for a while. I was lonely and knew almost nobody in the small town. They'd let me drink beer and he had a bunch of penthouses and hustlers that I'd read and whack off to.
One day she was busy making something in her tiny house that was pretty much a bedroom, sitting area, and kitchen and I was dead tired as teenagers often are. My bed was her couch and with all the noise I kept on getting woken up. George finally said "Go crash in the trailer. It's a lot quieter there" so I did.
It was kind of hot out on the metal trailer but I pulled off my shirt, socks and shoes and tried to sleep as best I could. I dozed in that way you do when it's just too hot but didn't hear George enter the trailer. My first realization was when I felt him grab my package and unbutton my jeans. He tugged them down in one motion underwear and all.
Now at this stage in my life I thing I was perpetually hard. Often so much it hurt and wouldn't go down. And I had a huge erection at that moment and I'm sure it looked even bigger on my skinny 150 pound frame. It slapped my stomach when the pants came off and George reached down and stroked it with a big hand. My hips came off the bed with the sensation and he used the opportunity to kneel down at the edge of the low bed and take me all the way into his mouth.
He sucked at it powerfully and I was both groggy from waking up but my whole being was focused on the guy sucking my dick.
Now I was so naive that I knew vaguely of blowjobs that girls gave but I had no clue about gay sex and what was even done. I guess I knew they sucked each other but much more than that was a mystery. The fact I had a man actually sucking on me sort of blew my mind and I felt guilt but my legs were also twisting in a rictus against the bottom the bed as the new sensations hit.
I might have lasted a couple minutes tops and arched and shot into his mouth. George didn't spit or anything so he must have just swallowed what was my large teenage load. He nudged me over and lay next to me after taking off his pants.
"Touch it" he said and grabbed my left hand and put it on him. It was warm and soft but it was the first cock I had ever touched at that point. "Shake it."
I didn't know what the hell I was doing. I didn't jerk off that way but apparently it worked for him. I shook him until my hand grew tired and he finally came and used a t-shirt to wipe off with. He dressed and I dressed and nothing more was said.
I was in shock at that point I think. That an overwhelming guilt. The next day I had a spot on my cock that was almost raw because he had sucked so hard and it hurt when it touched my clothes. I didn't know what to do and just tried to hide it and walk normally.
I'm not sure what he said to my grandmother who still seems like she was unaware to his nature but I found myself staying in his trailer that next night. I knew what was coming but quickly faked going to sleep on the separate bed.
I laid on my side, facing the couch cushion figuring I could protect my sore cock and give him little opportunity but I know now that he was excited at his new plaything. Pretending to sleep I heard him move over towards me and then he attempted to roll me on my back.
The idea I had at the time was that by going rigid and not turning over he couldn't touch my sore cock. I was horribly naive of course and didn't realize that sodomy was another option if I would roll over. I rolled on my belly and went rigid and I'm pretty sure by then he knew I wasn't asleep. He tried a few times to roll me over before grabbing the waistband and pulling the underwear I slept in over my bare bubble butt.
I had no clue at the time but I had one of those very round asses that combined with my slim but tall frame probably drove gay guys wild. Perky, round, with very little fat but a naturally curved shape. I resisted turning over again and after a couple of tries the couch sagged with his weight as he straddle my thighs and I could feel his hard, warm member rest in the crack of my ass.
He rubbed it up and down the crease several times before getting up and then coming back. There was a cool, slippery squirt of hand lotion in my crack and he rubbed it in with his cock. Thinking back he was probably tempted to sodomize me but was afraid I'd make noise and fight it. I hadn't said no but hadn't cooperated entirely and being outed for that in a small town at that time might have at minimum gotten a beating from some of the local lumberjacks or police. Being gay in that setting simply wasn't acceptable.
His finger slipped down up and down and felt my anus. It rubbed in the lotion and he tested the entrance. The initial penetration made me try to squirm away but he was sitting on my legs. That continued for several minutes but I think the uncertainty saved my virginity that day.
More lube got rubbed into my crack and he rubbed his cock up and down between my cheeks rapidly. The creased bubble half contained him and he picked up speed until there was suddenly a gasp and wet liquid spattering from anus to lower back as he came. A t-shirt wiped it from my body and he left me alone, underwear still pulled down to mid-thigh and slick residue still in my crease. I pulled them up ashamedly and went to sleep for real then.
That was our last physical contact. I was guilty and ashamed and he was worried I'm sure. He bought me little gifts that I accepted but wouldn't let him be alone with me. He was worried I'd tell I'm sure but one time he whispered to me that next I should suck him like he had sucked me. That it was only fair. I didn't say anything and the lack of acquiescence probably scared him off. A week later I went home.
George tried one more time to get me alone a couple of years later but my visit was brief and the opportunity never arose. About five years later he was dead from cancer and I figured I'd let it die with him.
Thirty Years Later
So here I was a 48 and I was thinking about my lack of experiences. What if I had let George continue? Sucking his cock and letting him put it up my ass. God help me I regretted the missed opportunity. This was pre-AIDS and the idea of having a man sodomize and fill up my rectum with his semen was somehow appealing now. And it wasn't something I would let anyone do now because of fear of diseases that had since spread.
Being used and dominated was so foreign to my current role of husband, father, and business leader. Where everyone looked to me to lead and the constant pressure to do so sometimes felt overwhelming. Yet that's what I wanted and it became an obsession. I'd fall asleep every night with the idea of being bent over and violated thoroughly. The cum leaking out of my dilated anus and sliding down my ball sack afterwards. Sucking that cock hard again and letting it spit cum into my mouth and on my face like a porn star. Like a whore covered in shame and guilt.
So I made secret accounts on a tablet. One that was non obvious and password protected. GPS and any other identifying items except IP address were turned off. I used my photography skills to take better than average pictures and tried to write a profile that would attract guys. I wanted them to lust after me, try to seduce me, and in the end take me. I wanted to be slut for it.
Most of them didn't get it but a few did. The verbal jousting and understanding seduction went a long ways. I also had problems getting away for a couple of hours as well as having the time to clean out before hand. That winnowed the field more because most wanted to get their rocks off now.
Then Steve started saying the right things. A divorced father of one in his early fifties with his own apartment. He lived 10 minutes away but we didn't run in any of the same circles thankfully. I had a Sunday morning free and set it up.
I was nervous as hell but cleaned out in silence while my wife slept. Followed it up by shooting two plungers of lube up my hole. I wanted to be lubed up like crazy because I wasn't sure I could take a cock and my own was fat enough that I doubted I could take anything similar without a lot of work. I wasn't sure how I compared either and his pictures didn't give me a lot of clue. I knew I was slightly about average at 6.5 inches long but it's 2.25 inches in diameter. The fattest dildo I had ever managed was 1.5 wide and that was a struggle requiring much time and lube.