Several years ago, I was in my early 40’s and freshly divorced after a 10 year marriage fell apart, primarily due to a lack of sex, none for over 5 years, attributable to my wife cheating on me with a co-worker for nearly the entire marriage. I discovered this by sneaking a look at her unlocked phone and finding messages and pictures. I was on my own, unbelievably horny, but having been out of the game for so long, I was at a loss as to how to even start. I had no interest in a relationship and only wanted a hookup, a lot harder to find. I spent a ton of time online, watching porn and masturbating, really yearning for the real thing. As time passed, I explored more and more types of porn to get off, which I think is the norm for guys in my situation, but I also leaned on the images I had seen on my ex’s phone to get off, something about seeing his dick pics, some with her in them, got me excited. Ultimately the porn I really started focusing on was cuckold, shemale / tranny, and guys on guys.
Eventually I’d had enough of self love and wanted the real thing, the easiest thing in my mind was to find a guy online to service me, so I started checking out some online sites to see if I could get some action, but never had the courage to contact anyone. One late night after a few drinks, I decided the best course of action was to place my own ad, if I didn’t go through with it at least I might get some dick pics to jerk off to later. My ad was simple, divorced white male seeking oral, possibly more, snapped a pic of my hard cock and just for the hell of it a pic of my nice ass. To my surprise, I started getting replies instantly, it was hard to sort through them, I was right that getting a guy to blow you was way easier. Most of the responses were to the point, with basic stats and offers to give me the best BJ I ever had. I settled on a couple of replies to engage in further conversation, finally choosing a guy who claimed to be partnered with another man but was in an open relationship, his name was Javier. I suggested that he come to my place if that was okay, and he agreed. He asked if I would be interested in his cock, I explained that I had never been with a man, so I didn’t think so, but told him let’s just meet and see where it goes. We exchanged numbers after a bit of back and forth and set up a meet at my place the following day, on Saturday afternoon. While I was horny and hard, I decided to hold out for our meet up and went to bed excited by the possibilities of the next day.
That morning I hit the gym, got home, trimmed my pubes, as he mentioned he preferred smooth or tightly trimmed and took a long shower, every time I thought about what was going to happen my cock started twitching. He texted me around 10AM and said he’d be at my place in a half hour. I tidied up, made sure all the shades were down low, lit some candles, stripped naked and put on a robe. Right on time, he texted me that he had arrived, I told him to come to the door, it would be open. I peeked out the peep hole to watch his approach and make sure his pics matched reality, and thankfully they were. He was 42, 5’8″, dark skinned, weighing around 170lbs, I was 43, 5’9″, and 165lbs, with an average 6 inch cock and a nice bubble butt. He came in and after a brief moment of panic and awkwardness, I welcomed him in, he kicked off his sneakers, and we hugged, that seemed to break the ice. He seemed pleased by what he saw, as was I. He said, I see you are prepared as he untied my robe and reached for my cock, which was already at half mast. He gave it a few strokes and started kissing my chest, then moved up and started kissing my neck. This was already more than I had anticipated, then he asked if he could kiss me, I was flustered but nodded yes. The kissing was amazing, and I could already feel my cock leaking. As we passionately kissed, his hands moved to my ass, gripping both cheeks firmly and pushing me into him. After this makeout session, which seemed to last for hours, he completely removed my robe, leaving me completely nude, and asked if it was okay for him to get naked too, again I could hardly reply and nodded affirmingly. As he pulled off his shirt, I reached down, unbuttoned and unzipped his pants, grazing his cock with my hand, making him smile. He slipped his pants and underwear off in one motion, leaving only his ankle socks on. I couldn’t help but look down at his cock, which was also at half mast, revealing his nice shaft and perfectly pink head. His cock was slightly longer than mine, maybe 7 inches but had less girth than me. With both of us naked, he once again approached and leaned in to kiss me, he put his arms around me, I did the same. He eased his hands down my back, again grabbing my cheeks and pulling me into him. As we kissed, one hand continued massaging my ass, the other pulled my shaft to his and he started stroking them together. He mentioned how much I was leaking, and said I wonder if it tastes good, again I nodded yes. He then started moving down my body, kissing my chest and stomach on the way to my cock. I was lost, I didn’t know what to do with my hands, so I just placed them on his shoulders as he went down. His lips planted a kiss on my hardened head, then flicked his tongue on my piss hole, teasing it, before circling my entire head with his tongue. He did this repeatedly, I thought I was going to cum right then and there, but if I thought that felt good, I nearly lost it when he swallowed my entire shaft in his mouth and throat. He could clearly tell I was in overload, and mentioned it looked like it had been a long time since someone treated my cock right. He slowly repeated the process, circling my head with his tongue and then swallowing my shaft, with his tongue working the bottom of my cock as it was engulfed by his mouth and throat.
I told him I was going to cum, which made him stop, he said not yet, and let’s go to the bedroom. I took him by his hand and led him to my bedroom, my cock rock hard and glistening with saliva and precum. He laid me on the bed and positioned himself on top of me, maneuvering his way to position himself with his head over my cock and his cock dangling above my face. He then resumed his slow passionate assault on my cock, I finally broke down and decided I need to return the favor for all the pleasure he was giving me. I reached up and put my lips to his cock. It felt so strange, soft but hard, so an odd sensation, this made him work even harder on my cock, as I choked on his as he started gently thrusting into my mouth. With his cock in my mouth, I garbled that I was going to cum, he fully held my cock in his mouth and I started pulsing cum into it. He was clearly adept at this as he kept his mouth on my cock and swallowed every spurt and drop I produced. He then shifted away from my cock and re-aligned himself to kiss me. I was hesitant but before I knew if we were passionately kissing and sharing my cum between each other’s mouth. I had tasted my cum before and wasn’t overly fond of it, but this was amazing.
I felt bad that his cock was still hard and he hadn’t cum yet, so I offered to jerk him off, but he asked if he could grind it between my cheeks and cum on my ass. I was totally taken aback but agreed, he asked if I had any lube or lotion or oil, I grabbed the lotion I used to masturbate, and gave it to him. He had me lay on my chest, place a bunch of pillows under my hips for better positioning and started applying lotion to my ass, rubbing it in, and spreading it along my crack. He continued massaging my ass for a bit before adding some more lotion to my crack and sliding his finger up and down. To my surprise, as he glided his hand he tried inserting his thumb in my hole. I pulled back but he said he was only seeing if I would like it and I should try it, so I let him continue with this, he inserted his index finger and started sliding it in and out, to my surprise it actually felt good. He then switched to his thumb, which was shockingly different, but still felt good after a while. He kept his thumb in place and I could feel his cock now poking the base of my balls and sliding up to his entrenched thumb. He did this for a bit before removing his thumb, perfectly timed with the upward stroke of his cock. He tried to push the head of his cock into my hole, I immediately pulled away, this was not what I bargained for, but he begged, to just let him try, if it hurt too much he would stop. He kept at it, gliding up and down, replacing his thumb with his index and middle finger, this was a significant jump in pain, but he continued to reassure me, and ask me to relax. The pain subsided after a bit, and he more vigorously thrust his digits in and out of me, finally removing them and again pushing his head to my hole. This time he successfully got some of it in and rested in that position. I was now asking him to please stop, but his mood suddenly changed and just said no, telling me he was going to take me no matter what. He put the full force of his weight on me and forced his way in, the pain of the thickness at the base of cock buried in me was overwhelming. He started moving fast, thrusting in and out of me, he even started slapping my ass and telling me what a nice bitch I was and that he was going to enjoy breeding me, I was in pain and shock at how the situation had turned, and was only hoping it would be over soon. After about 15 minutes of him pumping me, I could feel his cock get even bigger, then he paused, and I felt his cock twitch inside me, I could feel the warm, wet feeling of his cum filling me up, I was disgusted and enthralled at the same time. When he finally started to soften he told me not to move, he ran off into the other room, grabbed his phone and place his now limp cock by my wet and battered hole and took a few pics, he told me to turn around so he could get me in the pic, he wanted to share. I was ashamed but complied.
He told me after that if I didn’t want the pic all over the internet I would have to service him and his partner whenever they wanted, I was their play thing now…