This is the true story of my first time.
I'm a bisexual guy in my 50s. I've known since my early 20s I was interested in sex with men, but I didn't really start acting on that realization until about 6-8 years ago. I've always wanted to experience getting fucked but never had the opportunity. However, in that time I've discovered I really like sucking cock and have done so on numerous occasions. I love making other guys cum and I always swallow.
I've also developed a real fondness for prostate and anal play. Over the last several years, that has led me to completely rewire my sexual responses. I can have many different types of orgasms, not just the standard cum--shooting-out-of-my-cock ejaculatory type. They feel very different but they're extremely intense. My whole body will shake while a wave of extreme pleasure washes over me. In a lot of ways, they're like some kind of crazy edging because even though they're definitely orgasmic, they don't trigger that refractory period or any kind of postnut clarity. They're really a giant tease because as good as they feel, all they do is ramp up my horniness and desire. Total body anal/prostate orgasms without ejaculation are the ultimate sexual appetizer that leave me hungry for more. Not only can I have these kind of orgasms from anal or prostate play, nipple play can also trigger them. Sometimes, if I'm really horny and high as fuck, I can have these types of orgasms with no external stimulation. On several occasions I've even cum this way from giving head. If I'm in the right mood, as soon as the guy starts to fill my mouth, a total body wave rips through me.
Last December I decided it was time to get a Brazilian wax again. I like to do it occasionally for hygienic reasons and it's also very sensual. (I was also horny as fuck. Because of No Nut November it had been almost 6 weeks since my last orgasm and I desperately needed to be touched.)
I heard about a guy who had a good reputation as a waxer. His prices were decent so I made an appointment for a Sunday evening. I got over to his place around 6:00 and we got to work. He started me off by waxing my ass crack first. Instead of having lay me on my back and pull my knees up to my chest like a lot of waxers do, he had me get up on the table on all fours. I had never been in that position in front of another guy before. My cock and balls were hanging down between my legs and my ass cheeks were spread wide open. Once I was situated up there, he told me to drop down onto my elbows, which opened me up even more. I felt very vulnerable and more than little aroused at the same time.
After he got to work, I could definitely tell the advantage of this position compared to other waxers. It was much quicker and easier for him to finish the job that way. When he was all done, he put some oil on a cloth to help wipe away the little bits of stuck-on wax. As he rubbed the oil over my asshole and down to my taint, I couldn't help but let out a little grunt. He asked if I was okay and I figured I would throw out a little signal just to see what would happen. I said "Everything is fine, I'm just kind of, um, sensitive back there." He chuckled a little bit and said "I completely understand."
After he was done with my crack, he had me flip over into the standard frog position and he finished my balls and my shaft. He was super professional and efficient, and the session was actually pretty relaxing. We were having a nice conversation and immediately got very comfortable with each other. During the session, he mentioned he also did massage. Between my need for touch, and the intimacy of the session, a massage sounded like an amazing idea so I asked if he had time that night to give me one.
He said, "I'd love to but unfortunately, I've got another appointment coming at 7:00. Truthfully though, the guy's kind of a flake and he's canceled on me without warning a couple of times, so, maybe?"
By this point we were wrapping up so I said "Well, how about if I hang out in the area for a few minutes and give you a call about 7:15. If you don't answer, I'll know you're in session and we can set something up for another time. But if he does flake on you, I'll still be around and I can swing back by. How does that sound?"
"Great idea. Honestly, I kind of hope he no-shows on me again because he's kind of a jerk and it would give me a reason to cut him off permanently."
We said our goodbyes and I took off to grab a soda and withdraw some extra cash, just in case.
I was so excited, I only waited about 10 minutes to call him back. Sure enough, the guy hadn't showed up and he invited me back over. My hands were trembling as I started my car because I just had a feeling something interesting was going to happen.
When I pulled up in front of his house again, he was waiting in the doorway for me. I could tell he was just as interested in the massage as I was. We went back into the room, I stripped, and laid on face down on the table. I made sure I positioned myself with my legs spread a little wide. I also made sure my cock and balls were pulled down between my legs instead of tucked up under me.
He started the massage at my feet, which wasn't traditional, but it felt really nice. It didn't take me long to realize why he started there, though. He started working both hands up the inside of my legs, from my ankles up to my calves, then on to my thighs. He wasn't in a rush, but he also wasn't wasting any time moving up.
Before I knew, it he was running his thumbs along that crease where my glutes and hamstrings join together. It felt amazing and I realized I was arching my back and lifting my hips ever so slightly with each stroke.
Soon he was working on my glutes and running his thumbs up the inside of my ass crack. When he got to the top of my crack, he would flare his hands out along the small of my back, bring them down the outside of my hips to my hamstrings, then start back up again. With each repetition, he would press his thumbs in just at the base of my scrotum, then slide up until he was grabbing my ass. He was spreading my cheeks farther and farther apart as he slipped his thumbs deeper into my crack. His thumbs would come within millimeters of brushing across my hole but he didn't touch me there at all. He would pause every few strokes to add a little bit more oil to his hands.
He did this for an insanely long time, teasing me until I gave up any pretense of trying to be cool and chill. Started whimpering and moaning audibly. I was literally trembling with arousal. Without thinking, I blurted out "That feels so so good!" He laughed that knowing little laugh again and said "Your ass really is sensitive, huh?
I was so turned on by then that I started babbling like an absolute fool, "Just so you know, I haven't had an orgasm since the end of October, I've been edging like a fiend lately, and you can do whatever you want to me."
He chuckled again and as he started his next pass up my crack, he said "Oh really? So you'd be okay if I did something like this?" and pushed one of his thumbs against my asshole. I immediately opened up and he slid in with absolutely no resistance. I let out a guttural moan as he plunged into me.
He started working his thumb in and out of me, opening me up. I honestly didn't even recognize the noise I was making at that point. It was somewhere between a whimper and a moan. I just kept mumbling "Please please" over and over as I started rocking my hips up to meet his probing.
After about a minute of this treatment, he angled his hand forward so his thumb went deep inside of me and lodged up against my swollen prostate. He took his other hand and put it on the small of my back, pushing my hips down on to the table and pinning them there. As he started to massage my P-spot with his thumb, he curled his fingers up hard into my perineum. He began rocking his hand back and forth, sliding in and out of me as he rubbed the base of my cock from the outside. I tried to buck and grind against his hand, but he kept me pinned to the table. It was obvious he was running the show and that turned me on even more.
It didn't take long for me to explode into a thunderous prostate orgasm. It built from the center of my core then roared out through my entire body. I started shaking and flopping against the table like I was possessed. My asshole clenched down hard on his thumb, which surprised him. "Oh shit, are you cumming?"
