My First Time Bottoming

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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, mecidiyeköy escort 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 taksim escort bayan him. “Oh shit, are you cumming?”

I could barely even speak. “Y-y-y-eah. C-c-cum-cumming h-hard.”

“Damn man! I’ve never seen anything like that! So fucking hot!”

He kept fucking me with his thumb while I rode out the tremors. Eventually the trembling subsided and I was able to breathe normally again. He pulled his thumb out and kept going with the massage as I relaxed into a spacey bliss.

“That was amazing. I’ve played with a lot of asses but I’ve never seen anybody respond like that.”

“Yeah, my prostate can get fired up pretty quickly.”

He chuckled, “I can see that.”

His hands felt wonderful as he worked his way up my back. At this point the massage was fairly traditional but as he got up to the head of the table, I opened my eyes for the first time since we began and looked at him. His crotch was right at my eye level. I didn’t realize it before, but he was naked except for a pair of very tight, very sheer white briefs.

His cock, which I could see clearly through the fabric, was erect and straining against the material. He was maybe a little smaller than average but his cock was absolutely gorgeous. It had the most amazing shape to it, with nice up-curve pointing back at his abdomen. And he was impossibly hard. His shaft and head were deep purple and visibly throbbing. I hadn’t even thought about how what he was doing to me had impacted him but it was quite obvious he was just as turned on as I was.

I asked him if I could touch him and he quickly said yes. I let my hand fall off the table and ran it up the inside of his thigh, gliding across his hamstring. I started cupping his balls from behind and below, and massaging my thumb against his crack. He was rubbing my shoulders as I was fondling him gently.

I never wanted anybody, man or woman, more than I wanted him in that moment. I desperately wanted, needed, his cock inside me. After a few moments, I just simply said, “Will you fuck me?”

“Yes. Flip over.”

As I turned over, he motioned for me to move down to the end of the table. He slipped off his underwear and his beautiful cock sprang free. He positioned himself at the foot of the table, and pulled me down so my ass was hanging off of it.

He told me to pull my knees back to my chest. I could tell he was just as horny to get inside me as I was to have him because he didn’t try to tease me or drag it out at all. He just lined up his head with my hole and drove himself in. I was still relaxed and slippery with oil from his earlier work so he slid balls deep in one stroke. I was officially getting fucked by a guy and I loved the way it felt.

He grabbed my thighs for leverage and started stroking into me. Because of his curve, his cock head was in the perfect position to drive me crazy. Up until that moment I never really understood how women could say sex was really good even if they didn’t achieve an orgasm. But suddenly it all made sense. Getting fucked is such an exquisite experience. To feel the pleasure of him sliding in and out past my sphincter, as he rubbed my special spot with every stroke. I just wanted to stay in that moment, to feel that feeling, forever.

After several minutes of slow steady fucking, he pulled out and told me to scoot back on the table a little bit. As I made room for him, he climbed up, sliding his knees under my thighs. He lined himself up and slid back in, then put his elbows behind my knees. At that point, he bent me back and opened me wide. I quickly realized he was done with gentle and sensuous.

He started fucking me hard and fast. I was well and truly getting railed, and his cock head was pounding my prostate into submission. This was a whole different level of sensation. It was almost overwhelming. My own dick was semi-hard, thick enough to be flopping around in rhythm to his thrusts. I was leaking precum like crazy and it was spraying everywhere. I reached up and started playing with my nipples, which he liked. He started to talk dirty to me, which really turned me on.

“So you like my cock in your ass?”

“Oh God yes! Please fuck me hard!”

I could feel another şişli escort prostate orgasm building and I told him so. “I’m going to cum again! Please don’t stop! Please keep fucking me!”

“Cum for me! Cum on my cock!”

And I did. My eyes rolled back in my head as I half-moaned/half screamed. Another prostate orgasm rolled through me as my asshole clenched tight around him. When I realized how hard I was squeezing his cock I tried to milk him with my ring to increase his sensation. His breathing started to get erratic and I realized he was getting close too. I hadn’t considered what would happen at that point but my lust made the decision for me.

“Oh God, please cum in me!”

“Are you sure?”

“Fuck yeah, cum in my ass!”

That’s all it took. I could feel him pulsing as he shot into me. Not only was I bottoming for the first time, but I taking another man’s load deep inside me.

He pumped in and out a few more times, then gently let my knees down and slumped forward a little bit. We both rested there for a second, then he got off the table. I could feel his semen inside of me and felt like such a good whore. After a minute, I got off the table as well.

We both cleaned up a little bit, then climbed back on the table to rest. We were cuddling together and just talking, which felt strangely natural to me. I don’t know why, but it just seemed like the right thing in the moment.

After a couple of minutes of just talking, he leaned over and kissed me. I’d never kissed a guy before and I didn’t think I would like it but again, in the moment, it felt right. We started making out and for the first time during the session, my cock started to get hard.

He took a hold of me and started stroking me gently. “That’s right, you haven’t cum yet.”

“I came twice, remember?”

“Yeah, but I mean a regular orgasm.” Then he said, “I’d really like to suck your cock.”

“Only if I can suck yours, too”

We rearranged ourselves into a 69 position and got busy. I was way taller than him so I was able to spread his ass apart and rim him, suck on his balls, and take his cock into my mouth, whatever I wanted. That curve of his went down my throat just perfectly so I was able to deepthroat him very comfortably. (Holy shit! As I type this, I’m just realizing that I went ass to mouth with him. What a fucking slut!)

I kept deepthroating him while I gently played with his asshole and pulled on his balls. In the meantime, he was aggressively sucking my cock. I pulled my my mouth off him and said “When you get close, just unload. Shoot in my mouth like you came in my ass.”

“I just came pretty hard. I don’t know if I’m going to be able to cum again.”

“I really wanna to taste you. Would it help if I played with your ass?”

“Uh huh.”

I started rimming him hard, really going deep with my tongue, and spitting on his ass until it got nice and lubed up, then I worked a finger in. I found his prostate pretty easily and started sucking his cock with purpose. In the meantime he was gagging on me and taking me as deep as he could.

I could tell he was gonna be able to nut again when his hips took over and he started fucking my mouth. We were on our side but I rolled onto my back a little bit so he could use his hips and drive into my throat. At the same time I was massaging his prostate and fingering his ass. I also knew that I was going to shoot soon.

I was trying so hard to hold off because I was afraid if I came first he would stop and I desperately wanted that second load. Soon enough, I could feel his prostate start to swell up and he moaned around my cock as he started to pulse into my mouth.

That was all it took for me and I thrust my hips forward, going as deep down his throat as I could, and started to shoot. We were both grunting and thrusting as we swallowed each other’s sperm at the same time. It was primal and erotic.

We laid there for a few more minutes and then got cleaned up. There was no long session of cuddling this time because we were both just exhausted. I knew if I didn’t leave soon I would have a tough time driving home. We gave each other a very genuine warm hug, he gave me a bottle of water, and I took off.

So that’s the story of my first experience as a bottom. I took a load in each hole, had two massive prostate orgasms, and broke my 6-week denial spell with an extra kinky flair.

I still love women and being with them, but in all honesty, that was the greatest sexual experience of my life.

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