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My First Time Receiving Anal  

SubmissiveSon3 45M  
100 posts
8/30/2018 12:01 am
My First Time Receiving Anal


I can't forget my first time receiving anal sex, but then who can? Right? For years I have fantasized about it, and fucked myself with pens, bananas, almost anything that would fit in my ass, including a spray bottle of whip cream that when squirted, felt like a man's cum filling up my hole. But there is something special about having another guy's cum, their sperm, their DNA swimming around inside you. It makes you feel special, owned, possessed, you have actually shared a bit of each other, and though the sperm doesn't last long in your anus until it dries out, gets absorbed, or leaks out, for as long as I carried it around, I felt like the most important person on the planet. At least to the older man who just put a bit of himself into my body.

My first time was awesome. I was, like I am now, 39-years-old, but I look, feel and even sound younger, and I<b> shave </font></b>my chest, armpits, stomach, pubic area, bikini line, and dick and balls smooth, though mainly for comfort, if not for looks. I enjoy being the younger plaything, the sissy boy or to an older man, "older" in this case being 50 and up, and feeling his hairy, wrinkled body against my smooth boyish one. This older man, lets just call him "Ron," I met on Craigslist. In fact, I've met and hooked up with a few guys on Craigslist back when it had a personals section, like my other older fuck buddy, Jim. Now, thanks to some new law, it no longer has it.

We emailed and texted each other back and forth a few times, and finally decided to meet up. It would be at his house. His place was only a mile or so from mine, up the hill from Bankers Hill in Hillcrest of San Diego. I took Uber to it. It was about 10:00 pm, and the streets were dark and deserted. Good, I thought, I am not out as gay or bisexual so didn't want people to know why i was there. This was my first time in a long time hooking up with another man and my first time with Ron, and the first meeting is always a nervous one. He lived in a highrise, on the sixth floor of a 12 floor building. The building was secured, so outside the front doors I had to push a code into the intercom. Before I did, I hesitated for a long while, still nervous and worried, wondering if I should just turn around and go home. But I did want to be fucked so bad and I did promise Ron i would be there, so I was able to dig up some courage and enter the code.

"Hello?" An older man's voice asked, though it was slightly feminine with a lisp. "Hi, is this Ron?" I asked. "Chrissy?" "Yes," I answered. "Hold on,": he said. "I'll buzz you in. I'm on the sixth floor."

Again, thankfully, no one was around as I took the elevator up this relatively classy complex, thinking to myself This guy must have money, then walked down a long hall and around a corner to his condo door. Again, I was hesitant. But again, I was able to fight through my nervous feelings and knock on the door.


After answering, Ron opened it and standing there, slightly shorter than me, was a White man in his late 50s or early 60s with gray hair. We immediately embraced, something I prefer when I hook up with someone. I hate waiting, I hate talking, I just want to get right into it. Ron's condo was decorated with art and statues and other knick knacks he has gathered from around the world, and some antiques. He was a man who enjoyed the finer things in life, including champagne, and later explained he is a journalist and very active in the LGBT community. I am not. This isn't a lifestyle for me, this isn't all I am. I just like having fun, but on the downlow. Ron also explained he is all STD free like me and is on PrEp. I had no idea what that was yet.

I was still nervous, and wasn't good at keeping a conversation going. Suddenly, Ron came over to me, embraced me again, and started groping my entire body as he put his toingue down my throat. His breath smelled like champagne. His hands slid from my shoulders, down my back, to the small of my back, then all over my buttcheeks, before finally getting under my pants into my ass crack. I was doing the same to him, as I could feel his cock get hard against mine. He was so close to me, almost like glue, I have never had a guy want to cling so closely. I almost had to step back and thought I may fall over, he was so much all over and against me. "Lets go the bedroom," he suggested. I followed him down the all to the bedroom.

We continued making out, taking each other's clothes off while doing so, and groping each other everywhere. Ron was almost fine just having sex right there standing up, it was I who had to suggest we get into bed. I asked him to straddle me, like you would a woman, he got on top, his cock against mine, his hairy, wrinkled chest against my smooth, boyish one, like I always fantasized. Still with the kissing. Why do so many guys like tongue so much? I wanted to feel his lips, but he kept giving tongue. I moved my mouth around to kiss him not just on the mouth, but on is cheeks, neck, shoulders, and I started licking his ears. We were getting hot and sweaty, it got very natural and instinctive, the kissing, the groping, his cock rubbing up and down against mine. I was looking up at him, as a woman would to guy during missionary-style sex, but I am not fem. I am not feminine I am not T/TS/TV or anything, I don't dress up in women's clothes or put on makeup. I am all boy, I just like looking up at the older man dominating me and on top of me. It feels good to give up the control, to let someone else lead, do most of the work, to give up the pressure to perform, to be vulnerable, to be the submissive receiver.

As Ron was starting to gyrate and rub up and down on me, I tried to maneuver myself to where his cock would go behind my balls and slide into my butthole. "Want me to fuck you?" h said. I thought he would never ask! He got up and got a bottle of lube. Meanwhile, I rolled onto my stomach, my face getting buried in the pillow, my ass, naked and all up exposed like an animal in heat showing their ass to a potential mate. I saw Ron spread the lube all over his dick, then I felt his hand penetrate my hole, I mean he basically fucked me with his hand, making me gasp, as he spread the lube all over and inside of my ass crack. I think he used too much lube.

There I was, looking at a pillow, naked, with an older man about to put his penis into my still tight butt hole. My ass exposed and up. I was both scared and excited, anticipating what this would feel like for real! Ron got on me, after spreading my legs, his legs against mine, his chest against my back, his breath warming the back of my neck. Then I felt his dick slide into me, like an enema or those pens i used, but bigger and ironically though he was hard, it felt soft going in, maybe because of the lube. Once in, Ron started fucking me, in and out, up, up, up! I yelled out in pain, as he hit a spot that hurt. "I'm sorry," he said. "That's alright." From then on Ron found the right spot, he found how far he could go in without causing pain, and continued gyrating in and out, up and down. With so much lube. I had no idea if I was feeling his pre-cum or not. He was getting faster, breathing harder and harder, his hot, champagne-smelling breath on my neck, his sweat starting to drip on me, until finally I felt his body squirm and heard him yell out in ecstacy. I wanted to see the look on his face when he climaxed, maybe next time. Again, though, with so much lube, I had no idea what his cum felt like, though I knew it was now inside me.

Like a man that just ran a marathon, Ron fell on me, trying to catch his breath, his sweat flooding my back. He laid there for a while, almost passing out. I put out my left hand, and he grabbed it and squeeze it. I turned my head around as much as I could and we kissed again, again with lots of tongue. After another few minutes, I felt his cock slide out of me and he rolled off of me and on to his side. I got on my side and we were then looking at each other. He had a big smile on his face and said," I REALLY like you!"


Though i did have a lot of pre-cum, i didn't fully get off, so Ron, who explained earlier that hee doesn't give oral, he doesn't suck dick, was nice enough to give me a hand job. He started pulling on and stroking my dick until I finally came, until an eruption of cum blew everywhere. I think he pulled on it too hard though, because my dick hurt the rest of the night.

After we both cleaned up, Ron turned the lights off. We put our arms around each other and cuddled watching TV. Then he shut it off and we spooned until we both fell asleep.

I had a hard time sleeping in a new, albeit comfortable environment, so I got up real early and put my clothes back on. Ron was half awake and still smiling. "You have to go?" he asked. "Yes, I have a lot to do." He got up, still naked, put a robe on and headed to the kitchen to make some coffee. He also made me a bowl of cereal. We talked little more, and again, as I was sitting there eating, he came up, embraced me, and explored my mouth with his tongue.

It was so early there was no one else around still as i left. I didn't want to spend any more money on Uber, and it was downhill to my place not even a mile away, so i decided to walk back home. There I was, walking, my cock still smelling like cum, the back of my pants may have smelled, but no cum or anything else dirty was showing. When I got home I showered then laid on my bed going over what happened, so happy that I satisfied this older man and that it felt so good, me being fucked up the ass. I wanted his cum to stay inside me as long as possible, so even in the shower I didn't wash my ass very well.

I would meet up and get fucked by Ron a few more times, then we just sort of lost contact. That is a long story.

But that was my first time receiving anal sex, and I wasn't so nervous or scared about it after that, as long as the top, the guy fiucking me knows where to stop before it hurts. Like any guy, I enjoy receiving oral sex, and I need to get off, to climax even if it is through a hand job, but to me, anal sex is the goal of the hook up, what I hope our playing leads up to. Even if a guy just plays with my ass, squeezes and pinchse my buttcheks, spanks me, and fucks me with his finger. As long as my ass gets attention, it's all good.

I can never forget Ron. And I can never forget my first time receiving anal sex, when Ron fucked me. What about you? Your first time? And would you fuck me?

If you like what you read, please "like" this post, leave a comment, and look up my profile. I would love to get to know you!I am no longer a Gold Member, so to message me IM me, see and like and leave a comment on my other pixies, videos and blog posts where I can respond, and tip me, give me gifts, and friend request me! You might even like my other blog, just Google Search the terms "bimaleslutsd" or "bicurioussd," or search for "Adventures of a Bi Male Slut." i suggest searching Google images. Thanks! Love you! Kisses! {=} >>!
-{=}Chrissy, "SubmissiveSon3"








c0cksr1ng 61M
2960 posts
12/21/2018 5:24 am

I enjoyed staying with my gay uncle


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