The Prostate Massage

Craigslist: Prostate Massage.  GL 26, 5’9”/165 gym jock. Great music, excellent poppers and table full of toys. Worth it. South End.

What the fuck is a prostate massage? I mean, I love to get fingered and played with as much as the next guy, but a massage? I had to ask. After trading a few emails, I was intrigued. Hell, why not? I would love to have a guy spend an hour on my favorite ‘G’ spot. 

We set up a time to meet that same afternoon and I spent at least an hour prepping and getting squeaky clean for my “appointment.” I pulled up in front of his building in the South End right on time. My expectations were not that high; what does a 26 year-old really know about how to treat an ass? Still an hour of attention sounded exactly like what I needed.

I rang the bell and went up to his door; nice building. He answered the door in jeans and T-shirt. He was nice looking and friendly enough, but rather matter a fact about everything. He took me into his living room which had a sort of homemade draped area sectioned off as his “massage” area. 

Behind the drape was a massage table with a tray next to it with several different brands of poppers and a few dildos and lube, lots of lube. I thought, okay, this could get interesting.

He told me to get undressed and lay down on the massage table and he would be back in a moment. I took off my cloths and draped them over a chair. As I was undressing, I noticed my “massage therapist” pass through a few times and thought he was really cute and had a nice body. 

He took his shirt off, but left his jeans on. Nice smooth, defined chest. I laid face down and began to grind my cock into the table anticipating my massage.

He walked in and told me to roll over. When I do, he was squirting lube onto his hand and started opening my legs. The first thing he touched was my hole. I was surprised at first, then realized this was going to be all about ass. He slid a finger in and swirled it around and quickly added a second and then a third. He found my prostate immediately and rubbed all three fingers along it which caused me to moan out loud. 

He added more lube and said, “Ahhh yeah man, that’s it. Open up for me.”  He lifted my head up a bit and gave me a hit of poppers. He pulled his fingers out and slid a dildo slide into me. It was on the small side so it slid in easily; a nice warm-up. I focused on the buzz and the heat generating from my hole. It is so hot to have a guy working your ass while you’re lying back unable to see what’s going on. Sort of like being blind folded.

He started working the dildo in and out. The poppers were taking their full effect and I slid back down and exhaled and focused on the innermost part of my yearning, hungry ass. I was squirming in rhythm to his fucking and reached up and started pinching my nips. 

He pulled the dildo completely out and immediately, keeping rhythm, began alternating between the dildo and his three fingers. He stopped for a moment to add more lube and then slid four fingers into me and swirled them all around. “Yeah, I think you can handle a lot more than this little guy. Let’s see what else I’ve got here,” he teased.

With that I felt the cool tip to a much larger toy. I focused on the feeling as he put pressure on my hole. The head popped in. I gasped a little and then felt it slide right past my ring. I held my breath as the tip of the head went in me. Then he slowly pushed it all the way down to the base. 

This cock was big. As it slid in I could feel the lube gathering on the outer part of my hole and slowly drip down my ass crack.  I was feeling pretty full and tight. He lifted my head up again and helped administer my second hit of poppers, but these were different. This motherfucker was a connoisseur of poppers and knew what he was doing.  

This became evident because at this point I am flying; feeling flushed, nipples erect, balls tight, cock like titanium. My hole wants more so I push back on the big fucking dildo and exhale again, this time with a guttural moan. I start getting louder and he leans over and shoves the cock to its base again and grabs my left tit between his teeth and starts to bite down. 

I’m now on fire; squirming and moaning like a slut. All this and I have only been here for 10 minutes. This was fucking awesome.

He pounds the dildo into me all the way to the base again, but this time he holds it there. I’m stuffed.  I feel his finger circle the stretched out ring of my pucker; so fucking hot.  I feel pressure and then a pop. Again, I stopped breathing trying to figure out what had just happened. He had slid a finger in next to the fat cock. Damn, yeah! Oh hell, yeah. I am absolutely stuffed.

After several minutes of this, he pulls his finger out followed by the dildo giving my ass a much needed rest. I noticed his jeans were unzipped and could see his thick bush. Damn he’s a sexy guy. He reinserts three fingers in my ass and buries them all the way to the palm of his hand. He starts talking a little, telling me I have a hot ass and that it needs to be filled and often. I moan in agreement. His jeans are off now showing a seven inch very pretty cut cock; rock hard and dripping.

He lifts both my legs and slides the fat dildo back into me. He fucks me for a minute and pulls it out, lifts my head and feeds me more poppers. He then shoves his own rock-hard raw fat cock into me; all the way to his balls. “Oh yeah, man, fuck the shit out of me,” I begged. 

He started pounding hard and I held onto his shoulders in order to take the fucking like a pro. He pulled completely out, showing off his slimy, glistening cock to me and then shoved it back in. Pulls it all the way out, takes two steps back and then lunges forward and slams it all the way home again. He looked at me while pounding me, “Pussy needs some dick, huh?” I just moaned and concentrated on the fuck.

When he pulled his dripping cock out of my hole, he put four fingers back inside me. “I love the feel the inside of a freshly fuck butt. It is so warm and wet. Very hot, man. Can you feel this?” With that he started wiggling all four fingers in different directions. 

My eyes rolled to the back of my head. I just went to my happy place. He withdrew his fingers and replaced them with something very different. It was a strange feeling. I couldn’t tell what it was. My eyes were closed so I couldn’t see what he was using. I felt pressure and heard a pumping sound. The inside of my gut started to expand. I was getting full. Then I realized what it was. 

I was one of those inflatable dildos, which I had never used before. There was more fumbling around and I heard a hissing sound which was releasing the air from inside the dildo. The pressure inside the core of my ass was being relieved. Wow!

Now came yet another hit from a different bottle of poppers. I started to get really warm and flushed when I heard him say, “These I get from the Ukraine, they are un-fucking believable.” He started pumping up the dildo and I felt the girth grow exponentially. It must have doubled in size. Just when I thought I couldn’t handle it any more, he started pushing the dildo deep up inside me. I started squirming back down on it and started moaning and going crazy. 

The poppers were amazing. I wanted more. He was really getting into watching me take this huge fucking cock saying, “Yes baby swallow that huge fucking black cock, you whore. Is this what you came here for?”  This went on for a few minutes until, I uncontrollably started pushing the giant cock out of me letting out a deep animalistic guttural grown. The feeling was unimaginable.

I expelled it completely and he lifted the over-inflated swollen dildo up so I could see it. “Look what you took inside you, man. This is fucking huge.” I looked at the sleek slimy black cock and it made me shudder. I couldn’t believe that I took such a big cock in my ass. I started to really get excited because I knew this was a personal best. He deflated it a little; just enough to get it back inside me and pumped it back up.

“You can do it, stud. Hold that fat cock in there. Use your cunt muscles. Tighten it up. That’s it.” He pumped it some more. I was full and was straining to keep the fat black cock inside me. “Here, try the Ukraine poppers again.” I took a deep hit. “Come on stud. I really want to work your hole. Take another long hit and let’s bring this home.” 

I took another long hit from the other nostril. I heard and felt him pump the dildo up a little more. I was stunned for a moment and didn’t know what to do. On one hand I felt like I needed to shit this dildo out of me. On the other I wanted even more of it stuffed up my hungry hole.

My legs were spread as far apart as they could get. The poppers had me soaring and I felt him put a pair of tit-clamps on me. Then he started fucking the dildo in and out and was going faster and faster. I started moaning and groaning in a very guttural way. 

My head was reeling, my tits were on fire and my ass was working like a valve in a piston shaft. I was entering into a comatose state when he changed positions. He jumped up on the table straddling my face and helped me lift my ass off the table a bit. Without losing a single beat he continued to fuck that dildo all the way out and all the way back in again. It was making that nasty sloshing “fuck” sound that always gets me hot.

I opened my eyes from my stupor and saw his rock hard pretty cock, dripping a single strand of precum. I licked it and swallowed it to the balls. The sounds in the room were amazing. I was making this loud guttural moan and the squishy nasty wet fucking sound coming from my ass all the while I was choking and swallowing his cock to the balls. He reached back and tugged on my tit clamps and that’s when I lost it. I mean I totally lost it.

Cum started squirting out of me without anyone touching my cock. I didn’t feel an orgasm. I just saw cum shooting out of my cock. The first shot landed on my chest. Suddenly, he grabbed my cock and stuffed it into his mouth. That’s when I actually began to have my orgasm. I shot load after load uncontrollably into his mouth. 

As I was shooting, my ass was convulsing all around that fat black dildo and then my ass began to spasm and violently ejected the dildo out of my hole during a huge cum volley. It was like shooting a load of cum and taking the best shit of your life; all at the same time.

My “massage therapist” started groaning when he saw the dildo squirt out of my freshly fucked ass and started increasing the pace of his mouth fuck. I reached around and grabbed an ass cheek in each hand and pulled hard to stuff his cock even further down my throat. 

He let out a scream and started unloading. I slipped a finger into his tight pucker and he fucked back and forth even further. His cock was so deep in my throat that I could only count the pulses of his cock to determine that he shot 5 or 6 six powerful jets and deposited them directly in my throat.

We sucked each other dry and continued cleaning each other’s cock off. My heart rate started to slow down to normal and I regained my normal breathing. His cock slipped out of my mouth and he got up off the table. I looked over at the huge inflated dildo that had been buried inside me and was amazed. 

He read my mind, “Pretty awesome sight seeing you take all of that, man. You have a sweet ass.” I looked at my therapist’s pretty dick and up at him and said, “Incredible, stud.”

This 26 year-old knew exactly what he was doing. I slowly got cleaned up and dressed and paid my tab. As I left I had only one thing on my mind; I wanted my own fat black inflatable dildo and couldn’t wait to get one of my own.

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