Role-play with a NYC escort

The two studs that DP'd me earlier left me wanting more and after moving up to NYC I discovered that hiring a hot-as-fuck black escort with a huge cock who would bb my ass was easier than picking someone up off a regular site. Plus I could be really prescriptive with what I wanted, perfect!

One weekend, I came back from drinks at the recently re-opened Tavern on the Green where I had sat at the bar having too many glasses of wine. It was a hot summer night, I was alone and as I walked to the train, I decided that I needed some dominant daddy dick in me.

I cleaned up and surfed the available studs finding one young stud with "almost 9." I always take note if they say "always safe," leave it blank or put "sometimes." His was blank which meant that I could be barebacked into oblivion. I had only done this a few times, but I sensed that I wouldn't even have to ask for raw dick in me when he wasn't insistent on rubbers.

I should mention that my parameters for searching aren't exactly rocket science. I usually restrict the age from 25-30. Don't really like guys too much taller than my 5'9" and inevitably, I am going to select "at least 8.5" and cut." The rest as they say is negotiable.

I sent the intro text and he responded in seconds, even calling me right after. We chatted a little about what I was looking for and he was agreeable.

"BFE (boy friend experience)," I said, "lots of kissing, him in a jock strap, poppers, bb and loads of jizz for me." He told me he was on prep so bb was cool.

He didn't disappoint.

He arrived almost to the second as agreed which I appreciated, and upon arrival, he was exactly as his pics portrayed. 25, muscular, 5'11", cute smile, gorgeous, almost Tyson Beckford eyes and as I would soon learn, a sexy creative pig.

We kissed and made out, hands groping each other. I was in tight jeans wearing a jock and he was wearing what I would call almost leather pants. Sounds vile here but they were really well fitted and showed off his gorgeous ass and big package very nicely. He complimented this with a black tight t-shirt and carried a little bag of his tricks (lube, fresh poppers and other stuff which we never used). I think he was a bit into harder drugs, but despite being a slutty pig, I limit myself to poppers, wine, gin and weed.

So we kissed, and he was a great and passionate kisser. He popped the top button of my jeans open which gave him enough room to put his hands down the back and grab onto my round ass. We were mashing our mouths together, my hands running across these leather pants, and his hands gripping onto my cheeks. Occasionally, he'd move a hand to my crack and tenderly stroke my hole.

He let go of the embrace, reached down to his bag and pulled out what would turn out to be some of the strongest poppers I have ever snorted. He handed them to me, I took a couple huge hits and then dropped to my knees starting to rub my mouth into his crotch. His cock was bent over to one side and arched around his thigh. I slowly worked him over but there was no need to get him hard because I could tell that he was horny as fuck.

I undid his tight leather jeans and tugged them down revealing a hot jock strap with shoelace ties in the front. I was enjoying the sensation of licking his dick through the fabric so I was in no rush to unleash his cock and noticed that at the end of his cock, a spot of moisture from his precum was gathering.

He tasted so good, and while he wasn't verbal or aggressive, I could clearly tell he was enjoying the attention I was paying to his bone.

Almost teasingly, I undid the strings on the jock and tugged it down. The vision of his shaft running across his belly and thigh was porno-worthy. A thick meaty and veiny dick waited my mouth and I slowly ran my tongue across it, half of it was still shrouded in the jock.

By now he had pulled his t shirt off and his bod was amazing. As I got ready to suck dick, ran my hands up over his chest and tweaked a nipple only to discover that this stud would love his nipples pinched.

I took another hit of his poppers and let his cock bob out. It swung around into my face and as the rush of poppers took over my senses, I swallowed his dick and like a good pig went to pleasing this hot man.

He indulged me for a good ten minutes and moaned and groaned as I gagged on his cock. Spit was dripping from my chin and I became aware that my dick was achingly hard, still stuck inside jeans that were too tight.

I stood up for breath and he didn't leave me to suffer for very long. Within seconds, I was standing before this sexy man in my jock with his fingers running along my crack. It doesn't make sense biologically, but my ass was moist in excitement and I could tell that this stud was ready to fuck.

We went to the bedroom which had views of the Empire State and Chrysler buildings on the other side of east river. When he saw the 180d view from the bedroom he joked that he could wake up here after a night of fucking me.

On this first night, he nailed me hard and his favorite position was to have me on all fours but with my knees together and my head down on the bed. Arms spread out like an angel in front of me, and in that position, he would pull my curved dick back between my legs and stroke it while he fucked me. This position turned this fucker on and when he popped through the top of my ass he let out a little "that's it baby, can't get any deeper now."

He moved me around that night, fucked me in the living room on the ottoman admiring the view of Manhattan from the floor-to-ceiling windows and finished me off on the floor; me on all fours at the end of the bed. He pumped deep into my guts and grunted a huge load of his nutt inside.

He pulled out and muttered, "that was a big load for your greedy little hole, now push it out for me."

I obliged and staying in my position on the floor, I arched my ass up higher and pushed his load out of my ass. He swiped the cum as it dripped out of me and put a finger full into my mouth. I eagerly cleaned every drop.

We chatted a bit after this, laying on the bed, he cleaned up and got ready to leave. I remember standing at the door smiling like a little school girl as he kissed me goodbye with cum still dripping from my ass as he walked down the corridor to the elevators.

That was the first time we connected and the next time, maybe a few weeks later, I asked if he had any fantasies.

"You're the sort who probably has great suits and I bet you like wearing them don't you?"

He clearly had me pegged (I've said before, I am a bit of a geek with a hidden pig) and I agreed to be in a suit and tie for him. He also wanted me to be drinking whisky or something similar when he came in.

I expected him to be in the same but when I asked what he would be wearing, he said "gym shorts and workout gear, like I've just come from practice."

"Ok" I thought, that seems weird, but whatever, I'm a good boy, I do what I am told.

He arrived at the arranged time later that evening (punctual again), and I had some Johnny Walker on the go. Like he wanted, I was in a nice tight fitted navy suit under which I wore a jock straps. I even put on dress shoes for him and opened the door not knowing what to expect.

He walked into the foyer of my condo looking exactly like he said, like he had just been playing soccer with his mates and I had no idea what to expect.

Then he started in on this little role play.

"Look man, you're my agent," he said, "you gotta get me on this team, I work my ass off, I'm better than anyone else, and you know it, what do I have to do to get this?"

He had the cutest damn smile on his face as he did this and as far as I knew, totally unscripted. I played along and said that there was a lot of competition and if he wanted this, he was going have to prove me to that he was special.

I had by this time sat down, and he got up, grabbed the glass from my hand and planted a passionate kiss on my lips. He was almost whimpering and muttering, "I'll do whatever you want, even take your cum in my ass."

Ok, as you've read in my other stories, I am a big old bottom, but this boy was fine and I got very turned on thinking that I was gonna get some dick and dump a load in his hot ass.

So we started to undress each other and he was as gorgeous as before. I think he actually must have been training or something because he tasted salty and had a musty smell to him which I didn't mind one bit.

In no time at all we were both standing there in jock straps, my crisp suit crumpled in a heap on the floor and after moving to the bedroom he continued on with his little role playing, begging me to get him on this "team."

He fucked me like he had before, mainly from behind and after an hour or more, excused himself to the bathroom. I could tell that he was cleaning up, leaving me on the bed, stroking my dick.

When he came out a few minutes later, totally naked, I was actually nervous. I started out being a total top. Bottoms loved the downward curve of my dick, and as I've said in other stories, I'm by no means a small boy but after discovering my first black dick at 25, I had only topped a bottom on a handful of occasions. Now this gorgeous man who had been fucking me raw wanted my cock.

He slathered my cock with lube holding on tightly as he climbed on top of me.

He slowly impaled himself on my dick facing me, with that same sly smile on his face.

"Dam, that curve fucking digs in deep man," he said and asked me to hand him the poppers.

He took a big hit, I took a big hit and then while he held onto my head, he kissed me and took my 8" as I pinched his nipples. This drove him wild and he worked my cock into his guts.

His ass felt amazing on my raw dick. Smooth and silky, and he was down to my nuts grinding and moaning as the poppers rushed to his head.

His big beautiful dick stayed rock hard and bounced up and down hitting my belly as he rode my dick raw. Clearly this stud had been fucked before and he loved it.

"I told you, I want on this team, and my gf don't need to know that you fucked me," he said.

I moved him around the bedroom and finished fucking him with his feet spread wide apart and his hands up against the wall of the bedroom. Because my cock curves down, I dug deep and he would cry out in a bit of pain only to beg for more, or at times, he'd even grab my thighs and pull me back inside. He was moaning and groaning, still in his role and I played along fucking him raw, promising him that he'd make the team.

When I finally came up his ass, it was a nice load and I remembered him feeding me his cum the last time, so I told him to stay where he was, if he wanted this gig, he better push that nutt out so I can taste myself.

He swayed his hips side to side a little and then stopped. You could see he was pushing his guts out and then my load started to ooze.

I have never minded tasting my own jizz so I bent over and licked up as much as I could which turned out to taste wonderful. With a mouth full of my cum, mixed with his ass juice, I gently pulled him up, turned him around and wrapped my arms around him. I kissed him passing my cum into his mouth and back and forth. He greedily ate as much as he could and any that spilled out onto my face, he licked it clean and said "does this mean I get on the team?"

I had just blown a load but he was still hard so I took advantage of the moment and said that if he wanted on the team, he'd have to fuck me full of his jock babies.

"your gf's cunt isn't as nice as mine is it now?" I said teasing him.

I doubt I had to even ask because within another 30 minutes, his cum was buried deep in my hole and we were laying on the bed.

"Dam, it must suck to wake up seeing the Chrysler building like that dude," he said before dozing off in each other's arms.

He didn't stay the whole night but one thing was for sure, this stud was by no means a clock watcher. We played again a few times and he would always stay for 3 hours instead of one as arranged. I got to learn more about him, and I loved how he was into my ass. He was a struggling grad student, articulate, smart and genuinely a nice guy. I found myself falling for him and one night we even spent 4 hours just talking on the phone.

In retro, it was a mistake to do so, but I asked him out for a drink one night and suggested he meet me at the Tavern on the Green. I made sure my hole was extra sweet and clean for him, bought a new shirt, new poppers and lube, got to the bar and sadly, he never showed.

I got stinking drunk at the bar on gin martinis reminding myself that his and my relationship was a commercial one, and nothing else but couldn't help but smile knowing that he fucked like a machine and broke almost a decade of me being a complete bottom.