The Escort

by rustyfella

11 Sep 2021 3504 readers Score 9.4 (69 votes) PDF Mobi ePub Txt


One of my fantasies is to rent myself an escort. Should be easy enough, right? Not in my town! For all that it's a moderately big city, hustlers aren't all that common. There is a bar where they are known to pick up older guys. I checked it out. The boys available just weren't to my taste. Then there was the problem that the bar clientele, thought I was one of the boys looking to sell. Too young to be looking to buy I guess.

I even tried online. But once again, the available prospects just didn't appeal to me.

So, this fantasy went unresolved.

Then, for my thirty fifth birthday, I decided to make it happen. After all, Chicago wasn't all that far away. I'd checked the online sites for Chicago's talent and there were a few that were my type. I was looking for a man, not a twink. Unfortunately, most of the "men" were tops. I wanted to fuck some ass, not be fucked. Then one caught my eye. Axel. Younger than I wanted, yet he had a stocky man's body. Not pretty, more rugged features. A lop sided smile. In his online pics he had a nice amount of dark body hair. And perfect for me, A big round bubble butt. To really perk up my interest. The magical word. Versatile!

So, I contacted him through email. He was available for the dates I had in mind. I explained that it was my birthday weekend, and I wanted him for more than a quick fuck. He was surprised that I wanted him for several hours. I explained that I was looking for a companion to accompany me for the evening. I also let him know that at some point I would want to fuck him. Best to have that all up front to avoid misunderstanding. He was agreeable, and I booked him for ten hours.

Needless to say, his services for the night was a hefty sum. I used a gift card to put down a deposit. I wasn't going to chance using one of my credit cards. Plus using a gift card allows me to remain anonymous.

Once the main event of the trip was taken care of, I got down to making reservations. Splurged on a moderately expensive hotel room. Bought tickets to a play I wanted to see. I decided to take the train to Chicago. I didn't want to deal with driving and trying to find parking spots. Taxis or Uber was just a phone call away, after all.

Wow! I know it sounds like a whole lot of to-do. Here is where I admit I love to be in control. Not in a every thing has to be perfect way, but not so far off. I guess that's why a paid escort seems so perfect to me. I get to call the shots. And there's little chance of rejection.

Anticipation began to grow. It was always in the back of my mind. Then I was boarding the train for Chicago. I spent a few hours in the observation car enjoying the country views. When I disembarked, I was lucky enough to find a cab right away. My hotel room was all that I could want. I went out and explored the nearby shops and restaurants. Finding a restaurant that served good smelling Italian food, I made a reservation for dinner.

As Axel's arrival loomed near, I showered, trimmed my beard and got dressed. I had asked Axel to dress for a casual night on the town. I did the same.

Right on time there came a knock on the door. When I opened the door, I was really pleased. I'd heard sometimes the escorts doctor their photos to look better than reality. Axel looked better in real life.

I saw Axel's eyes go wide when I opened the door. Of course he had no idea what I looked like. He was likely expecting some old troll, who had to pay to get laid. Not a physically fit, thirty five year old, with dark red hair and a beard. While I'm not classically handsome, I'm not hard to look at either.

I invited him in and as he walked by, I checked out his ass. Yum! All nice ,round and firm looking.

As he turned about I continued my appraisal. Maybe five eight in height. Short dark hair. Squarish face. Heavy beard line. Snub nose. Brown eyes. Round ears that stuck out a bit. Lop sided grin. Thick neck. broad shoulders. Barrel chest. Stocky waist. Definite mound at his crotch. Sturdy legs. All in all, a seriously manly looking man. Maybe younger than I usually go for, but very acceptable.

He took a few minutes to go over the details of our deal. Since everything was in order and my reservation was coming due, I escorted him out. At the restaurant, I pulled out his chair for him. I wanted to exert that I was in control of the evening's festivity. As I was seating him I managed to catch a whiff of light cologne over his natural scent.

We ordered, ate and made small talk. Just like on a first date. Nothing too personal.

After eating I bundled us into a cab and headed to the theater. Axel was a bit surprised. I guess he was expecting a sort of slam bang ,thank you ,man, kind of night. ( Hey, I'm long lasting in the sack, but even I can't manage ten hours of sex!).

He certainly didn't expect dinner and going to one of the hottest new shows of the season. I thoroughly enjoyed the show and the presence of the hot young man next to me. He made no objection when I looped my arm over his shoulders. In fact he leaned into me. The hard warmth of his body, caused my dick to half inflate. When he dropped his hand on my thigh, my pants got pleasantly tight.

So, all plans seem to find a bump.

At intermission, as we stretched our legs, a rather flamboyant older man came bustling up to Axel. Apparently, he was one of Axel's regulars and had been quite pissed to find Axel unavailable. He tried to convince Axel to dump me and attend to him. He even threatened to remove his "patronage". The little pissant even appealed to me, thinking I was a date. He informed me that Axel was a common whore and not worth my time. Then eying me up and down, he suggested he'd be willing to pay for a three way.

The look of disgust on my face, must have been very evident. Because at that point he began to accuse me of being an uppity whore as well.

As he was quite voluble, heads were turning our way. People began to edge away from us, some with distaste on their faces.I could see a security guard making his way towards us.

At that point I'd had quite enough. I got up into his face and quietly, yet firmly told him he'd best remove himself from my presence. He went white, then red and began to bluster.

It was as he blustered and threatened, that the security guard came up to us. He saw me and Axel looking embarrassed, and a flamboyant man having hysteronics. When he suggested that Sir Flamboyant return to his seat and cease causing an uproar.

That sent the idiot over the edge.

He began to shriek and call curses down on the Guard's head. Diplomacy having failed the guard ordered him to leave. He claimed I threatened him. A lady standing nearby, who had heard everything, came to our rescue. She stated we had been minding our own business, when Sir Flamboyant had accosted us. She went further to say, the only thing she heard me say, was a perfectly reasonable request for him to remove himself.

I don't know who she was, but apparently the guard did. Apparently she had some clout at the theater. And the little pissant made the mistake of calling her a vulgar name. Just as someone who appeared to be management arrived with another guard.

He was at that point, unceremoniously and a bit roughly, expelled from the building.

I could tell the manager was about to ask us to leave as well, when the lady touched his arm. She shook her head and gallantly came to our defense. Adroitly, she left out any mention of the man's accusations of Axel's line of work. Made it sound like an ex lover causing a scene.

We returned to our seats, but the easy comradery had fled. Axel's was tense and extremely quiet. I feared he would call the evening off. Finally, I suggested we go find someplace to talk.

Luckily there was a bar just down the street. We got drinks and slid into an empty booth.

Axel's apologized for ruining the evening. I assured him that I didn't hold him at fault. He sighed, rubbing his eyes. Turns out Sir Flamboyant was his best client. I shared my opinion that perhaps this was a silver lining. Sir Flamboyant seemed a bit too possessive. That attitude would likely cause Axel trouble down the line. I also told him if he was that desperate to retain him as a client to contact him if he could. I would pay him for the time we had spent.

To my relief, Axel declined. A deal was a deal. Plus, it did no harm that I was treating him like a human being and not just a warm body to get off with. Sir Flamboyant could go sit on a church steeple and spin.

I suggested we call it and head back to my hotel.

Once back in my room, Axel began to act awkward. Hell , he was supposed to be a pro, yet he acted like an escort virgin. I raised my brows a bit, shrugged and went to my suitcase. Pulled out my pipe, my stash, a bottle of poppers, a condom and a bottle of lube. I deliberately, set the condom, poppers and lube on the bedside table.

Then I sat on the end of the bed and I lit my pipe and took a long drag. I held the pipe out to Axel. I was pleased when he took the pipe and hit it. When I'm in company, I prefer not to get high alone.

We passed the pipe back and forth a few times. I waited until I could tell he was feeling the hits.

I stood up and went to stand behind him. He didn't flinch, as I molded my front to his back. I reached around him to caress his body through his shirt. He leaned back into me.

Pushing my hard dick into his firm backside, I slipped my hands down the front of his pants, keeping them outside of his underwear. I fondled his hard on through the cotton fabric. His hands snaked around my hips to pull me hard against his ass. I nuzzled his neck, causing him to softly moan.

I slipped my hands back from inside his jeans, grabbing the hem of his shirt. I pulled it off and tossed it on a chair. My hands found their way back to his hairy torso. I explored his upper body by touch, stroking each ridge and muscle. His large nipples. His breath sped up in that big chest.

Soon my hands were opening the buttons of his jeans. Unzipping. I pushed those jeans down. I knelt down behind him, side of my face against his cotton clad round butt, as I eased his shoes from his feet. Then off came the jeans.

I ran my palms up his thick hairy legs and back down. Slowly stroking, feeling the soft dark hair on my skin. Each pass was farther up his thighs, until I was stroking against the full mound in his briefs.

What I was doing must have worked for Axel. I could feel wetness where his hard cock stretched the cotton pouch it was trapped in. I lazily continued stroking his cock, my cheek still pressed against his brief covered mounds. Then my nose was nuzzling between his cheeks, inhaling clean cotton and a whiff of man sweat.

His stubby fingers caught my hands, stilling them. Between the weed and the pleasure of touching his body, I'd gotten lost in the moment. I realized, I'd almost stroked him to completion.

He took over for a moment or two, guiding my hands to the waistband of his briefs. I sat back as I hooked fingers into the elastic and began easing the fabric down . Slowly, his round bubble butt was revealed. My eyes drank in the pale skin and the soft black hair growing from that skin. Thickest at the crack, it created a beautiful dark line.

As he stepped out of the briefs, his ass flexed in front of my hungry eyes. Legs spread apart, I could see the back of his fat round ball sack. I just sat back a short while, my eyes drinking in his heavy round ass, dick throbbing in my jeans.

I'm a total ass man. To me nothing is sexier than a big round butt. So much so, that I just as happy fucking homely faced men, just because they had beautiful asses.

Axel's ass was just about my idea of perfection. The added feeling that it was bought and paid for, was almost too much for me. It gave me such a heady feeling of being in control.

I reached out and gently cupped those hairy mounds. Hefted their weight. Stroked them.

Finally, I spread them.

There nestled in a nest of dense hair was a tiny pink pucker. It clenched as cooler air touched it, the tiny slit winking.

I loosed one hand to gently touch it. Axel's body gave a tiny jerk. His broad hands came back to help spread his cheeks. Gently I stroked over his little hole. I delved just the tip of a finger into it, feeling it pulse.

My face had drifted closer in fascination. I could smell clean man sweat and a whiff of soap. I licked the bottom of one hairy cheek. Then the bottom of the other. The hair so soft on my fingers, felt rougher on my tongue. I licked up the valley between his mounds. Axel let out a deep moan as my tongue slid over his pulsing slit. He pulled his cheeks further apart to give me more access.

I grabbed his sturdy thighs to steady him. Then began licking his little hole in earnest. His legs quivered in my grip. His ass was thrust against my face, inviting me to plunder his hole.

My cock began throbbing so hard, I was afraid I would come in my pants. Part of me wouldn't care if I did. Yet the greediest part of me wanted to be buried deep inside him.

I stood up behind him and gave him a gentle shove towards the bed. He turned to face me and sat down. I eyed his hard drooling cock, pleased that my attentions aroused him.

I knelt to remove my shoes. Without ceremony, I stripped out of my clothing.

Axel's eyes widened. I've had my cock likened to a pop can. While only about seven inches long, it's pretty fat. Okay, very fat. A definite hole stretcher. I actually saw Axel swallow hard at the sight. He knew I expected his hole to accommodate that fat club.

Yet, his cock didn't soften and continued to bead precum.

I made a bit of a show, going to the nightstand , dick bobbing, and grabbing the condom and lube. I ripped the foil open and pulled the rubber out. I uncapped the lube and coated my dick. I need the slick to get a condom on. Pulling back my foreskin, I slid the rubber on. Then lubed the condom.

I tossed the poppers down next to Axel in case he wanted them. I went to stand between his spread legs. Axel obliged me by laying back, grabbing his legs, tilting his hips up. I leaned across him to grab a pillow. I forced it under his hips, so he wouldn't have to hold his hips at that angle.

Axel sighed when I rubbed my cock against his pucker. Either he was a good actor, or he was excited as I was. Honestly, it didn't really matter. This was all about my pleasure. If he got pleasure from this, well and good. Nice side bonus. If he didn't, well he was being well compensated.

I ran a finger over his hole judging if my spit had dried. Deciding more lube was needed, I slicked up my fingers and probed him. He was so tight, I wondered if he actually bottomed very much.

He was hot and wet inside. The feel of his asslips clenching my fingers felt wonderful. The thought of stretching him with my dick made it feel incredibly hard.

I was done playing around. I wanted inside him. I grabbed my cock and nestled it at his slit. I gently pushed, my dick tip, separating his tight pucker. The little wrinkles began to disappear as his hole stretched. Axel was biting his lower lip.

When the head popped through, I paused. I like to savor that first breach. Feel the muscles of a man's pucker pulse around the back of my cockhead. While I enjoy the feeling, it has the added benefit of allowing my sex partner to adjust to the girth invading their ass.

Either Axel liked being stretched or he was adept at pretending to enjoy it. He arched his back to slide more of me in. I could tell when my fat cock slid over his prostate. He gasped and his eyes rolled up.

Slowly, I slid inside him, relishing the heat of his body on my dick. When my balls were pressed against his tail bone, I held myself still. Axel's hands were grasping his thighs, holding his legs up and wide. Giving me as deep an access as he could manage.

After a moment of indulgence, I began slowly long dicking him. Pulling most of the way out, just to slowly sink back in. Axel met my inward thrusts, angling his ass to take me deep. He moaned and told me how big my cock felt. Might have been an act. I didn't care. If he was acting to make me feel good, great. If he was actually enjoying being fucked? Even better.

For the next couple of hours, he was pretty much mine to enjoy. Selfish? Could be. Did it matter? Not really!

At any rate, Axel was saying all the right things, making all the right sounds and moves to make me happy. As I picked up speed he urged me to fuck him hard. His cock stayed hard and precum dribbled out in spurts when I drove into him. It was this that led me to believe it wasn't all an act.

Usually, I am a long winded fucker. I've been urged to hurry up and cum by more than one trick. I guess, renting Axel's ass was a bigger turn on then usual. It seemed like no time before I was slamming into him, feeling my cum ready to boil out inside him.

Then Axel moaned that he was going to cum. His whole body tightened as he convulsed. His cock began to jerk and white sports of cum spurred from his dick slit.

I continued pumping into him each thrust sending another spurt from his dick. Then I grabbed his hips and buried myself inside him as far as I could. I held his ass tight against me as I emptied my balls inside him.

When my shudders subsided, I slowly pulled from his body. His well pounded hole let me slip out easily.

As I withdrew, I leaned over his sweaty body and began to lick his cum off. I cleaned his cock, his belly and broad chest clean.

Then I knelt on the bed, draping his thighs over mine and watched as his breathing evened , the hair and his skin wet from sweat, and spit from my licking.

Axel made as to get up. I grabbed his thighs and held him in place. A meaningful look at the clock was to let him know he was still on the clock.

He rolled his eyes then grinned.

As I knelt there, Axel's burly body splayed before me, I got the urge to shower with him. Damned if the idea of lathering every inch of his body didn't send a pulse of heat to my spent dick.

Axel smiled when I suggested we take a shower together. "Don't like my cum drenched man smell?" He chuckled. I just rolled my eyes. " Yes, actually I do. But the idea of soaping you up and sliding my hands all over you trumps that!"

Axel's eyes widened and his softened cock gave a twitch. I could tell the idea had edit in his eyes too. He bounced off the bed and followed on my heels into the bathroom.

Now, one of the reasons I chose this hotel was the bathroom. There was a big jetted soaking tub. Which was great. But it was the huge shower stall that was my real reason. There were shower heads on three walls, each of which had three or four settings. Overhead was a huge rain head. There was a seat on one wall and a rail on the other.

Pushing a couple of buttons had the temperature of the water just right. I stepped in and pulled Axel in after me. I pushed him under the rain fall and stepped back to watch the warm water cascade over his body.

As the water worked it's magic, Axel's dick began to harden. I slipped around behind him to grab an herbal body wash.

He sighed as my hands began massaging the gel on to his shoulders. Such broad hard muscled shoulders. I worked my way down his arms. Hard biceps, strong forearms. I even massaged his big stubby hands and fingers. I stepped in close to travel back up his back from his waist.

Then my hands were slipping over his barrel chest. Massaging gel over his hairy pecs and stiffened nipples. Axel sighing as I tweaked each nipple, leaning his shoulders into my chest.

When I worked my way down his belly, Axel moaned softly. I soaked his stiff cock, my own hard dick poking his ass. Axel shifting his legs until my cock slid between them, the head nestled against the back of his balls.

Axel began to rub his full butt against my belly. My cock slipping around between his wet thighs. As much as I wanted to sink into that gorgeous ass again, I had neglected to bring a condom. I said as much to Axel.

"Go get it, Rusty! I know you want to". Axel bit his lip. " I want you to fuck me again!"

Dripping water all over I scrambled into the bedroom to grab the condom and lube.

I slid on the condom ,going back to find Axel braced against the rail, legs spread, ass on display.

I slipped back into the shower behind him, opening the lube. I slicked my fingers and slipped them into his ass crease, finding, then playing with his pucker.

First one finger sliding in, the moist heat of his gut greeting it. I wiggled it around, feeling for his joy gland. Finding it had Axel's burly body shivering and gasps coming from his lips. He began bucking his hips, fucking himself on my finger.

"More ", he demanded. He groaned as first a second then a third stretched his hole.

He began riding my three fingers hard. The sight of his hole clinging to my fingers on the out stroke, followed by the indenting of it going in, had a steady trickle of precum leaking from my rock hard cock.

" Now!" Axel ordered. " I want your big cock in me now!"

Pulling my fingers out, I wasted no time pushing my cock head against his hole.

Once he felt it begin to go in, Axel bucked his hips back, taking me in one long glide.

We both paused a moment, me reveling in being buried deep inside such a sexy man. Then Axel started screwing himself on my seven inch pop can.

He began talking nasty. He demanded to be fucked. Wet skin smacked in a rhythm of my thrusts. He demanded more, demanded I pound his hole. He braced himself on the rail as I grabbed his meaty hips and fucked for all I was worth.

He came with a roar, his spunk coating the wall then washing away between our feet.

His spasming gut pushed me over the edge. I buried myself deep and emptied my balls in the condom deep inside him.

After a bit, I pulled out and gasping sat on the tiled seat. Axel plopped down beside me. After we'd recovered enough, we quickly washed and stepped out to dry.

A quick look at the clock showed my alotted time was almost spent.

I went to a drawer and pulled out Axel's money. I handed it to him with a big smile. " Thanks for making my birthday special!"

Axel went and stuffed his money in his jeans.

Then still naked he plopped down on the bed. He grinned and crooked his finger at me.

Puzzled, I went to him. He took me by the hand and pulled me down beside him.

"It's late, I got no where I have to be and since it's your birthday, how about I throw a little free gift your way."

At my surprised look, Axel chuckled. " I wouldn't mind a bit of cuddling with you Rusty. You're A good guy and treated me special. Not like a piece of meat. So if you are up for it, how about I finish out the night for your birthday? "

In answer I crawled into bed, pulled him in with me. I spooned in behind him, wrapping my arms around him. Utterly satisfied, I soon drifted off to sleep. What a wonderful birthday!