This is one of my earlier stories. It’s all fiction, wishful thinking if you like. Simon
I’m in the escort business. Yes. Say what you want, call me whatever you like, a slut, a prostitute, a fuck-boy, I’m still an escort and I love it for both the sex and the money, not to mention the adventure.
I place ads in gay magazines, different ads with different names and different telephone numbers. This way I know what the guy calling me wants. I’m Chris for clean, vanilla sex. I’m Hugo for slutting. I’m Jack for hard, top sex. And I’m Daniel for company with older men. Since I am 22 years old, I can play all roles and I try my best to please my clients. Beside the escort role, I also advertise as a masseur.
Last night my Chris number rang. Nice.
“Hello,” a husky, deep male voice greeted me. “Is this Chris?”
“Yes, it is. How can I help you?” I used my sweet, but masculine voice.
“You have an ad for massage. How much do you charge?”
I liked this. I appreciated the fact that this guy wanted everything clear right from the start. “It’s 50 dollars for a full body massage. That’s not including any extras,” I added, letting him know that I am open for more than the massage.
He agreed and I gave him the address, telling him I was available. Around twenty minutes later, he was at the door. I had arranged the massage room nicely, with incense and soft light music and fairly dimmed lighting. I had put on loose, black satin shorts (sans underwear, of course) and a tight-fitting I-shirt, accentuating my lean body.
“Chris?” he greeted me at the door. My first impression was very positive. The guy looked in his early thirties, conservatively dressed, fit, and handsome, with a light beard. I knew this was going to develop into an interesting evening.
“Yes. Please come in.” I led him to the living room. My apartment has one living room, a bedroom, and a smaller room, which I use for the massages.
“Would you like to drink something? Coffee?” I always like to treat my clients this way, to make them relax. This guy was quite tense and I could tell that this must be his first or second time.
“Ummm…” he hesitated, a bit taken by my offer.
“I have something stronger than coffee, if you prefer.”
He lightened up and asked if I had any scotch. “Straight, would be fine.”
I smiled and left to get him the drink. When I got back, he was sitting on the edge of the couch, looking skittish. I handed him the scotch and excused myself. “I need to make some preparations. Please make yourself at home and enjoy the drink. I will be back in a few minutes.”
I knew that I had to give him some time to unwind and relax. And the scotch would be of great help. I waited for around ten minutes and returned. “I’m ready if you are,” I said with an encouraging smile and led the way to the massage room. Handing him a clean towel, I asked him to undress and I left the room. Again I waited for a few minutes. When I came back, he had the towel wrapped around his waist and was sitting on the edge of the massage table. He had a hairy chest, and I could tell that he was excited by the bulge tenting the towel.
I had him lie on his belly as I prepared some oils. I took off my I-shirt, revealing my smooth chest. I noticed his look of approval as he turned his head sideways to watch me.
Applying the oil on his shoulders and back, I started the massage standing at the side of the table. I moved slowly down his back noticing his bubble butt. Then I moved to the top of the table, and I started on his shoulders. I made sure my crotch as right at his head. Since I wasn’t wearing any underwear, my 22-centimeter dick (8.5 inches) showed a promising attraction inside the silk shorts, even soft. I wanted this guy for more than the massage but I didn’t want to scare him away by being too obvious either, just a tantalizing touch.
As I worked his shoulder muscles, my crotch a few centimeters away from his face, I made him place his arms down on both sides. Every now and then, I would lean further down his back, my crotch almost touching his face. He was breathing hard and I noticed his humping. Then I moved over to the side and returned to the lower back. My crotch touched his arm, and I could feel him tense. Pressing just a little, I made sure that he felt my dick through the shorts.
Very slowly, he placed his hand against my thigh. Since I didn’t move away, he was encouraged to start gently running his hand up and down my thigh. I was still not erected, but I also gently rubbed my crotch on his arm.
Turning his head towards me, he murmured, “Is this included in the massage or is it going to be an ‘extra’?”
“Don’t worry about it,” I said, putting more pressure on his arm, my cock starting to harden. “If you like what I’m doing, there wouldn’t be any problem.”
He reached for my cock. Sliding his hand under the leg of my shorts, he felt his way up to my balls. As he got hold of my dick, I slid my hands under the towel and started to massage his butt cheeks. He was already moaning, his hand trying to measure my cock size. I could tell he was fully turned on.
“Could you turn over?”
The towel was tented hard when he lay on his back. I took his hand and placed it on my crotch encouragingly as I removed the towel to reveal a thick, cut cock, rock hard, pointing straight up. He rubbed my erection through the shorts as I massaged his inner thighs and moved up to his balls. In my role as Chris, I knew that what he wanted was a mutual blowjob. Nothing fancy: just to get off while sucking on my cock. I pulled down my shorts and kicked them aside, standing naked next to him, my hand now around his cock shaft. He immediately turned his face sideways and took my cock in his mouth. I let him nurse as I stroked his dick using more oil on the shaft and the head.
The man was hungry. I fed him my long cock and he gagged and slobbered but never let go. His moans were getting louder with each swallow, as I gently inserted more of the shaft into his mouth. Moving my hand from his cock to his balls and into his crack, I massaged the area under the balls until he started squirming with desire.
I wasn’t sure whether he was here for fucking also. Many of the men I serviced were satisfied with blow jobs. I needed to test and see if I should initiate something. As I inserted a finger into his hole, he started. “Sorry,” I apologized. “I thought you might enjoy it.” I immediately removed my finger.
He let go of my dick for enough time to say, “It’s a first for me, but I think I’m enjoying this.” He squeezed my dick with his palm and licked at the tip. Bending over his laid-out body, I reciprocated by taking him into my mouth. I was able to go down the shaft all the way to the base. Flicking my tongue around the head as I worked the base with my pursed lips, I quickly brought him to the edge. When he shot his load, he actually bit my dick. I was glad that I was able to make him cum since I had another client for later in the evening.
I pulled out of his mouth, my cock dripping with spit and some pre-cum, and wiped myself, cock and mouth. He lay on the table, breathing hard, eyes closed, all muscles tense. I heard him murmur, “Oh, my God, thank you, Chris, thank you, oh my God!”
Excusing myself, I left the room to let him get hold of himself and prepare to leave. Around ten minutes later, he emerged, all dressed, with a just-fucked expression on his face. I felt a little disappointed that I didn’t get to fuck him. There would have been more money to make, and to tell the truth, I just loved to fuck.
“Thank you, Chris. This was beyond my expectation.” I smiled. “I’m going to be in town for three days on business,” he continued. “Is it possible for me to see you again?”
“Sure, ah… Mr…” I realized that I didn’t even know his name.
“John. Just call me John.”
Aren’t they all johns? I smirked internally. After all, Chris was not exactly my name either. “Sure, John. Just call me and we’ll arrange for something.” To me, he was CJohn, the vanilla guy, since he used the Chris phone number. This way I could tell one from the other.
CJ took out his wallet and handed me a hundred. I made to get him 50 back, but he shook his head. “This was worth it, Chris. Keep the hundred.”
“Thanks, John. I’m glad you liked the extra.”
When CJ left, I was elated. This was going to be a lucrative evening and I might be able to buy a new smart phone. Besides, I had a CJ client for at least two more days, and CJs were the easiest to handle, easy to be satisfied and always impressed by my equipment and my charm.
My next client was a house call. This guy used the Jack telephone line, and I was glad that I hadn’t let go and shot a load into CJ’s throat earlier. It looked like it was going to be much harder work. Being a house call, I quoted 100 dollars for the massage without the “extras.” The address he gave me was one of the plush hotels. I had never been there since it was too expensive for my budget or the budgets of my clients so far. So I was excited about the date. I worried about how the hotel staff would treat me once I got there, in jeans and t-shirt, toting a backpack that contained my massage stuff. The man said that he would meet me in the lobby.
I studied myself in the mirror as I prepared to leave after showering, to make sure I had the necessary rugged Jack-look that I was hoping would attract my client. The frayed jeans showed a nice bulge and the tight t-shirt outlined my abs and pecs. I applied some gel on my hair to make it spike a little, in a street-wise fashion. I needed to show a look of a hardened street guy ready to fuck. Inwardly, I wished I had spent more time in the gym developing my man muscles, but this would have to do. I was sure that as soon as my client viewed my equipment, all the other details would dissolve.
I entered the hotel lobby under the stern stares of the doorman, who I felt was following me inside. A middle-aged man in slacks and buttoned-down shirt approached.
“Jack?” he inquired and I realized that he had recognized the looks he was expecting.
“Yes,” I said glancing sideways to notice that the doorman had retreated. “I’m here for the massage appointment.”
The man smiled. Ignoring the beginning of white hair on his sideburns, I noticed that he looked quite handsome. I detected a bit of a pot belly under the fairly loose shirt, around which the pants belt strained. I was hoping that his wallet would be fat, too. In my business, I have serviced older, fatter men, not minding their out-of-shape bodies since they had shown so much zeal and appreciation in bed.
“This way,” he guided me to the bank of elevators, stopping for a few seconds at the reception desk and sliding what I imagined some kind of bill over the counter to the man behind the desk, who surreptitiously pocketed the bill, nodded and smiled at my man.
“You need to keep the staff happy,” he whispered to me as we approached the elevators. Inside, he said that his name was John. Of course, what else? So now in my mind, I filed him as JJohn as opposed to my earlier client, CJohn.
JJ led me to his room. What was I thinking? Room? The fucking place was a full suite, larger than my tiny apartment, fantastically furnished, with a hallway, dining-sitting area, bedroom, dressing room, and two bathrooms, the main one with a Jacuzzi tub. There was also a balcony overlooking the waterfront with a breathtaking view.
The guy walked over to the mini-bar and took out a bottle of wine. “Would you like some of this, Jack?”
I nodded, trying to take in the place. So this was how the high class, money-laden people lived. Well, for my JJ, this was how he would soon be fucked: royally.
Sipping at the wine, we stepped out onto the balcony. The suite was on the 19th floor, and I felt a bit dizzy with vertigo at this height. JJ stood beside me, close but not touching. With my free arm, I wrapped his waist and drew him closer. Even though I was much younger, probably as old as his son, I decided to take the initiative. I guessed that this was what he wanted by using the “Jack” number. He responded by pressing his hip onto my side and closing his eyes for a moment as I squeezed lightly on his waist. And, yes, I did feel the fat around his belly.
“So, Jack, can I ask how old you are?” he said between sips of wine.
I couldn’t admit to 22. But maybe he did want a young guy. Should I claim late twenties? Would this turn him off? I wouldn’t want to lose him as a client, not when he was so loaded. I decided to be enigmatic.
“Old enough to be your escort, young enough to be great fun,” I said with a smile, watching his eyes.
He stared at me for a moment, shifted his eyes down to my body, stopping at my crotch, and nodded his head lightly. “This is one of the very few times that I have been stumped by such a smart answer.”
Again, taking the initiative, I moved the arm from around his waist to the back of his neck, and pulled his face to me, placing a wet kiss on his lips. I heard him moan and felt its reverberations in my head.
“Shall we go inside?” he murmured huskily as we broke the kiss.
I followed him, watching his butt, bubble shaped and firm-looking even under the dress pants he was wearing. My dick liked that a lot and I promised him a good fuck.
“Let me get things set up,” he said as he disappeared into the bedroom and came back with a folded massage table on rollers. Wow! The man was prepared and ready. Slowly, I slid my backpack off and pulled off my t-shirt. I helped him unfold the table and make it fast.
Without speaking, and with his eyes alternating between my face, my naked torso, and my bulge, JJ stripped. All the way. He stood there, watching, waiting for my reaction, as I studied his figure. The pot belly was there, sure enough. He was hairy all over as opposed to the small chest hair patch that I had. I could barely see his dick through the thick, curly pubes. I wondered how he would react to my cock, which I estimated would probably be at least three times bigger than his.
Finally, he took a deep breath and climbed onto the massage table. “You can strip, too, Jack,” he suggested as he settled on his stomach, looking at me sideways. I undid my jeans buttons and slid them down, keeping my tight boxers. I noticed his eyes grow wide when he saw the bulge inside my underwear. My cock, now semi-erect, snaked down the leg, stretching the tight lycra fabric.
Fishing out my oil bottles, I started to apply some onto his back and to rub him up and down. As I did the shoulders, standing on the side of the massage table, I could feel the knots of muscle, and how they began to relax under my fingers. A few minutes later, I felt his hand on my thigh. JJ wanted action, it seemed, and he wanted it now. His fingers traced up and down my hairy thigh until they reached my crotch. Gingerly, he traced my dick. Still working on his shoulder, I moved to the top of the table and pressed my cock onto his upturned face. He moaned.
“I’m impressed,” JJ said as he moved his lips up and down my cock shaft, which by now was on its way to erection. I pressed onto his face harder, grinding.
“Do you like it this much, John?” I asked teasingly.
“Oh, Jesus, yes,” he groaned with lust. He moved one hand and tried to pull down the underwear. I immediately slapped it away. I felt I needed to prove to this guy that I was the one in control. He might be rich and all, but I got the dick and I was going to do the fucking, and he did use the Jack phone number
He kept his face glued to my crotch, but moved his hand back down to my thigh, caressing it.
I needed to do something special with this guy. “John?” I said, looking down at his balding head as he kissed and licked my bulge. “Does that Jacuzzi of yours work?”
He immediately got up, his eyes glinting. “Oh, yea, sure,” and I could detect the excitement in his voice. “Let’s do some Jacuzzi, Jack.”
He turned on the water to fill the tub, and as we waited, I pulled him to me and kissed him, this time with open mouth and deep tonguing. I pressed my erection onto his small penis and rubbed against him, one hand on the back of his head, controlling the kissing, the other caressing his firm, hairy butt. He writhed under my embrace. Age difference disappeared and it was as if I was the older guy, preparing a young kid for a hot fuck session.
Finally, the tub filled out. JJ added some bath oils and colored stuff from different bottles to the water, and he stepped into the tub, squatting and then sliding down into the now bubbly water.
Slowly, standing at the tub, I pulled down my tight boxers. My cock sprang up, 22 centimeters of hard fuck tool. The man’s eyes literally bulged. He couldn’t take his eyes off my hard cock, standing at an upward angle, revealing my balls. I stood there for a while, letting him drink in what he would later be getting up his man hole, all the way to the base. He reached for my cock, and I once again slapped his hand away. He settled back in the tub sheepishly, reaching for his own erection, now not only hidden by his pubes but also by the soap bubbles.
I climbed into the tub as he turned the Jacuzzi jet nozzles on, and I settled facing him, my legs stretched out along his sides. I started to relax with the warmth of the water, the scents of the oils, and the massaging effects of the sprays coming out of the nozzles. JJ kept his distance, like a good boy, all the while gazing at my face and every now and then licking his lips.
I couldn’t keep him in anticipation for too long. I didn’t want him to lose interest. So I sat up and made him slide on his butt between my legs towards me. Placing his own legs around my waist, he leaned over and we kissed. I took one of his hands and guided him to my hard cock under the soapy bubbles, and this time I let him explore. He palmed my hard cock, stroking me slowly as I tongued his mouth deep. I reached down and held his nipples between my thumb and forefinger and squeezed on them, making them hard, teasing them. His moans intensified.
I decided that by now, I should make the move to start the sex. I stood up, all soapy, my cock still angled upward and dripping and I thrust my pelvis towards him, inviting him. He eagerly held onto my thighs and gobbled my erection. Moaning loudly, he sucked on the head. When he tried to go down the shaft, he gagged. I immediately held his head and pushed deeper. With his lips open around my cock, he started to cough. I kept thrusting deeper. He looked up at me, his finger nails buried into my thigh muscles, as if begging me to let him breathe. Still holding onto his wet hair with both hands, I kept on pushing. I could feel my cockhead hit his throat. His gagging and coughing increased and the pressure of his fingers on my thighs intensified, digging into the muscles. I wouldn’t let him get off my cock. I pulled out a few centimeters, and a look of relief came to his face, which instantly disappeared as I shoved hard back down his throat.
Forcing him to take my long, hard dick turned me on more, and my cock got even harder and thicker. Once I felt his nose buried in my pubes, I started to grind against his face. He was still coughing and slobbering when I released the pressure off the back of his head a few moments later.
But would he pull back as I expected he would? Not on your life. He kept my cock buried down his throat and pursed his lips around the base. The coughing receded and I determined that by now he was able to control his gagging reflex. After a while, with me standing in the bubbly tub, and him sitting on his butt with my cock deep down his throat, he started to blow me. He never let go of my thighs. I caressed his hair and his face cheeks as he went down on me, pulling out till the edge of my cock head ridge and then swallowing back the shaft to the base. In response, I started pumping into his mouth.
With a gratifying look up at me, he took my hard pumping eagerly, now that he was more comfortable with sucking my big cock, which was totally in the mood for fucking.
Pulling him off my throbbing dick, I turned him around in the tub and made him bend over the edge. I wanted his ass. He wanted me to want his ass, too, I bet.
“Jack, please, wear some protection, ok?” he moaned as he offered his butt to be fucked. “There are some condoms on the rack behind you.” Sure enough, there was a packet of condoms, ribbed, right where he said it would be.
Quickly, I ripped open the wrapping and slid the condom onto my cock. It was a bit tight. Apparently, JJ hadn’t expected a cock as big as mine. Otherwise, he would have bought the large-sized condoms. I was a bit concerned that it would break, but I went ahead and rolled it down to around two thirds of my cock shaft. I knelt into the water behind him, and rubbed my cock shaft up and down his soapy crack. He ground back on me, moaning with anticipation.
Spreading his ass cheeks with my hands, being careful not to slip on the soapy porcelain, and enjoying the jets of water hitting my butt, I gave it to him. When I penetrated, he grunted with the immediate pain. His rim muscle stretched for me, and I paused with just my cock head inside him. Bending over his back, I pulled his head up by the hair, turning his head sideways, and I pushed my tongue into his mouth, and my cock started to get sucked into his hole. Thrusting, I went all the way to the base and paused again, grinding my groin onto his bubble ass cheeks.
Completely inside him, I bit on his lips and then moved to his earlobes as I started my fucking. I went a bit gently at first, but very soon, I was pumping his ass mercilessly. I felt I was going deeper into him with every hard thrust I made. His groaning and grunting told me how excited he was. His hole puckered on my cock shaft with every thrust. His tunnel spasmed wildly with every invasion.
I usually don’t come quickly. But what with CJ sucking my cock earlier, and now my deep fucking in the Jacuzzi, I couldn’t hold much longer. When I exploded inside him, I did so viciously. I was almost sure that the condom would burst with the force of my squirts. But I was way beyond caring. I pulled on his hair hard as I shot into the rubber, emptying my balls with repeated squirts.
“Take my load, bitch,” I hissed as more cum left my cock slit into the condom.
Finally, I pulled out, now anxious to see whether the rubber held. Thankfully, it did. I pulled it off my dick, which was still hard, and settled back into the now cooling water. JJ settled back also, facing me.
“You’re a hard fucker, Jack,” he groaned with satisfaction.
“Did you shoot your load, John?” I asked.
“Twice,” he smiled. Fuck! That was why his rim muscle was doing miraculous squeezing around my probing and thrusting cock shaft. He was shooting loads of cum, without even touching himself.
“This means that you have enjoyed the hard fucking, then?” I smirked, fully knowing that this was exactly what he wanted when he used the Jack-telephone line.
“Can you spend the night?” This came out of nowhere, taking me by surprise. I had never had such an offer before and I hesitated. “I mean,” he tried to explain, “it’s just that I enjoyed our fuck so much, I want repeats. Can you?”
I decided. “Yes.”
He beamed. Now, suddenly, I thought about the money side. Would he make me an offer? Should I stipulate a specific figure? How much should I demand? For one, he loved my fucking. Two, he was loaded. Three, it was he who suggested this. Man, I was really at a loss. He must have sensed this because he immediately told me that money was not an issue.
“What are we talking about, then?” I countered. “I have already agreed to stay for the night. I have not asked for extra money although I am certain that it will cost a bit more.” I was calculating the “bit more” part. I charged him 50 for the massage and there would be another 50 for the fuck. I thought that was kind of cheap. Maybe I should be looking at 500 for the night? That would be too steep, wouldn’t it?
Then he hit me with his offer. “Is 1500 ok?”
My jaw must have dropped and my eyes widened. One fucking thousand and five fucking hundred for one fucking night? I must have been dreaming. How many cell phones could I buy? Oh, my God.
I just nodded my head and I could see that he was elated. He reached out for his wallet which he had placed on the wash sink and counted 15 100-bills in fucking cash. Just like that! Oh, boy, I was going to fuck his brains out all night. He was going to be 1500-dollar sore by morning. I had the equipment to do it and I also had the stamina. All thoughts of CJ were blanked out by this.
“JJo…” I caught myself in time. “John, thanks, it is fine. Let’s get into the shower. I want to soap you all over and fuck you with water streaming over your body. Are you ready for some hot, rough showering?”
He beamed again and rubbed his ass, “Jack, you fucked me hard in the Jacuzzi. Let’s try the shower.”
“But first,” I decided on the rough part. “I want you to get down on your fucking knees and worship my cock.” I knew this was crass and vulgar, but I had to satisfy this dude in any way I could.
After a few minutes of allowing him to slobber on my rod, I told him I wanted to take a leak. I stood in front of the toilet bowl and let out a hot stream of piss through my now semi-hard dick. He watched, eyes open, jaw dropped. With my last squirts of urine, JJ heaved a deep sigh and stepped into the shower. The wad of money was still in my wet hand, and I rushed to where I had dropped my jeans and shoved it into the back pocket. Wow! 1500 dollars!
In the shower stall, I soaped him all over. My hands massaged his body, played with his tits and smallish dick. I fingered his hole and when he complained about the soreness, I slapped his butt and told him not to be a sissy. I could detect that he was really getting turned on with this rough treatment which, I had to admit, I was not used to. I usually fuck nicely, making love rather than fucking. I have always believed in a give-and-take relationship. But now I was paid as an escort. I was a male prostitute, to put it vulgarly. So I gave it to him, rough and hard.
Raising one of his legs, I thrust my hard cock into his hole without any preparation. I figured that my tub fucking should have prepared him enough. Besides, he wanted it rough. The soap made it easier for me to penetrate, but he cried out with the pain of my invading tool. This didn’t stop me as I roughly thrust my cock all the way to the base, my balls slapping his inner thighs, my fingernails digging into his thigh.
As I pounded his ass, JJ supported himself with both hands on the shower wall. His grunts and groans accentuated my fucking, giving me more impetus. We were like two animals grunting and moaning with lust. As I pumped deeply inside his body, I played his tits, squeezing hard; I grabbed his nuts and squeezed also. I slapped his butt cheeks. He responded with more intense moaning with a lot of “yeah”, “more”, “do it Jack”, “fuck me baby”, and “harder please harder.”
When I saw him reach for his dick, I slapped his hand away. I wanted him to shoot his load because of my fucking not because he was jerking off. I pounded harder and I could feel that he was about to reach a climax. I bit on his neck and squeezed his tits over and over, responding with “take my dick, bitch”, “I’m going to fill you with hot, creamy juice” (now that the protecting condom had been forgotten in the heat of the moment), and a lot of “fucking bitch”, pounding and squeezing.
All of a sudden, I felt the puckering of his fuck tunnel twitch hard on my pounding cock shaft and I knew that he was shooting his load. He arched his back against my chest and cried out as his dick released streams of cum onto the wall and the floor of the shower stall. I wasn’t close to losing my load yet, and I decided that it would be better if I kept it for further fucking since I was going to spend the whole night here. Also, I realized that I really should be more careful about bare-backing. I was almost certain that I wouldn’t be doing much sleeping tonight.
So I pulled out of him as the last drops of semen dribbled off his small dick slit. Turning him around, pushing him onto the wall, I held him tight with my hard, wet cock pressing on his belly, and we kissed. He was so hungry that he almost swallowed my tongue, all the while moaning with after-ejaculation pleasure, jerking against my pressing and throbbing cock. I made sure to finger his hole all the time to remind him that I will be using it over and over. There were fifteen hundred dollars stashed away in my back pocket, and I was planning on earning every cent.
He prepared pasta in the small but well-equipped kitchenette of the suite, as I lounged on one of the plush couches with only a towel wrapped around my body, enjoying the pleasures of the rich surroundings.
“Damn!” he exclaimed after he dropped the pasta into the pot of boiling water and opened the fridge under the counter/bar.
“What is it?” I asked, feeling all relaxed, even somewhat drowsy.
“The bastards haven’t put any vegetables or fruits in the fridge although I explicitly asked for a full stocking of stuff. I’ll call room service for salad. Any kind you prefer?”
Fuck! For me a salad was a salad: vegetables with some lemon juice and oil. What did he mean by “kind of salad”?
“I’ll leave this up to you JJoh… uh… John.” This was a smart way of avoiding to reveal my ignorance of sophisticated cuisine.
He laughed, noticing the difficulty of my saying his name. “What’s this JJoh.. thing?” Shit! How could I answer this without hurting his feelings? I didn’t want him to think that what I am doing to him was only to please him. I wanted him to feel that I was enjoying myself also and that my fucking was very real. Although it was real and I was enjoying myself, it was not my real preference in sex. CJ’s was more exciting for me: slow, easy love making building up to intense gratification.
I smiled to hide my nervousness. “Listen,” he said when I did not offer any explanation. “Why not use my real name? It’s Richard, ok?”
“Would you like to know my real name as well? It’s not Jack.” I felt I had to reciprocate. I also, and for the first time, felt that I needed to reveal more of my identity to a “trick” or a “John.”
“If you are comfortable with that, yes sure.” He smiled back.
“Ed,” I murmured.
“Ok, Ed. This sounds more like you than Jack. But I hope the Ed in you will fuck me like a Jack.”
“Oh?” I raised my eyebrows. What difference did it make to him whether my name was Ed or Jack? My dick was the same and my fucking was the same.
“I feel better to be calling you with your real name since I knew that Jack was a fake. I want the man who fucks me to be real not fake.”
I grabbed my crotch and said, smirking, “So all this time since we started fucking you considered this as fake? Didn’t it feel real enough for you?”
He approached me, also with just a towel around his waist. “Oh, Ed, it was real enough! My sore ass will vouch for that. You are an incredible fucker and I want a lot more of you tonight. But I like Ed much better.”
I didn’t take this any further as he picked up the phone and ordered the salad. Sitting in an easy chair facing me, he regarded me with what I felt more of a critical eye than before, less lustful, more judging, now that he had been fucked twice and ejaculated a few times.
“Why do you do this, Ed?” he asked in a low voice. I could hear the water boiling with the pasta cooking in it.
“Why do I do what, Richard?”
“Escort,” he explained.
Did he really need to ask this? Did he want me to admit to my being a prostitute, fucking for money? Fuck him! I decided to come right out and tell him.
“Not all of us are born into money, Richard,” I countered. “I need money and I have a hot cock with people willing to offer money to suck it and ride it. I don’t think there is anything wrong with that.”
“I see,” he contemplated. “So there is no pleasure for you, huh? Just fucking to make money?”
“Oh, Ricky baby, there is a lot of pleasure,” I smiled at him rubbing my semi-hard cock under the towel. “My dick must have told you that already.”
“What a smart kid,” he said and moved over to sit next to me on the couch, replacing my hand with his and massaging my dick. I kissed the side of his neck, licking over to reach his lips, biting on the lower one as he moaned. “You do wonders to me, Ed,” he groaned, trembling, pressing on my hardening cock.
I was already thinking of before-dinner fucking when there was a knock at the door.
“This must be the salad,” Richard said, standing up to answer the knock. The towel tented over my erection and I straightened to hide it.
“Should I go inside?” I asked. Perhaps Richard didn’t want to advertise who his evening visitors were or what they were doing to him.
“Oh, no,” he said as he approached the door. “The staff here are very friendly, especially when I am generous with them.”
I bet, I thought. I would be the friendliest person around, musing about the 1500 dollars for the night and the earlier 500 for the massage. I was 2000 fucking dollars richer. Add a 100 from CJ! Wow!
The guy who rolled in the trolley with three or four different bowls of salad was fantastically beautiful. I immediately hardened more when I watched him place the trolley next to the dining table.
As he prepared the bowls and plates on the table, Richard walked back into the bedroom saying, “Let me get you something, Dan.”
Oh? So he knew the waiter’s name? Hmmm. Had he done the guy? I wondered. Dan is definitely doable and I wouldn’t blame Richard for grabbing him into his bed. Dan looked sideways at me with a smile, and then moved his eyes down to my crotch where my erection was clearly visible. He knew the score and he smiled and I detected a quick flick of his tongue over his lower lip. I instinctively lounged back on the couch revealing my hardness invitingly. This could be good for business. Very interesting!
Richard called me from the bedroom. “Ed, I need to ask you to do me a favor,” he said as I walked into the room with my cock 20 centimeters ahead of me.
“Shoot,” I said.
“Is it ok with you if I asked Dan to stay for the salad and pasta?”
Oh, my God. My cock responded with a strong twitch. Now I got to fuck Dan, too?
“There will be another 1500 for you if you say yes,” he added in a whisper.
“YES!” I almost screamed. “Yes, Richard. That would be fine.” It was so hard for me to control my voice or the shivers that were streaming throughout my body. The money AND the sex! Fuck! How lucky could one get?
We walked back to the living area where Dan had finished setting the table and was waiting. His eyes immediately shifted to my tented crotch, and again there was the flick of the tongue along his lower lip.
“Dan,” Richard said approaching him. “How about staying and sharing all this with me and ah… Ed.” I noticed that he had pushed a couple of bills, probably hundreds, into Dan’s pants pocket. Did those kind of people ever handle tens or twenties? I guessed they even wiped their asses with 100-dollar bills.
Dan smiled, his gaze still glued to my erection under the towel. “Yes, Mr. Thompson. It would be a pleasure.”
He then approached me holding out his hand, “I’m Dan and it’s good to meet you, Ed.”
I took his hand and squeezed, pulling it down inches away from my erecting front. I could hear his breathing quicken.
“Ok, Boys,” Richard clapped his hands and moved to the kitchenette. “The spaghetti must be done by now.”
We sat around the table and ate. My erection receded and I discovered how hungry I was. Richard barely ate anything, but Dan also ate heartily. I knew that the three of us had similar thoughts: how would the coming fuck session be like?
The meal over, the three of us walked to the bedroom. No introductions? No making out? As soon as we were inside, I dropped the towel and sat on the bed naked, my cock limp and resting on my thigh. Dan was already impressed. His bulge showed a lot of interest. Richard did the same as me and pulling Dan towards the bed, he sat beside me and placed his hand on my cock. “What do you think of this equipment, Dan? Does Ed’s tool compare to yours?”
“Only one way to find out,” Dan responded by taking off his shirt and pulling down his pants. His briefs bulged impressively. Apparently he was also hung. Was Richard challenging us? Two hot, hung kids to service him?
And yes, Dan was hung. I felt a bit shamed when I saw that he sported a larger cock than mine. It was a monster of a cock. Thick, veined and a couple of centimeters longer than my cock, it erected curved sideways to the left, unlike mine, which erected upwards at an angle. I was starting to harden under Richard’s caressing and Dan’s huge dick.
As Richard bent to take my erecting cock into his mouth, Dan came over and presented me with his monster erection. I didn’t hesitate. I slobbered on his dick as I pumped up in and out of Richard’s hungry mouth. Already, I was having new sensations that I had never experienced before. So, ok, I was an escort and I was supposed to have experienced all kinds of sex. But this scene was totally new to me. In none of my relations as a sex prostitute had I experienced a cock so big. Most dicks were smaller than average, and the men much older. But Dan beat all. His body was a killer as well, lean and muscled and lightly hairy on the chest with thick pubes and hairy legs. I licked and sucked and slobbered, and so did Richard on my own cock.
A few minutes later, Richard released my dick and asked me to lie on my back. Straddling my hips, he held my cock, unwrapped a condom and rolled it down the shaft, and pointed the head at his hole. I felt Dan’s tongue licking up and down my cock shaft as I pressed on Richard’s fuck entrance. Dan’s hands were fondling my balls. I thrust up and penetrated. Richard’s hole was not so tight anymore and my penetration came easy and smooth. He pushed down until my cock was buried all the way inside him. Dan was still at my balls, slobbering and licking and fondling as I started fucking Richard’s ass with his meeting my upward thrusts with his downward push.
As I was enjoying the fucking, already sweating with Richard’s weight on top of me, I felt Richard settle and freeze his downward pushes, pinning me under him. I thought that he was orgasming, but I noticed that Dan was putting on a condom and lubing it. His monster cock glistened inside the rubber. So, ok, Richard wanted Dan inside him now. That was fine with me. I could do with a breather. But Richard kept pressing me down.
I started when I felt globs of lube applied to the base of my cock and into Richard’s crack, dribbling down to my balls. Could this be what I was starting to conclude? Was Dan entering Richard’s ass with my cock already inside?
I felt Dan’s fingers probing the stretched fuck hole and massaging my cock shaft inside Richard’s ass. Fuck! Richard was going to be double-dicked by two hard, fat cocks.
Sure enough, Dan straddled my thighs and I felt the head of his cock pressing down on my cock and stretching the rim muscle to enter. With all the lube, and with Richard apparently already experienced in taking cock up his ass, Dan entered. His cock slid over mine, pressing down on me.
I couldn’t describe the sensations. This was a first for me. As Dan pushed all the way inside Richard’s ass, he bent over his back, moving Richard’s head to the side, and started to kiss me. Now the two of them were on top of me. I found breathing to be difficult out of the weight of the two bodies and more out of the excitement of Dan’s dick pressing on mine inside Richard’s ass.
Slowly, as Dan pulled his length out, repeating the massage on my cock shaft, Richard kept his weight on me. When Dan pushed back in, I pulled out, neither cock totally exiting the fuck hole. We alternated, Dan’s dick pulling out, mine pushing in, and vice versa. This double fucking was making me mad with lust. I was fast building up to what I knew was going to be a huge load. My balls were aching. Dan felt so hot fucking both Richard’s ass and my cock, while I was doing the same to the both of them. There was no way I would be able to control myself and not explode.
This continued for some time. I had lost estimating how much time was elapsing. Except for the amazing sensations throughout my body, everything else went into oblivion. The alternating fucking made Richard go mad as well, crying out loud with every thrust of either of us. There were like thousands of “oh my God” and “Oh yeah” and “Dan, Ed, more, more” issuing through his lips. I could feel his body tremble and his dick pressed and rubbing between our bodies. There was a lot of slippery stuff on my belly and I figured that not all of it was lubricant, that some of it must be coming from Richard’s dick. How many times could this fucker ejaculate? I wondered.
When Dan finally pulled out, I felt huge emptiness although my cock was still buried deep inside Richard’s body. Slowly, Richard raised himself off me and my cock slid out of his hole as well. The three of us were panting and sweating. Richard knelt between Dan and me, removed the slick condoms off our pulsating cocks, and started an alternating blow job. Holding onto one cock and stroking, he sucked on the other. And then he moved to sucking the first and stroking the other. Dan and I were kissing like mad, tongues and lips and mouths. He tasted so delicious and I knew I was going to burst very soon.
Dan shot his load first. Richard gobbled and swallowed. The kid gave him such a huge squirting that Richard was choking with the flood inside his throat. Cum was seeping out through his gulping lips. I was almost there and the sound of Dan’s moans as he ejaculated made me ready to shoot my own. Pulling Richard by the hair, I took him off Dan’s cock, which was still squirting white semen all over the place, and pushed him down on mine, thrusting to penetrate the throat. Ignoring his gagging sounds, I fucked his mouth hard and deep, the juices erupting from my balls into my cock shaft. Again pulling on his hair, I pulled my cock out of his hungry mouth, and the first squirt hit him right in the face. It was so thick and intense that both his eyes and part of his right cheek were covered with semen. I directed my squirting cock toward Dan’s body and covered his dick, throbbing and leaking on his belly, with more cum. I cummed like crazy. Squirt after squirt of long streams of white juice exploded out of my cock slit onto Richard’s face and hair and onto Dan’s cock and balls.
Finally, I slumped back on the bed, almost unable to breathe because of the intensity of my ejaculation. Richard was cleaning both our balls and dicks and bellies with his tongue, his face covered with man juice. He didn’t seem to get enough of our cum.
Need I describe the rest of the night? Dan left after our threesome session, two hundred dollars richer. I could bet that Richard slipped him more bills as he left. Good for Dan. That was a great fuck.
I barely got a couple of hours of sleep. Richard was insatiable. All he wanted was cock after cock after cock, and mine was there hard and throbbing and ready to please. At one time during the night, the fucking turned more into rape, with my merciless pounding and slapping on his ass butt and pulling on his hair and squeezing hard on his tits. I was wild as I felt Richard receive all this with rising lust and desire. His cries were getting louder and I was a bit concerned about how thick the walls were and whether the occupant of the room next to the suite could hear the screams.
How many times did I fuck? No way could I answer this. It was continuous. Just before dawn, Richard was finally sated. Placing his head into the nook of my armpit, he fell asleep. I followed suit almost immediately. When I woke up two hours later, Richard’s mouth was already around my cock, sucking my morning boner. It didn’t take long for me to feed him his breakfast, thick and creamy.
Leaving the hotel, I had 3000 dollars in my pocket and a sore cock in my pants. As I approached the doorman, I fished out one of Richard’s bills and slipped it into his hand. His eyes widened when he glanced at the hundred-dollar bill that I had tipped him.
I felt very good. Actually, I felt excellent, heavenly. I enjoyed the night as much as Richard did. I didn’t feel like a prostitute at all. I didn’t just lie back and give him my cock to nurse or to fuck on. The night was memorable in all aspects.
Five minutes later, walking back to my place, thinking about the new cell phone I was going to buy with my newly earned money, I hailed a cab. What the fuck! This morning I was rich beyond my expectations. I felt expansive. I slouched back on the taxi seat and dreamed about double fucking and about hot Dan and about loaded Richard. By the time the taxi pulled over next to my apartment building I already had a raging hard on which I was sure that CJ was going to gobble and slobber on later today.
Oh, the miserable life of escorts!