Roommates Ch. 04byHerLittlePiggy©
'M4M. Generous men wanted. You host. Anything goes. Masculine athletic and naturally submissive but versatile. Shaved and ready.'
My cell phone rang and I quickly answered it. Twenty minutes later I was on my way to an upscale hotel on the beach. I had flunked out of Miami U and my parents had kicked me out of their house hoping it would straighten me out. I had been drunk all summer and working a part time job for spending money but when I was fired for being drunk at work they had enough.
I had been fucking anything with a pulse but somehow managed to avoid an STD. I dated a few girls, mostly fatties, but fucked a few boys on the side until I got kicked out of my parents house.
Without the cash for a security deposit I found myself sleeping in my car and showering at the beech. I had placed the ad on Craigslist and I was stunned at the response.
My first customer was a fat married guy who wanted to suck my cock. I met him at an upscale hotel while his wife was at work. He invited me in quickly and locked the door behind me.
"Can I see it," he asked excitedly wasting no time. He was short of breath and wide eyed as I quickly pulled my shorts down exposing my flaccid cock.
He reached into his pants and handed me a crisp $100. Then he dropped to his knees and took my dick into his mouth. He knew his way around a cock and in no time I was hard as a rock. His hands caressed my balls, stroked my shaft and played with my ass as his head bobbed up and down on my stiff rod. He took my entire dick down his throat without the slightest gag as his finger tickled my anus.
I came quickly from his very talented mouth and he swallowed my entire load. He then sat back with a proud expression on his face and looked up at me for approval.
"I have been fantasizing about doing that for years," he said as he stood up and wiped saliva from his chin with the back of his hand.
"So you've never sucked a cock before?"
"No that was my first time. How did I do?" He asked.
"You did fucking fantastic. I never cum that fast, you are a natural," I answered as I pulled up my shorts and walked toward the door. I was surprised how easy it had been to have sex for money.
"Can I call you again," he asked hesitantly.
"Of course," I replied. When he called a week later I had my first repeat customer.
I met Marcus a month after I got settled into my apartment. He had connections and he got me into clubs where I could get clients who would spend more to do more. I had to suck his cock at first but he was a player and we quickly moved past a sexual relationship into a purely business one.
Two months after I met Marcus I moved north to DC. I wasn't thrilled about leaving the warmth and comfort of Miami but Marcus said DC was where the real money was. He was right. I got cleaned up and spent money on nice clothes and an expensive haircut. I bought a decent car and found an apartment in an okay part of the city.
Marcus hooked me up with a female manager who had connections with many of the DC elite and soon I was making $1,000 to $3,000 a night fucking and getting fucked by the closet queens of American politics.
The strange thing was that while I was working as a gay prostitute, in my social life, which is admittedly slow, I was straight and I dated only women. I had found that because I had never been emotionally attracted to men but I did enjoy sex with them that it was easy to fuck men for money without any strings or emotional attachment.
Through my new manager, Susan, a lot of my clients were wealthy diplomats, high ranking government officials and high ranking military officers. They paid me to not only live out their fantasies but also to keep my mouth shut.
The first time I spent a night with a client in DC it was with a married lobbyist. Susan sent me to the Mandarin Oriental. I was dressed in a custom made charcoal suit with Bruno Magli shoes and a Brooks Brothers shirt and tie.
I left my clean but tired old '92 Mercedes 190 with the valet and called the room. I was surprisingly nervous when I knocked on the door.
The client answered the door in a pair of black silk boxers and nothing else. He was a short well put together man in his mid 30s with a well defined mostly hairless body. He introduced himself as Chris as he walked over to the amour and pulled out a thick roll of money. He pealed off 15 $100 bills and handed them to me.
"That's for the entire night," he said confidently. "What don't you do?" He asked as I tucked the money into my jacket pocket.
"You have me for the night and I will do anything you want," I said softly as I looked into his soft brown eyes.
"Good," he said, "get undressed." He moved toward me and wrapped his arms around my waist. He pressed his lips against mine and I kissed him passionately. I still didn't enjoy the intimacy of kissing a man but I had learned to fake it very well. When a person was paying $1,500 for a night with me they deserved a boyfriend experience and that is what they got from me.
I undressed as he watched and then stepped toward him wearing just an expensive pair of silk boxers. I leaned in and kissed him softly and whispered in his ear, "what do you like?"
His hands slid over my body as we kissed deeply. His cock grew hard and pressed against my body making my own dick grow stiff. We wrapped our arms around each other and kissed deeply as we ground together like two teenagers experimenting in homoerotic lust.
"I want to taste you," Chris said softly as he lowered himself to his knees. I looked down and watched as he buried his face in the crotch of my boxers and inhaled my essence. He kissed my cock through the thin silk and ran his tongue over my silk covered shaft soaking my boxers with his saliva.
"Mmm," I moaned as he nuzzled my dick. Chris pulled my boxers down and freed my hard cock. He took it into his mouth and sucked me hard and wet. He took my dick down his throat and noisily slurped on my bulbous purple head making me moan with unadulterated pleasure.
"Fuck me," Chris panted as he stood and kissed me deeply sharing the rich flavor of my precum with me. He led me into the bedroom of his suite and pulled his boxers off as he climbed onto the bed.
I noticed a box of condoms and a tube of lubricant on the night stand. I joined Chris on the bed and lay beside him. Our lips met and we kissed deeply. Our tongues entwined as we ran our hands over each other.
"Roll over," I whispered in his ear as I guided him onto his stomach. I kissed my way down his back and settled between his legs. My cock lay lewdly in the crack of his firm ass like a hot dog between a bun. I slid down and nuzzled my face into the crack of his ass. He smelled fresh and clean like soap and I parted his ass and ran my tongue from his taint to his tight sphincter making him moan and writhe with pleasure. I pushed my tongue inside him and tongue fucked him slowly as he ground his dick against the bed sheets.
My fingers pushed inside him as I poured lube over his ass crack. I sank three fingers inside him and massaged his prostate as I prepared his ass for my cock.
"God you are good," Chris moaned loudly as he bucked against my hand. I quickly rolled a condom onto my dick and lubed it up before rubbing it against his asshole.
"Do you want it?" I teased.
"Yes," Chris hissed as he looked back at me with pleading eyes.
"Turn over," I directed and he rolled onto his back and pulled his legs back to his ears.
I pushed my hard latex covered dick against his sphincter and with a slight pop it slid inside him. It sank deep inside her until my balls touched his ass.
Chris' eyes rolled back and a lust filled gaze spread across his face as I started to fuck his ass. His breathing was ragged and I could tell he would cum quickly as my dick stroked his prostate.
I fucked Chris with long slow strokes as he built toward a strong prostate climax. His body shook and cum poured down the side of his hard throbbing dick as he groaned with pleasure.
Unlike me Chris didn't lose his hard on after his prostate climax and we got into 69 position after I pulled the condom off my dick. I took his cum coated cock into my mouth as he lay beneath me and sucked my dick. I came first and Chris swallowed my hot cum and then pumped a huge load of thick creamy semen into my mouth. His cum was slightly sweet and I moaned as I swallowed it all.
Chris kissed me and spooned up behind me as we drifted off to sleep.
I awoke with Chris' hard cock pressed against my ass. He had just awoke and he quickly coaxed me down between this legs. I sucked him for ten minutes before he rolled me onto my stomach and rolled a condom onto his dick. He lubed his cock and my ass and then sank his man meat into my asshole.
Chris fucked me long and hard from behind. My dick grew painfully hard and I stroked it as he fucked me. I held myself on the edge until I knew he was ready to cum and I timed my climax so we came together.
Chris showered and dressed for work as I swished some mouthwash and put on my clothes from the night before. He kissed me at the door and tucked $200 into my pants pocket. "I'll be back in town in a few weeks," he said between kisses, "will you be available?"
"Of course," I replied as I squeezed his cock through his boxers.
I walked out the door with more cash in my pocket than I had ever had on me and I knew it was just the beginning.
I set up an offshore account with help from Susan and within a year I had over $200,000 in the account.
Word got around and my prices went up. I preferred one on one situation but I was open to group scenarios too.
One night, two years after I arrived in DC, I was laying in my posh Georgetown apartment when Susan called. Money had been rolling in and I was sitting on more than $600,000 in my offshore account depite moving to Georgetown and buying a few expensive toys.
"I've got a fun one that's right down your alley baby," she said playfully. Our relationship had evolved from purely business to a friendship of sorts and she knew all my foibles. Susan went on to tell me that she got a call from a middle age couple that wanted to experience a MMF threesome. The husband was bicurious and the wife was very interested in watching her husband's first time. "It pay's $3,000 and I am sure they will tip you well," Susan explained.
Two hours later I pulled up to a huge home in Great Falls VA and pushed the buzzer on the gate at the end of the driveway. I told them Susan sent me and they quickly opened the big wrought iron security gate. I eased my 2006 Porsche 911 up the driveway and walked to the door. I was dressed casually in a dark pair of Diesel jeans and a cashmere sweater.
An attractive but heavy woman in her mid forties answered the door. She was dressed casually sexy with a low cut sweater that displayed a perfect amount of cleavage and a short denim skirt that showed a pair of thick shapely legs with muscular calves. Her blonde hair was worn shoulder length and framed an extremely pretty round face. She had beautiful blue eyes that sat behind thin rimmed glasses, full lips and a warm pleasant yet slightly mischievous smile.
"Hello," she said as she extended her hand, "you must be Steven. I'm Gwen. We are so glad you could come on such short notice. Won't you come in." She led me through a big two story foyer into a large sitting room filled with rich antique furniture.
I nodded and took in my surroundings including Gwens full round ass. She looked to be about 5'7" tall and probably weighed 175lbs but it was well placed weight as she had huge breasts and a beautiful big round ass. I was hoping that she was planning on playing too because it had been a few weeks since I had hooked up with a woman and Gwen was just my type.
"Have a seat," Gwen said as she sat down on a richly upholstered couch and patted the cushion beside her. "David will be down in a few minutes. He was still getting dressed when you arrived."
She seemed a little nervous which was certainly normal given the situation but she quickly loosened up as we chatted on the couch. Our conversation flowed easily without any uncomfortable moments of silence and when David came into the room Gwen and I looked like old friends.
"Hi Steven," he said extending his hand as though he was meeting a business colleague and not a high priced male prostitute. "Can I get you anything to drink?"
I asked for a diet soda and he returned with my drink and two glasses of wine for him and Gwen. David sat down beside me and we all continued to talk about current events, their home and David's job in the private sector after 30 years in the military where he retired as a Colonel.
David was about ten years older than Gwen but he was in great shape for 55 and still wore his grey hair high and tight military fashion.
Our conversation had avoided the reason for my being there for the first 30 minutes or so but when we segwayed into an innuendo laced flirtatious topic Gwen excused herself and quickly returned with an envelope with money. She handed me the cash and I put it on the coffee table letting them know that even though I was there for money, it was secondary to their mutual enjoyment of the night.
I turned to face David and placed my hand on his thigh, just above his knee. "What is your fantasy?" I asked as I looked into his steel blue eyes.
Gwen leaned in behind me and wrapped her arm around my waist. Her lips grazed my neck and she kissed my ear as she whispered "we want to do it all." Her hand quickly found my cock and she started rubbing it through my jeans as she kissed and nibbled my neck.
David watched his wife get my cock hard as he slid his pants and underwear off exposing a long uncut cock. "I want to watch you suck my cock," David panted. He wrapped his fist around his hard drooling dick and pointed it toward me.
I leaned over and slid to the floor in front of David while Gwen quickly hiked her skirt up to her waist exposing her well groomed naked pussy. Her body was thick and curvy with a nice hourglass shape but a slightly protruding belly and a few rolls. I lowered my mouth onto David's cock and made a loud noisy show of slurping and sucking him as his precum tickled my tongue. His taste was bitter and briny but not unpleasant and I opened my throat and buried his long dick down my throat.
"Fuck I love this," Gwen sighed as she watched me deep throat her husbands dick.
I could hear the wet sounds of her fingers plunging into the depths of her soaking wet pussy.
"You like that don't you baby," Gwen said loudly as she watched me suck her husband's uncut cock. "You love that a man is sucking your dick don't you?" She was loud and confident as she chided her husband. Until then it had appeared that David was the dominant partner but all was not as it seemed.
"Yes," David moaned meekly. "I love it Gwen."
My head bobbed furiously over David's dick until his legs started to shake. He came hard and his thick cream filled my mouth.
"Don't swallow it," Gwen pleaded. She pulled me to her and kissed me deeply. David's cum sloshed between us and ran from our mouths as our tongues slithered together in a wet sloppy snowball.
David tugged at my belt and pulled my pants down to the floor exposing my tight silk bikini briefs. He buried his face in my crotch and licked my cock through the silk. He pulled my briefs aside and licked my smooth shaved balls as I slid lower on the couch. His tongue slid across my taint and lapped at my asshole as Gwen and I continued to kiss.
"Suck his cock baby," she cooed between kisses.
David pulled my underwear off and grabbed by throbbing dick with both hands. He noisily licked up the underside of my dick and slurped on my balls as he stroked my cock.
Gwen and I continued to kiss. I pulled her sweater over her head exposing her big near perfect natural tits. I quickly released them from the confines of her red lace under wire bra and I gasped in awe of her big tits.
"Do you like them?" She asked coyly and I nodded slowly. I kissed her deeply and then planted soft butterfly kisses across her neck and down her chest. I brought my hands up and felt the weight of her big firm tits.
"Ohhh," Gwen sighed as I started to nibble and suck on her perfect tits.
I continued to nibble, suck and lick her big breasts as my hands roamed over her body. My fingers slid between her thick thighs and glided over her smooth wet labia making her moan softly. I found her hard engorged clit and rubbed it making her shudder and shake.
"Don't stop," Gwen panted. "I am almost there.". Her breathing was ragged and her legs trembled as my fingers rubbed her hard clit faster and faster until she exploded. Gwen cried out loudly as she came. She pulled my head away from her shaking tits and mashed her mouth against mine. Her tongue plunged deep into my mouth and we shared an incredible passionate kiss as her husband continued to play with my cock and balls. David took my cock down his throat and sucked hard. His hands expertly played with my balls and stroked my shaft bringing me to the brink of orgasm but never pushing me across the line.
Gwen moved down between my splayed thighs and joined her husband. They took turns licking, sucking and stroking my cock for at least ten minutes.
"Lie down baby," Gwen said to her husband. She guided him onto his back and straddled his face in the 69 position. "I want to feel our guest inside me while you lick my pussy."
I moved behind Gwen's big round ass and sank my cock bareback into her tight wet pussy. I started slowly with long steady strokes into her soaking wet gash as her husband tentatively licked her clit.
Gwen came quickly as we double teamed her pussy. She cried out as she came and her big ass quivered enticingly while her cunt spasmed around my hard cock.
David began to lick my smooth shaved balls while I fucked Gwen. He had a long tongue and he occasionally dipped it into my asshole when I slowed my pace.
"Cum inside me lover," Gwen pleaded as I approached the point of no return. He big beautiful blue eyes looked back at me over her shoulder as she spoke.
I pounded my cock into her liquid core and buried it balls deep when it started to spit. I came hard and cum spilled from her hole into David's waiting mouth when I pulled out.
"That's it baby," she cooed as she watched her husband swallow my first load of cum. She lowered her well fucked pussy to his face and he obediently licked cum from her quim.
We moved upstairs to their bedroom and climbed under the covers of the big king sized bed. Gwen turned on a exceptionally graphic porn where bisexual men and women fucked and sucked anyone and everyone like a roman orgy.
Gwen lay between David and I. She stroked and squeezed our cocks and then moved down so her mouth was next to our semi-flaccid dicks.
David rolled over to face me and pulled me close. He pressed his lips to mine and kissed me deeply as his wife took turns sucking both of our growing dicks. She got us both hard and then reached into the night stand for some lube. I assumed I would be on the receiving end as she lubed her husbands cock but instead she laid down on him reverse cowgirl and eased his dick into her big round ass.
"Fuck me lover," she said to me as her eyes rolled back with the mix of pleasure and pain. I climbed between both their splayed legs and sank my throbbing hard cock into Gwen's wet pussy. I could feel David's cock rubbing against mine separated only by a thin membrane and the sensation was intense.
I fucked Gwen with long slow strokes as she bounced on David's dick. Gwen came hard and David followed quickly there after as we double penetrated his wife.