The Jiggly Gigolo

For years I'd had sex with some fellow employees, customers or their employees, usually after servicing heating, air conditioning or other systems. It had started shortly after I'd hit 260 lbs. and continued until Gary and I went monogomous in the early eighties.

Today I read the newspapar and came across an article about a "college" that trained whores and hustlers in Frisco. It went into details like business sense, customer service, ethics and everything that legitimate businesses would need.

I had been dicking on the job for a couple of years before I was introduced to the escort business.

My first time screwing customers was the associate minister of a church. He was a nerdish man in his late thirties who had seen my dick under my gut when I pissed in the church mens room. He was plain looking and noone could ever guess that his wife wasnt his only sex partner. As a matter of fact my cock wasnt the first one he's sucked judging by how good he sucked mine and swallowed my load with my dick still in his mouth.

I then had other sessions with a business owner who had dentures he took out and then at a city councilman's place. He claimed to be a city councilman but I'd never seen his name on the city roster. His ass was just right for my dick and he liked getting fucked as much as I liked cumming in him. He was also able to take my manly weight on him when I fucked his ass.

I had a few friends I fucked off the job and in the baths and sex clubs but for a while I was getting my rocks off at work and jobsites. It was convenient for me as well since I was fucking on the clock and didnt have to go out at night for a piece of hole. The bosses were part of it as they had also fucked the less masculine employees and some were versatile as well as bottoms. Pat was also a bottom who worked the same jobs and we had a good thing going. I had the bottoms and versatiles who didnt want reciprocation and Pat serviced tops and versatiles who didnt need to get dicked. Some large jobs were also great when there were versatiles or one of each type of men. A few times I'd fuck someone and turn him on then he'd stick his dick in Pat and get off. Other times I'd be fucking someone while Pat was wrapped around a man's love muscle. My tricks ranged from a nineteen year old who wanted to enjoy servicing a masculine man to a couple of oldsters with full dentures who gave me great head. My uncut often cheesy cock was part of the attraction since many cocksuckers were "mice" like Pat and my friend Mikey were and most likely still are. I didnt question it too much, just enjoyed getting my rocks off in the dudes. 

Pat had his clientele as well. His studs were usually men who were unable to score anything but a whore who'd rip them off by overcharging them due to their looks, age, hygeine or attitude. Pat was as much of a mouse as Mikey and two had fought over one fat old man with a donut of cheese under his foreskin and a crotch-odor that could have turned my stomach. At least Mikey had some shred of standards. He preferred us cleaner men with the worst trick being Hank after a week without a shower. Pat was so low that one time he was working on an adult facility as it was called. He had called the office asking for some replacement ducting to replace some old flex duct so I brought it out on my way to an afternoon call. I went in, looked and asked an old looking fat man if he'd seen Pat. I found the pile of old ducting and looked for Pat, decided to bring in my load for him and look fo him later. I returned with a dolly of straight ducts and another box of elbows. I then heard something and went to look. The old man's 44 year old son was laying back while Pat was sucking him clean. I almost wretched. The dude was a fat mouth-breather with dirty long nails, rotted teeth and the odor of poor hygeine. I turned before they could see me and headed for the mensroom. 

After I was finished hurling I dumped off the rest of the ducts and left. 

I can smell after a day's work in hot attics and stink after a week in the summer without a shower but that dude stunk bad, almost like the bums Hank pissed on in grubby alleys down town. 
I had a job at a plant once which added to my income. Part of my appeal was that nobody would ever think that anyone was having sex with a fat man like me and the dudes took advantage of that to swing on my uncut 6" shaft. I was in the wash room when a man came in to piss. He recognized me from a couple of years ago. We shot the shit and he sucked me off, then asked me if I had a suit. I told him the one I had didnt fit me since I'd gained weight. He said he'd get me a new one if I'd take an associate of his out for what he described as a business lunch. I agreed and asked him about the man. He told me he was in hs late forties and wanted to have a date disguised as a business meet.

I met the guys a week later after work. I decided that a decent suit would be useful and getting it free was even better. The man was an inch or two shorter than me and average weight. He wore glasses and had clear nail polish, a comb-over and looked like an executive type. We agreed and the next saturday we went to the mens shop. We both selected the suit with the help of a distinguished looking bearded man and a little fairy who had a negative attitude towards us manly heavyset men. The bearded man was nice to me and had to admonish the sissy. I got a good classic style in dark gray which would serve me a long time. My friend and I were invited by the store manager to a piece of his little punk. We took him up on his offer a week after my first escort date. 

The date was a success. We had lunch at a higher class place on his tab and then took a cab to his place. We started off at his place with a hug and kiss, then we stripped. He appearantly liked the bear I was and dropped to his knees in front of me. His head was under my gut and making my dick feel great. I swelled in his mouth as he sucked and licked and savored my foreskin and the little bit of smegma i had under it. I felt as well as heard his delighted humming on my dick which felt good in his mouth.

I then yanked back and suggested that I'd be more comfortable laying on the bed. He agreed and kissed my dick. I lay on my back with my legs closed which he straddled. He resumed sucking my cock and I didnt fart like I usualy do with lesser dudes.

He sucked like an expert and soon I came in his mouth. I figured I'd shot half a dozen spurts into it before I thrust a few times to get more off in it. He not only swallowed my cum like he had swallowed my little bit of cheese but kept sucking for several minutes while I told him how well he sucked my cock. I also felt his dick on my feet dripping pre-cum on my toes and hoped he was the kind to lick feet. He wasnt but I'd have Pat lick my slimey toes later. 

The dude sucked off of my dick and kissed it like his friend had told him to.

We shot the shit while he smoked. That was his only bad habit bsides his polished longish fingernails. He told me about growing up and having fucked his first broad in junior high school, knocking up another broad in high school and his dad being pissed at having to pay for the abortion. In college he fucked another broad as part of a train and after the last man left he scarfed her out. He found out he liked the taste of cum. 

He had had first gay sex as part of a train some men pulled on a sissy to punish it for being effeminate. He said the asshole was better than a woman's cunt and went on to meet and fuck more dudes when he learned about a sex club in the downtown industrial area.

He got his first BJ from a queer and liked it. He then met a large man with a small dick and let the stud break him in. He sucked the man and swallowed his load. They met every week and then the man wanted some of his ass. He agreed after the stud convinced him it would be gentle rather than the way they had turned out a punk. The big man enjoyed the good feeling of popping his tight cherry. It was painful but he got used to it over the next month and the man enjoyed his tight ass.

He had to be very discreet due to his social position which limited his gay action. He was glad to find I was willing to date him. 
After I'd told him about my first times I was ready for my piece of his ass.

He sucked my dick hard and left it wet. I greased up while he turned over, lay on his stomach and spread em. I mounted him and lined up my shot. He didnt need to giude my dick to his asshole since I'd been fucking ass for years by then. He winced at first when I penetrated him but I got it up his ass which was firm and tight around my 6 inches. I hilted myself and lay my manly 280 on him to let him feel the weight of a real man on and in him, and fucked him. As with most assholes I fuck his pain and discomfort turned into pleasure and he got turned on by the experience of a real man fucking him. I liked his ass which was about the right tightness for my whole cock. I had a beautiful piece of his ass and came just after he did. I kept thrusting to make my dick feel really great and pumped my eyebrows behind my glasses in victory, feeling as good as the stud in Deliverance after he came up the dude's ass. I had read the book in the '70's and liked the man conquering that fat punk. Of course I was pissed that the stud's partner was murdered before he could get the piece of mouth the character played by Burt Reynolds owed him. 

I lay on and in him while he told me he came from the experience and loved my studliness. I was going to pull out but he begged me to leave it in which was fine with me although I had to deal with his after sex cigarette which I would have enjoyed putting out on his ass cheeks to force him to really tighten up around my dick.

We had several repeat dates off and on but he found others who fucked him for free and were discrete as I was.

I had a number of dates, about 25-30 or more in all, ranging from a skinny junior executive who got sand kicked in his face at beaches to the kinds of high-level he-man studs who kick sand in the faces of sissies at beaches yet had long nails, loved to suck my cheezy cock, swallow all and take it up their powerful asses.

One was a muscle-bound studly looking guy yet he treated me like his best buddy and sucked me dry as well as loved getting fucked by me. He also spread his ass and lips for Slim Jack and loved his studmanship too. Our last series of dates was with Slim Jack and I simul-fucking him in both ends and him paying each of us my usual rate. We'd fuck him, let him rim us or lick our feet, then we men would swap ends and fuck him again, yank out, go into the bathtub, shove our dicks back in and piss in him.

One man had a thriving business and a son in his twenties who was in heat. He thought someone like me would be what he considered a safe date for his slightly less than masculine son. I had kissed the man and then he introduced us. His son and I hit it off because he liked my bearish masculinity and felt safe after getting burned a couple of times. 

Our first date was at the son's pad. It felt good when he sucked my dick. If I had any cheeze he never mentioned it but sucked me dry and kept sucking after swallowing my load. He had a good collection of smut. Some of the magazines were good and a couple of the movies were great. I liked the one with the fat man fucking a skinny one although only one man had masculine bitten nails and was only shown for a few seconds fucking some twink type. Another film had a cocksucker kneeling before a fat slob with a donut of cheeze under his foreskin. The perv sucked the man's cheeze and sucked him to orgasm. The shot of the cocksucker gulping it was good. Afteer we finished that I fucked his ass. he was glad I'm only 6" and uncut so I wouldnt hurt him too much and he came from getting fucked. He said he wasnt too turned on byme at first but after he had cum from my dick frigging his prostate and felt my manliness he wished we were lovers.

it was a great relationship. The punk's dad paid me by the week and I fucked the punk whenever I needed a piece of ass or mouth unless I had another date.
That relationship lasted a about a year and a half until the man was relocated.

One great time was nice for me but expensive as hell for the "john". It was a week vacation with a man who resembled me but had a full head of wavy blond compared to my balding curly brown. We posed as father and son but I knew it wasnt convincing even though he was 25 years older than me. We abandoned the scene ans just vacationed as two friends and spent a lot of time in private and in one of the ajoining rooms in some places and in a double at other places we stayed. He weighed about 230 compared to my 280-plus. Sex was in various positions ranging from my favorite of laying on my back while he sucked me off to him on his stomach while I fucked his ass. I also fucked him with him on his back with his legs up and spat in his mouth which he swallowed. We also did french with him kneeling before me, his head under my manly gut while I admired myself in the mirror. We also spent nights with my dick in his mouth. I was pleased when he asked me to piss in his mouth when I needed to piss or felt like pissing in his mouth. Needless to say I took advantage of that offer as often as possible and used his mouth the rest of the trip whenever we had privacy. I was also hoping he'd rim my fat ass but he never went that far although we both got rimmed after I fucked his ass at a baths. I taught him hoe to fart in a rimmer's mouth. The second time he got rimmed was a hot. he farted the cum I pumped up his ass into the freak's mouth and the freak swallowed it. I was disgusted but made up for it by taking a piss in the freak's mouth after I took a shit and let him rim me instead of wiping my ass.

That was the best vacation I ever had! I got paid as much as I did with an hour of overtime a day and had great sex.

I picked up the nickname "Jiggly Gigolo" due to the fact that my fat has shaken and jiggled when I walked or made any sudden motions. My gut still shakes now. My fat also shakes or rolls when i fuck someone depending on how fast I thrust in the asshole or the cocksucker's mouth. I had felt it a deterrant to scoring at first but that ended up as part of my bearish "charm" along with my uncut cock, masculine deeply-bitten nails and overall masculinity. I'm also one of the men who never has to take his glasses off to have sex since I'm a top and only my genitals are involved with sex with other guys although I do kiss my fellow tops as long as they never suck cock or rim or kiss anyone who does.

I had started balding in my thirties which added to my manliness. I'd started wearing glasses and biting my nails at eighteen and began gaining weight a year later after moving out and adopting a gainer diet although I weighed almost 200 as I was. I just felt better heavier and was stronger. My weight also helped in my job and was also able to use my weight to my advantage when I fucked ass with the bottom laying on his stomach. I'd just lay on him to keep him in his place when he wanted me to stop or pull out before I came in him.