Who would have thunk it? Me, Thomas Avery Jenkins, the well-known ladies-man, a cocksucker. How did that happen?
I was born into one of the finer Irish families in Boston, whose wealth had been depleted during the great depression of the 1930s. After leaving the military following WWII, my father began an earnest drive to restore the family’s wealth.
Even though, he was no longer wealthy, he had great connections and he took every advantage. The country was on an economic rebound following the war, and by the time I was born, my father was well on his way to achieving financial success. Most of his business dealings were legitimate, but some were not. On the surface, he was an enterprising business man.
Dad married well and that went a long way toward his success. My grandfather on my mother’s side was, a successful bootlegger during prohibition importing Irish Whiskey through Canada.
I was born September 4, 1948. At age six, I entered Kenley Academy, an exclusive all boys school where I excelled in my studies and later in athletics. By the age of sixteen, I had taken on the good looks of my father and was attracting the attention of many young ladies, and even some that were not so young.
I had not reached the age of seventeen yet, when a Mrs. Robinson type, deflowered me and took away my virginity and innocence. Her name was Mrs. Henrietta Marley. I not only got my first pussy from this high tone lady, but, my first blow job, as well. I was blown away by the experience and vowed she would not be my last. I wanted to become a gigolo and fuck as many of these high society bitches as possible.
All I could think of back in school was how much I enjoyed fucking Henrietta, and I would masturbate incessantly.
Apparently, Henrietta had spread the word among her lady friends that the young handsome Thomas Jenkins was well endowed and was available for the taking. Those that had a penchant for younger men would make their intentions known to me and soon I was fucking a number of wives from the high society crowd.
Henrietta taught me the finer points of orally servicing women and soon word spread of my cunnilingus skills. This attracted a certain Mrs. Constance O’Day. The oral sex we had was amazing. I swear this old broad could suck a golf ball thru a garden hose and she was just as impressed with my oral abilities. Constance was far from the best fuck I was enjoying, but she was by far the best cocksucker. However, Henrietta remained my favorite, perhaps because she was my first.
I continued fucking these fine ladies thru high school and college. And later learned that my father had fucked many of them as well.
After college I joined my father in business. I was shocked to find out that his legitimate import business was merely a front for a criminal enterprise. He was smuggling diamonds and other precious gems to avoid import duties and taxes. A very lucrative business. He was extracting high fees for his services.
Some of his business clients were from the crime underworld. Scary men who had trophy wives. Trophy wives that caught my attention. After years of fucking the old broads, these younger gorgeous ladies looked mighty appetizing to me.
I had developed a smooth sophisticated way with the ladies and gained a reputation as a silver-tongued devil.
Using my talents, I hit on Tiffany Colombo, the wife of an under boss. Tiffany was starved for sex as her hubby, Danny Colombo, had long neglected her for strippers at his Luv-A-Go-Go night club.
She was ripe for the taking and take her I did. She was one hot minx and we began an affair where we fucked like rabbits.
She loved lots of foreplay, as I did. She loved it when I licked her from head to toe. Especially when my tongue snaked thru the folds of her pussy lips. She was the first woman I ever made squirt, which she did, when I sucked her clit like a little cock.
By the time I entered her cunt with my big cock, she was on fire. Her pussy was hot, it was like putting your cock in an oven. I could not understand why Danny wasted his time with the skanks at the Luv-A-Go-Go.
We fucked so much and often we got careless. Danny had become suspicious that Tiffany was fucking around and had her tailed. Danny was informed she was meeting me in my apartment.
One day, while I was down eating her sweet pussy, Danny barged in as Tiffany was screaming, "Yes suck that clit like a cock!”
“What the fuck is going on here.” roared Danny.
“So, you like sucking a clit like a small cock, perhaps you would like sucking a real cock too,” Danny said.
Cold shivers ran thru my body, as I looked up and saw Danny and two of his thugs.
Then Danny opened his fly and out popped his cock. I thought I had a big cock, but his cock soft was almost as big as mine when hard. How big does that thing get, I wondered. I was simply mesmerized by the sight of it. I had never in my life considered sucking a cock, but the sight of Danny’s cock was having a perverse affect on me.
Danny presented his cock to my lips, and I started to speak, but before I could, Danny inserted his cock in my mouth. I felt his cock began to pulse and grow in my mouth. Instinctively I began sucking his cock. Damn I was enjoying this. I realized, for the first time, why the great cocksucker Constance O’Day enjoyed sucking cock so much. It did not take long before Danny nutted in my mouth.
I started to gag when Danny said, “swallow cocksucker,” which I did, noting how much I liked the taste of cum.
Before Danny left, I had sucked off both of his thugs.
Danny informed me that he was pleased with my novice cocksucking and expected me to only get better, which over time, I did, including developing the ability to deep throat.
By the way, Danny’s cock turned out to be over nine inches. And deep throating that monster took some real skill.
Danny and I have an arrangement, I still fuck Tiffany, but I’m now his personal cocksucker.
That is how Thomas Avery Jenkins, the ladies man became a cocksucker.
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