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  1. DIARY OF A GIGOLO 1
  2. DIARY OF A GIGOLO 2
  3. DIARY OF A GIGOLO 3
  4. DIARY OF A GIGOLO 4

DIARY OF A GIGOLO 1

Categories Diary, BDSM, Bi-sexual, Cuckold

Authror: CecilBCK

Published: 16 June 2018

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I was in my early teens when I first realised I had a much bigger cock than other boys my age.

I copped lots of good-natured ribbing about it when changing while playing various sports.

By the time I was twenty I had lost my virginity and very much enjoyed both males and females being impressed by my cock as well has having them pleasure it.

At twenty-two years of age I met a business lady who was a long way from home. Apparently she was married to a man who was the size of a jockey with an appendage of that scale. She had never had a bigger cock than his and was most impressed with my cock and my stamina. She also gave me the best blow job I had ever had at that stage of my life.

At twenty-five years of age I was far more sexually experienced than other men of my age. By then I had learnt much to my satisfaction that some men and women were prepared to pay for my services.

One older lady convinced me to set up a web page with contact details and a bio so I could offer my services. She even measured my cock with a tape measure she ‘just happened to have handy’ while I had a full erection, while she was sucking me. Her girlfriend was watching and wrote down the measurements.

“Wow, incredible, eight and a half inches long, and five and a half inches in circumference.”

By now I am in my mid-thirties. I run a legitimate business in the home decorating field, which also gives me the opportunity to meet lots of wealthy women.

I am white, Anglo-Saxon, five-feet ten inches tall, weigh 180 pounds and have a constant all over sun tan as a result of living in a warm climate. I eat and drink sensibly and exercise regularly.

I have some basic rules. No unprotected sex. Males can suck my cock, but no intercourse. Multiple clients are fine at negotiable rates.

When I meet my clients I always dress ‘smart casual’. When I undress for my clients, or they undress me, I always like to be wearing very brief underpants to highlight my cock and tease clients.

My favourite is a white athletic jock strap to contrast with my tan with the front part removed worn underneath skimpy briefs. When I remove the skimpy briefs my cock is framed by the jock strap and the thin straps of it on my well-formed arse look and feel good. And I love the feeling of my black and chrome figure-eight cock ring I wear for extra special clients.

I love the comments I receive when I undress, such as: “Wow. Magnificent. You are hung like a horse. Magic cock. Hello big boy.”

You might like to read about some of the experiences I have enjoyed and been paid for:

Margaret had heard about me and she wanted to arrange ‘something very special’ for her girlfriend while she watched. Margaret introduced her self when I arrived wearing stiletto heels, very tight fitting white slacks and a black silk blouse with just the bottom button done up. She was a knock out looking woman of around fifty and the effect of her cleavage in her unbuttoned blouse with no bra and nipples protruding into the silk went straight to my cock.

“You appear to like my appearance,” she smiled. Let me introduce you to the birthday girl, Julie. In the next room her friend Julie was sitting completely naked in a carver chair with her arms fastened to the chair with masking tape.

A little younger than Margaret she had a firm and sexually attractive athletic body.

“Julie has had a lesbian lover for two years. She is wondering if it is such a good idea and she hasn’t even seen a naked man for three years. I want you to show her what she has been missing. And I want to watch and enjoy. Can I help you undress?”

Without waiting for an answer she had my shirt and trousers on the floor in a flash. I had worn black briefs over my jock strap and both women had their gaze focused on them. Relishing the attention I dropped them to the floor exposing my very erect cock poking out of my crotchless jock strap.

“Fuck that is huge,” they both muttered in unison as Margaret removed her blouse, exposing a brilliant pair of tits with very erect nipples. She then removed her slacks to expose brilliant legs topped by a firm and well-rounded arse.

“I want you and I to show my friend Julie what she is missing out on in her lesbian relationship,” Margaret teased as started stroking my cock very close to where her friend was sitting.

“You are a big boy. A very big boy,” she murmured as she knelt in front of me licking the sides of my cock. “Can I suck your cock while my friend watches?”

She does and I tell her she is very good at it as she rakes her nails along my arse cheeks. I can see her friend becoming very agitated and straining against the tape binding her arms.

“Are you sure you want to remain a lesbian? You could be fucking this magic cock if you change your mind today,” she teases as scratches my balls, then squeezes them.

I can see her friend Julie is enjoying watching me receive and enjoy a very good blow job.

To tease Julie even further she stops sucking me and positions me in front of her in the chair so that the tip of my cock is touching her cunt lips.

“Open your legs and feel what you have been missing as a lesbian.”

She does and she is very wet as I manage to slide the tip of my cock into her, then some more.

“Oh fuck, that is so good. Quickly, untie me so I can have all of him. I want that gorgeous cock right up me. Now.”

As soon as Margaret unties the masking tape binding her arms Julie is all over me, hands raking my chest and arse, then two hands stroking my cock. She leads me to a double bed, and Margaret follows. Julie lies on her back, parts her legs and growls, “Fuck me big boy, fuck me, fuck me, give it all to me.”

I do and I can see Margaret watching very intently with her legs wide open and teasing her very erect nipples.

“Is he good Julie?”

“Fucking fantastic. Never seen or had such a big cock. Never ever.”

After two years of lesbian activity, she orgasms on my cock over and over, in quick succession.

I look up to see what the whirring noise is and see that Margaret is working a large vibrator in and out of herself.

“Come and masturbate for me and finish yourself off while I watch. I love watching a man masturbate and always wanted to see it happen with someone so big.”

To help me she scratches my balls and arse with her free hand as she keeps using the vibrator. Then she squeezes my balls and watches the pleasure on my face.

“I am going to cum very soon, very soon. Your big cock is such a turn on. Cum with me. Use two hands. Love watching you masturbating,” she screams as we orgasm simultaneously with her friend watching.

Suzie phoned and asked me if I was available to please both her and her husband. She told me they were in their early forty’s, successful business people and they liked to share a man around once a month.

I arrived at their penthouse at the appointed time and was pleasantly surprised to see they were an attractive couple and both sun tanned. Suzie was a German blond with a slight accent and her man was Austrian.

“Watch us undress, then we want to watch you get naked,” she said.

She had his shirt and slacks off in a flash and I was disappointed to see his penis was only two inches long, though he had an athletic body. Then he undressed Suzie. All she was wearing was a loose fitting dress with a long zip down the front, which he slid down slowly exposing Suzie’s brilliant cleavage. She shrugged out the dress letting it fall to floor and stepped out of it. Brilliant body with large, firm tits and nipples to match, very good legs and a well shaved pussy.

They were straight down to business. “We will toss a coin to see who has your first, ya? We both want to bring your cock to orgasm. The loser can watch.”

Suzie was the loser and helped me undress, loafers, slacks, shirt, bikini briefs and then my crotch-less lock strap. “Your cock is rock hard already, you must like my body. Sit in that chair and my man will start on you while I watch. Can I tease your nipples while he sucks you?”

I can see Suzie’s body in a wall length mirror and focus on it in order to keep my erection as her man teases my cock with his fingers and then takes it into his mouth. Surprise, surprise, he is very good and obviously very experienced at sucking a man’s cock. Suzie was standing behind me teasing my nipples and offering advice to her man. ”That’s what you call a cock. Huge. Not like your wimpy thing.”

Then to me, “He is very good at cock sucking isn’t he. I can tell you like what he is doing to you. Wait until you have me though.”

Then more advice to her man, “Scratch his balls, squeeze his balls, lick both sides, take more of it, take all of it.”

He does all of those and is determined show both of us how good he is with another man’s cock. He manipulates his lips and tongue with a man’s strength around my rock hard cock.

“Is he good baby?” Suzie asks, though neither of us sure which one of us she is asking.

I can’t hold out much longer as Suzie squeezes my nipples and tells him in a very agitated voice, “Scratch his balls, squeeze his balls, do it harder, harder, make him cum while I watch.”

“That was really something,” I tell them both as Suzie cleans me up with a warm towel.

“My turn now, while he watches,” she smiles at both of us. “You have lost that beautiful hard on you had. I will see what I can do to get it back for all of us.”

“Watch what I can do,” she tells two men as she takes my cock in her hand, strokes it, licks it and kisses it, then takes it into her mouth. The different feel of a second person’s mouth on my cock and her naked body has me rock hard instantly.

I promised earlier, “Wait until you have me. My other men all tell me I am very good. Some even say, very, very good. Put your cock ring on for me. Better still let me put it on for you. That is a big size and it is still tight on you. I love the way it wraps around your balls as well. Does it feel as good as it looks?”

It does I tell her as teases the sides of my cock with her tongue. She tells me to lie on my back on her bed. “Love your big cock. I want to use it to pleasure myself.”

She sits on my cock facing towards my feet and her husband. Until then I hadn’t realised how good her arse was, large but perfectly proportioned and dimple free.

“Love looking at your gorgeous arse while you are fucking my cock.”

“Good, most of my men do. Forty inches. Put it in your hands under it and slide me up and down the full length of your rock hard cock.

I do and she is very good in that position. I can feel her squeezing and alternating her cunt muscles against my cock and the feel of her big arse in my hands is an added turn on.

“Wish all my men were as big as you. Love your big cock. Your bio says you can keep it up for an hour. Let’s find out.”

She rides and teases my cock with great skill as she scratches my balls very teasingly. I watch in the mirror as she alternates by teasing her long, rock hard nipples. And watching her very well formed arse sliding up and down my erection is a constant turn on.

“I’m ready now,” she says looking at her husband thirty minutes later.

He approaches us with a cane in his hand, raises it and swings it onto his wife’s arse with barely enough time for me to get my hands out of the way.

“Again, harder,” she instructs. “You know I like it. That is so good while I am riding this huge cock. So very good.”

The next time I can feel the cane hitting her arse on my cock as it leaves a red welt on her arse.

“Three, four, five, one more like you always do. I love the pleasure and pain. I think he does too. Put your hands under my arse. Slide me up and down on your big cock. That is fucking magic, fucking magic. I’m going to cum. Cum with me.

“I told you earlier my other men all tell me I am very good. Some even say, very, very good. What do you think?”

“That really was something I had never had before. Feel free to call me any time.”

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