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

DIARY OF A GIGOLO 3

Categories Diary, Bi-sexual, Cheating, Cuckold

Authror: CecilBCK

Published: 12 July 2018

  • Font:

After a wide range of experiences as a gigolo, I developed a preference for a certain type of client: elegant, sophisticated women aged around forty five years old, with bodies anywhere between size ten to fourteen and not overweight. They were often a long way from home on business. Almost without exception these women would be very good communicators, uninhibited and able to articulate their sexual preferences. And if they enjoyed what I had to offer and recommended me to others that was an added bonus.

Wendy told me her girlfriend Karen was ‘a jealous bitch’. “She wants everything I get. But she is not having you. I want her to watch me have a monster cock.”

When she let me into her apartment I was amazed at how spacious and beautifully furnished it was, with heavenly choral music playing. Wendy was forty something, with long blond hair, very tall with long legs to match in tight leather slacks, killer heels and attractive facial features, though almost flat chested. “This is my girlfriend Karen. She doesn’t know why you are here yet. Don’t tell her, just let her watch and find out.”

“What shall we have to drink first? Champagne surely?”

As we sipped our drinks from obviously expensive crystal flutes Wendy asked, “Can you guess what he does for a job, Karen?”

“Car salesman, real estate, engineer?”

“Not even close. Come into the bedroom and find out. Sit in that chair by the bed watch and enjoy.

“Show us both why you are here. I will help you undress. Love your suntan and you have a great body. Like that Karen? Love your bikini briefs. You take them off for us.”

I do and that leaves me wearing nothing but a crotchless jock strap with my semi-erect cock fully exposed.

“Wow, very impressive,” the two women coo as one.

“You can watch and talk to us Karen and I might let you touch and feel him,” Wendy smiled as she started to undress.

First her silk blouse, with nothing underneath it apart from bullet like nipples. Then her heels, tight leather slacks, and tiny black g-string.

“Do you like my g-string? Take it off with your teeth. Like my shaved pussy?

“I used to be a model. A bit flat chested, but my long legs helped sell hundreds of products. How long since you have had sex?”

“Three days, and I love your long legs. So does my cock.”

“Good I haven’t had sex for months, seems like months anyway. I am really hanging out for a good fuck. You should be able to last for an hour if you had sex three days ago.

“Start by licking my nipples, then I will lick and suck your huge cock. It’s even bigger than when we started. Don’t forget my bitchy friend Karen is watching. I want to make her very, very jealous.”

I can see Karen becoming quite agitated as I lick and tease Wendy’s nipples. She then kneels in front of me and kisses along the full length of my cock. She then scratches my balls with her nails and squeezes them.

“Your cock seems to like that. I am going to suck your big cock now. Remember I want you to last for an hour. Stand behind him, Karen and tease his nipples and watch what you are missing out on.”

After a few minutes she moves to a carver chair, tells Karen to sit down again and watch.

She wraps those gorgeous long legs over my shoulders. “Lick your way up my thighs, slowly, then lick my cunt. Make me cum twice, then, you can fuck me.”

Licking my way up those sensational long thighs is very exciting.

I can see Karen get up and stand behind Wendy so she can tease her nipples.

“I can stop if you want me to,” she teases. “Cum for me while I tease your nipples, while he is licking your cunt. It looks good. Can’t wait to see him fucking you Karen. Cum for me.”

And she does, right on cue, then almost immediately she cums again.

“Love you licking my cunt while Karen teases my nipples. Even better I am teasing her by having you. Now fuck me, slowly and make it last.”

Wendy still has her killer heels on. She leads me to a higher than usual table near the foot of the bed and leans over it. Her long model legs look absolutely fantastic in her heels.

“Kiss my arse while I lean over. Make Karen jealous and envious. Then fuck me from behind. We can see ourselves fucking in that mirror.

“Like that baby? I do. I love your big cock sliding all the way into me. Are my long legs turning you on? I think so.”

I sneak a glance at Karen to see if she is watching. She has her skirt up over her knees and has removed her panties. I look closer and see that she has a vibrator teasing her clitorous.

“You two are turning me on. Love watching what you are doing. And I am very envious. Hold her arse with both hands and fuck her harder.’

I do exactly as Karen asks and my erection is throbbing for relief.

“Hold on baby, I am not finished with you yet. Lay on the bed so I can sit on your cock and pleasure myself. Do you like me sliding my cunt up and down your huge cock? Tell me, I need to know?”

“I love what you are doing, just love it. You are very good. I want to get on top of you now with those magic long legs wrapped around me to finish fucking you. Judging by the noise she is making, your friend Karen is enjoying watching.”

And what a finale that was for three people.

A few days later Anni had organised a hen’s night for a small of group of like-minded business women, all around forty-five years of age. She had asked them to dress to impress. Experience had taught me women of that age are very often rediscovering a sex life. Their children have left home and they have time on their hands. I was expected after their dinner at nine.

To tease the women Anni announced that a guest speaker was about to address them on the state of the economy. By now they had all had a good few drinks and they all groaned as one. I walked in dressed in very smart business suit, collar and tie as someone would who was going to speak on the state of the economy with twelve pairs of eyes were focused on me.

“I am sorry ladies, I seem to have misplaced my speech papers,” I smiled.

Then on cue Anni started to play some loud, recorded music with a big beat.

“Hot in here isn’t it?” I teased as shrugged out of my coat, then my shirt.

By now the women were starting to cheer and catcall.

I strutted around the room as a tease and to seek out the most attractive and flirtatious woman. A stunning brunette in tight slacks and stiletto heels caught my eye. I dropped my trousers to the floor and heard every voice in the room making catcalls. I certainly had their attention. I motioned for the brunette to slide my briefs off revealing my semi-erect cock hanging out of my jock strap. She had her hands all over me and with a room full of inebriated women watching and calling advice I was rock hard instantly.

I walked around the room offering each woman the chance to touch my very erect cock if they wanted to.

“We had a lucky door prize, you may recall,” Anni announced. “Our man can pick the winning ticket from the hat. And the winner can have our man to pleasure them with his big cock.”

Surprise, surprise, Anni was the winner, and she really enjoyed my big cock.

Brad phoned and told me he was in trouble with his wife, Jacqui. “She found out I have been having it off with my secretary. She says she will forgive me if I fire her and watch her have sex with a well-hung man while she calls the shots. Do we have a deal?”

On arrival Brad greeted me dressed in casual clothes. He was an attractive well to do businessman, around fifty years old. “Jacqui is looking forward to meeting you. She hasn’t had sex with ne since she found out I had been cheating on her, and she is determined to have her revenge on me by making me watch her have sex with you.”

“That’s absolutely correct, revenge big time,” she said, as she made her entrance, immaculately groomed and dressed in heels, very tight black silk slacks and matching blouse. Late forties, attractive facial figures, size 10-12, a few wrinkles, silver blond bobbed hair and a very good figure.

As she walked closer she strutted and turned to show her body for full effect. Her tight slacks highlighted her arse as she walked and her obviously bra-less tits wiggled.

“Come into my bedroom. He hasn’t been allowed in here since I caught him cheating. Sit on the chair and watch us Brad. I am going to seduce this man and make you suffer.

We start kissing each other like teenagers and help each other undress. First her blouse exposing a very good pair of firm tits, 34C I muse. Jacqui quickly has me naked apart from my black g-string. I slide her slacks off to reveal her shaved pussy unfettered by knickers. Then, my g-string.

“Like your big cock. My bitch husband is big, but not in your league. And you are much thicker,” she smiles as she fondles my erect cock with two hands.

“Lay on your back on my bed. I am going to fuck you in that position. I want to be in control. Do you like having my husband watching? Does that excite you? It excites me.”

She slowly lowers her very wet cunt onto the full length of my erection and slides along the full length of my cock while holding my gaze.

“Can’t remember the last time I was in control like this. Hold my arse and manipulate me up and down you big cock.

“Mmm, that’s very, very good,” she moans as she orgasms.

“Keep going baby, I am only just getting started. Look at my husband. He is naked and masturbating. I have never seen his cock that big. He must like watching us.

“This is supposed to be punishment for your cheating, not something for you to enjoy. Though I like watching you masturbate while I am fucking another man with a bigger cock than you.

“Mmm, that’s fucking heaven,” she moans as she orgasms again, staring directly at her husband, while he masturbates.

“We should do this more often,” she smiles at him. “You can fuck me later tonight. I have had my revenge.”

Lorraine was too old to have sexual intercourse she told me. However, she was happy to pay me to masturbate for her. She told me over the phone, “I have three reactions and categories when I look at an erect cock: so what, wow, and my God awesome. I hear that you are in the, my God awesome category, so don’t disappoint me.

When I arrived she asked what she could do to give me a roaring erection before I was naked for her. That question was enough to start an erection. I looked very closely at her and liked what I saw. Despite claiming she ‘was too old to have sexual intercourse’, she was an attractive size 12-14, fifty something woman, dressed in heels, a very short skirt and loose fitting silk blouse.

“What did men find most attractive about you that turned them on in the past?” I asked.

“My suntanned legs and arse.”

“Take your skirt off and show me.”

She does as she holds my gaze, very confident of what she is doing.

“What do you think, do you like my suntanned legs? Want to see my arse naked?”

“Yes I do but your blouse is hiding it.”

“Take it off for me then.”

I oblige and her tanned arse is something to behold. She has a tiny white g-string on which highlights her very well formed almost dimple free arse, complimented by a slim waist.

“You really do have fantastic suntanned legs and arse. Let me guess, forty-three inches?”

“No forty-four, show me what you have and then you can take my g-string off. I purchased it especially for you.”

“My God, your cock is awesome, have my legs and arse turned you on? I think so. Do you like my shaved pussy? I like the power my legs and arse have on men when I walk around naked in heels with all my wall mirrors. And I love watching a turned on man masturbate. And you are the biggest yet, so get started for me. I have some oil here to get you started. Would you like me to put it on your cock and hands for you.”

She does with one oily hand on my cock as she scratches my balls with the other hand.

“Now you. Use two hands,” she instructs standing in front of me with her legs apart.

“Do want to look at my arse while you masturbate for me, or my shaved cunt?”

“Both,” I grunt. “Walk around for me. I love the way your arse moves, love it. And love your legs in those heels. So does my cock.”

“Good, I love turning a man on with my naked body and watching him masturbate, especially one as well hung as you. Does it feel good? Is it better than a fuck? Do you wish you were fucking me? Would you like me to tease your balls? How long can you last for me?”

“About one minute if you tease my balls.”

Watch out for my next instalment.

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DIARY OF A GIGOLO 3

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