DIARY OF A GIGOLO 4
Introduction:
Janet wanted to watch her boyfriend suck a ‘very well endowed man’ while she watched.
When I arrived Janet was very effusive and obviously excited at the arrangements she had made. “You are a good looking man. Can’t wait to see your big cock, especially with my man Tony sucking it.”
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.
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Janet wanted to watch her boyfriend suck a ‘very well endowed man’ while she watched.
When I arrived Janet was very effusive and obviously excited at the arrangements she had made. “You are a good looking man. Can’t wait to see your big cock, especially with my man Tony sucking it.”
She was a plain looking woman, around forty-five years old, but, I mused probably with a really good body under the very plain, sack like dress she was wearing.
“Come into the bedroom and let’s get started. I am paying for this so I want to play with you first before Tony has you. Is it true you are eight and a half inches?”
“My cock loves a challenge, especially when turned on by a naked woman,” I smirked as I stripped down to my jock strap.
Without a word Janet shrugged out of her dress exposing her voluptuous naked body. Heavy slightly sagging tits with long erect nipples, trimmed pussy and good legs.
“Does that turn you on?” she purred as she pulled my jock strap down exposing my semi-erect cock. “Let’s see if you do have eight and a half inches. What can I do to help?”
At that moment her boyfriend Tony walked in dressed in very tight gym slacks, bare-chested and sat in a chair in front of us, side on to a large wall mirror. He was an attractive small man, though it was difficult to understand any attraction these two people may have had for each other.
“We have been discussing this scenario for days,” Janet said as she stood behind me and teased my nipples.
“You can start sucking his cock now Tony. You wanted a very well endowed man and that really is eight and a half inches. I am impressed and envious. You have my permission. Make it good for all of us.”
He was very, very good and obviously experienced. After a few minutes I watched as he stopped sucking and filled his mouth with small ice cubes, then recommenced sucking. The sensation of hot and cold on my cock was magic, especially as he alternated scratching and squeezing my balls, without speaking a single word.
Being able to watch my rock hard cock being pleasured by another man in the mirror with Janet watching naked and offering advice and encouragement to both of us was a real buzz.
It got even better when she started tongue kissing me with my rock hard cock in her man’s mouth while he worked on my balls.
And when she took some ice in her hands and rubbed it into my nipples while her man bought me to orgasm I was very well pleasured.
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Mary was a newly retired head mistress from an exclusive girls school. Over the phone she told me she had been divorced for years and was in need of a man to give her some attention. She told me she was fifty-five, a size 14, around 68 inches tall and still attractive.
At her insistence we met in a coffee shop so she could check me out as she was unused to paying to have a man. She was dressed in a black shirt and very tight fitting white slacks. What a pair of fabulous long legs with very well developed long thighs she had! She was the centre of attention and the male staff were mesmerised. “You fill those slacks beautifully,” several waiters and a customer told her.
She was beautifully spoken and super-confident, as would be expected from the head mistress from an exclusive girls school. “I have booked a motel room close by. I hear you are very well hung and I want you to fuck my brains out.”
As soon as we were in the door Mary was over me like the proverbial rash. Tongue down my throat, which really turned me on and gave me an instant erection. She had me undressed to my briefs in a flash, then pulled them down.
“Wow, hello big boy, what a cock and thick as well, magnificent. Lay on your back on the bed,” she instructed in the very firm tone.
“My legs have always been my strong point, and I can tell your cock likes them,” she smiled as she removed her slacks, then her shirt.
“My tits and arse are pretty good for fifty-five old as well, I think.”
She was correct. A big, though very well proportioned and still firm arse and good large tits that were starting to sag with big nipples.
She mounted my very erect cock and ever so slowly slid the full length of it into her very wet cunt lips. Nothing quite like a sex starved older woman who wants to fuck you silly to pass the time of day.
As she slid up and down my full length and ground into me, her language became very coarse and rasping. “My cunt is sopping wet for you. Fuck my cunt big boy. Fuck it harder, harder, much harder. Give me every bit of your big cock.”
After three huge screaming orgasms she remounted me so that her arse was facing me. Watching a very good, full size 14 arse, sliding up and down your rock hard cock, while you are holding it with two hands and being repeatedly told to, “fuck my cunt big boy,” was enough for us to orgasm together.
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June phoned and told me she was in town from another country on business. “I have been here for a week and the only local men I have met are boring old business types. And I am hanging out for a really good fuck, at least an hour. One of my female associates gave me your number. Are you available tomorrow afternoon?”
She was staying at the best hotel in town with a room on a very high floor with a commanding view of the harbour. As soon as she opened the door to let me in she repeated what she had told me on the phone, “I am hanging out for a really good fuck, at least an hour. You came highly recommended. Looking at you I don’t think I am going to be disappointed.”
Women who are able to articulate what they really want without any inhibitions, when it comes to sex are a real turn on for me. My first impressions were of a still very attractive and confident honey blond Nordic woman approaching fifty, whose face suggested she was perhaps slightly past her very best years, though with a stunning body. She was dressed in all black; silk blouse, knee length skirt, black stockings and stiletto heels.
“Undress for me and show me your cock. I am absolutely hanging out for it.”
I do and she whispers, “Wow, you are magnificent,” as she partly undresses for me, revealing unrestrained and very firm 38D tits with protruding nipples.
“Lick my nipples for me, I love having a naked man licking them, just love it. So does your cock I notice. Now take my dress off for me. Do you like what you see now? I purchased this garter belt and stockings especially for you.”
June has the type of body every man dreams about. Her garter belt frames her trimmed pussy, highlights her wonderful legs, accentuates her slim waist and very firm and well-developed arse.
“Like what you see? You are a lucky man. Before I fuck you I am going to masturbate with my vibrator for foreplay. Would you like to watch?”
Without waiting for an answer she sits on a chair with her legs straddled over it’s arms and starts teasing her clit with a vibrator, then insets most of it into her obviously very wet cunt.
“Stand in front of me so I can suck your huge cock while I masturbate. Mmmm, that’s heaven,” she manages to mumble as she orgasms.
“Enough foreplay, now let’s get serious. Show me how good you are. I am multi-orgasmic and I want you to fuck me to at least five orgasms with that magnificent cock.”
We start off in the missionary position and June wraps her legs around my back urges me into her very wet cunt.
“That’s fucking heaven,” she screams as she orgasms after just a few minutes.
“Now fuck me from behind. Harder, I want to hear you slap into my arse. You are a really good fuck, and that huge cock is a bonus,” she purrs as she tenses then orgasms again.
“Now doggy style,” she instructs as she positions herself on all fours. “Give me all of your big cock. Slam into my arse.”
She screams and orgasms again. “Now stand me up against the wall and fuck me from behind. Grab my arse cheeks and slam into them.”
Another orgasm. “You really are a good fuck. Let me show you what I can do,” June smiles as she lies me down on my back on the bed and slowly eases her lush body onto my cock.
“I do my kegel exercises every day,” she smiles as she squeezes and then releases her cunt lips along the full length of my cock. “You must be ready to orgasm by now? How much longer can you hold out for? Don’t hold back and I will cum with you. Cum for me baby.”
She is very good in this dominant position and she screams as we orgasm together.
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Barbara wanted to cuckold her much older husband with his permission – and with a huge cock, she told me over the phone. Having an attractive and very horny older lady sucking your cock while her husband is getting off on it and obviously enjoying it really is a buzz.
When I arrived at their suburban home I was not sure what to expect. “I’m Alex, Barbara and I have been looking forward to your visit. You can call her Barb.”
He was around fifty and looked and sounded like a typical accountant. “Barb is waiting for us in the bedroom. We do this on a regular basis and I really get off on it. So does she.”
The first thing I noticed in the bedroom was the subdued lighting and full-length mirrors on all the available wall space as well as on the ceiling over the bed.
“Hello baby, do I turn you on? I hope so because I want to cuckold Alex big time, with the biggest cock he has ever seen.
Barb was standing stark naked apart from stiletto heels in a corner with her back to me. I could see her face and front view reflected in the mirrors as she held my gaze.
“My friends who have had you told me you like good arses. Doe’s my big arse turn you on? Don’t answer me, let your cock do the talking. Alex likes to lick and kiss my arse while my cuckold watches.
Right on cue Alex commences licking and kissing her arse. “Barb is twenty years younger than me. She is a size twelve to fourteen with a very well developed body and an arse to die for. Take your clothes off and show us both your big cock.”
I do and I am very turned on by watching Barb have her glorious arse licked and reflected in all the mirrors.
“Your cock is awesome, magnificent, we have turned you on. Can I suck it now while Alex watches.”
Barb positions me so I am standing while she sits on a stool in front of me while her man keeps licking and kissing her arse. “Absolutely awesome baby. That is a mouthful. Are you looking forward to fucking me really, really, good while he watches? Do you like me teasing and squeezing your balls?”
I notice that Alex is now naked and playing with his roaring five-inch erection. “Fuck her from behind on the bed while I watch. Enjoy her glorious arse, fuck it really hard,” he instructs. “I want to really enjoy watching you fuck her with the biggest cock we have ever had.”
And he really did enjoy watching. He walked around the room so he could watch from all angles as he stroked his erection watching me fuck his wife while he offered encouragement to both his wife and me.
“Pull your cock out so I can see how big it is. Mmmm, awesome. Now slide it back in very slowly. Do you like that baby? Does it feel good? What else would you like him to do to you with that huge cock?”
“I want to suck it and make him cum while you watch as soon as I have an orgasm. And you can lick my arse at the same time.”
Barb positions me on my back and slides her very wet cunt up and down my rock hard erection. I am turned on by how much Alex is enjoying the show as I am sure Barb is. She cums very loudly then repositions me so I am standing while she sits on a stool in front of me while her man recommences licking and kissing her arse.
She is very good at cock sucking and watching her husband masturbating while he licks and kisses her glorious arse is enough to bring me to huge orgasm, followed by her husband.
“I told you over the phone I wanted to cuckold my much older husband with a huge cock with his permission. I did and it was very good for both of us. See you next time.”
