DIARY OF A GIGOLO 5
Introduction:
Tanya told me over the phone her girlfriend Sue was turning fifty soon. “She has been a single lady for two or three years now. She loves telling me how good she used to be at giving blow jobs to her men. However, she keeps complaining about lack of opportunities at her age.
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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Tanya told me over the phone her girlfriend Sue was turning fifty soon. “She has been a single lady for two or three years now. She loves telling me how good she used to be at giving blow jobs to her men. However, she keeps complaining about lack of opportunities at her age. She is very uninhibited and likes to boast how she was so good that her girlfriends used to ask to watch and learn from her technique and how having them watch was a big turn on for her and her men. And she still has a good body for her age. Can I book your services for next week for a surprise for her and a few of her girl friends?”
The day before Tanya phoned me for an update. “There will be six of us, including Sue. We are all well presented professional women aged around forty-five to fifty. We have been teasing her for a week by emailing her pics of very well hung men receiving blow jobs from older women and reminding her of her boasts and prowess. Dress code for the night is smart cocktail and dresses must be above the knee.”
I arrived as arranged at nine and noticed all the women were well lubricated with six empty bottles of expensive champagne on the table. There were numerous presents on the table including two huge dildos and a range of sexy black underwear.
“I forgot tell you ladies that I had organised a present for Sue and some very adult entertainment for you. This man is the entertainment. He has something most women want, a huge cock. Would you like to see it?”
For the first time I noticed that all the women were very smart in cocktail dresses well above the knee as Tanya had stipulated. All were now sitting cross-legged for my benefit with a very good dose of thigh. Sue the birthday girl with a voluptuous size 14 body and long blond bobbed hair had the shortest skirt of all, which highlighted her long well-developed thighs with a silk top unbuttoned to just above her waist which highlighted her large tits and very erect nipples.
Sue and Tanya took my hand and led me into a bedroom so I could change into the short black silk dressing gown I bought with me. They both watched intently as I removed all my clothes.
“Happy birthday Sue, like your present?”
“Yes I do, wow, magic, huge, what a cock, and sun tanned all over. Can I feel it and kiss it.”
She does and with Tanya watching I have a roaring erection immediately.
“Put my cock ring on for me?” I ask with a smile and enjoy watching and feeling Sue slide it all the way up my erection and then fastening the clip stud under my balls.
“Your cock is awesome with that on,” Tanya observes.
They both watch intently as I put on my crotchless black jock strap and a pair of briefs over that to try and cover my very erect cock.
Then they each took one of my hands and led me back into the room where the other women were.
“Enjoy the entertainment ladies,” Tanya smiled as she removed my dressing gown as five other women smiled at me.
“It’s Sue’s birthday so she can take his knickers off for us,” Tanya announced to catcalls and cheering.
“Do it from behind, so we can watch.”
The anticipation of six women looking at and perhaps wanting my erection was real buzz.
“Wow huge, magnificent, love the way it hangs out of your crotchless jock strap, and very thick. And that black and chrome cock ring is awesome.”
“Come here big boy so I can touch it. Like me scratching your balls.”
“Can I suck it Sue, or are you going to give us a show? You have been telling us for years how good you used to be and how you like others watching.”
“Love the jock strap almost as much as your cock. What an erection.”
“Don’t waste that erection.”
“Show us how good you are Sue. This has been especially set up for you. Fuck that magnificent erection with your mouth.”
I take in Sue’s voluptuous size 14 body as she approaches me and whispers loud enough for everyone to hear, “I am wet for you. Take my shirt off and kiss my nipples. They are rock hard for you. And I am going love five women watching. Pity their men can’t watch as well.”
The women were now almost silent as they watched me enjoy Sue’s large tits and very erect nipples with my tongue and lips.
“Take my skirt off and I will suck your huge throbbing cock while my friends watch. I have told all of them how very good I used to be at blow jobs.
I remove her skirt and love the look of the thick gold chain she is wearing around her waist and the impression it makes on her almost naked body.
“Now my knickers.”
I love the look of her large and very firm arse as she takes hold of my erection and leads me to a stool in front of a large wall length mirror.
“Some foreplay before I get serious with that gorgeous cock,” she smiles as she sits on the stool. I can see her large and very firm arse in the mirror and can’t keep my eyes off it.
I notice that the other women are now standing close by, their faces flushed with excitement at what they are going to watch.
Sue runs her nails up and down my chest a few times, then teases the tips of my nipples with her finger nails. She then grabs my arse cheeks and scratches them with her nails. “Like my foreplay big boy? Not finished yet,” she teases as she reaches for an ice block.
She teases my nipples with the iceblock, then runs it along both sides of my erection, and then my balls.
“I used to be very good at this, and I love performing for an audience. And your huge cock is my ultimate challenge. Are you ready for me? How long can you hold out for? You have been erect for at least ten minutes already. See if you last for fifteen minutes,” she purrs as she takes my erect cock with two hands and licks along its’ full length, one side then the other.
“Can I start on your huge cock with my mouth now?” she asks without waiting for answer.
After Sue’s teasing foreplay the feel of her lips wrapped around and pleasing my cock is magic, while I ogle her arse in the mirror, especially with five other women watching very intently.
“Wow, never ever watched this before. Love that cock in her mouth.”
“That is really something.”
By now Sue has her hands on my hips so she can manipulate my cock into her mouth. She then digs her fingernails into my arse cheeks as she increases the pressure of her lips on my cock.
“Like that baby?”
“Yes you are very good.”
She pulls back and my cock slips out of her mouth as she gently blows on my cock. At the same time I can see in the mirror and feel another pair of hands scratching their fingernails along and into my arse cheeks. Then teasing my nipples.
I watch as Sue fills her mouth with small ice cubes, cups my balls in her hand and resumes sucking my erection with a mouth full of ice.
“Is that good baby. We have been going for almost twenty minutes. Are ready to cum all over my tits while five women watch?”
Watching how the other women are reacting while having my rock hard cock pleasured is a huge turn on and a bonus. Their demeanour ranges from agitated, excited to raw animal lust. One woman has lowered her top and is teasing her extended, very erect nipples. Another has her hand down her skirt, obviously teasing her clitorous. Another is muttering, “Watching you two is so fucking good, so fucking good, I am so horny.”
“You haven’t answered me, do want to cum all over my tits while five women watch? Are ready to cum all over my tits while five women watch?”
“Yes and yes,” I moan as Sue has just the tip of my cock in her mouth as she slides her thumb and forefinger along the full length of my cock.
“Like that baby?” she asks as she continues sliding her thumb and forefinger along the full length of my cock and scratches then squeezes my ball with the other hand.
“Cum for me baby, your audience wants to see you cum over my tits.”
She increases the pressure she is applying on my cock and balls with two hands and sucks and licks the top of my cock.
“So good, Sue, so fucking good,” I groan as I tense, shudder and have a huge orgasm over her tits as she keeps stoking the full length of my cock with her thumb and forefinger while five other women watch and enjoy.
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“Are you available next Tuesday afternoon? My girlfriend Zoe has always wanted me to watch her fuck a really well hung man,” Vera explained over the phone.
“She is very proud of her sexual prowess and loves to regale me tales of her exploits when we sunbath naked together. She has even enjoyed me watching her fucking her men a few times. But she has never had a man with an oversize cock. It’s her fiftieth-birthday next week so I want to surprise her and watch her have and enjoy her fantasy. Don’t let her age put you off, she is attractive and has a ripe, voluptuous body.
I arrived at 3pm on the Tuesday afternoon and phoned Vera as arranged to let me in. She was wrapped in a towel and obviously naked underneath.
“We have been sunbathing nude and I have been teasing her about her huge cock fantasy while I rubbed oil all over her naked body,” she told me as she led me through the large and exquisitely furnished house to the pool area at the rear.
“I told Zoe I had a surprise for her birthday but she has no idea what it is. Get naked before we front Zoe,” she instructed as she dropped her towel.
“Wow, you are big, and thick as well. I would like that for myself one day, she smiled as she felt the weight of my cock as I took in her naked body and became semi-erect.
“Happy birthday Zoe, here is your surprise,” Vera smirked as she led me by my now full erection in front of Zoe who was standing stark naked with an all over tan near a drinks trolley.
Vera had told me on the phone she was attractive with a ripe, voluptuous body, and her deion was an understatement I mused as she stepped into a pair of stiletto heels she had close by. The heels accentuated her long legs, shaved cunt, large firm arse and very ripe tits with large erect nipples.
“Well hello big boy. Are you here to fuck me? I hope so, as Vera has been teasing and turning me on all day with her conversation and naked body. I’ve waited fifty years for a huge cock like yours. Vera likes to watch so make it good for both of us. Let’s have an open air shower together for foreplay. Then we can go into the bedroom and fuck.”
In the bedroom Vera sat in a chair near the bed and watched fascinated as Zoe kissed, licked and then sucked my rock hard cock with me lying on my back.
“Is that huge cock in your mouth worth the fifty-year wait? Can’t wait to see you fucking it, all of it. Show him how good you are.”
“I intend to,” Zoe replied as she straddled my cock and slowly took it’s full length so she was able to grind her pelvis into mine while using her cunt muscles to tease me, then slide right off me and do it again. And again, and again.
“Now fuck my brains out from behind big boy while Vera watches.”
I grab her large and ripe arse with my two hands and slowly slide my rock hard erection into her while looking at Vera who is teasing Zoe’s nipples.
“Is that good Zoe? What would you like me to do?”
“Just watch and enjoy and masturbate with your vibrator.”
Zoe really was very good with all sorts of subtle moves and sex talk to heighten the sexual experience of three people.
“Fuck my cunt big boy. Slam into my arse. Make me scream.”
After a series of orgasms Zoe led me outside and said, “Your erection has wilted. Lay on that rubber mattress and I promise I will get it back for you. Do you like golden showers? I hope so because I love to give them, especially with Vera watching.”
She squatted directly over my cock with her legs open and really let go with a strong hot stream directly onto my cock.
“Wow, your cock liked that didn’t it? You are rock hard again. I want Vera to give you a hand job while I watch. Would you like that? Vera and I would, very much.”
And she did with lots of verbal encouragement from Zoe.
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Fiona had a poodle, which she doted on. While I fucked her she insisted on the dog watching and she liked to talk to the dog.
“Mummy is being very naughty today. But Mummy has been hanging out for a good fuck with a really big cock.
“Mummy likes well hung men, especially this one. He is magnificent, what a cock, long and thick. And I want him to fuck my brains out while you watch and listen.
As she moaned and screamed while I fucked her, the dog would whine and howl in unison.
“Mummy is going to have a really big orgasm on this huge cock,” really set the dog off.
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Carol really was something. Two years older than me, Spanish descent, fantastic all over tanned body, brilliant legs, a beautifully proportioned forty-three inch arse and a very sexy out-going persona. She told me one of her long-held fantasies was having a man with a huge cock, who would fuck her glorious arse from behind.
She was a repeat client and the second time around she phoned one of her girlfriends, Pam, as we fucked to describe to her what we were doing. “He just told me he is fucking the worlds greatest arse Pam.”
“I can hear that,” she replied.
On the third time around her girlfriend Pam was there. “She is most impressed with what she knows about you so far. This time she wants to watch. Is that okay with you.”
Carol liked me to wear a tiny black g-string for her as a visual turn on. She knew as soon as she was naked, or even before, my cock would be bulging out it, as it was on this occasion with Pam watching.
“Wow Carol, that big, thick cock really is something. I am wet just from looking at it. And your arse really is sensational. I am looking forward to watching him fuck you.”
“Good, so am I, why don’t you make me jealous by playing with his cock before I have him? Use two hands, while he kisses my arse. That is a turn on.”
Carol then led me with a hand on my cock to her bed, with a chair close by.
“Sit there and watch Pam. Now lie down and fuck me from behind like last time, and make it last. I want to show Pam how good you are.”
Pam is watching fascinated as I slowly slide my cock into Carol with both my hands gripping her wonderful arse cheeks.
“I’ve always been in awe of your sun tanned naked body, especially your legs and arse. Watching a well hung man fuck you has always been a fantasy.”
“That is magic Pam. He is so big and he fills me up. Would you like him to fuck you one day while I watch? Lick my nipples for me Pam. Fuck me harder, slap into my arse.”
After what must have been thirty minutes, I looked up as Pam said, “You two have been fucking non-stop. What a turn on. You are both magnificent, big cock and wonderful big arse, perfect match and I love watching. Fuck her really hard, make her scream for me.”
As I looked closer I noticed that Pam was now naked with her legs wide apart with a huge vibrator sliding in and out of her very wet cunt and obviously very close to orgasm.
From prior experience I knew that Carol liked to orgasm with me on top of her with her legs wrapped around my back while grinding into her. Changing positions was also an opportunity to tease Pam with my now very moist cock as she used her vibrator.
“I’m going to bring Carol to orgasm now Pam, cum at the same time.”
A big turn on with two very horny women orgasming at the same time – and I did too.
Watch out for my next instalment.
