DIARY OF A GIGOLO 4. free porn video

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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.

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.

Xxxxxxxxx

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 mesmerized. “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 ass are pretty good for fifty-five old as well, I think.”

She was correct. A big, though very well proportioned and still firm ass 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 ass was facing me. Watching a very good, full size 14 ass, 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.

Xxxxxxxxx

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 harbor. 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 ass.

“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 ass. 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 ass.”

She screams and orgasms again. “Now stand me up against the wall and fuck me from behind. Grab my ass 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.



Xxxxxxxxx

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 a good ass. Doe’s my big ass turn you on? Don’t answer me, let your cock do the talking. Alex likes to lick and kiss my ass while my cuckold watches.

Right on cue Alex commences licking and kissing her ass. “Barb is twenty years younger than me. She is a size twelve to fourteen with a very well developed body and an ass 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 ass 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 ass. “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 ass, 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 ass 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 re-positions me so I am standing while she sits on a stool in front of me while her man recommences licking and kissing her ass cheeks.

She is very good at cock sucking and watching her husband masturbating while he licks and kisses her glorious ass 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.”

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Diary entry 62111

Diary entry 6/21/11Hi diary, It's me again!!Adriana is passed out after our wicked sex fest so I thought I'd bring you up to date! Anyway diary, you'll never believe my fucking day! Weird and wild I'd say!!Anyway you remember Rod? I'm trying to forget the creep, believe me! I wrote to you about him back in the spring time, remember? As you know I stopped banging him about a month ago when I found him with his cock in that slutty ho he works with. I do miss that mans monster missile, he is good...

Group Sex
1 year ago
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Diary of a house boy part two

April 11 Dear Diary, Wow, you should have been with us last week!!! Mr. Foxx took me along with him to San Francisco on business!!! Talk about a wild place, diary, I actually saw two men fucking out in the open in the park and nobody even gave it a second look!!! Mr. Foxx gave me one hundred dollars and sent me on my way to explore the city when he was at his meeting!!! I found this little place that advertised live dancing in private rooms, and since I'd never heard of anything like that...

Gay
2 years ago
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Diary 8211 My Son Made Me Topless Naked Model 8211 Episode V

Read (Chapter ON ROOF) Suddenly my son holds my hand and pulled me from sofa. He also took all camera and apparatus and dressed up. He simply drags me to front veranda. I was stunned and ashamed of my semi nakedness. If any neighbor awoke at this moment they can see me. But I kept quite. He opened main door and stepped up on stairs to go to roof. We came to roof. February’s 4 am is almost dark night and chilly. I shivered with cold and shame. I, a traditional Bihari lady, standing in open...

Incest
2 years ago
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Diary 8211 My Son Made Me Topless Naked Model 8211 Episode IV

(Chapter FRIDGE & HANDCUFF) Love and affection flows from my heart. I want to give him some precious gift. I know if I offer him choice, certainly he asks for mother’s vagina. My eyes are closing with sleep but with apprehension I said- ‘Beta’ I want to give you something precious, ask anything I have. Son Said- Ma’ you just gave me most precious photographs of yours. It is enough for me. Foolishly I insisted him- Ok but you can ask for anything I have. Son Said- Ma’ right now you can give me...

4 years ago
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Diary of a Bloodsucker

November 2nd, 1813 Vienna, mierda! I’m still in Vienna. Diary, I had hoped to be back in Almeria by this time. Back home, for the holiday, for the Day of the Dead. (There is no Day of the Un-dead, so I settle for the closest thing.) During the chaos of those revels, that last well into the early morning, victims are easy to come by. A woman or two disappears and no one notices. No one suspects my hand… But, I am trapped here in Vienna in this wine cellar, hiding like vermin, and I have been...

2 years ago
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Diary of a fledgling dominatrix 2

Introduction: Friday 9/20 and Monday 9/23 Dear Diary, Ethan gone. He proved himself unworthy and removed himself from the picture. I cant really articulate how I feel about this but every bit of it reinforces this.. self-awareness Im experiencing. Like, I am an entity, a whole, stand-alone person. I used to think of Ethan as a piece of me. An extension of self that I needed, but now I think I felt that way because it wasnt Ok for me to want things. Like, I only ever deserved what I needed. Not...

1 year ago
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diary pt1

I bought a house two days ago. I know it’s kind of strange for that to be the first thing you learn about me, but hey, I’m still trying to get used to the idea of having a house of my own, myself. It’s not very big, more like spread out. It has one floor, three bedrooms, a kitchen, a living room and a pool…the bare essentials. I’ve only moved in today so I’m still a bit disoriented when it comes to the house and everything in it. Well actually, there’s nothing in it. It’s empty and only now, as...

3 years ago
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diary pt1

I bought a house two days ago. I know it's kind of strange for that to be the first thing you learn about me, but hey, I'm still trying to get used to the idea of having a house of my own, myself. It's not very big, more like spread out. It has one floor, three bedrooms, a kitchen, a living room and a pool...the bare essentials. I've only moved in today so I'm still a bit disoriented when it comes to the house and everything in it. Well actually, there's nothing in it. It's empty and only now,...

3 years ago
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Diary of a Jailbird

October 17Dear Diary...You showed up in my first care package, and since I'm not doing anything else, I might as well write in you. =)Lemme tell you a bit about myself.  I'm Casey, Casey Shepherd.  I'm, 19, really tall...5 foot 11 to be exact (yay tall me!), weigh about 150 lbs, slender and toned from playing volleyball and softball, straight blonde hair, blue eyes, freckles, 38c, size 10 feet.  In the winter I like to go snowboarding.  If you haven't figured already, I'm a big tomboy.  All...

1 year ago
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Diary of a housemother part one

Dear Diary, My name is Tilly Crawford and for the past ten years I've been the housemother for the Delta House Fraternity here at State U. Another year of school started just yesterday and the boys have been getting ready for fraternity pledge rush week by planning parties and of course the open house to allow the new freshmen to get an idea if they'd like to join Omega House. It was long summer for me diary, I really miss being around the boys and of course my pussy missed the attention it...

Fetish
4 years ago
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The Kings Gigolo

I have always been a little keen on medieval times. I am by no means what you will call a history buff, I enjoy the primitive fashion especially the low neck lines and heaving bosoms and the barbaric behaviour but mostly the romantic interludes that are linked with so many hero’s and legends. On a smaller scale I have always been let’s say amused more than interested in the idea of time travel and teleportation from a very early age from the time I started to read The Chronicles of...

2 years ago
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Aunt Cathys Gigolo

AUNT CATHY’S GIGOLO I served my country honorably until I took a shot to the hip. Not much an Army Ranger can do without a useable hip. I was patched up pretty well, but still given a medical discharge, some very nice VA benefits, and decided to go to college full time. In my four and a half years of active duty I managed to get a full year of college. My Aunt Cathy runs a hair salon from her home about four hours from my parent’s place. About ten minutes from her house is a university I’d...

1 year ago
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Jack the BigDick Gigolo

My name is Jack, and I’m here to tell the story of how I got involved in the business of being a gigolo, male escort, social companion, or whatever you wish to call it.I was twenty three years old when it first began. I was a regular guy; I had a regular job working at the airport. I had a girlfriend. Nothing special.Except in one area, I have a very big dick. Almost nine inches long when I’m fully hard, and two and a half inches wide. Girls seemed to like the width more than the length I...

MILF
4 years ago
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  • 20
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Gigolo

Hi, my name is Al Whitley. Now that may not seem important to you right now. However, I think as you read this you may want to change your mind. I am your average personal trainer, working at Cindy’s Spa and Health Studio here in town. Not much of a job, you might say? Well, in a way your right; and you’re also very wrong. I call the place Cyn’s (sins) meat market and sweat studio. Ladies flock to the Spa looking to lose a few pounds and to get out of the house and away from the curtain...

Cheating
1 year ago
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How Sex With Boss Made Me Gigolo

Hi, ladies, bhabhies, aunties and girls. My name is Rahul(name change) I am from Noida. I am a call boy. Today I’ll tell you how I became a call boy. First, let me tell you about my self. I am 26years old. My height is 5.5”. I don’t have a physique like that of a stud. I am a normal looking boy. My dick is 7” long that can satisfy any lady/ girl. So now without boring you much let me come to the story. I’ll tell in Hindi now. Me ek MNC me kaam karata hun as a Manager. Meri boss Kolkata ki rehne...

2 years ago
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My First Massage Experience Made Me A Professional Gigolo

Hello all ISS readers. My special warm greetings to Girls/Bhabhis/Aunties, all female ones/House wives from #Odisha and #Chhattisgarh. Please give me feedback at “” after reading my experience. I’m Amitav aged 24 years, 5ft 8inch height, grey complexion and handsome athletic body. Now I am going to tell you how my body massage experience with my Aunt made me a professional gigolo one. I am from RAIGARH, CHHATTISGARH and had completed my B.Tech in 2015. Now I’m preparing for job staying away...

2 years ago
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  • 14
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Majburi Ki Chudai Majburi Me Bana Gigolo

Hi….. Readers this is my first story on Indian sex stories … I am interested to write this story in Hindi.. Mera naam sagar hai aur main up ke ncr area se attech area se belong karta hu aur mai college student hu. 25 yr young handsome and tall boy With a average tool.. Ek din hum sabhi college ke dosto ka plan bana kyu na aaj raat ko party ki jaye kisi disco me jaker, aur hum sabhi ne decide kiya hub sab friends club me hi millenge. Time ke according hum sabhi dost club gye aur drinks ki aur...

3 years ago
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Me And Aunty Sonia Made Me A Gigolo

My name is Tarun, I am a resident of Gujarat. I am a handsome guy to my height is 5.6 Feet. This story is a true story of how my boy, my aunt made me call. My aunt’s name is Sonia, their age 29 years, when they are very beautiful and sexy. Their butts are raised upwards to see if anyone stands Lund, the figure is 36 32 38. Aunt lives in Rajkot, he is a boy of 5 years. My uncle is a military, they remain out of the house. He visit 2 time a year. Join the paper after I got 12th, I was bored at...

Incest
3 years ago
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  • 19
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Aunt Cathys Gigolo

AUNT CATHY’S GIGOLO I served my country honorably until I took a shot to the hip. Not much an Army Ranger can do without a useable hip. I was patched up pretty well, but still given a medical discharge, some very nice VA benefits, and decided to go to college full time. In my four and a half years of active duty I managed to get a full year of college. My Aunt Cathy runs a hair salon from her home about four hours from my parent’s place. About ten minutes from her house is a university I’d...

Straight Sex
3 years ago
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  • 18
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The Gigolo

Laura puckered her lips as she applied the eyeliner. For years she’d had no idea why she puckered up when she put on eyeliner until a friend had questioned her about it several months ago. It had taken her three weeks of casual pondering before she suddenly realized there was no real reason for it. Her mother had always pouted when she put on makeup and she had passed the habit onto her only daughter. Laura in turn had passed it onto her three daughters. Her long blonde hair was beginning to...

Straight Sex
2 years ago
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  • 9
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NRI Lady Sex perience of Gigolo

Hi friends im back once again with real gr8 experience with NRI lady who kalp me for 24 hours Not wasting much time let start the story baat yeh november end ki hai i was just chatting on yahoo i met one lady from USA her name was Kajal we just chatted normal things then she asked me what u do i told her that i m gigolo by profession she asked me kahan se ho tum maine kaha mein gujarat mein rehta hu tho ek dam boli arre mein bhi abhi india mein aayi hu she came to bardoli phir mere se poochi...

3 years ago
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Mom Fucked By A Gigolo

It was hard, long, thick, and black. I had never seen a cock this big before. He was tall, dark, and muscular, maybe a gym freak. Or maybe this was just a job requirement for him. But mom loved it. She bent down and kissed the head of his throbbing fat cock. Then sat on her knees and took half of it in her mouth. It was so fat that she had to open her mouth wide to take it in. She looked up at him with a naughty look on her face while there was just a slight smile on his face. With his hands on...

3 years ago
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Diary of a fledgling dominatrix 2

Ethan gone. He proved himself unworthy and removed himself from the picture. I can't really articulate how I feel about this but every bit of it reinforces this.. self-awareness I'm experiencing. Like, I am an entity, a whole, stand-alone person. I used to think of Ethan as a piece of me. An extension of self that I needed; but now I think I felt that way because it wasn't Ok for me to want things. Like, I only ever deserved what I needed. Not anymore. Almost overnight I feel -- quite...

3 years ago
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  • 11
  • 0

Diary Confessions Tales of Week Two

Introduction: We are step-Siblings of four years and wish to share our journey. TALES OF WEEK TWO TORI-LEE We were officially one week into our life changing journey and I must have had more eye opening experiences than I could ever remember. My mind was going a million miles an hour taking in everything I was learning. Which, at 18, lead my hormones to go crazy. Id never even lived with guys before, so after 7 days sharing a 40 foot bus with my mamas new man and his son I had urges and...

3 years ago
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Diary of a Nazi Rape Squad

My name is Barbara Luttice   My name is Marla Eton.? I?m a 43-year-old Briton, currently living what I consider to be my dream life with Julio, a considerate, handsome, late-thirty-something Italian university art history instructor and avid painter, here in sunny Italy.? Ever since my stressful divorce from a Fleet Street solicitor four years ago, I?ve lived here in the beautiful Tuscan countryside, an hour?s drive from Florence, were I now work part-time as a visiting professor of...

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