January 2021 (continued)

Forbidden Fruit Newsletter (continued)
Share your sexy secrets
What Are Your Sex Goals For 2021?
To have more sex than in 2020
To finally try “that new thing” with my partner
Invest in myself with a high-end sex toy
Give my lover more & better orgasms!
Created with Quiz Maker LMS
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Guilty Pleasures Continued

Gigolo (continued)

I'M THE CLASSIC gigolo. I hook up with older women wanting an escort, lover, and friend all rolled into one. The darlings pay handsomely for my service. But when you have tons of money and are lonely, the price is a small one. Although I accept cash and gifts for my time, each companion is special to me.

For my twenty-first birthday, my grandmother took me to New York City for the weekend. After seeing a show, we stopped in the hotel bar for a nightcap. Once my grandmother retired, a woman in her mid-forties approached me. Her name was Gail. She bought me another drink and we went up to her suite.

She told me I had a lot to learn about pleasing women.

Gail told me to strip. She inspected my cock, jacking me with her small, delicate hands before wrapping her lips around the head. Before long she was sucking on it, taking it deeply into her throat. Without a second thought, I came.

She told me I had a lot to learn about pleasing women. She said that my body could be my fortune if I were smart enough to learn how to use it. The first thing I needed to learn how to do was control my cock.

At her direction, I licked her inner thighs and her outer lips

She led me to the bed. I lowered my head to kiss her nipples. I took my time, relishing the effect my caresses were having on her.It was a new experience for me to be concerned for my partner's passion. I trailed kisses down her belly as my fingers found their way into her cunni. Gail urged me downward. I had never eaten pussy before. As I positioned myself between her spread legs, she grabbed my head to stop me from diving right in.

At her direction, I licked her inner thighs and her outer lips, and then sank down to her tunnel, burying my tongue deep in her depths. Again, Gail urged me on, this time to her clitoris. As I parted her lips and found the hooded nub, she shuddered. I latched on to it, licking and sucking for all I was worth. She reached what seemed to be the mother of all orgasms and I stayed with it until she pushed me away.

Gail pulled me over onto my back. Straddling me, she sank her lovely pussy down on to my meat. She controlled our fucking by stopping and starting. She showed me how to prolong my erection. Half an hour later, I knew I couldn't last any longer. Gail was also at the point of no return and we climaxed together, holding each other tightly. It was another first for me.

As I gathered my clothes, Gail gave me a $100.00 bill. I didn't know what to say. I actually mumbled that I should be paying her instead. Gail smiled sweetly and tucked it into my hand. She told me to never under-value my services again. I promised.

At her prompting, I quit my summer job to act as her secretary for an upcoming tour of Europe. I explained to my parents that I would be arranging her schedule and taking care of all of the little details, thus freeing her to simply enjoy her jaunt. With that settled, I met Gail back in New York and we began my sexual education in earnest.

She had no interest in my body other than how it would please her darling Anna.

Gail taught me how to please an older woman, whether in bed or out on the town. I learned that many older women travel with young men - and young women too. At one party in Milan, Gail introduced me to her friend Amanda and her companion, Anna. Anna was Italian and spoke little English, but it was clear to Gail and Amanda that Anna wanted to fuck me. A compromise was reached. I would spend the evening with Amanda and Anna and the next night, Anna and I would pleasure Gail.

I followed them to their suite, unsure of the rules of the game, but Amanda set me straight. She had no interest in my body other than how it would please her darling Anna. She undressed Anna for me. Her hands and mouth roamed her young lover's body as I pulled Anna's head down to my cock. Amanda sat back to watch Anna suck my dick, urging her to take it all. Anna responded in a frenzy of tongue and lips, bringing me to the brink of orgasm.

Amanda had Anna bend over from the waist, giving me a good look at her luscious labes. She licked Anna making the Italian moan with pleasure. Moving to the bed, Amanda lay down, with her butt at the edge. Anna crawled to her, drawn to her benefactor's pussy as a bee is to honey.

Amanda cooed to Anna in Italian as she spread her legs for the girl to feast. I got between Anna's legs and slipped my hard-on deep into her. Amanda ordered me to describe how Anna felt, wrapped around my cock. I fucked her hard and fast, giving the older woman a running commentary of Anna's velvety softness.

I watched as their tongues intertwined around my prick.

It was a night to remember, but the next night with Gail and Anna managed to top it. It began with both women peeling off my clothes and giving me a double blow job that was unlike anything I'd ever experienced. As Gail licked my balls and ass, Anna swirled her delicate little tongue around my cock. I watched as their tongues intertwined around my prick.

Next, Gail arranged herself in a chair and patted her vulva. Eagerly, Anna and I licked her pussy, stopping to kiss once in a while. Anna slipped her tongue into Gail's asshole as I lapped at Gail's clit. Gail was going wild but she managed to pull Anna down to the floor for a 69. Gail was on top and it took me all of 2 seconds to decide to plunge my cock into her cunni. Every so often, I'd feel Anna's warm tongue lick my balls as I fucked Gail's pussy. When Gail came, she climbed off of Anna and had a short conversation with her. She looked surprised and then amused.

Anna agreed, even though she wasn't quite sure that she could handle it.

Gail explained that Anna loved getting fucked in the ass and that she would do anything if I would oblige her. It was another first for me… Gail had never asked me to fuck her butt before. Gail's counter-offer was that I would fuck her asshole, if she could fuck her pussy at the same time. Anna agreed, even though she wasn't quite sure that she could handle it.

Once again, Gail sat in the chair with her legs spread for Anna to lick her pussy. I stood beside Gail as she wet my shaft with her tongue. Kneeling behind Anna, I smeared K-Y on my meat as Gail instructed. Slowly, I let the tip of my dick slide past Anna's tight anal muscles. With Gail coaching me, I took my time, letting Anna's reactions guide my movements. Soon, I was balls deep in what had to be the tightest passage I'd ever had the pleasure to encounter. Anna lapped Gail's clit furiously, bringing her to a loud, satisfying climax as I slid in and out of her butt.

Gail padded off to the bathroom and returned wearing a strap-on dildo, that she claimed was to break my ass in sometime in the near future. I was too involved to answer at the moment.

Gail scooted beneath Anna and slid her plastic prick into Anna's twat. It was incredible. Gail and I got a counter-rhythm going and before long, Anna moaned as our double-fucking brought her to orgasm. I wasn't far behind her, shooting my load into her stretched asshole.

That first summer was over 3 years ago. Since then, I've met many other ladies. Oh, I still see Gail on occasion and she's certainly introduced me to many of my ladies. We're closer than ever but her interest in me cooled after that first glorious trip of ours. No matter, there are plenty more just like her… looking for a good time.

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