You would like Sherry. She's five-seven, one hundred thirty-five pounds, dark black hair, gray eyes, rather attractive, not beautiful exactly but she always got her share of looks. Some of that was due to her figure, she was pretty curvy with a very nice bustline, D-cups and naked she looked very good.
Sherry was thirty-six and had been divorced for, I think it was, six or seven years.
What I especially loved about Sherry was her manner and personality. Both of them.
There was the 'business and professional' Sherry. Conservatively-dressed, well-mannered, business-like.
Then there was the Sherry she lets out at other times: slutty, hot, kinky. They were both nice but the hot Sherry was surely the most fun. That's why we were together at the time this took place.
I was consulting at the time and between contracts, when she asked me if I wanted to go to Los Angeles with her, she had some business out there, but I could go along for the fun, and, oh, let me tell you, the sex.
Sherry was the hottest woman in bed I've ever known. I'll get to more of that in a minute but for now, I agreed and we flew out to Los Angeles to stay with a friend of her's who I had met several months before. Annette had a nice house with a pool so I figured it would be a short vacation for me while Sherry was conducting business.
Now, Sherry, in her hot, sexy phase, could be quite a tease. It wasn't unusual for her to go without panties and most of her bras were demi-cup to show off the tops of her lovely breasts.
Sherry loved her breasts. I did too, actually. I had never been with a woman with such sensitive nipples. They were large, brown ones and I could play with them, pinching them, rolling them between my fingertips, and sucking them, oh, she loved them sucked, and she would have an orgasm. From her boobs. And the longer I sucked her nipples, the more orgasms she would have. One sexed-up woman.
And cock? Oh, one of the first things she told me when we first met was that she adored sucking cocks. She had mine in her mouth shortly after. And, she often cums when I shoot in her mouth. She told me it's one of her biggest turn-ons, that first spurt hitting the back of her mouth. She really cums when it happens, I've seen it many, many times.
So, Sherry is classy to be around and super-hot in bed.
We often talk about sex and on the way out to Los Angeles, I asked her what her top fantasies were.
"Oh, you just want to get me wet and squirmy in my seat, don't you, Michael?"
"Yes, actually. But I'll wait to do anything about it. These lavatories are just too small."
"Heh, yes they are. I tried it once, don't bother. So, my fantasies? Hmm. Well, one is getting fucked while two other guys suck my boobs. So, three guys and taking turns. You know how I love them sucked."
"Oh, do I. And I so love sucking them."
"God, I'm getting wet already. So, any way, that's one. Um, the other would be to be blindfolded, tied to a bed, naked, in high heels, real '-fuck-me' jobs, and be enjoyed by two strangers however they wanted for hours and hours. Whew. I'm feeling warm. Tell me one of yours."
"Well, just to watch one of your fantasies take place would be pretty great, I think. Here, see how I like the idea," and I took her hand and put it under the newspaper I had on my lap.
"Yes, I just wish we could use that right now. Well, I can rub it a bit, I suppose," and she gave me that wicked grin that tells me she's feeling slutty. So, we talked and she rubbed and the flight attendant who walked by gave us a big smile and a wink, she knew we were having some fun at forty-thousand feet.
So, we rented a car and got to Annette's house and took our bags in. She told Annette that we needed some time to freshen up and we went back to our room and Sherry fucked me silly.
We did go back out and met Annette's son, Ryan, a sophomore in high school, going into his junior year in the fall.
Annette left for the weekend, leaving us to housesit and be there with Ryan.
Sherry had told me about Ryan, that she knew he was checking her out whenever she came for a visit, a typically horny young guy, full of spunk and no where to put it except in the palm of his hand. And, yes, he did seem to hang around her pretty closely. I noticed that right off.
On Saturday, after a nice long fuck in the morning, it was after lunch and I was dozing on the sofa in the den. I heard Ryan whispering to a friend of his we had met earlier, Lee.
"There she is. Talk about hot, huh? Would I love to fuck that. Look at her boobs."
"They sure don't sag, how old did you say she was?"
"Younger than my mom, she's thirty-six. Nice, huh?"
"I'll say, hot is right."
"I've jacked-off so much thinking about her, must be gallons by now. Even when I was twelve or so. She made me so hard. Boy, would I do her in a minute."
I rolled over and snored a bit, just to let them know I was there, though asleep, and they soon went out of the room.
But, knowing horny boys, having been one myself, I knew they'd be watching as long as Sherry was in that bikini and I really didn't blame them, she did look hot.
So, I decided to mess a bit with their minds. And with their hard-ons. I went out to the pool and sat down with Sherry and started kissing her. She asked me to put some more suntan oil on her, and since she didn't know the boys had come home, I made sure I got it everywhere I could, especially under her bikini which I pulled aside to get her nipples covered with suntan oil. As you know, she loves her nipples rubbed and played with so she certainly didn't stop me, no, not at all.
Her cell phone rang and she had a quick business call and ran off to get changed to meet a client for a drink. Luckily, she didn't run into the boys lurking around but I did see them later.
I told them that I had overheard their banter earlier about Sherry and knew they were watching when I was by the pool with her a short while ago. Taking it a bit further, I asked them if they would like to see some photos I had of her and they followed me into our room as I dug them out of my suitcase. Some were topless and the boys certainly were impressed with the object of all their unbridled lust and I left them to drool over them as I went off to shower. I did quietly sneak back to listen in and Lee took a couple of the photos and disappeared down the hallway, no doubt to hit the bathroom for a quick sperm reduction.
Knowing that I could probably swear them to everlasting secrecy, I asked them if they might just want a chance with the object of their erotic desires and they were quite eager. Did they want to see her naked and maybe even get to play a bit themselves. I had in mind to make the first of Sherry's fantasies come true so I reserved a motel room near Annette's house and simply told the boys to come to the motel and call me from Ryan's cell at exactly ten PM and I would give them instructions.
So far, so good.
When Sherry got back, I told her that I was busy while she was gone and had arranged for her number one fantasy to take place later that evening.
"The one with me with three guys, two on my tits and one in my pussy?"
"Exactly. I've got the place and the two guys. I figured we're far from home and I'll be there the whole time. I've got two really nice young guys lined up, I know they're really stoked for this."
"Geez, you've been busy, Michael. These guys aren't big brute types are they?"
"Nah, they're more like college guys, young, eager, really horny. Clean-cut."
"But, horny, really horny. Young and horny."
"Ahh, you're getting excited now aren't you? Pussy getting wet?"
"Wanna lick it and find out for yourself?"
I've rarely turned down an offer like that so I did get her naked and had some fun with her wet, hot pussy. But I did tell her I wasn't fucking her, that was for later. Oh, that got her, that got her good.
We went out to a quiet dinner as she quizzed me on the two guys I had lined-up. All I would tell her was what I had already told her and she was just dying to know more.
"I'll suck your cock forever and ever if you'll tell me more, Michael. I promise."
"In less than an hour, you'll know, Sherry, just keep your panties on."
"Can't, didn't wear any," she replied with her sly grin. I reached under the table and she was right. Wet and bare. And, really so wet. She widened so I could slide a finger in, then she clamped down on my hand.
"Now, I've got you, Michael, right where I want you."
"Come on, Sherry, let me go, it's just going to create a scene," and her thighs relaxed and I pulled out of her and sucked her juices off my finger as she smiled at me.
"Lovely appetizer, my dear," I said.
"You can have lots more later," she said as I smiled, knowing she would produce a lot of juices before I was through with my plans.
We were in the room shortly after nine and I slowly undressed her, kissing my way down her body, which she always loved. Then, I sent her to shower as I opened a bottle of champagne and poured us both some. I gave her some nice pussy-licking which she always, always loves, then a bit more champagne.
As we sipped away, I sucked her nipples and tweaked them between my fingers, as you know, she has super-sensitive nipples and she was dripping hot by the time ten o'clock rolled around, begging me to fuck her or at least let her suck me off. I let her suck me just a minute, then pulled back out of her mouth as she begged me to let her finish. I had her in a frenzy by then.
.... There is more of this story ...