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.
Then, just before ten, I took out my pair of fur-lined handcuffs and cuffed her wrists behind her back and put on her red stiletto 'come-fuck-me' high heels and a fur-trimmed blindfold and told her she was just minutes away from the two young men joining us for a night of ravishment.
Precisely at ten, Ryan called my cellphone from the parking lot outside and I went out to bring them in through a side door to our room. I told them that they were to be absolutely quiet, that Sherry was blindfolded and was expecting two young men that I had recruited but that she was not expecting them. I also told them that Sherry had agreed that the sky was the limit for the night and that she was willing to do anything we three wanted with her outside of causing her pain. Were they excited.
I opened the door and told her we were there, she was sitting on the bed and when the boys saw her naked, her hands cuffed behind her, blindfolded in those hot stilettos, they both gasped as they drank in her body, her generous breasts, nipples so aroused, womanly hips, gracious legs, dampened slit, everything they had hoped for and more.
"Get up, Sherry, walk around a bit, show these guys what you have," and she stood and took a cautious tour around the bed as the boys gaped at her. The bulges in their shorts were unreal.
Then I sat her back on the bed and spread her legs apart.
"Get a nice look at the star attraction tonight, fellows," as I knelt down and spread Sherry's legs then pulled her labia apart exposing her pink insides to her two horny admirers.
"I hope you like my pussy, guys, it just loves to be licked and fucked," she added, no doubt making them even more horny.
They were both crouched down, peering into the insides of the first naked woman they'd ever seen.
Then, I led Sherry to the sofa and had the boys come over and sit on each side of her.
"Now, fellows, take some time getting to know Sherry, I suggest that you all three make out for a while, no rush, take your time. I'm sure Sherry can warm you guys up and vice versa, so just enjoy each other," and the boys started kissing her, taking turns but they seemed to be holding back on touching her.
"I'm sure Sherry would love for you fellows to touch her, caress her, make her feel good wherever you want. I know she's not shy, she loves to be touched and kissed and sucked and licked just everywhere."
Their hands were immediately on Sherry's large breasts, fondling, squeezing, sucking her nipples, as she moaned in enjoyment.
She leaned back on the sofa, spreading her legs apart as Ryan and Lee ranged all over her, licking her pussy, fingering her, both sucking her nipples which made her orgasm as one of them was also fingering her at the same time. They just looked so excited when she started cumming and groaning and heaving her hips up and down. They were in boy-heaven. And, Sherry seemed pretty pleased herself.
"Mmm, oh, guys, just do whatever you want, just go ahead."
Ryan took hold of his cock and started to get between her legs but I shook my head and he held back. She would get fucked later, that was my plan. Then they were back to sucking her boobs, so I got down to lick that wonderful pussy of hers. She didn't last long, she was writhing and bucking herself into another grand orgasm. I've been with Sherry in a variety of sexual situations and I'd never seen her this stoked, this highly aroused.
So, I figured it was time for us to raise the stakes a bit more.
"You guys ready for more?" I asked and they both vigorously nodded up and down.
"Well, it's time to get naked," and they were both stripped in seconds.
I helped get Sherry down on her knees, her hands behind her in cuffs, then led Ryan up to her and motioned for him to step forward and put the head of his cock at her lips.
Sherry knew just what to do at the first touch. She opened and leaned forward to suck him inside and began doing what she does so magnificently. Lee and I attached our mouths to each nipple and enjoyed ourselves, Lee, especially, fingering her as well.
"Oh," Ryan moaned as I put my finger over my lips to silence him. I couldn't blame him for moaning, I've been sucked by Sherry countless times and she's a wonder.
I wasn't surprised when she got a mouthful of Ryan's cum in just a few minutes. These boys had been lusting after Sherry and were at a peak of horniness.
Soon, Lee took Ryan's place in Sherry's mouth and Ryan and I sucked her boobs and I had my fingers in her this time.
As expected, it didn't take long before Lee had yielded up his cum offering to Sherry and I took my place being sucked by Sherry. My cock took a while longer even as sexed-up as I was after all this and I loaded her mouth with a fine shot of my best semen, some I'd been keeping ready for hours.
I tilted Sherry back onto the bed and spread her legs out wide, then motioned Ryan up to put his cock in her and fuck her as Lee and I sucked her boobs. I only let him fuck her for a few minutes before I had him change with Lee who gleefully entered her.
Wanting to give her as much variety as possible, I loosened the cuffs and got her back on the floor on her hands and knees as Ryan fucked her doggie-style as Lee fucked her mouth and I pinched her nipples hanging down. She had several orgasms through all this, I've told you that Sherry is an orgasm machine, and after a few minutes of this, I decided it was fuck and cum time so I got her up on the bed, had Ryan get between her legs, he was the better-hung of the two, while Lee and I sucked her tits, Ryan drove into her fucking her just like a teen boy in his first pussy, which it was.
"UHHH, UHHH, UHHH, uh, uh," grunted Ryan as he cummed deep inside Sherry as she lifted her feet up so he could go deeper as he spewed into her. It was then that I stood up and pulled off her blindfold.
"Omigod, Ryan. Oh, shit, just don't tell your mom."
"I won't if I can fuck you all night," he shot right back with a big grin on his happy face. Lee pulled up off her left nipple and said, "I want to fuck her, too, I want to shoot her full of my cum. I get a turn."
"Yes, Lee, here, fuck me all you want," she said and he was immediately inside her fucking back and forth, rubbing her boobs as he went.
"Oh, Michael, you set this up all along, didn't you? You knew they wanted to fuck me, didn't you. And you set it up."
"I sure did, hon, look at the cum running out of that happy pussy of yours," and it was true, she had a wet, sticky spot under her that was destined to grow much larger before the night was over.
She laughed and said, "Well, Michael I think I owe you a lot of blowjobs to pay you back for these two horny boys."
She took Ryan's cock and began sucking it as Lee fucked her furiously as only a teen boy can do. He was soon spurting her full as Ryan stood there, his eyes closed as she pleasured him greatly.
The four of us were now relaxed and intent on having fun, the boys, taking and giving as much pleasure as they could, and, being mid-teens, they just went on and on. I mostly stayed on the sidelines offering suggestions to Ryan and Lee, to titty-fuck her, for example, among other things. We, all four, spent the entire night in sex and then checked out about eight-thirty and went back home.
Sherry and I went to bed and I knew the two boys did as well, they were literally fucked-out, and Sherry got some well-deserved sleep and woke about one.
I talked with Sherry about staying naked and she eagerly complied and I told the boys that Sherry was all theirs all day Sunday for their sexual pleasure and explorations as long as they asked me permission before they did anything.
She had them following her around all afternoon and was felt-up pretty much constantly as I gave them free access to her body except for fucking her or getting her to give them blowjobs.
I was planning that I would unleash them tonight after playing naked with her all day and that they would go wild fucking her crazy. So, they felt her up, finger-fucked her, sucked her boobs, ate her out, just everything short of penetration.
I asked the boys if they had any friends who might enjoy Sherry as well and they eagerly named off a number of other boys. My idea was a 'bukkake party' having all the young lads jack-off and cum on her as she knelt, cuffed in front of them. So, I told them to call them all and have them over by eight. Ryan had told me that all of his friends knew Sherry from previous visits and every one of them thought she was super-hot.
"Well, tell them this is their chance to have some fun with her, nice private adult-type fun."
So, the boys went off to make some phone calls while I took my own opportunity of having a bit of a feel and lick of our star of the show.