Cheryl's Circle Jerk

I guess this story starts on a lazy Saturday morning. Cheryl had spent the night at my place and we'd closed out Friday night with a couple hours of sex play before going to sleep. As much as I love morning sex, when I'd woken up this particular Saturday morning, Cheryl was still sound asleep, and I decided to let her sleep in a bit. I slipped quietly out of the bed, grabbed my robe and snuck out of the bedroom. After peeing in the hall bathroom, where there was less chance it would wake my love, I went into the kitchen to get coffee going. As the coffee brewed, I opened up my iPad and started browsing my various feeds. When the coffee was ready, I got myself the first cup and was headed back to my seat at the breakfast bar when Cheryl came wandering out of the bedroom naked. It's a view I always love and with my coffee in one hand I smiled as I said, "Good morning, lover. Sleep well?"

Cheryl smiled at me but didn't answer me. She kept walking until she was right in front of me, and then, without a word, dropped to her knees, opened my robe and sucked my cock into her hungry mouth. No guy in the world is going to object to such a greeting and I certainly wasn't going to. I leaned back against the counter, and just stood, sipping my coffee while enjoying an amazing good-morning blowjob from Cheryl. She licked, stroked and sucked my cock, sometimes stroking my length as she sucked or licked my balls, until I felt my orgasm getting close. I set down my coffee as I let her know I was close to cumming and her response was to increase the energy of her efforts. It didn't take much longer, and I was climaxing. Cheryl took the first few spurts in the back of her throat and then popped off my length, stroking the next few jets of cum onto her face and chest... until she could get no more cum out of me.

She smiled up at me and said, "Good morning." It was hard not to see a devilish woman as I looked down at her cum-smeared face smiling up at me, her hand still stroking my now softening cock.

"Good morning again," I said with a smile of my own as I caught my breath. "What brought that on?"

"What?" she asked with a smile as she stood up. "I need an excuse to suck your cock?"

"Not at all," I replied. "I was just wondering if anything particular inspired your hunger this morning." She let go of my cock and stepped over to the sink where she used handfuls of water to rinse off her face before drying her face and hands with paper towels. Then she answered me.

"Actually," she said, "I had an interesting dream last night that I woke up horny out of." She paused before adding, "Truth be told, I could suck another few cocks and still want more at the moment."

"Wow," I said, as I watched her get her coffee. "Well, you know I'm always willing to give you all I can, and I don't object to adding more playmates for you, but wanting several cocks for a random Saturday morning? That sounds especially horny and kinky, even for you."

She had her coffee made and went back to the bedroom to get her robe. I followed her, because why would I ever miss a chance to look at her delicious naked body? Together, each of us in our robe, sipping our coffee, we sat at the breakfast bar, and she told me about her dream.

"The dream I had," she said, "involved me being the only woman in a room with about ten men..."

"Didn't we just do that not long ago?" I asked (See the series about Cheryl's Gangbang.)

"Yeah," she said with a huge smile as she remembered the event, "but this wasn't a gangbang. Let me describe the situation." I nodded, acknowledging her implication that if I'd just not interrupt, she could finish telling me all about it. "I was in a room, on a mattress, and there were about ten men standing around me. I was laying on the mattress, masturbating with one of my toys, and the men were all watching, stroking their cocks. When I came, several of them did too. I can't tell you exactly how many men it was, but the dream kept jumping from me giving them a show to me orgasming just as they did and every man their shot his cum onto my body. Some of it was on my chest, some on my belly, some on my pussy, some on my legs... but only one -- you -- were shooting on my face."

I pondered what she had described. It didn't bother me at all. While we were absolutely emotionally monogamous, we had never been physically so, and we both enjoyed watching the other enjoy sexual pleasures. The things that surprised me about her dream as she had described it, were that she usually likes to get fucked, not just used as a target, and knowing how much she likes the flavor of cum, the fact that none of the men in her dream came in her mouth was kind of a surprise.

"So this dream really turned you on, huh?" I asked her.

"Yeah, it did," she said with a grin. "I don't know why in particular, but the idea of watching a group of men jerk off while they watch me toy my pussy to orgasm several times, and then they all give me their cum... yeah, it was just hot as fuck."

"I'll keep it in mind," I said with a grin, and then we moved the conversation on to what we should have for breakfast, etc. I tucked the information away and had a thought about what I'd do with it in the near future.

That's why, about three weeks later, when a swinger group we're familiar with announced a big hotel party, I reached out to the party coordinator. Her name was Lelsie and we knew her well enough I guess. She was our contact for the hotel parties coordinated by the group and on a couple occasions she had controlled a sybian while Cheryl had ridden it. I told Leslie about Cheryl's dream and asked for her help in setting it up to be reality. Could we find eight or more guys to jerk off on Cheryl while she gave them a masturbation show? Leslie seemed to feel that she could, assured me she would work on it and get back to me. The hotel party was almost six weeks from when it was first announced, so Leslie had that time to find willing participants. About four weeks later Leslie reached out to me to let me know she'd found twelve men who all were planning to be at the hotel party and would be happy to help us fulfill Cheryl's fantasy. Leslie also promised me she'd keep it a secret from Cheryl, and we moved forward with the plans.

And so, when the weekend of the hotel party arrived, Cheryl and I were packed up and driving down to the location. It was a few hours from where we lived, but we didn't mind the drive. We'd get there Friday evening before dinner and not have to leave until Saturday after a late check out. Knowing how the parties usually went, we'd be up until two or three in the morning playing and we'd get seven or eight hours of sleep before checking out and heading back home.

As we drove, I told Cheryl I had a surprise for her at the party. She asked a few questions but knew I wouldn't give anything away. At the end, she told me she was just really eager to see what it was and have fun enjoying it. We got checked in at the hotel, dropped our bags in our room and went down to the hotel restaurant for dinner. Our usual play evening meal was a grilled chicken salad as it was filling enough but not so much that our stomachs would get upset later with any type of rigorous movement.

The party itself was slated to start about eight that evening and we finished dinner by six. After saying hi to a few of the other couples we knew, we headed up to our room for a short nap, a fresh shower and then to get ready for the party. To our surprise, as we were taking turns in the shower, Leslie knocked on our room door. I had a towel wrapped around my waist as I let her in, and she went into the bathroom to talk to Cheryl who was still in the shower.

Now, Leslie had seen Cheryl naked before but it's still erotic to have a woman whom we saw maybe three times a year, just stroll into the bathroom and start having conversation with my naked lover. Cheryl didn't even blink, just greeting Leslie with a smile and then jokingly asking if Leslie wanted to join her in the shower. I really wasn't expecting Leslie to say, "Sure!" and then strip down, stepping into the shower with Cheryl once she was naked.

As I watched, dropping my towel and stroking my cock without shame, Cheryl and Leslie embraced, kissing passionately as their hands wandered each other's bodies. Where Cheryl was a very petite blond, Leslie was a curvy brunette, much larger boobs and much longer hair. I enjoyed the show as Cheryl rinsed off thoroughly and then they played with each other a little bit. Before they got out of the shower, Cheryl had dropped to hear knees and eaten Leslie to an orgasm. Leslie had pushed Cheryl up against the shower wall and fingered her to an orgasm. My dick was throbbing and dripping precum... and I was pretty sure it was going to stay that way unless I got into a really cold shower.

When they were drying off, Leslie said, "So, I have a surprise for you this evening if you're up for it."

"Of course," I am, Cheryl replied with just the quickest of glances my way. "Just let me know when and where."

Leslie giggled at how eager Cheryl was. As she pulled on her meager clothing she said, "After the party gets started, I'll come get you. You guys will be in the social room like usual, right?"

"We'll make sure we are," Cheryl replied. They gave each other a quick kiss goodbye and then Leslie gave my cock a stroke as she walked by me out of the bathroom.

"I'll make sure that gets taken care of too," she said to me as she pulled on my dick.

"I know you will," I said with a smile. After Leslie left, it only took Cheryl and I about another fifteen minutes to finish getting ready and then we headed down to the social room. Once there we each got a drink from the bar and then mingled, greeting some folks we knew and introducing ourselves to some folks we didn't.

At about 8:30, Leslie found us and took Cheryl by the hand. "You ready for your surprise?" she asked.

"Ready and eager," said Cheryl with a big smile.

Leslie turned to me and said, "You too. Come on. You get to at least watch."

"Oh, good," I said with a shit eating grin. I knew I was going to get to do more than watch, but I also knew Leslie was keeping info hidden from Cheryl to help build the surprise. We followed Leslie up to the third floor of the hotel and down the hall to the last room on the right. There Leslie stopped us and pulled a blindfold out from under the waist area of her dress. Turning to Cheryl she said, "You have to put this on, but only for a moment. Once we're in and have you set up, then you can take it off." I knew Cheryl had a bunch of questions she wanted to ask, but she didn't. She just nodded her head and stood still, accepting it as Leslie tied the blindfold onto her. After double checking that Cheryl couldn't see through or under the blindfold, Leslie knocked on the room door, I assume to alert whoever was inside that we were coming in, and then unlocked and opened it. I followed as she led Cheryl into the room by her hand.

Inside the room were about ten guys, I didn't take time to get an exact count, all standing around naked, talking and drinking. They all looked quite comfortable being naked in each other's presence and I realized that I recognized several of them from previous hotel parties. On the floor was a mattress, and all of the other room furniture had been pushed back against the walls. On a table to one side was an assortment of toys and a couple bottles of KY liquid. I realized that Leslie was gesturing for all the men to be quiet and knew that was what her knock on the door had been for; it was a warning to them that she was getting ready to come in with Cheryl and she didn't want to give anything away until Cheryl was in position.

Next to the mattress, Leslie stopped and then undressed Cheryl. My lover didn't voice any objection as her wrap-around dress was removed, which happened to be all she was wearing except for her shoes. It was, after all, a swinger's hotel party, and she had "dressed" for ease of getting naked and allowing playmates access to her body. She stepped out of her shoes and moved as Leslie directed her onto the mattress and then to laying down on it. With Cheryl on her back on the mattress, Leslie moved over to the table and picked out a vibrator, taking it back to Cheryl and putting it in her hands before turning it on.

"Now," Leslie said to Cheryl, "before I take the blindfold off, you have to get at least one orgasm." The entire room watched as Cheryl immediately began using the vibrator on her pussy, sometimes just circling the head of it around her clit and sometimes thrusting it all the way up into her sex. It took maybe three or four minutes before her orgasm arrived, with Leslie caressing, pinching and pulling Cheryl's nipples all the while. Once Cheryl's orgasm had passed, Leslie said, "Don't stop playing with your pussy," and then took the blindfold off of Cheryl.

Cheryl's smile grew as she looked around the room, keeping the vibrator working in and on her pussy, finally looking around to where she saw me. "Why are you still dressed?" she asked with a grin. "You'd better give me yours too," she said and then went back to looking around at all the naked men and growing cocks surrounding her. "All right, guys," she said, "I'll give you the best show I can, making my pussy cum as many times as I can, but you guys need to return the favor. Stroke those delicious looking cocks and cum all over me when you're ready." She looked over at Leslie and said, "Thank you, baby."

"My pleasure," Leslie said, "but you owe Frank your thanks. He asked me to set this up after you told him about some dream you had?"

Cheryl looked over at me with that knowing grin and said, "He's going to get special thanks later," and then she laid her head back, kept her eyes open, and focused her efforts on pleasuring her pussy. Leslie excused herself claiming she had some other hostess duties to attend to and gave my cock another stroke as she walked by me before leaving the room.

As she stroked my growing length Leslie quietly said, "If she can't take care of this later, make sure you find me, and I guarantee I'll drain your balls."

'I'll have to find you to thank you anyway," I replied and gave her a quick kiss before she left. Then I stepped over and took my place, standing closest to Cheryl's head, and looking down at my lover as she energetically masturbated while watching all of the men surrounding her do the same.

In the ten to fifteen minutes that followed Cheryl enjoyed three or four orgasms, each seemingly more intense than the last. The men stroked their lengths as they watched her, each using some of the KY liquid lube as necessary. Honestly, we passed it around like it was a joint, each man taking a little and passing it on. Several of the men jerked like I did... long slow strokes of my length while my other hand fondled and massaged my balls.

Moans from one guy on Cheryl's left made it clear that he was getting close to his orgasm, and he stepped just a little closer to where she was laying. Cheryl heard his moans and knew what they meant, and she began to encourage him. "That's it," she said huskily, "give it to me. Spray me. Cum on me."

He was the first to give her what she asked for, and his orgasm seemed to spur several others. I'd guess he shot about a half dozen thick heavy ropes of cum onto Cheryl's body, most of them hitting her belly and ribs. She moaned; her eyes locked on his cock as it spit the creamy jizz onto her.

Before he had even finished cumming another guy went off, this time near Cheryl's right leg. He moved closer, gave his cock a few last tugs and then began firing his load all over her right thigh, one or two spurts landing across her hands, the vibrator and her shaven pussy lips. "Yes," she moaned out. "Cum on me. Cum everywhere. Spray my tits and cunt."

The two men who had cum immediately backed off and made room for the other men to get closer. With a few minutes, two more had cum on Cheryl and she had another orgasm as they did so. One sprayed her chest while the other stepped between her legs and came all over her pussy, hands, toy and lower belly. Somewhere in the back of my mind I idly thought, "That's four..."

Then the next guy came. He was standing just to my right, so he directed his load onto Cheryl's upper chest, neck, shoulder and one streak across her right cheek. It just missed reaching her mouth which she had opened wide in anticipation. "Damn it, I missed," he said with a grin as he gave his dick a few more strokes, but just then the guy to my left stepped up and started firing off. Cheryl quickly turned her head to the increased sounds of moans and his first jet of cum landed right in her open mouth. As I watched, she came again while he jerked his load across her neck, chest and face.

"Six," I thought. As Cheryl came down from her orgasm, she kept toying her pussy, moaning and opening her legs wide. "More on my pussy," she said to the remaining men.

They complied. Number seven stepped over close to her left hip and when he came, he sprayed it directly across her hands, toy and pussy. She moved her hands and the toy out of the way after his first spurt, so the rest of his load liberally coated her sex.

I could feel my own orgasm getting close but slowed my stroking. I wanted to be the last to cum and I had yet to decide if I was going to do it on or in my lover. Cheryl was trying to catch her breath and had swallowed the little bit of cum that had landed in her mouth. She looked at the remaining guys... four of them I realized, not including myself... and said, "More, guys. Cover me."

Number eight stepped up and came all over her chest, leaving one streak on her neck and then trying to get his last spurt on her face but falling short, adding more to her chest. Number nine was near her feet but stepped between her legs when he started to cum, and I was really surprised when he did. His first shot of cum landed on her face and the robe of jism was so thick and heavy that it left a line from her forehead to her pussy in one continuous stream. He must have fired off another eight or nine such ropes of thick cum, and his load alone would have "covered" her to her liking. As it was, I realized that his cum clearly stood out on top of the other cream on her skin. It was like it was from a different species. Cheryl watched every spurt with a delighted look on her face and after the guy had finished cumming she looked up at me. I knew what the look meant. At some point, during one of these hotel parties, she wanted to play with that guy and feel him cum up in her. It was a lot of ejaculate.

Two guys were left, and they came almost simultaneously, one on her left and one on her right. The guy on her left aimed for her pussy while the guy on the right aimed for her face. The ended up leaving almost parallel streaks of cum diagonally on her body, finalizing what she was going to get from her surprise for the evening. I still had not cum and was holding off... barely. I still wasn't sure where I wanted to leave my load, but as I slowly stroked my cock, looking around at the men still watching Cheryl toy her pussy, covered in cum, I knew what I was going to do. Without fucking her in front of them, I was going to make it clear that she was my woman.

I knelt down to the left of her head, my cock directly above her face and increased my stroke speed. I knew it wouldn't take me long to cum and I was going to put every drop in her mouth. "Open wide," I said to her, our eyes meeting as another orgasm for her approached. She obeyed instantly. I moaned as my orgasm set in and she buried the cum covered toy up into her cunt as she came again at the same time. I aimed carefully and delivered several thick hot ropes of my sperm directly into her open mouth, onto her tongue, down her throat. I kept milking my length until her orgasm was over and she opened her eyes to look up at me, her mouth still wide open and all my pooled cum visible there. Then she smiled, closed her mouth and swallowed, drinking down every drop.