Cheryl's Gangbang 04 - The Event

(Author's note: If you haven't read the previous chapters of "Frank & Cheryl" you might want to, just to know the background on this couple and how they arrived at this point in their building relationship.

Physical descriptions: Frank is a divorced 35 year old, 5'-11" tall, 185 pounds and fit; brown crew cut hair, clean shaven, brown eyes. Cheryl is a never married 32 year old, 5'-01" tall, 110 pounds and very small framed. A-cup close-to-but-not-quite- B-cup chest with highly sensitive nipples. Dirty blond hair that she keeps cut short. They are both into fitness, so Cheryl's body, while petite, is curved and firm.)

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After a fantastic Saturday full of sex I got to enjoy Sunday with my love. Cheryl and I had enjoyed an almost pure vanilla bout of love making when we went to bed the night before. Sunday morning I woke up to her snuggling up against me. I was on my back as she put one arm and one leg over me. The room was warm and we were both naked and in my mind's eye I could see her sexy nude body partially covering mine. I saw the beautiful curve of her butt flow down to her curvy firm thigh where it lay over mine. I felt her hand caress my shoulder, down my chest, across my abdomen and down to my crotch. That hand found my semi-erect cock and loose ball sack. She began caressing and massaging my balls which caused my erection to grow. When I was at full hardness she giggled and then let go of me, rolling away and out of bed.

"What the fuck?" I asked with a grin.

"Gotta pee!" she said as she bounced into the bathroom. I sighed and realized I had to pee too -- but doing so with a full-blown erection was never easy. She came back out of the bathroom and jumped back onto the bed. She was on her hands and knees beside me, looking down with her face over mine. She smiled, leaned down to kiss me and then got back out of bed. "I'm going to get coffee started," she said as she grabbed her robe and headed toward the kitchen. "You should join me after you've let that relax enough to go."

Ten minutes later I joined her in the kitchen and our Sunday began. It was a mostly lazy and relaxing day. Sometime Sunday afternoon between lunch and dinner we ended up in bed again. She got on me in a 69 and came hard as I toyed her pussy with one of her favorite vibrating dildos, licking and sucking her clit to add to her stimulation. After she'd cum she kept riding my face and stroked/sucked me until she got what she wanted: my load of cum in her mouth. One of the things I loved about Cheryl was that she truly loved me cumming in her mouth. If I didn't do it at least once a week she got grumpy. She knew my body well and stroked me combined with licking and sucking my cockhead in just the right way to maximize my orgasmic pleasure. That also meant that she got the most cum out of me, which was a selfish motivation on her part.

We parted ways Monday morning, usually spending two or three nights of each week with each other, but some nights alone. As she left my place Monday morning, and after a long embrace including lots of passionate kissing, she said, "See you Wednesday, lover. Don't forget that this Friday is the big night."

"How could I forget?" I asked her. I'd been thinking about her pending bachelor party gangbang pretty regularly every time I saw her naked.

"I'm really excited about it," she said with an almost embarrassed smile.

"I know you are," I replied, still holding her. "And I'm looking forward to making sure you can enjoy it safely. I want you to answer your every desire."

She smiled a big smile up at me. "I love you so much," she said before reaching up on her toes to kiss me again.

"I love you too, baby," I said, smiling back. Then I smacked her on her sexy ass. "Now get to work before we're both late." I watched as she twitched her ass, sexily walking away. I sighed as I watched her go. I couldn't say I was deprived because I'd enjoyed a weekend full of sex thanks to her. Just on Saturday, including her, I'd fucked four different women and cum just as many times. Sunday, I'd enjoyed her again. I told myself it would be easy to go until Wednesday night (the next night we planned to spend together) before getting laid again. But the idea of her entertaining ten or more men in the coming weekend seemed to be keeping me on a sexual high.

The work week was tolerable, but some unexpected things occurred. First, Cheryl was told that the party had to be moved from Friday to Saturday and the organizer wanted to make sure she could still be the entertainment. She verified that she could after double checking with me (which she didn't have to do but I appreciated anyway.) Then when Wednesday rolled around, we were denied our time together. Cheryl's work sent her out of town for a client emergency and she wouldn't be back until Friday night. It was a good thing, at that point, that the party had been moved to Saturday night because otherwise she'd have had to cancel being there.

Friday night I was waiting for her at her place when she got home. I was already in bed asleep when she came in, stripped and joined me. After having gone a week with no cock I knew she'd be horny and needy. She was. To be honest, so was I. Within just a few minutes of her being in bed and us pressed against each other naked, I was hard, she was wet and I was pumping into her. I put her on her back and held her legs open while she rubbed her clit, adding to the stimulation of my cock thrusting in and out of her. She enjoyed several orgasms before I got mine, holding myself as deep into her as I could reach as I emptied my balls. After I'd cum I laid down on top of her, then rolled to one side, pulling my wilting cock out of her freshly fucked sex. She rolled with me, snuggling up as she liked to do: one arm across my chest and one leg thrown over mine. At some point, as we fell asleep, my cum began to drain out of her and onto my thigh but neither of us really seemed to care.

Saturday morning, we slept in and while we were both horny neither of us instigated anything. I think we were both aware of what the evening was going to bring and wanted to save our own play until afterward. I wasn't necessarily eager to have her after a bunch of other men had, but I did want to be the last cock she sucked and fucked before going to bed. I think she held off on her desires that morning just because she wanted to let her wants and needs build further.

We enjoyed the morning and afternoon together. She had to be at the party location at 8pm and didn't start getting ready until after we'd had dinner. I noticed she ate light, I supposed in anticipation of all the shaking up her body was going to get later. After dinner she took a long hot shower, giving her pussy a fresh shave and tending to all her other grooming. Out of the shower she dried off and instead of doing her hair as normal, she pulled it back in a high tight ponytail, and then braided what was hanging. She used hairpins to secure the ponytail down the back of her head. I was curious as to why and she answered that it kept the guys from using her hair as a handle. A ponytail or braided hair was too easy to use and she didn't want to risk a neck injury if the men lost control or more than one of them was trying to direct her. I had to admit that it made sense and was struck by the practicality of such planning. I guessed it was something any hooker would know if they'd done group events. I wasn't sure the average woman would know such a thing.

I left the room before she got dressed because I wanted to enjoy the striptease she was sure to do as much as all the other men in attendance. She told me she was ready at about 7:15 that evening. I was ready to go as well dressed in business casual clothing that wasn't restrictive. I didn't expect to have to fight anyone but if I had to experience any physical conflict, I wanted to be able to move well.

While she finished getting ready to go, I put together the small cooler I planned to take. It had a dozen bottles of water and a few small bottles of various liquors. I knew what Cheryl liked and I would be providing her 100% of her drinks for the evening, so I had a variety available for her.

We held hands as we walked out to my car and I held the door for her as she got in. She had a "purse" that was more like a small piece of luggage. I knew that inside it was lube, some toys she wanted, a container of baby wipes and a few other assorted items. She was quiet as we drove and I wondered if she was nervous. I both wanted to ask and didn't want to disturb her if she was somehow otherwise mentally preparing herself for the coming event. As we were pulling up to the event location, she reached over to take my hand. "I love you," she said, still looking straight ahead.

"I love you, too, baby," I replied. "You okay?"

She giggled. "I didn't expect to be nervous but here I am."

"Why are you nervous?" I asked.

"Because I haven't done this in a long time," she replied, "and I've certainly never done it with the man I love, who loves me, watching." She paused. "I guess there's still a part of me that expects some judgment or negative reaction from you at some point."

"Stop," I said, squeezing her hand. "I love you. I've yet to judge you. I'm not going to start now. Just do your thing and have all the fun you can. When it's over, we're going home together and falling asleep in the security of each other's embrace." It must have been just the right thing to say. She squeezed my hand back, smiled and then let go as she got out of the car. From that point forward I was acting as her escort and bodyguard, not her boyfriend. She carried her bag and I carried the cooler as we went in.

The party was being held in a suite at one of the higher end local hotels. We already had the room number and went up the elevator in silence. Cheryl was dressed in an extremely sexy fashion but not so as to look slutty or like a hooker. Her dress was a very nice dinner dress that was cut on the side of sexy rather than conservative. She had on hose, and I assumed they were thigh highs but I wasn't sure. The dress actually came far enough down her thighs that I hadn't been able to see much of them. The dress was tight but not so much that I could see lines from any of her undergarments. Her heels were 3" which looked much higher on her five-foot one-inch frame.

At the top floor we got off the elevator and went to the suite. It was one of only two on that floor. We knocked and the door was opened by a good looking guy, perhaps a little younger than we were. White, about six feet tall, dark curly hair neatly barbered and brown eyes. He was clean shaven and dressed in slacks and a salmon colored polo shirt. When he saw Cheryl, his whole face lit up.

I wasn't surprised when she stepped toward him and he wrapped her up in a big hug. As I quickly learned, his name was Jerry and I already knew that he had known Cheryl in her life as a prostitute. I was barely aware of what they were saying to each other as I looked around at the living area of the suite. It was a large room with two sofas, several chairs, a bar that had several bar-height stools, and a dining table with four more chairs. Through the living room I saw double doors that were open with a king bed visible in what must have been the bedroom. To the right of that was another open door and it looked like it had another smaller bedroom too. Apparently, everyone else had been told to show up at 8:30 as no one else was there besides Jerry.

Cheryl introduced me as her escort and bodyguard and reviewed the rules of the evening with Jerry. He had told everyone that if they wanted to attend anything beyond purely watching the striptease, they HAD to bring a current STD report that was dated less than a week before the event. It had to be surrendered to me, along with their cell phone to gain entry. Jerry said a total of 13 men had been invited, including himself and Cheryl smiled pretty wide at that. I knew that our conversations all week had revolved around the potential of ten men, but 13 would just make her evening more fun... if I knew her at all.

Cheryl assured Jerry that she would review all of the rules of the evening after everyone had arrived, and until then, it was just time to relax. She took her bag into the big bedroom and put it in a chair that was situated in one corner. After putting the cooler behind the bar, I walked around the suite, looking behind every door and checking every area. I wanted to be thoroughly familiar with the layout and what was where. When I walked back out to the main room, Cheryl was sitting on one of the barstools and Jerry was behind the bar pulling out bottles.

"What would you like to drink?" he asked both Cheryl and I.

"Nothing, thanks," replied Cheryl with a smile. She saw the questioning look on Jerry's face but I gave him his answer.

"The only person allowed to make drinks for Cheryl this evening is me," I said. "She may know and trust you, but she doesn't know anyone else and her background has taught her to avoid taking drinks from strangers. To avoid any potential issues, I will make and deliver all her drinks to her, no matter what they are. From here on, the cooler stays where I am and I stay where she is."

Jerry looked a little surprised. "Wow," he said after a minute. "That's a bit of a change from the last time I saw you."

"A lot has changed since then," Cheryl said with a smile, "but what hasn't changed is that you can count on enjoying watching me do a great striptease and then spend an evening pleasing all the men who are admitted."

"Well, that's all that matters I guess," said Jerry. I could tell he was excited about getting his chance to enjoy her sexually at some point that evening, and I knew that one of the things that had changed was her involvement in a relationship with me. Jerry and the others may not know that, but she did and I did and that special knowledge just made the evening better -- to me anyway.

At almost exactly 8:30 there was a knock at the suite door and I stepped over to it. Opening it half way, I put my foot behind it so it couldn't just be pushed open and greeted the first group of attendees. There were four men and they started to step in, stopping short when they realized that the door wasn't opening any farther and I wasn't moving.

"Good evening, gents," I said with a wide smile. Just being polite. "I'm Frank and I'm here to make sure Cheryl is safe for the evening. Each of you has a current STD test from what I understand?"

Three of the men reached into pockets of jackets or pants and started to pull out papers. One of them looked at the others and said, "You were serious about that? She's a hooker. We gotta be disease tested?"

I answered him and my voice was far less pleasant. "Yes, she's a professional escort and everyone was told that if they wanted to participate, it's an unprotected evening. For her health and that of everyone else attending, every participant is required to show a current, recent disease test. If you don't have one you can't be admitted."

He bucked a little bit at that. "Who the fuck are you to tell me I won't be admitted? I was invited and I can come in whether you like it or not."

I didn't move and I kept my voice flat. "I'll repeat this: everyone was told that to get in they had to have a copy of their current disease test results showing them disease free. If you don't have one, you can't come in. If you try to come in, you will fail."

He wasn't ready to challenge me physically by himself, but he did make the attempt to recruit a friend. I didn't realize it but Jerry had stepped up behind me. Big mouth in the hall turned to the guy next to him, "C'mon... we can take this guy and then do what we want for the evening."

The guy he was talking to said, "Fuck off, asshole. You were told. Don't be a dick."

Jerry jumped in as well. "Everyone was told," he said. "Don't ruin everyone else's weekend just because you thought the rules didn't apply to you."

Big mouth looked around another few minutes and then turned and walked back to the elevator. His three friends all handed me their test results which I reviewed and then handed back. I didn't want to keep them and, if I was one of them, I wouldn't want a stranger to have them. "Phones," I said, holding out my hands. Each of them surrendered their cell phone which I placed in a basket inside the door on a small decorative table. "Come on in," I said, the smile returning to my face.

"Help yourself to the bar," Jerry said, shaking hands with the guys and slapping one or two on the back. "Just don't get drunk because you definitely want to be pure sober to enjoy later."

Each of the men smiled and greeted Cheryl who accepted handshakes, hugs, kisses on her cheek and a hug from the last guy. Across the next half hour, the evening flowed with very vanilla social time. The guys circled around Cheryl and engaged each other in conversation. Several offered her drinks and she assured them all that she was fine with what she had. I went through the routine at the door a couple more times and had to turn away another guy who thought the disease test requirement was a joke. So, after everyone was in and the door was locked, Cheryl had eleven men, not including me, waiting to see her do a little dance, display herself gradually through the striptease and then have their turn at her sexually.

I could tell she was happy.

At 9:30 Jerry announced that it was time for the entertainment part of the evening to begin and he accepted a CD of music from Cheryl to play while she danced. Before she started, she arranged where everyone was sitting so the groom was alone in a comfortable chair, at the top of a circle of the sofas, other seats, etc. At first I tried to keep track of everyone's name but I realized it was a losing battle. I knew there were eleven men. They ranged (roughly) in age from mid-twenties to about fifty. There were seven white guys and four black guys. Some of the "white" guys were probably Italian, of Hispanic background or had another Mediterranean region cultural background. All of them were well groomed, were neat, seemed fairly fit and dressed decently. I realized that all of them, had Cheryl been available, looked nice enough she'd consider dating them, depending on their personalities.

Once everyone was seated and the music was queued up, Cheryl got up from her barstool, threw back what was left of the first drink I'd served her (a mixed cocktail I knew she liked that had just enough alcohol to help calm her nerves), and then stepped over into the middle of the circle. Before she started the music, she gave a short speech.

"Hi, there," she said with a smile, looking around the circle, turning as she went and making eye contact with every attendee. "In case you didn't know," she said, "my name is Cheryl. Throughout the evening, if you specifically need or want my attention, use my name. I won't answer to anything else. That said, once some of the more... intense fun starts later, if you want to use any other language to refer to me, I don't care. I don't mind being called a whore and I'm very proud of being a slut, so such terms don't bother me at all. Just don't say 'hey, whore,' because I won't answer to it. I'll just assume you're talking in the midst of the moment. If you need my attention, say my name." She kept looking around and saw everyone nodding.

"Next," she continued, "while I will appreciate everyone's good intentions and attempts to be nice, I will not accept a drink from anyone except Frank." She pointed at me. "As you all learned at the door, he's here as my escort and bodyguard." She paused and took a breath, I assumed to gather her thoughts, but I realized she was trying to figure out a polite way to say what came next. She apparently just decided to be blunt about it. "Later, when the fun really gets going," she said, "I'm happy to say that almost anything goes. However, if I say STOP or NO, I mean STOP or NO. It's not optional, it's not 'in a minute' or 'when you're done." It means right that moment and if you don't, Frank will. His only purpose here is to assure my safety and comfort. I decide both and he will respond... enthusiastically if I need his assistance." She stopped and looked around again. "Does everyone understand? We are all going to have a lot of fun later, but it will be stopped and probably ruined for everyone if Frank has to get involved. So pay attention, okay?" She looked around and everyone nodded.