Cherry Doubles Down

This story is a sequel to the story titled Cherry's Gangbang.

~~~~~~

As promised, Brad called me three months after our first gangbang party, corresponding to the end of another quarterly sales contest. When I realized it was him, I felt a wave of excitement, rising from my lower areas.

He didn't waste any time. "Cherry, are you up for another party?"

I reacted instantly, without asking for any details. "Yes! Last time was completely awesome. Let's do it again."

"Great," he responded. "That's great." He seemed pleased but hesitating.

"Is something wrong?" I asked.

"No, no. Not wrong. But it's going to be different this time."

"What do you mean?"

"Well, my team didn't win. But it's okay. The winning group, another team of eight, won fair and square."

His voice changed to a tougher sound. "We'll just have to kick their asses next time."

I laughed and assured him, "I have total confidence you can do it. But, what happens to our party?"

Brad hesitated again, then said, "Um, nothing really. It should be the same format but with the other team."

"I'll miss you, but okay if you say so. Is there more?" I still sensed he was withholding something.

"Cherry, there is one thing..."

"Here it comes," I thought.

"What, Brad? Just tell me."

"It's only seven men."

"Didn't you just say eight?"

"Seven men and one woman, a twenty-six year old beauty named Andi."

"Oh. Another woman. How does she fit in?" I wasn't thrilled.

"She's the leader of the winning team, very successful in her work. And the seven guys on her team are all in love with her. They admire her but, off the record, admit to sexual interest too. They have been fantasizing about Andi for a long time, but back in our home town dating within the team isn't permitted, would never happen. But now they're going to Vegas together, different story."

"How does Andi feel about it? Have you talked to her?"

"Yes, of course, but very discreetly. I didn't want anyone to know in case she turned it down. But just the opposite. She had her own imagination at work. She claimed to be excited and happy when I brought it up."

"What else did she say?" I asked.

"She actually prefers a gangbang party over dating. She likes the idea because everyone gets taken care of at once, without jealousy."

He asked my opinion, "Cherry, they all say they want this, but your guidance will be crucial. Does this work for you?"

"I've joined with women in a gangbang. It opens up a lot of new possibilities if you use your imagination. But it can be tricky too; there has to be chemistry."

He didn't add anything so I asked, "Is there a way for me to meet her?"

"I'm already ahead of you. Andi will be arriving in Las Vegas Sunday night for a technical seminar that lasts all next week, nine to five. You can help her get ready. She'll be at the Hilton and will contact you."

Brad knew there were risks, but he was hopeful, "If you two get along, she's in and I think, with your help, she'll be great."

"I'll do everything I can to make it work," I told him.

~~~~~~

Early Monday evening, Andi called. She seemed very charming on the phone. We talked about meeting right away, deciding that the best idea was dinner in her room at the Hilton, so we could have a private discussion with no one else around. I had rearranged my work schedule, free to be with Andi in the evening.

When she answered her door, I was delighted to see her welcoming smile and hot body, casually dressed in a tee shirt and jeans. She was shorter than me, with brown eyes, shoulder length straight black hair, parted in the center. To me she had a delightfully untamed, wet and wild, outdoor look.

She radiated energetic confidence. Plus, she really filled out the tee, braless, showing nipple bumps.

"It won't be a chore to have sex with this one," I thought.

Andi seemed to be having a good reaction to me as well. "What do I call you?" she asked cheerfully.

"My real name is Peggy Trent, but you can call me Cherry. Brad and his group all do."

After a quick hug at the door, she led me to the couch. Room service carts were already in place with two fillet mignon dinners under silver domes surrounded by all the trimmings, side dishes, bread sticks, and a bottle of champagne. A separate cart of desserts was there too along with a coffee urn, ice water, and an assortment of bottled drinks.

"How many people are you expecting?" I asked her, amused at the quantity.

Andi shrugged, "Brad told me to spare no expense, to have fun and make sure you did too."

We made jokes about it while she got the food ready and I poured coffee. We talked easily, like old friends.

She wasn't shy about why we were there. Apparently she had given it a lot of thought.

"Brad told me," she began, "that you had a gangbang with his team after they won the sales contest three months ago. According to the buzz, it was epic."

She paused, then asked, "Are you okay talking about it?"

"Sure, it's not a secret. And my inhibitions went out the window as soon as I started in porn."

"Yes, Brad linked me to some of your movies. Whew!" She grinned at me.

"What do you think, then?" I asked.

"It's already my biggest fantasy to be the center of a gangbang. I get totally hot when I think about all those men doing everything with me."

"Have you experienced that in real life?" I asked.

"Yes and no," she responded, oddly.

"Tell me," I probed, taking her hands in mine.

"Here's what happened. I was at a bar with two guys from the gym, drinking, having fun. They bet me I was too chicken to have sex with both of them on the pool table in front of everybody."

"Ooo, hot," I reacted. "Tell me more."

"I think they were just joking around. They didn't realize the idea made me intensely hot, helped by the drinks. They weren't serious, but I just hopped on the table and started to strip. Everybody in the bar crowded around the table to watch, screaming and clapping. That only made me hotter."

"This should be a movie!" I encouraged her. "Downloads by the millions."

"Really, but the guys chickened out. There I was, just wearing a thong, all hot and wet, but they went limp on me."

"Losers," I commiserated.

"I was really ready for it. The way I was feeling, I wanted every dick in the crowd to do me."

She appeared embarrassed, trailing off, "It's what I wanted."

"Are you looking for revenge or something?" I asked.

"No, no. It's all good, all good. I made up with the guys. I told them I was too drunk to remember."

She brightened, "When you meet my team, I'm sure you'll like them. This time I'll finally get to live my dream."

I was curious, "Do they know you're doing this? Your team?"

"Brad and I discussed that. It would be fun to surprise them, more exciting if they didn't know until the party started. But that might be too much. I have to work with these guys. So Brad's going to call Tony to brief him the night we arrive in Vegas, to explain why I'm spending my time with you. They'll have a few days to get used to the idea."

"Where does Tony fit in?"

"He's assistant team leader, my alternate. I report to Brad who is the overall VP of Sales in addition to running his own team."

She paused, then said, "You know, we only beat Brad's team by four percent in the latest quarter. Someday they'll be back, or another team. We have seven teams around the country."

She looked at me, excited. "Imagine the party if we had all the teams at once!" I got a whoosh of heat as we shared that fun thought.

I looked at her as we ate and drank quietly for a few minutes. Not only was my impression of her good as a partner for the party, but I was drawn to her, excited by her presence. She had an energy that harmonized with me somehow. I was very encouraged.

"How did it go your first time?" she wanted to know.

"Hmmm. Circumstances were quite different. My early porn movies were tame: masturbation, one or two men at most, maybe a girl-on-girl scene."

"Gradually the number of male performers grew and the focus shifted to how much cum they could dump on me and what I did with it. By the time I did 'Bad Girl Downtown,' my ten man gangbang, it wasn't shocking or anything, just more guys sticking their cocks in me and getting off."

She got quiet, suddenly confronting the reality.

"Are you okay?" I asked.

"Yeah, but I'm afraid I'll walk in the room and freak out. Maybe it's too much, even though I think I want it."

"Andi, Andi. Don't worry. We have all week together, every evening plus Saturday. We can get you ready."

She hugged me, letting a few tears flow, then rested her head on my chest.

"I don't want to blow this. I'm not afraid of doing it. I don't have any doubts about that. It's more like I'm cast in a play and afraid I'll forget my lines or something."

"Ah, no problem with that. Your natural sex drive is a lot more reliable than your memory. Once you get started you'll lose yourself in it, get carried away with the arousal and the feelings. You'll do fine."

"Where do we start?" she asked, sitting up straight on the couch.

I had one question, very important. "How do you feel about sex with a woman, me in particular?"

"Oh, I should have said something. I've been bisexual with girlfriends. We have a good time."

We sat silently, then she realized what I was waiting for.

"Oh, me and you. I'm impressed and amazed by you. I can't wait to find out how you are as my sex partner."

I responded by kissing her. The simple mouth kiss rapidly evolved into a tongue exchange, very deep and very wet. She responded easily, naturally, as I felt my own arousal growing.

My hands went under her shirt to her boobs, feeling their weight, the softness and curves. Her nipples pressed into my palms as my fingers kneaded her. I moved closer, pulled her onto my lap, then we fell onto the couch, entwining together, pressing our bodies into one. I hooked one leg around her and rubbed my pussy on her thigh as we ground, moaned, and panted.

Overcome by breathlessness, I broke off the kiss, gasping for air, then went right back to Andi's luscious mouth, loving every minute.

"Oh, this is going to be great," I told her at the next break, getting the biggest, dazzling smile in return.

A few minutes later, we were in bed, our clothes were scattered around the room, my tongue was in her sweet pussy and she was in mine. That was just the beginning of a night of extreme passion, inventive sex play, and complete evaporation of any anxiety about the party, scheduled for a Friday night, three weeks away.

~~~~~~

Each evening that week we had dinner together at the Hilton or nearby. Afterward, in her room, I showed Andi something new from my black bag. The carrier, really an ordinary compact duffel bag, became a symbol of her erotic progress. Its contents included dildos, vibrators, butt plugs, cum-like lubes, restraints and much more.

We made a lot of jokes about the unending contents of the bag.

"Harry Potter must never know what use we made of the Extension Charm..."

One of the first things I did for Andi was to get her started on anal training. I knew at least some of the men would expect that and many women require a little help to get going.

The first time, she objected when I showed her a giant dildo.

"That? You expect me to fit that in my butt?"

"Yes, but not right away. Here, start with this. Put it in."

She lubed up a slim vibrator and lay on her back, sliding it inside her ass without problems.

I kissed her, whispering, "That's right. Now slide gently in and out, get used to the idea."

She had already been prepped internally, the way I taught her, so she was clean and ready.

She got the giggles, reaching up to me for another kiss.

During the kiss, I replaced the vibrator with a butt plug, a size or two larger than the slim vib.

"Okay? I asked, while licking her nipples.

"Yeah, that stretches me just a little, easy peasy."

"Now try this." I showed her how to use a dildo in her pussy with the butt plug still in place.

"Oh, oh, ...that's new!" she exclaimed.

I shoved my tongue deep into her mouth to give her something else to focus on. When she seemed ready, I used a vibrator on her clit until she had an orgasm. It started small, then exploded as all the parts meshed.

I held her, rocking, until she could talk again. She breathlessly exclaimed, "Oh my God, what was that?"

She was panting heavily, flushed and sweating in my arms, both amused and alarmed.

"The butt plug forces your pussy into a tighter space. When you climax, it's more intense," I explained.

She was still breathing hard. "You got that right. I didn't know..."

"We're getting you ready to accept anal sex from guys, but it's not only for them. Anal does a lot for you, not just your partner. Of course, at the gangbang you won't need a butt plug."

"Why not?"

I laughed at her. "Because I hope you'll have a dick in your ass, sweet little thing."

We had the best week, with sessions like that, gradually expanding Andi's world. I was delighted to find her eager to try everything and to work on any obstacles. By the end of the week, she was doing it all.

As a final exam on Saturday, I kept Andi busy for over two hours while I reamed her in all holes using imaginative combinations of the sex toys and my strap-ons, including all the XL sizes. At the end, she was spinning up another orgasm, one of many. I buzzed her clit with my tongue while my hands manipulated the vibrators in her pussy and ass.

I went to her head while moving the dildo from her pussy to her clit.

"Now you just relax," I purred in her ear, giving her a little lick from my tongue.

"Oh, Cherry, so good, fuck me more, oh, oh, oh ... "

She was about to come, giving little sweaty signs I had learned to expect from her.

She gave a strangled gasp, and began to buck and stretch as the orgasm hit her.

And right then I squirted a warmed can of Super Vanilla Fun Whip in her face, ear to ear, including into her open mouth.

Startled, she shrieked and gurgled, but increased her thrashing from the orgasm as I moved the pressurized whip cream to cover her entire pelvic area. I pulled the vibrators out and gave her more from the can blasting directly into her pussy and ass. I reinserted goop covered vibrators in every hole and her mouth.

She couldn't stop her intense noises and the violent movements as I overwhelmed her senses with the cream on top of everything else. She screeched, shook, shouted, "No! No! Oh fuck, yes, yes..."

I covered her breasts with cream, then sucked her nipples through the gooey stuff. It was much too sweet, but otherwise a lot like massive amounts of cum.

I used my hands to spread the fake jizz everywhere including inside every hole, crack, and fold of her body. Beyond that, I got it into her hair, nose, ears, and between her toes.

She sat up and started to fight me, laughing hysterically. I kept assaulting her with the whip cream, giving her more as she tried to escape. We both laughed ourselves sick.

Finally, we fell back on the bed, tightly hugging, rubbing together to feel the slippery cream between us. I put one hand in her pussy, scooped it out and fed it to her, wiping my hands on her face, going back to her cunt and ass for more.

When she settled down, she lay beside me, head on my tits, glazed with cream, grinning from ear to ear.

I traced her nose with one finger. "At the gangbang, we're going to do that with cum. Okay?"

"I can't wait," she replied, smearing my boobs as she spoke.

~~~~~~

At the end of Andi's training week we added up all the hours, Monday through Saturday.

"That's more sex than I had the rest of my life," she told me with a laugh.

I hugged her, we kissed with lots of tongue and fingered each other between the legs.

I painted her face and pushed my slippery fingers, pungent with her slime and mine, into her mouth. She eagerly licked them.

"I think you're ready," I told her.

~~~~~~

Andi's team - Tony and six other men - flew in to Vegas with her, arriving three days before the party. Once here in Vegas, she spent all her time with me. We shopped, walked on the Strip, watched some of my videos, and talked endlessly as I attempted to answer her last minute questions.

Tony called, to tell Andi everything was cool with the men about her central role in the event.

He added, "Cool isn't the right word. They're thrilled, this is a fantasy come true. For them and me too." Andi was was relieved and happy to hear that.

Tony asked us to approve the party suite. Brad had put a hold on a large luxury apartment on one of the top floors of the hotel. Along with plenty of space, beds, and couches, it featured an oversize sunken hot tub plus lots of other amenities.

The suite had two bedrooms, each with a king size. The hot tub was integrated with the main bedroom, centering the large tub against the outside glass wall. The view was spectacular.

After meeting Tony there for a quick tour, we agreed it was perfect.

~~~~~~

On party night, Andi and I went to the suite together, about a half-hour before the men were due.

We changed from our street clothes and helped each other fuss with hair and other prep. The plan was for us to be in the hot tub enjoying the bubbles while Tony greeted the men and got everyone in place. I started the tub's high pressure jets and air bubble generator that whipped the warm water into a frothy foam. A built-in heater automatically maintained the water temperature perfectly.

When we shopped together we had chosen tiny bikinis to wear in the tub, at least at first. Mine was Cherry Red and Andi's was Deep Blue.

We got in together right at ten o'clock. The tub was roomy enough for both of us to stretch out from opposite ends.

The first men arrived a few minutes later. Tony told them to strip down to underwear and gather around the spa.

Andi and I sat in the sublimely warm water, playing sexy kissing games with lots of visible tonguing and hands on each other.

As the men gathered, they applauded us and gave appreciative comments. In a few minutes, all seven men were there, watching our play time, hinting they were ready for more.

Tony asked for quiet.

"Cherry, we only know you from rumors. Could you say a few words?"

"Okay, sure. I was a porn actress in LA when I was eighteen, but live here in Vegas now."

From the crowd, "Brad sent us some videos. Sizzling hot, Cherry."

"Thank you so much. Brad and I met when his sales team won the last performance contest. He recruited me for that party, the only thing like that I've done since leaving the industry ten years ago."

Someone called out, "Best party ever, so I heard."

I grinned, "I hope so. It was exciting fun for me too. We'll make tonight at least that good."

"You got that right," rang out, followed by group "Hooah!'

I put one foot in Andi's crotch and gyrated her with my toes. She yelped, then giggled, both joyous and nervous.

I smiled, "I've been getting to know Andi. I have to tell you, she is great!"

Everyone agreed with that, enjoying my ease with her and the sexual implications.

Looking around at the eager faces, I was glad to be with them and feeling aroused by thoughts of what was about to happen.

I turned to Andi, reaching through the swirling bubbles to slip the knot and remove her bikini top. Her boobs settled partially in the turbulent water; her cleavage was magnificent.

"I think she's fabulous, I know you agree," I said, smiling broadly at the men with their eyes glued on her tits. The applause and shouted compliments had an effect on her. She turned red as a lobster, looking down but smiling broadly.

I stepped out of the tub and used a huge towel for a quick dry.

"You've wanted to get in her panties for a long time, truth?" I challenged them.