Chapter 4: First Encounter

Sheri dropped me at my car with all my ‘toys’ from the Triple XXX store, and I drove to my apartment. I got naked and spread out everything after cleaning them. Sheri had recommended that I slowly insert the dildo into my vagina until little remained outside of me. That proved to be a delightful task. Any doubt I had about having retained my virginal hymen disappeared with that exercise. I felt full but no discomfort.

Once I’d achieved penetration, she wanted me to use the vibrator on my clitoris until I’d had five orgasms. I lay back in bed with the vibrator plugged into the wall. Oh, holy shit fuck, that really felt good. I came almost immediately, and then quickly ramped up to the rest in record time. Why hadn’t I discovered these when I was twelve?

Sheri had then given me a piece of paper with a website and ten short video clips that I was to watch as I manipulated the dildo and-or vibrator on my body. The clips were all blatant pornography and got me really hot and bothered. The orgasms I had while watching the array of short videos handled my being horny, and also brought me a lot more pleasure.

The tenth video started after I got the right URL address into my computer browser. As the video started, I again started to pump the dildo into my pussy. This video was labeled ‘Group Sex’ as its genre.

I lay back with my right hand on the dildo, and then I sat up with a jolt. The two girls in the video were Sheri and Maryann! I swore aloud, something Sheri was trying to get me to do more of. “Be more earthy, Brie,” she’d tell me. This time I said, ‘Holy Fuck’ aloud instead of ‘Golly Gee’.

I watched the ten-minute clip, and then paid the monthly fee so I could subscribe to the site and download the entire video. I downloaded the hour-long version and watched my two new friends fuck and suck their way through four men, obviously loving every second of the small orgy. Sheri and Maryann were almost drowning in semen at the end of the video. They’d even ‘snowballed’ some of the fluids back and forth; I heard them refer to what they were doing in the video with that term.

I slept well, but dreamed of being in the orgy with Sheri and Maryann. I guess that was what she wanted to happen. That was what I wanted to happen, too.

In the morning, I dressed as she’d instructed, including omitting my underwear and bra. I also inserted the ben wa balls into my vagina – three highly-polished solid balls, each about an inch in diameter and weighing several ounces. The combination made me have to clench my Kegel muscles in order to hold them inside; that was the idea. I was developing those muscles so that I could use them during sex. The balls also felt really nice and arousing inside my vagina. One of the balls had another ball inside it for additional stimulation. I learned how to move to get that one working in a special way. I was going to have what Sheri called a ‘snapping pussy’.

I got a thrill at work when I had to walk into and sit in a meeting with my project team. I could barely keep my skirt from riding up and revealing my pussy, and when I stood, I was clutching onto those balls lest they drop out of my pussy and really embarrass me: ‘Hey, where’d this big silver marble come from?’

Sheri and Maryann came by my cubicle shortly before lunch. I went with them to the cafeteria. She asked whether I’d watched all of videos she’d recommended the evening prior.

“I did.” I said neutrally, with no indication of what I’d seen.

“You watched the last one?”

“I even subscribed to the website and downloaded the full-length feature.” I still didn’t acknowledge that I’d seen them in the video.

Maryann asked, “And ... you liked it? Did you recognize anybody?”

I frowned by way of teasing, “Recognized? Yes, I really liked it. The acting was good and seemed so real.” I couldn’t resist, and cracked a smile.

Sheri poked at me and laughed. “So, do you still want me as your mentor? I’m a porn queen – a fucking porn star.”

I laughed, “You were great, but so daring to have done that. I’m so impressed. Did you do many videos?”

“Maryann and I have done about six. It’s fun, plus we get to spend several hours fucking handsome guys. Someday, I’ll ask you to try it; that is, if I’m still your coach.”

I told her, “You were so bold and empowered, and so happy in what you did. Of course, I want you to mentor me. Those are the kind of emotions and feelings I want to develop, although being in an orgy may be overkill.”

Are you wearing the beads?

“Yes, I can barely hold them in at this point. They’ve been inside me since seven this morning.”

“You can take them out for the rest of the day. Wear them about four hours a day for the rest of the week. To have good sex, you need strong Kegel muscles. You want to be able to ‘milk’ the guy’s cock that is inside you when you start having sex; it’ll feel so great for both of you.”

“I can’t even envision that, although the dildo was very nice last night.”

“A warm and wet cock is better, especially if it’s pounding into your hot little vaggie.” She sighed. “God, all this sex talk is making me horny.”

Maryann said, “After work, we’re getting drinks again at Epoch. Dress for sex appeal, babe.”

I nodded. “My cocktail dress, CFM heels, and makeup kit were in my car, per Sheri’s instructions to always be prepared. I went out after lunch and retrieved all of it. I also left the ben wa balls wrapped in tissues on the seat of the car so I wouldn’t forget them later.

After the rush of people to leave the office, I did what Sheri does. I stripped down to just about bare skin in my cubicle, and then put on my thong and then my new sequined cocktail dress and sexy shoes. I spent ten minutes in the ladies’ room on my makeup, too. The two girls had given me multiple lessons in makeup the prior weekend.

I met Sheri at her office and she gave me a complete inspection. I passed. Maryann came in and also gave me the once over.

Sheri laid out the evening. “We’ll have a drink and eat bar food for dinner. I expect since the three of us are ‘hot’, we will get approached. Brie, you will have a decision about how far you want to go with one or possibly all of the men. At your level of experience with men – like none – I recommend you take it slow. The progression I recommend is handjob and oral sex – both giving and receiving, and then, if you feel ready, penetrative sex. I guess you could go ahead but I still worry about your readiness without experience with those preliminary activities. Don’t be afraid to set a boundary and stick to it.

I just nodded. My insides were in knots again.

For a Thursday night, Epoch seemed very busy. We got a table on the upper tier where we could kind of look down on the dance floor, and at the general bar area.

Sheri seated us so that we were on display as people looked up at the half-balcony. I got seated against the railing with Maryann across the table. Sheri was facing the table and over the railing to the main area. By the devilish look on her face, I could tell she was flashing the crowd. As usual, the music was almost too loud to talk over.

Maryann got a cellphone call, and even with her six feet away I couldn’t hear her part of the conversation. Eventually, she pointed. I followed her finger.

On the far edge of the crowd sitting at a table were Owen, Luke, and another man I didn’t recognize. Maryann filled in the missing data, “That’s Jake. He’s hot. The three asked whether we’d join them for dinner at the Marina? After dinner, they suggested going back to Luke’s apartment to dance ... or whatever.”

Sheri just grinned.

The butterflies in my stomach felt more like fighter jets bouncing off the canyon walls as they went to war.

Maryann studied me and said, “I hope you’re ready for this.”

“What?”

“The three of us have dates for tonight – a triple date. Jake, Luke and Owen are taking us to the Marina Restaurant for dinner in Jake’s Hummer, so there’ll be lots of room, so, drink up ladies.”

I started to blubber. “I can’t ... I’m not ready ... I won’t know ... what should I talk about...”

Sheri chuckled, “Brie, this will be baptism by fire. If you still have your virginity at the end of the evening it won’t be from lack of trying by three of the most handsome and most masculine men on the planet. These guys define tall, dark, and handsome, and they are divine lovers.”

“But ... I’ve never ... I’m so inexperienced ... I won’t know...”

“You will by the end of the night,” Maryann teased. “Remember what I told you. Just so you know, Sheri and I are very non-possessive with our dates. We swap partners all the time. It’ll be more fun with three of them. We’ll each fuck all three of them. This will be so great. You may not need to fuck any of them if this works out right for you.”

Owen bowed and kissed my hand. He was so suave, and handsome. The muscles in his arms were so large they threatened to rip the sleeves on his nice short-sleeved shirt. Jake and Luke weren’t too different.

I purposefully excused myself to use the powder room. I had insisted that Sheri at least tell the three men how inexperienced I was at dating, flirting, or anything beyond even that. She promised. For two of them, it was a reminder from when we met a week or so earlier.

I guess she told them, because when I reappeared, everyone looked at me. I turned pink. I mumbled, “I’m sorry, I just ... grew up in a simple way of life. I didn’t know what I missed until late in college but I was too scared to do anything until recently.”

Owen came and put his arm around me. “Baby, we won’t do anything you don’t want to do. We’ll take care of you and help you grow and evolve. We’re not out to hurt you either emotionally or physically.” He pulled me to him and kissed the side of my head in a tender way. I almost cried at how nice he was being to me.