Shifting Gears Ch. 04-05

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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 escort izmir 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.”


“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 izmir escort bayan the side of my head in a tender way. I almost cried at how nice he was being to me.

Jake and Luke nodded and looked on sympathetically.

We piled into the large Hummer, and Jake drove us to the restaurant. The place was nice and even kind of upscale but still casual. We no sooner sat down in a boy-girl-boy order around the table than Sheri leaned over to me and said, “Brie, give me your little thong right now.” Everyone heard her request and looked to see what I’d do. I knew she was both teasing me and giving me a test of my fortitude to follow a salacious request.

I hitched myself back and forth in my chair as I surreptitiously jerked my new thong undies from between my legs. I was aided by the amazingly short skirt of the dress Sheri and Maryann had me buy. Eventually, I reached past Luke and handed my thong to Sheri in a tiny ball.

Instead of hiding my lingerie, Sheri opened it up to examine. It was a scrap of cloth with some fancy straps. She showed everyone. She held the gusset of the thong to her nose and inhaled.

She turned to Luke, and said, “Smell this. What does it make you think of?”

Luke inhaled so hard I thought the thong might shoot up in his nose. He grinned at me and said, “It makes me think of a very hot young woman sitting next to me and how much I want to make love with her later tonight.”

Sheri grinned, “Right answer.”

Owen reached over and got smelling rights on my thong next. I was blushing. He winked at me as he let me put the balled-up thong in my small shoulder purse. The contents of the purse now included my thong, my cellphone, lip gloss, several tissues, a Tampax, three rubbers that Sheri insisted I carry, breath mints, my Visa card, and two twenty-dollar bills. I also had a couple of business cards in there in case I lost my purse. Sheri had instructed me in what to carry and why.

The three men were gracious and suave. My heart fluttered looking at each of them. I kind of wanted each of them, but didn’t. They were all on their best behavior, charming, and funny. They were all hunky and muscular. Each wore dockers and a sport shirt, along with loafers of some kind.

Jake knew one joke after another, and had all of us laughing or groaning depending on what he said. Midway through dinner, I kind of sat back and looked at the group. Everyone really liked each other. There was obvious affection that even I’d started to offer with touches and pecks on the cheeks as rewards for something.

I thought, THIS is the life I want. I felt joyous and happy. I was laughing, had a bevy of friends around me, a growing sense of intimacy, and the promise of a longer-term life just like this. Picking Sheri was the right thing for me to do, even with her somewhat scandalous behaviors — ESPECIALLY with some of her scandalous behaviors. For a second, I almost cried at how I’d missed all of this earlier in my life.

I watched Maryann do a French kiss with Jake. They were hot together. She came as part of the deal with Sheri, and I felt glad they were best friends. She’d also kind of adopted me as a ‘Cause’, and her suggestions were good ones. Occasionally, she’d moderated some of Sheri’s more outrageous suggestions for me.

After we’d eaten, Jake led us into another part of the restaurant where there was some dancing. We were perhaps the youngest patrons of the place, but that was all right. We danced and carried on for an hour, and then Luke suggested we continue our triple-date at his apartment.

In seconds, we were back in the Hummer and on the road. A few seconds after that, and we were in Luke’s bachelor pad. The lights were dim, some gentle jazz was playing on his stereo, and he had drink set-ups with exactly the right number of glasses and snack plates already waiting for our arrival. He obviously knew about this ahead of time. I wondered what pre-planning had gone on that I wasn’t aware of.

Without anything spoken, Maryann paired off with Jake, and Sheri with Luke. That left Owen and me, and that was fine with me. I liked Owen a lot.

We immediately picked up where we’d left off dancing to some of the music, only Owen pulled me closer and we started to kiss. I worried that my inexperience in making out would show, but he didn’t say anything. What he did do was keep coming back for more and more, and I was glad of that fact.

I thought I got better with practice. I’d kissed a few boys in high school and college, but nothing like this. Of course, I’d kissed Sheri and Maryann, too, when we had our first sex session together. They didn’t say anything, so I guess I passed muster with them, as well.

Somehow there was a break in the action, and I found myself dancing with Luke. The next thing I knew I was kissing him. I saw Owen making out with Maryann, as Sheri and Jake were wrapped up in each other.

Luke was a little more forward. His right hand cupped and massaged izmir escortlar my breast through my top. We could both feel my unclad boobs develop nipples about as hard as little granite pebbles. The difference was that my nips were very sensitive and sending all sorts of ‘heated’ messages throughout my body, especially when he lightly pinched them through the material. We kissed with more tongue action.

Jake picked up where Luke left off when we changed partners again. The design of my dress allowed me to shrug off the top portion leaving me bare from the waist up without the rest of the dress falling over my hips to the ground. That’s what happened.

Jake then massaged my breasts as we swayed to the music and pretended to dance. He knew just what to do to turn my temperature up. When he leaned in and started to suck on my nipples, I thought I’d rocket into orbit high above the earth. That was really nice. Only Sheri and Maryann had done that to me a few weeks prior.

When I rotated back to Owen, he latched onto my left breast with his mouth, and showed me what heaven might look like. He was leaning over slightly, and this gave his hands an advantage in that one of them could also stroke my bare legs and then sneak under the hemline of my dress and brush against my bare pussy. My undies had remained in my purse.

If I thought the sucking of my breasts were taking me into earth orbit, Owen’s fondling of my wet slit and occasional touches to my clitoris were a mission to Mars. I almost leapt in the air as he repeatedly stroked along my sex. I was flooding the area with my emissions, too. Again, I could smell my own aroma.

I heard Sheri say, “Switch.” I moved back into Luke’s arms. As I did, I saw Sheri strip the last of her clothing away with Jake’s help. Maryann was already nude and in Owen’s care.

Luke tugged at my dress. I nodded and let him help me pull the garment up my body and over my head. I was nude and wearing four-inch CFM heels. Sheri had told me I looked like ‘Sex on a Stick’ that way, and that meant that I was highly fuckable. We were all planning to keep our heels on as long as possible.

Luke picked me up and carried me to one of the three love seats he had in his living room. The three were arranged in an open ‘U’ so that everyone could look at the television set. Just then, the TV was off.

Luke and I went back to French kissing. He tasted really good, and I guess I did, too, because he seemed to be devouring me. When we weren’t kissing, he was suckling my breasts and keeping my nipples hard, and also fondling my pussy.

I helped Luke lose most of his clothes. I found I liked the feeling of skin-on-skin as more of our bodies could rub together. We eventually rubbed our nude bodies together, and then I had one of his fingers in my vagina.

I thought how that finger probably felt like a skinny penis. Even as I had that thought, I could hear Sheri’s voice inside my head telling me to call ‘it’ a ‘cock’ and not a ‘penis’.

Two fingers felt like a more robust cock, about like my dildo. The advantage was that he was also using his thumb to stroke right where my clitoris was. I wasn’t on a journey to Mars; I was turning inside-out and seeing stars from beyond the known universe.

Suddenly, I was in Jake’s arms and he was the one with fingers inside me. On the loveseat I just left, Maryann had mounted Luke’s body and sunk her naked body down onto his cock. They were fucking. God, they looked hot.

On the other sofa, Sheri had devoured Owen’s cock with a blowjob. She had his entire shaft in her mouth. He was good sized, so part of that must be down her throat in some way. I’d never done that to a man, but I had watched a lot of porn with that activity under Sheri’s guidance, so I had the general idea.

I shifted around and started to go down on Jake. He liked that idea. I broke away for a moment, “God, Jake, your cock feels so good.” As I sucked him some more, I thought he grew another inch in my mouth. He was large.

A further switch, and I was back to Owen. Maryann was now being fucked by Jake. Luke was eating Sheri’s pussy as she moaned with her legs waving around in the air.

I sucked on Owen and he tasted a little like Sheri. I guessed that she might have had him inside her briefly or she might have been sliding her wet slit all over his cock as they made out. I started doing that; Owen’s eyes rolled up in his head.

I whispered to him, “Eat me.” Sheri had told me that those were important words to remember.

Owen knelt on the floor in front of the sofa, spread my legs, and plunged into my pussy tongue first. Thirty seconds later, I orgasmed.

Chapter 5 — A Change in Status

I wanted to change my life. I found a quote that said, ‘If you want to change your life, you have to do things you’ve never done.’ I was doing just that, and right that instant the things I’d never done before were sexual.

I was back in Owen’s arms again after circulating to the other two men — Luke and Jake, as my girlfriends fucked them in various positions. I had not fucked anybody, and that was the plan for the evening. I was to get my feet wet, as Sheri called it, in a highly sexual situation.

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