Breaking Up

Many thanks to Jenna for all her hard work in editing and improving this story from a previous version.

*

I saw her across the room, and I looked away immediately, but not before I saw that she was looking at me.

That split second was enough to satisfy my curiosity. Yes, she was still a knockout. Yes, she still dressed like a slut. Yes, I should probably keep my distance so she couldn't damage me any more than she already had.

The year after we broke up was hard on me, but after that things started getting better, and the last five years I've dated some really nice girls. None of them worked out, but the relationships all ended well, and a couple of the girls are still friends. Not like Jezebel.

Part of the reason I decided to come to this reunion party was a test I was giving myself. It wasn't a real reunion, because the only people here were those who never left town or, like me, had returned after graduating from college. But a dozen or so classmates thought it would be fun to get together and did most of the organizing. They kept the cost low, so a lot of people were here in the hotel ballroom, maybe 150, talking and dancing to the music we were listening to back in school.

I had some guy friends here that I saw all the time, and I told them I wasn't going to hang out with them. Other than that, I had no game plan, except, of course, to check out the girls. I thought there was a good chance Jezebel would show up. I knew she had come back to town, because I'd spotted her a few times, but I'd always kept my distance, and I was sure she hadn't noticed me.

"Hi Tommy."

It was her voice, at my right elbow, and I was embarrassed, because I jumped when I heard it.

"How have you been?" she said.

"I'm fine, Jezebel," I said. "How have you been?"

"Terrific," she said. "You don't have to be afraid of me. I won't bite."

"That's about the only thing you won't do," I said. I was trying to say it in a joking way, but my voice betrayed me.

"Are you still mad at me?" she asked. Was she sincere or toying with me? I assumed the worst.

"Only when I think about you," I said.

"Well, I've changed a lot."

"It doesn't look like it."

"Oh these clothes? They're a costume. I'm dressed up like the high school slut I used to be. But I don't wear stuff like this anymore."

"I wouldn't know."

"Oh yes you would. I've seen you looking at me a few times, even though you pretended otherwise."

"How observant of you."

"Are you still the sweet, naïve boy who falls for evil bitches?"

"Are you asking if I'm still stupid enough to fall for someone like you? I hope not."

She ignored my answer. "I'd like to see you in my room later. Even though I don't drink like I used to, I rented a room in this hotel just in case I have a little too much. My girlfriends are all coming up, too. You remember them."

"I sure do," I said. "And that's why I won't be at your party."

"Well, think about it," she said. "I brought along a couple of things to attach to my bed. It could be like old times." She laughed as she saw me pretend not to react.

"I think you're taking me seriously," she said. "I told you I've changed, and if you come up, I'll prove it."

"No way, Jezebel," I said. "As you can see, you still can inspire a lot of emotions in me, but one of them isn't trust."

"I'm sorry about that," she said, "but the night is young, and there's plenty of time to reconsider. See you later."

She walked away, and I tried to keep a poker face watching her mesmerizing butt, which was covered tightly with some kind of cloth that molded itself to her and magnified every bounce, flounce and jiggle. Around me, jaws were dropping. She definitely was the hottest girl in the room and enjoyed demonstrating it. The same old Jezebel, I thought.

We had been dating for four months as seniors and having a lot of great sex, at least I thought so. My friends had warned me about getting mixed up with her, but I didn't listen to their stories, because they were all second hand. I should have realized that each story was so similar that there had to be some truth to them.

The word was that no boy interested her for long. While she was with them, things seemed to be great, but when she got tired of them, she moved on quickly. The bad part was that before breaking up with a boyfriend, she enjoyed embarrassing and humiliating him, sometimes in freaky ways.

When she stopped being nice to me, I figured I was about to be dumped, but she was still great in bed, and she would sometimes apologize for being mean, so I foolishly stuck with her.

One thing I liked about her was she was way ahead of me when it came to sex. She told me she got a lot of stuff from the Internet, but when I looked at porn, I never saw the things she wanted to do. I liked the adventure of keeping up with her. When we tried something new that she really liked, she turned into a crazy animal, which always turned me on.

One night when I came over to her house, she told me that her parents and younger brother went to one of his band competitions for the weekend, so she was home alone and wanted to try something that she had read about called restraint.

"What does that mean?" I asked.

"It means you're tied up, so I can do what I want to you," she said.

"I don't think I'd like that."

"I thought of that," she said, "so I'm only going to tie up your arms. That way we can get the effect of restraint, but it won't be like you can't move at all."

"I don't know."

"Come on, Tommy. Tell me you don't like those kinky things that I find on the Internet. You can at least give it a try."

"Well, if you promise to untie me whenever I ask you to," I said.

She didn't answer right away.

"OK," she said, "here's what I promise. The second I hear you ask me to release you from your restraints, I will untie you. But otherwise you'll cooperate and do what I tell you, OK?"

"OK," I said, "but I don't like this."

"Let's go to my parents' bedroom. They've got a huge bed and there's much more room around it." She took me by the hand and led me up the stairs. After closing the blinds, she turned on every light in the room, and I blinked because it was as bright as daylight. She began taking off her clothes and motioned for me to do the same. I slowly followed her lead while staring at her. The combination of her hot body and her obvious excitement aroused me so much that my I was aroused by the time I was naked. She grabbed my penis and pumped it a few times while giggling.

"Lie down on your back," she said. "These are the restraints. See, they are soft so they don't hurt, and I'm attaching them to your wrists now with these Velcro strips and making the attachments tight. Each restraint is attached to a belt that can be made longer or shorter, and later I'll connect the belts. But first I want to get you into position.

"This is a new position that I learned about. It's called the Viennese Oyster. I thought of you when I saw it because you are on the gymnastics team and very limber. Other guys might pull some muscles, but you won't have any trouble. So first I want you to put your arms straight down your body. I have it. Just grab your dick with both hands. That's it. Now I'm going to drape the belts coming from your wrists down between your legs so they don't get tangled.

"OK, now lift up both legs and bring them straight back. I'll guide them for you. Good, keep them coming back. See how I'm placing your feet behind your head. Can you cross your feet back there and lock them. Yes you can. You are really limber. That looks perfect. Now I'm going to take your hands off that big dick and bring them out and lay them over your thighs and drop them onto the bed at your sides. Now I'm taking the belt that's connected to each wrist and dropping it over the side of the bed. One second while I crawl under the bed. That didn't take long. I'm back up here. Now quickly, the last thing.

"This is called a ball gag that I'm pushing into your mouth. I can see you're resisting, but I read about how to do this. I keep pushing with one hand and with the thumb and index finger from the other hand, I pinch your nose shut so you can't breathe through your nostrils. Eventually, you have to open your mouth like you are doing now. There, I've pushed it in, and there, the strap is around your head and tight so it won't come out. See how you can breathe through the hole in front, but if you try to talk, you can only make a gurgling noise?

"I snapped the hand restraints together quickly under the bed in order to get to the ball gag in. But now I'm going under there again to make some adjustments. One second.

"OK, I'm back. I adjusted the belt connecting the hand restraints to pull your hands up a little and further out. That way they push your legs further back and pull them apart, so your ass is high in the air and spread open. I can see right into your asshole, and it's pretty dark and scary in there."

I had started feeling uneasy when I was crossing my feet behind my head, but when she pulled my hands over my thighs and locked them together with the belts underneath the bed, I was totally surprised. I started to say something, but she was too quick with the gag. I tried to struggle for a moment and realized she had me totally helpless. Now I lay there disgusted with myself as much as I was angry at her. This was what I had been warned about. She was kissing me off and humiliating me at the same time. Then I heard the doorbell ring.

"Stay right there," said Jezebel and laughed as she left the room. She returned a few minutes later with the five sluts she hung around with. They were her entourage, and all of them dressed and acted like Jezebel. I knew one of them from my advanced math class.

When they saw me, they screamed in delight and began talking a mile a minute. They wanted to know how Jezebel got me in that position, why I didn't object ("I promised him that if he asked me to release him, I would, but I don't hear him objecting, do you?"), what was she going to do now, could they take photos?

"OK, girls," she finally said in a loud voice. "You're here because you're my best friends, and I wanted to share my greatest achievement with you. You know I like to give my boyfriends a goodbye gift when we break up. Tommy's gift is one he's going to remember the rest of our lives, and so will we.

"What I've done is put Tommy into the Viennese Oyster position. I've only seen girls in this position in porn videos, but I thought it might work for boys, too, and it does. The idea is to make the girl totally open and vulnerable for whatever the guy wants to do to her. Her pussy is sticking out and wide open, and so is her ass.

"But tonight, it's Tommy's ass and dick, and we get to do whatever we want to them. I've got some ideas that I'll tell you about, and I'm sure you will think of some more. Let's write them all down and decide on the best ones. We'll leave Tommy to anticipate the fun while we go over here and work on our list."

I heard nothing but giggling after they went to the far end of the room. When I turned my head, I saw them gathered around Jezebel, who was writing on a pad and looking at me every once in a while. When they came back to me, all of them except Jezebel were so excited that they were almost bouncing off the walls.

"I have to apologize for these girls, Tommy," Jezebel said. "I knew they were liars, but I just found out that all of them are also virgins and none of them has ever let their boyfriends get past first base. They've been using me to pretend like they've been around. Of course, they've watched a lot of porn, but they're too scared to try anything.

"So tonight is going to be a hands-on sex education class for them, with you as the demonstration model and me as the teacher. I'm going to share our list with you now because they'll get even more excited watching you when I read it, and so will I. Would you believe that everyone in this room is in the top 25 of our graduating class? But we like to have fun, too. So here's the list.

"First, we're going to explore the male genitalia and male sexual response. I'll show the girls how to use their hands first and then their mouths to get a man really worked up. You know how I can get you all frustrated until you're dying to come and how you explode when I finally let you get off? I'll teach them my techniques, but then for fun, we're going to lift your legs further back and push your dick right into your mouth.

"That sounds like it will be difficult without your cooperation, but all I need to do when we're ready is put this swimmer's nose clip over the end of your nose and plug up the hole in the ball gag. You'll hold your breath as long as possible, but when we see that you are close to passing out, we just pull the gag off and you'll open your mouth wide to gasp for air. That's when we'll push your tool in and pull your legs back further to keep it from falling out. Once you're inside your mouth, we'll get you to start sucking yourself by squeezing your balls until you cooperate, and once you're sucking they'll use their hands on your dick, and I'll use my tongue on your balls because I know it drives you wild. It shouldn't take long. When we see you are getting close, one of the girls will dip her index finger into the lube jar here and push it as far as she can into your anus. You know when I do that it always sends you into a giant orgasm, and your jism is going to explode into your mouth so hard that it will be coming out your nose as well as choking you until you start swallowing it. Yes, I know it will, because it's happened to me.

"Part two will be experimenting with the limits of the male anatomy. We're going to take turns putting things into your anus. I've brought along some different size dildos, and most of them vibrate, so we'll get you hard again by the time we're done. If any of the girls is as adventurous as me, they'll join me in sticking fingers inside you, and stretching you even wider. To finish off with a bang, I'm going to get on top of you and show them how to pound out an orgasm on top of you in both directions, while they are pushing fingers and then their fists into you. We'll be really careful, but I know we have much smaller hands than some of the people I've seen doing this in videos on the Internet, so I'm sure we won't hurt you. You'll probably have a sore ass for a few days, though.

"Part three will be the first orgasm with a boy for any of the girls who aren't too scared. They all said they wanted to do it, but we'll see when the time comes. I told them how good a tongue man you were, and so each of them will sit on you in whatever position they want while you bring them off. Most of them will be facing you, because they want to see as much of your tongue as they can and also watch your expression, but at least one of them wants to experience 69, so you'll get another chance to come.

"Finally, I'm going to demonstrate some more extreme sex to them. They all think it's disgusting, and I may agree, because I've never tried this, but we're going to lift your head up with some pillows, and then I'm going to back onto your mouth with my ass. I'll pull my cheeks apart and cover your mouth with my asshole. We'll take the nose clip off for this, so you'll be able to breathe while you eat out my ass." I heard the girls making fake gagging sounds as she described this, but my gagging reaction was real.

"After that, we'll clean you up, release your hands and call it a night. In case I forget later on, I want to tell you right now that you've been the best boyfriend I've had up to now, and I really appreciate the fact that you aren't telling me to stop our party. Now we need to prepare before we get started.

"It's lucky for all of us that Paula's mom makes her volunteer as a candy striper at the hospital, and she's really gotten into it, because she enjoys finding ways to embarrass the male patients who wear those gowns that open in the back. When she found out that men are really humiliated by being given enemas by women, she began volunteering to help with that, and she's an expert. She doesn't even mind the smell, so we're going to leave now and turn the air conditioner all the way up. She brought some stuff from the hospital, so you're going to be her patient while she cleans you out. She promised us that there wouldn't be a speck on the sheets when she calls us to let us know you're ready. When she's through with you, your insides will be as clean as a whistle, and then we can get to work on our list. See you later."

As Jezebel walked away, I thought about the ordeal I had gone through that night. I had stopped remembering the pain long ago, but the humiliation still came back to torture my mind, like it was doing right now. I felt my face turning red, and I was feeling a little dizzy as I walked out of the room and down the hall into the hotel lobby. I kept walking until I was outside the revolving door and standing in front of the hotel, breathing the cold night air. It took me five minutes to regain my composure and return to the party.

What helped me calm down was thinking about what had happened after that night. Jezebel had moved on to another sucker, but her girlfriends had begun acting strangely. One by one, they came on to me. They asked me out and hinted that they were ready to lose their virginity to me. Then they did more than hint. Then they almost threw themselves at me and offered to do anything I wanted them to.

I was still too shaken up by Jezebel to respond at the time. One of them was persistent, and I finally asked her why they were so interested in me now.

"I don't know about the others," she said, "but I have sex with my boyfriend now, and I like it. One time, I found myself thinking about that night with you when I was with him, and I had the most incredible orgasm, nothing like I ever had before. Now I do it all the time. And I'm sure that if I was actually making love with you it would be even more fantastic."

I was curious to find out how the members of Jezebel's posse felt five years later. I knew that whatever their response was, I wouldn't care, so it was just an experiment.

One by one, I asked each of them to dance, and as we danced and talked, I asked them what they had been doing and told them what I had been doing. I never mentioned anything about sex or that night. They all told me they graduated from college with good records and had good jobs and great boyfriends, and they all said that they were sorry about what they had done to me.

As we talked, I saw each of their faces getting rosy. A few of the dances were slow dances, and by the time the song was over, their bodies were molded to mine, and I had been groped thoroughly in the front and in the back. The conversations all ended the same way. They were all ready to cheat on their boyfriends if I wanted to call them. I didn't ask for them, but within an hour, five scraps of paper with phone numbers had been put into my pockets.

Jezebel got involved in this strange drama, too. Three of the girls sort of clung to me, and I ended up dancing a second dance with them. Each time, Jezebel cut in, and the girl reluctantly walked off. Jezebel didn't say a word until the dance ended, when she said, "Thank you," and walked off.

I had finished my experiment and was feeling good about myself as I talked to other old classmates. The party was in full swing, and I decided I was happy that I had come. Then Jezebel interrupted a conversation. "I'm sorry," she said sweetly to the girl I was talking to. "I need to tell Tommy something urgent." She took my hand and pulled me off to an empty space.

"I'm getting tired of this," she said. "I'm going up to my room now, and I'd like you to come with me."