Chapter 3

The next week found Dennis and the others busy with classes, of course. Final exams were up soon, so they had to study as hard as ever. They had a few quickies, but nothing serious until after finals were over. Thankfully, they were all likely to pass, although Jake would have a C average overall. There was also the matter of finding jobs after they graduated.

However, when Friday night arrived and the finals were completed, the four of them were quite prepared for some extracurricular fun to celebrate their release from their studies. Three of them, however, were a bit thrown by what Jake sprung on them when he got sufficiently drunk. The young future graduate put on a dress and brought out a strap-on dildo for the girls to use on him.

"Jake, are you telling us that you want to be a woman?" Dennis queried, being accustomed to a lot of strange behavior by his roommate, but not this.

"Well, not really. I just want to dress up as a girl now and then, in order to let people fuck me like a woman. I've particularly had fantasies of you gals taking my ass that way with a dildo. I am not sure about the rest. I'm willing to look into it. Could you guys just humor me and fuck my ass tonight? Call me 'Janice', too. Don't worry, I'll take the ladies first and Dennis can screw them while they use me. Think about it, girls. You could be the meat in a sandwich. Please, just give it a shot?" Jake begged them.

"On one condition, I'll agree," Dennis answered with a grin.

"What's that?" April inquired, truly puzzled.

"That Jake lures Sarah back here, so that you girls can also use the strap-on with her. Tell her that you changed your mind and you want to be with her, desperately. Tell her that you are willing to do something very pathetic and submissive to show your contrition. Say nothing about me, of course. Let her think what she wants about that. If I know Sarah, she won't want any kind of weird, kinky photos of herself going online, even if they show her in a less humiliating position. We have to get her where she will be ready to comply with us. How does that sound, ladies?" Dennis snickered as he laid out their trap for Sarah.

"Excellent! I would love to see Sarah put in a hopeless situation, where the four of us have leverage on her. We could do any number of things to punish her, such as make her service all of us orally without any guarantee of an orgasm herself. Or we could pimp the bitch out. She's a real shrew, so anything that we do to her is deserved. The way that she stood you up and tried to turn you into a cuckold is unforgivable. So, what do you want to do with Sarah once she's our property?" Lorraine urged her lover with a wicked smile.

"Well, mostly, we could let Jake have her. After all, since you gals are my main lovers and I'm your primary beau, Jake deserves to have someone who is his first. That way, he doesn't feel left out when the 3 of us want to be alone together. However, I certainly like some of your nasty ideas to punish her. Mind you, being Jake's fuck-toy will be a good punishment, too. She would hate to be under someone else's control, let alone someone that she considers beneath her. I know Sarah. She's a snob toward even her lovers, if they aren't well-bred enough for her. What do you think, Jake? Want to have Sarah as mainly your bitch, to use as you wish? You don't have to date her or anything, and you can make her indulge these kinks as well, if you so desire. The point is that she'll be mostly your responsibility and chattel. If you want her to lick my cum from your ass or your cum from April's or Lorraine's, that will be your choice, not hers," Dennis offered his roommate.

"Or your cum from our asses, right?" April giggled.

"Well, that goes without saying, babe. She likes creampies, so she should get to enjoy all of them that she wants in the future, with our help," Dennis chuckled viciously.

"Well, what guy can turn down having a live, breathing blow-up doll of his own? I'll especially enjoy having her take my cock up her ass while the three of you fuck me and each other. The look on her face while a transvestite sodomizes her will be worth millions, if you ask me. Naturally, she won't get much in the way of lube," Jake grinned his agreement with the devious plan.

"Well, of course, not. We all owe the cunt a seriously sore butt hole. Especially given how she treated both you and Dennis, but especially Dennis. The girl needs to learn that equality and respect are a two-way street, right, hon?" April smirked at the visions in her head of that spoiled brat getting her ass reamed by a cross-dresser.

Who said that transvestites were always wimps? Judging by Jake, they were quite wrong. Sarah would be taught lessons tonight that would never go away, much like the pain in her posterior that she would get from two hard cocks and a strap-on dildo. April knew that Sarah was a bit racist toward blacks and Mexicans, so to have one of the latter use her sexually and have more power than her would just exacerbate the humiliation of the blackmail and gang-bang. She was about to be screwed in every meaningful sense of the word. Her contempt for those not like herself wouldn't last the evening in the slightest. Both April and Lorraine hated gender feminists like Sarah, who were bigoted against men instead of just wanting equal rights, not to mention closet racists in many cases.

"Oh, without question. Respect is earned, so she has a long journey to getting mine. She certainly doesn't have my forgiveness, nor will she anytime soon. I'm not one of those folks who spout trite sayings about 'anger poisoning one's soul', and other such rubbish. Yes, I believe in karma and I believe in retribution. With your help, ladies, I'm about to get that. As are you, Jake. I hope that you don't mind my referring to you as a lady, given your choice of attire tonight. Make no mistake, buddy. We'll get plenty of tail tonight, especially me, and the four of you will get plenty of cock as well," Dennis commented with a certain look of eager and sadistic anticipation.

"Well, let's go out for a bit, so we can surprise Sarah. April, Lorraine, and me, that is. Jake needs to be here as the bait. Don't worry, Jake. You'll get your pegging and then some. It will just wait until Sarah has been duly penalized herself. Well, she can start fucking your ass, but we want to catch the two of you in the act. Like I said, it won't matter to her that you're the one receiving it. She couldn't abide the idea of being caught with her pants down. That's exactly what we're counting on. You have less to lose than Sarah, who has some conservative and wealthy relatives considering her for an entry-level position in their firm. She doesn't want to be associated with such 'scandalous' activities. She's ideal for this kind of blackmail, since she's kinkier than she admits to her friends and family."

Sarah was pleased that Jake seemed to grovel to her and accept whatever terms she wanted. She had long wanted to see if she could get a man to be faithful to her, while sharing her with other men. A cuckold was handy, though two were better from her perspective. She didn't really care if that was fair or not. She just wanted to see if she could get away with it. After all, her body and her money had always gotten her whatever she wanted, even when she had to fuck minorities to do it.

Well, she'd do that some time again, mainly to reinforce her control over Jake. She also loved to keep a man from even stroking himself or looking at porn, so that he would be obsessed with her needs. That was why she rarely sucked a man off, and then only grudgingly. The whole point of having a man around was to use him for one's own purposes. His interests would only be served when that suited her.

She didn't know what exactly he wanted to do for her, to "make it up" to her. However, it had to be good. Maybe it was another man, and the sight of Jake eating his cum from her pussy. That would be nice. Who knew, but she might even let the man fuck Jake, if he wanted that. Sharing a man with another man was different, if it suited her and proved her power over him. That was particularly true if the man found it humiliating. When a man was such a fool for her that he would even suck cock to please her, that was the ultimate sign of female dominance. It was too bad that Dennis hadn't come around, but she supposed that some men still had balls. That was a damn shame, except that they were sometimes useful for a fuck. Aside from that, balls on a man were an obstacle to her desire to rule them.

When she arrived, Jake acted very loving and tried to kiss her mouth, but Sarah ordered him to kneel and kiss her shoes instead. She then demanded to know the surprise, at which point the remaining roommate presented his ex with a strap-on dildo and a dress. He told her that he wanted to dress up as a girl and let her fuck him in the ass like a woman with the dildo. Well, this wasn't quite the ideal surprise for Sarah, but it had its appeal to her malicious side.

She grinned with evil pleasure at the idea of getting very rough with Jake and teaching him how it supposedly felt for women. Well, it mostly did feel that way for her during sex, since she hadn't found a man who could get her wet from penetration, except for Dennis. This wasn't something that she would admit to Dennis, or Jake, for that matter. Admitting it might mean confessing that sex wasn't always a chore for her. Frankly, she still didn't know why Dennis made her cum so easily, but he did, damn him! Why did he have to reject her terms, again, when this pathetic fool accepted them, worse luck? Well, she'd have to make do with Jake, at least for now.

"Can you go a little easier on my butt, Sarah?" Jake pleaded with a mix of fake groveling and true agony. She was a bit rough on him, in fact, for one whose bi experiences had been mostly oral. The anal part was still new, though he did want to explore it a bit. Sarah, of course, didn't need to know any of that. She would learn the truth in time, when she was already trapped.

"That's Mistress Sarah to you, and the whole point of this matter is you making up to me for dumping me, remember? Now, stop griping and spread your cheeks further. Just so you know, I'm not letting you cum tonight, at all. You'll make me cum several times, however, or I'll have to use this on your ass again. I might whip your cock, too, before I ride you. Yes, I'll fuck you tonight, but I will be on top and will not let you cum. I'll stop when I have cum instead. That will teach you to drop me because I am too selfish or unfair to you.

"The whole idea of our relationship is that I come first, which I thought that you understood and accepted a while ago. Evidently, I was wrong about you, just as I was about Dennis. Well, at least you learned and are taking your punishment, if not quite like a man," Sarah cruelly chided him for complaining about the rough buggering.

"Oh, and don't even think that because I am fucking your ass, that I'll let you fuck mine. You're the one who takes in the tush, not me. That's what butt sex is for, faggots and perverts like you, not respectable women like me," the evil ex taunted him more, unaware that Dennis and the girls had returned with their digital camera.

"So, what does that make you, Sarah Huntley? Because you're going to take it in the rear and on the chin, as well as a few other places in the very near future. Since you're so cruel to men, minorities, and those in the GLBT community, you need to be taught some empathy for us. Who better than me, your ex-boyfriend who actually had the balls to stand up to you?" Dennis announced, as April took the pictures that they had planned.

One thing about April Gomez was that she knew how to take the perfect pics, from the best possible angle. She was a natural photographer, as anyone who really knew her could have told Sarah. The heiress found herself a bit thrown back by the whole experience of knowing that photos of her in a "sexually deviant" act could be sent to everyone in her social circle. Dennis and the others had the power, so she was definitely scared and angry about this situation.

"How dare you photograph me without permission! This is blackmail, isn't it? What do you want? An apology for cheating on you, Dennis? You're not getting it!" Sarah said, as she started to pull out of Jake and try to reduce the damage.