Dennis April And Lorraine Ch 03

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.

Lorraine stopped Sarah by blocking her and pushing her back into Jake, though the blonde now controlled her victim's pace of fucking. While she did that, April took more pics of them in a compromising state and Dennis grabbed some lube. He just didn't use much, as he shoved his cock between his ex-girlfriend's cheeks and started taking her hole. She was definitely a virgin in the anal sense, but he didn't care. The senior just wanted some payback on the bitch who stood him up and two-timed him while he had been faithful to her.

"Alright, I'm sorry! Just don't send those pics to the Net. Do you know what my family would do if I was disgraced that way? Please stop this and let me go! I'll make it up to all of you, one way or the other! Even you, Jake!" Sarah wept, but pointlessly.

"Listen, you uptight little ice princess! I'm tired of your attitude and your belief that men are just playthings to be treated as you wish, and then discarded solely on your terms. What's good for the goose definitely is good for the gander here, and you're getting it as good as I can give you! So, shut up and keep fucking Janice! That's Jake's name when he is cross-dressing. He's not afraid to be himself, unlike you! That's why blackmail wouldn't work on him, just as it won't on us. We don't care if you snitch about our lifestyles, because we have less to lose. We stick together, anyway.

"Get used to this new life, Sarah. You're our bitch until we say otherwise. You're especially Jake's property, until he decides that he doesn't want you. You can be sure that he's going to fuck your ass as hard as you're fucking his, so you might as well enjoy yourself. Oh, and whether you cum or not tonight is up to Jake. That's only fair, given how selfish you have been with him. Now, when I'm done with your ass, April is taking over. She'll be followed by Lorraine. They got a new strap-on dildo today, as well as the new digital camera. I guess that you'll be very sore at the end of tonight, but none of us care at all! You don't give a damn about anyone but Sarah Huntley, so the feeling is mutual!" Dennis declared between thrusts in Sarah's once cherry asshole.

Sarah wasn't crying now, but some other fluids had started to flow. She felt damp between her legs, as if she were actually aroused by the experience of having her ex-beau ram her sphincter mercilessly. She tried to concentrate on Jake's butt, which she now realized he didn't mind having sodomized as much as he minded the severity of her invasion of it. Even so, her own stretched pucker took up most of her attention, in spite of her best efforts to ignore it. What she didn't know was that Dennis intended for her ass to be kept ready by constant use of butt-plugs and enemas. He also hadn't fucked anyone yet that day, so he had to slow down a bit to keep from cumming too soon. This was his first time in Sarah's ass, so he wanted to relish the experience as much as possible.

However, no matter what he did to hold back, Jake couldn't restrain himself, due to the effect that the dildo had on his prostate. He came and let the cum ooze down his shaved legs. This caused April and Lorraine to kneel and lick up his seed, which they happily shared through a tongue kiss. This sight finally, of course, brought Dennis to his own release, and his jism filled Sarah's bowels.

"Well, I guess that she has enough lube now, doesn't she? Lorraine, can you suck Dennis a bit to get him hard again? I have an appointment with Sarah's derriere. Alright, slut, brace yourself for some real pain!" April told her "bottom girl", as she shoved the dildo in as deeply as she could.

If Dennis's cock in her ass was painful, the agony of April's strap-on in her pucker made Sarah shriek at the initial entry. She kept using Jake's tush, but it was no longer such a joy for her. It was just one more way that she was made to pleasure the group. Sarah was sure that she wasn't even slightly bi, so being forced to take a woman into her depths did nothing for her at all. All that she knew was that a plastic dick was lodged in her rear end, and it hurt like hell. She actually missed Dennis's cock in her butt and looked forward to Jake's.

"Can you please lighten up on my butt some, April? I know that you don't like me, but damn!" Sarah found herself begging the Latina.

"Ignore the racist bitch, April. She didn't listen when I asked her to go easier on my tush! Just go for it until you cum!" Jake urged from underneath Sarah, which angered her so much that she rammed him harder again.

"Hey, don't punish him for telling the truth, shrew! After all, he's now in charge of you, like I said!" Dennis warned Sarah rather sternly, while reveling in the warmth of Lorraine's throat.

April did exactly as Jake urged her, which took a while. Sarah, meanwhile, realized that she had been caught and was being punished for her hypocrisy and callousness toward others. She dreaded Lorraine's turn, but part of her just wanted this to be over. The most humiliating part was that they were right. She was a bit prejudiced against blacks and Mexicans, so losing Dennis to a Hispanic girl and having to take her dildo up the ass made things very tough on her pride. Lorraine she could understand, as she was tall and blonde. She was another white girl. April, however, was a Tejana girl. It hurt Sarah's ego that Dennis would want the petite, busty woman from another race over herself.

When Lorraine took over, she made a point of being ruthless as possible in pounding Sarah's bottom. It soon became so intense that Sarah could barely think of using Jake's butt. Her own posterior was simply too sore to think about much else. Despite this, she was now quite wet. Even if she disliked being buggered by April and Lorraine, Sarah had found some part of herself that had adjusted to the experience by this point. She even discovered a bit of arousal once more. It wasn't that girls were topping her, but that someone did so. Sarah had been introduced to her submissive side, which she didn't think even existed. This side of her didn't care that she was straight, or at least was superficially.

"So, I can smell you getting wet, Sarah. You're enjoying this, aren't you? Well, remember what I said. Your climax depends on pleasing Jake, so don't piss him off. If he denies you an orgasm, we will help him do so. This is going to be a very delicious weekend, both sexually and in terms of revenge. You'll never have the same attitude about men, bisexuals, cross-dressers, or minorities again, will you? Bigotry is an ugly thing, Sarah. So is what we're going to do to you from now on. This is a permanent arrangement, if you don't want your family to learn about your life.

"Oh, and forget getting married to some wealthy fool. Your social life is under our control, especially Jake's. We won't have you lie to and cuckold some unwitting and well-meaning man. We'll determine what social events you're allowed to attend and when. The same with political demonstrations. We'll also control your career, to some extent. You can take the job with your family's firm, but each promotion means that you'll have to suck up to us more to keep us from exposing you to your family and friends. That's just how your life will be, plain and simple," Dennis announced, as April resumed taking pics of Sarah, this time with Lorraine and Jake.

Once she finished photographing much of the threesome, April started doing what Lorraine had done earlier. She sucked on Dennis very hungrily, loving the taste of his cock. There was something about her boyfriend that she craved from the very first night of playing pool, and by now, the lust was mixed with stronger emotions. She also had some feelings for Lorraine, already, but that was no issue. He was their beau, not just hers or Lorraine's. They were his girlfriends, and that was not even remotely in question by now.