3 comments/ 283891 views/ 23 favorites Matchmaking Trap Ch. 01 By: SEVERUSMAX Roberta was a 43 year old bartender, working weekends to make enough to keep her house, after her husband's death. She was also incredibly gorgeous, with soft, sensual skin, that cried out for a massage. She kept her hair cut fairly short, but it was still a beautiful jet-black, and she managed to seem quite feminine, despite her tomboyish exterior. She had loved being married, because, unlike many wives, she wanted sex every day, and made sure that she got it from her late hubby. She also knew about his affairs, as she had been his mistress during his first marriage, and she had simply not been able to give up his 9 inch cock. His sexual freedom was something that she had learned to accept as a necessary consequence of his higher libido. Roberta had a grown-up son, named Chad, who was engaged to a woman named Deanna, a tall, slender brunette with a tendency to wear up-scale clothes. Chad and Deanna seemed your typical, run of the mill engaged couple, busy planning their wedding and working their jobs, while trying to fight off "cold feet". What Roberta didn't tell her son and his bride-to-be was that she had trouble finding anyone new, because her deceased husband's cock had been so large, that it simply raised the bar for other guys, so to speak. She would fuck them, to try them out, but if they had small dicks, she would let them off easy, without much comment. Chad and Deanna had made some attempts to set her up in the recent past, but their tastes were more conservative, all involving PC, pussy-whipped "Mama's boys". They tended to have small cocks, and were often reluctant to take the initiative in bed. None of them would have made the grade, and she hated to hurt her son's feelings about it. One day, on a Monday night, as she sat with her son, talking about her loneliness, he kept insisting that she could find someone, if she just kept trying, and didn't give up. Roberta, however, kept noticing that he had potential to be tougher, like his Dad, if he could just break free of his college indoctrination. They had filled his head with politically correct claptrap about sensitivity, until he was a hyper-sensitive pansy, as far as she was concerned. She also noticed his penis, which was about the same length and width of his father's phallus. Gradually, as she continued to stare at his groin, she began realizing that this was her solution. She had the ideal lover right there in front of her, carrying his father's genes and, most importantly, his father's dick. She was willing to swing, but she only wanted to be permanent with a well-endowed, dominant sort of guy. This gave her an idea, and she immediately began to carry it out. "Chad, if you are so sure that I can find a steady boyfriend, I challenge you to prove it! Try to make a match for me, and let me judge your success or failure, according to my standards! You'll have 6 months, or I get my prize! If you win, I will marry the man, but if I win, I get to use the largest cock that I know about, daily!" "Alright, but whose cock is that, and what does that have to do with me?" "I'm your Mom, so I've seen your dick a few times, and I wager that it's as long as your father's by now, making it the largest of which I am aware. That's your cock I was talking about, and you just agreed to bet it!" "Mom, that's disgusting- incest? Besides, I'm committed to Deanna, and I won't cheat on her." "You're also committed to this bet, which is more explicit a deal, and, therefore, more binding. If you really think you're right, it shouldn't be a problem, should it?" "I guess not. You're dead serious about fucking me if I lose?" "Yeah, because you need to loosen up a little, and I can help you there." "Ok. Well, you have a deal, as I said." Chad didn't really worry, except for the slim chance that he might lose, but he expected to win the bet, so he decided not to tell Deanna. He did seek her help trying to arrange dates for his Mom, but he didn't give her an idea as to the reason for his urgency. They began planning in earnest, still clueless to the fact that his Mom knew for almost a certainty that she would win. Few men had cocks as large as her son's, and few, if any, of those men would be on her son's list. He was undermining his own side, and he didn't even know it. Roberta was getting everything for her moment of seduction. The schedule had to be right, since she had to be making her move when Deanna was unlikely to catch them red-handed. She knew that her son would never tell his fiancee about something as "scandalous" as incest, so he would be there alone, ready to fall into her clutches when the time came to act. Date followed date, sometimes ending in sex, sometimes not, depending on how PC the fool was, but, Roberta thought, the lucky ones at least got a lay out of it. The poor dupes who wanted to "wait" wouldn't even get that much, since she wouldn't give a 2nd date to a guy who didn't put out. Roberta, as she expected, found all of them lacking in the "dealbreaker" category- the size of their cocks. No man was equal to her son's penis, and she was hardly surprised about that. Chad's confidence began to sink as the months wore on, and he was starting to have anxiety about the growing probability that he would be trapped into committing incest with his Mom, thereby cheating on Deanna. What choice would he have? He couldn't renege, because she was giving every a man a chance, even to the point of acting like a slut, which both disturbed, and surprisingly, on one level, aroused him. Could she really be that picky? What was wrong with her, if she didn't want these respectable men? Deanna noticed his nervous behavior, but she passed it off as pre-wedding jitters. She thought that increasing the frequency of sex would solve it, but it didn't, and she was beginning to wonder if he was no longer sure about his interest in their upcoming marriage. Even so, she made every effort to convince him that his sex life was not going to be over if they wed. He, of course, knew it wouldn't, but couldn't tell her that, and definitely couldn't tell her why. Finally, just 2 months before the wedding, Roberta's time limit had elapsed, and Chad went to her house to find out if her last date had achieved a relationship. He was extremely scared as he rang the doorbell, and his Mom answered the door in a rather surprisingly conservative dress, not indicating what she had in mind yet. "Well, Chad, it's been 6 months, and you know the deal. This last guy was nice, but, sorry, no dice! You haven't helped your cause, picking out these weak, groveling kind of fellows. I'm sorry, but your tastes and mine are different, and that has cost you the bet. I have won, and I expect you to honor our agreement. I get your big manhood inside me every day, and you'll just to live with the fact that you're having an affair with your Mom." "Mom, how can you do this? I am your son, and you are thinking about me in a sexual manner, as an object for your lust?" "Chad, how can you seriously try to wiggle out of your promise? Besides, we are all objects of some kind to everyone. No chance, son, that I will let you out of this one! You need to keep your agreements, like your Dad and I taught you!" "But, incest? Seriously, why do you want to fuck me?" "I want your big cock, plain and simple, and I'm gonna get it, so just accept that fact! No one made you bet your cock on my love life, but you did, so live with it, son!" "Alright, when and how are we doing to this? Deanna can't know, Mom, because it would crush her." "Nice of you to care about your fiancee like that, but she'd survive that, I suspect. Anyway, I want you here and now! Take off your clothes!" Chad quickly complied, as he was afraid that his Mom would divulge the bet to Deanna if he didn't. Once he was buck naked, Roberta looked at him lustfully, seeing that marvelous male sex organ free from his pants and underwear. "Oh, wow, to think that I helped make this hot, young stud, who's about to fuck me! That thought really pleases me! I carried you in my womb, and now part of you is about to inseminate me. I love the irony of that fact!" Roberta then dropped her dress, to reveal that she was not wearing any undies. She leered at him suggestively, motioning with her fingers for him to join her in the master bedroom. As she led her son into the bedroom, she took out some hand-cuffs, grabbed his hands, and slapped them on him. He was stunned, and looked at her to ask why she had bound him. "I've got to keep you from escaping and breaking your contract, my boy! You're far too hesitant for me to trust you, aren't you?" "Will this always be the case?" "No, because you'll get used to fucking your mother, I'll make sure that you like it, and you'll soon be taking control in our sessions. I want that, you know? I want you to dominate me. Otherwise, however, I will dominate you, until you learn to accept my new dual role as your mother and your mistress! Now, lean over the bed!" He did as she ordered, and she realized with some disappointment that he took after her in submissiveness. Okay, she thought, I'll have to dominate him, but I will just go out and find bossy men elsewhere. If Chad is getting it on with 2 or more ladies, and he is actually accepting my control over him, he will have to share me, too. Roberta took out her late husband's belt, which she still kept to hurt herself, and started striking Chad with it, which caused him to welt and flinch in response. She was angry at him for disappointing her with his submissive nature, but also smart enough to know that she had won him, and this came with the territory. Casual encounters with domineering men would have to suffice. Perhaps she could fuck them in front of him, and that would excite him a bit. Then, of course, she would give him sloppy seconds. He could then go running home to his "faithful" fiancee and her boring, Victorian morality. She kept spanking him as she thought about this, and she could tell that he was enjoying it, which only confirmed his masochistic nature. Oh, why couldn't he have been a dom, just like his dad? she thought. At last, when he was hard enough, she turned him over on his back, and swiftly mounted him, getting his cock deep inside her pussy for the 1st time. He was groaning with considerable pleasure, as he felt the confines of her cunt on his dick. She tightened up a bit for him, flexing her vaginal muscles to stiffen him further, and thereby increased the strain on his scrotum, until he just had to cum inside his mother's warm pussy. "Oh, that's right, Chad, my son! Yes, cum for me, now! You can do that right, can't you? You may be a pathetic submissive, but at least your cock is great, and you have plenty of semen! Oh, God, I'm very glad that I won this bet! Your ass is mine, and I'm going to use it! I own you, since you clearly want it that way, and I'm determined to keep you in compliance with our deal. Understand? You wanna be a slave, fine, but be Mommy's slave!" "Yes, you own me- keep fucking me, Mom! I never knew this was so great! Thank you, Mom, I'm glad that I lost!" "You're so great, I want to fuck you twice a day! Report to me during your lunch break, every day, and right after you clock out- is that clear? Whatever is left goes to your fiancee!" At that, she grabbed a butt-plug, and without lubricating it, she shoved it up his rectum, making him squeal with the pain. She looked at him sternly, and then snickered as she thought of something. "I'm going to have you keep that up your ass during the work days, and then you'll return it to me for washing at nights. You'll be getting your ass fucked alot, by all of my other sex partners, all of whom are men. That way, you'll be excited when I ride you, as your prostate will be stimulated by the cocks and the butt-plug. I will have the plug kept in your ass as I ride you, so you'll be under constant pressure, and will eventually have to cum inside me." "Mom, I can't do guys! Ow, this hurts!" "You will do guys, and if you want to stop hurting, seize the initiative and take control of me! Act like a man, and I'll treat you like one, with respect, but otherwise you're my boy-toy, for me to use as I wish! I am only dominating you, because you are willing to let me, so you have only yourself to blame here! Oh, and as I implied, we'll always do it cowgirl-style, because you're a passive weakling instead of a real man, despite your manly cock. I'll even fuck your ass with a strap-on, now and then, if I wish it. By the way, masturbation is strictly forbidden in my house, so don't even think of touching yourself while you're here!" "Ok, Mom, but please pull it out of me!" "No! You're taking it, and I'm going to keep fucking you, while you take it, so get used to it!" She rode him for what seemed like days, making him cum repeatedly, and draining his balls in the process. He was evidently loving it, so she knew that her decision to assume permanent control was a wise one, since he'd make a poor excuse for a master! Finally, however, she released him, and made it clear to him that his duties would be specified to the letter the nights before, so he'd better pay attention. If he failed her, she would tell Deanna about the wager, and he knew what that would mean- the end of the engagement. She had him by the balls, literally, but was partly so hard on him because she had really craved his dominance, and found him sadly lacking in it. Oh, well, maybe he'd give her another son, who would dominate her. She certainly hoped so. See part 2 for the next part of his seduction by his Mom... Matchmaking Trap Ch. 02 Roberta knew of but one way left to get Chad to display any latent dominant tendencies- she had to get him angry enough to act on them. If she broke her promise not to tell Deanna, Chad would get mad at her, and probably retaliate. That's what she wanted, and so, sure enough, she went over to Deanna's, with some other info on her mind. She knew, although Chad didn't, that Deanna was cheating on him with her ex-boyfriend Donny- a hyper-sensitive, love-struck, pansy, lame excuse for a man, if there ever was one! "Deanna, you bitch, I know about Donny! Think that you've got the last laugh? I've been fucking your fiance- how's that?" "You've been committing incest with Chad? I know that he's got a big one, but still- that's gross!" "Well, you're no one to talk! Face it, both of you cheated on each other, so get over it! I bet Chad that none of his candidates to marry me would pass muster, and I won! The prize was his cock, he knew that when he accepted the deal, and he took it anyway! I have him, so don't even think about trying to take him away from me!" "Hey, Roberta, calm down! I want Chad, but I want Donny, too! I will accept an understanding, since we're both cheaters, as you say, and we might as well accept that each of us is going to take a lover on the side now and then. I once believed in monogamy, but, hey, now I am involved with 2 different men! That tells me that more one than companion is possible, and if so, then there must be something to multiple sex partners." "Ok, so you'll accept my love for Chad?" "Yes, Roberta. I must admit that I was shocked because incest is more unorthodox than swinging, but, 'in for a penny, in for a pound', I suppose! Besides, especially lately, I've gotten used to Chad's big cock, making Donny's dick an amusement, but little more, I assure you! I like him, but he doesn't measure up next to Chad. I knew that it was only a matter of time before Chad wanted other women, but I was afraid that he would want them instead of me, not along with me. That's why I hesitated to tell him about Donny, and why I started fucking him more often, so as not to lose him. That has only made me want his cock even more, of course." "Well, I want Chad, too, so I think that you should know that I will be coming along on your honeymoon- no ifs, ands, or buts about it, okay?" "About what?" Chad was standing in the living room, and he could tell by the way that they were talking that his Mom had broken her word, and told Deanna about their incestuous affair. His blood was boiling, and he had to punish her, now! Suddenly, the submissive side of Chad yielded to what Nietzsche once called "the will to power". "You told her, didn't you, bitch?" "Yes, I did! Does that make me a bitch? I'm not jealous, you know, so I didn't tell her to get you all for myself, but if you want to punish me, go ahead! I've been craving it for a while!" "Is that why you told her- to provoke me to punish you?" "Yes." "Very well, bitch, but from now on, these are the rules: first, this is my house, so I am the master here; second, at your house, you remain in charge, because I like both submitting and dominating; third, Deanna is my slave here, but yours there. Also, since you declared your plan to make me fuck guys when I'm obeying you, you'll have to fuck girls when you're here. Is that understood?" "Yes. Deanna was going to share you, anyway, since she has been cheating on you with Donny, doesn't want to stop, but also doesn't want to provoke you into leaving her." "Is that so, Deanna? Have you been cheating on me with Donny?" "Yes." "Yes, Master. You heard what I told Mom- this is my place, and I now feel the desire to control it!" "Yes, Master." "So, you want Donny, that wimpy weasel, with his 4 inch cock- isn't that what you said? It's 4 inches, Mom- her lover's cock is only 4 inches!" "Yes. I want Donny, but only because he's such a sweet, adorable guy, that I can't pass him up. I don't respect him, though. I do respect you, in fact, I even fear you a little, now, since you have all the leverage here." "Do I? Good. I suppose by 'leverage', you're referring to my penis, which both of you apparently want." "Exactly, Master. I'll do whatever it takes to stay with you, I promise! Just keep me, don't break it off!" "Relax, I said that I'd keep you, and I will, but since I've gotten so pissed off earlier, I've rediscovered my old, aggressive self. That means some changes are due. Understand me?" "Yes, Chad- I mean, Master." "What about you, Mom?" "I'm yours- my dear son. If you want this taking turns thing, so be it." "And you, Deanna? You want to keep fucking Donny, don't you?" "Yes, Master, if that's okay with you. I won't fuss over your Mom, or any other girls, I promise." "Very well. We understand each other, now, don't we?" "Yes." they both said. "Now, I seem to recall being requested to punish someone, who deserves it, anyway, for breaking her promise." Roberta was grinning from ear to ear, as her son put her across his lap, removed her slacks, and began pounding her panty-clad ass with his hands. She squealed repeatedly from the pain, but he knew that she loved it, as much as he loved giving it to her, and she didn't ask him to stop, so he continued. As Deanna watched her future mother getting spanked by her own son, and rather mercilessly at that, ignoring her tears and screams, she couldn't help but put her hands up her own dress, sink them into her panties, and tickle her labia. Soon, she was playing with her clit, and even fingering her vagina. "Oh, God, Chad! I want my turn! Spank me next! I've been so naughty, cheating on you with Donny, and all! Spank me for being such a slutty, unfaithful fiancee!" "You'll get it, too, I promise! Even though I am as guilty of cheating as you, I am your Master, you are my slave, and I can punish you for anything, including something that happened before your bondage, and that I did as well! You want it, so I'm not being cruel by giving it to you!" Meanwhile, he kept right on spanking his Mom, getting her so wet that she was soaking his pants, and he decided to punish her for that as well. "You got your cum all over my pants! Look at this mess, Mom! What a dirty, slutty woman you are, getting your juices from your much desired spanking on my pants! I think that you need a lesson, before Deanna gets spanked. Bend over the dining room table, now!" She did as he ordered, and Chad grabbed her cheeks, spread them, and then suddenly, without any preparation, rammed his manhood into her butt! The shock of the pain was at first almost unbearable, but she just let it happen, and she even began to moan and sigh, to indicate her apparent pleasure at the penetration of her posterior. "Oh, my God! This hurts so much, but don't stop yet! I am a naughty Mommy, breaking my promise not to tell Deanna about us! Punish my ass with your cock- fuck me as hard as you wish!" "You've really been a bad girl, Mom! Haven't you?" "Yes, I've very bad! Keep hurting me with that cock of yours- I need it!" "You want this kind of discipline, too, Deanna? You've certainly earned it, but I'd love to give it to you, anyway!" "Oh, yes, Master! Your Mom and I are clearly cut from the same cloth! We're both wicked girls, and we badly need, and want, to be punished! Fuck my ass just as hard as hers! Give it to me that way- I want to be sodomized, too!" "You're really loosening up, Deanna! Good for you!" Roberta said between groans. "Yes, I love being a naughty one!" "You're a dirty, whoring slut, aren't you, Mom?" "Yes, I am! I'm your bitch, and you can fuck me any way you like!" "You're my bitch, too, aren't you, Deanna?" "Yes, I am your slave, your whore, your bitch!" Roberta groaned a little more, and then so did Chad, as he shot his sperm into her sphincter, and she squealed from the warm, delicious feeling it gave her to have her son's semen in her butt. She had the most satisfied look on her face, and she begged him to fuck her ass every day that she visited him. "I want to be yours, in every way, so fuck me in every hole, any time I come over, please!" As he pulled out of Roberta's ass, Deanna simply planted herself on top of her fiance's mother, leaning over her, and pointing to her own ass, even spreading her own cheeks to accomodate her new master's cock. "I want to get fucked on top of your Mom- I want her to feel my orgasm, as it drips onto her ass! Please- it will our first threesome together!" "Alright, but you'll have to give her some added pleasure- masturbate her as I ride your ass!" "Oh, fuck, yes- do her that way, while she is touching my butt with her cunt! That way, we can both feel it!" Chad simply slammed his dick, straight from his mother's ass, into Deanna's derriere. She was proving to be as much of a masochist as Roberta, and this was hardly contradicted by the way that she enthusiastically took him inside her bottom, while pressing up against Roberta's. Roberta, for her part, really squirmed at this point. Somehow, the feeling of her son's fiancee's pussy brushing up against her bum really excited her, getting her even wetter. The skin on skin contact of the shaved cunt with her smooth, soft buttocks was undeniably sensual, and she began to moan again, delighting in the raw, visceral sensation of it. What's more, Deanna really was playing with her sex, which just exacerbated the intensity of the approaching mutual climax. Deanna loved the wetness from Roberta's pussy, and she even licked her juices off her fingers, telling her partners that she found them delicious. That proved to the final step that forced Chad to cum. He gushed a gigantic load of cream into her buns, and she just let out a shriek of animalistic ecstasy. She was definitely letting go, completely giving in to the orgasm. That was it; Roberta came now, drenching Deanna's hands and fingers, and giving her a virtual bath of girl-cum. Too exhausted to give Deanna her promised spanking, Chad offered her a rain check for the next day, and she, equally fatigued, took it. They all toppled over at this point, as soon as Chad had withdrawn from Deanna's butt, and they all fell asleep right there, with prima facie evidence of their menage a trois. Little did they know that Donny was planning to visit the next day. See part 3 to find out what happens when he catches them! Matchmaking Trap Ch. 03 Chapter Three: Donna Donny rang the doorbell at Deanna's, thinking, well the hell is she? "It's Sunday, for Christ's sake, she is normally home, and she said that Chad fishes on Sunday mornings." Donny could not help himself. He did feel badly for poor Chad, but the lucky guy was getting to marry Deanna! Donny had little experience in sex, due to his small penis, so he did not understand the alpha male's urge for multiple partners. Donny was leaning more in the sub direction; he was perhaps a little too sensitive, and despite the fact that he was fucking another man's fiancee, he never considered any other way of life than monogamous marriage to a single babe, as long as she was beautiful and sexy. Deanna was very hot, and Donny long worried that she was way out of his league. Simply put, Donny was an obsessed, pussy-whipped romantic fool. Deanna could do no wrong, as far as he was concerned, so he simply accepted her decision to keep fucking both him and Chad. That's not to say that he wasn't jealous. He was just so pathetically grateful that Deanna had seemingly rediscovered her interest in him that he was willing to tolerate anything, even a double standard on her part. He didn't know yet that she only fucked him as a standby, when she wanted sex of some kind, and that he still was not and never would be the love of her life. She couldn't love him, because she didn't respect him. He was a groveling dog, and she knew it. This one-sided deal took on a new dimension, however, when he rang the doorbell again, and Roberta finally answered the door. "What are you doing here, Donny? Are you looking for Deanna?" Donny was very embarrassed and anxious. What was Chad's mom doing at Chad and Deanna's house? Had Deanna been caught? "Well, I'm, um, uh.." "Here to fuck Deanna?" "What?" "You're here to fuck Deanna, aren't you?" "What the hell kind of question is that?" "Don't change the subject- I know about the 2 of you fucking on the side, and so does Chad!" "Well, I'm sorry about that, but I can't help it. I'm in love with Deanna! I make love to her, instead of just fucking her!" "Chad does both, and she prefers his cock to yours, you pussy! He not only fucks her, he does it wildly and roughly, just the way that your ex really likes it! She is bored with your pathetic lovemaking!" Donny was shocked. His sweet, gentle Deanna, the love of his life, wanted to be used and degraded? "That's sick! He's degrading her!" "No, he is satisfying her, which you'll never do! Guess what Chad is doing to your ex as we speak. Don't know? I'll tell you what. See for yourself!" She led him into the dining room, where Deanna was bent over the table, as she had been the night before, and Chad was spanking her butt rather mercilessly. She was crying, and Donny felt like helping her, but then Roberta grabbed his arms and held him back. Just then, he heard her scream. "Yes, I like that! Oh, Master, spank me some more! Hurt me again! I'm your sex slave, and I'll do whatever you say!" Donny was absolutely flabbergasted. Deanna was getting her butt struck by this ruthless pig, and she was not only taking it: she was loving it! "You see, Donny, Deanna is a sub, not a goddess! She doesn't want some fool pining for her and groveling for her favors. You amuse her, nothing more than that! She loves Chad, not you, and she wants to marry him! He dominates her, and she loves that!" Upon hearing Donny's name, Deanna looked up and bit her lip. "Oh, Donny, I'm sorry that I forgot to cancel our session. Too late, anyway, to hide it. Chad and Roberta know all." "Why do you like that sick stuff? It's perverted!" "It's what I want, and I don't think that it's bad at all. I like you, Donny, but Chad has shown me a new side of himself, which has made me happier than ever. I'm in love with him, not you. I still want to keep fucking you, however, if you'd like that." Donny's dick gradually rose in response to that last remark. She still found him attractive! He knew now that she never intended to get back with him, and certainly didn't intend to be exclusive with him. He could either accept Chad's dominant role in her life, and allow Deanna to walk all over him, or give up the sexiest woman he'd ever known. What to do? "I only want you, Deanna. Why don't you want only me?" "Because you only have a 4 inch dick, which is really sad for you, but I can't be content with such a sorry penis. Also, Chad is strong and manly, whereas you are weak and effeminate. You're a boy-toy, nothing more. Chad doesn't just want me- he has Roberta too. He's a stud, a real man, who fucks around as he wishes. Face it, you were dealt a terrible hand: a sweet, but too nice personality and a small penis." "There is one solution for him, you know!" Roberta spoke. "What's that?" Chad asked, quite curious as to what should be done for such a pitiful case of a weakling. "If he can't be a great stud, we should help him by making him a hot babe!" Deanna looked at Donny, and had to agree with Roberta. The answer to Donny's problems lay between his legs. She really felt sympathy for the guy; life must be hard on a man with a small dick. Her future mother and new, part-time mistress, had the right idea: turn his weakness into an asset, by feminizing him! He already had the sweet, sensitive nature of alot of women displayed many times. (Of course, many women didn't.) "That's a great idea! Donny, you make a lousy guy, but you'd be a really terrific gal! What of it, Donny? Want to be a woman?" Donny couldn't believe what he had just heard. They were proposing to solve his problems by changing his sex into one more compatible with his hyper-sensitive, passive-aggressive nature. But, he did have one fear: the pain of losing his dick! "What about my penis?" "Would you really miss it? It's only brought you pain, due to its unimpressive size." Chad pointed out. "But the pain?" "You can be given anesthesia. We can do it in stages, anyway, starting with feminine clothes, then female hormones, and finally, the replacement of your genitals with a vagina." Roberta replied. "But I'm not gay!" "You won't have to do it with guys! You can be a lesbian! Lesbian sex with me, wouldn't that be more fun for both of us? You wouldn't have to worry about your erection, and if you ever wanted to penetrate me, you could use a strap-on dildo, which is likely to have more impact than a little dick." Deanna told him. They were rapidly eliminating his excuses. He knew that they all wanted him to become a woman, for both his sake and Deanna's. Well, he'd seen the army slogan "Be All That You Can Be" once, and that seemed to sum up the issue. He had more potential as a woman than as a man, plain and simple. If you can't be hot as a guy, why not turn heads as a girl? "Alright, I'll be your girlfriend, if I can't be your boyfriend!" "Splendid! We can start today! You were always rather cute, so making you a girl just makes better use of your assets." Deanna stated. "What's my new name?" "Donna. Logical alteration of Donald, or Donny, as it were." Chad suggested. Deanna and Roberta nodded their agreement. "Well, Chad, I'm a slave, so I can't keep him as a slave, can I? We can be lovers, but he needs a master or mistress better suited to the task of controlling him. I'm too submissive for that." "I'll own him here, and Roberta will dominate him at her place, just like you." "Sounds like a great plan, son. However, if we're going to turn 'Donna' here into a girl, we should stop using masculine pronouns, shouldn't we? She needs to learn to think of herself as a woman." "Agreed. Donna is her name, and she shall be referred to in the feminine from now on." "Okay, so, Donna, we need to start feminizing you right away, alright? We'll start with undressing, if that's fine with Master here." "Very good, slave. That will work. Donna will take off her old, masculine clothes, now." "Donna" did as she was told. She stripped down to total nudity, revealing, sure enough, the smallest cock Chad had seen since puberty. She really did belong to the beta male category, and soon she would be a female instead. "Alright, Deanna, I want you to take her into the bathroom and shave all of that unladylike hair off of her body. Get her nice and smooth." Shaving her took a while, but Deanna knew what she was doing. She eventually had her completely bare of body hair of any kind, except above her neck, of course. The beard would have to be dealt with by electralysis. Meanwhile, however, wax would do. Donna winced in agony as she ripped the stuff off her face, but she let her do it anyway. Finally, it was time to apply makeup, and she did an expert job, as she was a stylist. "Okay, now. Look at yourself in the vanity mirror and see the lady you're becoming, alright?" Donna did so, and she saw that she really was looking more feminine by the minute. Her hair was even re-styled in a feminine way, which was all that Deanna could do for her, given its shortness. She was looking at a woman, it really seemed, and she had to admit that it made her hard to see her own reflection. She was getting aroused by a woman besides Deanna for the first time in months, and that woman was herself! What could she do? She wanted to thank Deanna for doing this for her- turning her into a lovely, graceful woman. She moved over to kiss her ex-girlfriend, and was pleasantly surprised at the passionate liplock that followed. Deanna was kissing her back, more erotically than she had ever kissed during their relationship. Obviously, the Pygmalion-like work was having an effect on its creator, who was excited by the woman she had made out of Donna. "I see that Donna interests you alot, Deanna." Chad said from behind her. "Yes, Master. Donna is much sexier than Donny, and she is truly ready to be dressed up as a girl and fucked like one." "You want to fuck Donna in a lesbian manner?" "If that's ok with you, Master." "It is. Fuck Donna in the ass with the strap-on." "Yes, Master." Deanna then led Donna by the hand to the master bedroom, where she took out the dildo with a thigh harness, and began to put it on her. Donna was looking rather worried, but Deanna assured her that one day she would get her turn, although that wouldn't happen while she still had a dick. "Your dick is not going into this pussy ever again. You are a woman now, and women don't shoot sperm into pussies. No masculine behavior is permitted after today, because you are a lady, and a lady behaves in a feminine way." She directed Donna to lie down on the bed, on her stomach, and then she mounted her, taking the lube first and applying it to Donna's virgin butthole, before she inserted her dildo into her bowels. She began to ride her rather fiercely, apparently unconcerned about the inevitable pain of the initial sodomy. Fucking Donna's ass was an incredible new high, as she found herself spanking and fondling those smooth, reddened cheeks. This shaved bottom had a wonderful feel to it, and Donna was evidently beginning to enjoy the experience. Deanna kept butt-fucking Donna for what seemed liked a whole day to the poor transvestite, but soon, the prostate was showing its reaction. Donna's cock grew, and she suddenly ejaculated, in a way that would be considered premature, if she was going to penetrate a pussy. Deanna looked at the amazing scene in front of her. She was butt-fucking a man who looked more like a woman, and the transvestite was cumming from the excitement. This made Deanna cum herself, and then she heard chuckling and giggling. Chad and Roberta were clearly enjoying the sight of Deanna's ex taking it up her ass. Chad winked at Deanna, and she blew him a kiss. There would be no more question of who was the man Deanna loved, because the only rival was now her woman instead. Matchmaking Trap Ch. 04 Donny (or "Donna" as she was now called) found his new life a tad frustrating, to say the least. She was not permitted to cum at all until the change was complete. It was agreed by her new owners that she was going to be happier and more fulfilled as a woman than as a man, so she was being gradually feminized. NO male behavior was allowed during the transition, since that would mentally reinforce the idea that she was a man instead of a woman. This included ejaculation. That was not to say that Donna wore a chastity belt or any such nonsense. In fact, this made it more stressful for her, since she could physically make herself cum, but had to restrain herself. She was not to play with her dick or anything. This did NOT prevent her from being aroused or stimulated by Deanna or Roberta. At times, it took ALL of her willpower to keep herself from cumming and being punished by Chad for doing so. Her new life had its drawbacks for sure. There were SOME benefits, though. She no longer had to act tough, which she knew that she wasn't. When she lived as a man, she found certain things humiliating, such as getting pushed around by another man. Now she could let a macho guy like Chad control her without embarrassment. Another advantage was not having to worry about impotence or the size of her cock. That four inch weakling would not fail her again. She could have sex with Deanna and not feel inadequate, even if she was frustrated by not being able to cum. She also engaged in "lesbian" intercourse with Roberta, which turned out to be surprisingly pleasant. One thing that she feared was that she would have to sleep with men at some point, despite the reassurances from the 3 people who now controlled her. Donna was NOT interested in guys and wanted only to service the 2 women in the household (they had all eventually moved back into Roberta's house, where Chad had assumed complete control). Increasingly, however, she had been shown a LOT of gay porn by the group and heard suggestions that she might actually enjoy it if she gave it a chance. In the meantime, Donna found her body changing. The female hormones eroded any resemblance to a man, aside from her "manhood". Her hips widened, shoulders narrowed, body fat increased, and muscles shrank. Her voice softened and more curves appeared around her waist. She found herself watching more "chick-flicks" and female-oriented TV. Chad, Roberta, and Deanna had even pooled their money to get her breast implants. Chad generally didn't like such things, but there was no alternative for a "she-male" such as Donna. She NEEDED some breast enhancement to be more feminine. Ultimately, she both dreaded and desired the final change: the replacement of her male genitals with female ones. She knew that the surgery would hurt like hell, but she also wanted to get the transformation over with at last! She would FINALLY be allowed to cum (when her privates had healed enough, that is)! There would be no more torture or teasing by denial of sex. She would even get to penetrate Deanna again, albeit with a strap-on instead of a real cock. All of this planning was soon altered, however, when Deanna persuaded (not forced, as that would be breaking her word) Donna to experiment with men one night. She offered to take her out to a bar and pay for the drinks herself, at least until some guys decided to buy them some booze. With any luck, some men would accept her proposition of "blowjobs only" with Donna, while Deanna would "go all the way" with them. Chad had no problem with this, as he was busy fucking Roberta that night and wanted to eventually enjoy Donna's favors. The only difficulty was that guys at the bar might suspect that something wasn't right when one of the girls didn't completely put out, while the other one did. They decided to explain that away by saying that she was having her period that night. Most men shied away from fucking a girl when she was "on the rag". Well, they met some guys, alright. There were two in particular, a tall German named Erich and his American business partner called Justin. The former was handsome in a more classic sense, with blonde hair and blue eyes. The latter had a darker complexion and jet-black hair. Nevertheless, he was suave and exotic, which appealed to Deanna in about the same way that Chad's swarthy look turned her on. Erich offered to buy Deanna and Donna drinks. Deanna accepted on behalf of them. She clearly took charge of her girlfriend. She ordered margaritas for both, which the German gladly covered. He was apparently the wealthier of the two men. What she didn't know was that he was part of a ruthless crime syndicate in the former East Germany. It had started as a black market enterprise to survive the Communist era and grown rich since then. Justin was not so nice, either. He was involved in a radical Puerto Rican terrorist group seeking independence for that island. They worked together on crimes and split the profits. They were simply enjoying a little R and R that particular night. Naturally, these were NOT the sort of men who would necessarily go along with an agreement such as Deanna intended to propose to them. She was playing with matches and about to get burned. Neither Justin nor his German gangster friend were the sort to balk at force when it meant getting laid. After all, they were criminals anyway. What was one more crime? "So, you ladies want to fuck, senoritas?" Justin finally asked them with surprising candor. "Well, I want to fuck. Donna here is having her period. I don't think that she feels QUITE so sexy tonight," Deanna explained. "So, what will she do? Watch?" Erich demanded in his guttural Prussian accent. "I think she might be persuaded to do a little more than THAT, buddy," she answered him. "Meaning what exactly?" the German probed. "Let's just say that she will help you get ahead," Deanna informed him. "Ah, a fellatrix, then?" the terrorist asked for clarification. "Precisely. She will suck you off, while I let you fuck me. You can take turns using me and her, or simply take one of us for each of you," the real woman offered, while her transsexual lover giggled at their secret. "Very well. We will accept. I will treat my German guest here to the full thing, as is only proper for a host. Meanwhile, I will content myself with oral sex. I'm a little too jealous by nature to share a woman," Justin agreed. "Okay, that will work for us," Deanna accepted. Everything went fine for a while. Justin and Erich took Deanna and Donna back to their hotel room and ordered them to undress. Donna balked at completely disrobing, at which point Deanna reminded the men that she was menstruating. They still seemed to believe the claim and let her keep her skirt on. At first, both of the women fell to their knees and sucked the guys' cocks. Deanna thoroughly enjoyed this experience, as she had not been with too many real men aside from Chad. Most of her other sexual activity had been with Roberta and Donna. That was satisfactory most of the time, but this was a pleasant change for her. The taste of the German's thick cock delighted her a lot. It had more texture, at least partly due to the fact that he had a foreskin, unlike Chad or Donna. That didn't mean that she preferred Erich's meat, but it was a good dose of variety. She was also happy that the gangster kept his dick clean. She had heard that was more difficult for uncircumcised men, but it was not impossible. His 7 inch manhood was delicious enough to affect her pussy, which began to be drenched. The smell of her sex demonstrated to the German that she was eager and ready for a more thorough penetration. "Get on the bed, so I can fuck your soaking cunt, slut," Erich commanded her. Deanna didn't hesitate to obey him, planting herself on the bed with a thud. She assumed the missionary position, lying on her back, but the German criminal roughly turned her onto her belly. He then shoved his cock inside her pussy, brutally entering her. While it hurt when he thrust so deeply into her, he was smaller than Chad's meat, which had already been in her. She was wet enough to accept him anyway. In fact, the feeling of such a forceful invasion of her sex excited and aroused her completely. This was precisely the sort of man who turned her on the most: a powerful and domineering guy with few inhibitions. She loved being ravished by such a strong fellow. While this happened to Deanna, Donna busied herself giving Justin a blowjob. The radical was getting more excited by this experience, as was the she-male. However, the man started to wonder about what it would be like to fuck this babe's tight hole. After all, a woman's period didn't make her ass bleed. "Take off your skirt and bend over, slut," he finally instructed Donna. "No, I'm on my period. I don't fuck when I'm on the rag," she refused. Deanna would have added her objections, but she was too busy getting her pussy reamed by Erich's hard manhood. He made sure that she didn't try to stop now by pinning her to the bed. There was no way that he would let her interfere with his "comrade" getting laid. In spite of herself, Deanna found this roughness so stimulating that she came at last. Encouraged by that fact, the German pounded her cunt longer, determined to spill his juice inside her. He slammed his meat into her several more times, until he emptied his balls into her sex. Even though she was satiated, Chad's fiancée still didn't move to rescue her ex-beau. She was too exhausted at the moment to do more than watch with mixed emotions as Justin, impatient with Donna's hesitation, pulled out of her mouth and removed her skirt. As the transsexual hadn't worn panties that night, it was obvious to everyone in the room that something "extra" was present. The fully erect dick, at its unimpressive 4 inches, was a proverbial "smoking gun". Both men stared for a second and then grinned at each other. This particularly frightened Deanna and her old flame. What did those grins mean? "Bend over the fucking bed, bitch. This is your LAST warning!" Justin screamed at Donna. "You still want to fuck her?" Deanna inquired, stunned at this decision on the terrorist's part. "Yes. She still has THAT hole available and I want to fucking get laid! You deceived us! For that, you should be punished too, but Erich here doesn't have more than one load a night. Your penalty will be to watch your friend here get it up the butt, with no lube by the way," the Puerto Rican announced. "Well, you broke the agreement," the lady complained. "You're one to talk about dishonesty! Next time you want to go out with a she-male, let the men concerned KNOW that she is a tranny! You never gave us a chance to decide if we minded! You need to be taught a lesson, you sanctimonious tramp!" Erich declared. "Hold her down, amigo," Justin told his friend. The German gangster was happy to do what his partner asked of him. He even removed his belt from his pants and used it to restrain the woman as her paramour prepared to take a cock up the ass. To make sure that she didn't squeal, a sock was shoved into her mouth. Erich then pulled out a Luger and pointed it at her head. "Shut up, spread your cheeks, and let my friend here enjoy you! Otherwise, I will blow this cunt's head off!" the mobster threatened Donna. The tranny obeyed, since she still loved Deanna and didn't want her to die such a gruesome death. The initial thrust of Justin's cock was worse than she feared, since there was no lube. The she-male felt as if she were being impaled on a stake like the victims of Vlad Tepes. It made her half-wonder if the man was gutting her like a fish. The feeling reminded her of the scene in Braveheart where Mel Gibson's character was disemboweled by the English during his execution. There was no attempt by the revolutionary to be gentle with her. He brutally ravaged her, taking her butt hole with no compassion or mercy. The more furiously he rammed her, however, the number she became to the agony and the more she relaxed enough to appreciate the pleasure of the dick in her backdoor. Even so, she was certain that her ass would be too sore to use for a few days. Erich laughed as he watched his partner bugger the poor transsexual so roughly. She was being raped and sodomized, but she actually liked it now. That hardly shocked him, though. Things like that happened in Berlin a lot these days, especially in the "leather culture" of gay men's night clubs. He ran a few of those establishments, though solely for profit and fronts for his criminal activities. Sadomasochism was quite a popular lure for his businesses. "Your friend loves it up the ass. I can tell that she delights in the pain and forcefulness of the act. She is what patrons of my bars would call a 'bottom'. That suits her, especially given where she is taking it right here! She loves to be hurt and controlled. I hope that she finds a man who can give her what she wants. In the meantime, however, it's Justin's job to punish her," the German taunted Deanna. A moment later, the terrorist finally shot his load into Donna's butt. The two men laughed as they cleaned their dicks and got dressed again. Even though the she-male was still hard, they made her put her clothes back on, then untied her lover and told her to do the same. "We are done with you sluts! I hope that you have learned not to trick men in bars when it comes to sex. In the future, honesty would be the best policy," Erich joked. "Si. Comprehende, muchachas?" Justin broke into his father's native tongue. "Comprehende, senor," Deanna agreed, glad that her 2 years of high school Spanish weren't wasted. "Good. Now, get out, both of you! Vamos!" the Puerto Rican commanded them. Without even protesting that Donna needed to cum, the frightened pair left the room and hurried back to the bar. They weren't very drunk, so they got in the car and raced back home. They both feared that the two men might change their minds and decide to kill them. They seemed a LOT more dangerous than at first and neither lady would put murder past them. The hard-on stopped being a problem by now, since the she-male's fear caused her to go limp again. The event had nevertheless taught them something else, which they agreed to mention to Chad and Roberta. Donna didn't need to be a complete female to attract men. A tranny like herself still had something to offer them, while being able to help the man of the house satisfy his favorite women. Donna would hopefully get to keep her cock and even cum on occasion, although that would be up to Chad's discretion. Of course, the she-male would probably have to earn it by servicing the Master's cock, but that wouldn't be an issue anymore. Provided that Chad didn't murder the two rapists and end up in prison, the future should be just fine, Deanna thought. Now if I could just find a new skirt to replace the one in which I peed on myself during the assault. Chad will want sex after hearing about this and he won't want his fiancée smelling like piss. I don't mind sharing him with Roberta, but I will NOT let her have him to herself on this night or any other. Once we're done with that, I'll propose a meeting of the minds and try to give Donna back the privilege of cumming.