Matchmaking Trap- Chapter 4

Donny (or “Donna” as she was now called) found her 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.