Maing of a Sissy Whore

Pimped Out

If you haven't read the first 2 chapters, it might be a good idea so that this makes more sense. Your call, and I hope you enjoy either way!

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Jeff stepped off the bus feeling defeated as he walked the five blocks back to Brad and Kayla's place. He couldn't even think of it as home now, since Kayla was sure to kick him out tomorrow. He was jobless, broke, and hungry. And after failing at today's search for work, Jeff felt desperate. He didn't have anyone in this town who he could call a friend, except Brad. And Brad's girlfriend, Kayla, had made it really clear that he either paid his way on rent and food or he was out on his ass. Homeless! Jeff was about to be homeless and he couldn't wrap his mind around it.

The closer he got to home, his mind drifted back to the scene with Kayla and Brad. He still could not believe that she had made him suck Brad off in exchange for dinner. Most of all, he couldn't wrap his mind around the fact that he had actually done it! Or understand why every time he thought of himself kneeling there in front of Brad, mouth full of cock, his own cock started to harden.

He steeled himself for the worst as he walked up the path to the front door. Just as he was about to fish out his key, the door swung open and Kayla stood there in tight cutoff shorts and a white crop top tee which contrasted with her smooth chocolate skin. The tee had been cut into a deep v-neck and Kayla's amazing tits were bouncing invitingly as if they might fall right over the top. She looked him up and down.

"Didn't get a job, did you?" she said with a half-smile.

Jeff hung his head and shook it as he replied "No, Kayla. I tried everywhere, I swear. I must have walked miles today and talked to at least twenty places, but no luck. If you can just let me stay tonight, I..." his voice started to break "I will be out tomorrow."

"What you need right now is to relax. It's been a long day. Why don't you go take a shower and get refreshed and then let's talk."

Jeff perked up at this, thinking maybe she had finally taken pity on him. He quickly agreed and headed for the shower.

Kayla followed and said, "Hand me those dirty clothes before you jump in, so I can toss them in the wash with the stuff I have left."

Happy to have someone do anything nice for him, Jeff went into the bathroom and quickly stripped. He wrapped a towel around his waist and opened the door to hand Kayla his clothes, then jumped into the hot shower and let some of his troubles melt away.

Twenty minutes later, Jeff stepped out of the bath feeling refreshed and hopeful. He had a towel wrapped around his waist but had to hold it together with one hand as the only towel in the bath was a small one. Kayla must have put the others in to wash.

When he walked across the living room to his bedroom, Brad was sitting on the sofa and gave him a quick head nod as he played Xbox. Kayla was in the kitchen grabbing something from the fridge, and her cutoff shorts rode halfway up her ass as she bent over. Jeff stopped for a moment and stared, his dick quickly rising to attention under the towel. Before she turned around, he headed into his room.

Closing the door behind him, Jeff let the towel drop to the floor and stood there dumbfounded. Had he walked into the wrong room? No, that couldn't be. This was only a two-bedroom place and the other room was Brad and Kayla's. But nothing he saw made sense! All his stuff was gone, and the bed looked completely different with a pink fitted sheet and one pillow with a pink pillow case that had "princess" embroidered in white on it.

The dresser was the same, and Jeff quickly stepped to it so he could grab some underwear from the bottom drawer. But when he pulled the drawer out, it was filled with sheer women's panties. He opened the other drawers and found nothing but a couple of pairs of stockings, some garter belts, and four bras with what looked like silicone breasts in a box.

Panicking, Jeff ran to the closet. As he was about to open it, he noticed the door had been altered. There was a hole in the middle, about waist high, and the edges of the hole had been covered in gray duct tape all the way around. The door handle of the closet was different too, with a lock on it. Who in the fuck puts a lock on a bedroom closet? He thought this as he opened the door, only to find 4 hangers inside. Each hanger had a different colored see through babydoll or similar women's lingerie hanging from it. There was nothing else.

The sound of the bedroom door opening broke Jeff out of the reverie he was in and he spun around. Kayla stood smiling in the doorway, with Brad standing shirtless behind her.

"What do you think sweetie? Do you like what we've done with the place?" Kayla chuckled as Jeff realized he was completely naked. She deftly kicked the towel behind her, and he had no choice but to stand there exposed.

"Kayla...Brad, what the fuck?" Jeff couldn't even think of what to say. "Where is all my stuff?"

"It was put into storage, as collateral for the rent you owe."

"And all this" he motioned around the room "what is this?"

"This room has been set up for our new tenant, Princess." Brad said as he reached around and gently tweaked Kayla's right nipple through her tee shirt.

"Who is Princess? You guys are kicking me out tonight? I can't leave like this, please." Jeff heard how whiny his voice was and he hated it. He also hated that his dick was getting hard as he watched Brad fondle Kayla in front of him. She giggled as she watched him become fully erect.

"Princess is a sex worker, which is a very honorable profession. She needs a job and food and a place to stay. And we need rent paid." Kayla smiled "Princess is you, bitch."

Jeff's mind was reeling, and he felt light-headed and slightly dizzy. "Kayla, what are you talking about? Look, I just want to leave okay? Give me back my stuff and I can be gone tonight."

But she shook her head "Too late for that, honey. Rent is due and we are counting on you to come up with your part. If you leave now, it will be after Brad kicks your ass and then throws you out the door naked." Jeff looked at Brad and realized they were serious.

"Guys, I don't know what you want me to do. I don't have a job and I can't get you the money in time to pay the rent. I am sorry."

"Sweetie, when you took care of Brad the other night, I realized you have at least one skill that we can use." As she said this, Kayla stepped further into the room and then stepped aside. Jeff saw that Brad wasn't just shirtless, he was naked, and his hefty cock bobbed in front of him from where it had been rubbing against Kayla's ass.

"You want me to suck Brad off as rent?" Even as he said it, Jeff knew he would do it if that would guarantee him a roof over his head and food. He was desperate.

Kayla laughed. "Oh, you will suck Brad's cock whenever he wants, slut. But paying the rent is a full-time job. Brad says you are okay as a cocksucker, but you need practice. I did some research and we think that considering your lack of expertise, and the fact that you are a sissy not a real girl, the best we can get right now is probably 20 bucks per blowjob."

Jeff sat down hard on the pink bed. They wanted to whore him out?

"Now, your portion of the rent is $400 per month," Kayla continued as if she were breaking down a normal roommate agreement "figure another $200 for groceries and incidentals. So that is $600 per month living expenses. If you are going to go out and get your own customers, then everything you earn will go towards your expenses and anything extra is yours. On the other hand, if you need me to arrange clients then my commission is half of your fee."

As Kayla went on, Brad stepped over to the bed in front of Jeff and placed the head of his cock to Jeff's lips. It felt as if he were outside his own body, watching the scene, as his mouth opened obediently, and Brad began to gently fuck Jeff's face. Kayla grinned and said "Good, getting practice already."

"So, basic math says that if you get all your own clients that would be $600 divided by $20 a pop which means 30 cocks to suck for this month's expenses. On the other hand, if you need my help then with my fee that will be 60 cocks for you to reach your goal. More if you want to have spending money or buy back any of your boy clothes."

It was clear that Kayla was turned on by the whole thing. Her breathing was getting heavier and she had unconsciously begun touching her nipples as Jeff took Brad's cock down his throat. Meanwhile, Jeff could feel Brad starting to swell and throb in his mouth. Was this really happening? Were his roommates going to whore him out for rent?

Kayla continued "Now, we don't have any time to waste if you want to stay here. So, I took the liberty of setting up a little meet and greet..." she paused, then giggled "Haha! Meat and greet, get it?" As she said this, Kayla went behind Jeff and pulled his arms behind him while Brad continued to slide his slick shaft in and out of Jeff's mouth. A clicking, ratcheting sound startled Jeff as he felt something close around his wrists. Instinctively, he tried to pull his hands away from Kayla but couldn't. She had handcuffed him? Jeff suddenly felt claustrophobic, desperate to get free. But he was unable to move as Kayla held his cuffed hands down and away from him while Brad gripped his head in both hands and began skull-fucking him in earnest.

Brad's excitement was evident as his thrusts became deeper and more forceful, the head of his cock touching the back of Jeff's throat and triggering his gag reflex. Jeff tried desperately to pull away but Brad was too strong and suddenly shoved the entire length of his dick into Jeff's mouth. As panic filled Jeff's mind, he felt the cock swell and jets of sperm begin shooting against the back of his throat. After about the fourth spasm of his orgasm, Brad relented and pulled back until just the head of his penis rested inside Jeff's lips and the last spurts of cum flowed out over his tongue.

The only sounds in the room now were heavy breathing and then a thick gulp as Jeff surrendered. The remaining silence was broken by the sound of the doorbell, causing Jeff to jump and Kayla to giggle excitedly. "Sounds like our guests are here for your first work shift, slut."