Pimping Out My Roommate

[LittlePoundCake]

CHAPTER ONE

I cursed silently as I heard the front door open and shut.

It’s not that I was ashamed of what was happening, and certainly wasn't that Jessie would disapprove... but the old closet case with his face between my cheeks had jumped out of his skin at the noise, scraping my hole with his short beard. Bubble butts chafe enough, I didn’t need the help from a sandpaper-faced dad imagining his wife walking though the door.

"Who is it?” He asked in a stage whisper. “Do you have a roommate? A partner?"

I laughed and jiggled my ass in his face. “No, just my roommate. She’s cool, I just didn’t expect her home this early. I’m sorry.”

He relaxed a bit. “Oh okay, cool… so like a girl-girl or like you?”

The million-dollar question with Jessie. I called her a she, and she looked like one a lot of the time… but she definitely wasn’t trans, she was whoever she wanted to be on any given day. Most days that happened to be a bleach blonde faggy little bottom boy who wore booty shorts and makeup to the club… but that was why we got along. We were the same height and same tiny build, though Jessie had thicker, more girly legs. She was white, I was black, but give her too much time tanning and me too many dark nights smoking and we might have been cousins.

Tiny, gay little cousins.

“Like me for sure.” I responded, rolling over on my back and pointing at the wall of polaroids next to my bed. “She’s the blonde in half the pictures.”

Half the pics on the wall were us at the club dancing and wearing practically nothing. He was into it, you could tell, and that suited me just fine. The more turned on he was the quicker he’d finish in me. I wasn’t big on fucking, if I’m being honest. Put a gun to my head and I’d say I preferred topping, but the closeted white men who supported my business usually wanted to top, and the ones who wanted to bottom weren’t my type. On any given day I’d rather put the TV on, light up my pipe, and just lose as many hours as I can. I liked company and liked touching, but sex just wasn’t the way I liked to get high.

Jessie was good for that. She didn’t smoke tina with me very often but would do an edible and stay with me, watching old reruns of Top Model and complaining how much better it was than RuPaul, or making me pose for new pictures to use on my apps. If I’d been inside for too many nights, she’d force me into one of the skimpy outfits she wore on OnlyFans and drag me to the club so we could dance and drink.

“Does he do this too,” the man asked. “I’d love a three-way if he’d be interested…”

“Sorry, she doesn’t hook. She does cams and OnlyFans.”

“That’s a shame,” he whined, “I’d be happy to pay him or pay you if you could make it happen.”

That took me by surprise. “You’d pay me…. to have sex with her?”

He shrugged, “Money’s going someplace, right? Paid you $200. Give you five if you can get her in here with us.”

This was new territory, and I could use the money. Higher rates meant a nicer class of clientele, but fewer. Could I even do it? I thought I probably could, given some proper scheming.

Was it wrong?

“So?” the man asked. I had been thinking too long. I made a snap judgment and grabbed my phone to show him some pictures from Jessie’s OnlyFans.

“She doesn’t hook so if I try to drag her in here for a three-way it will be too obvious. It would have to be sex with her or sex with me.”

“Her.” He responded immediately, the scumbag closet case.

“Great, $500 and I think I can make it happen.”

He paused, grappling with the idea of paying that much for one little twink. In the end the pictures on my phone and the memory of whatever haggard mother of his children was waiting at home for him brought him around to my side of things.

“$400.”

“Done. Wait here.”

As he Venomed me the remainder I pulled a small pouch from my desk drawer and loaded a glass pipe with a new crystal, some of the good stuff. Grabbing my torch and the pipe I went out to see Jessie. The little blonde boy was sitting on her bed in her typically too small panties, playing with her phone.

“Hi, Gay! How was your day?” She said, glancing down at my still naked, swinging cock and sticking her tongue out. “I was about to shower, unless you need it.”

“My day was fine, but I have a client in with me. I’m so sorry.”

“Oh my god, no, I’m sorry! I didn’t mean to come back early!”

“It’s no biggie at all, he’ll be gone in a few minutes.” I frowned and showed her the pipe. “Hey, do me a favor. Can you try this? I didn’t get it from Amos, and I can’t tell if it’s got a weird taste. I need a second opinion.”

She sighed, and I could see her debating. “C’mon, please?” I said, “Just one take, just for my peace of mind.”

She grabbed the pipe and lit the bottom of it with the torch, twisting it in her fingers as the crystal melted inside. As smoke filled the chamber she took a deep breath, probably too fast, sucking the white smoke from the burning glass bowl. Her technique wasn’t quite as artistic as mine, but she still exhaled more than I thought she’d gotten.

“Tastes fine to me, I think.” She said, handing it back.

“That’s because you’re a shitty tweaker,” I snipped. “Here.”

Jumping up on the bed I lit the torch again, twirling it in a proper wave while I heated around the bottom. Still heating it, I stuck the tube in her mouth and said, “Breath in SLOWLY, bitch.”

She did a fantastic job this time, but I acted like she didn’t. “Oh my god you suck at this, girl, keep breathing in deeper so you get some. Now hold it in, do you see what I mean about the taste?”

She shook her head.

I groaned, “Ugh, maybe I’m being paranoid since it wasn’t Amos.”

Jessie exhaled a truly insane amount of smoke, making her room hazy. As lightweight and inexperienced as she was, she was toast.

I rolled the hard way off the bed, using my cock to push her panties into the crack of her bubble butt and making her laugh. “See? Nothing. You need to smoke with me more.”

I twisted and pulled from the pipe for a few seconds until it had cooled, then returned to my room and the horny man waiting there....

[WimBi]

Grrrrr! I like where this is going...

[TopDad2]

Great, imaginative start! You've got skills, and I can't wait to see where you lead us!!

[RawSubDad]

Great start, I’m hard and hoping for more chapters to cum

[ejaculaTe]

Pretty clever start... I'm ready for the next installment.

[Guest]

Can’t wait to read more! 

[LilBimbo]

Love where this is going

[LittlePoundCake]

CHAPTER 2

I had never understood young people who won’t fuck old men. If I absolutely had to get fucked, I’d rather be with an experienced adult than a sweaty, closeted college frat boy who’s never heard of lube and hits like a jackrabbit with Tourette’s.

Pull up the Myers-Briggs of gay boys who DO sleep with mature men, however, and there are three types of twinks.

The first are the twinks who only fuck older men for money but would never hang out with or date them. Obviously an acceptable profession in my book, but a poor, one-dimensional way of looking at the men who were our best and most fulfilling customers.

Next are the twinks who want to be hunted by a confident, silver wolf daddy. They want a sleazy, sexy, horny old man to separate them from the herd and bring them to a back alley where they can submit to the cumdump fantasies they dream about at night. They want to be demeaned and used by someone with infinitely more experience than a child like them could ever hope to achieve.

Lastly, there are the twinks with low self-esteem and daddy issues. No way to sugar coat it, these are the twinks who had cystic acne in high school and considered themselves worthless, but as puberty waned and their skin turned smooth they discovered hair dye, liquor, and bars full of old men just waiting to give them the unconditional love and appreciation that no parent or classmate ever did.

Jessie did fuck older men on the right day, and she was the poster child for type three.

I returned to my bedroom and shut the door behind me. My new friend was sitting on my bed stroking his hard cock to a picture he had pulled off the wall. I went to lie down next to him. The picture was one of my favorites of us posing in tight, tiny catholic school jumpers I had stolen from my sisters. In a fit of blind insanity last year we had found a creepy trucker to bring us to the Pride festival in Chicago, and had worn the tiny skirts at the parade.

It was good memory, and it made me feel a little bad about what I was doing. I pushed it aside.

“He good? How are we doing this?”

I heard the shower thud on outside and pushed my doubts out of my head. “When she gets out of the shower, she’ll be ready to go. Now stop calling her ‘he’ and maybe you’ll actually get to fuck her.”

I explained Jessie’s special brand of low self-esteem and dysphoria until we heard the shower turn off.

 

****

 

Jessie opened the bathroom door, still dripping a bit. Thanks to the tina her shower had taken a longer than usual, but she’d made it through eventually despite her increasing horniness and her fuzzy brain not focusing on simple tasks. She’d put a couple fingers in her ass part way through, making the shower take even longer and doing nothing besides making her even more horny.

Maybe Cam would fuck her. He didn’t want to very often and never when he was sober, but once in a blue moon she could catch him in a sweet spot between starting to smoke and arriving in Loo Loo Land.

She padded down the hallway to her bedroom, toweling off her hair. As she did, Cameron’s door opened and a gentleman no older than 50 stepped out, tucking in a fitted white button up and carrying his jacket, tie, and belt. They both stopped short, and Jessie quickly pulled her towel from her head to cover her small, naked cock.

“Oh my god, I’m so sorry, I was just in the shower.” She expected the man to be awkward at being caught, the way closet cases usually were, but he smiled and started forward again.

“Wow, are you the roommate? You’re beautiful…. you look like a princess.”

Caught off guard, Jessie giggled and blushed. “Oh wow, thanks so much!”

The man circled her. “You have such a beautiful body, I’ve never seen a girl like you before.” As he reached her his hand wrapped around to her bare ass. “Oh my god, and this ass…. Its so round and sexy. You’re so hot, I would do anything to make you my girlfriend…”

His hand felt warm, almost hot, as it grabbed a handful of her cheek and squeezed. She felt the horniness rising again as he complimented her and instinctively pushed back into his hand. His other hand wrapped around her to grab her waist and she was pulled to face him, still holding the towel.

“That’s all so nice to say, but I was about to go get dressed…”

“Oh, I don’t mean to keep you, I can let you go…” The man said, reaching around to squeeze her ass with both hands. “Please, can I just play with it for a second before you go, just for a minute… You’re the most beautiful girl I’ve ever met, I would be crazy not to look at you for a second.”

He felt so warm and she was getting so horny, Jessie didn’t quite know what to say. Her head was fuzzy and she tingled as he touched her. He was so nice, and she didn’t want to be rude…

She smiled and turned around, walking backwards a few feet to the edge of their living room and sticking her ass out as she walked to give him a show.

“Oh baby, you’re so beautiful…” The man was following close behind, unbuttoning his pants. He pushed her forward to bend over the back of the couch and she felt him grab her ass and give each side a gentle shake. He groaned softly and dove in with his tongue, pushing past her cheeks to lick her tight hole. The sensation was incredible, her head was swimming and she felt like her entire body was wired to his tongue. He licked her softly at first, then pushed deeper inwards. Her hole, still relaxed from her fingers in the shower, opened for his tongue.

She tried to pull back to reality as he pushed a finger inside. “I really should go, but thanks for all the things you said, you’re really nice…”

He didn’t stop. “This is the best pussy I’ve ever seen… I can’t believe how tight and pink it is, and this beautiful little clit.” He reached between her legs and began to rub her soft cock as he attacked her ass with a second gentle finger and shook her cheeks more, causing her to moan.

Her brain melted again as he stood up, letting his pants fall down and revealing a large, rock hard cock. He rubbed it on her hole as she moaned in pleasure, and her horniness took over entirely as she crawled over the back of the couch and turned around to suck his cock. It was an amazing cock, she decided. How could anyone with a cock like this and such nice things to say be paying for sex, even if Cam was hot. It made no sense.

“Ugh baby, you’re so good at this…” The man said, making her blush. She worked even harder as he reached back and squeezed her ass again, reminding her what she really needed. She spread her legs as far as she could while kneeling on the couch, revealing her small, pink asshole and rubbing her small  cock on the couch beneath her.

He came around the side of the couch and stood behind her, stroking his slick cock as she pushed her ass back towards him. They both moaned as he rubbed his cock on her hole again, then he pushed forward, burying his cock to the hilt and making her cry out.

“Yeah, baby, you like that…?” He pulled out and pushed all the way in again, making her moan as her fuzzy brain begged for more. “You love when I fuck your pussy, don’t you?”

“Oh god, yeah… fuck my pussy….” She gasped as he began to fuck her harder, slamming his cock into her hole and driving her into the couch. Pinned between her body and the fabric, her own cock tingled. There’s no way Cam wouldn’t have heard them by now… maybe he was smoking more of the tina he had given her and had headphones in...

The man behind her grabbed her hips as he drove his hard cock into her, making her moan and cry. She felt his grip tighten and his pace quicken and knew what was coming. With a groan, he released a load of thick cum into Jessie’s hole. His cry of pleasure and the warmth and pressure of being filled with his cum made her own cock begin spilling cum onto the couch beneath her.

The man fucked her for a bit longer, releasing more spurts of cum into her and then slowly pulling out. As he pulled his head from her hole, she pushed her butt up to try to keep his cum in her until her hole closed. A slut’s habit.

“Good girl.” He said, reaching down and giving her ass one last shake. He pulled his pants up, grabbed his things and left, running to his car like he was worried a satellite would catch him fucking the two little twinks inside the apartment.

I snuck out from where I had been hiding in the hallway. Jessie was still spread out on the couch with her head resting on the back of the couch. I could tell her brain was mush from the combinations of drugs and dick she hadn’t been expecting to get. I tiptoed around the edge of the couch to stand behind her and started taking pictures of the load leaking from her asshole. Jessie heard the *click* of the digital shutter and snapped up.

“Jesus Christ, Cam, get out of here!”

I grinned, “Bitch, I’m not the one fucking random closet cases as they leave the apartment! Now get that ass up, you can post these. Fucking slut.”

She groaned and reached back to place her hands on her cheeks, pulling them apart gently. “Oh my god, what is wrong with me? This is because you made me smoke!”

I laughed. “Excuse me for not wanting to die of a bad batch, Jessie. Don’t blame me for your slutty choices!”

She crawled off the couch and pointed at her cum stain on the fabric. “Fuck me, I got it on the couch.”

I pushed her towards the hallway, taking her curse out of context. “You want fucked, go get on Sniffies. I’ll clean this up, then you and I are going to smoke more tonight.”

I went to the kitchen and almost laughed out loud thinking about it. I had made $400 bucks and I hadn’t even had to get fucked. Jessie had a blast and nothing bad had happened. I even took pictures for her to put on OnlyFans, so she could make money too.

No matter which way I thought about it there was no downside, and I knew I wasn’t even getting started.

[Sluttybottom71]

Fuck yes, somebody please pimp out my hole

[JeffSLmmPigDadd]

Nice sTarT