The Deal Sammy Made for Rent

Whimpers escaped his lips. In between, he breathed in air in gasps and moans. Each one muffled by the pillow that his face was buried into. Behind him sat a beautiful person. A pair of hands gloved in white latex. They had slender effeminate facial features. Their body was lean and muscular. They seemed almost ethereal, bathed in the dim light of the bedroom.

A loose band t-shirt concealed their upper body, and they wore a tight pair of boxer briefs below. They traced their gloved fingers between the butt cheeks of their bound subject. A squirm in reaction. A smack across the ass cheek, followed by a gentle "shhh." They reached their hand out to a bottle of lube and pumped out two large globs into their hand. Spreading it liberally over the asshole in front of them, they began penetrating with their fingers.

One finger became two, and the boy's moans grew louder as the fingers began pushing in and out faster than before. Each thrust expertly rubbed against his prostate. Between his shaking legs his penis was fully erect and dripping with precum. A gloved hand wrapped around the cock and began stroking in a repeated milking motion. Cum began oozing out. The boy's moans became a slowly weakening groan, his whole body beginning to shake. His asshole tightened like a wrench around his penetrator's fingers.

"Good boy, Sammy, I think we've done enough for the day," a serene, gentle voice, the person removed their fingers slowly.

They removed their gloves and dropped them in a bin filled with previously used medical gloves and condoms. A few minutes passed as they uncuffed the young man and let him stretch out his legs.

"Dinner will be ready soon. When you get dressed, meet us down there okay?" A sweet smile spread across their lips.

Sammy nodded between his ragged breaths. His ass and cock are sore from being worked over. The person, his housemate Shana, had decided he needed to be cleared out today. Maybe he had been caught staring lustfully or watching something sexy on tv. Shana was the most fastidious of keeping him in check. Part of the deal with his living situation.

Sammy lived in a house with three other people. A woman, Eileen; and two enbies, Tommy and Shana. The rent was cheap, and food and utilities were provided. But for a man to live there, there was one special condition. A man may live there, they must keep their sexual urges in check. No visitors or partners of an intimate kind. To make this request more reasonable, the three other roommates offered to provide a sexual release for Sammy. He applied originally because he figured there was no way he'd get called. Given the affordability of the rent he went to check it out. He was given a tour, met the three other residents, and informed of any smaller rules that weren't mentioned in the article.

That was when Sammy asked about the 'sexual release clause.' Tommy worked in the medical field and informed Sammy that the releases would purely be preventative and in no way for pleasure. The other two reassured him that maybe sometimes it would be for pleasure. With really no better offer and any reason to say no, Sammy moved in shortly afterwards.

He's lived here for about four months now and his experience has certainly been a roller coaster. The first few weeks were a bit rough, and in Tommy's strict but capable hands, Sammy was introduced to a whole world of sexual release he didn't know existed. Full-body orgasms, prostate orgasms, milking machines and several others. Soon, Eileen and Shana joined in the effort. With the time, Sammy had grown accustomed to the routine of being milked by one of his housemates on a regular basis.

In a now moist spot on his bed, he processed his latest orgasm at Shana's hands. They had been going at him for about two hours. Shana always found edging Sammy brought out a more prominent ejaculate, meaning he wouldn't have to be milked again for a longer time.

After a few more minutes of relaxing his sore body, Sammy sat up and began cleaning himself off. He redressed and headed downstairs for dinner. As he rounded the corner into the kitchen, he spotted his three housemates. At the stove cooking food was Tommy. Tommy was a little on the shorter side, with a boyish haircut to match their softer features. Across their nose was a modest pair of glasses. Lifting their head and seeing Sammy enter, Tommy smiled and greeted him. At the table sat Sammy's other two roommates, Eileen and Shana. Shana was dressed the same as before but had added one pair of sweatpants to compliment their shirt. Their hair sat on one side, the other shaved except a small patch by their left ear. Their black hair and pale complexion almost made them look monochrome. Eileen had her hair up in a ponytail, loose curls falling where they pleased. Still dressed from work, she twirled a glass of white wine in her hands.

"Hey Sam, how are you feeling?" She asked, taking a sip of wine.

Taking a seat next to her, Sam gingerly sat down and chuckled.

"I'm fine, you know, work wasn't too bad," his cheeks were still a little flush from before.

Sammy tried not to actively talk about their releasing of him. Not unless they brought it up. Sometimes he'd hear them discussing it between themselves. To him it was just a weird point in his life. He never felt used, usually, and they didn't mistreat him.

"You've gotten so good at being quiet Sam. Shana said she didn't need to gag you earlier," Tommy approached the table with plates of food, passing them out.

Sammy blushed and gave a simple "uh huh" before taking the food. Shana smirked a little as they ate. The rest of the meal went on as normal. No more mention of it. Just regular bitching about work and classes. After dinner, they gathered in the living room to drink a few beers and a silly movie. By the time ten pm rolled around, Sammy was heading upstairs for bed. He had work tomorrow.

He dressed down to his boxers and headed for the bathroom across the hall. All he had to do was brush his teeth and pass out. Sammy then noticed something concerning. A pressure in his boxers as his cock swelled. He rolled his eyes and quickly finished brushing his teeth. If he got caught with even a slight erection one of the girls would milk him. He just wanted to get to sleep.

Eileen may let me off the hook, he thought, but no way, she won't be up here for another hour. I just need to make it to my room.

Sammy's room was right across the hall from the bathroom. He headed for the door, clicked out the light and took a single step towards his room. And he froze.

Standing at the top of the stairs was Tommy, mid-yawn. Their eyes narrowed as they spotted the bulge in Sammy's boxers. Letting their shoulders slump and sighing, Tommy walked to Sammy's door and opened it.

"Wait in here for me Sam, okay?" They gave him a tired look, but not upset.

Sammy's sighed and walked into his bedroom. He heard Tommy walk down the hall to get tools from their room. While he waited, he set out his stuff for tomorrow, plugging up his phone and shutting off his computer. Tommy came back in and closed the door behind them. In their hands was a pair of purple nitrile gloves, two condoms, and a device that was composed of a remote attached to a massage.

"Shana must not have edged you long enough earlier if you're already hard again" Tommy began pulling the gloves over their hands. It was snug around their fingers.

"Go ahead and get on all fours for me Sam."

Sammy pulled down his underwear and crawled onto the bed on his hands and knees. Tommy tore open the condoms and placed one over the massager. The other one they set aside. Lubricating their gloves, they grabbed ahold of Sammy's cock. A quiet gasp escaped his lips. Tommy began jerking Sammy off, rubbing both hands one after the other over his cock. The gasps became a soft moan as his cock went from semi hard to rock solid. Tommy then slowly rolled the condom over Sammy's hard cock. They could feel his cock pulsating in their hand. Tommy gave a cheeky extra squeeze which caused Sammy to jump in surprise.

"Okay Sam, I'm going to get this massager in you and we'll finish this up quick."

Sammy nodded as he let his head sink into the pillows. Tommy then began spreading lube over Sammy's asshole and the massager. They placed the tip of the massager at the entrance of Sammy's hole. Gently rotating the rip around his hole, watching it react as it puckered and loosened. Tommy started to press in. Sammy let out a moan as the massager pushed past his entrance. The moan turned to a hiss.

"Slow, slow."

Tommy pulled back a little, working the massager in just the entrance. They gave Sammy a few seconds before trying again. A hiss escaped his lips followed by a few whimpers. Tommy withdrew the toy and began lubing up their fingers.

"Hmm clearly the other two haven't been thorough enough recently. I'll have to make sure Eileen is spending enough time working your asshole," they began fingering Sammy, "you shouldn't have trouble taking that massager anymore."

Sammy moaned and whimpered as Tommy vigorously fingered his ass. He could feel them twisting their finger in circles, and then adding a second. A bit of drool came out of Sammy's mouth as Tommy worked a third finger in his ass. Tommy spent five solid minutes of fingering his ass with two or three fingers until they felt satisfied.

They once again reached for the massager and this time was able to push it in with little resistance. Sammy had regained some composure, but just the feeling of the massager in him putting pressure on his prostate made his legs wobble. A clicking sound went off and immediately his legs gave way. The massager had begun vibrating, the waves going straight into his g-spot. He couldn't hold back another moan, this one deep and loud.

"Oh damn, I forgot a gag," Tommy said.

They upped the speed of the massager two more times before setting it aside. Reaching forward, they then covered Sammy's mouth with their hand. Sammy moaned deeply into Tommy's gloved hand as he could feel himself getting closer. The vibrations didn't stop and Sammy came. His cocked pulsed against the condom as he filled it up.

Arms and legs shaking, Sammy collapsed into a heap. Tommy pulled their hand away, strings of drool running from their palm to his lips. With a little smirk, they wiped the spit on Sammy's ass. They removed the massager which caused one more small whimper.

By the time Tommy left his room, Sammy had passed out.

-

Sammy woke up the next morning feeling a bit sore after the previous days sessions. By the time he woke up, the other three had already left for work. After having confirmed this, Sammy laid back in bed a bit longer, and touched himself to the thought of what Shana and Tommy did.

Despite his morning arousal, Sammy managed to go all day without being caught with an erection. He kept this up for a few days in fact. He had a few close calls, including an encounter with Eileen on a trip to the restroom late at night. She had essentially been sleepwalking and missed the full cock pushing on his boxers.

When periods like this occured, Sammy could feel the roommates watching him. For how long this had been going on, he had kind of dialed in on what they look for, and why they do it.

Eileen kept an eye out normally, but especially when she was horny. She actually enjoyed milking Sammy. She was also the one who actually has penetrative sex with Sammy. Not always, but when she felt like it.

Shana was the best at picking him out. They also seemed to know when he was horny or not. It almost seemed like a game to them, and if they could "unintentionally" tease Sammy and then declare he needs a milking, she won. It also seemed like the act of milking was a science project, exploring what makes Sammy squirm and moan.

Tommy was the toughest to pin down. Usually it seemed like they weren't looking, but they would also sometimes bluntly ask Sammy if he was hard or not. The blunt nature draws an honest answer out of him most days. But it also seemed like Tommy was the most begrudging to do it. Except for those select moments where Sammy can swear they have a huge grin plastered on their face.

It had been four days since his last milking and Sammy had been content with jerking off and avoiding being stared at for too long. But that night something had gotten into Sammy and he couldn't stop thinking of arousing thoughts. He got home from work and put on a baggy pair of sweatpants and spent the majority of the evening in his room.

When he emerged a bit later, he headed for the kitchen in search of dinner. The house was quiet, and he seemed to be the only one home. With relief, he took his time preparing food and enjoying a beer. He's mind wandered as the night went on and he enjoyed his dinner. The buzz kept Sammy from realizing he was getting hard again. As he walked into the kitchen again to start cleaning up, a voice to his side startled him.

"What's that?"

It was Eileen, sitting in a chair enjoying a beer herself. She looked like she was trying her hardest to conceal a big smile.

"Dinner?" Sammy replied, gesturing to his empty plate.

"Not that, Sam. That." She made a little circle in the air pointed at his crotch area.

He glanced down to see his erection had returned from earlier. Now that it had been pointed out, he could feel how tight he was. Eileen made a "tsk tsk tsk" and walked up to Sammy. She pulled on his shirt until he was an inch from her.

"Come on, upstairs," a growl escaped her lips. She let go of his shirt and headed for the door.

His heart beat excitedly. Sammy set down his plate in the sink and followed her out. They headed upstairs and she ushered him into her room. Eileen's room was primarily covered in art supplies and a bit unkempt. But her bed lay open, blanket pulled aside. She gave Sammy a gentle shove onto the bed and pulled off his shirt. Bringing her nails to his chest, she drags them down slowly, leaving a trail of red marks along the way. Sammy hisses in pain. Reaching down, Eileen began removing his pants and continued until she had stripped his completely nude.

Bare naked before her, Eileen observed Sammy and dropped her pants as well. He smiled up at her bashfully. Eileen reached into one of many numerous drawers around her room. From it she pulled her tools; a box of gloves, a handful of condoms, a bottle of lube, a roll of electrical tape, and a gag. The gloves went on first, black and extra tight. Then came the electrical tape. Eileen loved Sammy being in her complete control. She taped his wrists and ankles together, leaving his ass spread wide and his cock completely out. By this point his erection was close to full. The gag went in next, Eileen giving Sammy a gentle kiss before making sure it was firmly in place. Lastly Eileen rolled a condom over his cock.

With flushed red cheeks, Eileen tittered at the sight of Sammy. She pumped out some lube and quickly began rubbing it all over Sammy's ass and cock. It started slow, rubbing his cock up and down. She twisted one hand around the head and another up and down the shaft. Sammy's muffled breath picked up and so did Eileen. Her grip tightened suddenly. Sammy groaned. She nibbled on her lip and moved a hand between his ass. Gently she inserted the tip of her finger.

"1, 2, -" Eileen pushed her finger all the way in.

"3." She let out a pleased sigh.

Sammy's cock began to twitch as she rubbed his prostate. Her finger curled rhythmically, Sammy moaning in tandem. Drool began leaking from behind the gag. Eileen started working her finger in a screwing motion, twisting and pulling. Her other hand continued to firmly jerk off her bound housemate. Both motions going fiercely, getting faster and faster. Sammy's muffled moans and whimpers grew louder. His cock erupted with cum, filling the condom to the brim.

"Oh fuck yes, cum for me you beautiful bitch," Eileen let out a lioness-like moan.

Eileen slowed her hand around his cock, but didn't remove her fingers yet.

"Don't get comfy. We're not done," she slapped his face gently with her free hand. She then pressed down and pushed a second finger roughly into Sammy's asshole. He whimpered loudly.

Twisting her fingers back and forth caused Sammy's body to shudder. Eileen pulled out and applied more lube before pushing her fingers back in. While she fingered his poor ass, her other hand rubbed across Sammy's face. Stroking his cheeks and lips, spreading the drool from underneath his gag. She squeezed his cheeks and forcefully made him look at her while she worked out his ass. Eileen could feel herself get soaked just watching the look in his eyes. Satisfied with finger fucking him, she stood up and removed her gloves.

Sammy breathed slowly as he watched her walk around the room in search or more fun. She grabbed a fresh pair of gloves, and emerged from around a corner with a harness. Inside a ring at the front of the harness was a blue cock shaped dildo. Sammy watched her in a haze as she rolled a condom over the cock and approached him again. She replaced the condom on Sammy with a fresh one. Eileen returned to fingering him, gentle this time. However, she quickly lubed her strapon, and presses it against Sammy's asshole.

"Now deep breath for me, beautiful."

She began pushing her cock inside him. Sammy's breathes became gasps as the cock spread him. Eileen didn't stop until the full length was in him. She could see how tightly he was pulling at the tape. After another twenty seconds, she began to thrust into Sammy. Picking up a rhythm caused his cock to bounce repeatedly. The motion made Eileen smile.

By this time, Eileen had begun to moan as well. Each thrust sending shockwaves through her body. As her rhythms picked up so did Sammy's gasps. His whole head was swimming as the strapon repeatedly hit his g-spot. Eileen watched as Sammy began to cum again, all without touching his cock.

She still wasn't done though. Before Sammy had time to process his orgasm, Eileen had begun flipping him over. Sammy's bound hands and feet left him laying their, ass pointed in the air exposed. But it wasn't long before Eileen's intention were shown. Standing just enough to be above his ass, Eileen leveled her cock and began pushing it again. Gripping both of his ass cheeks roughly, Eileen began truly fucking Sammy. Rapidly her cock went inside of him. He felt like she was jackhammering him. The overstimulation from the first orgasm and Eileen's second fucking began to make all of Sammy tingle. She stopped suddenly and removes her cock from his ass.

Eileen removed the tape from his wrist and ankles, and ordered him onto all fours. As soon as he was comfy Eileen penetrated him once again. Gripping his waist roughly, she continued her assault on Sammy asshole. Taking a moment to breath, Eileen pulled him all of the way on her strapon. She then reached forward and began undoing the gag from his mouth. With her free hand, Eileen curled two fingers into Sammy's mouth, making him taste her gloved fingers. With her fingers in his mouth, Eileen proceeded to keep fucking Sammy.

This time she reached a fever pitch. Sammy's body quaked and shuddered as he came closer and closer. Eileen herself was having trouble keeping up the tempo as she got closer and closer to orgasming. Finally the rhythm broke and both giver and receiver quaked as the first waves of orgasm hit them. Sammy couldn't hold himself up any longer and fell forward. The sudden drop caused Eileen's strapon to come out of his ass with a wet "Pop!". Eileen herself felt it wash over her as her orgasm faded. But she had one final task.

Eileen loved playing with Sammy and tormenting him after milking. Her most common way was to keep trying to milk him after he had already cum. This time however, Eileen grabbed ahold of the two condoms filled with Sammy's cum. She emptied one into her gloved hand and started smearing it over his ass before fingering a big glob through the entrance. The second she emptied into her other gloved hand.