Roommates Ch. 07 - Sleepover

Jaina was scheming. Josie's brother was coming to sleepover for the long weekend. Josie had told her about how he was a virgin. How he had been saving himself for his ex-girlfriend. Only to find out she was cheating on him the whole time. How much it had devastated him, made him give up on dating, and even lose interest in his classes and hobbies. With his grades faltering, their parents decided it might be nice for him to get away for a bit and have some fun. Jaina was determined to make sure he did.

The first thing she did was lead a bare, collared, and leashed Josie through the dorm to Evan's room. She explained that Josie was no longer allowed to wear clothes in their room, so she needed someplace to stay for the weekend while her brother visited as he wasn't ready for that yet. Josie acknowledged being loaned to Evan until Jaina came back, that she was to be his plaything and follow his orders. That until Jaina came back later that weekend with some clothes she was to remain nude except for her collar. Though it was a bit humiliating to be passed around, Josie's nipples were erect and her thighs were slick with her juices so it was obvious that as much as she pretended she got off her submission.

That taken care of, Jaina went downstairs and waited for Jon. When he arrived she arose from her seat and with arms wide enveloped him in a hug. She stepped back as he laughed and asked if she ever wore clothes anymore. Smirking and running her hands down over her completely nude body seductively she asked if that's what he really wanted? As she led him back to her room she took on a more serious note letting him know that his sister had told her all about his recent troubles. That not all women were bad and she was going to give him an amazing weekend to prove it. He flushes, slightly embarrassed and deflects telling her that's not necessary. She ignores that and leads him into her room, shutting the door.

Quickly she leads him over to her bed and kisses him passionately. Her hands run through his hair as her tongue plays with his. Dazed, he allows her to pull off his shirt before she lifts his hands, settling them on her chest. As she kisses him again her hands cover his, encouraging him to grope her boobs. Slowly he massages her tits, playing with her nipples, causing her to softly moan into his mouth and press harder against his hands, further encouraging him.

One of her hands slips down, cupping his groin, finding him erect and straining against his pants. She pulls away from kissing him and looks devilishly in his eyes, noting it is something that needs to be taken care of. She maintains eye contact as she slowly drops to her knees, hands reaching out to remove his shoes and socks, before undoing his belt and fly, her hands sliding inside his boxers to push they and his pants down to his ankles, baring his erection to her eyes. She stares at it hungrily, licking her lips, before helping him step out of his clothes and pushing him back to sit on the bed, spreading his legs. He stares at her with wide eyes as she leans forward, her tongue licking him from base to head, causing his eyes to roll back in pleasure. After several long licks she opens wide and engulfs his member, sliding slowly down until he fills her mouth, her lips kissing the base of his cock. Wrapping one hand around the base to hold him steady, she begins a rhythmic bobbing with her mouth as he leans back and whimpers in pleasure. Suddenly his cock swells and she tightens her lips around him, throat undulating as she swallows the seed he sprays down it.

He falls back fully on the bed, panting as she affectionately runs her tongue over his crown, cleaning him, before sliding it up and down his length to build his erection back up. When he's fully hard again she stands, straddling him, her arms on either side of his head looking deep into his eyes before she lowers her hips and buries his cock inside her. She pauses for a moment as she's bottomed out, grinding on him, and leaning forward to aggressively kiss him before pulling back and focusing as her hips rise and fall, riding him aggressively. Their breathing increases for several minutes before she cries out, her pussy clamping and pulsing on his erection as she cums. Already incredibly sensitive, it only takes a few seconds of this before he tenses and orgasms inside her.

She rolls over and lays on her back beside them as they both pant faintly. She offers him a sultry smile and congratulates him on losing his virginity. He smiles goofily, thanking her, still a bit overwhelmed by it all. She slowly strokes his head until he drifts off to sleep.

He doesn't hear the knock on the door but the murmuring outside and the three women entering and standing over him wakes him up. He jumps slightly and makes a move to cover his groin before Jaina sits beside him and stops him, leaving him exposed. He's not alone though. Jaina is still nude and she introduces a nude and collared Anna as one of her submissives. Anna stands a bit meekly but eyes his groin with obvious interest. Then she introduces a topless and smiling Edna before reprimanding her for wearing clothes in her room as it's not allowed. She reaches out and drags Edna's skirt to the floor, baring her body to his eyes before telling her as punishment she has to clean up Jon before she gets her reward.

Enda kicks the skirt aside and drops to her knees, reaching out to grab his half erect rod and cleaning it with long, enthusiastic licks, leaving it standing at attention. Jaina then tells him that the two other girls had agreed to help her show him a good time. Then she laughs and admits that Anna was ordered, but she doesn't mind does she? Anna bites her lip, trying to look upset, but her thighs rubbing together in heat and nipples poking out betray how much she loves submitting and surrendering total control to Jaina.

Jaina takes Anna's hand, leading her out onto the balcony. The sun is starting to set, but anyone could look up and see her as Jaina positions her leaning over the railing, her tits exposed to the courtyard below, and forcing her to spread her legs. This causes her slick, excited vagina to open up slightly and be presented to Jon. She then tells him that Anna is his to use, but he has to fuck her out here. That Anna loves being used in public where anyone can see her. How it's good for him to experience different types of sex and this will introduce him to public sex and domination. At first he is hesitant but as Anna looks back and begs him to take her he gains confidence. He stands and moves behind her, pressing himself right up against her gushing slit. Her begging increases in intensity, asking him to use her, to show everyone how dominant he is over her. How he has complete control over her body and how it's used.

Grabbing her hips he slides inside and slowly builds up a rhythm with his thrusts. Movement to the side catches his attention. Edna and Jaina are watching them out of the corner of their eyes as they make out passionately, scissoring their crotches together. The intensity of their humping increases in concert with his, and suddenly one of his hands reaches forward, grabbing a handful of Anna's hair and pulling her head back as he thrusts harder inside her. She moans in pleasure at his aggressiveness before tensing, her pussy clamping on him as she cums loudly. This pushes him over the edge as well and he buries himself to the hilt, painting her insides with his seed before leaning forward on her back, panting softly.

Edna remarks on how hot the show was and points out several people watching from nearby balconies and even down in the courtyard. She moves over and pulls him out of Anna before dropping to her knees. Jaina orders Anna over, spreading her legs, and pushes her head down to service her as she watches them. Edna tells him how much she loves having men fuck her tits. She slides his messy cock between them, using her hands to push them together forming a tunnel, before begging him to use them. He places his hands on her shoulders, enjoying the sensation of his overly sensitive cock sliding between her soft tits, as he humps them slowly. He warns her as he gets near and she surprises him by asking him to cum over her tits and face. The thought surprises him so much he tenses and unloads on her, leaving her covered.

She licks him clean then stands and thanks him before leaving to go back to her room, shamelessly strolling bare and marked through the dorm as she basks in enjoying her new kink. Back arched, tits forward, sultry eyes meeting any that look at her totally confident in her sexuality and how she shows it.

Jaina orders Anna to take him in the shower, wash him, and put him to bed after his eventful day. She complies, offering to give him another blowjob but he declines, spent, and they simply cuddle nude as they drift off to sleep.

Jaina decides to go check on Josie. No one responds to her knocks on Evan's door, but it's unlocked so she lets herself in. Following the sounds of sex she walks out on the balcony to be greeted by the sight of Josie being fucked from behind by Evan while his roommate holds her head and fucks her mouth. The two boys continue using her holes for several minutes before emptying themselves inside Josie, pulling out, and ordering her to her knees. Then Evan orders her to lick them both clean before letting her stand. Only then do they notice Jaina, smirking, phone in hand having recorded the whole show to add to her collection of blackmail on Josie. Josie blushes slightly but her smile betrays how much she is enjoying it and she doesn't object to it being captured and kept beyond her control.

Jaina hands Evan a dress, telling him Josie's not to put it on until tomorrow when she meets her brother for breakfast and to spend the day with him. He holds it up in front of him, remarking how short and light it is and that with no undergarments she'd have to be careful to not put on a show. Jaina just remarks that she's lucky to be able to wear anything, so if Josie doesn't like it she can show up wearing just her collar instead.

Jaina tells her about her brother's adventures and how much fun he had. How his explorations of and adventures with multiple females had seemed to increase his confidence. How she was certain that he'd be more open and sex positive now, so her showing a little skin wouldn't bother him. She then starts to leave reminding them they have full use of her submissive until tomorrow. Evan and his roommate grin, before looking at Josie hungrily as she bites her lip. As Jaina is exiting the suite, she can hear her asking how she can serve them.

The next morning she wakes Jon up, slowly stroking him, before sliding her leg over and plunging down on his erection. She bounces up and down, pressing his hands onto her tits, before they both have a small but satisfying orgasm. They shower together before she begrudgingly slips a sundress over her head at his insistence and leads him down to the dining hall to meet Josie. There he genuinely compliments his sister on her outfit and how confident she is wearing something that barely covers her. He also thanks Jaina profusely for helping him get over all his ex put him through and give him confidence to try again.

Before going to spend the day with his sister, he asks what their plans are for spring break. Jaina admits they do have plans, that she'd found an adults only resort where the entire grounds were clothing optional and how much she was looking forward to being completely nude for an entire week and exploring her sexuality wherever she felt like it. As she said this, she looked suggestively at Josie who could only gulp, realizing that it was probably her fate as well.