Hungover Roommates

Cleo woke up to the sound of her phone buzzing. Text message.

"Fuck," she muttered. Swallowed once. Her mouth was dry, head pounding. All the classic signs of a hangover that was going to last all day. She rolled over and checked her phone. It was from her roommate, Joanna.

J: U up?

Cleo sighed and started typing.

C: Yeah. Super hungover

J: Me too. Way too many shots last night...

Cleo waited as the typing icon started and stopped while Joanna worked on the next message. Cleo was pretty sure she already knew what it was going to say.

J: Wanna come into my room for a bit? Maybe bring some of the toys... :)

Cleo smiled. It was Saturday morning and she had nothing to do. Why not?

C: Sure. Gimme a sec.

Cleo got out of bed and went to the bathroom. Splashed some water on her face and brushed her teeth. She was wearing some boy shorts for underwear and a black t-shirt. She'd at least had the decency to take off her bra before passing out. Cleo rinsed her mouth and then dug around in the cabinet beneath her sink, which was where she kept her sex toys. She had a few vibrators, a strap-on, two butt plugs, and some light bondage stuff. Cleo thought it over and went with a small bullet for herself and the big vibrating dildo for Joanna. She liked that one when she was hungover.

Cleo and Joanna had been roommates for almost a year, and they'd been fooling around with each other for the last few months. They usually did it on hungover mornings like this when neither of them had gotten laid. It was an easy excuse to get some pleasure from the closest possible source. Afterwards, they carried on like regular roommates, drinking coffee and bullshitting about boys. Cleo had come to terms with her bisexuality a long time ago, but she got the feeling Joanna wasn't quite as open. Whatever. It was fun, and Cleo made sure to avoid setting expectations for whatever it was they were doing with each other.

She padded down the hallway with the toys in her hands. She was already getting a little wet thinking about what was going to happen next. Joanna might not have her sexual-identity totally figured out, but the girl was a good fuck. No denying that.

Cleo knocked on Jo's door twice and then stepped inside. Her curtains were thin so the room had plenty of morning light beaming through the window. There was a short red dress and a pair of stilettos in a pile on the floor. Jo was lying in bed with the sheet raised over her head. She slowly pulled it off her face and peeked around the fabric.

Cleo held up the big vibrator so Jo could see it. "Help has arrived," she said, smiling.

"Thank god," Jo said, sitting up in the bed. The sheets dropped to reveal Jo's breasts, which were on the larger side — double dees at least. Despite their size, Jo's aureolas were small and pale, which Cleo liked. It was unexpected. They had really different tits between the two of them, Cleo wore an A-cup bra and had big, dark aureolas and permanently hard nipples. They were poking through her undershirt right now.

Cleo climbed onto the bed and sat across from Jo. "So, how bad is it?" she asked.

Jo leaned back on her headboard and put a hand on her forehead. "I feel like death. We went to the Rec Room last night and I got totally out of control. I think I cried at one point. So embarrassing. What'd you do?"

Cleo and Jo had totally different friend groups, which was one of the reasons they could do stuff like this without things getting awkward.

"Just went down to O'Connel's Pub. Total bro-fest."

"Find any hot guys"

"Ha, yeah I gave my number to one kinda cute guy. He was a total moron though. I doubt he'll ever text."

"You never know," Jo said. "I'm kinda glad you didn't go home with anyone, though. That way we can play."

A smile crept across her face as she slid her blanket further down the bed. Jo had slept totally naked. She had a nice body—the idiot bro from last night would have probably called her "thick" or something obnoxious like that—but Cleo thought she was beautiful. And Jo always carried herself with a confidence that turned Cleo on. Case in point, Jo spread her legs without a hint of self-consciousness. Her pussy was fully shaved, and she had "innie" labia that opened a little as she parted her legs. Cleo could see a little wetness between her lips already.

"Such a pretty pussy," Cleo whispered.

"I bet you say that to all the girls," Jo said, running a hand over herself. "But thanks."

Cleo smiled and started massaging Jo's left calf, slowly rising up her thigh. She grazed her pussy when she switch to her right leg and worked her way down. "Here," she said. "I have an idea. We'll have a little spa-session to fix that hangover of yours. But first.."

Cleo picked up the big vibrator and turned it onto a slow pulse setting. She spit on it for a little lube, and then gently pressed it against Jo's pussy and started rubbing it around her clit and labia.

"Mmmmm," Jo murmured. "That's good. You can push it in, my pussy got wet as soon as I heard your footsteps coming down the hall."

Cleo pressed a little harder and the vibrator slipped inside with a little slurping noise that made Cleo's clit tingle. She moved the vibrator in and out a few times, getting turned on when she saw the sides of the vibrator turn wet. "Ok take a breath," Cleo said, then she pushed it all the way inside Jo's pussy. The vibrator was about eight-inches and really thick at the base, so it stretched her out. Cleo left it in there.

"Oooh, fuck," Jo said.

"You like?"

"Mmmmhmmm."

"Ok, don't move, just relax and let it stay there. I'm gonna rub your feet while you get off."

"Ha, spa treatment indeed."

Cleo took some moisturizer from Jo's bedside table and squirted it in her hands. She started rubbing Jo's feet slowly, running her thumbs along her heels and soles.

"Yeah, just like that. So good." Joanna closed her eyes and took some deep breaths. "So fucking good," she said again.

Cleo smiled and kept rubbing. When she was hungover, she tended to get depressed and horny at the same time. She'd learned a couple years ago that it was the perfect mixture of emotions to do intense dom/sub play. She'd gotten super into it with one of her ex's from several years ago and it escalated until he started tying her up in the shower and pissing on her tits while she masturbated on her knees. Thinking about that again got her pussy soaking wet, but she wasn't sure Joanna would go for something that intense. At least, not right away. So Cleo decided to ease Joanna into the idea.

"Am I a good servant for you, Jo?" she asked playfully.

Joanna opened her eyes and raised an eyebrow at her. Cleo gave a little nod to show she wanted Joanna to go along with it.

"Yeah, sure, you're a good little servant. Is that what you want to be?"

"Definitely," Cleo said firmly, voice getting a little thick in the back of her throat, which always happened when she was getting humiliated a little. "You can make me your little serving slut, if you want."

"Oh really?"

"Mmmhmm," Cleo said. "It turns me on a lot. You can be kinda mean to me, if you want."

"Ok, let's see," Jo said, obviously distracted by the eight-inch dildo vibrating inside her pussy. "First of all, servants shouldn't have any clothes on. Strip for me."

"Yes, Joanna." Cleo backed up off the bed, pulling away the covers so she still had a good view of Joanna, who was basically spread eagle now and massaging her own breasts. Cleo could see pussy cream dripping down the bottom of the vibrator and sticking to the sheets.

Cleo took her shirt of quickly, then slowly removed her boy shorts and kicked them away. She had thick, black pubic hair that she hadn't shaved in a while. She liked the look on random guy's faces when they realized they'd have to deal with a full bush if they wanted her pussy. Standing naked in front of Jo as she looked her up and down turned Cleo on in a powerful way.

"Is there anything you'd like to see me do to myself, Joanna?" Cleo asked.

"There is," Joanna said. Cleo could tell she was starting to get into it. Probably surprised by how much she liked ordering another girl around. "I want to see you pull on those little tits of yours."

"Of course." Cleo slid her hands up her body and then pinched her nipples between thumb and forefinger. Then she slowly pulled them away from her chest, which sent little shocks of pleasure through her body. She stopped when she'd pulled them about two inches.

Joanna looked at her with glazed eyes. Her skin was starting to flush around her neck and between her breasts. "I think you can do better than that, Serving Girl."

Cleo pulled harder, wincing a little.

"Harder," Joanna said with a hoarse voice. "Pull on those little mosquito bite tits for me."

Cleo pulled as hard as she could. It hurt but it also turned her on so much that a trickle of pussy juice slid down the inside of her left thigh. Joanna saw it and started rubbing her clit a little faster. "Oh my god that's so hot. You are such a fucking slut to get turned on like that."

"Does it please you?" Cleo asked, short of breath. Her clit was pounding.

"It's gonna make me fucking cum, Servant."

Cleo pulled even harder, half-afraid she was going to rip her own nipples off but not really carrying. Joanna's legs started to shake and a few seconds later she closed her eyes, arched her back, and started moaning. "Ooooooooh fuck. Fuck. Fuck. Fuck."

Joanna came so hard that the vibrator twitched up and down inside of her for almost ten seconds. It was one of the hottest things Cleo had ever seen. When Jo was done, she swallowed and opened her eyes. "God that was so good. I don't know why that turned me on so much, but ordering you around is super hot."

Cleo let go of her nipples and let her hands rest at her sides. Her nipples were burning-sore and sticking out so far they actually drooped towards the floor a little. It wasn't exactly hot to look at, but it was so demeaning that it almost made Cleo cum without touching herself. "You don't have to stop," she said, locking eyes on Joanna. "You can ask me to do anything you want, literally anything, and I'll do it. I'm so fucking horny now."

"Seriously?"

Cleo nodded. Joanna smiled deviously. "Ok, I'm gonna test the truth of that. Get back on the bed and get on your knees in front of me.

Cleo obeyed, situating herself so that she was sort of straddling Jo's left thigh.

"Take the vibrator out of me," Joanna ordered.

Cleo smiled and grabbed the back of the vibrator, then slowly slid it out. It made a nasty slurping noise and a bunch of pussy juice slid out behind it.

"Now deep throat it," Joanna said. "I want to see you gag on it."

Without a word, Cleo started blowing the vibrator. Jo's pussy was all over it, creamy and wonderful. Cleo moaned and put two fingers inside her own pussy. She started cumming almost immediately in long slow waves, and moaned as her orgasm flowed through her body.

"I didn't say moan on it, serving girl," Joanna said. "I told you to gag on it."

Cleo had a pretty tight gag reflex, so she started choking as soon as the vibrator was more than five inches down her throat. But once she started choking, Joanna started rubbing her own pussy and laughing at her, which made Cleo start cumming again as she choked. She deep-throated the vibrator until she couldn't take it anymore without puking, and pulled it out of her mouth. A long string of spit slid off the vibrator and stuck to her chest.

Cleo took a few deep breaths then looked at Joanna. "What else do you want to see me do with the vibrator?" she asked.

Joanna chewed her lip for a moment.

"I want you to stick it up your own ass."

Cleo hesitated. She'd had plenty of anal sex in her day, but never with something quite this big.

"Right now, slut. You said you'd do anything. I want to cum again watching you push that big cock up your tight little dirtbox"

Cleo felt that familiar thickness in the back of her throat that she couldn't get from anything else besides kinky sex like this. It had been a long time since someone had really dominated her, too. She wasn't going to pussy out now.

"Okay, Joanna," Cleo said, faking a meek little voice and adjusting the vibrator in her hand. "If that's what you want to see, I'll do it."

Joanna picked up the bullet vibrator from the bed and pressed it against her clit. Turned it on. "I'm waiting," she said.

Cleo scooped up some of the spit that had gotten on her tits and rubbed it along the shaft of the vibrator. Then she let a long string of spit drip out of her mouth for good measure. Cleo was more turned on than she'd been in months, but she knew this was really going to hurt.

Without another word, she twisted around and pressed the tip of the vibrator against her ass, making sure to hold it from behind to Joanna could see it clearly. She did her best to relax her muscles, took one long breath in, and then exhaled at the same time she pushed the vibrator up her ass. She got it about halfway inside before the pain caught up with her.

"Ah, fuck," she muttered. The last guy who'd fucked her in the ass had been an asian guy with a four-inch cock. This was about a hundred times more painful.

Joanna smiled with glee. "I can't believe you did it! That is so fucking dirty! How does it feel serving girl?"

Cleo smiled. "It feels amazing. Do you like seeing my ass stretched out like this?"

"Mmmhmm," Joanna mumbled with her eyes fixed on Cleo's ass. She looked like she was going to cum again pretty soon. "But I don't think you're finished yet."

Cleo smiled. The pain was subsiding and it was actually starting to feel really good. Anal play had a tendency to make her squirt, too, which she had never done in front of someone before. "Do you want me to go the rest of the way?" she asked.

"Yes. Turn it on first, as fast as it goes, then shove it all the way up that slutty ass."

Cleo pushed the vibrator on and cycled through the settings until she reached the fastest one. Almost immediately, she felt shots of pleasure banging around from her g-spot to her clit and back again.

"That's it," Joanna moaned.

Cleo didn't need anymore encouragement. She took one more breath and then pushed the vibrator all the way into her ass. She didn't care if it got stuck in there, she didn't care if she had to go to the hospital after this. Her mistress had given her an order and she followed it without question. It was that simple.

"Holy fuck," Cleo gasped. She'd never felt anything so intense before. Without thinking she started rubbing her clit furiously. "Holy fuck holy fuck!"

"That's it!" Joanna screamed. "I knew you'd like it you fucking whore!"

"Am I a good little serving slut?" Cleo asked through clenched teeth.

"So fucking good!"

"Can I cum for you, Joanna? Please let me cum for you. I'm gonna fucking squirt everywhere!"

"Do it, yes fucking do it I wanna watch it!"

All the pleasure and vibration in Cleo's pussy tightened up, she felt the unbelievable urge to piss, and then she started cumming in huge waves. She squirted all over Joanna's leg, pussy juice splashing up along her tits and all over her bedsheets.

"That's it!" Joanna screamed. "Squirt all over me you disgusting little cunt!"

Cleo didn't know how long it went on for, but when she was done, Joanna and the sheet beneath her were totally drenched. Cleo's fingers were shaking and her pussy was swollen and aching.

"Holy shit, Cleo, that was the hottest thing I've ever seen. I came like six times watching you." Joanna was breathless.

Cleo thumb the vibrator off—the button was just barely poking out of her ass. But she didn't take it out. There was one last thing she wanted to do.

"Since I did all of that for you, will you do one thing for me, Joanna? It's...pretty out there."

"More out there than ramming an eight-inch vibrator up your ass while I masturbate?"

"I want you to piss on me," Cleo said. "I want to kneel in front of you and have you piss all over my tits."

Joanna hesitated. "You sure?"

"Positive."

Joanna chewed her lip again and lightly fingered her clit. "Fuck it," she said. "Kneel on the floor for me, slut."

Cleo did as she was told. Moving around with the vibrator in her ass felt so good, she never wanted to take it out. Joanna got off the bed and stretched her neck and hands a little. Then she stepped in front of Cleo so that Cleo's face was lined up with the top of her pussy. When Cleo looked up she could see Joanna's fierce eyes staring at her from between her big tits.

"You're disgusting, you know that, Cleo?"

"I know."

"I can't believe you'd ask for something so gross. It's pathetic."

"I know it is," Cleo said, her clit throbbing. She was so humiliated and turned on at the same time she didn't know what to do. She could barely breathe. "I know I'm disgusting but I need it. I want to feel it trickling down my body. I want you to laugh at me while you do it."

Joanna grabbed the back of Cleo's head and pulled her hair so that her chin was facing the ceiling.

"Close your eyes, slut," Joanna whispered.

Cleo obeyed. For a moment, nothing happened. Then she felt a hot splash of liquid hit her in the throat. Then another. And then finally a steady stream of Joanna's piss splattered her neck and tits. The smell and warmth overwhelmed Cleo, who started fingering herself right away. Within a few seconds she was cumming and moaning and telling Joanna she never wanted it to stop. And for a while, it seemed like it never would. For a few precious seconds, Cleo forgot about her hangover, her shitty job, her silly dreams, and even herself. There was just the warm, disgusting, wonderful feeling of another girl pissing all over her.

It was a strange place to find transcendence, but Cleo didn't care. It was fucking amazing.

When Joanna finished, there was just the sound of her breathing and the tap-tap of piss dripping off Cleo's body. She looked up at Joanna.

"I want to shower with you," Joanna said. "I want to take a three hour nap in your bed. And then I want to do that again."

Cleo smiled. "I live to serve."