Rooming with my Slutty Mom Ch. 03

Our Story Thus Far

Bailey Jay Devine signed up for the all-girls dorm his freshman year of college, hoping to experiment with crossdressing away from Ava Devine, his overbearing, oversexualized mom. Unfortunately, Ava decided to go back to school as well and the two ended up being stuck together as roommates. After accidentally getting stuck watching his mom having wild sex with another student, Bailey was blackmailed by Riley, the Junior down the hall, into secret crossdressing, chastity, and continued spying on Ava's prolific sex life. Now Ava is secretly aware of Bailey watching her and increasingly turned on by her experimenting son, while Bailey is haplessly falling for Riley and struggling with an increasing fascination in Ava and her many lovers.

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Finals week went by in a blur after the girls sleepover in Aubrey Hall. Ava never let Bailey know that she'd been awake when he'd felt up her tits and ass in their sleeping bag, and certainly didn't let him know how she'd wished he'd pushed a little bit further, instead of getting spooked with just the tip of a finger up her ass. And neither of them mentioned making out together during the game of Spin the Bottle that Riley had instigated, although both masturbated to the memory more than once in the days that followed before wallowing in a sea of guilt as post-orgasm clarity took hold.

The last day of fall semester after completing his last final, Bailey went to visit Riley's room, nervously twirling his ponytail (Ava and Riley had both suggested he keep wearing his hair like that after his sleepover makeover). As usual he was wearing leggings and a flowy top that Riley insisted was 'totally unisex', and underneath he was wearing the pair of Ava's panties he'd 'borrowed' for the day (a white lace thong with a line of pearls that made Bailey's ass feel delightfully tingly) and a coordinating white lace bralette that Riley had bought for him.

"Hey Bailey, back so soon?" Riley asked as she answered the door. "Don't tell me Ava found another guy to fuck already, it's only been what, two hours? Come in and take your seat and tell me all about it."

"No, that's not it, I was hoping that we could talk before winter break. About... stuff."

"Stuff huh? That sounds ominous. Well I need a shower anyway, come in and tell me all about 'stuff' while I get washed up."

Bailey followed Riley into her bathroom and watched mesmerized as she stripped. Riley was about 5'3" with a thin athletic build and perky B-cup tits with a round little ass to match. She paid no attention to Bailey as she prepared for her shower, even giving him the perfect view of her ass and pussy as she bent from the waist down to the floor while getting undressed. Any other guy would have been on her in a heartbeat, but Riley had systematically broken Bailey to her will over the past semester and she had the key to the chastity cage she'd kept him in for the past two months dangling securely from her anklet. She had as much to fear from him as she did from the Teddy Bear sitting on her bed.

"What, never seen a girl other than your mom naked before?" Riley asked as she stepped into the shower. "Spill, what's on your mind?"

"Well with the semester ending we're not going to see each other for a few weeks," Bailey started as he watched Riley start rubbing suds all over her body. "So I thought that maybe you could take me out of this cage now?"

"Take you out? But you're still gonna be watching your mom get laid during the break, right? God, I bet she's got a whole crew of guys back home that have been missing her all semester and are ready to run a train on her." Riley slid one hand down between her legs and began giving some extra attention there. "If I take you out then you'll be jerking it to your mom the whole time, and that's nasty."

"I won't, I promise!" Bailey protested frantically. "You can't just keep me locked up in this things forever."

Riley stuck her head out from the shower and fixed Bailey in a withering gaze.

"You don't tell me what I can and can't do. How do you think Ava would respond to hearing that her son was dressing up in her panties and getting off to watching her fuck? I promised I'd help you, and that's what I'm doing. Someday maybe you'll be ready to be let out, but for now I saw the way you nearly creamed your shorts kissing Ava at the sleepover. The cage stays on."

"Yes Riley," Bailey gave in with a sigh.

"Good pet. Now, show me your gratitude for my help."

Riley extended one leg out from the shower, warm water and suds running down it onto the mat. Bailey went down to his hands and knees and leaned in, gently kissing the key resting on Riley's ankle, then gagging slightly as she took advantage of the moment to slip first her big toe then half her foot into his mouth.

"There, that outta shut you up while I give you the rest of your instructions for the break. If you do everything I say, then maybe I'll give you a special treat when you get back."

Back at Ava and Bailey's home, Winter Break was slightly chilly. It was as if the two no longer quite knew how to live together without being full roommates. Bailey tried dressing up in the pajama set he'd been given by Riley for the party and asking Ava if she'd like to have a sleepover, but she declined, secretly worried that it would lead down the same path of incestuous lust as before. So, all Bailey could do was follow Riley's instructions and hope for the best. Her first rule was that he had to continue wearing a new pair of Ava's panties every day, but he was worried about what would happen if he were caught in his mom's room, so he improvised and started taking the panties she'd worn the day before from the hamper, then replacing them the next day after he'd borrowed them. Bailey loved the way they smelled of Ava, but he couldn't help but notice other smells as well. Riley's guess about the train of men waiting for Ava's return was spot on, and every pair of panties Bailey borrowed bore the signs of his mother's liaisons from the day before.

Unfortunately, Bailey also couldn't realistically hide in Ava's room to watch her fuck, so he was forced to follow Riley's second rule while listening through the wall separating their bedrooms. Every time Ava got fucked he had to fuck himself with one of the dildos that Riley had sent him home with. They were different sizes, and he was supposed to ask Ava before each date about how well-equipped the man was, then try to match him. At first Ava had been taken aback by Bailey's curiosity, but she tried to rationalize it as him showing an interest in her, and one she got started talking about dick her natural passion took over. So before long she was giving him every juicy detail about the delicious cock she'd be enjoying next. Riley tried to judge what position his mom was in based on the sounds coming through the wall, then matched it, imagining what it must feel like for her to get fucked like that.

That quickly led to Riley's third and final rule for the break. Whenever Bailey came, he had to catch whatever dripped out of his cage in his hand and eat it. Riley said that disposing if the evidence was the best way to not get caught. At first Bailey had been worried that he'd hate it, but after a first few tentative licks he thought it was fine. Honestly, it didn't have a whole lot of flavor, and he wasn't sure why so many girls made a fuss about swallowing it. It had a kinda fun texture even, and Bailey usually played with it in his mouth a bit before finally swallowing it down.

Finally Winter Break ended and Bailey and Ava piled back in Ava's car for the drive to school. As soon as they started driving, it felt like the ice around them thawed. The pair started gossiping about what they thought all the other girls in Aubrey Hall had gotten up to over the break, talked about what classes they were taking in the Spring, and at Bailey's prodding Ava admitted that she was really looking forward to getting back to her stable of college hunks. Once they were settled in Ava declared she was taking a nap and Bailey decided to hop over to Riley's room to claim his reward.

She was waiting for him, and eagerly ushered Bailey into her bathroom, insisting that it was his turn to shower in front of her and that his reward would come after. Eager for the promised reward, he hopped in and started using the body wash Riley handed him, taking care to keep it away from his scalp as instructed. It tingled a bit, but once he got used to it Bailey thought it felt nice. The shock came when he stepped out of the shower and saw that every last bit of hair below his head was gone, washed away down the shower drain.

"Damn, that stuff really works as advertised," Riley said as she traced a hand along Bailey's smooth body. "You should be good for at least a couple weeks, then you'll need to come by for another round."

"You mean you did this on purpose?"

"Yeah, I mean, it's not like you were that hairy before, and you look so much nicer now. Besides, it was the last step to getting your big reward, are you ready to cum without a dildo up your butt? Then get up on my bed on all fours. Now."

Unable to believe he was finally getting out of his cage, Bailey scrambled up and assumed the position, feeling the cool air tingling over his whole body. Apparently losing all his body hair had made him extra sensitive. A thrill raced through him as he felt Riley grip his chastity cage firmly, and he held his breath as he waited for the click of her key being inserted to release him. But instead he was surprised by the feeling of wet, warm pressure starting on his exposed sack and running up between his cheeks. The sensitivity his body had felt was nothing compared to this, and Bailey moaned and dropped his face into the bed, lifting his ass higher in the air as Riley started again from his silky smooth balls, licking up along his sensitive perineum, and finishing with her tongue prodding at his twitching hole. Then she pulled back an inch and blew a stream of cool air along the path her tongue had just taken.

"Riley," Bailey whispered. "I can't... it's too..."

"Shhh..." Riley said as she reached her hands up to start playing with Bailey's erect nipples. "Don't ruin this by talking, just enjoy your reward and give me all of your cum."

Then Riley set about eating Bailey's ass in earnest, digging her face in deep to prod him with her tongue, then sliding down to suck his balls into her mouth, gently scraping them with her teeth. When she felt that Bailey was close, Riley took his whole package into her mouth, biting down slightly and causing him to yelp in pleasure and pain. He nearly passed out when he climaxed, coming to as Riley rolled him over and opened his mouth, letting all of his cum dribble in before sealing it with a kiss.

As the Spring semester started, Ava tried to turn over a new leaf with Bailey. She knew she couldn't give up her regular fucks with all the campus hunks (a woman has needs), but she could at least stop telling Bailey when they'd be coming back to the room so that he didn't have advanced warning of when she'd be having sex. Somehow it didn't seem to matter though, as every time she brought one of her lovers back to the their room, she could hear the quietly familiar sounds of Bailey watching them from under his bed. If she'd known about the tracking app that Riley had installed on her phone it would have made much more sense, but as it was Ava was left wondering if Bailey spent all his time under his bed just waiting for the chance to watch her fuck. And to be honest, although she did her best to avoid the situation, Ava still got off on knowing that her son was secretly watching and did her best to put on a show for him each time. If he was going to go through all the trouble of hiding under the bed and waiting around just to watch her have a little sex, she owed it to him to at least make it worth watching. Though she did wonder where he scurried off to once he thought she wasn't watching afterwards.

For Bailey, meanwhile, the added challenge of needing to track Ava's location to figure out when she was bringing a man back to their room was more than made up for by Riley's new approach to getting the deets from him after. She seemed to really enjoy making him struggle through coming up with coherent words to tell her all about his mom's exploits while her tongue was buried in his ass, and before long she started using a strapon to peg him during "story time" as well. It had been a surprise when she'd first mounted him and forced his legs wide with her knees, but he figured it wasn't really any different than using a dildo on himself, except for the rhythm and power Riley fucked him with was way better than he could manage on his own. At the end of each session when he'd finally given her all the details of what he'd watched Ava do, Riley would slide a hand under him and give Bailey permission to cum. Then as he licked it from her hand she would rub his head with her other hand and tell him what a good job he'd done for her.

A few weeks into the semester after one of their sessions together, Riley went into her closet while Bailey played with the cum he'd lapped from her hand and recovered from yet another mind-blowing milking.

"Hah, swallow your little treat already Bailey," Riley teased as she stepped out holding some clothes. "I got you something, take a look."

Bailey examined the clothes Riley casually tossed on the bed. There was a pink and purple tartan skirt with black lace trim around the bottom and a short white top that tied together in the front. A pair of long white stockings with bright pink bows at the top completed what Bailey instantly recognized as a slutty schoolgirl outfit, just skirting the line between clothes and lingerie. He ran his fingers over it, at once wanting to follow through on his original wish to experiment with dressing and living as a girl and wondering if he could ever wear something so provocative.

"Oh Riley, I don't know. I don't think I can..."

"I'm not asking you to think," Riley cut him off as she approached him. "I'm telling you what to do. Go to your room, get all dressed up in these clothes, and doll yourself up with your mom's slutty makeup."

Riley ran a hand down Bailey's back as she spoke, then stuck her thumb into his ass while cupping his package with the rest of her fingers. Bailey gasped, still sensitive from his milking.

"Do it, and I'll unlock your cage and let you fuck me."

Riley gave Bailey a swat on the ass and he leapt into action, quickly putting back on his normal leggings and top and scooping up the clothes Riley had gotten for him. Ava had left for dinner with her lover after their pre-date fuck, so Bailey knew he had the room to himself and set to work. The schoolgirl outfit was easy enough. He'd never worn anything that slutty before, but he knew his way around girls clothes well enough to wear them with confidence, especially with how he looked with his body hair gone. So fully dressed he pulled up a seat at Ava's makeup station and set to work.

Riley, meanwhile, set to work of her own, pulling out her cell and calling up Ava.

"Hey Ava, sorry to disturb you, I know Bailey said you had a hot date tonight."

"Oh, he talks to you about that? Well what's the matter?"

"I just thought you'd like to know I saw someone strange sneaking into your room on my way out of the dorm, and I'm worried about our little Bailey."

"Oh dear, do you think you could go back and check on him for me?"

But as Ava asked Riley hung up and turned off her phone, and all she heard was the dial tone on the other end.

Ava quickly made her excuses to her date and rushed back to Aubrey Hall, worried sick over her poor little boy. She unlocked the door and entered to see the stranger Riley had warned her about, some little slut in a schoolgirl costume using her makeup to put on what looked like a full bimbo face. But as the girl turned toward the sound of the opening door, Ava saw that it was none other than Bailey.

"Bailey?!? What are you doing with my things? and what are you doing wearing that outfit?"

"Mom? I can explain. I just..."

"You what? Did a group of mean boys steal all your clothes again? You know I've fucked those boys, and none of them knew a thing about taking your clothes."

"No, they didn't. I just wanted to try... something different. Please don't be mad at me."

"Oh, stop your bawling. Your makeup is enough of a mess already, you look like a cheap whore."

Ava pulled Bailey in to a consoling hug.

"You don't need to hide anything from me dear. After all that you've seen... I mean, I've just felt so close to you since we've started rooming together, and I hate to have something like this come between us."

"Really?" Bailey asked with a sniffle as he lifted his head. "You mean you're okay with all of this?"

"I mean, most of it," Ava replied with a laugh. "Your makeup is atrocious dear, we'll have to do something about that."

Bailey sat back in the chair and let Ava wipe away his first attempt and start again with a more practiced hand. As she applied his makeup he held still and listened as she reflected on his situation.

"You know sweetheart, you really have such a beautiful face. I never really noticed before, but with a touch of makeup you really look more like a girl than a boy. And there's the way you've been dressing recently, I know you think those clothes are unisex, but it's time to stop kidding yourself. You've been dressing like a girl and it suits you. Plus there's the whole mess where the university accidentally put you in a girl's dorm. Maybe the universe is trying to tell you something, and maybe you should start listening."

"Telling me what?" Bailey asked, both dreading and hoping for the answer.

"That you're a girl. My girl. My sweet, beautiful, charming little girl. Now look in the mirror and tell me what you see."

Bailey turned and saw a beautiful face staring back at him with green eyes that popped from the smoky eyeshadow arrive them, a cute button nose, and kissable red lips drawing slowly back into a smile.

"Mom! I look... Amazing! Thank you!"

"Oh sweetheart, I'm so glad you like it. I just want to help you be the best you can be."

A thought occurred to Bailey as he turned back to his mom.

"You know Mom, there's something else you could help me with."

"Anything dear."

"Maybe we could practice kissing some more?"

"Oh I don't know about that," Ava said, biting her lip at the thought but unwilling to cross that line again.

"But you said that girls practice kissing together all the time, and you said that I'm your girl, right?"

"Right, I know, but we..."

Ava cut off as Bailey leaned in with his soft red lips slightly parted and his eyes closed. She had just a moment to pull away, but she couldn't muster the will to do so in the split second she had, and so she remained frozen as Bailey closed the gap and pressed his lips into hers in a tender and trembling peck. That small tremble set off an avalanche in Ava's heart as she returned Bailey's kiss with wild passion. While Bailey had initiated the kiss, Ava quickly took full control as she escalated into fully making out, probing into his mouth with her tongue as her hands roamed all over his body. His slutty outfit drove her wild as she bit and pulled on his lower lip while sliding her hands up his short skirt and grabbing his bare ass. Ava could feel the liquid heat building in her core and flowing downwards until her pussy was soaking wet and needy. She knew that if Bailey just figured out what to do with his hands and reciprocated by sliding one up her skirt there'd be no stopping what naturally came next. But just as Ava was about to give in and pull her son's hand in to launch the next stage, she caught herself and pulled away, struggling to catch her breath.