Rooming with my Slutty Mom Ch. 01

Having hot mom sucks, and Bailey knew that better then most. He loved her, and she was all the family he had since his dad had bounced long before he'd been born (all Bailey had to remember him by was his middle name 'Jay' and his mom's story that he'd been named after the drink he'd been conceived to), but that didn't make being her son any easier. When he was younger it wasn't too bad. Sure, sometimes one of his friends would suddenly ghost him because their mom thought their dad was being a little too friendly with his mom, but at least there was a consistent male figure in his life. Well, more accurately a consistent series of male figures. Women like Ava Devine didn't stay single for long.

She had a bubbly, outgoing personality and an electrifying smile with soft brown eyes, waves of rich, slightly curly, auburn hair, and dusky skin that gave her a slight exotic vibe. But what really brought the guys around was her figure. At 5'4" and a trim 135 lbs, Ava packed a surprisingly curvy 34G-24-36 build onto her tiny frame. By the summer after graduating High School when Bailey was 18, he had learned exactly what that made her. A certifiable MILF.

That was about the time that all his male friends started getting really weird. They always wanted to come over and hang at his house, but honestly didn't seem all that interested in doing anything with him. Instead, they made excuses to be anywhere they could see Ava, openly ogling her as she tanned in the back by the pool in her bikini, or when she came in sweaty wearing form-fitting yoga pants and a sports bra after a jog. All the perving on his mom made Bailey feel awkward, and he quickly found himself spending more and more time hanging with girls. He'd never been particularly masculine, standing a bit shorter than the other boys his age with a slight frame and narrow waist that made it seem as if most of his weight was in his cute bubble butt. Combined with his beautiful almond-shaped green-blue eyes and lustrous dark brown hair that he preferred to keep long, most of his friends parents actually thought he was a girl until he corrected them.

Once Bailey figured out why so many men were into his mom, and just what was happening when they 'wrestled in mommy's bedroom', he tried his best to be anywhere else. Usually that meant crashing with his girlfriends for sleepovers. At first some of their parents had been a little leery of letting an 18 year old boy spend the night, but in general they quickly came to the conclusion that their daughters were honestly probably safer with him they they were on their own. For all of his mom's reputation around town, Bailey was known for being sweet and a little shy.

All that meant that although they'd once been close, Ava and Bailey gradually drifted apart, until finally as Bailey was getting ready to leave for college after the summer he turned eighteen the thing he was most excited for was finally getting out of his mother's shadow and living his own life. And the second most exciting thing...

Well, Bailey had always been curious, trying on his mother's clothes when she wasn't around, enjoying their soft touch and the euphoric swishy swishy of twirling in a skirt. During his sleepovers with his girlfriends they'd always been painting each other's nails, or styling each other's hair, or trying on outfits and modeling them for each other. At first he'd just watched, but they were always eager to dress him up too and really give their makeover skills a challenge, and before long he spent most of his time at friends' houses in 'girl-mode' before changing back to his drab boys clothes when he headed home. Ava was just too much, and he wasn't ready to come out to her about his curiosity, but college was the perfect opportunity for Bailey to really see how the other half lived. He signed up for a girl's dorm, thankful that his name was androgynous enough to pass, and spent the summer secretly amassing a new wardrobe of girls clothes, dreaming of exploring new horizons on his own.

Bailey and Ava rode together in awkward silence down the highway. Ava had insisted on dropping 'her little boy' off at college, and was cheerfully asking him all sorts of questions about what his plans were. Bailey kept his answers short as possible, eager to finally be on his way. When they got to campus, he tried to grab his bags and run, but Ava popped out of the parked car and started waving to the upperclassmen who were waiting around to help unload. Bailey felt all the nightmares of growing up with the town MILF return as Ava flirted with them, asking if big, strong men like them would be able to help with their bags while touching each of them with oohs and aahs.

Ava wanted to come along to see Bailey setup in his dorm room, but he insisted that they say goodbye there. Ava pouted a bit, then relented and pulled Bailey in for a tight hug. In spite of the distance that had grown between them there was something immediately relaxing in being hugged by Ava. Bailey stood maybe an inch taller than her now, but with her stiletto heels Ava still had a few inches on him, and she wrapped one hand around the back of his head, caressing his long dark hair as she pushed his cheek down until it rested on her chest. The expanse of exposed skin on the top of her large breasts was soft and warm from being kissed by the afternoon sun. Bailey melted a bit, wondering for a second how he'd let things get so weird between them. Then he heard the guys holding his bags catcalling, asking when they got their hug and making motorboating noises. He stepped away from his mom, ready to finally start a new chapter all on his own.

The upperclassmen helping Bailey gave him an odd look when he told them he was assigned to Aubrey Hall.

"You know that dorms for girls, right bro?"

"Yeah, I do," Bailey shot back, pitching his voice high. "Now are you guys going to take me there or not?"

They looked him up and down for a moment, clearly not quite sure what to make of him. Bailey had worn his most androgynous clothes for the trip, and had hoped for the chance to change before meeting anyone on campus.

"Lots of hot chicks in Audrey, maybe some of them can rub off on you."

Bailey sighed and tried to take it in stride, following them until they finally reached his new dorm. He rushed through the check-in process as fast as he could manage, trying to keep his head down and make as little impression as possible on all the girls swirling around him. He wanted the chance to be one of them. To really be one of them, not just the token guy at the sleepover that the girls thought it was funny to dress up. He didn't even know if it was possible, but he didn't want to mess it up on his first day. Fortunately, nobody took much notice of him, and before long Bailey was carrying his bags into Room 265 in Audrey Hall, his new home.

Not wanting to raise any further questions, Bailey quickly unpacked and changed into new clothes, discarding his saggy jeans and boxers and replacing them with a plaid skirt and white cotton panties with a cute little pink bow in the back. Then he took off his shirt and put on the training bra with gel forms he'd saved up for. He'd tried on panties and bras at the sleepovers a few times to fit in, but this was the first time he had the proper padding to give himself just a bit of a bust. He quickly pulled back on a new tee, this one much tighter through the body, and admired the way it hugged the new curves on his chest. Finally he setup shop in front of the bathroom mirror and began doing his makeup. He had plenty of practice at doing it for his girlfriends, and he'd been on the receiving end of more than a few makeovers, but this was the first time putting on his own face, choosing just how he wanted to look. He was just putting on the finishing touches when he heard a key turn in the lock and the door open. Bailey turned with a smile, eager to meet his new roomie.

"Hey roomie, nice to meet you, I'm sure we're going to be the best of friends!"

Bailey couldn't believe his ears. Then he couldn't believe his eyes. It was Ava! What was his mother doing here in his room, and how on earth had she found him? It was probably those dumb meatheads she'd been flirting with.

"Mom, what the hell are you doing here?"

"Mom?" Ava asked, looking confused before beginning to inspect her son more closely. "Wait, Bailey? Is that you? You look so pretty! What happened to you, what happened to your clothes?"

"I..." Bailey scrambled to think of a plausible lie. "Those guys you were flirting with stole all my stuff, some of the girls here helped me out by giving me some of theirs."

"But honey, why are you in a girls dorm in the first place? Was there some kind of mistake?"

"Yes, there must have been. But how did you find me here, and why are you here at all?"

Ava gestured sheepishly to her own suitcases to either side of her.

"Well you know I never finished my degree after you were born, and I thought that now would be the perfect time to jump back in. I thought that we might even bump into each other on campus or share a class together. I didn't think we'd be roommates! How wonderful!"

Bailey paled. After all those years living in Ava's shadow now she finally had the chance to live on his own and experiment a little, but some cruel twist of karmic fate had set them up as roomies. He took his mom's hand and marched with her to the administrative building. It was a total zoo, and when they finally got to see a housing coordinator she struggled to answer their questions. Bailey's question of how they'd been assigned to room together seemed to be something to do with the system assuming they were sisters due to sharing the same last name and home address. Ava's questions of why her son was placed in a girl's dorm caused even more puzzlement, with the admin eventually concluding it must have been a clerical error due to Bailey's androgynous first name while eying his clearly feminine look. The only firm response they got was to their question as to whether anything could be done about it.

"Absolutely not. All housing assignments are final for the semester, you'll just have to make due. Thankfully since you're mother and son it won't be a problem for you to room together, and we'll just let the rest of the girls in the dorm know about Bailey's situation, and ask them to extend him every courtesy while he's a guest in Aubrey Hall. Just do your best to fit in Bailey, and I'm sure you'll have a marvelous first semester."

Bailey had to be scraped up from his chair by Ava as she took him back to their dorm room and began making plans for their semester together. Less than an hour in his new life had imploded.

Back in Aubrey Hall, Bailey quickly tossed his stash of girl clothes and accessories, still unwilling to open up to his mom about that side of him. After a trip to the thrift store he managed to cobble together enough clothes to make it between laundry days. After that brief glorious moment in the mirror before Ava had come crashing into their room, it almost hurt to go back to drab, boring boy clothes. Fortunately, the girls in Audrey Hall mostly took well to the news if their lone male resident, treating him like their collective little brother and making him into something of a dorm mascot. Any concerns they had about a boy living in their dorm quickly evaporated when they saw him, and were entirely forgotten when they learned he would be chaperoned in the dorm by his mother.

And how they all loved his mother. Ava quickly became the unofficial dorm mom. All the girls went to her for fashion advice and for tips on how to handle boys. Bailey was forced to listen and blush as Ava coached girls on how to make sure guys got just the right view down their cleavage or up their skirts, and how to 'accidentally' rub up against the boys they liked, and even tips on how to give the best blowjob their boyfriends would ever get. The girls always told Bailey how lucky he was to have the coolest mom ever, but he just wanted to run and hide.

But if Ava was popular with the girls in the dorm, she was an absolute rockstar with the boys on campus. Word of the hot new MILF freshman in Aubrey Hall spread like wildfire, and Ava and Bailey's room was soon inundated with guys stopping by to say hi and ask if there was anything they could do to welcome them to campus. Of course, they showed no actual interest in Bailey, but ate up Ava's constant flirtations with a spoon. He them throw themselves at Ava and saw how she teased them with little glimpses just like she'd taught the girls in the dorm, keeping them interested and easy to control. But it clearly wasn't just a one way street. Bailey could tell that his mom was loving all the young male attention, and he quickly learned to make himself scarce when she made up a reason for him to leave the room. He didn't want to know what she was doing with half the male student body in their room, though he'd overheard enough growing up with her to have a decent guess.

After the first couple weeks, Bailey got a little more adventurous with his clothing, still not going full girl-mode, but definitely crossing into the feminine side of androgynous with some basic leggings and tops with more flattering cuts that accentuated his waist and hips. He hoped it wouldn't be enough for Ava to notice, but of course she did, she loved fashion almost as much as she loved the attention of young studs.

"Bailey, that outfit looks so cute on you, I just love the way it makes your little tush pop." Bailey tried vainly to brush away Ava's hands as she gave his backside a little squeeze. Even after all these years he hadn't gotten used to how handsy his mom was and her total lack of personal boundaries.

"Ummm... Thanks Mom, just thought I'd try something a little different."

"Oh good, I was wondering if some of those bigger boys were teasing you again by stealing your clothes. You know I can always talk to them for you, they seem to like me."

"No, it's fine, really. I just thought maybe now that I'm in college I could try some new things."

"Well you look lovely. Did you pick those clothes out all by yourself?"

"No, Riley from down the hall helped me," Bailey admitted shyly.

"Well I'll have to thank her later for making my sweet little boy look so cute."

Bailey wasn't sure just how much thanks Riley would need. She was a Junior with sparkling green eyes and brown hair with bangs, and she was a petite 5'3", but there was something subtly forceful about her that made Bailey feel weak in the knees. She'd spotted Bailey in the halls when he and Ava had gone to the administrative office to try to sort out their room situation, then had seen him later on presenting as a boy. She'd cornered him at a dorm social and asked about the crossdressing incident she'd observed. He tried to tell her the same story he'd told Ava, but she clearly didn't believe it.

After that, Riley had taken a definite interest in Bailey. She had actually been the one to buy him his new clothes, insisting that he would be so much more comfortable in them, and that the girls would really like his new look. She forced him to try them on right in front of her, and Bailey thought that he caught her biting her lip as she watched. But she was right, Bailey did feel more comfortable in them, and if Ava didn't mind, then he supposed he could experiment just a little. Maybe it would even be enough to get Riley interested in him as more than a project to dress up. Bailey had experienced plenty of being the dress up doll for girls at sleepovers growing up, but he wanted something more. As intimidating as Riley was, the thought of her liking Bailey's new look was enough to power through the odd stares he got at times on campus.

After a week of wearing leggings and tops that Riley insisted were totally unisex, Bailey's cravings for more bubbled over. He wanted the swishing feeling of a skirt around his legs and the soft touch of panties against his skin. His all too brief moment of freedom had been ruined when Ava had come crashing through the door, so he decided it was only fair that she be the solution to his current needs. He started raiding his mom's panty drawer.

Bailey buried her face in piles of sweetly perfumed satin and lace, trying to ignore the fact that all of them belonged to his own mother. Finally he forced himself to choose a single pair and stole them to wear for the day. Then the next day he slipped them into the laundry basket and took another. Then another. Then just stealing her panties wasn't enough. Bailey knew Ava's class schedule, so he waited until she left for her morning history class, then raised her closet.

He started with a matching lavender bra and panty set, checking himself out in the mirror. His ass looked amazing in the lacy thong, but the bra looked ridiculous on him with the massive G-cups sticking way out from his chest. Bailey grabbed fistfuls of Ava's panties and stuffed them into the cups, filling them out. Then he looked through the rest of her clothes until he found a cute little sundress that made him feel giddy inside. Bailey tried to block out his memories of Ava wearing that dress while flirting with his classmates that she'd gotten to more their lawn for free last summer. And he especially tried to block out the memory of finding the same dress on the living room floor later that afternoon while loud sounds echoed from the master suite down the hall.

For all his past memories of the dress, today it was perfect. As Bailey took in his reflection, he felt himself getting hard in his mom's panties. Masturbation was another activity that she had severely curtailed by becoming his roommate, and the euphoria Bailey was feeling had him ready to blow. He checked the time, still half and hour until Ava would be back from class, or longer if she stayed behind to flirt with the professor again. He pulled out his laptop, browsed to some porn, lifted up the front of his dress, and started jerking himself off. Within a minute Bailey felt he was ready to blow, but he didn't want it to be over so quickly, so he brought himself to the edge, then stopped stroking, reveling in the feel of the thong rubbing between his ass. Then he started again, building up to the edge, then backing off while breathing deeply, savoring the scent of Ava's perfume wafting up from his stuffed bra.

Bailey checked the clock again, still fifteen minutes until the earliest Ava might be back. It was time for the big finish. He began stroking hard, ready to finally let loose. But just as he was about to finish, Bailey heard the unmistakeable sound of a key in the door. He slammed his laptop shut and stuffed his crying dick back down into his panties, frantically looking around the room for a place to hide. Just as the door cracked open Bailey took the only available option, diving under his bed. He fought to calm his breathing as he heard Ava enter, giggling with a companion.

"Well it looks like my roommate isn't here, so it's just the two of us. All alone."

"You know I've got a girlfriend, right Mrs. Devine?" Bailey heard a male voice answer back.

"Call me Ava. And I've heard all about your girlfriend. The other boys were telling me that you think she gives the best head on campus?"

"Well yeah Mrs. Devine, I mean Ava. She's really good, and she's the best I've ever had. And she's my girlfriend."

Bailey could see two sets of feet standing inches away from his face. He wanted to run, but knew that his only hope was to hide here and hope they didn't notice him.

"I think that's your problem. You've never been with a woman before. Here, let me show you what you've been missing."

Bailey heard the guy's startled exclamation as Ava dropped to her knees, deftly undoing his belt and zipper on the way down. Her never had a chance, as before he could even think of an answer his cock had been sucked deep into Ava's throat. The sounds reaching Bailey under his bed were primal and inescapable. Ava's blowjob was sloppy and wet as she gagged herself on the cock she was eagerly devouring. And her helpless prey was moaning loudly as she nearly sucked the soul from his body. All of which made Bailey painfully aware of what his mom had interrupted when she came back early from class.