Brian and Bree, and Mitch Ch. 01

Nis 23, 2024 // By:analsex // No Comment

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Author Note – This is just part one. If the story gets attention I’d love to continue it. I LOVE feedback and I LOVE suggestions. I hope you all enjoy!


“Hey, so I’m going to be at Sarah’s all night,” Mitch said as he was walking out of the door, “Brian, it’s Friday night. Get out and do something this time.”

“Man, I had class all day, it’s been a long week. I think I’m just going to call it an early night,” Brian replied as he sat down on the couch with a beer, “Besides, I just know my boss is going to call me to go into work tomorrow. Just go and sex Sarah, I know she’s been holding out on you until finals were over.”

“Alright man,” Mitch said chuckling, “Don’t get into any trouble, I’ll see you tomorrow.” Mitch shut the door and locked the deadbolt from the outside out of habit. Mitch and Brian were roommates in the dorms at college, and have been roommates in this place for the past two years. Mitch and Sarah have been dating for over a year, Brian liked that he got the apartment to himself most of the time. Brian got up and went over the window, taking another sip of beer and looking out the blinds as Mitch drove off.

“They’ll probably get married one day,” Brian mused to himself as he finished his beer and went upstairs to his room. He didn’t bother to shut the door any more when Mitch was gone, half of the time he said he was going to be gone for the night he was gone for two or three, Brian figured it was all the marathon sex his 23 year old roommate and his 21 year old girlfriend were having. Brian went to his nightstand and pulled a key out, then to his closet and his locking wardrobe. Living in a college town Mitch and Brian threw parties often at their apartment, and they both decided that having a locking cabinet in their own rooms was a good idea, it definitely worked to Brian’s advantage. Brian is about 5’9 and slender, only weighing in at about 135 pounds. He kept his curly dark brown hair a bit longer than shoulder length and in a pony tail, he joked often with his guy friends that chicks loved to play with it, which usually kept him out of the butt of jokes. He took his hair out of the pony tail and shook it out, letting his curls fall to his shoulders. Admiring himself in the mirror, he brushes his hair, teasing the layers he has cut into it out into a nice flowing mane. If someone were to look at him from behind, they would definitely see the hair of a young girl.

He turned the key in the lock of his wardrobe and it opened with a click. This was his secret, no one knew it except for him. His wardrobe is full of girl’s clothes, make up, shoes, and make up. He looked over the collection that he had amassed since he was 18, almost six years now since he left home. When he was a teenager he always admired the girls in his school, especially the way they dressed, and always gravitated towards them. He had always had more female acquaintances than male friends, the only notable exception was Mitch, his first college roommate.

He set his beer down on his nightstand and decided what he would wear for the night. He pulled out a pair of pink and white cotton bikini panties with a cute floral pattern and laid them out on the bed. Next, he pulled out a 34C sized pink bra with white polka dots on it and laid that next to the panties. He then laid out a pair of black cropped tights, a short black skirt with a nice lace trim, and finally a pink sleeveless blouse. He looked over the items and then pulled the lowest drawer of the wardrobe open and revealed his favorite part of his collection, a sizable assortment of shoes from high heeled pumps and sandals to flats, sneakers, and flip flops that would make any girl his age envious. He pulled out a modest pair of pink and black plaid flats and laid them next to the bed. Looking over his outfit, he smiled and nodded to himself as he finished his beer, he loved the next part, when he gets to become Bree.

Bree then put on some dance music and hopped in her shower. She and Mitch were lucky they found an apartment that has two master suites, they each had their own bathroom. Bree had all assortment of feminine products in her shower, if Mitch ever asked Brian he’d again just say, “The girls love that stuff man.” She soaped herself up with a nice gardenia scented bar of soap into a nice rich lather, and then shaved every inch of her slender, slightly tanned frame. It didn’t take long, she was blessed to only have a very small amount of fine body hair, she did have to take special attention to her pubic area, pulling her scrotum tight and shaving the small amount of hair there, then pulling her small cock tight and doing the same. She was barely two inches long when she was limp, but all the extra attention to her private parts began to excite her and she swelled to her erect four inches. After shaving, she took care to clean out her anus with a douche, she did this almost daily which kept her clean, “Just in case,” she thought. Being completely clean and shaved she then rubbed herself, moaning slightly. Her cock twitched slightly as she gripped it with her slender fingers, her other hand reaching around herself and sliding bağdatcaddesi escort a finger between her firm round ass cheeks, she didn’t penetrate herself, she just caressed her asshole which made her cock twitch and strain even more in her hand. After just a minute or so of pumping her cock twitched and spasmed let loose a modest stream of white cum into her hand and onto the shower floor. She moaned and groaned in euphoria as the last drop spilled down, after she recovered she licked her fingers clean of her own cum, rinsed off and hopped out of the shower.

After blow drying her curly brown hair and teasing it out again, Bree retrieved a make up bag that rivals any girl she had ever met and set about making up her face. She selected a smokey jade green eye shadow which she applied skillfully, she took the care to apply highlights and mid tones to her eyelids the way she had learned from videos online and her old high school drama friends. Bree always loved make up, and when she was in high school drama she loved being made up by the girls in the class, and they loved doing make up on her. After curling her long eyelashes, she then applied her darkest black eyeliner, black mascara, a modest amount of blush to her cheeks to even her complexion, and finally a light pink lipstick which pulled the look together quite well. Still naked standing in the mirror she winked and blew a kiss at herself, anyone from behind would have thought they were looking at a gorgeous teenaged girl, except of course for the cock and lack of tits.

The music still playing in her room, she danced over to her bed where her outfit was laid out and she got dressed. She tucked her cock between her legs and her balls into her abdomen then pulled her panties up over them. Bree had gotten used to the discomfort over the years, and in fact it was starting to become more comfortable than letting it all hang out. Next, she pulled up her tights, reveling in the feeling of them caressing her smooth shaved legs. She admired herself in the mirror, a flat stomach and a flat crotch. Then she put on her pink bra and the silicone breast-form inserts she purchased on the internet. She thought to herself that she loved how most of her clothes were more cute than sexy while she pulled her blouse over her head, and pulled up her skirt and zipped it up in the back. “But I do need to get some sexy clothes one of these days,” she said to herself in a voice a few octaves above how she normally talked.

Before putting on her cute flats, Bree walked over to the chair in her room with a bottle of pearl green nail polish and toe spacers. She had gotten good at painting her nails quickly, and within five minutes she was done with her toes and set to work on her fingers. She had also gotten very good at removing the paint, “I do have to work and live as a boy after all,” she thought to herself. After painting her nails, she opened her window and lit a cigarette while waiting for them to dry. It had been only about two hours since Mitch left, and the sun was making its way down the sky. She admired the many colors of pink that the sun was casting into the blue sky and onto the white clouds. She tossed her lipstick stained cigarette butt into the coffee can on her window sill, and being satisfied with the nail polish being dry, she put on her flats and danced her way downstairs to grab another beer.

Dressing up for her wasn’t always a sexual thing, sometimes, Bree just liked to prance around the apartment and pretend she was a real girl, anyone looking in the window at that time would just see a college aged girl singing into her beer bottle, probably just getting ready to go out for the night. She turned up the music and sat on the couch and enjoyed her beer and another cigarette. Her head started feeling delightfully fuzzy from the few beers she had enjoyed, she just smiled and waved her head from side to side with the beat of the music. She felt so comfortable done up, and felt confident in the fact that Mitch would probably be gone until Monday morning, she didn’t even notice when the deadbolt clicked open. She did, however, notice when the door swung wide open.

She froze with fear on the couch as Mitch had practically kicked the door in, he was looked obviously pissed off.

“That fucking bitch!” Mitch yelled out, apparently not noticing his roommate sitting on the couch, or the way she was dressed, “She kicked me out!” Mitch shouted as he stormed into the kitchen, “I need a fucking drink.”

Bree didn’t know what to do, she just sat there frozen, the ash from her cigarette falling onto her lap.

“Brian? Where the fuck are you man? I’m having a cri-” Mitch stopped as he spotted the girl sitting on the couch, “Wait, what,” he blinked a few times as the person on the couch just stared at him wide eyed, like a doe caught in headlights, “What? What the fuck? Bri…” Mitch stammered and put his beer down on the counter, “Brian?” Bree looked down, her cheeks turning bright red from embarassment,

“Umm.. It’s… I,” Bree stuttered in her normal boy voice trying to buy time,

“Dude, what the fuck,” beykoz escort Mitch repeated himself, “What the fuck?” Bree thought she was going to die of shame, until she thought to herself,

“Just own it Bree, just own it. You can do this,” the last part she spoke under her breath in her femme voice, “I, umm.. Look, Mitch, I’m.. Uh, how do I say this,” she shook her head as if trying to force it out of herself, then took a drag of her cigarette and a sip of her beer, “My name is Bree.”

“Brian?” Mitch looked confused, Bree stood up and walked over to her roommate and best friend of nearly five years,

“No, my name is Bree. But, it’s still me, I’m still the same person you’ve always known. I’m sorry I never told you about this,” she put her hand out to shake his like they were meeting for the first time, Mitch just stared at her and shook his head,

“What… What’s going on here? Some… Some kind of freak,” Mitch was still stammering as he backed away from the girl who stood before him, Bree couldn’t tell what was going on in Mitch’s head. She always knew him to be fairly open minded, but it took him a while to get there. She put her hand down, and looked at her friend and fought back the tears welling up in her eyes,

“I know this must be a shock, but,” she trembled and her voice was shaking, “I’m still your friend, right?”

“I don’t know.” Mitch continued backing away until he was resting against the kitchen counter, “How long has this,” he just gestured at her,

“As long as you’ve known me,”

“And, are you, like… Gay?” Mitch could barely maintain eye contact with her,

“Not really, I mean,” Bree replied meekly, “I’ve never actually been with a guy,” Bree’s face began to flush again in embarrassment, “But, I mean, if the right guy came along,”

“Stop,” Mitch interrupted, he sighed and took a long drink out of his beer, draining the bottle in one go, “This is a lot to take in,” he reached into a cabinet and pulled out a bottle of whiskey and a glass, “Already had a shitty day, and now this?” he said, almost to himself. He poured himself a glass of whiskey and downed it,

“Mitch, I know this is pretty weird,” Bree spoke up again meekly, “I understand if you don’t want to live with me any more,” a few tears rolled out of the corners of her eyes,

“Do you want a drink?” Mitch asked, finally in a more normal tone. He pulled a second glass down and poured them both a drink. “Look, this is really weird for me,” Mitch handed a glass to Bree, they both downed their whiskey, “But, shit, you’ve been my best friend for a long time. You’ve also been the best roommate I’ve ever had.” He refilled both their glasses again, “This changes a lot of things, but it doesn’t change that.” They both just stared into their drinks,

“So, you’re not mad?” She looked up shyly,

“Nah, not mad. This will take some getting used to though,” he downed his drink again and poured himself another, “So, Bree, huh?”


They talked for a while smoking cigarettes and having a few too many drinks. They talked about how Brian has been dressing up as a girl for a long time, and how Bree feels more confident and more fun than Brian does. Feeling a bit more comfortable with each other, they sat on the couch, albeit as far away as they could from each other.

“I have to admit, you do look good as a girl. At first I didn’t recognize you, I thought you had a girl over!” Mitch was finally chuckling as he spoke like he normally did, and after sharing a half bottle of whiskey with Bree they were both loosening up, Bree even kicked off her flats and was sitting with her legs to her side on the couch.

“Oh you flirt, even when the girl is a boy you just can’t contain yourself. What would Sarah think?” Bree joked with him,

“Well, about that,” Mitch looked away,

“Oh, Mitch, I’m sorry, I didn’t mean-” Bree felt awful, she obviously hit a soft spot with her friend,

“No, it’s okay. You know, she is only 21, she’s right, she hasn’t seen the world. She only came to this town for school, and she’s going to be graduating and leaving soon. She doesn’t really want me to come with her,” Mitch said somberly, “Plenty of fish in the sea, right?” he raised his glass to Bree,

“Of course! To fish!” She jokingly toasted with him,

“To fish!” Mitch repeated, and downed the last of the whiskey, “Dude, I mean, can I still call you dude?” Bree just nodded, she didn’t care, “I am toast, I need to hit the sack,” Mitch stood up,

“Me too,” Bree stood up and as if all the whiskey came crashing down her at once, she nearly fell over drunk. Mitch, out of instinct or reflex, reached out to grab her and put her back on her feet,

“Oh, you gotta be careful,” Mitch said and suddenly released her as he realized that he was holding Bree like he would hold Sarah. If this were to have happened just two days ago, Mitch would have just laughed at his drunk roommate. Mitch’s face turned bright red, “I, uh, gotta go to bed.”

“Yeah.. Uh, yeah I want a cigarette first,” Bree’s face was as red as Mitch’s. She just looked down and fumbled caddebostan escort for another cigarette, Mitch pulled his lighter out and light the cigarette, the slender white cigarette being held daintily between her painted and manicured fingers for whatever reason entranced him, their eyes met, “Mitch, I,” but before she could say anything else he pulled her in close and planted a kiss firmly on her soft pillowy pink lips, she feigned pulling away but after a second just gave in and parted her lips as he slid his tongue into her warm and waiting mouth. Suddenly, he just pushed away from her leaving her with her eyes closed and mouth slightly parted.

“I can’t do this, I’m sorry, I’m just drunk and,” Bree just blinked at Mitch,

“Just shut up,” she interrupted him by pulling him close to her by his collar and kissing him passionately, this time her tongue parting his lips and exploring the inside of his mouth, Mitch being nearly a half foot taller than her, she has to stand on her toes to do this. Mitch returns the kiss and wraps an arm around the small of her back pulling her into his larger frame and warm arms. They kiss while his hands roam the small of her back, squeezing her round feminine bottom, and her tight waist, her hands just laying on his muscular chest. She pulls away from him after about ten minutes of kissing like this, “I’m sorry about Sarah,” she winks at him coyly, “Is there anything I can do to make you forget about her, at least, just for tonight?”

“You already have, Bree.” Mitch replies as he pulls her into his arms again. Bree can feel the growing bulge in his pants as their pelvis areas grind together as they kiss passionately again.

“I want to feel your cock,” Bree finally whispers to him. It doesn’t take long before she is on her knees, deftly removing his belt. Mitch pulls his shirt over his head and then undoes the button and zipper to his jeans, Bree then pulls his pants down to his ankles. The bulge has grown steadily larger while this is happening, and Bree can feel her own cock stirring between her legs and it is not straining against her panties and tights. She rubs Mitch’s cock through his boxers and marvels at its length, all those years living together she had never seen Mitch even in his underwear, let alone this up close and personal. She kisses his stomach right above the elastic band on his boxers and breathes heavily on his skin, sending shivers up his spine. Finally, she slowly pulls down Mitch’s shorts and his eight inch cut cock nearly hits her in the face as it springs forth, fully erect. Bree licks her lips and looks up Mitch and slowly begins to kiss and lick the throbbing purple tip of his rock hard cock.

“Ugh,” Mitch moans as Bree kisses and licks the head of his cock, “That feels so good,” he runs his fingers through her luxuriously silky brown hair, “Don’t stop,”

“I don’t plan to,” Bree purrs and winks at him before parting her lips and let’s Mitch pull her mouth down onto his long hard cock. He slowly slides his cock into her warm mouth and moans as she wraps her slender fingers around his cock and begins pumping. With her other hand, Bree begins to rub her own cock through her tights and panties, a wet spot begins to form as precum begins to leak out of the tip of her cock. She moans as his eight inches hits the back of her throat, Mitch then begins to pull slowly out of her mouth and repeats the process. Bree’s own cock begins to twitch between her legs as she rubs herself more vigorously, her cock begins to ooze with cum in her panties, she pulls Mitch’s cock out of her mouth and gasps and moans as she cums loudly.

“You are so hot Bree, fuck, keep sucking my dick.” Mitch says breathlessly, Bree shakes her head regaining her senses after her own orgasm and begins stroking Mitch’s cock with both hands and fervently flicks the tip of his cock with her tongue before working her way down with her tongue licking his scrotum and sucking his balls slightly. Mitch’s knees almost give out with the sensation of her warm tongue and wet lips on his balls. “Oh my god, don’t stop!” Mitch cries out as he grips the sides of her head and pulls her mouth down onto his cock once again hitting the back of her throat. Bree had never sucked another man’s cock before, but she has practiced on her many dildos, and she always knew what she liked when she received blowjobs from her life as Brian. After only a few more minutes of her bobbing up and down onto Mitch’s cock she could feel him tensing up. “I’m going to cum, oh god, Bree, I’m going to cum!” She doesn’t stop sucking, she only looks up at her best friend and roommate,

“Uh huh,” she moans onto his cock, that’s all Mitch needs to hear before he begins to cum, she pulls him out just enough that only his tip is in her mouth and he lets loose jets of cum into her wet and waiting mouth. Bree nearly gags on the cum, not because of the taste, but the sheer volume of his hot seed. Mitch convulses as drops of cum begin to peek out of the corners of her mouth. When he is done, he pulls his cock out of Bree’s mouth, and she just looks up at him, smiles and swallows, licking her lips to get the rest of the cum that had dripped out of the corners of her mouth. She stays on her knees for a moment, still stroking his softening cock and massaging his balls gently before Mitch pulls her up to her feet and hugs her close. He kisses her softly and gently on her cheeks and forehead.

Ben Esra telefonda seni bosaltmami ister misin?
Telefon Numaram: 00237 8000 92 32

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