Continuation of Brian/Bree’s adventures. Thanks for reading everyone! Bree is my favorite character that I’ve ever written, and I will definitely be continuing writing her story.


“What ever I want?” Mitch looked deep into Bree’s eyes, she sheepishly nods up at him,

“I’ve always wanted to please a man, I’m just glad it could also be my best friend.” She replied, her voice trembling with nervous excitement, “Just give me ten minutes, and meet me in my room. Okay?” Bree tugged at her skirt to hide her butt and growing erection as she slinked out of the bathroom and upstairs. Mitch went back into the living room and pulled his boxers and jeans back on. As he lit a cigarette and opened a window, he just thought to himself and smiled.

Bree shut the door behind her as she got back to her room. Her heart is pounding, she couldn’t believe she had just done that. She can still taste the cum that her best friend of many years had just blasted into her waiting mouth, and she loved it. She quickly hopped out of her skirt and found a new pair of panties in her wardrobe. Thumbing through her items she found a pair of black mesh bikini panties with a lace floral trim, she slipped them on fighting her semi erect penis back between her legs. Next, she pulled off her blouse, and took off her bra. She grabbed a black bra with pink lace and put that on instead, taking care to position her silicone inserts. Bree giggled as she imagined one flying out as she pictured Mitch’s strong naked frame pounding her from behind, “No time for that just yet, Bree. Focus!” She thought to herself as she went back to her wardrobe to find a pink and black lace baby doll top, she laid that on the bed and pulled out a pair of open toed, black t-strap pumps with a four inch heel. Right after she put on her lingerie top, and slipped into her heels, she rushed over to her bathroom and sprayed herself lightly with her favorite perfume and put on some lip gloss. Then there was a light knock on her bedroom door.

“Can I come in?” Mitch called in softly, his mind had been racing the entire time he was downstairs. He had fantasized about being with a transgendered woman before, but those fantasies usually just ended with him masturbating to internet porn. He had never imagined that it could be his best friend and roommate who would fulfill those fantasies. It all began to make sense to him now, Brian had always acted a little bit feminine, but Mitch knew he had girlfriends in the past. He knocked at the door again, and Bree opened it immediately. She stood in front of him, the guy Mitch has known for years but dressed in the sexiest lingerie he had ever seen.

“How do I look?” Bree asks him, almost purring, “I hope you like it.”

“You look,” Mitch replies after a moment of speechlessness, “amazing.” He puts an arm around her slender waist, and plants his hand at the small of her back and pulls Bree’s small frame into his. She stumbles slightly in her heels from being pulled so suddenly, but he catches her. She enjoys that she can still look up into his eyes even while she’s wearing heels. After staring in each other’s eyes for another moment, he leans in to kiss her. His tongue darts into her parted mouth, which she gently sucks for a moment before returning his passionate kiss by allowing her tongue to enter his mouth.

“I just love how you kiss me, Mitch.” Bree says interrupting him for a moment. She takes his hand and leads him over to her bed, which she sits at the edge of. Mitch leans down and kisses her on the lips again, this time taking her face into his hands and holding her there while he explores her warm mouth with his wet tongue. While Mitch is kissing her, she quietly undoes his pants again, letting his jeans fall to the floor she begins to rub the outline of his rock hard eight inches under his boxers. His cock twitches and stirs as she caresses it with her fingertips and stroked her lover’s scrotum and balls through the fabric.

“Oh… That feels so good,” he moans breaking off his kiss. With a tug, Bree pulls his boxer’s down and Mitch steps out of them. She just leans back and admires him for a second, with his 6’6 inch muscular frame and eight inch cock, no wonder the girls all flocked to him and not Brian for all these years. He climbs on to the bed while laying her down next to him, he continues kissing her while fondling her fake tits through the lingerie. She moans into his mouth as she places one hand on his hard throbbing cock and begins to stroke it slowly, massaging the balls gently before working her way up to the tip. With her other hand, she untucks her own small but turgid penis from between her legs and begins stroking it slowly as well.

“Do you want to fuck me?” Bree asks, staring straight into Mitch’s eyes, “Because, I really want you to fuck me.” She is too turned on to be nervous at this point, and doesn’t wait for him to answer before she moves down to his crotch and begins to lick and suck on the rather large tip of his big dick. He moans and lays back, she positions herself to where Mitch can fondle and play with her ass, and he does. She only stops sucking his cock for a moment to tell him that the lube is in the top drawer of her nightstand. He reaches over and pulls it out, applies some to the tip of his index finger and pulls her panties to the side and begins playing with her asshole, caressing it gently and making sure it is nice and slick before sliding just the tip of his finger in. She stops sucking his cock and moans when he does that, and gets up onto all fours while he starts finger fucking her slick asshole.

“I really want to fuck you Bree, your ass is so tight and so hot,” he says staring at her pink puckered hole and her smooth, round butt cheeks. Mitch leans in and starts kissing her on the cheeks of her butt and down the backs of her thighs, all still while fingering her. Bree grinds her butt into his hand until his index finger is completely engulfed by her asshole, she grunts and moans while her sphincter closes hard on his finger.

“Stop,” she says breathlessly, “stop teasing me, baby… I need your cock,” she looks back at him and continues, “I need your cock in me.” He pulls his slick finger out of her ass, which she sees and grabs his hand and licks and sucks his finger clean. Bree never minded ass to mouth, as long as her ass was clean. This drives Mitch wild as his cock twitches as she sucks on his finger, he then applies some more lube to her anus, and liberally applies it to his cock, even though it was still wet with her spit from her mouth just minutes before.

“Bree, you are so fucking hot,” he says as he positions his cock at the entry of her tight sphincter. Bree props herself up with one arm as she reaches down with her other hand to begin slowly stroking her own four inch cock. Mitch teases the tight asshole for almost a minute before slowly pushing the head in.

“Oh, oh God, it’s so big, oh God…” Bree squeals out as she slowly becomes impaled on his massive cock. “Don’t stop, don’t stop, don’t stop!” She moans as she grips the sheets on the bed. Mitch just throws his head back and slowly drives his cock into her until he is grinding firmly into her butt cheeks with his pelvis. He grabs her hip with one hand, and holds her panties to the side with the other as he slowly pulls his cock out of her. He continues to slowly insert then slowly extract his giant dick in and out of her tight ass for another few minutes until her sphincter becomes a bit more relaxed and used to the size of it. “Just fuck me,” she purrs as she turns her head to look him in the eye, “Just fuck me!” With that she bucks her hips and pushes herself hard all the way down onto his cock and squeezes it as hard as she can with her sphincter muscles.

“Oh fuck!” Mitch cries out as his cock is massaged by Bree’s surprisingly strong ass muscles. He let’s go of her hip with one hand and digs his fingers into her hair and pulls it gently but firmly until Bree is barely holding herself up with her own hands. Mitch then pulls her close to his chest and supports her with his other hand letting his hips buck and his cock drive deep into and out of her warm and tight asshole. Not having to hold herself up any more, Bree reaches down to massage her own balls and tug on her own small cock as she gets fucked hard from behind. She strokes her own small cock with the same rhythm that he pounds her with. He showers her neck and shoulders with kisses as he continues impaling her. The sounds of him kissing her, as well as her stroking her own cock, are utterly drowned out by the sound of their balls gently slapping together and the wet sounds of their fucking.

“Mitch, I’m going to…” She gasps out as her balls tense up and her entire body shakes and trembles as the orgasm rips through her. Her sphincter muscles expand and contract, pumping his rock hard cock, as her own cock twitches and drips out her sticky white cum onto the sheets and her hand. Her body goes limp for a second and Mitch just catches her, but doesn’t skip a beat fucking her. He lays her body down onto the bed, keeping only her ass up slightly in the air. He grabs onto her hips again and begins to fuck her harder, as her ass spasming like that only drives him crazier with lust. She just pants trying to catch her breath again while he continues pounding her ass. She’s played with her own sex toys, and even got an ex-girlfriend to fuck her in the ass with a toy once, but it’s never been like this.

“Your ass feels so fucking good, I never want to stop fucking it.” Mitch keeps pounding away as he places one strong hand on her back and pushes her down into the bed. Bree just squirms and writhes in the pleasure she is receiving from being fucked, she just moans as she tries to look back at him fucking her.

“I want you to cum in me,” she says straining her neck to look him in the eye, “I want to feel your hot cum shoot into my ass. I want to feel your cum fill me up and drip out of me.” She licks and bites her lip as she turns back to the bed. Mitch stops just long enough to flip her over onto her back.

“I want you to see me fucking you. I want to watch your face as I fill you with cum,” he replies to her panting, he pulls her legs up to her chest as he slows his pace down. He slides a finger into her mouth, which she sucks on like it were a cock as she reaches up and caresses his chest and plays with his nipples. Her cock twitches to life again and starts dripping and oozing with a clear fluid as another orgasm begins to tear through her body from Mitch’s fucking hitting her prostate just right. Her eyes roll back into her head as she jerks under him, the orgasm rolls and builds in her as her sphincter involuntarily squeezes and contracts around his rock hard cock. “I’m going to cum!” Mitch cries out as he pushes himself as deep into her as he can, his whole body tenses up and the cum begins to shoot deep into her bowels. She throws her arms around her lover as they both shake and writhe in their own orgasms, he kisses her deeply, pushing his tongue into her warm mouth as the last of the cum spurts inside of her. They kiss for a while as Bree just grinds her ass into his softening cock trying to pump every last drop from it.

“That… Was… Incredible.” She pants into his ear as Mitch’s limp cock pulls out of her. He holds her where she is, her legs up by her chest as her asshole spasms and twitches, gaping slightly from the fucking she just went through. She puts her hand down to scoop up the cum that is now leaking out of her ass, she hungrily licks it off her fingers. She continues moaning in the afterglow of the marathon sex session they just had.

“You are so hot, Bree.” Mitch finally says as he lets her go and stands up, his now flaccid cock just hanging off of him, dripping with cum and lube. She eyes him hungrily, wanting to lick his cock clean, but he goes into the bathroom and wipes himself off. She does the same. He returns to her bed with her after she changes into a nightshirt and he pulls his boxers back on. She lays her head on his chest and eventually drift off to sleep in his arms.

Bree wakes up the next morning, her eyes still filled with sleep she can’t believe what happened last night. Mitch isn’t in her bed any more, she looks around groggily and steps out of her bed. She opens her door and peeks down the hall, his door is open, and she can hear him on the phone. She tip toes down the hallway and lets herself into his room. He’s looking out the window, so he doesn’t notice her come in. She reaches out and grabs his butt playfully, he almost yelps into the phone, but just turns around and gently pushes her hand out of the way, and motions for her to leave.

“This isn’t a good time,” he puts his hand over the phone and dismisses Bree. “Oh nothing, that was just Brian.” He says as he returns to his conversation. Feeling no small amount of hurt and shame, she leaves his room and goes back to hers to take a shower and change for the day. Now that she was out to her roommate, she figured she would just stay en femme. She laid out an outfit for the day, something casual again, pink cotton panties and matching pink bra, skinny jeans, a black tank top, and finally the flats she had on the day before. She hopped into the shower, did her hair and applies some make up, nothing fancy, just a smoky black eyeshadow, liner, mascara, and finally a little concealer to even out her tone. Just as she was coming out of her shower, Mitch knocked on the door and called in to her, “Hey so, umm, Sarah is coming over today. She wants to come and get me so we can talk. I’m sure she wants to say hi to you too, so, maybe today isn’t the best day to be all.. You know, all girly?” Bree’s heart sank as she listened to the muffled words through the door, but Mitch probably just figured it was a drunken one time thing.

“Maybe it was a mistake,” she thought to herself. “Alright, no problem Mitch.” She called out to him in her boy voice. Sighing, she set about taking off her makeup, and removing the color from her fingernails. She then put away her girl clothes and put on her everyday male attire. A pair of jeans, sneakers, and a t-shirt. He still wore his panties underneath his boxers, but now Brian just put his hair back into his normal tight pony tail and went downstairs. Sarah was already here and runs over to him and hugs him in greeting.

“Hey buddy! How you doing? I haven’t seen you in ages,” Sarah said to Brian, “Your hair is getting so long!” She playfully tousled some of his curls.

“I’m good,” Brian responded, “Class has been going well, I’m just glad it’s almost over. I heard you’re not sticking around after you graduate?”

“Yeah, that,” Sarah said back, letting go of his long hair. “Well, yeah, you know, I’ve lived two places my entire life. I want to get out and see more of the world.” She stood back and he was able to admire her for a second. Brian always liked Sarah, and they were friends before Sarah started dating Mitch. He liked the way she dressed especially, today she was wearing a tan knee length sun dress and tan wedge sandals with cute blue straps. She stood just barely 5’6, but with her heels on she is as tall as Brian, and her straight blonde hair was kept short, falling just above her jaw line. “I know you guys talked last night when he got back, thanks for helping him out, he must’ve been kind of freaking out.”

“Yeah, we definitely had a bit of a talk.” Brian responded, feeling more than a little embarrassed, he hoped that Sarah couldn’t notice his cheeks flushing.

“Well, I hope that you don’t totally hate me. You understand why I have to do this right?” She asked him.

“I do, Sarah. I couldn’t hate you.” He told her, she reached out and hugged him as Mitch was walking down the stairs.

“Hey Sarah,” Mitch said as Sarah let go of me and walked towards him, “Ready to go get breakfast?” She nodded at him. They left, Mitch didn’t even look twice at Brian, and as Brian watched them go he couldn’t help but feel jealous at this girl. He tried to shake it out of his head as he ate his own breakfast. Soon after breakfast, like he predicted yesterday his boss called him in to cover a shift at work. Work went well as it helped keep his mind off of his situation, but he couldn’t help but let his mind wander as he recalled passionate moments from the night before.

While Brian was at work he received a text message from Mitch that read, “Hey, Sarah asked me to come with her after she graduates. I think I’m going to go with her. We should talk when you get home.” He couldn’t help but almost cry when he read that, he had just spent the most amazing and passionate night of his life with Mitch as Bree, and now in one fell swoop he’s losing his roommate and she’s losing her lover. Brian could barely keep his mind on his work for the rest of his shift, and after it was over he took his time going home. He stopped at a bar for a drink, thinking to himself that if he doesn’t go home that he won’t have to have that talk. When he finally got home, Mitch was there waiting for him.

“Hey, I thought you’d be off a while ago,” Mitch said as he got up from the couch, “We need to talk.” They sat at the table after Mitch grabbed two beers from the refrigerator. “Last night was amazing. I’m not going to deny that, and you are a beautiful girl, but last night Sarah broke up with me. I was angry, drunk, then very horny. I don’t think that will happen again, because Sarah and I are back together, and I’ll be leaving with her when she graduates.” Brian just stares ahead and drinks his beer as Mitch continues, “I hope we can still be friends, and you know since I’m still on the lease for the next six months, I’ll continue to pay my portion of the rent, that way you don’t have to look for a new roommate just yet.”

“Yeah.” Brian responds, “Thanks.”

“Hey man, I’ve been with Sarah for over a year, I think she might be the one, you understand that, right? You understand that last night was just a one time thing.” Mitch explains, “You’re my best friend, I think we need to keep it at that. I can’t lose you as a friend, Brian.”

“I know. I couldn’t expect you to-” Brian stops and looks away and drinks some more of his beer, “Forget it. I understand man, Sarah’s great.”

“Thanks for understanding, Brian.” Mitch pats him on the shoulder and finishes his beer, “I’ll still be here for another two months before we’re ready to move out of state, and before you ask, I already told Sarah I did have a one night stand, she said she didn’t want to know who it was, and that she understands because we were actually broken up.” Brian quietly fumed to himself, but felt better that Mitch was at least being kind of honest to Sarah.

The next few weeks went as it used to go, except for Mitch spending more time with Sarah. Sarah graduated and Brian finished his term, and Mitch was making plans and trying to find a job where they were moving to. Mitch actually got called in for an interview in the new town.

“So, I wanted to tell you guys, I got an interview!” Mitch said excitedly as he poured the wine for Brian and Sarah at the dinner table.

“Congratulations!” Sarah said lifting her glass up,

“Here here!” Brian joined in lifting his glass and they all toasted, “So what is it for?”

“A job, you idiot,” Mitch shot back with a grin and wink, the kind of humor that Brian is used to from his roommate, “Nah, nah. I’m kidding, it’s basically the same thing I’m doing now, just for more money and better benefits. It’ll be a bit more responsibility than I’m used to,” he explained, “But I’m definitely up for the challenge.”

“Well, I hope you get it buddy,” Brian responded, “Job hunting sucks, especially right now. When is the interview?”

“Well, it’s next week Monday, so I’m going to drive out there on Saturday and stay until Tuesday, I also want to explore the town a bit since we’ll be moving there,” Mitch said, “So, you’ll have the house to yourself for the weekend.”

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June 2018
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