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One Evening on the Halloween Weekend

Transgender
2011-09-23

Carlita Bonner is a 5 foot 6, 105 pound woman in her early 20s, who possesses blonde and dark brown hair, gorgeous, perky C-cup breasts, soft, puffy nips, pinkish-redddish lips, has long, wavy eyelashes, and recently garnered a slight tanned skin.  

 

She was a femme girly girl, as she loved to shop, recently broke up with her boyfriend, has had lots of sex with men, and painted her nails pink.    She trims the hair above her vagina in the bathroom with a razor before donning clothes.

 

She ponders what to wear in her college dorm room, as she decides between a pink dress or a white tank top and a blue skirt, before putting on a shiny, green sequined halter top with a black mini-skirt underneath.  

 

Meanwhile, she shares a room with two people, one boy and one girl.    The girl on the opposite side of Carlita’s room is listening to a CD on her headphones, as she has brownish red hair, wears a bright red lipstick, is a B-cup, and is wearing a black shirt and jeans.   She is very much into goth and punk, and pretty much keeps to herself most of the time.   She goes by Cathy Reynolds as her name, as she is 5-8, and weighs 120 pounds.

 

The third roommate is a guy named Garth Buford, and is 6-4, 210 pounds.   He has pale white skin, brown hair, and is a walk-on quarterback at the college, as somehow he ended up in a room with the two women.

 

After Carlita finishes dressing in her mirror, she watches TV as Gary talks to Carlita about the dishes he had to clean up.

 

Gary says, “Carlita Stephanie Bonner, it’s almost Halloween, and I still do all the work in this apartment.   You and your goth roommate use all my money to buy clothes, and you guys leave me to do all the dishes.  What the hay?”

 

Carlita puts a finger in her mouth and uses a vibrator as she puts in her pants to soak her pussy before talking.

 

She says, “ I dunno, Garth.   Don’t I like pretty?  Plus, you’re a great fuck buddy!”

 

Carlita purrs, as she gets up to lean to kiss Garth, but Garth pulls away.

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Garth pouts, “Well, I’d be okay with your overspending and sluttiness if you were putting more time into the books.   You don’t even have good grades!  With your gpa, I don’t know how you’d stay in college!  I know the problem. ”

 

Carlita retorts, “Enlighten me, sugar. ”

 

Cathy replies, “That she’s a slut?”

Offended, Carlita objects and says, “Hey!”

 

 

Cathy goes back into her corner before saying, “But it’s true.   You bring a random boy every week or so, and it’s annoying.   You act like I’m barely here. ”

 

Garth replies, “Not the whole answer I was looking for, but yes.   You fuck too many guys, because you actually want to be one. ”

 

Carlita scoffs, saying, “ I don’t see how me fucking a bunch of guys makes me wanting to be a man.   I don’t want a penis, I want it inside me.   I’m the horniest person there is.   Whip it out, big boy. ”

 

Garth almost does it, before saying, “No wait, this is wrong!  You just want to fuck my brains out, just so you can relieve yourself of the guilt from not studying or spending everyone else’s money.   I have no words for you. ”

 

Carlita replies, “Wow.

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    That is weak sauce, Garth.   I could do better than that. ”

 

Garth replies gamely, “Try me. ”

 

Cathy replies wistfully, “Maybe she can give me a try.   Perhaps I could make things right. ”

 

Puzzled, Carlita says, “We’ll see.   I gotta go…. . to the library, to get my learnin’ on. ”

 

Unsatisfied, Carlita leaves to go to her car to drive to the store, before opting to hang out in the library to meet some guys.   Meanwhile, Cathy chases after her, and claims that she must return some books as well, while Garth goes to the gym to lift weights.

 

Carlita walks into the library, and heads into the bathroom, before being stopped by Cathy.

 

Cathy meets with Carlita, which startles her, as Cathy throws her against the wall before talking.

 

Cathy says angrily, “Okay Carlita, listen to me.   I’ve had enough of your behavior, and I feel you’ve been a shitty roommate.

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    You have had sex with too many guys without acknowledging my presence.   We need to iron some things out, and I have some ideas in mind. ”

 

Unnerved, Carlita retorts furiously, “Whoa, whoa, whoa, Cathy, I don’t appreciate your hostility, missy!  What’s it to you?”

 

Cathy scratches her head.

 

She then says, “Alright Carlita.   I apologize for my actions, but I’m only trying to help you!  I know the solution to how you’ll improve your grades.   Dress like a man for Halloween, as my little twinky gay boy, and maybe I’ll your homework for you and teach you stuff. ”

 

Carlita frowns and says, “How is that the answer?  I am a girly girl, and I love having sex with dudes. ”

 

Cathy retorts, “Well, I think you should be a manly man, and I want you to get inside my pants, understood mister?  That way, you’ll get Garth off our backs. ”

 

Carlita reluctantly agrees, and replies, “Okay.   But can I just be referred to the pronouns and keep the way I dress?  So it’s just for Halloween?  That’d be great, and I can be seductive. ”

 

Cathy replies, “Nope.   It doesn’t work like that. ”

 

Carlita asks, “Then what should my man name be?  Amy.   That’s a great name. ”

 

Cathy laughs and says, “No, that’s a terrible name for a dude.

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    It shouldn’t be too close to your actual name…. how about either Carl or Earl?”

 

Carlita replies, “How about Steven.   I like that name…. and I think it fits real well. ”

 

Cathy gives her a thumbs up, while she ponders ways to find ways to get into Carlita’s pants.   Later that day, they go back to the dorm room, where Garth is still away, lifting weights and is hanging out with some guys at the gym.  

 

Content, Cathy grabs a pair of scissors to hack off Carlita’s hair.   Afterwards, she outlines a careful, dark brown goatee on Carlita using eyeliner.   Meanwhile,  Carlita takes off her tank top, as Cathy binds Carlita’s breasts, and binds it carefully using ace bandages.

 

Meanwhile, Cathy fishes for a strap-on with piles of dildos in Carlita’s room.

 

She asks, “Carlita, I have two questions.   Do you have a strap-on, and can you pee standing up?”

 

Carlita laughs, before saying, “Funny questions to ask, chatty Cathy. ”

 

Frustrated, Cathy gets a funnel cup, and manges to find a way to make it into a STP device.

 

She says to Carlita, “Here.   You’ll use this.

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    Try it, standing up. ”

 

The first few times, Carlita misses the toilet completely, as she pisses on her funnel and on her legs, before getting frustrated, and whips out a dildo to please herself.

 

Cathy yells angrily, “Carlita, no!  You need to try again, mister. ”

Carlita replies, “But it’s sooooo hard!”

 

She tries again and again, to no avail, but she tries one last time before successfully being able to pee standing up as it streams flowingly into the toilet, like a man.   Later, Cathy gives Carlita men’s jeans that Garth wears for her to try on, and a pair of oversized sneakers.

 

Later on, Cathy manages to get a fake ID for Carlita, and they go to an adult store to buy a strap-on with a dildo attached to it.    She also buys one for herself, just in case.

 

At the counter, Cathy slyly tells the young butch, “It’s for my boyfriend.   He’s gay. ”

 

The butch lady at the counter replies, “Well, you two make a sexy couple.   I love to fuck him, that’s for sure. ”

 

She winks at Carlita, thinking of her as a strikingly beautful, but mysterious man, as Cathy and Carlita leave.

 

 

In the car, Carlita puts it on, underneath her pants.   She grabs a mirror, admiring herself, as she looks like an androgynously handsome, blonde haired man with a dark brown goatee with breasts and a vagina hidden inside his clothes and strap-on penis.   Afterwards, Cathy uses the scissors to put a whole into the strap-on penis to make it into an STP penis packer.

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Afterwards, Cathy proudly declares, “Carlita, from now on, you are now Steven.   My gay, twinky lover boy, who’ll be with no lady but me. ”

 

Steven/Carlita replies in a high-pitched, nasally, effeminate voice, “But…. I-I…  Okay.   But can you wear a penis?  I’ve only been full-throttled by guys, and it would be weird to do this alone. ”

 

Grudgingly, Cathy accepts.   She draws a thin black mustache and goatee on her face around her lips, as she uses Steven’s mirror to cut her hair.   She uses a chest binder to bind her breasts, before donning an STP strap-on penis packer, and pulls up men’s pants up her waist before finishing off by wearing black socks and a pair of oversized men’s sneakers.

 

Cathy replies, “Alright.   But only if you promise to be dominant. ”

 

Steven replies, “What?  But I like being the submissive one. ”

 

Upset, Cathy replies somewhat furiously, “Well do you want to do this or what?  This is my fantasy, and we have to do this if you want to talk to me more. ”

 

Steven replies, “Fine.   I’ll go along with it.   But you have to promise to fuck my ass.

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  ”

 

Cathy replies, “Will do mister.   And my boy name shall be…. Arnold. ”

 

Steven asks, “Cool.   I was thinking either that or Raymond. ”

 

Raymond/Cathy replies, “Good.   It shall be Arnold Raymond.   And I guess we’re twinky gay boys, now. ”

 

At a Halloween house party somewhere off campus, Steve and Arnold show up dressed in flannel clothing with hip hugging jeans to meet some of Garth’s friends and other people.

 

Garth doesn’t even recognize them, as he says, “Hello, boys.   What are you dressed up as?  A grunge rock band?”

 

Raymond frowns, as he says, “Precisely. ”

 

Meanwhile, Steve exclaims gleefully, “Cool!  I didn’t know that was our costumes!”

 

Garth replies happily, “Well guys, punch and pie is on the house, and there’s beer in the fridge if you plan on drinking tonight.   Well shit, everyone’s drinking tonight, so let’s get started!”

 

As he directs the two boys away to the fridge in the kitchen, he walks with them before retreating to the living room.   He stares briefly at their butts, as he notices skinny men’s jeans on both of them, with Steve sporting a rather rotund, somewhat large, plump buttocks, as Raymond having a smaller butt.

 

Garth can’t help but think that Steve was really attractive, which was weird because he dates women only.

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    But something seemed odd about this fellow.   He smiled as if he knew him, and seemed twinky enough to want to get inside his pants.   Shaking off the feeling, he grabs a beer before deciding to talk to more people in the living room.

 

One of Garth’s friends, the school fullback, talks to the two boys in the living room.

 

The school fullback says, “Hello boys.   Name’s Calvin.   Must be cool to watch the football game on a Thursday. ”

 

Arnold replies wistfully, “Yeah…I guess some games can be on Thurdays, right?”

 

Calvin chuckles as his belly shakes, as he says, “You’re a funny one, Arnold.   Brilliant sense of humor. ”

 

He then says, “So what brings you boys up here?”

 

Steve replies gleefully, “Oh, we’re just here because we came to see Garth-“

 

Arnold nudges Steven, as Steven forgot that they weren’t supposed to reveal this information.

 

Steve continues to say in a raspy, effeminate voice, “I mean we read a flyer about the Halloween party, and it looked super cool!”

 

Calvin looks at Steven up and down quizzically before accepting the answer.

 

He says, “Cool.    You guys are new to the school, right?  I’ve never seen you boys before.    What year are you, and what are your majors?”

 

Arnold replies hesitantly, “We’re sophomore communications majors. “

 

As he finishes saying this, Steve starts to rub his (prosthetic) penis inside his pants, as he starts to masturbate himself furiously with the TV on.

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Meanwhile, Garth looks at Steven, and notices him masturbating with the game on.

 

Garth exclaims scornfully, “Steve, what’re you doing?”

 

Steven apologizes profusely, saying, “I’m not sure, Garth, what do you think I’m doing?  Will I be punished?  I’ll let you see my ass!”

 

Garth replies sternly, “Steve, do not relieve yourself in the room.   Go to one of the bedrooms to do this. ”

 

Arnold laughs with a chortle and replies teasingly, “He can be such a bisexual twink at times.   I’ll give him a talk. ”

 

Calvin says calmly, “Cool.   I’ll send a pretty lady to him upstairs after you iron some things out with your boy.   Her name is Caroline, by the way. ”

 

Steven and Arnold retreat to an empty bedroom upstairs as Steven runs upstairs crying, bawling his eyes out, as streaming tears drop down his reddening cheeks.   Arnold and a curly haired, busty blonde haired woman chase after him, as they get to the empty room, before locking it.

 

As they lock the door, the busty blonde woman lustily approaches Steven.   Caroline, the blonde woman, is wearing a silver sequined halter top, with a black miniskirt and is wearing black high heals as she goes with Arnold to console Steven.

 

Caroline says, “Poor Stevie popped his boner on the floor watching a football game.   Want me to caress it?”

 

Arnold looks at Steven, telling him to say yes.

 

Steven bobs his head up and down as he wipes his tears from his eyes using a tissue.

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Caroline uses her right hand to stroke Steven’s (prosthetic) penis up and down, as Steven coos out ooh and ahhs, as he feels a buzz inside his pants.   She then opens his pants before going down on it as Steven tries closing his pants.

 

Caroline blows on Steven’s penis, as she drools on it, and licks her lips after she cleans her mouth.

 

Feeling satisfied, Caroline replies, “Hope you liked that mister!  I didn’t know you shaved down below.   Most men I know have hairy penises.   Yours is refreshing. ”

 

Arnold hugs him while Caroline hugs Steven as well.

 

Arnold goes up to Caroline, before saying, “Caroline, I have an idea.   I think we should blind fold you while we double team you and have a threesome.

      Cool?”

     

    Caroline exclaims enthusiastically, “Cool, cool, cool!  I’ve never been double teamed by two boys before!”

     

    As they blindfold her, Steven and Arnold strip, as they now wearing nothing except binders displaying bound breasts across their chests, and STP strap-on penis packers harnessed between their butt and thighs.

     

    Arnold fucks Caroline’s vagina, with Steven humping Caroline’s butt from the ground.

     

    Caroline moans, as she rubs her vagina.

    She says, “Oh, ohhh, ohh, ohhhhhhh!!!!!    Yes!!!!!!”

     

    Arnold thrusts his hips back and forth, with a hand on his hip, as each pelvic thrust slams a new sensation into Caroline, while Steven is shaking his hips off the ground, while spasming a little bit each time as he powerfully grinds into Caroline’s ass.

     

    Caroline then yells, “I love you, men!!!!!  Cum inside me!”

     

    Arnold continues to fuck Caroline’s vagina silly while Steven grinds on Caroline’s butt, as he slaps it exasperatingly.   Afterwards, they cum lightly through their penis packers onto Caroline’s tits, as she licks it off, loving every minute of it.

     

      

     

    They finish as the trio kiss, hug, and make out simultaneously.    Feeling the soft bodies around her, Caroline wonders if they are cisguys or trans midway through, but liked the hug nonetheless.

     

    Caroline replies, “Can I remove my blindfold, gentlemen?  That was such a lovely evening. ”

     

    As they kiss, Arnold says smilingly, “ I don’t know…. ”

     

    Caroline replies cheerfully, “Alright, men.   I’ll respect your wishes.   I’ll get dressed and let you guys finish dressing in there, and come meet with me to watch TV downstairs.   And Steve, call me tomorrow if you or Arnold want to hang out with me for lunch. ”

     

    Later, Caroline gets a dress put on for her by the two men, and she promptly removes her blindfold after opening the door on the way out before quickly closing it.   She thanks the gentlemen on the way out before leaving to go to the living room.

     

    Meanwhile, as both Steven and Arnold stand shirtless, they decide to engage in sexual acts with each other.  

     

    Arnold proceeds to hump and pound Steven’s buttocks, as Steven’s butt gets flushed as if it were on fire with each powerful thrust from Arnold.     Meanwhile, Steven gets out a rubber dildo and sucks on it with his mouth.

     

    Arnold whips Steven’s buttocks as he slaps it, with Steven furiously sucking on the dildo and rubbing his clitoris underneath the penis packer.

     

    Steven exclaims, “Oh Arnold!  You’re my master!  Hit me harder!  Harder again!  Sir, I’m such a gay boy!”

     

    Arnold replies as he slaps Steven’s buttocks, “ You got it, mister!  Who’s my twink?  Who’s my twink? You, my boy.

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        You’ve never fucked a vagina before, right?”

     

    Afterwards, Arnold kisses Steve’s butt, as they pull out a double dildo from underneath the bed. To use between their clitorises as the strap-on penis are still harnessed between their buttocks and thighs.

     

    They both lay on the ground, as they insert the toy inside themselves, as juice oozies out from both of the men’s pussies.

     

     

    They move and sway back and forth as they use their butts to jostle for position of the double dildo.   With one hand, they cup the dildo inside their hands, while they jerk their penises with the other.

     

    Steven grabs his penis with one hand, while feels the sensation of his pussy with the other as he stares into Arnold’s eyes.

     

    Steven cries, “Yes, Arnie!  Yes!  Pummel that dildo inside my pussy!  Yes, dammit, yes!”

     

    Arnold strokes his dick, and says, “I love you, Steve!  Such a nice twink.   Do me harder, yes!”

     

    The men continue to hump themselves lustily, using the double dildo, as they grind each other, all the while feeling their wet pussies cum inside their strap-on penises as they finish climaxing.

     

    Arnold laughs with Steven, as he says, “Steven, we’re so gay. ”

     

    Meanwhile Garth walks into the room, unlocking, wondering if the boys were finished consoling with each other.    Right after the two finish climaxing, Garth walks in on them.

     

    Startled, the two boys put aside the double dildo, and rush to put on pants and a shirt.

     

    Garth says to himself, “Hmm.   I have bisexual transguys having gay sex with each other in Caroline’s bedroom.   Wait…are you any chance my roommates?”

     

    Putting on a shirt, Arnold says pleadingly, with his hands clasped, “Please don’t tell anyone.

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        We’ll be good, we promise. ”

     

    Garth replies, “Alright.   Your secret’s cool.   I’ll tell them you guys are having a talk with each other.   See ya when I get back. ”

     

    Afterwards, Steven sucks on Arnold’s red-haired, firebush vagina, as Arnold strokes his dick.   He buries his face into Arnold’s pussy, as he licks the juices clean, while Arnold returns the favor to Steve.   Arnold licks the blonde and light brown hairs of Steve’s pussy as he licks his vagina while Steve strokes his penis.

     

    Later, the two kiss, as they bind each other’s breasts, as they finish putting on their clothes.   They bump fists with each other, before noticing that the hand-drawn goatees on each other’s faces are starting to fade, so they go into the bathroom to use more eyeliner to make the goatees look more realistic.   Afterwards, they head downstairs to greet the group on the way out.

     

    Calvin meets the two boys, as he says, “ It was good meeting with you boys.   Arnold and Steve, right?”

     

    Steve replies enthusiastically, “Yup!  Yup-a-rooni!”

     

    Arnold gives Steve an awkward look, before saying to the group, “Well, Garth, Calvin, Caroline, and Lester, Dave, and Jenny, it was good to meet all of you.   Have a good evening and good night. ”

     

    Arnold and Steve wave the group farewell, as they walk out of the house, while the rest of the group retreats to the living room to watch a movie.

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        Meanwhile, Arnold and Steven hold hands together before walking to their car.

     

    Arnold says, “That was a nice night, Steve, right?  How was that?”

     

    Steve responds, “That was lovely.   I think I want to do this again. ”

     

    Arnold replies, “So are we girls or transmen?”

     

    Steve responds, “Perhaps both.   But I do love thinking of us as gay, bisexual transmen, who’ll fuck hot ladies from time to time. ”

     

    The boys do a chest bump with each other as they go inside the car and drive off.

     

    .

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