Do You Think I'm Sexy?

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A straight man is seduced by his crossdressing roommate.
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"Do you think I'm sexy?" Brian asked as he walked into the kitchen, pulling up his running spandex so that they stretched against his butt cheeks. He shook his short, sandy blonde hair and gave me a smile. All of the ladies always talked about Brian and would constantly drool over his lithe body and handsome features. Brian, however, wasn't interested in women, and had been making weird advances towards me since we became roommates.

"I told you, Brian," I sighed, looking away from him, "I'm not into guys and I have a girlfriend."

"I'm just playing with you," Brian laughed, trying to raise his pitch to a girlish giggle. He bounded away, off for his evening run, peaking over his shoulder to see if I was watching.

"Maybe I need to rethink this living situation." I murmured, turning towards my room.

-

"Do you think I'm sexy?" Brian asked, bending over in his purple yoga pants to show off his round butt.

He struck different poses on his yoga mat, stretching his limbs and trying to give me a view. Over the last few weeks, Brian had put on a few pounds, and it really showed in his lower half. His skinny thighs had a bit more thickness to them and his ass had become more pronounced, producing a little jiggle when he walked.

He smiled at me, fluttering his eyelashes to emphasize his deep blue eyes. I found it startling just how feminine he appeared, not just in his shapelier body, but in his face as well. Was he wearing makeup? Or was his face just naturally that soft?

"Dude, I'm not gay," I shook my head, "Why are you making this weird?"

"Just teasin' you," he laughed, his voice seeming higher than usual. "Don't be so serious."

I walked back to my room, taking a moment to shake the picture of Brian's shapely booty out of my head.

-

"Do you think I'm sexy?" Brian asked, sitting next to me on the couch.

I paused my video game and turned to him.

"Brian, you have to stop..." my rant was cut short as I took in his appearance.

Throughout the last few weeks, his sandy blonde hair had grown long and shaggy, coming down over his ears. His heart-shaped face perfectly framed his big blue eyes, petite nose, full cheeks, and puffy pouty lips.

He wore a light blue spaghetti string tank top, which revealed the straps of the white bra he was wearing underneath. The weight he had been gaining seemed to be distributing to his chest, as a pair of A cups filled his bra.

Brian also wore some tight skinny jeans, which hugged his thick thighs and wide hips snuggly. With the pear shaped lower-half he was growing, he had more curves than my girlfriend! His arms were completely hairless, and the cuffs of his jeans were rolled up, showcasing hairless calves and ankles, along with a pair of dainty feet that were pedicured and painted a matching light blue.

"B-Brian," I stammered, "Why are you dressed like a girl?"

"I just felt like looking pretty today," he giggled, his voice much softer and more feminine than usual. "So, what do you think?"

"You look..." I paused. I wanted to tell him he looked great, but admitting that was kind of gay, wasn't it? It's not like I was into dudes. But at the moment, he definitely didn't look like a man. He was kind of cute. I closed my eyes and banished the thought from my head. "You're getting on my nerves, man. You can't keep making these crazy passes at me. I have a girlfriend and I'm not gay!"

"It's not gay if I look like a woman, is it?" Brian smirked, his plump lips curving upwards into a devious smile.

"Wh-what?" I mumbled, thinking through the odd sentence. "Of course, it is! You're a guy! I'm done with this conversation."

My heart raced as I got up from the couch and walked towards my room. Brian's feminine body was imprinted into my head as I stalked away. The more I imagined his wide hips and voluptuous body, the more I felt my pants start to strain against my stiffening cock.

It was just a coincidence, right? I was hopped up on caffeine... and I hadn't seen my girlfriend all week. Surely, that was the reason my body was reacting strangely.

I went back to my room and masturbated to relieve the tension. The image of Brian may have entered my thoughts a few times...

-

"Do you think I'm sexy?" a soft, seductive voice asked as I sat at my computer. I spun to see a woman in the doorway to my room, leaning against the frame. She had long sandy blonde hair down to her shoulders and a strikingly gorgeous face. She wore a short black skirt, black stockings up to her knees, and a white blouse.

Her body was chubby in all the right places, bombarding my eyes with bountiful B cup breasts, a soft mid-section, thick thighs, and wide hips that would make any man's jaw drop.

"B-Brian?" I gasped, recognizing his familiar, yet nearly unrecognizable face. "Oh my god, you've changed so much!" After a two-week long vacation, Brian had returned to the apartment completely transformed. His weight had increased even more, giving him ladylike curves that most burlesque dancers would envy.

"You didn't answer my question," he cooed playfully, walking into my room with a shake of his dangerous hips.

"N-no," I exclaimed, though I could feel my face flushing red. "Get out of my room! This is so wrong!"

"If it's so wrong," Brian giggled, his blue eyes glancing down to my crotch, "Then why are you so turned on?"

My cock ached as it pressed firmly against my jeans. Though my willpower made every attempt to stay strong, my body betrayed me. I was desperate to touch him and feel his warm flesh squish in my hands.

"I-I'm not gay!" I yelled, though it almost sounded like pleading, "I have a g-girlfriend." Even I said the words, it was difficult to picture what my girlfriend even looked like. Right now, Brian was all I could imagine. And he looked far more feminine than my girlfriend ever had.

"Why don't I be your girlfriend for the night?" Brian smiled warmly, those delectable lips still pouty and smug. I imagined how good they would feel on my neck, on my lips, and around my cock.

"I said I'm not gay!" I protested even further, despite my raging hard on, throbbing in my jeans.

"It's not gay if I'm a woman, remember?" Brian giggled again, and this time I almost bought it, imagining our two bodies intertwined as we kissed.

"Get out of my room!" I stated firmly, getting up to shut my door, though the process was awkward with my stiff erection.

I gasped as I sat down on my bed, wondering what the hell I was doing.

"Suit yourself," the female voice said from behind the door.

Powerlessly, I began to touch my cock, envisioning Brian's bombshell body in my bed next to me.

-

"Do you think I'm sexy?" Brian whispered into my ear.

Though I managed to avoid him for several weeks, it was inevitable that me and my roommate's paths would cross eventually. Over the course of those weeks, Brian's shape had gotten even more out of control as he continued to gain weight. His motherly C-cups were impressive and stuffed his lacy bra with pillowing breasts. His midsection had accumulated some more chub, creating a soft tummy that looked like a joy to squeeze. Brian's thighs were tree trunks, thick with stocky fat that gave him a wide berth, tapering up towards his even wider hips which made doorways challenging. The added pounds also added some more softness to his face, giving him full cheeks and an irresistible pair of plump bimbo lips that called for a warm kiss.

The feature that drove me the craziest, however, was Brian's ass. His bouncing booty was out of this world, jutting out behind him like a shelf and jiggling violently with even the slightest movement. I had been dreaming about his ass every night for the last week, imagining its size and girth as I slept. Every morning I woke up with cum stained bedsheets. After not seeing him for so long, his fat bubble butt was even more impressive in person; bigger and more hypnotizing than even my dreams could conjure.

When we finally ran into each other in the hallway, my heart raced in my chest. I tried to think of my girlfriend and how loyal I was to her. I tried to remember that Brian was a guy and that I was a straight man. None of that mattered once Brian entered my view and I was instantly drawn in by his fat, feminine body and beautiful face.

We stood facing each other in the hallway outside of my bedroom. The plump boy turned blonde bombshell slid over to me, getting close enough for me to smell is floral perfume. As Brian leaned forward, his warm breath lingering on my neck, his plump breasts gently brushing against my chest, he repeated himself.

"Do you think I'm sexy?"

"Yes," I whimpered, reaching to wrap my arms around Brian's body and pull him in close.

We descended into a furious make out, his lush lips squishing against mine, his sweet tongue darting inside of my mouth. My hands wandered across him, gripping all of his feminine curves and squeezing them tightly. I played with his soft breasts and tummy, admiring his matronly figure. My fingers worked down towards his dynamite thighs, which were nearly bursting out of his nylons. I could not wait for those legs to spread and constrict me.

As we kissed deeply, I knew it was wrong. I knew that it was gay. I knew that I was cheating on my girlfriend. But I didn't care. I couldn't care. Brian was my dream girl. Both my heart and cock throbbed in sync, completely in shock at how little control I had over my own impulses, but also in heaven and never wanting the moment to end. My cock pulsed painfully against the constraints of my pants, and Brian seemed to take notice.

He slid onto his knees down in front of me and helped me work my pants down around my ankles. As I took off my boxers, my dick sprang free, completely hard and aching for release. Brian licked his lips and smiled seductively, his big blue eyes hungering for my cock.

"Let mama help you with that, baby," Brian pouted, his pink bimbo lips parting as he leaned forward to consume my shaft.

The entire length of me disappeared down his throat as his fat lips slid down to the base. We both moaned in unison and my eyes rolled back. Brian's head began to bob up and down slowly, slurping as he worked my dick in and out of his gaping, warm mouth. It was the best blow job I had ever received. After only a few pumps, I was near ready to burst.

"No," I whimpered, gripping his sandy blonde hair, "I don't want to cum yet."

As much as I wanted to explode in his pretty mouth, I feared that when I came, the fantasy would end, and I'd feel nothing but shame and regret. I wanted to push that moment as far into the future as I could and enjoy the present. I wanted the moment to continue for as long as possible.

With my shaft still entirely in his mouth, he paused and gave me a wink. That saucy look on its own almost sent me over the edge, but I held on, though I suffered even more as he very slowly pulled my cock out, tickling the head slightly with his hot, coarse tongue.

"I think I know what you want," Brian smirked, some of my precum drooling from his puffy lips. He stood up and began to slowly undress.

He dropped his skirt down between his feet, revealing a pair of hot pink panties. His package bulged noticeably, clearly erect and pulsing in his womanly lingerie. Brian was such a bombshell of a woman that I had nearly forgot about the one male aspect of him that remained. And now that I saw it, it could not be ignored. As he slid down his panties, his meaty cock catapulted to attention, surprisingly rivaling my own in size and girth.

Right there in the hallway, he instructed me with a gesture from his long, beautifully painted index finger that he wanted me to drop to my knees. Still unsure of how far I wanted things to go, but completely wrapped up in Brian's spell, I did as he commanded, lowering myself until I was eye level with his mighty love stick.

As his round mushroom cap stared directly at me, slippery with cum, my control was completely relinquished, and I dove forward, taking as much of the shaft as I could into my mouth. My jaw burned, and my cheeks strained as I took in his meat, nearly gagging from the sudden intrusion. It was a sensation I had never experienced before; sucking on a penis. In my head, I continued to tell myself that I wasn't gay, though the lie was palpable considering I was stuffing a huge cock as far into my throat as it would go.

I gave it a few long strokes, sliding back and forth, licking the underside of the shaft with my tongue, taking in the feeling and the lavender scents of his body. My tongue and lips wandered the length of him, enjoying the smooth, velvety texture of his sensitive skin. I felt it throb and jolt within my cheeks, and I wondered if I was doing an okay job. After only half a minute, I had to pull his shaft out and gasp for air, making sure that my gag reflex didn't trigger.

"It's okay, hun," Brian cooed with a sexy pout, "It's your first time. You'll get better at it, I promise."

"I-I'm sorry." I whispered, ashamed, tasting the cum that had briefly leaked into my mouth. It was a foreign, salty taste, but not unpleasant.

I felt embarrassed. Not that I had just sucked a cock, but that I was bad at it. I continued to tell myself I was straight and only into girls, and yet here I was, on my knees and disappointed that I couldn't continue pleasing Brian's fat dick.

"Don't worry, darling," Brian grinned devilishly, grabbing my arms and leading me into my bedroom. He climbed up onto the mattress, his fat thighs wobbling as he bent over in front of me, presenting his ridiculously huge ass. "Why don't we get the real party started?"

Without a moment of hesitation, I leapt onto the bed, cock still erect and removed the rest of my clothes. I reached over and removed Brian's tank top and bra, groping his plump breasts as my hands passed over. He moaned from the slight touch on his nipples and let out a giggle. Soon, I was completely naked, and the only thing Brian was still wearing was his pair of knee high stockings, which seductively framed his plump legs.

His ass still presented to me, I positioned myself behind him, aimed my erect dick directly between his meaty cheeks, and plunged slowly but firmly into his tight asshole.

We both gasped from the sensation and my fingers squeezed Brian's fatty ass flesh in front of me. The warm feeling of his ass gripping my cock tightly was unlike anything I had ever experienced. I began to move my hips, pounding his blubbery butt as my dick firmly penetrated his deep expanse.

"Oh, fuck!" Brian yelled from his hands and knees, letting out a series of girly squeals as he squirmed in front of me.

His screams of pleasure only became more intense when I reached around his wide hips and gripped his hard cock, which was still wet and sticky with my saliva. I began to pump his dick in unison with my humping, loving the feeling of his slippery man meat sliding through my hand.

Our moaning continued as I rammed into him again and again. His smooth, tight hole had a vice grip on my unit; it almost seemed as though my cock could be trapped in there forever, and at the moment, that kind of imprisonment sounded like absolute heaven. My balls slapped against his thick upper thighs as Brian's hefty balls swung back and forth in tandem.

Within a few more thrusts, I was ready to cum and I could tell Brian was too. My pace increased, and my force became more vigorous. I wanted my cock to go as deep into his fat ass as it could possibly go. With a loud, girlish moan, Brian's cock throbbed and began to shoot cum all over the bed. The warm seed oozed down my hand and into my palm, making his entire meat shaft slippery as I continued to jerk it to completion.

Unable to hold on a second longer, I let out a final gasp, plunged myself deep into Brian's round butt, and released wave after wave of spunk. His rectum constricted, surrounding my cock with his tight insides, causing another groan to escape from my lips. I squeezed his love handles and ass cheeks in unison with the pulsing of my spunk. That rhythm slowed as my cumming deescalated, and a tingling sensation washed over my exhausted body.

As the last of my jizz was spent, we both collapsed onto the bed, my cock becoming limp inside of Brian's bubble booty, and his slippery dick going soft in my hand. He hummed as I continued to gently knead his slick, cum covered penis between my fingers.

Exhausted and in complete disbelief, I passed out, replaying the best sexual encounter of my life again and again in my mind as I dreamed.

-

"Do you think I'm sexy?" Brian whispered as he planted a soft kiss on my cheek, gently stirring me awake.

"More than anything," I smiled, brushing his cheek and drawing him in for a warm embrace.

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AnonymousAnonymousabout 5 years ago
Ignore the nincompoop! Great Story ❤

I like your story it is very hot but my only complain is Brian wasn't prepare for anal. Example, lube or fingering and stretching. Seriously, like ouch! I hope you continue this story and ignore the less than savory comment. He/she or non binary individual don't know what their talking about some trans woman do have sensitive nipples and so what if it is physically impossible to have an antiquate amount of adipose tissue for breasts, the creator isn't referring to thou so shut it and calling someone, who reached menopause and get botox a "bitch" is just downright insulting. As for the realistic nature of your story don't worry about it because there are people, whom are late bloomers such as myself for spontaneously discovering I am attracted to both sexes. Besides, this is a fantasy a fictional work for the purpose of pure pleasure so what is the point of bitching? Anyway, on a positive note and encouragement I hope you continue to write because you have a knack for it and I am eager to read. As for the rest of you, whom happen to come across my comment stay safe, happy and have a sexy day! Love and kisses y'all XOXO 💋

AnonymousAnonymousover 5 years ago
Horribly inaccurate

Firstly, one cannot will fat to center where you want. If he managed to get enough chest fat to fill C cups, you’d have to have an enormous amount of abdominal fat. Besides, breast tissue is very different from fat, and falls differently. His “breasts” would look like a menopausal Botox bitch’s breasts.

Secondly, it’s highly unlikely Brian here would moan from a brushing of the nipple. Women tend to have very dense nerve endings in their nipples, where as men usually don’t have much more than the same amount of nerve endings as normal skin. It would most likely be like stroking an arm.

Lastly, while possible, it’s unlikely MC would be so intoxicated by a cross dresser that they’d not only break the standard rules of their sexuality, but also cheat on their girlfriend, and somehow maintain the cognitive dissonance required to convince yourself you’re straight while gagging on a dick.

300bowler300300bowler300over 5 years ago
PLEASE

MORE OF THIS HOT, HOT STORY, GREAT START, THERE HAS TO BE AT LEAST ONE MORE CHAPTER OR MORE...! BETTY jo xoxo

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