Brandy - Cover

Brandy

Rachael Ross 1982 - 2012

Chapter 3: The Pouring Problem

Romantic Sex Story: Chapter 3: The Pouring Problem - We're not in Kansas anymore! Transgender romance blooms for Brandy when she leaves home for college life. Assigned a room at the freshman boys' dorm, Brandy always knew she was supposed to be a girl, but she never knew it would be this much fun... and complicated!

Caution: This Romantic Sex Story contains strong sexual content, including Consensual   Romantic   TransGender   Interracial   First   Safe Sex   Oral Sex   Anal Sex   Masturbation   Petting   Cream Pie   School  

My first party at college was a big one and not only that, it was a frat party too! I'd never seen so many men in one place in my entire life, so I was feeling a little bit of everything. I was excited, nervous, frightened, happy. I dunno. Mostly I just felt ... horny.

My best friend Darla and I had gotten there a little late maybe, but probably not. The party was in full swing by nine thirty and I figured it would probably go all night long. It had that sort of feeling to it, not that I would know anyway. I'd never been much for parties, but I was at college now!

"God! Have you ever seen so much cock in your life?" some girl said and the rest of us giggled nervously, well I did anyway.

Some of those girls just grinned and shared little knowing looks with each other. They were the older girls, the ones who'd been at college for a few years and knew what was going on. The freshman like me, who'd been in high school just three months before, we were getting our first real taste of higher education.

We were standing in little groups here and there for the most part, the girls I mean. There were probably three boys for every girl, but from what I overheard those odds would go down because the boys liked to get there early and the girls liked to get there late. By the time midnight rolled around it would be more like one-to-one because college girls love to party too! I hoped so because to tell the truth, I was feeling a little like that Custer guy surrounded by the Indians and I didn't want to be massacred or anything. I just wanted to meet some guys and have fun and...

"Hey," some guy said, sort of squeezing between me and Darla and he was a little drunk it seemed to me.

"Hi," I smiled at him, but just a friendly one.

"Are you that dick chick?" he asked me, kind of loudly too, since the music was going and all. "I heard about you."

"What?" I blinked at him and I might have blushed, just because I didn't really want to be the center of attraction at a frat party.

"You gotta dick, right?" he grinned and sorta gestured at my skirt, a short black one, with his drink, sloshing beer onto the carpet.

"Get out of here!" Darla smacked the guy's head, like slapped his left ear with her palm while I was still trying to think of something to say.

"Ow! Bitch!" The guy jerked and spilled more beer, giving Darla a real dirty look, but his ear was probably smarting!

"Asshole!" she said, staring at the guy for a second until he left us.

"Sorry," I said, but I didn't know why I was apologizing for him. I wasn't ashamed of who I was or anything and I didn't try to hide it at all, but I didn't exactly advertise either. I just couldn't believe anyone could be that rude.

"Don't worry about it," Darla rolled her eyes at me. "There's guys like that everywhere."

"Do you really have a dick?" one of the girls standing nearby asked me and a few people were looking me up and down and whispering.

"Yeah," I shrugged and took a little sip of my beer, but I really don't like that stuff very much. It's like a rule though, you can't go to a party and not hold a drink.

"But you're so pretty though," the girl laughed and she was pretty too, sort of petite with nice hair, just a shade red of auburn.

"Thanks," I smiled and I'd made myself up pretty nice.

I had that short skirt showing off my legs and it was tight, so I was showing off my nice round butt too. A red blouse with my lacy red bra underneath it. I didn't really have any tits at all, just hard puffy nipples, but the bra gave me the illusion at least. My blonde hair was loose and falling around my pretty face in a golden cascade. I'd dyed my hair twenty minutes off the bus and I loved it because it went so well with my blue eyes.

"Is it hard?" she asked me and then made a face. "Not your dick! God! Sorry, I mean..." she laughed and even blushed a little. "But, you know, being, um..."

"Queer?" I asked and I giggled at the look on her face. "Not really," I shrugged. "I'm just me, so ... Is it hard being you?"

"What? Oh," she rolled her eyes and knew I was teasing her, but I had a good point too.

"Hey, I'm gonna go mingle," Darla told me. "You gonna be okay by yourself?"

"Sure," I nodded. "Just don't get lost!"

"Wish me luck," my best friend grinned and kissed my cheek before slipping into the crowd. The frat house was a big one, really huge, and it was full of people.

I went off to mingle too, since standing in the corner with a bunch of shy girls wasn't doing anything except make my nipples itch. There were a lot of guys and most of them looked pretty good. Some of them looked real good in fact and while I wasn't the hottest girl in the place, not by a long shot, I knew I looked good enough to eat and I was getting a lot of hungry looks, believe me!

Unfortunately, it is kinda hard being a cross-dressing fag, even though I'm really not one of those at all. I'm like nine-tenths girl and until I got naked nobody was going to be able to tell I wasn't. But I wasn't going to lie to anyone either or try and trick a guy into taking me someplace quiet, making out for like an hour and then giving him the big surprise. That wasn't me at all. I didn't just want sex, I wanted a guy to go with it, you know? A real boyfriend and that meant he had to know and understand everything right from the start.

"Hey there! Whoa, don't walk by," a young man smiled at me, turning away from a conversation with his two friends. "I'm Wayne."

"Hi Wayne," I smiled back and I'd been getting hit on a lot, so I was starting to get used to it. He was nice looking anyway, tall and sandy haired with wire-rim glasses that made the boy look smart.

"What's your name?" he wondered and his friends were looking at me now as well.

"Brandy," I told him. "Are you in the fraternity?"

"Me?" he shook his head. "Nah, I'm just here for the free beer. How about you?"

"No," I scrunched up my nose and giggled. "I'm not in the frat either."

"Heh!" he laughed at my little joke. "You're frosh, right? A freshman?"

"Yeah," I nodded. "I guess it shows, huh?"

"Hmmm ... I dunno," he took the excuse to give me a long up and down look. "You look pretty good from here, I think."

"Thanks," I pulled some hair out of my eyes and gave him a petulant smile, I think. I'd been sorta practicing that one.

"So how do you like college so far?" Wayne asked me and that was my chance to let him I know I wasn't completely the girl he thought I was.

"It's great," I said. "I'm living over at Hereford Hall, so that took some getting used to, but..."

"Hereford?" he lost some of his smile. "That's one of the men's dorms."

"Yeah," I agreed with a little nod and an apologetic smile.

"But..." He looked at me again and he still couldn't tell I wasn't a girl because God had made me right, all except for that one little thing between my legs.

"You're a man?" one of Wayne's friends asked, just to make everything crystal clear. All three of those guys had been interested, the other two making eyes and waiting their turn if Wayne got shot down.

"Um ... Just a little bit," I admitted and my heart was going fast, as it always did at the moment of truth. I didn't want to be laughed at anymore than the next girl does, you know?

"Shit," Wayne snorted and that was that.

His two friends looked a little uncomfortable as well and I suppose it's kinda hard for a young man to admit that he was attracted to another man. All three of those guys knew that about each other now, that they liked me, and after a few minutes they'd laugh about it and it would be okay again, except I'd have to be someplace else. The only good thing was that there were a lot of boys there, like I said, and while rejection really does suck, I wasn't going to give up that easily!

"You're a transvestite?" a cute, guy with beautiful brown eyes stared at me. I wasn't sure if he liked the idea or not.

"No, uh-uh," I shook my head. "I'm a transsexual," I told him, wondering if he'd understand the difference and suspecting he wouldn't.

He left me with a quick blink or two and I just shrugged, looking around for Darla and that was hopeless. It was a couple hours after we'd arrived and now the place was packed, even though most of the party had moved outside. Half the campus probably showed up at one time or another that evening and a lot of the kids stayed for at least a little while. I'd been having fun, despite about a dozen dismal failures with an equal number of reasonably attractive young men. I'll admit I was starting to lose hope and my mind had wandered to Keith, my roommate at the dorm, and I wondered what he was doing.

Keith had been my fuck buddy for a little while, until that very afternoon when we'd sort of ruined it. He had a serious girlfriend back in West Virginia and I kind of wanted to be his serious girlfriend here in Washington. Keith liked me a lot and he almost didn't mind that I had boy parts, but he wasn't completely comfortable with me yet. At least, not enough to want all of me, and the thing with Suzanne, his girlfriend ... It all bummed me out.

"Hi," a warm voice interrupted my brief melancholy and I smiled up at a good looking black guy as he offered me a plastic cup. "You look kinda empty," he said. "So I thought I'd fill you up."

"Oh!" I grinned and gave the man a little of my pink tongue in appreciation of his innuendo. "Thank you. I'm Brandy," I said, accepting the beer and determined not to drink any of it.

I'd managed to get by without a cup in my hand for nearly half an hour, but rules are rules.

"Yeah, I know," he nodded. "Hereford Hall, right? Undeclared major, the sweet little blonde from Kansas?"

"What?" I blinked at him and then laughed. "Have you been stalking me?"

"No!" he said with a pained look and then grinned. "Well, maybe a little. I overheard you talking to some other guys. I just had to work up some courage."

"Really?" I gave him a doubtful look.

He was big and healthy, muscular the way I like my men to be. He had unruly black hair, not kinky, but just really thick and wavy sorta, I took in his rich coffee colored skin and soft brown eyes and tiny dimples when he smiled ... Wow! All of that was making me feel good inside. He didn't strike me as the sort of guy with a huge confidence problem, not the way he was looking into my eyes just then.

"I'm Dave Deere," he held out his hand and I gave him my fingertips.

"Dave Deere?" I laughed and he gave me a little frown as he held my hand gently.

"Like the tractor, yeah ... What's so funny?"

"Nothing," I shook my head. "I'm sorry. You have a really nice name. I like it."

"Okay," he smiled then and let go of my hand. "I thought maybe you didn't believe me."

"Why, uh ... Why wouldn't I believe you?" I wondered with a curious look.

"Ummm..." That seemed to confuse Dave for a second and we were both just sort of smiling at each other. It was strange and kinda funny.

"Hey Dave..." A red-headed giant suddenly put a huge hand on Dave's shoulder. "Some of us are heading off campus, you wanna come?"

"No. That's okay, man," Dave told the guy and he smiled at me. "I'm fine right here."

"Cool," the guy gave me a grin and turned away. "Look out little people!" he said loudly, sounding an awful lot like thunder rolling through a valley and people did look out.

"That was the biggest guy I ever saw in my life," I said. "Did you see him?"

"Who? Lenny?" Dave nodded. "Yeah, I see him every day."

"He was huge!" I giggled, feeling sort of dumb.

"He's pretty big," Dave laughed, enjoying my reaction to his friend it seemed. "He's got a big ass, I know that much."

"What?" I gasped and spilled some of my drink as I burst out laughing.

"He's my center, yeah," Dave said, as if that explained anything.

"The center of what?"

"The football team," Dave was looking at me curiously. "You don't know who I am?"

"Uh ... You're Dave, right?" I giggled and I knew I wasn't drunk, but I sorta felt like it just then.

"I'm the quarterback for the Lions," Dave told me.

"Oh," I blinked at him and I had to think about it for a second. "That's the football team!"

"Yeah," he grinned at me. "I thought that's why ... Never mind."

"Why..." I just shook my head. "Can we, um ... Can we like, start over?"

"Yeah," Dave agreed. "Let's do that, but not here ... Do you want to go for a drive? My car's outside."

"Sure," I smiled and I was more than ready for some fresh air.

I spotted Darla as we made our way out of the frat house. She smiled when she saw Dave holding my hand, leading me towards the door. He was well over six feet tall and muscular, and handsome like I said, and Darla just gave me a little thumbs up and a questioning look, like how far was this gonna go? I shrugged and smiled back, not knowing exactly what was going on with this guy, but it did look promising so far.

Everyone knew Dave too, or so it seemed. Every other person we passed said hello to him, especially the girls, and I might have felt a twinge of jealousy when he'd smile back. But it was my hand he was holding and I ignored a few catty looks as we passed. Some of those girls were serious too, especially the ones wearing their college cheerleader outfits. They knew they were hot and I had to admit I'd always wanted to be a cheerleader, silly as that sounds, but I'd been a boy until just recently and in rural Kansas, boys didn't get to play with pom-poms.

"This is a really nice car," I said as Dave opened the passenger door of a little black Porsche for me.

"Yeah," he said, watching my legs as my skirt slid up my thighs. "Don't tell anyone it's mine though."

"Why?" I asked him with a giggle, tugging my skirt back into place, but he didn't answer until he was in the driver's seat.

"College rules," Dave said. "Student athletes aren't supposed to accept gifts."

"Oh," I shrugged at that. "So, um ... Whose car is this? If someone asks, I mean."

"Hmmm..." Dave grinned at me as we pulled away from the curb. "We'll just say we stole it."

"Oh yeah!" I rolled my eyes. "That'll be better."

"I'd be in less trouble probably," Dave chuckled and he was looking at me as much as at the road. "You know, you're really beautiful."

"Am I?" I flirted with him, combing my fingers through my hair. "But you know..."

"You live at Hereford, yeah," he nodded. "I heard you talking with the other guys."

"And you don't care?" I wondered, because I really wanted to know before we went too far in any sense of the word.

"I care," he told me seriously. "That's why I wanted to meet you."

"Okay," I felt warm all over and my tummy was tight, but in a nice way. "Most guys, um ... they kind of don't like my ... you know..."

"They want you to be a girl," Dave suggested and I nodded.

"Yeah," I said, thinking of Keith mostly. "They can see me like this and forget everything else."

"Is that what you want?"

"I am a girl," I giggled nervously because I'd never really talked like this with anyone before, certainly not a guy I'd just met!

"You know what I mean," Dave looked at me and his gentle eyes made my heart thump.

"Ummm..." I shook my head. "No. I like who I am. I don't want to change myself, at least not that much. I want just want bigger boobs."

I laughed when I realized what I'd just said and I could feel my face burning with some embarrassment. This wasn't exactly the sort of conversation I'd envisioned for a first date, if that's what this was. It felt like one anyway and the truth was that it wasn't only my first date with Dave ... It was my first date ever! At least as Brandy and my dates back in high school didn't count at all, believe me. Three dates with three different girls just to please my parents, and none of them had been very exciting. My one kiss with a girl had felt kind of ... Well, I wasn't a lesbian, put it that way.

"Oh?" Dave was looking at my chest and nodding, but he didn't laugh at me and I was grateful for that.

"You think so too, huh?" I asked him, just because I was already embarrassed, so I didn't figure I could hurt anything.

"Maybe," he teased me with a shrug. "I think I'd have to get a closer look first."

"A closer look?" I giggled at that. "We'll see. Where are we going anyway?"

"Just driving," Dave said. "Where do you want to go? I could take you back to my place, but..."

"But?"

"But I don't want you to think that I think your that kind of a girl," Dave smiled and then frowned. "I think."

"Stop it!" I laughed at him. "No. I don't want to go to your place tonight."

"We could go park by the lake," he suggested.

"Oh, is that what kind of girl I am?" I teased him.

"Well, a guy has to try," he said, pulling into a Denny's. "Otherwise he isn't serious."

"Really?" I asked and he was parking near the restaurant. "I don't want to date a guy who isn't serious."

"I don't want to date a girl who parks on a first date," Dave turned in his seat and his eyes were bright and brown under the fluorescent lights.

"Then it must be fate," I said lightly, licking my lips and feeling my heart still thumping. "But what are your friends going to say?"

"If they're my friends, I won't have to worry about it," Dave said.

"And if they're not?" I asked him softly, really hoping I could believe the man.

"Then I don't care what they say," Dave whispered and we could have kissed right then. It was the perfect moment and we were both feeling it, but the waiting was so much better.

"Are we going to go inside?" I wondered after a long ten seconds of just looking at each other.

"Yeah," he smiled at me, showing off his perfect teeth. "I want to watch you eat some pie."

"You do?" I looked at him doubtfully.

"Oh yeah," Dave said. "You can tell a lot about a girl by how she likes her pie."

"That sounds almost ... obscene," I giggled. "What kind of pie do you like?"

"Cherry," Dave grinned. "What else? How about you?"

"Me? Hmmm..." I had to think about it. "Banana cream pie, I think. That sounds pretty yummy."

"You like the cream pies, huh?" Dave nodded like that meant something.

"Yeah ... so?" I was smiling and feeling self-conscious for some reason.

"Nothing," he shrugged. "I just figured a girl from Kansas would go for something more..."

"Old fashioned?" I giggled. "I'm not in Kansas anymore."

"No, you're not," Dave chuckled. "Don't move. I want to do the gentleman thing."

"The gentleman thing?" I shook my head as Dave got out of the car and moved quickly to open my door. "Thank you."

"You're welcome," he said, taking my hand in his and that was feeling really nice as he helped me out of his car.

If anyone in there wondered at the big black man being with the pretty blonde girl, I really didn't care. I don't think Dave did either, but I had to admit that part of me wondered if he didn't like me just because I was white. I didn't think so and I certainly wasn't attracted to him only because he was black, but I wasn't so naïve that I wasn't aware of the possibility. My first few weeks at college had been an eye-opening experience, especially once I'd met Darla and started socializing with some of the other women on campus. Black men were a favorite topic, believe me. It was like they were the flavor of the month or something for some of those girls.

I put it out of my head though. Dave was being very sweet, even charming in a cool and casual way, and I was enjoying myself quite a lot with him. He could have picked up any number of pretty white girls at that party, but he wasn't looking for a girl, I reminded myself. Or at least not a girl who wasn't like me and that was a whole other topic. I wanted to discuss it and understand Dave's interest in me better, but not sitting in the middle of a Denny's!

"I had a real good time tonight," I said a little reluctantly, just because I didn't want the night to end.

"Me too, Brandy," Dave said, turning off the engine and it was very quiet suddenly in the parking lot of my dorm.

He was reluctant too, I thought, but being the perfect gentleman as he'd been all night long. Aside from a little innuendo here and there, a little playful teasing maybe, Dave hadn't done anything except make me feel comfortable. And special. And warm all over. I was very warm, sitting in his little sports car and wishing I didn't have to say goodnight to the man. I wanted to do other things and my nipples were hard and my tummy tingled and my girlish cock had been hard all night long. I was keeping my hands in my lap, trying to hide the small tent in my skirt. Well, I was probably just imagining that, but still...

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