Brandy - Cover

Brandy

Rachael Ross 1982 - 2012

Chapter 2: College Complications

Romantic Sex Story: Chapter 2: College Complications - 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  

"Hi Brandy!" Darla grinned and sat down at the table with me.

She was my newest best friend and really nice. I liked the way she was always smiling and we had a couple classes together, which was how we met. She hadn't known that I was only mostly a girl at first, Darla had figured I was just another pretty girl going to college, but I'd told her about how I had some boy parts too. It had made me a little nervous, because some people get kind of weird about stuff like that, but Darla had just smiled and nodded her head.

"I guess that explains your little tits, huh?" she'd teased me and I'd made a little face because I was kind of self-conscious about how all I really had were puffy nipples. But it was all okay after that and she was real easy to get along with.

"Hi Darla!" I smiled into her big brown eyes and she was cute, the way all eighteen year old girls are. Her face was pretty when she smiled and she was sorta big in her hips and thighs maybe, but not fat or anything. Just healthy and really round. Her boobs were big too, but I didn't hold that against her. I was already looking at getting some big boobs of my own!

"What are you looking at?" She leaned over, pulling some black hair out of her face and tucking it behind her left ear. She had hair like mine, sorta long, below her shoulders and straight, but mine was way blonde!

"Boobs!" I giggled and showed her the brochure thing I'd gotten from a plastic surgery clinic in town. Except they called it cosmetic surgery and a boob job was called a breast enhancement, but it was all the same thing.

"Oh wow!" Darla grinned. "Are you gonna get a boob job?"

"I want to," I sighed. "But it's kinda expensive."

"How much?"

"Like three thousand dollars," I said, looking at her and I got a sympathetic smile.

"That's a lot," Darla agreed.

"They have an installment plan though," I told her seriously, but Darla laughed at me. "I mean it!"

"You're gonna lay-away some new tits?" She shook her head. "You're crazy, Brandy!"

"It's not lay-away," I told her. "I just have to pay a third of it right away and then I can pay off the rest for like, um..." I frowned and tried to do some math in my head.

"Forever?" Darla suggested with a giggle and I pouted at her.

"I just really wanna have some boobs," I sighed, looking at the brochure again and reading how it promised me perfect C-cup breasts overnight.

"You got boobs!" Darla reminded me.

"Yeah," I glanced at my t-shirt, a baby blue one that said 'Blow me down!' on it with Popeye's grinning face on the back. My hard little nipples were under my bra and that sorta made it look like I had some real tits, but I was still pretty flat.

"Hey, lots of guys like small tits," Darla told me. "And you're so pretty anyway, like who's gonna notice? As soon as you smile, guys melt."

"They do not!" I giggled but sometimes they did and we both knew it. Darla was a little envious of me, but it didn't spoil our friendship at all. I was envious of her tits.

"Yeah they do," Darla nodded and then perked up with a big grin. "Hey! Speaking of guys, how about we go meet some tonight?"

"What? Where?" I asked, cause meeting new guys was serious fun and we both liked to do it.

"There's a party over at the Kappa Omega House," Darla said. "Those frat guys? They're gonna have rush week pretty soon and so they're throwing a party so everyone can see how cool they are."

I laughed at that and Darla was giggling. Guys were so like that!

"A frat party?" I shook my head slowly. "I don't know. I heard some bad things about those."

"Heh!" Darla stuck out her tongue at me. "I heard good things about those! Everybody's going too. Like half the guys on campus are going to be there."

"Yeah, but..." I made a little face, " ... how many girls are gonna be there? I don't want to walk in and find out it's just us, you know?"

"All the girls are gonna be there too!" Darla said, rolling her eyes at my reluctance. "God! It's the first big party of the year, Brandy. We have to go!"

"Wellllll..." I giggled. "Okay!"

"You're so easy!" Darla laughed at me. "We'll go around eight, okay? Wear something sexy."

"You think?" I teased her and Darla laughed.

"Not too sexy though! I wanna have a chance too!"

"Yeah, right!" I bumped her with my shoulder. "Okay, eight o'clock. You come get me?"

"Yeah, I'll come by the dorm," Darla nodded and I knew she wanted to see Keith again. He was my roommate and so totally hot! Darla was in total lust with him. So was I.

I needed a thousand dollars, that's what I was thinking as I made my way to my afternoon psych class. I could get new boobs overnight with a measly thousand bucks. Except a thousand bucks wasn't really very measly when all I had was about a hundred eighty seven in my jewelry box. Daddy had sent me some money, but that had gone to pay for my books and I had to pay for staying in the dorm, that wasn't free. I'd gotten student loans for my tuition, but I hadn't even seen that money. It went straight from the bank to the college without even saying goodbye to me.

Maybe I needed a job. That would be tough though because I had a full course load and I wasn't exactly a rocket scientist, I knew that. I got by, but I had to do a lot of studying too. Working would be nice and having new boobs would be great, but if I didn't graduate college ... I didn't want to wait tables my whole life! School had to come first and then boobs, I decided. Besides, some guys did like girls with really small tits and Darla was right, most of the guys I talked to didn't even seem to notice once I gave them a smile.

But some did and that made me frown.

I needed a rich boyfriend, I thought with a giggle. That drew some curious looks and I blushed, since I was sitting in the middle of fifty other college students listening to the professor lecture us about psychology. I should have been paying more attention, but I was busy thinking about other stuff.

Actually, any boyfriend would be kind of nice. Keith would make an awesome boyfriend. He was from West Virginia and everytime he said something I had to bite my lip cause his accent was soooo sexy! I was from Kansas, I didn't even have an accent, so far as I knew. And his big muscular body and his soft brown eyes and short brown hair. And his cock? Oh my God! Keith had a really amazing dick. It was big, but I never measured it or anything. I didn't have to. Think big and that was Keith's penis. Big and handsome, I should say, because just like the rest of him, Keith's manhood was very attractive!

I felt my own little cocky throbbing in my panties and I was getting a wet spot because she likes to drool when I got hot inside. What a slut! My penis is small, not really tiny, but just small and pinkish and sexy looking. I have sexy balls too, hairless and soft between my smooth thighs. I wasn't ever planning on getting the whole operation or anything. My cocky and balls were a part of me, you know? I should have had a real pussy, probably, since I was mostly a girl and all. But God had given me a penis instead and I trusted Him more than just about anyone else. I just wished He'd given me some really nice tits too!

Or a thousand dollars. Please God?

"Hey Brandy!" Stu was smiling at me and he was the first boy I'd met at college. He was in my psych class and now we were walking out of the lecture hall together.

"Hey!" I smiled back at him.

"What were you giggling about?" he teased me and I saw his eyes checking me out.

Stu liked me a lot, I knew that. He'd dyed my hair for me and lived in the room next to mine. He didn't mind if I didn't have real tits. I knew that because he was always looking at my legs and butt mostly. I was wearing my pink denim shorts too and they were small and tight and lots of guys had noticed, but Stu was really enjoying the view as he deliberately let me walk in front of him.

"Ummm..." I smiled over my shoulder at the young man and caught Stu's eyes on my firm, round butt. I didn't have boobs, but I had a great ass! Maybe that was God's way of making it up to me.

"Heh!" He looked up and he was busted and knew it, but that just made his smile bigger and the pink in his cheeks looked pretty sexy.

"I was thinking I need a rich boyfriend," I told him seriously.

"Oh yeah?" he narrowed his eyes slightly and we were walking side-by-side.

"Hi Brandy!" A guy I didn't even know smiled at me as he walked past and I smiled back. I did a lot of smiling at college.

"Are you rich?" I asked Stu playfully, just teasing him.

"Um, no," he admitted. "But if you ever want a poor boyfriend, I could, I mean..." he cleared his throat and I kept waiting for him to ask me out, but he never did.

"Hmmm?" I looked at him and Stu was turning a little red.

"Hey Brandy, what's up?" a boy asked me and he was Mike? Or Nick, maybe, I forgot, but he was cute and sat next to me in my chemistry class.

"Hi!" I gave him a little wave and checked out his butt as he walked by. That was funny cause he was checking out my butt too and Stu coughed lightly. "Sorry..." I made a little face and Stu was smiling. "Anyway, can I ask you something?" I wondered.

"Yeah, sure," he nodded.

"Do you think I'd look good with big boobs?" I asked him, stopping for a second so he could get a good look at me. "Not like huge ones or anything, just ... nice ones?"

"Ah, well..." Stu swallowed hard and he as taking a good look too!

"It's okay if you do," I reassured him. "I won't get mad if you don't like my tits or whatever. I think I need bigger ones."

"I, uh ... Brandy!" Stu laughed.

"What?"

"I'm not gonna say a word, okay?" he told me. "My dad warned me about questions like that."

"What? He did?" I giggled and we were walking again.

"Oh yeah," Stu nodded. "When it comes to girls and their bodies, dad told me, there's no right answers."

"Heh!" I stuck my tongue at him. "Your dad's pretty smart, huh?"

"Well, he was married three times, so..." Stu shrugged, " ... maybe not."

"Three times?" I shook my head at that. "My mom and dad have been married twenty three years and they're still going strong."

"That's cool," Stu said and I could tell he meant it. "I'd like to find someone like that."

"Me too," I agreed. "When I get married, I want it to be forever, you know?"

"Yeah," Stu smiled at me.

"Hey, are you going to that party tonight?" I asked him. "Did you hear about that?"

"What? That frat party?" Stu asked and then he grinned at me. "Why? Are you going?"

"Yeah," I nodded. "Me and Darla. We're gonna see if we can meet some boys, you know. Have some fun."

I was saying that just to tease him mostly. I really liked Stu a lot and we were friends, you know? But I kept wondering what it would be like to go out with him sometime and just see what happened. Maybe we wouldn't really connect, but that would be okay. We'd still be friends, except I heard about girls who dated their friends and then they weren't friends anymore. It was different afterwards, so maybe ... It was sorta confusing and maybe it was better this way.

"Nah," Stu shook his head. "I'm not into the frat thing. I'm sure you'll meet a lot of guys though."

"Yeah," I smiled, but I could hear a bit of wistful frustration in Stu's voice and I wondered when he was gonna ask me out and what I'd say when he did. I really liked him as a friend.

"Hey Brandy ... Hi Brandy ... Wassup Brandy?" A bunch of guys greeted me in the dorm kitchen because we all wanted a snack as soon as classes were done.

"Hi guys!" I smiled at all of them and dropped my book bag on the table. Maria frowned at that so I moved them quick, putting my bag gently on the floor. She was the cook and from Haiti and it was her kitchen for sure!

"Hey, Brandy?" Carl, who was a big, athletic sort of guy and very cute was looking at me. "You think I could borrow your anthropology notes?"

"You want my notes?" I laughed at him. "Where were you today?"

"I got stuck in the registrar's office," Carl explained. "I missed the class. How about it? You wanna come up to my room?"

"Ohhh!" One of the other guys teased us and some of the boys grinned and chuckled. "The old borrow-your-notes trick, eh?"

"Shut-up," Carl waved them off.

"How about I just give you my notebook?" I asked and Carl was hot for me, I thought. He'd been a little quiet about it at first, since I wasn't exactly a girl and all, but by now he was getting over that and the other boys were used to me.

Carl always gave me a lot of eye and while we were only a couple weeks into the school year and I'd just met those guys, a lot of my dorm-mates were getting used to having a girl living with them. A kinda girl, I should say. They all knew my not-so-secret secret and at first it had been weird, you know, a lot of whispers and comments behind my back. But now? The guys were okay with it and some of them, like Carl, didn't really care about my little cocky, or what the other boys might think of them being interested in me.

"Awww..." Carl grinned and leaned against the counter, standing kind of close to me, looking down with his soft green eyes. "What if I can't read your handwriting?"

"Hmmm..." I sighed theatrically, like it was a huge chore to go up to his room.

"Please? Pretty please?" he was teasing me right back and I giggled.

"Okay, I guess I can come up for a little bit." I was feeling all kinds of sugary inside when I said that!

"Great!" Carl nodded and he was ready to go right then.

"I gotta have something to eat first though!" I told him. "I'm starved!"

"Carl will give you something to eat, I bet!" a pudgy boy named Barry said, but he was always saying stuff like that. He had kind of a dirty mind. Well, we all did probably, but he liked to tell us about it.

I blushed and Carl looked at the boy like he was going to hit him, but the other guys were laughing. It was a pretty good joke and everyone in that dorm took a rubbing at one time or another.

"You don't talk like that in my kitchen!" Maria gave Barry a solid thwap the head with a long wooden spoon and that was funny too. Then she said something in French, I think.

"Mmmmm ... Carl..." I sighed and he was kneeling on his bed behind me as I sat on the edge of it.

"What?" he whispered, massaging my shoulders with his big strong hands gently. "Don't you like it, Brandy?"

"Yeah, but..." I arched my back because it felt really great, the way his fingers were digging into my soft muscles, kneading my flesh and making me warm all over.

"I just want to repay the favor," Carl's voice was deep and gravelly when he talked softly and I liked it. "You should lie down and let me give you a real massage."

"Ohhh ... um ... yeah ... no ... Carl..." I laughed lightly and he was working his thumbs along my spine, rubbing my back through my thin t-shirt.

"A full body massage," his lips were close to my right ear and his breath tickled me so that I shrugged my shoulders. "I'll make it feel real good for you, baby."

"Baby?" I giggled and put my hands on top of his as they moved around my narrow waist to my flat tummy.

"Hmmmm ... You don't wanna be my baby?" he breathed and moved his face against my hair, snuggling me as his hands moved up and down my stomach, getting a little higher and my nipples were on fire.

"I should go," I whispered, feeling my hard little cock spasm with anticipation. I pressed my thighs closed, kind of rubbing them together and his hands were sliding up to feel my tits.

"You should let me take this off for you," Carl kissed my hair. "You're so beautiful, you know that?"

"Ohhh..." I shivered as his hands pressed themselves against my flat chest and stiff, swollen nipples. He was tugging at my bra through my shirt and I was still holding his hands and I forced myself to push them down.

"Please?" Carl whispered and his tongue slipped into my ear for a brief second of pleasure. "Nobody will ever know. I promise."

"Everyone already knows," I giggled and shook my head, wondering why I was saying no to the man. "I have to go."

"Brandy..." Carl sighed, but he let me go because he really was a nice guy. They all were.

"Maybe next time," I told him, catching my breath and tugging my t-shirt back into place. "I just ... I have to think about it, okay?"

"Okay," he nodded. "Yeah ... I understand..."

"Okay," I gave him my best smile and grabbed my book bag before I left his room.

As soon as I was in the hallway and the door was closed, I leaned against the wall and closed my eyes, taking a deep breath and wondering if I was crazy or something. Carl was hot and he wanted me. We could have been doing it right then, but I'd said no. What was wrong with me? But I knew what it was. I had to live in that dorm with all of those guys and if I started having sex with one of them, well ... Only two things could happen after that. Either I'd end up having sex with all of them, which I didn't want to do at all. That would be sort of bad.

Or, I'd end up with just that one guy and everyone else would be unhappy about it. Boys were worse than girls sometimes and I didn't want to see anyone fighting or anything dumb like that. It was another reason I hadn't done anything with Stu and why I'd probably say no if he ever asked me out. I couldn't have a boyfriend in the dorm where I lived, not with some two dozen other boys feeling rejected and jealous. It wouldn't work and maybe I was being too cynical about it, worrying too much and not giving them enough credit, but could I really afford not to?

I had to live there!

Of course, every rule has its exception and mine was sitting at his desk, turned away from it with his bare feet on his bed, talking on the phone when I entered my room. Keith. My baseball playing roommate and a situation which had its own rules and regulations, and little clauses in fine print at the bottom of my heart. We really lived together, him and me, and so everyone assumed we had sex. Keith took a lot of good natured ribbing from the other guys, but he was popular and so cool about it that nobody could really get mad. Mostly the guys were just jealous of his good luck for getting me as his roommate.

"I know, yeah ... I miss you too, sugar pie," Keith was saying softly into his phone and he looked at me as I entered the room. "I'm thinking about you all the time, you know that."

I smiled, but didn't say anything. I knew I had to be quiet because that was Suzanne on the phone and Keith was pretty much engaged to her. They'd been high school sweethearts and she was still in high school, just starting her senior year. As soon as the girl graduated they were going to be married. I'd seen Suzanne's pictures, Keith had a bunch of them, and she was a very pretty girl. Blonde like me and kind of fragile looking with a nice smile. I could see why he loved her and it must have been hard being apart like they were.

"Yeah ... I'm alone ... why?," Keith said into the phone and they talked everyday almost. "Oh yeah? You're in bed, already? I know it's later there, but ... Oh, what else are you wearing ... That's all?"

I bit my lip so I wouldn't giggle and pulled my t-shirt over my head, watching Keith's brown eyes traveling up and down my body while he listened to his girlfriend. I took off my bra too, reaching behind me to unclasp it. My nipples were dark and really swollen. I'd just started taking some hormones and they took a big chunk out of my weekly allowance, but they were worth it. I wasn't going to get real tits that way, but maybe smallish A-cups eventually, I hoped. Right then I was still pretty flat chested though, looking like a twelve year old girl with big, hard nipples poking out. Keith seemed to like that look though and I laughed silently.

"Oh, yeah ... You're making my cock hard now..." Keith said softly. "I can almost see you laying there ... Those beautiful tits of yours, all hard for me ... Is your pussy wet?"

I unbuttoned my shorts and pushed them down my legs, stepping out of them and not bothering to hide my stout little penis as it made a bit of a tent in my white g-string. I'd bought a package of three, wondering why they cost more than regular panties since they were so much smaller. It was comfortable and I really liked the way the thin material pulled up tight against my balls and across my anus as it disappeared between the round cheeks of my butt. I turned around, walking to my dresser just so Keith would get a real good look at my ass. It was the sexiest part of my body for sure and a lot of guys loved it.

"Hmmm, Suzy ... I want to love you hard, girl..." Keith was rubbing the bulge in his jeans and I looked at him, biting my lip and lifting my eyebrows inquisitively. "I want to feel your lips around my cock ... I love the way you make me feel so good..."

I nodded and I knew he was talking to both of us, Suzanne and me. I was Keith's roommate and after we'd gotten used to each other I'd become his fuck buddy too, which was a funny thing to say. Darla had called us that after I'd confessed to her about Keith and me. She'd said we were fuck buddies and I'd laughed and blushed and nodded happily.

It was way cool for both of us. We didn't promise each other anything, just relief from the tension and stress of being in a new place so far from home. Usually we just jerked off, or I should say that I jerked us off. I'd get on Keith's bed with him after the lights were out, bringing a towel with me and I'd usually give him a hand job while he stroked my hair and shoulders and thought about his girlfriend on the other side of the country. Sometimes I'd suck him too, but we'd just started that and it was rapidly becoming our favorite thing in the whole world. Or at least mine.

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