Brandy
Chapter 6: The New Thing

Rachael Ross 1982 - 2012

Romantic Sex Story: Chapter 6: The New Thing - 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  

"I don't know," I sighed. "Maybe I'm just one of those girls who falls in love too easy, you know?"

"Are you sure it's love?" Stu asked me, picking black olives off a large pizza we'd only half-finished.

"I don't know that either!" I giggled and scratched my blonde hair with both hands. Kind of a frustrated scratch, like, "Arrrgh!"

"You sound like a pirate," he chuckled and some guys at the next table over smiled at me.

"I mean, I love Dave ... Okay?" I looked at my friend and Stu nodded.

"Okay."

"But I love Keith too," I said, sitting back in the booth and making a face. "It's so totally not fair."

"Since when is love supposed to be fair?" he wondered with a soft sigh, sitting back on his side of the table and smiling at me.

"Ohhh ... I'm sorry," I frowned. "I've been talking about it all night, huh?"

"Well, the night is young anyway," Stu shrugged and I figured he was just about the nicest guy I'd ever met.

Plus he had a crush on me and I knew it, but he was too nice to do anything about it except be my friend. It made me feel like a bitch. Sorta. Sitting there with a boy and whining about my love life, about other boys, and making him give me a shoulder to cry on. That wasn't very fair either, especially since I was trying very hard not to give him any sign that I might be interested in him, because I could have been interested real easy if I wasn't careful.

Stu wasn't like Keith or Dave. He wasn't big and muscular, he wasn't famous or anything like that. He was just a cute looking guy, like 5'10" maybe with short black hair and warm brown eyes, and a great personality. He'd stopped shaving and was working on a scruffy, roguish look that I liked a lot. It didn't make him look tough or anything, just kinda like a beat poet from the fifties and I could definitely see him with some blue tinted shades and a bongo drum.

Or ... maybe not. That woulda been too weird.

Anyway, I needed him to be my friend more than anything else. Like the brother I never had, you know? A guy I could just hang out with and feel comfortable around, that was Stu. My boy next door and the first friend I'd made at college when he'd helped me dye my hair. And he was shy! Not like he was afraid of me, but he'd taken a long time just to ask me out for pizza and a movie. We were going Dutch too, at my insistence, because letting him pay for everything would have made it a real date and like I said, I didn't want to lead him on. We had to be friends and that's all.

"You had sisters. Right?" I asked him, just to change the subject and Stu nodded.

"Yeah. Three of them, two older and one younger."

"Hmmm..." I smiled at him. "You're pretty lucky. I never had anybody."

"Maybe," he laughed. "Being the only boy didn't make me feel very lucky."

"Why not?"

"Sisters are mean," Stu said. "If I had to fight one of them, I had to fight all of them. Them against me, every time. I couldn't win."

"What? They used to beat you up?" I giggled.

"Oh yeah," Stu grinned. "When we were little they did. All the time."

"What about when you got older?"

"Then they found other ways to torture me."

"Torture?" I rolled my eyes. "They did not!"

"You don't know, Brandy," Stu said with a laugh. "And my sisters were friends with every girlfriend I ever had, or one of their sisters. It was a small town, so they all knew each other anyway."

"What's wrong with that?"

"Everything," Stu said. "I mean, there's some stuff a guy doesn't want his girlfriend to know and..."

"Like what?" I narrowed my eyes, smiling as I leaned forward a bit.

"What? Oh ... Um ... I don't know, just stuff," he shrugged.

"Just what stuff?" I smiled at him. "You can tell me."

"Nah," he shook his head and reached for his Pepsi. "It's too embarrassing."

"Stu!" I whined.

"It's not a big deal anyway," he said and Stu had to be teasing me then, I was sure.

"Please? Come on, you brought it up! Tell me!"

"Okay," Stu looked around and leaned across the table, so I did too. This had to be good, I figured. "My sisters used to tell my girlfriends how ... ah ... never mind..."

"God!" I frowned at him. "Why?"

"Because it's embarrassing. I keep telling you that."

"So? Please? I won't tell anybody else, I swear."

"It's kind of a ... sex thing," Stu cleared his throat. "You know?"

"A sex thing?" I dipped my head and giggled.

"Yeah, okay..." he lowered his voice as we leaned together over the pizza, " ... see, I used to, um ... jerk off and I used to..." he paused again.

"What?" I whispered back. "It's okay. I used to be a boy, remember?"

"I used to jerk off in my sister's panties," Stu finally admitted and I grinned at him as his face turned red.

"You were wearing your sister's panties?"

"What? No!" He looked at me like I was crazy. "I mean, I'd just use them, sorta wrapped around my ... you know ... and ... do it."

"Why?"

"Because, uh..." he looked around again, " ... I had a crush on my sister, Janey."

"You did?" I blinked at him.

"My younger sister, she's a year younger than me," Stu shrugged. "She's just ... hot. I don't know. I still like her."

"Like her..."

"The way I'm not supposed to," Stu agreed. "I think about her when I ... you know..."

"Oh," I nodded.

"We never did anything," Stu said quickly. "I never even told her or anything."

"But she knew you were using her panties?"

"Yeah," Stu blushed again and smiled sheepishly. "She caught me a few times. Well, they all did, but Janey used to blackmail me for pocket money."

"She did?" I giggled at that.

"Yeah," he shrugged. "You know, ten bucks here, five bucks there. Not much and I didn't mind. I'd have given it to her anyway."

"And they'd tell your girlfriends?" I shook my head because that was kind of mean.

"Sometimes," Stu nodded. "They probably told all their friends."

"That's weird," I decided.

"Yeah."

"I mean, that's like one of the weirdest stories I ever heard," I grinned at Stu and he waved his hand at me, like telling me to shut-up.

"So now you know my dirty secret," he chuckled.

"Do you still, um..." I pursed my lips, " ... have some of her panties?"

"Uhhh..."

"You do, huh!" I giggled and stuck my tongue out at him. "That's pretty cool."

"You think so?"

"Well, not cool," I shrugged. "But it isn't really bad or anything."

"Yeah, but Janey's my sister," Stu narrowed his eyes at me. "You don't think that's out there?"

"How would I know?" I asked him. "I was an only child."

"Hmmm..."

"You should tell her."

"Yeah right!" Stu looked at me like I was seriously crazy. "You must be an only child."

"Why not?" I smiled back at him. "She's your sister, what's the worst thing that can happen?"

"Uh ... She'll cut off my balls?" he suggested sarcastically. "Or tell our dad, that would be worse."

"But you don't know," I said. "She might want you to cum in her panties while she's wearing them."

"Now that's weird!" Stu decided and I giggled.

"Well, if I was your sister..." I said, rolling my eyes playfully.

"What?" he asked with a grin.

" ... You wouldn't have been jerking off," I told him. "And you wouldn't have been looking for a girlfriend either."

"Oh yeah?" Stu licked his lips. "Why's that?"

"I don't know," I shrugged. "Why do you think?"

"I think you're teasing me now."

"No!" I made a face because when he said that, it reminded me of Carl. "I'm just saying, I wished I had a brother like you when I was growing up."

"Yeah?"

"Yeah," I nodded. "You're sister was lucky. All of them were."

"Maybe," Stu shrugged. "So, um ... What's your dirty secret?"

"Mine?" I laughed at him. "You see it!"

I sat back and sort of opened my arms, like there I was and inviting him to look at me. I'd worn my sexy cool black blouse, the one that looked like wet silk, and my short red skirt, the tight one that really hugged my ass and thighs. My blonde hair was loose around my made-up face and I knew I looked pretty hot. Guys had been checking me out all night and Stu hadn't been able to take his eyes off me.

"Yeah," he sighed and then looked at his watch. "Oh. Hey, we'd better get going if we're going to make the movie."


Half an hour later we were sitting in a dark movie theater, an old one called The Chateau, watching some old movie because that was the only kind they showed there. I didn't mind. I liked all kinds of movies and this one was Sunset Boulevard with Gloria Swanson and William Holden. It was kind of romantic anyway and there were a surprising number of people there, mostly couples it seemed like, or a lot of girls paired up. Roommates without dates probably, who just wanted to get out of the dorm or whatever.

I wasn't entirely sure romantic was a good idea though, since I'd been trying not to give Stu any ideas. I probably had though, just because of how I looked and some of the stuff we'd talked about, and how much fun we were having. Just being friends with a boy was hard work and I wondered how other girls managed to do it, if they really did. It always seemed like it in the movies, but then again, in the movies the boy and girl who were just friends in the beginning ended up falling in love at the end.

Stu wasn't waiting for the end. Twenty minutes into the movie I felt his arm behind me, you know, kind of resting on the back of my seat. I had a small popcorn in my lap, just because you can't go to the movies without getting popcorn, that would be weird. So I ate my popcorn slowly, watching the movie mostly and trying to ignore the couple sitting two rows in front of us as they'd begun to make out as soon as the opening credits had started. A lot of the couples seemed to be making out and I wondered if this theater wasn't like the local parking spot for boys without cars, you know?

"Mmmm..." I sighed softly as I felt Stu's fingers on my right shoulder and he was sitting on my left. I'd kind of meant it like a warning sound, sort of telling him I knew what he was doing and he shouldn't because we were just friends.

"Hey..." he whispered and when I looked at him, Stu kissed me.

His hand held my shoulder then and I knew I shouldn't, but I let him do it. I mean, I let him kiss me, gently at first and then deeper as I let his tongue slip inside my mouth. I had really mixed feelings, because I'd wanted to kiss him for a long time already, for weeks really, but I didn't want to kiss him either. So I thought I'd let Stu kiss me real nice, have that one kiss, and then I'd tell him we shouldn't be doing that. I mean, we couldn't be doing that.

Oh, it was nice though! Stu's tongue felt a lot different than Keith or Dave's. It seemed smaller and more gentle, moving lightly across my own tongue as the boy teased and tickled me nicely. He turned out to be a real good kisser and I grew warm all over, my tummy getting tingly and my barely there tits getting tender all over again. I chased Stu's tongue into his mouth and explored him with soft sighs as he leaned into me. His hand started rubbing my back and shoulder, sliding down so he could reach under my arm and find my right breast beneath my thin blouse and lacy bra.

I hadn't even realized that my own hand rested on Stu's thigh. It slid up and down his trousers, all by itself, it seemed. But I felt his leg beneath my fingers as my hand went little higher, a little more towards the inside of his thigh. I swear, I didn't plan it or anything, but I found my hand on the bulge of his cock, the stiff tent Stu was sporting from his crotch. I squeezed him, getting a little moan that I breathed into my burning lungs. We were seriously making out and that one kiss had turned into something else.

"Stu..." I finally breathed after a solid half hour of making out with him, " ... we have to stop."

"I don't want to," he replied in his own breathless voice, smiling and licking his lips.

Stu's hand moved under my blouse as we were turned towards each other, and he'd managed to push my bra up, sort of, exposing my right breast and puffy, burning nipple to his fingers. His other hand was on my thigh, stroking my leg through the black stocking I wore, high enough to find the lace top of it only a few inches short of my thong covered cocky. I'd grown stiff there, my girlish penis throbbing and wet with precum. Stu's larger and much more manly cock felt swollen under my hand and I'd been sort of jerking him off through his pants, or at least rubbing him a lot.

"Please," I whispered after another long, three minute kiss, "I have a boyfriend, Stu."

"Brandy..." he sighed and then we were kissing again.

I wasn't stopping him and I didn't know what was wrong with me! I knew if I really told him no, like seriously, Stu would stop. He wasn't going to try and force me, at least not in any way except by kissing me, and how did that work? Why wasn't he stopping? Why wasn't I making him stop? God! I was sucking his tongue, moaning into his mouth as Stu played with my nipple. My Achilles heel. I arched my back to press my tit against his hand, gasping into the boy's mouth with pleasure.

That theater felt like a sauna. We were both hot and sticky, damp with sweat, and I bit Stu's bottom lip gently, nibbling on him while I played with his cock. I'd unzipped him, somehow, and I only barely remembered doing it, but I had. I'd opened Stu's trousers and reached inside, finding him hard and eager with arousal. He'd shifted slightly and groaned into my hungry mouth as I'd freed him and now I held his naked cock in my fist, stroking him up and down slowly while we made out.

A few minutes later, Stu's fingers were in my hair and he pulled my head down gently, but insistently to his lap. I didn't say a word either. I just opened my mouth for him, taking the head of his cock between my bruised and swollen lips, and started sucking him off in the middle of the movie with like sixty people sitting all around us in flickering light.

I bobbed my head up and down, finding Stu's penis to be a very nice size for sucking. Not too fat or thin, not too long and definitely not too short. He seemed the perfect size for my hot, wet mouth and I took half his cock easily while I held the other half in my fist and jerked him off. I did everything for him too. I washed his cock with my tongue, tickled the underside and around the smooth head. I swallowed his precum with soft, wet noises that I was sure the people sitting closest to us could hear.

"I'm gonna ... cum..." Stu whispered after five minutes or so and I let him cum in my mouth because anything else would have been a real mess!

His semen wasn't so thick as Keith's maybe, but it was just as hot and salty, creamy as it filled my mouth and I didn't swallow it. I wasn't exactly sure why at the time, but I just kept my lips tight around the glans and pumped Stu's cock with my hand, milking him for every drop he could give me. After half a minute, when he'd finished cumming, I pulled my mouth away carefully, holding that fresh load of man cum in my mouth as I sat up.

"Oh, thanks, Brandy..." Stu was smiling and nodding and he didn't mind when I reached for him, pulling the boy close for a kiss.

His arms went around me and our lips met and opened, and then my tongue, covered with his hot goo pushed into his mouth. A large gob of semen passed between us and I felt Stu stiffen, almost jerk as if he wanted to get away, but I held him to my kiss as I pushed his own cum into the boy's mouth.

"Mmphh..." Stu sort of gagged for a second, but maybe he just had to get used to the idea, because after a few seconds of surprise, we were snowballing his orgasm like crazy!

I'd never thought of it before. Never, ever in my life had I imagined making out with a guy while my mouth was full of his cum, but that's what we were doing. Stu's tongue wrestled with mine, like it was some sort of game as we struggled to keep our lips sealed tightly and work his semen back and forth between our mouths. The creamy stuff became thin as it mixed with our saliva and some of it spilled from the corners of our mouths, but mostly we passed it back and forth. Neither of us swallowed, except maybe little tiny ones here and there, and after a few minutes our tongues were bathing in the stuff.

The rich flavor was delicious. The salty musk and the texture and even the smell of Stu's semen, all of it was good for me. My cocky threatened to spill in my panties and I squirmed in my seat. Only when we really became desperate to take deep breaths, to collect our senses and drink cool air into our flushed bodies, did we both swallow thickly and break our kiss.

"Uhhh ... whoa..." Stu said in a ragged voice and I nodded.

"Yeah," I breathed. "Did you like it?"

"I think so," Stu said, kind of blowing out a deep breath, and he blinked at me, realizing that he'd just swallowed some of his own cum.

We were both wet with it too. Some semen and spit had leaked out of our kiss and I wiped at my chin and neck with a tissue from my purse. Stu was putting away his still semi-hard cock and glancing around the theater as if someone would know what we'd just done, and maybe they did. For sure some of those people knew I'd been giving him a blowjob! They probably didn't know that I'd pushed a big load of cum into my boyfriend's mouth afterwards though. Except Stu wasn't my boyfriend and I frowned at that as I fixed my clothes and ignored my hard cocky, figuring it was all her fault anyway.


"God! I'm such a slut," I frowned, holding my face in my hands as I sat in Darla's room during lunch on Tuesday. Usually we sat outside to watch the boys and let them watch us, but the weather had turned cold with rain.

"No you're not!" she rolled her dark eyes and talked around a tuna salad sandwich. "A slut gives it away to anyone."

"I can't believe I did that," I whined, and I'd been doing a lot of that lately. Whining. "First I sucked off my roommate and then I sucked off Stu ... Two guys in the same night!"

"Well..." she shrugged. "Maybe you are a slut, Brandy."

I frowned at her.

"But only a little one," she said quickly. "Come on. Those guys are so hot anyway! Any girl would do it."

"Would you have done it?"

"Me?" she grinned at that. "I'd have done them both at the same time. Keith is just ... Youch! And Stu is unbelievably cute ... I swear, it's not your fault."

"Yeah it is," I sighed. "I told them I have a boyfriend."

"So?" Darla snorted. "A guy doesn't care about that, believe me. So long as your boyfriend isn't in the same room ... and wide awake ... guys could care less."

"That sucks," I decided. "I didn't think Stu was gonna try anything."

"Shut-up!" She took another bite of her sandwich. "That's like saying you didn't expect the sun to come up."

"Yeah."

"You're not a slut anyway, Brandy," she told me. "Sluts do it with anybody. That's not you, right?"

"I hope not," I sighed and then giggled kind of sarcastically. "But there's twenty more guys at the dorm."

"Yeah right," she said. "Just avoid them and..."

"I live with them!"

" ... don't ever, never ever say anything to Dave about it."

"Great." I closed my eyes.

"He'll definitely think you're a slut if he finds out you blew two guys in one night!"

"God!" I frowned because Darla was giggling happily.


"Hi!" A tall blonde girl smiled at me, a very attractive one with long legs, full breasts, and a cheerleader outfit in blue and gold. The only thing missing were the pom-poms.

"You're Brandy, right?" a somewhat smaller girl, but no less gorgeous with her long black hair and toffee eyes, asked me. She was a cheerleader as well, wearing the same pleated skirt and tight knit top as her friend.

"Yeah," I nodded, frozen in the act of feeding a dollar to one of the vending machines in the college commons. I'd been planning on getting a Diet-Pepsi, but they were out, so I figured I'd get an iced tea instead.

 
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