Brandy - Cover

Brandy

Rachael Ross 1982 - 2012

Chapter 5: Really Bad Ideas

Romantic Sex Story: Chapter 5: Really Bad Ideas - 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  

"Ouch!" I said softly, wincing as I sat down for my anthropology class.

Nobody noticed, I hoped. Amidst the chaos of forty-some students finding their seats, turning off celphones, finding books and notebooks and netbooks, and especially on a Monday, because everybody was talking about their weekends and...

"What's the matter, Brandy?" Darla asked.

She was my best friend and confidante, and I giggled, blushed, and stuck-out the tip of my tongue at her.

"You didn't?" she blinked at me. "You did! Oh my God!"

"Yeah," I grinned as she started laughing and some of the other students were watching us. Well, a lot of the guys looked at us anyway, since Darla was dark and cute and I was blonde and decidedly hot.

"Last night?" she asked me and I nodded.

"Yeah," I leaned close, which was easy because we were in an auditorium, kinda like a movie theater except brighter. "He took me to the Lions Den."

"The Lions Den?" Darla narrowed her eyes. "What's that?"

"Kinda like a frat house, I think." I wasn't exactly sure why the football team would have their own house and I really didn't know how to explain it!

"Did it hurt?" she wondered.

"A little," I replied softly, "but only at first, after that it was just ... Hmmm..."

"Oh God!" Darla gasped happily.

"I'm not a virgin anymore," I giggled.

"Did he..." she paused and looked around, then lowered her voice even more, " ... Did he use a condom?"

"What? No. Uh-uh," I shook my head. "Why would he? It's not like he's gonna knock me up."

"Duh!" My best friend rolled her eyes. "I just mean, you know ... safe sex, Brandy. Come on."

"It was safe," I whispered back. "I never did it with anyone before."

"Not you! Him!" Darla sounded a little exasperated and I blamed it on my blonde hair. "He's ... gay, right?"

"No!" I blinked at her and sat up straight, wondering why she'd think that about the guy. Of course, I knew why she'd think that, but she didn't know Dave! He wasn't a fag, not at all.

"I'm sorry," she sighed, frowning a little. "I didn't mean it like that, okay? I just mean, you don't know where he's been."

"Where he's been?" I almost smiled, but I didn't want to let Darla off the hook that easily. "He's been with me. Dave's a nice guy."

"You should make sure," she decided and then the professor wanted our attention as he started his class.

I knew what Darla meant. She wanted me to make sure my new boyfriend was clean and healthy and safe for taking bareback in my butt. Even if he hadn't been having sex with fags or whatever, there were a lot of girls running around with all kinds of nasty bugs. It had even been mentioned in the college orientation handbook. "Practice Safe Sex!" written in big, bold letters along with the address and phone number for the local public health clinic.

But Dave wouldn't have anything like an STD, would he? No way! Now I was thinking about it though, because some of those bugs you just can't ever get rid of, you know? And some of them will even kill you ten years later when you're not even thinking about it. No! That was insane. Dave was wasn't like that. He'd be careful, except he hadn't even asked me if I was clean and of course I was, but he couldn't know that. And he'd probably had a lot of sex with a lot of those bimbo cheerleaders that the football players were banging two at a time in the Lions Den, and...

It was kind of freaking me out and I gave Darla a dirty look for totally spoiling my beautiful mood. She didn't notice though and it wasn't her fault. She was just being my friend. It was my fault for not saying anything the night before, but I'd been a virgin! How was I supposed to know I was supposed to worry about that stuff? This really sucked, and that was the reason too, because I'd been a virgin and now I wasn't and maybe I just wanted to be scared of something.

"Hey, you can cover for me in psych class, right?" I asked Darla as we packed up our stuff.

"This afternoon?" she asked and then shrugged. "Sure. Why?"

"I have to go to the clinic," I said and I caught the look on her face. "Not because of last night. I just need to get my hormones."

"Oh," Darla nodded as we stood up. "Yeah. I'll get the notes for you."

"Cool," I smiled at her.

"You should get tested though," she told me. "I mean, as long as you're going to be there anyway."

"Hmmm..." I made a face, but I'd been thinking about that too.

"Hey," some guy was smiling at me. "You're Dave Deere's girlfriend, right?"

"Uh..." I blinked at him. "Yeah."

"Great," he nodded. "He's pretty awesome."

"Okay," I giggled, thinking this was pretty weird. "I'll, uh ... tell him you said that."

"That's Deere's girlfriend?" I heard someone else asking and a few other comments as well, mostly about how good Dave is at football and how hot I was for being his girlfriend. It was really weird.

"You're getting famous," Darla laughed and I just shrugged, wondering how long it would take before the whole campus knew I had a dick. I'd be real famous then.


I really was kind of sore after losing my virginity to Dave the night before, so I'd dressed down in comfortable jeans and a t-shirt, with panties and a bra underneath. Mostly I'd wanted to wear clothes that would go with my sneakers, my baby blue Skechers, because high heels would have been seriously uncomfortable! It was a long five blocks to the Sunrise Clinic, which was a woman's health clinic and since I wanted female hormones, that was where I'd gone.

It sounds kind of strange to say I was seeing a gynecologist when I didn't even have a vagina, but Dr. Hurst was a nice enough lady and she didn't seem to think it was too awfully weird. She'd explained to me that I wasn't the clinic's only transgendered patient, but I was the prettiest one. Or so she'd told me and I believed her. I mean, if you can't trust your gyno ... who can you trust?

"Just wait here for a few minutes," the nurse told me after drawing some blood and having me pee in a cup. "The doctor will be with you shortly."

"Thanks," I said, rubbing my arms as I sat on a chair. Why are examination rooms always so cold?

At least I didn't have to get naked or anything. This was my fourth visit and the first one had taken awhile, since I'd had to fill out a lot of paperwork, but getting a new prescription only took a few minutes. Dr. Hurst just wanted to see me and make sure I wasn't getting sick or going crazy or anything. I guess it was a big responsibility putting people on drugs, so I didn't really blame her. I just wish she'd give me more than ten days worth at a time.

"Hi, you must be Brandy. Sorry to keep you waiting," a man smiled apologetically as he entered the room, closing the door behind him.

"It wasn't too long," I gave him a confused smile, taking in the white lab coat he wore over a light blue dress shirt and charcoal slacks. "Uh ... Where's Dr. Hurst?"

"With another patient," he told me. "I'm Dr. Benson and ... Would you rather wait for her? It could be awhile."

"Um ... No, its okay," I said and I guess he'd caught the look on my face. The place was a clinic though, with a bunch of doctors, and they were all busy.

"So? How are you feeling?" he asked, taking his own seat on a stool with squeaky wheels. He was a good looking man, except too young to be a doctor, I thought. Like barely thirty years old maybe, with black hair and blue eyes and smelling like aftershave.

"Good," I shrugged, watching as he opened the thin folder with my file in it.

"Uh hmmm..." he nodded. "You've been taking the pills every day? Your estrogen and progestin?"

"Yeah," I agreed. "Just like Dr. Hurst told me to."

"Okay," he looked up. "Any tenderness or swelling..."

"Um, sort of," I said, blushing just a little. "My breasts are pretty tender. Kind of ... sore sometimes."

"Okay," the doctor smiled. "Can you take of your shirt for me? Anything else? Headaches or nausea? Rashes or irritation? Anything like that?"

"No," I said, pulling my t-shirt up and over my head, shaking my blonde hair loose and I hadn't worn a bra or anything.

I felt a little shy, you know, sitting there while Dr. Benson rolled his stool closer and examined my breasts. They'd grown a little in the month since I'd started taking the hormones, but not all that much. Not like I'd hoped they would and I wouldn't even fill an A-cup yet, but my brown nipples were fat and swollen, and they were definitely tender.

"Oh!" I made a little face as Dr. Benson pressed his fingers just under my left nipple, kind of hard too. I mean, he was being gentle and his hands were soft and warm, but he really pressed hard that time, kind of rubbing around like he as feeling for something.

"Does that hurt?" he asked.

"Not really," I licked my lips. "It's like, um ... I don't know..."

"Just tender?"

"Yeah," I nodded. "Tender."

"Okay," he smiled at me. "That's alright. It looks like you have some bruising."

"Ah," I giggled nervously and I did blush then. "My boyfriend, he kind of ... He likes to kiss me. There, I mean."

"A little nibbling too, I bet," he chuckled. "There's no pain when he's doing that?"

"No," I took a deep breath. "It feels good."

"Good," Dr. Benson smiled and I shrugged, feeling like a little girl for some reason. "How about your testes?"

"My what?" I blinked at him, knowing what he was talking about, but... "My testes? They're, um ... Fine."

"You haven't noticed any changes down there?"

"No," I shook my head. "Should I?"

"Probably not yet, but with continued treatment your testicles may shrink somewhat," he told me. "You might experience some difficulty in achieving erection and your orgasms may be noticeably less, uh ... energetic."

"Oh!" I laughed softly, making a little face. "No, that's, um ... everything still works okay."

"Alright," he nodded. "Well, you seem to be responding well enough. I can put you on a thirty day treatment cycle and we'll check on your progress every month."

"Okay."

"Did Dr. Hurst mention counseling?" he asked me. "Have you considered talking with someone about your situation?"

"I'm thinking about it," I told him, but I'd really decided I was pretty okay with whom ... and what ... I was.

I didn't need to see a psychiatrist and try and figure out why I thought I was a girl, it seemed perfectly obvious to me. To most other people as well really, but Dr. Hurst had assumed that someday I was going to get the big operation too. She'd given me a pamphlet about SRS, Sexual Reassignment Surgery, and I hadn't gotten past the first paragraph! A pussy would be nice, but I was kind of attached to my penis and I thought my cocky was pretty anyway. It didn't make me any less of a woman, in my opinion, and who else's counted?

Dave liked it anyway, I thought with a smile, and I pulled my t-shirt back on while the doctor filled out a new prescription for me.

"Um ... Dr. Benson?"

"Hmmm..."

"I was wondering ... I mean, um ... I wanted to know if, uh..."

"What is it, Brandy?" he looked up at me.

"Last night, I kind of had ... sex?" I didn't know why I made it sound like a question. "And, uh, well ... We didn't use a, um ... condom ... or anything."

"Oh," he nodded seriously and I could feel my cheeks burning.

"I was a virgin," I giggled and rolled my eyes, because he probably didn't need to know that. "But, I don't know if ... I mean, he might have had a lot of other girlfriends and..."

"I see," Dr. Benson cleared his throat and put his pen down. "We're you, uh ... giving or receiving?"

"Receiving," I said with a hard swallow and admitting to someone I barely knew, even my doctor, that I'd been having sex in my butt...

"Were you bleeding afterwards?" he asked me and I nodded.

"A little," I agreed. "I kind of wiped myself after and, uh ... there was a little blood."

"Okay," he said. "Why don't you remove your pants for me and get on the table."

"Take off my pants?" I blinked at him.

"Your underwear too," he nodded. "Would you like me to get a nurse to join us?"

"Oh," I shook my head. "No. I'm ... I guess not. It's okay."

"How well do you know this man you were with?" Dr. Benson asked, retrieving some surgical gloves out of a box, like the kind Kleenex tissues come in.

"Dave?" I shrugged. "We went on three dates."

I didn't want to tell him that I'd just met the guy the previous Friday. I figured that would sound bad, like I was some kind of a slut or something. Three dates made it sound almost sorta reasonable, like maybe I'd known him for a week or two.

"And you were a virgin until last night?"

"Yeah," I agreed, folding my jeans and putting them on the chair so I stood there in my socks and a pair of white satin panties. I was really glad I wasn't wearing a thong!

"Take off your panties too," he reminded me. "And have a seat up here. Was it painful?"

"At first it was," I told him, avoiding his eyes with mine as I pushed my panties down and sat on the cold examination table. "But after awhile ... It didn't really hurt very much at all."

"On your tummy for me," Dr. Benson said, standing up beside me as I rolled over. "What kind of lubricant did you use?"

"Lubricant?" I bit my bottom lip and I guess my tone of voice said it all.

"Brandy ... tsk ... tsk..." he clucked his tongue. "All right, let me take a look. You should always use a water based lubricant, okay? Like KY Jelly, not petroleum jelly or cooking oil..."

"Okay," I agreed, wincing slightly as the doctor spread my butt cheeks and made little humming noises.

He used lubricant and it was cold and wet and then I winced as Dr. Benson pushed a long, gentle finger into my tender rectum. He kept talking all the while, telling me how important it was to wash myself thoroughly before and after, to use condoms, especially with sexual partners I didn't know and trust with my life. I swear he said that! But of course he had to tell me about AIDS and HIV and all that, and generally he was giving me a verbal spanking because everything he was telling me to do, I hadn't and we both knew it.

"Ummm..." I kind of sighed as my butt warmed around the man's finger and I felt my little cocky growing stiff against the padded table I was laying on.

"Just a little more," Dr. Benson said softly. "Does this hurt?"

"N-No..." I breathed, kind of spreading my thighs a little wider and I couldn't help it when my butt sort of squeezed around him with a little contraction.

"Good," he said, pumping my asshole slowly, moving his middle finger in and out and going a little deeper every time.

"Uhhh-huh..." I shivered slightly and my cocky was definitely getting hard and I shifted my hips, wriggling my butt.

"You're very small inside," he told me. "There's some swelling and..."

"Oh!" I jerked with a jolt of pleasure when his fingertip found something soft and sensitive and he massaged it gently while my ass spasmed eagerly.

"Your prostate might be slightly enlarged," Dr. Benson kept his finger there and I just blinked and nodded. "But it seems to be just fine."

"Y-Yeeeah..." I agreed with a sigh and then he was pulling his finger out of me and I frowned at the emptiness.

"You have some bruising, some small lacerations," he finally told me as he peeled off her gloves. "You'll want to keep yourself very clean and abstain from anal sex for at least a week, alright?"

"Okay," I agreed, accepting the tissues he offered me so I could wipe the lube from my butt.

"You also want to talk to your boyfriend, Brandy," Dr. Benson told me seriously. "You need to discuss your sexual histories with each other and talk about safe sex and what it means. Okay?"

"Yeah," I nodded, not wanting to turn over because my cocky was hard beneath my tummy as I lay there.

"I'm assuming he goes to the college?"

"Yeah. He's, um ... He's Dave Deere. The quarterback?"

"David Deere?" Dr. Benson narrowed his eyes. "He's your boyfriend?"

"Uh-huh," I smiled and gave him a tiny shrug. "I didn't know who he was at first. I mean, I don't know anything about football, so..."

"I see," he smiled at me. "Well, he's ... kind of famous around here."

"That's what I heard," I laughed and it was kind of cool to be dating the biggest sports hero in town.

"Okay. Well, you need to talk with Mr. Deere and I'll make a note for the lab and ask them to check your blood for STDs," he said. "It might be too soon to tell anything for sure, so just keep your eyes open for anything unusual."

"Okay," I nodded as I finally bit the bullet and sat up slowly, putting my hands in my lap and trying to cover my excitement. For some reason my penis just didn't want to get soft and I blushed as Dr. Benson glanced at my erection and smiled, but he didn't say anything about it.

"And we can check again when you come for your next visit," he continued without batting an eye, "but I don't think you need to worry."

"I don't?"

"Probably not," he told me. "Nothing is certain, but I'm sure your boyfriend is getting regular check-ups."

"He is?"

"The college takes care of people like Dave Deere," he chuckled. "Believe me."

"Oh," I nodded. "I guess they would, huh."

"We'll know for certain after your next visit," Dr. Benson assured me. "In the meantime, just be careful and be smart. I don't want to give you any bad news, Brandy."

"I know."

"Good," he smiled and seemed ready to leave, since my short follow-up had tuned into a full exam. "Anything else?"

"No," I said and then tilted my head slightly. "But if, um ... we're both healthy and everything, can we do it without a condom sometimes?"

"You shouldn't," he said with a little sigh. "But if you want to, then ... Just wash yourselves thoroughly with a good anti-bacterial soap afterwards and you'll be fine."

"Okay," I smiled and blushed, but I'd had to ask. I'd really liked feeling Dave cumming inside me and I wanted to feel it again.

The bad part was paying my bill. The clinic charged sixty dollars just to see a doctor, but getting my blood tested and all that lab stuff would cost more. I had about two hundred dollars in my purse, and my dad's credit card in case of an emergency, but I didn't even want to imagine the look on his face if he saw a bill from a woman's health clinic! He'd probably figure I was paying for an abortion, which almost made me giggle. He'd be pretty happy if I had a girlfriend, so it would be one of those good news, bad news things ... until he found out the truth.

"You're all paid up," the receptionist told me. "Here's your receipt. Do you need to make another appointment?"

"Uh..." I blinked at her. "I didn't pay yet."

"It's all taken care of," she smiled. "So ... next month, is that right? I have the third at two o'clock or..."

"Yeah. That's fine," I nodded, feeling very confused.


"Hey!" I smiled into the phone. "Are you spying on me?"

"Spying?" Dave chuckled.

"Yeah, I just walked through the door," I told him and that was true. I hadn't even made it to the kitchen when the dorm's phone had started ringing.

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