tagTranssexuals & CrossdressersI'll Learn Better Someday

I'll Learn Better Someday


Author's Note: This story contains futanari (hermaphrodites, dickgirl, whatever definition works for you).


Part One: I'll Learn Better Someday


I heard my room-mate make a shit-ton of noise as she staggered into our unit; Jess was laughing real loud as she slammed the door and locked it; then it seemed she stumbled over the wooden crate we used as a coffee-table, because she yelled, "Ow!" and then cursed up a blue streak.

"Fucking piss shit!" she spat out... and then she laughed again. Jessica was giddy like that, in a cute way.

"Dumb bitch," her boyfriend Kevin rumbled in exasperation, and I raised my eyebrows at his presence. Jess was taking a huge fucking chance, bringing Kevin over so late, but whatever. If she wanted the RA to have a little talk with her in the morning, that was her problem, not mine.

"Lauren!" she hollered and pounded on my closed door. I shook my head as if she could see me, and then frowned. "Laaaaurreeeennn... you 'sleep?"

"Of course she's asleep, come on," Kevin snapped. "Fuck me sideways, Jenn, you're such a fucking pain sometimes."

Even though I really hated Kevin, he always sneered at me like I was gunk on the bottom of his shoe, I had to agree with him on that one. The problem was that when Jess wasn't doped up to the gills or drunk as a fucking sailor, she was actually really nice. That's fucking weird, right? But she was; silly and as friendly like a puppy, but ultimately harmless and sweet. She just... did stupid shit and fucked around and then expected everyone to help her out of her problems. Which we did. So I guess all of us, her friends and family, were just as dumb. It didn't help that she was pretty, in a wasted kind of way. Long wavy brown hair, big blue eyes and a really nice body. She was going to look so messed up in ten years or so if she kept going at this rate, but here in our oh-so-productive college years, she was hot stuff.

"Jess," Kevin groaned at the other side of my bedroom wall. Our rooms were narrow and not very well sound-insulated; I had to bite my lip when I was getting myself off at night, so Jess wouldn't hear, and I had no problem hearing them kiss through the thin walls. I squirmed in bed and tried not to touch myself. I don't like touching myself sometimes; I got parts where parts shouldn't be on a girl. My mother said it made me special. Right. Try having to hide a working dick in a high-school full of self-concious and cruel teenagers, and see how special you'd feel to always be dressed in baggy clothes and not showering after PE. That's so special, I wrote all about it in my super sparkly pink diary, only not really.

Now I could hear Kevin say, "Yeah. Fuck, take it," and I heard thick, slurping noises. Jess was over there sucking him off and I had push aside my self-pity to shove my hand down into my loose shorts and grab the base of my cock. She was probably on her knees on the floor while Kevin sat on the side of the bed, one big meaty hand on the top of her head, pushing her head down to take his dick in her mouth. I bit my lip and squeezed. Fuck.

"Kev," she whined after a few long moments. "Stop that, stop doing that, my jaw hurts, come on. Get up, get it in me."

There were shuffling noises, a heavy thump as the headboard of her bed was pushed sharply against the wall and then the regular sounds of a quick fuck. Kevin wasn't much into the romance and foreplay, that's for sure, but I guess Jess wasn't too picky tonight. Vaguely, I wondered what she'd had. Alcohol, definitely. Weed, most likely.

Kevin grunted and Jess panted, a sharp whine escaping at the top of each of her exhales. I pumped my dick once, slowly and tried not to laugh when Kevin went, "Fuck fuck fuck yeah fuck," and it was all over. A man of endurance, that was our Kevin. Jess complained incoherently and there was more rustling.

"Later," Kevin said and closed her door, none too gently. I heard the outer door open and shut as well, and I got up immediately, knowing that he didn't have a key to lock it. My dick throbbed in complaint but I ignored it to make sure that that the deadbolt was turned. Otherwise, some shithead might just walk in and steal the small television my mother bought for me.

I had every intention to go back to my room and jerk out a fast one, but I felt obligated to just look in Jess' room, make sure she was okay. That turned out to be a bad idea; her overhead light was on, fluorescent light cascading over her sprawled frame. Her make-up was smudged, blood-red lipstick smeared, mascara and eyeliner creating dark circles under her eyes. Her hair was spread all over her pillows, making her face appear oddly angelic, but from the neck down she was completely wicked: her blue top with the thin straps was yanked up, revealing her flat stomach and the twinkle of her navel-piercing; her tight skirt was shoved up over her hips, legs sprawled wide to reveal the shorn mound and puffy, gleaming slit of her pussy.

My dick was so hard now; my nipples were so stiff they felt sore as they brushed against the cotton of the large t-shirt I liked to wear to bed. I think I licked my lips as I went into her room, my eyes tracking the pale line of her legs. There was a tied-off condom on the floor beside her bed and I toed it away with a grimace as I stood next to her. She shifted, her eyes fluttered open and she gazed up at me blearily.

"Hey, it's Lauren," she murmured and dropped her gaze to where I had my hand down my shorts. "Whazza matter?" She tried to sit up but flopped back down, laughing weakly. "Fuck."

I got on the bed with her, feeling as if I was a million miles away from my own body, but it was like I couldn't stop myself. She smelled like she'd been swimming in vodka, the sickly-sweet smell of marijuana was a fog in the forest of her hair, but that didn't stop me from pulling her shirt up all the way and clamping my mouth over the closest breast, like a hungry baby. She moaned and wriggled, pushing up into my mouth and I worried her nipple between my teeth.

She grabbed a handful of my hair and pulled my head over to deal with the other nipple, which was already crinkling in anticipation for my mouth. I licked around it, teasing the soft pink flesh before sucking on the hard nub. I still had the one hand between my legs, jerking the hard flesh and rubbing my thumb over the leaking fluid escaping out of the slit of my cock. All that was going through my head was fuckher fuckher fuckher, a persistent train of thought was not stopping at any station at this time.

I'd fucked someone before. My mom's kid sister, Michelle. She was about two hundred pounds, with the same lush cascade of red hair as me (probably the only lovely feature either of us possessed) and we'd had sex a couple times when my mom was out working nights at the hospital, so I understood the general mechanics. I think my mom knew, too, but she didn't say anything. But Jess was miles away from my aunt Michelle, especially when I had the presence of mind to pull my hand from out of my shorts and rub my fingers against Jess' wet cunt, feeling for her clit and listening to her gasp when I managed to find it.

"No, too much," she said sluggishly, even as her hips swivelled with the movement of my fingers. "Ow ow, fuck." She must have been playing with it, trying to get off as Kevin fucked her. I pulled my mouth away from her breast and took a deep breath; this was all kinds of wrong, but I had wanted to do it for so long. Wanted to fuck her. I shucked off my shorts and the overly large t-shirt and moved to kneel between her legs. When I grasped my cock and aimed for her pussy, she lifted her head a bit and blinked at me again.

"Lauren," she said and looked down. "Hey. You got a penis thing."

"Yeah," I said desperately, shifting up close and putting the flared head right against those moist, fleshy lips. "I.. I got one, I'm gonna fuck you. I'm gonna fuck you with it. Please."

"I think it's just a dildo," Lauren said and then she moaned as I sank into her. She was soft and wet inside, and I braced my hands on either side of her head, dizzy with sensation. The walls of her pussy clenched around me, sucking onto the shaft of my cock greedily as I pulled back. She went up on her elbows, almost collapsing back anew but she managed to keep up; she whimpered as I shoved into her again.

"Oh fuck, it feels so real," she said and grabbed onto one of my breasts, pinching one of the nipples really hard. I let out a little cry of pain and pummelled into her, but she just kept pinching. I yanked her hand away, and she looked up at me with that half-stupid, watery-eyed expression and said, "Yeah, fuck me."

I went down closer, mashing our tits together and wriggling one arm behind her neck. Her breath puffed warmly against my mouth every time I sank into her, and I thought about kissing her but I just didn't do it. Her eyes were half-lidded even as she gripped my ass, urging me to go deeper and harder, and there was a burning ache in my thighs and back, but I wouldn't stop. I pressed my forehead against her cheek and arched my body a little so I could look down between us and stare at my cock as it pistoned into her. It gleamed with her juices, and I loved the look of it so much that I paused a little to admire it.

She tugged on my hair and bucked up, her pussy swallowing me whole again. I kept on watching as she did some of the work, raising and lowering her hips in an almost dream-like manner.

She whined my name after a few more seconds, her nails scrabbling in demand on my lower back, and then she cried out sharply as I slammed into her again. Sweat was pouring off me, our hair was damp and the air around us was thick with the smell of sex and our mutual cries.

"Ah!" She said suddenly, trying to wrap her legs around my waist and failing miserably. She started to tremble, and her cunt sucked at me. "Oh, shit, I'm.. I'm coming, I'm--"

"Yeah," I urged breathlessly, trying to move quickly so I could come too. Aunt Michelle taught me well, I gotta say.

"Fuck! Lauren, yessss, fuck!" she shrieked; shocked, I clamped one hand over her mouth and her cries were thankfully muffled as she came. I felt a familiar tightening in the lower part of my stomach and balls, and pulled out of her. Streaks of pearly come splattered onto her belly, and even as high as the valley between her breasts, which were hickey-bruised from my lips and tongue. She lay there limply as I coaxed the last of my jizz to dribble onto her stomach. I don't think I would have gotten her knocked up, the doctor had said that I didn't have much viable sperm. Still, there were a few.

There were a bunch of other things to think about, too. I'd fucked her without a condom. I didn't know what shit she had, even though she told me she insisted on using protection with Kevin. Damn it.

And I'd fucked her without her... like, her consent or she wasn't in her proper frame of mind or... fuck. I got up quickly, my cock gone fully flaccid and pulled on my clothes real quick. I was at the door when she said my name, very softly, but I didn't look back. I just darted into my own room and locked the door.


The next morning, I came out of my room and started guiltily when I saw her draped in one of the beanbags, the one that had duct-tape on its side because someone had been playing around with a box-cutter one day (it was me, okay, I admit it). She was dressed in a large t-shirt and she gave me a tired, but genuine smile.

"Morning," she said and went back to watching her cartoons. It was a Saturday, and it was the first time in the two years of my higher learning that I wished I had classes. I had to find some reason to get out, I couldn't be in the dorm-room with her right now.

"Hey," I said and escaped into the bathroom.

"I'm so fucking sore," she said in a loud tone so I could hear her while I was washing my face and then giggled. "Sorry about last night."

I froze with my towel halfway to my face; a few long seconds ticked passed before I managed to say: "...for what?"

"Weren't Kevin and I really loud? I'm sure I was, I was so fucked up, you know?"

"Oh. Yeah." I tried to sound non-committal as I dried up and hung my towel on its rightful place on the rack. "Yeah, it, uh... I wasn't bothered or anything."

"Best roomie ever." She beamed up at me as I came out of the bathroom and then her brow wrinkled. "I had a weird dream, though. About you!"

"Me?" My throat felt as dry as the Sahara.

"Yeah!" Her blue eyes drilled into mine, and then she smiled lazily. "I dreamed you had a dildo and all, except it wasn't, it was a real dick. You... we had some amazing sex, for real."

I laughed. It sounded so nervous and false to my own ears, but she laughed too. "Wow, that's totally crazy, Jess."

"Isn't it? It's such a lucky thing that I'm clean and shit. I mean, if you had a penis and you fucked me with it when I was all messed up, then I'd probably catch something from you, instead of the other way around. Don't you think?"

I stopped my strained chuckling instantly, but her smile kept playing around her lips. It looked the way a cobra might smile before it snaked after prey. Suddenly, she didn't appear like the ditzy, daffy chick that everyone said she was.

"No," I whispered, feeling relief and dread curl around my stomach; the dread was winning out, though. "You... if there was a situation like that, I'd be really clean, too."

"Right." She nodded firmly, her gaze still locked with mine. I wanted to run away, but it felt as if she had me nailed to the floor.

"I got this stupid assignment. Calculus! I hate that," she said and stretched as luxuriously as a cat. "Oh man, if you had that cock for real, that would be so crazy! I'd totally use it against you." She grinned again, all white teeth and warm good humour, but I felt so cold. "I'd tell everybody and I'd tell them you fucked me with that freaky thing when I didn't want to... unless you--"

"I'll do it for you," I said from between stiff lips. "No problem."

"Great!" She giggled and then turned back to the cartoons. "That's totally awesome of you, Lauren."

Trying not to breathe too hard, I went back into my room and sat on my bed, staring at the wall. Even though she'd pinned me down like that, what a fucking bitch, all I could think about was when I could bury myself in her hot cunt again, or even in her ass. I bit my lip as I imagined forcing myself into that greased up, tightly furled hole.

Then I smiled a little. She'd said the sex was amazing.

So maybe...

Just maybe...

Part Two: I'll Teach You How This Goes


I was painting my toe-nails when Lauren came into the small room that served as our tiny TV room/living-room/dining-room; she looked tired and a lot displeased, and she gave me a wry look when I grinned at her.

"Hey!" I greeted her with great cheer and she shook her head, tossing her hair over her shoulders. Lauren's hair was red... not the orangey-type, but a deep rich earthy colour. I kept telling her to put some highlights in, make it pop a little more, but she always ignored me. I figured, like everyone else, she thought I was some fashion-crazy bimbo and I was totally okay with that. Why should I disabuse them of their snap judgements? Besides, I like clothes and fashion. If that makes me a bimbo, then I'll take it.

She slunk past me and went into her room; she was about three or four inches taller than my own five-foot-three, but she always managed to hunch herself over. She hid her hazel eyes by always gazing down at her feet and wearing this really old baseball cap. Lauren had some really serious image-issues, compounded by the fact that there was a whole lot more to her than meets the eye.

Oh man, I used the word 'compounded' in a sentence! My Lit teacher is gonna be super proud, honest to goodness.

"Where's your Calculus book?" she yelled at me, sounding really pissed off now and I snickered as I blew on my nails. I liked this purple shade, and it was quick-drying too.

"On my bed!" I sang out in reply.

She stomped out of her room, stared at me grumpily and pushed open my door to retrieve my notes and the sheet of paper with calculations to be solved. Lauren was super-smart; she was majoring in Chemical Engineering or some shit like that, so my Calculus was probably easy-peasy for her. Since she'd been doing my assignments, I've gotten no less than an 80%.

I wriggled down into the bean-bag chair and smiled serenely as she came back out of my room and went into hers. I tilted my head back and gazed up at the ceiling, ignoring the cartoons on the TV for a moment as I thought back to the night about two weeks ago, when I found out her secret.

I had been so fucking out of it. I'd had a lot to drink at this frat-party; a girl named Clover gave me a joint, and by the time Kevin got me back to my dorm-room, my head was floating miles away over my head. My dad's a pastor, one of those holy-rolling types; I've been rebelling this way since I was thirteen. I don't really have any other excuses than that, really.

I remembered going down on Kevin, and then he was fucking me. I made him use a condom, too. I'm not too book-smart, but I'm not stupid either. He left right after, he's kind of a dick, and then it was like I sank down into a dream.

I had opened my eyes to see Lauren standing over me. I think I said something to her and she had her hand down her shorts for some reason. I thought that was kind of funny, kind of cute, but I didn't laugh at all. Then, I felt someone sucking on one of my nipples and that's something I really really love.

My eyes had been half-opened and I saw Lauren's messy red hair at the edges of my vision, her lips and tongue working over my breast; even though Kevin and I had just fucked like five minutes before, I was still kind of horny; weed does that to me. I hadn't even come with Kevin, anyway. I grabbed onto some of her hair and pulled her head over to my other breast, moaning when she latched onto that one as well.

When she had stroked at my clit, I wanted her to stop because it felt a little sore; Kevin had been rubbing at it earlier, but his fingers had been too dry, his touch too rough. When she stopped doing all that and ended up all naked between my legs, I looked down... I thought she had a strap-on, but I couldn't see the straps. But it felt so thick and warm when she pushed it in, and my whole body went boneless and weak as she fucked me. It was so good; I mean, it was mostly hazy, but so fucking good. I wished we could have fucked all night, had some breakfast and gone at it again.

When I came awake a little later, I was still sprawled in my bed with my clothes pulled up, the bedroom light bright over my bed; traces of jizz were white-dry on my belly and tits, and my nipples felt deliciously tingly. Kevin never came on me and he never paid much attention to my breasts, that was for sure. I had gotten up, my head still all woozy and blinked at my bedroom wall, wondering about my dream.

After I'd cleaned up and put on my pyjamas, I decided to creep into Lauren's room, just to have a look. Lauren was a heavy sleeper; she didn't even move when I pushed open the door and walked over to her bed. She was sleeping on her back, which was absolutely perfect because I all I had to do was pull down her sheets, and slide my finger underneath the waistband of her shorts. She stirred a bit when I touched her sleep-warm skin, but she didn't wake up as I lifted the top of the clothing and peered in.

I was so astounded at what I saw. Lying limp between her legs was a fucking penis. I must have made some sound of surprise, because she shifted around and mumbled, and I was out of there so fast.

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