tagTranssexuals & CrossdressersThe Tomboy And The Tranny Ch. 01

The Tomboy And The Tranny Ch. 01

bySelbryth©

So I was looking at this chick Tyan, from I don't know where, but she's at the same college I'm at now, and she's well, she's totally gorgeous, and so me, stupid, plain-jane me, was just looking and thinking all these incredible 'things' about this girl, and well, I just all of a sudden realized my pussy is totally wet and I have to sit and wait for my jeans to dry up before I stand.

Whew!

But that's the way it always was for me. My friends have always said I'm pretty and whatnot, and I sorta one-quarter believe them, but the proof is in the pie and my pie just hadn't gotten even so much as a thumb in it after 22 years of faithful service! I mean, okay, I masturbate like constantly - (which is twice a day) - and I'm not really a virgin because I busted myself with a dildo (blood and everything, yuck!), and so...I guess it's just easier to say that I'm this wallflower who never has the nerve enough to even ask anybody for a date - not that I ever got asked myself, hence my mostly disbelief in that I'm pretty (I mean, who is Jennifer Tilly's sister anyhow - that's who they say I totally look like, except shorter!) - and so I just watch. And I was watching Tyan and getting wet.

She was taller than me (I'm 5'4" so just about everybody's taller than me), and real slender and pretty. No, gorgeous. Like one of those fashion models sort of beautiful. Long legs, really feminine and all that. If you look at me, you'd think it was a mop head on a stick with a couple of nipples sticking out sometimes. I have my hair down to my shoulders and it's dark brown, but though I think my hair is kinda cute, it never helped anything!

But this girl: just so totally graceful and gorgeous with gorgeous hair and pretty hands and pretty feet even! Everything about her was gorgeous. Like she was this princess or something. A real 'lady' if I ever saw one. Part of me was wishing I looked like her and another part of me was wishing I could just jump out of my closet and bury my mouth between her legs. So yah, I was having 'thoughts' about her - but from a distance.

I remember I went back to my dorm room after the first time I saw her and I just masturbated my brains out. I mean my brains just fell out on the floor. I was wasted and so happy inside and out I just melted and went to sleep. Then I woke up and masturbated again, imagining Tyan in bed with me (this whole romantic sorta 'morning after' thingie!), and that day was a pretty good day for me.

Then I saw her again and this time instead of a dress and heels, she had on shorts and rubber flip-flops and she was like way too tall for me and too leggy and so beautiful I masturbated two times in a row that night. It was all leg-stuff, like me kissing her legs and hugging myself to them and then sorta squatting on her leg and masturbating back and forth along it - that kind of kinky stuff, you know?

And then I was at this swim meet (I'm on the college team), and, you know, just bopping around in my Speedos, not thinking anything about it 'cause I spend most of my life dressed like that, and I looked up and there she was staring right directly at me. I almost sucked the whole pool into my lungs! Later when I was recovering on the sidelines, one of my team mates was calling me and waving me over and there she was standing on the other side of the fence, smiling and waving at me.

At me!

I mean, I actually turned and looked behind me to see if there was someone else she was looking at because, well, Nobody has ever wanted to see me, you know? And so I walked over and Tyan's eyes were all lit up like she was seeing a vision or something, and I figured probably the Angel of Death was walking right behind me (since I just almost drowned) or something (so I didn't look), and I smiled and she called my name and I was surprised she even knew it! I mean, I was glad I was already soaking wet because seeing her like that, talking to her, made my whole pussy just melt down into the crotch of my suit, but you couldn't see anything thank god.

And she was saying stuff, like introducing herself and saying things about how incredible I was, and the whole time it was like I had cotton around my head or something. Everything was muffled and far off and I was staring straight ahead - which is, for me, eye-level = boob-level on her - and I wanted to just hug my face into her tits and die there. I mean, I'd already almost drowned, so this wouldn't be so bad. And then I heard her say something about "...coffee later on...?" and my mind sorta came back and I looked up and nodded. I couldn't even speak. I think I coughed, and she nodded back to me and said something about "Oh my, I think they're calling you back!" and they were, so I turned and almost walked off the side of the pool and made a fool of myself.

But...I knew it would've looked like the most graceful thing compared to what was in store for me. I mean - a 'date' with a girl I'd had countless mental affairs with already? All those endless miles of leg and cute ankles, and biting her tushy and all that? My tongue in her ass-hole? Then one of my team mates slapped me on the shoulder, wishing me luck and I took my place and actually won my heat. It was like I was in a dreamworld, but I was so horny, all this energy just swelled up inside me and I really dug in and got to the finish first!

Afterwards, after the shower and everything - and seeing three of my cute team mates making out with soap and fingers and everything didn't help! - I felt like I was going to vomit. Just upchuck my guts out and they'd have to rush me to the hospital and put them back in and I'd wind up missing the 'date' and my world would still be secure, you know? I started to think about alternate ways out of the dressing room so I could sneak away, and then there they were, this pair of incredibly beautiful feet with rubber flip-flips on (no paint on the toenails, so that made it sexier for me!), and then a looong look up the loooong legs, quickly past the short-shorts and bare tummy, the tee-shirted chest, and the Tyan's eyes just beaming at me! I felt totally light-headed, like I was gonna faint or something. But then she said "Let's go!" and I followed after her like some weird little elf-dog-thingie, and she got bothered by that so waited till I caught up and then we were walking side by side.

There wasn't much of a crowd, but someone stuck a paper and pen in my face and I sighed my name, and when I looked Tyan was smiling down at me and I...I just fell in love with her. She was so beautiful it was stupid, and I was acting stupid, so it...sorta matched!

Then we were away from the pool and heading off into the actual sunset because it was like just about five o'clock, and we were going to the campus coffee shop which was west of the pool. It was sorta blinding actually and I had to squint, but right beside me, like a tall shadow, was this girl! I kept wondering if I was trapped in one of my dreams and the alarm would go off any moment and ruin it, but then Tyan was saying something, so I brought my mind back to at least hearing distance.

"I don't know," she said quietly - which matched the quietness of the sunset. "It's going to come out strange and stupid, but...sometimes I think of you and my insides just melt. You're just so totally cute - all over - and well, I just couldn't hold back anymore. I wanted to actually meet you, you know?" I think I must've nodded. My brain was frozen and numb. Hearing all this stuff from the girl I'd had such a huge crush on, just totally blanked me out. So I guess since I didn't say anything, she just went on.

Sighing, she said, "I don't mean to offend you or anything. I just wanted to have coffee with you and hang out a little. But I just want you to know, first off, that I'm sexually attracted to you, to put it bluntly..."

That was pretty blunt, but I've always had this thing for blunt objects. I thought of her knees and how I'd fantasized about riding them with my pussy just squishing back and forth over them until they were well polished and shiny! I thought of my dildos and how blunt-tipped they were and how I'd recently started crossing my feet under me and rubbing my pussy on my heels. Pretty blunt, but really nice!

"And the other thing is," she went on, "Is that...I'm not exactly what I seem to be." And then I knew it for sure. She was an alien. A really gorgeous, hot and sexy alien creature, but alien just the same. Female though - that was a real plus. But then I was thinking about all the other advantages were of having an affair with an alien; she probably had a space ship of some sort, probably, from the cute way she was dressed, a two-seater, like a space-Beemer or something. Enough room. Maybe I'd just go with her. She could abduct me and do all sorts of experiments on me and I wouldn't mind because I'd be off this world and not have to deal with shit any longer. Just go away.

Escape.

And the experiments could be great too. Like she could insert things into me and suck stuff out, and well, as I was thinking all these things I realized my panties were soaking wet - and not from my having not dried off properly in the locker rooms! Then it was like this other alien voice was speaking, and I almost choked when I realized it was me!

"Well," I was saying, real slow and calm, which is not like me at all, "I'm not exactly what I seem to be...." I was impressed with myself! I sounded so mysterious and deep and all that stuff!

"What are you really?" came the question, and I didn't feel so secure anymore.

"I may seem to be a confident jockette," I said in my normal run-on manner of speech, "But I'm really a neurotic little mess, if you want to know, who's never been on a single date because I'm so plain and unattractive and who spends my alone-time masturbating until my brains fall out on the floor. There's actually little stains where my brain lands every time!"

She laughed, but it wasn't 'at' me. I fell further in love with her, which was surprising because I didn't think that was possible.

"And so guys never look at me," I said. "Never a second glance. Well, okay, not a first glance because I'm like invisible to them. Under their radar. I've got a flat chest and narrow hips and so I guess maybe a gay male might find me attractive in a weird way. Actually, I never thought of exploring that side of things. Maybe with a dildo strapped on, I could pass, no?"

Tyan had tears in her eyes, from trying not to laugh too loudly. But I had an image of me with a dildo on and a cute guy in front of me with his ass to me and me just about to--

"So..." I went on after taking a breath, "Since no guys want me, I started to get into thinking about other girls, you know? Like girls think differently - obviously, and you should know - and they want different things, and I...don't really know if I care to find out what guys really want. Like I said maybe a gay guy would have me - for a moment - and so that's just about it."

"You are the 'cutest' person I ever met!" Tyan breathed. She was still gasping for air so I let the 'cute' comment pass by. I hated being 'cute' and nothing more. "I just never met someone so...interesting and pretty on the inside. Some of the girls here on campus - really nasty, ugly insides, you know?" I nodded. I knew. A few.

More than a few. So beautiful they were dead inside, having focused so much on their outsides.

"And you're so different from them," Tyan went on. "So sweet and unassuming. Like a breath of fresh air, or an alien from another planet. A hottie though!" She laughed again but it was a nervous laugh this time.

"Me? A hottie?" I asked. I thought there was some porno chick standing behind me waving at her or something. I did glance back to make sure. Nothing there but the shadows of the trees. Tyan was nodding though. We'd stopped walking and now we started again - toward the coffee house.

"Yes," she said. "Everything about you is hot - physically. You're so well conditioned you can see every muscle, every bulge - but you're not like a weightlifter or something. You're so feminine and smooth and graceful and...sexy. There's no other word for it."

"Wait!" I said, "If you'd be willing to sign an affidavit of the 'sexy' part, maybe I could get some dates, no?"

"You're 'on' a date, silly," Tyan whispered, "And I'm loving it already..." She sighed and then continued, "But there really is no other word for it. Sexy. You're sexy and you're, I dunno - you've got this aura of sensuality all around you; like you exude some sort of erotic vibe with every step you take. I just can't ignore it. I mean, every part of you turns me on, and I have to admit, even though you'll think it sounds stupid, that I've pretty much memorized every part of you; the swimsuits you guys wear don't leave much to the imagination, you know?"

My lower lip crinkled against my upper teeth as I thought it over. I was nodding slowly and trying to swallow what had just been said to me. I couldn't believe it - didn't really want to in case it was just all some joke someone had put this girl up to - but I did suddenly feel as though I'd been a nude model in art class forever! Like I was exposed even now and couldn't do a thing about it because it was already in someone else's mind.

"I've sorta memorized you too," I heard myself say! I couldn't believe it. If I had tape I would've taped my mouth shut right then and there - or gotten string and needles and sewn everything shut.

"Really!" Tyan said happily. I nodded, I think. Then we were going into the coffee house and it was noisy and busy and loud music was playing and people were yammering and the smell of fresh brewed coffee took my mind off what we'd been saying. We went and ordered to-go, and leaned against a wall, waiting for the order.

When we left the place it was already dark and our cups of coffee were just steaming away. Sorta like the way I felt inside. If I'd been inverted at that moment, and my panties pulled off, my pussy would've been just steaming - probably even foaming! Pussy Latte. But then there we were, strolling along the well lit walkway with darkness and tree shadows everywhere else and I didn't even know what to say - not that I ever thought I would.

"So..." my tall friend resumed, "If I've memorized you and you've memorize me, then...I guess the only thing to do is to check each other's notes. Like...find out if our memories are as good as we think they are...." That one took me a moment because I'd been glancing at Tyan's feet and noticing how they almost glowed in the light, and my mind was filled with those thoughts and not what was being said. Then it hit me and I nearly choked on my coffee.

"Sure," I said, with complete brilliance. I was such a orator, let me tell you!

"But like I said," she said softly, "I'm not what I appear to be. I...I'm probably not what you want either way, but...I don't care anymore. I just have to be with you, even if it's only for a moment..."

I was thinking, 'what the fuck are you talking about tall-lady?' and then she said we could go to her place and I nodded again because my place was totally decrepit, and then we were riding the elevator up to the eleventh floor and I was thinking - okay, I 'think' I'm going to actually have sex tonight - with a real person and not just a dildo! I was really trying to force that alien concept into my mind, but it just didn't want to go in there. It was like it was too unreal or something. But I went along with it, knowing I'd probably wake up any moment and have to get out of bed and get to class.

Then we were in her place and she locked the doors and turned the lights down and sat on her couch. I just stared. Her legs were just so outstanding! But then she slipped her top off and my eyes were right there and all I could think about was her nipples and how hard they were and how beautiful her tits were. And then I felt a need to show good faith and equal the playing field so I just stripped totally naked; everything off, even my watch and necklace. Then, in the dusky shadows from the indirect lights I noticed something push up - or downward, actually - at the crotch of Tyan's shorts, and her hands quickly were there, pushing it back down. The only thing I was thinking was 'alien clit!' and then I was just overcome by it all and forgot about everything. My skin felt like it was on fire, I was so horny, so I went right to her, knelt in front, undid her short-shorts and pulled them down. Her panties were beautiful and white and lacy (of the kind I always meant to get but never got around to), and as her shorts slid down those loooong legs, I mashed my face into her crotch and inhaled. I didn't care if I looked foolish or overwrought or whatever, I just needed to smell and feel and kiss and hug, so I did. Even if she was an alien and some sort of weird fleshy shaft would now jut out and implant spore down my throat, I didn't care. I just kissed her crotch right through those panties, and breathed in her wonderful woman-scent and would've died happily just like that, but then Tyan touched the sides of my face and made me look up.

"...I said I was different..." she whispered, and her eyes were all glossy for some reason. I mean, mine were but it was out of sheer joy at finally having my face jammed into a girl's crotch, you know? That was when Tyan got her thumbs down the sides of her underwear and pushed them down and my mouth was just salivating! I breathed in and out and then fabric was being replaced by smooth, hairless skin and I rubbed my forehead on her tummy, and then more fabric was gone and my mouth was right there and I felt ticklish hairs on my lips, and the doink! and something bumped me under the chin. I kept smelling and nuzzling my face into her now bare crotch, and she finally took me by the face again and made me stop. She pushed my head back and the thing that bumped my chin now stood straight out at me. It was so beautiful I just opened my mouth and pushed my lips tight around the head of it! I squeezed my lips and something like honey oozed off and dripped on my tongue. I rubbed my tongue tip along its underside and then pulled back slightly and pushed all the way onto it.

Now I'd learned from some sorta weird intimate play with my dildos, that I could deep-throat them - even the eleven incher - by holding my breath and then pretending I was 'yawning' like first thing in the morning; makes all the muscles spread out at the back of the mouth. I'd done that lots of times, so now I did it again and took the whole thing into me - into my body! It was so sweet. So hard and not overly long and I felt like I was about to orgasm just from doing that. I heard this sweet, soft gasp from far above and just fell in love with Tyan on an even deeper level! I pulled back and enjoyed the feeling of that inch-thick thing sliding out through my wet lips. It was so wonderful! I finally let it pop from my mouth and pushed it up with my nose and forehead and just rubbed my face against the bottom of it. More stuff oozed out and I rubbed my face into it, breathing deep and totally loving Tyan's scent.

Then my tongue reached out under it and found a soft, smooth fleshy pouch and I rubbed it and licked it and felt the two round things inside the pouch and then I pursed my lips against one of them and sucked it and found I could actually suck it gently into my mouth! So there I was, on my knees, totally with everything just exposed (and wishing I had more to expose), slurping away, and then Tyan's hands were touching my face again and I looked up and saw her just beaming down at me! It made me so happy I almost came from it! But her eyes were all half-lit and real 'bedroom eyes' and seeing that on another person, especially one I was eating out, really brought me over the edge. I mean I wasn't even riding my heel or anything - just kneeling there with this wonderful ball between my lips - and I came. So weird. But I figured it was because it was so real and so intense! And I guess it was the same thing for her because she was mumbling stuff, just over and over and on and on (sorta like the way I think), and saying stuff like, "Oh my god, my god, sweet, soft, pretty lady, my god, oh my god..." and I was thinking, 'she talking about herself, as in 'lady?'

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bySelbryth© 4 comments/ 54926 views/ 24 favorites

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