The Great Leap Forward

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My desires are altered forever by a manipulative older TV.
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lilblkboy
lilblkboy
61 Followers

[[names changed to protect the naughty]]

I had just turned twenty a few weeks back. After spending a couple of years fantasizing, a few months ago I had finally decided to try meeting a transsexual girl and satisfy my curiosity. By then I was certain that I was at least bisexual, but had no attraction to masculine men at all. After first meeting Diamond, a performer at one of the local drag bars, and then Rachel through a mutual friend, I befriended Dionna after I approached her online. Dionna was in her late thirties and a lifelong closet transvestite, never married. Like myself she'd had only a handful of partners. But she had certain desires that were starting to become impossible to ignore, and she wanted to indulge them. Specifically she wanted to seduce a hot younger man, but was still too nervous to go out in public. Eventually we exchanged pics. She was of Anglo descent, with wavy dark brown hair and very pale skin, black eyes and a somewhat solid build, a few inches taller and a little thicker than my own. I found myself most especially drawn to her powerful legs and narrow hips. Finally a convenient time window opened for her and she invited me to visit one evening.

I got there a little after seven as agreed. Dionna answered the door already dressed in a tight pair of jeans, a simple sweater and sandals. We both grinned at the same time, relieved that each actually looked like our photos. "Hi Ashley," she said, "Come on in, living room's to your left. Have a seat anywhere."

I did so, and she joined me in a few seconds. I thanked her for her good directions and told her I was very glad to finally meet. "And I love the way those jeans fit on you," I added. "You look incredible, Dionna."

She blushed prettily and smiled, clearly pleased. "Well, I wanted to look a little subdued...for now," she admitted. "I'm glad you like it, thank you. And you're very handsome yourself. So you don't think I'm too old for you, do you?"

"Not one bit." We held each other's eyes for a long time, not saying anything further. After a bit she offered me something to drink.

"All I have is wine, water and fruit juice," she explained. I thought wine was perfect, and she disappeared into the kitchen, returning shortly with two glasses of Merlot. We made some small talk about jobs, family, and the usual, until after the second refill the conversation inevitably turned to other matters.

"So I'm a little new to this," she said. "I've been dressing up since high school, but I've haven't met up with anyone in almost two years now. You seem so nice...I'm glad I met you."

"Well don't worry, Dionne," I replied. "I've met a few other girls, but I wouldn't call myself experienced at all. I'm still just feeling things out too. What I am sure of is that you shouldn't have any reason to be nervous or doubtful. You look spectacular." I finished off my glass, still a little nervous even though I was well on my way to being quite tipsy. Dionna still looked relatively normal, with only a slight flush revealing any effects.

Suddenly she got up. "Excuse me, Ashley, I'll be right back. Make yourself comfortable, okay?" She refilled both our glasses once more, then walked to the back of her house.

After about five minutes she returned, and I could only stare open-mouthed. Apparently Dionna had taken her own advice, having changed into a satin shift with strapless bra, a narrow lace thong, stockings and a garter belt, all in brilliant emerald green. She came and stood in front of me, towering over me even with the low heels she was wearing, which lifted her to nearly six and a half feet, She twisted and turned about a few times, making sure that I could get a good view of everything she had to display.

"So do you like me, Ashley?" she asked in a low voice. "Do you think I'm pretty tonight?" I took a breath, trying to keep from sounding too eager...but that didn't quite work out. I was heating up very quickly.

"Oh yes, Dionne, yes you do, baby," I answered as I spread my legs, but just barely stopped myself from rubbing my rapidly reacting penis. "Dionne, you are definitely one of the hottest girls I've seen. Are you going to let me have you tonight?"

"I don't know," she teased as she sat down next to me. "It depends."

"On what?" I asked. She opened my pants and slid her long fingers inside. I felt her nails brushing over the skin of my shaft, which was now fully hard.

"On whether you'll be my playmate," she said, squeezing me playfully.

"Isn't that what I'm doing?" Slowed down by the alcohol, I was a little lost.

"Not yet baby. But you will be, once you become my girlfriend."

Oh, I understood then. Strangely, I hadn't ever considered the possibility, having lacked any curiosity about what I might look like as a female. I didn't really have much inclination to experiment, even though I was so turned on that clear thinking required some effort.

Dionna leaned in closer, throwing her other arm around my neck and reaching under my shirt to caress my chest. As I squirmed and tried to press myself against her roaming hands, she nibbled on my ear and whispered, "I know you'd look so sexy, baby. And that would make me soooo horny...hornier than I am now. We could be two hot lesbian girls, rolling around in my bed fucking each other's brains out. I've been wanting and needing and dreaming of that for soooo long but never found the right person...."

She stripped my shirt off and pressed her bright red lips around one of my nipples. "Mmmmm, you're already smooth," she murmured as she licked me. "Smooth down here, too," she added, as her other hand brushed over the bare skin of my crotch. "I wouldn't have to do much at all. I'll just put you in some lace lingerie and let nature take its course."

I opened my mouth to say something, but it was forgotten as she bit down hard and slipped a fingertip into my ass. Before I could stop myself, I drew my thighs toward my stomach and ground my ass against her finger.

Dionna's hands withdrew and she grinned triumphantly, her eyes blazing down at me with crazed anticipation. I'd never had anyone act with this intensity of desire for me before, and it was intoxicating. My confusions and nervousness vanished like leaves in a forest fire under that gaze. "Let's go now, Ashley. Don't resist me anymore."

I turned my face to hers and kissed her passionately. I dimly sensed I had been expertly manipulated, though I wasn't sure exactly how or when. What I did know was that I was completely in her power now. "Okay Dionna." My voice was barely audible, but she could see my surrender in my eyes. "Make me your girl lover."

Dionna led me into her bedroom. I didn't know it then, but I'd never be quite the same afterwards.

Half an hour later, I stood in front of her floor-length mirror, staring at my reflection in bemusement while Dionna sat in her bed watching her creation. She'd found some of her older clothes for me, which fit nicely. I watched silently and unresisting as she dressed me nearly identically to herself, except that I was all in white, with dark lipstick, silver eyeshadow and a short dark blonde wig. Until that moment, I hadn't noticed how easily my body could mimic that of a slender (if somewhat underdeveloped) girl.

"I love your frame," Dionne purred, watching me admire my image in the mirror. "It's so narrow--" She slipped behind me and caressed my hips and ass. "--everywhere but here."

I left my reflection and joined Dionna in her bed. "I'm going to remember this forever, babygirl," she whispered. That was true enough, as there were two digital cameras covering her bed from opposing angles. Didn't matter, since I'd be nearly unrecognizable on video except by very close inspection. And I enjoyed being recorded anyway.

"Lie down," Dionna ordered, and I lay flat on my back. She crouched down and covered my stomach and thighs with slow licks and kisses. Her light touch was driving me crazy, especially when she concentrated high on the insides of my thighs. I was tensing and my breath came in rasps. Very shortly I'd learn that my thighs were my body's most intense erogenous zone, surpassed only by my anal region. "That feels so good, doesn't it, my little girl-toy?" she asked. "I know it does. I'm having so much fun with your hot little body. I love the way it responds to me...especially when I do this..." Dionne pushed my knees against the bed just under my armpits, which tilted my ass six inches into the air and exposed me completely. Her face dropped nearly out of view and for the first time I felt the incredible pleasure of a soft wet tongue pulsing against my hole. Instantly my breathing became ragged and I began pushing my ass toward her lips, trying to force her tongue inside me. She teased me for half a minute and stopped. "Hm...I think my baby girl is an ass slut," she announced. "But from now on you'll think of it as your pussy. And it's tight too. I guess you were scared to let those other tranny sluts play with it, weren't you?"

I nodded my head. Still uncertain and nervous, I had only been willing to top in my previous experiences.

"Well that's okay. When I'm done, you'll always think of your pussy as your main sex tool before you think of that pretty little piece of meat up there." My mind fogged out with pleasure again as Dionne resumed eating my ass. She went from lapping it greater and greater pressure to jabbing it directly into its center. Soon it relaxed and opened itself to her tongue, and I began gasping once I felt her tongue penetrating me at least an inch and a half deep. I heard myself moaning and begging her to suck my pussy and tongue-fuck it deep. I promised her she could have me any way she wanted as long as she kept going.

And then she stopped. "That's enough for now, babygirl." She kissed me savagely, biting my lips, sucking my tongue and leaving the smell and taste of my own ass on my lips. I matched her with equal intensity. Finally we drew apart. "Almost time for your next lesson, Ashley baby. Are you ready?"

"Oh yes, Dionna...whatever you want with me, baby, I'm ready," I moaned. I could still feel my ass--my pussy--twitching on contact with the cool air. I needed it to get penetrated again...right now...and I shamelessly babbled this aloud in Dionna's ear.

Dionna shifted back to her previous position, leaning forward with her arms locked under my knees and exposing my pussy once more. I felt three large drops of warm fluid splash against it, then felt something very hot and stiff forced against it with ever increasing pressure. "Time to see what it feels like to be fucked, Ashley. You're going to love it, I promise. Now strain and push out with your muscles." After a few beats, I managed to do so...and Dionne's stiff dick bored right into my slick hole, sinking it until Dionna's nuts swatted against my cheeks. It happened so quickly that the pain didn't really register until I instinctively tried to force her back out. My muscles clamped around her shaft, which hurt even more. "You're holding your breath, babygirl," Dionne noticed. "Breathe, then relax. Your pussy will open up in a bit. It's uncomfortable because I'm so thick, but you'll find out that thick cocks are the most satisfying. Once you realize that you're taking all that meat, being stretched until you can't stretch anymore....mmmmmm."

I couldn't speak just yet. I was still concentrating on relaxing my entire body. It took a little longer than "a bit." After three or four minutes the outraged throbbing dulled down to a hot soreness. "Can't...really...wait...baby..." Dionna suddenly gasped, withdrawing her dick a few inches, then thrusting in a regular rhythm, using almost her entire body weight to drive herself into me. The throbbing began again, but soon shifted into a maddening cycle of intense pleasure followed by faint stings of discomfort as the edge of my hole was stretched in and out by Dionne's thrusts. At the same time I became aware of a spreading euphoria unlike all the others I'd felt so far. Dionna felt it too as I stopped moving with her thrusts and went nearly limp, while I simply watched her cock slip back and forth. "Mmmmm it's happening, isn't it?" she asked, growing ever more excited. "Your little g-spot is waking up and your mind is fixating on the concept of accepting a hard dick. That's what it will define as real sexual pleasure. That's what...it means...to have...a pussy...."

Her last words went out in time with her increasingly manic pounding. But she was so right. These new sensations were more intense and less localized than any other kind of contact I'd had, except for the two or three championship blowjobs I'd gotten. It felt so intense that I didn't even want to masturbate, even though my dick was completely hard.

"I'm going to cum soon," Dionna rasped. "Your hot little pussy is draining me quicker than I expected. Rub your dick, baby. I want you to cum while you get fucked. Do it now." My hand went to my shaft and blurred up and down as I watched Dionna's motions become a little more jerky and erratic. Her entry angle changed and the sensations grew even more intense, spreading over my entire groin and--

"Uhhhhhh!" I suddenly gasped, feeling an overwhelmingly intense series of contractions in my ass while my dick swelled and released four thick spurts of cum that stretched from just above my navel to my lips. Three more smaller shots followed, dribbling over my fingers and getting smeared over my shaft. The world just dimmed away while I continued to feel what I could only think of as aftershocks for another ten or fifteen seconds. Dionna released my knees and tilted my back to a nearly vertical position. She stood up in a half-crouch and braced my back with her knees, then began stroking her own cock while staring hungrily inside the hole she was just pounding. Then her eyes shut tight and her face crinkled in a terrible silent ecstasy as she released a thin watery stream of cum that coated the entire crack of my ass. Slowly she let me lie flat again, still quivering with her own spasms. She let out one long rasping breath and then a short whoop.

Finally she focused back on me. "Oh my god that felt so good, babygirl. Mmmmm I haven't had a fuck that hot in years. And it's all on video. So good...just can't believe how good that was. Are you okay? Are you hurt?"

"Just fine," I replied in a shaky voice. "I just need a minute. That was the fuck of the century, no joke. I can't believe my first time was that good. You might have spoiled me for everyone else in the future now."

Dionna smiled, but didn't say anything to that as she lay down next to me. I replayed the whole chain of events, trying to preserve every bit in my memory. It occurred that I had just gotten the most insanely pleasurable fucking of my life from a transvestite, all while I was dressed as her fantasy fucktoy. But I knew I enjoyed all of it, especially the physical and emotional satisfaction of giving up my body to another's pleasure. I said as much to Dionna a few minutes later, after resting enough to talk again. "You're a true bottom, babygirl," she said, like this was the most obvious thing in the world. "Like I said, you'll find more satisfaction by receiving a hard dick than supplying it. And you're definitely more than a little submissive, or I wouldn't have been able to agree to letting me use you so thoroughly. Long story short, you enjoy being a bitch." I thought this over silently. I wasn't convinced of this yet, but it did make a bit of sense. Time would prove it, one way or the another.

"You'll see, baby." Dionna insisted. "But for tonight...I really want you to spend the night with me. I'll take half a sick day tomorrow...I want to spend the whole night that sexy little brown body inside out. Please?"

My stomach did a little flutter. I considered that Dionna had almost certainly exploited my inexperience and hair trigger libido to get what she wanted tonight. I didn't know if she was going through a very long dry spell and would use any hot hole that made her an offer. I didn't know if she now wanted me specifically, but would ignore me after tonight. Perhaps I was just strongly imprinting on her since she deflowered me. I suddenly became aware of the fact that I was still extremely horny...and I missed the friction in my ass...pussy.... And I missed the hunger in her eyes as she prepared to overwhelm me with her thick cock...and the satisfaction transforming her face once she realized my body was uncommonly responsive to her own. I wanted my body to be the one that made her feel that kind of intensity again...if only for one more time.

"Yes, Dionna, I'll stay."

*******

*******

lilblkboy
lilblkboy
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5 Comments
xploring96xploring96almost 7 years ago

So great telling of what it is like for a sub to learn the pleasure of giving themselves up to a woman with a cock. That your pleasure comes from giving them pleasure. I would love to be her bitch. Sexy!

AnonymousAnonymousover 10 years ago
Good,

Almost mirrors my first time being fucked, but certainly not the last, would love another t/v to fuck m,e.

stephaine69stephaine69about 13 years ago
love it and wished it was me receving that

very good story and wished it was myself ther

AnonymousAnonymousabout 13 years ago
Cant wait to hear more

i was stroking all the way through it, i want more!!

AnonymousAnonymousabout 13 years ago
Know the feeling,

Very well told and so realistic, I was hard all the way as it tripped my memory bank, my first also being a t.v. with better equipment than mine, Pauline from Blackpool you will never be forgotten.

Please tell us more.

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