Going Gurly Ch. 01: Cara's Clitty

My stories are all true recollections of events from my life, as accurately as I can remember them, with two exceptions:

1. The names of my partners have been changed for their privacy; and

2. I have omitted any references to safe sex, because reading about people fiddling about with condoms is not to my mind very sexy, and in stories you don't need to be as sensible as you do in real life!

*****

The arrival of the internet in the mid-1990s was a wonderful thing for a shy young faggot. I'd only had one real life sexual partner, but via the joys of cybersex I was able to have dozens of men fucking my mouth and ass.

And it was pretty much always them fucking me: while my real life experience was limited, I'd done enough to know I much preferred the 'bottom bunk'. I loved being on my knees sucking cock, and being finger-fucked had left me a quivering, moaning mess. The idea of being fucked was a major turn-on.

Eager to prepare myself for being fucked for real one day, I went to an adult store and purchased a vibrator. Nothing too fancy: it was a simple pink tube with a tapered end, probably six inches long and three-quarters of an inch wide. I also bought a healthy-sized bottle of anal lube to go with it, and began experimenting. Initially I could only penetrate myself with the first inch or so, but within a couple of weeks I could comfortably take the entire length, leaving only the base protruding from my well-filled ass.

The vibrator then became a regular part of my masturbatory adventures. I'd fuck myself with lubricated fingers, then grease up the vibrator itself and lie on my back, legs spread. For a little while I'd tease the steadily buzzing tip against my hole, imagining I was lying underneath a man and it was his cock pressing against me.

You want it don't you, slut? You want this hard cock in your ass. You want to be fucked. I'd picture the man grinding on top of me and taunting me, calling me names, until eventually I'd whisper a response to this imaginary lover.

"Yes sir, I want you to fuck me. Please fuck my slutty ass."

I'd slide the vibrator in, slow and easy, until it was nestled deep inside me. Oh you like that don't you, slut? Like that big cock deep in your faggot fuckhole. Show me how much you want it.

"Please sir, I want your big cock to fuck my faggot ass. Pound me, fuck me, use me. Make me your cumdump."

By now my own cock would be standing stiff as I began to slide the vibrator in and out of my well-lubed ass, imagining a big strong man atop me, his cock thrusting in and out as he called me filthy names. Cocksucker. Sissy. Fucktoy. Bitch. Whore. Faggot. Real men fuck sluts, but you are a slut. A worthless, cock-hungry bitchcunt cumpdump slut. Well take my cum, slut. Take a real man's cum in your cunt, because that's what this hole is and that's what you are.

I'd let go of the vibrator now, leaving it buried deep inside me as I frantically jacked my cock until I creamed all over myself.

Afterward I'd have to sneak to the bathroom and wash up both my toys and myself, of course, but even that had its pleasures. I loved how easily my fingers would slip inside my ass as I cleaned up. You've just been fucked, you little tramp. More than once I ended up masturbating again in the bathroom, staring at myself in the mirror and whispering abuse at myself.

"Cunt. Slut. All you're good for is being fucked."

It was around then that the internet delivered again, as I discovered shemale pornography. Soon my computer's hard drive was filled with images of these vixens; seemingly feminine except for the soft cocks dangling between their legs; being ploughed by men. I masturbated over the pictures again and again, always picturing myself in the shemale's role, wishing I was in their place, until the thought finally came to me: why couldn't I be?

Sure, I wasn't as feminine in looks as the gurls in the porn pics, but I could wear female clothes and if I did, then the kind of sex I craved would be obvious right? Why else would a man dress as a woman than to signal he wanted the feminine role? Well, of course it's actually a lot more complicated than that; some crossdressers are straight and some prefer to be tops and human sexuality is much more wide and varied than my naive 22 year old self understood. But it made sense to me at the time and I sound gravitated to crossdresser-friendly online sites, trying to find a local gurl to help me get started.

Initially this search was unsuccessful, though I did find plenty more people willing to cyber with my new 'Anna' persona! This didn't always work out so well, as I quickly discovered that some men want a t-gurl for her cock, and I had no interest in topping, but other times I would be left a cummy, breathless mess.

And then I met Cara. She was an experienced crossdresser, willing to help me learn the ropes, and she was local to me. She warned me ahead of time that she wasn't particularly passable; but but then, I didn't expect to be either. And she admitted to being bi-curious, which was important to me since I was in this for the cock!

So we arranged to meet.

Cara was in boy mode for our initial meeting. S/he was about 30, plump like I was, but rather shorter, and dark whereas I am fair-haired. We chatted briefly in a 'get to know you' kind of way, then headed back to her place.

The first thing we did was go through her wardrobe. She had several dresses, including a black one that I would have liked to try, but which barely covered her ass and would therefore have been ridiculous on me. She also had a pair of heeled boots - alas, again too small for me - some skirts and blouses, and an assortment of nighties and underthings: panties, bras, stockings and hose.

"I don't own breast forms." she explained, "But I use balloons with a bit of water in them to give me boobs. So, you want to try some of this on?"

I nodded. "You bet."

We divvied up the clothes and, apparently feeling a little bashful, she sent me into another room to change. I stripped and began to become Anna for the first time. I'd declined panties, so I put on the pantyhose first, feeling the satiny material cling snugly to my cock. Next came the bra. Cara had explained that I should put it on backwards, then fasten it at the front before twisting it into the right position and putting my arms through the straps. This took a bit of fumbling on my part, but I got there in the end. Then I slipped a tan dress over the top. It was a bit on the short side, given I was taller than Cara, but at least came to a couple of inches under my ass.

Heading back into the main room, I waited for Cara. After a few minutes, she emerged. She was wearing the black dress, black fishnets, and her boots, along with an auburn wig (alas, her only one).

"I brought the make-up." she lifted a box in her hand. "Let's start with you."

I sat there, meek and still, as Cara applied foundation, eye shadow and lipstick to me. Then I watched as she applied her own, in a rather more 'goth' style than she'd done mine.

Afterward, Cara let me look at myself in a full length mirror. I certainly wouldn't win any beauty pageants, but with a wig or properly styled hair I thought I'd get by at a distance, like Cara herself could do.

"Do you like being dressed?" she asked

"Yep." I turned so I was looking over my shoulder at the mirror, and pulled my dress tight over my ass. Mmmm, look at that fuckable shemale rump. The boys will pound that bitch until she can't see straight.

My naughty thoughts were interrupted by a few more lessons: how to sit like a girl, and how to sound more like one (mostly "don't worry about pitch, just keep the volume low"). But after that we finally ended up on the couch together, not quite touching.

"So ..." Cara looked a little nervous. "You've been with guys before right? Did you like it?"

"I did. But we don't have to do anything if you don't feel comfortable. It's up to you."

"I think I want to try it."

I leaned in and our lipsticked mouths met in a wet and sticky kiss. I opened my lips and her tongue probed into my mouth, thrusting against mine. I suckled on it briefly, the licked my tongue tongue into her mouth.

As we continued our gurly make-out session I slid my hand between her legs. She parted her thighs and I ran my fingers up her fishnets until I found her pantie-covered cock. She was already semi-hard; probably had been since dressing up; and felt pleasantly thick-shafted though not especially long. I palmed her cock and gently rubbed it, feeling it swell against my hand.

Cara soon returned the favour, her fingers caressing my swelling shaft as we continued our sissy tongue kiss. Look at us, a pair of girlyboy faggots, frigging each others clit's.

I broke our liplock. Cara's lipstick was now smeared, and I was sure mine was too. "Ready to go further?"

"Yes!"

I'd intended that I'd take the next step but before I could, Cara slid off the couch and started pushing up the hem of my dress. I lifted my ass to help her, and as soon as the dress was out of the way she grabbed the pantyhose and pulled them down, letting my sissyclit spring forth.

"That's the problem with pantyhose." she grinned, "You've got to take them off to get to the fun stuff."

Any answer I might have made was cut short when Cara enveloped the head of my clit in her lips.

It might have been her first time sucking cock, but it definitely wasn't the first time she'd ever thought about it. Cara showed no hesitation about swallowing me deep, bobbing her mouth up and down my shaft and smearing away what was left of her lipstick.

"Mmm, good girl." I laid back and enjoyed her oral ministrations, savouring the sight of another sissified cumslut on her knees. That's where you belong. On your knees, worshipping cock like the faggot cumdump you are.

"My turn." I touched Cara on the shoulder. She released my cock and got to her feet, then rested one hand on my shoulder for balance while I pulled off her knickers. "Here, take a seat on the couch."

I knelt in front of my crossdressing lover and swallowed her clit. She was circumcised, and my original impressions of her length and girth were accurate. She fit easily into my mouth.

I bobbed my head up and down, slurping hungrily with each retreat from her cock. As I did so, I inched my knees back until I was basically on all fours, with my forearms taking my weight on the couch. I could feel my own cock swaying between my splayed legs, and knew both it and my ass were exposed by my hiked-up dress. Any man who walked in now would see exactly what you are: a sissy cunt fucktoy with a mouthful of gurlcock. They'd probably rip down their pants and fuck your asscunt, without saying a word, because they know that taking cock is all you're good for.

Releasing Cara's cock from my mouth I kissed my way down her shaft and then lapped sluttishly at her balls, running my tongue all over the fleshy sac. I loved the feel of her saliva-slicked clitty rubbing against my face, marking my cheek with pre-cum and spit. I sucked first one globe into my mouth, then the other, slavishly laving them with my tongue.

Cara moaned with pleasure and hooked her legs over my shoulders, pulling my face deeper into her groin so that my whole world became nothing but her clit and sissyballs. I licked, lapped and kissed with literal gay abandon. Look at you, a slaveslut even for a sissy's cock. You worthless faggot fucktoy.

Finally Cara let her legs slide off my shoulders and I came up for air with a new suggestion.

"Want to fuck my face?"

At her nod, I lay on my back on the floor, arms stretched above me. Cara straddled my face, her knees either side of my head, then guided her cock back into my open mouth. This down, she leaned forward, pinning my wrists to the ground with her hands, and began to slowly pump her hips.

I lay in darkness, Cara's dress having draped over my eyes, pinioned to the ground as her clit slid in and out of my wet, cocksucking mouth. It was stuffy and a bit hard to breathe, especially when she thrust her clit deep, her sissyballs pressing on my chin and her belly on my nose.

It was wonderful.

Pinned, helpless, just a wet hole to fuck. This is where you belong. Take that sissyclit you stupid cunt. I surrendered myself to the role of sissy fuckhole, meekly accepting every thrust of cock, sinking into an internal monologue of self-abuse. Whore. BItch. Cumdump. Take that sissyclit because you're not even worth a real man's cock.

Finally Cara pulled away from me. I stared up at her, slightly breathless and a bit disappointed she hadn't cum in my mouth - something I was yet to experience.

"Let's want each other off." she said.

So we went back to the couch, sprawling side by side, my left hand stroking her clit and her right hand stroking mine. I came first, spattering my thighs. Then Cara did, leaving my hand sticky with her sissygoo.

"So ..." she asked after we got cleaned up. "Do you like being a gurl?"

"I think so." I deadpanned. "But we'd better do it again to be sure."

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Cara and I hooked up numerous times over the next few years, until she had to move away for work. We had a lot of firsts together, after this first time getting gurly. She gave me my first wardrobe items, was the first to cum in my mouth, and was also the first to put me in a collar ... which I'll talk about more next time!

xxx

Anna_subCD