The obligatory disclaimer: This is a work of fiction. As such, all characters are figments of the author's twisted and deliciously dirty mind. Any resemblance to actual people is strictly an unintentional coincidence. If you are under eighteen or are offended by things of a decidedly sexual nature, you shouldn"t be reading this. For those under eighteen, experience has taught me, as it will teach you, that life will mess with your mind enough after you reach adulthood. You really don't need a head start.
Now, without further delay, back to the story!
14
Frank's Wicked Mind
"I gave that hypocritical son of a bitch a blowjob, Frank," I protested, following her poo-pooing of my rant concerning the questionable parentage of the Good Reverend Artemis Collingswood.
"Did he enjoy himself?" she asked, rather obtusely.
"He experienced the Second Cumming, if that's what you mean," I replied.
"Second Cumming?" She did a doubletake and eyed me with an incredulous expression then leaned back and smiled.
We were sitting in her tiny kitchen at her microscopic kitchen table. She wore this delightful blue spaghetti-strapped blouse that did next-to-nothing to hide her pointy nipples, and yet-another pair of her short-shorts. The effect served its visual purpose.
I had on my usual jeans and a black tee-shirt, but I had added a blue button-down shirt (at the moment, unbuttoned) to my ensemble – mainly so I'd have a pocket in which to carry my cigarettes. What I didn't know was that by the end of the night, I'd be looking a lot more like her, and she'd be looking a lot more like me.
"You've been waiting all damned day to say that, haven't you?" she accused.
"Damn right!" I responded. "Can't expect me to let a golden opportunity pass by."
"Hmm," she intoned, still giving me the stink-eye, but I could tell there was a hint of curiosity behind it. "Did you enjoy yourself?"
A certain part of my anatomy twitched. I nodded and gave her my best wicked smile. "I think I'm going to learn to love sucking cock." But then my recently offended brain rebounded and I tried to bring the conversation back to the fraudulent bastard and his Municipal Moral Codes. "Don't you see what they're doing? Doesn't it piss you off?" I asked this second question in an effort to tweak her inner-radical, but for some reason she shined it on like an annoying and insignificant bit of trivia.
"You said it yourself. None of this has been approved by the City Council," she continued her poo-pooing. "Assholes like that crop up every few years and blow their hot air all over town. And then the Gay Community throws a bunch of lawyers at them and it all goes away. This time won't be any different."
"Are you sure about that?" The part of my brain containing the fact of the Mayor's introduction of that two-faced son of a bitch asked this question. Another part of my brain, however, couldn't take my eyes away from her perky nipples, and still another region within my Medulla Oblongata had fixated upon the evil plan my lesbian friend and her strapon had for me this very evening.
"Yes," she declared. "I am. And since I'm much smarter than you are, you should bow to my superior intellect and quit changing the subject away from the blowjob you gave last night."
"The subject," I countered, "is the man I gave it to."
"Fuck him," she replied.
"No thanks," I passed. "His ass does nothing for me."
"His cock apparently did," she observed.
"Yes," I smiled. "It did." And just like that my fears and suspicions and the sinking feeling in the pit of my stomach that this time was different, that this time they wouldn't just sweep it aside in a flurry of legal ministrations, dropped down into my groin area and once again, my mushroom head took over.
??
It's possible, perhaps even probable that what later transpired would have happened in any case, regardless of whether or not I allowed myself to be distracted by my lesbian friend and her phallic symbol fashion statement. After all, it is the epitome of conceit to suggest I alone could have stopped Reverend Collingswood and his Moral Goon Squad from following through with their repressive and dastardly plans.
But that's the funny thing about guilt. It doesn't require reason or a strong basis in fact, only an internal causal link between one thing and another; the notion I could have prevented it had I not been so consumed with the idea of Frank fucking me up the ass.
??
"Well aren't you just the nasty slut!" My lesbian exclaimed.
"Jealous?"
"Of your cocksucking adventures? Hardly," she replied. "I like innies, not outies. You may feel free to have all the dicks your little heart desires."
"Thank you ever-so much."
"You're welcome," she said.
An enigma occurred to me. "Wait a minute," I began. "If you're all about the innies, then what the hell is this twisted, yet delightful fantasy you have about fucking me with a strapon?"
"Um, errr..." she sputtered, her inconsistencies showing.
"Uh huh," I challenged.
"It's simple, dumbass," she replied, resorting to insult in an effort to deflect. "I've fucked my female lovers before – and will again, thank you very much. The only difference is, you're a mutant, as has already been established. There's something indefinably weird about you. You're a freak of sexual nature," she explained (or attempted to).
"Oh, it's back to that again, is it?" I asked.
"We've never left it." She beaned me in the chest with a salt shaker and then continued. "To be honest—"
"That'll be uncharted territory for you," I interrupted.
"Bite me," she snapped. "To be honest – shut up – there are times I wish I'd never met you, because then I wouldn't have to deal with all these weird erotic feelings I have for someone with the wrong parts." She held up her hand like a traffic cop to stop me from making the smart-assed reply she knew waited just behind my lips. "And it's not even the parts that are the problem, because I still don't want anything to do with that thing between your legs. It's the fact that you're a man – or a boy – or whatever the hell you are. It's your male-ness. By all rights, I shouldn't want anything to do with you beyond pure, platonic friendship. I shouldn't – in any way, shape, or form – get soaking wet when I think about you. It really pisses me off," she finished, not looking the least-bit pissed.
I let her last declaration hang in the air like...I don't know...some hanging thing, as I gazed at my confused friend. Finally, I asked what seemed to be an obvious question: "You love me, right?"
"Eeeyoo," she replied with an exaggerated lip curl, eyeing me like something she'd scraped off her shoe.
"Fuck off, bitch," I retorted with affection. "You know you do."
"I suppose," she grumbled.
"To me, sex is a natural extension of love," I explained.
"Yeah, but you're a freak."
"That's as may be," I laughed. "But, if you love somebody – if I love somebody – it's natural to want to give them pleasure. I'm sure even a dim bulb like you doesn't need me to explain the correlation between pleasure and sex." She answered me with her middle finger, but I carried on, undaunted. "Fine, have it your way. Let me just leave you with this: Love means never having to say I'm sorry you turn me on."
"Spare me the Hallmark platitudes, freak-boy," she said, but her smile said something else.
"Fine...whatever... Be that way," I said. "I'm a freak, a mutant. I suck as a human being and should be cast into the pits of Hell for loving a mental deviant like you. Feel free to keep your twisted fantasies to yourself."
We sat there, staring at each other, for an indeterminate period of time, until she finally replied by sticking her tongue out at me. I countered with a wicked expression as I licked my lips in an exaggerated manner.
"So..." She let the word hang there, with a wicked look of her own dancing across her eyes.
"So...what?" I asked with perfect innocence. I knew she was changing the subject, or – more to the point – bringing the subject back to where we started.
"Are you going to go through with it?"
"Whatever do you mean?"
"Are you going to let me...you know?" Her verbal coyness seemed completely out of character. She must have been nervous. Truth be told, so was I.
??
Her sudden reserve no doubt resulted from the notion that doing what she was talking around doing would forever change the nature of our relationship. But it wasn't about the sex itself; rather, it was about the nature of the act.
As I said, we had had sex (of sorts) in the past, so it wasn't a question of adding a sexual component. Frank was a horny little so-and-so who liked a good spanking from time to time, and I had been more than happy to indulge her fetish. Being spanked gave her intense orgasms, and I – number one – enjoyed giving them to her and – number two – loved playing with her glorious bottom, especially when she allowed me to lick and nibble, provided she could lie on her belly or sit on my face (thus covering it) and pretend I was a woman.
There was the rub, so to speak. As long as she could pretend I had the right plumbing, then her lesbianism remained intact – at least as far as her twisted and securely rationalized mind was concerned.
Like all good sex, it's a mind-fuck, but engaging in the other kind of fuck – the physical act of fucking me – made the façade logistically impossible. Short of her wearing a blindfold from the moment we started removing our clothing (which up to that point had never happened – we had never been completely naked together, choosing always to retain some manner of clothing – mainly my own, covering my male protuberance), she couldn't perform the actual fucking without seeing my "outie," which would then burst her fantasy bubble.
It was all a bunch of bullshit anyway. With the extraordinary number of times I'd had her lying across my lap – and, therefore, right on top of my erection – as I spanked her, she'd have to be blind, deaf, dumb and bereft of any nerve endings not to notice my incorrect anatomy. Little did I know the lengths to which she was prepared to go in order to preserve her illusions.
??
"I have no idea what you're talking about," I lied.
"Are you going to let me..." still unable to say the words.
I took pity. "Am I going to let you fuck me?"
"Are you?"
"Is a bear Catholic?" I asked, mixing my metaphors. "Does the Pope shit in the woods?"
"How much wood would a woodchuck chuck if a woodchuck could chuck wood?"
"About a cord-and-a-half, from what I understand."
She burst out laughing and bowed to my superior smart-assedness. "You win!"
"What's my prize?"
"My strapon up your very nice ass," she replied, finally breaking through her verbal fantasy walls.
"I'm ready when you are."
"No you're not," she declared, her smile going into wicked overdrive. "You're nowhere near ready."
"What the fuck are you talking about?" I questioned.
Her answer sent a chill up my spine and a ten-thousand volt charge straight to my dick. "First we need to go shopping."
15
Shopping with My Lesbian
"With your tushy," Frank said, giving the topic of discussion a playful squeeze, "I'm thinking you need thigh-highs and a garter belt." We were wandering the streets of our fair community, browsing the windows of the various and sundry boutiques as we passed, sipping cups of specialty coffee we'd picked up along the way. She had changed from shorts to (delightfully tight) jeans, but kept the nipple-displaying spaghetti-straps.
The late-afternoon sun felt warm, but nowhere near as heated as the area between my legs, which I had to cover with the tail of my periwinkle blue button-down shirt as best I could in an effort to avoid causing a scene. "Do you, now?" I replied, swearing silent vengeance for what this little wench was putting me through.
"I do," she answered. "And I know just the place."
??
Prior to being informed of the costume portion of Frank's evil plan, I'd never given much thought to wearing women's clothing. Maybe it was the absence of a mother and, therefore, the lack of a readily-available wardrobe. Who knows? Since then, however, and over the passage of time, I've found it necessary to have two closets: one for my male wardrobe, and one for my female. I'll give you three guesses as to which is bursting at the seams. You'll only need one.
That said, I do not consider myself to be any of the plethora of trans-whatever labels. For me, gender doesn't enter into it. I dress and act like a woman when the situation (or the mood) calls for it; likewise with the masculine side of things. From my experience, and having a decent knowledge of history (yes, I have interests that don't involve sex) the labels we, as a society, seem to slap on absolutely everything have gotten us into far more trouble than they're worth. Granted, this is a complicated world and we are under constant bombardment from input of all shapes, sizes, colors, ethnicities, philosophies, religions, orientations and viewpoints, and so a certain degree of labeling is necessary, if only to keep everything straight. But just as with the biological categorizations of class and phylum and whatever else there is, these subsections are supposed to be the beginning of our exploration – not the end. All too often, the thinking stops as soon as the label is applied.
I'm just saying...
??
She pulled me down a side street and to a small, out-of-the-way clothing shop called Cloth Dreams, featuring (if the display window served as any indication) outfits not normally worn in public, and deemed too ribald for the homogenized sensibilities of the average American mall. Frank, it seems, had been there before.
"Get your delicious butt over here!" the proprietor, Constance McGuire, squealed upon seeing my companion. She engulfed Frank in a none-too chaste embrace, grabbing a healthy handful of the delicious item in question.
Constance (Connie to her friends, among whom I now count myself), appeared to be in her mid-to-late thirties, and stood about five-foot-ten, with a slender build and nice, long legs encased in white thigh-high stockings beneath a pleated skirt, with the hem resting at the junction between stocking and bare flesh. Her blouse was a sheer number in white that did nothing to hide the red bra beneath. The same shade of red colored the patent-leather shoes on her somewhat large feet. She wore her honey-blonde hair in long rivulets, giving her a decidedly fresh-fucked look. It framed an interesting, somewhat angular face featuring brilliant green eyes behind round spectacles. Her lips were the same color as her bra and shoes.
"Is this him?" she asked, devouring me with her eyes. She spoke with a warm whiskey voice, like one of those old-time actresses: Lauren Bacall, Sally Kellerman; the kind that oozes sexuality. As it turns out, she used that voice on a regular basis as part of the weekly Drag Queen Breakfast at the Orpheum, but I did not know this then.
"This is him," Frank confirmed.
"I approve. I approve. You lucky, lucky girl!"
"He's got the wrong plumbing, Constance," Frank said, feigning annoyance. Her dancing eyes told a different story.
"Not for me!" she declared. "I can't wait to get him naked."
"Excuse me?" I blurted as that thing in my pants sprang to life.
Connie noticed. "Oh now I really can't wait!"
Frank explained. "She's going to make sure everything fits properly."
"Is that so?" I asked. When Frank first told me what she had in mind, I didn't know how to react. One the one hand, we would be entering uncharted territory, which had pretty much been a running theme since I journeyed into Zebulon, a scant four days previous. Getting fucked wasn't the question. I'd been thinking about it for months – maybe years – and I had finally gone and done it, albeit in a mildly unsatisfying manner. I had not, however, thought about dressing for the occasion until my lesbian friend broached the subject. On the other hand, the idea – once planted into my dirty, delighted mind – had caused an unexpected, yet definitive response from my already over-active libido. The whole thing had me about as turned-on as I had ever been. And that's saying a lot.
"Okay," Frank said, taking the bull by the horns, "this is what I want," and then described in precise detail the clothing she wished me to wear. Connie, for her part, proceeded to flutter about the store, bouncing from one rack to another, piling various items into her arms and occasionally adding a few suggestions of her own.
When she had everything she needed, she smiled at Frank, tossed her the store keys and told her to "Lock the door. I'm closing early," and then took me by the hand and guided me back to one of the dressing rooms.
"Okay Big Boy," she said with relish once we'd entered the six-foot square cubical and closed the curtain. "Strip." I did as she asked. It seemed the polite thing to do.
Having done so, I stood there naked, with perhaps three feet between us, and with the object of my masculinity jutting out in front of me like a not-so dangling past-participle. She, in turn, stood staring in what appeared to be lustful wonder, her mouth slightly open and her eyes focused on but one thing.
"Oh, honey," she said, after what felt like several minutes of silence. It wasn't, but the actual time involved didn't matter. Truth be told, I enjoyed every second of it.
And then she said something that took me by surprise: "This could pose a problem."
"Huh?" came my ever-so intellectual response.
"I may have to do something about it," she answered with one of the most overtly sexual smiles I think I've ever seen, as she took a step closer. It did nothing to alleviate either my confusion or my erection. Seeing the stupid expression on my face, she elaborated. "There's no way we can do the tuck with it in that condition."
"Tuck?" I asked, furthering the proof of my ignorance.
"Well if we don't," she answered, "the front of your skirt will bulge."
Just then, I happened to notice the exact same condition occurring on her. It seemed there was a bit more to Ms. Constance McGuire than I'd thought. "You mean like that?" I enquired, looking at her eyes but pointing somewhere else.
In similar circumstances, some might have darted their eyes downward, blushed a deep, embarrassed red and stammered something beside the point. Others might have tried to pass it off as an illusion. Not Connie. She just continued giving me that sexual smile as she put hands on hips, stood there on display, and asked, "You like?"
"Maybe," I answered. "Difficult to say, under the current conditions."
"Conditions?"
"You still have your clothes on."
"That can change."
"Yes, it can," I agreed, giving back a smile of my own. "But we also still have Frank standing around out there," I added, hooking a thumb toward the shopping area.
"We could ask her to join us."
This brought me to absolute, rigid attention and appeared to have the same effect on Connie. Reality brought me back to Earth. "She's not exactly a big fan of cock, you know," I countered as I took a closer step of my own, and as the back of my hand "accidently" brushed the front of her skirt, causing the temporary tent to twitch and dance like a ballerina with epilepsy.
"I do know," she said, taking me in her hand. "But I also know the reason for your new wardrobe, so perhaps in your case, she won't mind so much," she added, giving it a pull. "She might enjoy watching."
"Hmm," I replied, and then, without taking my eyes off Connie, said, "Oh, Frank?"
"Yes, dear?" my lesbo-friend answered from somewhere out in the shop. "Is there a problem?"
"No. No problem," I said then added, "But I was wondering if you'd like to watch me give Connie a blowjob."
Silence.
More silence.
Still more silence.
I had begun to think perhaps I'd gone too far, when she asked, "Are you dressed yet?"
"Not yet," I said.
Another pause, and then: "Go ahead and get dressed. I'll be back in a half-hour. Don't start without me!" she commanded, and with that and a jangling of the bell above the door, she departed, leaving Connie and I to wonder just what our mutual friend had on her delicious, dirty mind.
16
Hair, Makeup, and Oral Temptation
The ensemble Frank picked out for me started with a pair of sheer black thigh-highs with embroidered roses criss-crossing up the legs like barbed wire, and a matching pair of thong panties. A black garter belt connected everything to my hips and nestled beneath a red spandex micro-mini skirt and a black sleeveless pullover blouse featuring a taper at the top where the material wrapped my throat. Shoes had been problematic, given the difficulty of finding women's footwear capable of fitting me on such short notice, so we just went without.
Connie had been right. My male plumbing created a fashion faux pas, but unlike the shoes, it came with the package, as it were, and so there wasn't much we could do about it. The damned thing didn't seem to want to go down; can't imagine why. I tried my emergency standby image of Hillary Clinton naked, but it didn't help. Neither did Connie's heroic, yet masturbatory efforts to tuck it away. Aside from the manual stimulation caused by her attempts, it either pushed out the front of the skirt when pinned upward into the garter belt or ruined the effect in back when tucked downward, quite a bit like the scene at the climax of Ace Ventura, Pet Detective. Since my backside was to be the focus of Frank's attention, and as this fantasy was to a large degree hers, we decided to leave it bulging in front.
And as for the back, once she'd gotten me dressed, Connie spun me around and let me look at my posterior in the dressing room mirror. "Dammit!" I exclaimed. "I've got a nice ass!"
"Yes you do, sweetie," she agreed, and demonstrated just how much by giving it a playful rub. This, however, did nothing to ameliorate the small mountain at the front of my micro-mini.
As it happened, my "unsightly bulge" mirrored Connie's pleated skirt. Her solution to that particular dilemma was to remove her panties altogether and let it all hang out, so to speak. This resulted in a marvelous tenting effect, but also made it difficult to remain patient as we waited for Frank's return. My new extra-special friend occupied our attention by seeing to my hair and makeup.
My body was and is, for all intents and purposes, hair-less. I could (especially back then) go for as long as a week without shaving and you wouldn't notice much of a difference. I had none on my chest, very little on my arms and legs, and not a whole lot more on my genitals. The color and embroidery on the stockings covered my legs, and my arms (in the right light) could belong to a woman who frequented the local gym. The panties (what little there was of them) covered the small patch of pubic hair. My butt (which Connie persisted in fondling, thus causing no small degree of blood flow between my legs) was smooth as a baby's.
I am more lean than muscular, but all those years of Tae Kwan Do had given me quite a bit of tone, so while my shoulders (exposed by the strapless blouse) didn't look overly masculine, my arms appeared to belong to a female gym-rat. I could live with it. I liked muscular women – and so did Frank – provided they didn't exhibit too many of those scary veins often found on female body builders. Gotta draw the line somewhere, I suppose.
Connie then fiddled with the shoulder-length hair on my head. This exacerbated the problem between my legs, because the tent at the front of her pleated skirt kept drawing my attention. This may have had something to do with my special lady hairdresser straddling my legs as I sat and she stood messing with my hair, placing the object of my interest a scant three-or-so inches away from my salivating oral cavity. How I managed to refrain from gobbling her extra-special large clit before Frank returned is beyond me, but I muddled through, somehow.
The temptation to perform fellatio notwithstanding, I concentrated on her coiffeur-manipulating efforts as she folded, spindled, mutilated and sprayed my hair into submission, managing to give me a similar fresh-fucked look to her own, even though neither one of us had, as yet, been freshly fucked. But before she could do anything to rectify that discrepancy, however, she needed to set about applying makeup to my face.
I have since learned how to do this for myself, but at the time, I hadn't a clue. She subscribed to the less-is-more school of cosmetics, and so didn't do a whole lot: a bit of eye-liner, a touch of color to my cheeks, and a moderate amount of lipstick matching the color of my new micro-mini. The end result, though minimalistic, left me speechless.
I'll be damned if I didn't look like a girl – and a pretty hot one at that!
We had little time to admire her handiwork (or to deal with the tent situation), however, because a couple of minutes after she finished, we saw the triumphal return of Frank. And what a return it was!
My lesbian friend had arrived dressed as a man.
...To Be Continued...
Dear Reader, I continue to hope you are enjoying this story. I don't know because so few of you have commented. Come on...I'm looking for validation here...Or at least trying to find out if any of you are actually reading this. Please let me know. E-mail to wyldenights at yahoo dot com and by all means, support Nifty!