Now He's Got Me Doing It

Everyone here is eighteen or older

***

Penniless students, roommates. Scholarship, trust fund, school taken care of, room, board, books but no ready cash. A city filled with bored young ladies looking for excitement but expecting their escorts to foot the bill whether out of necessity or societal expectations. They get good at picking out those young men in the same economic despair as themselves. That wouldn't be so bad but the sneer they develop, that patent dismissal adds injury to the hopeless.

We knew one another well before he outlined his proposal. Slipping a few ales out of a fraternity party for our clunky noisy fridge, we celebrated incipient drunkenness with casual talk.

"Been meaning to show you something," his voice slurred.

Up for anything I nodded.

Opened his closet, reached to the rear where a few hangers mounted who knows how many years ago permitted surreptitious storage behind the usual racked goods. Pulled out a...

"Dear All the Saints and Sinners, Where did that Come From?"

My voice was slurred as well. It was an upscale frat and we'd polished the timing to enter as potential pledges when the brothers had time to become uniformly tipsy if not more. The Sergeant-at-Arms, intended to prevent the entry of slobbish cadgers of free alcohol, lay snoring by the front doorstep, always a good sign. His friends still standing but no more effective at grading visitors than he was at the moment (the odor of weed added to that of ethanol-laden perspiration as it was that kind of frat.) A good visit was drinking three apiece at the party and slipping at least that many, apiece, into deep pockets before leaving while sipping on number four...

The dress sexy, body-con, bright pastel pink with a bodice that would offer a lovely temptation while decidedly not signalling 'hooker' too loudly, the hemline mid-thigh or a bit lower. It appeared pressed and clean and all I could think of was to gawk at the pretty dress and then him and then the dress again.

A sober moment ensued in which I added, "...and Why, oh Sir, does One Possess It?"

The presence of something at least intended if not sometime worn by an actual female sobered the two of us for the following presentation and discussion. Romy explained what he called The Grift. Acknowledging that Women Always Drink For Free he'd turned a lifelong hobby of Crossdressing into a college gag. The clothing must be Found, Purloined, or at least purchased with Someone Else's Money (or Credit Card). That rule applied to any additional accoutrements required for Proper Presentation - i.e., Wig, Jewelry, Makeup, Grooming Services, Disposables (such as hosiery), and Undergarments.

"So we dress up as girls and guys buy us drinks?"

"Essentially, Yes. Extra points are awarded if a meal is included and also Entertainment, you know, Movie or Show or Dancing..."

The face of my roomie was deadly serious but I was credulous.

"Excuse me (What?, then laughter), but even properly tarted-up I don't think we'll look exactly like official members of the fairer sex? Are you insane?" (He was/is but in a pleasant way that makes him a good roommate.)

Roomie explained the Second Rule. "There are Young Men, Older Men, and especially Really-Older Men who prefer to associate with Special Girls such as ourselves, or rather, the feminine persona's we adopt for The Grift. For one must first nurture one's inner Femme then one must become... Her. Unreservedly."

I shook my head as this was all too much. Two unbelievable Rules so far and I imagined there would be more. His smile struck me as he watched the gears grinding behind my eyes and I was taken with the sensation that I was Actually Considering It.

"But what about... Sex? Don't these wealthy bastards expect... Something... in return for all the trouble and expense of escorting Fair Maidens about, feeding them, entertaining them? Does Not This... Grift... turn us offically... Gay?"

He smiled. "Once one adopts one's female self, puts Her in charge, one is essentially A Woman. Is it Gay for a Lady to interact intimately with a Gentleman? She is not without scruple or expectation or consideration as to what characteristics are required of a Suitable Escort. He must be intelligent, imaginative, respectful and pleasant."

"You didn't say Handsome."

That grin, how beguiling I'd begun to find it. "Handsome is as Handsome Does. It is a Totality - The Face might have been used to frighten errant children but attached to hips on which are slung trousers weighted by a leather Wallet filled with large bills and many credit cards one finds enchantment and dare I say it, Fulfillment."

I sat slowly on my rack and the resulting whoof told me it was time to replace the sheets.

My Muse turned and hanging the dress on one of the outer hooks, reached again behind and pulled out another. Attractive and fresh from a Cleaners, a complimentary shade to the first, same while different in cut and couture, he placed it on an adjacent hanger so as to view the two side-by-side. One could almost imagine the two young ladies, out in search of a Cure for Their Ennui and stories to tell their grandchildren.

All I said was "We'll need Shoes."

"Do not worry, young acolyte. I've already made the Spa Appointment for tomorrow. The lovely Esme' of The Bobbi Pin will serve as our Mother Superior and the Fair Ladies of Hair and Nails will groom and tutor us in Deportment and Demeanor."

"Do not those born to this have a certain resentment of our plan to emulate them and experience something they might readily consider theirs alone?"

"Mother S. answered me on my first visit in this way: 'More Young Men Should Learn the Challenges of Womanhood from the Inside.'" She specializes in assisting Special Girls and encourages her employees to enjoy the challenge.

"How are you paying for all this?"

He responded by opening an old wooden crate on the floor of the closet, reaching behind the attractive hems of the dresses. Silver and stacks of Bills filled the crate to halfway.

I cocked an eyebrow at him. "Purloined?"

"In a manner of speaking."

"Are we to be Whores?"

"Certainly not. Proper Young Ladies, rather. Our Favors are not For Sale. You'll find Gentlemen Yearn to Display Their Gratitude for a Giggle or Smile, the touch of a Finely Manicured Hand on their Shoulder, completely apart from..."

I waited.

"...Those Pleasures reserved for Ones With Whom The Lady is Especially Fond..."

_______________________________________________________________________

In Part Two The Adventure Begins with a Visit to A Proper Salon and Hilarity Ensues as Mother Superior Coaches Us in Standing, Sitting, and Walking in Heels. Some thoughts are given as to Which Bathroom Do We Use?

To Fast Forward,

I wake slowly, my hand running down my body to find me wearing nothing but panties. My skin is sleek and smooth if a bit dry. Out of the covers at the bottom peeks five toes with nails still polished to match the color of my fingernails.

Despite quite a bit of Champagne I feel no headache or sour stomach - it must have been The Good Stuff. My God, I think, I never even had to pour a glass! I smile, smell coffee.

A gentleman walks into the bedroom, his middle-aged paunch the only favor given his years, the rest fit and even muscular. He wears nothing but an erection and carries two cups of coffee.

"Two sugars and one splash of half-and-half," he smiles kindly but lasciviously looking down on me. My face must be atrocious and I resolve to never present myself without preparing. My hair is mussed, all wigs, extensions and so forth and I pat it in the way Esme' taught me, smoothing what I can with my palm and fingers. I hold the sheet over my chest, again in a way learned earlier in the week. Both feet are peeking out now and appear quite feminine.

We sip our coffee and he notices my staring at his erection.

A soft laugh. "Sorry, not leading the conversation. I took two blue pills late last night - wanted to be sure..."

I giggle and smile demurely up at him. Softly, not quite a whisper, I say "My stallion..."

We kiss close-mouthed as neither of us has taken the opportunity to brush our teeth but still it is a lovely kiss, his hand on my shoulder, my arm still guarding my breasts. The other hand finds the soft flesh that covers his steely shaft and I stroke my lover slowly. The coffee warms and settles my belly so the excitement I feel there is held in my hand.

Still covering myself for I am a demure young lady, I slide to the edge of the bed and placing my coffee cup on the side table I cup his testicles in that palm and take him into my mouth. The drop of his love at the tip of his penis touches my tongue and other flavors mingle left from last night. How I love to please him in this way, the accompaniement to my transition to this world, a real desire to offer and to give myself to this male person.

My eyes closed, he cups my head in his palms and adds gentle thrusting to my bobbing over him. I let the sheet fall away and display my breasts to him, the HRT having at least given me the faintest bulge of tissue behind full, dark aerolae and plump nipples. In only a few weeks I've grown to love the sensitivity and to adore wearing a brassiere full time.

I moan with pleasure and that's enough to stimulate him to push me off of him firmly but gently and then to turn me about so I'm on my hands and knees. I sink my upper body to the sheets and proffer my bottom wordlessly, that act so natural and real I don't even conciously display myself so erotically, it just happens. He slathers himself with the light lotion on the side table and presses against me and I feel myself open to him, parting to permit his intimate intrusion (wanted, if I think about it.)

Even my gasp of pleasure is high-pitched and feminine and I hear him chortle with pleasure that he's possessed me once more. Slowly, torturously he slithers inside me until his thighs meet my buttocks and I am fully his. I press back against him, knowing him, wanting him, moaning more plaintively to be loved. The sensation is exquisite, his bulk filling me, touching that place inside that has awaited him all these years.

Strong hands on my hips, he has me, has his way, takes me for the third (?) time since we met, each time more expertly, more assuredly, no need to be timid or tentative, he knows what I can take, what I like, what I love. Each thrust firm, full, strong and I shudder with more and more delight, wiggle like a paid courtesan to ensure his full pleasure but more to give myself to him body and soul. Wanting, needing, having, filled with delight and then in time with the shudders of his ejaculation as he presses so hard against me he is like a steely statue.

One hand reaches around and under and he strokes my clitoris lovingly, insistently. It feels lovely, wonderful and my heart is full and loving for the attention. I even love the feeling of his tumescence waning inside me, the slowly slipping away that signals he is fulfilled with our lovemaking. He pushes me flat then lays beside me and takes me in his arms for a proper kiss, the taste of coffee covering the night terror of our mouths. But his arms surround me and it is what he desires and I am his, right?

I look up from his kisses and see his wife standing by the door. I blink and wonder what she thinks. Though she'd given me permission to accept his love she'd not watched us before now. Her face is neutral, perhaps a bit serious and then I realize she is lustful.

"My turn," she says gently and raises her skirt then pushes her panties down her thighs.