In a Neighborly Way Ch. 02

Our most must hysterical moments though, were Skip's practicing in the three inch heels—for the third time this week. The dressy heels I had bought him from a discount shoe store matched his dress, were modern, chic club wear, and fit perfectly. At this point getting used to their fit, especially around his toes, he practiced standing still, yet wiggled inside his shoes time to time. From his square, guy-ish standing position, I coached him on how to stand like a lady and how to emphasize his curves and to reduce his frontal area—turn slightly sideways, outside knee inward and heel up, hand on waist, chest up while thinking about pointing his nipples upward, shoulders back, and spine straight with a little arch in the small of his back. Then, I'd have him switch directions. Finally, he walked—a disaster waiting to happen. Just what had he been practicing? I instructed him to walk with his feet closer together; placing his leading foot almost in front of his back foot. I had him practice turns, walking and stopping, taking narrower poses, posture, posture, posture, and then smile, smile and smile, as he walked and stopped. Then, I gave him a piece of gum to chew. He had to start all over, but it was funny and fun. I told him that we would walk across the street to KrisTy's house in our normal clothes and shoes, apply remaining full make up once there, and then get dressed for the evening. I also guessed that he wouldn't be walking around much in the heels and he'd be taking them off sooner rather than later. Skip was relieved. I then instructed Skip to get a book, place it on his head, and practice walking without dropping it. Ha, ha, ha!

Skip: It was quite a week since we engaged our neighbor KrisTy. Silence on Sunday between Kit and me—lost in our own thoughts about the night before. Admittedly, I fantasized about getting KrisTy's pants off. Not that I didn't enjoy the attention KrisTy and Kit bestowed on me, but I enjoy "giving" as much as "receiving."

Later in the week, Kit's been all about screwing and sucking the daylights out of me. Wow, we should have tried taking a mutual lover a long time ago. I haven't had much time this week to log here. I was a bit taken back by the transsexual cocktail theme for this coming Saturday, but decided it best to go with their plan. I could tell Kit was planning our next sex interlude with KrisTy. Maybe that was the reason for her sexual appetite this week. And, again, I was surprised when she started us on fiber three times a day at mid-week, explaining that it would help with regularity and cleanse our rectums. I pretty much put two and two together about some anal play, especially when Kit insisted she stick me with an anal trainer butt plug on Saturday morning and again at noon with yet a bigger one! Luckily, those little anal shooter tubes she had really helped.

Besides practicing how to walk in three-inch heels, the next big surprise for me was the suggestion of an enema. That idea, I wasn't too sure about. But Kit's "five o'clock enema" was delightful, as she warmed up some pre-mixed rectal enema bottles in a sink of hot water, and we had fun filling and cleaning each other's rectums and anuses, especially after wearing butt plugs, which I found out Kit had been wearing also to train her anus. After Kit shaved me face to toe, a real "trust me" kind of experience, she gave me one fantastic blow job—coaching me between mouthfuls of my cock about the evening's party and to enjoy it and to go with the flow. Down on knees, sitting back on her heels, with the shower hitting the back of her shoulders, she coached me, sucked me, submissively and domineeringly, all in one deliberate, alternating rhythm and well thought out act.

When her coaching was finally done, Kit pushed in for a throat capture of my dick's head—none too soon, as my cock felt like it was going to burst after all of the sexual attention in the shower. She now my Sub, and me now her Dom, I held her head steady, close to me, and shot my new buildup of cum down her throat, and I kept my cock stuck in her throat for the whole load. When I quit squirting, I allowed her to pull away slowly and then lingered, while she licked the slowing droplets from the tip of my penis as I laid it midway in her mouth. I wondered how I was going to keep myself hard all night at KrisTy's—but, then, really, I was sure KrisTy had plans enough for that not to be a problem! Kit washed us up extra well with some orangey fragrant soap, sort of tingly, but nice, with a double wash of our genitals and butts—from a squeeze bottle of facial cleanser that KrisTy had given us to use. Very refreshing—squeaky clean!

Finally, Kit had me try on my "outfits" for the evening. In my tightly back-laced corset, with matching spandex shaping panties (made with "undetectable" lace around my cheeks) that strongly bound my cock and balls rearward, garters, and stockings; she had me standing, walking, turning, talking, and chewing gum in those three-inch heels. With all the fiber and reduced food diet this week, finished with the enema, this cinched up outfit slimmed at least four inches off my waist, if not more! I loved my dress, cocktail black, enough room for me to move, but cut enough in the middle to show off my V-shaped waist, flaring out over my hips and pleated in the contemporary cut, and hemmed to about four inches above my knee—enough to cover my garter captured stockings, but short enough to reveal it all while I was sitting if I wanted to flirt. Kit showed me how to sit, not showing off and to reduce my frontal area, i.e., not to sit like a guy. To top off the outfit, Kit had bought a wig made of human hair, closely matching my hair color, in brown with streaks of blonde, also picking up the color of my sun struck eyebrows; a shoulder length wig; a professional cut, worn by most of the business women in our age group today.

This dress-up activity and my "look" reminded me of my early teenage days after school alone in our home, with mom and dad at work, and my exploring mom's panties, bras, slips, and stockings; trying them on, in her heels, and admiring myself in the mirror.

Kit said, "You need more work gently controlling your hair to emphasize speech and emotions." Also, "No staircases in your heels" she warned. In front of our bedroom mirror, I practiced more standing, walking, and sitting. In our chair and on our bed, I practiced sitting lady like, changing the angles, emphasizing my new found curves, and subtly transitioning to the beckoning show of long legs, my garters and panties; combining it all with a flirty look, head tilts, and hair control. This could be a fun night!

Kit said we needed to wear some casual clothes, a t-shirt and some shorts, for our walk across the street, and we'd pack in a pull along utility cart our dress clothes, make up, and some overnight things for a potential sleep over. She also laid a foundation of make-up on my face for a smooth unbroken canvass to use when KrisTy and she applied my final make up for the evening. Kit dried and set her hair and applied a similar foundation to her face. I walked around more in my outfit.

Though I asked a few times, Kit never revealed her costume to me for our cocktail party tonight. She did say I must understand that KrisTy sees her transsexual cocktail party as sort of a gender-bending experience—an experience for us to share together while having some good clean fun to indulge in the sexual aspect of our "other gender's" side. Kit was having a bit of a time getting her mind around KrisTy's concept, but I think I was understanding it pretty well.

Soon, seven o'clock neared, and my heart raced. I was venturing into new territory. I was excited but nervous. Since our shower together and all things that happened there, I hadn't given my ass another thought. I had thought about my new transwoman role: Should I be domineering or submissive or should I just go with the sexual playtime as it unfolded? I guessed, maybe all three. I did want to put my mind into my feminine role—I had to concentrate more on seeing, feeling, acting, and even hearing like I think a woman does, yet not to get so bogged down in the cognitive mechanics of it all such that I couldn't enjoy the night's experience.

We grabbed a bottle of red wine, set our home security system, locked the house, and pulled our utility cart filled with impersonations across the street.

Ding, dong. KrisTy came to the door. Foundation-only make up, hair in rollers, roomy khaki slacks, an old worn out beach t-shirt, and fuzzy bedroom slippers. The only things exceptionally attractive in KrisTy's look were her ample Ds hiking her t-shirt in front, slightly exposing her great six-pack abs. Was this really the way to start a sexy evening? Kit smiled and led our way through the door into KrisTy's home. Kit looked pretty vanilla too. Indeed, I looked like a ghost with my plain foundation face and nondescript clothes. My libido had temporarily tanked.

In Chapter Three, Kit and Skip morph into their transsex roles for KrisTy's Saturday night TS Cocktail Party.