In a Neighborly Way Ch. 03 Act 01

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Couple Engage Trans Woman Neighbor.
7.9k words
4.57
20.2k
12

Part 3 of the 3 part series

Updated 06/07/2023
Created 03/19/2016
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KristyT
KristyT
26 Followers

(Summary: A couple sexually befriends a beautiful woman neighbor. In Chapter 1, they get together for the first time, as couple invites her over for an evening BBQ. Wife serendipitously sexually engages neighbor, and neighbor eventually seduces them both that evening. But, neighbor lady never takes her pants off the entire evening! Couple decides to each keep a journal of their affair with neighbor—memoirs for reading in old age. All agree to another get together the very next Saturday night at neighbor's house. In Chapter 2, during week, wife and neighbor make arrangements and prepare for Saturday evening. Eventually, neighbor keeps a journal too, at the couple's desire; and over time, all agree to publish their memoirs. Neighbor lady does final edits and integrates them all for publishing. In Chapter 3, couple joins neighbor at her house for her Saturday evening Transsexual Cocktail Party.)

Chapter 3: Saturday Cocktails at KrisTy's

Act I: Skippy Training

KrisTy: In my first entry, since Kit asked me to write my memories of our neighborly affairs, I am nervous about hosting Kit and Skip in my house for a party. I've probably demanded too many preparations. I hope I haven't spooked them. I hope they pleasantly surprise me, as much as, I hope that I pleasantly surprise them! I am of mind to come to my party dressed as the jack of spades, full tux, high shine shoes, cummerbund, pleated shirt, and bow tie; and hair slicked straight back and with clear-only satin nail polish. Though, over dressed for the evening, I worry that it would blur gender lines too much for my guests. I will wrestle with this urge vs. how I will really dress for tomorrow evening—probably right up until the party. And, how will my evening's persona affect Skip's and Kit's view of me? If I come as I am, will they be confused; or, maybe, in doing so will it confirm, when they first see me in the evening, what they may already suspect? If I come to my party as a man, I would come as a transman, and this would throw them off a bit, then as the night progresses, they may think I betrayed them. But, this is a transsexual cocktail party; do I not need to cross the line too? Oh, such a dilemma that I've caused for myself with this idea of a transsexual-themed party. Uggg.

But, on the positive side, no matter how I dress for the evening, I will be dressed for the theme, at least some variant of it. When we strip off our outerwear veneers to our lace and frills, we will reveal our evening's own pretension, and I will eventually lay before them my life's choice.

Skip: My initial reaction coming into KrisTy's home, was, "Wow! What exquisite taste in decoration!" She welcomed us with hugs and cheek kisses, and led us into the kitchen. Along the way, I felt her warmth and undertones of sensuality in her colors, furnishings, and the art. Serving up martini cocktails and toasting all of us for many happy adventures together, she toured us around her house, not bragging on anything, but she let us observe and answered questions we had about this or that. One art piece struck me, of nine oil-painted canvases, framed as one and arranged three by three, depicting a man in the upper left and morphing, no, maybe transitioning, to a woman by the lower right canvas, who was strikingly similar in facial structure and with same piercing blue eyes, as best as it might be in its artistic representation—of KrisTy. How odd I think.

In her upstairs bedroom, she had bright, sunny color tones; and, up-beat art: A watercolor of a woman and man frolicking in a flowered meadow and another with a naked man on a sunny beach; and other various forms of art objects—abstractly sensual and some obviously sexual in their implication. Her bed was a queen adorned with lots of pillows and a soft comforter. Above her bed, was a large oil painting, stretching horizontally almost the width of her bed of two lovers, obviously genuinely attracted to each other, lying side-by-side, beckoning each other, and both naked, with the woman facing us with a wonderful bosom and with her top leg and knee lying forward -a modest nude painting—a well-done painting, with much taste, and perfect for her bedroom. Her single life was further told by her state-of-the-art LED TV and stacks of DVDs in her bedroom, many of which I could tell were marked XXX. She had updated her bathroom—exquisite! The bedroom had two walk-in closets, and she had a massive, L-shaped and well-stocked make-up table in the corner between the bed and the bathroom. A simple and bright bedroom; expressive, utilitarian, and perfect for her.

Touring us down the hallway further, we peeked into her office—the business end of her life, where she managed her region's sales force—filing cabinets, telephone, computer equipment, and a sprinkling of medical products were organized for efficiency. Degrees, certificates, and plaques of appreciation graced its walls.

A large central bathroom opened into the hallway; yet, again, updated, but this bathroom was enlarged a bit and also opened into the next bedroom. For bathing, one entered its glass enclosure over a very low threshold into a multi-stationed shower, complete with many shelves and seats of different heights and a bidet, all set on a floor slightly angling from all four sides to the drain. Adjacent it, through a glass door at its right side, was a sunken tub, big enough for three or four people, equipped with whirlpool jets and a couple of handheld shower wands, where one could easily transit between the bath and the shower and at the same time keep the water and moisture all inside its enclosure. KrisTy pointed out a non-obvious door, as it was similarly tiled, at the back of the tub, which she said opened directly into her shower in the bathroom adjacent to her bedroom. How convenient! What a great design! This is a bathroom of the ancients. This is the bath I've always wanted!

Next up on our tour of this floor, designed a little different than our house, was a second master-sized bedroom, which connected to the bathroom just mentioned. This room was much different than one you'd see in just about anybody's home. Central to its décor was a very large, if not the largest, king-sized bed I'd ever seen. It must have been a stock king-size bed; yet, it appeared large, draped with a white, lightweight duvet, piled with pillows of various sizes, and the bed supported by a large four poster frame—a padded headboard was mounted directly to the wall, and the frame had no footboard. The poster did not support a tester or canopy. Lighting in the room came from recessed ceiling lights, which KrisTy said were selectable for color and brightness. Night tables with drawers flanked each side of the bed. At the end of the bed was a matching dresser. KrisTy said a large walk-in closet joined this bedroom.

At this point, we returned to the main floor to freshen our drinks. And, here, still looking like pasty mimes, because of the foundation make up we'd already applied before arriving for the party, KrisTy started to cozy up to us, drawing us in closer to her with her light touch, smiling, musing with small talk, and bestowing simple but intriguing kisses on each of us. Soon, we were standing toward each other, in our trifecta, admiring, touching, kissing, drinking, and enjoying our new found relationship. Timing it right, she turned to pursuing the party: Dressing was the first order and then enjoying some hors d'oeuvres and music. We climbed the stairs once again, this time to use the make-up table in her bedroom.

Kit: KrisTy has a uniquely decorated house, and I'd have to say that it stirs your sensual and sexual awareness. As I saw her décor, touched its fine fabrics, emotionally felt the mood of its colors and art from room to room, and touched some of its artistic figures; its ambiance made the insides of my thighs tingle and my vagina wet a bit reminding me of my appreciation of these things. If I lived in this house, I'd be raving horny all of the time. The large bathroom upstairs was first class. I would spend my evenings in its bath, enjoying bubbles, and liberally masturbating with the wands often.

With a second martini, we reposted to KrisTy's bedroom to apply our persona's make up for the evening's party. She insisted that we start with Skip, and then, dismissed him to dress and tour the rest of the house on his own; then KrisTy and I helped apply each other's make up and got dressed. All went well, with much laughter and teasing as we made Skip into a lady. KrisTy knew make-up tricks to feminize his face; well, knew more like a professional it seemed to me. With his wig, long eyelashes, and lipstick; he was certainly a striking, German-bred, mature dame der nacht. In truth, as they say, a woman looks her best at 40 years of age; and, I'd have to say that Skip looked every bit as beautiful and alluring. Indeed at KrisTy's final touches, I gasped at his facial transformation. Why, I'd have picked her, ah, him, ah, this gender bending is difficult; but anyway, I would have picked her up at our local watering hole or maybe even whistled at her from my car for curb service. Awesome. I couldn't wait to see Skip dressed!

KrisTy: I must say, with a little bit of work and my artistic flair for the erotica, Skip's make up turned out exceptional well. I think I could repeat this look and even teach him and Kit how to replicate it and change it up a little here and there for different looks for different occasions. With the wig and eyelashes Kit had bought, Skip looked like the girl friend, who I'd take bar hopping and dancing with me and who I'd seduce in the a club's bathroom stall before the evening was done. I could tell that Kit was totally taken aback in the final moments of his facial transition; and, I think she discovered a new attraction for her husband appealing to her woman-on-woman desires. In the parlance, Skip was definitely "passable." My challenge one day will be dress Skip in casual clothes and apply a lighter make up and see if he'll pass—maybe for a run through the local clothing stores to try on some dresses.

Next, I turned to Kit's make up. She had to finally reveal to me her "transition" gender for the party. She wanted to dress and act like a man, giving the best performance that she could. (Kit didn't disappoint us this evening.) My basic strategy was to harden her make up within the blond boundaries of her hair and eyebrows and white complexion. While I was making her up, Kit said she and Skip had meet in the upper Midwest, where they grew up in a region settled by German immigrants in the late 1800s. With very little mixing, they were ethnically and racially German and of Saxon genetic descent. They had tried a couple of times for a child, but each time she had miscarriages. At the second, she decided to have her tubes tied. They are used to a childless life, but wonder about the consequences of a lack of family support in old age. Finishing her "bad boy" make up, as much as you can do without presenting a completely "theatrical" face, I pulled her hair tightly straight back and braided it downward below her collar. I finished her with barely there lip color—not too glossy. We decided to leave her manicured and painted fingernails, just to keep the gender confusion going a bit. Upon my urging, she did round and dull her dominate hand's index and middle fingers' nails with a file. Kit went off to dress.

It was the "moment of truth or not," so to speak; or maybe, was it my "truth or dare" epoch?

With a heavy chested sigh, I decided to reach out to my masculine side. To stay true my party's theme, I too had to transition. Again, I applied a "bad boy" look, hardening my make up more than I did with Kit's, which made my dark blue eyes' intensity stand out more—my eye color inherited from my Swedish mamma. My rich Italian skin, from my poppa, was a succulent, swarthy brown and could take much darker make-up tones. I straightened and widened my eyebrows a bit for a more horizontal look. I blended in some dark shadows to emulate a chiseled face. Finally, I pulled my hair straight back and braided it like I did for Kit's. I dressed: Black, sheer, thigh-high stockings; black, opaque, very tight but stretchy, women's low-rise boy shorts; black dress pants, narrowing at the ankles, with a black satin stripe down each leg's outside; black thin leather belt; white, very tight, super-hold athletic bra to reduce my breast line as much as possible; white men's poly t-shirt; white men's dress shirt with squared-off tails, worn outside my pants—collar open; square chrome cuff links each liberally dotted with a stone of black onyx; black shiny men's sport coat from my heavier days, which fit just fine over my shoulders and constrained bust; and laced, black, high-gloss dress shoes.

I descended the stairs, rounded the corner to my kitchen, and the masculine Kit and feminine Skip were sitting and chatting in my adjacent family room. Both, stood upon my entry; all of us, looking pleasantly shocked at each other in our new personas. While we are all about the same physical height and of gym-fit build, Skip certainly stood taller in her three-inch heels than Kit and me in our oxfords. Kit was sort of dressed as I was, in a black, dressy casual, sport jacket, but a pink open-collared men's shirt—nice gender blending I thought. I absolutely loved Skip's dress with its narrow waist and flared skirt line. Her three-inch heels were dressy, flattered her calves and ankles perfectly, and gave a small lift to her ass. Her smallish bust portended her propensity for sports, and the top of her dress fit them perfectly. We let the night's party begin and descended to my basement's bar and lounge area to warm up more to each other. Skip took off her heels for the short trip downstairs—smart.

Skip: Kit and KrisTy looked as much like men as they could, maybe KrisTy more so. Yet, with the "bad boy" make up and outfits that still told of underlying curves, they were both definitely sexy. Sexy, especially, when they started the evening as closely "tight" as two men could be—inseparable buddies, as close as they could ever be. KrisTy produced from the bar's frig a plate of raw oysters she had shucked earlier in the afternoon, left in their half shells, and laid on ice; poured us another martini; and dimmed the lights. In the adjacent "rec" room, she changed down the lights there too for a soft, dim warm glow, basking the room in sexy brown and cream colored tones. Adding to our visual and oral delights, KrisTy set her stereo to softly play an album of a lounge singer on piano backed with strings—sexy, sweet, easy to get lost in the erotic-moment-type of music—perfect for their seduction of - me. They beckoned me with flirty rejection; taunted me with brushing touches of my "breasts" and occasional upstrokes of my thighs; dominate sensing with small hugs, touches of my neck, short whispers of promises of the flesh, toasts of enduring friendship and future adventures, teasing licks and slurps of an oyster here and there, and boasting of their sexual prowess in the sack.

For my part, I wanted to play along. It was not easy for me to surrender my male dominance. I struggled at first with my conflict between ego and role reversal. I enjoyed their sexual advances and male-dominate swagger. Two bulls strutting their stuff. But, this wasn't a fight between two bulls; it was cooperation between two males intent on having their way with the female of the moment - me. So, for the sake of the party, and for the sake of a good time, I made the transition. In a slightly high, feeling-good state of mind, I willed my mind to accept their domination, me a submissive—with some pushback, as I wasn't "easy," yet, I figured. So far, into this adventure though, I wanted to facilitate their success, but somewhat on my own terms. Soon, I was ordering another drink for all of us from the bar, and my hands were innocently touching their shoulders, arms, and taut waists and brushing by their fly fronts. Mustering up my best softest, silkiest, and sexiest low voice, I played my part. I whispered to each of them, in time, my desires to see their cock and feel its hardness, to suck their throbbing dick, to show them both a good time together—a threesome, and for them to play with my hard "clit." Screw me hard and show me a good time, and I'll swallow your cum from endless orgasms, the likes of which you've never experienced before tonight. No more drinks were forthcoming from the bar.

Kit: I didn't know how this was going to go. Skip seemed reluctant at first—not knowing how to handle our teasing advances. Then, he made a transition. I saw his mind change gears. He started to playfully return our teasing. Sensing our lead, he returned our touches and taunts and whispered not-so-sweet, nasty nothings—he deserved to be slapped—"she" deserved to be so fucked—a virgin ass, no more.

KrisTy: I could tell it was time to take my party to the rec room, as we all had transitioned enough. We stretched out together on the big semi-round, couch, and Kit and I propped ourselves on the large pillows, facing Skip who was then nicely trapped between us at the couch's apex. Kisses and nuzzles and touches and rubs on Skip, while Kit and I stretch over her, to kiss and caress each other too. As our tempo increased, soon Kit and I had removed our jackets and opened a couple of more shirt buttons. Our hands simultaneously felt their way up Skip's flared dress to finger her garters and tops of her stockings and lightly finger her very hard clit, which was bound tightly under her dress and tucked back—folds of her genital skin camel-toed in front! How sexy. Kit was surprised at its hardness, asking, "Does Skippy's clitty need attention?"

Skippy replied with her eyes and a soft smile.

To which, I suggested taking our adventure upstairs. Skip slipped out of her heels, and I led them to the upstairs master guest room. Kit thought maybe we should try out my bedroom, but I said the guest room was much better equipped for our evening's fun.

Skip: KrisTy was quick to throw off the bed's duvet, revealing two sheets tightly fitted to the large king mattress. In the closet, she pulled out some white fluffy towels and a white, terry-cloth covered, large wedge-shaped pillow. Asking us to get comfortable, she said she'd return in a minute, slipping into the adjacent bathroom. In the meantime, Kit removed her pink shirt, revealing her well flattened breasts in her sports bra; took off her shoes; and dropped her trousers, revealing black, boy shorts and thigh high stockings. With a little more scrutiny, it looked like she may have some sort of strappy bikini or some such thing under her shorts—kind of odd. I stripped down to my corset, which covered a skimpy black A-cup bra; garter; and stockings. I had had the mind to put my stretchy tight panties over the garter for easier shedding later in the evening. But, at this point in the evening, I did have to free my ever so stiff cock, and I placed it horizontally in front of me to the side in those ever so tight panties.

KrisTy returned with a decorative, insulated bucket, filled with hot wash cloths, a big bottle of lube, and many lube shooters. Placing the bucket on a night table, she opened its top drawer to reveal an assortment of condoms, stating that the ones in this drawer would fit us "all" fine. At this point, in her professional nurse way, she established some ground rules. First, "should" we decide to penetrate an ass, then use a condom for our own protection. Use a silicone shooter to lubricate the anal opening and then shoot most of its contents in the rectum, and then use some silicone from the big tube on "our" condom covered cock prior to penetration. During the "act," relube once in a while. When finished pleasing that love port, remove the condom and put it in the red, plastic waste can next to the door to the bathroom. Also, take a warm washcloth and wipe around our genital area, wipe our hands, and be a dear and wipe off our partner. Deposit the washcloth in the blue plastic container next to the red can.

KristyT
KristyT
26 Followers