In a Neighborly Way Ch. 02

(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 next Saturday night at neighbor's house. 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.)

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Chapter 2: We Can't Wait—The Set Up

Kit: The week while KrisTy was away on her business trip was a very long week for me. I did need some time to get used to the idea that Skip and I had taken a shared lover into our marriage. Sunday, Skip and I didn't speak of it to each other, but I could tell we were both deep in our own thoughts about our sexual encounter with the neighbor lady the night before. On Monday, slightly testing the waters, I texted KrisTy and Skip in a message saying that I enjoyed our time on Saturday night and looked forward to our time together next Saturday evening at her house. Both of them responded that they too were looking forward to the upcoming weekend.

Skip and I had great sex Monday night and again on Wednesday evening. I think my simple text had cleared the air between us all. Indeed, he seemed to be a lot more appreciative of our lovemaking this week, and he lingered inside me longer than normal. With Skip's cock hard and throbbing inside my very wet pussy, we both admitted to each other that we couldn't wait for Saturday evening's three-way tryst. Skip came hard, thrusting as deep as ever, setting off my best cock-crushing orgasm, which I had not achieved in a very long time. Whew!

Monday night after making love to Skip, KrisTy happened to text just me to say she was unwinding with a glass of red wine and thinking about us. She was thinking about a "theme" party for us Saturday night. She had been playing with a few ideas and was now firmly thinking we should make it a "transsexual" themed "cocktail" party, and asked if Skip and I would be interested in this sexual twist, seeing how it was just our second get together. She noted what I had said about my open attitude about sexual orientation, my apparent delight in anal play, and that I might like this theme; but, how about Skip?

I replied I would like it all, would convince Skip, and asked her what we needed to prepare. She would text me a plan on Tuesday, noon.

Before Skip fell asleep, I asked him if he'd mind a transsexual themed night with KrisTy on Saturday, to which he said he'd like anything the two of us cooked up. So, while I was in the bathroom cleaning up from our sex, I texted KrisTy, "The TS Saturday night theme is ON!"

Tuesday, KrisTy replied with the following:

"I want our TS theme to be fun, but not a theatrical drag party, so take special care in your outfits. Since you have to walk across the street in daylight, you might want to arrive in your normal casual clothes and put your dressy items and make up in a roll along box. Don't forget some nighties and toiletries should you decide to stay the night, which you are welcome to do. Once at my place, we can finish Skip's make up and then you can both dress in cocktail-party wear. Please ensure Skip understands he's dressing as a lady and should act so—not like a 'Queen.'

"Wear or bring along theme-based underclothes/lingerie. Here are some ideas:

"Skip, dressed as a TS, could have a bust. You can improvise cheaply. However, do buy him a stretchy, bikini pantie to hold his cock and balls securely. Stockings secured with a garter belt will look nice. You can buy a shaping corset and separate matching shaping panties and add the garter belt too. This combo would be more versatile for Skip than those which are full "pantie to bust" with garters. And, don't forget at least three-inch heels—get him practicing soon.

"He can probably wear the corset under his cocktail dress well enough. Find a nice wig to match his natural hair color and eye brows, put on some foundation make up, and we'll finish his makeup when you arrive. False eyelashes will be the 'flutter of the night' for all of us 'ladies,' so, get a couple of pairs for him too.

"As for you, you can choose to come as a female or as a transman (oh, minus the fluttering lashes). In the latter role, you'll want masculine cocktail attire and want to harden your make up quite a bit—maybe a 'bad-boy' look. You might like to get a nice strap-on cock, where its harness anchors in your pussy (for your own enjoyment and for thrusting support) and, one in which, the harness straps around your waist and under your crotch securely. Keep the strap-on cock size to about 7 inches, firm, but soft to touch—average male girth. Make the cock detachable, so you can detach it so it won't be noticeable under your dress pants. If you come as a transman, buy some silky boxer shorts and wear a tight-fitting sports bra to hide your breasts-well, as much as, that might be possible.

"If you come as a transwoman, then dress the sexiest you've ever dressed, planning to cum a lot at a cocktail party, knowing you're going to get 'layed' a lot. If you come fully transitioned, then while 'full combat' may be currently fashionable, you may like a barely-there thong bikini with easy access and matching bra. If you come as a "pre-op" transwoman, then the same advice for a strap-on harness and cock, mentioned above, applies. Oh, don't forget the spiked heels!

"In our sister town is a lingerie store that specializes in these things. Slip over there around 2 pm any weekday to pick up what you need without a lot of customers to bump into. The weekday afternoon sales associate is young, but a very knowledgeable and a friendly transitioning man to woman—tell "Gigi" that I sent you. She'll fix you up with the right items, and she can even suggest and coordinate fashionable and useful items for our party."

In one last comment, KrisTy said she wanted Skip and me to start drinking a liquid fiber solution three times a day. She said to take at least one heaping teaspoon in the morning, one an hour before lunch, and then again an hour before dinner—starting this evening and continuing through Saturday morning. This regime would make us more regular and cleanse our bowels somewhat. Along with the late afternoon enemas, which she would discuss on Friday afternoon with me, we should attain more obstruction free and cleaner rectums and anuses for some great anal sex Saturday evening. I replied we occasionally used a sugar-free fiber product so that would be no problem. Enemas?

So, on Wednesday in mid-afternoon, with KrisTy's "How To," I stopped by the very provocative lingerie store that she suggested and met the nice young woman, Gigi, the only clerk that afternoon in a very customer-empty store. She was probably in her early twenties, very thin, with skin as pure as the driven snow. Her very dark brown hair was thick and shoulder length, well brushed and not overdone. Her make up simple, but accented with medium long lashes and well-shaped eyebrows. Flat breasted as a slate pool table; but, oh, what fantastic shapely, toned, bare legs in simple heels, with a straight sleeveless dress plunging at her bare, no-bra chest and hem short enough just to cover her hot pink panties. Oh, gawd, to be twenty-five years old again—I'd have her in the back room in minutes. "Gigi" would be on my fantasy-to-cum-list for some time in the future—I hope Skip will like her too!

Gigi filled out my shopping list. She had many suggestions and appealed to my thrifty nature; me wanting value and inexpensive prices. She gave me instruction on how to tuck Skip's manhood into a pantie, how I would anchor my strap-on harness in my pussy lightly coated with lubricant, and how to attach and detach the cock in the size I wanted to use. Finally, as I was leaving, she wished me well, said she hoped to see me again, and maybe I could tell her later how the products worked. Well, I thought, I'd be sure to do just that.

While Skip and I were making love on Wednesday, I asked him to kneel on the bed and to lean forward on his elbows. There, I sucked his cock and licked his balls, and practiced pulling his cock rearward, trapping his balls to either side of his shaft. I sucked and licked him well for his cooperation, and I introduced him to one of my fantasies by finishing with a soft licking of his anus and a nice poke with my index finger, which he appeared to like tremendously. Liked, so much so, that he aggressively fucked me that night—me sinfully submissive.

Thursday, KrisTy texted me to ask if I would be home early on Friday afternoon, as she would be arriving at our local airport about 1 PM and that we could get together, whenever I got home, for some tea and make a few more plans for Saturday night.

I asked if I could pick her up from the airport, as I would be leaving work early and driving by the airport on my way home about that time.

She said, "Yes," and gave me the arrival door. She would phone me on my cell the minute she disembarked the plane and would give me an update on when she might have her luggage from the carousel.

On Thursday evening, I had Skip try on his new 3-inch heels. He sort of feigned disinterest, but said that he would practice walking in them this evening and next. Hmmm, maybe he wasn't so much for this dress up occasion. I was a bit worried, to say the least.

On Friday, almost exactly at 1:30 PM, KrisTy walked out of the airport at the designated door, in casual business attire with two-inch pumps, dragging a large wheeled bag with an overhead-compartment-sized bag in tow directly behind it. I exited my car to open the hatch for her bags. KrisTy appeared to be chatting and walking with a man, then waved goodbye, and upon meeting me, slipped her arm around my back and gave me a friendly, "hello, nice to see you" kiss. Peeking over her shoulder, I could see her male friend was curiously watching the show.

As we drove home, she said he had started talking to her at baggage claim, having taken an interest in her on the plane, and asked for her phone number, which she didn't give him. Interesting, I thought, as I remembered my single life.

Dragging her bags inside her house, I decided to take the "hello, nice to see you" kiss, to an "I missed you" kiss. Holding KrisTy tight against me, I kissed her mouth open to allow my happy tongue's dance. After a week of thinking of KrisTy, I wanted her, and I wanted her now. I was hot from being outside, she was hot, and our kiss just steamed things up more. I moved my hand toward the side of her waist and started to undo her pant button, but she stopped me cold. Kristy reminded me of Skip's and my marriage vows "to share," and this wouldn't be "sharing," now would it; never mind that she would, otherwise, happily lay me for the first time, right here in her kitchen and right then. She was right, of course, and we regained some semblance of composure.

KrisTy talked pleasantries for a while about her trip, but soon got us back into planning for her transsexual cocktail party on Saturday. In her concept, she wanted us to experience an uninhibited personal crossing of genders and participate in its glorious plum, transsexual play. She rambled on briefly about sexual orientation and blurring lines, but then abruptly waived off her thoughts—postponing them for a more serious discussion between the three of us sometime when we feel the need for intellectual comfort. Changing the subject, she asked about our purchases, whether I liked the lingerie shop, if I had met Gigi, and wasn't she an absolute treasure? She said she had bought a few things on her trip for Skip and me to prepare and to enjoy tomorrow night.

Opening her big suitcase, she pulled out a brown plastic bag and revealed a bubble wrapped set of black plugs in three sizes, a box of "anal shooters," a medical supply carton of four sodium-solution disposable rectal enema bags, a bottle of silicone lubricant, and some facial cleanser.

Before I could comment, she started with her nurse-kind-of instruction, based on her thinking that some very virgin or at least mostly unused anuses where going to soon be plied. Me agreeing, she continued that she wanted to show me how to use the anal shooter lubricant tubes, and she wanted to insert the small anal plug in my ass—right then! I was to follow an anal stretching set of instructions for me to use tonight and tomorrow on myself and Skip.

After dinner tonight, I was to insert the medium plug, and leave it in through the night. Early in the morning, I was to insert the big plug, and at that time insert the medium plug in Skip's anus. By noon, I was to swap the big plug into his butt. I wasn't to forget to wash the plugs well a couple of times before inserting them each different time.

At 5 PM, we were to accomplish a few final preparations in the shower. While in the shower, I was to remove his big anal plug, clear each other rectums with the enemas until "the water ran clean," shave Skip closely face to toes, and wash each other spic and span with the facial cleanser. The facial cleanser contained a diluted solution of salicylic acid, some scrubbing beads, and an orange fragrance for a fresh smell and feeling—use over our whole bodies, face to genitals to toes—rinse well. After all that, while still in the shower, she wanted me to give him the best blow job ever, and during which thanking him for his participation and patience, encouraging him to stay open minded that evening with KrisTy and me, and this blow job, of blow jobs I was to give him, right then, was demonstration of my love for him and also a down payment on his prolonged hard-on sustainability tonight without having KrisTy pinch off his orgasms, at least not so many times as she did last Saturday night.

Agreeing with an, "Ok," and a gulp, as I thought about the tasks ahead, KrisTy asked me to drop my skirt and panties and to put them on the adjacent chair. While doing so, Kristy washed the small anal plug a couple of times in her kitchen sink with dish detergent and rinsed it well. Drying it, she asked me to lean forward over the kitchen table, with my butt outward as possible toward her. "Fine," I said, and thought I would sex this up a bit and gyrated my pussy at her as I leaned over the table. She didn't miss the show and hummed approvingly.

KrisTy opened the box of Anal Shooters, unscrewed the long cap on one tube, and showing me the way, said to start gently squeezing the contents out as it entered the anus and when it was inside enough that my fingertips touched my anus, or Skip's, then to finish squeezing all of the lube out of the tube. The lubricant was a sterile silicone lube that was not harmful to the body. She then asked me to step so my feet were about shoulder-width apart; then to rotate my toes inward—pigeon toed—whereupon she squirted a small amount of lube onto her middle finger's tip and asked me to relax. Spreading my cheeks slightly more with her other hand, she lightly massaged that bit of lube on my anus, then said she was going to insert the tube; and then, she did so, inserting the thin, long nozzle of the anal lube shooter.

She kept me in that position, with the shooter inserted, while she took some of the silicone lube from the bottle she had bought, and showed me how to coat the plug generously on its entire length. Then, she instructed me to look back toward her and to drop my chin about an inch, to relax my sphincter muscles, and to push against the plug with my anus, again saying not to squeeze my sphincter, as she inserted the plug past its thickest part, to the point where my anus relaxed against is indentation just before the base.

She massaged the plug up and down and sideways a few times, slightly stretching my anus, pulled it out, played with my anus with its tip, reinserted it—I had pushed again—and this time it popped right in; and she completed with a rotation so that the lengthwise base of the plug laid along inside my butt crack. I had craved it for so long. I had wanted Skip's cock in my ass for so long. I was hoping KrisTy was going to be able to coax that sexual side out of him Saturday night. Certainly, if he would go along with the butt plug anal training, then KrisTy might have a good plan. My ass was so ready for Saturday night. KrisTy took a kitchen paper towel and wiped off the excess lube from around my cheeks, and she instructed me to get dressed. I turned around, leaned my butt backwards against her kitchen table, pushed against my new gift to make sure it was firmly intact, rubbed my hand down my recently shaved pussy, rubbing its slit up and down a couple of times, and ending with my index finger swirling my clit; and I asked, "Aren't you sure you wouldn't like a little bit of this now? Even, just a little taste to keep your interest piqued for tomorrow?" Gawd, I'm a slut.

KrisTy was firm, "Sharing, means sharing. Bring your things over at 7 PM, we'll have a martini cocktail as a toast, and we'll finish Skip's makeup, and ours—all together—to start the party rolling."

On my way out her door, I remembered I was going to talk to her about one last thing. The memoirs. I told her that Skip and I decided after last Saturday's unique experience to each keep a journal of our relationship, which would include our sexual relationships—ergo, also including her in the logs as part of our relationship with each other, and what we were feeling—memoirs-of-sort for reading in old age. After some discussion this week, Skip and I wanted to ask KrisTy if she minded and if she'd like to keep a similar diary if she wanted and had the time. Sometime, we might get together and read through them, to relive our moments, maybe in old age. KrisTy happily agreed, saying she would write what she could, though it might be more along the technical and medical style of writing, and that she could foresee such an assemblage of memoirs leading to other things useful and exciting, like a blog, a literary post, or maybe even a steamy novel.

With her laugh, a kiss, and squeeze of my ass, she bade me farewell until tomorrow.

Driving the short way to my house across the street with my new toys and sitting the scant distance on my anal trainer, I was hot and I was bothered—in a good, very horny way! But, I didn't want Skip to know what was harbored in my ass. I knew I had to fuck him hard Friday night, as a show of faith in our marriage—and, I knew because I was so horny that our sex was going to be very good. And, indeed, all went well, as he enjoyed my domineering ride on his cock after dinner. As his conversation drifted off, he mentioned he had practiced again when he came home after work in the heels, and while they fit, he was still awkward; then, he fell asleep early for a Friday evening.

Saturday, I made him try on his new feminine clothes, and I introduced him to KrisTy's desire to limber his asshole for what might come that night. He was a bit reluctant at first—maybe he was acting the shy, innocent "part," but eventually he was willing to give it all a go. He knew he was dressing up as a full woman for a cocktail party, probably fuck us all while in his corset combo; and, if we stayed the evening, he had a nice nightie that sacked down around his body, with requisite girly frills, hemmed just long enough to land below his butt and manhood in a sexy, revealing way. That said, I also had a nice pair of matching bikini panties for him to wear with the nightie, if he so wished.