In a Neighborly Way Ch. 03 Act 01

Likewise, when manually stretching an anus, which she encouraged before penile penetration, the same rules applied; so, use a pair of nitrile gloves, found in the condom drawer, and use generous amounts of lube. Dispose of gloves in the red can. Remember, please use the warm wash cloth liberally for cleanup. She caveated, since we'd already affirmed our disease-free status last week, we may penetrate oral and vaginal ports freely, as long as "our penises" and surrounding areas were adequately clean. For a good cleaning if we needed, she directed us to use the bidet in the adjacent bathroom, and that she had plenty of towels and washcloths there also—but, not to reuse them. Otherwise, no biting, no hickeys, and no bruises. We all agreed to the house rules. Luckily, we didn't have to sign in blood. At this point, I wondered how many "penises" would emerge tonight.

Kit: I loved KrisTy's, revealed to us just then, sex room. I couldn't wait to try out the sex wedge. I admired KrisTy's attention to detail on safe sex and cleanliness. Clean, safe fucking is definitely more liberating. KrisTy pulled off her dress shirt, tossed her shoes, and we all dived into the great big bed—awesomely right firmness and pillow-top softness; soft pillow cases and sheets, but not too slippery. Ahhhh, heaven. KrisTy and I started loving on Skip, with plenty of handsy play, reaching for her clit often, stroking it softly with gentle fingering and teasing. I could tell she-Skippy was horny; she was ready for more detailed attention. So, I started my slow crawl down her body, slipping my hand under the top of her corset and under her training bra; and, KrisTy was likewise squeezing her other nipple and kissing her neck, ears, face, and lips. Soon, I was licking between her corset and panties; and at this point, I asked KrisTy to toss me some gloves, lube, shooters, and condoms.

I pulled Skippy's very tight panties down and fully off, encircled Skippy's clit lightly at its base with my left hand, pulled myself up to it, wetted my lips liberally, enveloped its tip, and slowly increased my sucking pressure. I wanted to make her big clitty, red, swollen, and sensitive. I sucked, licked, and played with it like I want sexual attention given to my real female clit. I squeezed around its base hard and increased the depth and intensity of my suck. Alternatingly, I licked around the edges of her genitals and ignored her clit altogether. Her clit hardened even more, and I massaged her (imaginary) pussy area deep from her clit to her anus and back. Soon, she was dripping precum, and it felt finely slick in my mouth. I stroked her pussy for more.

Then, with my gloved index and middle fingers, I pushed hard against her locked, tightly closed ass. KrisTy kissed and played with Skippy's face and neck and tweaked her nipples, keeping her upper body satisfied and slightly distracted. Drooling some spit, mixed with her precum, down her pussy and onto my fingers, I made another incursion, pushed in past her ass's gate, lingered, pushed in and pulled out, explored deeper, expanding its entrance wider each time, and all the while I held her clit tightly and ever so lightly licked and sucked its tip. With a quick dive, my fingers went for her P-spot, stopped, prodded, and massaged. She definitely had changed her attention to me, and she started rocking down on my fingers and thrusting her hips to dive her clit deeper in my mouth. With my hand locked on her clit, my fingers hooked deeply in her ass, and my thumb massaging her Cowper's; I licked, kissed, and sucked her sweets spots in between, visited her clit, briefly now and then, just to let her know I was still paying attention to her aching desire.

Skip: Soon the men had me stretched out on the bed and Kit was sucking the end of my clit hard and penetrating my ass with her fingers. KrisTy was keeping me slightly distracted with some great kissing around my neck, with nipple squeezes and twists, and with the occasional lingering deep tongue-plunging kiss.

KrisTy started into a sexual inquisition of me, "Is your ass virgin? Do you want it penetrated?" Immediately, she kissed, rimming my lips, and then drove her tongue in me hard, lingering enough to explore my throat—then, retracting her kiss as quickly.

"Yes, and yes."

"Have you penetrated Kit's ass before? Do you want to?"

"No, and yes." She pinched my left nipple extremely hard—citing retribution for my failure to service Kit's ass.

"How do you want this to go? I don't want any hard feelings at the end of the night between you and Mr. Kit. Who gets fucked first, missy? By whom, to whom, and how?"

So, KrisTy, "he" was letting me choose. Remembering that Kit and I are a couple, KrisTy was giving me a chance to decide on the order of penetration—how thoughtful. And, by Mr. KrisTy giving me a choice, he gave me a sense of managing my own destiny—how chivalrous.

I wanted Mr. Kit to have my ass first, and I wanted Mr. Kit's ass first.

To which, KrisTy agreed, saying, "Fine choice. In return, while Mr. Kit has your ass, you will suck my cock; and then, while you fuck Mr. Kit's ass, I will penetrate you both at will."

I nodded agreement. At that, KrisTy had me remove my shoes, turn over, and lay on my stomach on the long side of the big wedge positioned at the foot of the bed, facing uphill and with my legs drooped over the end of bed—me standing, bent over the edge of the bed, lying uphill on the wedge, and facing KrisTy. KrisTy asked Kit to find a length of double-braided five eighths-inch soft nylon line tied to each post at the foot of the bed, asked me to spread my legs wide, and told Kit to tie my ankles securely, but not too tight. As KrisTy gave the order, KrisTy found two similar lines nearby and tied my wrists, stretching them toward each post at the head of the bed.

KrisTy: At this point, Miss Skippy had given her consent. My buddy, Mr. Kit and I would ramp up (pun intended) her evening. Having tied Skippy spread eagle, butt open to the world, and head draped over the base of the wedge, Kit knew exactly where this was going. Of course, Kit did hear Skippy's desires for the night, and she smiled at me in agreement. Kit slipped off her panties, and I saw her harness. From a small bag, she produced the "average" cock as we'd discussed earlier in the week, attached it to the harness, slipped on a condom, and lubed her stiff, but obviously flexible cock well. Still wearing the glove, Kit took a lube shooter and squeezed it inside Skippy's ass, backing it out with a little lube still squirting along the way.

Meanwhile, I asked Skippy if she trusted us, and she affirmed it. I then said that she would find the experience more electrifyingly sexual with some more props, and she desired it. I took a black, thick, rectangular length of cloth from a drawer in the other nightstand and folded the cloth once, making a blindfold, which I put around Skippy's eyes and tied behind her head. I said soothingly in a low voice, "Remember, trust us, sweetie. Concentrate on your sexual feelings and sensations—get the most out of them. This is our night together; to always remember."

Kit: KrisTy surprised me with the bonds and the blindfold. I knew it was time to mount my new store-bought penis to my harness, of which its anchoring plug had been touching off sexual pangs in my vagina periodically this evening, then even more so. Mr. KrisTy adjusted the room's lights to a low pinkish red glow, and turned on some battery powered "tea lights" around the room. Very sexy.

Once I was lubed up and had lubed Skippy's asshole well, KrisTy came over, and asked Skippy to turn her feet and toes inward, drop her jaw, and to push against my cock. It was just how she had instructed me, and it was just how I had instructed Skippy during her anal training. And, so, it was familiar, and Miss Skippy took my cock without any complaints. KrisTy instructed me to aim upward toward her back bone for the initial penetrations, cycling slowly and exploring deeper with each stroke in her ass. Once all the way in, I could then press downward toward her P-spot and massage it with my cock. Ms. Skippy was rocking back and forth on my cock's shaft, and I could tell she was tightening and loosening her ass depending on which direction I stroked to see what felt best to her. When I massaged her P-spot a few times, KrisTy reached down to milk Skippy's clit to check for any precum. When Skippy dripped some for us, KrisTy caught it with her fingertip and shared it with me, each of us licking a portion. I kept stroking easily, and had my fun fucking Skippy from behind. Skippy was giving me low appreciative groans.

KrisTy: Once Mr. Kit was riding Skippy, it was finally time for the next stage of Miss Skippy's fucking. I slipped my tight boy shorts off, crawled back on the head of the bed, and faced Skippy. The lights were dim. Mr. Kit was rocking on Miss Skippy, and Kit was in his own world. I coaxed Skippy along, "Are you enjoying your fucking?"

He groaned, "Yeah."

I told her it was time to take another cock, this one in her mouth. I told her not to bite it. "Are you ready?"

Skippy groaned louder, "uh, huh."

My very male cock was hard, as hard as it had been in a long time. I hoped that my self-wank earlier in the afternoon would give me more staying power this night. I had not had intercourse with anyone in a very long time. The short encounter with Kit and Skippy last week had fanned the flames recently laid low and only flickered by masturbation.

I set up Miss Skippy and me for a great throat fucking. "Let's start with a little help, shall we? I am going to squirt some numbing liquid in the back of your throat to make sure you enjoy my cock. Open (a couple of wide sprays to the back of her throat). Swallow. Open again (one longer, narrow shot to the very back of her throat). And, swallow again. Open your jaw slightly, but keep your lips tight together. I am going to put some lube on your lips. Do you feel my cock against your lips? Keep your lips tight as I push past them into your mouth. I'm only putting my head into where your teeth pass the edge of the glans, but don't bite. Ah, that's right. Please add some flat, soft tongue licking under the base of my penis, near its tip. Yes. Circle its tip with your flat tongue and add some sucking power. No too much. That's right. Let's do some tongue and teeth play with its length, shall we?

"I am going to pull my cock out of your mouth and rub its head and its shaft on your face, your nose, your neck, and rub its head back and forth along your lips. I want you to feel comfortable with my cock. I want you to love my cock. You should get to a place in your mind, your heart, and your soul, where you desire my cock, you desire to touch it, you desire its touch on your face, on your body, in your hands, alongside your clitty, between your cheeks, inside your ass like Mr. Kit's, and most of all you will fantasize about my cock in your mouth for ever and a day. You will want to suck my cock, touch my cock, and stroke my cock to give me the most sexual satisfaction I will ever experience in my life. In return, I will caress your body with my cock, ply your throat with its throbbing head, and will explore your sissy pussy with its length and massage your P-spot as deep as possible to bring you explosive orgasms."

Skippy nodded as I rubbed my cock and its head around her face and neck, pressing on her nose, lips, and ears.

"This time Skippy, you're going to gently nibble my cock from the side, like a corn on the cob, teeth gently teasing its top and bottom sides as I slide it alongside your mouth; repeat; and, of course, alternate all of this with straight-on licks and sucks of its head." She compiled well.

"You appear to be a seasoned cocksucker Skippy. Are you practicing elsewhere, or are you just dreaming about sucking me in your fantasies? Are you a good learner? Does Skippy always want my cock to please me at any time?" I kept her mouth filled, not really wanting an answer to my teases for Kit's sake. I may have gone a little too far with this intense sissy training. Only time will tell how this works out.

I ached for some deeper cock capture. "Skippy, you are going to practice taking my man cock as far down your throat as possible—more each time." I reassured her that the angle of her neck would be perfect for her attempts at allowing me to slide my cock down her throat. "Is your throat numb yet"

"I, ..., I can't tell."

"It's fine then. But, let's use a little more lube. Open your mouth wide, stick out your tongue wide and catch a drop of lube—it won't hurt you and it doesn't have any taste—gently swallow it to just coat your throat. And, yet again, catch another drop of lube on your tongue and hold it in your mouth—don't swallow it. I'm going to put some more lube on your lips and coat my cock with it too."

Looking at Kit, I said, "Go with the same rhythm and stoke as I do while penetrating Skippy's mouth this time." She nodded.

In my attempt at completely bending Skip's gender, I asserted, "Skippy, think of your ass as your female vagina. Think of Mr. Kit's penetrations past your vulva and thrusts deep into your vagina as stirring deep sexual nerve-ending feelings, stimulation not starting from what you knew as your penis, but from deep strokes inside your vagina. Think of the glory of having two cocks penetrating as deep as they can in your feminine, sensual, cock-sucking mouth and your sissy cock-craving pussy. Think of each man giving you all of his cock—each looking for your orgasmic eruptions to trigger their ejaculations—and think of their hot cum squirting inside you. As they fill you with cum, think of squeezing your vagina inward and upward repeatedly to capture and save it; think of swallowing it straight down your throat, and when my jerking and squirting in your mouth subsides, think of lightly lapping the last drops from my cock's underside and its tip, gently sucking its final drops from the very tip. Remember my cum's taste, remember you will want more, remember its flavor and warmth, and remember the feel of it squirting in your throat, in your mouth, and crave more of it squirting everywhere possible in your body and on your skin."

"Ready? Again, Missy Skippy, push against my cock with your lips and make it a tight entry. I'm going to push in deeper this time. Oh, yes. I'm going right up to the back of your throat. Take a couple of deep breaths and hold your breath on the second." On cue, Kit had exited and repenetrated half way in Miss Skippy's vagina.

"I'm going to push my cock just past your tonsils." Skippy was starting to gag a bit. "Hold your breath some more, ignore the gag reflex, and I'm going in your throat deeper. Hold your breath. Calm yourself." Likewise, Kit had plunged as deep as her cock would go in Skippy's vagina.

That was far enough for the first time. "Skippy, let's try it again. Catch your breath. Ok, take two more deep breaths and hold it; I'm going all the way in. Push your nose against my pubic bone and your chin against my balls. Hold it, hold it, hold it. Feel the head of my cock throbbing in your throat."

Kit: Balls? Throbbing head? I had pretty much been going with the flow as Mr. KrisTy had been directing Act One with Miss Skippy tied to the bed and taking cock from us in both ends. The room was pretty dark. I was enjoying myself and acting out my fantasies. I was not only screwing my husband, in a good way; but, I was also fantasizing about some strap-on action with other females, KrisTy being my first subject. It didn't surprise me that Mr. KrisTy had a cock of his own tonight. Luckily, I thought, we'd eventually throw off the harnesses, and get our own vaginal desires satisfied tonight, in some combination. At the time, it was fun stroking Skippy's vagina. Once in a while, when I was deep inside her, I would reach down and stroke the glans of her clitoris and check for any emulsions from its tip; and, any that I milked from her P-spot, I'd lick off my fingers.

Soon, according to Skippy's script, Skip should be fucking my ass, for which I've been waiting 20 years. Maybe, with Skip in my ass, I can be fucking KrisTy with my cock—my addition to Skippy's script.

I'm thinking though, KrisTy must have one deluxe synthetic cock hanging off her harness if it has balls and she can make its head throb. I must have missed that one in the lingerie store. I wished the lights were a little brighter in the room so I could see with what she had been using to ply Miss Skippy mouth.

Skip: I can't believe KrisTy has me liking her cock so well, cherishing it, and wanting her to get it deeper in my throat. I'm all in, no, she might be all in soon. And, Kit's sync'ing her thrusts in my ass are wonderful.

Kristy had me believing Kit was fucking my "vagina," and had me thinking I could change my gender orientation and nerve senses to feeling and orgasming to dueling vaginal and oral penetrations—Kit rubbing my clitoris on every deep thrust.

I made the transition as KrisTy made "his" last and total penetration down my throat. Kit was resting his whole body hard against my back side with his hips thrust far forward against my butt. My nose was solidly against KrisTy's pubic bone and my chin deeply buried inside his scrotum with his balls extending under my chin. Like a vise squeezing me tight from both ends, I was solidly fucked. Neither Mr. KrisTy nor Mr. Kit moved for what seemed like eons—me without a breath. I could feel the head of Mr. KrisTy's cock throbbing, intentionally on his part, deep in my throat—each pulse longer and its head bulbously bigger on each throb.

KrisTy: Miss Skippy had taken my cock all the way, as far as it could go in her throat—her nose and chin locked hard against me. Mr. Kit had driven into Miss Skippy's vagina as deep as he could go and was holding in the moment with me. And, then I saw Mr. Kit reach around Miss Skippy and grasp again what I figured was the tip of her clitoris and start a slow, soft clitoral manipulation. That was it for me. I couldn't hold my orgasm back any longer. Starving for a human's orgasmic-beckoning touch, intercourse, and sexual relief, I exploded a large salvo of cum. I shot directly down Miss Skippy's throat. She couldn't move.

Because I wanted to give her the pleasure of feeling and tasting my hot cum in her mouth, after my second squirt down her throat, I backed off enough to finish cumming in her mouth; and, while still penetrating deep enough to fill her mouth, my cock left little room for my continued spurt, which started gushing out the sides of her mouth. Knowing that I only had a couple of pumps left, I pulled back just far enough to ejac right on her tongue. I lingered, and Miss Skippy fulfilled her duty and gently licked the ending, slower-to-emerge, long connective streams from the base of my cock's head to its tip, finishing with a slight suck on its end and soft tongue licking slightly into its urethra. I bent down and kissed her lips softly, licked my cum from around her lips and dripping down her chin, and tongued her mouth for our intimate communion before her last swallow. In a low soft whisper, I sealed her sissy fate, "Always remember sharing my hot, life-giving cum in our kiss. Remember my cum filling you, remember us sharing it, remember its thickness and taste, and desire more cock and more cum for all time, my sweet sissy lover."

Kit: When KrisTy came in Skippy's mouth—down her throat—I couldn't tell if this was fake or not. The heat of the moment had caused me to orgasm around the vaginal anchoring plug of the harness. My orgasm wasn't its greatest, but it certainly relieved the sexual pressure we had all been building up. And, I was softly stroking Skippy's clitoris at the time, where at KrisTy's orgasm, Skippy totally squirted what must have been her whole P-spot's extra savings. I tried to capture as much of it as possible in the cup of my hand. When KrisTy pulled out of Skippy's mouth, I exited Skippy's vagina. I took a towel and wrapped it around my still well-lubed cock and walked to the head of the bed next to KrisTy. I raised the cup of my hand, and said to KrisTy, "Let's share this." To which, we licked my palm dry and kissed each other in one long passionate kiss, swapping Miss Skippy's sticky love juice. While kissing KrisTy, I reached down and pulled the blind fold off of Skippy's head. Tossing it aside, I reached between KrisTy's legs to feel his amazing lifelike cock, with which he had just used to throat fuck my darling Missy Skippy.