Pilot Training Ch. 02 - Surprise Guest

Over the last three months, Denise has become sort of a regular around my apartment. With her flight schedule, she ends up spending a Saturday night here in Mobile every other week and a couple of other nights in between. I've taken to picking a seemingly random night about every third week to summon her.

I figured her out in her first session. She's been married to the same man for well over a decade while both pursued their careers. He's not very imaginative so they've basically fallen into a rut. On top of that, he tends to be a gentle lover. Denise enjoys that immensely. But she's also a rather timid lover. The kind of woman who won't go beyond the vanilla unless she's pushed there, and pushed hard to get her there. But once she's there, she enjoys it even more than the traditional.

For about a year she was hearing stories about my friend Andrea. A dominatrix who is also a flight attendant for the same airline. Like me, she's not shy about putting her adventures out there for all to see. At least on semi-private web sites where she has some control over who sees them. Knowing her, I'd bet everyone at that airline had heard rumors within a week, and half of them had probably seen some of the pictures she posted. I know Denise was hearing the rumors but no one ever pointed her to Andrea's web pages. Denise told me that much.

Eventually, Denise ended up as the captain on the same plane Andrea was working. I still haven't figured out if that was just a coincidence or if Denise purposely took the route to meet her. But it was on one of those flights when Denise finally opened up and asked Andrea if she knew anyone who might be interested in guiding her through a few adventures. Andrea sent her to me, and I didn't waste any time. Andrea had called me about midway through the flight. I had Denise come to me as soon as she landed just to keep her off balance. And it turned out to be exactly what Denise needed. Needed to get in an especially humiliating way.

This weekend I'm having Denise over for her fifth session. She arrived Saturday evening after her inbound flight, and I need to send her on her way to the airport by about 3:00 pm this afternoon for her scheduled 6:00 pm departure. Since she arrived I've been tormenting her sweetly while always ensuring that she's unable to climax or even get her fingers to her pussy to do it herself.

To date her husband Leon has been good to work with. That's one of my rules, I never "whip behind a spouse's back." But I also don't care how involved the spouse is. While some prefer to be fully involved, even going as far as to enjoy submitting beside their partner, others prefer to know nothing. Leon has been kind of in the middle. He's been interested. He's kept tabs on what I've done with Denise. He's very eagerly allowed her to demonstrate a few new and very slutty skills I've taught her. But he's avoided anything that appears to be more than marginally painful or unpleasant for Denise. Despite the fact that Denise loves it. I've noticed that he doesn't seem to shy away from things that humiliate her unless they also appear unpleasant or gross.

On Denise's second session I subjected her to an hours-long "interrogation." First I placed an eight-inch-long and 1.5" thick vibrator in her bottom, the vibrator having been modified with a small tube running through it's inside. That tiny tube connected to an enema bag and allowed the fluid to fill her butt while the vibrator was inside her. And vibrating. A two-inch-thick and five-inch-long dildo, modified with small electrodes on each side of it, stuffed her pussy full. She was strapped snugly to a wooden chair which a dozen hard leather straps that ensured she couldn't move more than a fraction of an inch. The room was pitch dark, except for the quintessential bright spotlight in her eyes. It goes without saying that she was naked and that sitting ensured the toys remained deeply inside her. With the vibrator doing its thing, I started asking her very intimate questions. First I drew out every detail of every sexual experience she could remember, including an honest appraisal of Leon's performance. Then I moved into drawing out just as much about her fantasies, even her most secret ones. Anything less than an absolutely shameless and honest answer brought her punishment in various forms such as a cropping to her thighs, stomach, breasts, or whatever else was bare of the restraints. Punishment came from the dildo as well, which sent sparks of electricity into her very eagerly teased pussy. It took a little time, and a good amount of pain for her, but after crying like a baby and begging for mercy she finally gave up and spilled her secrets to me. I sent Leon a well-edited clip of her interrogation, cutting out the parts I knew he wouldn't want to see and the parts about his performance (which were neither flattering nor derogatory bu more neutral in her opinion). That clip has been one of his favorites, despite Denise's obvious discomfort as she sat there moaning with torturous pleasure at the same time she was groaning from having her butt so over-full.

The hardest thing for Denise to admit was three times she'd had a fantasy involving a woman. In none of those did she go any further with the woman than merely touching. I've heard that enough. Almost every woman who comes through here has had a fantasy involving a woman though very few would ever act on it. I'm certain Denise wouldn't have either until her husband agreed to allow her to experiment but only with a female. If she'd thought I'd have pushed her to have sex with me, she never would have come. She expected play, not actual sex, which is exactly what she should have expected.

But it gave me an idea. An idea that was reinforced when I saw how her body reacted to Sophie's sweet touches. So last night, once Denise was airborne, I sent her a message summoning her to my apartment and telling her that she was not to contact anyone beginning immediately. To encourage her, I used the app I'd put on her phone to temporarily shut it down. Then I sent Leon a text: Leon, I've summoned Denise for her layover, so don't expect her to contact you until she's back in the air tomorrow evening. There's something I'd like to do with Denise. I'm very sure she'll love it more than you can imagine. I want her to be in a threesome. I can arrange it this weekend if you are available to be the man in that threesome Sunday morning around 9:00 am and are interested. Let me know, and I can give you specifics if you want them. Interested? Can you be here tomorrow?

It took him about twenty minutes to text me back, which is unusually long for him. Yes, I can be there. There's a flight that will get me in at 8:04, I hope. Denise has taught me that ETAs are about as reliable as the post office is with checks. I'm booked on it, and a return on Denise's flight home. What do you expect of me?

So I sent back: Great, text me when you land and Uber it over to my apartment. I'll be ready when you get here. I plan for you to have sex with Denise. I, my slave, and another woman will be there. The other woman will be "with" Denise. After that Denise and the other woman will serve us while we relax for a bit. Almost like personal waitresses. That's something you could have Denise do at home if you decide you like it. Then a quick thank you for coming from Denise. If she's a good girl, she'll get her relief by supervised (and public) masturbation. Then you can take her to the airport for her flight. I don't plan anything unpleasant for her, however, be warned that Denise decides if she gets punished. If she misbehaves she'll have to be disciplined for it. I can't make an exception just because you're here. My rules have firm consequences, and that's important to Denise. You're welcome to stop anytime if you're ever uncomfortable with anything. Denise isn't, but you are. It's about 20-25 minutes from the airport to my place, so I'd guess you should make it right around nine. It doesn't matter, Denise will wait for you.

He texts back that he's interested and asks me about the other woman. All I text back is that "she's cute," "obedient," and will not know who Denise or he is. I know I'm saying nothing about her, but that's my intention.

After breakfast, I take Denise to the playroom and tie her in a chair. Then I blindfold her and put some earbuds in her ears playing music and canceling out the noise. That way she can neither see nor hear what's happening around her. She loves that. She loves the tense anticipation as she sits there wondering what's going to happen. The suddenness of feeling a touch without even a split second of warning that it's coming.

The woman I've selected for this is Macy. She's 26, 5'7", 138 pounds. She has golden-brown wavy/curly hair down to her shoulders, brown eyes, and a wide mouth framed by full light-pink lips. She also a great set of 36-C breasts that a decently firm and rounded topped with wide rings of faint-pink and nipples a slight shade darker that swell up like half marbles harder than stone. And a well-trimmed dense, but short, triangle of jet-black fur for a bush. Not to mention a very firm and rounded bottom. I'm fairly sure that neither of them will recognize her even though she works for the local Fox TV station. She does the traffic reports weekday mornings. A year out of college, a girl has to start somewhere! "Cute" might have been a bit of an understatement: she's pretty enough for a network TV slot, even if it is in a lower-ranked market like Mobile. Ever seen a fat or ugly girl reporter on TV?

Macy is married as well. She claims to be heterosexual, but I count her as bisexual, although I'll admit that she'd prefer a male partner, she definitely has some degree of interest in women. Because of her recognizability, I've avoided another female with her, but a couple of sessions back I tied her down and had Sophie tease her body endlessly. Her response to that assured me that she's hungry for a woman, just won't admit it. Then again, her greatest fear is being publicly outed which would certainly cost her her career. Which makes Denise the perfect partner for my little experiment. She won't know who Macy is, and has her own reasons for not spilling any secrets.

Macy arrives promptly at 8:00 Sunday morning. I have Sophie collect her clothes as Macy undresses and lock them away in the filing cabinet one drawer below Denise's things. Then I blindfold her before taking her to the playroom. No reason for her to see Denise or know there's someone there. Sophie comes along as well.

We help Macy to lie on a contraption I've built (or rather designed and had a few cute frat boys build for me) just for this. It has a narrow table for her back to lie on, with a short 8" wide piece of wood for her head. Then it has two 4" wide slats sticking out at the bottom 45-degrees from the table for her legs. There are leather cuffs underneath the table for her wrists. And leather straps for her legs, hips, and shoulders. Those hold her fairly snugly to the table. The table has four legs, plus one more on each leg slat, all six of which are metal screw tubes that allow me to adjust the table's height.

It also has an "A" frame built over the top of it. Once I have Macy firmly tied to the table, I go untie Denise from her chair and take the headphones away so she can hear my commands. I walk her over to Macy, guiding the blindfolded woman to Macy's side. I start by putting my hands to her head and nudging her to lean forward until her lips touch Macy's hard rounded nipple.

Denise gasps out with shock as she realizes that it's woman's breast under lips. I swat her bottom hard with my hand and firmly tell her to start teasing it. She already knows what to do. I've used Sophie's breasts to teach her. But now she must know that it's not Sophie lying there. She steadies the nipple with her soft lips and slowly caresses it with her tongue.

Macy moans out in her high-pitched girly voice. I put Denise's hands to the firm mound, her left to steady it and her right to stroke it's underside with her fingertips while she's licking around its nipple.

I guide Denise through everything, having her tease both breasts fully. Then having her kiss Macy full on the lips, with tongue, long and hotly. Then having her kiss down Macy's body, teasing her more, while keeping Denise's mouth from her pussy. But letting it get close enough for Denise to smell Macy's feminine muskiness as she's kissing her inner thighs.

I try to guess when Leon will show up. When my phone vibrates with the silenced doorbell, I send Sophie to fetch Leon. Even before Sophie is out of the playroom, I take Denise and nudge her up to the top of the table. I start by spreading her feet wide enough that I can see the tendons at the creases of her thighs start to strain before I strap them to the bottom of that "A" frame. I stretch her hands up to its point and lock them there with handcuffs. Then I snug a wide leather strap, like a belt, across the small of her back where the "A's" cross piece is to keep her hips somewhat where I want them. After that, it's just a matter of turning the legs to raise Macy's head up a couple of inches until her lips are fully against Denise's pussy. The "A" isn't perfectly straight up and down; it has about a 30-degree lean to it which has Denise stretched tautly and leaning forward. That puts her pussy in a perfect position for a tongue lashing.

"Skanky..." I coo to Macy, "be a good little bitch now and eat that pussy!" I go on to instruct Macy exactly what I want her to do to Denise's pussy. She obediently puts her lips around Denise's hard clit, using her teeth very lightly to steady the steely nub and slowly circling her tongue around the captive nub. In about a second Denise is screeching desperately needy moans.

I swat Denise hard on her bottom, leaving a light handprint on her globe, and remind her that she's not allowed to climax until I tell her to. That she's to suffer this pussy eating to amuse me with her squirming and screeching. Until I'm no longer amused. And if she's amusing enough, I might remember to allow her some relief. She screeches even louder. I pull Macy's blindfold off, leaving her a good view of Denise's butt and not much more.

It takes several minutes, but I expected it would, for Sophie to return. When she does she has Leon, leading him by his hand. And now he's wearing only his boxer shorts, which I uncharacteristically allowed him to keep as a concession to his modesty. I only did that because I don't know him well enough to know how he'd respond to my customary treatment. For all I know, it might get him good and excited. But it might turn him off too.

I take his hand from Sophie, shushing him with a finger to his lips. I lead him around to Macy's side where I allow him to get a good look at the nude woman lying tied to the table. He can see Denise as well, stretched taut above Macy. But he knows what she looks like. His eyes are on Macy's nakedness. Mostly on her rounded breasts as their nipples strain to new heights of hardness and her pussy as it oozes her honey into her fur. Unlike Denise's pussy, Macy's has a wide slit that now, with her legs splayed, is gaping enough that he can see her pinkness between her puffy lips, and the ends of her deep-pink folds.

"Just nod. Not a sound. Is this bitch pretty enough to eat pussy?" I have to raise my voice above Denise's incessant screeching moans. He quickly nods. Anyone would. Macy is an attractive woman. "That slutty bitch seems to be enjoying this bitch's hot tongue on her skanky pussy, isn't she?" He nods just as vigorously.

Denise screeches very hungry and loud moans. She squirms hard against the straps. The chain of the cuffs even rattles as her taut arms struggle against the cuffs. Her head snaps from side to side as her shoulders squirm hard. But so far nothing has knocked the blindfold from her eyes.

I put his hand to Macy's breast. That's all the encouragement he needs to start playing with it. It's not long before Macy is squirming around a little herself. And I see Leon's cock sticking up under his boxers.

I slip my hand into his boxers. As my fingers wrap around his stiffness I feel the slightest of flinch from him, as if he's surprised that I'm touching him. Or maybe surprised that I'm gentle and tender. Maybe he expected me to be rough and mean. That would just be so stereotypical!

I casually stroke it, but only a couple of times. "Ohh... that's ready!" I keep my light grip on it and nudge him around to stand behind Denise. Releasing his cock I push his boxers down to his ankles. "Let me start this," I say softly and sweetly, but with a bit of firmness to my voice. Hopefully enough that he knows I'm not asking.

With a nod from me, Sophie reaches over and pulls Denise's cheeks wide apart. With Denise leaning forward it also bares the densely-furred mound of her pussy. And it's sopping wet fur.

Sophie uses the tips of her fingers to pull Denise's lips open, exposing her cream-covered pinkness and folds. It gives a great view of Macy's lips snug against that pinkness right atop her unseen clit. And of the honey steadily flowing from her tunnel.

I guide his hard shaft towards that sopping wet tunnel. Once the very tip of it is touching the entrance I slip my hand back to the root of it, letting my palm lie against his balls. I put my other hand to his bottom and nudge him to come forward slowly. I watch as his cock inches into her sopping wet pussy. As soon as she can feel herself being stretched by that average-sized cock Denise's screeches turn to even needier near-screams. She squirms more energetically, which I'm sure Leon would have thought to be impossible. Now her hips are even thrusting backward, trying to drive herself down on that cock, at least for a fraction of an inch before the straps stop her.

I guide him through two very slow strokes. Denise screams her desperate moans steadily though them. On the second stroke, I keep him moving the extra quarter-inch until his cock slips fully out of her pussy. I hear Leon gasp slightly as it slips out. But Denise doesn't quiet down.

I've talked to Leon a little over these three months. He's been a help to me by talking about Denise. But I've also learned a little about him. I know that he's never tried anal. He would like to, but his aversion to his lovers being uncomfortable has always kept him from asking anyone for it. Or mentioning his desire to try it. Why talk about something he's confident he doesn't actually want because of the side effects? But these last few months I've taught Denise how to relax her butt and allow herself to be used that way without it being bad for her.

Leon stiffens up as I put the tip of his honey-slickened shaft against Denise's tight-and-tiny asshole. Denise knows exactly what's pushing lightly on her muscle, and what she's expected to do. She's done it enough, just with toys instead of men. She pushes back forcing her ring to loosen up. As it turns to rubber his cock slips right through it. Denise cries out, but hotly not from pain. I keep hold of his shaft and guide him to slip slowly into her. Denise screams out urgently desperate moans at an even louder volume. Her body squirms as hard as ever, adding a shivering shudder to it.

I guide him to put all of his shaft into her bottom. Moving my hands to her hips, I stead his pace as I get him fucking her. I set a casual pace, steady but neither rushed nor too slow. On the first stroke, I can see her asshole tighten up hard as her butt cinches down to snuggle his cock.

Denise screams girlier and needier moans with every tiny motion.

I tenderly caress his bottom with the flat of my hand. "She loves this! Just stay steady for her and enjoy that bottom." I take my hands away letting him go. He tries hard to keep his pace.