The Escalation

Hearing this seemed to soften her intense gaze, she smiled coyly and started planting gentle kisses all over my face and neck and chest. Bringing her lips up to mine we kissed as long-time lovers do, caressing each others heads and flicking our tongues playfully around the other. While we explored each others mouths I ran my hands down her sides to her ass and gripped tightly, spreading her ass wide and then squishing her panties between her cheeks.

I slid my fingers under the elastic band of her lacy underwear and went to push them off her round ass when she stopped me with a surprised look and muttered something about "getting herself ready first" before hopping off and hurrying into her ensuite bathroom. Once again confused and disoriented from the constant tangents this night had taken so far, I laid down on her king-sized bed and looked up, realizing for the first time I'd been in the room that she had a full-length mirror on the ceiling. Glancing around the room I recognized an assortment of out-of-place furniture pieces that resembled medieval torture devices. Handcuffs attached to one wall, a rack with hand and foot fasteners, a peg board hung with all manner of leather whips and toys. I sprung out of bed.

My curiosity led to confusion as I scanned the room and a sick feeling started to wash over me as I came to the realization that I was in a dungeon, of sorts. The room started to blur a bit as I made my way to the bathroom door.

Knocking rapidly and starting to sweat, I pleaded with the occupant, "Candice, um, what's, uh, going on?" Silence. "Candice?" Still nothing; then after a few seconds, the hard 'click' of the lock disengaging.

Wading into the room carefully I was faced with a different woman than I'd been in the presence of all night. Instead of the confident, take-charge persona that commanded our whole night, a mere shell of that woman sat hunched over the on the edge of the tub.

"I'm sorry, Phil, I can't go through with it," she said meekly into her cupped hands, "I let it get too far and I should have just stuck to the plan, but you're such a sweet guy and I caught feelings and I'm so sorry and I can't do this to you."

Confused and reeling, I was starting to get angry, "What does that even mean, what is going on, Candice?!"

In reply she opened the cabinet under the sink pulled out a latex mask, a ball gag, and a Polaroid camera. Still not getting it, I asked, "Ok, but why, Candice? What is this for?" As her head sunk deeper in her hands she simply turned the ball gag around to face me.

'April Fools, Fucker!' was printed on the front in white letters and, just below it. 'Love, Jake' with the kiss emoji stamped beside.

A tidal wave of realization smashed into me and was carrying my brain out to sea as I stumbled back out of the washroom and back onto her bed, completely beside myself. From deep inside I let loose the craziest, cackling laugh I think I'd ever released. Laughing maniacally until I couldn't catch my breath and my sides started to kill, Candice poked her head sheepishly out of the bathroom door; it was her turn to be confused.

"Wait, what? You're not mad?" she squeeked out, face half-covered by the door frame protectively.

"Oh, god, no I'm not mad," I honked out, gasping for air, "I mean I am, but not at you and not at this!" I gestured around the room. Regaining my composure, I patted the bed and gestured her to come and sit beside me. "I'm mad at myself."

Reluctantly Candice slid into the room, took a seat next to me on the bed in her urban dungeon and waited for me to demystify my reaction. I spent the next five minutes regaling the long and storied history of mischief and debauchery Jake and I had wrought upon each other over the years and by the end we were both cry-laughing on her bed.

"So, he hired you to catfish me, fuck me, tie me up, whip me, and take pics to send back to him? I get that right?"

"Yeah, pretty much, everything except fucking you, that was my decision," she explained, flashing that soft look we shared before the ruse fell apart. "I don't have sex on the job, but I got carried away and I just couldn't bring myself to embarrass you on film. I was just going to fuck you and tell him I couldn't match with you on Tinder and pay him back the advance." She went on to explain that she worked as a professional dominatrix, had a high-class clientele made up of many of the city's elite and she never mixed business with pleasure.

"So, what happened to the plan?" I asked, ego starting to inflate.

"You caught me in a moment of weakness, I suppose," she said, that hungry stare flashing to the surface momentarily, "and your dick felt so good in my throat that I couldn't help myself." My cock starting to inflate now, she kissed me lightly on the cheek, gauging my reaction before catching herself again and putting her hands up to her face in shame.

"What's wrong? I told you I'm not mad," I reiterated, draping an arm over her shoulder to comfort her.

"There's one more thing I haven't told you yet and I'm sorry for leading you on," she said, blushing, "it wouldn't have been an issue if I had just done the job." And with that she stood up off the bed, reached between her thighs, snapped open the underside of her panties, and from between her legs flopped out a smooth, flaccid cock.

Speechless, my mouth dropped open when she pulled that black monster out. Six inches soft and tucked I couldn't imagine what it would be like hard, but my brain tried to do the math while Candice eyed me up and down, nervously assessing what my reaction. I'd never been with a trans woman before and never would have guessed she wasn't cisgender. She was still easily the most beautiful woman who'd taken me to bed, so I let her know as much.

"Wow, um, well that is something. I'm not mad and maybe it's because you're the hottest woman that's ever had my dick in her mouth but I'm still up for whatever was about to happen earlier," I told her."The making-out-on-your-bed thing, not the bondage, punishment and humiliation thing," I clarified.

I stood up, walked over to her, attempted to mimic her hungry stare (poorly), wrapped an arm around her and kissed her. Perhaps a little surprised she took a half-second to reciprocate but then embraced me as well and we pulled each other in close. As we held each other she began to melt in my mouth, our saliva making sweet music as we kissed, and it felt good to put her mind at ease. Deciding when to move the action forward became obvious; the tap of her girlcock hitting mine from underneath as it became engorged was a clear indicator that she was back into it. This time I turned towards the bed and looking back to her with a hard smile, I reached down and grabbed her swelling black hammer and led her back onto her mattress.

Once we were laying down beside each other I released her now footlong rod and seeing the juxtaposition of it on her lithe frame brought something up from beneath the depths of my horny brain, and an idea started to form.

"Were you supposed to send Jake some pics when you had me all bondaged up, or whatever?"

"Yeah, he wanted just one pic tonight to prove it was done. The Polaroids were for you to keep," she said, embarrassed again.

"Ok, and sorry, one more thing," I asked, trying not to ruin the mood further, "does Jake know you're a trans woman?"

"No, I mean, I don't think he would've known. I don't advertise it and only a handful of people even know that I am. I might lose clients if they knew their dom had a dick. Why do you ask?"

I was all smiles. "I need your help with something then, before we take this night wherever it goes, but feel free to say no..." I let the words hang in the air.

"Jake's paid up for a whole night, so I'm all yours. What do you need?" she answered, curious but a little concerned.

I told her my idea and she loved it, laughing mischievously alongside me.

It was almost 1am by that point and right around 1:30am Jake's phone dinged with a message he'd been waiting for. Opening the text from Candice's number he sat on the edge of his bed, wife sleeping soundly next to him, and started to giggle insanely when he saw the picture that came through.

Naked except for my boxers and on my knees with the latex mask over my head, my hands were shackled behind my back. I had a dog collar around my neck attached to a leash that ran up into the background, where Candice was holding it taut, dressed in full dominatrix gear. In my mouth, the custom April Fools ball gag was covered in saliva. In my eyes, genuine terror.

Oh my god! So fucking hilarious! he texted back, then right after, You can let him go now and tell him I put you up to it. He shouldn't be that mad. *fingers crossed emoji*

Jake sat up and waited for my eventual call, leaving his bedroom so his wife wouldn't hear me screaming at him. When his phone dinged again not 5 minutes later, he thought, "that was quick, he must've ripped that leather shit off in a hurry," laughing to himself.

Instead, there was another pic.

Kneeling beside Candice, still fully restrained, my eyes were wide with fear. Right next to my face was Candice's fully erect 12-inch dick.

Jake almost fell off his dining room chair.

Whoa! I hope that doesn't cost extra, he joked, seriously, you can unshackle him now, he's probably shitting his undies, haha.

No reply. The next pic came 30 seconds later. Taken from the ground facing up at me, the mask was off my face and veins were bulging on my forehead. Tears streamed down my face, my eyes eliciting absolute horror. Behind me Candice was grabbing my bare ass with two hands and looking down on me with that practiced, hungry stare, assumingly burying her whole dick inside.

Jake sat up straight and rubbed his hands through his hair nervously.

Jesus Christ STOP! This wasn't part of the deal! He typed furiously. Then a second later called the number. It rang and went to voicemail. He dialled again and again.

In place of an answer, another pic came through.

This time the pic came from above looking down on my still kneeling form, head cranked back and twisted gruesomely to face the camera, two hooks in my nose attached to a strap pulled up over my head, Candice tugging on the other end behind me. In her other hand, floating just in the foreground a prod of sorts, electricity arcing across the tip.

"Fuck, fuck, fuck, fuck," Jake muttered, panicking and pacing his dining room floor. He power-dialled Candice's phone then switched to mine, calling my cell over and over. Nothing.

The pics kept coming in.

For the next 10 minutes, Jake received 5 more pictures, all of me in seemingly various forms of torture and/or non-consensual sex, progressively escalating in intensity. At 1:48am Jake received a final picture. In it I was doubled-over, covering my nakedness, hands over my face in fear, the flash of the camera reflecting off the metal bars of the cage I had apparently been locked in.

"I'm going to jail," he thought, sweating and reeling. Spamming our phones with texts and calls he begged for me to answer or for Candice to stop, and when that didn't happen, he started to consider his options. Not wanting to call the cops in a different city and tell them that he effectively hired someone to rape and torture his best friend "accidentally," he texted me.

I'm sorry, Phil, I fucked up bad. I'm driving down there right now. I'm gonna get you out of there!

To Candice he sent, I'm coming down there now. Please don't hurt my friend anymore!

Jake put a shirt on, got in his car, and started the 150-mile drive, leaving his oblivious wife sleeping in bed, still trying to reach either of us.

At that very moment, however, Candice and I were full-on making out on her bed, unconcerned with the flurry of texts and calls, having silenced our phones after she sent the last pic. After staging the photos to instill maximum fear into Jake, Candice and I snuggled up close on her bed to release the pictures, cackling together as every response he sent detailed his descent into madness. She had helped me to exact revenge, and we celebrated a plan well executed by resuming where we left off, before the night went off the rails. That night we kissed and ground our bodies together and she blew me to completion, me returning the favour with an awkward hand-job, the first I'd ever provided for a dick that wasn't my own.

Although the penetration and torture were simulated that night, Candice and I dated for a while afterwards and she showed me the multitude of surprises a trans relationship provided, teaching me more about myself and my body than any woman I'd ever met up to that point; but that is a story for another day.

At 3am I left Candice's condo building and made my way into the back of an Uber, heading home. I checked my phone to see over 50 missed calls and about the same number of frantic texts from Jake, each more manic than the last, who was now probably crossing state lines.

I scrolled to the bottom and this time I sent him a picture. In it, Candice and I were staring at the camera beside each other, tongues pushed out at the viewer, peace sign in her hand, my middle fingers popped out in front. When my cell rang immediately after, I answered it.

"April Fools, you asshole!"