Happy Birthdayversary! (breaking him in)

After having spent the day preparing I found it hard to relax. I suddenly got nervous; what if something went horribly awry? I tried to grab some sleep but gave up after about an hour and decided instead to shower, then head over to make my final preparations. Finally everything was in order and I returned home to collect my accomplice. We made our way to tia's house where Izzy was to take away our car while I took tia's. I'm still very amused by the thought that I stole his car to kidnap him in.

At long last I crept into his room, plastic knife in one hand, dirty panties and vet wrap in the other. Climbing on top of his sleeping form I growled “do as you’re told and you won’t get hurt bitch” as I pressed the knife to his throat. I shoved the panties into his mouth and wrapped the vet wrap a few times around his head, over his mouth, to hold them in place. A few more wraps around his eyes, then I rolled him over and wrapped the last 1/3 of the roll around his wrists, binding them tightly behind his back.

With Izzy on one side and me on the other we led him out to the van. Barefoot, blindfolded, bound and gagged, and wearing nothing but the girly tshirt and sheer ruffled panties I’d ordered him to put on earlier. Though he was clearly still groggy from sleep I could also see him trembling in blissful anticipation already. It must have been an exquisite torture being led outside, practically naked but still feminized, with his slave role so blatantly on display, right out where all his neighbors (for all he knew) could see him! And with the knowledge in his mind that wherever I was taking him, whatever I was doing with him – he would be trapped there and at my mercy, with no id, no money, not even a pair of pants to get home in.

We pushed him into the back of the van and shut the door, then I gave Izzy a quick kiss goodbye and got in. I drove away from our destination at first, keeping a careful eye on the clock and a careful ear out for my captive in the back of the van. After about ten minutes I turned and headed back to sandpit manor. I reckoned that would surely confuse him about where I’d taken him. The drive was thankfully uneventful (I remember him farting, and me giggling about it) and when we arrived I backed carefully into the drive, all the way up into the carport so that our doings would be obscured by the house, the high fence, and the van itself as well as by the darkness. I waited til the interior vehicle lights had gone out before I opened the rear hatch to let him out. His steps were hesitant but he did not stumble as I guided him across the leaf-littered drive and up the steps into the house.

I’d laid everything out beforehand so when we got there all I had to do was push him down onto the waiting mat and get down to my dirty business. First I wanted to make sure his allergies didn’t interfere with my plans. I dashed into the kitchen and retrieved a glass of water and a shot of Irish Crème liquor. Then back out to where I’d left him bound and helpless on the floor. I grabbed a handful of his hair and pulled him up on his knees, then unwrapped the panty-gag from around his head. “How did you like the taste of those, slave? I wore them for two days so they would be nice and filthy for you. Here,” I continued, arranging the panties so the saliva-wet crotch covered his nose, “since I went to all that trouble let’s just keep them on you so you can continue enjoying Mistress’s lovely scent.” He whimpered and shivered in response.

After securing my panties around his head I popped the allergy pill out of its wrapper. Of course HE didn’t know what kind of pill it was as I held it to his lips and ordered “Swallow this bitch”. When he accepted the pill I gave him a sip of water to wash it down, and followed it with the shot glass: “And this too. ALL of it bitch. That should keep you nice and compliant.” I cackled as I pushed his head back to the floor. Let him think I’d given him hormones, or a tranquilizer, or whatever other possibility his fertile imagination supplied. I was confident the pill plus the shot would be enough to soundly push the ‘drugged into helplessness’ fantasy button.

Next I finally undid his hands and, while he groaned and shook the kinks out quickly shimmied into my waiting strapon harness. I grabbed his collar and leash and the red suede shackles and knelt beside him again. As I secured the collar around his neck I calmly stated “you notice I’m not asking if you want this. You’re mine now whether you like it or not, and I WILL do as I like with you.” He trembled again, and I continued, clipping on the leash and securely fastening the shackles around his wrists and ankles. “Now I want you on all fours slave” I barked, smacking him again with my crop, “like the bitch in heat that you are.” I squatted down, perching on the small of his back. Stroking his ass in his pretty polka-dot panties, I outlined what was happening to him: “you’re my sissy whore now, and I’m gonna break you in real good before I start renting this sweet sissy ass out. Gonna make sure you get plenty of practice fucking and sucking so you’ll be able to take it like a pro when I start sending johns to you. You feel that?” rubbing my dildo along his buttcrack “You’ll be feeling every inch of it real soon.”

I stood and administered a couple more whacks along with another warning to do as he was told, then crouched down beside his head. His lips parted obediently as soon as I brushed them with my plastic penis and I slid right inside that warm wet hole but I whacked him a few more times with the crop anyway, warning “I’d better not feel any TEETH, lazy bitch” He moaned and sucked me deeper into his hungry mouth. I held his head with one hand twined in his hair and the other at his jaw, admiring the way it looked to stuff his pretty mouth full. And of course telling him all about how pretty he looked and what a good sissy cocksucker I expected him to be, what a fine addition to my stable of whores.

After a few minutes I announced that he’d sucked my dick enough to get me good and hard, and moved around behind him. I pulled down his panties and planted a kiss on the soft white roundness of his ass then straightened up and began rubbing my cock in his crack. Saying “see how hard you’ve got me bitch? How excited I am at the thought of raping you?” I squirted a glob of lube onto the shiny purple head of my cock then rubbed it around his tight rosebud. As I pushed it in I could feel his asshole twitching around it. He moaned then gasped in pain. I pulled out, added some more lube, and pushed back in several times until I felt he’d relaxed enough to accept me. Then I slid in deeper and deeper til he groaned as my pelvis pressed against his ass.

After I’d gone to the trouble of find the special batteries for the vibe I was damn sure gonna use them, so once I was planted deeply inside him I fumbled around, wiggling my fingers between the harness & my body until I found the button to turn it on. Then I settled in to bugger him really, really well.

I came lots of times while I fucked him, small orgasms made infinitely more potent by my murmuring to him each time: “there bitch, that’s another trick who just shot his jizz into your horny ass. Are you ready for the next one? Too bad, cause there’s another hard cock waiting to fuck you…” Filled with the triumphant feelings of kidnapping him, enslaving him, raping him I became a one-woman gangbang. I was high on the rush of control and insatiably aroused.

At some point I decided to switch cocks. He were so receptive, so pliant beneath me…I was so filled with the sense of power, the idea that I could do anything to him…that I wanted to fill him up with something bigger than he had ever taken before. So after one more orgasm (that’s one more trick pumping a load into your horny ass slave…) I pulled out and, as quickly as I could manage with excited fingers fumbling on slippery lube-wet snaps, I changed to my disturbing alien dick.

I took advantage of the lull in the sodomy to commence with the next level of his ‘breaking in’. My plan had been to rape his ass right away, figuring the buttfucking would break any possible resistance (ha!), and then while he was putty in my hands to begin his sissy transformation. I announced it was time to begin his feminization and pushed him once more up on his knees. As he knelt before me I informed him that we’d be getting him a nice big set of knockers implanted soon, but for starters we were gonna make those cute little nipples as big and pink and puffy as possible. Which naturally means using the nipple suckers. I lifted his t-shirt and laved each nipple in turn, sucking and biting it before attaching the small black suction device that would make it swell and redden.

While I gave the nipple suckers time to work I teased him, stroking his throbbing cockette and speculating about how it might get smaller and more useless once he’d been on the hormones for a while. That’d be ok though, since nobody was interested in using that silly little thing except to torment him with. That it might even make it easier on him once he was locked in chastity all the time. I noted also how the nipple suckers poked through his purple t-shirt, looking for all the world like big fat female nipples perched atop full breasts. I told him how mouthwatering they looked on him, and how charming it would be once we got those implants done and he had big fat boobs for me to play with all the time. How much I would enjoy sliding my cock in between them, tit-fucking him, having yet another way to use him.

After a few minutes of this I judged that his nipples must be sufficiently swollen; with casual brutality I flicked the suckers off both of them at once. They might be red and puffy already but I was not at all ready to stop torturing them, so I bent to nibble and suck on his nipples some more. I got a little carried away perhaps, actually chewing on them more than nibbling. He whimpered and yelped but didn’t pull away from my sadistic caress. I was reluctant to remove my mouth but other urges were growing so I impulsively clipped a clothespin on each nip then moved to the other side of his body.

I used a carabiner to quickly clip his hands together behind his back. Then reached around to tease him about how it made his tits stick out. He yelped when I pushed him forward to lie atop the waiting cushion. It must’ve hurt a lot lying on top of those clothespins like that; he yelped and tried to lift his torso away from the cushion when I settled my ass on the back of his thighs. “Mistress, please…” he whimpered

“What is it slave?”

“The clothespins, they’re too much”

“Well I guess you should beg me to take them off then.”

“Oh Mistress please, your sissy would do anything for you but they hurt so bad Mistress will you please please take them off?”

“Oh, all right, you big sissy” I turned around, straddling his legs, and used his hair to pull him to his knees. Lifting his shirt I ripped the left pin off one nipple, then the other. He yelped and I pressed my fingers against them, soothing that first sting but then making it worse by pinching and twisting on them myself.
But I was in the middle of something, so soon I shoved him back down, face-first, onto the cushion. I leaned over and grabbed the pair of red fishnets I’d laid out and (with the minor interruption of having to unfasten his ankle shackles) sensuously slid them up his legs. He shivered and moaned as the soft stretchy net spread up his legs. Then I opened his other birthday present: a brand new pair of slutty black pumps with 4” heels and a delicate ankle strap. I pulled his feet up one at a time, sliding them into the sexy arched shape of the shoes and fastening the straps securely around his ankles. Then his shackles were returned, and my pretty whore was really looking the part.

I paused to admire my work, stroking his luscious thighs and squeezing his buttcheeks. Then I moved up to his head; I meant to make him suck my big hard cock before I shoved it up his ass. I rubbed it on his (still blindfolded) face, smacking him with it, taunting him about how good it was going to feel to have that entire, massive piece of meat up inside him. How much his slutty whore self was gonna love it, even if it hurt. I get such a rush literally rubbing his face in it like that. And then I slipped behind him once more, pushed him down onto the cushion, spread his cheeks and (adding another quick glob of lube) slid it in. Inch after inch he took it, moaning and whimpering like it hurt but wiggling his cute ass around and humping back against me to take more and more. Soon I was buried to the balls inside him and he was groaning as I swung my hips back and forth. I wanted him to feel every fucking inch of that cock, to feel utterly, completely filled. And USED.

I’d snatched him from his bed just after 3am and when I finally let him up from that first round of sodomy it was six. So I figure I spent nearly two hours fucking that sweet sissy ass. And I know he’d never taken anything that big before. So yeah, I’d guess that I accomplished my goal. *evilgrin*

I must have cum at least 6 or 8 times, maybe more, but up to this point they’d all been those little popcorn orgasms: plenty of ‘em, but none really satisfying. And by now my lust was at a fever pitch. I wanted to cum again, good and HARD. So finally, reluctantly, I pulled my strap-on from tia’s ass and wiggled out of the harness. I unclipped the carabiner holding his wrists together and tugged the leash, prompting him to clamber up on all fours. I knew just how I wanted to accomplish this so I shifted to the sofa and reached for gizmo, our combination gag & dildo. I fastened the strap around his head and pulled it to me, aiming the black rubber phallus at my throbbing pussy. I draped my legs across his shoulders, closed my eyes and began to move, grinding my cunt against his face and frantically rubbing my clit. After just a few minutes I was swept away by powerful waves of pleasure, bucking and clenching my thighs around his head.

When I came down from these ecstatic crests I unwrapped my legs from around his head and unstrapped gizmo. As is our usual custom I presented my end of it to him to lick clean, but I only gave it a few cursory swirls in his hungrily sucking mouth before laying it aside. I was hungry now myself so I scampered to the kitchen, grabbing a glass of orange juice and a couple of donuts. I returned to my seat on the sofa and pressed the glass to his lips, allowing him a sip of juice before feeding him a big bite of donut. He moaned in delight, swallowing the sugary morsel and saying “Mistress, you just crossed the line into complete decadence.” “Oh no my pretty slut," I responded, "I’m just getting started.” When we’d finished devouring our snack I licked my fingers and gathered him in my arms. Unwinding the vet wrap from around his eyes I announced “welcome to your new home bitch.”

to be continued...