I take a deep breath in and put on a straight face before knocking on your apartment door. This is going to be a fun night for the both of us, I can hardly contain my excitement. The door opens and you look me up and down before stepping aside and letting me in. The bottom half of my thigh high stockings and heels are all you can see of my outfit, since I have a long coat on over everything else. I don't want you to get distracted with what I’m wearing. I put my bag on the floor and order you to strip, something I hardly ever do, especially in such a demanding tone. I pull out an unlabeled bottle of lotion and tell you that I want to put it on you, I can tell you're thinking this is going to be some kind of pampering experience and you're getting ahead of yourself, already starting to crawl into bed.
"Did I tell you to lay down?" You stop and look up at me, "Stay standing." I had to work quickly as I don't want it to start taking effect before I finish, I don't need you panicking while I try to cover you completely. I start with your arms and then your front, I've always loved running my hands all over your body, but with the lotion, I can see exactly where I've been and where I still need to go. I make sure to spread your ass and to get it all over every inch of you. Down to your legs, where you've never shaved before. I can't wait to see the final product. You were always so resistant to go all the way for me, but if you're not completely willing, I can always trick you into doing what I want. I know I have no time left as it's already taking effect. You know it's not lotion now and you're getting a bit anxious as it starts tingling and prickling at your skin. You start whining about it, asking me what it is, “Shut up,” I scold you, “you’re fine.” I tell you to go rinse off and you run to the shower.
I hear the water shut off and give you a moment to dry off before stepping in. I catch you still staring at your new smooth body when I walk in, hand on your thigh, sliding up, completely unobstructed. When you notice me standing there, you open your mouth to say something, but I cut you off before you can, “Now that is the body of a real sissy,” I take your hand and lead you back out to the bedroom and take out another bottle of lotion, this time a freshly sweet fragrant one to gently massage into your skin, soothing away any lingering tingly feelings from before. Piece by piece, I take things out of my bag and put them on you. A cute pink thong sliding up your legs and resting on your hips, I make sure to pull the back up just a little higher, to really wedge it in between your cheeks and assure that it rubs against your bare asshole. Your favorite, silky white stockings, I put them on as slow as I possibly can and you feel just how nice they are, gliding on, molding to your hairless legs, and becoming a second skin. Deep feelings of regret sink in as you wonder why you never let me shave your legs before. “All this time, you’ve been missing out… but it’s okay sweetie, we’re going to make up for it tonight.” I put the garter belt on you and attach the straps, playfully snapping each one once in place, letting them surprise you with each velvety sting. The next item out of my bag is a short pleated skirt, I hold it open and you step into it. It’s a little tight, but I pull it up your long legs, rocking it back and forth along your thighs to make it fit. Your eyes widen as I pull out the next piece, a pair of red satin 6 inch fuck-me heels, they’re strappy and detailed with self-tie bows in the back. I know you’re in love with them, you can’t hide it, biting the corner of your lip to stop from smiling only makes you look more excited. It’s a good thing you’re standing right next to your bed because as soon as I put them on you, you barely have a second to admire them before you lose balance and fall backward.
Before you have a chance to sit back up, I'm already climbing up onto you, settling in and straddling your cock, now very apparently bulging beyond the lacy pink thong. "I knew I should have caged you before we started, I can't trust you not to be hard while I'm doing this to you, sick little pervert" Another bottle comes out of my bag and I start applying it to your chest. "Close your eyes," I tell you, "wh–why..?" "I said close them." I found the perfect breastforms, matched to your skintone, as realistic as they make them. I press them firmly to your chest and hold them down for a few seconds as I wait for the adhesive to take. You open your eyes as soon as the cold material touches you and are in shock, but there's no back tracking now. Just remember that you wanted this. You'll be telling yourself this a few more times before the night is over. The last item of clothing, to complete your outfit, is a pink corset. I stand you up and wrap it around you, lace up the back and pull tight on it. I want to create curves on you, your waist is already so thin, we definitely need to show that off. "Under the corset, your new tits look almost real," I reach out and tap them, "Hehe, they even feel real."
I know it's going to be a little tough for you to stay in this position, but I need you to kneel down for a bit while I apply your face. I take my time blending the foundation color, shaping your eyebrows, adding lash extensions for that extra girly flutter. Eye liner, rose colored eyeshadow with gold shimmer, a thick coat of mascara, it's all coming together. Suck in those cheeks as I hold your chin up to find the ideal place to brush on the blush. Pucker your lips for me as I put the lipstick on, a deep red rouge subdued under a sticky layer of clear cotton candy flavored gloss, just to make you shine. Sensual, sultry, sexy. Beautiful. The finishing touch, a long blonde wig, cut and styled to flow just over your shoulders and lay on your breasts, I secure it with a few carefully placed bobby pins and you’re complete. “Stand up and spin around for me, honey” I can’t wait for you to see yourself as I lead you over to the full length mirror. Speechless, you start touching everything, playing with your hair, running your hands down your sides, discovering the curves of your hips, rubbing your legs together and feeling the nylon stockings catching on itself.
You turn around as you hear my coat hit the floor. The elevator eyes are inevitable as you turn your attention to me in a red corset, crotchless panties, and the sheer thigh high stockings you can now see in their entirety. Your gaze, stopped on my harness, is interrupted and shifted, now fixated on the massive fleshy dildo I’m pulling out of my bag. You watch intently, unblinking, as I send it through the harness, and insert the other end, designed to be shared, into myself, exhaling and letting out a soft moan once it’s in place. “On your knees, my sweet sissy boi toy, show me what you can do.” You drop down to your knees and crawl over to where I’m standing, sitting up and taking the cock in your hands, open wide and wrap your freshly painted lips around it, as deep as you could. I look to see where the marks were and furrowed my brows a bit, “You can do better than that.” On the next stroke, I hold the side of your head in place and thrust forward, enough to gag you, enough to feel you push back. With each movement of the cock, every ounce of force and pressure applied by your tongue, lips, and mouth, the part inside me moves and stimulates me. It’s getting increasingly difficult for me to stay standing as my knees are getting weak.
I nod over to the bed and you take your cue, climbing into it and getting on all fours, presenting your ass to me. I slide my hands up your thighs and lift your skirt slowly, letting the fabric brush up against your skin. I pull your thong aside and am met with your clean, pink asshole. It looks so inviting, I can't resist and bend over to taste you, tease your hole, and lick circles around it before dipping the tip of my tongue in. Your breathing deepens, even though the corset is holding your body tight. The lube is cold on your virgin asshole, I press my thumb into it, massaging it, loosening you up, preparing you. I line the cock up to you and start to stretch you out, I'm dripping watching you open up for me. You start letting out groans, letting yourself become more vocal, getting more into it and I see you start to rock back and forth, bucking back on the cock, desperate for more, but unable to take it all so quickly.
The notification light on my phone is blinking and I pick it up and text for a little bit. You're clearly annoyed as the cock slips out of you and you turn around to see what I'm doing, questioning the pause in action. I just look back and smile. "I have one more thing for you," I say as I get up and walk over to your door. You sit up and readjust your skirt, not knowing what else I could possibly have in store. Your smile is wiped clear off your face when I open the door and a tall, muscular man walks in. The blood in your body rushes to your face, turning you a bright red and making your ears hot. No one other than me has ever seen you fully dressed, and you're horrified that I didn't even ask if I could invite someone else to play.
He chuckles with a half smirk when he lays eyes on you, "she looks fucking hot, you did a good job," "I know," I tell him, mirroring his smirk. I make my way over to where you're sitting and stand you up, gently tuck some hair behind your ear, and smile at you, "I can't make you a real sissy, sweetie, but he can." I turn back to the man and feel you crouch back behind me, still very unsure about the situation. "Don't be shy," he walks over to us and I take my hand, place it on your shoulder and push you down to your knees. You reach your hands out to undo his pants, the bulge already starting to grow in anticipation, you unzip him and his cock springs out, hitting you across the cheek. It's hot to the touch, longer than yours, thicker than yours, heavier, more solid, undeniably better in every way. You take hold of it and move your open mouth towards it, saliva already in excess on your tongue, you take your first taste of a real man's cock. That's all it takes to send you into a cockdrunk haze. The cock is almost completely in your mouth now, as much as you can handle without actively gagging, slobbering all over it, licking, sucking, swirling around with nothing short of pure vigor. One hand massaging his swollen, heavy balls, the other wrapped around the base of his cock, stroking him in rhythm with your bobbing head. You're earning your prize, he takes hold of your hair, pulls on it while simultaneously pushing your face into his body, your nose pressed firmly against his abdomen. You don’t need to breathe, what you need is his cum, pumped directly down your throat and into your belly. It’s exactly what you want and you take it like it was owed to you.
As he pulls his cock out of your mouth, some of the cum comes along with it, dripping over your lips. I lean in to lick it up and kiss you, pushing the leftovers back into your mouth. I feel you swallow it and whisper that you are such a good girl in between breaths. He's not done though, before you know it, he's scooped you up off the floor and tossed you on your back, onto the bed. He takes one of your legs in each of his hands and pushes them back, leaving you exposed again. There is no hiding your excitement, your little clitty is harder than it’s been all night. He lubes up his cock and places it at your hole, just as I had done earlier. He's not as gentle with you as I was, he pushes his rod into you much more forcefully, barely giving you any time to adjust. There are tears forming in your eyes as you shut them tight, realizing that there is no going back. It is in this moment that you're no longer enjoying a kink, you've let it become a part of who you are, a pretty little sissy slut. A whore for big cocks, a fuck toy to be used, a cum dump for men to empty their balls into both of your willing holes, and you don’t care. This is who you are meant to be.
He continues fucking you, pulling almost completely out and then driving himself back into you on every stroke, I crawl over and straddle your face, turning my attention towards your cock, putting it in my mouth, sucking you with as much enthusiasm as you had shown him before. The smell of masculine sweat and cum with the flowery lotion I applied earlier mixes well. I am intoxicated, watching his cock like a piston pumping in and out of you, seeing you stretched out as much as you could be. Your moans muffled by my wet pussy, you can only lick me in unison of his strokes. Every time he pushes you, I get moved along with you. I have my hand on his hip, starting to control his pace as I get closer to cumming. The feeling builds exponentially on itself and you lick me harder, sloppier, I grind down on your face and feel the impending orgasm take over my body. The moans escaping me send vibrations down your cock and my pussy spasms and leaks onto your pretty face, you can't hold it anymore and cum into my mouth as well.
I rolled off in a messy pile to the side and he picks you up, your body weak from cumming, you wrap your arms around his neck and legs around his waist. He bounces you up and down on his cock for only a moment and then he tosses you back onto the bed, this time on your front. He picks you up at your hips, placing you on your knees, and mounts you. His other hand smashing your face into the mattress. His cock gets even deeper inside you in this position, he's more free to fuck you with wild abandon, rougher than before because he's about to finish. At once, he thrusts into you and holds your hips firm against his body, you feel his cock pulsing, pulse after pulse as you feel each rope of cum running deep into your boi pussy. It gapes when he removes himself, and I hold you open, diving my face in and lapping up as much as I could, holding it in my mouth and then going over to kiss you again. You know it's not polite to waste cum.
Source: reddit.com/r/sexystories/comments/36f092/no_going_back_fmmsissyfeminizationfpov
Awesome!
Great story. You’ve turned me on, thanks lol
This is amazing. I want to be a sissy like this so bad.