“John’s definitely cheating on me — after all the kinky stuff we do in bed, even.”
My friend Amanda looked at me, disappointed.
“I don’t get why guys do this to me — I do whatever they want, and they still want more,” she continued, “like — what other girl would dress her boyfriend up in her lingerie and fuck him? And he would make me dress super girly and babyish too; it was just weird.”
My ears perked up at this — and I felt my dick harden in my pants. I had always had this exact fantasy of cross-dressing and forced feminization, which, as a guy, was always an uncomfortable topic to bring up with women. I tried to maintain a look of surprise.
“Wow, yeah, that is something — he would make you do all that?” I prodded her to tell me more.
“He was very specific about all of this, yeah. Like he bought us matching outfits and made me pretend that I bought it for him, and wrote really humiliating things down that he would want me to say to him. Once he made me film us while dressing him up as a Playboy bunny, like the whole outfit, tail and everything. Of course, he made me wear a matching pink one while we did it. And mine? The tail was a butt plug that he made me wear all night. My ass was sore for days.”
I had a fully formed erection now, and I crossed my legs. I tried to imagine sultry Amanda, curly hair dancing outward, dark-skinned long legs clashing with the sequined pink leotard, already-strained by her big ass, helping little John into the slutty costume. I could barely focus on Amanda anymore.
“I just want to get back at him somehow, you know? Really embarrass him — I thought about like telling people about all this, but I wasn’t sure if that’s fair.”
Immediately I wanted to help. John was a cute guy, mid-20’s, medium build and white. He was smaller than Amanda, both thinner and shorter. Shaved, with long hair, and forced into a cute little dress would be my wet dream. And knowing that he would get off on it too was especially arousing.
“Well,” I suggested, “I think I might have a way to help out,” I ventured cautiously.
Amanda looked at me, skeptical.
“It wouldn’t be public humiliation or anything; just you and I would know. But he would certainly learn his lesson.” I didn’t want to reveal too much. I had never told anyone about this fantasy, and I wasn’t sure how Amanda would feel about it.
“How?” she asked.
I tried to confidently smile to avoid any questions.
“It’s a surprise. Just give me a few days at your apartment, and any photos or videos you have of John dressing up or anything similar.”
She looked concerned.
“I don’t know — I mean, I’m in some of those — it’s kind of embarrassing for me, too.”
I pressed harder.
“Amanda, we’ve been friends for years. I’m not going to comment on whatever you do in your personal life, and it’s not like we haven’t already talked about this.” I spoke nonchalantly.
“Well — okay — I mean, I’m going out of town for work next week from Thursday to Sunday. Is that enough time?”
My heart was racing.
“Yeah, that’ll be perfect. John will regret ever cheating on you, and I’ll make sure that he is ready to apologize to you when you get back. I think he’ll even try to make it up to you somehow.”
“We’ll see. I’m not sure if he’s that good of a guy,” Amanda laughed.
She pulled out her phone and started forwarding me text messages, photos, and videos. I was already imaging what we would do together. By the time she was back, I’d teach John to be a very good girl, at least for me.
Getting home, I eagerly started to preview what Amanda had sent. John hadn’t bothered to hide anything. Photos of him in leggings or just cute shirts turned into full frontal lingerie shots. I started playing with myself as I watched John slip into club dresses, short and glittery, posing with Amanda. John tied up with the dress pulled up, a thong and penis bulging prominently displayed. John dressed up like a ballerina: a pink leotard and tights, a special tutu extending far out from his waist, hands held high over his head.
Amanda’s more humiliating shots entered later into the photos. A picture of her in what was very clearly a little girl’s pink princess dress on her hands and knees, looking up into the camera. Her normally curly hair was in pigtails with white sheer stockings around her legs. She was on a leash, held by John in what was a fairly conservative Mommy-look. Dressed in a yellow-print flower sundress with white heels, he looked like a housewife letting a little girl play dress-up.
I watched the bunny video. The 20-minute clip featured the two hopping around, John’s hands posed like little paws as Amanda pulled his dick through a cut in the outfit and sucked on it. He sprayed cum all on the front of her outfit, up her tits and into her face, smearing his cream along her black skin while she patiently sat for him.
I took notes on what John liked to wear. He was clearly a princess-type sissy; the more lace and ruffles, the better. I printed out a few pictures of him, one after another, to display. Him and Amanda in matching pink prom dresses that ended mid-thigh, pressed up against each other. Him as a sexy schoolgirl, lollipop in between his lips, legs so wide apart that the white panties were clearly visible under the tiny pleated skirt. Him in a classic little black sparkly dress, ready to go flirt at the club.
None of these photos or videos, though, involved him with a cock. Amanda hadn’t put him on his hands and knees, spread his ass, and took his sissy virginity yet, apparently. He hadn’t reciprocated Amanda’s sexy blowjobs with his own lips around a strap-on yet. And that was where I was most excited. I was going to make sure that John got the experience of being a proper sissy. His lips were going to suck on the tip of my cock until his knees were sore and he had cum already, just begging me to finish so he could be done. I’d make sure he grew to love being pegged with a strap-on, all dressed up. And once he did, I would re-introduce him to Amanda as a new sissy toy — one that would pleasure her new boyfriends and embarrass him completely.
The next day, I arrived at Amanda’s apartment. John was due in a half hour or so. Amanda had lied about leaving for the weekend, telling him to meet her here. I had to prepare. I slipped into one of the outfits he bought Amanda — a sparkly, pink-and-white take on a French maid’s outfit. I pulled the bright pink ruffled thong up my legs and felt as it slid into my ass. My cock immediately popped out of the fabric, and I tied a long baby pink ribbon around it into a cute bow, draping it artfully. White thigh-high stockings went up my newly-shaved legs, and I puffed up the little pink bows on the front of my thighs. My hand strayed to the front of my panties, already aroused at the sight of my little toes wiggling in the stockings. I slid the petticoat onto my waist and spun slightly in the mirror, up on my toes, like a little ballerina. The petticoat was practically a tutu — it extended almost straight out 6 or so inches, barely reaching my bottom.
I spun around again in the mirror, straining not to play with myself. I didn’t even have the dress on, nor had my pretty little boy toy arrived, and already I was ready to cum. I slipped on the white silk gloves up to my elbows, and marveled at how girlish and dainty my hands looked. The ruffled choker went around my neck, white frills on top and bottom while a shiny pink ribbon wrapped around the middle, tied off in a cute bow at the front. It matched the bra — stiff from the underwire, white lace, with a little bow.
I finally slipped the dress over my head, immersing myself in the silky pink girlishness. The fact Amanda wore this previously, sliding her perky breasts into this dress, feeling it along her smooth midriff, and sweat in it while John meekly fucked her enhanced the feelings of sluttiness. I tried to smell her perfume in the fabric.
Pink heels and a dainty hair box headband completed the look. I twirled the feather duster between my fingers as I strut across the room, my ass accenting each step with a cute wiggle. Bending down, I glanced back at the door. The lock clicked. I puffed the petticoat out slightly more, and made sure I was going to be the first thing he saw on walking in. I didn’t want to scare the little boy too much.
“Sweetie?” I spoke effeminately out to the entry way. “A little surprise is in here for you.”
John walked in and stopped before he could speak. I stood up fully, letting my skirt cover up my panties again, and seductively walked toward him. I held one hand behind my back, keeping what I was holding out of his view.
“Hi John, I’m Lexi, your house help for the weekend.”
John took a small step back, still silent. I kept approaching him as he backed up to the wall, still swaying with each step, my skirt swishing back and forth.
“Amanda couldn’t be here this weekend. She wanted me to come by and keep you company.” I walked up to him, looking down at his face. My heels now brought my to slightly above his eye level, and I stopped only a foot away. I ran the feather duster along his chest, and knelt down, sliding my hands to his waist.
I stopped on my knees and paused with my lips in front of his crotch, kissing it gently.
“Do you think I could be of service to you, sir?”
John started to nod, and started to speak.
“Wow — Amanda — who are,” I rose quickly and put my finger to his lips, telling him to be quiet.
“Shhh, sir. I’m here to help you. I’m like your babysitter. And right now, I need to get you ready for our weekend together.” I giggled and batted my eyelashes, my feather duster still tickling his body up and down.
“We’ll have lots of playtime together. Can I get you ready now, sir?”
John nodded, mumbling inaudibly, struggling to think coherently as my fingers found the way to his penis, stroking along the front of his pants.
“Good, sir.” I stood up slowly, my chest arched out as I gave him a full view of my sissy cleavage, keeping his eyes on my chest, as I reached behind him. “Now, I do have to put this in, which might be a little uncomfortable, but I know for a strong man like you, sir, you can take it.” I smoothly pulled the ball gag that I had in my hand around his face, pushing the ball gag up to his lips. John’s eyes widened as he felt his lips open, and I naturally fitted it into his mouth. I strapped it around his head and secured it, supporting his head in my hand. The feather duster was caught between our chests and I smiled sweetly at him, wiggling my chest against his.
“Doesn’t that feel better, darling?” My gloved finger came to my mouth, and I thoughtfully curled the silky tip around my glossy lip, nibbling on it seductively.
“Now, what else…” I toyed with him, pretending not to know what to do. His hands meekly came up to my waist, rubbing along the frilled skirt and my silky curves.
“I’m in such a pretty outfit, aren’t I?” I smiled at him, bringing my shoulders together to highlight my chest more. I slowly turned around, remaining in contact with his body, and I purposely shifted to have my little butt slid along the front of his pants. I paused right as I felt his bulge meet the middle of my ass, and I slid up and down slowly, bending at the knees like a stripper. One hand hung around his neck, and he stayed still as I showed off.
“Wouldn’t you like to be dressed up like this too?” I turned back around and stood up, nibbling at his neck.
“Amanda showed me a couple of very cute pictures of you — such a pretty little girl.” I felt him clench up as he realized I was aware of all of his habits, and his eyes widened again.
“Personally, I love pretty, little, sissy, girls,” punctuating each word by whispering in his ear, pausing for a moment, “I fuck them, spank them, and let them suck me, and cum all over their sweet faces.”
“Let’s get you out of these gross little boy clothes. I have the prettiest panties picked out for you, wouldn’t you like to see them?” I teased him.
John nodded. The poor boy was still in shock from his fantasy being fulfilled, and better than any girl could do. John clearly needed another sissy to play with. I led him to the bedroom, hooking a finger into the top of his pants and pulling him behind me.
John’s outfit was neatly laid out on the bed, and I could almost feel his dick get harder as he looked over it. I giggled. It certainly was something, all designed to give any sissy an instant orgasm. First up were the classic, ruffled pink and purple panties, with “Sissy Princess” embroidered in cursive on the back. Pink thigh-high stockings with little purple bows at the top laid next to 2″ pink strappy heels, showing off the sissy’s toes. The dress made up of a satin, ballerina like leotard, with frilly flowers lining the breasts and neckline. Pink ribbons held the dress along the sides and back, crossing each other. Two short petticoats puffed out the short skirt of the dress, meant to barely cover any girl’s butt, and it puffed out widely to the side. A tiara and choker laid above the dress.
“You certainly look like the sissy princess, ballerina type, even as a guy.” John walked up to the bed and started feeling the outfit.
I started undoing his pants, allowing his dick to spring out, fully erect, as his pants and boxers fell to the floor. He stepped out of them for me, and allowed me to pull his shirt off, holding his hands above his head. He stood naked except for his gag, completely subservient to me. I clasped my hands together girlishly.
“Dress up time! Soon it’ll just be us girls.” I toyed with the few inches of his penis. “Does little sweetie want her panties?” I used a baby voice to mock him slightly. “Of course she does!”
I laid John on his back and put his legs in the air.
“Ballerina toes, baby,” I gently instructed as I slid the panties up. His dick was already wet as it disappeared under the ruffles. The stockings went on next, one after the other, and soon I had two sweet little sissy legs waving at me. The heels clasped around his feet, easily fitting into the straps, and I latched the silver buckle onto his ankles.
“We should get you some cute ballerina slippers, shouldn’t we?” I moved his legs up and down in the air. “I bet you would love to do a little dance for me, all dressed up in a sequined little girl’s outfit, hair and makeup done? You would look so adorable.”
I pulled him off the bed in preparation for his dress. “Hands up like a ballerina now!” I held the petticoats for him to step into, his hands held above his head. His bare chest was now the only thing ruining the picture of the sweet sissy, and I held up the dress for him. The satin felt so good to pull over his body, and I could almost see his skin tingle as I gently pulled it along his sides. I straightened out the ribbons. “Keep your cute little pose, dear, especially now that you’re dressed up.” I adjusted the choker onto his neck, and slid the tiara into his longish hair.
I stepped back and clapped gently, excited. “You look like the perfect sissy — little ballerina twirl for me, baby.” I spun my finger around in a circle as John hesitantly took little baby steps around, hands still held up in an oval above his head.
“When you face me again, kneel down,” I instructed. I grabbed a small makeup bag as John knelt down. His dress covered up his legs, spreading out in a wide circle. His heels jutted out from the back, and he meekly put his hands on his lap as he waited.
“Some finishing touches to be especially sexy,” I commented, as I applied lipstick, “pout, baby, give me nice big lips that boys love.”
I grabbed his chin, moving his head up and down as I inspected my work.
“Hmm, I should have thoroughly shaved you from toes to head, but I’m a little impatient to play.” I started to slowly lift my own skirt up, slowly, and his eyes drifted down to the mass of frills.
“You have to pat your pretty pink lips dry — why don’t you give me a quick little thank you kiss on the front of my panties, sweetie.” My penis bulged out of the panties, just peeking above the ruffled top, and the thick outline was clear. John anxiously rocked back and forth as he eyed the hard cock coming closer to his face.
“Just a little baby kiss,” I gently prodded him, “smoochie smoochie,” I snickered. John gave in at this point and started to lean in, his shiny lips puckered.
I moaned slightly as his lips came to my panties. The soft pressure on my cock caused some pre-cum to leak from the head of my cock, and I couldn’t stop myself from holding his head there on my panties. I rotated his head slightly, forcing him to kiss around the girth of my cock.
I pulled him back. “Look at that! You left your mark.” A pink smudge was clear on the front of the panties.
“But it will show up much better on my cock, won’t it?” I slipped my fingers into my panties and pulled them down to my thighs. My cock immediately sprang out into John’s face, bouncing off his cheek. Without any prompting, his hand came up to hold the base of my cock and held it to his lips.
“Good girl. Give it a nice suck for me.”
John obeyed, and I moaned louder as his lips enveloped the head of my dick. I coaxed her further.
“You look so sweet with that cock deep in between your lips — don’t struggle too much sweetie! Looks like your eyes are getting a bit red already, but you can’t be a sexy sissy and a crybaby while giving blowjobs. Being a sissy can be hard work! And soon I’ll cum for you, ok, darling?”
She looked up at me, still sucking eagerly, and moaned in agreement. I kept rubbing my chest, playing with my tits and feeling the lacy bra tight around my nipples.
“Fuck, yes – you’re going to suck the cum off my cock once you’re finished taking a few photographs for me too.”
I rotated her plump little ass around, draping her on the bed. I grabbed her hair and pulled her head back.
“We can’t leave that pretty mouth of yours empty, can we?” I inserted the gag back into her mouth, clasping it safely around his neck.
I pressed myself up against John, feeling how our pretty dresses were the only thing keeping John from losing her sissy virginity. John struggled a bit, squirming around as she started gyrating against me. She pumped her hips, pleading with me for sexual release. I flipped the petticoats and skirt up, loving the sounds of our dresses rustling up against each other, the pink and purple ruffles weaving together. The panties were damp in the back from sweat, the “Sissy Princess” label a darker pink than ever. I could just barely see John’s little balls encased in the panties, tucked back. I bent over and gave them a little suck through the panties, tempting John into her new sissy lifestyle even further.
“You’re going to cum so hard in your pretty outfit when my cock gets inside you, won’t you? Empty your sissy balls into the cute little girl’s dress for me, right?”
“Mmph,” John mumbled around the fat ball gag snugly fit into her mouth, a meek attempt at a high-pitched girl’s voice. She clearly needed more training.
“That didn’t sound like an excited sissy girl! Now, is my new baby going to submit to her new sissy lifestyle?”
“Yeth!” John squeaked around the gag, this time satisfactorily girlish enough. I gave her another encouraging kiss on the last of her manhood.
“Keep going,” I demanded.
She continued her sexy little moans, appropriate only for the dirtiest of pornography videos. No real girl would sound like this — but my new sissy would learn.
“Do you remember how much you pressured Amanda for anal? How you liked to finger her and stick your thumb into her ass when she was tied up, even when she said no?”
John froze, the frantic thrusting of frills and ruffles ceasing suddenly. I put my hand on her cock and balls, running it along the length.
“Didn’t you say how sexy it was when she acted like a total slut for you? Dressing up in all of that absurd, expensive lingerie? Making her pout for you and play with herself with dildos while you filmed and masturbated once she was filled with plastic cocks?”
I started squeezing gently on John’s balls, pressing them against her ass through the panties. Her manhood was my new play toy.
“Yummy — I get horny too, thinking about all that — lucky for you. She told me about it, and gave me all the photos and videos, and told me all of the naughty things that you liked.”
John started squirming again as I pressed harder, my painted nails digging into her little balls. She tried to turn over, her hands looking to escape the fuzzy pink handcuffs.
“Uh oh baby, don’t get too excited. Amanda will be here in 3 days, so we have lots of time to recreate every single photo and video, and even make some new ones too. And you’re going to finally live all those fantasies that you made Amanda do for you, because you were a scared little boy.”
I punctuated the last few words with hard spanks on her bottom. I leaned over, looking at her face. John was crying now, her big red eyes spilling tears. They ran along the big cock and her stretched out mouth. She looked scared.
“But now, you’re a sexy big girl — don’t you think you’re ready to be the sissy star you always wanted to be?”
I retreated, standing up behind her, and started to pull her panties down. Her smooth legs kicked behind me, a heel nearly hitting my thigh, and I stopped to clutch her balls again.
“You liked it when Amanda struggled, right? That’s good, she’ll like seeing you act like a little baby when it’s time for you to become a woman. Maybe she’ll come home with a guy for you.”
I ran my cock along her ass, sliding it smoothly in between her legs.
“Yikes, someone has a hairy pussy — you should let me shave you later. Now, feel my big girl cock.”
I dropped some lube on her ass, and I felt her shiver from the cold liquid. The head of my cock moved smoothly now, wiping it up and around her sissy clit. I pushed in, feeling her clench.
“Boop!” I giggled as I felt my head slip in. “I’m going to fuck your sissy ass until my new sissy cums all over herself. The slutty videos and photos I’m going to make with your ass and mouth are going all over the internet, to your work, to your friends, to everyone that wants to plunge their cock inside of you.”
I was pumping smoothly in and out, pulling her smooth ass into my hips, the dress falling all over.
“Fuck me, you little slut!” I spanked her hard, and she finally responded.
John started moving her ass into me, groaning through her gag. I continued spanking her, and picked up her discarded panties from the floor.
“Your pretty panties are wet with precum — I know you fucking enjoy this. You need to be a little sissy.” I wrapped them around her cock and started stroking as I pumped into her.
John started moving quicker, her head flat against the bed. I got harder every second I saw the sparkles on the back of her dress move closer to me, and thrust in further.
“I’m going to call you Sissy Jenna from now on, okay? If you want that, just spurt a little baby cum into your panties. Show me you’re a good sissy and I’ll keep you here, indulging in your sissy fantasies, teaching you how to be a big girl for Amanda. And once she comes back, you’re going to act like a simpering little sissy girl, ready to take real cock for her whenever she wants.”
John moved feverishly now, her sissy ass moving up and down my cock. Our frilly dresses shook all over, and I watched my cock poke out of the frilled skirt, the sparkled top gleam in the lights, our matching dresses moving in sync as she struggled to prove herself as a good girl. And with a final exhausted push, I felt wetness on my fingers as she came into her panties, filling up the fabric with evidence of her sissyhood.
“Fuck, that’s so good, Sissy Jenna. Cum into your panties for me.” I continued fucking her limp body, holding her perky ass up with my cock. I needed to cum.
I stuck my fingers in my mouth, imagining sucking off my new sissy as we played together, a little obedient sissy baby willing to perform for my every whim. I started to cum into her ass in waves, filling her up with my big girl cum.
I pulled out, exhausted, and flipped her onto her back. She looked at me with big eyes, the ball gag still sticking out of her mouth. I pulled it out, replacing it with my messy and shrinking cock, letting her suck the warm cum off it like I promised.
As she meekly licked around my shriveled cock, I held her chin and smiled.
“Good girl, Jenna. You’re going to be such a good sissy.”