Katelyn's New Sissy Pt. 01

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors and laughing salesgirls, the pacifier was built with a cartridge to release a liquid of my girlfriend's - well at the time, my Mommy's - choosing. First, it was the included with packaging Baby Cumlover - Ensure sexy babies with slutty futures love the taste of cum - cartridge, which was filled with real looking (and tasting) cum that would shoot into my mouth at the touch of the girls' remote control.

The girls found it hilarious, especially when they used the extra-large cartridge. Pictures of my squirming on the end of the Sissy Peni-Pacifier, not able to swallow fast enough with what looked like cum all over my face and dripping onto my outfit, got framed in the store right beside the pictures of me licking my lips and fingers making sure I swallowed every teeny bit. On a return visit, a 19-year old blonde salesgirl, one of the most attractive girls I'd ever seen, tortured me by demonstrating the Sissy's Special, a customizable cartridge, and how my girlfriend could fill it up with everything from baby food to her pee. I had to be dried off with a towel after the salesgirl tried it, lowering herself over my face and proceeding to fill up the toy.

I had been humiliated in practically every way, from being initially sissified, to growing up from a sissy baby to a sweet little girl, to a naughty teenager girl and finally the slutty college girl phase. I'll share those stories with you eventually. The slutty college girl phase had been going on for quite a while, which explained the strenuous sexual training and the panties I was currently wearing. My toes were painted bright pink, with a flower on the big toe, and there were holes in my ears where she made me get them pierced at the mall. Other than this, I looked perfectly normal. She preferred to keep me in a state where I could look masculine for various events, even as immediately after the event ended, I would be locked into my car seat on the ride home or changing into an outfit of her desire in the car to go out later. It was more embarrassing for me as well.

It was a Saturday, and she had rolled over and woke me up by yanking on the silky pink ribbons that had bound me to the bed frame. Last night she had a few girlfriends over who were interested in exploring some dominatrix type experiences. They practiced on me, tying me up, spanking me over their laps, binding my legs up high in the air, and practiced with their new dildos. By the time the fifth girl made me beg to be fucked by performing a strip tease and lap dance for the room, I was pleading to be set free with tears coming from my eyes as I wiggled myself over her skirt. Of course, they ignored me, stuffing their wet panties in my mouth.

My girlfriend had dressed me in a new pink leather minidress, with matching pumps that locked on my ankles and gloves that went up my forearms. The tiny thong she put on me left no protection from the girls' prying fingers and dildos. Within 5 minutes of serving drinks, I was impaling myself repeatedly on one of the younger girl's middle and index fingers making loud, exaggerated girlish moans. My girlfriend always made me practice these in front of a camera and make me watch them with her later, occasionally telling myself to play with myself while I enjoyed the slutty sissy on the TV. I would pout to the camera, looking like I was in ecstasy from the various toys that made their way inside me. "Ohhh yes! Oh my god it's so big, deeper, fuck me harder!" My high-pitched voice would alternate between squeals of pleasure and airy moans, "God your dick is so good, fuck my sissy pussy, oh please yes!"

At the party, the younger girl pleasuring me particularly enjoyed my exclamations of sissy-hood, getting me to lisp out "I'm a sexy little sissy, I'm a slutty little sissy, please let sissy cum in her pwetty dress pwease Mommy pwease," over and over again, while my hands stroked my breasts and the front of my panties. The women would cheer while the vivacious girl kept smiling, accompanying her fingers with slaps on my panties whenever I thrust myself back on her fingers. It wasn't enough for anyone to fuck me. My girlfriend insisted that I would be an active and willing participant and taught me to use my hips to get as deep as possible. She stuck a dildo to our kitchen wall one day, and every day while she made breakfast, I would have to press myself up against it, bending over so my butt would hit the wall every time I took the dildo inside me. I would stay in this position until I finished into a small bowl she would set out.

She didn't keep me in chastity very often, instead preferring me finish frequently to girlish pleasures. After the morning dildo practice, for instance, she would add my cum to the baby food cartridge of the Sissy-Peni Pacifier. Even as I grew out of my sissy baby phase, she enjoyed watching me furiously suck on the enormous veiny pink shaft so much that she started feeding me through it. She told me that it would improve my form, and anyway, a sissy like me needed something to fill my mouth anyway.

Within a few minutes of the younger girl adding a third finger inside my ass and other women coming over to stroke my penis, I came all over the woman's hands with a real moan of pleasure.

"Oh, thank you so much ladies. Oh my god that felt so good. It feels so good to be fucked like that, like a slutty sissy like me should be. Please let me be fucked again soon."

My profuse thanks were interrupted by the woman's fingers in my mouth, sucking up my cum as a reward for my sissy behavior.

This had continued for hours. By the time I was allowed to go to bed, each of the women had their turn, promising to bring the real thing over next time. I was exhausted from their playtime. The pink leather minidress that I modeled for them had been taken off and replaced with a thin, lacy pink bra and matching panty. Both had tiny bows along the edges, and the padding filled me out, "emphasizing my femininity," as one woman put it. They left the pumps on me. The guests had taken various pictures with me, contorting my body into every pose they had ever seen in a magazine or TV. My blonde hair extensions were sticky with cum that I couldn't swallow, and I laid on the floor of the living room, still in the last pose they wanted: on my back, with one flirtatious finger on my lips and the other clutching the front of my panties. I had moved from a pose once before and was punished with a visit from a professional photographer and outdoor photo shoot, as well as months of spankings and other inventive punishments.

My girlfriend, Katelyn, came back in the room and tickled me under the chin.

"Well who's the sexy minx that all the ladies wanted to fuck tonight?"

I looked up weakly.

"Me Miss, me. Thank you so much for bringing them over, I had such a good time. My pussy feels so used."

She smiled at me as she pushed her thumb in my mouth to suck. I responded with my whole head, pushing it down to take the length in and riding my tongue down the length of her finger.

"Good girl - you're getting much better at that - better than most girls. You sissies always know how to please. I spoke with the girls, and they would love to make this a weekly thing. I even told Lauren that she could babysit you sometime, won't that be fun? You remember her right, in the little black dress, who made you send out the Snapchats of you kissing that massive black dildo? She promised to not let you leave without trying her new dominatrix equipment on you. Aren't you the lucky sissy?"

I looked up from her thumb with nervous apprehension and nodded.

"Good girl. Now, go get in our bed. I have a special present for you being such a perfect little sissy."

We still slept in the same bed, except for my sissy baby phase, where I was confined to a baby crib on the side of her bed, replete with multiple dildos and a TV that she would play videos of other sissies on as I went to sleep. It was still there, and occasionally she would dress me up in the baby outfits and make me sleep there. For now, she preferred me by her side and I the same. When we cuddled, she would take the traditional man's spot; my head would rest on her chest, or I would be the little spoon. It was comforting, especially considering my daily humiliations.

Tonight, however, I would be spread eagle across the bed. The ribbons tied to the bedposts were elevated and lying on my back with my legs up in the air gave me no doubt to what she planned to do. I won't bore you with the story - it was much of the same, giving her oral while she toyed with my emotions and body. She had a new vibrator which she used, first on herself, then on me. As far as sissy rewards go, this was a better one.

The morning, as I've mentioned, was a usual Saturday. A few hours after I woke up, though, she gave me a sealed letter, and told me to visit this address. It's a sex shop - and no doubt, another humiliating excursion for me.

I walked in. Immediately inside was a collection of scintillating outfits. The one that caught my eye was proudly displayed on a mannequin. It was a modified hot pink leotard; the sides were cut out, and the tight fabric around the breasts was outlined with pink lace. Two frilly armlets outlined the forearms. The midriff was largely bare, except for tight straps connecting the top and bottom halves of the outfit, linked with gold hearts, and forming a larger heart that surrounded the belly button. The back of it was formed through thin twists of fabric, showing most of the upper back and connecting at the lower waist. The bottom was tiny, as revealing as a thong, and had a slit in the front and the back - perfect for a sissy like me. A flouncy, ballerina tutu was attached, barely a few inches, sticking out and covering nothing. Sequins adorned the edges of the tutu and the bottom piece and formed stars on the two sides of the butt.

Looking at it, I immediately felt a hardening against my panties. I wanted to model it for the ladies. I saw me curtseying in front of clapping women, my penis sticking proudly out with a ribbon tied around it in a bow, and a butt plug sticking out of the back of the costume as I stretched and pirouetted for everyone. I wanted Katelyn to put on "I'm a Barbie Girl," and film me dancing in front of a mirror, trying to seduce myself with a finger in my mouth and me shaking my butt. I was fully erect and all I could think about was being called a pwetty wittle sissy baby ballerina with my lips around someone's dildo. I felt pathetic and submissive, and I loved it.

I let myself fantasize for a few more minutes on how I could be humiliated. I was wasting time though, so I moved on. The other outfits were just as tantalizing to a horny sissy like me. French maids, Playboy bunnies, Disney princesses gone slutty, and "innocent" schoolgirls. The costumes made the lingerie look boring, even though at any other time I would love it. Dominant black, lacy pink, and virginal white hung from hangers from floor to ceiling. I wanted to hold every piece up against my body, to see how silky it was.

I moved on. The normal assortment of toys and filthy movies were stacked on shelves. Katelyn and I already had enough toys - what we didn't have, her friends would purchase and leave at our house so their boyfriends and husbands wouldn't find out. Inevitably, Katelyn used them all on me. None of the other women had tried anything similar with other men like Katelyn had with me, but they always bring it up and laugh about it. I get teased frequently about having a partner to play with, but as of now, the women have satisfied their amusement with plastic imitations, thankfully. I'm not sure if I'm ready, or want to go that far - but I know, if Katelyn and the ladies wanted me to, I probably wouldn't put up much resistance.

Two blonde women, one young, one old, stood behind the desk. At least it wasn't a guy. The older one was a bit intimidating. She was a bit taller than me by a few inches, and slightly thicker with very large breasts. Whereas I'd consider her attractive, the younger girl was downright sexy. Strawberry blonde hair, perfect figure...a girl who would never give me a second glance on the street. I fingered the envelope nervously while approaching. The other women in the store weren't paying attention to the lone man, luckily.

"Hi, so, I have a bit of an unusual request to make." My voice was too high as I was nervous. It sounded dainty, and I coughed as the women looked up.

"What can we do for you, sweetie?" The older women looked me up and down, and the younger girl barely diverted her attention from the computer.

"Well, my girlfriend told me to come here and hand you this envelope. I'm not sure what happens after that - we're just mixing it up a bit, you know."

"Oh! Katelyn sent you, right?"

I nodded. This was worrying. If she had to call ahead, there was probably something elaborate planned for me. The older woman took the envelope, shaking her head in recognition. The younger girl was looking back up at me, grinning slightly, but interested. She almost had a hungry expression on her face, and it was familiar to me. Her eyes looked exactly like the ladies in line, strap-on attached, waiting for the other women to finish up with me, wanting to experience the giving rather than the receiving side. Her lip curled up slightly.

The older women finished reading the letter and put it down on the desk. The younger girl quickly grabbed it and started scanning.

"Glad to see you came. We'll get started in just a second. What size do you usually wear?"

I knew automatically she was referring to women's' lingerie.

"Usually a 4-6," I mumbled.

"Cup size?" She asked. My face grew redder. The hot blonde girl smiled sweetly at me.

"A."

"Well that's quite alright darling. We have plenty of cute items that will fit you. If you want, head to the back changing rooms, and Sophia here will be with you in a few minutes." Sophia, the younger woman, smiled even wider.

"Don't worry, this'll be fun!" She got up and headed to the costume section, and I turned to sit in the waiting room. A few steps later, she tapped my on the shoulder.

"Why don't you take everything but your panties off, too." She patted my bottom gently and then pinched it and strode away. With this gesture, I began to feel even more uncomfortable.

I chose the larger changing room and took off my male clothes. Two full length mirrors reflected my image, a petite, fairly muscular, white male wearing flashy pink panties. I couldn't hide my body's excitement, however, and the tip poked through the waistband.

I tried pulling the panties up, but they simply rode further up into my butt and still wouldn't cover everything. I settled with pushing it over to one side and sitting down on the small bench. A black negligee was hanging against the wall, slightly transparent, and I wanted to put it on simply for modesty.

The door opened and Sophia came in with a bunch of hangers and outfits. I quickly scanned them - near the bottom was my favorite outfit, the sexy, slutty ballerina that I would be perfect as. Sophia saw me examining the stack.

"Cute, right? I bet you'll look really sexy in a few of these. Stand up." She looked at me critically as I rose and twirled her finger in a circle to indicate my next movement. As requested, I shuffled around in a circle. I heard her giggle as she read the back of my panties. She was still laughing when I finished turning and came close to me. She fingered one of my nipples.

"Wow. I mean, wow. I want to meet your girlfriend. You are absolutely adorable. Do you think she'd let me rent you for a bachelorette party in a few weeks?" She laughed. I didn't - I knew what Katelyn's response would be, and I was apprehensive about what the drunk women would make me do at out on the town. Sophia's finger drifted down and pulled at the waistband of the panties. My penis popped out. You could still see the flowers and stars that the women from last night drew on it.

"Aww, that's so cute. You have little tattoos. Did you do those yourself in front of a mirror?" Sophia kept grinning. She gripped me firmly around the shaft and gently started stroking up and down.

"Do you like this?" I nodded, looking at her in the eyes. Her other hand pinched my nipple, twisting it slightly. Her mouth went to my ear and blew slightly.

"You are going to be such a fun doll to play with." My whole body tingled and I moaned slightly, but audibly. Sophia pulled back and smiled.

"Lay down," she commanded. I did as I was told. She stepped over me, hovering over my face. I could see up her tight green short skirt to her black panties. Her heels were on each side of my head, a few inches tall, and matched her grey button up. She unbuttoned the blouse, putting one hand on her breast, and began to kneel down, pinning my arms down beneath her legs. She pulled her skirt up to her waist, and her womanhood hovered a few inches above my face. I could smell the sex, and the dampness of her panties showed. She looked down at me and rubbed her clit against my chin. Her butt rubbed against my chest, and she continued touching her breasts.

At this point, I already wanted to cum. I was so hard, and the soft panties just encouraged the feeling. After a minute or so of her pressing herself against my chin, she moved up and covered my mouth and nose, putting most of her weight on me. My mouth opened hungrily and I started using my tongue against her panties. The fabric was slightly scratchy, but wet, and I could feel her outline to guide myself to do what Katelyn taught me. Sophia started moving her hips slightly faster. She shifted her weight slightly and pulled her panties to one side and thrust herself down on to my tongue.

"Oh!" She made a small exclamation as I brought my tongue up against her clitoris. She was breathing much heavier now and moving her hips faster. I matched her pace with the strokes of my tongue, making sure I pulled away every few seconds to breathe without fully stopping.

"Oh my God yes, just like that. Don't stop." I kept my tongue still as she rubbed herself against me harder.

"Fuck yes, fuck, ugh, yes!" Her body stiffened slightly, one hand still inside of her bra and the other on my chest. I could taste her cum trickling down into my mouth, and I licked all around gently. She looked down at me.

"Wow, ok. Now I'm definitely meeting your girlfriend. She is lucky." She turned back to look at my still engorged cock imprisoned by the slim panties and smiled. Pre-cum pooled on my belly and darkened the edge of the silk.

"Aww, poor baby. Don't worry - I'll make sure you get to cum before you leave."

Sophia stood up, straightening out her skirt, adjusting her panties, and buttoning up her shirt.

"Let's keep that playtime in between us, sweetie, and I'll reward you later." She looked around at the pile of outfits.

"We should probably get you all prettied up before doing anything else." She looked down at me and used one foot to prod at my cock, pushing it around in my panties.

"Stand up girly." She reached over to the pile and pulled up the first outfit. At this moment, I felt completely humiliated. I had almost cum while being forced to give a gorgeous blonde girl oral sex, while wearing hot pink, sequined "baby girl" panties, and all I could think when I saw the outfit she held up was, "how cute" and "I wonder what it will feel like on me." It was a sexy sailor outfit, with a polka dot white and navy-blue vest that would hug my curves and reveal my breasts. A short navy-blue skirt flared out, ending right before thigh high white stockings edged with blue lace. 3"-inch blue, strappy heels were waiting on the floor, and a sailors cap was folded in with the outfit. The tag showed an attractive brunette, her butt visible under the skirt and bending over to show her cleavage, blowing a kiss to a buff sailor in the distance.