Fetish cross dressing stories
Read 169 free cross dressing erotic stories on AdultRead
“I’m going upstairs to change for bed,” she said, "Fifteen minutes for a clean up and a change into my nightie, then I’ll come down again.” “I’m going to pull your panties down, but only so far, then I’m going to take my peignoir off, you can put it on if you like and then you are going to give me the best fucking that you can, but I don’t expect it to be as good as I want, so you might have to keep trying until you get it right. Sal’ went wild, berserk, she screamed, pushed backwards hard against me, then pulled away a bit before pressing back against me again, her butt hole was gripping my finger as in a vice.
Closing my eyes, sucking on the gag, I feel Her whip come down on my back and panty-clad ass over and over again. Taking another drag of Her smoke, She arose from Her seat and brought the gag down around my neck, "So slut boi, are you ready to finish your training for the day?" Nodding my head up and down, my cock became instantly hard imagining that I would be allowed inside Her. Bringing Her hand down to my throbbing cock, She whispered in my ear, "Thats the response I was looking for. Does my little sissy slut like Mistress' sweet pussy? Nodding yes, Mistress rose off my still hard, wet cock and walked out the door.
White knee-high socks and black Mary-Jane shoes make him the perfect sexy school-girl. Louise opens the door looking ravishing in her red, satin blouse and tight, black leather trousers. This is obviously the same Belinda he has known from years ago, last seeing her at Louise’s wedding evening reception. “A lovely color purple, Caitlin looked like a princess didn't she Alan? Mummy Belinda puts a blonde, little-girls wig on his head with a pink bow. Belinda sits close to her friend so that both mummies have full access to their new foster-daughter. Louise strokes the front of his dress while Belinda inspects his mobile. Louise places her hand over his mouth making sure he feels the warmth of Belinda’s snotty substance.
Meanwhile Fitz decided that Steph needed to meet some of his friends in the tattooing community. When she wasn’t seeing Fitz or his brother, Steph was spending time with Amanda. Steph especially liked kissing and licking Amanda there. Steph listened enraptured as Amanda described the beautiful pain of having needles pierced through her areolae and nipples. After the two women made love again they decided to introduce Phil to Amanda and his cock cage. Steph and Amanda went shopping for Phil. Steph found Fitz straight away, kissed him hungrily, and looked around. I fucked some huge cocks tonight and if you think I’m going to go back to your pathetic dicklet you’ve got another thing coming.
My first thought was: sure I can wear them under my boxers and no one will ever know but that plan went out the window when Karen specified with a giggle and that special smile she had - like poison come to dinner - that I was to wear no other underwear than those panties. Of course, I knew that this was somehow all related to the surprise reward she had promised for completing my birthday dare and the thought of what Karen might have planned for us kept me in an aroused state all through the school day. Having said this Karen took Molly by the hand and led her into her mum's bedroom, pushed her roughly onto the bed and pulled the yellow summer dress over her head exposing her naked body to me before climbing on top of Molly.
I would have thought it completely entertaining for my hot Ex and her hot friends to have some random guy all dressed up as a maid serving drinks to everyone at a Halloween party. And there I was, dressed up as a maid, locked in chastity, licking the high heels of my Ex's hot friend in front of an entire crowd of people. And with that, I had to face the realization that I would finally meet the man with the cock who was currently fucking my Ex...while I was locked up in chastity...unable to get hard or have an orgasm...at least until my Ex said it was allowed.
Anticipating the night I did as I was told showered, shaved and proceeded to put on my Red garters with Black stocking and my very tight black bodysuit. When I returned to work wearing my sexy underclothing, the feeling of my Garters rubbing on my legs and smooth ass cheeks. My Mistress first rubbed my backside, then my legs and then proceeded to hug around me making sure she had both of my tits in each hand and squeezed whispering how much she loved me. Then I was ordered to go and make sure I was stuffed and to shove it in and out, because she wanted me to enjoy the feeling of all that cock going in and out of my hot pussy.
"You've been visiting some rather strange sites on the net, darling," Laura said with a rather supercilious smile as Jack's face turned very pale suddenly. "I think you need to be punished, darling, for being so naughty," Laura said ever so sweetly, and Jack felt his penis start to harden in his pants at the thought that his pretty wife was about to give him the feminine discipline he so craved. "Jackie," Laura continued, "since you're behaving like such a naughty little boy, I'm going to make you ask me, and you will call me Mommy, whenever you want to use the toilet." Jack blanched when he saw that she had found one of those little wooden training toilets that small children learn how to do their business on.
Time seemed to inch by as I watched all the women prancing around in the lingerie, offering up lap dances while the girl on center stage seductively moved around the stage continually eyeing Jenny, like a bird hunting prey. Just as I was about to break down and start rubbing my swollen cock, Jenny whispered something in the ear of the dancer who let on a dark smile as she looked in my direction. I do not think I have ever moved as quickly as I did in that moment, and was almost instantly on the couch beside Jenny feeling the cool wetness of her cum on my balls as my cock pressed hard against my jeans trying to stand up, but restricted by the tight material.
I quickly pulled the suit on, trying to keep control of my erection, pushing my cock down to at least pretend that I wasn’t massively turned on by this moment. “Now slave, try to enjoy.” she said, standing in front me of me, slipping off my trunks she’d been wearing. “Now, deep breaths little slave.” she said as she came towards me, pulling the swimsuit away from my ass. I looked up at her wet pussy, she lent over me and pushed her hand down my chest over the swimsuit to my cock, she reached under the swimsuit and pulled it out, slowly moving her fingers around the head.
Sally said, “So, let me get this right, you’re wearing stockings, a suspender belt, a cami, satin knickers, a tight white blouse, (Which you’ve soiled by the way) a tight black skirt, a starched pinny, a mop cap AND my high heeled mules, and you don’t have an erection?” Yes Mistress, er…. “I know exactly what dress to put you in, you could have it on in one minute from now, and I will get it for you, but first take a few minutes to look” Sal’ said, ”Feast your eyes on all of them, and feel them, if you want take all your clothes off and enter the wardrobe naked, you can walk among them, feel the different fabrics against your skin, several at a time, I’ll close the door, you can do it in the dark if you like.”
I didn’t really need to stroke myself, I just shot a load of cum into the panties, then falling to my knees, my face level with the dresses, I grabbed hold of my cock, wanked hard and shot spurt after spurt onto the wardrobe floor, my head fell forward and was engulfed in the long silky floaty dresses that smelled of Sally. I went into the laundry room to see her placing each item of clothing individually into the machine, in went a cotton blouse, in went a denim skirt, in went a nylon housecoat, in went everything, one item at a time and nothing exciting at all, no undies, no nighties or anything that could be anything but work wear.
I really don’t care what other people think my sexual orientation is, I have a strong desire for the feminine look but it’s just that I want it to come with a cock,” I say finishing my drink and gesturing to Emmy for another. I pull my head back a little to get a closer look at this writhing cock between my hands and I see it start to spurt it’s hot glowing white cum all over my face. I start rubbing its now sopping wet head up and down my ass crack and can’t help myself as I pull my panties aside to place my puckered asshole on to the head of the cum lubed shaft between my hands.
I step on gingerly, being careful not to expose my stockings and suspender belt or let my cum filled condom slip off my cock, butt plug still vibrating away in my ass. As I see them part the light comes on in the house and I can see Emmy standing on the other side of the window, wearing very little, her legs spread apart slightly in a Wonder Woman-like pose, hands on her hips. The doors slide open slowly in front of my face and Emmy takes up position beside me, her fingers reaching down my ass crack giving my cummy asshole a little rub. I can feel the hands holding the panties release my ass and the cock slowly pull out of my asshole.
"Your tiny little pathetic excuse for a cock couldn't pleasure anyone, which is another reason I like to keep it all locked up," my Ex said pushing me up to attention on my knees with one foot and lightly kicking my chastity with the other. This was the most humiliating thing I had ever done, being locked up in chastity, dressed up in sissy girly clothes, and forced to fuck my own ass, resulting in the unfortunate leakage of cum onto a saucer which I knew my Ex would want me to clean. Being forced to eat my own cum off my Ex's feet, locked in chastity, and dressed up as a sissy little maid was about the most humiliating act I could ever think to be doing.
Then she giggled, “You’re right she said, lets get cleaned up and changed, I feel a bit of a mess, all that dried cum around my pussy and down my legs, and I expect you feel the same, don’t you?” “I’ll have champagne and OJ I think, I don’t mind if I sleep for a few hours, It’s 3am” she said, “and it’s been a very long day, and night. “No” I said “Lets take it easy for a few hours, and get some real sleep” I’ll have a chocolate drink I think, not a soda pop, do you still want your Champagne?” “No chocolate would be nice, and relaxing.”
And she knew I couldn't help myself but listen to them with my cock all locked up, being dressed up in a sissy corset and nylons, listening to them having sex knowing I had no way of getting myself off. "Oh God, I can't...I can't...It feels so good, but it's so huge...it hurts, but don't stop, please, I can do it, please, let me feel your cock deep inside my tight ass," she kept saying. "Sounds like your problem since I'm going to fuck your brains out until you can hardly talk," her bull of a boyfriend said. There was a surge of intensity after he said this as they both moaned loudly, her because the humiliation was just what she wanted and for him, because she obviously was working her tongue a little extra in anticipation.
The Ex wasn't answering my calls so I decided to say screw it and go to the gym despite my chastity situation. Then, as if by some sixth sense, I began to notice each and every female in visible distance, especially the hot brunette in the row in front of me wearing only tight spandex shorts and sports bra "Can I get you anything?" I asked approaching her table, my cock instantly trying to produce a spontaneous erection that was hindered by my tight little cage. You look like you just got punched in the balls," Kara said. I didn't realize wearing a chastity device would mean no longer standing up to pee unless my cock was aligned just right with the opening at the end.
"Eager little slut, aren't we." Shaking my head yes, I close my eyes and let them roll back into my head as I feel pure ecstasy. I take it between my lips, sucking on it gently, kissing it lovingly, flicking it one more time with the tip of my tongue until I go back down to her sweet hole, licking all the way from her cute little rosebud to her pussy, circling around her pussy once, then diving my tongue in with everything I have. Riding my face, her deep breathes now become screams of pleasure, "Don't stop slave, right there, mmmmm, yes, yes, ah, mmm, oh fuck yes, tongue fuck your mistress' pussy!!!!
Granny Ella wore bifocals when she was out driving, but if she stayed in the house she wore a pair of gold half-round style reading glasses that were hung from an eyeglass chain of small pearls. I still have the bra you came in and I know you like cumming on my gold half-rounds - these." Granny pointed to her gold half-glasses covered thick in cum with a now-spent cock hanging over them. "Harold, for your kindness and love for your Granny Ella I have decided that you are old enough to start enjoying what an older woman can do for you. Ella wanted to be fucked good and hard like any woman who has not had it for some time.
I feel a little uncomfortable and strained but that all disappears as Emmy buries her face between my ass cheeks and starts to lick my asshole. “Oh Humph, you do look good with your cum on your face, and those panties, oh my well they have been through a lot haven’t they?” She says with a caring whisper as she lets me slip back down onto the bed. She takes a moment to collect up the beads of cum from my face and wipe them on the panties in my mouth before leaning in and giving it all a big slow lick while looking me straight in my eyes.
They made me come multiple times and they both had monster cocks. I decided that I liked big cocks and Phil just didn’t cut it in that department. And you’ll go along with it too because you love me and want me to be happy, don’t you, Phil?” Phil allowed himself to be horrified but deep down he knew Steph needed a big cock to satisfy her and, if he was honest with himself, he really wanted to see it happen. He went to bed and masturbated furiously thinking of Steph being fucked by those two huge cocks. Steph cleaned Steve’s cock of her own juices while Fitz fucked her with passion. Phil looked sheepish until Steph noticed a wet patch on her knickers.
Then I’m going to have another bath, a real one, a long one, with all my oils and potions in it, I’ll be in there at least an hour and I DON’T want to be disturbed, sir.” she laughed. "You’re on your own for a few days, I’m afraid and I want to phone around a few of our shops and see if they’ve got any “Seconds” that I can maybe take up to head office. Enjoy them any time, day or night, except for those dresses!"Sally said. I‘ll get dressed, but I am going back to bed later," said Sal.
Hayley has Alan in her arms, cuddling him tightly against her breasts. “This is your Mummy Laura, smile for mummy, Holly Grace.” “You’re my pretty Holly Grace and Laura is another yummy mummy.” “Noisy plastic baby-panties, look so cute on Holly Grace. Laura introduces Nikki to their new sissy-baby. Hayley is delighted at the sound of her baby gulping milk from Nikki. Becky pulls Alan from Nikki’s breast, picking him up in her arms. Helen had gone to another room, having an interesting chat with Alan’s second cousin Emma-Jane. Baby Holly Grace stares awkwardly at Nanny Gross. “Ah Holly Grace, want my tits, out they pop babes, begging to be milked.” Becky takes Alan back to Hayley.