Fetish crossdressing stories
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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.
"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.
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.
Leaving the panties for last, I scooped them up with the black plug - just to make sure to follow Goddess' orders - and the half empty bottle of lube which I was quickly running out of with the new introduction to my alluring, Mistress. Grabbing my phone, I quickly snapped a shot of my cock and the plug now three quarters in my ass. Letting out a soft moan, I took another picture from above my head, looking down at my chest and panty-encased cock. Unable to resist anymore, I laid back and began stroking my hard cock through my panties, moving them down to release my tumescence.
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.
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.
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.”
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.
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’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.
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.
"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!!!!
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.
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 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.
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.
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.
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.
If his wife wore a silk blouse that day, it meant that later on, they would have sex. Now, with Vernon being more open about his fetish and his love of silk, they found ways to add it to their sex life. Vern loved the way the silk ropes felt around his wrists. Sex was always exciting when his wife tied him up with the silk ropes. Vern loved that his wife was okay with his silk fetish, and Karen loved that they had re-invented their sex life. Yes, he really did like silk, and he loved that his wife wanted him to dress up in her silk panties, or tie him up using lengths of silk
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.
We both know that pathetic tiny dick of yours is useless." Or "a real woman could never be satisfied by a sissy like you" or "Oh, how I wish I had a real man with a real cock to fuck me! Licking her and sucking her clit was something I enjoyed vastly more than fucking her, and her way of letting me climax was either my masturbating for her or being allowed to rub my cock against her toes or feet. You are my sweet sissy lover in your pretty panties, and you treat me like the queen I am, but I want to be a girl sometimes and be fucked hard by a guy." "You need a real man for a lover, Mistress, not a silly little sissy like me." I was near coming.
I should be, I was an old pervert in a mall, looking up the skirts of young girls and cumming in my panties. Maybe I will take you to the mall and let you flash some old pervert who gets off looking up girls skirts" teased Lauren. "Look Lauren, now that he is dressed and thinking about looking up skirts of young girls, he is getting hard" laughed Arlene. I want to take pictures of your panty showing as you try to walk down the stairs and try to look ladylike" Lauren continued. I was standing with a hard cock in my panties, dressed like a girl in front of my 22 year old daughter and SHE was going to shave my legs and paint my toenails.