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Sissy Stories

sissy

Impromptu Fun

There’s a lot of fun on offer, if you look in the right places

I used to think it was really difficult to stumble on some fun when you're seeking action. I've read the stories about fun in toilets, but felt I must have only visited straight guy loos, as there was never any action. I was ready to give up on it when I decided one day to try something different and went out dressed with black holdups and a blue satin thong underneath my male clothes. I brought a backpack containing knee...

My Sister’s Ex PT4 - Owned and Controlled

Rich takes total control as he enjoys creating daring tasks for Sophia and punishments when needed.

I had gone to sleep that night feeling extremely content. I had just had the most amazing sexual experience and had also submitted my control over to Rich, my sister’s ex and now I guess my dom. I awoke the next morning in a dream-like state, expecting to find Rich’s strong arms wrapped around me as we spooned. How wrong could I have been? Instead, I was all alone in my bed and indeed the apartment too. I decided to get u...

My Sister’s Ex PT3 - My Bed, My Submission

Sophia’s adventures continue as my sister’s bully ex takes total control.

So here I am, standing in my sister's living room, wearing no underwear and having received a heavy pounding from her bully ex-boyfriend. I was in total shock and panic that my sister was upstairs, upset at what she had most definitely heard from me and Rich. What the hell would she think, finding her brother dressed like a slut in her living room? I hurry to unlock my phone and book an Uber ASAP. In my moment of panic, I...

My Sister’s Ex Pt1 - My Favourite Blue Dress

My sister’s bully ex notices me dressed and I can't resist

My name is Sophia and I’m a twenty-one-year-old sissy girl who loves to dress femme all the time. Over the past few years, I have got more and more daring with my feminine side, going out in public dressed. It was on one of those adventures I discovered a nightclub in town that was a hotspot for the LGBTQ+ community. I would often go there fully dressed and make new friends, drink, dance and have some fun. It was on one o...

My Sister’s Ex 2 - Becoming His Slut

Submitting to my sister’s bully ex as things escalate to new desires.

It was four days since I deepthroated Rich to a huge orgasm in the living room of my sister’s house. I wasn’t sure if he would keep to his word and keep my true identity intact but I thought that if he was intending to expose me it would have happened by now. I also had the photo of me holding Rich’s cock in my hand as insurance should he ever threaten to expose me in the future. I told myself I’ll never be in that positi...

Crossdressing Journey: Tentative Steps - The Next Evening

The climax of two fun nights in Bath with a fellow bi guy

This continues after the exploits of the morning before breakfast. I spent the day with a heightened level of arousal in anticipation of what might unfold tonight. I didn’t set any expectations, so that I wouldn’t be disappointed, and instead just thought about my lover’s cock. All I knew was that I was expected to wear my black high heeled over-the-knee boots and a short skirt or dress. I was more than happy to satisfy t...

Anonymous

Sissyfication by my friend

My friend makes me his submissive slut

Part 2 After that incredible night with my friend, I tried to process it all in my head. I wasn't gay? I had a girlfriend and enjoyed sex with her but also enjoyed what I did that night with my friend. For a couple of days I avoided my friend, mainly out of embarrassment but that didn't last long as he had sensed this and suggested we meet to clear the air so to speak down the local coffee shop. Invitation accepted I made...

Now I understood. They were making porn videos. I was to be a part of it. Well I'm sorry, ladies, gentlemen, I did not sign up for that. I wondered if my wife knew? I did not want to make a scene, so decided to play along and see what transpired - but I was not going to allow a record to be made on video, of that I was adamant. Now I had been noticed, I was introduced to the two husbands, using their real names and their...

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Anonymous

Finally my sissy dreams are realized

My friend seizes his opportunity to sissify me

After that memorable night with my friend I tried to process it, I wasn't gay? I did have a girlfriend. I didn't fancy men but a man dressed in sexy slips and nighties and dresses, well they definitely caught my eye and I did enjoy that unexpected night with my friend, a friendship that we built on over a couple of years until he got a job in London. So over several weeks I thought alot about that night which at first I f...

This morning, Sissy got up to see a note from Mistress stuck to her chastity cage bag saying “Put this on Sissy, we are going to have a dressing up day today and then we are going to fuck” Excited, Sissy put her cage on straight away, looking forward to some naughty fun. When Mistress got up she walked over to Sissy and felt in her panties to make sure she was caged. Mistress:- Are you looking forward to your dressing up...

The art club visits

Another fantasy

Sissy is tied face up on the bed, arms and legs spread to each corner. Sissy is in full pink sissy outfit but with a hood over her head, only sissy red lips showing. She cannot see anything. As Mistress secures her, she leans towards Sissy’s ear while grabbing Sissy’s locked up cockette and squeezing it. Mistress:- Oh! I forgot to tell you Sissy. This afternoon, the Art Club are meeting here. Sissy gasps and struggles aga...

Cucked Sissy

My biggest fantasy

Sissy is sitting on her bedroom chair, wrists and ankles secured to the chair arms and legs. Sissy is in full make-up with pink wig, glasses and earrings. She is wearing her pink dress. Underneath, she is wearing a sissy pink bra filled with her fake boobs, panties, pink stockings, pink suspender belt and pink sissy socks. Her little sissy cockette is locked away in her pink chastity cage. Mistress secured her to the chai...

I was frequenting gay dating sites for many years now, but it was only a curiosity of mine, to see other men naked and read stories about their encounters. I began returning more and more often, absorbed by gay fantasies, to the point I imagined myself in them. I was hoping to meet someone just to talk about my curiosities, but one guy caught my attention, with a friendly message. He was 43, so about 13 years older than m...

Sissy for black cock parts 1&2

A fantasy I want so badly

So I just can’t get the idea of being humiliated and forced to suck black cocks due to me turning myself into the desperate little sissy white boi I am becoming But I tried to get it out of my mind and date women like I thought I should So long story short I ended up dating a beautiful woman that I met online but i was unaware that she had somehow hacked my internet and she knew all of my kinky hidden desires and I was a...

So I have not had any sexual contact with anyone but my own hand for nearly 3 years and I’m pretty sure that I will never get to feel the torch of a woman ever again and I have no one else to blame except myself So I was married to the love of my life for 21 years and we had an amazing sex life and what I lacked in the cock department (4 inches) I definitely made up for it with my tongue and fingers skills and the fact th...