Sissy Blackmail Stories

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Sissy Blackmail Stories
My name is Raul, I am from India. Since an early age I had a ...
Hi, this is my story and since I was little I have always been curious ...
My name is Sam. I grew up in a small town of Avonshire. I was ...
Hi, my name is Tommy and I’m 20 years old. I live in a very ...
I arrived home, from work, on the Bank Holiday weekend, of Easter. The following week, I was taking days off that were owing to me, so the forecasts were good, and I was happy. As I entered the house, I heard chatter, and recognized my mom and aunt Marilyn’s voice.
“Hello son, look who is here.” mom spoke, as I gazed at aunt Marilyn. I had always and still am, very fond of her, and fantasized about her, when in bed and in the shower. I know it is wrong, I told myself, but that was my secret.
Mom: “Aunt Marilyn, is here, to ask you, if you would like to spend some of your days off work, at her home.”
Me: “Yes, I will accept the offer mom, and thank you aunt Marilyn.”



Well we sat down to a meal and my aunt slept over that night, so we made an early start in the morning.
Aunt Marilyn: “Did you sleep well Graham, as we got into the car?”
Me: “Not really aunt, as I was excited about this stay with you. ”
I waved my mom goodbye. The journey took us about ninety minutes, and arrived in Park Close, a cul-de-sac, with six bungalows there. It was a tranquil area, and in the countryside. I liked the closed in hedges of the lanes, we drove down, were beyond the hedges, laid open fields of grass and crops.
My valise case (a small travelling bag), just carried my bathroom kit, a few underpants and tops, a pair of blue jeans, a white ladies blouse, full sleeves with a Peter Pan collar, a pair of white knickers and ladies beige slacks, with a button and zip, side fastening.
Aunt Marilyn, showed me around and where everything was. Then we left, to go for fish and chips, to eat at Tally’s. On return, aunt took a shower, and offered me to take one after her, which I did, to freshen up.



About an hour later, aunt, telling me, as I was reading a woman’s magazine of hers, that she just be over the road, to chat to her friend for awhile.
Me: “ Yes aunt, go ahead, is it okay if I do this crossword aunt?”
Aunt Marilyn: Yes sweetie make yourself at home.
I was still with a bath towel around my waist, male sarong style, not female, with it covering my bust.
Once aunt left, I had the urge to peek into her boudoir, and there on the bed, was a lovely shade of pink, nightdress. Oh gosh, as I stared at it, but dared not touch it, in case aunt had placed it, in a certain way. Weakness of a man overcame me, and I found myself holding it up in front of me, then dropping the towel, to the carpet, and stood in front of the mirror, and with a rampant erection, as I had not mastur-bated for about five days. Oh gosh, as I was now mesmerized, then it touched the top of my pe-nis. Oh no, as I hoped my precum had not stained it.
Then to my horror, my aunt’s voice at the door, saying, ” if you like it so much, why not put it on.”
Me: “ I can explain aunt Marilyn. Please don’t tell my mom.”
Aunt entered the room, locked the door, and came toward me.
Aunt Marilyn: Now my teenage niece, we best get you into your nightdress, and early for bed.
Taking the nightie from me, slipped it over my head, not mentioning my arousal.



Aunt Marilyn: “Pink, does become you, Jane, Very cute indeed. You shall wear it tonight and if you make a mess in it, you will hand wash it, and you will wear another one of my nighties, each night, until you leave. You see Graham, I mean Jane, as I unpacked your valise earlier, I noticed a certain few items, that only could belong to a girl wearing them, so to confirm it, made an excuse to leave you alone for awhile, to discover you, in a compromising position, which I have done. Now my sweet young niece, we best go and watch the film on DVD, ” THE WOMEN.” Tomorrow morning, you shall wear what I put on my bed for you. Any argument or protest, then your mom will be contacted. Do you understand Jane?”
Aunt Marilyn: “ Now, when you need to use the bathroom, you will sit down to pee. You are now my niece, a girl. We are going to have such fun, while you are here. Oh you’re going to see some change in you. ”
I sensed my boyhood, being overtaken by a new ultra-feminine existence, while at aunt Marilyn’s.
What a wonderful way to get caught.
Lovely story, could use some sharpening up concerning your writing grammar but I did love it. We all want an aunty like that, to be told what to do to bring our feminine side out. Kisses hon.
Beverly
had a similiar experience ,but my aunt had a strapon that she used very well it vibrated on her pussy as she laid the wood to me felt great.
Could of been oh so much better and longer.
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My name is Raul, I am from India. Since an early age I had a ...
Hi, this is my story and since I was little I have always been curious ...
My name is Sam. I grew up in a small town of Avonshire. I was ...
Hi, my name is Tommy and I’m 20 years old. I live in a very ...
I work in an outsource management company, with more woman than man and the company has many outlet across the country.Paul is my boss who turn around each outlet every six to twelve months.
Work is very difficult, working under pressure. Paul is very straight forward at work and many staffs have bad times with him. So far, I do my work correctly in time and he appreciates it and even some time he invited me for a drink.
For me going to work was a pleasure, wearing tight jeans, shirts and always my panties with lace.No body is aware of my cross dressing.



I still remember that Friday afternoon, I went to the bathroom and few seconds later Paul came in too. We did pee and then by surprise, with a smile Paul told me to keep well my panty lace well inside my jean and went back to his office. I was really confused of what to do now as my boss just saw what I have been hiding at the office for years. I went back to my desk and told my colleague that am not feeling well and that am going to leave earlier.
Arriving at home with my confusion about what I will tell him now as he already noticed me wearing panties and that he is really harsh at work. I started getting stress and pressure my raising in my head. The office called but I didn’t rely and even on Monday morning I sent a sick message to the office.
I was taking the decision to resign from work as Paul already knows about my cross dressing.in fact I was aiming for complete transformation in the years to come. But I was at a point where everything is a mess.
So I decided not to go to the office for some days and then send my resignation letter. On the next day still stressed as I am, the house and myself we’re in a mess. I heard the ring bell. I went to open the door with my sexy jean short and with my surprise, Paul my boss was at the door step.
I panicked, took a deep breath and after some minutes, I opened the door. I invited him inside, he was in a causal dress and we sat in the living room. He brought a shopping bag and was asking about my health and even told me to take some more days off. I didn’t know what to say, I went in the kitchen to bring some drinks and there I stared crying as I didn’t want any one to that at my work.
Then Paul, came to me to give me a big man hug and whispered in my ear that he likes me very much and that the bathroom incident was not an issue as he likes to love trans woman. I could understand what was going on and continue to cry in his arm.



Then after a while he brought me on the sofa and told me that he wants to give me a chance to live like I wish to and gave me the shopping bag of a sexy short jean, T shirts, black panty and a bra. He told me that he wish to live with me and to set some goals together.
But for now he wants to bring me out for a ride to relax myself and he is off for some days and kissed me unexpectedly on my lips. I was embarrassed by the move but he reassure me that it’s personal matters and even told me that he will bring me with him to the move and will support my transition as I wish.
I dressed up and he invited for a ride and was amazed looking how sexy I was in woman dress.At the door step he hugged me and gave me a harder kiss on my lips unexpectedly. I was so happy inside to live that moment but very shy from outside.
He made me ride to a remote cliff where we were able to enjoy the summer wind, then on our way back home he stopped to order Take away dinner. We had dinner at my place, he was really handsome, caring and what I really appreciated on that day was the hugs he gave me.
After dinner, we had a long discussion about myself, that I would go for transition and for gender reassignment, I want to live my live as a woman. I appreciated the talks and while sitting on the sofa, he came closely to me gave me a hug kiss , turned me around, caress my neck and continue to drag me until I can resist him.
I felt in his arm while he continue to kiss me everywhere. It was as if my dream coming true. I was roaming, exciting and feeling his body and man order. Then I removed his clothes and things goes harder and stronger.



I couldn’t stopped myself and he as well. I took his name more than a time with pleasure and eventually made him arous-ed more and more. He bent me on the sofa from the back, gently for the first time and penetrated me. Then made me sit in doggy position, shut my mouth from behind and started riding me. I was on another planet with him.
He didn’t give me time to understand, as if he also didn’t had se-x for long. Finally I gave him what he wanted a good Bl## Job and we were set exhausted. I roamed on him and sleepy.
He picked me up from the sofa and bring me to my room in his arm. We slept together..
What a lovely story… that would be a fantasy also for me…
Such a wonderful outcome of intimacy. So many reading the story are envious.
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“Today is going to be a good day,” Jason told himself as he was getting up from bed. Jason is an average 16 year old boy. He has light brown hair that goes a little past his ears, is 5’6 and is a bit on the overweight side. He does well in school and doesn’t get into any trouble. Jason hopped out of bed and went to the bathroom to take a shower. He needed to get ready so that he can go to the mall with his little sister Katie and her friends. This was going to be the first time that he went to the mall with Katie and her friends. He never really hung out with his sister but since it is a three day weekend and their parents won’t be back until Monday, Jason decided that he will hang out with her for once. While Jason was in the shower he picked up his sister’s pink razor and started to shave his legs. As he was finishing up shaving both of his legs, Jason froze feeling confused. “Why am I shaving my legs?” he thought to himself. He didn’t understand it. He had never done this before but for some reason he really wanted smooth legs. After pondering this dilemma Jason decided to finish shaving his legs and then went ahead and shaved his armpits smooth. After he had gotten out of the shower and gotten dressed he went downstairs to find his 12 year old sister Katie. She was wearing a pair of blue skinny jeans with a coral t-shirt that had a glittery peace sign on it and she had a white headband in her shoulder length brown hair. Around her neck she had a necklace made from a black string with a small mesmerizing ruby red tear drop stone. “Are you ready yet?” she told him. “You took forever to get ready. We need to go pick up Britney and Amy.” “Sorry, I took a little longer today because I needed to shave my legs,” Jason told her. Panic entered Jason’s body as he realized that he just told his sister about shaving his legs. Luckily for Jason, Katie didn’t seem to care as she quickly ushered him to his car. The two siblings had picked up both of Katie’s friends and arrived at the mall. Britney and Amy were both 12 and were just as girly as my sister. Britney was shorter than the three girls with Amy being the same height as Katie. Britney had long black hair that she tied to a high ponytail on top of her head and Amy’s hair was blond and went to her shoulders. Amy was wearing black leggings that had little pink and white hearts over it and she had a black long sleeve shirt that a design of a butterfly made out of rhinestones. Britney had a blue floral tank top with blue shorts. As they stepped out of the car and began walking into the mall the girls began giggling as they looked at Jason. Katie whispered something to the two girls and the giggling grew louder causing Jason to feel uncomfortable. Suddenly Britney spoke up, “Hey Jason are you okay? You look a little nervous.” “Hey, I have an idea. How about we take Jason in here so that he can relax a little before start shopping.” Amy said as she pointed into a nail salon. “That’s a great idea. I always feel so relaxed whenever I get my nails done,” said Katie. Jason just stood there frozen by the conversation the girls were having. He wanted to say something but for some reason couldn’t. “Maybe it won’t be too bad,” Jason thought to himself as the girls pulled him into the salon. “It’s not like I have to get my nails painted,” he told himself. The girls sat Jason down on one of the chairs by the window and then went up to the counter. As they were telling the woman at the counter what they wanted, the woman kept looking back and forth between Jason and the girls. Finally the woman said something to the other workers and my sister and her friends went to a the rack on the wall full of nail polishes. As they were looking at the polishes, Katie and her friends started giggling and Katie went back to the receptionist with a bottle of nail polish. The woman laughed from whatever Katie had told her and she looked at Jason again. After the girls finished picking there colors, Jason and the girls were escorted to the pedicure chairs to start the procedure. As Jason sat down, his nail technician took off his shoes and socks and rolled up his pant legs which brought a giggle from the woman due to his shaved legs. Jason just closed his eyes as he tried to get over his embarrassment. Jason was just glad that the salon was slow due to being early in the morning. As the procedure went on Jason started to enjoy himself. The pedicure actually felt good and he was kind of glad that girls made him do this. The nail technician grabbed a pair of yellow toe separators and then placed them between Jason’s toes. Jason started to feel nervous again but told himself that she probably just wants to put clear nail polish. Jason calmed down as the nail technician coated his toenails with a clear polish. After she was done she grabbed a bottle of bright pink nail polish. As she took out the brush out of the bottle and brought it to his big toe, Jason told her to stop. Jason hesitated to say something as the technician looked up to see what he wanted. Jason wanted to tell her that he didn’t want his toenails painted. He really wanted to but he found that he couldn’t. Just trying to tell her was starting to give him a headache. “Jason,” Katie said to grab his attention. He turned to look at her but his eyes immediately went to the jewel on her necklace that had appeared to start glowing a faint red. Suddenly Jason turned back to his nail technician and said, “Can you also paint a flower on my big toes?” The salon filled with giggles from what he had said and his technician responded through the giggles with a yes as she went ahead and started painting his toenails with the pink color. Jason could not believe what was going on. Here he was getting his toenails painted and instead of telling the woman to stop, he tells her to make his toenails even girlier. He could not believe his eyes when he looked at his toes after the technician had finished. They were a barbie bright pink and he had a little white flower that had glitter on the edges of petals on the corner of both of his big toes. When she asked him if he liked them, Jason was unable to stop himself from responding with, “Yes, they are lovely.” He was given yellow disposable flip flops and then led to a manicuring table where the woman started working on his hands. As the manicure started, Jason was panicking about why he couldn’t stop this and about what she was going to do to his fingernails. As the procedure went on however, Jason began to worry about why he was starting to like the color on his toenails. “It’s not that bad. At least it looks pretty. I mean I don’t hate it,” Jason thought to himself. “At least it’s on my feet where no one can see it.” His fears reignited as the nail technician began to place acrylic nails on to each of his fingertips. He again wanted to say something but he couldn’t bring up the strength to say anything. Soon each of his nails sported 1 inch long acrylic nails. Jason watched as she took the same pink nail polish she had used on his toes and started to coat his new acrylic nails with it. After each nail was bright pink and girly she grabbed even more polishes and glitter and began adding pale pink flowers to each nail with glitter all around each flower. Jason had been so distracted by the procedure that he didn’t realize that Katie and her friends had already finished there mani pedis and were now watching and filming him get his nails done. “Jason, what do you say to her for making your nails all pretty?” Katie said, her necklace glowing once again, her necklace glowing once again. “Oh my gosh! Thank you so much for my fabulous nails. I like, love them so much,” Jason said flamboyantly. As Jason and the girls were leaving the salon Jason turned to look at Katie as her necklace began to glow a cool blue. As the girls were teasing him over his girly nails, Jason’s blood drained from his face as he saw a familiar blond teenage girl walk up to him. It was Stephanie, the girl who sat in front of him in his algebra class. The girl that Jason had a crush on since he first seen her. She looked at Jason’s nails and started laughing. “Hey, aren’t you in my math class? You’re name is Jason right?” Jason didn’t know what to say and started to stammer. “I like your nails. They’re really pretty,” She said as she grabbed his hand to get a closer look at his nails.

As Jason and the girls entered Sephora, Jason’s heartbeat increased when he noticed that the Sephora was packed full of women. While his sister and her friends were giggling about what they were going to do to Jason, Jason was trying to think about how all of this happened. He needed to know why he couldn’t stop his sister from feminizing him, but every time he did his head would hurt. He could only vaguely remember the previous night. She had done something to him but he just didn’t know what.

Jason snapped out of his thoughts when he heard a woman speak. “Hello, welcome to Sephora. My name is Lisa. Is there somethi
“MUM JACK DID IT AGAIN!” Screamed a 15 year old girl, “i said I was sorry Hannah, it was an accident” replied Jack timidly.Even though he was a year older Jack was quite scared of his little sister, he was a very slender boy and didn’t ta
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