Being Sissy To My Brother In Law
- 2 years ago
- 26
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Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else.
One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite.
I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on opening the door my eyes fell upon the lovely red and black whale boned basque that I had bought her last Christmas, which had suspender straps and was a much better option than just a belt for holding up the fishnet stockings I retrieved from the drawer.
While slipping on the panties I noticed a ruby red lipstick on her bedside cabinet and decided to try some. Using her portable mirror I managed a decent look on my lips and the put on the basque and fishnets.
I planned to sit on the sofa and watch some porn while teasing my cock through the lovely satin but as I was finishing clipping the stockings up the doorbell rang.
My heart skipped a beat but I quickly composed myself, thinking it would just be the postman and as I had a full-length dressing gown I quickly donned it and went to answer the door.
Opening the door just enough to show my face and torso I looked out. To my utter shock there stood my brother in law.
“Oh, err hi Chris, what are you doing here?”
“I’ve got a flat tyre and need to borrow your car jack,” he said.
“Oh, err ok, hang on there while I get my keys and you can get it out of the garage,” I stuttered.
“I may as well have a cuppa while I’m here,” he said, barging past me.
As I walked into the kitchen he was looking down at my feet and, with a shocked look on my face I realised the stocking bottoms would still be visible beneath my dressing gown.
“What’s this Dave, getting ready to go out somewhere,” he said with a sneer. “Nice lipstick too.”
“It’s, it’s not what it looks like Chris,” I stuttered as my face reddened.
“Let’s see just what it does look like shall we,” he laughed as he grabbed at the cord that was holding my dressing gown together.
The front of the gown fell open and my outfit was exposed to his leering eyes.
“Well, well, well, so this is what you get up to behind closed doors is it?” he said, with a big grin on his face.
“Please don’t tell anyone Chris,” I begged him.
“Ha ha ha, your legs look quite good in fishnets but I’m not used to seeing a bulge in a pair of women’s panties. You look like a slut.”
“S…sorry Chris, give me a minute to put some jeans on and I’ll make you that cuppa.”
“You aren’t going anywhere you sissy,” he said, grabbing my arm.
“Please Chris, let me get changed.”
“Not a chance, now take of that dressing gown and parade around like the big sissy that you are, or I will text all our friends and family telling them what your into.”
“Chris, please don’t humiliate me.”
“Do it, or else,” he snarled.
Reluctantly I did as he ordered. Dropping the gown to the floor, I started mincing around the room, my face as red as a beetroot.
He was laughing at me and as I passed by him for the second time he slapped me across the arse.
My cock was becoming semi erect and this did not go unnoticed by Chris.
“Aw look, the big sissy is getting a hard on. Now bend over because you deserve punishing for getting aroused you pervert,” he hissed.
I hesitatingly bent over a little in front of him, only to be pushed further forward by one of his big hands.
Next thing I knew my arse was subjected to a severe spanking, which, even though a male was administering it was getting my cock hard. After a minute or so the smacking seemed to be getting replaced by rubbing and squeezing of my arse cheeks.
“Look what you have done you slut,” said Chris, grabbing me by the hair and turning my head towards his hips. Right in front of my eyes was a bulge shoving at the front of his pants.
“I need sorting out,” he said as he unfastened his pants and pushed them down his legs. “Get on your knees sissy boy and suck me.”
“No chance Chris, I’ve never done that to a man. If you want it relieving you are going to have to wank yourself,” I said defiantly.
“Do it now or I will tell all about you.”
I had no choice but to get down on my knees in front of him.
His uncut cock was bouncing slightly as it throbbed in front of my face and I couldn’t help thinking of the number of times I had wondered what it would be like to suck on a cock. Well now I had no choice.
Moving my face forward I touched his tip with my lips and then tasted it with the tip of my tongue.
He then wrapped a hand around his member and rolled back his foreskin, fully exposing his member to me.
“Stop messing about and suck the fucking thing you pansy,” he barked at me.
Parting my lips I slowly took him into my mouth and sucked a little on it. It was much better than I was expecting and began sucking more greedily on it for a while, then moving back to suck hard on his bell end. Chris was moaning with pleasure.
He had started thrusting in and out of my mouth and I could feel his bell end hitting the back of my throat, when suddenly he gripped the sides of my head with both of his hands and forced himself right into my mouth. His cock went down into my throat and I found that I could no longer breath.
A slight panic came over me but he pulled out long enough to catch a breath, before thrusting deep down my throat again. After a few minutes of this onslaught he pulled out of my mouth and pushed me aside, where I landed on all fours.
“How did you like it pansy?” he smirked.
I was too busy spluttering to answer.
I felt his hands caressing my arse cheeks again, and then he was sliding my satin panties down. He placed his hands on my bare skin and squeezed my cheeks, pulling them apart and ran a finger over the crack of my arse.
It felt so good.
“You do know that I’m going to finish myself off in your arse, don’t you, you wimp?”
I hadn’t thought of any of this going so far and heard myself saying, “Just go easy Chris as I’ve only used a small vibrator up me before.”
He was already rubbing his still wet cock up and down the crack of my arse as I spoke. He nudged his bell end against my hole a few times until the head popped inside.
I let out a slight moan.
“Shut up and take it you bitch,” he laughed, and gave my arse a hard slap.
He shoved some more until half of his length was inside me. God it was filling, but it also felt damn good. It was much better than the little vibrator I had been used to using.
As he started thrusting in and out of me, I reached for my cock and began wanking.
“Don’t you dare play with yourself, you dirty little pansy,” Chris growled at me as he pulled my hand away from my swollen member and firmly slapped my bollocks.
The feeling in my tingling nuts actually felt good.
He then grabbed a fistful of my hair and thrust all the way into me, making me gasp. I never imagined a real cock would be so filling.
As he began thrusting in and out of me, with his bollocks slapping against my arse cheeks, he gripped my hair tighter and pulled me towards hm. I was audibly gasping at the fullness of his length, but wishing it would never end as I was in ecstasy.
I started bucking towards his cock, greedily taking it all to the hilt and he then let go of my hair and gripped both my arse cheeks with his big hands, squeezing them roughly.
“You’re actually enjoying this aren’t you, you dirty slut,” Chris laughed. “Beg for it bitch, beg me to fill your sissy arse with my cum.”
“Please Chris, please shoot your hot cum up my sissy arse,” I pleaded.
With a few more deep hard thrusts, he grunted and I felt his cock start jerking. I could feel the heat of his cum shooting inside me as he gripped my arse tightly and pushed into me as far as he could.
When he had finished pumping into me, he pulled out and I fell sideways onto the floor, my knees shaking.
Chris shuffled round on his knees until he was by my head. “Now clean me up you dirty whore.”
After the first experience of having him in my mouth I eagerly reached forward, grasped his cock and licked and sucked at it. I could taste the saltiness of his cum lingering on his flesh.
Shortly after he pushed me away and pulled up his jeans.
“From now on you’re going to be my personal little sissy to use and abuse whenever I want,” he said with a big grin on his face. “I’ll be round next week and I will have a couple of mates with me for you to pleasure too so make sure you have your slutty clothes on again.”
He gave my arse a stinging slap and walked out of the door.
The satin panties were still down around my knees, so I quickly pulled them off and wrapped my right hand around my swollen cock. Wanking furiously I was soon shooting thick gobs of cum, which splattered down onto my belly.
It seems I’m going to be a sissy for more than just my brother in law…Next week cannot come too soon.
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Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...
Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...
The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...
Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...
My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...
The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...
An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...
The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...
MatureSISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...
Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...
SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...
My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...
This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...