Kinky Sissy Boi Slumber Party

Kinky Sissy Boi Slumber Party

After an enjoyable, late night out at a party for the birthday of our friend, Hank and I had a few drinks. We don't drink that often, so I knew that we would come home feeling pretty good.

I had a surprise planned for Hank. I announced that I planned a kinky slumber party...for two. Everything was planned while Hank was away on a fishing trip.

I told him to go to the bedroom and to get undressed and sit on the bed and wait for me to come to get him. He sees the TV remote on the bed with a note that said "Hun, press play, sit back and relax and I will be back for you as soon as I have everything ready." I had some of his favorite hypnosis discs loaded in the DVD player. He was happy.

Once the scene was set, I went upstairs to get him, I was dressed in a black nightie, black nylon stockings and hot pink pumps. He was lying back on the propped-up pillows until he noticed a blindfold in my hand, then he sat up giving me a curious grin.

I blindfold him, grabbed his cock to guide him downstairs and stood him at the entrance to the den facing the kitchen. I removed the blindfold, and there was a spread of snacks on the kitchen table of whole carrots and ranch dressing. He asked why the veggies were not sliced and I told him they don't need to be sliced to eat them at this party! Hank is intrigued. Then he sees chunks of chocolate in a glass bowl next to a bag of huge marshmallows. He asks, "Where are the graham crackers?' I said I will be using something else in place of the graham crackers. Next to the chocolate is a tray of various fruits, apple slices, strawberries and mango slices with a sweet cream cheese fruit dip. Little did he know, there was another snack that was being saved for a surprise...in the freezer!

In the center of the room on the floor were 2 sleeping bags, several pillows, a pile of blankets and several chairs. It was summer so Hank was confused as to why there were so many blankets and asked why. I said, in good time my little sissy boi. You need to just relax and take it all in as it unfolds, sweetie.

Over the back of the sofa was a little pink frilly nightie with pink panties, white stockings with a white garter and some pretty pink heels...and a wrapped present. I tell him to go over there and slowly put on his outfit but don't open the gift until he is dressed.

I sat in the recliner, lay back and opened the lamp table drawer. He looked over and saw a drawer filled with all sorts of vibrators and dildos. As I grab a vibrator, he flashed a sexy, devious smile...so HOT! Then he looked again, and his eyes got wide...I had a strap-on in the drawer! Nothing was said. I am sure it was because he really didn't want to know what I planned to do with it!

As he put on his sexy pink nightie and accessories, I laid back and put the vibrator on a low, teasing setting and rubbed it on my clit as I played with my left nipple. He is so hot in his sissy boi clothes; I have to hold back from attacking him because I have SO many fun things planned. I want the erotic feeling to last all night!

"Now it is time to open your gift, sissy boi Hank." He removed the baby pink wrapping paper from the box, which had a card taped to the top. The card said, "My sissy boi Hank, you are the sissy boi I always dreamed about, and I love how much it excites you to dress like this. I was so happy when I first asked you to do this because it turned me on so much to find that you also had this desire. This gift is something you mentioned in our discussions on this topic, and I hope it helps complete your fantasy, it completes mine. "

I tell him not to open the box yet. I can't resist, I have to go over to him before he takes off the lid. As he lifts the lid, his jaw drops, and he can't believe his eyes. His very own beautiful, giggly set of silicone B cup tits! He takes one out of the box and starts playing with it, rubbing it on his face, he looks like a kid on Christmas morning.

These stick to the skin, but it has to be free of hair. He tries to make it stick but it won't. I tell him to come with me. I take him to the half bath where I have the razor and shaving cream ready, and the sink filled with water. I removed his nightie and rubbed the shaving cream all over his chest. I slowly and carefully start shaving his chest as I play with his cock. I got some of my Wild Honeysuckle lotion and rubbed it all over his smooth, hairless chest. Oh my, it feels SO good...and he smells nice too!

We go back into the den, and he asks me to put his tits on to be sure they are on correctly. Since the lotion has mostly absorbed, the tits stick perfectly. I tell him to close his eyes, and I walk him over to the mirror. I tell him "Open your eyes." When he does, he is so pleased with how they look, he has to touch them. I turned him around to face me and I pressed my tits against his and grabbed his ass and pulled him tight to me and said, "You are going to have your first female orgasms tonight, hope you are ready." He says, "Oh dear, I am so ready to do this with you!"

I tell him there is more to this slumber party he has yet to see. He says, "There is more? I can't imagine." He has no idea what Mistress Alessandra has planned for him. There is one very important part of this girly sleepover which is going to blow his mind!

The door to my office is always closed, so he thought nothing of it. But I had the best part hidden inside. I asked him to go to my office and get my glasses. As he opens the door, he stops dead in his tracks. He backs up and turns to look at me and is speechless!

In the room is a fully stocked white makeup vanity, one all his own with professional lighting. It is filled with all the tools and supplies to make him look like a woman.

On the other side of the room is a clothes rack with a few sexy dresses, sequin miniskirts, more nighties in white, red and black with matching stockings, garters and shoes. But the best outfit on the rack is a sexy black and white maids' outfit with a frilly skirt, apron, and panties, including the white lace hat!

I told him to open the closet. There he finds is a small table in with 3 different wigs: blonde, black and brown. He sees a bag under that table and walks towards it. I said, "Who gave you permission to approach the table?" He stops, turns around and said, "I am so sorry Mistress Alessandra; I was not thinking." I could tell by the look on his face that he knew there would now be consequences for his misstep.

I ordered him to exit the closet and to stand in the corner facing the wall. He is going to pay the price for interrupting my plans. I walk towards him and all he can hear is the slow, determined clicks of my heels on the wood floor. "Put your hands behind your neck and lock your hands together." His trembling reply was "Yes ma'am". I put a blindfold on him and reached around to slap his cock to find it getting hard, so I gave it a really good smack.

He heard me walking away as I entered the closet and opened the bag that he was so curious about. In this bag there are various sizes of pink Velcro hair rollers I planned to use to curl the hair of the wig of his choice. Now these rollers will have another purpose.

I had him unlock his hands and told him to reach in the bag not knowing what he may find. As he feels these prickly cylinders, his brow furrows with wonder. I told him to select 2 and I took them from him and told him to put his hand back behind his neck. I put his cock in my hand and slipped on the 2 rollers as he gasps from the roughness.

I made him turn around, making sure his blindfold was securely in place. He hears me pull up the chair from his vanity. I sit down and start teasing the head of his cock with my mouth and tongue. He moans with pleasure until he realizes that the harder his cock gets, the more the rollers dig into the shaft of his cock. The head of his cock begins to turn red; I move to squeezing and licking his balls as my finger plays with his asshole. I asked if he had learned not to give in to his impulses. He said "Yes, Mistress, I will never assume I can give in to my own will when I am your slave." I stop touching him and leave the room so his cock can go down enough to remove the rollers.

I was so proud of how well he took his punishment; I told him we can now get back to the rest of the evening.

It is time to give each other a makeover. I take him back to the half bath and I lather up his face. We cannot do a proper makeover with his facial hair if he is going to pass as a woman. I order him to shave himself because I don't want to cut him.

I sat him at his vanity and opened the top to reveal foundation makeup, contour compacts, blending sponges, several colors of eyeshadow, eyeliner and lipstick. There are also false eyelashes, dozens of makeup brushes as well as a few bottles of various shades of pink and red nail polish. He is so excited to play with all of this makeup!

I told him I would be right back, just sit here and soak up all of his new toys. I come back into the room wearing the strap-on under my nightie. I told him that he would be playing with his cock and mine while I do his makeup. He had heard that girls get kinky at their slumber parties, he didn't expect this but is pleasantly surprised!

His foundation is on, and his skin looks very smooth. I put some vivid purple eyeshadow on him with frosty pink under his eyebrows. I applied black eyeliner on his upper and lower lids and put on his fake eyelashes. To make him passable as a woman, I contour his masculine features, so they look soft and smooth. My sissy boi is looking so beautiful! A few last touches with his rosy blush and bright fuchsia lipstick. He thought he was done but no! I told him to open the bottom drawer of the vanity where he finds another gift. I told him that his makeover is not complete without this final touch. It is a bottle of his favorite feminine scent, a bottle of Tabu perfume.

After all of these activities, we went to relax in the den and unroll the sleeping bags so we can sit an play some games. I decided to tell Hank what we are going to do with the blankets and the chairs. I tell him when I had slumber parties in high school, we would sit around and talk about boys, dicks and sex. We would build a fort so the parents wouldn't fully hear what we were saying. I started placing the chairs in front of the recliner so I could drape the blankets over them to make a roof and walls.

I poured us both a glass of Riesling and grabbed the trays of carrots, fruit and dip then we crawled into the fort. I asked sissy boi if he has ever sucked a cock and he said no. Since I was still wearing my strap-on, I told him he was going to know now. He was hesitant, so I told him to put his head on my lap. I stroked his hair as I rubbed my cock on his face. Then I took my shoes off and started rubbing my stocking feet up his legs to his balls and cock.

I figured if I got him horny, he would not think about me putting my cock in his mouth. He thought I was doing all of this because I wanted to please him and because it is the fantasy he told me about. Even though we have been together for a while, I have never told him a secret fantasy of mine, but tonight he is going to know.

His cock got hard as I rubbed my feet on it. He put his hand at the base of my cock as he rubbed my clit, this pleansantly distracted me. I told him that before we continue, I needed to tell him about a fantasy of mine. Just as he has fantasized about me dominating him while he was dressed as a woman, I have also had a similar fantasy of dominating him dressed as a man.

I asked if this bothered him, and he said not at all because that was the other part of his fantasy that he had not yet shared with me. I was thrilled! I told him we will complete this fantasy of his for the kinky slumber party and then talk about how we want to do this role switching another time.

I put my cock in his mouth and told him I am going to do it like you guys do to us girls. So, I get on my knees with my cock over his face and fucked his face. It is his first time, so I don't want to get too aggressive, but I still did it a little forcefully. While he is enjoying sucking me off, I reach for his cock and start stroking and twisting it hard. Just when I think he is about to cum, take my cock out of his mouth and my hand off his.

He looked so disappointed. I said, "You can't cum yet, the night has just begun!" He smiled and moaned; I know he enjoys being edged...and I like watching him enjoy it!

I now asked him if he has ever eaten pussy as a girl. He said no and that he doesn't know how, he is still a virgin. I told him this is what girls do to explore sexual things before they do it with a guy, so this is part of the slumber party tradition. To ease him into it, I told him I was going to teach him how to do it. I told him to select whatever fruit he desired and put it in my hole and eat it from my cunt. He selected the mango slices.

I got onto the recliner and spread my legs open. The mango went in easily as I was already wet from watching him suck my cock. As my pretty little sissy boi stared eating the mango and working his way to my clit, I put my legs over his shoulders. As he was finishing the mango slice, I could feel his tongue on my hole, my stocking thighs squeezed his head as he felt my heels dig into his sides.

I told him to dip a strawberry into the fruit dip and put the dip all over my pussy. Take a bite of the strawberry then lick the dip until you get to my clit. When you do, I want you to suck it in and out of your mouth as you flick your tongue on it. It was feeling so good, but I wanted more. I instructed him to put a carrot in my cunt and to pour ranch dressing on it telling him I want him to imagine that it is a cock that just came in his mouth. I wanted to see the "cum" all over his face and lips. I then leaned over and licked the "cum" off of his face.

I was so ready to climax, so I opened the drawer of the lamp table and grabbed one of the dildos and told him to fuck me with it. As I am about to cum, he stops!

For denying me the orgasm I deserved and getting off track from the slumber party I planned, I informed him that his cock is going to be spanked until it is red and swollen! Then I will force him to lick and suck my cunt as he fucks me with my dildos. If he didn't make me cum in 2 minutes, his cock and balls will get additional punishment. I should have known that he was being bratty, he gets off on cock and ball torture.

Well, he was shocked because I told him that for disrupting the evening, starting tomorrow, I will be Master Butch for the next 2 days as a punishment for disrespecting Mistress Alessandra and interrupting the evening I planned! He will not be allowed to wear his training bra, matching panties, lace garter belt or nylons. His cock will be locked in a metal chastity cage for 2 days and he would be my gay slave for me to butt fuck him as much as I desired. He knew it was going to be rough 2 days because I get off on pegging my sissy boi!

Now, we will get back to our sissy party. We go over and sit on the couch and on my way back, I grabbed a bottle of pink nail polish and announced it was Mani/Pedi time! I told him to remove his heels and stockings and to do it slow and sexy, like a striptease because guys really get off watching a girl do that. He wasn't sure and asked me to show him how to do it. So, I get up and lift my leg to remove my shoe, then I put my foot on the coffee table and slowly unhook my stockings from my garter belt. Then I gradually roll my stockings down my leg until I get to my ankles. I grab the toe of the socking which makes the stocking unroll, and I drag it across his face down to his hand that is stroking his cock.

When he does it, I can see my absolute favorite sight, his gorgeous cock and balls hanging between his legs! I love seeing that when he walks around the house naked and bends over...OH MY GOD, so hot!

I have him lean back and get comfortable as I sit on the coffee table. I lift his leg and put it between my legs so I can paint his toes as he sips his wine. This pink looks so good on him! I do the other foot and then move to his hands. Before painting his fingernails, I have another surprise. I am putting fake nails on him and then painting them. I love how excited he is about his special sissy boi night!

He wanted to paint my nails, but he always does that, so I told him we can skip that so we can get to the game I have planned.

I go into the laundry room and come out with 4 different colored balloons. We are going to play the Secret Message Balloon Pop game. To play this game, you select a balloon, then you sit on it until it pops, when it does, there is a secret message in the balloon that tells you what you have to do.

Hank selected the red balloon first. It is so funny because his balloon will not pop no matter how much he bounces up and down on it. So, I told him he could use the heel of his shoe. His note says to put on as many wooden clothespins on his cock and balls for 5 minutes. For each clothespin, I will give him a hand job for 15 seconds. When the 5 minutes is up, he has to keep all of the clothespins on for 2 additional minutes. If any of the clothespins come off before the 2 minutes is up, he gets NO HAND JOB! He was able to put and keep 8 clothespins on, so he got a 2-minute hand job.

Now it is my turn, I chose the purple balloon. It says to go melt the chocolate on the table and use the marshmallows to paint warm melted chocolate on the other person's body and lick it off. He lays down on the floor and I first put several marshmallows under his balls and tell him to keep his legs together. He giggled when he learned that his cock and balls are being used in place of the graham crackers.

I start by putting chocolate on his chest and nipples then down his stomach to his cock. I get a HUGE glob of melted chocolate and put it on the head of his semi-hard cock. It slowly dripped down to his balls. He said, "Oooh, that feels good dripping down my cock!"

I started licking it off his nipples and then down his stomach. Now if move to his balls and suck each one into my mouth as I run my tongue all over it so I can get all the chocolate off. I grab the base of his cock, and I start stroking it, getting chocolate all over my hands. I start licking his shaft and put his cock in my mouth. I move it in and out of my mouth as I run my tongue all over his cock. I now have chocolate covering my face and hands. I got up and I straddled him, then leaned over to kiss him and got chocolate all over his pretty made-up face!

It is his turn again; he selects the green balloon. The message in this balloon says to find something from my office to spank the other person with and give them 25 good whacks. He goes into my office, and I can hear him rustling through the drawers of my desk. He finds my favorite plastic ruler, 18" long and 2" wide that I have had since 1981, ironically it is the year we met. I was hoping that is what he would select! Had he noticed the wooden paddle hanging from the doorknob behind my door, he would have surely come out with that, he LOVES spanking me with anything wooden!

He came back and is so turned on; he is rubbing his cock. Part of his fantasy was to be my sissy boi and dominate me. He sat on the couch and told me to bend over his knee. He gave me my first whack and then rubbed my ass cheeks. He didn't give me my 2

nd

one right away, he waited about 30 seconds, raising my anticipation. He suddenly grabbed the waistband of my panties and pulled them tight between my ass cheeks to hold me still like the reins on a horse.

I love when he spanks me, I almost had an orgasm! When he is done, he gets up and goes to the bathroom. He came back with my Wild Honeysuckle lotion and rubs it on my ass cheeks because he is always so considerate when he dominates me. This relaxed me but because he so enjoys being a Dom that I should have known something was going to happen that I didn't expect. I am thinking he is getting more lotion for my ass, but NO! Suddenly, I feel a lubed-up dildo touching my ass and it did NOT go in the hole I wanted!