A young man is caught by his sister wearing her clothes one day! Now he must participate in her slumber party and do what she tells him otherwise there will be consequences!
I’m not exactly sure why I became so fascinated with the feel of silk and other slippery material. My mother was a fanatic about Halloween. We had this huge box in the attic filled with Halloween costumes and masks. You could dress up as kings, queens, demons, heroes or animals. King Salomon or Cleopatra; slave or harem girl; were only a sample of the costumes.
When I was maybe nine or ten my sister and I got the box down from the attic and began to try on costumes so we could select what we wanted to be for Halloween which was in about two weeks.
My older sister was a bitch to say the least. We fought all the time but on this occasion we had a common interest of selecting a costume so we were working together for a change.
I was telling her that I really wanted to fool everyone and not be recognized. I was dressed as a pirate and she was a cute harem girl. My sister was attractive but short. She had already developed breasts and had short pixie cut brunette hair.
She smiled at me and said, ”If you really want to fool everyone, you should dress up as a girl.”
She handed me a school girl costume which consisted of a short plaid pleated skirt and a white blouse.
“Go put them on and let me see,” she said.
I went into the adjoining bedroom and put the skirt over my jockey briefs and the blouse over my white tee shirt and returned. She looked me over and lifted the hem of the skirt and told me the briefs would never do. She handed me a silk camisole and silk panties and told me to go put them on. I stripped down and put the feminine underwear on. It felt cool and slippery. It felt good. Then I redressed in the skirt and blouse.
“Better. Now spin around and let me see,” she said.
I did as requested and she told me that she thought it could work.
“You know if you exposed yourself a little more no one would even think you were a guy. Let’s try something a little bolder, switch costumes,” she said.
She took off her see-through silky blouse and slipped out of the equally see-through pants. She quickly scooped up her silk panties and put them on. She was standing there in her underwear. Sure I had caught glimpses of her in her underwear before, but not changing into them right there in front of me. I took off the school girl costume.
“Now put on the harem top”, she instructed. I did so and she handed me the pants and added “You’ll have to strip completely and then stuff yourself into them. She just stood there with one hand on her hip and watched me. I turned around and slid off the silk panties and pulled the harem pants up into place. I had to stuff my junk into them before I could turn around to face her. The harem pants were made up with a hot pink string bikini made of satin material and there were two inch wide pieces of satin that fastened with snaps around each ankle. I tied the strings at both sides of the bikini. The top had a two inch band running around the chest and another band around the neck. It had snaps from the back of the collar down to the chest band. I slipped both arms in and she did the snaps. Other than the bands of silk the blouse and pants material was made of sheer nylon. She smirked a little then put a wig on my head and said, “With a little make up you can fool anyone. Go look in the mirror.”
I walked over to the mirror and gasped at the sight. She was right I hardly recognized myself dressed as I was. I also noticed how nice it felt to walk in the silky material. She put on the pirate costume and paraded around and I continued to relish the feel of walking around in the harem costume. I asked, “Do you really think you can apply enough make up to disguise me completely?”
“Sure I can. We’ll practice tomorrow.”
I responded, “Okay but let’s keep this a secret.”
Ever since that Halloween I always liked the feel of satin or silk against my skin. I really did not give the incident much thought. I remember several years later when I was about thirteen and I had to help with the laundry I would secretly handle my sister’s underwear as I folded it for her.
One day I got brazen when I delivered her clothes to her room. No one was home at the time and I decided to try on some of her things. I went from one outfit to the next in utter abandonment. I got so into it that I did not hear my sister return to the house. I did not realize she was standing in the doorway until I saw the flash of her camera. She ran away and I could not chase after her because I was wearing her bra and thong.
I pulled off her things and got dressed as quickly as possible and went looking for her. I found her in the kitchen. She just sat there with a sly silly smile on her face. She was three years older than me, now sixteen, and we both picked on each other constantly. “Did you just take a picture of me?” I asked.
“Yes I sure did, actually two pictures.”
“Give me your camera” I demanded.
She just smiled at me and Said, “No way. You had no right to go through my things and put them on your body. But you did look cute in them”, she retorted. “Don’t worry; I’m not going to tell Mom. Just relax. Maybe I’ll even let you try them on some other time” she said impishly. I just shook my head in disbelief and walked away. What could I do she had caught me red handed.
I just couldn’t get over how I felt wearing my sister’s clothes. It was exciting and forbidden. I liked the feel of the silky fabrics and the way I could flip up the hem of her short skirts to reveal my thigh and ass. It was just so much fun. Over the years I continued to invade my sister’s room and wear her clothes whenever possible. My sister would accuse me of being in her things every once in a while but I would always denied it. I guess I must have gotten bold or just plain stupid.
I began to try on her clothes almost every time she was out of the house and I felt I had enough time to play with her things. My sister was a flirt. She loved turning guys on my wearing sexy clothes or rolling her shirt shorter after she left the house. Her clothes became even more fun to play with because she was buying really sexy lingerie. I even found a condom in her drawer under her bras. I think over the next couple of years I tried on all her underwear and half of her skirts, blouses and dresses.
Deep inside my head I knew my sister was on to me. I just didn’t want to stop. I was now eighteen and my sister twenty-one. Sure enough it happened. She caught me red handed. I was fully dressed in her clothes.
I had on a bright red bra and thong set with a matching garter belt and thigh highs. I had put on her new white pleated flared mini skirt and long sleeved red silk blouse. I was twirling about in front of her full length mirror. I had one hand holding the hem of the skirt up and the other hand stroking my breast. My sister snapped a picture on her phone and ran away.
About two weeks went by and she told me to meet her at her girlfriend Karen’s house on a Saturday afternoon about two. Karen had also developed a really nice set of boobs and all the guys were commenting about her jugs so I had no problem agreeing. Karen was blonde and very attractive. She was also more on the wild side.
I arrived and went into their living room. My sister told me that no one was home except the two of them and she wanted me to play with them.
“You want me to play with you? What do you mean, play?” I responded.
“You heard me, play” she said with a sly smile.
“Do you remember those pictures I took of you a couple of weeks ago? Well I was wondering if you want me to show them to Karen,” she asked.
“Stand over here in front of us and take all your clothes off. Do it now”, she demanded.
“You wouldn’t!” My sister just grinned at me.
“Alright, alright I’ll do it, give me a second”, I said.
I slowly stripped off everything except my briefs and stood there hoping that my sister would tell me okay.
Instead she barked, “I said everything. Take them off now.”
I tugged the briefs down and off my legs and stood completely naked in front of both my sister and Karen. Karen snickered and whispered something to my sister who then began laughing hysterically.
“Karen told me that she wants to see your penis erect, so start touching yourself until you are hard” my sister demanded.
I started masturbating in front of them and got myself worked up so that my dick was standing at attention. Karen went and got a juice glass and told me to cum into the glass. I kept stroking until I came into the glass as instructed. They both applauded. My sister then told me to drink it. I refused and she added that if I drank it she would give me the pictures and I could get dressed and leave. I shrugged and swallowed. It was salty and slimy but I had to do it to get those pictures.
Both girls laughed and laughed at me. My sister fished in her purse and handed me the two pictures which I then realized Karen had probably already viewed. I got dressed and left. I burned the pictures as soon as I could and hoped that this most unpleasant event was behind me.
Six or seven months went by; however, one day my sister came into my room and told me that she was going on a sleep over. She explained that she was in charge of the entertainment for the night.
“So what has that got to do with me?” I quipped.
“Sweetheart, you remember those pictures I took of you? Well, I made copies.” She informed me.
“You did what! You never told me that you made copies. You bitch! I exclaimed.
“You never asked. Besides I thought they might come in handy some day and guess what, they did.” she smirked.
“Listen just ring the bell at this address at ten tonight or your sweet cheeks will be shown to all the girls at the party. In fact I’ll provide copies for each of them to take home.” she growled.
“You can’t do this. It isn’t fair. I’ll never forgive you. I pleaded.
“Just be there, who knows you might even enjoy it” she added with a smile.
There I was promptly at ten ringing the bell at someone’s house. My sister answered the door and escorted me into the living room where about ten young women, all in their twenties, were sitting around in their nighties. Some had on pajamas, others baby dolls but almost all were pastel colors.
My sister addressed the women telling them that she had put each of their names in the bowl she was holding and each would have a chore to do. She then asked me to draw out the first name from the bowl.
“Linda” I announced.
Linda came forward and my sister told her to take off my shirt. Linda very slowly unbuttoned my shirt and gently took it from me much to the appreciation of the crowd. My sister offered the bowl again and I called out the next name.
This sequence continued until I was down to my briefs. Wouldn’t you know it the next name out was Karen? Boy did she ever milk the moment. She tugged and tugged at my briefs until I thought the crowd of women was going to attack her and not me, for taking so long to strip me.
One of the women yelled out, “Nice butt!”
My sister then exclaimed that it was not over and those not yet picked were actually the lucky ones because the fun was just now beginning. I drew the next name and my sister announced that Jennifer was about to show us her technique of a giving a proper blow job.
“Okay ladies, take notes while I show you how it is done,” Jennifer said.
Jen knelt down before me and began to give me one of the best blow jobs I can remember. The women began chanting and encouraging Jen to suck harder.
Jen reached around and grabbed my ass and I shot right into her mouth with full force. My sister gave us warm towels to clean up and told me to sit down on a chair she provided.
She then told everyone that she didn’t think it was fair that everyone was dressed and that I was naked. She then handed me a pair of thigh highs and told me to put them on.
I hesitated and she winked at me and motioned me to continue. Once I had them on she handed me a beautiful pink lacy bra. She followed that up with a matching pink thong which I had to stretch the spandex around my jewels to get them covered.
She then passed a micro-mini flared skirt to me followed by a sheer white blouse. She came up behind me and pulled an attractive blonde wig into place on my head. She then gave me a pair of pumps to slip on my feet.
She asked me to walk around the room to show the girls what a nice body I had. It was interesting the way the short skirt swished about. I noticed that the heels made me sort of sash-shay as I walked. I could feel the nylon thigh highs rub against each other and the silk thong tighten up around my balls. When I returned to the center by the chair my sister put a pastel pink blindfold over my eyes.
“Okay, now for the next name Paul,” my sister said.
I fumbled in the bowl and handed my sister the next name. “Nikki” she shouted. I heard someone come up next to me and then everyone either shrieked or laughed. There was some delay and then everyone applauded. My sister guided me around to the back of the chair and asked me to lean over and place my head on the seat. This of course positioned my ass high in the air much to the amusement of the ladies.
Next I felt the thong being pulled down my legs and off my ankles. My sister twirled the thong around in the air which received more laughter. Rose asked what the object was that Nikki had in her hand.
Cathy laughed at her saying, “Don’t tell us that you’ve never used one of those.”
Nikki said, “It’s a dildo that my mother uses on my dad. Mom doesn’t know. I saw them at it one night.”
Someone was rubbing my ass and then slipped a few fingers covered with ointment into my ass. They were forcibly pushing their fingers, in and out, into my ass. I felt something hard against my anus. It wasn’t flesh. It was soft and flexible but also somewhat ridged. It kept a steady pressure and slowly it pushed into my ass.
Slowly advancing and stretching me open. It kept relentlessly pushing in. Someone grabbed my balls and I yelled out. The sudden reaction caused me to relax my sphincter for a moment and the object slid all the way in. I was full. I felt the woman’s hand on my back as she withdrew a little and then plunged forward again. She slapped my ass hard and the women shrieked with pleasure at the spectacle.
Nikki kept slapping every once in a while for emphasis. She slid into me again and again slowly at first and then picked up some speed.
She was fucking me with a strap on dildo. I then felt lips on my dick and knew someone was going to make me cum while I was being fucked. I figured this wasn’t going to stop until I came again so I closed my eyes shut and pictured the most beautiful girl blowing me. The cheering and applause was deafening.
Jennifer called out to the girl sucking my penis, “Looks like someone was taking good notes.”
“Or she already has prior experience giving a blow job!” declared another voice.
The girl was good and I felt my testicles pull up tight within my scrotum ready to explode once more.
The girl took the entire length, and letting it slowly out. She would then nibble and tease my joint before taking me in again with her mouth.
The dildo continued to violate my rectum and the combination was driving me over the edge. I let out a moan as I spurted my cum into her warm waiting mouth.
After recovered from being “taken” by the girls, my sister said it would be fun if everyone helped put makeup on me and turned me into the girl I wanted to be.
My sister said that there was only one name left in the bowl. She pulled it out and announced that Rose was the lucky winner. Rose was blushing as she approached.
She whispered something in my sister’s ear and the my sister said, “Ah that‘s so cute! Rose is shy and doesn’t want to do it in front of everyone. What do you say ladies? Should we allow her to do it in private?”
There was some discussion, but eventually they agreed that Rose could take me into the bedroom and close the door.
“Come on Paul,” Rose said as I felt her hand leading me away from the rest of the girls.
It was well past one in the morning when Rose and I immerged from the room. Many of the girls were asleep or dozing in chairs or on the floor and others were busily talking. Rose and I came out of the room adjusting our clothes. Rose went to the kitchen to rinse her mouth. I got dressed in my regular clothes and quietly left the house.
I didn’t talk to my sister for more than a week. Finally she came to me and told me she was sorry and asked if I had a good time anyway. I told her, “Actually I did except for the dildo part.” She kind of laughed and we hugged. She then whispered to me, “You should see the video.” And then ran away as fast as she could.
The End....
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