tagTranssexuals & CrossdressersCaught by my Sister

Caught by my Sister


It was 10 o'clock on a Friday night and I was all alone in the house. My Mom, Erica, who was in her late 30's and recently divorced was enjoying her new found freedom by going out with he girlfriends. My sister, Jane, was out with her friends for the night and that left me alone as usual.

My name is Brian and I am an eighteen year old high school senior. I don't have a lot of friends so I often end up home alone on the weekends. I am 5'6 with short light brown hair and a medium build. Being a swimmer, I have a slim, toned physique and broad shoulders.

This particular night was not unlike any other Friday for me. I waited until my mother and sister left for the night and then had my own fun.

I'm not sure when it started, but I love dressing up in my sister's clothes. Don't get me wrong, I've always been attracted to girls but I love the soft silky material of her underwear pressed against my hard cock. When I am lucky enough to have a whole night with both of them out of the house, like tonight, I usually go all out in my sister's room.

Tonight I chose my favorite pair of her silk panties. They are dark red with black lace trim. I love sliding them up my bare legs as I stand naked in front of her mirror.

Since I am a swimmer I have been shaving what little body hair I have for years. Recently, I also started to shave my pubic hair so my balls are completely smooth. I couldn't believe how good her panties felt against my bare balls the first time I shaved. I almost erupted into her panties as I rubbed myself through the soft material the first time.

I picked out a pair of black thigh high stockings and slowly slid them up each leg. Next I pulled out a pair of her high heels and slipped my feet into them. I liked to practice walking around in heels while wearing stockings. I liked the way that they made my legs look and also how the cool air felt as it flowed over my stocking clad legs.

I was standing in the middle of her room when I heard the door knob turn. I froze, unsure of what to do. Jane walked into the room and stopped dead in her tracks when she saw me standing in her room dressed in her panties, stockings, and high heels. My hard cock was visibly straining against the soft panties when I noticed her staring at my crotch.

"Brian! What the fuck are you doing?"

"I'm so sorry, I thought you went out for the night."

"So that makes this ok?"

"No, I just didn't..."

"I always knew you were a pervert, but this is insane! I come home to get ready for a party and I find my baby brother perving out in my panties."

She stormed across the room and stood in front of her full length mirror. As she looked herself over I saw a wicked grin appear on her face.

"Well, I can't go out looking like this and neither can you."

She turned to me and said "Get out of here so I can get ready. I'll deal with you when I'm done."

I was stunned and embarrassed standing there. I could barely think straight, and didn't have any reason to argue with her. I turned towards the door and started to leave her room.

"And don't you dare think about changing!"

I looked over my shoulder and looked at her as I left. It was hard to tell but she didn't seem as angry as I thought she would be. I walked down the hallway to my room and sat on my bed to wait for her. About a half hour later she appeared in my doorway.

She looked stunning. Jane is a little shorter than me with a similar frame. She is athletic but very feminine. Her breasts are not very large but are very perky, she often goes out without wearing bra, and has shoulder length blond hair. Tonight she was wearing a tight white t-shirt that was thin enough to clearly show off her black lace bra underneath. Her skirt was short and loose around her hips with a hem that fell several inches above her knees. To finish off her outfit she wore a pair of tight black high heel boots that came up to her knees.

I always felt guilty when I would check out my sister before she went out for the night. I knew that she was a slut, everyone in my high school knew that, and would take advantage of the fact that she always wore skimpy outfits around the house.

"Come on, we don't have much time." She waved her hand at me indicating that I should follow her and led me back to her bedroom closing the door behind us. I noticed that she had laid an outfit out on her bed.

"Since you like to dress up so much I thought it would be fun to show you off."

What was she talking about? I've never even thought of leaving the house dressed in her clothes before.

"What do you mean show me off?"

"Well, since you never get out of the house I thought that you might want to come out and party with your big sister."

"I don't know about this."

"You don't have much of a choice. Either you do what I say or I'm telling everyone about you."

Shit, she had me.

"There's no way that this will work. If I go out wearing that everyone will know I'm not a girl."

"Don't worry, I have it all worked out. Come over here and turn around."

I felt her hands reaching around me and realized that she was putting a bra on me. After she snapped it into place I turned and looked into the mirror.

"How is this going to help anything?"

As I said that I saw that she was walking towards me with something in her hand. As she stuffed something into each cup of the bra she told me that she bought these inserts years ago because she was jealous of Becky Anderson's boobs. After she was done adjusting me I lifted my hands up and squeezed my new chest.

I couldn't believe it. I had breasts!

The bra that she chose for me was a black strapless padded bra that completely covered the inserts so that it actually looked like I had natural breasts. She pushed my arms up over my head and wrapped a black silk corset around my chest. I felt her struggling with the back and then she pulled it tight. All of the air was pushed out of my lungs as she tied it closed. She could tell that I was having a hard time breathing and said "Don't worry you look great. You'll be able to breathe just fine."

Next she knelt down in front of me and looked up at me as she slid a loose skirt up my legs. I was lost in her eyes as her hands moved up my thighs to position the skirt. Her face gently pressed against my crotch as she reached around my waist and zipped me up. Before I knew it she was standing in front of me again. Her lips were inches away from mine as she stood there looking into my eyes.

I was in a trance I was so hot right now.

I felt her take my hand and pull me over to her bed and told me to sit. She pulled up a chair and started to apply makeup. After a few minutes she pulled out a set of fake nails and glued them on. After she finished with my nails, she reached out and put a small black necklace around my neck, she called it a choker and said that it should cover my adam's apple. She told me not to move as she sprayed a mist of perfume all over me.

The final piece of my new outfit was a dark red wig. She spent a lot of time making sure that it was straight and I could feel her clipping it into my hair in several different places.

"We don't want this coming off tonight, now do we?" She said as she gave me a sexy wink.

She sat there admirering her handiwork when I heard a car honking outside.

"Perfect timing. It's our ride. Come on Bria... How about Suzy. Come on Suzy, it's time to party!"

Jane got up, grabbed her purse and headed for the door. I moved in front of the mirror and looked at myself in awe. I wasn't a shy teenage boy anymore. I was now a sexy woman. I couldn't believe how hot I looked. My cock was straining against my sister's panties. I heard another honk and ran down the stairs.

It wasn't until I walked out of the front door that it finally hit me. I was about to go out to a party in drag. If anyone found out my life would be over.

Jane's friend Amy was waiting in the driveway. They both looked anxious so I quickly locked up the house and hopped into the back seat of her car.

"Amy, this is my cousin Suzy from out of town. She is staying with us for a little while and wanted to have some fun."

"Hi Suzy. I love your outfit. You look very sexy!"

I couldn't believe it. She actually thought I was a girl.

I was about to open my mouth when I realized that my voice would be a dead giveaway. I cleared my throat and made my best attempt at a high pitched female voice.

"Thanks, you look great too."

Jane turned back and looked at me from the front seat with a big grin on her face. "Don't forget to pick up the boys Amy."

"Don't worry, Jarred's house is on the way."

As we drove across town I was starting to feel a little more comfortable in my new role and made a few brief attempts to join in the conversation to test out my new voice. We pulled up to a house and two guys came running out. One of them walked around the car and they each opened a door to enter. I didn't have much of a choice and slid to the middle seat as they both pushed themselves in flanking me on both sides.

My sister turned around and introduced me to the boys. "Jarred, Alex this my cousin Suzy. She is staying with me for a little while. Oh yeah, and she's kind of a slut!" A big grin spread across her face as she said the last line and then turned around.

The guy on my right side turned to me and said "Hi Suzy, my name is Jarred. You smell great."


The guy on my left side held up his left hand and took my right hand in his. "My name is Alex. I love your outfit."

He let go of my hand and his right hand moved onto my left leg. He gently caressed my thigh through the stockings as we drove away.

My head was swimming. I was getting hard while another guy was touching me. Does this mean that I'm gay?

Since the backseat didn't have a lot of room I ended up putting my left hand on top of his as he continued to caress me. I could feel Alex leaning into me and push my hair away from my neck. His warm breath against the nape of my neck made my whole body tingle with excitement.

"Mmmmm, you really do smell nice." He moaned into my neck as his hand slid a little further up my thigh. I squeezed his hand nervously as I felt his wet lips pressing against my skin. My head rocked back and I let out a little moan.

The car came to a stop on a quite street lined with dozens of other cars and Amy said "We're here!"

All of a sudden the doors flung open and everyone poured out of the car. Alex still held my hand in his as we walked up to the house.

My sister came in close to me and whispered into my ear.

"It looks like you were enjoying yourself back there. Just be careful, you can only go so far. We don't want anyone to find our your little secret do we. Have fun tonight!"

She gave me a peck on the cheek and grabbed my ass through the skirt before breaking off to catch up with Amy.

I was thankful that I had spent so much time practicing walking in heels, but I was still having a hard time keeping up with everyone else as we walked up the long driveway.

The party was in the "rich" part of town and the house was gigantic. It took us nearly five minutes just to walk up the driveway. As we approached the house I could hear loud music mixed with laughter pouring out of the open windows. Thankfully, I didn't recognize most of the people at the party as we worked our way inside. The lights were dim and most of the people were dancing in the front room. Jane and Amy led us right to the kitchen where the drinks were. Amy poured a round of shots while my sister mixed up drinks and passed them out to our group. Everyone held up their shots and drank them together. I've never really drank before so I followed their lead. The shot burned my throat but I noticed everyone else drinking their mixed drink after the shot. I again followed their lead and found that the sweet drink helped wash the shot down.

"Let's do another one!" Alex shouted as he slipped his hand around my waist and pulled me into him.

I was starting to feel a little warm after the second shot. Alex again slipped his strong arm around me and pulled me towards him. I held my drink in one hand and wrapped my other arm around his waist. He held me against his tight stomach as he leaned in and kissed me. I was surprised at how good it felt when his lips pressed against mine. I let my head fall back and my mouth open as his tongue worked its way into me.

This was my first kiss and I had no idea what I was doing.

His tongue swirled around inside of my mouth and I desperately tried to think of what I should do. I dropped my drink and brought my hand up to his neck. His skin felt warm and soft as we kissed. His hands reached around me and slid up my thighs under my skirt. He massaged my ass through my sister's panties while he ground his crotch into mine.

Alex broke away from our kiss and pulled away from me. My skin felt cold as he took his hands away. He grabbed my hand and pulled me into the next room.

The lights were all off and people were dancing all around us. He led me to the far corner and sat down in a chair pulling me between his legs. His hands against explored my legs and thighs, but I knew where he was going next. I could only think of one way out.

I lowered myself to my knees and crawled up to him. He looked down at me a with a knowing grin and started to unbuckled his pants. He lifted his ass up enough to slid his jeans and underwear down to the floor. In an instant I was staring at his rock hard cock inches from my face.

Up until now, my only experience with a cock was my own. I had never even thought of another man in this way before, but sitting here dressed up like a slut in my sister's clothes made me feel so sexy and feminine.

I started out slow and let my hands rub his thighs. He felt warm to my touch and his skin was soft. I pushed his thighs apart and slowly inched myself closer to him. My hands moved up his thighs until I reached his cock. I slowly wrapped my hands around his balls and gently played with them as his cock stared at me waiting for me to take it.

My right hand cautiously moved to the base of his hard cock and I wrapped my fingers around him. I could feel his shaft twitch to the rhythm of his pulse as my hand slid up his cock. I was amazed at how soft the skin was when my hand finally wrapped around him.

I gave him a gentle squeeze as my left hand continued fondling his balls. I felt his hands behind my head pulling me into him. The tip of his cock was getting closer and closer. I closed my eyes and opened my mouth.

The tip of his cock pressed against my lower lip as he guided me onto him. I opened my mouth wider and felt his hot flesh slide into my waiting mouth. My tongue slid along the bottom half of his cock as I continued to lower my face onto him. I closed my lips around him when I felt the tip of his cock brushing against the back of my throat.

I moved my hands to either side of the base of his cock to balance myself and started to suck. I didn't know what I was doing but it felt good to me. I hoped that it felt good to him too.

I moved my mouth around as I sucked him and then slowly pulled my head back up the length of his cock. I stopped with the tip of his dick resting on my tongue and swirled it around him. I could taste his salty pre-cum dripping onto my tongue and found the courage to continue.

I slowly worked my mouth back down the length of his cock while I slid my tongue around as best as I could. I kept this up for a few minutes until I could feel him pushing his hips into me as his cock filled my mouth. My nose was pressed against his pubic hair when I felt his cock twitch and fill my mouth with his hot sticky cum. I swallowed as much as I could as it flowed into me stream after stream. I could feel it dripping down my chin as his cock slowly started to shrink in my mouth. I pulled my mouth off of him and collapsed into his lap.

"There you are, I've been looking all over for you!"

I looked up and saw my sister standing over me with a devilish grin.

"Come on Suzy. I've got a friend I want you to meet."

She pulled me up and led me out of the dark room. I followed her upstairs into a dimly lit bedroom. There was a tall guy standing in the corner.

"Matt, this is my cousin Suzy. Suzy, this is Matt, don't worry I've already told him all about you."

Matt moved over to me and took my face in his hands and pulled my mouth to his. Our tongues met as he passionately kissed me. His hands slid down my body and then moved back up my thighs pushing my skirt up. I loved that everyone wanted to rub my ass so much. I felt so sexy in his arms.

"Suzy, Matt here has never has had sex before and I told him that you would love to help him out."

My sister pulled me away from him and pushed me towards the bed. She turned me around and pushed my forward, bending me over onto the bed. I felt her pulling the back of the panties to the side as she rubbed something cold onto me. Before I knew it I felt her slip a finger into my asshole. I pushed my legs further apart and let out a soft moan, pushing my hips into her hand. She pulled her finger out of me and it was replaced by something much warmer.

I felt it pushing into me and realized that it must be his cock. In the dim light he must not realize that he was about to fuck my ass. I was so excited waiting for him to enter me. He slowly pushed the head of his cock against my asshole teasing me.

My whole body tensed up as he finally thrust his cock inside of me. My knees were shaking as his hard cock pushed further into me. His hands held my hips and pulled me towards him as he slowly developed a rhythm with his thrusts.

I looked up and saw my sister positioning herself in front of my face with her legs spread wide apart. She pulled her skirt up around her waist as she slide her pussy under my face. I could smell her musty odor as she pushed my head down to her shaved pussy.

My tongue reached out and licked her as Matt slammed his cock into my ass. My moan was muffled by her dripping pussy. I lapped at her pussy like a madman. She tasted so sweet as her juices mixed with Alex's cum in mouth.

I moved my tongue back and forth until it slipped inside of her. I could hear her moaning as I pushed deeper into my sister's tight pussy. I could feel her clit rubbing against my tongue as I worked it in and out of her. Her thighs clamped down around my head as she came. Her sweet juices dripped out of her pussy as I tried to lick up every drop.

Matt kept pounding my ass as my sister lay exhausted in front of me.

Matt kept pumping his throbbing cock deep into my ass as I noticed my sister reaching her hand down to grab my cock. My penis was aching to be freed but she just rubbed me through her panties while Matt fucked my ass.

Her hand moved up and down the length of my cock faster and faster when he pulled my hips into him. He buried his cock deep inside of me and I knew what was coming.

His cock twitched and swelled up inside of my ass. His hot cum shot deep into me, filling me up from the inside. The sensation of his cum filling me up while my sister stroked my cock through her silk panties pushed me over the edge. I felt my cock exploding into her panties as Matt continued to shoot his cum into me.

He shot three large bursts of cum into me before finally pulling out.

"Wow, you were right Jane. Your cousin is a great fuck."

I heard a zipper and then a door close.

"You did good tonight Suzy, but it's getting late. I called a cab for us, it should be here by now."

Without missing a beat she got up and fixed her skirt. I followed her down stairs and out of the front door to the waiting cab. We both hopped in and the cab took off.

She didn't say a word to me as we walked into the house. Before we even made it up the stairs the front door opened again and our mom walked in.

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