tagTranssexuals & CrossdressersThey're My Sisters Too!

They're My Sisters Too!


To recap, I sneaked into my sister's bedroom through the adjoining bathroom and dressed in some of her clothes. My best friend Chris caught me. He was shocked at first but then quickly recovered especially after I sucked him off and he exploded in my mouth. After a short recovery, he ended up fucking me in end. Then with Chris' cum dripping out of my ass ....

"That was incredible!" I gasped.

"Yes it was!" said a strange voice.

Well actually not strange but not Chris' voice. We both turned around to look. Standing there with hands on hips and legs slightly apart was my sister Cheryl. She was dressed in a fitted business blue pinned striped suit. The skirt was about 3 inches above her knees. The jacket covered a crisply pressed, white Italian cotton shirt unbuttoned three down.

Chris looked at me then at Cheryl then at me again. Before I could say anything, Chris grabbed for his clothes and tried dashing out of the house. As he scrambled to his feet, Cheryl tripped him and dropped him face first. She placed her four and a half inch heeled stiletto in the middle of his back.

"Stay there." Cheryl ordered Chris then just turned and stared at me.

"I .... Ah .... I can explain." No I couldn't. There was almost nothing I could say that could explain what Cheryl just viewed.

Cheryl went to closed her bedroom door, then stood over me and stared; legs slightly spread, arms across her full bosom. I tried to stand up but Cheryl placed her high heeled shoe on my sternum and pushed me to my ass. "Don't even try to go anywhere either!" She ordered me. "What the fuck are you doing in my room? In my clothes? On my bed?!"

What could I say? My panties, um her panties were pulled down to my knees; her stockings were wet with Chris' and my cum; my dick was still as solid as when Chris was fucking me.

"Cheryl!" I started. "I'm sorry."

"What? Sorry you got caught you fucking little pervert!" She screamed. "Sorry my ass. Actually it's going to be your ass that's going to be sorry!"

"No. I just always loved to wear women's lingerie. Mom stopped buying sexy things and I knew you had some beautiful stuff so ..."

"YOU wore Mom's underwear?" Cheryl said aghast. "You're sicker than I thought!"

Cheryl stared at me. "So what about Chris?"

I tried to explain further. "Well after you left for work, I snuck into your room and found ..."

"My favourite lingerie?" Cheryl finished my sentence. "I thought there was something weird happening to my stuff but couldn't figure it out. It was you, wasn't it?"

"Yes it was me." I admitted sheepishly. "Anyway, I got dressed and Chris caught me when I wasn't expecting him. Things just happened. I sucked him off until he came in my mouth. Then he sucked me for a bit until he recovered enough to fuck my ass. That's when you walked in."

"Well unfortunately for you, the building had a black out and the air con wasn't working so they closed the building and gave us the rest of the day off." Cheryl told me. "Fortunately for me; unfortunately for you."

Suddenly an epiphany stuck Cheryl. She looked directly into my eyes and smiled.

"Chris, get dressed and go. I'll deal with you some other time."

Chris my ever faithful BFF (Bum Fucking Friend) gathered all his clothes and took off faster than Bolt on steroids. I'll deal with him some other time too.

"Sam! Stand up!" She ordered.

I obeyed. My shriveling penis was still dripping cum.

"You know, you're kind of cute all dressed up."

I could see her mind work. I didn't like what I was seeing.

"Pull up your panties. I don't want to see your puny little excuse of a dick."

I pulled them up and fixed my now shrunken penis beneath them.

"You can keep them, too. I don't want them after you soiled them with your cum!" Cheryl said with disgust.

I immediately started feeling a surge of blood rush towards my groin. Cheryl watched my growing erection with amazement.

"Well from your excitement, it seems like you really like wearing girlie things don't you." There was no denying Cheryl's statement. The little boner I sported under my panties was extremely obvious.

"Lay down on the bed.... Face down."

I looked at her in puzzlement.

"Do it now or I'll tell Mom!" I was warned.

As I laid down on Cheryl's bed, I heard her move around to her bedside table, slide open the drawer and retrieve something. She then climbed on the bed and straddled me across my back. I felt her buckle a strap around my right wrist, then my left before pulling my arms behind me and locking them together.

"What are you doing to me Cheryl?" I asked as she dismounted me.

"Well something Greta and I play around with when we're alone." Cheryl responded. "Now to make sure you can't deny anything..."

"Click! Click! Click!"

"Huh?" I muttered as I turned my head towards the sound. Cheryl was taking pictures of me with her cell phone. Pictures of me dressed in my hot lingerie.

"Now for some frontals!" Cheryl forced me on to my back.

"Click! Click! Click!"

"There! If I ever have any problems with you, I'll send these to all your friends!" Cheryl chuckled.

"Click! Click! Click!" Close ups so there was no mistaking me for anyone else.

She pulled one of the leg holes over my swollen dick. "Click! Click! Click!"

"Just to show your friends you really enjoy dressing like a sissy girl!"

Over the weeks, Cheryl enjoyed her power over me. She made me wear some sleazy French maid costume she had from Halloween. It included a short skirt, tight lace up corset with a push up bra, some with black fishnets and garters and a pair of black high heels. I cleaned her room and did all her chores including cleaning the bathroom. Actually I kind of enjoyed it. But the best was when Cheryl made me wash out all of her sexy underthings. I slowly and carefully rinsed everything afraid she would stop me if I did it wrong.

Sometimes as a reward, Cheryl would buy or give me some lingerie of my own including a pair of pink lace panties, white stocking with satin garters and matching bra and one of her silk camisoles. Other times, Cheryl would lay on her bed and watch me jerk off while dressed as her maid.

While she was at work, Chris would still come over almost daily. I'd show him some of the outfits Cheryl bought me. It was fun parading in front of Chris dressed in my girlie things. I would pretend to be a fashion model and let Chris feel me up. Cheryl started making me shave all over so my skin was soft and smooth to the touch. Chris would always get so hard and always ended up coming in my ass.

One late afternoon, I was dressed in a kind of school girl outfit: white blouse with a red push up bra underneath, a short red tartan kilt and white thong panties. I pulled up a pair of white knee hi's and wore a pair of 5 inch strappy black heels.

I kneeled in front of Chris and pulled down his jeans. His cock was already solid. I took it into my mouth and was just starting to take him down my throat when the adjoining bathroom door opened.

"Is that all you two do all day?" It was Cheryl. She had caught us again but wasn't as pissed as last time. "Don't let me stop you. In fact, I insist you continue."

Cheryl grabbed a chair and sat down as I started to pump Chris' cock in and out of my mouth. Chris for his part didn't skip a beat. His cock remained its optimal hardness as he grabbed the back of my head and started rocking his hips.

I peeked over at Cheryl. She had pulled up her skirt over her thighs and was fingering herself through her black panties. Her other hand was under her shirt pulling and pinching her nipples. She signaled her approval to me by staring me right in the eyes and smiling.

I dropped to my hands and knees with my ass towards Chris. Chris was a bit wary of continuing.

"Chris! Please fuck me from behind!" I pleaded.

Chris fell to his knees between my legs. He slowly pulled up the hem of my kilt and flipped it over my ass. He pulled the thong string from between my cheeks and placed the head of his cock on rear entrance.

"Do it Chris!" Cheryl told him. "Fuck him like the girl he wants to be."

Chris wasn't that big and since he had been fucking me so often now, my ass was use to him and I needed no lube. With some slight pressure, his bulb pushed into my hole.

"Oh yeah!" Cheryl moaned. "That's fucking hot! Put it in all the way!"

With one slow push, I felt Chris' cock penetrate me as deep as he could go.

"Pump his ass!" Cheryl was ordering Chris like she was producing a porno. "Hard! Harder!"

Chris was fucking me as hard as he could now. I could barely support myself on my hands.

"Fuck Sam!" Chris grunted. "It's still so tight! I'm going to cum!"

"Cum in his ass Chris!" Cheryl commanded. "Fill his ass with your cum!"

"Arrgh!" Chris grunted as I felt him start to spasm. The first spew entered deep into my bowels.

Chris always could shoot huge loads, this one was no exception. It felt as if a quart of his cum filled my ass.

The action was enough for Cheryl too.

"Fuck YES Chris! Cum in her ass!" Cheryl screamed. "I'm c... c... u... mmm... ing!"

I watched Cheryl orgasm as a huge flow of her pussy juice soaked through the crotch of her panties. Chris fell backwards onto the floor. His boner still angry red and pulsing. My ass was still pointing upwards, Chris' cum pouring out and down my legs.

After a few moments, Cheryl spoke. "Chris, get out of here before our mom comes home."

Chris groggily gathered his shit and left.

"Sam." I snapped to attention from Cheryl's voice. "Help me get undressed and wash out my panties. You and Chris made me soil them so you can clean them."

I stripped Cheryl and covered her with her kimono robe. I collected her things and rinsed out her delicates.

"Hi kids! I'm home!"

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