tagTranssexuals & CrossdressersThey're My Sister's!

They're My Sister's!


I've always had a "thing" for Women's underwear; panties, bras, stocking, lingerie, the works. When I was growing up, I often donned my Mother's sexy stockings and panties when alone in the house. Not that I had any sexual feelings towards my Mother, I just loved having my body surrounded by silk and satin. The feeling was amazing. Later, my Mother kind of went slack and didn't bother buying new frilly things as the old ones wore out. Guess she couldn't be bothered anymore after Dad took off somewhere. Granny underwear did not do anything for me.

My sister Cheryl is a gorgeous, 24 year old, "up and coming" secretary who worked at a law firm. She always dresses to the nines to go to the office; nothing overly sexy but professional with that hint of "je ne sais quoi." Always stockings and never pantyhose which are rinsed and hung to dry in our adjoining bathroom.

Cheryl is about 5 years older than I but we are about the same height, 5' 7" with similar bodies build-wise 35-26-36 except she had busts. 35-C's to be precise. Not into sports or anything, I was pretty slender for a guy.

The laundry was common loads and we often got our clothes mixed up. I would put on a pair of jeans not even realizing they were hers until much later. Sometimes I would find a pair of her panties mixed with my briefs. If I was really lucky, they would be a sexy thong or T-back. I would wear them around and jerk off in my bedroom before returning them to their rightful owner.

This summer, I went into Cheryl's room a lot while she was at work. I could easily use the common passage through the bathroom to sneak into her room even if Mom was home and "borrow" her set of bra and panties to walk around in.

It was a hot mid-July morning. I was bored stiff, literally. I had been surfing nylon stocking porn all morning and had a huge 5-inch stiff in my shorts but was tiring of the same slut poses so it was starting to soften. I needed something else to distract me from my boredom.

I made sure Cheryl's and my bedroom doors were shut. I pulled off my t-shirt and pulled down my shorts before entering Cheryl's room. I went over to her dresser where I knew she kept her lingerie and opened the drawer. The sweet, perfume smell wafted upwards into my noses and made my head spin and my cock hard.

I carefully moved items around looking for something special and there it was; a full black lace and satin strapped widow under padding support. The back was lace up but the front had hook and eye closures. The stitched-in boning narrowed at the waist and had three stocking straps hanging down on each side. It had to be pretty new since I hadn't seen it before.

I brought it to my cheek and took in a deep sniff. I swear I could still smell Cheryl emanating from it. I wrapped it around my body and felt her body warmth, and then with nervous fingers, I managed to hook the front. It fit perfect! Our bodies were identical and I needed no adjustments (other than no breast).

I looked and found matching French cut panties. I slipped my right then left foot through and shimmied them up my legs. The gusset cradled my cock clit like it was made for me. I rubbed my pee hole of my uncircumcised cock and felt the pre-cum start to leak. I didn't want to dirty my new panties like this but it was too late. It felt too good and big wet spot started to form.

In her stocking drawer, I found a pair of black fishnets. I sat on the edge of her bed and rolled them up my hairless legs. Not that I shaved them, I just had little body hair to speak of other than my head and a sparse patch of pubic. I clipped the suspenders even though the stocking were really stay ups. I just love the feeling of garter straps on my legs especially as I walked.

I looked in the mirror and admired my reflection. My body was perfect. Pointing my toes really showed the slim muscles of my legs, but the fishnets really didn't go with the outfit so I removed them. I rummaged through her draw again and found a pair of sheer black stockings. The toes and heels were reinforced with pink and had Cuban heels. The tops were pink lace with a pretty pink bow. I slipped them on and clipped them. Perfect.

I went to her closet and found a short skirt to put on. Too short for her business attire but perfect for evenings out.

"Shoes! I need shoes!" I said to myself.

I bent over to look in her closet and found a number of 4 ½ " heeled strappies. I searched and found the ones; black with a small open toe. I reached down to pick them up when I heard a familiar voice.

"Nice ass Cheryl."

It was my best friend Chris. I froze. I didn't know what to do. What would I say? Should I stand up or stay bent over and try to ignore him.

"Have you seen Sam? Your Mom said he was up here." Chris asked.

I slowly straightened up and turned around with my shoes in hand. Chris looked from my toes upwards to my head and down again. His expression went from grinning excitement to jaw dropping amazement.

"Sam? Is that you?" Chris was shocked. "What the fuck is ....?"

"Err. Hi Chris." I was totally red faced. "Umm. How did you ....?"

"Your Mom let me in and told me you were in your room. When I opened your door and couldn't find you I saw Cheryl, I mean you bent over in her closet." Chris said. "Why are you dressed like that?"

"They're Cheryl's clothes." I answered. "I like wearing women's lingerie. It feels so nice against my skin."

Chris is my best friend since grade school. Neither of us was athletic and was of similar built, maybe just a tad taller. Neither had a lot of life experience. As we grew up together, we would jerk off together to the free internet stocking porn. Sometimes we would jerk each other off, but I never let Chris know of my other fetish of wearing lingerie.

"I think you look great!" Chris told me. "Even sexy."

"Fuck off!" I retorted. "You think I'm a weirdo!"

"No, really, I think you look hot. Put the shoes on!" He instructed me.

With trepidation, I slipped on the black strappies. The heels made me taller than Chris.

"Fuck Tim. From the neck down, you look like a real hot slut!"

I didn't know if that was a compliment or not. I took it as a compliment.

"You think so?" I asked as I went towards him with a practiced stride. I stared down into his brown eyes.

Suddenly I felt his arms around my waist and him pull me towards his body. He grabbed hands full of my ass and started to grind himself into me. I could feel his stiffness grow against my leg.

I'm not sure why I did it but it felt so right. I held his head with both hands and gave him a deep, hard, wet, French kiss. His tongue danced with mine as we exchanged saliva.

I dropped to my knees. The tent in his shorts belayed any shock he may have initially had. I unbuttoned his shorts and let them fall to his ankles. We had long both agreed that when we were together to surf for porn, we would not wear underwear (stupid I know, but it got in the way when we whacked off together). His boner was proud. It was the same length as mine but a bit thicker (we measured them).

I looked up at Chris. He smiled and nodded. I grabbed the base then opened my mouth and closed it around the head. It was really the first gay thing we've ever done. It was a bit salty at first, but the texture was amazing; soft yet firm.

Slowly I started to move my head back and forth like I watched on the porn site. I was able to take in almost half before Chris grabbed the back of my head and starting thrusting his hips into my face. I had to relax my throat to avoid gagging on him and then I was able to take the rest with a little effort.

"Fuck Sam!" Chris exclaimed. "You're an amazing cock sucker!" Not that either of us really knew from experience, just from watching the internet.

He continued to pump his cock in and out of my mouth. His head fell backwards as he gave me a few hard and final thrusts with his hips. His white hot goo spurted out and filled my mouth. I had nowhere to spit it out in Cheryl's room so I just swallowed it.

My tummy now filled with Chris' cum. He slowly pulled out his cock from my mouth, but I pulled him back and finished cleaning the remainder of his spunk off his shaft.

"Wow!" Was all Chris could muster.

"That was a huge load Chris." I told him as I stood up. "I don't ever remember you shooting that much even when we jerked each other off!"

By then, my boner was tenting my skirt. Chris reached under my skirt and between my legs. I spread my feet a bit as his hot hand started to caress my balls and the underside of my shaft. Without a word, Chris dropped to his knees. His fingers grabbed the sides of my panties and pulled them down my thighs. The suspenders prevented him from pulling them down further. Chris opened his mouth. I plunged my cock into his waiting throat. There was no gagging reflex.

"Chris, you took the whole thing without gagging!" I said.

Chris stopped sucking for a second. "I've been practicing on a dildo to see how much I could take."

"What?" I asked. "You what?"

"I bought an 8-inch lifelike cock started throating it." He continued. "You're a little smaller by comparison so I can take you easily."

With that said, he went back to sucking my cock. I could feel the head of my cock hit the back of his throat. He took it all. His tongue even lapped my balls as his nose mashed into my sparse pubic hair covering. I was just about to cum when Chris stopped.

"Turn around." Chris told me. "Bend over face down on the bed."

I did as he said as I felt Chris lift my skirt over my hips. His fingers spread my ass cheeks. Then I felt the wetness of his tongue prod my asshole. Chris could extend his tongue out almost 4 inches. He used all of it as it pushed into me.

"Fuck Chris!" I gasped. "Don't stop!" as I felt his tongue wiggle inside.

I wanted to whack off, but I couldn't reach it. I really needed to cum badly.

Chris suddenly stopped. I turned around to complain but as he stood, I noted his cock was stiff again.

His left hand held me tummy down on the bed. He used his feet to spread my legs wider. He took his monster in his right hand and moved it towards my virgin hole.

I felt the fat head press against the rear opening. I turned and watched as a big gob of spit fell on to his knob. Chris slowly started to work it into my hole. Unbelievably he was able to enter my well lubricated entry with only a bit of effort. First the head spread the opening a bit more; he pulled back slightly and then pushed in a little firmer. I felt it pop in.

A slight pull back then Chris pushed it in deep and all the way.

"Fuck Chris!" I moaned. "That feels so fucking good!"

Chris started pumping me slowly at first, but gradually picked up the rhythm before he started to really pound my ass.

"Sam!" Chris shouted. "I'm going to cum again!"

"Do it Chris!" I moaned back. "Give it to me!"

"I'm going to cum in your ass." Chris grunted. "Right now!"

With a final few hip thrusts, I felt his shaft pulsate as his balls emptied into my bowels as mine emptied onto the bedspread and carpet.

Chris collapsed on top of me as we both panted for breath. His deflating cock slipped out of my backdoor as I could feel his second load of day dribble out and down my legs.

"That was incredible!" I gasped.

"Yes it was!" said a strange voice.

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