My heart was pounding out of my chest. My mind was racing. The door was definitely opening. I there was no were to go quickly. I was going to be seen. I couldn't imagine this happening. Someone was about to find me dressed up in a sexy feminine outfit complete from head to toe, trying my hardest to look like a hot girl.
The door opened and I saw my sister. She looked up after putting away her keys and saw me and just stopped for a moment. She stared at me and just said "Hi".
Some how I managed to mutter back "Hi."
She told me that she had finished up at her job early and came home. The way she was talking was like nothing was out of the ordinary. I was still in shock but she seemed unfazed.
"What's up?" she asked. "Why are you so quiet?"
"Uhhh," was all I could mutter. My mind was still racing and I didn't know what to say much less to think.
"I think I can figure out what's wrong. You weren't expecting me home so early and were surprised to see me. Right?"
My mind was clearing a little and I said, "Yeah, I guess that is part of it."
"And I can probably guess the rest too." She said. "You weren't expecting to be seen looking like that."
"Well, that is certainly an understatement." I replied, my mind coming back to me a little more.
"I can understand that." She said.
When I first hear the door opening I had never expected this calm response.
"Now there is one other thing." I told her. "I can't believe how calm you are. When I heard you at the door I was expecting whoever came in to be in shock, disgust or horror. But you seem like it is just the same-old same-old."
"I am surprised, a bit shocked, but not horrified or disgusted." She said. "I doubt anyone expects to see their brother dressed in a blouse and skirt with high heels and stockings and wearing makeup and with long painted fingernails. But, who cares? You aren't hurting anybody, right? So what difference does it make? How is it different from when a woman wears jeans and an old lumberjack shirt or when I borrow you sweat pants or t-shirts? I assume those are mine since the look so familiar."
"Yeah, they are." I said, relaxing considerably.
My sister was less than 2 years younger than I was. We were very similar in many respects. She was just a shad shorter than I was, but we were about the same weight. She had a more feminine shape than I did and was an attractive petite woman. I was just a skinny guy. When we were much younger people thought we were twins. As we grew up and into our teen and college years we drifted apart, as is so common with siblings, but still stayed close.
"Since I steal your stuff all the time, I guess I can't complain." She said. "Though I probably look better in your stuff than you do in mine."
"What do you mean?" I asked. I had spent quite a bit of time to look like this and thought I looked pretty good.
"I'm not trying to insult you. It's just that it takes practice and help to be a good looking woman. You seem to have a little practice but no help. Your style is a little awkward. I can help if you if you like."
My heart was beginning to pound again. I couldn't believe my ears. "What do you mean?" I asked.
"I could give you some tips some of the things that girls share with other girls. The things we read about in magazines. So you can look more naturally female and less like a guy in drag."
"I don't know what to say except, sure!" was my response.
For the next couple of hours my sister taught me many skills and tricks on how to look more feminine. She showed me tips about applying eye makeup, nail polish; how to gently roll on stockings and hook the garter straps; how to make sure that my legs were as smooth as possible when shaving; the best way to walk in high heels. On and on she went demonstrating on herself.
Then she told me it was my turn to put into practice what I was just taught. She said that she was going to pick out an outfit for me and I would have to get ready by my self. She told me to go wash my face while she was getting everything ready. I went to the bath and washed my makeup off and when I returned she showed me my outfit. Her choice was unmistakably feminine and sexy. The kind of outfit that would have heads turning in a room as soon as the woman wearing it walked in. she had picked out a basic "little black dress", form fitting and coming just over my knee. To wear underneath she had picked out a silky and lacy black panty, bra and garter set. For my legs were thigh high, lace top, back seam stockings. She had also picked out a pair of 4" black stiletto pumps.
"Well, there you go." She told me. "Your nails are already good and there is nothing wrong with the way your hair is. If you remember what I taught you, you will look like a knock-out. I'll see you in a while" I started to get ready, my heart pounding and my mind on cloud 9. This was the sexiest outfit I could imagine and I was going to be wearing it. I carefully tucked my member up and back between my ass cheeks to keep it out of the way before it got too rock hard. I started with the stocking like sis had said and then fastened the garter belt. My cock was already swelling and I rushed to pull on those silky panties to help keep it in place. The elasticity of the fabric helped but my member was straining. Next I picked up the bra and found a small pair of breast forms. I guess these were what my sister used when she wanted to seem more "well endowed". They fit well in the cups of the bra, so I had to assume she had other larger bras to accommodate her natural breasts along thit these supplements. Then I pulled on the black sheath dress. It was tight enough in some places and loose enough in others to make me actually look like I had a figure. Finally, I slipped on the stilettos. I was looking good already. I sat at her makeup mirror and applied my makeup just as she had told me: nothing too heavy or cakey. Following her tips made a dramatic change to my face. The makeup was noticeable, but it wasn't overdone or flashy, just classy and sophisticated.
I got up and went to present myself to my sister. She looked and stared, more than before when she had first walked in on me. Now I was the first to speak.
"What do you think? You are awfully quite. Any critiques?"
She took another second, just staring at me and then spoke up. "Now I am shocked! I didn't expect anything this good. You kook awesome! I can hardly believe it."
"I guess you were a good teacher." I replied.
"Thanks, but this is more than just my teaching. You walked so gracefully." She said.
"Well, this isn't the first time I have worn 4" stilettos." I confided.
"OK. But that is just part of it. You look so feminine -- from head to toe. The transformation is amazing. And I mean from head to toe. I can't help but notice that there is no 'bump' were there should be on a guy but not on a girl." She said.
"Yeah, I learned a while back how to avoid a bump like that." I told my sister.
"It sure does work. Where do you hide it?" she asked.
"Up between my legs between my ass cheeks. When you wear tight fitting panties they help keep everything in place. It's a little uncomfortable but it works. I guess girls have to go through some discomfort to be sexy." I answered.
I hadn't been thinking about it before but my cock was beginning to strain hard for release from its satin sheath. Dressing like this always got me turned on and rock hard. I could be hard for hours as long as I stayed dressed like this even if I came several times.
"Well that is one thing genetic girls don't have to deal with. I don't think you should have to either." My sister said as she walked over to me.
She lifted up the skirt to my dress and thrust her hand down my panties. The shifting of the satin allowed my fully engorged cock to spring out. My sister grabbed it and felt its engorged pre-cum covered head. I could hardly believe what was going on. Just a couple of hours ago I was home alone. Now here I was looking like one of the sexiest women I had ever seen with my sister's hand on my cock. I was light headed, nervous and excited.
"Wow, you sure have a big cock." My sister observed as it stuck out of the top of her panties. "I wasn't expecting that."
"Why not?" I asked?
"I have a bit of a confession too." She said. "You aren't the only one who gets turned on by guys dressing like girls. It turns me on too." I guess there is something to be said for genetics.
"I have read so many storied on-line about cross-dressing guys and their small cocks that it seemed like it had to be that way. But obviously not!"
I had read those stories too and also noticed that every cock mentioned seemed to be described as 3" or less. Mine was no monster at almost 7" but not tiny. I was flattered and didn't know what to say.
My sister wasn't waiting for a response anyway. She pulled me closer to her and brought my hand under her skirt and down her panties. The panties weren't silky like mine but the folds of her vulva were velvety and smooth and her cunt was already dripping with her juices.
"There is no way I am going to let a hard on like that go wasted." She proclaimed.
The thought of what she said scared me and excited me all at once. My cock responded also by leaking out more pre-cum. Could my sister be suggesting what I thought: fuck each other? I didn't know what to think. My head was spinning. My mind was racing again and I was hesitating.
My sister made even clearer what she wanted, "I want to taste that cock of yours and then I want to feel it inside of my dripping cunt."
I wasn't thinking straight. I was responding on pure desire. My hard-on was raging out of control. I was filled with lust.
"Are you sure?" I asked.
"Yes, I want it bad." She answered. She pulled the dress over my head and led me to the couch where I laid down. The pulled the panties off of me leaving me wearing the stockings, garter, bra and stilettos. My cock was throbbing now at full attention. My sister bent over and smelled the pre-cum soaked panties. "I need some of that cock!" she said.
She licked the head and tasted the pre-cum then licked my cock all the way down the shaft. I was on the brink of cumming. My cock was throbbing and swollen bigger than it had ever been. My hips began to quiver and my balls began to tighten. My sister knew I was about to cum and took be entirely into her mouth and began to suck and bounce her head up and down, slurping the head. I only lasted a few seconds before I exploded in my mouth. She kept sucking and stroking the shaft of my cock and massaging my balls with the other. I shot my load deep in her mouth and throat with my cock shooting over and over again. It was the most intense and longest orgasm of my life.
My sister licked up the last bit of my cum from the head of my cock and then moved and kissed me sharing the last bits of my cum with me. She thrust her tongue in my mouth one last time and squeezed against me.
"Too bad you didn't last longer." She whispered to me.
"Do you think I am done?" I asked.
She looked at me with a bit of surprise. She looked down at my still hard cock. It was a little less swollen but still rock hard and standing at attention.
"I hope you are ready, because I will be like this for a while." I said.
"You bet I am!" she squealed.
She pulled off her blouse and skirt and then her panties and bra. Her exposed breasts revealed fully erect nipples ready for attention.
I laid her back on the couch and began to suck and fondle her breasts and nipples. She immediately began to moan loudly with excitement and delight. She was squirming and guided my hand to her still wet cunt. I fondled her pussy lips with my fingernails and she started to arch her back in anticipation. I lightly touched her clit and she moaned deeply. She was ready to come. I kept one hand on her tit, caressing it and playing with her nipple and quickly moved down to give her cunt attention with my tongue.
I slid one finger in her hot, tight wet cunt and started to flick her clit with my tongue. She was moaning loudly and I could tell she was about to cum. I moved one finger gently to the opening of her ass and slid it in. her hips bucked up wildly and her thighs clamped on my head. I kept licking her clit and fingering her cunt and ass and came over and over. Her juices ran all over dripping down from her cunt to her ass and onto the couch.
When she finally recovered enough from her orgasms she demanded again, "I need that cock in me!" She was totally wild and uncontrolled at this point. I was just as hard as ever and the smell and taste of my sister's cunt had my dick swollen and throbbing again.
She grabbed my ass and pulled my hips towards her. Then she guided my cock into her dripping hole. She was incredibly tight but since she was so wet I slid right in. I slowly began to thrust my hips rocking back and forth penetrating her deeper and deeper. She began to raise her hips up again and shudder and my cock responded to her heightened arousal. She came first and the clenching of her cunt on my dick put me over the edge and I came again.
Her second set of orgasms seemed to last as long as the first set. My own orgasm was almost as strong as the first but still much stronger than any other I had ever experienced.
I lay on top of her deep in her pussy for several moments and then slowly pulled out. Her cunt was still twitching. Pulling out made me shudder again and squirt out a few more drops of cum on her.
She looked down and was amazed. My cock was still hard. "Do you think it will be like that much longer?" she asked.
"Why, do you have something else in mind?" I asked back.
"Yeah, I still have one hole which hasn't felt that cock yet." She replied. "I want you to fuck my ass."
"I still have enough in me to do that." I assured my sister.
"Good, then what are we waiting for?"
She slipped her fingers into her pussy, wet from her own juices as well as my cum and started to massage her ass hole. I did the same and spread some of it on my cock head also. She slid a pillow under her ass and raised her arms over her shoulders exposing her ass to me. I leaned over and gently pushed the head of my cock against the opening of her ass. My cock didn't slide in as easily as it did with her cunt but she relaxed her muscles and soon my dick slowly slid into her.
She let out a little gasp and I stopped.
"No! Don't stop, keep going." My sister demanded.
I resumed pushing my cock into my sister's ass and we both began to moan. I reached down with one hand and began to stroke her pussy lips and clit. With my other hand I was groping and teasing her tit. She began to moan faster and louder. I was slowly gliding my cock into her tight ass enjoying every second of it. This was the most excited I had ever been. Here I was wearing 4" stiletto heels, silky stockings with a garter belt and bra on, made up to look like a hot woman while thrusting my dick into my sister's ass. It was all so taboo and I was so turned on.
It didn't take long for either of us to cum again. This time I came first. The swelling and pulsing of my dick brought my sister over the edge again for the third time. Her ass clamped down so hard on my cock it almost felt like it would squeeze it off. It felt awesome.
After my sister calmed down some I pulled my cock out of her and lay down next to her. My cock was finally softening and getting smaller.
All she could do was gently whisper, "That was great. We have to do this again."
"Absolutely," was all I needed to reply.
