Alex, The Closet Sissy

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A short sissy story.
966 words
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My name is Alex, a closet crossdresser. 18 years old, never had a date. Too skinny, too weird, too feminine. I wore my hair long but not a hair on my body tho, not very athletic. Just a 5'3" skinny 125lb pale white boy with long black hair. Who loves dressing like a girl every since my older sister, Sam, moved out 1 years ago which left her old room unsupervised. I'm not transgender, but I am a Sissy tho, I just love the feeling of women clothing on me. I been aroused by girl's clothes & the role they played in porn for as long as I could remember. Ever since she left every chance I got I would slip into Sam's room and try on some of the sexy outfits she owned. Anything to feel so complete and sexy. I longed to wear skirts, dresses, stockings, bras, panties and heels. The panties were my favorite tho especially with my very feminine body, cause for a skinny boy. I had a very nice bubble butt.

People have often mistaken me for my sister, since we kinda looked the same, with the same petite pale body. She was flat chested with a cute booty, like me. She was the small slutty girl in school, especially her senior year, she always had different guys at the house on the weekends when my parents left. I didn't know if she thought I was asleep or if she didn't care but all weekend long I could hear her moaning & screaming. Being the young dirty boy I am & was, I would jerk my small 3" cock to the sounds of her getting fucked till I cummed all over myself. But I wasn't jacking off to the thought of my sister but to the thought of me taking her place. The way she screamed for the cock, was a feeling I always wanted to feel. The same when I watched porn, my eyes were always fixed on the cock. The big, juicy, cock. I just wanted a taste it & to feel like a slut. So, once my sister moved out.. I started raiding her room. Dressing & fucking myself every chance I get.

This particular day was like any other day for me. My parents were gone on a trip for the weekend, like always. It was Friday morning mid-summer. I had nothing to do & nothing planned. So, I walked in my sister light pink room, with posters of hot muscular MEN & boy band all over the wall. She left everything since she was spoiled & was gonna buy everything new for college. She left her clothes, makeup & a nice dildo that I called "Big Daddy", I found in a box hidden in her closet. It was 9" realistic black dildo with a suction cup. So, I picked out my favorite outfit and feminine transformation began with undressing completely from my boy clothes and then slipping on into a pink lace thong, being especially careful to tuck my small cock back between my legs. A tight pink tank top that i found said "cum slut" huge in the middle of it, hugged my chest while leaving my mid-riff exposed. Following that, I found a mini blue jean skirt. The skirt was small that you could see almost half of my pale bubble butt. Long thigh high white socks with 3 pink stripes, ended with some slutty pink heels. Put my hair in pigtails & applied a heavy coating of pink glitter lip gloss.

I looked like such a slutty tease, walking around my sister room. Taking pictures & being such a sissy. Until I couldn't wait anymore, I pulled "big daddy" out the box & suction "daddy" right to the wooden floor. Lubed it up & pulled up my skirt & moved my pink thong to the side, squatting right over it. I worked that cock head into my waiting pink boypussy! I moaned & screamed in ecstacy as I slid down that big 9 inch cock! I raised up and lowered myself onto "big daddy" again & again, moaning even louder! I was loving being a cock slut! I had been waiting all day for this. I pulled my small hard cock from my panties and let it flop as I bounced on "big daddy" & feeling the balls of the dildo hit my ass and my boypussy stretched to a delight. I was in ecstasy bouncing on it, wishing it was a real cock.

Finally, I removed the skirt, left the pink thong on & laid on my back, throw my heeled feet in the air behind my head. So, in this position allow my small hard cock to hang right over my face. With my thong pulled to the side, it left my pink opened soft boypussy exposed in the air. I slid the dildo back in me & pounded the dildo into me hard, and fast. Trying to get me to explode cum all over my face and into my mouth. So, just as I gave the "big daddy" the final thrusts into my ass, my own cock exploded in a rush of moans and dirty talk, "Fuck me with that big black cock! Fuck my ass! Cum on my face! Give me that juicy cum! Shoot that cum in my mouth! I want to taste your cum!" And I did, I cummed everywhere, all over my lips and in my mouth. I quickly swallowed my juicy cum & stayed in the same position with "big daddy" still balls deep in me. I was in so much ecstasy, I officially became a cum slut. I loved it, the taste and the feeling. Just missing, a real cock. Maybe next time... ;)

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5 Comments
AnonymousAnonymousabout 5 years ago
Nice Story

I loved the BBC Dildo, just needs to be caught by his sister and her big black boyfriend, or his dad and his dog. Also needs some Bdsm.

AnonymousAnonymousabout 5 years ago
Great Story

This could be the beginning to a great story. Especially when you get caught by your sister and she agrees to help transform you!! But, seriously, your english needs some work. Good luck and I look forward to reading more.

AnonymousAnonymousabout 5 years ago
Can relate

I had two older sisters when they both moved out I was free to indulge in my feminine world. When my parents would would take a vacation, I would stock up on my feminine hygiene needs and clothes. I would call in sick either on a Friday or Monday and be dressed all weekend. If it was On a Friday I would be hairless by Friday morning. Thursday evening I would have cleansed myself out. One Friday I was completely dressed as a woman and my older sister stop by to check on me as she knew I called in sick. After knocking on the screen door she was heading back to her car as I said hello, she turned and looked me got in her car and left. She came back about thirty minutes later and ashed if I wanted to talk I said I did. But when I said can we have a woman to woman talk she said we can never have a woman to woman talk and I said a woman to whatever than. She asked how I knew what sizes to get I said I looked in the catalogs for how to measure for my size. I would go to the store and get what size I needed. What I really wanted was for her to take me out dressed as a woman but that never happened..

PijaconchaPijaconchaabout 5 years ago
Sexy story

Too bad a male friend didn’t catch you, take over and make you suck him dry. Please continue his journey...

AnonymousAnonymousabout 5 years ago
torn

I'm torn. I want to say I liked it, but I can't because I'm crying about how poorly educated people are. This story is good, but the telling of it is awful. Constant changes of tense, horrible confusions of plural and singular.

For instance: "Who loves dressing like a girl every since my older sister, Sam, moved out 1 years ago which left her old room unsupervised." It's not even a complete sentence. Should be ... ever since ..., not ... every since ... One year is singular, not plural, should be one year, not 1 years.

And that's just one sentence in the first paragraph.

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