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Crossdressing for my friend

663 words | 14 |4.33
By

Dressing up to be my younger friends ‘sister’

I was about 19 at the time. My friend was barely 16. I’m 5’9″, 130 lbs, brown hair and blue eyes, hair was slightly longer then. C was 5’5″, brown hair and brown eyes, about 145 lbs, and BIG at about 9 inches hard (love that is true too!). He had asked me if I really crossdress, and I told him yes. I had sucked him off for his them girlfriend before. So he asked to come over and play.
I was fairly nervous, I hadn’t dressed up for anyone before but I was also excited. He got to my house and waited outside my door well I changed. Nice white mini skirt and a white tank top. Pink bra to make it look like I had a chest. Tiny little SpongeBob panties to make it more kinky. Blue thigh highs and done blank wedge sandals.
I sprayed on some perfume and called him in.
C- hey. You look good.
Smiling I waved him over and crossed my legs on the bed. He say next to me and I kissed him. “Thanks…”
He was already hard and I loved that. Kissing him again I rubbed his cock through his pants well he groped my ass. He tried taking control, pushing me into my back. I grinned and took one show off, rubbing my silky covered foot over his cock. He took my other shoe off.
Watching him he kissed the sole of my foot and closed his eyes, sucking my toes. I was hard and panting in my tiny skirt. Pulling him up I kissed him again, pulling him over me and kissing his ear I whispered into his ear. “Take my skirt off baby boy.”
I have never been undressed so fast before! He only took the skirt off and was kissing me again well I stripped him naked. He was soon naked on top of me, hard cock dripping pre onto my belly. Wrapping one hard around his cock he lifted my shirt and bra and kissed and licked my nipples, making me moan.
After a few minutes I kissed him and nibbled his ear, grinding against him I rolled us over and grinned down at him. He played with my cock a little but this time? This time was about him. Holding his cock up I pulled my panties to the side and rubbed him over my asshole. I got the flavored lube and put some banana lube on his cock before slowly kissing down his body. I admit, I couldn’t deep throat him. I tried though.
Looking up at him I kissed and licked the head of his cock before sucking it into my warm, wet mouth. Flicking my tongue around the head. He grabbed my hair and pushed down, forcing me to gag and drool. He didn’t stop though, he kept moaning and whispering “that feels so good big sis!”
I was ready to cum! Pulling off I straddled him and aimed his cock at my tight little asshole. Slowly sucking down I moaned like a girl, hands on his chest, my cock slapping his belly. I rode him slow, bouncing and whimpering. He stretched me so good~
Kissing him I rolled my hips and rubbed my cock, kissing his neck, his ears, his jaw. He moaned he was about to cum. Forcing my way down I moaned for him to cum in his big sister~
He came so hard, holding my hips against him as I came on his belly and chest. Slowly lifting off I groaned and made him suck my cock clean before feeding him my cum, scooping it off his body and having him suck my fingers. The panties were slowly getting stained with his cum leaking from my hole.

This is all true, and we played often if you want to hear more. I have a SC if you want to talk more. My SC is ablack756
Tell me your age and that you liked my crossdressing story.

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14 Comments

  • Reply PansyMalcolm ID:4173w6rlt09

    Mmmm love it. I am a closet CD and have had several illicit meeting where I dress for random men, playing the ‘girl’ and getting a hole full of semen

  • Reply [email protected] ID:1eb5z42y4fwx

    I love dressing up and being used as a fucktoy for men.

  • Reply Candy ID:4tamr8m

    Love it! If anyone wants to say hello I’m [email protected]

    • Dani ID:3tlqguykt0b

      Hi there.

    • Dani ID:3tlqguykt0b

      I need your cock in my ass

  • Reply Want More ID:99wekc4z

    Love to hear more

  • Reply BlackHart ID:2bgoti1ghj

    Post more stories! I cross dress all the time!

    • Dani ID:3tlqguykt0b

      Bet your hot.

    • Dani ID:3tlqguykt0b

      Bet your sexy

    • Dani ID:3tlqguykt0b

      I want to lick your man pussy

  • Reply Danny ID:3057hz2fii

    Hot

    • Greasemagnet ID:8bw8pby20d

      I love dress up in my French maids outfit. White stockings and suspenders but no knickers so my friend gets a good view of my sissy pussy and cock every time I bend over while he sits there naked with hard cock ordering me around.
      Then he will tell me to bend over the table and lift my dress,exposing my pussy..I feel him spread my ass cheeks then feel his hard cock pushing into my pussy.

    • Undefined in VA ID:7zv2v71m9j

      I and 4 of my buds have a poker night (we call it investment planning) every Thursday night. As entertainment there will be 1 or 2 teen boys (12 and 14) dressed in short skirts serving snacks and drinks. Half way through the evening cards are forgotten and we stretch boy pussy and play with boy clits. Personally I love spit roasting that 12 yo … gives damned good head. His dad taught him well!

      undefined804 on Wickr

    • Ablack756 ID:fx7ith209

      Glad you thought so hun. Should I post a part 2? We’re I fucked him?