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Okay so, five years ago I got back into crossdressing, messaging men, and just generally being slut online. That isn’t the important part, my breaking point happened after a few weeks of being teased and shown dicks. I was salivating for a cock in my mouth, fantasizing night and day about having one inside my ass. Anyway, the frustration came with an inspiring, and absurdly stupid idea. I was gonna go out.
I got dressed up, purple plaid skirt, a cute tank top, lipstick to match the skirt, and a pair of short heels, what I wasn’t wearing were panties. I had pulled the skirt up high as well so that when I walked the bottoms of my ass cheeks could be seen. I made a little sticky note with instructions, bought enough condoms earlier in the day to fill a small jar, and grabbed a pair of handcuffs (the real kind that used for my job at the time) and the key. I left the house at night, jar, sticky note and cuffs in hand and walked the number of blocks to a nearby park.
I walked along until I found a bench on the main path, set the jar down, taped the key to the small of my back and the sticky note above it. I bent over the bench, and hand cuffed myself to the bench. The way I’d pulled the skirt up made it so my ass was fully exposed when I bent over. The note said simply: “Free fuck, use condom, free me and get a bareback bj.”
And I waited.
The first guy who came across me said “what the fuck?” Got closer. Said,” oh fuck yes.” He slapped my ass put a condom on after stoking himself for a bit, then slid inside me. He finished quick, made my dangling cock drool then slapped the spent condom on my ass. This followed eleven more times. Eleven more men entered me, fucked me, and slapped the spent condom on my back or ass, or just oulled it off and came directly on my parted cheeks or balls. Some stayed closed others made a mess of my tank top and skirt.
I came twice, milky, running squirts that spattered my thighs and the bench. By the eighth guy my legs had given out and the bench was holding me up, my legs dangling. Lucky number thirteen came up, said “shit he was right.” I assume one of my earlier customers had told him. He came around was probably late twenties, had a beard, kind of a gut. Anyway he pulled the key off my back and uncuffed me. I looked up at him and true to my words on the note I started undoing his jeans and took his soft cock into my mouth. He moaned and called me a good slut. He hardened in my mouth (love that feeling) and I deep throated him. He lasted maybe two minutes before he came in my mouth. I showed him his semen in my mouth then swallowed. I said thank you, gathered up my half full jar of condoms, the cuffs and key, and walked the long blocks back to my house, legs shaking. Cars that passed me honked probably noticing i was covered in semen on my back. I made it home and nearly passed out from how tired i was but managed to get through a shower and then bed. I smiled though cause I had a warm treat in my tummy.
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