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Halloween Handjob

Posted by: Author: Age: 19 Posted on: 8 comments
8 likes 11408 views Category: Masturbation Male-Male Tags: dress up, hooker, paid, brother sister, blowjob, halloween

Last Halloween I was trying to think of what to dress up as when Mom suggested I dress as a hooker. She had a grin on her face, knowing the idea would embarrass me and I'd never do it. She loves doing that. Anyway, I thought what the hell, I'll do it, so I told her it's a great idea but what can I wear. She goes to her room and brings me a white corset, old-fashioned looking, the type with whalebone in. She also gave me a pair of white stockings and a pair of tiny white panties. Wear these! she tells me. When I see what she wants me to wear I'm embarrassed. Am I daring enough to wear such an outfit? I ask about shoes, she says her feet are too small but she can borrow some from a friend who has quite big feet. She calls her and I hear her say she wants to borrow some shoes, "the sluttiest you got". Anyway, she brings the shoes round and my outfit is complete. That evening I put on my hooker outfit. Mom helps to lace up the corset, quite tight but not too restricting. My hairs fairly long so she goes crazy with the hairspray, giving me 'hooker hair', then uses her makeup on me and finally makes me wear false nails and then tells me I'm all set to walk the streets. Anyway, we go out, meet up with a few friends and start to do the whole halloween thing, but I'm walking quite slowly in the six-inch stripper heels she borrowed for me and I get left behind, then a car stops alongside. "How much for a handjob?" At this point in time I'm feeling so very horny because of the tightness of the corset and the feel of the stockings and shoes and I get kind of carried away, enjoying the role, and I tell him "30 bucks". I'd no idea how much a handjob costs and in hindsight probably sold myself too cheap. Anyway, he slides into the back seat and opens the door and tells me to get in. So, we're in the back seat and I figure I'd better do something so I start to unfasten the guys pants. He sees I'm having trouble with my long nails and apologises and starts to unfasten his pants. Before no time, he's naked from the waist down and I'm face to face with his cock. I pause nervously then I put out a hand and carefully hold it, then grasp it a bit more firmly and start slowly jacking him off. Obviously when I jack myself off the angle is different so it's a bit awkward at first but I soon get a feel for it. It's quite a large cock, larger than mine, I estimated about nine inches. He's grunting his approval as I'm slowly stroking his cock, gradually picking up speed. My face is quite close and for some reason I get the urge to lick it, so as my hand is masturbating him I flick out my tongue against his cockhead. I'm really getting into this, I quite surprise myself when I realise I'm enjoying it. At this moment in time I'm in quite a position of power, existing solely for his pleasure, to make him cum. At this moment in time his cock is my whole world, I exist only to pleasure him. My hand is stroking his cock, slower now because I wanna make this last, I'm enjoying it too much. I continue to slowly masturbate him with my right hand, my left hand on his thigh to steady myself, my tongue flicking at his cockhead. I already tasted his precum as I continue to stroke away at his long shaft when he grunts that he's gonna cum. Suddenly panic floods over me. He's gonna cum on my corset and Mom's gonna see it and she's sure to ask questions. I wrap my lips around the head of his cock as I continue to slowly jack him off until suddenly I feel a hot feeling in my mouth as he starts to cum. I continue stroking his cock, milking him into my mouth. I have to swallow it all, I think to myself, I can't get any cum on myself. Load after load of his cum seems to fill my mouth as I masturbate him, stroke after stroke, he fills my mouth. I keep going, determined to get every drop, then when I'm sure I've got every drop I stop, licking the head of his cock one last time. He thanks me and pays me my $30 and I get out of the car and he drives off. It'll be Halloween again soon and I really wanna dress as a hooker again. Do you think I should? What if Mom asks why? Maybe I should tell her what I did last year.

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