Dressing up

The couch, the television, the vanilla boy, I’m bored.

“I want to dress you up.” He looks over at me, then looks back at the television.

“Come on, it will be fun, we can put a dress on you…no, my skirt, the black mini. You will look sweet. And that cute top with the flowers…”

“Ssshhh…I’m trying to watch this.”

“… and stockings, my thigh highs… not sure my shoes will fit you though… maybe. And make up…’, I touch his lips, ‘… lipstick, eyeshadow, mascara for those beautiful lashes… you will be gorgeous…”

“Errmm… how about… no.”

I sidle up closer to him and touch his thigh, leaning into his ear, “…no? But really, it will be great fun, we can be girlfriends, it’ll be sweet… you will look beautiful…”

“Look, I really don’t want to, ok?”

“I will help you get undressed first…” I whisper in his ear as if I haven’t heard, and I touch him, undoing buttons and zippers as I talk about each article of clothing, “…your shirt first… then your jeans…”, he shifts a little at my fingertips on his fly, “… your boxers…”, and he eases his arse up off the couch towards me a little as I touch him, “… then when you are naked, I will dress you again… it will be fun, I promise…”

“No! Look, I’m trying to watch this…”

“… I’m thinking really red lipstick, that would be great, and that plum coloured eye shadow… your eyelashes are going to look amazing with mascara on…”

“Oh for fucks sake!”, he jumps to his feet and storms off towards the bedroom.

I watch him leave and sigh.

The couch, the television, I’m bored. The program finishes, another one starts. Bored.

I hear him come back into the lounge room and turn towards the sound with a scowl. I look at him and he blushes and does a kind of shuffle.

He is wearing my highest heels, awkwardly, they are too small, and his legs are encased in black stockings, his blonde hairs sticking out here and there. My black mini sits well on him, he is lean in the hips, I am stunned that it fits so well. He has on a pink shirt, stretched tight tight across his chest, unable to do up all the buttons, I see a black bra underneath. His lips are red, red red, and slightly smeared, his cheeks pink (with eyeshadow, I think), his eyelids have some colour I can’t quite make out, and his lashes, even from here, are luscious and thick with mascara.

I smile at him and he looks so shy and embarrassed I could throw him to the floor and fuck him right there. I go to him and put my arm around his waist and kiss him chastely on the cheek. My voice drops a tone and I feel a little silly as I put on a bit of a gruffness.

“C’mon in sweetie, I’m glad you could come over.”

He picks up my tone immediately, “Errrmmm, thanks for inviting me over,” he replies primly and allows himself to be led to the couch.

“You look beautiful,” I tell him as he sits down awkwardly, the skirt riding up his thighs.

I openly ogle his legs and he self consciously pulls the skirt down a little and looks at me accusingly. I stroke his stocking encased thigh and lean into him, my mouth at his ear.

“Your legs look very sexy,” I tell him, my hand sliding up under the skirt feeling stocking turn into skin.

He pushes my hand away, again gives me another accusing look and turns his face to the television.

I press in closer to him and try another tack, my fingers touching the buttons of his blouse, stroking his chest, playing at the top of his bra.

“I love this shirt,” I tell him, “but really, showing your bra like that is a little slutty.”

My fingers slide into his shirt and under the cup of the bra to find his nipple. He slaps my hand away.

“Stop that!… Please!”

I am starting to get turned on with this game he is playing with me because I can see how it will go and I already feel the aggression rising.

I turn his face to me by his chin, ‘What did you come here for if not for this?” I ask and shove my hand up his skirt.

He forcibly pushes my hand away, and tries to slide away from me.

“I came to watch TV with you, that’s all!” he shrieks.

“I don’t think so,” I reply, and lean into him and I kiss him.

His mouth answers me even as he tries to back away, and I grab his hair and hold his head still as I take his mouth. When I pull away, his lipstick is smeared all over his mouth. I wipe my mouth with the back of my hand.

“You come here dressed like a slut, what did you expect?” I hiss at him.

“You said I looked beautiful,” he says plaintively, convincingly.

“No, you look like a slut, look at you in that tiny skirt and your buttons half undone and too much makeup!” I snarl, “You want this!”

His eyes widen, “No!” he manages before my hands are all over him.

I’m undoing his shirt buttons and grabbing at his bra, lifting it up to get to his nipples, pinching them, and I straddle his lap in that tiny skirt and I can feel his hard on through it which is both obscene and sexy and I pull at his nipples and bite his neck and he is still protesting and ineffectually trying to stop me.

“Stop, please stop, I don’t want this!”

“Yes you do, you slutty bitch, I know you do!”

I slide back in his lap a bit so I can get my hand up his skirt and feel where the stockings stop and his skin begin, I feel lace and his cock sticking out of my panties and knowing he put my panties on is somehow incredibly hot and I try to shove the skirt up to his waist so I can get at him and he lifts his arse off the couch to let me.

I pause and look down at him under me and he is incredibly hot. His mouth smeared with lipstick, his eyes framed dark with mascara, his shirt half off, his bra pulled up to reveal his nipples, his skirt bunched around his waist, his lace panties pushed aside, his cock straining for attention.

I grab both his wrists and hold them behind his head, leaning into him, rubbing against his cock.

“Didn’t I tell you this would be fun?” I ask him.

He looks up at me and nods.

“Tell me you’re a slut,” I whisper in his ear, “Tell me you want this and I will give it to you.”

And he does, and I do.

Loves: 2
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  1. slutboi: You’re very welcome, glad you liked it. Oddly, I am not actually a fan of cross dressing, and that is one of the very few times I have done it. Of course the hotness is in the fact that he did it for me even though he didn’t want to.Ferns

  2. I’m not a fan of cross-dressing either – which is why this did it for me, too. He does it because he’s fascinated with the arousal it’s giving her . . .This reminds me of one of my earliest ever fantasies. For some reason, I just HAD to read this as though it happened in a sleazy motel room. The woman had to have cropped hair . . .Well, re him: you got the blond hair bit right. You must have read my mind. :-)The panties wouldn’t fit, of course – they’d be very, very tight!Yum, as always.xxxx

  3. anonymous xxxx: “He does it because he’s fascinated with the arousal it’s giving her”. Absolutely right – he did it to please me. Vanilla boys can be very accommodating like that. Sleazy motel and cropped hair huh? Interesting.And very very tight is ok, I can live with that…Ferns

  4. Mab: Thank you for back-reading and commenting on old stories.

    I completely understand your disinterest in cross dressing. The thing that works for me in dressing a boy is that incredibly sweet shy embarrassment, that change in demeanor – knowing he is mortified, but he does it anyway and then gets turned on despite his discomfort. It's a powerful mix.


  5. Amb: “damn, I'm not big on cross dressing either but this is hot. I love the game you two play.”

    I loved it also, and I totally agree… reluctant boy who does it anyway… hot hot hot!!


  6. Phoray

    “Of course the hotness is in the fact that he did it for me even though he didn't want to”

    I feel the same way about strap on sucking. A boy who doesn't resist either is not very hot to me at all.

  7. Phoray: “I feel the same way about strap on sucking. A boy who doesn't resist either is not very hot to me at all.”

    *smile* My last used to worry that he didn't resist things that I wanted, and that it would spoil it for me… It didn't. I am flexible like that.

    But this one, the vanilla boy, his resistance was just about perfect.


  8. I would be surprised if this one is still vanilla…

    mmmmmm having someone do anything for me that I know they don't really want to do just trips my trigger!

    Thanks for churning up an oldie but a goodie Phoray

  9. Sweets: “I would be surprised if this one is still vanilla…”

    *chuckle* Yes, I'm curious about that too. I had never heard of BDSM at this stage, so I'd have called myself vanilla also then (though I'd not have heard of the term 'vanilla' either… heh).

    “mmmmmm having someone do anything for me that I know they don't really want to do just trips my trigger! “

    Yes! “Good boy.” swoon


  10. Well, hello there, awkward boner. Never been turned on by cross dressing before. I think it has something to do with the woman “making” the guy do something that is a turn-on. The part about the woman being bored and wanting to use the boy for entertainment is pretty hot. Thank you for confusing me. :)

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