Halloween Dress-up

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sirhugs
sirhugs
2,465 Followers

"Would you rather I just fuck you right here?" she growled. "Should I pull your clothes down and slide my cock inside you?"

As perverse as it was, Sally's conduct sent shivers down my spine. I managed to shake my head, and to take each succeeding step more quickly until I was finally moving fast enough that my arms were stretched out far enough behind me that Sally's cock was not bumping me each time I climbed.

"That's it, girly, shake that ass," Sally taunted me as I wriggled away, ever upwards. I was amazed to notice that my cock, rather than fading from disgust, was bobbling excitedly.

I stumbled where the curve of the stairs shifted to the right, my nose ending up buried in the carpet, my body stretched out. Sally took advantage of the moment and pressed her entire body against mine from behind. She shoved her cock hard into the crevice of my ass, though my briefs prevented her from penetrating. Her breath warmed my neck, and then her moustache ticked my lobe as her tongue teased inside the ear. I tried to relax and just enjoy the pleasant parts, especially her heavy tits mashed against my back, although the layers of clothing diminished that sensation.

"I think your ass likes my cock," Sally whispered. Until she said that, I had not been aware that my hips were indeed humping up off the stairs, meeting her thrusts.

"We better get you dressed before your treat," she finally said, pulling back and roughly hauling me upright. I had always known Sally wasn't a small girl – her self-consciousness about her body was a reason she never dated- but her strength amazed me. This time, I needed no urging to climb as fast as I could up the rest of the stairs.

Once we reached the landing, Sally deftly untied my hands and without a word propelled me into her bedroom. Which was right in front of us. She slammed the door behind me. Through the oak, I heard her say, "I'll wait out here until you are properly dolled up."

The first thing I noticed was the outfit she had laid out fir me on the bed. It was a maid's uniform, in just the right classic cut and style to match Sally's gentleman butler- a soft dark fabric with a white collar cut in an only modestly revealing "V", and a knee length skirt. Much more the "Gosford Park" look than like a xxx movie French Maid.

Beside the dress lay a strapless white lace bra and a matching pair of boy cut lace panties. "The panties are my stepmonster's...I thought hers might fit you better. Neither of you has any hips." Sally's deep tones rumbled through the closed door.

Black stockings and a garter belt were also ready.

I wondered for a second about the bra, and then saw the box of tissues perched beside the ensemble on the bed. I had never realized until now that my best friend's tits likely made her chest the same size as mine.

A floral scent was wafting out of the en suite bathroom. I stepped over and saw that Sally had run a tub full of lavender bubbles. A razor sat on the shelf beside the old fashioned claw foot tub. I understood what I needed to do to wear the stockings. I quickly discarded the rest of my clothes and climbed into the warm water, enjoying the bubbles tickling my nose. I felt like a kid again. For a second, I wished that Sally and I were both four so that we could share the tub. Then my throbbing balls reminded me that sharing the tub with Sally all grown up would be much more fun. After we finished our treats, she likely would need another bath herself, and I planned to do my best to share it, although I realized that meant submitting to her will.

A handy body sponge sat by the razor on the shelf. I soaked it in the foam. As I coated my body with soapy suds, I admired my own hard nipples bobbing at the surface. By concentrating on them, I was able just barely to rest stroking my cock. I knew even a modest touch might make my load explode out of the aching tip of my head. Sally would not like that.

I lifted each leg out of the water, drizzling suds down the inside of my calves, letting the moisture trickle down between my thighs. This just forced me to look at my throbbing hardness. It looked larger than ever, perhaps a trick of the candlelit bathroom filled with mirrors. I risked brushing the underside of my manhood, fondling the soft flap of skin which linked the mushroom to the shaft. As my fingers rose up around the head, I detected a thin coating of precum leaking out.

"Don't take all night, sissy, or I'll be forced to come in there after you," Sally shouted in her deep voice.

I wished suddenly that I really was a girl, that I could pinch my nipples and pet my pussy until I climaxed, and still be able to recover and share sex with my master Sally. I slowly caressed my nipples, pretending that I had soft breasts, kneading my chest. In a trance, I lifted my right leg up onto the edge of the tub. Before reaching for the razor, I slipped my left hand along my side, caressing my body. My bum lifted up off the porcelain as my fingers curled around beneath me.

My finger slid into my anus, piercing the sphincter ring with ease. I had never stimulated myself there before, but perhaps because of Sally's playfulness it seemed so natural. My cockhead bobbed above the surface of the water and a few drops of cum spurted out. I decided to hold off and focused on shaving my legs smooth enough to please Sally.

Shaving my legs was not really very hard. The soap bubbles sufficed nicely to make the razor slide in even strokes up my skin. I was not very hairy to start with, so the tougher spots like knees and ankles were already pretty bare. I did get one tiny nick on my right shin, but otherwise, the work proceeded quickly.

"Don't forget to shave your groin as well," Sally shouted through the door.

This was tougher. My pubic hair was dense, and curly, and seemed to merge with the fuzz on my thighs and belly. I had to carefully lift my throbbing shaft up and away from my scrotum. If I wasn't careful, the handling itself would cause my load to erupt, thus frustrating Sally.

As I gingerly eased the blade along my taut ball sac, Sally spoke again, "I'd come in and do it for you, but I want to see you all dressed up."

I finished up by carefully trimming the hairs off my perineum, the little stretch of skin between my balls and ass.

"I'm as soft and smooth as a baby's bottom," I told Sally.

"Then dry off. Use lots of powder, so that the clothing slides easily."

"What if I don't know how to put the things on?"

"Just try."

"Aren't you the 'there is no try, just do' Yoda chick?"

Sally laughed in her normal manner, briefly reminding me of my gal pal. "They were sold out of that costume."

The fluffy white towel was soft against my skin, but pearls of semen sprayed across its surface as I fondled my balls in folds of cotton. Satisfied that I was dry, I looked around the bathroom, only to discover that the single tin of powder was lilac scented. I hesitated, but I decided I had gone too far to disappoint Sally now. I sprinkled trails along my arms and rubbed it on my legs and chest. I was careful to coat my scrotum and cock without trigger an orgasm.

"I don't hear fabric shimmying onto you tender young body," Sally called through the door, resuming her gruff manly tone.

As I moved into the bedroom, I noticed a bottle of brandy set on the dresser, with a small glass. I quickly downed a shot to fortify my courage. I liked it so much I had another, and then another.

"Us girls prefer crème de menthe," I giggled, warming to my role.

"Hurry."

I decided to start with the panties. They slid on easily, just like briefs, though my engorged cock could not fit in any way I tried. I did not attempt any more because my balls were drawing up inside my body, and the pressure in my shaft was threatening to burst. I just left the cockhead poking out of the waistband, which sank down to just above my balls.

The bra was next. I had never put one on, of course, but had seen it done in the movies. I fumbled only briefly with the clasp. Since the cups were empty, it was not difficult to fasten the garment below my nipples. I struggled a bit with the straps, but wormed them over my shoulders more easily than I expected. A few handfuls of tissue and I was ready to admire myself in the mirror.

Once glance told me that I looked fine for the current game, but that if Sally intended to take me out to Chad's party, she better help me put some makeup on.

"Don't forget, I like full firm tits," Sally called through the door.

I took her hint and doubled the stuffing in the bra. I then took a few extra minutes to shape and shift the mounds, so no tufts stuck out the top, but the curve, I hoped would look natural. In order to check, I slipped the dress on, despite not having put on the stockings. Although the fake cleavage had no nerve endings, adjusting my tits sent shivers through my body. I noted that the look of the dress was ruined by the tenting action of my erection. No matter how I waggled that, I just got more excited. If I kept going, I would surely stain the fabric.

I sat on the edge of the bed and tried to figure out the garter belt, but no matter which way I looked at it, I knew I could never get it on. Around one thigh, maybe.

"If the garter belt is a problem, don't worry, those are stay up stockings- Lycra is a wonderful thing," Sally said.

I tentatively rolled a stocking up my left leg. As the strangeness faded the softness of the silk sent shivers again up my spine. With my smooth legs well shaved, I now understood how dressing up made girls feel special.

"Are you ready?" Sally grumped from outside the room.

I knew that just a Sally's moustache made her costume real, I needed a crowning touch. Sure enough, Sally had thought of everything. A blonde wig and a lacy maid's cap were neatly displayed on a vanity. I took a moment to settle these in place over my short hair, pausing only long enough to adjust the curls falling across my forehead.

"Come and get your treat," I trilled, pitching my voice into a falsetto. I sprawled across the bed, one elbow propping me up, my legs crossed daintily, but my left leg crooked so that my skirt slid above the knee.

Sally burst through the door, every inch the butler, and stood, hands on hips, admiring me. I know I blushed as she smiled.

"You are a beautiful girl, but that lump under your dress has to go."

With no further fanfare, Sally dropped to her knees at the end of the bed and flipped the skirt up above my waist. My cock surged vertically, despite the chilly air. It was fully exposed. Sally grasped the base firmly in her fingers and turned it about, admiring it. "This is beautiful too," she said, still using her mannish voice.

The deep growl and the visual of the moustache hovering inches above my slit were odd, but the gentle pumping action of Sally's hand prevented any loss of erection. A few beads of cum tentatively spurted out of my cockhead, the rest restrained by Sally's grip.

"I've always wanted to taste this," she said. She inched forward and lowered her head slowly, just barely flicking her tongue across the tip of my helmet, licking up the goo, and looked up smiling. Her teeth glinted with pearls of cum. The gob stuck in her whiskers made my squirm a bit. She rewarded me by giving my cock a rough squeeze.

"Lay still and let me eat your overgrown clit," Sally demanded.

I relaxed again; falling back on the mattress as she ran her tongue around the rim of my cock, then licked the whole head like an ice cream cone. She cleaned all of the precum off of it.

Despite Sally's instructions, my hips had a mind of their own. They began bucking up off the bed, meeting Sally's lips, fucking her face. After the first few strokes, I no longer noticed the whiskers tickling.

"Bad girl, getting so horny so fast," Sally said as she lifted her head.

She reached over and slipped her hand under the edge of the top of the dress. She gave my nipple a twist until I yelped. Before I could respond, she again lowered her head over my cock, bobbing up and down the shaft with increasing speed. Her grip on my root never relaxed, so my sperm was trapped, urgently demanding an exit.

"Have you ever done this before?" I asked, amazed that she was not gagging as my full length disappeared into her throat.

In response, she twisted her head to signal "no". The resulting tongue whipping action around my shaft made the tingles run from my nose to my toes. I reached out. With my right hand, I found Sally's left nipple under her shirt. I grasped my own left nipple, massaging them both in stereo.

Suddenly, Sally pulled back, a strand of cum forming a rope from my tip to her lips. Taking a fresh grip on my shaft, she pumped it harder, aiming the tip at her open throat. The first spurt of semen missed her mouth, striking her on the cheek, and getting caught in her moustache. Her tongue quickly flicked up to catch most of it. But I knew that as soon as she finished with my climax, she would expect me to groom her. I knew that's what maids are for.

Sally had found her aim, and the second blast rocketed up to the roof of her mouth and from my reclining position, I saw the slimy cream slip back into her waiting throat. She briefly closed her mouth and rolled a ball of the goo on her tongue. Once again grasping my still full cock tightly, she shoved forward and forced her lips onto mine, forcing my mouth open. She swapped the snowball into my mouth and waited until I swallowed.

"You are going to be a fine slut," she growled, "my slut."

Then she slid down my body and took my cock back into her mouth. Several more shots of cum erupted into her throat, each one swallowed as if Sally hadn't eaten in weeks. The final drops leaked from the corners of her mouth.

As my shaft softened on her tongue, Sally collapsed satiated to the floor. I decided to take a risk and act on my instincts. She did not complain as I followed, slipping off the bed to sit beside her. I carefully arranged the dress to cover my lap, and crossed my knees daintily. Gently, I took her chin in my hand turning her face towards me. She smiled dreamily. For the first time all night, I saw clearly my best pal behind the costume. I softly stroked the moustache with my finger tips, and then darted my tongue out, cleaning the bits of stray sperm. Sally shifted, and sucked my tongue deep into her mouth.

After moments which seemed to last forever, she broke the clench. "That's enough tricks out of you, girly," she said, bit she was unable to stay in character, her deep voice breaking into girlish giggles.

Her hand slid up my leg. "Oh, you're excited again already. We can't have you going to Chad's party like this."

She lifted her hips off the floor and struggled out of the trousers, her underwear slipping off with the pants. Bunching my dress up at my waist, she bunny hopped on top of my erection. My rod slid effortlessly into the depths of her pussy. Sally used her legs to pump herself up and down my cock as my hips again showed a life of their own.

I expected to encounter the resistance of a maidenhead, and paused in my response.

Sally again was way ahead of me. "I lost that flap playing with carrots a long time ago, honey," she giggled.

I felt like I was floating on a cloud, in heaven. The strangeness of our clothing no longer matter as Sally's fingers slid under us to milk my still swollen balls. My shaft throbbed, aching still from the last orgasm, but seeking more release. Sally's strong abdominal muscles began flexing in counter point to her up and down motion, wringing my cock. Shivers of excitement shot through my body with each twist. I seemed to drive up higher off the floor in response. Sally then in turn shoved down harder.

I worked a hand between the buttons of her shirt and found her tit, massaging the meat first, and then touching the nipple, gently at first and then with increasing intensity.

"Oh, gosh, that feels great," Sally moaned.

She reached out and grabbed my other hand, sliding it around her ass until my fingertip pierced her sphincter. Now, my cock was ramming her cunt and I was finger fucking her ass as we bounced along the hardwood floor. The deep my finger sunk, the more Sally creamed with joy.

While we fucked, Sally wrapped her fingers through my wig, and drew my lips to her mouth, kissing me deeply, sharing the remnants of my first load of cum. As we exploded in orgasm together, Sally held my face in her palms. I could feel her tears running down our faces.

As Sally collapsed to the floor, we heard distant church bells tolling midnight.

"I guess it's too late to go to Chad's party now, Halloween is over," Sally said.

"Happy Halloween" I replied. Although I had yet to achieve my goal of seeing her nipples, it was the best night of my life. As she snuggled against me, I asked "are you sad you missed the party?"

"No, I think my trick already earned me the best treat."

Just then we heard the door knocker.

"Trick or treat," we heard. The voices sounded like Raggedy Anne and Andy. Maybe they had figured a way past the gatehouse. Perhaps we would party after all.

"Look at you, you're a mess," Sally scolded me. "Straighten up while I go greet our guests."

sirhugs
sirhugs
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AnonymousAnonymous5 months ago

This is a totally amazing story and I definitely want to read more of your stories. Especially the next story that follows this one.

fd8984596fd89845969 months ago

That was certainly and exciting read!

Tx_twistTx_twistover 1 year ago

Thank you, loved the story. I've often dreamed of doing that with childhood neighbor girlfriend.

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