We had been texting for a few days following our date, even spending a few late nights sending erotic messages to each other. Jackson seemed desperate for another date and I couldn’t stop thinking about his cock.

I lay sprawled across the suede sofa in the front room playing with my hair, wearing a bra and thong, some shape pantyhose and a pair of six-inch black high heels. I’d become accustomed to wearing ladies’ clothes at all times and felt so natural in them now.

My phone flashed as a message from Jackson appeared on the screen. ‘Please, let’s just meet for coffee. I really want to see you again.’ I left it for an hour or so as not to seem too eager before texting back to arrange a time and place to meet.

I’d had my eye on a particular dress for a few days. It was a silk burgundy off the shoulder midi dress with a thigh-high split that hugged my figure tightly as I pulled it on and tugged it over my ass. I wriggled in front of the mirror to find the dress shape, noticing my tiny cock pressing against the material as I tucked it back into my panties.

I teetered around the room, striding and spinning in front of the mirror like a catwalk model as I admired how cute and sexy the dress looked. ‘You naughty girl,’ I said to myself, pushing my ass out and bending down to grab a small purse from the floor.

Feeling incredibly sexy, I touched up my lips with some gloss and blew myself a kiss before heading out of the house. When I arrived at the caf,e Jackson was already sitting waiting for me. His eyes lit up when I entered the room and he rushed over to kiss me on the cheek, asking what I’d like to drink.

After ordering, we found a table in a quiet corner and went to sit down. I crossed my legs slowly and seductively trying to tease him and gave him a flirtatious smile. He complimented my outfit and told me how beautiful I looked before asking me how I’d been. He listened intently, clearly trying to make an effort to show he was interested he was in me and not just my blow job skills.

Not much happened during our coffee, other than him being incredibly courteous. I was about to leave, bending down to grab my purse when he reached over and grabbed my hand softly, leaning in to whisper. “I want to make it up to you.” He said.

“Make up for what?” I asked, pretending not to know what he was referring to, which was clearly a reference to his premature ejaculation a few nights before.

“No one’s ever made me come that quick. I swear! It’s just, when I looked down and saw you, how sexy you looked and how good it felt, I just lost control.”

I didn’t reply and instead, just stared back at him, gesturing for him to continue.

“Is there any way I can make it up to you?” He pleaded, sincerity in his eyes.

 “Maybe,” I replied cheekily, sliding my foot between his legs and rubbing my heel against his crotch, his cock instantly hardening at my touch. “What are you willing to do?”

He paused, leaned in further and spoke softly, “anything you want, baby.”

I trembled at the thought, biting my bottom lip, a wicked smile crept across my face before responding. “Meet me at this address tonight.” His eyes widened and his cock stiffened as I passed him a note. Then I stood up, turned around and strutted out the cafe wiggling my ass as I left.

Back at the house, I stripped my dress off and began searching the wardrobe looking through Teresa’s sexy costumes. I wanted to wear something that would drive him crazy and make him beg for me. Teresa had accumulated a large collection of naughty outfits and there were too many to choose from.

She had a really sexy bunny outfit that consisted of a black corset with zipper closure and matching faux leather mini-skirt complete with cute bunny ears. I had worn this before, playing with myself and remembered how horny it had made me feel. I continued to search, finding a very cute and playful schoolgirl costume with black tie, crop top and plaid mini skirt.

‘No, not dirty enough.’ I thought, continuing to look, stopping abruptly at a skimpy garment that hung in the corner of the wardrobe. Sliding the other costumes across to get a better view my tiny clitty leaked into my silk panties as I pulled it out. Dangling from the hanger was a low-cut, strapless black faux leather mini-dress with lace-up detailing and garter straps.

I unhooked the lace and stepped inside the mini-dress, pulling it tightly up my smooth legs and over my ass, sucking in my stomach as it stretched over my chest. ‘Yes,’ I thought. ‘This is the one.’

After several minutes struggling to position my breast forms and tightening up the lace, I donned a long silky wig and clipped on some fishnet stockings. Looking down I realized my heels just didn’t work, kicking them off and slipping on some six-inch pointed stiletto thigh-high stretch boots.

‘You nasty bitch,’ I said to myself, spinning my hips as the faux leather squeaked. ‘I can’t meet him like this,’ I thought, reaching back inside the wardrobe to grab a long ladies’ overcoat that hid my outfit perfectly.

Before Jackson arrived, I cleaned up the room and packed a bag with some important items. I sat shaking on the bed. I was really nervous and went downstairs to find something to drink, drowning a few glasses of vodka to calm my nerves.

The room was set and I felt a little tipsy which was helping to calm me down when I heard a soft knocking at the door. I stood up in my boots and took several long strides over to the door, checking through the peephole. Jackson stood sheepishly on the other side of the door. He had made an effort, wearing a smart suit jacket over a crisp white shirt and black pants.

I opened the door and ushered him inside, quickly closing it behind him. We embraced and kissed softly as he held me tight in his arms. I began leading him up the stairs toward the bedroom, wiggling my ass as he followed closely behind. As we entered the room I pointed to a chair by the bed, ushering him to sit down and await further instruction.

“I have a few surprises tonight, but before we start I have something I want to ask. If this is going to happen, you have to do everything I say, no exceptions. Do you agree to follow my instructions?”

He nodded, “yes, definitely yes.”

“Good,” I said. “Now are you ready to make up for last time?”

He nodded again, “yes, baby, anything you want.”

I tip toed around the room, dimming the bedside lights then confidently strolled over to the chair. Standing in front of him, I slowly undid my coat, sliding it off my arms and dropping it onto the floor. His eyes went wild with lust and desire at the sight of my sexy outfit. “You like?” I said, with a wicked smile on my face.

He nodded and grinned stupidly as I walked passed him brushing my ass against his face. “Take your top off and give me your hands,” I said, gently pulling them behind the back of the chair. Inside the bag was a set of fluffy pink handcuffs that despite looking a little cute, were actually very sturdy. I took them out and secured them over his wrists, locking him to the chair.

As I wandered back around the chair I noticed a giant bulge growing between his legs, bending over and rubbing my ass against his crotch. I slid seductively onto the floor and turned around to unbuckle his belt, caressing him as I pulled off his shoes and pants.

Jackson sat in his briefs staring down at me, the shape of his huge cock clearly visible through his tiny whities. I wanted him so badly, peeling them off his legs and watching with lust as his cock sprung out and trembled in front of me. I arched my back and leaned in, running my tongue over his soft balls and sucking his testicles gently.

The faux leather creaked as I bent over, squeaking and stretching against my curvaceous ass as I licked around his foreskin, teasing the head of his penis with my tongue and stroking his shaft with my tiny hands. He was panting and moaning and I could tell he was getting excited, letting go quickly as I leaned back onto my legs.

“I know you want me,” I said. “But first I’m gonna tease you.” I stood up looking down at him, his fully erect penis trembling in the air as I began to dance seductively. “You want this ass don’t you?” I exclaimed, bending and shaking it in front of him. He nodded frantically, his eyes darting between my ass and face, not knowing where to look.

I was still worried about my tiny surprise that was starting to grow under my sexy thong. I didn’t know what he would say if he saw it and quickly moved behind him, reaching into the bag, pulling out a blindfold and tying it around his head. “Now I’m gonna fuck you Papi,” I whispered in his ear.

I grabbed a bottle of lube and squeezed some onto my fingers, rubbing it around my pretty pink hole. His whole body quivered and tensed when I added some lube onto the head of his cock, caressing his penis sensually. The mini dress was already inches above my ass as I slowly bent down, reverse cowgirl, pulling my thong further to the side and hovering over his writhing manhood.

Taking a deep breath, I reached down and held his cock between my legs, slowly lowering myself onto him as the tip pushed softly into my boy pussy. “Oh yes,” I cried out in a really girly moan. He groaned behind me, lifting his hips and pushing his cock in deeper, his face pressing against my back as he moaned.

I’d been fucking dildos for days, but nothing compared to the feeling of real cock. I lost control of my inhibitions and started riding him harder, taking him deeper with each bounce, screaming like a nasty slut. “Fuck me, Papi, mmm, yes. Fuck me with your big fat dick!” His groans became louder, pounding my ass with his pelvis from the chair.

“Oh shit, oh shit.” He mumbled, clearly enjoying the feeling.

As I pushed back against his crotch his cock began hitting my g-spot perfectly, inching me towards an orgasm. I heard him call out my name from behind, “Oh Melanie! You feel so fucking good.”

I could feel my tiny cock harden and press against the faux leather dress. A question popped inside my head once more as I arched my back, taking his whole length inside my tight boy pussy. ‘What would he say if he saw my tiny surprise?’ I thought.

Without warning, I felt a warm sensation inside my ass and his cock began twitching and convulsing against my g-spot, followed by the familiar sound of grunting coming from behind me.  

‘What the fuck?’ I thought. “Did you come?” I asked impatiently.

As I stood up slowly, his cock slid off and come dribbled out of my gaping hole and onto my stockings. “Really?” I murmured.

“I’m so sorry, baby,” he pleaded, “you just turn me on too much.”

“What happened?” I asked, desperately wanting to know the answer.

He paused and lowered his head. “I think it’s because of how naughty this all is.”

My heart raced and I felt a hot flush run over me. “What do you mean?” I asked nervously.

“Well, you know.” He said. “The thing that makes you different from other girls. The naughty thing we haven’t talked about but that makes it so much hotter.”

I panicked, wobbling in my heels as I freaked out, comforted only by the fact that he couldn’t see me through the blindfold. After a few awkward moments, I finally spoke. “Do you still like me?”

Without hesitation he replied. “Of course I do, can’t you tell! You turn me on so much. Please let me see you, baby,” he begged.

I rearranged my dress and walked over to the chair, slowly removing his blindfold and unlocking the handcuffs, before sitting down on the edge of the bed. Jackson slowly got off the chair and sat down next to me, gently putting his arm around me. “I really do like you,” he said in a comforting tone.

I looked up into his big brown eyes, in awe of his strong jawline, juicy lips and gorgeous smile that made my whole body tingle. He looked right back at me with a look of desire before he finally spoke. “Let’s make love again.”

Without hesitation we began kissing, our tongues lashing together as we passionately embraced. I felt Jackson’s rock hard cock rub against my legs as we fell back onto the bed, feeling him dry hump me through my mini dress.

“I want you!” He moaned, grabbing hold of my boots and lifting my legs into the air as he guided his huge dick in between my thighs. My tight dress lifted and bunched up around my waist, exposing my ass but still concealing my tiny cock.

I whimpered in pleasure as I felt his huge cock penetrate me once more. “Yes, Papi, fuck me deep. I wanna feel your balls touching my ass.” The bed rocked and creaked as he ploughed his cock into me, the clapping sound echoing around the room as his hips slapped against my ass.

Sweat dripped off his muscly arms and down his chest as he pounded my ass, pushing my legs back further. His eyes were wild as he continued ramming his cock deep inside me, fucking me like a wild animal. “Oh, Melanie!” He screamed, ramming his cock so deep I yelped in surprise.

The sensation sent enormous pleasures through my g-spot making me squeal and orgasm, filling the inside of my dress with hot sticky come. I looked up at Jackson as he pounded me and begged him, “come for me, Papi!”

He thrust a few more times before quickly pulling his cock out my gaping hole and spraying come all over me. Covering the dress and shooting a few shots up onto my chin and lips. He collapsed next to me and I cuddled up beside him, both of us completely exhausted by the frantic fucking.

Curled up together on the duvet, I lifted my head and softly asked, “I think I might need to get cleaned up, do you mind?” 

“No of course not. Do you want me to stay here or should I go?” He replied.

“No it’s fine, make yourself at home. Mi casa su casa.” I said. 

To be continued…

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com with this note attached, it has been posted without my permission.

<a href=”https://www.lushstories.com/stories/crossdressing/-house-sitting-for-the-holidays-part-1.aspx”> House Sitting For The Holidays (part three) </a>

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