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.