How did I end up in this position? This was the thought running through my head as I lay face down across the bed. My mind flashed back to the moment it all began. It was a beautiful Sunday morning with a cool springtime breeze blowing through the open window. I was cleaning the house. I hated cleaning, mostly because it is never fully done. No matter how much cleaning you do, there will always be more. I'd have much rather been out enjoying the nice spring day, but it had to be done. Then it happened, I found a pair of lacy blue panties, left behind by a recent one night stand, under the bed.

I rubbed the smooth fabric between my fingers and an idea popped into my head. Seconds later, I was pulling the tiny garment up my legs and luxuriating in the silky caress of women's panties on my genitals. Naturally, the panties were too small and they ripped a little as they stretched around my hips, but they felt so good, I was hard as steel immediately. I finished my housework with my swollen cock peeking out the top of the lace panties, then flopped on the freshly made bed and jerked myself to an explosive orgasm that covered my chest with hot cum. That was the beginning of my Sunday morning routine. The sexy feel of the panties and promise of a body shaking orgasm turned the drudgery of housework into foreplay.

Of course, after a few weeks those too small panties were in a sad shape, and if my newly discovered hobby were to continue, I needed a new pair, preferably in the right size. However, finding women's panties in my size proved a tougher task than first thought. That is until I discovered a site dedicated to crossdressers. I was a bit apprehensive about purchasing through the site, but they assured security and discretion so I entered my card number.

I had only intended to purchase a couple pairs of panties initially, but I had always loved women in stockings and grew hard as I wondered what it would be like to wear them. By the time I entered my credit card information, my order included six pairs of panties in various styles, two pairs of stockings, and a red silk camisole. I authorized payment and immediately started stroking my hard, leaking dick. For the next week I was in a constant state of arousal waiting for the order to arrive.

I came home on Friday and found a surprise waiting on my doorstep. I hadn't expected the shipment to arrive until Monday but was happily surprised to find the plain brown box waiting for me on Friday. I rushed inside, tearing the box open as I went. I pulled each item out of the box and laid it out on the bed, rubbing each silky smooth piece over my bare skin as I did. After a quick shower, I tried on all six pairs of panties, modeling each pair in the mirror.

Then it was time for the stockings. I was already hard and dripping when I sat down and slipped my foot into the first sheer black stocking. The feel of the stocking stretching around and sliding up my leg was indescribable. I almost had to stop and stroke my impossibly hard member before pulling the second one on. With stockings and panties in place, I slipped the cool silk camisole over my head and tugged it down around my torso, giving a soft moan at the silky embrace. I admired myself in the mirror, feeling sexy, and began stroking my slick member.

Every inch of my body was being caressed by soft silky sexy material and I was more turned on than I'd ever been. Far too soon, my thick shaft erupted spraying hot cum everywhere. My legs trembled and my body shook as I groaned. After cleaning up, and putting on fresh panties, I made myself some dinner, then crawled into bed and stroked myself to another powerful orgasm. I spent the whole weekend dressed in my new clothes and had too many orgasms to count.

Since that time, I have gotten out of bed every Sunday morning, taken a hot bath, then slipped into female attire, and cleaned my house top to bottom before stroking myself to orgasm. Over time, I added to my wardrobe with every sort of lingerie' available. My fetish has always been about the clothing and how it feels on my skin. I never wanted to feel like a woman or have a sexual experience with a man.

That is until a girlfriend asked if I'd ever had a prostate massage. I'd never heard the term before, and when she described it, I said absolutely not! But, after a little coercing and a promise that I'd love it, she had a small vibrator buried in my ass, driving me wild while she sucked my cock. The full body shaking orgasm that followed got me wondering if just maybe those gay fellas were on to something. Never ever had I imagined anal play could provide any kind of pleasure. Boy were my eyes, and ass, opened.

After that, I purchased a few anal toys and added them to my Sunday routine. I also started watching some crossdresser porn and fantasizing about being taken by a man while dressed as a woman. I loved the way the girls in the videos looked and started shaving my legs and pubic hair. Oh, my lingerie felt so much sexier on smooth bare skin. As excited as I got fantasizing about sucking big hard cocks and being fucked like a woman, it was just that, fantasy. I had no intention of making it happen.

That Sunday started the same as every other. I got out of bed, grabbed a cup of coffee and settled in to a nice hot perfumed bubble bath, soaking in the warmth as I shaved my body smooth. After my bath, I applied a generous amount of my favorite lilac scented lotion to my freshly shaved flesh. I slipped into my favorite pink and black lace panties and sheer black stockings and matching garter belt, and bra. Then, sitting before the mirror, I carefully applied my makeup.

I had only recently added makeup to my routine and used it sparingly, but the results were dramatic. I brushed out my long brown hair and selected a red silk blouse, short black skirt, and knee high, low heeled boots. I had a few pairs of heels but had not yet mastered the art of walking in them. I admired the results in the mirror. My short skirt left the tops of my stockings exposed and my blouse showed the cleavage created by my bra. The subtle touches of makeup gave my face a nice feminine look and I smacked my red painted lips at the slut staring back at me from the mirror.

Once dressed, I set about my cleaning duties with growing anticipation for my coming reward. I scrubbed the bathroom, mopped the kitchen and dusted the whole house, loving the feel of my short skirt swishing against my thighs and riding up to expose my panty covered ass whenever I bent over. I was just about done, with my hard cock poking out the waistband of my panties, and leaking profusely when, sensing something was amiss, I glanced out to the patio and started with horror. The moment I had always feared was suddenly at hand.

Standing there, on my back patio, staring open mouthed at me through the glass door, was my neighbor, Jack. I had lived across the street from Jack for five years and we were good friends, despite the difference in our ages. Jack was twenty years older than me, and retired, but we got along well and helped each other out often. I had been discovered! I stood, unable to move or react in any way as Jack glanced nervously about, then ran for the gate.

Panicking, I ran to the door and called after him. "Jack, wait!" I called.

Jack stopped with his hand on the gate, but did not turn around.

"Uh, sorry, I was just, ah... wondering if..." His voice trailed off.

"Jack, just let me explain," I pleaded, feeling ashamed that he couldn't even look at me.

"No, no need to explain, I shouldn't have come back here. I just thought maybe you were back here," he replied haltingly.

"It's okay, Jack, just come in and give me a chance to explain," I pleaded again.

Nodding, Jack slowly turned and walked toward me, his eyes glancing about nervously, unsure where to look. He followed me inside and I motioned for him to have a seat on the couch.

"I uh... didn't know you were ah... homosexual... " He began.

"Jack I'm not. I'm not gay, I just like the way the clothes feel. I just wear them around the house sometimes, when I'm feeling, ah, horny," I explained.

Jack furrowed his brow as he looked me over. "Well, why the makeup then?" He asked.

"Uh... well that's just...well it makes me feel sexier," I shrugged, my face turning red.

Jack gave a slight laugh and smiled a little. As he did, I noticed his gaze travel down between my legs and linger there. As I sat across from him, my short skirt had ridden up, exposing my black lace covered cock, which had shriveled upon being discovered. Jack's lingering gaze gave me a little thrill. I liked knowing a man was checking me out, it made me feel even sexier and my dick began swelling again.

"Well, I have to admit, you make a pretty good looking woman. I didn't realize it was you at first," he said, his eyes roaming down my stockinged legs and back up to my exposed panties.

I tugged at my skirt trying to hide the swelling in my panties.

"Well, thank you, kind sir," I batted my eyes at him, gathering from his joking manner that we were okay.

He laughed again and rose from his seat, "my pleasure ma'am. I'll let you get back to work then," he said.

I stood and crossed to him, "Jack, please don't tell anyone about this," I begged, placing a hand on his shoulder.

Jack turned and our eyes met, his musky scent filled my nostrils and I suddenly had an urge to kiss him.

"No, I won't tell any... hmm, you smell good," he replied, stepping closer and inhaling the sweet lilac scent of my body lotion.

His hand fell lightly on my hip as we stared into each other's eyes. His tongue flashed across his lips moistening them and he leaned in. Our lips touched, we just stood with lips touching briefly, before we both accepted what was happening and really kissed each other. It was so different from kissing a woman and I loved it.

Jack took me in his arms as I ran my fingers through his silver hair, pulling our hungry mouths together. His rough hands squeezed my ass as his tongue explored my mouth. Blood surged to my already stiff cock as Jack's bulge rubbed against me. Slipping my hand between our warm bodies, I caressed him through his pants. Jack moaned into my mouth and slipped both hands up under my skirt to knead my panty covered ass.

In that moment I was transformed, I wanted Jake to take me, to make me his woman. I wanted to worship his cock with my lips and tongue. I wanted Jack to make me feel like a sexy woman. Pulling my lips from his, I trailed my hands over his broad chest as I sank to my knees before him. I sucked at his growing bulge through his jeans while unbuckling his belt. Sitting back on my heels, I opened his jeans and tugged them down, along with his boxers, exposing his thick, semi hard, seven inch cock and big low hanging balls. Jack stared down into my eyes as I kissed and licked his wide mushroom head.

"Ohhh, good girl," he breathed.

A naughty thrill ran through me, both from his words and my first taste of cock. I inhaled his masculine scent and slid my lips over his thick knob. His warm member filled my mouth and my own cock throbbed in my panties. I had imagined sucking a cock many times, but the taste and feel were so different, and more intense than I ever imagined.

I pressed the spongy tip against the roof of my mouth with my tongue and moaned. It felt so natural having his cock growing hard in my mouth. I bobbed my head, sliding my hot lips up and down his pole. Jack's thick cock swelled to full hardness against my tongue, inflaming my desire and I pumped my mouth faster on his shaft. I took as much as I could without gagging. Jack moaned, placing a hand on my head and pushing his dick deeper in my mouth.

Pulling my mouth off Jack's warm cock, I sat back to admire his swollen member in its full glory. Jack stared down at me, mouth open and panting for breath. I smiled up at him as I lifted his stiff rod and leaned in to lick his heavy balls.

"Oh mmm," Jack grunted as I sucked one big testicle, then the other.

I lapped and sucked at his heavy balls before running my hot tongue up the underside of his thick shaft and sliding my lips over the swollen head. Slowly and deliberately, I slid my lips down his shaft swallowing as I went, trying to get the entire length in my mouth. Five or six attempts later, my lips briefly sealed around the base of his shaft before I had to pull back gasping for air. Jack let out a loud moan and placed his hands on either side of my face to pull me to my feet.

Grabbing my ass, he pulled my body against him. He kissed me hard as his hard cock ground against my own. Jack devoured my mouth and kneaded my smooth ass with his rough hands. My arms wound around him and stroked his back as he moved to kiss and bite my neck.

"Mmmm, take me to bed, Jack. I want you inside me," I breathed in his ear.

Jack looked at me with hunger in his eyes then led me to the bedroom. Turning me to face the bed, his hands massaged the small tits created by my bra as he kissed and nibbled my neck and shoulders. He gently pushed me forward, bending me over the bed. His rough hands moved to my ass. His fingers curled in my panties and tugged them down just below my smooth ass. I felt exposed and vulnerable as my smooth cheeks were pulled apart and a finger flicked over my puckered hole.

"Lube! Jack, use the lube on the nightstand!" I almost shouted in a panic.

I heard the cap pop and my entire body began to quiver with anticipation as cool lube drizzle on my virgin hole. Jack used his thick finger to smear the slick substance around my eager hole. Around and around it went, teasing me, then finally, slight pressure and my tight rosebud yielded to the penetrating digit. I had fingered myself numerous times before, but this was so different, so much better.

"Ohhh," I moaned, squeezing my ass around Jack's thick probing finger.

Jack pushed in and out varying his rhythm and making me squirm. He added more lube and stretched my tight entrance with a second finger. My eyes fluttered shut from the pleasure and I pushed back wanting more. Jack took his time preparing me, lubing me up and stretching my hole with a third thick finger. Digging deep until he found my prostate, making me moan with pleasure.

"That's my girl. You ready for me baby?" Jack asked, letting his fingers slip from my needy hole and sliding his hard cock between my cheeks.

"Yes, please fuck me," I answered, reaching back to hold my smooth cheeks open for him.

"Don't worry, sweetie, Daddy will take it slow," Jack's voice was a low growl.

He continued sliding his hard shaft through my crack and across my slick entrance. I pressed my face into the bed and pulled my cheeks wider.

"Please Jack, I need to feel you inside me," I begged.

Jack pressed his thick swollen tip to my tight pucker and began to push. My tight virgin ass began to stretch around his hard cock, and I thought, how did I end up in this position? Jack continued to press and I tried to relax, hoping it wouldn't hurt too much. I felt my hole stretching over the thick mushroom tip and just when I thought it was too much, it slipped past my tight ring causing me to moan.

"Ohhh, your pussy's tight," Jack said, leaning over me and kissing my shoulder.

Slowly and steadily, Jack pushed his thick cock into my tight ass, while kissing and nibbling my neck and shoulders. His cock was only slightly bigger than the dildo I normally used on myself, but the warm fleshy member felt so different from the cold latex. I pressed my face into the mattress and groaned loudly at the warm ripples spreading from my ass through my body. I felt Jack's pelvis against my ass and knew his full length was inside me.

I'm Jack's girl now, I thought, squeezing my ass around his thick knob and pushing back to grind against him.

"That's my good girl," he said, kissing my neck.

Just as slowly as he'd entered me, Jack withdrew, before slowly filling my ass with his hot hard cock once again. Once lodged fully in my tight hole again, he ground into me, sending tingling waves of pleasure from my ass throughout my trembling body. Several more long slow grinding strokes had me moaning and squirming on the bed, begging for more. Jack changed things up with several short rapid strokes that hammered my prostate, causing my own hard cock to erupt into the sheets beneath me. I screamed as my body shook in orgasm and Jack laid his full weight on me while continuing to pump and grind his thick cock in my tight hole.

I lay pinned under him, taking his cock and groaning with pleasure, knowing I was completely his. Jack's stamina was impressive and jolts of pleasure wracked my body as he rode my ass. If only I had known it would be this good, I'd have started fucking men years ago.

"Almost there baby, Daddy's got a present for you," Jack grunted as he pushed up off me and took hold of my hips. He began rapidly thrusting his full length into me with enough force to shake the whole bed. The sound of our bodies crashing together echoed around the room as he pounded my virgin ass.

"Mmmm hmmm, oh fuck, fuck me!" I panted.

"Oh yeah, that's my dirty girl," Jack grunted, driving harder into me.

His thick cock hammered my prostate with each forceful thrust and I gritted my teeth as the electric heat wracked my body.

"Oh, mmm, baby... " Jack moaned as steaming jets of cream coated my bowels.

"Oh, oh, god, mmm," I moaned at the feel of another man's hot cream filling my ass.

Jack's cock slowly deflated as he gave me a few more gentle strokes before collapsing on the bed beside me. He pulled me into his arms and we kissed softly as he held me.

"That's my good girl," he said, as we lay together.

He stroked my hair and promised he would be back next Sunday if I was a good girl. I don't know if I can wait that long, though.