I never wanted it to happen. Or at least I always thought I wanted to keep it a secret. I had always been fascinated by women's clothing, for as long as I can remember. One of my earliest memories is of, at the age of four or five, wearing a pair of thick, woollen tights from my dressing up box. I loved the way they made my legs feel and that stayed with me ever since.
Throughout my childhood and teenage years, I would, from time to time and when the opportunity arose, try on my mother's clothes, as so many other crossdressers must have done. I've never been more than a few inches taller than my mother, so her wardrobe was the perfect playground for me, despite her reserved and conservative dress sense. Even so, I loved to put on her raciest lace panties and matching bra along with a pair of tan nylon stockings and enjoy the mixed up feelings of terror and exhilaration.
Over the years I experimented and whenever I had more than an afternoon alone in the house, I would dress up fully as a woman. My favourite outfit was the tennis skirt and top my mother no longer wore. The short white skirt left me feeling sexy and exposed, while the tight vest top clung to my chest. After putting on lipstick, eyeliner and mascara my cock would soon be straining against my white cotton panties and begging for release.
Lying back on the bed, I would be transported to Nirvana as I lifted my skirt and pulled my panties to one side to release my hard cock. While my one hand would stroke my erection, my other would alternate between caressing my thigh and playing with my nipples. My inevitable release was always satisfying and I relished the drowsy feeling which came over me as I lay on the bed with my own cum slowly drying on my chest and tummy.
More than once I came close to being discovered as I lay dozing on my bed in a deeply compromising position, and I would have to dive into the bathroom and take a shower as my parents returned home. Frequently I would hide the clothes I had borrowed until I had an opportunity to return them, desperately hoping that their absence would not be noticed.
These close calls would often be followed by prolonged periods of guilt and self-loathing, in which I could refuse to acknowledge my needs and not indulge my desire to dress for months at a time. Soon, however, I would be back to dressing whenever and however I could.
My crossdressing really became serious once I left home to go to University. I was able to afford a small flat of my own and for the first time I was free to explore my feminine side without fear of discovery. My flat was on the second floor at the back of a modest block. The large windows in my bedroom come living space overlooked a pretty little park, while on the opposite side of the park there was a taller block of flats.
After a few weeks settling in to my new home, I launched myself into creating my first female wardrobe from scratch. I made most of my purchase online through Ebay because I was too scared to even consider walking into a high street shop to buy women's clothes. I did, however, get up the courage to buy stockings and tights with my grocery shopping, reasoning that the cashier would assume I was picking them up for my imaginary girlfriend.
I had soon amassed a collection of clothes which I could only have dreamt of before. These ranged from the classy and sexy like my tight black pencil skirt and a gorgeous red halterneck minidress to the down right slutty and trashy like a hot pink micro mini skirt which barely covered my bum and a selection of naughty lingerie any hooker would have been proud to call her own. I also bought my own makeup and two wigs: one a short, blonde bob and the other and shoulder length auburn one with a slight wave to it.
Almost every spare minute I had was spent in my flat dressing up and sinking deeper and deeper into my feminine side. I was always careful to close my blinds before starting my transformation and would religiously tidy all signs of my other life away afterwards. I dressed entirely for my own pleasure and had no desires to share my fetish with anyone else or to leave the flat as a woman. Although dressing turned me on no end, I had no delusions that I made a convincing woman and so saw only the potential for humiliation and ridicule beyond my own door.
Unbeknownst to me, however, my other life was soon to spiral out of control and to change in ways I couldn't have predicted.
It began on a normal afternoon. I returned to my flat from my last lecture of the week and, stripping off my boy clothes for the final time before a weekend of femininity, I jumped in the shower to shave off what body hair I had. The feeling of freshly shaved smooth legs is one I still haven't gotten over and my cock was rock hard before I'd even finished. Stepping out of the shower, I was in a particularly slutty mood and decided to play the whore for my evening entertainment. I started with a sexy black lace thong, teamed with a hot black basque which helped to give me the illusion of a cleavage. The tight feeling around my torso left me breathless and I could feel my cock throbbing against my panties. I sat down on my bed to pull a pair of sexy nylon stockings up my legs and attached them to the suspender straps of my basque. Standing back up I completed the outfit with a tight red leather miniskirt which clung to my ass like a second skin. Sitting back down to apply my make-up and done my auburn wig, I relished the feeling of my stocking clad legs rubbing together, sending a thrill of anticipation through my body.
My transformation complete, I was ready to indulge my fantasies. I walked over to my bed, swaying my ass and lay back. Letting my hands play across my smooth legs and over my tummy for a while, I eventually released my cock from under my skirt and panties and began to masturbate slowly. I closed my eyes and let my mind wander...
...I'm standing in a darkened room. It feels small and warm. I can hear soft footsteps behind me but I feel a knot of excitement and anticipation in my stomach. The footsteps stop right behind me and I can feel their breath across my neck. I can feel my heart beating in my chest as I wait for something, anything to happen. Part of me thinks I should be afraid and run away, but I only feel safe and secure.
He steps closer to me and I feel his body press against my ass as he wraps his strong arms around my waist. It feels wonderful to be held and I reach down and wrap my left hand in his. I reach my other arm over my shoulder and caress his unseen face. He is taller than diminutive 5'5" frame and he leans down to gently kiss my neck and jaw line. His lips grow more insistent and as I twist my neck around I melt as we share a kiss. His hands begin to roam across my body as his tongue pressing against my lips and parts them to meet my own tongue. Our kisses grow more passionate and without letting our lips part, I turn my body to face his and press myself against him, tilting my head back in the process. I drape my arms around his neck and feel his own wandering down my back to cup my ass through my skirt.
I'm putty in his hands and as he lifts my ass I wrap my nylon clad legs around his waist. As I do so, my tight skirt rides up and his hands find my bare ass cheeks. He easily supports my weight as my ass comes to rest against his crotch. I can feel his hardening cock rubbing against my balls through his pants and it comes to rest between my ass cheeks. I feel so feminine wrapped around his torso and a strong desire to be fucked by this man rises within me. He seems to sense this and with me still in his arms and our lips locked together, he carries me across to a bed in the corner of the room.
When we reach the edge of the bed he throws me down on to it and I get my first clear look at the man who is about to fuck me. He's tall and muscular with deep blue eyes and strong features, but I only have a moment to take this in before all I care about is his hard cock taking my virginity.
He stares into my eyes for a moment before roughly grabbing my waists and flipping me on to my chest. My face is pressed into the bed and once more I cannot see my lover. His hands slide up my legs and under my skirt, letting it ride up higher onto my back and fully exposing my ass to his stare. His hands leave me and a squirm in anticipation and lust, wiggling my ass in encouragement. Instead of feeling his cock sliding between my cheeks as I expect, however, I gasp in shock as his tongue begins to explore around my hole. My own cock throbs with pleasure as his tongue finds its mark and he begins to alternate between sliding it across my hole and probing, deeper and deeper into my pussy. I try to relax and push back against his tongue and moan in pleasure. All too soon I'm left feeling open and exposed as his tongue leaves my hole and I try to prepare myself for what must be coming next.
I hear his pants hit the floor and he grabs me by the waist once again and lifts my ass into the air, pushing my head and shoulders into the bed. I feel exposed and vulnerable, knowing I am completely under his control. His assault, when it comes, is so sudden and violent that I am left breathless and cry out in shock. The pain is intense as his cock presses into my tight asshole. Tears spring to my eyes and a burning sensation fills me, and yet the fullness I feel is wonderful and my cock is harder than ever.
He waits for a moment with his cock buried in my ass and I just become more accustomed to the feeling when he starts to pull out and then drive back in to my willing hole. I begin to push back against him in time with his strokes and we soon build up a steady rhythm.
His hands are round my waist once more as he builds up his pace. All I can think of is the cock that is filling my pussy and I feel so feminine I almost forget about my own cock until he reaches round and grasps it in his hand. It doesn't take long before we are both releasing our pent up loads, mine onto the bed below me and his deep into my ass. As he cums, he pulls his cock out of my ass and lets the last few drops fall on my back, before wiping his cock on my nylon clad leg...
Back in my flat, I was playing the fantasy through my mind as I lay on my bed, stroking my cock with one hand while the other was playing with my asshole. Just as my climax was building, there was a sudden knock on the door and my reverie was shattered.
My eyes shot open and took in the scene in my room - the floor and desk littered with sexy clothes and make-up and me, stretched out on the bed with my cock sticking out of my tight skirt. In that moment of panic I remembered that my landlord was due today to inspect my flat. How could I be so stupid! There was no way I could put him off.
There was another loud knocking on the door, "Mr Taylor, time to inspect the flat."
"Yeah, I'll be there in a minute, I've just stepped out of the shower!" I called back, trying to keep the panic out of my voice.
I knew there was no time to stash my clothes away properly, so I would just have to hope his inspection was not too thorough. My biggest problem were the clothes I was wearing and my make-up.
I dashed into the bathroom and wiped my make-up off the best I could. My eyes looked raw and my face flushed but at least I wasn't wearing lipstick anymore.
I hurried back into the living room grabbing clothes and make-up as I went and threw them all into the bottom draw of my wardrobe, adding my wig to the pile. I knew I didn't have time to change, so I shut the draw and threw on my bath robe. I was about to open the door when I remembered my nylons. Looking down I could see my nylon clad feet and calves so I pulled on a pair of jogging bottoms and socks as my landlord knocked on the door once again.
"I haven't got all day Mr Taylor!"
"Sorry, I'm coming now."
With a quick check in the mirror to reassure myself that my secret was safe, I opened the door to my landlord.
"Sorry for the wait, I forgot you were coming today."
"Hmm, well luckily your the last for today so you haven't set me back," he said. "Now, let's see, have you had any problems with the flat, no breakages or faults to report?"
"No, everything's been fine, thanks,... all fine."
"OK, well, everything seems fine in here. I'll just check the kitchen and bathroom and then I'll leave you to your evening."
As he moved to walk past me into the kitchen I tried to step back to give him room, but as soon as I did, I knew it was a mistake. I felt the backs of my legs hit the edge of the bed and couldn't do anything to stop myself falling. At the same time, my robe was caught between my legs and the bed. Within a matter of seconds I found myself flat on my back with my robe flung open, exposing my basque to the world.
"Well, what do we have here?"
"Please, I didn't mean for you to see this, I'm sorry."
"Don't be sorry, I'm not. I always thought you were quite cute. Why don't you show me the full package sweetie?"
"No, please, can't we just forget this ever happened?"
"Oh no, I don't think so babe, not unless you want your nearest and dearest to find out what you get up to behind closed doors. No, I think we could have some fun with this. Who knows, maybe if you're a good girl, I might even make it worth your while."
Looking in his eyes, I knew he was perfectly serious. I also knew that I couldn't let my friends or family know about this part of me. At the same time, I felt the woman inside of me longing to be fucked and when he referred to me as a girl, it sent a thrill down my spine. In that moment I decided: I would play the part for him and do whatever I could to please him. If I enjoyed it then who knows where it could lead? If not, at least I would have bought myself some time to find a way out of this situation.
I stood up, leaving my robe behind, and reached out to softly touch his hand with mine.
"OK then hun," I said in my most feminine voice, "why don't you make yourself comfortable while I get ready?"
"That's more like it," he said, placing a hand on my hip, "I'll wait right here on the bed. Don't be too long."
I took what I needed from my wardrobe and shut myself in the bathroom to get ready for the second time that day. Having fixed my make-up and wig I took of my pants and socks to reveal my skirt and nylons once more and took a moment to compose myself. I couldn't deny the fact that I was turned on and was feeling more than a little nervous about how he might react. Happy I had done all I could to make myself look pretty, I stepped out of the bathroom.
I was pleased to see a look of surprise and then lust pass across his face as he saw me, and I got the impression he was quickly reassessing the situation.
"Wow, you do look hot as a girlie! Come over here, let me see you."
I slowly walked towards him, using my hips to sway my ass, and did a little twirl in front of him.
"Do you like what you see?"
"Hell yes, you're more beautiful than I imagined." He reached out and ran his hand up my leg. "Your legs look fantastic and your bubble butt looks so feminine. Come, sit on my lap."
I sat sideways on his legs with my arms around his shoulders and felt his hands caressing my legs and my back.
"Do you have a girlie name, sweetie?"
"Hmm-mm, it's Lucy."
"And have you been with a man before Lucy?"
"No, you're my first."
"Well I'll have to be gentle then."
He pulled me closer on his lap and leaned in to place his lips on mine. I closed my eyes and let him kiss me. As I began to return his kiss and part my lips, he leaned back onto the bed and pulled me down on top of him. My leg came to rest between his and I could feel his bulge pressing against my knee. Meanwhile his hands had found my ass and were massaging my ass cheeks.
As his kissing became more passionate, my lust took over and my hand found its way to his crotch and began to fondle his package.
"Mmmm, have you found something you like, Lucy?"
"Mmmm, it feels so hard."
Sitting up, I unzipped his pants and pulled them off his legs along with his boxers, revealing his semi-hard cock, while he pulled his shirt off. Kneeling next to him, I leaned in, letting my hair brush his member, before taking it firmly in my hand and starting to stroke it. I could feel it growing in my hands as I played with it when I felt his hand on the back of my neck. He gently guided my head closer to his cock, leaving me in no doubt what he wanted. I tentatively brushed my lips against the head of his cock, before flicking my tongue out to get my first taste of his precum.
"Oh, that feels good," he moaned. He tasted better than I expected too, and I felt ready to give my first blowjob. Holding his cock firmly by the base, I ran my tongue along the underside until I reached the head, gently placing it in my mouth and sucking. I was rewarded with a moan as I moved my mouth backwards and forwards over his hard cock, letting my tongue tease his head and gradually sucking more and more into my mouth. His groans of pleasure told me I was doing something right and his one hand returned to fondling my ass while the other began to force my head to bob faster and faster over his hot cock.
As his hand slipped under my thong between my cheeks to press against my asshole, I moaned over his cock which seemed to drive him on even more. He brought his hand away from my ass and offered me his finger. Releasing his cock from my mouth for a moment, I took his finger into my mouth and sucked on it greedily, before returning to his cock for more. Soon, I felt his hand return to my ass and his finger slipped inside my hole, bringing out a groan of pleasure from my lips.
As his finger probed my asshole, I sucked hard on his cock.
"Oh God, I'm gonna cum Lucy."
I felt his orgasm build and sucked one last time, before feeling his hot cum hit the back of my throat. At the same time, my own cum exploded from my cock, soaking my panties. I swallowed the first spurt of his cum, but let the rest leak out around his cock, coating my chin in his juice.
Letting his cock fall from my mouth, he pulled me up to lie next to him and I draped my nylon clad leg across his cock. I was shocked when he leaned across and kissed my cum soaked lips. We French kissed passionately, sharing the cum between us, before falling into a satisfied sleep where we lay.
I felt like a whore, and I'd never felt so content.