And Then It Happened For Real

It was the late 90's. I was 19 years old and I knew was developing differently from all the other boys. With hindsight it was obvious, but at that time, not so much.

For example, unlike most of my peers who were into Radiohead, REM or Oasis, I had an absolute, devoted love for The Spice Girl and their message of Girl Power.

I'd get confused about the unnatural effect Mr. Knight, the cool, cultured, mature gentleman, with his luxuriant moustache, that lived near to us had on me.

The mere act of him smiling at me whilst nodding a greeting as we passed one another on the pavement, would make me blush and go weak at the knees.

Even more intriguing to me though, was the way that some of the other boys, the older, tougher ones, could intimidate and excite me at the same time.

I was pretty introverted, I wasn't particularly popular and my social circle was pretty small, so I suppose, I lived a lot in my own head.

There would be lots of introspection and self-analysis.

I knew I wasn't fully emotionally developed and my mother would often urge me to grow-up.

I had moments where my confusion would sometimes almost over-power me. Whenever I felt these moments coming on, whenever I would feel particularly anxious or unsettled, I discovered a strategy and I found the place I would go.

I would wait until the house was empty and then visit the perfumed, delicate mystery of my mothers bedroom, only there could my puzzled, confused mind begin to relax.

In her room, I felt safe to have the thoughts and feelings that I assumed other boys didn't have. In her room, I felt free to explore, to experiment, to seek the reassuring comfort in my feminine side and to embrace it.

I didn't know where this overwhelming emotion to be more girly came from, but when I submitted to it and openly accepted this inner desire to dress up, to feel the delicate satins, silks and nylons against my skin, all I knew, was that it made me feel somehow more complete.

There were days when I knew my Mother would be out the house all day. From the moment she closed the front door behind her, I wouldn't waste a moment.

I would take full advantage of these few hours, grab these opportunities and use them to dress fully.

My mother and I were approximately the same height, approximately 5"7', although she, being the daughter of farmers, had a more robust figure, which luckily for me, meant most of her clothes fitted me almost perfectly.

My mothers wardrobe was quite conservative, her outfits although expensive, were more demure that revealing.

I did however find certain items that I could never remember seeing her wear before, things that I assumed were from her younger days that she couldn't bear to throw out.

There was a black leather miniskirt that hugged my hips as well as a frayed hem denim miniskirt with pockets too small for anything, but most delightfully, there was a pair of classy, deep brown, knee high leather boots with a strap below the ankle and a decorative brass buckle attached, they had 3 or 4-inch heels.

Thanks to the fact she was of a larger stature than me and albeit with a bit of a squeeze, actually fitted quite well.

With no one in the house, I'd be luxuriant in her lingerie, a garter belt on my hips and its tight straps running over my thighs, the clasps tightly holding up my stockings.

I'd pull on the boots, zip them up, chose either of the miniskirts then take my time to match them with the variety of her various blouses and tops.

Occasionally, I'd wear lipstick and sometimes some eye-shadow.

Not being particularity tall and being mostly legs, which, if I do say so myself, looked amazing in nylon stockings, which I adored pulling on and was very careful never to ladder.

I wasn't muscular, though my slender torso was toned from my weekly swim.

My penis wasn't particularly long or thick, about 6 inches when hard, but when I was dressed and it was cutely constrained in panties, it tingled and evoked thoughts of such uncontrollable naughtiness,

I would look into the full length mirror, marveling at my reflection and immediately, whatever negative, stressful inner thoughts I might have been having would instantly evaporate to be replaced with mental images of such lust.

I could be so lost in them that at times that I could barely breath.

After a few weeks discovering this side of myself, I started to look, with envious eyes, at all the girls my own age and older that I would see going about their day.

To me they were so lucky. They were free to express their sexuality, to wear things that highlighted their best features, and, to my mind anyway, they all seemed to carry an air, a confidence, something that I could only imagine came from knowing they were sexually desirable. I would get so jealous.

I began to try my best, within reason, so as not to give myself away, to model myself on them.

I started keeping my entire slim, pale skinned body, hair free and soft by using my mothers delicately scented depilatory and moisturizing creams.

I started growing my chestnut coloured hair longer and dreamed about the day that it would be long enough for me to wear pigtails in cute ribbons or brushed back into a bouncing ponytail.

Alone in the house, I would practice my walk, up and down the hallway I'd flounce in my mothers boots, never tiring of hearing the heels click-clack on the polished wooden floor.

Toe to toe with a flick of my hips I tried to master my natural wiggle, imagining I'm sending the flirtatious signals with my body language, as I had observed the other girls do when around the boys they liked.

I would fantasize that I was walking toward Mr, Knight, passing him on the pavement, thrilled as I felt his eyes drink me in, moving up and down my body, totally checking me out as I sashayed closer to him, trying to tease him, to make him want me.

This was my secret and I loved this side of me.

It got to the stage where I knew every item of underwear my mother owned.

This was so intimate, so personal. I knew I didnt want to be caught and humiliated, so I made double sure that anything I borrowed from my mother was cleaned, folded and returned exactly where I'd found it.

Eventually I began to feel ever bolder and I started to wear her things beneath my everyday boy clothes, finding it ever so naughty and exciting to be out in public, talking to boys and occasionally girls, all whilst feeling my sissy secret as it delicately caressed my soft skin.

My best friend David, at 6ft, was taller than me, and he was just as slim.

Unlike me, he was blonde, he wore his hair short and because he was beginning to develop the broad shoulders of his father, he got quite a lot of attention from girls.

We had been friends for a few years, ever since we were paired off together for a high school science project. During this short time together we found that we had mutual interests and hobbies.

We would talk to each other about nearly everything, without the feeling of judgement or the derision that the other boys would sometimes display when they felt inadequate about subjects they didn't know or had no interest in.

It was one of the things that strengthened our friendship, always having each others backs when experiencing the mild bullying, it enhanced our instinctive trust and mutual respect in one another grew.

We were both fairly academic, we'd talk about our futures, art, books and music although he would tease me mercilessly about Mel B, Posh, Baby, Sporty and Ginger but all in good fun.

We never spoke about it, but we both knew we would miss each other in the autumn, when our plans meant we would leave our respective homes and attend colleges at opposite ends of the country.

It was a mid-summer afternoon. David's parents had gone away for the weekend, and we were in his bedroom.

David had gone to make coffee, I was flicking through one of his photography books. I was so engrossed in the subject matter that I didn't hear him come back in. I nearly jumped out of my skin when he spoke.

"Of all things, I never had you down for having the hots for musclemen."

The subjects in the book were clearly swimmers or athletes of some description. The artful, black and white presentation was manipulated to enhance the beauty of the masculine, to explore and celebrate the perfectly honed male physique.

The models physicality was impressively defined as they stood in Olympian style poses with javelin and discus, evocative and professionally shadowed thanks to the photographers lighting.

I had been mesmerised by their manliness, he had caught me off guard.

I panicked and tried to splutter some inane excuse or other, he just smiled a knowing smile telling me that he was only joking.

Despite my best efforts to contain myself, I blushed furiously, he had hit a sensitive nerve and to me it seemed so obvious that I had been caught.

The redder my face turned, the more flustered I became, David was more openly concerned, in an effort to return me to normality he actually told me to relax, reiterated that he was only joking, but this just increased my anxiety.

I was so embarrassed, internally it frightened me that he suspected something and that was such being my friend by not openly saying anything.

I was struggling to regain my composure. The fight or flight instinct was screaming for me to flee, again panicking, I stood up from my chair and quietly said that I had to go.

David, clearly shocked at my erratic behaviour and with a puzzled, hurt look on his face, reached out to stop me. His fingers reaching out to stop me, grabbed the waistband of my shorts attempting halt my escape.

The thick elasticated waistband stretched with the momentum of my exit motion, it pulled away from my body and in the process exposed the pale skin of my hip but also the sheer, white silk, bikini cut panties that I was wearing underneath my shorts.

I saw his eyes widen, his jaw drop and those few moments, they felt like a lifetime.

"What is this?"

His eyes meeting mine as his grip on my shorts loosened. I should have run but my legs refused to respond.

I could see he was waiting for my reply.

I was speechless, I was exposed, caught, all I could muster was a coy smile and a defeated shrug of my shoulders.

Honestly, I thought our friendship was over.

"Come on now, you cannot go now. Stay, come sit back down."

He took my hand, which startled me, then, as he smiled at me so warmly he relaxed me.

Our eyes never leaving each others face until he spoke, softly, he reminded me that we were friends. What he said next completely shocked me, he told that he loved me and that to him, actually we are so much more than just friends.

My throat was so dry I couldn't speak as I felt the tears well in my eyes, he deftly put his soft fingertips to my cheeks and wiped them away.

Then he did something so unexpected, so astonishing. He leaned in and kissed me gently on the lips.

At that moment I thought my head and heart would explode. I could hardly breathe and I felt the most incredible flush of excitement in every part of my body.

Then in an almost inaudible whisper he told me.

"I have wanted to kiss you for years."

I couldn't believe what I was hearing. I couldn't fathom what was happening, so replied in the only way I knew how, truthfully.

"Me too."

I leaned in towards him and I kissed him. I think I did it because I wanted to make sure what he had just done had actually happened.

David responded and his mouth opened as our lips met and it seemed that this second kiss went on for ever.

Deep down, I suppose that I knew it was inevitable. I knew that I loved him more than just a friend.

He had occasionally featured in my fantasies, though mostly they involved the handsome Mr. Knight seducing me, but there had been times and naughty thoughts, when I was dressed where I would masturbate, fantasizing that this would happen.

My mind was racing as we let our tongues dance in each others mouths. I am who I am so I allowed him to lead, I let him pull me over onto the bed beside him.

I melted into his arms as he lay me down onto his soft quilts, my head on his arm, allowing him to maneuver me beneath him as we lay together.

Looking up into his beautiful, smiling face, the absolute thrill of this moment.

His hands running over my compliant body, along my legs, up my arms and into my hair. I was enjoying giving into him, consenting to him taking control of me and the situation.

I helped him pull off his T-shirt and kissed the soft skin of his chest, inhaling his scent.

My lips found a nipple and I heard his gasp as I tightened my mouth over his stiffened nub, sucking on it then gently, softly biting it.

My head was in a whirl, I was actually with another boy and not just any boy, my boy.

Then, it was my turn to gasp, pushing me gently backwards I lay back as his fingers found the top of my shorts.

"Lets see what you're wearing then you little minx."

I was so thrilled, it was as if he knew exactly what I wanted to hear, I was loving every second of this.

I lifted my butt allowing him to pull my shorts down and then off completely, exposing myself, in my cute little panties, to another persons gaze for the first time ever.

David purred as he ran his fingers over the sheer fabric, my smooth shaven clitty below, straining at the material, the pre-cum leaking from my pulsating head leaving a darker spot as his fingertips traced along the outline of my swollen shaft.

Pulling at my sweatshirt hem he lifted it, revealing the almost matching camisole vest I wore underneath, so delicate and sheer it was almost invisible.

"Wow! you really are a sexy sissy girl aren't you?"

I giggled like the dirty girl I was feeling at that moment, absolutely loving the sound of these words he was aiming at me.

I reached for his shorts, tugging at them and having them off in an instant.

Seeing the impressive outline of his erection as it pushed against his tight white briefs, screaming for release and it made me gasp loudly and involuntarily.

I slowly licked my lips in anticipation. I'd fantasized so hard about this moment, craved for it, never ever expecting it to become a reality least of all with my best friend. My mind officially blown as the realization washed over me that I was about to taste cock for the very first time.

I pushed him back into his pillows and crawled onto my knees.

With my eyes focused on his beautiful face, I eased his underwear down his thighs. My concentrations then moved down his body and to his strong, thick penis as it sprung loose from his briefs and made my mouth actually water, it was so very hard, so big, thick, throbbing with its masculine power.

My tummy spun with the excitement, was this actually happening?

I lowered my head and opened my mouth, preparing to do that most feminine of things, I was a dirty girl about to give my man a blow job.

I could smell his musk, it filled my nostrils and I trembled, his sweat, the scent of his manhood, testosterone, his dominance over me. Inhaling him was driving me wild and I willingly gave in, embraced it, submitted to my every effeminate urge.

I reveled in what I was about to do, what most girls my age had probably already done.

I took his hot velvety head into my mouth and it was delightful.

We moaned in unison as my lips wrapped around his thick member, pulsating its beat in my mouth.

My head lowered down until I gagged, withdrawing slowly, I continued tasting him, then down again, up, down, up down, his beautiful prick in my slutty mouth.

I ran my tongue around his purple, salty dome and sucked as much of his meat into my cock hungry mouth as I could.

As he grabbed my hair and slowly fucked my mouth, something inside me clicked, something outrageous yet not unexpected. The girl in me wanted more, I looked up wantonly from his crotch, my doe eyes pleading as they met his, reluctantly removing his dick from my mouth and in a soft voice I pleaded.

"I want you inside me."

"I need you to fuck me."

David's smile grew even wider, sitting up he playfully, yet determinedly, grabbed my under my arms and threw me onto the bed and as I fell onto my back, naturally, instinctively , my legs opened wide and I giggled in a voice I did not recognize.

He eased my mothers delicate panties down my legs until they hung off one ankle, then gripping me by the hips, he spun me around.

Now more than ever I felt subservient to him, on my arms and knees, pointing my boy pussy up towards him, I had never felt more alive.

His strong fingers gripping my butt cheeks, spreading them. I felt his warm breath on my crack and then his wet tongue found my bud. I panted with animal lust, this feeling was so incredible.

I was being eaten out by a gorgeous man, my pussy was being licked and I was in my sissy heaven.

My pussy now slippery from his saliva, his tongue disappeared, and he began to finger-fuck me, first one then two, the intrusion made me yelp as he stretched my virgin hole to its limits making me moan loudly with the erotic pain his digits were inflicting on me.

He called me a naughty bitch, he called me his dirty whore, his sissy slut and I begged him for more.

"Oh yes David I am your slut, oh yes."

As he fingered me I pleaded, I begged, I couldn't wait.

"Please fuck me, oh please please David."

With my head pushed into the quilted covers, my ass stuck up and wiggling to invite him, I heard his nervous laugh and a moment later felt his cock at my desperate entrance and I nearly fainted.

This is what I wanted, this is what I needed, it was actually happening, yet I still could not believe it.

Slowly, firmly, determinedly he slid his thick meat into me.

The pain, the abject agony of him inside of me, the heat mixed with the stretching of my hole was agonizing. Then it eased and as quickly as it appeared it seemed to disappear, leaving me with the utter, unbridled joy of feeling this beautiful man inside me.

Tenderly, lovingly, he eased himself in, then out, in then out, as I got used to this unique fantastic sensation. I was taking the final step the step, finally, I was the girl I wanted to be.

I was pleasing my man with my body, giving myself to him doggy style, I started to push back against him, I wanted every inch of him inside me, I moaned, he moaned.

I was overwhelmed girly desires, my tight little boy pussy gripping him and milking him, I could feel the salty tears on my cheeks as he fulfilled my female lust for cock.

With my skimpy camisole around my shoulders, he gripped my hips and started thrusting into me, faster and harder, his incredible heat, his tremendous cock as hard as iron, battering into me. My high-pitched moans urging him on.

"Ooh yeah David, fuck me hard, fuck me hard, oooh yeah fuck me."

I felt him tense up, I heard his first grunt. His fingertips gripping solidly on my hips and with one almighty thrust and his full shaft buried inside me, he shot his load.

I felt every jet of his cum as his cock exploded, as he filled me, spurting into me, confirming me as his sissy whore.

Then at that moment, with his seed starting to escape and run down my crack, I was rocked and without touching my own clitty I was blown away with the force of my own orgasm as it tore through me.

I cum harder than I ever thought possible, jet after jet of my own ejaculate left me, my climax soaked his sheets.

Collapsing together onto the bed, entwined, locked together, my stomach covering the wet puddle of my own making.

Our sweaty bodies exhausted, we panted and sighed and his arms wrapped around me.

Eventually, his spent, flaccid cock slipped out of me with a sloppy plop and we giggled.