As my teen years progressed, my little feminine traits and preferences somehow became more important to me, and felt increasingly natural. I identified as a guy, and I was nowhere near truly understanding my sexuality or the path I would take in life. But the first steps were happening.

My friendship group was wide and diverse, but socialising focused mostly with a small group of girlfriends. I was sporty and enjoyed playing tennis, some competitive running, and swimming - all with guys - but I had no desire to take that male camaraderie any further.

I had gravitated naturally towards the girls as we progressed through high school, and as hanging out replaced the more specifically boys’ or girls’ activities of childhood. I was comfortable with the girly chats and giggles. I was also very much at ease at the times we needed to listen and help support our friends through the drama and upsets of those teen years. Especially as we passed sixteen and beyond, when our looks, relationships or even an unfortunate pimple, could seem to bring the world crashing down! Although unspoken, I knew these girls would be there for me as I passed further along my inevitable path towards coming out. I’m certain they already knew this, too.

Hanging out, of course, included sleepovers, and the girls had always made me a welcome participant. Even as now we’d turned seventeen, the girls’ parents still understood I was not a “regular” boy, cosied up under duvets with their daughters. In fact, at this age, I could now choose to buy girls’ soft cotton PJs to wear. I would select pastel colours, often pinks. Paired with T-shirt tops, rather than the flimsy vests the girls wore, my PJ shorts would stretch like theirs across my ass and reveal more than a glimpse of my pert little cheeks.

At these later sleepovers, I started to shave my legs. This helped me to fit in, and also felt so gorgeously feminine. The girls told me that their boyfriends’ preference was to be smooth, and shaved all over. We didn’t show each other, but I too started to shave smooth around my little dick and all over my tight teenage ball sack.

I had always been a willing make-up model for the girls, and a keen student of their cosmetic skills! Outside of the haven of the girls’ bedrooms, I’d sometimes wear a little light foundation, a dusting of a dark pink or tan blusher on my cheekbones, and some concealer on my teenage pimples and eye bags. I’d also dare to wear a lightly frosted lip balm in the safety of the girls’ company as we headed into London for shopping, or to the local mall, or to the cinema. Otherwise, a cute, fruit-flavoured balm on my lips was the closest I’d get to wearing lipstick… yet!

I could easily choose to wear quite gender-neutral fashions. Skinny jeans were “in”, which was great news for me. I’d pair them with Ugg boots, Converse sneakers, or some ankle boots in winter. I enjoyed shopping with my group of girlfriends, and I would eagerly buy similar T-shirts and tops to theirs. TopShop on Oxford Street was a regular destination in London for us. I favoured their faux-vintage T-shirts, decorated with faded beach scenes, old advertising logos, or girly little slogans. Cut with a loose fit for girls, these shirts fitted my male body more snugly. They were thin and soft and felt great, being the nearest to openly female clothing that at sixteen and seventeen I dared to wear.

I’d look on longingly as the girls shopped for their cute panties in stretch cotton or pretty lace. Skimpy boy shorts and thongs were their favoured styles. I made do with guys’ soft cotton boxer shorts, but always in pastel colours or with suitably androgynous designs, such as sweet cartoon characters, polka dots, or cutesy hearts. I was, however, already very aware of my growing preference for female attire. When the time came for me to finally have my own panties, I knew from shopping with the girls what size I would need and the style and fit I would choose. That day really couldn’t come soon enough for me.

An activity that crossed genders and social groups was skateboarding. I loved to hang out around the town’s car parks and shopping areas to practise my tricks. I wasn’t the best, but I was respected as a decent rider and enjoyed hanging out and shooting the breeze with kids from other schools and of different ages. One, Sam, was one of my extended group of skateboarding buddies. He was eighteen, and in his final school year, one year ahead of me.

I had such a secret crush on Sam! He was good-looking, with wavy hair that looked both unkempt and, at the same time, meticulously cared for! Sam was effortlessly cool. He possessed mesmerising brown eyes and the cutest sprinkling of freckles across his nose and cheeks. My slightly androgynous dress sense and my group of fashionable girlfriends seemed to make me cool in some eyes. Fortunately, these seemed to include Sam’s beautiful brown ones!

Sam lived a few railway stations away from school and closer to Central London. He and I had only ever hung out as part of a group, and with the year between us at school, we had a fairly arm’s-length friendship. So I was surprised when, away from the skate chat groups and forums, my cellphone pinged with a direct message from him. My heart skipped a beat, of course, but I really only expected the message to contain a simple question about a local skating spot or to request someone else’s number.

“Hi,” started the message. Then, unbelievably, continued with “going to Southbank Saturday. Come too?”

Southbank, in central London, is a legendary skateboarding spot. Originally an urban concrete seating area next to the River Thames, its graffitied walls, blocks, and angled surfaces are now a magnet for skateboarders.

“Yeah!” my shaking fingers tapped out in response.

“Cool. Kingston station at eleven?” came the reply.

“Sure!” was my attempt at coolly disguising my elation.

But my elation reached new heights as the next ping on my phone, seconds later, announced a single “x”. I think I probably pinched myself.

Saturday morning came, eventually! Multiple outfit options were finalised, with pale skinny jeans, a white long-sleeve T-shirt, and my favourite tan-coloured short canvas Levi’s jacket. Some bangles from the girls completed the outfit. Skateboard under my arm and a cotton satchel bag over my shoulder, I boarded the train.

My phone pinged. It was from Sam: “Had mum’s errands. Sorry, twelve ok?”

Almost at his station, an hour’s delay would barely dent my excitement. So I strolled from the station into the sunshine and on towards the decent selection of high street shops that Kingston-upon-Thames offers.

Wandering into a large department store, I almost subconsciously drifted into the large, brightly lit lingerie department. I was often drawn through such areas with a mix of fascination and temptation. For some reason, this time, I felt the confidence to actually browse for my first female underwear.

I picked up and put down a few possible selections. Thongs still seemed a little risqué. High-leg or regular panties didn’t seem like they would be a memorable first purchase. So I settled on a set of three lace boy shorts, one of each in black, white, and a deep cerise pink, held together on a little plastic hanger.

The assistant took my payment and popped my panties into a small bag as my heart pounded with excitement. I excitedly retraced my steps back towards the station, my panties, yes, my panties, tucked in my shoulder bag. I felt grown-up, girly, and very content.

Sam wasn’t as late as he’d expected and smiled warmly as I approached. He greeted me with a light tap on my shoulder. I think I’d reached peak excitement buying my little panties, and now I was actually quite relaxed being with him.

We’d chatted excitedly about our skateboarding during the short train journey, then ridden our boards carefully through pedestrians on the five-minute ride from Waterloo Station to Southbank.

The skate area was busy, but we soon found our space to get started. We’d had an exhilarating forty minutes amongst some great quality riders before an older guy and I collided, and I unceremoniously landed hard on my butt! We both apologised as the guy reached to help me up. “It’s OK,” interjected Sam as he arrived at speed. “I’ve got them,” he added and pulled me up by the hand. “Them,” I reflected to myself, as the pronoun Sam used. Interesting!

“Let’s go chill,” Sam suggested, and we headed into one of the areas housing cafes and bars, alongside galleries and theatre spaces. I excused myself and, in a bathroom, inspected the developing bruise at the base of my back. My shoulder bag on the floor next to me had fallen open, and I excitedly noticed my new panties.

On a whim, I entered one of the bathroom stalls, removed my shoes, jeans, and boxer shorts. I snapped the little plastic threads holding my panties on their hanger and nervously put on the gorgeous cerise pink pair. I smoothed the soft lace across my butt with both hands. I tugged them up tight to expose the cute little bits at the base of my butt cheeks. The panties felt so good. I felt so feminine. I quickly dressed again, bundled my boxer shorts into my bag, and went back to Sam.

“Hey,” he said, “this movie was mentioned in my Media Studies class at school.” He nodded at a black-and-white poster, with the title and text in French. The man and woman dancers photographed in shadow on the poster looked intriguing. “Looks cool,” I replied.

Some fifteen minutes later, we were sat and ready in the near-empty little bougie art-house cinema. The seating was only part cinema-style, and Sam had chosen us a large, rich blue-coloured velvet sofa. We sank into the soft material, me in my customary position of sitting with my legs tucked to one side and under me. With my legs to my right and Sam close to my left, I naturally sank further against him. This he seemed to respond to welcomingly. He lifted his arm closest to me to rest gently on my shoulder.

As the lights dimmed, I looked around the small auditorium. Three other people were there with us: an earnest-looking student type at the front and a couple diagonally opposite from our own position. We were in the far back corner.

Being this close, I could hear Sam’s soft breathing. He must have sensed my proximity and, without looking at me, whispered, “How’s your back, after that wipeout?”

“It was more on my butt, but yeah, OK, thanks,” I replied.

He slipped his hand from my shoulder and slid it between me and the soft material of the sofa to rest his palm against the base of my back. He was touching my bare flesh, as my shirt had ridden up as I’d settled into my seat.

“Aww,” he teased as he patted my back, rapidly followed by a small gasp and “Whoa!”

Sam’s hand had come into contact with the thin elastic waist of my panties, and the lace sitting below!

Rather than pulling away, though, I was delighted when Sam applied gentle pressure on my back with his fingertips to move me a little forward in my seat. As I did so, I hastily unbuttoned the front of my jeans. He slid his hand down onto my lace-clad butt. Subtly signalling with his palm for me to lift a little, I did as told, and two of Sam’s fingers started to tease my tight little hole through my panties.

I leaned in closer to Sam. He responded by gently holding my chin between the first and second fingers of his other hand. We started to kiss softly. It seemed very natural, with neither of us needing to take the lead. As our lips moistened from the contact, our mouths opened a little more, and our tongues flicked around each other and across our teeth. It was heavenly!

Withdrawing from my butt momentarily, Sam’s right hand reached to our mouths. I willingly and hungrily wet his fingers. I raised myself again slightly from our seat, and this time, with his hand inside the back of my panties, Sam slid a finger into me. I gasped lightly against his lips as we continued to kiss.

This was the first time I’d been caressed in this way by someone else. It felt so different from the soapy fun of fingering myself in the shower, or late at night in bed. Sam gently, but masterfully, had his middle finger deep, deep inside me. He made little circular motions with his fingertip as I matched his rhythm and movement with my hips. I couldn’t maintain our kissing while feeling like this. I needed to lean my head on his shoulder, eyes closed, letting out the occasional muted whimper of pleasure.

I slipped my hand from Sam’s shoulder and, with my fingers, slowly traced the line of buttons on his denim jacket down to his waist. I was lost in the moment, as my tummy tingled from the gorgeous attention he was giving to my tight butt. We started to kiss softly again as I popped open the waist button on his jeans. The buttons of his fly were next, and I then slowly slid my hand onto his soft cotton boxer shorts. The times I had fantasised about a moment like this! Now, it just felt so natural.

My hand brushed against Sam’s hard cock, still within his boxers. I hooked my thumb into the waistband and pulled down slowly. His cock sprang up against the back of my hand. I reached to position my palm and fingers against his shaft, and I started to slowly stroke. His cock felt thick and quite veiny and, as I let my fingers wander, I could feel his tight foreskin stretched around the head. His breathing deepened as I gripped harder and lengthened the strokes. So much bigger than mine, it was a very pleasant, new experience to hold and control Sam’s girthy cock.

I couldn’t remember feeling excitement like this before. My gorgeous crush Sam now worked two fingers deep in my tight hole, while I gripped and pulled up and down on his rock-hard cock. I was so pleased that I’d bought, and then put on, these panties. I felt so sexy and girly, doing and feeling things I’d only dreamed of. I pulled away from Sam’s lips. He smiled at me, and I felt so special.

Pausing my pulling on his cock, my hand wrapped around the base of his shaft. Maintaining eye contact in the dim light, I started to slowly slip down his body, being as discreet as possible. I was so pleased that Sam had chosen this sofa. I was so pleased Sam had chosen me! Now I was ready for the next step in my girly journey.

Resting on my knees, I used both hands to properly release Sam’s cock from his jeans. Gently pulling back his foreskin, I leaned forward. My mouth opened expectantly as I flicked my tongue across the head of his cock before closing my lips around it. I had imagined this scenario a thousand times. Now it was happening. I had a guy in my mouth, and I was going to satisfy him.

Sam gasped as I started to gently bob my head up and down, my soft, warm lips tightening a little around him. A lasting memory of this, my first time, was how hot his rigid cock was.

As I paused for breath, Sam’s pre-cum dribbled onto my tongue. I cupped his tight balls, then restarted and quickened my head movements up and down.

Sam took his hand from under me and gripped my shoulders as he started to fuck my mouth, in time with my head movements. I glanced up in the semi-darkness. Sam was lost in the moment, head back, groaning softly. I longed for his thrusts to be deep in my ass and vowed to myself that Sam would soon be the one to take my girly virginity at that end of me, too!

I tightened the grip of my lips as I went hard up and down, up and down, savouring every second and every part of Sam’s oh-so rigid cock. It felt so intense, and I knew that giving my body and emotions to men would be the future for my sex life.

Sam gave one last hard thrust deep into my mouth. His balls tightened, and I felt a couple of intense, hard shudders run through his lap. He gasped, and the next shudder ran hard from his balls, through his shaft, and against my lips. My first taste and experience of thick, hot cum followed seconds later. I gripped his hips so that I could enjoy every moment, and savour every drop of him in me.

It felt so natural to hold Sam there as he stroked my hair. He had coated the inside of my mouth and top of my throat. It felt amazing! I released his hips a little and, just as naturally, devoured his load in two deep swallows. I licked my lips provocatively towards him.

As I slipped back up into my seat, Sam smiled and, with his finger, gently hooked a string of his cum from the side of my mouth and onto my lip. I licked it from his fingertip, and I could taste the sweet sweatiness of my own butt on him.

Again, I felt deliciously feminine as I pulled up my panties and fastened my jeans. Then I leaned across to Sam and bent down to lick off the last of his cum from him. I tucked his softening cock back into his boxers as he started to fasten his jeans.

We held hands as we slipped out of the still-darkened auditorium. My panties felt tight from Sam’s attention to my rear. And at the front, my own dampness now felt cool in the outside air.

“That was amazing,” Sam giggled.

“You just, just… had me so turned on, Sam,” I managed to reply as I squeezed his hand.

We stopped and hugged, both aware that we’d feel that we’d sadly need to be a little less amorous on our walk back to the station. Not for the first time that afternoon, I made a vow to myself. I decided and promised the girl inside that she would become the girl on the outside too, and that walking with a guy like Sam, hand in hand, would be the most natural thing in the world.

That thought reminded me of a moment from earlier. “Sam,” I started, “it was very thoughtful when you used ‘Them’ as my pronoun earlier.”

“I guess you’re not ready for ‘Her’ yet?” he replied.

My eyes filled up. He truly understood me.

Sam sensed my emotion and went on, “But you’re so much more than a simple ‘Them’ to me.”

He continued, “Hmm, surely there’s a cuter option.” After a pause, when his beautiful eyes were deep in thought,

“What about in French, or something like that?” he continued. “Something you and I will understand.”

“What, like, Il, Elle, On, Ils…?” I parroted from our French class recitals of pronouns.

“Yes!” He stopped me. “Yes, Elle, of course! I will call you, Elle!”

A tear ran from one of my already welling eyes. Sam wiped it from my cheek and smiled softly at me. Elle had been born in that moment, and her future was mine to write.