Starting to become a young woman in my late teens was a time not only of challenges, but also of great excitement and delights. Looking back, it is difficult to pinpoint every milestone but, like any teenager, I mostly recall the usual rites of passage. First kiss, first drink, driving a car, first trip without parents, and so on. But for girls like me you can add, for example, no longer feeling comfortable using the boys’ bathroom, starting to actually feel comfortable needing a bra… and feeling even more comfortable letting someone’s hand inside my bra!
So, at seventeen, I felt able to be making positive physical and emotional steps. There were the outside influences and happenings around me, such as building an empathetic group of friends, or being acknowledged as the new “me.”
And then there were the things within the new me. Elle no longer felt like an alter ego, or even just a part of me. Instead, I was part of her, and I was gradually becoming able to fill more and more of her shell and all aspects of her as a person.
And, thinking back to those rites of passage of the young Elle, all the pieces of emotions, physical changes, and outside influences had come to a head with her (my) first serious date as a transitioning seventeen-year-old.
It had been three or four weeks since my eighteen-year-old crush, Sam and I had our skateboarding date. We’d shared our exciting climax of making out, with me experiencing wonderful desires and sensations as a girl. Sam seemed to have enjoyed his own climax, into my willing mouth! You can read all about that in my previous story in this series.
Our date had been during the Easter break from school. On our return for the Summer semester, Sam was heading into a major set of academic tests. At eighteen years old, this final year of school for him culminated in a set of exams which would determine which university, if any, he would qualify to attend. Huge! For me, a year younger than Sam, my school year would end with some trial exams. But effectively, I had it easy!
Life outside of preparing for the exams would be put on hold by Sam and his schoolmates. Even long-term romances would pause during this pressured time. So, I was not concerned that our fling had not progressed. But, after having such a hot time with Sam, me being delightfully fingered, and enjoying swallowing his cum – I was feeling that my trip into this aspect of my girly life had been amazing, but short-lived.
Sam and I made do with a few late-night web calls. In equal measure, we would chat about his preparation for the exams, our shared interest in skateboarding and, I’m pleased to say, our interest in each other. Sam seemed to enjoy the opportunity to unload mentally, and then in our later calls, start to unload physically, as I teased and played for him in my growing collection of cute girly PJs and underwear.
I would lie on my bed, webcam on, gently stroking my little smooth dick for him, through my panties. I’d enjoy stretching out temptingly, my arms back past my head, and my legs long out in front of me. I especially delighted in my newly smooth-shaved chest and armpits. I was starting to look, and feel, so feminine.
I’d slowly roll over onto my front, the thin material of my panties purposefully pulled up into my butt, as Sam enjoyed the sight of my smooth cheeks being presented to him. I would slowly finger myself for him, before turning back to face him on-screen, to ensure that I saw him pulling hard and fast on his impressive cock.
Sam, I was flattered, would explode to this sight of me. I would really get off on using my newfound femininity. Most times, I would climax too. Moaning softly in my best girly tones, I’d pull my panties down at the last second, to spray my soft tummy with hot cum, shudders running through me at the intensity of sharing these moments with Sam. How I longed to taste his cum again, as I had that one time in the cinema.
As our excitement ran away on these calls, Sam and I became braver and would gasp in whispers how I would so willingly offer myself to him, and how hard I’d like him to fuck me. Sam managed to prise from me that I was a virgin, but he was never very forthcoming about his own experiences. I knew he had dated a number of girls, and his family spent Summers at their property in Ibiza. Adding in his charm and good looks, I figured he’d had plenty of opportunity to lose his virginity. And, as I had promised myself at the end of our date, I planned to give my own to him just as soon as I could!
My friendship group of girls of course asked all about me and Sam. I’d mostly tell them everything! But we were mindful of not drawing conclusions about Sam’s sexuality, and certainly would not gossip about him beyond our group.
To relate better to MY emerging sexuality, during our date Sam had accidentally christened me as “Elle”. This, as you can now see, has stuck as my real “forever name”. But back then, as a seventeen-year-old in high school, and barely having started transitioning, it simply wasn’t possible to use my lovely new name.
But my girlfriends wanted somehow to acknowledge me as the girl I was becoming, and they loved the name “Elle”. So, with their usual mix of kindness and sharp wittiness, they adapted my name into the nickname of “Smell”, or “Smellie.” Why? Well, it meant they could acknowledge me as ME, without broadcasting everything about me to the world before I was ready.
As I think back, I can see now, that by adopting these nicknames, we were also gently stepping away from the boy version of me who had brought me through my first seventeen years. A boy who, of course, I will never forget, but who sadly I have now asked the world to forget.
As the weeks had passed, even if I was not ready for coming out, my resourceful side had kicked in, and I was making things happen. I, illegally I guess, had started buying estrogen hormone gel online. It wasn’t actually that difficult to find, and the restricted credit card that my mum allowed me, could be used to buy this girly liquid gold.
With teenage verve and attitude, I applied the feminising gel liberally. I soon noticed minor changes, mostly that I became more at ease with myself. Certainly also, my skin started to become softer.
Lying naked at bedtime, the sticky gel would dry on my thighs, as per the instructions on the dispenser. But, not as in the instructions, my balls and chest also got a coating! In the half-light of my room, my hopeful gaze down along my body would have to wait a few months before the hormones got my little boob buds showing.
I was also shaving, or tentatively waxing, much of my body. And, in the privacy of my room, I would practice feminising how I stood, how I walked, and even sometimes the pitch of my voice. All of this in secret, other than me telling just the closest three or four of my girlfriends.
And so the weeks passed until, finally, Sam and his cohort were approaching the end of their exam season. As he and I lay on our beds one evening, idly chatting on screen, Sam was visibly starting to relax. He laid there completely naked, gently stroking his rock-hard cock as I applied my hormone gel, and idly told him about my day. As if this budding boy-girly boy relationship was the most natural thing in the world!
“Hey, you need to tell the girls that you’re all invited to Oscar’s place for an end-of-exams party, Saturday” he said, smiling, as he stretched his thick, veiny cock for my obvious pleasure.
“Amazing, that’ll be fun,” I replied, trying to be cool about it!
“End of school for my year, baby girl. It’ll be wild!” he added.
My school year, one behind Sam’s, was a rich hunting ground for his friends. Lots of pretty, preened seventeen-year-olds from well-off South West London families. And I knew my girls would not disappoint!
With much excitement, Saturday evening came. Six of us gathered early at one girl’s house, to get ready. Tiny, colourful thongs and matching bras were slipped on by the girls. New crop tops or bodysuits, mostly paired with little miniskirts, followed.
My confidence, during these early days of transitioning, was growing. Encouraged by the girls, and knowing that this party would be a fairly safe space, I’d brought along a more feminine selection of options to our getting-ready meet-up. Besides, on the webchats with Sam, I had upped my girl game, and I felt that I could keep the momentum going. Plus, we had vodka, and I was getting brave!
So, I emerged self-consciously from the bathroom and into the hubbub of my girls, wearing my new dark blue thong and matching bralette top. I was painfully aware that I, of course, brought a penis to these gatherings! I’d practiced tucking at home, but was concerned that was not going to be a comfortable option for the whole evening and, besides, it really didn’t feel like the authentic “me”. But I worried if the authentic me would actually be well-received, in knickers!
But instead, bless their hearts, “Elle!” came the heart-warmingly positive reaction from my friends. And I was pushed, front and centre, to sit at one of our makeshift makeup stations.
A couple of the girls applied a little foundation to my face and to points around my forehead and neck. Some bronzer was then brushed on. A dusting of a couple of natural summery, tan-shaded blushers came next, to enhance low-lights in the contours of my face. My eyes were treated to the subtlest of eyeshadows, transitioned beautifully through smoky grey tones. My brows are fair, and were plucked just a little, and enhanced with a light-coloured pencil. Finally, shimmery little highlights were applied to bring out my cheek bones.
We avoided eyeliner and anything on my eyelashes, to keep my overall look subtle. Similarly, my lips were layered simply using just one shade of a very light, frosted pink, with a slightly glossy top coat then applied as a top coat. This pink matched the nail gloss I’d painstakingly painted on earlier. My look was rounded-off when one of the girls created the cutest, tiny bunch in the back of my hair, using a little band.
I looked, and felt, smoking hot!
Dressing next, I put on a new pair of dark grey, slightly shiny, leggings. Not gym-wear shiny, but a soft, casually-smart look. I ensured the leggings were worn snugly at my bottom, offering the clear and, I hoped, enticing contours of separated bum cheeks as defined by my thong underneath. To help prevent my blushes on arrival at the party, I added a long, washed-out vintage denim Levi’s shirt on top. This covered my bum at the moment, but would be tied higher at my waist later.
I put on little pink ankle socks, then fastened the laces on my red Adidas trainers. Into my little shoulder bag, I threw makeup essentials, mints and a little tube of lube (yes, it may happen, I thought!). A Hollister body mist dropped into the bag next, after a quick spray all over. Bangles, phone, and I was all set!
Our high school was free to attend, but academically selective. So my schoolmates were from a range of backgrounds. This diversity I think helped the acceptance of me as “Elle” (or, for the meantime, “Smellie!”). Certainly, parental pressure also helped reduce bullying, for fear of the indignity of being kicked out of school!
Parents were presented with a range of paid additional extras at school, including tutoring and extra subjects (thank goodness, as this was my route into my love of art). The school has an enviable record of university success – hence the pressure for Sam to keep a low profile those last few weeks.
The diversity at school also meant that our homes ranged from small social housing apartments, through relatively modest suburban homes, like mine, to large southwest London mini-mansions around Wimbledon. It was in one of these upmarket pads that Sam’s friend was holding the party. The parents were away, and its spacious rooms, terrace and garden made it the perfect location for this fun summer’s evening.
Having finished our communal getting-ready, we “girls” arrived like a whirlwind at the house and, of course, all immediately squeezed into a downstairs bathroom to tweak our appearances! Suitably prepared, we exited en masse and set out through the rooms of the house to see how the party was going.
It was going well! A mix of our schoolmates, plus people we didn’t know, were mingling, laughing, drinking, and dancing. Comments were passed on outfits and, I was delighted to hear that my clothes and appearance were well-received. A couple of white wines later, I summoned the courage to tie my shirt at the waist and unfasten a few of its buttons. The full effect was revealed as I’d planned. A glimpse of my bra top, and a (fairly!) confident wiggle of my tightly-clad bottom, and I was in full party mode on the makeshift dance floor!
We were having such a fun evening! Lots of girly laughs, a few more plastic cups of the cheap white wine, and, when he and his cool friends eventually graced us with their presence, some VERY flirty looks and smiles between Sam and me!
As it got later, energy levels dipped. The music switched to a slower, more chilled-out vibe. Couples started to break-away from the main rooms. Little groups formed to smoke much-valued (but generally not very potent!) joints outside. Friends hung out and chatted. And a large group from Sam’s year group set-off to a local nightclub. Being eighteen already (in the UK) they had that option.
So the party house had become much quieter. Those of my friends who hadn’t dispersed for some kind of alternative fun with boys, crashed, along with me, on and around some huge, plush sofas. I’d managed to find a cold bottle of wine and was enjoying it, cosied up with one of my buddies, Emma. She was sitting on the sofa, while I was on the floor, leaning back onto her legs. Nearby, two of our friends were sitting on guys’ laps, giggling and starting to make out. Those miniskirts seemed to have had the intended result!
Although Sam and I had made flirty eye contact several times during the evening, I assumed now that he’d headed with his friends to the club. But no! He appeared, as casually gorgeous as ever, at our sofas and squeezed in behind me, between Emma and the end of the sofa.
“Hello!” I leant back and greeted Sam, casually and warmly. Reflecting on how content I was feeling with the evening, I shifted a little to lean on his leg.
“Hey, you,” he replied, and “May I?” signalling to my wine.
As he didn’t have a cup, I passed him mine. I noticed my light pink lipstick had left a cute imprint from my mouth, on its rim.
“Perfect, thank you,” he acknowledged with his cute smile.
Watching with interest, as she tried to regain some modesty by adjusting her skirt, one of the girls on the laps opposite grinned at me and, in a stage whisper, said to me, “For fuck’s sake, Elle, why don’t YOU sit on HIS lap!”
As I blushed and scowled back at her, Sam leant over me to pass me back my cup. “Works for me” he said, smiling.
“HA!” mocked the girl, in triumph. Emboldened by the wine and by the chilled, late-night vibe, I sheepishly joked “Okaaaayyy” and pushed myself up by my elbows, to then wiggle my bottom sideways onto Sam’s lap, with my legs hooked over the arm of the sofa.
“Excuse me for not third-wheeling!” huffed Emma in mock annoyance, and shifted away from Sam.
He rested a hand lightly behind, rather than actually on, my waist. And with the other, reached for my wine again. I topped it up from the bottle and passed it to him. Our fingers brushed, and Sam allowed his to linger on mine.
I smiled as we held each other’s gaze. Although the moment was SO right, I was pretty sure that Sam would not kiss me here. However, he was clearly relaxed, as most of his friends had left for the club, and the low light of a few failing candles offered us some intimacy. I glanced around. More people had abandoned the sofas. My friends opposite were busy with their guys. Emma had left, unnoticed.
I felt Sam’s hand behind me move onto my bum. He started to lightly and slowly caress the smooth material of my leggings, pulled tight against my pert bottom. I sensed he was trying to identify a panty line. Not from these little knickers, I thought to myself! I felt girly butterflies in my tummy thinking about the very real chance of Sam exploring my thong. He gripped my bottom more tightly, and ran a finger from his other hand, along my outstretched leg.
I put down the wine bottle and rested my hand holding the cup on the back of the sofa, next to Sam’s shoulder. I draped my other arm across his other shoulder and shifted slightly to face him more closely. I naturally, and gently, bit my lip. He pulled hard at my bum as he drew his other hand up and next to our faces. He kissed his finger before placing it gently on my lips. “Let’s find somewhere,” he whispered. I nodded surreptitiously, still holding my lip in my teeth, excitedly and subtly provocatively.
We slipped away from the room, Sam reaching back and leading me by my finger. From the large hallway, Sam turned to climb the stairs, me in tow, and became very excited! There was no one around as Sam nudged open a bedroom door, beckoning me to follow with a flick of his head.
I remember slow RnB was playing low on the built-in Sonos system, in a thoughtful nod to what the room was mostly going to be used for that evening!
Sam leaned in to kiss me passionately, as I sensed him push the door closed behind me. He clicked the door locked, before placing that hand on my hip. I threw my little handbag across onto the bed, then wrapped my arms loosely around Sam’s neck as we kissed deeply. He resumed his grip on my bum, pulling me tightly towards him at the waist.
With one hand remaining on my rear, he brought the other between us and started to unbutton my shirt. My heart was racing as I dropped an arm from his shoulder and started to fumble with the waist button of his jeans. Momentarily, I moved my hand to pull open the loose knot in my shirt. It fell to the ground behind me as, below, I levered off my shoes at their heels.
My hand slipped into the front of Sam’s jeans. I started lightly stroking his cock through his boxers. I was surprised that he wasn’t fully hard, but I think that was because this was new territory for us! So, I slid my hand inside, and I felt both his confidence and the hot flesh of his cock, soon starting to grow!
Sam broke away from our kiss, to take in what I was wearing. He smiled as he ran a hand across my lacy bralette, then pulled down at the waist of my trousers. Removing my tight leggings needed my help, so I pulled them down and stepped out of them, as Sam kicked-off his jeans.
He took both my hands in his and, with a small gap between our bodies, visibly enjoyed the choice I had made (for him!) in underwear. He reached for my waist, as he whispered, “Elle, I’ve wanted this so badly.”
“Me too, Sam, me too,” I replied.
Still holding my hands in his, he took a few steps backwards across the deep carpet, to the bed. He sat, and as I moved my hands to take off his T-shirt, he kicked off his boxers, before falling back onto the bed.
He was SO hard now! I leant over him and wrapped my lips softly around his cock. I gently rolled back his foreskin as I flicked my tongue around the head, before taking him back into my mouth. Sam reached behind me, hooking fingers around my thong, and stroking my bum. My own cock was also now rock hard and straining at the front of my panties.
Sam groaned as my head moved up and down. Suddenly, the door handle rattled. I stopped and looked up, checking that Sam had indeed locked it. He had, and I returned my attention to him. Gripping his shaft at the base, I wrapped my lips around him and started running my mouth up and down again.
Pre-cum was dribbling heavily from Sam now, as I moved my head faster. As he groaned, I started to wonder if our time together would be just a blowjob again. He was obviously enjoying gripping my bum, and caressing it through, and around, my lacy thong. Sam wasn’t taking any interest in my cock, and that was OK with me. Still, though, I was hard against his hand at times, and so it was evident how much I was enjoying this.
As I really started to quicken my pace of sucking, and going fully over him with my mouth at each thrust, Sam must also have been thinking how long he’d be able to last! He gently took my chin between his fingers, stopped me, and moved to take his cock from my mouth.
Sam ran his fingers across my chest, taking his time across my hard nipples, and clearly enjoying that I’d dressed in my pretty underwear. He hooked his hand under my arm and gently signalled for me to move up the bed to him. As I did, he pulled at my panties. By arching my back to help, and by hooking the light lace with one of my feet, I’d soon kicked them off. Sam held my bare hip, and very gently pushed me to roll slightly away from him. As I stretched my lower leg, I tucked my other leg upwards, consciously offering my ass to him. He responded by starting to gently caress my tight little hole with a couple of his fingers. The whole lower half of my body felt almost numb with excitement!
I reached out across the bed for my bag and took out the little tube of lube. I flicked the cap open and reached back to squeeze some onto my bum and onto Sam’s fingers. He worked his fingers into me gently, as I gasped in ecstasy at the sensation of him opening me up. I felt him shift closer to me, and the hand I had behind me was brushed by his hard cock. I squeezed the lube again behind me and felt it more between my bum cheeks. Sam rubbed his hand into this lube, and I could sense that he was also applying it around his cock.
“Elle,” I thought to myself excitedly, “It’s happening, babe!” As I’d wished and hoped, Sam was going to be my first.
In seconds, I could feel the warm, soft pressure of Sam’s cock against my little hole. I tucked my upper leg slightly higher, and felt Sam slowly and gently entering me. I can still recall the rush of emotions and physical sensation, and I still get almost the same tingle in my tummy.
“OK?” whispered Sam.
“Yes, I’m fine, Sam,” I replied softly. And, as he held my hips, his cock moved deeper into me.
I’m not going to mislead you here, reader, by telling you I didn’t feel some discomfort at this, my first time. But the elation of this intimacy with Sam was so incredible, that I needed more and more of him inside me. I reached out, full stretch with both arms above my head, and gripped the bedding. Pushing myself gently back onto him, he was past the initial tightness of my hole, and giving me my first experience of entering my innermost cavity. This, as every time since in my life, took me to the next level of intensity.
His thrusts started, deep inside me, slowly and firmly. As he gripped my hips, I pushed back and whimpered and moaned. I could feel and hear Sam’s breath as he quickened. One of his hands came around to my chest and found a hard nipple. He pulled and rubbed at it, and the intensity of my pleasure deepened.
“Sam, yes, yessssss!” I gasped as he thrust harder and deeper. He kissed my neck as he pulled hard on my nipple. He slowed his thrusting inside me.
Sam slowed further and pulled gently out from me, as I enjoyed the same incredible sensation as he again passed my deepest points. He lay next to me, on his side and, by gently resting his hand on my hip, motioned for me to turn towards him. I rolled onto my back, my arms still partially stretched above me, and my legs bent. We smiled, and Sam leaned in to kiss me. He rested a hand on my chest and started to play with my nipples again.
We started to kiss harder, his other hand now cupping my face. Sam nudged my knee with his, signalling for me to open my legs. With one of my hands, I felt around at the top of the bed for the lube. I squeezed some into my hand again and applied it to my warm hole. As Sam shifted to roll softly onto me, I took his still-rigid cock fully in my palm and spread the silky gel onto him too. My hand lingered to grip and stroke him a few times. He gasped lightly, then took his intended position over me, him resting on his knees.
Together, we guided him back snugly inside me. My eyes closed with the sheer intensity of the sensation. He lowered himself to rest on his elbows, keeping his weight just off me, and I hooked my arms loosely and lovingly around his broad shoulders. I had never felt closer to being the young woman that I was becoming.
Sam, I knew, had dated girls, and school heresay was that he had slept with them. As he again started to slide up and down inside my body, I realised I was benefiting from his experience. For his age, I also now realise that he was a masterful and caring lover. He lightly kissed my forehead, my face, and my lips. My head tilted back in the moment, eyes still closed, me gasping and moaning. He kissed my neck and started to thrust faster and harder, while moving himself up onto his hands.
I can’t fully put into words the intensity of emotions and physical pleasure I was experiencing. I held him tightly as, without wanting to sound too rude here in my story, I was fucked soundly! I groaned and Sam grunted and gasped as he drove into me… and drove us both to new heights! My own little cock was leaking, of course, brushing at times against Sam’s tummy. I didn’t cum from penetration, dear reader, that would have been too much of a treat for my first time! But Sam soon did!
I arched my back as Sam held a final thrust deep, deep inside me. I gazed longingly up at him; his eyes were closed in ecstasy. I felt a shudder run through him and pass into me, as his cock released waves of hot cum. Time froze as I locked my arms around him. Finally, with a gasp, he relaxed, opened his eyes, and smiled at me. I held his face, and we kissed deeply.
The handle of the locked door rattled again.
“Come on,” I whispered, starting to slip out from under Sam. His body and spent cock looked beautiful in the half-light. He patted my bum, and we set about retrieving our clothes and dressing.
After a few more kisses, Sam opened the door. There was my friend Helena, peering nosily over Sam’s shoulder. Her and my eyes met. “SME-LIEEEE!” she exclaimed, in mock indignation.
Elbowing past Sam, with her boyfriend (one of Sam’s friends, and the same age) in tow, Helena kissed me on my cheek and whispered into my ear, “You’re OUTRAGEOUS!”
I blushed, slightly lowering my face as Helena was, for some reason, reaching over to the back of my head.
I realised she was unceremoniously pulling the cute velvet band from the pretty little bunch that the girls had put in my hair! Helena is a gorgeous, mixed-race girl. The same age as me, and, since we were little, she has always had a beautiful shock of long, dark, shiny curls. I had been so proud of own little hair bunch that evening. What was she doing to it?
As she passed towards the bed, she had released her beau’s hand, and was pulling her long hair back into a tight bunch, using my hair band. I realised that the minx was readying herself to give her boyfriend head!
“Me, outrageous?” I mouthed to her.
She winked and giggled back, “Girls will be girls, eh, Elle?”
With that, she gestured to her boyfriend to close the door behind them, as Sam and I exited the bedroom. Sam was already reaching behind his back towards me and beckoning. He took my fingers gently into his, and he led me along the landing. The door duly locked behind us.
The house was noticeably much quieter now. As we moved along the landing to the stairs, a whole new set of feelings passed through me. Emotionally, I was ecstatic. I’d lost my virginity in a way that felt so right, and I’d taken a significant, and very conscious, step along my journey. I was also closer to being in love with someone than I’d ever been.
Physically, I was experiencing, for the first time, that odd sensation of having a rear that feels both full and empty at the same time! I guess many of you will know what I mean, but right then it was very new to me.
I gathered myself together before we entered the lounge. I fixed my ruffled hair and, reaching behind me, I tried to rearrange my damp thong to feel more comfortable in my bum. Sam smiled to me over his shoulder. I felt both satisfied and naughty, as Helena’s words came back into my mind: “Girls will be girls, eh, Elle?”
I was positively beaming back at Sam, as I thought to myself, “Oh, we will. Oh, we will!”
