So, the shy boy who started university graduated three years later as a proud (but, to be honest, still slightly shy!) young woman. Elle had been born as I came out, started my hormone therapy, and ultimately changed my Christian name and gender officially.
Four years on, and at the time of writing, I’m twenty-five. It sounds a bit clunky to describe me like this, but I’m a transitioned, full-time trans woman. I have not had gender reassignment surgery and do not plan to. My feeling is that my gender need not be defined like that, and I’m perfectly happy as I am. But, of course, to get here has been a journey, to say the least.
I’m the third of four siblings, having two older brothers and a younger sister. We lost Dad when I was eight years old and, as a result, we’re a very close family. This love and understanding have been instrumental to the support of my transition. But the freedom of my second and third university years, as I passed twenty and turned twenty-one, was really when I decided and acted upon my future as Elle.
But what next after uni? I so needed space and time to truly find myself. I wasn’t ready to commit to a career, so on a whim, and with my fresh new passport, I set off for a summer working as a waitress in the very LGBTQ-friendly Spanish resort of Sitges. A friend of one of my brothers had gotten me an intro at a busy bar-restaurant and, within a day of landing in nearby Barcelona, I was waiting tables and bar and sharing staff accommodation with the loveliest bunch of summer workers. We were a mix of girls and boys of various nationalities, and mostly around my own age.
My roommate was Olivia, also a trans girl, Italian, and way more confident and sassy than me. She’d had breast augmentation—not particularly large boobs, but pert and noticeable! And, as I had already noticed when she walked around our room in very brief thongs or shorts, before she fully let it all out and crashed naked on her bed. Olivia (Liv) was VERY well endowed!
Now, I had never been blessed in the pants region, and my hormone therapy (plus extra oestrogen gel that I purchased myself to apply heavily) kinda stopped any development in that area. Shaved or waxed, plus softened by the hormones, my little underbelly and balls were as pink as a typical English rose. My small dick, cut and neat, was easily tucked away inside my panties. My little natural boobs, gradually developing from the hormones, plus a few exercises and a lot of wishful thinking, didn’t quite jiggle in the same way as Olivia’s. But I too dared to be naked in our room. I was ecstatically happy to be living my real life at last. I just didn’t have bella Liv’s olive-skinned, hung, uncut but equally smooth presence.
We both had long hair—mine naturally dark blond and gradually becoming streaked by the sun, usually worn in a ponytail or down, while Liv’s was dark and often tied in a knot with her waitress pencil stuck through it.
Liv’s English was excellent, from a classy education, and we spent many hours sharing our experiences and dreams as we lay on our beds, sunbathed together on the beach, or cuddled up under a blanket at the many after-work beach bonfires. We became close and enjoyed finding ourselves pairs of cute guys on holiday, often German or Scandinavian, as we both had a thing for tall, athletic, fair-haired men.
Sitges has a strong gay culture, and we rarely surprised the guys we hooked up with what was in our panties. But even so, from experience, I always made sure, whilst first making out with guys, that I’d lightly brush my cock against their hand or leg while still dressed so that they knew what was beneath my tiny miniskirt or shorts. Of course, if they’d started chatting us up on the beach during the day, there was no hiding in our bikinis that these two pretty British and Italian girls had more than usual within the flimsy material. Certainly, many of the holidaying dads took a lot of interest too, and I noticed them often needing to hide a semi in their shorts as we smiled at them, adjusting our thong bikinis or slowly applying our sunscreen!
But let’s get back to the real deal and the boys that Liv and I would pull. I’m not bragging or exaggerating that, during the course of that summer, I was fucked hard and regularly: on the beach (day or night); on top of the stacks of rental sunbeds; against the wall behind various nightclubs; in the bathrooms of bars; reverse cowgirl on a quiet backstreet sidewalk; once in a swimming pool; and, of course, back in guys’ various hotels.
I’d sucked cock in more places, cars, and quiet corners than I can remember. Liv and I never double-teamed (I will post the story of when we were absolute cum dumps, along with two gorgeous Black cis girls, for a group of guys on a superyacht—but that’s for another day), and we coordinated which of us would go fuck elsewhere and which could take a boy back to our room.
More of those exploits in later stories, but right now I want to fast-forward to two weeks before the end of our summer season. Liv and I had kissed and messed around several times. We cuddled and snoozed together like many friends do, and, as one or both of our cocks responded, our kissing had been accompanied by mutual wanking and some slow, sexy oral and pussy eating. I loved how Liv would caress my tanned boobs and work my nipples hard—pinching, sucking, and biting. My hormones often made my nipples hard for days, and Liv’s dominant biting treatment of them made me sweat and groan and feel a delicious soreness for days later.
In return, Liv adored me eating her smooth, dark pussy for what seemed like hours. She’d lie face down, bum raised, as I’d gently part her pert cheeks to allow my tongue to explore her. Cupping her balls in my hand, I could feel the pulse of her hard cock, as my other hand slipped a finger or two alongside my tongue into her gorgeous, smooth, sweet hole. We both paid for regular waxes of our bum cracks, and wow, I enjoyed the benefits. The coconut smell of her aftersun cream and that warm, fresh, slightly sweaty scent of her hole will stay with me forever. She’d sigh and mutter something in Italian as she gently worked her pussy further back into my face. Perfect!
But we hadn’t fucked. We had this heady mixture of sensual lovers and devoted friends, confessing and sharing so much. I know Liv topped guys, but that wasn’t—and still isn’t—really my thing. As we lay in bed one night, she told me she saw me as a butterfly (sorry, cliché!), growing as myself through the summer, and that, although she’d heard and even seen me being fucked, she knew it wasn’t yet the time for us. Even now, as I type this, I can feel that same longing feeling deep below my tummy that I felt back then, wanting to feel her inside me.
One night, it was like two or three in the morning when I heard Liv let herself quietly back into our room. That week, she’d been seeing a good-looking British guy who was holidaying with his wife and kids. He could slip away from their hotel for a couple of hours, saying he was drinking with a few guys, when the truth was he loved the dominant Olivia to fuck his butt hard against a wall in a gay club.
Unusually, back in our room, she went straight to the shower. I thought no more of it and fell back to sleep, facing away from our bathroom, to the soft hum of our ceiling fan.
I felt a soft kiss at the top of my back, and Liv’s arm softly stretch out along my waist and hip. Nothing particularly unusual about that.
“Night night, bella, I hope you had a fun evening,” I whispered.
Her response was to gently pull closer and slip her hand from my hip to my limp cock, gently stroking it with a couple of her fingers.
“I had fun,” she whispered. “But all I could think of was fucking you, Elle.”
I raised my leg slightly, and she cupped my growing cock in her hand.
“Liv,” I whispered, “that’s all I’ve thought of for fucking weeks,” and giggled, still not assuming this was going anywhere.
I felt her move away a little and sensed her stretching back across towards the little cabinet that sat between our beds. Seconds later, I could tell she had hold of the lube we kept in there, and she’d liberally squirted some into her hand. I felt the cool, silky lube being lightly spread across my ass. My little hole twitched in anticipation, and shortly after succumbed to two of her fingers slipping into me. I gasped softly as she slowly rotated her fingertips before she withdrew them again just as far as the lower side of my rim. Stretching me gently downward and open, I could feel as she ran her rock-hard cock along the palm of that hand before deftly guiding her tip into me with the two fingers that had been opening me up.
Again, I could feel the cool, silky lube, this time on the exposed tip of her cock. I love an uncut cock, and Liv had clearly slipped her foreskin back for us to both enjoy every single millimetre as she slowly and confidently slid into me. I raised my leg slightly more and gasped again as she slid fully into me. I felt my own cock dribbling pre-cum against my leg.
I sensed this wasn’t going to be the hard-fucking girl I’d heard in action so often. Instead, she stayed deep inside me, working her hips slowly and rhythmically. It also wasn’t the girl who insisted on condoms as she had fucked her way through the summer. Liv was inside me bare—raw, call it what you like—we were flesh against flesh as I felt the warmth of her cock and an intensity matched by her quickening breathing and grip on my hip.
Still, she ground inside me and pressed her waist harder against me. She was indeed balls-deep, but in such a sensual way. The intensity of feeling was like nothing I’d experienced before. She moved her hands to my shoulders, me still on my side. I pushed back in time with her slow rhythm, keeping our hips close as she gripped tighter on my shoulders. Her breathing quickened as she kissed my back, then sucked on my neck, clearly to mark me as hers.
She moved one hand to my hair and stroked the long ponytail I had made for sleeping in. As she gripped and pulled it harder, I let out a little squeal of ecstasy. She pulled harder—we were both enjoying the effect.
Liv arched her back and started to thrust more now, still the full length of her rock-hard cock deep inside me as I gasped and groaned with her every move.
Harder now, and still staying deep inside me, she shifted our weight slightly so I was facing into the bed a little more—enough of an angle for her to ride me harder. Her hand moved from my hair to my butt, gripping my upper cheek, pressing it and parting my butt crack, exposing and stretching my pussy wider. This she used to quicken and lengthen her thrusts as I tried to suppress my squeals of delight. Harder and harder now, my cock leaking as I guess hers was too deep inside my pussy—my achingly hot pussy, stretched and owned by this Italian beauty.
“May I, I want to…” she started.
“Cum inside me,” I interrupted.
Barely five seconds passed.
“Ohhhh, I’m cumming, Elle,” she whispered breathlessly as my own balls tightened and twitched. My rock-hard cock shot my cum across my open leg and onto the sheet as Liv stopped her final thrust deep in me, held me tight at my hips, and pumped her own seed deep, deep in my ass. I tightened in complete ecstasy, feeling every movement of her in me and the warmth of her twitching balls resting on my butt cheeks.
She released her grip, and my cheeks softly came back together. We lay for ages, her cock limp but big enough to still be just inside me, my own cum starting to dry on my leg and setting on my sheet.
That night, we kissed and held each other with a new gentleness. And the following morning, even after showering together, I could feel her thick cum gradually working its way out from me and onto the string and gusset of my little thong, cooled by the summer breeze around my tight black miniskirt as I worked the restaurant.
And as I returned the smile of a guy sitting in the restaurant with his wife and kids, Liv flashed her own gorgeous Italian smile at me. Despite my tan, I blushed as she knew I’d just realised I wasn’t the only one there who’d been fucked by her last night.
