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My Best Friend Is a Femboy

My Best Friend Is a Femboy

by Hourglass_twin_erotica
20 min read
4.81 (47200 views)
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I met my best friend when I was only five years old. Myself and Ash were in the same reception class and while I don't remember it all these years later, my mum always tells me that when she came to pick me up that day, we walked out of the school doors hand in hand, already the best of friends. Maybe it was an early sign of what was to come for us later in life, but no-one could have predicted it back then, least of all me.

Over the years we got closer and closer, a shared love of comic books and sports bonding us until the point that we were virtually brothers. Ash had a troubled home life with an absentee father and an on again, off again alcoholic mother meaning that he spent as much time in my house as he did his own. My parents treated him like a second son, ensuring he was well fed and taken care of, even when his biological parents were unable to. At first we had to share a bed if he needed to stay the night and it wasn't uncommon for us to wake up cuddled next to each other for warmth, especially during the winter months when the windows would ice over in the mornings. Most guys would find it weird being so physically close to their friend, but for us it was totally normal and I can still recall the nights I held him close in my arms as he cried after being screamed at or flat out abandoned for days at a time by his mum. He told me I made him feel safe and loved in a way that she never could, something that brought tears to my eyes and that fills me with an immense sense of pride to this day.

As we entered our teenage years, we became the targets of school bullies who loved throwing homophobic slurs at us and claiming that we were secretly a couple. Of course it wasn't true and we largely ignored it, but I could tell that it upset Ash a lot more than myself. I didn't think much of it at the time, he'd always been a sensitive guy and so it was what I would expect from him, nothing out of the ordinary or peculiar by and stretch. Being a teenager is hard enough without worrying about being insulted and harassed every day, so it was a real rough time for both of us and it brought us even closer than before. We were both overjoyed when we finished our exams so that we could move onto college, safely away from the boys that had spent years victimizing us as they went straight into work, or onto benefits as we continued our education. Life got easier as we studied for our A Levels and we remained as close as ever. When selecting Universities, we made sure to pick the same ones so we wouldn't be separated and even managed to arrange to live together in the same flat, just the two of us, which was when things started to change.

It was fair to say we both grew into different people over the years, Ash becoming borderline obsessed with anime whereas computer programming became my own personal passion, but these differing interests didn't drive a wedge between us, in fact, they only made us closer. We would snuggle up on the sofa to watch whichever show had captured his interest that week and he would always keep me well supplied with drinks and snacks when I was knee deep in a coding session. It was the perfect living arrangement, but it couldn't go smoothly forever as one fateful day, Ash's laptop suddenly stopped working without warning. He walked into the living room looking distraught, tears forming in the corner of his eyes as his lip trembled. With his family being so poor, his second hand laptop had been a gift from my family a few years earlier, something he relied on for his studies as well as watching his precious anime and the thought of it being broken had scared the hell out of him. "Bruce, please, can you fix it?" he pleaded with those big adorable brown eyes of his staring up at me, all his hopes riding on the one person that had never let him down.

"Let me take a look," I replied, taking it from him and opening the lid to take a quick look. "I have a lecture in a few minutes, but I can try and see if I can fix it when I get back?" I offered hopefully.

"Oh my god Bruce, thank you so much!' he exclaimed as a tear rolled down his cheek, quickly wiping it away so he could give me a huge hug as I stood up to meet him. He held me tightly, his small frame against my much more muscular body, skinny arms wrapped around my waist, face buried in my chest as I stroked his hair softly. As much as we had changed in terms of our personalities, we had also changed physically too, him remaining slender and petite while I had grown taller and broader which was only emphasized further when I'd started weightlifting a couple of years earlier. I told him not to worry about the laptop and after grabbing my bag and jacket, I said goodbye before heading out for my day of studies.

Returning to the flat in the late afternoon, I found it empty and after grabbing myself a drink and some food, I turned my attention to his broken electronic device. The first thing I tried was plugging in the charger, quickly confirming the problem was power related as the charging light didn't come on. Retrieving my set of tiny screwdrivers I used on my PC set-up from their place in my bedside table, I took to work loosening all the screws to take a look under the hood. My initial suspicions were correct, the fixings holding the battery in place had come loose and after some quick twists with the phillips head to get the connections back in place I was ready to reaffix the back of the machine and see if my handiwork was a success. Upon plugging in the charger, the little orange light on the side lit up and I was able to power on the machine, smiling to myself, satisfied at a job well done. Fixing techy things was one of my favorite things to do and I was usually tinkering away with something, so this was less of a chore and something I reveled in. I knew Ash would be so happy and relieved when he got home, but as it booted up to check there were no other issues with the laptop a sudden, strange temptation overtook me.

Without even thinking I opened the internet browser and a message popped up. "Do you want to restore your last session?" My finger hovered over the trackpad for a second, debating what I should do. It would be an invasion of privacy to do this, but it was Ash, my best friend. There were no secrets between us and whatever he had been browsing before the issue would probably be completely innocent. Throwing caution to the wind, I pressed downwards and several tabs suddenly appeared, each loading one by one via our cheap, slow as fuck student WiFi. The first one was what I had expected, the anime streaming page he used to watch his shows, but as I clicked through each of the open windows, things got more and more surprising. A lingerie website? Maybe he'd met a girl and he hadn't told me? But why would he keep a girlfriend a secret? It didn't make any sense. The next tab was some kind of comic strip with a main character that bore a striking resemblance to Ash. In the panels he was debating what to wear for some kind of date, choosing through a selection of stiletto heels before applying some makeup. The next several tabs were all from a porn website, one I had frequented numerous times myself and I once again hesitated before opening them. Hadn't I already gone far enough? A little curious voice in the back of my head told me no. I needed to know what he'd been looking at. Loading up the first page, I realized that I'd never seen this type of adult content before, it was femboy porn, each and every tab. Pretty, effeminate guys dressed up like girls, wearing makeup and sporting various shades of brightly coloured hair, stroking their throbbing cocks, giving soft, wet blowjobs and getting their arses pounded as they moaned and whined pathetically.

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I had an uneasy feeling in my stomach, my mind starting to put the pieces together, but I still didn't want to accept the reality that was staring me in the face. Only one tab left and as I opened it, I was relieved to see that it was a blog of some kind. It looked pretty innocuous at first glance, but as I started reading through the most recent posts, the truth about my best friend slapped me in the face like a freight train. Ash... is a Femboy. The blog detailed his daily musings about his life and it appeared that there was no subject he didn't cover, but the central theme was the same throughout. He talked about outfits he wanted to try, experiences he wanted to have and how he feared what would happen if those he loved found out his dirty little secret. Well, unbeknownst to him, that exact scenario had just happened.

I was still reeling from this discovery when I heard the key turning in the lock and there was only one person it could be. I froze, instantly locking up and unable to react, sitting dumbly on the sofa, laptop open in front of me as Ash stepped inside, dropping his bag on the floor before looking over at me, a huge smile on his face as he saw his computer up and running. He bounded over towards me, "oh my god Bruce, you're a lifesaver...," he said before trailing off as his eyes fixed on the screen. All the color drained from his face as he saw what I was looking at. His secret life had been exposed and the look of pure fear that spread across his visage broke my heart. "I..., I can explain...," he started to say as we both stared at each other, scarcely blinking as time stood still, seconds dragging like hours, trapping us in this horrible moment.

"It's o... okay," I finally managed to croak out, throat dry, heart pounding as I could see Ash bordering on a full blown panic attack as he trembled where he stood. He'd suffered with them all his life and I was an expert on how to deal with them by this point. I finally snapped out of my stupor, standing up to wrap my arm around him and bringing Ash down to sit on the sofa with me. His breathing was rapid and erratic, this was an especially bad one and so I clutched him to my chest and gently whispered to him, helping him calm his breathing as I felt his small body shaking like a leaf against mine.

It took almost ten minutes, but once he had calmed down and the attack had passed, we talked for a long time, late into the night as the sun set outside. He explained how he had always known there was something different about him, but that it was only once he'd left his home and moved into the flat with me that he'd properly been able to explore those feelings. He'd found a community of similar people online and realized that his more feminine side wasn't anything to be ashamed or embarrassed of. Over time, he had started to experiment, buying some skirts, growing out his hair, but he still wasn't ready to confide in me about it. Tears were shed by both of us and by the time we both went to bed, I promised him that I still loved him and just needed some time to process things. We both went to our separate bedrooms, sharing a tight embrace before saying goodnight and closing our doors behind us. I tossed and turned in bed for hours until I finally managed to get to sleep, my dreams continuing my inner turmoil throughout the night as my brain tried to process what I had discovered.

We didn't see each other until the next evening and I could tell how anxious he was as soon as I entered the flat. He was sitting on the sofa, instantly pausing the anime he was watching to turn and look at me. He was wearing a little crop top that I hadn't seen him in before, showing off his slender midriff and where it widened out into his hips. His skin looked soft and smooth and he already seemed more comfortable being his truer self, which made me smile, the relief immediately obvious on his face at seeing a positive reaction. We talked some more and I explained that I was fine with everything that he had told me and that he should feel able to be himself while we were at home. He was overjoyed, wrapping his arms around my neck and kissing me repeatedly on the cheek as his happiness overflowed. It was nice seeing him back to his usual self again and from that day forward, our home life changed drastically.

He would spend his time out of the flat in "boy mode," looking no different to any other young man on campus, but when he returned home, he shed his costume like a caterpillar escaping from its chrysalis, turning into the beautiful butterfly that he was always supposed to be. He would close all the curtains, before going to his room, applying his makeup, fixing his hair and getting into his femme attire. At first it was subtle. A cute little crop top or corset before progressing onto skirts and fishnet tights. I couldn't deny he looked good in them and sometimes it was hard for me to remember he was the same boy I'd grown up with. It was wonderful getting to see him like this, a flower in full bloom, beautiful and confident. Joy radiated from him and while the first few days were awkward for us both, we quickly slipped into a routine and eventually it felt entirely normal for him to be dressed like the cute little femboy he was whenever we were at home.

A few months later, things had reached a happy status quo when one day, without any warning whatsoever he came out of his bedroom in an outfit I'd never seen before and my jaw damn near hit the floor the second I laid eyes on him. He looked shy and flustered standing there in a black lace bra, panties, stockings and suspenders, hands covering his crotch as he entered the room, unable to make eye contact with me. I did my best not to ogle him as I chopped some vegetables on the kitchen counter so I could make us our evening meal, but it was hard to resist looking. I'd recently encouraged him to start working out with me and he'd clearly been working on making his body more feminine. His arse looked peachy and jiggly, his arms and legs looking a little more filled out, thighs soft and inviting with a hint of chubbiness that was irresistible. He took a seat on the sofa and turned on the television as we exchanged nervous glances at each other from across the room, both too afraid to say anything. Eventually he got up to grab a drink from the fridge, forcing him to stand right beside me. My eyes burned into the knife as I chopped an onion, every fiber of my being burning to look at him but doing my best to resist. He shouldn't look so good dressed in women's underwear, but I couldn't deny that he suited it, especially as the look was accentuated with his long blonde hair tied in a pair of cute pigtails and soft makeup that showed off his feminine features.

After retrieving a beverage he made his way back to the sofa and I found myself involuntarily looking over my shoulder, staring at his arse as he walked. His panties had ridden up a little, pushing up both of his cheeks as they shook and jiggled with every step. Between his legs I could see a cute little bulge where his balls were nestled up against the fabric and I couldn't look away. I was pulled out of my fervent ogling when he turned around the arm of the sofa, his eyes seconds away from facing me and catching me leering at him, my head quickly snapping back to the task at hand. Shaking myself to try and clear my thoughts, I resumed my chopping until our dinner was ready to go into the oven. Turning around I saw that Ash was still sitting on the sofa, eyes focused on the screen as he absentmindedly twirled one of his pigtails with his fingers. I could see how red his cheeks still were and I debated going into my bedroom to avoid what was sure to be an awkward interaction, but I stopped myself. Putting myself in his shoes for a second, I realized that I was the only person he could be himself around. He was probably waiting for some kind of positive affirmation from his childhood best friend. As tough as this might be, I would be a coward if I didn't walk over there and sit down next to him.

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Taking a deep breath, I walked across the room, Ash shuffling along the sofa to give me room, being careful to make sure that he didn't accidentally expose himself as he moved. I took my place next to him as we both sat, as stiff as statues, a rising tension in the air with each passing moment of silence. "So, new outfit?" I asked, immediately regretting the stupidity of my question, resisting the urge to facepalm myself.

"Yeah..., I thought I'd try something a bit more..., provocative, you know?" Ash explained before silence once again fell between us. God this was so awkward, I could barely handle the tension as we continued to glance at each other. I swore it felt like Ash was inching closer to me, but it was probably all just in my head. He cleared his throat before speaking again. "So, what do you think of it then?" he asked with a shaky voice.

I swallowed hard, an audible gulp sound breaking the quiet before I spoke, "yeah, it looks really nice, you suit it. Very sexy." I couldn't look at him, staring at the television instead and hoping the sofa would somehow swallow me up and remove me from this situation, but the furniture stubbornly refused to devour me and so I soldiered on as best I could.

"Thanks Bruce, that means a lot to me," Ash said candidly, reaching out to squeeze my hand, which just about made me jump out of my skin as I turned to look at him, our eyes meeting before I looked downwards. My eyes stopped at his crotch, which was no longer covered by his hands and there was no denying the small bulge hidden behind his panties. My best friend was sitting next to me wearing womens underwear and he was rock hard. I felt Ash withdraw his hand from mine and realized that he'd also looked downwards and noticed where I was looking. His cheeks were burning red with embarrassment and as we looked at each other my eyes returned to his barely contained boner. Before I realized what I was saying, a masculine defense mechanism kicked in, one that I'd relied on back when I was a teenager when I needed to try and deflect.

"Wow, your cock is so small," I said before clasping my hand to my mouth. Ash had opened himself up to me, allowing me into an incredibly vulnerable part of his life and I'd just insulted him in an incredibly embarrassing moment. I couldn't believe how much of a moron I was, but there was something even more unbelievable waiting for me once I looked at him again. I was expecting to see pain, humiliation and possibly even tears but instead I only saw arousal. He'd liked what I'd said? What the fuck was happening? Before I could think anymore Ash was leaning forwards and his lips were against mine. My mind told me to push him away, to be disgusted, but I wasn't. As I felt his small body against mine, his soft lips meeting with my own, I wrapped my arms around him and kissed him back. It felt like the floodgates had opened, years of friendship and repressed feelings being realized in one confusing, beautiful, intoxicating moment.

I could hear him moaning softly as we made out on the sofa, he sounded so feminine, felt so good and in short order it wasn't only Ash who's member was throbbing and swollen. He turned his body so that he could climb onto my lap, my hands grabbing his peachy arse, the feeling of his lace underwear on my palms, Ash whining gently as I groped him. "Fuck Bruce," he whispered in between kisses, "I've wanted this for so long..."

"You have?" I asked, still trying to process what was happening. Ash only nodded shyly in response, moving a strand of hair from out of his eyes, smudged lipstick from our kissing matching his red cheeks. He looked so cute and vulnerable, I'd never seen him like this before, but I could definitely get used to it.

"We can stop if you want," he murmured and I could see him withdrawing into himself as he questioned if he'd gone too far, pushed past the confines of our friendship and permanently damaged our relationship. I knew I had to act quickly, grabbing him by the hips and pushing him over on the sofa so I was on top of him. He squealed as I towered over him and there was that same look of arousal in his eyes as when I'd commented on the size of his member.

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