Discovering the Feminine

I had dabbled in dressing as feminine for years, it somehow felt right to me, i was a heterosexual male 80% of the time, and a heterosexual female 20%, but that 20% stayed behind closed doors to the world... until i showed Ryan.

Ryan went to my university and was my friend. He was pale, with green eyes and was tall, skinny with abs and we hung out a fair bit, I was one of the only people who knew he was bisexual. At a sleepover hanging at mine once he told me, and in return I told him my secret, he was the first person to ever know that I crossdressed and became Kelly sometimes.

Some months later, we were talking on Skype when he asked me something that took me totally off guard.

"Can I meet Kelly do you think?" when Ryan and I were on Skype chatting and he asked me that, I nearly fainted.

"Wh...why?" I blurted out, my cheeks were so hot. It was one thing him knowing I became a girl sometimes, but seeing her was totally different. My boy life and my girl life were totally separate, and I was terrified of mixing those worlds.

"I just... I've always been curious as to how she looks... I don't wanna offend you it's cool if not."

I hesitated... and said "fuck it. Give me an hour and I'll call you back." My parents were away for the night, so the house was mine. I got in the bath, put on my girly songs playlist and shaved everything. I was hairless, and my brain was switching to that girly princess mode that boys loved. I went to my hidden bag, tucked away at the back of my wardrobe, and emptied its contents onto the bed. I picked my pink bra and thong, and slipped them on. My dick was hard, which was frustrating, I couldn't have that being visible when I showed Ryan, but this process always turned me on, the pink thong made me feel so feminine and sexy.

In my underwear I did my make-up, admittedly I use a lot of make-up, it's not easy passing as the other gender what can I say? I put the black hair extensions into my hair, and it fell over my shoulders and to about my nipples. I put on the off the shoulder t-shirt, slipped into my girl jean shorts which hugged my ass, and sat down facing my laptop.

I was nervous as fuck, my girl voice wasn't brilliant, and no one had ever met Kelly non-sexually. I called Ryan on skype, and we sat in silence, he gasped and I just could not speak.

"Wow...Kelly, it's nice to meet you... you're beautiful." This may sound stupid but I nearly burst into tears, it just felt so liberating.

I smiled at Ryan and said "nice to meet you." My girl voice sounded okay, and Ryan looked kinda shocked to hear that voice coming from me. I stood up and span for Ryan, showing off my outfit.

When I sat back down, he quietly said "your butt in those shorts looks amazing..." As crazy as it sounds, I was stunned. I mean I should have seen this coming, Ryan was bi-sexual, my friend for years, and wanted to meet Kelly... but I'd also spent the longest time sitting on the PlayStation with him, sharing a bed with him when I stayed over, and he never made a move at all. Of course I now realise, he didn't fancy the male me, he fancied Kelly. And to be honest Kelly fancied him too.

"You should see it out of these shorts..." suddenly I was confident, horny, and my heart raced as I stood up, turned away from the camera and bent over. I slowly pulled my shorts down to reveal my thong covered ass.

"Oh my god." I heard Ryan say, I stood straight and my shorts fell to the ground, I looked at the camera over my shoulder and my mouth dropped open. Ryan's 6 inch cock was in his hand, he was wanking it... to me!

"Keep going" he said, so I bent back over for him, and pulled my thong down. I sucked my finger before I reached back and pulled my ass cheek open with one hand and start finger fucking it with the other. I could hear Ryan fapping away to me, I felt sexy and empowered.

I finger fucked myself for a bit, going up to two fingers, before pulling out and sitting back down, my erect cock leaking onto my pale legs. Admittedly it was quiet and a little awkward but we both were having fun.

I started jerking myself looking at Ryan, I spread my legs either side of the laptop so I could reach down under my leg and tease my asshole as I rubbed my cock. I let out some girl gasps and moans as my balls tingled,

Eventually Ryan whispered "I'm gonna cum..." I jerked faster, wanting to cum together. Sadly we couldn't, I was too nervous from it all, but Ryan came all over his shirtless body, he was so sexy... this did help me get there, as I imagined licking the cum off his abs, and fairly soon after he did I came into my hand, and then ate it for Ryan, he gasped as I did it. I was used to licking up my own cum and knew boys would love watching me do it.

It was quiet for a bit so I broke the silence and said "so I'm Kelly..." we both laughed, and chatted for a bit, he got to know Kelly, how she was different from the boy me, what she liked and didn't like, what turned her on and off... we eventually had to go.

Over the next week or so we Skyped a few more times, until Ryan said "Kelly, my parents are out the house tomorrow, wanna meet up in person?" My heart went crazy and my stomach flipped. Ryan definitely wanted to fuck me...

"Sure" I said, knowing that tomorrow was gonna be an amazing, new experience for Kelly. I was nervous, it was summer so we weren't in university halls, Ryan assured me he had a free house though, so i packed my bag with girl clothes and got ready for Kelly's first adventure outside my own bedroom.

I turned up at Ryan's the next day with my backpack filled with my girl clothes and make-up, I would have come as Kelly but couldn't risk being recognised leaving my house. Ryan welcomed me in and we sat in his room on the PlayStation for a bit like we used to, after an hour or so I decided I'd change.

"Brb" I said and stood up, taking my backpack into his bathroom. It took me about half an hour to get everything right, I was wearing the outfit I had on when we first skyped, it felt right and the pink thong i was wearing under my jean shorts made me feel sexy as hell. I had a white vest on top with a lightly padded bra too. I walked into his bedroom and seductively said "hello stranger."

Ryan mouthed wow and despite my nerves I walked over to Ryan and planted my red lipstick covered lips on his. He held me tight as we kissed, and his hand squeezed my ass, I moaned into his mouth, I saw fireworks as I kissed my best friend, he ran his hands through my long hair extensions. We broke the kiss and I laid on his bed, he climbed on top of me and we made-out, I could feel his erect cock poking against me as we kissed.

"Off" I muttered, pulling at his jeans, he stood up and threw his top off and slipped out of his jeans. "God" I moaned as I got on all fours and crawled along the bed to him, I could see his hard cock in his boxers and I wanted it. I playfully pulled his boxers down with my teeth, I loved his cock, the way it hung from his body looked so sexy. It was clean shaven, and looked beautiful on his body.

I wrapped my hand around his hard throbbing cock, continuing to hold it as I stood up while slowly jerking his cock. I unbuttoned my jean shorts and let them drop to ground, along with the thong that i stepped out of as well, I kept my top half dressed, but knew he'd love the sight of my naked ass whilst I went down on him. I got back on all fours, my bare ass in the air as I took Ryan's cock into my mouth, it tasted so good, I used one hand on his shaft while I sucked his cock, I tried to maintain eye contact as I did like the girls in porn, I wanted to be perfect for him.

He eventually stopped me and I looked up at him, "turn around" he said, I got into doggy on the bed and to my shock I felt Ryan spread my ass cheeks and start licking my ass. I moaned gleefully as he tongue fucked his little slut. The pleasure was incredible, he licked such big strokes that my balls were being licked too, I wiggled my butt in his face and moaned his name as he licked me.

"Fuck me baby" I eventually blurted out, Ryan got on his knees behind me and teased my asshole with his cock, before slowly penetrating me with his prick. I gasped and bit his pillow, it hurt at first but I knew how amazing it was about to feel. Ryan slowly started fucking me and the pain subsided, he held my hips as he slowly fucked me, I was in heaven. My cock stood on end as my best friend started to fuck me harder. I was gasping and moaning as he pounded my ass, my rock hard cock flailed around and dribbled cum everywhere.

I'm not sure what caused it, it was probably the excitement of fucking my friend, but out of nowhere I knew what was about to happen, even though I hadn't touched my dick once "Ryan baby I'm gonna cum!" I nearly screamed, my cock was tingling and pre cum was leaking out of me.

He moaned and pounded harder "ooh yes cum Kelly" he demanded, I squealed and my eyes rolled as he kept fucking me, I couldnt help but cum on his bed, gasping and panting as cum leaked out of me.

This sent Ryan over the edge and he said "I'm cumming baby oh god your ass is too good."

I thrust against him wanting his cum and wow did I get it, Ryan thrust his cock into me and gasped as he shot his load inside me. I felt his warm cum deep inside me, it was so much, my first ever creampie, it felt amazing. He slowly pulled out of me and I felt his cum follow, dripping down to my balls. It was so warm, the flow of cum dripping out of me confirmed to me that I had done a good job, I felt so sexy knowing I'd pleasured him.

I laid there, exhausted, as his cum dribbled out my butt, he kissed my back and I smiled to myself, however my heart dropped, and panic set in, when I heard Ryan's front door open to his house "shit" Ryan said, I was white as a ghost...