Since I had first started my maturing I had never really seen myself as being my male body. Whenever I would have sex dreams it would always be from a women’s point of view. Eventually, it became my second self. I didn’t especially hate my male body, I just was never especially fussed about it or at home in it. I had no frame of reference on whether my cock was anything to write home about because my only reference point was through porn. 

During my later years, I started to experiment with my sibling’s clothes. Augmenting my body to make a more pleasing, more feminine body. I was a skinny little shit at the time and hadn’t broadened out and had the very attractive long hair look that any self-respecting male rocks when they care very little about their appearance.  So at a glance in poor lighting, I looked like a girl.

I loved being in girl mode, I would wait till every opportunity to go back to this skin. As soon as my family were out for a trip I’d wait, watch the car go, give it some extra time and go straight to raid the cupboards. How I loved it. I’d get dressed up, walk around in it, feel so confident, so alive so much more me. The fabric just felt so much more comfortable, so much more delicate, softer. Like even down to the undies, its madness I would feel the difference even if the thong in no way supported/held my gentlemen’s vegetables. I would swear that males undies of the time were made of cardboard and barbwire, girl pants were of butterflies and angel song. I would take pictures of myself, look at myself in all my forms, and inevitably do quite a bit of wanking because I was a teenage boy alone in the house.
One time I very nearly got caught by my dad, I had taken a bra and undies and had worn it to bed. When my dad came to say good night he noticed I had the covers up super high luckily he didn’t go any further into the investigation. 

I don’t believe my family would have much beef with if I followed through with the transition, we’re a liberal open-minded family and I grew up on listening to Eddie Izzard so the whole cross-dressing and body dysmorphia shouldn’t be too alien to them. 

I had never pushed the whole wanting to be a girl thing that much with myself growing up as it was still the era at school where if you weren’t straight with no extras then you must have issues and I was already bullied and unpopular as it was so wasn’t planning on adding fuel to the fire.

But when I went to uni I was able to explore this side of me with less dread of being caught and under the guise of Halloween, so for those three years, I like many other men at uni would opt for dressing up as a sexy lady every year.  

On one year we had the annual ‘Fetish ball’ where the logic was you’d go to the SU/club in your fetish and have a fun night out. But essentially every male went in drag and every girl went in a corset. 

During this occasion, I had tried not to fall into the usual trap of being too slutty and having overly ambitious boobs. I had got a nice body con knee-length dress, it sort of gave the impression I had rounded hips and the pattern was significantly distracting that it drew the eye away from my neck and head, not that I had a massive visible Adam’s apple. Black tights and 32b white lace bra, which I then went onto over stuff with bog roll to which I later found out was the hottest thing on planet earth and that socks though lumpy are far more comfortable.  Makeup was handled by a friend of mine who came in an amazing corset that almost sent the little men in my head into meltdown. So all brainpower was funneled to looking vaguely up and not down onto the boobs followed by face into boobs.
It was a heroic effort and I deserved a medal.

With my outfit set, my make up applied darkness set I set out with my corseted friend, my bff’s first time out to the fetish, who had gone all out with a mock necrophilia look, and me, reasonably realistic girl.

They went in the usual manner, queue up for ages to get a small drink that you’ll finish within seconds and repeat. My blood alcohol hadn’t reached the level where I could walk up to strangers but I could chat to people stuck in the queue and badly flirt. At some point, I have no memory how I ended up with a guy dressed as the man from cast away. I challenged him to find me someone who would be willing to do stuff with me, and we did a few laps of the club before leaving and making our way back to his. How or why I went along with what was happening I’m not sure. But I was reasonably sure I was about to find out if men were of interest to me and maybe play some xbox. I was mainly in it for the xbox.
 

Like a true gentleman, he offered me a brew and we sat down and plonked the tv on. We sat there for a bit before he started feeling up my leg, up towards my cock. 

He told me he wasn’t gay, I asked the totally watertight.

“Are you clean?”

He said yes and so I allowed him to continue to try and get my cock to harden. 

It was very much asleep when he started but after persistence, I did harden, and out of guilt for not giving him any attention I tried my hand at tossing him off at which point my member completely dwarfed his, so at the very least I learnt that evening that the girls I had slept with weren’t lying that I was big. 

His blow job skills were top-notch, very passionate, really put his all in, and for a long time was champion BJ of my cock. My skills of wanking him were either amazing or he was already ready to cum, because he lasted minutes. I stroked him up and down his shaft doing that thing where you curve your wrist as you pump. Played with the head, caressing the helmet with my finger so sensitive so alive. Soon into it, he came for the first time. His sticky juices flying out of his hard cock landing on my hand and his cock.
He looked at me and said

“Want a drink?”

I replied, “Sure.”

And followed him to the kitchen.

“Do you want to fuck me over the table? Can just put your cock between my legs and fuck me like that. Not down for proper anal just sort of simulated," I asked without fully comprehending I had suggested it.

“Sure," he replied abandoning making drinks, taking me by the back of my neck and wrist, and forcing me down onto the kitchen table. Rounding behind me and smacking my rear. My cock quivering. Hardening at the thought. With his hands by my waist, he kicked my legs open enough to slide his cock between my thighs and slid in. starting slow with big deep thrusts. Taking a handful of my bog roll breasts. Squeezing hard he increased his speed faster harder, pushing deeper.

“You like this? You fucking slut!” He panted.

“Keep going," I replied squeezed of breath.

“Oh fuck, oh fuck!” He exclaimed pulling out from between my legs and shooting his big load all over my ass. His cum soaking into my tights.

He made me finish on myself which made me feel like a princess, then he walked me back to campus and I went back to my room alone feeling like I must swing more so to the straight side of the bi scale so that would be straight by straight gay.