The Turning Point Date

I dressed since I was younger. But I considered myself straight. I figured it's a hobby of sorts, that I simply admired women so much: I wanted to be like them. Besides who doesn't want to be admired. It became a challenge to master the craft, to complete the illusion as much as possible. First it was just about learning how to look as fem as possible. I would read women's fashion magazines for ideas and started steering toward shemale porn. All the time not realizing or acknowledging what was really going on.

Next, it was online chat. Could I attract men through conversation and my personal photos of my hobby? Sharing my photos and chatting with men appreciating them was rewarding and motivated me to push further.

I decided to try going on a date as woman, Certainly that would be the ultimate to actually attract a man as a woman enough for him to want to take you out. The one date turned into several dates with different men some concluding with a level of physical intimacy. This would bother me at times, that perhaps I had gone too far and would result in purges; as if trying to remove the demons from my soul.

But the fact is, although I considered myself straight, I liked it. Each time I would return and start my craft all over again but a bit more advanced from where I left off. Over this period after there was one man that became a somewhat regular, if you can call it that. He seemed to understand the process and would patiently await my return each time joining a bit further in the play. Ron was an older mature big man, shaved bald head, harry chest, large stature. I was tall but he was even taller than I. He had a grey trimmed beard and was an old fashioned hopeless romantic of a guy. The kind of guy that opens every door for you, and pulls out your chair.

One warm summer day after tanning in a thong at a private beach cove, I looked down at my bronzed glistening oiled up smooth skin, my now shoulder length hair blew in the breeze. I kept my skin smooth now from head to toe as I told myself 'hey thats what athletes do it looks better'. Thats when my cell phone vibrated, it was Ron he want to come over for a Noon cocktail. I responded ‘yes’ and proceedEd to clip my bikini top back on and slipped my teal and white striped tube dress, with side leg slit over my bikini. Tanning like this although private yet in public was yet another of my hobby challenges I had graduated too.

I got home in time to take a quick bath and pant my nails. I slipped on thighs (I knew Ron liked those), lacy bra and g-string under a burgundy bodycon dress. My yoga had paid off putting curves in all the right places. I slipped on my heels and admired my work in the mirror. Hair styled, make-up on point, fresh nails and a rockin outfit. I was pleased. I secretly was hoping Ron would be as well. It didn't take long to find out. The door bell rang and Ron entered my apartment. He poured a drink for us both and suddenly reached around my waist from behind and kissed my shoulder.

One thing I had always avoided in the past was kissing another man. I could orally please him but kissing was off limits. Somehow Ron broke past the barrier and I found myself making out with this bearded giant. It wasn't long before my skirt was hiked up and I was on my back Rons weight pressing against me, my long legs wrapped around him. He was inside me working his magic when it happened.

I turned my head to admire my work, long smooth legs in sheer black thigh highs, heels pointing outward with this man between them. He began kissing my neck and I suddenly felt light-headed. What was happening I thought. I suddenly felt different. He was deep inside me as he switched to kissing my lips. He exploded inside me, a warm rush came over me. Was I having feelings of Love for/from another man!?! As if he read my mind Ron at whispered in my ear. "It's okay baby, you're straight, you're a woman and I am a man."

Turning point

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