Old Friend Made New

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A story about my first time with a trans woman.
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When I was in elementary school, I had a friend named Dylan. Dylan was always very effeminate. I remember asking him one time when he came over to my house to spend the night if he was gay. We were in fourth grade at the time, so there wasn't an answer to this, not really. We knew what gay was, in theory, but we didn't actually know what it was in practice. Dylan said no, he wasn't gay, but that he sometimes felt like he wanted to be a girl. I said I thought that was cool, and we went about our 10 year old business.

Years later, in High School, we took drama together. It was at this time that Dylan started to wear feminine clothing, growing out his hair and wearing very slight touches of makeup. We weren't good friends with each other in HS, but we sat across from each other in Drama for 3 years, so we were at least friendly.

A few years after graduating, I saw her on our local bar-crawl street, looking stunning in a green dress, her hair styled, no longer worrying about dumbasses that called her names. Our town was friendly but there are always a few.

"Dylan?" I called out as she walked by.

She froze in her tracks and turned, then smiled warmly. "Daniel!" she cried as she ran over and gave me a hug. I could feel her breasts pressing into me as I pulled her close. My heart started to beat a little faster.

"You look... Wow, you look incredible!" I told her as I stood back, my hand on her hips, my eyes moving up and down her body.

She smiled and blushed.

"Stop, you're sweet," She said, still smiling. "What are you up to tonight?"

"Nothing much. Just came here for a drink after class. What about you?"

"I just finished up at work, I was on my way to my car to head home for the day."

"Oh yeah? Well, I'm glad I saw you. You need to add me on Facebook." I told her, blushing furiously and kicking myself inside for the lame line.

She laughed again. Looking at me slyly, her sandy blond hair glowing in the evening light, biting her lip in thought and looking as sexy as ever doing so.

"Would you like to come over? We could smoke a little, hang out like old times. It has been forever," She said, squeezing my hand slightly.

My heart pounded in my chest. I looked at her beautiful blue eyes, gazing intently at me, and she knew my answer before I ever opened my mouth.

"Let's go!" I said, but she was already pulling me out the door.

------------------------

On the way to her house, I tried to figure myself out. I was young at that point, and having been raised in the South, my views on sexuality were very black and white. I wasn't a dick, I just didn't know that there were options outside gay/straight/bi. Whenever anyone asked me about my sexuality, I would usually tell them that I hate being put into boxes. That's true, I really do, but it was mostly because I knew that trans women were attractive to me, and trans didn't fit the binary gender standard. I didn't know pansexuality was a thing back then.

There are so many things about that first time with her I would take back now. I'd known her my whole life, and thinking of her as a woman was completely natural to me. I wanted her to know that, that I didn't think of her as a man at all, or a crossdresser, that I thought of her as a woman. It's all excruciating to look back on as someone more educated in human sexuality now.

Credit where credit is due, though, Dylan just laughed when I said stupid things. She told me I was sweet, that I was cute. My intention was clear, and that mattered to her.

When we got to her apartment, we sat on the couch and I rolled us a joint. She went to use the restroom, and when she came back out she was in the sexiest hot pink and black babydoll, with matching lace boy shorts.

"I hope you don't mind. It's been a long day," She told me.

I took her in completely now. Her toenails painted light pink, silky smooth legs leading up to her sexy body, her stomach flat and taught. She swayed just a little, letting the babydoll twist in the slight breeze she created, her budding breasts perfect behind the lace, the nape of her neck, her ruby-red lips, smoky eyes, and long voluminous hair. This gorgeous creature in front of me, who I had known almost all my life, had become the woman she had told me about almost 20 years previous.

I took a deep drag off the joint, standing and walking to her, pulling her to me and placing my mouth on hers, exhaling slowly. She breathed in, taking the smoke into her lungs as our tongues intertwined, lightly dancing together, our hands roaming each other's bodies.

I pulled away as a slight moan escaped her lips.

"I don't mind at all," I said, smiling slyly as I took a seat again. "Not one bit."

I winked at her like a dork. She laughed again, playfully hitting me as she sat down beside me.

"You suck!" She said teasingly as she took the joint.

I think that is the fastest either of us had smoked anything before. As we extinguished the final embers, she pulled me to her kissing me again, the longing of the past five minutes making us forget any and everything else. It was like lightning shooting through us both, every nerve ending in our bodies seemed hyper alert as our hands and mouths explored each other. Dylan pulled my shirt off as my hand went inside her lace babydoll, teasing her nipple as she moaned.

Gasping, she pulls away from me, looking me firm in the eyes.

"Bedroom. Now." She said.

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9 Comments
AnonymousAnonymousabout 8 years ago
Loved it, need more!

Ignore the naysayers, as a trans woman myself, I enjoyed the sincerity of this story. It's progressive tone, regarding trans women as real women, was a really nice change of pace from the standard transphobic bullcrap here. Please continue this story!

DianeRedfernDianeRedfernabout 8 years ago
More please

Agreed - love the set-up but I want MORE. SOON.

Hugs & kisses,

Di

LustKnightLustKnightabout 8 years ago
Tease!

Entirely too short. I don't insist that every chapter tell a complete story, but this was little more than a cruel tease. It also felt very rushed.

AnonymousAnonymousabout 8 years ago
More please

Liked it. I hope you add more soon.

AnonymousAnonymousabout 8 years ago
To short

Liked it though. It just it off to soon.

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