Aria (NSFW, first time, trans, tg, autobiographical)

It all started when I had returned from my first deployment to Afghanistan.

Nothing bad had happened to me or anyone I knew while I was there, but knowing you could be blown up or shot dead without warning, at any moment had an effect on me, I didn’t realize it until I got home.

Basically, the little voice in my head that told me I shouldn’t do things to allow myself to have fun because of some moral abstract had turned off. I guess the thought was, I could have died at any moment, and there were a lot of things I had denied myself… I guess I no longer wanted to deny myself!

I was 38 years old and married with children. Life at home and life in the bedroom was very “vanilla.” Nothing to complain about, but nothing to write about either.

I had duty at the barracks on base, basically a senior person needed to be present to keep an eye on things in case something happened. They gave you a room to stay in overnight, and the next day it was someone else’s turn.

That night, on a whim I decided to put an ad out on craigslist, just fishing really, looking to see if something would come up. I ended up chatting on my phone with a few ladies, but after a bit most of them went by the wayside due to incompatible circumstances. The only one left at 1a.m. was “Aria.”

I really wanted to make this happen. We had traded pics of our bodies and after getting comfortable enough, faces. She was of average height, on the thin side, long, straight, brown hair, nice abs, tiny perky boobs and ass. I was trying to arrange a meeting, but I got the sense she was stalling. I would normally have been more subtle, but I was tired of being the subtle guy, so I out-right asked her about it. What’s going on, why don’t you want to meet? I guess she responded well to the direct, honest approach.

That’s when she told me she was trans.

She apologized profusely, she said she had wasted my time and was afraid that I would be mad. Once I had a chance to get a word in, I asked her; What if I didn’t care? What then? Her reply was what I had been praying for: she told me I could pick her up in 20 minutes.

By 2 a.m. I was parked outside her house. She came out in sandals, leggings, a camisole and a thin sweater over that. Her hair was up in a high pony tail. When she sat in my truck she smelled wonderful; a light scent of soap and roses. It was a ten minute drive back to base, and about 15 minutes after I had picked her up we were in my room at the barracks.

On the way back we had talked a little more about her transition. She had been on hormone therapy for a few years and was happily living full time as a woman. As I looked at her in my room she had a classy appearance. Fine, aristocratic facial features. High cheekbones, narrow chin, elegant nose and refined make-up. She had thrown on house clothes so-to-speak, but the whole effect was elegant.

She enjoyed undressing me, slowly removing my uniform piece by piece. She took her time between garments to kiss me deeply, lick and nibble on my ears, neck, nipples and belly button. She mouthed my cock through my underwear until I was hard enough for the head to peek out above the waistband.

Then it was my turn to return the favor. After kissing her and using my lips to tease her face, ears and neck I pulled her camisole up and off. I sat back on the bed and puller her to me, letting her stand before me, her firm tits right at face level. I spent five minutes using my mouth to worship her tits before sliding off the bed and kneeling before her. I then mouthed her tiny cock through her baby blue panties before finally pulling them down and tasting my first cock.

She said the hormones made it hard for her to get hard or cum, but it didn’t take long for her little cock to rise within my mouth, just filling it. I didn’t know what came over me, but I put my all into that first blowjob. She was completely hairless, I kissed her all around, I sucked her little balls and rubbed her cock on my face and lips.

Before I really knew what was happening, she stiffened in my hands and filled my mouth with one swallow’s worth of cum. It was salty, slimy and gone in an instant as I eagerly swallowed the evidence of her pleasure from my attention!

She reached down and pulled me up to stand and kiss her, breathing words into my mouth in bewilderment. No one had ever made her cum by oral before! I felt awesome and thanked her for letting me. She then pushed me back onto the bed and began to worship my cock and balls. I kept my pubes trimmed short and my balls shaved, I really didn’t like hair down there, not mine or on other people.

She lifted my legs and had me hold my knees back as she dove into my asshole with her tongue. My mind was thoroughly blown! It was my first time being rimmed and it was unforgettable. She spent ten minutes worshiping my ass before returning to my cock and balls.

She then climbed up my body and sat up, smashing her balls against my spit-slick cock and grinding her soft cock against mine. Leaning forward and reaching behind her, she tried to put my cock in her ass. She only managed to get the fat mushroom shaped head in and began to ride the head with tiny motions of her hips. I could tell she was uncomfortable, but she wanted to please me badly.

I told her to give it a rest, but she wanted to flip over and have me fuck her. So she lay on her back, spread her legs and pulled her knees back to her tits to let me position myself in line with her gorgeous asshole. She tried to relax, but we only got a couple inches in. We got into a rhythm, we were able to get almost three inched deep, and as amazing as it was to be having anal sex with this gorgeous creature, I’m not into pain, not giving or receiving, so I called it quits.

When I stood up out of bed she quickly got on her knees in front of me and went to town on my cock with her mouth, when I was getting close to cumming, she told me she wanted it on her face, sending me over the edge! She pulled her mouth off my cock as I started cumming and tilted her face back, stroking the rest of it out of my cock onto her smiling face! When I was spent, she used her hands, fingers and tongue to swallow every last bit, smiling wide the whole time. We really made each other happy that night.

It was getting close to 3 a.m., so she showered off quickly, and I was dropping her off at her place about 20 minutes later.

From that night forward, if I had a chance to be with someone, do something I hadn’t before, I went for it!

Source: reddit.com/r/eroticliterature/comments/9tkr5z/aria_nsfw_first_time_trans_tg_autobiographical