Transition for Love

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Trans woman finds true love.
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This is a work of fiction. Names, characters, business, events and incidents are the products of the author's imagination. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All persons portrayed in this work are above the age of 21.

I always felt like I should have been born a woman. Growing up, everyone just thought I was gay but I didn't feel the same. I was attracted to men but not gay men, hence I led a lonely, sexually self-fulfilled life. I yearned for the touch of a real man.

I started transitioning in college but my parents were unsupportive and the requirements of the university, at that time, was that I had to live completely as a woman and undergo periodic counseling for two years before I could receive any assistance to begin a medical transformation.

At the start of my junior year, I was pronounced mentally stable and cleared to undergo the treatment. At the same time, I was able to change my birth certificate and driver's license, too, and finally was able to mentally break free.

By graduation, I was wearing A cup bras, my hair was long and lush, and for the most part I felt pretty good about myself. Most of the trans women I knew had genital dysphoria but I never did. I loved my clit as I started calling way back when and it gave me a lot of pleasure.

Being the nerd that I am I researched the hell out SRS and the levels of sexual gratification that trans women experienced after the surgery and seemed like I could achieve the same level with my clit and my anus.

I dated a few men through the years but never let them get past first base. I had read the horror stories about women being beaten up because the men they were dating thought they were being misled. I tried dating women and few times and had sex with them but I had no desire to go down on a woman and intercourse was OK but I felt I should be the one getting fucked. Dildos didn't do much for me. I needed the real thing.

It wasn't until after I graduated from my MBA program that I started working for a company that actually had medical transition benefits but I had to wait until I was fully vested to receive the full treatments.

After five years of pouring my heart and soul into this career I was able to take a leave of absence to get breast augmentation and facial and body feminization surgery. I was now a B cup and everything about my physical appearance screamed woman, hot woman at that!

After my surgeries were 100% healed and quite a bit of physical therapy my company moved me to a new location where I was to lead their Tax Division. I quickly found a trans support group and started making friends. After one of the sessions, one of the women that I was friendly with suggested that we go to the gay bar that was having a Drag Queen night.

We Ubered there and the party was in full swing. Some of the drag queens were beautiful and I could barely tell they were men. Sondra and I struck up a conversation with a couple of women whom I guessed were lesbians - I have horrible gaydar. They were surprised to learn that we were trans.

A little while later I just returned from the toilets and grabbed my drink when across the room I locked eyes with this guy. He was older, short cropped gray hair and a beard.

Of course from what I could see there was nothing that I could tell that made him appear gay but what do I know, except a nice looking man in a gay bar can't be straight.

I smile at him and he smiles back then starts moving towards me.

He introduces himself as Marc, compliments me on my hair and shoes, what a smooth operator knows exactly how to prime me and offers to refresh my drink.

After some preliminary small talk about this bar and tonight's event I ask him why he's here and what he is looking for. His answer is totally unexpected.

Marc's recently divorced and admits that he's pansexual but hasn't been with anyone in 10 years! He admits the last time he had sex was with his wife and it ended badly.

I was curious to know what happened and he told me. He said he was inside her and then got a cramp and had to pull out. She had already gotten off when he went down on her so when he came back after walking off the cramp she was asleep and he decided to go masturbate and ironically he did so to gay porn but he was still attracted to women.

I thought to myself that this could be the guy I have been waiting for.

It was my turn to open up to him and I gave him a brief history of my transition. He was transfixed. He couldn't believe I had never been with a man. I told him I haven't found Mr Right for Me, that is until this evening. His face lit up.

Then a Donna Summer song started playing. I know, how cliche, right, after all this a gay bar.

I grabbed his hand and led him to the dance floor. He had some quirky moves like it had been a long time since he danced and I admired his effort. After a few numbers a slow song started and he pulled me into his arms.

He confessed he was a horrible dancer and had not done anything like this since college. I wasn't really listening and instead just looked into his face. I could feel my bulge pushing against his.

We just rocked back and forth looking into each other's eyes. When his hands dropped to my waist I pushed them down to my butt, he got the message real quick, and he squeezed. I reached behind his head and pulled his mouth to mine and we kissed.

It was like fireworks going off. I have kissed a few people in the past, both men and women, but this was so different. I felt him pour all his pent up lust and passion into this kiss and I return it equally so.

When the song ended, so did the kiss, and I was left breathless. I asked him if he would like to come back to my place. I wasn't going to let this one get away, at least until I was totally sated.

He said he would love to. I led him back to my friends where my purse was and Sondra was all smiles and high fived me. Then she turned to Marc pointing a finger into his face and protectively told him not to hurt me. He said 'the way Carla just kissed me, if all we do is kiss tonight I would be happy with that.'

I just about came in my panties when he said that.

He led me out of the bar and we walked hand in hand to his car. Another cliche was that he drove a Mini Cooper. I asked him if he was sure he wasn't just gay. He chuckled and then kissed me holding our bodies close together. Then he opened the car door and helped me into the car.

Getting in on his side but before starting the car I leaned over and kissed him. I put my hand on his bulge and he quietly moaned in mouth. I started opening his zipper but he put his hand on mine and whispered in my ear 'not here.'

It was a short drive to my apartment. He had a stick shift and kept his right hand on it the whole drive. It was erotic to watch him opperate the stick. I kept my hand on his thigh and we chatted a bit about the city and where we worked.

When we got to my place he told me that he worked around the corner.

There was a quick kiss in the elevator but once inside my apartment I pushed him up against the wall and kissed him with wanton abandon while I ground my bulge into his.

We were both breathing hard when I couldn't take it any more and I dropped to my knees in front of him. Looking up at him I opened his pants. He looked down at me, biting his lip in anticipation for what was coming next.

I pulled down his pants and underwear and marveled at his penis. It wasn't big and it wasn't small, a little bigger than my clit and he had an exciting aroma. I pushed my face into his crotch and breathed his manly scent, my nose coming into contact between his thighs and balls.

Pulling back, I cupped his balls in one hand and the other I moved to his butt cheek and guided his penis in my mouth.

Pursing my lips I slowly pushed the head of his penis in between them and stopped so that I was just sucking on the head. I held the shaft with my lips and swirled my tongue around the head, paying particular attention to his frenulum.

He laid both hands on my shoulders which I appreciated and ohh and ahh'ed with my oral skills. My clit was frustratingly hard and my panties were wet. My excited nipples were driving me nuts. Whenever I shifted my body my panties would rub my clit and my nipples would get teased a little, further exciting me.

I let go of his balls and put my other hand on his other butt cheek and then pulled him deeper into my mouth. I stopped when my nose was buried in his pubic hair and I could feel the head of his penis at the opening of my throat.

I never thought I would find myself in this position. It always seemed demeaning and subservient but now that I am here I can't believe how erotic it is as I give this man pleasure with my mouth. My body was brimming with excitement. My hole was clenched tightly and it was pulsing with excitement.

I am glad I didn't have my plug inside me otherwise I would have lost it by now and I get the distinct impression he is going to want to return the favor.

I slid my tongue back and forth and he was moaning appreciatively. I wanted to taste his sperm badly.

He said my name and told me he was close. I looked up into his eyes. They were half lidded in his ecstasy. I pulled off half way when I heard him give a little grunt and then his penis was pulsing in my mouth.

His sperm was hot and viscous. It filled my senses and he tasted similar to me, only a little weaker. I swallowed quickly but not all because I wanted to savor him, but there was still a lot coming.

I could feel him wanting to thrust but I held him at bay. I continued to suck and swallow until he stopped pulsing.

Finally, he called me 'Sweetie' and told me he was getting too sensitive.

Pulling off, a string of cum and saliva connected my mouth to his penis and then broke and landed on my chin and neck.

He leaned down to me and took my head in his hands and kissed me hard on the mouth. His tongue probed my mouth and sucked my tongue.

Breaking the kiss he told me that was the most intense orgasm of his life. Then he scooped up the cum string on his finger telling me I missed some and put his finger in his mouth and sucked on it.

He stepped out of his pants, just leaving them there and pulled me up to him telling me that I am overdressed.

Taking him by the hand I asked him to follow me and I led him to my bedroom.

I turned around and told him to take off his shirt while I took my dress off.

I am glad I wore my panties on the outside of my garter belt tonight.

I took off my panties and then sauntered up to him. He put his arms around my waist but before I let him kiss me again I pushed my sodden panties up to his nose and told him how horny he made me.

He shocked me when he started sucking on my panties and then whispered in my ear that he really wanted to suck on my clit.

I kissed him and then told him to get on the bed.

I straddled him and then walked on my knees until my clit was right before his lips. His hands went to my butt again and he squeezed it causing me to moan and thrust forward, pushing my clit into his mouth. It was hot and wet and felt amazing.

I almost couldn't control myself as I grabbed the back of his head and pulled his mouth and pushed at the same time. I squealed in excitement and I could feel the vibrations of his mouth moaning on my clit.

I pulled his hands off my butt and put them on my breasts. He didn't need any encouragement as he squeezed them and then grabbed hold of both nipples and twisted them back and forth.

A shiver shot through my spine and I felt something rise up from my core. I clenched my hole and I felt my clit get bigger as I uncontrollably thrusted deep into his mouth. I felt this incredible wave of pleasure radiate outwards and drive through my clit.

I let out a shriek and then I felt my clit pumping into his mouth. It was the most incredible feeling I have ever felt. Way better than doing it myself, there was just no comparison.

I looked down at him. His eyes were closed and my cum was leaking from his mouth but I could still feel his muscles swallowing everything I gave him.

The euphoric feeling I was experiencing combined with the beautiful sight of my slick clit thrusting in and out of his mouth was such a beautiful sight that I teared up and started to cry. I was so filled with emotion that I fell forwards grabbing onto the headboard, my clit slipping from his mouth and crying.

He got up next to me and kissed my neck and asked if he hurt me in any way but I quickly turned to him and told him no and then I was kissing him and we fell on the bed, me on top of him, and continued to kiss until my tears stopped.

Rolling off him we turned to one another. I told him he just made me the happiest woman in the world. He smiled and then told me he loved sucking on my clit and couldn't wait to do it again but I had other things in mind.

Looking down at his hard penis I told him to wait there and I got up to go to my dresser and pull out some lube.

Pouring some lube into my hand I used it to slicken my hole and then leaning over I put some on his penis to do the same.

He sat up as I crawled into his lap and took hold of his member and guided it to my hole. I pushed out as I sat down on him and his penis slid into my hole, excruciatingly slow and I could feel its texture stimulate nerves inside me that I never knew existed.

Once I was seated fully in his lap I kissed him hard but held him there in my channel while I relaxed around his penis.

I won't lie. It hurt, ever so slightly going in, but I felt so full and complete that in no time the pain took a backseat to the overwhelming feeling of being complete.

Surgeries aside, having a man inside my body made me feel like a complete woman. The feeling welled up inside of me again and I started to cry again.

He tried to pull out thinking I was in pain but I just held onto him tighter and through my sobs told him how he was making me feel and that I love him so much. Oops, did I just say the "L" word?

I started to blush and I wanted to apologize but he kissed me hard on the mouth and hugged me even fiercer.

While we were kissing, I started to move up and down on him but I felt something stir inside of me and couldn't get enough friction in the position we were in.

I leaned back and he came with me and now he was on top of me and he started thrusting into me. It felt good but it still wasn't what I needed but I let him carry on for a bit until I got the feeling that he might be close and then I stopped him.

He looked at me with a puzzled look and then I moved so that I was on my stomach. I tucked my knees under me and opened myself to him.

He re-entered me from behind but instead of laying his body on top of mine he picked me up and my back was to his chest. Turning my head and kissing him, he gave me a small thrust and I felt his penis rub against something inside me that sent a shiver through me. This is what I wanted.

He started thrusting in earnest and his penis felt insanely large inside me and it was creating a feeling that once again was going to make me cry.

He was undeterred by my tears and started kissing my neck and my ears. His hands moved to my breasts and squeezed them. The pressure inside me began to build. There was a heat radiating from my core and a feeling of immense pleasure that started to boil from within.

My clit was rock hard and bouncing with each of his thrusts.

My muscles gripped his penis fiercely and he was moaning his love for me in my ear.

Everything came to a crescendo when my clit started shooting cum and my orgasm ripped through me like a title wave. I could feel his penis pumping inside of me and it felt warm and delicious.

Finally we stopped. He held me tightly and we were both breathing hard.

I turned my head to look at him and we both smiled and then I kissed him.

Pulling off him, I felt his penis slide out of me followed by a wet fart and a splatter of cum. We giggled at the noise as I turned around and laid down in my own cum and pulled him on top of me and we started kissing again.

After a while we stopped kissing one another and we just lay side by side looking at one another and caressing each other.

I asked him if he wanted to spend the night and he told me he would love to wake up in my arms tomorrow morning and make love to me again.

I kissed him and then told him we can't sleep in all this cum and I got up and led him to the shower.

We didn't do much in the shower except kiss and caress one another. Once we were dried off he helped me remake the bed while I put the bed spread in the washing machine.

I came back to the bedroom to find him already in bed waiting for me. I turned out the light and crawled into bed with him. We kissed and then I turned in his arms as he held me tightly and went to sleep feeling the most content that I have ever felt in my life.

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2 Comments
PlayMeARolePlayMeARoleabout 2 years ago

Absolutely amazing, as a middle aged newly transgender woman, this is exactly what I want in my first time with a man. I wish I could give this a sixth star!

dnsontndnsontnabout 2 years ago

Tender, sensual, a delightful read!

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