My First Time as Sara... Pt. 05

I've become Sara now for just about a year. One year of exploring deeply who I was, my past, my history and who I've become at this moment.

I was no longer just John, the meek man who was dumped by his fiancé for not being man enough. That skin was shed. Instead I became Sara. I became empowered and in charge of my life. It was as if panties and heels, cute girl next door dresses and sultry and sexy lingerie gave me a sense of empowerment.

I also had Steve with me the entire way. He became in a way my charge. From that first moment that he saw me in full dress to this very moment, he was there for me. He cared for me and has even told me that he loved me. I have a man who told me that he loved me.

I cared for Steve, and despite my indiscretion with Josh, I cared for him deeply. I wanted to say I loved him but either fear of rejection again or something else that held me back from saying that I loved him.

One night, after another amazing night of watching movies and amazing sex, he popped the question. It was sweet how he did it. While I'm nestled in his broad chest, him stroking my hair, he told me of everything he was feeling. How he was deeply in love with me. How he saw a future with me, with us. Then he pulled out the ring.

It was perfect. Small and dainty but elegant at the same time. On the light coming in from the safety light it sparkled and shined. In that moment I was overwhelmed. I mean he loved me for me. There was no worries about him finding out what I really was. He loved me because I was Sara.

I sat up to look at him and told him I needed time. Time to think about all of this. It was so sudden and too much to handle in that exact moment. It made for an uncomfortable rest of the night. I know he was expecting me to say yes right away and when I said I needed time, his face dropped.

Over the next few days I thought about it. It consumed my every single free minute. I didn't want to make any decision like this lightly. It was a decision that had me question who Sara was deep inside.

While I cared for Steve, I didn't want to be a wife. It wasn't that I wouldn't be a good one but I felt that there was far more to explore in who I was than what I was at this time. In my world, I was John and then when I was home or with Steve, I was Sara. The conflict of two personalities couldn't exist. Where John was safe, Sara was more dominate, more exotic and more free.

I had to be Sara always and how I saw Sara was not a wife to a loving man. I saw Sara as a woman every man. A woman that was a desire to any man who wanted her. She was strong and in charge of herself and her sexuality.

I was a coquette and this allowed me to move in this world as free as I wanted. I would live my life as her and her alone and explore it and the men that lived in it. I wanted to be always Sara.

The breakup with Steve was hard. It was devastating. It devoured my soul and I will never imagine how it affected him other than what pain I felt was minimal to his. Even years later, I still see his tears. I still feel our last embrace and our last kiss.

I took the months following to not only heal but to make hard decisions. This included making the decision to be full time. I no longer had a need to keep any remnants of John. He was never the person I was all those years. When I wasn't dressed as Sara, I was sad. I was alone.

I found a doctor and started my hormones. I quit my job and found a place that actually had better pay and closer to my home. They also understood about my situation and worked with me. To everyone that worked there, I was Sara.

I also spent time on my wardrobe. You'll be surprised what thrift stores and such contain for the new woman on the go. The best part was the lingerie shopping. Soon I had a closet filled with frilly skirts and dresses with shoes to match. I also had a dresser filled with lingerie galore and cute jeans.

Sara was like a flower in spring. Sara was in full bloom.

The greatest advantage to all of this was my sexual awakening. Becoming Sara full time allowed me to explore not only myself sexually but also to find my own path. Being a coquette opened up a door of sexual freedom. I also realized that Sara had to have a purpose. I found gratification in being a fantasy for men. Sara would fulfill any mans fantasy and any fetish he needed satisfied.

I had so much fun flirting with guys. I would become the woman they desired to be with. The woman they imagined when they stroked their hard cocks in the middle of the night. I'd be the girl they wished their girlfriends or wives would be.

I met Jerry a few months after starting my hormones. He answered my online ad and sounded amazing. He was in his mid twenties and used to be a swimmer, so he was very lean and muscular. He was cute and looked conservative in his photos. When we finally met up later in the week, I was greeted by a guy in khaki shorts and a golf shirt.

I dressed how he asked me to. In the emails, flirting back and forth of course, he liked the secretary look and I wanted to make sure when we met, I fit that need. I came to the bar in my tight black pencil skirt, boots with about a 4 inch heel and this cute cotton button down shirt. I even went to have my hair and nails done. I looked sexy.

We sat at a small table in the bar and talked. Honestly it was hardcore flirting more than conversation with any kind of substance. I told him about what made me start dressing and that I was on hormones. He smiled at that.

He was in a relationship with a girl that was not as sexually adventurous as he was and this frustrated him. She never dressed sexy and he even told me in bed she was like a dead fish. Her being adventurous in bed was having sex at the foot of the bed. I laughed so hard I almost spit out my drink.

After a few hours, the innocent flirting went to being more physical. His hands on my leg, holding my hand and even a cute little kiss on my cheek. In-between all of that was compliments of how sexy I was, how sexy I dressed and he even said if I was ok with him trying to screw my brains out, he'd make me his secretary. It sounded enticing.

We decided to go back to his place. I was in the middle of moving to a new place, so it was easier to play there.

His place was nice. One of those overpriced apartments in a high rise downtown. I'm sure I'm not the only girl he's brought here and I won't be the last. Fancy furniture to compensate for something he lacked.

He pouted me some wine and gave me a tour of his place. It was cute, most definitely a guys place. I loved the hardwood floors, how my heels clicked on them.

When he took me to the bedroom, I walked around while he was in the doorway and when I looked back he had a smile on his face a mile wide.

"We could have some fun on the bed you know," he said, sounding so cheesy.

"Or we could just fuck on the couch," I retorted.

He smiles, let out a laugh and started walking back to the living room. I followed, taking the last sip from my wine glass.

I told him to sit on the couch and put my glass on the counter. I the stood a few feet from him and started to take off my shirt, unbuttoning it slowly snd letting it fall to the floor. I had on a really cute pink bra with white lace on the cups. So far the hormones gave me perky A cups and the biggest plus was it made them extremely sensitive.

I walked sexy like to him and knelt on the floor. I started with his belt and with no effort, took his belt off and had his pants down to his ankles. As he slid off his shirt, I licked his stomach and made sure I looked him in the eyes.

Eventually I found what I was looking for. His cock was getting hard and moving in his boxers. I made sure that I freed it and as I pulled his boxers down to his ankles, I bathed his cock with my mouth and stroked him slowly with my hand.

I loved swirling my tongue around his engorged and swollen head. Every time my lips wrapped around his cock, he moaned loudly. As my mouth slid up and down his throbbing dick, he would thrust, his hands in my hair. Soon he was thrusting harder and faster and while I loved his fucking my face, I wanted him to cum in my sexy ass.

I slowed him down as I took my mouth off and slowly and gently stroked him. I looked deep into his eyes and smiled.

"Let's see if your girlfriend ever does this," I say as I stand back up and take a few steps back.

I slide the zipper on my skirt down and let it fall to the floor. I lick it to the side and stand in front of him. I'm wearing my sexy pink lace boy shorts and my nude stay up stockings. He starts from head to toe and as he locks with my eyes, he smiles. He slowly strokes his own cock, up and down.

I walk to him and moves his legs open with mine. I grab my purse from next to him and take out my small bottle of lube. I put some on my hand and strokes his cock for him. It glistens in the light and I feel it throb in my hands.

I use my other hand and slide my panties past my tight little ass and over my boots. He fixated on my hard clit. While the hormones have made it slightly smaller, and I wasn't that big to begin with, the hormones didn't stop from getting hard.

He slid his tongue towards my hard clit and I lifted his head to look at me. I smile and then he started to stroke my cock as I lubed up his.

I moved his hand away from my clit and then straddled him. I could feel his cock against my cheeks and as I kissed him hard, I took my lubed up hand and guided him straight to my wet and wanting sissy ass.

It felt so amazing as his swollen head penetrated my tight little hole. It made me shiver as I slide my ass down his shaft, plunging his warm and fleshy cock deep into my ass. I wanted to do all the work and did as such, sliding my ass up and down.

His moans drove me wild. His hands on my breasts made me moan and groan. I worked and grinded on his dick, hoping he would hit my spot and make me cum.

As I was working his dick, he would thrust hard. It made me almost roll my eyes Into the back of my head as his balls slapped my smooth ass. It felt amazing that as he fucked me harder and harder and as I slide up and down his shaft, my clit was rubbing on his stomach and within minutes I exploded, my warm little amount of cum mixing on both of our stomachs.

He grabbed my hips with both his hands and pounded my wet and well lubed ass. I could feel his cock fill every inch of my ass. I let him pound me hard and fast. I feel him twitch and I know he's going to cum.

I slide off and get on my knees. As much as I want him to cum in my ass, he's been so amazing that I want to leave him wanting more. I take his now nearly throbbing cock and stroke him the rest of the way. As he erupts, I aim his cock and let him shoot his hot, creamy cum into my mouth.

I take the first two right into my mouth and let it slide down my throat. It tastes sweet as he shoots another all over my face. I take another that goes in my hair and then as every good girl should, I envelope his still hard cock and swallow the rest. As he starts going limp, I take him out of my mouth and lick my lips.

Naked, I walk to the bathroom and clean up a little. As I stand in the mirror, I see a woman who made this mans night. As I cleaned off my sissy cock, I actually spurted again and almost fell to the floor in an orgasmic trance.

As I walk back to the living room, he's still on the couch, trying to catch his breath. I put on my skirt and blouse and before I left I walked over and put my panties back on, kissing him hard and promised him that next time, he'll have my ass.

Two weeks later, at my new place I delivered on my promise and he fucked me in my bed, filling my ass with very wet and very sticky shots of cum.

I'm loving being Sara. I'm also guessing he did as well.