Exploring My Life as a Woman

I am a small waifish little man, about 5'6", with soft skin and very little muscle tone since I've never worked out in my life. Always imagined myself being a girl instead of a guy because I am so feminine in appearance. Now that I am single and on my own, I've decided to live as a woman. I live in an area of the city where nobody knows me so there is no risk of being found out, not that anyone would really care anyway. My work from home job is very lucrative and it keeps me well supplied in clothing and lingerie. I've gotten to know several of the girls through the company I work for and became very close to them. One of the girls and I became very close. Miranda and I became so close that she was like a sister that I never had. I shared with her about my alternative life and she was very excited to volunteer herself as my personal guide to all things woman. She was the one who showed me all the great shops around the city to get all my wears at a good cost and how to apply makeup. My hair is pitch black and naturally long so there was no need for wigs. I loved the transformation that she had a key role in helping create.

Miranda asked me if I wanted to meet anyone and I confided that I had never been with anyone intimately and to be honest the idea scared the hell out of me. She assured me that she would set me up with a nice guy and to leave it all to her.

About a week later, Miranda called me and said she had a guy friend she wanted me to meet. She told me that there were no worries because she knows that he is bisexual and me being Trans is not an issue. I was relieved because the last thing I wanted was to be found out in a private moment and having the shit kicked out of me. She set up a date for us to meet for dinner and drinks at one of the local fancy restaurants. Miranda came over and helped me pick out my outfit, undergarments and fix my hair and makeup. I work a sexy two toned black and grey dress that came down to my lower thighs and the top was loose enough to just keep me slightly conservative but not enough to turn him off. I wore a sexy pair of black silk panties and matching bra underneath and black heels. I was so nervous... Miranda gave me a drink to calm me down a bit and the time came to go meet up with Brad...

I met up with Brad at the restaurant and we immediately hit it off. Talking and smiling at each other all through dinner and several glasses of wine. He paid the dinner check and asked if I would be interested in going back to his place for some drinks, and of course I said yes. We arrived at his apartment and before we could even get through the door he turned and kissed me. Wow the electricity that went through me was insane! We finished the sweet kiss and moved into the living room. He then went in and got us some drinks and we sat down to talk some more. Brad then confided that he was instantly attracted to me from the moment we met at the restaurant. I just giggled and said the attraction was mutual. He moved closer to me and kissed me again, this time a lot more slowly and seductively. My body was on fire! He kissed me more passionately and his hands began to explore my body, slowly making their way down to my passion. I stopped kissing him for a moment and he looked at me questioningly. I asked him if Miranda had told him "everything" about me. He smiled and said that he knew.

We went back to kissing and I felt so completely relieved and so fucking turned on! I had never been with anyone before and I so loved this feeling! He drew his hand up the hem of my dress and raised it ever so slowly all the while kissing me so softly and sensuously. This man was driving me insane! My panties now exposed and my little cock hard as a rock pushing them to get out. Brad kissed down my neck and then slowly got down to his knees in front of me. He looped his thumbs through the sides of my panties and began pulling them down. My little hard cock sprang into view as I gasped with anticipation. Brad smiled as my panties dropped to the floor. He wrapped his hand around my cock squeezing it tenderly coaxing a bead of precum to surface from my tiny hole. He bent forward and licked it off with his tongue and that sent me through the roof! My moans of pleasure filled the room as he then engulfed my little cock all the way into his mouth. Sucking so softly up and down on it as he ran his hands up and down me! I was in pure heaven!

My body was writhing and I knew I was so close to cumming. I did my best to let him know this but I was out of control! This was my first time ever having my cock sucked and he was a true expert! The first wave of my orgasm hit me and my cock pulsed at I came into his sweet mouth! Over and over, jets of cum hit the back of his throat. He just kept sucking on me even more passionately! Finally my orgasm subsided and he let my softening cock fall from his mouth, a little string of cum leaving me on his lips. I was in total euphoria, literally cum drunk along with the alcohol that we had. He came back up and kissed me so tenderly. He gathered me up and carried me into his bedroom. Oh my God this night was only going to get better!

Brad carried me to his bed and helped me get out of my dress and bra. Then began kissing me so passionately, once again causing my insides to turn upside down. I helped him get out of his clothes and just stared bug eyed at his massive cock! It was gorgeous! I reached out to it and wrapped my hands around it pulling him closer to me as I sat on the bed. So silky smooth, long perfect shaft, tapering slightly to a bulbous mushroom head, at least 9 inches long. I was mesmerized by it, slowly running my hands up and down his length, while his hands ran through my hair. I looked up at him and said that I had never done this before but I hope I do well for you. He just smiled and gently pulled my head closer to his cock. I pointed it at my lips and noticed his precum flowing from the head. I put my lips on him and he groaned as they spread over him, taking that thick meat of his into my mouth. I ran my tongue around it tasting the sweetness of his juices as it flowed. I couldn't get much more than the head in but he didn't seem to mind with all the moaning he was doing. He was stilling running his fingers through my hair and around my head tenderly as my mouth worked its best on his gorgeous man meat.

My GOD his cock tasted like heaven as I began moving up and down as far as I could go, each time being able to take a little more in. With one hand I gently massaged his heavy balls and the other moving up and down on his lower shaft as I sucked him deeply. He began to move in rhythm with my mouth causing just a little more of his cock to go ever deeper until it started to touch the back of my throat. I fought off the gag reflex because I wanted to please him the best way I could, and still at least half or more of his cock wasn't even in my mouth. His moans became louder and he started really fucking my mouth. It was all I could do to keep up. I felt his cock swell even more and as he cried out, the first jets of his cum went streaming right down my throat as his cock head lodged itself deep. I was swallowing as hard as I could and it seemed as if he turned on a hose as his hot cum just kept flowing. He locked my head in his hands as he just barely pumped into me with each pulse. My GOD I was going to drown in this man's orgasm and I LOVED IT! He finally started to relax and his cock began to soften, I kept a grip on it and milked every last drop of his sweet pearls out of him. I released him from my mouth and continued milking him, getting every drop almost like I didn't get enough. He tasted so FUCKING GOOD! I looked up at him and smiled then asked if I did okay. He half laughed and moaned then bent down and kissed me softly. "You did awesome my dear," in his very sweet husky voice.

Brad lay down next to me on the bed both of us still out of breath and the taste of his cum still on my tongue. I turned to face him and he came in close for some tender kissing. We chatted for a bit as he ran his hand up and down my body, my hand rubbing up and down his rock hard abs. He clearly worked out, ALOT. He told me how beautiful I was and I could feel my blush burn into my face. I just smiled and said thank you. He moved in and began kissing me again, slowly and methodically getting more and more passionate. My body melted into his as he pulled me ever closer. His hand found its way down between us and started stroking on my hardening little cock, my moan of approval escaping my lips. He moved down kissing his way down my tummy and then placing a tender kiss on my cock head. He gently turned me over on and started kissing down the small of my back, working his way down the crack of my ass. He reached under me to pull my bottom up towards him, exposing my rosebud to him in all its glory. He kissed around my opening then on it, slipping his tongue inside me. I thought I'd cum right then and there!

His tongue was working in and out of my tight little hole feverishly while he continued stroking my little cock, driving me absolutely insane! He paused for a minute, reaching over to his nightstand to get out a tube of lubrication. Then back to my ass he went giving me my first and best rim job ever! He then moved back up my body from behind. I could feel his very hard cock rub against me as he did sending shivers up my spine. He kissed the back of my head then around to my ear. He whispered to me that he would be very gentle with me because he knew it was my first time. I nodded my head as I felt his bulbous cockhead pushing against my ass. He reached down for the lube and squeezed out some on his fingers putting some liberally on his cock and then on my little rosebud.

Then I felt his cock find its way to my entrance where he massaged it around my opening. I tensed up a little and Brad reassured me that he would be gentle with me. I knew he would but I also knew how big his cock was. He began pushing gently on my opening as I tried my best to relax, my sphincter not wanting to open but slowly doing so. Finally it gave way and the head of his cock popped inside. WOW! I cried out at the pain of it. Brad stopped moving and hugged me close to him allowing me to try to adjust to him. Slowly my body relaxed and my now wide open asshole began to accept his member. He began to slowly move again pushing more of his huge fucking cock into me! He pulled back a little then in more, my ass relaxing more and more. The pain dissipated and the feeling replacing it was incredible! I could feel his cock pushing against my prostrate as he pushed ever more into me. He would pause then pull back and then push back in still allowing my insides to adjust and get lubricated for him. Deeper and deep he went until finally I felt his balls resting against my perineum. My GOD it felt like he was in my stomach! I moaned loudly as tears of pain then pleasure came from me. I was his and he knew it. Mounted like a captured animal on him unable to move with his weight on me.

Brad then started to withdraw slowly almost all the way out and then pushed deeply back in, my cries of pleasure coaxing him onward and inward. His strokes in and out increasing into a steady rhythm, FUCKING me like I have never been FUCKED before! Well it was my first time. I was like a doll on a stick for him. He reached around me to stroke my little cock as he continued his assault in my ass. I was in HEAVEN! Deep strokes in and out faster and faster he fucked me, both of us moaning and groaning in pleasure. I could tell he was about to cum as his cock pounded my colon, his breathing becoming more labored. I whispered to him between moans to fill me with his sweet cum. He drove home deep in me crying out as his orgasm overtook him. His hot cum burning my insides as it squirted relentlessly out of him. My body could take no more as my own orgasm ripped through me and cum flooding from me onto the bed.

Brad slowly began to relax and I could feel his awesome cock start to soften inside me. He wrapped his arms around me and pulled me with him as he went to his side on the bed. He kissed the back of my neck and held me so close never letting his cock completely break free from my ass. I could have stayed like that all day. Finally his cock slipped out of me as he turned me over to softly kiss me again. We stayed like that arm in arm cuddling for the rest of the night, giving in to our sleep and dreams of the night away.