After graduating from college with a degree in financing, I was lucky to land a job in a large firm in New York. I couldn’t believe the money I was making to get out of college, but I didn’t complain.

I loved my job. The people I worked with were great. The only thing missing in my life at this point was a relationship. I didn’t want to jump into marriage but let’s face it. I haven’t had a date in over a year.  It’s not that I did not have an interest in women. My six-foot-five frame and athletic build usually gave me a step up to meet others.

I was not too fond of meeting someone at a club or bar, so I started looking to see whom I might encounter since most couples meet at work. It was a large company with many different departments, so I thought my chance to meet a confident professional woman would be good.

I started walking through the building, paying more attention to the people I encountered. I didn’t want to jump into something quickly, so when I saw someone who interested me, I would try to find out as much information as possible about them before asking them out.

There were a few women whom I dated for a while, but I just never felt that connection to take it to the next level.  Then one day, as I walked through the lobby at work, I noticed a vision of beauty. She was five feet eight inches tall with beautiful long black hair and a fantastic smile. She had beautiful long legs, an amazing ass, and large breasts. 

Over the next few weeks, I made many inquiries about this woman. I found out she worked on the fourth floor, and her name was Sandy. The more I saw her in the building, the more and more I became infatuated with her.

I approached Mary, a woman who also worked on the fourth floor, to get more information.  When I asked her about Sandy, I saw in her eyes that she was a bit surprised and, to be honest, looked like she was going to laugh at me. I pressed her to tell me what was up. Then holding back her laughter, she kindly informed me that Sandy was a transgender woman.

I stood there in shock and couldn’t believe what she was telling me. “You’re fucking with me, right Mary?”

Mary became supportive when she realized I was serious and became very supportive of me and comforting.  I was dumbfounded. It was hard to believe this was not biologically a woman.

The days went on, and I became fixated on Sandy. I would go out of my way to see what she looked like that day. My mind raced thinking about her. Even when I masturbated, my thoughts were of Sandy. I felt like I was a teenager trying to hook up with the hot girl in the class.

I started justifying why I should keep this option open.  I mean, it’s not like I haven’t been with another guy. When I was younger, my friend and I experimented before we started dating girls, and another time when I was in college, I found myself with another man for a weekend. I was battling back and forth with my inner demands.

Friday night came, and my co-workers went to happy hour after work. There is a popular sports bar where we work, and we adopted it as our unofficial party zone.  We all let off some steam, and as happy hour ended, our crowd dwindled when many headed to their homes. I had no place to go and didn’t feel like heading home to an empty apartment, so I ordered another drink as my last co-worker left.

I didn’t pay much attention to the crowd when everyone was there, but I am now sitting alone. I scanned the place. That is when I saw her. Sandy was sitting in a quiet corner, having a drink and eating her dinner.

I watched her from afar and decided there would be no harm in going over and talking to her one employee to another.  I walked to the bar and got another drink. Stepping back from the bar, I walked by Sandy’s table. It was do or die now.

I introduced myself and told her how I had seen her in the building. We talked briefly before I asked if I could buy her a drink. She graciously accepted and asked if I would like to join her. I quickly accepted her invitation. I ordered our drinks and sat at her table.

We chatted for hours. I couldn’t believe how enjoyable it was to chat with Sandy. We had many things in common. As we talked, my mind was going to other places. Places that were very pleasurable to think about.  The night flew by, and we suddenly noticed the place was empty, and the staff was cleaning up and getting ready to close.

We finished our drinks and left the bar. I asked where she was parked, and Sandy told me that she only lived a few blocks away and could walk home. I offered to escort her home. She told me that wasn’t necessary. I insisted, telling her in good conscious I could not let a beautiful lady walk home alone.

I offered my arm, and Sandy took hold of it as I walked her home. We continued to talk about many different topics, and before I knew it, we were at her door. I told her how I enjoyed the evening and spending time with her. I thanked her for an incredible evening and told her I would love to spend more time together. (I was not even thinking about sex, just as friends since her company was so enjoyable.)

Sandy suddenly became guarded and defensive. “I’m sorry, did I say something wrong,” I asked.

“No, you didn’t do anything wrong. It is you may have a different idea of me. I am not what you may think.”

“What do you mean you are not what I think you are? I know all about you, and the only thing I can see is that you are a beautiful and exciting woman who is a lot of fun to be with. That is all I need to know.”

Sandy stood quietly for a few seconds. She then turned and opened the door to her apartment and turned to me.

“Would you like to come in for a nightcap?” she asked me.

I have to admit that took me by surprise. It seemed forever that I stood there before I heard myself accepting her invitation, and we headed into her apartment.

We sat on her sofa, and she asked if I would like a drink. I told her how much I would love one and watched as she got up and made me a drink. I sat there watching Sandy as she made my drink thinking everyone must be wrong. There is no way Sandy is not a woman. She is gorgeous and, honestly, more feminine than some of my past dates.

Sandy returned to the sofa and handed me my drink. She knelt next to me on the couch as we talked. She asked me if I was sure that I knew everything and asked if I was comfortable with it all. I acknowledged that I was comfortable and understood everything. Suddenly, all my doubt and confusion left, and I knew I wanted to be with Sandy.

Sandy slowly leaned into me and gave me a soft kiss on my lips. I smiled, then placed my drink on the table next to me. I turned back around and pulled Sandy to me as I kissed her. A hot passionate kiss, our tongues exploring each other’s mouths, and our hands exploring each other’s bodies.

My hand found its way to her breast, and I caressed them as our kiss continued. Sandy’s hand moved up my inner thigh to rub my cock over my pants. My cock is already hard as it strains against the material of my pants. Sandy undid my belt and undid my waistband.

She kissed my face as she moved close to my ear and whispered to me, “Are you sure you are ready for this?”

I was way past the point of no return. I knew I wanted this and had no second thoughts about it right now. I moaned, “Oh yes, I want it.”

Once Sandy heard me acknowledge how I wanted it, I watched as her well-manicured hand slid into my boxers to take hold of my by-now rock-hard cock. I closed my eyes and moaned loudly as I felt Sandy’s hand on me. As Sandy caressed my cock I worked on unbuttoning her blouse and removed it before I unclasped her bra.  Her giant, firm tits rested on my chest as she leaned into me.

She was kissing my chest and guiding my cock to her tits as she rubbed it over her tits. I was in heaven as I felt my hard cock on her soft tits. But when Sandy moved down and licked the tip of my cock, I almost lost it right then and there.

I wanted to give Sandy the same pleasure she was giving me. I slid my hand down, caressing her ass, and tried to slide it up under her skirt. Sandy stopped me and told me, “Not yet. Just sit back, relax and enjoy.”

Sandy slid down my body and wrapped her succulent red lips around my cock. She looked into my eyes as I watched her mouth engulf my cock. Her big beautiful brown eyes were so hot as she took my cock in and out of her mouth. Sandy removed her mouth from my dick and jerked me off as she took my balls in her mouth. She looked so sexy, first sucking my cock and then sucking on my balls. She worked her way back to wrapping her mouth on my cock as her head bobbed up and down on me. The passion was so intense as my moans became louder. I watched as my cock disappeared into Sandy’s mouth and backed out again.

My breathing became heavier, and my moans louder. Sandy was excellent as she used her mouth and tongue, bringing so much pleasure. I felt my juices boiling from deep within my balls. I was on the edge. Sandy sensed it and bobbed her head up and down on my cock faster, taking me to the base and then back to the tip. My body started shaking as I thrust my cock upward. I screamed that I was going to cum. Sandy didn’t stop. She continued sucking. I thrust into her mouth, and my dick tensed and spasmed as I shot stream after stream of hot cum into her mouth.

I felt Sandy’s lips tighten around my cock as she sucked and milked every last drop out of my cock. She kept me in her mouth until my dick went limp and crawled back on me. We kissed a hot passionate kiss. I could still taste my cum on Sandy’s tongue. It was such a turn-on.

Sandy placed her head on my chest as I caressed her body and told her how amazing she was. Sandy looked at me and asked if I wanted to go to her bedroom. I couldn’t move fast enough to get in there.

We entered her bedroom and walked over to the king-size bed. My still loose pants were dropped to the floor, where I stepped out of them and took my shirt the rest of the way off. I stood there naked in front of Sandy, who had her shirt and bra still off but was still wearing her skirt and heels.

I moved to Sandy and reached around her waist, undoing her skirt. I pushed it over her hips, and it fell to the floor. She stepped out of her skirt as I took her in my arms again. Our naked bodies were tight together as we once again kissed. As we kissed, I pulled her panties out at the waist and pushed them downward. I felt her lady cock pop out onto my arm. I stepped back, looking at Sandy, smiling as I whispered, “You’re gorgeous.”

My eyes locked on Sandy’s beautiful sexy body. It was such a turn-on seeing a sexy woman like Sandy standing there with a hard thick seven-inch cock. I guided Sandy onto the bed and lay next to her. My mouth kissed her body, and my hand stroked her cock. I kissed down her neck and to her tits, taking her right nipple into my mouth as I sucked on it. My hand slowly stroked her. Her moans filled the room.

I left her right tit and kissed my way over her tummy and lower, still holding her cock I licked around the tip of her cock. Hearing her moan louder was such a turn-on. I licked it more, tasting the droplets of precum on her cock. My hand caressed her balls as I wrapped my mouth around her cock and sucked her to the base. She let out a loud moan as I took her.

“Oh yes, suck my lady cock,” she whispered.

My lips slid up and down on her rock-hard cock. Sandy’s hands were on the back of my head as she pushed my head on her cock. Faster, I bobbed my head up and down. It has been so long since I had a cock in my mouth that I forgot how much I enjoy it. Sandy moaned louder and louder she begged me to suck her faster.

I could sense she was close, so I tightened my lips around her cock and sucked faster. Sandy’s voice broke as she begged me for more, “Yes, OH god, yes, suck my cock. I’m going to--!”

“CUUMM!”

Her hips thrust upward as she filled my mouth with her cum. I sucked and swallowed, not wanting to miss a drop. Once Sandy’s cock went soft, I crawled next to her on the bed as we held each other tightly.

We made some small talk before Sandy asked me where would we go from there. She told me she had no intentions of being a fuck toy hidden in the shadows. She wanted to be seen with someone who would not be ashamed to be with her.  I told her outright that I had no idea where it would go, “but I do know I think you are a fantastic woman. I love being with you and would love to see where it goes.” I went on to tell her how I would never want to keep her in the shadows.

She smiled with the pleasure of what she heard. Her hand moved down over my stomach, and I felt her take hold of my already hard cock. She went on to tell me how she was an open person, and she stated her mind when she wants things.

I told her I would have it no other way and emphasized how important communication is in a relationship. She smiled and looked me straight in the eye. Wiggling my hard cock, she said, “Good, because I want you to fuck me now.”

We kissed before Sandy moved onto all fours on the bed. I moved behind her as I massaged and kissed her tight ass. My hand rubbed her balls and cock as I paid attention to her ass. Sandy moaned as I kissed her ass and caressed her cock. It turned me on. I wanted to hear her moan more, so I opened up her ass and rimmed her man cunt. As she moaned louder, I licked faster and eventually wiggled my tongue into it.

Sandy was ready, as was I. I took my cock in my hand, guided it to her man cunt, and pressed it against her hole. Slowly I pushed in. She gasped and groaned, begging me as I went deeper into her.

With my cock buried deep in Sandy, I rubbed and caressed her lower back and ass, feeling her relax as she stopped clamping down on my hard cock in her. I took hold of her hips and started thrusting in and out of her, slowly at first, then pounding faster and harder. The sound of our skin banging into each other filled the room. Sandy begged me to fuck her harder. I felt my orgasm start to build, but I didn’t want it to end just yet.

I pulled out of her and moved her onto her back with her ass at the edge of the bed. I stood next to the bed. I reached down and stroked her hard cock before I bent down and took her into my mouth again. Getting her cock nice and wet. I took her legs, hiked them up in the air, and stepped back into her as I thrust my cock back into her. She moaned and screamed with please as I fucked her hard. My hand took hold of her cock as I stroked her as my dick rammed into her.

As Sandy continued to beg me to fuck her, I thrust harder and faster, ramming my cock so deep in her. I was at the edge and tried to hold out as far as possible. I couldn’t go any longer. With one hard deep thrust into her, I emptied my balls deep.  Filling her cunt with all I had.

My hand continued to stroke Sandy as I filled her with my seed. It drove Sandy over the edge as she exploded all over her stomach and my hand with a huge load. With my dick still in Sandy, I leaned down to her kissing her before I took her cock in my mouth and licked her stomach to clean her up.

We both collapsed on the bed holding each other tight, and fell asleep.

The next day we picked up where we had left off, spending the day in her bed before I left to go home so I could get ready to take Sandy out to dinner that night.

We have been going strong ever since.