To say I was a loner was an understatement. The day I turned 18, only my older aunt showed up, with a store bought cake. I have lived with her for 5 years, since my parents went to jail for drugs. Being homeschooled, I spent most of my time downstairs, usually done with my work in about 3 hours, with the rest of the day to goof off.

At my age, for a boy, I was only 5’6” and 135 lbs. With shoulder length brown hair and blue eyes, I can still hear the teasing from back when I went to school. It stuck with me but it wasn’t until later that I realized why. Having found some clothing and makeup left behind my my older cousin, my curiosity got the best of me. A few YouTube videos later and I spent many nights learning makeup techniques and utilizing the cute clothing she forfeited.

My birthday night was no different, alone, I made it downstairs around 7 and began my regimen. By 8:30 I was dressed in a black business skirt, red blouse, stockings, garter and matching bra and panties. Embarrassingly, I realized I looked like a girl, and having no experience with the opposite gender, I was the closest thing I had to a girlfriend. Grabbing my phone, I started taking the normal pictures. But tonight something came over me.

I was no stranger to pornography, but as I was searching I came across a chat site for men. Knowing I looked like a girl, I thought what the hell. What harm could it do? Logging in I found out it was for men, looking for men. Admittedly, being dressed like a girl for several years, the thought had crossed my mind more than a few times. Creating a profile, a fake name, I logged in and posted a tame picture. Within several minutes I had several men wanting to chat. One in particular wouldn’t go be up. He was much older. He was 57, older than my biological dad.

He started off complimenting me. Telling me that he knew that I was male but I was a very convincing woman as well I thanked him and deep inside was honestly intrigued at how far I might be able to take this conversation. As we chatted he told me that he was married, had been for years, but that their sex life had died long ago. As we talked more, he asked if I had ever been with a man before.

Telling him that I had no sexual experience must have been the magic button because this seemed to get him started. He asked tons of questions. And as I answered them I learned things as well. I was honestly getting very turned on talking to him. The dirtiness of the whole thing, the fact that he was older and married made it more comfortable. As we talked I learned that he was only 15 minutes across town from me. Eventually he asked if I would ever like to meet.

I really don’t know what came across me, other than having no friends and being alone most of the time, I quickly said anytime. He informed me his wife was home but that he owned a local hardware store nearby and if I wanted I could come by. As nervous as I was, I agreed. I quickly went to the bathroom, fixed my makeup and hair and grabbed my keys. My aunt wasn’t home and wouldn’t be back until later. I could quickly sneak back in.

I arrived at the address provided. As instructed, I walked to the side door and into a dimly lit office. I could hear someone in a nearby bathroom. I heard a flush and then the door. He walks out and turns to me and smiles. I was shaking inside but didn’t want to show it. He was at least 6’2” and probably 250 lbs. I felt very small. He asked if I wanted to sit. I walked over to the couch and sat as ladylike as possible. My skirt was short enough that it barely hid the tops of my stockings.

Again he asked a ton of questions, like how long I had been dressing. Things like if I thought I was gay or interested in men. I informed him that while watching porn I often caught myself looking at the men’s cocks and getting turned on, imagining what it must feel like to be the woman. But it usually ended with me getting off and that was it. Have never been brave enough before. As we talked, I could watch his eyes travel my body, and honestly I think he had caught me looking at his crotch a few times. He was definitely showing a little.

When he asked if I had ever been near a man, I shook my head. He stood up and then grabbed my hand. He said quietly, just tell me when to stop and I will. He slowly pulled me to him and simulated dancing. I had to admit it was a strange feeling being held by a man, especially someone his size. His hands on my lower back and mine on his sides. My head was near his chest. Before long I could feel him pressing into me and could definitely tell he was getting harder. He broke free and motioned me back to the couch. Sitting me down. He asked if I had ever seen a cock before. Explaining just in a public bathroom before. He laughed a little and slowly unzipped his pants. Standing only a foot or so away, he reaches in and pulls his half hard cock out and lets it fall. My eyes immediately locked.

Noticing my state, he said “I’m gonna walk a little closer. Tell me when you are uncomfortable” I nodded in agreement. Slowly he walked forward. Now only 6”’from my face his cock was certainly getting bigger and more erect. Not knowing what to do, he kept getting closer until his cock was poised at my lips. Not sure why, I slightly opened them and he lifted his cock to my mouth. All the time spent alone must have caught up with me cause something in me broke. As his cock inched its way into my mouth, I relaxed.

I could hear him moan a little and that wrecked me. I took my hand and wrapped it around his cock and closed my mouth around him. Having watched enough porn, I imitated what I I saw. The taste, the texture and smells were intoxicating. For minutes he stood there pumping his cock into my face. Pulling back, he stood me up and turned me away from him. Lifting my skirt he started rubbing my ass. He kept saying how cute and feminine I looked. Before I knew it he began rubbing his cock against my ass. I have had my fingers in there but his cock was a good 6” and I was hesitant to agree. But something told me I didn’t have much choice.

With very few words, he walked over to a small table and pulls out a tube of something. Still leaned over the couch, he takes his fingers and wipes the substance against my ass. And as I looked back, he was coating his cock. Walking forward to me, he places his cock against my opening and applies pressure. He kept whispering relax which is exactly what I was attempting to do. Just a few seconds later I felt the head pop inside. Feeling me tense up, he stayed still. After he felt me relax, he started pressing again, I could feel him inch by inch enter me. Before I knew it his stomach was against me. I can’t explain the fullness I felt but it felt so wonderful, and right.

Feeling me squeezing against him, he must have taken this as a hint. He started slowing moving in and out. After a few minutes he was using the full length to fuck me. It was an amazing feeling to have a masculine older man behind me, pushing his cock inside me and moaning softly. Hearing his breathing it made me want to be his subject of pleasure so I started pushing back against him to meet his thrusts. Fucking me hard for at least 10 minutes I felt him tense up. Then he bottoms out inside me and I could feel him unloading against the walls of my ass.

He stayed inside me for a minute or two more until I felt him slowly pull out. Squeezing my cheeks together, I pulled my panties back up and turned to face him. He softly said thank you, and I melted. I looked down at his softening cock and reached out you both hands and held it firmly. We near and talked for about 30 minutes more before he said he had to get back before his wife got suspicious. He locked the door and walked me to my car. Giving me a kiss on the forehead and squeezing my ass. He said I will text you in a bit. I drove home with his cum still inside me. My trophy.

This began my first sexual relationship with someone which lasted for more than a year until they moved away. We still stay in touch. I have found another daddy now but it cannot compare to my first time and my birthday present!