18 yo - The Craziest Year

Two years ago, when I turned 18, the sky fell out. My mother split from my step-dad, he goes to jail, she disappears and I was sent to live with an older aunt. Months later, after getting settled, she gets sick and had to be hospitalized for some time, so I was sent to live with her brother, my great uncle, Robert. And before you ask why I just didn’t move out on my own, being raised in a dysfunctional and very poor family, those weren’t viable options for me at the time.

Being an only child, I have to admit I was a little sheltered. I was always small as a child, but now that I was 18, I had only grown to be 5’6” and 135 lbs. Convinced I was going to become a famous singer one day, I let my dark brown hair grow past my shoulders. I took my share of ridicule in public, along with the occasional whistles when someone thought I was a girl. No vehicle and no way to get a job, the first few weeks were tough.

Robert, was always loud when he was around. At family gatherings, he always was the first to drink too much, and the first one to pass out. The few times he spoke to me back then, it always seemed he bonded to me over music. He played guitar and spoke often of being in local bands. We always talked about getting together and playing through some songs. It never happened, but we always discussed it.

Now an awkward 18 yo young adult, living in a bedroom in his single wide trailer, occasionally saying hello, we really hadn’t had many conversations since my moving in. At 64 yo, he stood 6’2” and easily weighed 240 or more. Always kept a close haircut, and shaved his face religiously. He was retired now, but always woke up and went out for breakfast at a nearby diner. Married once years ago, never again.

One morning, I woke up and walked into the kitchen to grab some cereal. Sitting at the table, in a pair of running shorts and a tshirt, legs curled under me, looking though my phone, I heard his car pull up. He goes to check the mailbox and then into the kitchen door. Walking by, he smiles and says hello and sits down to look through the mail. I finish my cereal and slide out of the chair and make my way to the sink. For some reason I looked up to see a reflection of Robert staring at me. It sure if he loathed my presence or just didn’t know what to make of this long haired skinny person. I make my way to the bathroom and to the sink to brush my teeth.

I looked up to see my hair a mess, having went to sleep immediately after taking a shower the night before. Very curly and with blue eyes, I could see why I got call calls prior. But looking at the long mirror on the back of the door I became quickly embarrassed. My shorts had ridden up the crack of my ass and my cheeks were visible. Is this what Robert had seen? I was mortified.

I made my way to my bedroom. Brushed my hair, checked my shorts and then walked back out. I began cleaning the kitchen as Robert sat on the couch. Grabbing the trash I made my way outside. The sun felt warm, so after dropping the bag in the can, I stood looking out over the back yard. Looking.around from the deck, out of the corner of my eye I could see him staring. I acted as if I didn’t notice

Our conversations picked up, mostly about music. A few movies and tv shows together, one night he asked if I needed a job. Interested, he informed me that a friend owned a music store and needed someone to work during the days. Two days later, I interviewed and got the job, Robert took me each day, and our conversations grew. We had a lot in common. More than I knew at the time.

A month or so went by and I started getting more comfortable. When Robert wasn’t home, my laptop and porn seemed to pass the time well. One evening, while coming across a cross dresser porn, I became curious what it would be like to actually wear makeup. A day or so later, I asked Robert if he would take me by Walmart on the way home, he sat in the truck as I went inside to buy needed toiletries but passed the makeup and thought what the hell. I spent the next moments picking out a large kit that seemed to have everything you would need. Concealing it in the back of the truck, I quickly put it away when I got home.

Night came, Robert went to his room and I made my way to a shower and then to my room. I grabbed the makeup and my desktop mirror. Found a few YouTube videos and practiced. What I saw looking back at me shocked me. First, I looked a lot like my mom but second, I looked like a girl for sure. The taste of lipstick and the image of a woman staring back at me made me horny. I made my way to my bed and found some porn and masturbated. Sneaking to the bathroom, I washed my face and went to bed. I still couldn’t believe what I had seen.

The relationship with Robert became much more chatty. Robert started joking a lot more and I could tell he was more comfortable having me around. One morning, while I was eating, he walked out in his boxer briefs to grab a cup of coffee. As shocked as I was, the first thing I noticed was his sizeable bulge. Almost as if he wanted me to. I remember going back to my room strangely aroused. What was happening to me?

My others grew more and more. The more I practiced makeup the more I wanted to try more. One afternoon while on break from work, I made my way to a thrift store. Looking around and being curious, I found the women’s section. Other than an older lady, I was the only other person there. Noticing a darn blue slim business suit with a skirt, I tucked it between two dress shirts I found. Finding a set of heels my size, I quickly made my way to the front and checked out. It’s all I could think about for the rest of the day. At bedtime that night, a Friday with no work tomorrow, I began my transition.

Smoky eyes, red lips, hair to one side and a set of reader glasses I had picked up. I grabbed the suit and began putting it on. Standing there looking at myself, I was amazed. Up to this point in life I had not had sex with anyone, but I wouldn’t fucked me. I practiced posing, sitting and walking. I masturbated that night, undressed and at 3 am made my way out of my room to the bathroom to take off the makeup. In shorts and no shirt, virtually hairless, I quietly turned to the left. As I turned I quickly noticed a light from the refrigerator door. Robert was standing there getting a water. I looked directly at him and quickly turned away and made my way inside the bathroom and locked it. Washed my face and sulked to my room.

A week or so went by, no mention of that night. Our conversation went from music, to my plans, to family, to his past and everything between. One evening he said he had a few things to pick up at Walmart. Having a few curiosities about bras, panties and whatever else I could find, I made my way to the other side. Finding a black set of high rise panties and matching bra, I quickly grabbed thigh high stockings and made my way to the self checkout. Looking around, I paid and made my way outside. We made our way back home with beer, liquor, groceries and the lingerie I had hidden under three or more bags.

I made it to my room and hid the garments. Not knowing what had come over me, I changed into my shortest shorts, barely covering my ass. This time, I slipped on the bra and put a hoodie on over it. And then thought wtf, dropping my shorts I slipped on the panties. Just the silky feeling had me horny as fuck and I couldn’t wait to dress further tonight. Checking myself in the mirror, ensuring nothing could be seen. I made my way out of the bedroom and into the living room. Running for a soda, I heard Robert say “ grab a beer, don’t be such a pussy!” They are in the bottom drawer. So I did.

I jad o my drank a few beers in my life and taking the first sip. I think Robert noticed I didn’t like the taste. He quickly stood up, grabbed the beer and said stay there. He returned with a glass of Coke mixed with crown. I could smell it long before I could taste it. This was more me. A few sips in, Robert opened the conversation with “so, how long have you been gay?”. I was floored. I stammered, I am not gay, what makes you say that? He quickly stated “it’s obvious, honestly, I have thought that about you for years. You are built like a girl and move like a girl” I quickly corrected him and stated “well. I am not gay so….!”

More than a few drinks in, he apologized for offending me and asked me not to be angry, he was picking. I was also feeling the effects of the drink I had drank half down. We sat in silence for a few minutes until he said “ well even if you aren’t gay, your makeup the other night looked good”
And laughed. “You saw me” I said quietly and he said yes, and quickly added it was ok. My secret was safe. Looking down into my drink I heard him say “ you need to be careful if you ever go out dressed, guys will not believe you aren’t a girl and will try to get your attention”. With the alcohol clearly talking now, I said “really, that convincing huh?”. He just nodded and looked back on his phone. And what he said next changed everything. He said “you know, you don’t have to be ashamed, you can dress here all you want. No judgement”

Grabbing my now empty drink, he made his way to the counter to mix another. Something about being waited on was so sensual. Having to pee, I made my way to the bathroom and clearly intrigued, I texted him and asked would you like to see me dressed one day. He quickly replied yes, very much so. Knowing what to do. I grabbed my makeup and began work won my face and hair. Very tipsy I made my way to my room, dropped the shorts and holding. Trading for the suit and glasses. One private secretary look coming up. My legs were shaking as I turned the corner to enter the hall.

Part 1 …..more to come …true story!

Related Posts

More Related Posts