The Summer That Changed My Life!

This is a l-o-n-g story! Enjoy the read.

My name is James Jacob Johnson. All my friends call me Triple-J. My dad calls me James, my mom calls me Jamie. I don't like being called Jamie; it sounds too much like a girl's name to me but that's the nickname mom settled on, so I just have to deal with it. I'm an only child. My dad isn't my real father; my biological father died before I was one year old. My dad married my mom and adopted me shortly after I turned three. He's the only dad I've ever known.

This is the story of the summer that changed my life forever. I had just graduated from high school. My dad's brother, Uncle Dave and his trophy wife, Gloria, were going to spend most of the summer in Europe. They were loaded. Rich. More money than they knew what to do with rich! Uncle Dave had gotten in on the ground floor of one of those tech start-ups. He had money, money, money! They didn't have any kids, and I was his only nephew.

He asked me to house-sit for him while they were gone that summer. I leaped at the chance. Not only would I have their huge house all to myself, but Uncle Dave promised to pay me. I would make way more money than I would at some lame summer job. He left me a credit card to buy groceries, I wouldn't have to spend any money on food at all. I had turned eighteen in the spring of my senior year, so I was already legally an adult and would be able to stay at the house by myself.

Oh, a little about me. I was an art major in high school. I'm a pretty good artist if I say so myself. I had gotten a full ride scholarship to State University, room and board, books, art supplies, everything! No way could my parents have afforded that. We were not poor, but both my parents worked full-time so we could be comfortable. Not even close to crazy rich like Uncle Dave!

I'm pretty small for a guy. I'm only 5' 6" tall and weigh 125 lbs. I was on the swim team in high school. I know Dad wanted a linebacker for a son, so I decided to at least compete in something. I was pretty good, made all-conference a couple of times but that was about it. I swam butterfly so I had great abs, great legs, and a great butt. And of course, my cardio was amazing.

Even though I wouldn't be swimming competitively anymore, I still depilated almost daily. I had gotten so used to being hairless for swimming, that I hadn't gotten out of the routine yet. The one concession I had made was to allow my hair to grow out. It was shoulder length; I was rebelling after having to shave my head all those years! LOL!

I arrived at Uncle Dave's the morning they were leaving. Dave greeted me warmly and thanked me again for what must have been the thousandth time since I first agreed to house-sit. Gloria was polite but cool, I don't think she thought very much of my side of the family. Uncle Dave gave me all the codes to all the doors and gates on the property. We had been to their house a number of times in the past, so I was pretty familiar with the layout. Their Uber was already loaded for the ride to the airport. Gloria got in and Uncle Dave shook my hand again. This time he didn't let go. "You have no idea how much I appreciate this, Triple-J! I only have one rule, NO parties. No friends can visit. If there were any accidents, I would be the one ultimately responsible. Promise me!"

I looked him right in the eyes. "Uncle Dave, I promise! None of my friends even know I'm staying here this summer. What you're doing for me is so awesome. I won't betray your trust!" What I didn't tell him was that I didn't really have any close friends, let alone enough friends to even think about inviting them to a party.

He looked at me for a long moment and smiled. "I know you won't Triple-J!" He hugged me one last time and he got in the Uber for the drive to the airport. Their property was surrounded by an eight-foot-high brick wall. There was an Olympic sized swimming pool that pretty much took up the backyard except for the patio surrounding it. I knew I'd be spending a lot of time in the pool. I went inside and decided to explore.

I knew the downstairs well from all the times we had visited. I'd never been upstairs before so I immediately started up the stairs. There was a guest bedroom right at the head of the stairs, Uncle Dave told me that was where I would be staying. I peeked inside, Uncle Dave had already put my two suitcases on the king-size bed. There was an adjoining bathroom so I wouldn't have to leave my room to take care of my personal business.

There were a couple more guest bedrooms on one side of the hall, and a large bathroom and laundry room on the other side. At the far end of the hall, was Uncle Dave and Gloria's bedroom. I opened it quietly and tiptoed inside. I have no idea why I was being so quiet, but I couldn't help myself. It was the biggest bedroom I had ever been in! The bed itself was bigger than anything I had ever seen. It was way bigger than king-size; it looked like you could sleep a family of four in it, easily!

To the left was a bathroom and closet area. I looked in and could tell it was Uncle Dave's side of the bedroom. To the right was another bathroom and closet area, this had to be Gloria's side. All the makeup on the counter told me I was right. I walked into the closet and just stared. It was huge; it looked like three or four walk-in closets combined!

Down the right-hand side hung all manner of women's clothing from formal gowns and cocktail dresses to skirts, blouses and dress pants. At the far end were shoe cubicles. The cubicles ran from floor to ceiling and wall to wall. Color, style, heel height, you name it, Gloria had it. She probably could have opened her own shoe store! The left-hand side was covered with dressers. On top of the dressers sat a couple of dozen wigs on wig stands. All were different colors, lengths, and styles. On top of the dresser nearest the door, were three full size jewelry boxes. Each box contained all types of earrings, rings and bracelets. Behind each box was a necklace stand with necklaces matching the jewelry inside.

I started opening dresser drawers randomly. Lingerie of every style and color, all matching sets. Bras, panties, garter belts, waist cinchers, corselettes, corsets, full slips, half-slips, camisoles, thigh highs, stockings, pantyhose filled every drawer. At the time, I didn't know what most of that stuff was even called. My good friend Google helped me learn the names of all those things later on. Gloria must have kept some kind of inventory somewhere; I have no idea how she could have even begun to remember where everything was otherwise.

One dresser held all her sports gear, leggings, tights, workout bras, swimsuits including both one-piece and bikini style. I don't know what possessed me, but I held up one of the one-piece suits against me and realized it would fit me. I had never thought about it, but Gloria and I were almost exactly the same size, except for those luscious breasts of hers. I had masturbated thinking about Gloria before, she might be cold and aloof, but she was gorgeous and sexy! I shook my head and put the swimsuit back in the drawer.

The last drawer I looked in had all of Gloria's sex toys in it. Dildos, butt plugs, ben wa balls, edible lubricants, bondage items, I had no idea what most of these items were called let alone what they were used for but again, my friend Google helped me figure it out. There was an old driver's license of Gloria's in the drawer also. It had only expired less than a month ago.

I went into her bathroom and started going through all the drawers. They were filled with makeup of every kind. Then, in one drawer, I found tits! I guess they're called breast enhancers. They fit underneath yours, pushing yours up and out while giving you more volume and support. Again, I have no idea what got into me, but I grabbed a pair of them and pushed them up under my tits. I looked in the mirror and was stunned to see I had a small pair of what looked like women's breasts on my chest. When I realized what I was doing and how I looked, I blushed beet red and threw the enhancers in the drawer.

I ran out of their bedroom and down the hall to mine. I started unpacking my suitcases hoping the busy work would get my embarrassment out of my mind. What the hell had I been thinking? It was lunchtime and I was starving. I went downstairs to get something to eat. I was on my tablet, just porn surfing when I got linked to some pictures of crossdressers. I'd seen them online before and hadn't thought much about it. Heck, there were some who were so good looking, I had jerked off to them. No penises though! I only looked at the gurls who didn't show their cocks. I wasn't interested in that!

Looking at those pictures made my mind return immediately to Gloria's closet and bathroom. A person certainly had everything they needed if they wanted to imitate those gurls online. I shook my head and decided to go for a swim. A workout was just what I needed. I enjoyed my time in the pool, it was relaxing and fun. Afterwards, I wandered around the grounds, enjoying my walk while I cooled down.

I took a nap and woke up refreshed. This was going to be an awesome summer. I wasn't on anyone else's schedule. I could do what I wanted, when I wanted. Uncle Dave had stocked the beer fridge and the wine cooler to the limit. I had enjoyed an occasional adult beverage in the past but never over-indulged since I always seemed to be in training. I grabbed a beer and sat down on the deck of the pool in a lounge chair. I had my tablet in my lap and was porn surfing again. Links to crossdressers came up, and I checked them out.

A lot of the gurls looked absolutely amazing, to the point I was wondering if they really were girls just posing as crossdressers. I started doing a more general search and was amazed to find some of the before and after pictures. "It's almost like these gurls are artists themselves with their ability to transform themselves from one gender to another so completely." That thought got my competitive juices flowing. Hell, I was an artist and a damn good one. If they could do this, so could I.

I prepared dinner and continued to let these thoughts swirl through my brain. I finally decided to put all such thoughts on hold. I was going to go online and play some Dungeons & Dragons with the group I'd been with for the past few months.

I woke up late in the morning, and my first thought was about competing against these gurls, trying to look as passable, no not just passable, but as beautiful as they did. I brewed some coffee and sat down with my tablet. I entered some crossdresser websites, and it soon became abundantly clear to me I had the wrong mindset. This wasn't a competition; it was a celebration of all of their femininity. They all supported one another and cheered each other on.

I timidly created the bare outlines of a profile but there was no doubt my femme name was going to be 'Jamie.' (Thanks, Mom!) I started talking with some of the gurls, they were very supportive and encouraging. They directed me to some online makeup tutorials and wished me good luck. One gurl in particular, whose name was Maria, gave me what turned out to be great advice. "Jamie, before you start to put on any makeup, make sure you are at least dressed in the lingerie, stockings and heels you're going to be wearing. I always feel so much more feminine when I sit down to do my makeup. It really helps me; I swear it does."

I went upstairs to Uncle Dave and Gloria's bedroom. I took my tablet into her bathroom and began to explore more closely. I brought my tablet with me because I was going to create an inventory map and database. No way was I going to move things around and then not put them back where they belonged. I got out various makeups, different types of brushes, sponges and application pads. I began to research them, what their purpose was, how to use them. As an artist, I wanted to be as familiar with my medium as possible.

My stomach growled and I realized I had spent the entire day learning about makeup itself. I hadn't even started putting any on yet. But that was the way I always learned new things. I wanted to feel comfortable and confident that I knew what I was doing.

I put everything back where I had found it; took my tablet and went downstairs to make some dinner. For some reason, I decided to open a bottle of wine. I usually wasn't much of a wine drinker, only on the holidays with family, but something inside me told me it was time for some vino'! I found what I thought was a feminine looking goblet and gently poured a quarter glass of wine down the side. I gave it some time to breathe while I was cooking. I took little sips while preparing my meal and then refilled my glass when I sat down to eat.

I checked the profile I had created and realized I had a message. "Hiya sexy! I can't wait until you get brave enough to post some pictures. I can just tell you're gorgeous!" It was signed, 'HotMan4U!' I almost spit my wine across the table. Holy shit! I was getting hit on already. By a guy! I logged off immediately and decided to go swimming again. The exercise and fresh air helped clear my brain. I toweled off and began to explore the grounds again. It was dark by now and as I walked around, lights would come on and illuminate the area I was in. Motion sensors. I hadn't ever really thought about it before, but it was comforting to know no one could approach the house without being bathed in light.

I spent the next few days with my tablet in Gloria's bathroom. Using the makeup tutorials, I began to experiment on me. It was a process. I definitely didn't like the way I looked that first day, by the middle of the second day, I was beginning to like what I saw in the mirror but still wasn't satisfied. I took some selfies and began to compare them to pictures of other gurls to see what I might be doing wrong. I ate dinner thinking about how I might try some different things tomorrow. I absent-mindedly logged into my crossdresser profile; I had another message from the same guy. "Hi girlfriend. Don't be so shy. I'd love to see some pics! XOXOX!"

I got brave and messaged him back. "You're too kind. I'm still not completely happy with how I look but I think I'm getting close. In the meantime, maybe you could send me a picture of your face, so I know how you look!" I hit send and logged off immediately. What the hell was I thinking?

I fell asleep with a glass of wine on my nightstand and my tablet in my lap. I was looking at pictures of gorgeous crossdressers online wondering if I was being foolish, wondering if I could ever look that good.

By the end of the third day of experimenting with makeup, I thought I was starting to get it, but something still seemed to be missing. As I lay in bed that night, just before I fell asleep, I remembered what Maria, my chat room gurlfriend had told me, "Jamie, before you start to put on any makeup, make sure you are at least dressed in the lingerie, stocking and heels you're going to be wearing. I always feel so much more feminine when I sit down to do my makeup. It really helps me; I swear it does." I dreamed of myself wearing feminine underthings that night. When I woke up in the morning, I realized my underwear was moist. Clearly, I'd had a wet dream.

After a very small breakfast and coffee, I went to Gloria's bathroom again. I ran the tub as hot as I could stand it and poured in some of Gloria's floral bubble bath. I played some light jazz on my tablet while I soaked; I always found that kind of music very sensual. After a long time just luxuriating in the scented water, I got out and toweled myself off. I really didn't have much in the way of facial hair, but I shaved as close as I could and then shaved a second time. Looking at myself naked in the mirror, I took a deep breath, grabbed my tablet and walked into Gloria's closet.

I pretty much knew where everything was by now, but I had my tablet with me to take pics so when I put things back, I could put them back exactly how I found them! I went to a dresser I knew had bra and panty sets, and just stared. I finally settled on a crimson red satin and lace bra and French cut panty set. This was it. I either stopped now or had no idea where this might lead me. I took another deep breath and stepped into the panties. As I pulled them up my legs, I was in sensory overload. I was panting, nearly hyperventilating from how wonderful the material felt as I pulled the panties around my ass cheeks and settled my very small cock into them.

I'd been teased unmercifully in the swim team locker room by the other guys because my dick was so tiny. It was less than 2" long when soft and barely made it past 3" when erect. I know because I measured myself. I put the bra on backwards, clipped myself into it and put my arms through the straps. I adjusted it until it felt comfortable. (Online tutorials can be so helpful!) I giggled as I thought of an imaginary conversation. "Hi mom, it's Jamie. I'm in Gloria's closet trying on one of her bras. Can you tell me how to get into this thing?" I giggled again, no way would that go over well.

I found the matching garter belt, slipped that on and threaded the garter tabs through the legs of my panties. Gloria had stockings galore, including a lot of unopened packages. I decided to stick with what was already opened and grabbed a pair of suntan-colored nylons. I took them to the back of the closet and sat down on a velvet stool next to the shoe cubicles. I guessed this was where Gloria picked out her shoes and put them on for the day.

I rolled the stockings up my legs and clipped them onto the garter tabs as I had learned in a video. I was not prepared for the glorious feeling of the way the nylons felt against my hairless legs. I was rubbing my legs together, crossing and uncrossing them to see how my thighs felt against one another. More time had passed than I realized, it was almost as if I was hypnotized by the feeling of the stockings on my legs. I looked down and my cock was erect; I could see the drop of pre-cum soaking through my panties.

I shook my head and looked at Gloria's shoes. I settled on a pair of red T-strap stilettos with 3" heels. They fit like a glove. I stood up and immediately lost my balance. My ankles were wobbling. I sat back down and pulled up another tutorial online, this one was about how to walk in women's high heels. I watched it multiple times, took a deep breath and stood up. I waited while my feet and ankles got used to the feeling. When I was able to stand comfortably, I began to walk towards the closet door.

It took a few times of walking up and down the length of the closet before I felt I was getting the hang of it. Heel to toe, small steps, walk slowly, lean slightly back, one foot in front of the other, roll your hips slightly, walk in as straight a line as possible, arch your foot just a little. I was saying these things in my head like a mantra as I practiced walking in the heels. Soon, I headed out into the bathroom and sat down at the makeup counter again. I reached over into the breast enhancer drawer and pulled out the same pair I had held up to myself the first night. I slipped them into the cups of my bra and adjusted them. I stood up again and walked to the full-length mirror on the back of the door. I gasped, even without makeup, it seemed as if an attractive young lady was looking back at me.

I sat down and began to apply makeup again. I wasn't sure why, but it felt different this time. It almost felt as if an invisible hand was guiding me. I just felt so much surer of myself. It reminded me of how I felt when I was using a new medium in one of my art classes and realized I had finally gotten the hang of it. I took my time, wanting everything to be perfect. I put on candy apple red lip gloss to finish everything and really looked in the mirror at my entire face, not just the area I was working on. I gasped. I was beautiful. Not just beautiful but breathtakingly gorgeous.