Growing up I spent most of my time around women. Not having a male figure in my life, I found myself gravitating and relating more to women. Not to say that I wanted to become one, but I think I became more sensitive to them. That is until I reached high school and all the manly things started to show more. When the puberty changes took place and I started getting more involved in sports, my attitude changed to where women became more of an object and something I could win over. Needless to say, I lost a lot of friends because of that. The few close friends that stuck around, made it clear how dumb I was acting.
I recall a conversation I had with arguably my closest friend at that time. We talked about almost everything. There were many times where she and I would debate for hours about complete nonsense. On one occasion, I made the comment that men had to work harder at building and maintaining relationships. Women had their physical features to their advantage – to establish the relationship then held their physical assets hostage in order to mold the relationship the way they wanted.
My friend, of course, thought I was full of crap, but we were teenagers and not experts in psychology and certainly not experts in how solid relationships actually worked. She told me that I had no idea what it was like to be a woman and that relationships are not built on physical features alone. She added, that if I knew how much work a woman had to go through to make themselves presentable – I wouldn’t believe the utter crap that came from my mouth.
I think we finally agreed to disagree, but for the next couple of days, I gave that conversation a lot of thought. It was the summer and all I had was time and my thoughts were all I had to combat the boredom. I was convinced that I was right, and I wanted a way to prove it not just to her but to myself as well. The question was how. I thought about it and decided to perform an experiment, timing how long it takes a man and a woman to get ready in the morning for a long day. I wanted to make sure there was no way I could be proven wrong, so I walked through it- on paper – every step of the experiment – from sunrise to sunset.
Then I needed the tools. For a man, that was easy, but for a woman, it was a little more complicated because I didn’t have them. I wasn’t sure what I needed, so I used my mother as a reference point. I watched her get up in the morning and go through her step by step process for getting ready for work – noting every detail right down to how she matched her makeup to her clothes and shoes. I am sure I looked like a perv and was probably not that inconspicuous carrying around a notebook.
After she left for work, I raided her closet, but since she was a bit bigger than I was, it was difficult to find the right combination of apparel. Fortunately, my aunt, who was only a few years older than me and roughly the same height and build, had what I was looking for. I stopped by her house and raided her closet instead… picking out things I saw her wear only once and that I thought she looked good in. Following my mother’s lead, I took a number of things… dress, skirt, bra and panties, nylons and a garter belt. I then hit her bathroom and found a couple of hair clips, although I figured, I would not use them since my hair was short. I concealed everything in my backpack and brought them back to the house and hung them in my closet.
I then proceeded to begin the experiment starting with what I knew. I logged everything I did as a man – from the time I woke up to the time I was ready to leave the house. The process took roughly 20 minutes and included an eight-minute shower followed by a brush of the teeth and a comb of the hair. I then threw on my underwear and socks followed by a t-shirt and pair of jeans. After sliding on my shoes, I was ready to go. Pretty easy… and quick.
The tough part was to see how the other half lives. As soon as my mother left for work the next day, I continued the experiment. I jumped in the shower and proceeded to shave my legs, which was nothing short of impossible. After the shower, I jumped out and dried off. I slid on the lace panties and put on the bra. After adjusting the straps, I took a look in the mirror and thought this is not that big of a deal. Outside of the shaving, the process didn’t seem too different.
I snuck out of the bathroom back to my bedroom, hoping that my mother didn’t come back to the house and catch me in the act. I put on the nylons, which were tough because they were snug and a little awkward to put on. Once I had them on and straightened, I attached them to the garter belt out around my waist. I put on a pair of my mother’s pumps and struggled to walk around in them. I wasn’t even close to being ready and I was starting to realize I might have been wrong about my hypothesis.
I pulled on the skirt and put on a white dress shirt I had in the closet. I walked back to the bathroom and took another look and from the neck down I didn’t look half bad. My chest was still a bit flat, so I stuffed it with tissue, which made me look a little more believable. I grabbed the hair clips and held them up against my hair. After trying different spots, I slid the clip along both sides of my hair above my ears.
The toughest part was the makeup. I took my mother’s compact and rubbed powder all over my face. The first time through, you could see every spot I missed. I tried over and over to get it right but eventually gave up and moved on. I then took a big brush and brushed on some red blush. Remembering how my mother did it, starting in a small circle then moving it up my cheek towards my ears. Again, I had difficulty getting it right, to the point where my face was starting to look more like a clown, but, I finally got something right. I pulled the red lipstick and slowly rubbed it right along the edge of my lips, pressing them together and puckering to make sure they looked good.
When I was done, I walked over to my mother’s room and stood in front of her full-length mirror. Going over every inch from head to toe, I was found myself moving my body and posing in a very lady like fashion. Getting up on my toes watching my calf muscles tighten up through the nylons; turning around to where my butt and the back of my legs were reflecting off the mirror. As I looked at myself, I realized how great I looked and it was a major turn on – and as long as I didn’t look up at my face, I was a very believable woman.
I walked back to my room, removed the top and skirt and grabbed the black dress and tights. I had some difficulty zipping it up but once I did, I ran back to the mirror and again admired how it looked as it hugged my body. The dress was so tight; I noticed the slight bulge of my penis poking against the dress. The more I looked at myself the more I kept imagining long flowing hair, a better make-up job, and maybe a little bit bigger butt.
The next thing I knew, I heard my mother unlock the door and I looked up and it was 4 hours later. I somehow went half the day getting dressed and staring at myself as a woman.
I ran and locked myself in the bathroom where I turned on the shower and changed clothes and washed off the makeup. I wrapped the clothes in a towel and carefully went into my room. My mother came and knocked and just before she walked in, I threw all of the “evidence” into my closet. When she walked in and noticed I appeared nervous, she asked if I was okay and I went on the defensive and yelled at her for barging into my room.
Through the evening and into the next day, I kept thinking about the entire experience. I realized how hard it was for me to look presentable and also realized that I was both right and wrong. Women do use their physical gifts to get what they want, but it takes a lot of work.
Now that the experiment was over, I came to the conclusion that I needed to continue the test. I didn’t know what I was doing which is not typical for an experienced woman. I needed some help but wasn’t sure how to get it. One thing was clear though… I had to continue the experiment until I was “satisfied.”
Over the next few months, I couldn’t get passed my little experiment. I continued the attempts to get better at finding the right outfit and spending less time getting ready. While still in secret, I often wondered what it would be like to go out dressed, but the spike of my anxiety level every time there was a noise near the front door kept me focused on the real task. I started to get the hang of the dressing part of the experiment. I was able to find the right combinations to wear that were quick and at the same time sexy. I even started to look outside the house to perform more research. I spent time at the mall where I could watch the makeup counter from a distance and even purchased an outfit or two for “my girlfriend” and “my sister”.
Doing this was not without its challenges. Lack of a wardrobe was only one of the problems, but TIME seemed to be the biggest challenge. I had to find a way to have private time to dress and still be able to be what everyone expected me to be and what everyone saw.
The wardrobe problem was slowly being handled with visits to my aunt’s house and my occasional “gift shopping”. As before, I would raid my aunt’s closet and find outfits I could wear and at the same time, bring back what I took before. Since I spent so much time there anyway, it was never really noticed – or so I believed.
My close friends were becoming more and more distant as we were all preparing to go to college. For me, college was already set. I had a few weeks left at home before heading off to school, so I wanted to take advantage of the private time I had before it was gone.
During those last couple of weeks, I was able to dress almost every day, and while I began to perfect my look, the last day before I left for college was the most traumatic. I already had a few intimate essentials that I either kept or bought on my own while sneaking through the women’s department at the mall.
The last day started like most. I usually got up before my mother, so I got a jump-start on the day. I rushed to the bathroom and put on a new red lacy bustier and started to feel really sexy in my tan pantyhose. Once I was done I snuck back to my room and jumped in bed. I should have known the day was not going to be a good day when my mom decided to come in and try and get me out of bed to take out the trash.
She tugged on the blankets trying to get me up and I fought and argued with her long enough that she gave up and I told her I would take it out… which of course I forgot to do.
Once she was gone, I continued through the day. I went back to the bedroom and put on a new dress. Then to the bathroom where I fixed my new blond wig and started putting on make-up. I had gotten better over the last few weeks but still struggled with the eye shadow and eyeliner. When I was done, I went back to the mirror in my mom’s room and began to admire myself once again. The difference now was that I was keeping an eye on the clock so I wouldn’t run out of time.
The black dress hugged my waist tightly and it was a tough chore to get the zipper up from the side, but I was finally successful. Covered from the neck down in all black was interesting for me. I really felt sexy and aroused. It started to show when I turned to the side to admire my profile.
I slipped on the flats I “borrowed” since the high heels were tough to walk in and proceeded to parade around the house. I would try and walk like a fashion model and sit like a woman with my legs crossed making sure my private area was covered, but still showing a little leg from the slit in the dress. The more time passed, the more aroused I felt.
I found myself spreading my legs as the dress slid up my pantyhose covered thighs and proceeded to rub myself causing my penis to try and penetrate through the panties and pantyhose. I went back to my room and laid in bed continuing to pose and enjoy the day and that is when things took a turn.
My closest friend, Denise was coming by so we could hang out together. I had completely forgotten, and wouldn’t you know it – my mother left the door unlocked. Denise is the reason why the experiment started in the first place. We had discussed it over and over again and while I conceded that women had a tougher time, I was still trying to convince myself it took the same amount of time to get ready as men… a battle I was losing fast – and one that I was accepting and learning to love.
I never heard her knock on the door and never heard her come in. When she saw me in my room, she was floored.
“What are you doing?” she asked.
I freaked and was scrambling to get covered up, but it was no use. I couldn’t even play it off as a joke. I just sat there silently hoping she would leave. No such luck.
“Is this why you kept asking me all those questions?” she asked.
Again, I was completely silent. She sat down on the bed and I was powerless to move. She took a hold of the blanket I was using to cover up and pulled it away uncovering what I had done. Still aroused, she pulled the bottom of the dress down to try and cover me up. She then looked at my face and hair.
“Come with me.” She said.
I didn’t want to, but she took me by the hand and escorted me to the bathroom and had me sit on the toilet and started to wipe away the makeup I had on. She then proceeded to teach me how to apply it properly. Starting with the foundation, then working on the blush and eye shadow. She finished up with the eyeliner and lipstick – matching the colors perfectly.
“See, isn’t that better?” she asked.
I just stood there staring at myself and wondering why I couldn’t do that. Her makeup job made me look more believable than ever. She then walked me back to the bedroom and showed me how to sit and how to stand and even how to walk. I never said a word I just took her instructions and never questioned her. She then had me change shoes and even after hinting that I couldn’t walk in high heels, she helped me put them on and held my arm as I tried to maintain my balance as I walked in them. The more I did the less I needed her help. Within an hour I became a pro. We continued practicing through the morning and I started to relax more, and we started a conversation.
“Can I ask you a question?” she asked, “Do you want to be a woman?”
I never really thought about it, but I just shook my head “no.”
“Are you gay?” she asked.
Again, I signaled to the negative.
She then did something I never expected. While we were sitting next to each other on the bed, she leaned over and kissed me on the lips. She had never done that to me before. We had been friends for a long time, but we never even attempted to explore that part of our relationship.
After she kissed me, I took her by the hand and kissed her. Before we knew it, we were making out right there on my bed. She began to caress my thighs still covered in nylon as I rubbed her naked legs.
She then got up and while she and I continued to kiss, she unbuttoned her tight blue jeans and began to slide them down along with her pink underwear exposing her tight pussy. I took a firm grip of her ass and pressed her to me where her breasts were firmly up against my face. I began to caress her back and tight butt as she continued to stroke my hair and lick my ears, neck, and shoulders.
She then stood me up and tried to unzip the dress I was still in. After several failed attempts, I helped her unzip it and she proceeded to help me take it off. She reached around me and unhooked the bra with ease and then continued to kiss me before moving down and gently biting my chest. We began to lay on the bed and continued “playing” when her hand slid down my chest and stomach down to my crotch. She touched my penis, which was already rock hard, and I thought I would rip right through the pantyhose.
She continued gently rubbing my penis and with her other hand, guided mine down to her pussy. She pulled down the pantyhose far enough to where my penis popped out and she continued to stroke me. She then got on top of me and slide her body down mine until she was facing my rock-hard cock. She then began to lick me gently making sure I was nice and wet, then engulfed my penis and began sucking so hard I thought she would rip it right off.
It was clear we didn’t know what we were doing but we were willing to help each other learn what we liked and disliked.
“Slow down.” I said, “Not so hard.”
“Is this better, she said as she loosened the grip of her mouth and slid my cock in and out of her mouth.
“Yeah… Oh god yes,” I said.
“Do you like this?” she asked.
“Yes”, I said as I held my hand on the back of her head.
“I like it when you dress up for me.” She said.
I was a little nervous to respond, so I didn’t, but I was really turned on by the notion. She then slid back up – keeping her body in contact with my cock. She kissed me gently on the lips and I could feel her guide my cock into her tight pussy.
“oooOOOO… Yes.” She whispered.
“OOOO… that feels so good” I replied.
“Oh my god, you are so big.” She said loudly as she began to slide up and down the shaft, “I love it when you are inside me.”
I remained silent simply enjoying the feeling and the commentary.
“Do you like it when you are inside me?” she asked.
“Oh yes,” I said.
“I want you to dress like this and fuck me all night long,” she said.
She continued to ride me, and I was ready to cum so I bounced her off of me and she grabbed a hold of me until I came all over myself. She took her finger and rubbed the cum all over my stomach and then laid on my chest until we both started to doze off. About an hour later, I woke to find myself still dressed and her still in my arms.
“Why didn’t we do this a long time ago?” she asked.
I slid my hand up her back and said, “I don’t know, but I’m glad we did.”
She picked up her head and we continued to kiss… UNTIL.
“What the hell are you two doing?” my mom said.
We both were now trying to cover up as my mother blew a gasket looking at me in pantyhose and Denise completely naked in bed together. Denise covered her head under the covers and for some reason; I was trying to protect her – yelling at my mom to get out of my room.
After she left, we knew the walk of shame was next. We both went to the bathroom and got cleaned up. I then walked Denise to the front door and told her I would come by later.
From the back room, I could hear my mother yell out, “No you won’t.”
I ignored my mother’s comment and watched Denise head home. I then proceeded to head back to my room where my mother was waiting for me.
“You know this is not over,” she said as she held the dress in one hand and the bra in another.
I didn’t have anything to say, so as I had done most of the day, I remained silent.
“You think we didn’t know what you were doing,” She said.
She explained that my aunt had called her asking about her missing wardrobe and since I was the only one who had been by, she suspected me. I tried to deny it at first, but the evidence was in plain sight.
“What are you some sort of sissy?” she asked.
Again, I remained silent.
“If you want to be a woman, that can be arranged.” She said angrily, “You now have to go explain to your aunt what you were doing in her clothes.”
I was completely mortified and just ran out of the house over to Denise’s. After I explained to her what was said, Denise did not seem too concerned. I, on the other hand, didn’t know what to do. Denise, however, had an idea that initially made me feel worse.
“I think you and I should go shopping and pick out something nice for you. Get you all dressed up and take you over to your aunt’s house and show her how great her new niece looks,” She said.
I, of course, was not amused.
“Of course, I am kidding, Let’s go talk to her together,” she suggested, “I will just tell her it was a prank and things got out of hand.”
While believable, I wasn’t sure I could go through with it, but there was no stopping her. She picked up the phone and called my aunt and began to explain. After they got off the phone, it appeared that things with my aunt were okay, but we still had one more person to deal with. Denise and I went back to the house where my mother had calmed down a little but was still angry. Denise again explained the same story to her, but it didn’t have the same effect.
“I hope you have fun at college,” she said, “Just make sure you don’t pick up any strange boys.”
Still upset, she demanded I pack up my things and leave the house a day early, so Denise and I packed up the car and I dropped her off at home before leaving for school. Denise was very sorry we got caught but was thrilled at where our relationship had moved to. We were already making plans for our first weekend visit together.