Yes I Am Jennifer Your Son!

by Christina Cox

 

So there I was…waiting all dressed up. I do not know how to put this, I really thought I was an everyday normal boy. But, in the past year, I noticed I did not do things or shall I say admire things other boys my age admired. I am Jonathan Drake, a somewhat normal 13-year-old boy who likes to wear dresses, make up and heels!

I really thought about this hard enough and my mom should know I guess. I am very confused. Mom and I have always been close. But I never thought I wanted to be mom, or hell…dress like her. My mother is an RN and she is very smart and beautiful. I was her little man, I was in theater and played baseball. Why did I start having these desires of dressing like a girl?

It really started about a year ago, I was helping mom do laundry, and a pair of her panties got mixed up in my clothes. I was in my room organizing my clothes and found them. They were silk and shiny. Just the touch was enough to be an exhilarating feeling. I figured what was the harm in just trying on her panties. So I tried them on, and laughingly they were a bit larger for me. They felt so incredible though. So I questioned does all women's clothes feel this good? Why do they get to wear soft silky smooth feeling clothes, when men wear just plain cotton clothes?

So part two of my change was when my mom would go to work, I would investigate what other articles of clothes felt like. My mom worked the afternoon shifts into the night and was usually home by 10:00 or 11:00 at night. She trusted me to be at home alone and would rent me movies or video games. Sometimes I would stay over the neighbor's house, but when I was alone, I would see what mom had in her closet.

My first encounter was bra and panties. She had big hoots; 36c's to be exact. You have to start with the foundations and work your way up. So I went through her drawers and saw a pair of lace panties. I quickly changed and tried them on. I went through the drawers again and found a matching bra. I did not know at first how it really worked, but after close trial and error I figured it out. In the same drawer she had many stockings. I was not sure, but they were like large silky socks. I quickly tried those on and to my surprise they felt elegant on my somewhat close haired legs. They made my legs feel so smooth and silky. I was in a daze with the feeling I was getting! I felt excited, happy, and somewhat relaxed all at the same time! That first time was an unbelievable feeling. But then I pursued to try on her heels, they were believe it or not somewhat a little larger for me.

They were also an experience. She had dozens of heels, flats, and boots!

As time went on I began to practice in dressing in various outfits. She was about my size, except in the panties, which fit, a bit larger. I had no ass, so they seemed a bit baggy. I should say for self-teaching myself to walk in heels, I do not think I did such a bad job. She had a variety of heels from low heels to strappy to a few fun stilettos. Geez, the stilettos felt so exhilarating as they picked me up about 5 inches off of the ground. The platforms were nice too! So I would spend some of my nights fully dressed clanking around the house in heels until I got comfortable and felt right in them. It did take me a good month to learn to balance myself in stilettos—hee hee!

Well, finally after I would doll my self up, I would pursue make up of course. I have no clue what to do here. I just tried to put lipstick on and tried to look at some women's magazines to look at their faces and be like them. There were some night's I was just too perfect. Mom had this gorgeous red party dress that I would wear with red heels that made me look like a hot teen prostitute! I just wish I had the hair. I never tried nail polish or went as far as a dolled up wig.

So now here I was, I decided it was a year since my first encounter with the black silk panties. I was dressed up in a red silky short sleeve form fitting top, had the black bra and panties on with socks stuffed in the bra, also wearing her black business mini skirt, and my legs all drenched up in her darker tan ultra smooth pantyhose. Yes! Pantyhose, the ones you wear like pants. I slipped one leg up to my knee then slipped the other side on and had to wiggle the set up to my belly! They felt oh so so so good. My privates became so hard and filled with excitement. I had to release and clean myself and continue dressing. After I did, I felt completely fine and relaxed. So I decided, I need to tell mom.

I really enjoy this, she needs to know, I do not know why I feel this way, but I just know I feel right when I am in a skirt and pantyhose. So I gathered myself and put on a pair of black velvet 3-inch heels she had. They felt fine, I did not want to shock her and make her think I was already a cross dressing slut wearing her 5 inch heels—ha ha! I really loved this red top; it was so silky and clinged to every inch of my body. So I took one final look in the mirror, saw the clock was 8 pm and decided this is how I would present myself to mom. So now I wait. And I waited. And waited. Finally, I heard her pull in and I quickly ran to the door and unlocked it so she would have to come to me. I prepared myself in the living room and waited. I was frightened and nervous to see me like this. I was so in fear of her shock, but this was the only way she can see the true me.

"Jonathan, Jonathan, can you come out and help me with the groceries?", she cried from the door as she pushed it open.

" Um, I can't really do that now, mom, can they wait?", I answered.

She did not answer. Apparently she had gone to the car to retrieve some of the bags.

She returned with some of the bags and placed them by the door and called again,

"Jonathan, can you please give me a hand, at least grab them at the door and take them to the kitchen", she called. And I heard her briefly whisper to herself, "Lazy kid!"

So I began to walk to the door figuring it would be safe to grab groceries from there and she would not see me until she was inside. I walked in my heels, clickity clack on the hard wood floors. I was at the door and grabbed a few bags and took them to the kitchen.

She was locking up the car and taking the remaining bags from the car. I placed the bags on the kitchen table and began to head back to the front door, then it happened as if it was in slow motion. I felt like a runway model walking down the hall to my front door, and as I got closer, my mom came around and walked in. She did not notice me as her head was down…she closed the door, and then heard some heels walking closer to her. The bags stopped rustling and she quickly turned up and around and looked at me like a deer in headlights!

She screamed, "Who are you!?", with her back trying to unlock it. We were about six feet apart. And then I said to her for no real reason, " I am Jennifer, your son".

She was uphauled, almost tearing. She began to stare, and began to speak in dismay, or rejection," No, no, you can't be him, you can't, no…..no, no, no, no, no!" And then she started to cry, and she just looked down at the ground and grabbed her head in rejection.

"No, why, no, why me, why him, no God, please, oh please", she clammered.

Then I began to feel her regret, her only son, now a crossdresser, and who knows what else, gay, transgender, mostly confused.

Then when she saw me cry, she came close and said,"Oh God, no, there there" And then we hugged. We hugged for what seemed like an eternity as I towered about three inches over her as I was wearing her heels.

Then I said, "I did not know any other way to explain it to you".

She just looked at me and said " Well, I guess I have been missing a lot of what has been happening to you, and part of that is my fault….hmmmm…well, you do look very pretty, almost too pretty. But son we need to seriously talk."

So she gathered herself pulled me out at arm's length and her crying began to stop. She was trying to sort out the whole situation in her head.

Then she answered, " It is late, we need to discuss this in the morning, you can't sleep in my clothes either, as for the panty hose and underwear, their yours now. I do not like wearing other people's personal items… but the skirt, heels, and blouse go back. As for sleeping, I have a nightie-teddie that might fit you. You do look gorgeous, a lot like how I was when I was 18. God, why me. Let's put the food away, and we'll talk all about it the morning. Sound like a plan."

"Yes, mom and thank you", I replied as I dried my tears.

"Not a problem", she paused then exclaimed, "Jennifer !", with a laugh in her tone and rolled her eyes.

 

(to be continued)

  

  

  

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