Developmental Generation Ch. 01

Developmental Generation Ch 1

Growing up was an ordeal. Born premature and underweight didn't help. Plus everyone on my father's side developed asthma and so I had to take medication for that. As a result I was put on pills early in my youth to help me cope. Later, I used an inhaler. One of the side effects which seemed to affect me the most was growth. Now a twenty year old adult, my height is barely five-five and my asthma still with me. Fortunately, the other side effects were minimal to none... or so I thought.

My father was killed in a traffic accident when I was about three. On the highway, a speeding dump truck driver wasn't paying attention to the slowed traffic ahead, smashed into Dad's car and sandwiched him into the semi in front. But it was fortunate for my mother and me that Dad had provided for us and money wasn't an issue. Mom worked part time at an office and so as a youth, I spent a lot of time with her. She tried to be both a father and a mother to me but ultimately the mothering part won out.

For me, I always tried to please and help her out as much as I could. I did my best at school and at home. But later, when I think of it, I think she pined for a daughter if Dad was still alive. Even so, her only true love was her husband. She did go out but hasn't found another.

As for school, I had a few friends. Much as I tried, sports wasn't my thing and they excelled during their grow spurts. One of the guys I hung around with in my senior year, had swiped his dad's Penthouse and showed it to us. The pictorial had a couple of hot looking models with big tits making out while dressed in lingerie. Then entered some male model with a big dick who ends up fucking both of them. I was pretty sure the four of us had boners in our pants.

Later at home, I stripped down my pants to jerk off. With my small hand gripped my shaft, about a half inch stuck out the top uncovered by my fist. As I stroked my uncut wiener, I thought about the lingerie the models were wearing and then I imaged myself wearing the same. I came really hard. So hard, my cum spurted from my dick, arced up and hit me on my face and chest. "Ooohhh... Fuck! Uuuhhh! Uuuhhh!"

It took a minute to recover before I quickly cleaned myself up. I threw the soaked Kleenex into the trash but it fell on the floor. My waste basket was overflowing with cum filled tissues. I picked it up delicately with two fingers and shoved it onto the pile.

So, yes. I masturbate a lot. Porn on the internet was too easily accessed. After seeing the Penthouse spread, more and more I started looking at women dressed in lingerie and having sex. Then I saw her. This gorgeous, woman with long dark hair. Dressed in lingerie, she danced around on her own as she removed her lacy bra and freed her nice, firm boobs. She looked directly at me with her brown eyes that penetrated deep into me. Then her perfectly plump, painted red lips blew me a kiss, I pulled out my already hardened dick and stroked it.

She continued to gyrate around clad in shear, seamed stocking, garters and matching thong panties. With her ass towards the camera, my mouth watered to eat her perfect bum. When she rotated around and my fist pump stopped. There was a lump where her camel toe should have been. Then she pulled her thong aside and a cock fell out. I looked at the video description. "Chanel Santini rubs one out."

"What the fuck?" My jaw dropped. I had landed on a trans-site. I didn't even know transsexuals existed never mind the existence of trans-sites. I watched her as her hand held onto her thicker-than-mine shaft and stroked it. My own hand moved in unison.

Then another girl joined her. She had short, dark hair with a baby-ish face. She knelt down and took Chanel's cock into her mouth. The scene was so hot as she took her length down her throat. Chanel held the back of her head and thrusted her hips into her face.

Guiding her up by cradling her face, Chanel led her to a chesterfield. It took me by surprise when Chanel pulled down the girl's panties so her cock popped out. "Another one?"

I looked at the video tags. Along with Chanel Santini, Daisy Taylor was listed.

Chanel took Daisy into her mouth. When she thought it was hard enough Chanel took Daisy's rock hard cock into her ass. I shot my load.

After that, I started researching Chanel Santini, other trans and their videos. Each one made me cum harder and harder. Especially the ones where they are dressed in lingerie.

Then it happened. Mom asked me to bring down my dirty laundry. Hers was already folded and done. Atop the pile were a couple of panties and bras. I couldn't help but pick them up. Holding one of her bras by the straps, I brought it up and placed it on my chest over my tee shirt. I replaced it and then held the panties to my hips. I dropped them back onto the pile, I dashed to my bedroom and jerked off.

The more I watched trans-porn, then more I thought about Mom's underwear, the more I jerked off. A number of times, I borrowed one or two of her panties and rubbed them against my cock to jerk off. A couple of times I slipped her panties and bras on. I was careful not to spew on any of her things. In between laundry days were the worst. I had to use my imagination and the memory of using her panties as a jerk-rub.

That day after school when Mom had gone to her office, I knew I had some time for fun. Even though I was alone, I snuck into her bedroom making sure no one heard me. I carefully opened one of her drawers and my eyes popped at the bonanza of treasure. I had come across her stash of incredibly hot lingerie.

Now Mom wasn't a nun. Unlike my short stature, Mom stood about five-ten or eleven. She had a nicely shaped body with C-cup boobs. I had heard my school mates call her a MILF. When she did go out on a few dates or to the office, she made sure she was nicely dressed. None of her dates seemed serious especially when they found out she had a kid.

Her drawers were filled with different bras and panties and garter belts and stocking. Some were lacy others were satin. Most of her panties were either thongs or G-strings, the ones that weren't were tiny bikinis that rode high on the hips.

I stripped off my clothes and stood pathetically in front of her dresser mirror. I reached for a red lace bra. I was shaking like a bowl of Jell-O. I picked it up and hooked it on. It was a bit loose and of course the cups were empty. I found a red thong and stepped into it. As I pulled it up, the thin back slat ran into my ass crack. I pulled them up tighter. There was a big red bow with long red tails dangling from the back. I tried to tuck my hard dick inside the fronts then noticed a dark, wet spot appear. "Shit! Well too late now."

I figured out how to put the garter belt on. This one had four dangling straps hanging from each side. She had some red fishnet stocking rolled up. I slide them up my legs and attached the garter clips to the welts. Of course they sagged since Mom's legs were longer and I didn't want to re-adjust the strap length. I thought it looked sexy. The small, hard lump inside my panties thought so too.

I dashed back to my room and watched more tranny porn as I rubbed my cock through the thong. I squeezed and pinched my nipples. The dark spot grew larger in the panties. I needed to cum.

I laid back on my bed and pulled my dick out the waistband. The amount of pre-cum leaking out from me, coated my fist. It acted as a great, slippery lube too. My hand was a blur. I pinched my hard nipples hard. Arcs of white spewed out onto my face and chest. "Uh...! Uh...! Uh...!"

"Abby honey, I was wondering what you wanted for din..." Mom entered my room. She quickly retreated and close the door behind her. "Oh! I'm sorry, Honey!"

"Fuck!" I swore. Even if I had the chance of covering up, I had nothing to cover up with. It was very evident she saw me wearing her lingerie and jerking off. I took off her cum-soaked bra and panties and used another tissue to clean up. I tossed the used tissue into the basket where it fell to the floor. "Fuck!"

Dressed in my normal clothes, I sheepishly exited my room. Mom was sitting quietly in the living room. When she saw me, she patted the place beside her. "Abner. Sit, please."

I looked at her ashamed. Ashamed at masturbating. Ashamed at being caught. And ashamed at being caught wearing her underwear.

Mom looked at me sympathetically. "First. I'm not angry, I'm sorry. Your door was open so I assumed it was okay for me to enter. Second, masturbating is a normal function. I do it too. Especially when I think of your dad. Third, it's also normal for young lads to experiment and wear women's things. You're not the first or the last to do it."

I started to cry. Mom was so kind and loving, I could feel it in my heart. Then Mom looked at me with a bit of indifference or uncertainty.

"You know, even some adult men enjoy wearing women's clothing." She was right. I had come across a number of crossdressing sites. There was a pregnant pause before she spoke again. "Actually, your father enjoyed dressing up. And his father before him."

If you hit me with a bat, I couldn't have been more stunned than I was now. I looked back at Mom not really comprehending what she just revealed to me. "Dad wore women's clothes?"

"Yes and so did Grandpah." Mom confirmed. "They use to have contests to see who could dressed best or sexiest and stuff. They would model themselves for me and Laura (Dad's mom)."

I still couldn't believe what I was hearing.

"Let me say that when you were born, both of us were ecstatic and loved you very much. I love you very much and never regretted having you. But your dad always knew if we had another child, I would wish for a daughter but it wasn't to be." Mom said Dad had become sterile. "So he let me dress him up. It was fortunate that we were mostly the same size and could swap clothes."

My mind was reeling. After eighteen years of life, I had discovered transsexuals and transvestites and that not only did I love wearing lingerie and my father and grandfather did too. And both my mother and grandmother were more than okay with it.

"I was going to cook but let's order pizza instead." Mom suddenly announce. She went on-line and put in our order. She smiled at me and said. "Come with me to my bedroom."

I followed her and entered through the doorway with much trepidation. She told me not to worry and relax. She went to her walk-in closet and pulled out some boxes. She turned to me and said. "These are some of your dad's girly things. If you want, you can look through them and keep whatever you want. Of course, he was bigger than you so the clothing probably won't fit without alterations. I can do that later. And we'll have to get you some of your own bras and panties!"

I took the box back to my bedroom and opened the lid. There were a number of bras of various types. And panties! Some of them with matching bra but most of the bikinis were too baggy for me to wear but I wouldn't care. He had a few French tap pants with elastic waists that I could get by with and a few garter belts that were slightly loose around my waist. Most of the belts had three or more straps dangling from each side.

Dad was a bit taller than Mom and so his stockings of course wouldn't fit. Later, Mom showed me to fold over the tops and attach the clips so they didn't sag so much. She also bought stockings for me that were more to my height.

At the bottom of the box, were a couple of smaller boxes. I picked one up, took off the cover and was surprised to see a set of boobs looking back at me. The lid said "B" while the other one was marked "G." I removed that lid and a pair of huge boobs made their appearance. Both the B's and D's had big, pink nipples in the middle of a big, darker pink aureole.

"Oh! I see you found your Dad's boobs!" Mom said at my doorway. "We bought the smaller ones first to see what they were like. Both your Dad and I loved the bigger one. They're self-adhering so you don't need glue. Want to try them?"

I enthusiastically nodded my head up and down. I removed my top and Mom helped me place them on my chest. We tried the smaller ones first. They felt nice and secure and I could walk around braless if I wanted to. The G's were much heavier and bounced more but I quickly got used to them. "Wow, Mom! I love these!"

Over the next couple of days when I didn't have to leave the house, Mom allowed... no she persuaded me to dress as I felt. And so I would select items from Dad's box. I'd always start with breast forms and always the bigger one. Even supported by a bra, they jiggled around. Today, Saturday, the bra I chose was a vibrant red, lacy, demi-cup that barely covered my big nipples. Even though Mom told me I should wear them the other way, I pulled on the matching red, bikini panties over my hard dick before hooking on the garter belt and clipping the red seamed stockings. I told Mom. "I love it that I can't pull my panties down all the way!"

The top was a white opaque nylon mesh shirt with a low Vee-neck. You not only could see the outline of my bra but the red colour too. The tight fit made my nips really pop. I put on a red, wrap-skirt I found in the box and tied it around my waist. It was still too big but I made it work. The hem was about mid-thigh and more than adequately covered the small bump of my erection but I guess on Dad, the length would have been much shorter; probably bum length.

I found some shoes I could wear. Fortunately, Dad had a small foot for a big guy. Today I pick a pair of white mules with a high heel. I slipped my foot into the shoe. It was still a bit big and loose and the four-inch stiletto heel wouldn't help much either but I quickly got used to them and took to them like a duck to water.

As I combed out my shiny, black, shoulder-length hair, Mom knocked on my door. "Abby honey... Oh my! Don't you look pretty!"

I smiled back at her please that she was pleased. I took a step towards Mom to hug her but turned an ankle due to the loose fitting heels. Mom helped me up and made sure I was okay. We went to her bedroom and she had me sit down at her dressing table. She started to apply make-up to my face and explained how to do it so I could try it on my own.

The mascara really thickened my naturally long lashes and the shading on my lids really made my eyes pop. A little blush accentuated my cheek bones and the cherry red lippy made my puckered lips plump. When Mom brushed my hair a different way, I was really amazed of how feminine I looked.

Mom looked really pleased with how I appeared. Then suddenly said. "Let's go shopping!"