School Daze Ch. 01

"Come on, Timmy!" My mom, Jackie Taylor called out at me. "We need to find some things for you to wear to school."

"Do I have to?" Nearly nineteen years of age, I was way past that point where I hated going clothes shopping especially with my mother. But obviously to her, I wasn't responsible enough to go on my own.

During my short life, she'd always pick out stuff I didn't like. Or she'd buy something for me on her own. If I said that I didn't like it, she would say "What's wrong with it?" and stick it in my wardrobe anyways. Then she'd complain to me about not wearing it after she bought it specifically for me.

I was barely awake and crawled my ass out of bed. I was going to go downstairs in my PJ's but Mom told me to change so we could leave right after breakfast. Bleary eyed, I got dressed in the dark and went to the kitchen where I found my younger sister already dressed and eating. Just turned eighteen, Jessie already showed signs of being a women. If Mom's figure was any indication, Jessie would be a very shapely woman. Mom's big breasts, curvy body and round bum would be the envy of many models. And Mom made sure that her long legs were consistently on display.

I choked down some cereal my sister insisted on getting Mom to buy but I hated. Barely finished the last spoonful before we all got into the car and drove to the mall.

Jessie knew exactly what she wanted and dragged us all over. Style and name brands were utmost important in keeping up with her peers. I'm not sure if Mom agreed with her choices but while I thought they were a bit risqué, she didn't object to any of the outfits Jessie selected. But I found it really embarrassing when Mom and Jessie entered into Victoria Secret Pink. I wanted to wait outside but Mom said it wasn't safe and needed to keep an eye on me.

I was fuming at the fact that I was inside a women's lingerie store waiting on my sister and mother to buy some new bras. What could be worse? It could always be worse.

"Hi Timmy!"

I turned to see who called my name. It was Jenifer. I had the hots for her. My best friend John's sister. She was a few months older than Jessie and her BFF. Together, Jessie and Jenifer with similar bodies, blond hair and blue eyes, could have been twins. She was actually pretty hot. And I guess by association, so was my sister.

"Buying some new panties and bras for school?" Jenifer giggled.

"Jessie and Mom made me wait inside for them." I answered slightly red faced at being recognized.

"Hi Jenifer." My sister greeted and hugged her friend.

"Hi Jess. Hi Mrs. T." Jenifer replied back and continued to tease me. "I was just asking Timmy if he was buying some new panties and bras for school."

I really hated it when they all laughed. Even some of the other customers within ear shot chuckled or supressed a smile. Then the worst part.

"No. We'll have to go to the boy's store to buy him his panties!" Jessie said pretty loudly.

More laughter from everyone.

I didn't care anymore and just stomped out of the store. When Mom and Jessie finished inside, they found me sulking on one of the benches outside of the store.

"Oh, c'mon, Timmy." Mom smiled. "We were just teasing."

"Oh, but Mom! I think he would look so cute in some of the panties we bought." Jessie continued to taunt me. "But I think we would need to get him some padded training bras. Mine would be too big unless we stuff the cups with socks or something!"

"Jessie!" Mom gave my sister a mock scolding.

It took a bit before I calmed down as we went to get my stuff. I wanted to get some jeans and khakis and picked out a couple of pairs. Mom wanted me to try them on to see how they looked and fit. In the empty change area, I found an empty stall and closed the door behind me. I let my pants drop and then stood there gaped mouth. When I got dressed this morning, I didn't realize the underwear I put on was actually one of Jessie's. They must have been mixed in with my stuff. They were baby blue. And it had a "PINK" written on the back side.

Suddenly, the door opened. "How do the pants fit?" Mom asked.

"Look!" Jessie pointed at me. "Timmy is wearing my panties!"

Mom covered her mouth to hide her smile. Standing beside Jessie was Jenifer. Both of them pointed and laughed. Jenifer giggled out. "He looks so cute in them!"

I yanked the door back closed and pulled up my pants. I stormed out of the booth, out of the store and got on a bus to head for home. When I got there, I stormed into my room and slammed the door shut.

I yanked off my pants and was about to pull down Jessie's panties when I looked at myself in the mirror. They did look cute. "What am I thinking?!?!" I ripped them off and threw them in the trash.

Mom and Jessie got home a number of hours later. Mom called out. "Timmy! Are you home? Can you help us with our shopping please?"

I was still fuming and refused to provide any assistance to the banes of my existence. But soon there was a gentle knock on my door. It was Mom. "Timmy? Can I come in please?"

"No!" I shouted back.

"Please?" Mom asked again through the closed door. "I'm sorry we embarrassed you today."

The door cracked open a bit. When I didn't protest her invasion, Mom entered. I sat on my bed pouting.

"Oh, Timmy. I'm really sorry. We were just having fun at your expense and we're sorry." Mom looked at me for forgiveness. "I'll order some of you favourite pizza for dinner tonight and I'll make it up to you later."

"Okay." I relented until Jessie appeared.

"Hey, Panty Boy! Where's my panties?" Jessie demanded. "Do you still have them on?"

"Jessie! Stop it!" Mom scolded my sister; this time for real.

+++

Next day, I went over to John's to see if he wanted to shoot some hoops. I rang the doorbell before walking through the unlocked screen door and into the house. I looked out the back patio door and found Mrs. Jenna Davidson and Jenifer basking in the warm sun. Mrs. Davidson and Mom could have been the two older twin sisters to Jessi and Jenifer.

"Timmy? Is that you?" Jenna called out as she shaded her eyes with one hand and beckoned me with the other. "Come out to the back."

"Yes, Mrs. Davidson." I answered back. "Is John around? I wanted to see if he wanted to shoot some hoops."

I walked on to the deck. Both of the women wore white, tiny string bikinis that barely covered their private parts.

"I said it is okay to call me Jenna. Mrs. Davidson makes me feel too old." Jenna smiled. "John was going to stay home but he ended up going on a business trip with his dad. He's be back tomorrow or next day after."

"Oh. Well I guess I'll take off then." I was about to turn to leave.

"Take off?!?" I heard Jenifer suddenly get a voice. "Did you finally take off those cute baby blue panties?"

"Jenifer!" Obviously, she had told her mother of yesterday's events. "If he likes to wear panties, that his business. Some guys like to wear women's things! Now apologise to Timmy."

"I'm sorry, Timmy." Jenifer looked deep into my eyes. Her apology seemed sincere.

"Maybe our guest would like a soda?" Jenna directed her comment to Jenifer. "Hey, Timmy. Would you like to use the pool?

Jenifer smiled as she rose from her lounger. Her young body was incredible and I was able to mumble back. "That's okay. Yeah a soda would be great. I didn't bring my swimming trunks."

"We can figure something out." Jenifer took me by the hand and led me to the fridge. Inside the kitchen, she turned to me and said. "I AM really sorry about teasing you. Will you forgive me?"

How could I stay angry at this? "Yes."

"Thank you!" Jenifer pressed her hot bod against me as she gave me a hard hug. Then she giggled. "You really did look cute in those panties. I kinda like them on you. It really turned me on!"

It turned out to be a turning point moment; Jenifer and I became an item although often mentioned, any subsequent panty wearing by me never occurred and was soon forgotten. I had moved away to for college. It was just out of town so coming home on the weekends was easy. For my birthday, Mom and Dad bought me a small little commuter car to scoot around the college town in or easily drive home. And it was big enough for me and Jenifer to make out in.

+++

Of course I didn't want to pay for it at campus so I often came home to do laundry. The dryer was already filled so I needed to empty it before I could dry my stuff. When I opened the dryer door as if my magic, some baby blue panties tumbled out and fell to my feet. All the memories of what happened ago came flooding back. Being seen in them. Being seen in them by Mom, Jessie and Jenifer. Looking at myself in the mirror and thinking how cute they looked.

I now forgot all about my wet clothes. I brought the panties up to my face and rubbed them on my cheeks. I took in a deep inhale and breathed in the clean fragrance. I ran up to my room and stripped off my clothes. My dick was rock hard. My hands were shaking as I held open the waist band to step into them. I slid them upwards over my legs and over my hips. The bikini panties could not contain my boner that was sticking up through the top.

I looked at my dresser mirror but could not get the full view of myself, but Jessie had a full length mirror in her room that I could use. Dressed only panties, I quietly tip-toed out of my room and towards Jessie's. I wasn't sure why I was sneaking since no one else was home.

The mirror was on the back of her bedroom door so I had to close it to view myself. The panties looked incredibly cute and I loved the way they made my bum look. My leaking pre-cum made my knob all shiny and slick as I rubbed myself. My other hand automatically started to play with and tweak my hard nipples. I closed my eyes and bit my lower lip. I took full strokes as my mind was lost in its own thoughts. I was about to cum.

The door creak open. "You can try out my new red nail polish..."

I opened my eyes. Staring back at me was my sister Jessie and my girlfriend Jenifer.

"Oh my gawd! Timmy! What the fuck?" Jessie screamed out at me.

Jenifer just stood there staring at me gape mouthed.

Initially stunned I stood there with my dripping cock in hand. When I regained some sense, I tried to leave. Jessie stopped me and pushed me back into the room closing the door with all of us inside. Unbelievably, I was still rock hard even after being caught out.

"Fuck, Tim!" Jessie cursed. "Why are you wearing my panties? Look at your boyfriend, Jen. He's got a boner from wearing my panties and he's jerking himself off!"

"Jesus Timmy!" Jenifer shouted at me. "Wha...? Why...? Uuuh...?"

I tried to leave again but Jessie pushed me backwards again. I fell onto her bed.

"No. You stay there!" Jessie warned. She jerked her fist towards her mouth. "Jeez Jenifer. I thought told me that you take care of your boyfriend? Hmmm...? Maybe we should say your girlfriend?"

Surprisingly, I still had my erection. In fact, it was harder and bigger than I've ever felt it before. Seemed my erection wasn't lost on either of the eighteen year olds either.

"Jen? What do you think? I think he enjoys wearing panties. Remember at the store? Maybe it wasn't an accident." Jessie asked her BFF. "Maybe he wants to join us girls. But he needs to be initiated."

Jenifer still a bit stunned, nodded in agreement.

"Well? First I think we need to give him a proper girl name." Jessie said to Jen who seemed to have recovered a bit. In fact, after she seemed to have recalled the incident, she seemed really excited by it.

"Yeah! How about..." My girlfriend paused thoughtfully. "I know! How about Tina?"

"Yeah! That's a great name. What do you think about your new name, Tina?" Jess asked of me.

"No. Let me go or I'll tell Mom!" I protested.

"Okay. Go tell Mom. Tell her that we caught you in MY bedroom wearing MY panties jerking off your pathetic cock!" Jessie opened her bedroom door. "Or I can do it. M..o..m..!"

I thought Mom was still out and I was safe until I heard.

"Yes, Jess. What is it?" Mom called back.

Jessie looked at me. "Should I tell her? Maybe come up and look at her pantie boy son?"

"No Jess! Don't! Please!" I begged.

Jess turned and shouted at Mom. "Can Jen stay for dinner? Can she sleep over?"

"Yes, of course." Mom replied. "I'm just making a roast chicken. And Jen! Don't forget to call your mom and let her know you're staying here."

"K, Mrs. T. I'll call her right away." Jenifer called down.

Both of them were smiling ear to ear as Jess closed the door.