Aunt Pamela And Leslie Ch 03

I spent the days after my second visit with Aunt Pamela trying to decide what I would wear on Friday. She told me to wear something feminine, but I didn't have anything really feminine. The girliest article of clothing I owned were the stretchy, velvet shorts I'd worn on Tuesday.

And after doing poorly on a pop quiz in my History class, I knew I had to do something drastic. I hoped if I arrived in a scandalous outfit, maybe Aunt Pamela would go easy on me. It wasn't until Thursday evening while doing my laundry when I decided upon the perfect outfit. In the lost-and-found box in my building's laundry room, I noticed a white dress shirt. When I picked it up, I found it was big enough to hang to the middle of my thighs.

After running it through the washer and dryer with my whites, I folded it neatly and carried it up to my room. As soon as the door shut behind me, I stripped off my clothes and slipped into the dress shirt. I rolled the sleeves up to my elbows and buttoned the shirt, leaving only two buttons on the top undone. When I stepped in front of my mirror, I knew I found what I had been looking for. I looked like a girl who was wearing a men's shirt. It was perfect. While staring at my reflection, the idea of being taken to Aunt Pamela's punishment room brought a tear to my eye. I stood there and cried while looking at my sad, worried reflection.

On Friday, after I'd finished my morning classes, I raced back to my room and took another extra-long shower. I scrubbed my entire body twice. I needed to be perfectly clean for Aunt Pamela. I brushed my teeth, used mouth wash and combed my hair neatly to the left. Only then did I slip the dress shirt onto my naked body. I dug through my closet and found the white flip-flops my Mom had bought for me to wear in the dorm shower. At the time she bought them, she didn't know if I'd have to use a community shower. Thankfully, I wound up in a private room with its own bathroom.

Before leaving my room, I looked at myself in the mirror one last time. I knew Aunt Pamela was going to love seeing me like this. But the walk across campus and the several residential blocks I'd need to walk through made me flush with embarrassment and shame. People would see me. Both my fellow classmates and residents of the town. They would stare at me. They would wonder if I was a girl or a boy. They would wonder if I was wearing anything under that shirt. It sent a chill up my spine.

Before leaving my room, I picked up the framed, 8x10 portraits of both my Mom and Gam-Gam. While looking at my Gam-Gam's picture, I promised I would tell Aunt Pamela that I'd never referred to her as my Grand Mother. She had always been my Gam-Gam. She had reminded me of that when I'd called her after my most recent visit with Aunt Pamela. During that call, I'd slipped and called her Grand Mother.

Her reply came quickly, "Well aren't you a formal boy! Baby, you've always called me Gam-Gam. Now that you're in college, are you going to start calling me Grand Mother?"

I was standing naked in my room while I spoke with her on the phone. My little penis was very stiff and I couldn't resist touching it while I spoke with her. I giggled, "I'm sorry Gam-Gam. I don't know why I said that."

"It's okay Sweetheart. It just sounded odd when you said it. I pictured you wearing that cute, sailor costume I bought for you last Halloween. I remembered you looking up at me telling me you were too old to wear that costume. You were just adorable!"

Biting my lower lip and squeezing my penis, I said, "Um, Gam-Gam, do you remember the velvet shorts that were a part of that sailor costume?"

"Oh yes. Those shorts were the best part of that costume. They made your little butt look absolutely delightful. And they were short enough to show off your shapely legs. And let's not forget how they emphasized your little penis! They were the perfect shorts for you!"

I shivered while squeezing my penis, "Well, um, Gam-Gam, I brought those shorts with me to college. And I actually wore them just the other day."

There was a moment of silence. "Did you now?"

I squeezed my eyes shut and uttered, "I did. And I got lots of compliments too."

When she spoke, her voice was warm, but teasing at the same time, "I'm sure you did get lots of compliments. You know, I have always wanted to keep you dressed in clothes like that. Sweetheart, would you like me to go shopping and pick up some more cute clothes like those shorts?"

My voice cracked and I had to let go of my penis or I would've squirted. "Yes, please Gam-Gam. I'd like that very much."

I knew someday very soon I would receive a care package from Gam-Gam. Until that moment, I'd never asked for clothes from her. She had always given me gifts like that on her own. But now I'd asked her for sissy clothes and I was both excited and terrified at the prospect of what she may send.

After forcing myself to return my thoughts to the present, I turned Gam-Gam's picture to face the front of Mom's and held them both against the bump of my erection. On my way to the door, I slipped my school ID into the shirt pocket. Before giving myself a chance to think too much about it, I left my room and made my way out of my building. When I stepped outside, I saw dozens of people walking in small groups. Luckily, none of them seemed to be looking in my direction. I lowered my chin and began flip-flopping across campus.

Before I got to the closest building, I began to chant in my head, "My Mom, my Gam-Gam and my Aunt Pamela are the only women who will ever love me and my tiny penis." When I heard a group of guys shout foul things at me, I began to chant my comforting words out loud while walked even quicker than before.

My heart was pounding, my face was flushed, while humiliation and shame were burning deep inside of me. I was walking across campus wearing only a shirt! It was the very first time I'd ever been in public wearing only one piece of clothing! What would my Mom think? What would my Gam-Gam think? I giggled to myself when I realized they would both have loved to see me running around in so little clothing!

Soon enough, I left campus and after that first block, I slowed down and began walking at a more leisurely pace. A few cars did drive by, but no one honked or shouted at me. They simply passed by and watched me walking for as long as they could.

Eventually, I began to approach Aunt Pamela's home. When I turned up the walkway leading to her door, I moved the photographs away from my erection and held them in one hand. With my other hand, I began to undo buttons on my shirt. When I stood on her doorstep, I undid the last button before knocking on her door.

I stood there, holding my framed pictures of my Mom and Gam-Gam. The only thing I wore was an over-sized, clean, white dress shirt. While I listened to her heavy footsteps approaching the door, I shrugged my left shoulder and my shirt slid down to my elbow. I stood there at her door, my shirt was completely opened, my stiff little penis was pointing toward the blue sky and I held a portrait of my Mom in one hand and my Gam-Gam in the other. My chest was heaving with each breath I took. The warm sunshine on my naked skin was so erotic. And I'd never felt so exposed.

When the door opened, I completely lost my breath and my penis nearly squirted right there on her doorstep. Aunt Pamela wore a light blue, silk blouse that draped over her enormous breasts majestically. The heavy gray streaks in her hair were pulled back into a loose bun. For the first time, I saw Aunt Pamela wearing jeans and tennis shoes. She looked classy-casual. She was as beautiful as ever.

After letting her eyes wander over my body several times, she grinned and said, "My Sweet Leslie, you look absolutely delicious! You didn't walk all the way here like this, did you?"

My back arched and I moaned, "No, I walked over here with it buttoned up. I undid the buttons when I got here."

"Sweetheart, were you without panties during the whole walk?"

Biting my lower lip, I was about to answer her when I breeze caught my shirt and blew it off my other shoulder, leaving it dangling from my elbows. I squeaked, "Yes, Ma'am. I came all the way here in just this shirt."

After leaving me standing outside her door for that conversation, she finally invited me into her home. I stepped out of my flip-flops as I crossed the threshold. When the door was shut behind me, she took the pictures from my hands. She asked me to stand in my normal spot on the carpet in the middle of her living room while she took a seat on the couch. I kept my elbows bent with my arms out to my sides to keep the shirt from falling all the way off.

As soon as she was seated, I timidly said, "I'm really happy to see you again Aunt Pamela."

She smiled and said, "Oh, I think I'm even happier to see you. It's not every day a boy shows up at my door wearing as little as you are."

I giggled and said, "You told me to wear something feminine. But I don't have anything really feminine. So, I thought I would try wearing as little as I could. Do you really like it?"

"I love it, Sweetie. Now, why don't you introduce me to these two ladies." She held the portraits on her lap. She raised the picture of my Mom and looked to me.

My voice squeaked with I said, "That's my Mom."

"I expected her to be more petite, like you. But she has a build like my own. Just look at her chest. Those are some big boobs! She is a very pretty lady, isn't she Leslie?"

Biting my lower lip, I said, "Yes. I think she is very pretty too."

She set that picture down on her lap and picked up the second picture I brought. Holding it so we both could see, she asked, "This must be your Grand Mother."

My hips squirmed in a little circle as I said, "Gam-Gam. That's Gam-Gam."

Aunt Pamela smiled at me, first motioning to the first picture, "Mom" and then the second picture, "Gam-Gam, right?"

I bit my lip, nodded my head. She set my Mom's picture back down and held onto Gam-Gam's. "Well, Gam-Gam looks like a strong-willed woman. Was it Gam-Gam who bought you those cute little shorts you wore earlier this week?"

Biting my lip, "Yes, Ma'am. And when I called her on Tuesday afternoon, I told her I had worn the shorts and gotten lots of compliments. Gam-Gam said she would get me some more cute things to wear."

Her eyes wandered up and down my body as I stood before her nearly naked. She spoke in a raspy voice, "If we're lucky, Gam-Gam will get you a little dress. I love that you showed up in that shirt today, but I would really love to open my door and see you standing there in a cute little dress."

My voice cracked when I said, "Whatever she sends, I'll wear on my visits to see you. I promise." The shirt I'd been wearing fell to the floor when I let my arms fall to my sides. Now standing there completely naked in front of Aunt Pamela, my feelings for her were reinforced by just standing naked in her presence. I moved my hands behind my back and struggled to keep from touching myself.

Aunt Pamela must've known how horny I was. In a calm voice, she asked, "Sweet Leslie, is this how you were dressed when you called Gam-Gam? I trust you called your Mom like this too?"

My voice cracked and my penis throbbed. "Yes. I was naked. I was stiff too. I called Gam-Gam on Tuesday. And I've spoken with my Mom every night, just like I always do. And I got naked every time."

Her eyes were wandering up and down my body. "It's a shame you weren't Face-Timing with them. I'm sure they both would have loved to see you so excited." She held up both pictures. "What do you think Leslie? Would your Mom and Gam-Gam like to see you naked and excited?"

My voice cracked, "I-I-I don't know."

She smiled while still holding up the pictures. "Well, I do know. You are so cute. They would both love to see you completely naked with a very stiff little penis."

I stood there on the verge of orgasm, naked before Aunt Pamela, looking from her face to my Mom's picture and then to my Gam-Gam's picture. In a soft voice, I whispered, "I'm really horny Aunt Pamela."

She smiled while rising up from the couch. "I know you are Sweetie. But we have things to do before we can address this." With that last word, she reached out and drug her finger along the underside of the pink, squishy head of my penis. She raised the finger between our faces and then began to coat my lips with my juices. I parted my lips after she'd coated my lips and sucked her finger clean while she slid it in and out of my mouth.

"Your Mom and Gam-Gam should be here right now."

She didn't wait for me to respond. Instead, she took my hand and led me toward her desk in the corner of the room. We left my shirt laying on the floor. Once at her desk with me perched on her knee, she wrapped one arm around my naked body and rested her hand on my hip. She logged into my student account and maneuvered to my grades. I shivered on her knee when my grades appeared on the screen. She went through my schedule class by class. When she opened my 104 US History class, I panicked.

"I'm sorry Aunt Pamela! It was a pop quiz! And History has never been my best subject. There were only ten questions and I only missed one. But that gave me a..."

She interrupted without looking away from the monitor, "That gave you 90%. Leslie, I'm very disappointed. 90% is far less than the 98% I know you're capable of maintaining." She finally looked at me, "You know what this means, don't you Leslie?"

Tears were already forming in my eyes and beginning to run down my cheeks. I sobbed, "Yes. It means I'm going to be punished."

I could see how disappointed she was while she stared into my eyes. "Oh yes, you are in for a very serious punishment. You're going to be glad you came over here dressed as you did. Because your little bottom is going to be far too tender to wear anything else."

I began openly crying. I had a good idea of what I was about to receive. And the thought of being punished by Aunt Pamela made me very emotional. I had disappointed her. I had disappointed my Mom and Gam-Gam too. I deserved to be punished. But the pain frightened me. When Aunt Pamela last punished me, she didn't hold back. She used all her strength and really punished me! It hurt so bad!

Aunt Pamela went through the rest of my grades while I remained perched on her knee, crying my eyes out. After learning the History grade was my only failure for the week. She placed a finger under my quivering chin and turned my head to face her.

In a stern tone, she said, "Leslie, you've known this was going to happen since you received that grade on Wednesday. Have you been worrying about it this whole time?"

Through my sobs, I somehow managed to say, "I-I-I forced myself not to think about it. I-I-I hoped if I came in just my shirt, you might..." I trailed off and began openly crying again.

She asked, "You hoped I wouldn't punish you if you arrived in just that shirt? Leslie, I can't let a grade a poor as this go without a punishment. You deserve to be punished, we both know it." She opened a drawer and pulled out a box of tissues. She withdrew a tissue and wiped my tears. After tossing it in the trash, she pulled out two more tissues and held them beneath my nose. In a very maternal sounding voice, she spoke a single word, "Blow."

We soon stood up and she guided me to the door leading to her basement. On our way, she asked me to get the pictures of my Mom and Gam-Gam. I held the two framed pictures and followed behind Aunt Pamela. I was extremely emotional and couldn't stop sobbing. Tears were rolling down my cheeks and my breathing was coming in gasps. Even with my emotions going crazy, I couldn't resist watching Aunt Pamela's big bottom sway from side to side as she descended the stairs.

When we arrived in the basement, I found it had changed very little since my last visit. It was windowless but brightly lit. The soft blue walls and white ceiling gave me an oddly calm feeling. The circle of white linoleum in the center of the room contained Aunt Pamela's spanking bench. A piece of furniture I'd become acquainted with on my first visit to her home. The white carpeting throughout the rest of the room was completely free of furniture except for her throne-like chair which was positioned on the backside of the spanking bench and two wooden chairs that sat close to the front of the spanking bench. Those two wooden chairs were the only new additions to the room.

Aunt Pamela instructed me to place my Mom and Gam-Gam's pictures on those two chairs so they could witness my punishment. With fresh tears rolling down my cheeks, I carefully positioned each picture. I was sobbing and struggling to catch my breath, but I managed to get them both standing upright with the help of the fold-out stand on the back of each frame.

When she told me to take my place on the bench, I began bawling. I wasn't crying, I was blubbering, sniveling mess. But I soon found myself restrained onto the spanking bench with several Velcro straps. My upper body was resting on a padded shelf. On either side of that raised area, my elbows and forearms were strapped to their own horizontal, padded areas. My knees and skins were also strapped onto their own padded platforms behind me. Just like before, my knees were positioned apart several inches apart. I was restrained in a hands-and-knees position, perfect for what I had coming.

Bound securely to that bench, I couldn't help but look at the pictures of my Mom and Gam-Gam right in front of me. It felt like they were watching me, like they could see me, naked and strapped down, ready for my punishment. In a very pathetic sounding voice, I whimpered, "I'm sorry Aunt Pamela! I'm sorry Mom! And I'm sorry Gam-Gam! I promise I'll do better! I promise I'll never need to be punished again!" And then the tears began dripping from my face and my sobs echoed around the room.

Aunt Pamela crossed the room and walked to the wall in front of me. She opened the scary cabinet that contained all her terrible tools of punishment. As the doors opened, I saw the paddles, crops, canes, floggers, and straps. A chill ran through my body and my vision blurred when my eyes filled with tears. I blinked them away and watched Aunt Pamela making her selection. She chose a long, thin wooden paddle. It looked to be as only an inch or two wide and at least a foot-and-a-half long. There was a contoured handle with a leather loop to hang it from.

She held that paddle in her hand while she turned and walked back in my direction. I shivered on the bench and began to apologize over and over for my poor grade. I babbled on about how much I loved her and knew she was going to spank me, but I begged her not too anyway.

She knelt down between the two chairs near my head. She gently laid her hand on my tear-streaked cheek and explained, "My sweet Leslie, you deserve this punishment. I explained what I expected of you during your first visit. Do you remember that conversation?"

I murmured that I did while still crying and sobbing uncontrollably.

She stroked my cheek and explained, "Sweetie, I'll accept nothing less than a 98% and you got a 90% on that quiz. That is an 8% difference which means you'll be getting 8 swats from my paddle."

My sobbing paused while I lost my breath and I struggled to catch it again. Tears continued to roll down my cheeks while I apologized over and over to Aunt Pamela, my Mom, and Gam-Gam. I knew in my heart it wouldn't make any difference no matter how many times I apologized or what I promised. I was going to get those eight swats from her paddle. And I had a strong feeling this was going to hurt more than anything I'd ever endured before.

Aunt Pamela rose to her feet and walked back into position. I was left staring at the photographs of my Mom and Gam-Gam. My body shivered and goosebumps rose and fell on my body in waves. My wrinkled hole was flexing and my little penis was shriveled up like a raisin. I was an emotional wreck!