Aunt Pamela and Leslie Ch. 03

Several moments passed before I felt the rigid wooden paddle gently bump against my bare cheeks. Aunt Pamela rubbed the paddle up and down over my bottom. While she did, she said, "Leslie, Sweetheart, I don't want you to count these swats. Instead, after each whack, I want you to tell me, your Mom and your Gam-Gam you're sorry and that you love us. Can you do that for me, Sweetheart?"

My eyes darted between my Mom and Gam-Gam's pictures. I whimpered between sobs, "Yes. Yes, I can Aunt Pamela."

"I knew you could." She pulled the paddle away from my cheeks and let me suffer for several long seconds before asking, "Sweetheart, are you ready?"

Biting my lip, I nodded my head and fought to get control over my sobbing. Just when I'd nearly caught my breath, the sound of that paddle swishing through the air made my butt cheeks clench up tightly. And when it made contact, it felt like I'd been hit my car! My entire backside felt like it was on fire and I thrashed about against my bonds. It hurt so bad!

It took me several moments to be able to breathe after that first impact. Aunt Pamela patiently waited for me to somewhat recover during this time. And a few moments later I remembered what I'd promised to say. While still wailing in misery, I screamed out, "I love you Aunt Pamela! I love you Mom! I love you Gam-Gam! And I'm sorry I did so bad on my quiz!"

While the last word was still leaving my lips, I heard the sound of that paddle swishing through the air again. I clenched up tightly to prepare for the impact. But I quickly learned, I could never prepare myself for that level of pain. I screamed out and thrashed against my bonds, but it was pointless. I wasn't strong enough to break free. Drool was falling from my lower lip and chin. My nose was running and tears were raining down on the floor.

After a time, my eyes cleared enough for me to see my Mom's picture. I knew my Mom would never punish me like this. I'd always been very well-behaved and my Mom wasn't the type of woman to punish me in this manner. However, I believed my Mom would have enjoyed being in that room watching me being punished so severely. I imagined her sitting in the chair where her picture sat. In my fantasy, she was grinning while her eyes wandered over my naked body. And each time the paddle struck my bare bottom, she would squeeze her thick thighs together.

Glancing to the picture of my Gam-Gam, I knew in an instant, if given the opportunity, my Gam-Gam would love to be watching this terrible event in person. Even more than that, I knew deep down inside of myself that she would love to wield the paddle Aunt Pamela now held in her hand. I truly believed inflicting a punishment such as this onto my naked, skinny body would make Gam-Gam's day.

While my mind wandered with the thoughts of my Mom and Gam-Gam, I didn't realize Aunt Pamela had moved in close enough to whisper in my ear. "Sweetheart, don't you have something to say?" Her fingernails dragged across my naked back and my little penis swelled up a bit.

My voice cracked in between sobs and wails long enough for me to say, "I love you Aunt Pamela, Mom, and Gam-Gam! And I'm really sorry for what I've done!"

Just like before, the paddle whistled through the air before I'd even finished speaking. I screamed out in a high pitch and immediately repeated what I'd just proclaimed. This time, I'd barely screamed out the first three words, "I love you..." when Aunt Pamela grunted and that paddle whistled through the air again.

The next four stokes landed in quick succession, one after another without time enough for me to say what I'd promised to say. Over my crying and wailing, I heard Aunt Pamela trying to catch her breath. My tears continued to rain down on the floor. My nose was running like crazy and a long string of drool connected my lower lip to the floor beneath me.

I gasped and struggled to talk, "I love you, Aunt Pam... Aunt Pamela." I looked at my Mom's picture and uttered, "I love you Mom." Then to my Gam-Gam's picture. "I love you too Gam-Gam."

Aunt Pamela let the paddle slowly and gently slide up the insides of my thighs. She let the edge of the paddle slide against my poor, wilted penis and caused it to swell up a little. She slid the paddle back and forth along the underside of my skinny, little penis and up between my cheeks. In that deep, gravelly voice, she said, "Baby, do you wish your Mom and Gam-Gam were here right now?"

I whimpered softly, "Yes. I feel bad about keeping my visits with you from them." I paused for a moment before uttering, "My Mom, my Gam-Gam and my Aunt Pamela are the only women who will ever love me and my tiny penis."

She began rubbing the paddle over my tender and enflamed bottom with the paddle. "It's good that you feel bad about keeping such an important secret from them. It shows that you're a good boy. And wanting them both to be here and see you like this, that shows how much you really love them and how important they both are to you."

The paddle moved away from my cheeks and I heard Aunt Pamela grunt. The air whistled around that paddle and I clenched up again. The last stroke from the paddle was by far the most powerful and painful. I screamed out in agony and wailed like never before. But at the same time, all the guilt and bad feelings I had were washed away. It was as if Aunt Pamela's paddle had cured me of all the bad things I'd done. It was a truly freeing feeling. Even if it was terribly painful at the same time.

While I continued to scream and cry, Aunt Pamela crossed the room and hung the paddle up in the cabinet. After closing the doors, she crossed the room to the stairs. She paused to look at me for a moment, still strapped to the punishment bench and crying wildly. She eventually climbed the stairs leaving me there to stare at my Mom and Gam-Gam's pictures.

She was gone long enough for me to mostly stop crying. I sniffled my nose while the tears began to dry on my cheeks. My eyes bounced between the pictures of the two women in front of me. I again imagined those two women really sitting on the chairs in front of me, seeing my naked body with my bottom which had to be red and angry looking. My little penis struggled to swell up to its full size at the thought of them sitting before me.

I had just begun chanting, "My Mom, my Gam-Gam and my Aunt Pamela are the only women who will ever love me and my tiny penis." When Aunt Pamela began descending the stairs.

In her hand, she carried a canvas bag with handles. She examined my bottom for a few moments before stepping around so I could see her. In a voice that sounded concerned, she whispered, "Oh my! Your bottom is going to hurt for quite a long time."

She then moved back behind me to have a seat in her chair. She began preparing things that I couldn't see. While she worked, she said, "Leslie, Honey, do you remember earlier this week when I said you would be punished during every one of your visits? Special punishments fit for a special sissy boy such as yourself?"

I tried to look back and see what she was doing, but the punishment bench kept me from turning around far enough. I answered in a soft voice, "Yes, Aunt Pamela."

"Well Sweetie, you're going to get those special sissy punishments even if you have been properly punished for misbehaving or doing poorly in school. That is what we're going to do right now." She let that sink in for a few moments before continuing, "Leslie, I think you're going to love and hate this punishment at the same time."

I whined, "What is it, Aunt Pamela? What are you going to do to me?"

She didn't answer when she stood up from her chair and approached my backside. She undid the straps around my ankles and resecured them so tight I couldn't move my feet at all. I tested the bonds again and found there was no way I would ever escape without help.

While still standing behind me, Aunt Pamela slowly dragged her fingernails from my hips to my armpits. I squealed loudly and fought to break free. I was laughing and squealing at the same time. I'd always been extremely ticklish and somehow Aunt Pamela figured it out! Her fingernails danced in my armpits and down my sides. I shrieked while struggling to get away from her fingernails.

Aunt Pamela purred, "Leslie, Sweetheart, haven't you ever been properly tickled before?"

Her fingernails danced their way over my ribs and down to my hips. I screamed and laughed and shrieked all at the same time. I begged her to stop. But that only made her tickle my body more enthusiastically.

She continued to purr, "Sweetheart, every time you come to visit, I'm going to tickle you just like this. I'll never grow tired of doing this."

It felt like she tortured me with her fingernails for hours, but it probably only a minute or two. When her touch left my body and I heard her step away. I tried to catch my breath while realizing tears were rolling down my cheeks again. I looked into the eyes of my Mom and Gam-Gam's pictures and wondered if they'd ever wanted to tickle me like this.

I heard Aunt Pamela approaching me again and fought to look back at her. "What are you doing? Aunt Pamela please stop! I can't take anymore!"

"I'm betting the bottoms of your feet are quite ticklish. I'm going to sign my name on the bottoms of both of your feet with this..." From behind me, she reached around and held a ballpoint pen in front of my face.

I screamed, "NO! PLEASE!! My feet are the most ticklish parts of my body! Please don't!"

The pen moved out of my line of sight and I was left looking at Mom and Gam-Gam again. In a high-pitched squeak, I began to chant, "My Mom, my Gam-Gam, and my Aunt Pamela are the only women who will ever love me and my tiny..."

That was as far as I got before the tip of that pen touched the bottom of my left foot. It felt like I'd been electrocuted. I screamed at the top of my lungs and fought against the straps holding me down. I was laughing, screaming, giggling and crying all at the same time. I tried to chant again, "I love my Mom! I love my Gam-Gam! I love you, Aunt Pamela!"

The pen finally pulled away from that foot and I was left gasping for air with tears dripping onto the floor. While still struggling to calm down I continued to chant, "My Mom, my Gam-Gam and my Aunt Pamela are the only women who will ever love me and my tiny penis."

I could feel Aunt Pamela's warm breath on the soles of my feet. "Oh my, you are a ticklish boy. Does Mom know how ticklish you are? What about Gam-Gam? Has she ever held you down and tickled you?"

While my eyes shifted from my Mom's picture to Gam-Gam's, I whimpered, "They know I'm ticklish. But they never tickled me so bad."

"That's a pity. If they did, they'd see how much you enjoy it." With that, she reached between my legs and let her finger slide down the length of my stiff penis.

I squeaked, "Why is it stiff?"

She whispered, "Silly boy, you're very excited about all this tickling! In my experience, gently boys always get excited when they get tickled."

As she finished that sentence, the tip of the pen touched my right foot and she began signing her name. She wrote slowly and I guessed she was using large loopy letters. If I hadn't been strapped down, she would have had to scrape me off the ceiling. I was screaming and laughing and begging for mercy all over again. But it was different with this foot. I knew my penis was stiff and throbbing. It was still torture to be tickled like that, but it was also making me very horny! And I couldn't stop imagining my Mom and Gam-Gam sitting right in front of me watching the entire encounter.

When the tip of that pen drew a line from my heel, all the way across the arch of my foot to the beginning of my big toe, I screamed loudly and a little pee squirted out of my penis. As soon as it happened, I couldn't believe I'd actually peed! I was so ashamed, but I was still trying to catch my breath and recover from the tickling I'd endured. I squeaked, "I'm sorry Aunt Pamela! I couldn't stop it! I'm really, really sorry!"

Aunt Pamela pulled the pen away from my foot and whispered, "There is no need to apologize. That was just adorable! You were laughing so hard you went pee! Leslie, Sweetheart, you are so precious." Before releasing me from the bench, Aunt Pamela rubbed my tender bottom down with a greasy medicated ointment. She used a gentle touch and the pain from my spanking quickly began to fade. It didn't completely go away, but it dulled enough that I could easily deal with it.

The sound of the Velcro being ripped open echoed around the room while she unstrapped me from the bench. Aunt Pamela helped me to my feet because I was a bit off-balance, my legs were rubbery and my bottom still tingled. Before we made our way back upstairs, she grabbed the pictures of Mom and Gam-Gam in one hand and held onto me with the other.

My bottom was slippery from the ointment and my penis was standing up perfectly straight. It bobbed with every step I took. While we crossed through her living room, Aunt Pamela glanced up after staring at my penis and said, "Leslie Honey, is your penis shrinking? It looks even smaller today than it did earlier this week."

Using my fingers, I pressed it so it pointed straight out in front of me. Biting my lip, I looked up passed Aunt Pamela's giant chest into her eyes and said, "I don't think so. But I guess it could. Does it really look smaller?"

She looked down at me and very seriously said, "Yes it does. It looks quite a bit smaller. Sweetie, I think we should start measuring it during your visits. That's the only way we'll know if it's shrinking."

Biting my lip, still looking up into her eyes, I whispered my mantra out loud, "My Mom, my Gam-Gam and my Aunt Pamela are the only women who will ever love me and my tiny penis."

We stopped walking while standing in her living room. Aunt Pamela leaned down to whisper in my ear and one of her giant breasts brushed against my cheek. "That's right. And it doesn't matter how tiny your penis is. We'll always love you."

She had me stand on my rug in the middle of the room while she took a seat on the couch. After propping up the pictures of my Mom and Gam-Gam on either side of her, she leaned down and opened her sewing basket which sat on the floor under an end table. She pulled out a fabric tape measure from inside the basket and beckoned me toward her by wagging her index finger in my direction.

A shiver shot through my body and ended in the squishy head of my little penis. I'd been tempted to measure my penis before, but never worked up the nerve to actually do it. I knew I was small, much smaller than other guys my age. But I was really afraid to learn my true measurement.

My penis continued to throb as I stepped between Aunt Pamela's spread knees. Before she laid the tape measure on my penis, she looked into my eyes and spoke in a soft, sincere tone, "Leslie, just remember, it doesn't matter how small your penis is, your Mom, Gam-Gam and I will always love you."

My voice cracked when I uttered, "I know Aunt Pamela." From her eyes, I next looked at the photograph of my Mom and then to my Gam-Gam.

Holding the tape against the top of my penis where it met my stomach, she then stretched the tape out to the very tip. I couldn't look down and see the measurement. I squeezed my eyes shut and didn't wait long to hear Aunt Pamela's reaction. She gasped loudly. "Oh my! It's not even 3 inches long! Sweetheart, it's even smaller than I thought it was!"

My back arched and a soft moan left my lips. In a soft voice, I whispered, "My Mom, my Gam-Gam and my Aunt Pamela are the only women who will ever love me and my tiny penis."

She adjusted the tape to double-check the measurement and chuckled while saying, "That's right Sweetheart. Your little penis is just too small for anyone else to appreciate." I whimpered softly after looking down to see the tip of my penis just short of the 3-inch mark.

Aunt Pamela left the tape measure laying over my little penis and asked, "Leslie, do you want me to make your little penis squirt?"

My hips were squirming around in circles. My bottom was still tender and slippery from the ointment. I was naked and very horny in front of Aunt Pamela and the pictures of my Mom and Gam-Gam. I squeaked, "Yes please."

She smiled while rolling up the fabric tape and putting it back in her sewing basket. "Run outside and cover the picnic table with the tablecloth by the backdoor. And don't forget to bring along your Mom and Gam-Gam's pictures so they can watch. Get up on the table on your hands-and-knees, just like last time. I'll be out in a few minutes."

My voice was squeaky when I uttered, "Aunt Pamela, can't we stay inside today?"

She rose up from the couch and pulled me into an embrace. My face was drawn into the pillowy, perfumed cleavage of her bosom. She wrapped her strong arms around my skinny, naked body and spoke in a soft voice, "Baby, as long as the weather remains warm, you'll be getting your rewards in my backyard. Now run along. I have a few things I need to prepare."

After our embrace ended, I watched her leave the room before I gathered up the two framed pictures and headed toward the backdoor. On the way, I picked up the tablecloth she had mentioned. I stood at the backdoor and took a deep breath. I already knew her backyard was relatively private. But stepping outside with a stiff penis and tender bottom wasn't something I'd ever get used to. I held both the table cloth and the pictures against my little penis.

Cracking the door open, I peeked around her yard and found it to be just as I remembered it. Seeing no one peeking through the bushes or trees, I stepped outside and the door closed behind me. Without hesitating, I raced to the raised, octagonal wooden deck in the middle of her lawn. Gently arranging my Mom and Gam-Gam's pictures on two of the chairs, facing the table. I giggled and my hips squirmed from side to side while I remembered what Aunt Pamela had done to me during my last visit.

I threw the red-and-white checkered cloth over the table and arranged it so it looked neat and tidy. Glancing around the yard once more, I climbed up on the table and tried my best to imitate the position from my last visit. On my knees with them spread apart. My shoulders resting on the table and I faced the pictures of Mom and Gam-Gam.

On that table with the sun shining down on my pale body and a warm breeze blowing across my naked skin. I remained on that table for several minutes before I heard Aunt Pamela's back door open. When I turned to see her, I smiled and saw she was carrying the familiar crystal pitcher and her craft bag. She took a seat at one of the remaining places. Once comfortable, she said, "You look perfectly adorable, as usual!"

I giggled and my hips squirmed around again. My little penis was super stiff and leaking its excitement. I giggled, "Thank you, Aunt Pamela."

She replied, "Sweetheart, you don't need to thank me. I need to thank you! You are a true ray of sunshine in my life."

While she spoke, she began pulling items from her craft bag. The crystal pitcher was set aside until it would be needed. The familiar crystal bowl was placed directly beneath my desperate penis. The last thing she brought out from her bag was an electric toothbrush. I looked from that toothbrush to Aunt Pamela's eyes. She had a smile on her face and before I could ask, she turned the toothbrush on and it began to vibrate before my eyes. Very slowly, she moved the toothbrush under my body. With the bristles of the brush facing away from my body, she touched the plastic backing against the underside of my penis, just below the squishy pink head. I squealed and my hips began to grind in lewd circles. The vibrations of that brush were quickly driving to the verge of orgasm.