Aunt Pamela and Leslie

Aunt Pamela rose up and walked behind me. I fought hard to regain control of my emotions, but it was too much. No matter how hard I tried, I couldn't stop crying. She stood behind me and off to one side. I felt her rest the leather strap against my bare bottom. She rubbed it across my naked cheeks and told me I needed to count the strokes for her. She was afraid she'd lose count and give me more than I deserved.

She asked if I was ready and I softly whimpered that I was. She pulled the strap away from my cheeks and time seemed to stop. The room was completely silent while I waited for my punishment. The first sound I heard was Aunt Pamela inhaling and then grunting. That was followed by a swishing sound as the strap passed through the air. It seemed to take a very long time before it made contact with my bare cheeks. But when it did, it felt like the skin of my behind exploded from the inside out. I screamed and tears began pouring from my eyes. While I wailed, drool begin to drip from my lips.

I fought against the straps holding me in place. I deserved to be punished, but the pain of that single blow was far more painful than the grade I'd gotten on my quiz merited. I screamed out and begged Aunt Pamela to release me from the bench.

Aunt Pamela calmly reminded me to count. I somehow managed to scream out the word, 'One!' As soon as the word left my lips, she inhaled, grunted and the strap whistled through the air and struck me again. I screamed out the word 'Two!'. The third and forth swings came in quick succession and I didn't have time to count them. But I did manage to scream out 'Five!' when that one came. My butt cheeks felt like they were on fire! With each crack of the leather against my bare behind, it felt like the skin was being split apart. It was far more painful than I ever could have imagined.

After the seventh swing, Aunt Pamela came around near my face. I was crying uncontrollably and still struggled against the straps holding me in place. But no matter how hysterical I'd become, I couldn't miss the fact that Aunt Pamela's glorious cleavage was left exposed for me to admire. The cups of her massive white bra still hid the majority of her breasts from my hungry eyes, but it was the closest I'd ever come to seeing breasts.

Aunt Pamela stroked my hair and kissed my cheek. She told me I was halfway done. She kissed me again and asked if I wanted the remaining seven strokes quickly or spaced apart from one another. I begged her to have mercy and let me go with only the seven strokes. But she knelt beside me patiently, letting the tip of her finger trace the edge of her bra and waited for me to answer her question. I whimpered between sobs that I wanted it to end quickly. She kissed my cheek again and told me I was a very brave boy for taking my punishment so well.

She moved back behind me and didn't ask if I was ready or give me any warning at all. The seven strokes of that strap came quickly and with full force. I screamed and clawed at the bench. I'd never cried so hard before. The pain of that punishment was indescribable. I never imagined anything could hurt that badly. I felt the burning, searing pain in the very core of my body.

After the fourteenth stroke had been applied, Aunt Pamela crossed the room and returned the strap to its place in the cabinet. She turned to face me and I watched while she straightened up her dress and closed the buttons she'd undone. She shut the cabinet doors before returning to my side. Her fingertips brushed over my back before she began unstrapping me from the bench. She told me the punishment was over. She told me I'd been very brave and because of that, she felt I deserved a reward. She asked if I wanted a reward.

While still bawling, I managed to ask her what type of reward. She intentionally avoided touching my extremely tender bottom while her fingertips drifted between my legs and touched my little pouch of balls. She then dragged her fingertip along the underside of my wilted penis. In a gentle voice, she told me she knew how brave boys liked to be rewarded for good behavior.

Feeling her touch on my most private places helped to distract me from the punishment I'd received and stop my crying. I managed to calm down relatively quickly. With her finger sliding up and down along my small penis, I whispered that I'd like to be rewarded very much. She removed her touch and continued to unstrap me. She told me the basement was only for punishments. She'd never reward a boy until we'd left that room. Once I was unstrapped, she helped me to my feet. She had to hold onto me or I would've fallen. My legs felt like jelly after the brutal strapping I'd received. My butt felt like it was on fire. Raising my leg to climb the stairs was almost unbearable and Aunt Pamela basically carried me to the main floor of her home.

Our first stop was the bathroom where she warmed a cloth under the sink and washed my face. I stood there passively while she wiped away the mess. Yes, she had just finished beating me. But the act of her washing my face was so tender and kind, I separated what had occurred in her basement to the woman I was with now.

When she finished, I moved to look at my behind. But she stopped me from doing so. Instead, she guided me to a small room off of the living room. The little room was decorated with a soft, pastel yellow color. The room was equipped with a table and chair with a small chest in the corner. On one wall hung a large television screen. And after Aunt Pamela had helped me climb up on the table on my hands and knees, she turned on the camera hung on the opposite wall behind me. Right there in front of me, in full color on the giant screen was my bright red, angry looking bottom. I clearly saw the edges of where the outer most straps had landed. My cheeks were already bruising in parts and I knew I'd learned my lesson. I'd study much harder for my next quiz.

Aunt Pamela pulled the chair up behind me but was outside of the camera's view. In a soft voice, she told me before I received my reward, she needed to tend to my bottom. She opened a drawer of the chest and pulled out a glass jar with a metal lid. I watched on the large televisions while she set the jar between my knees and removed the lid. Aunt Pamela told me she was going to apply a bit of ointment to my bottom. She said it would dull the pain and speed-up the healing process.

She scooped out a large glob of the clear, oily substance on her first two fingers. She raised those fingers toward my abused bottom and just before she made contact, I flinched. Aunt Pamela reminded me that my punishment was over. All that would happen from that point forward would make me feel good.

I bit my lip and watched as she gently spread the ointment over the outer edges of the red and bruising areas of my cheeks. She then worked in concentric circles closer to the most painful parts. I flinched and squirmed while she gently applied the oily substance. It soon became apparent that it was helping with the tenderness and pain. When she asked me to arch my back, her greasy fingers slid between my cheeks and grazed over my tingling little knot of a hole. I squeaked in a high pitch and arched my back even more.

Aunt Pamela spoke in a soft voice, she asked if I'd ever been touched there before. She already knew I hadn't, but I told her so anyway. She asked if I liked being touched there. I didn't need to answer that question, my hips pushed back against her finger and a soft moan escaped my lips. Her finger didn't penetrate me, she simply slid her oily fingertip over the tight knot of muscle. It was a delicious feeling that made me squirm on the table top.

All too soon, she removed her hands from my body and wiped them on a cloth. My still, bright red bottom was now glistening with the ointment she'd applied. Thankfully, the tenderness and pain had faded a bit. I was now prepared for the reward she'd promised.

From the chest, she retrieved a small, clear crystal bowl. She placed the bowl directly under my little penis. Reached underneath my stomach, she began to caress my stiffening penis. I squeaked and told her that no one had ever touched me like that before either. When I turned my head to look at her, she told me to keep my eyes on the screen in front of me. Biting my lip, I returned my gaze to the large screen television.

Looking at my bruising cheeks on the television wouldn't allow me to completely focus on the pleasure of her gentle touch. The dull pain and memory of the spanking I'd received were displayed larger than life right in front of me! Even with my tortured bottom on display in front of me, it didn't take long for my penis to become completely erect. And when it did, Aunt Pamela pointed it straight down toward the crystal dish.

In a soft voice she said, "Leslie Sweetie, I think you have the cutest little penis I've ever seen! It's absolutely tiny!" Before I could react to her words, she began stroking my inexperienced penis up and down. I felt dizzy and a tingling feeling began to radiate from my stomach. She continued, "I've always loved playing with little ones. Have you ever measured this little guy?"

My back arched and I moaned that I had. She asked how little it was, but before I could respond, she pulled out a small, pink plastic, 6-inch long ruler from the chest of drawers. While aiming my erect penis straight down, she placed the ruler right beside it.

We both looked at the giant screen in front of us and she moaned, "Three inches! You are just precious!" She reached back into the chest of drawers and pulled out a laminated chart. She laid it on the table, directly under my head. It was designed like a bar chart with each of the bars being a penis. On the far right, the images were thick and noted as measuring +12-inches. The penis' shrunk in size and changed from realistic images to cartoon-ish representations as I followed the chart to the left. The smallest, cartoon drawing of a penis on the chart was noted as measuring 3 and a half inches. My little, 3-inch penis wasn't even on the chart!

I whined, "Aunt Pamela!" And then looked back up to the television and watched my little penis drool a large clear drop of my excitement into the crystal bowl. My back arched deeply and when it did, my bright red cheeks spread apart. The pale white crease between them looked so out of place, not to mention my little, pink, balloon-knot of a hole.

Aunt Pamela spoke in a matter-of-fact sort of way, "Leslie Sweetie, you must know that you'll never be able to satisfy a girl with this tiny little thing. It's simply too small and too skinny. There isn't a girl alive that would able to feel this inside her. Angel, you're so lucky that we met. I may be the only woman alive that can appreciate such a tiny, little penis."

I knew every word she spoke was the truth. I moaned and goosebumps popped up all over my naked body. "My Sweet Leslie, it's okay. You've earned your reward. Squirt for me. Let it go. Let this little peepee squirt out all of its cream for your Aunt Pamela."

My back arched and a rather high-pitched moan slipped out from inside my body. I watched on the giant screen directly in front of me as my little penis shot out a long stream of pure white cream. It covered the bottom of the crystal dish and another long stream erupted from inside me and further filled the dish. Aunt Pamela stroked me up and down until the last drop of my cream had fallen into the dish.

After giving me only a few moments to recover, she moved the dish on top of the chart directly below my face. She'd placed the bowl over the smallest penis' on the chart, leaving the giant images of cocks out for me to see. The pool of my cum resembled heavy cream and had an erotic scent. I bit my lip and briefly considered taking a lick of it. But that thought passed quickly when Aunt Pamela positioned a matching crystal pitcher under my penis. I watched on the giant screen as she aimed my little erection directly into the pitcher and told me I needed to flush out my penis after every orgasm. If I didn't, I would be in danger of getting a bladder infection. She kissed my naked hip and said, "Go pee for me. Let it go for your Aunt Pamela. It's okay Sweetheart, let it happen."

I couldn't take my eyes off of the screen in front of me. Aunt Pamela's finger and thumb kept my skinny, little penis aimed right into the fancy, crystal pitcher. I fought against the humiliation of the act that was about to occur. It would happen, there was no denying that. I would pee in the pitcher while this mature woman I'd just met, aimed my penis for me. I only needed to accept the shame of the act.

After swallowing hard and fighting back tears, I whimpered, "I love you, Aunt Pamela!" As those words left my mouth, I released my bladder and the sound of my stream striking the pitcher filled the room. The sound quickly changed as the pitcher began to fill, it became that of my stream striking a pool of liquid. I watched the event occur on the television in front of me. I couldn't believe it was really happening. My back was still arched deeply enough to allow my cheeks to part and expose my little wrinkled hole. My penis was being held by Aunt Pamela's finger and thumb and aimed straight down into a crystal pitcher. And from my skinny little erection, a stream of light yellow urine was spraying downward. The level of my pee was rising slowly, it would wind up accumulating an inch or two in the bottom of the pitcher.

Aunt Pamela kept my penis aimed directly into the pitcher and whispered, "I love you too, my sweet Leslie."

My entire body burned with shame while I urinated into the pitcher. I'd never had anyone watch me go to the bathroom like that. And I sure hadn't ever had anyone hold my penis for me! It was by far the most embarrassed I'd ever been. But the act was also strangely arousing. My penis tingled and swelled throughout the event. When I'd finished and after Aunt Pamela tapped off the last few drips from my penis, she kissed my hip again and told me I was a good boy.

She reached up and tilted the bowl of my cum to one side, making all of it ooze to one side. In a soft, kind voice, she asked, "Sweetheart, does your little wee-wee always squirt out this much cream? Or did you do this to impress me? Because there is nothing more precious than a teeny-tiny penis that squirts out big, adult-sized cumshots."

I moaned softly while still straddling the pitcher between my thighs, looking down at the small bowl containing my cum. I spoke in a soft voice while unnecessarily explaining if I don't touch myself for a day or two, it squirts out in big globs. But if I play with myself a lot, it only comes out in a few drips. But I played with myself last night and this morning. It should have only been a few drips. I couldn't understand why I'd squirted out so much.

She sounded pleased with my answer and while telling me she couldn't wait for my next visit, she reached up and tapped the pad of her index finger against the quivering, wrinkled hole between my cheeks. After I squeaked and my hips jumped up against her finger, she told me if I was a good boy until my next visit, she would introduce me to some of the special toys she keeps for well-behaved boys that enjoy having their bottoms played with. While not penetrating my little hole with her finger, she did rub around the ring of tight muscles with her fingertip. She asked if I was interested in exploring her collection of toys for my behind.

"Yes please!" squeaked out of my mouth. My penis was perfectly stiff and the squishy pink head was pressed against the crystal of the pitcher.

In a kind, understand tone she said, "We will, during your next visit, I promise Sweetheart."

Aunt Pamela helped me down from the table and had me carry the bowl of my cream while she carried the pitcher of my pee. She led me back to the bathroom and I stood nearby while she cleaned both of the dishes with soap and water. After drying them off, we walked back to the yellow room where she put them away in the chest. From there, she guided me back to the living room and took a seat on the couch. Before allowing me to get dressed, she had me turn my back to her so she could examine the damage done to my bottom.

She had me stand beside her knees, facing away from her. I bent forward while Aunt Pamela laid her hands on my hips. She told me I was going to be tender for a day or two. I could feel her warm breath on my bare cheeks and my little penis responded accordingly. It was pointing toward the ceiling by the time she'd turned me around.

I stood right in front of her completely naked with a very stiff penis while she retrieved a fancy looking pen and black, leather-bound book from an end table. She flipped through the pages of the book until she found the first blank page. She wrote down my full name, address, phone number, email address and the blocks of time I would be busy in class. Flipping through the pages to the back of the same book, she found her schedule for the following week and told me she had an opening the following Tuesday at 1:30 pm.

My pink penis throbbed at the thought of spending more time with Aunt Pamela and her eyes zeroed in on it as it jumped. I bit my lower lip and shuffled from one foot to the other. I was still rather embarrassed to have this mature woman see my naked body. It didn't matter that she'd stripped me naked and spanked me. Nor did it matter that she stroked my delicate penis until it squirted and even held it while I peed. I wasn't used to having anyone look at me the way she looked at me.

In a soft voice I told her that when I'd read her advertisement on the school's bulletin board, I got the impression I'd need to pay her. Aunt Pamela smiled while reaching up and tickling the underside of my dainty penis. She told me she enjoyed the company of special young boys such as myself. She explained that she loved to play with little penis' and punish tight little bottoms. I didn't need to worry about paying her with money. I would pay her by always being prompt, honest and never missing a scheduled meeting.

She told me that she expected us to begin meeting weekly. And each week we'd sit at her computer so I could log into my account at the University. She and I would review my grades from the previous week. Aunt Pamela told me I'd be punished for any grade less than 98%. It didn't matter what class or if it was a quiz, test, midterm or final. All of my grades would need to be 98% or better.

Aunt Pamela said she knew I longed for a maternal figure in my life that would appreciate my hard work at school. She knew deep down inside I needed to be punished if I didn't do my best. And more than anything else, she knew I needed to be properly rewarded for achieving the 98% goal she'd set for me. She told me that she would reward me in a way my mother never would. She would take my precious little penis between her fingers and make me squeal and squirt like no one else could. She would introduce me to dildo's, vibrators and plugs for my cute little bottom.

I stood before her with my hands laced behind my back. My little penis was very stiff and drips of my arousal were oozing from the squishy pink head. Those juices allowed Aunt Pamela's finger to slide up and down along the underside of its petite length with ease.

She didn't look up at me. Instead, she kept her attention focused on my throbbing penis. "Leslie Honey, will this tiny excuse for a penis ever be able to satisfy a girl?"

I bit my lower lip while my penis throbbed and a large drop of my juice further lubricated her fingertip. I whispered, "No."

She grinned, "Sweetheart, can you think of anyone who could ever appreciate such a teensy-weensy penis?"

My breathing was coming in gasps as I neared another orgasm. In a higher than normal pitch, I squeaked, "Just you Aunt Pamela! Only you!"