Aunt Pamela and Leslie

By fantaseeboy.



 
 

When my Statistics class drew to an end, I raced out of the room while struggling to keep from crying. I’d never gotten anything less than an ‘A’ on a test. And my very first quiz in my Freshman year at University I’d bombed with a ‘B.’ I was devastated.

As I dashed down the hallway, I passed a bulletin board, and a pink slip of paper caught my eye. It was half-covered by a more recent announcement of a faculty luncheon. After lifting the luncheon announcement, I was able to better examine the pink half-sheet. It was an advertisement of sorts for a place called ‘Aunt Pamela’s Emporium.’ The font used on the ad was loopy and feminine in nature. Questions were written out on the sheet.

Are you homesick? Do you miss the encouragement of your mother? Do you need a hug? Do you need to be cuddled? Do you need to be scolded? Do you need to be punished? A visit to Aunt Pamela’s Emporium may be just what you need.

Along the bottom of the sheet, a phone number was listed multiple times, and each number was cut so it could be torn off. Not a single phone number had been removed from the sheet.

I bit my lower lip and tore the phone number from the sheet. I held it in my hand while I walked back to my dorm room. When I was finally alone in my room, I laid the small piece of paper with the number for Aunt Pamela’s Emporium and my Stat’s quiz on my desk. The handwritten ‘B’ glared at me, and I knew I’d have to call Aunt Pamela.

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My own mother had always been distant and rarely showed any signs of affection. She never once raised a hand to me, and I couldn’t recall ever being punished. I’d always been a good student, well-behaved, small-statured, polite, and timid. I have never been the type of boy who needed to be punished, but I had often felt I deserved to be spanked or even worse. Aunt Pamela seemed like the woman I’d needed in my life for a very long time.

I picked up my phone a half dozen times to make the call, but I kept chickening out. After almost an hour, I let the call go through and heard Aunt Pamela’s maternal, educated voice for the first time. She sounded very kind and understanding. Her voice was how I wished my mother had spoken to me while I was growing up. I knew I’d made the right decision calling her. But I was very worried about the cost. I was a college student and didn’t have much to spend. When I mentioned this to Aunt Pamela, she told me not to worry about the cost, and it would work itself out.

Aunt Pamela worked out of her home in a quiet residential area, just 8 blocks from my dorm. During our conversation, she told me she’d had a recent cancellation, and if I could make it to her home at 2:00 pm, we could have our first meeting. It was only 12:30 pm, and I told her I could make it.

Aunt Pamela told me I needed to shower and arrive at her home looking nice. She wouldn’t stand for a young man who didn’t care about his hygiene or appearance. She warned me to be prompt, or she may not let me into her home. She also told me to think about my reason for contacting her. She wanted me to be prepared to tell her why I felt I needed her in my life.

After hanging up the phone, I spent the next hour scrubbing, combing, and generally cleaning myself. I even shaved my face, even though I didn’t need to. I’d never been especially hairy and only shaved once a week. Even then, it wasn’t really needed. I put on my best khaki’s, a button-up collared shirt, brown leather boat shoes, and a matching belt. I glanced in the mirror on my way out the door and thought I looked good, a little juvenile, but good.

The walk to Aunt Pamela’s home went by quickly, and I soon found myself standing on her doorstep. Glancing at my phone, I was glad to see I’d arrived 5 minutes early. I tapped on the door timidly and waited. Moments passed before I heard the sound of someone approaching from inside. The door came open, and there stood the woman whose image should be displayed by the word ‘mother’ in the dictionary.

She was a full-figured, substantial woman. She had wide hips, enormous breasts, and thick thighs. Her heavily greying hair was neatly styled in a loose bun. Her face was wrinkled in all the expected places of a woman her age. She had dark blue eyes, a warm smile, and perfectly applied subtle make-up. She stood several inches taller than my 5’4″. She wore a below-the-knee, light-blue dress with a white floral print. Her legs were encased in nylons, and on her feet, she wore low, white heels. Around her neck was a string of pearls, and she wore rings on two fingers, neither of which was a wedding band.

She held out her hand and said, “You must be Leslie.” She reached out and offered her hand. I looked up into her eyes and timidly said, “Yes, Ma’am.” I then reached up, and she took my hand without shaking it. She just held it. She briefly squeezed my small hand in hers, and I felt her strength and my penis tingled in my pants.

She glanced at the thin watch on her opposite wrist, “You’re 3 minutes early. I do appreciate a young man who is prompt.” She still held my hand in hers when she led me into her home. Her living room was decorated in the same manner as my grandmother’s home had been. There were family photos on the walls, the furniture and decorations were not modern, but a classy, older style. She guided me to the sitting area of the room and took a seat in the middle of her couch. She had me sit close beside her, so close that our legs were touching. She wrapped her arm around my shoulders and boldly asked why I’d called her.

I stuttered and mumbled a response. I wasn’t expecting Aunt Pamela to get right to the point of our visit. For some reason, I expected us to get to know each other before we got down to business. Aunt Pamela pulled me closer against her and kissed the side of my forehead. She told me I didn’t need to be nervous. She told me whatever we discussed would remain between the two of us. She went on to add that no one would ever know what the two of us did in her home. She kissed my forehead again and told me she could be trusted.

For whatever reason, I believed her wholeheartedly. Her words got me talking, and once I started, I couldn’t stop. I told Aunt Pamela about my distant relationship with my mother and how I’d longed for us to be much closer. I went into detail about how lonely I was growing up. I told her how I’d always pushed myself to do well in school and how I’d hoped it would make my mother proud, but she never seemed to notice. I explained that I’d never had many friends. She listened to every word I said and asked questions when she didn’t fully understand.

After I’d told her I’d never had a girlfriend, Aunt Pamela interrupted and asked if I’d ever had intercourse. I blushed deeply and whispered, “No, Ma’am.” She squeezed me against her large, soft body and told me it was nothing to be ashamed of. Without pausing, she then asked how often I masturbated.

I wanted to crawl under a rock! I was so embarrassed! When I tried to tell her I didn’t masturbate, she refused to believe it. She had me look at her in the eyes and asked if I was honest. She told me she wouldn’t stand for a liar. I was so humiliated! But I somehow forced myself to tell her I did it once or twice a day.

Aunt Pamela told me to be clear and use complete sentences. She asked what it was that I did once or twice a day. She held a single finger under my chin and forced me to maintain eye contact while answering her. My voice cracked, and my penis became completely stiff while I said, “Aunt Pamela, I masturbate once or twice a day.” It was extremely emotional to make that confession, and I felt a few tears roll down my cheeks while looking into her maternal eyes.

She told me I was a good boy and that I should always be honest with her. I nodded my head, and I promised I would. Aunt Pamela held me against her for several moments. We were just sitting together with her arm wrapped around my shoulders. It was the most human contact I’d had in a very long time. The more I snuggled against her, the tighter she held me with her arm. If I had been a cat, I would have been purring.

After several moments, in that calm, understanding voice of hers, she said, “Leslie, Sweetheart, I want you to stand right in front of me on that rug.” She motioned toward a round, floral patterned rug in the center of the room. “I want you to hold your hands behind your back, look right into my eyes, and tell me why you’ve come to visit me today.”

My legs felt like jelly when I rose off the couch. I took small steps to the center of the room before slowly turning to face Aunt Pamela. Lacing my fingers together behind my back, I fought against my embarrassment to look her in the eye. Biting my lip, I then told her about the quiz I’d taken in my Stats class. I told her I’d never gotten anything lower than an ‘A,’ and the ‘B’ on that quiz was unacceptable. The longer I spoke, the more difficult it became not to cry. As I neared the end of my wretched tale, I was sobbing uncontrollably.

Aunt Pamela sat on the couch with her hands folded in her lap and her perfect posture listening to my confession. She waited until I regained some control over my emotions before speaking. Without sounding pleased or disappointed, she asked, “Leslie, do you believe you should have done better on the quiz?”

I whimpered the word ‘yes’ between sobs.

In that same neutral tone, she asked, “You didn’t come here for a hug or for me to tell you everything would be alright, did you?”

I whined, “No!”

She frowned for a split second before asking me to tell her why I’d come to visit her. Just as I began to speak, she cut me off and told me to look her in the eyes. I sobbed and gasped from breaths while raising my chin to look at her. Tears were rolling down my cheeks, and my chest heaved with each breath I took. “I, I, I came for a spanking!”

Aunt Pamela let me sob for several moments. She sat there and watched me cry. When I’d regained my emotions to a point, she told me she’d get me a tissue in a moment. But before she did, she wanted to let me know that when she punished a boy, she did it with purpose. It wouldn’t be a light, playful spanking. It was going to hurt. I would cry, and I may scream. I would have difficulty sitting for a least a day afterward.

I stood before her, sobbing and knowing I deserved to be spanked. I struggled to look at her, but a look of disappointment had appeared on her face. The same look I should have gotten from my mother for every grade I’d ever earned below an ‘A.’

After giving me another minute to cry, Aunt Pamela spoke again. She explained that she only punished boys in her basement. She went on to say that boys were only allowed in her basement when they were completely naked. And once the basement door closed, there was no turning back. I would receive whatever punishment she felt was appropriate.

My emotions had taken over again, and I was all out bawling. While I stood there crying, Aunt Pamela stood up and retrieved a box of tissues from the next room. I hadn’t taken a single step for the center of that rug even after she returned. She offered me a tissue, and I accepted. While I wiped my tears and blew my nose, she began to unbutton my shirt. I shivered and looked up into her eyes.

In a gentle tone, she said, “Leslie, Honey, you know you deserve this. You obviously didn’t study very hard. We both know you should’ve gotten an ‘A.’ I’m going to give you the spanking you deserve. Do you understand me, young man?”

I nodded my head while Aunt Pamela slid my shirt off of my shoulders. She folded it neatly and laid it on the arm of the couch. She guided me to the couch, and after we’d both sat down, she took my legs in her lap and removed my shoes and socks. She folded my socks and slipped them into my shoes.

As I stood back up in front of her, I realized I was about to become naked! She reached out and began to remove my belt. I whimpered softly, and my hips squirmed away from her. Aunt Pamela looked up into my eyes with a stern look on her face. She asked what I was doing. I stuttered and tried to tell her no one had ever seen me naked before, except for the doctor. I was worried about her seeing me naked!

She pulled my belt off through the loops of my khaki’s. She then unbuttoned my pants and lowered the zipper. While she worked, she told me she’d seen many young men naked before. She asked if I was worried about her seeing how small my penis was. I bit my lip and nodded my head. She looked up into my eyes while informing me that she already knew my penis was teeny-tiny. While she spoke those belittling words, she pulled my underpants away from my petite erection and then lowered them to my ankles with my khaki’s. My hands shot down and protected my skinny, little hard-on from her gaze. I shivered with shame while sobbing once again and stepped out of the last of my clothes.

Aunt Pamela folded my pants and underwear and placed them on top of my shirt. Without even trying to get a look at my naked body, she rose up off the couch and took my hand. This left me with only one hand to keep my modesty protected. Tears rolled down my cheeks while she led me to a staircase leading to her basement. I followed her obediently, never once even considering leaving this woman’s home. I deserved whatever punishment she felt was appropriate.

As we stepped into the large room that was her basement, Aunt Pamela closed the heavy door behind us. The sound of that door closing sealed my fate. I would be properly punished for the first time in my life. While cupping my little erection in one hand, I looked up at Aunt Pamela and apologized for doing poorly on my quiz.

Her face was still masked with disappointment. “I’m sure you are sorry, Leslie. But saying you’re sorry doesn’t forgive you for your unacceptable grade.” She reached out and cupped my chin in her free hand. “Angel, I’m going to give you the spanking you deserve. This afternoon you’ll get a punishment to make up for all the times your mother should have taken you over her knee. It will be a spanking you won’t forget for a very long time.”

Tears rolled down my cheeks, and my chest heaved while I struggled to breathe between sobs. Hearing her mention my mother while I stood naked beside her was unnerving. I could no longer look at her and shifted my attention to the room I’d been brought to.

The basement was windowless but brightly lit. The walls were painted a very soft blue, and the ceiling was left painted white. The floor was covered with white carpeting except for a large round area in the very center of the room, which was covered with an equally white linoleum. In the center of that circle of linoleum sat a scary-looking piece of furniture that Aunt Pamela explained was her spanking bench. A large, comfortable-looking chair with a light blue floral print sat just outside of the linoleum. The only other thing in the room was a large wooden cabinet mounted on one wall.

Aunt Pamela sat on the chair and told me to cross the room and open the cabinet. Using both hands to hide my little penis, I took small steps until I stood in front of the cabinet. I glanced back at Aunt Pamela before opening the doors. I began bawling once again when I learned what the cabinet contained. Hanging neatly on the insides of both doors and all along the back of the cabinet were instruments of punishment.

There were paddles, crops, canes, floggers, and straps—all of them in a variety of sizes and designs. I’d fantasized about being punished with all of them. But as I stood there looking at them in real life, the reality of what was about to occur settled in on me. While my teary eyes took in the contents of that cabinet, my hands fell away from my erection. When I turned to face Aunt Pamela, I didn’t cover myself. I was going to be punished. That was the only thought on my mind.

While I stood there looking at all the terrifying contents of the cabinet, I never thought about running from the room. Aunt Pamela had warned me that once I entered the room, there was no turning back. Aunt Pamela was so easy to talk to. She insisted upon honestly, and I knew, no matter how embarrassing it may be, I would never lie to her. I needed her in my life, and I deserved the punishment I was about to receive. I no longer cared if she saw my nudity. In all honesty, I hoped she’d take pity on me after learning how underendowed I was.

Her eyes wandered up and down over my naked body several times. She learned how little body hair I had. She saw my pale, pasty skin and my tiny, pink penis after studying my skinny, nearly hairless body for several moments before she finally spoke. She told me to choose a leather strap to be punished with. She explained that a strap would be the appropriate tool for the poor grade I’d earned on my quiz.

My eyes were blurry with tears when I turned back to the cabinet. Four black leather straps were hanging on the inside of one door. They were arranged in order of length. I figured the longest, widest strap would be the most painful. But the thin, split short strap also looked dangerous. Without thinking too much more about it, I reached up and took one of the middle two. It was as long as my forearm and about as wide as four of my fingers. It was split in half, almost to the handle. I carried the strap across the room and handed it to Aunt Pamela.

She held it on her lap and told me I’d chosen well. She said it was the perfect strap to teach me the lesson I needed. Rising up, she took me to the strange bench. The bench had a padded area for my upper body to rest on. There were padded armrests that sat lower and on either side of the area for my body. In the back, there were rests for my knees and skins. The leg-rests could be spread apart and were already positioned so my knees would be several inches apart. When in position, I’d be in a position on my elbows and knees. There were Velcro straps in various locations on the bench to ensure I couldn’t avoid my punishment.

Aunt Pamela looped her arm around my naked hips while we stood side-by-side, looking at that bench. Between sobs, I asked, “Do you really need to tie me down? I’ll hold still. I promise.”

She pulled me against her large, soft body and reminded me that my punishment was going to hurt. And in her experience, naughty boys could never hold still during a proper thrashing. She went on to tell me being restrained was the last thing I should be worrying about.

With tears rolling down my cheeks, I followed Aunt Pamela’s instructions. I knelt on the bench, and she secured my legs in place with a strap just above my ankle and another just below my knee. Bending forward, she secured the straps above my wrists and below my elbows. Lastly, she wrapped the straps around my thighs, lower back, and just below my armpits. None of the straps were uncomfortably tight. But I was fully aware that I would not be able to avoid that terrifying strap.

When I was adequately secured onto her punishment bench, she knelt down near my face. I was unable to avoid glancing down her dress at her cavernous cleavage. It was the first opportunity I had to do so, and she caught me peeking. As I glanced away and blushed deeply, Aunt Pamela undid the topmost button on her dress, exposing even more of her heavenly cleavage. She laid a finger under my chin and guided my eyes back to her chest. With my innocent eyes fixed on the magical place between her gigantic breasts, she slowly undid the next button, which allowed me to see the sturdy, utilitarian bra she chose to support her ample chest. My little penis became completely erect, and I was transfixed on Aunt Pamela’s magnificent chest.

With a warm smile, she stroked my hair and asked what percentage I got on my quiz. Her question brought me back to reality, and I bit my lip while fighting back the tears. I told her I’d gotten an 84%. She then asked what percentage I should have gotten. I told her no less than 98%. She smiled and told me she wasn’t very good at math, but she believed that it was a 14% difference. She kissed my forehead and told me I’d be getting 14 strokes from her strap, one for each percent. My sobs turned back into all-out-bawling once again, and she hadn’t even struck me yet.

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 drips 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 fourth 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 from 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 outermost 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 little tingling 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 tabletop.

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. Aunt Pamela asked how little it was, but before I could respond, the woman 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 matter-of-factly, “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 the 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, and 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, understanding 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 of 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 as no one else could. She would introduce me to dildos, 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!”

She looked up to see the desperation on my face. I was on the verge of orgasm when she removed her fingertip from my penis. She asked me to make her a promise. Aunt Pamela told me from that moment forward, whenever I masturbated, she wanted me to be naked. And while I played with myself, I was tasked to chant a sentence over and over until I came. “Aunt Pamela is the only woman who will ever love me and my tiny penis.”

At the same moment, I was about to make that promise. She instructed me to practice. She wanted me to masturbate while she watched. I squirmed where I stood and blushed to my very core. Aunt Pamela had done things to me no one else ever had. I had told her things I never thought I’d share with anyone. As I reached around to take hold of my little penis, I felt like crying and giggling at the same time.

I’d never even kissed a girl before, so the idea of playing with myself while Aunt Pamela watched was incredibly shameful. I’d confess that I touched myself shortly after we’d met. But talking about it and doing it were completely separate things.

Aunt Pamela leaned back on the couch and watched as I wrapped my first finger and thumb around my delicate penis. I was unable to look at her. I was so embarrassed. After I’d rubbed myself up and down a few times, she told me to start chanting. My voice cracked with the first word I spoke. But I forced myself to continue.

While stroking my penis in front of someone for the very first time, I whispered, “Aunt Pamela is the only woman who will ever love me and my tiny penis.”

She told me to say it louder. I repeated the sentence in a normal speaking volume. She told me to say it again, to chant it over and over. I stood there masturbating in front of her, and every time I said the sentence, I raised my voice. I eventually found the strength to look at her. She was leaning back against the couch with her legs crossed gracefully and her hands folded on her knee. She had a playful grin on her face and looked very satisfied.

“Aunt Pamela is the only woman who will ever love me and my tiny penis!”

As I approached my orgasm, I felt like I was shouting out the pledge. I moved my free hand beneath the pink head of my penis. I couldn’t imagine letting myself squirt onto her floor. I cupped my hand and prepared to catch my cream.

“Aunt Pamela is the only woman who will ever love me and my tiny penis!!”

When my little balls pulled up inside my body and the familiar wave of tingles shot up my spine, I screamed, “I love you, Aunt Pamela!”

My toes curled, and my knees turned to jelly. Muscles throughout my body began to twitch and spasm. My eyes rolled up, and I stopped breathing until my little penis had dribbled out its first glob of my juice. I kept stroking my penis as it continued to drip out more cream, adding to the small pool in my palm.

When the massive wave of emotions and pleasure had passed with my orgasm, while the humiliation settled in of all that had occurred that day, I forced myself to say it one more time. “Aunt Pamela is the only woman who will ever love me and my tiny penis.”

She smiled while her eyes drifted over my naked body. “Yes, I am, Sweetheart. How could anyone else ever love you with such a tiny, insignificant penis?”

Tears formed in my eyes, and a knot of humiliation grew in my chest while she rose up off the couch and approached me. She gently took hold of my hand with its small pool of cum. While looking right into my eyes, she raised it to her lips and quickly slurped up my cum. She released my hand and moved closer to me. She took my head in her hands and tilted it to the side. I watched as her lips moved closer and closer to my own. When they finally met, her tongue snaked out of her mouth and between my lips. She slowly transferred my cum into my mouth, and I swallowed it almost immediately.

Aunt Pamela continued to kiss me after I’d swallowed my cum. It was the first time I’d ever been kissed. With the taste of cum still on my tongue, I looped my skinny arms up around her neck while my feeling for her increased exponentially. Her hands slid down my naked body until they circled my narrow waist. The kiss eventually ended and left me gasping. I giggled while looking up at her.

She asked me how my first kiss was. And I squirmed and slithered around in her embrace while trying to tell her how wonderful it had been. She kissed me gently on the lips to put an end to my babbling. She then told me as long as I kept visiting her, I’d get many more kisses just like that one.

Aunt Pamela kissed me once more before releasing me from her arms. She informed me that it was time for me to leave. Another of her special boys was due to arrive soon, and she knew how awkward it was for her boys to meet each other.

I hopped around gingerly when she pulled my underpants over my tender bottom. When my khakis were pulled into place, I whimpered and squirmed as they pushed my underpants against my poor bottom. She pulled on my shirt and buttoned it up. We both knew my bottom was very tender, and I would struggle to sit on it for some time. So instead of having me sit on the couch to put my shoes and socks on, she knelt on the floor, and I braced myself against her while she put them on my feet.

She took my hand and guided me to the front door. She reminded me of my promise and of my next appointment time while opening the door. I bit my lip and told her I couldn’t wait until I could see her again. She wrapped her arms around my waist, and mine looped around her neck. She hugged me in a warm embrace for a few seconds before gently kissing me on the lips. She then sent me on my way with a very gentle pat on my bottom.

The End.

 

*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.

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