Aunt Pamela and Leslie Ch. 03

Moving to my dresser, she opened the top drawer and pulled out a clean pair of briefs. Turning to face me, she held them on the tip of her finger. "I do hope Gam-Gam sends you panties." She then turned back to the drawer and dropped the underpants from her finger as if they were filthy.

After rifling through all my belongings, Aunt Pamela moved my desk chair so it sat near my bed. "Leslie, do you still want to play with yourself?"

Biting my lip, I looked up into her warm, brown eyes. "Yes. Is that okay?"

She grinned, "Of course it is, Honey. Why don't you lay back on your bed and show me how you masturbate?"

Aunt Pamela had seen me naked. She'd punished my naked body and even made me squirt. She'd even watched me go pee into a crystal pitcher and lick up my mess. But playing with myself while she watched was somehow taboo. It was a thing I did privately. Having her witness that act sent a shameful shiver radiating through my body.

But I wasn't about to disappoint her. Moving the small towel with me as I scooted back on my bed so I laid with my head on my pillow. Settling down on my bottom, which was still tender, I then spread my legs and bent my knees. My hands slid over my naked and highly aroused body while Aunt Pamela moved her chair to the very edge of my bed. She sat there and we stared into each other's eyes while I touched my body.

After my goosebumps had risen and fallen and my body was left covered with a thin layer of perspiration, I let my hand make its way down to my rigid penis. Taking the pink spike between my first finger and thumb, just below the squishy head, I began to slowly and gently run up and down.

We broke eye contact when my eyes dipped to admire her mountainous chest and her eyes wandered down over my naked body. She asked in a soft whisper, "Did Mom teach you to touch yourself like this?"

My back arched and thoughts of my Mom filled my mind. I squeaked, "No. It's just how I've always done it. Am I doing it wrong?"

She gazed down upon my flushed body and answered, "No, you're doing it perfectly. I thought your Mom or Gam-Gam may have taught you how to touch yourself. You're so gentle with it." Her chest heaved before she finished her thought, "That is exactly how I would have taught you how to touch yourself."

Hearing her approval made me feel proud. My back arched and my penis throbbed beneath my fingertips. Aunt Pamela's eyes drifted back up my body and until our eyes met once again. Aunt Pamela had kept her hands folded in her lap up until that point. Very casually, she slipped one hand below my bent leg and gently pressed on the base of the plug buried in my bottom. I squealed and clenched my cheeks, pulling the plug even deeper inside of my body.

I whimpered, "Aunt Pamela! It feels so wonderful!"

She smiled down at me while working her touch against the plug into a rhythm. She began to match the pressure she applied to the plug with the stroking of my penis. My vision got a little pink and cloudy. I'd never felt anything quite as magical as that. If I didn't know better, I would have thought I was floating.

As I neared my orgasm, she whispered softly, "Sweetheart, I earlier asked you to text me before you played with yourself. I also said you weren't asking permission. I said you were simply telling me what you planned to do."

Staring into her eyes, I squeaked, "Yes! I know!"

She grinned and went on to say, "Well, I've changed my mind. I want you to call me instead and you will be asking my permission to masturbate. Do you know what that means, Honey?"

Biting my lip and squirming on my bed, I whimpered, "It-It means you can say no."

She smiled, "That's right. And if I'm unable to answer the phone for any reason, you'll have to wait. You'll need to hear me give you permission before you play. Do you understand?"

My back arched deeply and my little balls pulled up into my body. My skinny, pink penis throbbed hard and I squeaked, "Yes! Yes! I understand! I promise! I promise I'll call and get your permission before I touch myself!"

She continued to press the plug in and out of my bottom in time with my stroking. The pressure was quickly building inside of me. Aunt Pamela looked perfectly happy while watching me quickly approach my orgasm. I struggled to maintain eye contact with her as the pleasure mounted inside of my body. In a soft whisper, she said, "It's okay Sweetheart, squirt for me. Squirt for Mom. Squirt for Gam-Gam."

In a louder voice than I would've like to use, I squealed, "My Mom..."

My penis throbbed hard and squirted out a long line of my creamy love onto my stomach.

I then squealed in that same loud tone, "My Gam-Gam..."

My penis squirted out the second line of its love. It wasn't as long as the first, but it felt even more intense than the first.

Squealing once more, "And my Aunt Pamela..."

The last line of creamy goodness didn't squirt out with as much power as the first two, but it was big and left a pool on my stomach. I then squeezed out the last drops while whimpered, "Are the only women who will ever love me and my tiny penis."

Without wasting a moment, Aunt Pamela had me pull my knees back toward my chest. While still not fully recovered from that most intense of orgasms, she took hold of the plug's base. Working slowly and patiently, she began to work the plug out of my body. Without looking away from the plug and my still stiff penis, she asked, "Who do you love?"

I held my knees tightly against my chest and whimpered, "I love you. And I love Mom. And I love Gam-Gam."

In and out, in and out, a little bit at a time until my wrinkled hole was stretched taut around the widest part of the plug. From there, my body pushed it out all on its own. Holding the plug by its base, she rose up from the chair and left for my bathroom. I let my legs fall onto the bed and flinched when my tender bottom rubbed against the towel. I laid there and took some time to recover from all that had happened.

Aunt Pamela cleaned the plug that had been buried in my bottom. When she returned, she set the plug down near the pictures of my Mom and Gam-Gam. I rose up off my bed and found my legs were very rubbery. I giggled while giving myself a chance to regain my balance. Aunt Pamela crossed my room and took me in her arms.

While embracing me, she whispered, "Leslie, Honey, I should be going. You need to rest this weekend and give your bottom time to heal."

I snuggled my face against her blouse, into her cleavage. I whispered, "Do you have to go?"

She squeezed me tight. "Yes, I do have to go. But I'll see you on Tuesday. Between now and then, I'm going to check your schedule. We need to start seeing each other must more often. How would you feel about visiting me Monday, Wednesday and Friday?"

Pressing my face even deeper into her cleavage, I said, "I'd love that. Actually, I wish I could visit you every day, even the weekends."

She rubbed my naked back with her large, warm palm. In a playful tone she said, "Well if you show up on my doorstep wearing a dress, that wish may come true."