Gwendolyn - Cover

Gwendolyn

Copyright© 2026 by yfnsp

Chapter 6: Rules are Rules

“Come on, Mike, don’t look so shocked,” Gwendolyn admonished me. “We both know you thrive on my assertiveness,” She grinned and raised an eyebrow. “And you adore how much I love sex! You love to obey me when I am at my horniest. This isn’t any different.”

“It feels different,” I said sullenly. “I can’t stand the idea of someone else having you!”

“You’re thinking of it all wrong. No one’s ‘having’ me.”

I stared at her.

“I’m using them. I’m in control. Always!” She was fierce and magisterial.

It was small comfort. My face must have shown how I felt: bereft. She caressed my cheek again and then leaned in and kissed my on the lips.

“Trust me, Mike. I know best. You know I do. Have I steered you wrong yet?”

She certainly was sure of herself, and I was not. That much I could admit. And I knew that I was not going to stop her from doing whatever she wanted.

“You’ll see. It’s going to be glorious. Anyway, it’s not like it’s already happening. I don’t even have anyone in mind “ She picked up her bag. “I’ve got to go, two classes back to back. Want to meet back at your room at four-thirty?”

“Okay,” I mumbled.

“Good!” she said brightly. “I have a surprise for you.” She kissed me on the lips and walked away.


Gwendolyn was in the room when I got back. She was siting at my desk looking through my postcard collection.

“Darius let me in,” she said by way of explanation. “He was just leaving, going to the gym.”

“Cool. I’m glad you didn’t have to wait in the hall.”

“He said he knew who I was when I introduced myself. So you told him about me?”

I blushed. “I told him I had a girlfriend now.”

She got up and put her arms around me. “Yes, you do!” she said emphatically. She kissed me and groped my rapidly hardening cock.

“He’ll be gone for a least an hour, so we have plenty of time.” She gave my now erect cock a squeeze and stepped back. “I have a new test for you. Are you ready?”

I nodded. “Yes, Gwendolyn.” I was already in worship mode.

“I want you naked. Right now!” she commanded, and she began taking off her clothes too.

We stood facing each other, both of us naked. She grasped my rigid cock and smiled up at me.

“You see? My cock is always here for me. Always ready. Like you. That’s how I know it’s mine.”

She squeezed it gently, proprietorially. I moaned quietly, quite unintentionally. A trickle of precum began to run.

“I want you to lie down on the bed,” she said. She released my cock and licked the precum off her knuckles.

I lay with my head on the pillow and my arms at my side. Gwendolyn got on the bed and sat on my lower legs facing me. She was so beautiful and regal despite the questionable throne. Her naked form was tantalizing. She picked my cock up off my belly where it was leaking precum into my navel.

“For this test, you have to lie perfectly still. No moving. Except your mouth; you are allowed to speak. Okay?”

“Okay,” I said, remembering just in time not to nod my head.

“Now,” she said, stroking my cock very slowly, “you aren’t allowed to cum until I say so, understand?”

“Yes, Gwendolyn,” I said reverently. My arousal was synonymous with worship.

“Good boy,” she said, increasing my euphoria. “So, do you want to cum in my hand?” She continued her slow, gentle strokes. “So I can feed you your cum from my hand?”

“Yes, please, Gwendolyn,” I answered, enchanted. It was a dream. To be milked and fed by Gwendolyn’s divine hand!

“Or,” she pronounced authoritatively, “would you rather cum inside my pussy?” She watched my face, her eyes wide with excitement and mischief.

“What?” I was so surprised that it took a couple of beats before I managed to say, “In your pussy!” I almost forgot, in my excitement, that I was required to lie still. I took a deep breath. “Can I? Can I cum in your pussy?”

“Yes,” she said, sounding a little smug, but oh so sweet, “but you still can’t move and you can’t cum until I tell you.”

“Yes, Gwendolyn,” I said fervently, “I understand. Yes! Please?”

Gwendolyn scootched up my legs on her knees, got herself in position, and lowered herself onto my cock. I watched, observing her physicality with awe. She bit her lip in concentration as she reached for my cock beneath her to line it up. She settled down on it, slipping it easily between her slick lips, hot and snug and deep.

I let out my breath in a long jagged sigh. I didn’t realize I’d been holding it. I had to concentrate to keep from thrusting my pelvis. My arms wanted to envelop her. I wanted to roll her over and pound her cunt with savage thrusts. The urge to fuck her, to possess her, was so strong!

I banished the thought as soon as it occurred, feeling guilty, knowing it would destroy everything. I took a calming breath and focused on Gwendolyn as her pussy pressed into my groin and rocked ever so gently against the root of my cock.

I felt her weight on my thighs. It felt like possession. Remaining passive, I was completely under her control, a tool for her pleasure. And pleasure is what I saw now in her face, the transformation from concentration to bliss.

“Ohhhh,” she sighed, her face lighting up in pleasure, “your cock feels so good inside me!”

I watched her raise herself nearly all the way off my cock and lower herself again, grinding her wetness into my bare pubis. Again, I had to resist thrusting to match her movement, as she repeatedly rode my cock up and down, in and out, grinding, and gyrating, all while her internal muscles clenched and throbbed, massaging my shaft with an exquisite variety of pulses.

My cock was pulsing too, getting too close to the tipping point. I didn’t know which was affecting me more, the magic that Gwendolyn’s pussy was working on my captive cock, or the spell she cast on my fevered brain with the sensuous movements of her lithe body as I watched her pleasure herself, the glow of her perspiration, the slight sway of her firm breasts, and the intense expression of gratification on her radiant face.

I clenched my pelvic muscles to try to keep from cumming.

“Ooh, what are you doing to me?” she panted, “Don’t cum yet! Are you cumming?” She froze, clamping her pussy muscles. I could feel her juices running between my thighs, drenching my balls.

“I’m trying not to!” I cried out desperately. I closed my eyes. I thought about my old dog on the day she died. It worked; It took the edge off. I clenched again, making my cock flex.

“Ohhh,” Gwendolyn was moaning. She leaned forward, grinding her clit back against the root of my cock. She planted her hands on my chest and bucked spasmodically.

“Cum now!” she gasped. “You can cum now...”

I came. I erupted. I felt my balls contract. I felt huge pulses of cum coming in waves, shooting up and out like ballistic missiles. I’m afraid my hips bucked; my butt muscles were clenching; I couldn’t help it.

Gwendolyn came too then. She threw her head back and bore her pussy down hard, achieving maximum penetration, and made the most adorable keening sound, a suppressed wailing scream. And she collapsed on my chest. And I put my arms around her and ran a hand through damp hair.

“Is it okay to move now?” I whispered, raising my head to kiss her forehead, tasting her sweat.

She laughed out loud and stretched forward to meet my lips with hers.

“No, not yet,” she said, pretending with me that I hadn’t already. “I’m not finished with you yet.” She smiled in a way that I had learned meant she had something devious in mind. I thought I knew what it was.

“Okay. You’re the boss,” I said, grinning back at her and placing my arms back at my sides. And I was once again awash in gratitude.

“You are so amazing!” I gushed. “I see what you did. What you did for me.” I started to choke up. “You let me cum in your pussy without breaking the rules.” I gazed into the depths of her eyes. Mine were tearing up. “Thank you, Gwendolyn,” I said with heart-wringing reverence.

“Smart boy!” she beamed. “You were very good, too. You waited, you didn’t cum. I thought you were going to ... Your cock moved inside me, it was so ... Did you do that? because it moved. So you moved.”

Now her expressive face took on her admonishing look. “Did you move?” she asked, her eyes twinkled, though.

“No, Gwendolyn, that only happened because it was so hard not to cum. Please believe me.”

 
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