Masturbation Month 2024 #26 (Link to Part One)

---

Cynthia got out of the bath, dried off, and went straight over to their toy drawer. She rooted around in the back and found both items she was looking for.

“Yes!” She said to herself and began to formulate her plan. She didn’t have much time. Frank was quick with his clean outs. Tonight, she was going to put him in charge of the ride. Great idea.

Cynthia donned her favorite turquoise bra and panty set and relaxed against the pillows on the bed. She stashed the items from the drawer under one of the pillows. Tonight, she was going to make Frank do all the work. He was right, she felt tired, but that absolutely did not mean his ass was off the hook for tonight. Nor did it mean his cock would be set free. A week was a week, damn it!

When Frank came out of the bathroom he whistled in appreciation. Cynthia looked relaxed and sexy as hell; her cheeks flushed from the bath. She wore that bra that made her girls look so yummy! His cock, once again, started to fill its cage. He laughed at that. You would think that after all these days of not being able to get fully erect in the cage, his cock would stop trying, but clearly that wasn’t in the cards. Not when Cynthia’s breasts were all dressed up for him.

“What’s your pleasure, Ma’am?”

He was curious how his fucking would unfold tonight. Nothing was sure besides a penetration of his ass. She already made that clear.

“First, bring me the paddle.” Cynthia pointed to the toy drawer.

Oh! A little fear shot through Frank. Unexpected. His butt was still sore from his beating the night before, and still sported a few marks. But he did as he was told.

She patted her lap.

“You, here, now.” Surprised at her curt tone, Frank laid across the bed, his ass over her lap.

“So Frank, did you listen to your cock tonight, and try to convince me to let him out?”

His heart sank. This was a punishment! How severe remained to be seen.

“I did Ma’am. I am so sorry. Please forgive me. I remain, of course, ‘down for the whole ride’ as I said before.” There it was. His best effort at verbal atonement.

“You are forgiven. Your punishment will be equal to the number of times your ass is fucked before that cage comes off. Three, on each cheek, my love.”

“Yes, Ma’am.” He grabbed up the bedspread, feeling the need to hang onto something. Cynthia didn’t mess around with punishment strokes. He was grateful she hadn’t asked for the cane.

Cynthia swung the paddle as fierce as the limited positioning of the bed allowed. She delivered 3 strokes on each cheek, and Frank yelped in pain every time the paddle connected. The heart-shaped red marks pleased her. Frank was trying desperately not to squirm, but she knew his ass was on fire. She flipped the paddle over and soothed him with the soft fur.

“Thank you, Ma’am.” He spoke the words softly.

Cynthia gave him a little time to recover before she gave him his next task.

“Go get one of the dining room chairs and bring it in here. And get the purple blanket from the closet.” Frank took a deep breath, got up off Cynthia’s lap and went to fetch the items.

When he returned, she directed him to drape the blanket over the chair. Then she brought out the things she’d secreted under the pillows.

Walking over to the chair, she held up their thigh harness with a dildo already inserted, and he suddenly understood. In short order, she sat with the harness securely fastened around her right thigh. The toy was in the medium range of what his ass could take, but it had lovely curves and an angled head. They’d only used it once. It was one of their newer toys. This looked like fun!

“This time you are in charge of getting your ass ready, Frank. So, take as much time as you need before you have a seat and show me that you really are ‘down for the whole ride’.” There were those words again. “And I would suggest getting the lube, so that ride is a little smoother.” She smiled as he wordlessly nodded his understanding.

Lube retrieved from the bedside drawer, Frank reached around and applied some to his ass. Sure, his cock was still pouting, but his ass was now certainly going to get the railing it craved, because he was in charge of the ride! Eager to sit on that lovely toy, stare at Cynthia’s amazing breasts, and fuck himself, he stepped up to her.

“Goodness, my slutty boy is eager!” Cynthia exclaimed with delight. She wanted to warn him to go slow but decided to trust him and stay silent.

“I am, Ma’am. I am. Now that I told my cock to shut up!” They both laughed.

Frank let himself down on the toy exceedingly slowly. So slowly that his legs trembled a bit with the effort. When the head pushed inside him, he moaned. Cynthia had turned the toy in precisely the right direction, and it pressed up against all the right spots inside his ass. Sinking down on it all the way, Frank finally rested his weight on Cynthia’s leg.

She grinned at him. Frank’s eyes were wide with that look of awe, surprise, and vulnerability he always had when she fucked him. He was positively swooning. This was going to be a good show with Frank in charge of the ride. She kissed him, long and soft, tongues played together, and grabbed his caged cock, giving it a soft tug.

The post Frank is in Charge of the Ride appeared first on Ruby Ryder – Pegging Paradise.

Frank is in Charge of the Ride