Chastity Resort Pt. 01

"I love the way you can look so damn cute and hot as hell at the same time. You've got that girl next door look, but with a body that just begs to be fucked." With that, I pulled Anna up and onto me in a quick swoop. She leaned down and we kissed like horny teenagers. My hands moved from her soft curvy hips up the sides of her trim waist and found the rounded swell of her breasts. Anna moaned into my mouth and I knew I had her. My hands moved to the front of her thin tank top and her breasts filled my hands. I massaged them gently, but avoided her nipples. I loved to tease her.

She broke the kiss and leaned back. She cupped the underside of her boobs, lifting them up, and asked "What about these? They could be bigger." She jiggled them a few times and the exposed flesh at the top wobbled like Jell-O. Her nipples were hard and clearly visible through the thin gray material.

"No way. Any bigger and they'd be droopy. They're the perfect handful."

"That's not saying much with the size of your hands..." She smirked and ground her ass against my caged cock. She slid her hands down to her hips and squeezed them. "And my hips...?" She prodded. I loved how her hips widened in this sitting position and the way her thick thighs spread across my stomach. Even with her legs spread, her purple yoga pants were so tight against her pussy I could see the small flower print of her panties through the thin material.

"God, I love your curvy hips. You know I can't keep my hands off them." It was true, I was always wrapping my arm around her when we walked, resting my hand on her hip and my arm across the top of her bubbly ass.

She moved her hands behind her and put on a pouty face. "But I know you think my butt is too big." She feigned a frown.

"Ha-ha, that's funny!" I couldn't believe she had gone there. "You know how perfect I think your ass is. You have just enough muscle from all those squats, but they're hidden under all that soft round bubble butt layer. That's what gives you such an awesome walking booty." She knew exactly what I meant. I had told her many times before how sexy she looked as she walked, her ass cheeks rising and falling rhythmically, even rolling left and right with each step at the top and bottom of their travel because there was just too much meat there to contain. Honestly, the way her ass danced when she walked truly was mesmerizing. I know it probably sounds like I'm describing a fat ass, but hers was a true "phat" ass. It wasn't flabby or out of round. And remarkably, there was zero cellulite dimples. Most women understandably have at least some dimples when their muscles flex, but not Anna. She was blessed with perfectly smooth, unblemished skin not just on her back side, but her whole body.

"Hmm, I'm not sure I believe you." Anna continued to frown as she climbed off my lap and stood by the edge of the bed. She looked back over her shoulder at me and rose up on her toes as she caressed her ample cheeks with her small hands. I knew exactly what she was doing. Her butt was her most sensitive erogenous zone...there was no faster way to turn her on than for me to play with her butt and thighs. I swear she could almost orgasm from an ass massage alone.

I sat up on the edge of the bed and touched a hand to her ass. She backed up toward me, causing her ass to bounce as she parked it just inches from my face. I slowly began caressing a check with each hand. She bent forward and back slightly as I explored her leggings-covered posterior. My hands roamed down the sides of her hips, and up the backs of thighs until they rested in the crease at the base of her glutes. I lifted upward and felt the weight of her round cheeks in my hands as I jiggled them back and forth. My thumbs rested in the inside of her thighs, lightly grazing the lips of her pussy.

Anna moaned with desire. "Oh, Tim, you know how to drive me wild!" She spun around to face me, which put her pussy level with my face. I looked up into her half-closed eyes as I grabbed her ass firmly and pulled her pussy mound right into my lips. She grabbed my hair with both hands and pulled my face tight to her. I breathed in deeply, her sweet intoxicating aura filling my nostrils and making my head spin with lust. I kissed her mound softly, circling around her clit, teasing her. I had to taste her. And she had to be tasted.

She stepped back and turned so her back was to me, hooked her thumbs into the waistband of her tight yoga pants, and shimmied out of them in the sexiest way possible. She was left with a pair of white cotton panties that were probably 2 sizes too small. As she stood up straight again, the panties gathered in the deep crack of her ass, one side disappearing almost entirely and leaving half her ass hanging out. She faced me, slipped her panties to the side, and walked her pussy right into my waiting mouth. All thoughts of teasing aside now, I devoured her pussy. Licking, sucking, smacking, kissing and flicking my way over her sex, I worked from the back to the front to the back again. Anna was writhing against my face, smearing her abounding juices all over my face. I drank her in like a savage. I couldn't get deep enough, fast enough, wet enough. After only 1-2 minutes, her orgasm started. It didn't build slowly and gently; no, it hit like a freight train. Her knees buckled and she fell forward on the bed, trapping my head under her. I licked and sucked ever more fervently, grabbing her panty-clad ass in both hands and pulling her in as tightly as possible. She grunted savagely and ground her pussy against my mouth. After what seemed like an eternity, Anna slowed her movements gradually, shuddering as she came down from the most powerful orgasm she'd ever experienced. She rolled off me and onto the bed, panting heavily, her eyes closed and mouth gaping open. She looked absolutely stunning with post-orgasmic glow.

I knew better than to rush her, but at the same time my cock was throbbing with pain. I looked down at my swollen purple balls and trapped penis. It too was purple and swollen, the head trying to squeeze itself through the pee hole at the end of the tube.

I lay next to Anna and she sighed deeply and smiled. "That was...amazing! I had no idea a person could cum that hard! Your little penis could never have done that"

"Well, I'm glad my mouth is useful to you!" I said with more than a hint of sarcasm.

"Hey! I don't like that tone, little man! I might just never let you cum again! You know better than to talk back to me in bed!" Yes, I did. All too well. For our last anniversary I had treated Anna to an all-day pampering session that led to me pleasuring her for 2+ hours that night. In the morning, I had asked for some relief of my own. She was extremely disappointed in my lack of sacrifice and self-restraint and didn't let me come for 2 weeks.

"I'm so sorry honey! I loved giving you so much pleasure, even if it was only with my mouth. But look at my cock! I haven't cum in a week and I'm busting out of this stupid cage! Please unlock me! I need to cum so badly!!" I slipped to my knees beside the bed between Anna's legs and pleaded with her. "I'm desperate!"

Her gaze softened and she raised herself on her elbows to look at me. "That does look painful. I'm sorry hun, you know how I get carried away sometimes. Give me the key and I'll unlock you."

My face fell in disbelief. "What?!" I cried. "I don't have a key! They said they gave you the key!"

"No, they never gave me the key."

My head dropped onto the bed, and I cried out in frustration, "Nooooooo!" My sexual appetite was through the roof, with no way to relieve it or bring it down.

"There, there baby. I know how frustrated you must feel. I've teased you all week with no release and now you've just eaten me to the best orgasm of my life! You must be ready to explode!" She paused and looked at the clock on the bedside table. "But it's 6:00, and the front desk is closed...we'll go see about getting your key first thing in the morning."

I moaned, dejected and beaten down. I crawled onto the bed between her legs and laid my head at her thighs, inches away from her wet and tired pussy. I breathed in the rich scent of her orgasmic juices, and wondered how I would make it through the night.