Natalie

Natalie is a friend of mine, she's about forty years old, slightly resembles Minka Kelly. She enjoys wearing thin black tank tops that cling to her skin and outline her features like the landscape of the Sahara. It's hard to discern where the body ends and the tank top begins — along with it usually goes a small jacket of sorts and a pair of jeans. Her brown hair reaches the bottom crease of her breasts and her eyes are laced with innocence.

That was just my first encounter with her over Craigslist; she looks the type of person who would be reluctant to enter into such an activity but her texting tone shone with eagerness. She had the deep, raspy voice of a chainsmoker and a black lace choker was around her thin neck as we met outside my car in a Safeway parking lot in the middle of the night.

I drive Natalie over to my apartment — one living space, one bathroom. It was filthy since I hadn't cleaned it for almost a month. I apologized to her for the mess and turned to her once the tour was over.

"Take off your clothes," she instructed.

I quietly obeyed, pulling my shirt over my head and then unbuckling my belt. The jeans came off, and then the boxers. I couldn't hide what popped out; thinking about the next year or so had gotten me hard and my friend down below stood at attention.

"Why's my dick hard already?" Natalie teased. "Are you up for this or not?"

"I am. I just haven't jerked off in a while."

"That's not how chastity works. You start fresh."

"What do you want me to do, go into the bathroom right now and rub one out?"

"No, that's gonna take too long."

"I think I know my dick better than you do."

"Your dick?"

My blood ran cold. "I'm sorry," I apologized. "Your dick."

"That's more like it," Natalie replied with an evil stare, licking her crimson-red lips. I noticed that she wasn't even looking at me anymore. She's was looking at my friend, who was hard and standing at attention. Natalie didn't even make her intentions explicitly known to me before she pushed me over and sent me crashing onto the carpet with a loud thud.

"Stay still," she muttered. "You motherfucker." She slowly got on her knees, fishnet leggings tugging out from under her jean shorts. She unhooked her looped earings slowly, taking her seat damn time. All I could think about — and hope for — was feeling the inside of her hot, wet mouth suckling on my hard cock.

"Getting impatient?" she cooed as she watched my dick twitch from eagerness, pointing right at the ceiling.

"Yeah," I answered, trying to inject some levity into the situation. "He is."

"Shut the fuck up," Natalie snarled.

My blood ran cold again. "I'm sorry."

Natalie breathed onto her fingers, warming them up from the cold air outside. She slowly leaned over me and gently wrapped her smooth, thin fingers around the shaft. I exhaled slowly from the sensation, breath oscillating with the changing pressures of her grasp. She slowly moved her hand up and down, from the base to the neck and back. The veins in my cock became even more engorged.

I leaned back and closed my eyes. I felt her hand changing its angular momentum everything she reached the head, providing some extremely precise pressure applications to the head in a different spot every time. Her hand grew warmer the more she jerked me off, and I felt the organs within my pelvis awake from their several-month slumber. Soon thereafter, when I became used to the sensation and believed once again that I could last some length of time, I felt something coming down on the tip: it was her hot, moist breath — my vessels engorged once again. My eyes remained closed, but I knew that her lips were mere centimeters away from the tip, which excited me even further. I instinctively lifted my pelvis — only to hit nothing. She had obviously retracted her head.

"Don't fucking move, you piece of shit."

"Yes, ma'am."

She continued to jerk me off slowly and surely, until I had reached the point of adaptation once more. Then, I felt the warm breath on the tip again, and I restrained my pelvic bone. I exhaled deeply as her pursed lips, wet from the lipstick, made contact with the tip and slowly rolled over the glans and eventually engulfed the entire head. She didn't go any further but instead pursed her lips a little, taking the head in her mouth and only the head. I didn't feel anymore contact on the tip, until her tongue — somehow pleasurably stiff and comfortably soft at the same time — started dancing on the top of the head with the gentleness of the ballerina and the intensity of a mop. I groaned as she pressed harder with the underside of her tongue and gently caressed the area where the foreskin wasn't. Then, it slowly lifted back up — I took this chance to inhale — and her head moved downward, engulfing the rest of my cock. First, the head rubbed against the roof of her mouth and slid to the back of her throat as her soft, warm lips reached the base. I almost busted right there and then. And I probably would have, had Natalie not immediately retracted. Her gag reflex didn't seem to exist.

"Jesus Christ," I muttered. She seemed amused, letting out a warm breath of air that wafted over the shaft and made my cock ever the more hard. Her tongue came back into action, running itself along the shaft, to the side of the head, and then the same way to the other side. In the middle, she just left her tongue slide underneath my cock and take me further down into her throat. Slowly, she lifted her head back up, letting it slowly out of her mouth, dripping in precum and saliva.

Then as soon as it was out, it was back in again. I moaned as she bobbed up and down on my member, sending tremors through my body and hormones cascading through my brain. After four or five bobs, I was done. Every warm feeling in my body suddenly rushed through my vas deferens and shot out my cock into the back of her throat. I opened my eyes — she was completely naked, her smooth, perky breasts all out for me to see. Her thighbrow softly separated her midriff from her toned thighs. Her lips — puffy and wet-looking — wrapped around cock almost physically pulled the cum out of me. Her beautiful, brown, innocent eyes did the rest of her job, and every time I shot a rope down her throat they seemed to slightly flicker. Fifteen convulses later — she held me in her mouth the entire orgasm — I was empty.

Then, when she figured I was done, Natalie opened her mouth for me to see: it was a pond of milky fluid, something I had donated exclusively for her. The sight of her, her body, her beautiful hair, and her unrelentingly innocent eyes, and her mouthful of cum, everything was just perfect in that one moment. Only one thing made it even more perfect: she swallowed and licked her lips — once shiny crimson, now bright pink. The contraction of her throat as she swallowed — as well as the smile that followed — forced one final rope out of my cock, spraying her breasts unexpectedly.

"The fuck was that for?" she asked.

"I'm sorry," I tried helplessly. "Now, I can put the belt on?"

"Go wash yourself up."

I walked over to the bathroom and quickly rinsed myself off, making sure to clean up whatever fluids had landed on my frontal area and to shave off my pubes. After I was clean, I grabbed a towel and went back to the living room. Natalie was dressed again and was holding the chastity belt in her hand.

"Your cum tastes pretty good," she remarked, perhaps out of guilt for degrading me constantly — even if that was part of our agreement.

"The key is to just eat pineapple," I replied with a smile.

"Shut the fuck up and get over here."