Chapter 5

Author’s Note: Thanks for your patience with me being a bit off schedule for updates. Things are almost back to normal! Appreciate the feedback, votes, and criticism.

Over the ensuing weeks, Jess settled into a pattern of seeing Jonathan Summers, her hedge fund sugar daddy, twice a week. He was surprisingly loose-lipped with her about his business plans, and I began to make use of that for my own ends. My bank had wanted to facilitate one of his offerings for years, but he was loyal to a local outfit. Jess had provided me enough details that I felt increasingly confident that I could predict one of his next moves, which happened to target a client of mine. Summers might well be playing right into my hands, and if I handled it right, I could be looking at mega money.

That was all well and good, exciting in its own right, but it was nothing compared to the electric shock being sent through my cock at that moment. There was a mane of blonde hair draped over my thighs, covering the eager mouth of Rita Johnson as she gave me a sloppy, desperate blow job.

Jess was at Summers’s house for one of their weekly trysts, which still came at a lucrative $2,000 per meeting, and I was tickled when Rita texted me out of the blue to say her husband was out of town, and she needed some fun. It had been months since I’d seen her. She had almost tackled me onto the couch when I greeted her at the door, immediately begging to give me head.

“Well, it’s good to see you, too, Rita,” I said as she slobbered on my cock. The white t-shirt dress she wore rode up her thighs. Her legs, shapely from her frequent tennis matches, had a golden hue from the sun.

She pulled back and attacked my face with an aggressive kiss. I’d never seen her in such need.

“I don’t know why, but something came over me a couple weeks ago,” she said.

I returned her kisses with equal fervor. “What’s that?” I asked. My hands roamed, inevitably starting with her perfect tits, which were as firm and supple as ever.

“You’ll see,” she said. Her hand took a firm hold of my still-exposed cock. Meanwhile, my own fingers had found their way under her dress, and her thighs and pussy were a sticky mess.

“Whatever it is,” I said, “you’re leaking like a faucet.”

“Kat and I had lunch recently,” Rita said. She inserted my cock into her pussy and adjusted her thighs around mine. “She misses you.”

“I miss her, too,” I said, luxuriating in the velvety folds of Houston’s favorite weather girl.

Rita rode me slowly and kissed my neck. “She told me that she still obeys your rule that you’re the only man allowed inside her ass,” she whispered.

“I’m flattered,” I said, a bit disarmed.

“And, like girls do, we got to talking,” she continued. “I was so curious about why she loves anal sex so much. She was describing it to me, specifically why you were the best anal lover she had ever had. I confess, it made me curious.”

My eyes grew wide as I began to understand where this might be going.

“So Kat gave me some tips,” she said. “And she told me how to work up to it by playing with myself and using toys.”

My cock was achingly hard, and I felt an embarrassingly early orgasm starting to tremor within me.

Rita stopped her rhythmic movements, perhaps sensing I was too close. She put her nose near mine and looked me dead in the eyes.

“Kat told me exactly how to prepare,” she said. “For the last two weeks, I’ve been working up to it and practicing and hoping I wouldn’t chicken out at the ultimate moment.”

I arched my eyebrows but grinned at the same time.

Rita stood up, turned around, and gathered up her skirt as she bent over. A pink, heart-shaped butt plug was lodged in her ass. She looked over her shoulder at me with a wicked smile.

“Of course, you know pink is my favorite color,” she said.

I took a deep breath. “You’ve come a long way,” I said.

“Kat taught me how to work up from smaller to bigger plugs,” she said. “She told me how you helped train her breathing to make the penetration easier.” Her eyes were shimmering. “Now I only have one last test left.”

“And I’m the lucky boy who gets to christen your ass?” I said.

“Something like that,” she said flirtatiously.

I threw myself into the task with unbridled enthusiasm. We moved to the bedroom, where I sorted through a variety of sex toys in the night stand to fish out some lube and took control of the situation with Rita. She had taken off her dress and lay gorgeously vulnerable across my bed.

“Do you want some coke to maybe numb yourself a little?” I asked.

She shook her head. “No,” she said. “I want the real experience.”

“Get on your hands and knees,” I ordered, motioning her to the edge of the bed. She did as she was told.

I knelt before her, ass proudly in the air. I licked her pussy gently, then slowly rotated the butt plug out of her ass. Her rosebud was so obviously tight, it made my cock pulse. I began licking her asshole. She had prepared. I could taste the slightly bitter and floral body wash she had used.

“Fuck it feels so good when you do that,” she groaned. “My husband won’t rim me at all.”

“He’s missing out,” I said tersely and got back to work.

I worked her ass with my tongue for a few more minutes, before introducing a finger. This was all a practiced progression. I started with one finger, moving it around liberally, allowing her anus to get familiar with motion and different areas of exploration. I ate her pussy while I did so, then added a second finger in her ass. She moaned and pushed back against me. The training with the butt plug had helped put her at ease with some anal exploration. The real test was approaching soon.

“Are you ready?” I asked, cupping her ass cheeks in each hand.

She took a deep breath. “Let’s do this,” she said.

My cock was throbbing. It had been years since I had taken a virgin ass. I took a mental picture and savored the moment. No one had been in this ass before. Not her husband. How many of her 178,000 Instagram followers had fantasized about doing this very thing? I smiled. This was a privilege.