Traffic Girl - Jess Ch. 05

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.

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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.

"Rita, you stretch before you play tennis, right?" I said. Now was the time. I held my cock just behind her asshole, gripping it just behind the head.

"I do," she said, looking over her shoulder.

"And when you're stretching, you can get deeper into the stretch when you exhale?" I continued.

"That's right," she said.

"So what we're going to do is control your breathing like when you stretch before tennis, okay?" I said.

"Okay," she said.

"I'm going to put in just the tip of my cock first," I said. "But before I do? I want you to take three or four deep breaths. Just like you would while stretching or doing yoga."

"Okay," she said and complied. She took one deep breath, then another. I liberally applied lube to her ass and my cock.

"When you exhale this time, I'm going to push in," I said.

She inhaled substantially. I saw her rib cage contract and pushed the head of my cock past her sphincter. She let out a long, low moan.

"How does that feel?" I asked.

"Better than I thought," she said.

"Good," I said. "Keep breathing like that. I'm going to give you a minute to get used to my cock. But then I'll start pushing in deeper when you exhale."

"I want it," she said.

On each exhale for the next couple minutes, I slowly pushed my cock deeper into her asshole. It gripped me like a vise.

"Holy fuck, I feel so full," Rita gasped.

"I'm all the way in, baby," I said.

"Jesus, I've never felt so full in my life," she said.

"Does it feel okay?" I asked.

"No pain," she said, breathing heavily. "This feels good in a really weird way."

"I'm going to add a little more lube and start fucking you, all right?" I said.

She grunted her assent. I pulled my cock halfway out, slowly, and poured lube onto it before moving it back in. The strokes were long and extremely slow at first, but Rita was very good at focusing on her breathing. I sensed no indications she was in pain. So I picked up my pace gradually.

"Oh my god," she moaned. "Fuck. Fuck yes. Goddamn, I can't believe you're in my ass."

"I told you I'd fuck your ass," I said cockily. "You're my anal slut now."

She started rubbing her clit furiously, and I took that as an invitation to fuck her faster. The friction was exquisite. I marveled at how tightly her anus gripped my cock. It was hypnotic to watch. I couldn't believe my good fortune. I was fucking her ass hard now, pushing my full length as far inside her as I could. Rita was screaming in pleasure. Juice dripped down her thighs as she finger-fucked herself while I pistoned in and out of her ass.

"Oh fuck! Holy fuck! I'm going to fucking cum! I'm going to cum!" Rita screamed.

Her asshole squeezed tightly, but I kept up my strokes. I watched her legs quiver as the orgasm took over her entire body. The intensity of the situation caught up with me. I couldn't wait to fill her ass with cum.

"Oh god! Oh god!" she moaned. "That was so intense. So intense!"

Her legs buckled slightly, and I pushed her ass down on the bed. I readjusted and continued to fuck her ass in lazy doggy style. My load was boiling up in my balls.

"I'm going to fill your sweet ass now," I growled.

"Please," she begged. "Please give me that cum."

I unloaded. It was a powerful, full-body orgasm. It felt like her ass was milking the sperm out of me. The ropes shot deep in her bowels, and she let out a moan that sounded almost like a laugh.

"Oh fuck, I can feel it!" she said.

I was spent. It was an exhausting and intense fuck. And an absolutely brilliant one.

"Okay, baby," I said. "Now let's practice that breathing one more time. I don't want it to hurt when I pull out."

She calmed her breath and, on a long exhale, I took my cock out of her ass. I lay down next to her. Her eyes flickered brightly. We kissed.

"I didn't expect that," Rita said. "That was... I'm at a loss for words. It was amazing."

I put my hand under her chin. I kissed her again.

"You are a phenomenal student," I said.

"I don't think I've ever cum that hard," she said. "Seriously. That was so intense. Incredible."

"Thanks for trusting me," I said.

"You should thank Kat for convincing me," she said. "It was really her pushing me that made me curious to want to actually try it."

"We haven't talked in a while," I said.

"Give her some time," she said. She rolled onto her back and stretched. "Oh god. I'm just realizing right now that wearing a skirt with no panties here maybe was not the smartest idea. I'm going to leave a trail of cum behind me."

I sucked on one of her nipples and smiled. "It's a shame you can't go home to your husband with my cum leaking out of your ass like that," I said.

"You like being a dirty boy, don't you?" she said playfully.

I continued playing with her tits. "You have no idea," I said. "And I think I can help you from leaving a pool of cum wherever you go."

I retrieved her butt plug and showed it to her. I flashed her a wicked smile.

"I'm going to plug you again," I said. "And you can keep my cum inside you as long as you want."

"That's so kinky," she said.

"Do you want to grab a shower?" I said, finally getting up off the bed.

"I actually need to get going," Rita said. "Kat knew I was coming over, and she wanted to meet for a drink as soon as we finished so I could tell her the details."

My heart started thumping.

"Speaking of kinky," I said.

Rita smiled. "Like I said," she said, "she misses you." She had put her dress back on.

"Make sure she knows you're wearing the butt plug," I said. "She always loved it when I would plug her after I came in her ass."

"I can feel your cum in there," she said. "It's such a strange feeling."

I kissed her and said, "You'll get used to it. Say hi to Kat for me?"

"I'll tell her that you miss her, too," Rita said. She smiled and waltzed out the door.