Adventures with Leslie

Chapter 11 – Cashing In

My Saturday in Seattle with Leslie had been amazing. I had not cum that hard that many times in one session for a while. My marathon sessions with Emma used to be my favorite part of this game. It was nice to get back to that somewhat and Leslie was a filthy little minx, which I loved.

The week dragged on, overshadowed by the thoughts of Saturday's tryst. I had to snap back to reality. I knew I was going to receive a call from Emma at some point. So, it was no surprise when the phone at my desk rang on Thursday afternoon.

"Hello," I answered casually.

"We need to meet about your divorce settlement," Emma stated.

"Of course we do, just say when," I agreed.

"Tomorrow night, 5pm at the office," she detailed.

And then, the routine hang up.

After what felt like a month's time, 4:30pm on Friday arrived. I left work and headed to see Emma. I entered the office suite after my drive over and was delighted, as always to see Penny sitting at her desk. I strolled up and smiled at her, waiting for her to get off the phone.

"Hey there gorgeous," I said to her as she hung up the phone.

"Hey there yourself," she replied. "How was Seattle?"

"Exhausting," I revealed, chuckling to myself.

"It sounded like it," she retorted, making me think she knew more than she was letting on. "Emma is expecting you, go right in."

I hated to leave her but I proceeded into Emma's office and sat down. Emma was reviewing a document in her hand when I arrived. She finished her review and looked up at me. She put down the paper she held and removed her glasses.

"No bullshit, what is important to you," she asked bluntly.

"Important to me how," I inquired.

"Important in this settlement with your soon to be ex-wife," she explained.

"Well, obviously, I would rather not pay alimony and I would love to keep the house," I admitted. "Other than that, I am flexible."

"You may not get both of those," she advised. "I may be able to work a deal for you that gets you one or the other."

"I trust you," I conceded.

"I knew I picked a good one when I chose you," she flattered me.

"You are the angel that rescued me from an ordinary, mundane day-to-day existence and delivered me to a complicated place that makes me feel alive," I professed. "Are you ever going to get back into the game?"

I leaned forward in the chair I was sitting in and awaited her response.

"Never say never," she quipped.

"Em, I am taking off for the weekend," Leslie interrupted as she stepped into Emma's doorway. "Oh, I didn't realize you were here."

She had her briefcase and car keys in her hand and was ready to leave, though she seems startled by my presence.

"We were preparing for next Wednesday's meeting and hearing," Emma informed her. "Have a great weekend."

"You too," Leslie responded. "And you have an assignment tomorrow. Penny has cashed in her win from the poker game. She will call you in the morning with your instructions. What she says goes tomorrow."

"I understand," I confirmed for her.

She headed out without another word. Emma and I sat there staring at each other for several more moments before I stood up.

"I will see you Wednesday," I surmised.

"Yes you will," she replied flatly.

I turned and headed for the door when her voice stopped me.

"As for the game," she declared, "there may come a day when I jump back into it, but that day is not today."

I didn't say a word, I just listened. When she was done speaking I left her office and headed home.

I did my best to have a productive Friday night, not knowing what was to come the following day. I cleaned the house, did laundry and even got to watch an entire ballgame. Sweet.

The ringing of the phone woke me. I had apparently spent the night on the couch and sunlight was now peaking through the blinds on the living room windows. I grabbed the phone.

"Hello," I answered, half awake.

"Rise and shine, boytoy," Penny giggled at me. "It's my day."

"So I heard," I admitted. "What can I do for you?"

"Ok, so here's the deal," she began. "I also cashed in my shopping spree from Jack. I am headed to the mall. I will be at your house at 6pm. I want a candlelight dinner and I want you to wear a suit."

"Ok, consider it done," I assured her. "Anything else?"

"A nice wine," she added. "If you impress me I might have a surprise for you."

I was about to say something when she hung up. They were all so good at that.

I spent the rest of the day preparing. I cleaned the kitchen and dining room thoroughly and set the table nicely. I called and ordered dinner from a nearby restaurant and had them deliver it. I was not about to attempt cooking. I showered and put on my grey suit with a white shirt and blue tie. I looked sharp. Everything was laid out as instructed when Penny arrived. The doorbell rang and I lit the candles on the table.

I answered the door to see Penny, holding 8 or 10 shopping bags. I let her in and kissed her on the cheek.

"I need to go change before dinner," she advised me. "Where is the bedroom?"

"Top of the steps, first door on your left," I told her.

I retreated to the dining room and waiting, ensuring again that everything was perfect. Penny returned from upstairs, now ready for dinner. She had changed and was now wearing a stunning black halter dress that had a long opening between her breasts. The dress was long and made her look incredible. My breath was taken away.

"Wow," was all I could muster in response.

"Just what I was going for," she giggled. "I will have to thank Jack when I see him."

"Dinner is served, my lady," I informed her.

I pulled out her chair and seated her. I poured her a glass of wine and uncovered her dinner, which was already on her plate. I sat across from her and we ate in the candlelight, no television, no radio, just the two of us.

Conversation during dinner was light and easy. It consisted mostly of Penny recapping her poker win over the girls, volleyball win over Jack and her day of shopping. She had a lot of energy. I was enthralled just watching her talk, though I very much wanted to rip her cloths off and take her.

When we were done with dinner, I cleared the table and poured her another glass of wine.

"Would you like desert," I solicited.

"I am desert," she stated. "But not yet. First let's play a game."

"What kind of game did you have in mind," I asked.

"Mall Madness," she informed me.

"I am not sure I know how to play that one," I confessed.

"Then I will explain the rules," she countered. "I will give you a fashion show of some things I bought today at the mall. Every time I come down wearing something new, you have to lose an article of cloths. Does that sound like fun?"

"I think I see the game, but how does one win," I wondered aloud.

"If I still have outfits left when you are nude, I win," she explained. "And if you still have cloths on when I am done, you win."

"Fair enough," I agreed. "What's the prize?"

"The winner gets to decide what we do for the rest of the night," she answered, standing up from the table.

"That's a big prize," I stated. "I'm in.

Penny headed upstairs and I sat on the couch and waited. She had a lot of bags when she came in, I am sure she was confident she would win, but it was worth playing anyway.

She returned first in a nice black suit with a white blouse and black sling back heels. She looked great. She twirled around in front of me and removed my suit jacket, tossing it over the back of the couch. My dick began to stir in my pants. Penny headed back upstairs to continue playing.

When she appeared next she had on a simple white tank top and denim capri pants, with pink sneakers. She looked adorable, but not like the sexpot I was used to. It was a charming offset to her normal sultry side. I watched carefully as she strode across the living room as if on a Paris runway. I removed my tie and tossed it on top of my jacket as she headed back up the stairs.

Penny's next ensemble was a yellow string bikini. I groaned when I saw her. Her body was tight and firm as she crossed the living room in front or me and turned to show me her magnificent bottom. My cock was solid as a rock now. I removed my shirt and tossed onto the accumulating pile to my left. She disappeared again and left me waiting and wanting more.

This time when Penny returned, she had on what can only be described as club wear. She had on a metallic gold backless top with thin straps. My pole throbbed seeing that and almost burst out of my pants when I saw the white pencil miniskirt she was wearing beneath it. I had no doubt she had nothing on underneath it. To compliment it she had on 5 in clear stiletto heels with an open toe. I removed my shoes but did not take my eyes off of her. I knew I was leaking juice into my boxers. Penny retreated upstairs again which gave me a minute to collect myself.

Outfit number 5 was white tank top and tennis skirt set. It was very cute but Penny pushed my buttons by twirling around and causing the skirt to flair out, revealing her uncovered pussy and ass. I pulled off my socks and tossed them aside, running out of items to discard. She was gone again.

Penny reappeared wearing a one piece black halter jumpsuit and the clear stiletto heels. I was in awe of her frame. She walked in front of me and twirled. I stood and removed my pants, adding them to the pile. There was a rather large wet spot on the front of my boxers.

Instead of heading back upstairs to seal her victory in this little game, Penny pushed me back down onto the couch. She sat down on my lap and began grinding her ass cheeks on my crotch. I was gushing precum like a garden hose. She was relentless as she pushed me close to the edge and then retreated. She stood and walked back over to the stairs. She blew me a kiss and disappeared.

I was in agony but delighted at the same time. She didn't take long to reappear. Her game winning outfit was simple, a pink lace tank top, pink lace thong panties, pink thigh high stockings and the clear stiletto heels again. I stood up and discarded my damp boxers. Penny strolled over to me and grabbed my cock with her right hand.

"I win," she said as she started to stroke me.

I covered her hand in clear liquid.

"I guess you get to plan the rest of the night then," I uttered.

"Like that was ever in doubt," she laughed.

"You look amazing," I complimented. "What do you have in mind?"

"Well, I am not really a stockings kind of girl," she revealed. "I only bought these because I knew you would think they were hot and because Jack was paying."

"Both are good reasons," I concurred.

"I want you to ruin them," she disclosed. "I want you to cum all over them."

I spun her around and pushed her down onto the couch. I took one of her legs over each of my shoulders and leaned into her body. I ripped her thong off of her and tossed it to the side. My swollen cock found her hole immediately. I pressed myself into her. She was soaked and ready. I pushed myself into her pussy more firmly each time.

I used the couch for leverage as I attacked her gash with my rod. I rammed my pole into her over and over. I felt her sexy shoes on my shoulders and I leaned my head to the right. I licked her stocking covered foot in her sexy shoe as I plowed her box mercilessly. I implanted my shaft inside until I could not take any more.

I grabbed her ankles and pushed her legs back, bending her in half. I withdrew my cock and blasted off all over her stocking covered thighs. I launched streams of fluid onto her pink thigh highs. I crashed next to her but Penny sat up and began removing her shoes and stockings.

"Thank you," she said, tossing the cum covered stockings aside. "I like my legs bare."

"You are gorgeous either way," I admitted.

"Aw, that's sweet," she toyed with me. "But I'm not in a sweet mood tonight. Take me upstairs."

I stood and scooped her up into my arms. I carried her up the stairs and laid her on my bed. I stood over her and looked down at her outstanding body.

"What kind of mood are you in Penny," I inquired.

"I am in the kind of mood that leaves me satisfied," she growled.

"Just say the word," I pressed.

She flipped over and got on her knees, presenting me her backside.

"Fuck my ass," she ordered.

I reached into the top drawer of the nightstand next to the bed. I extracted a bottle of baby oil that I began distributing on Penny's firm bottom. I rubbed in the oil and pushed a finger into her ass. She had already placed two of her own fingers into her pussy and was working her clit.

I moistened her up before climbing onto the bed and settling in behind her. I pressed my cock to her anus and inserted it slowly. I push in gently until my full girth was swallowed by her bung. I inserted myself over and over into that tight brown hole. My thrusts picked up pace each time and Penny was moaning loudly as I fucked her and she finger-banged her cunt.

"Cum in me," she begged. "Please."

I grabbed her hips and began ramming her with speed and force. My nuts tightened quickly. Penny screamed as she came, three fingers in her box and my swollen rod pressed to the hilt inside her ass. Hearing her scream sent me over the edge. I launched multiple large, gooey spurts into her rectum.

I collapsed next to her as we were both breathing heavy. I pulled her to me and held her tight. I smelled her hair and committed it to memory. She was special among the other women in this game. I didn't quite know why, but she was unique to me.

"Penny," I whispered, "when will the game end?"

"Hopefully never," she wished. "But all good things do end. Just enjoy the ride."

That was the last thing I heard before I drifted off.

I woke to find the sun filling my bedroom and no sign of Penny. There was a note on the pillow next to me that I read.

Leslie's orders said my prize ended at midnight, so I had to go.

The game always kept me guessing.