I spotted her as I walked inside my local CVS drug store to buy a few things. She was leaning on the counter in front of the register and appeared to be distressed about something or another. What I really noticed was the way her tight faded jeans covered her legs and shapely ass. She had a white blouse with her midriff exposed to show smooth creamy skin. From my view, I saw her shoulder length blonde hair. A well put together specimen of a young lady indeed.

I didn’t give it much more wondered and after I purchased my stuff and walked outside I again saw her sitting on a ledge still looking forlorn. From this angle I could see her face, creamy skin, and pale blue eyes.

I couldn’t help myself and I walked up to her, “Miss, you OK?” She looked up, and gave me a fake smile and lightly said “No, I guess not.”

“What is your name dear?” She told me it was Jen. I asked what the issue was and she went on to tell me that her boyfriend had just broken up with her and had drained all the money from their joint bank user account. She had a rechargeable debit card but she’d just found out she only had about one hundred bucks or so left on it. “I got a job but I don’t get paid again for another two days.” She sighed.

“How old are you Jen?” “I just turned 24” was her reply.

As a middle aged married man with a Dad body, I should not have been thinking the thoughts I was thinking about this young lady. However beauty of her youth combined with the fading of mine caused me to take a shot. I opened my wallet.

“Tell you what, here’s $500, take it and go back in the store and recharge your card.”

Jen looked rather cautiously at me, “Really, I could not do that,” and then a few seconds later she added “Hey, what is the catch.”

“No catch, I just wanted to try to help you out. Here you can have it, no strings attached.” I responded.

The look through those amazing teared-up eyes was a mixture of doubt and hope as she accepted the money. I then added, “But if you want more maybe we can make an arrangement?”

She glared “I’m no hooker!”

“Of course you’re not; I just gave you $500 for no reason. Why would I think you’re a hooker? All I am suggesting is that if you want to spend the afternoon with me, I’ll help you out with another $500.00 at the end of the afternoon.”

I saw a hint of interest in her eyes when she asked “what would I have to do for the extra $500?”

“Simple, go to lunch with me and then spend the rest of the afternoon in a hotel room with me. When were done, I’ll give you another $500 and you can have the room for the night.” I explained.

We both knew her next question was unnecessary. “What do you want to do with me?”

“Jen, you are a lovely young lady, I’m an older married guy with a belly. It would be one of my life’s pleasures to spend the afternoon enjoying how you taste and feel.”

Jen replied, “I’m not sure.”

“Fair enough, tell you what, here is another $20 on top of the $500. If you want to spend the afternoon with me, go reload your debit card and come back out and tell me what you decide. If you decide not to, just walk right past me and I wish you all the luck in the world.”

“”So, what is the extra $20 for?” Jen asked, looking genuinely puzzled.

I explained, “Well if you want to go with me, I want you to use that money to buy a tube of KY gel for me to use on you.”

“Don’t people use that for anal sex?” Jen asked.

“Yes and your ass is so gorgeous I will want to enjoy that too, just letting you know.”

As she walked in the store, I wasn’t sure if I went too far. The view of her perfect little ass swaying in those jeans kept my attention though. About 15 minutes went by and I started to figure she had exited the building by a different door and I was starting to get back in my car. Then, I saw her walk out of the store with a CVS bag in her hand, as she came up to me she said. “I like Olive Garden.”

As we got in my car, she opened the CVs bag to show me a tube of KY Jelly that she had purchased.

I’m not a big fan of Olive Garden but I was that day. I had a light lunch while she feasted on some shrimp pasta dish. She had two glasses of wine to my one and genuinely seemed to be enjoying herself. We talked about our jobs and trivial every day stuff.

As we got back in my car I told her I know of a Hampton In nearby and asked if that were OK.

“Sure” she said while she grinned.

Getting into the room was routine and she walked in before me, when I closed the door behind us, she looked at me and told me she was nervous.

“Jen, you can change your mind and leave and Ill still give you another $500, lunch alone was lovely enough for that.”

She smiled, “can we shower first?”

I undressed first, I was obviously excited and it showed. I’m not huge but not small and she seemed to be Ok with how I looked. As she pulled off her blouse I got to look at her perky breasts in probably what was a C-cup. When the bra came off her sweet nipples pointed out at me. Removing those amazing jeans revealed a red thong. I asked her to turn around so I could gaze that the amazing ass while she peeled off the thong.

She was an absolute specimen. It appeared she kept her pussy waxed and it was perfect. As tasty as her ass looked in the jeans, it looked even more delicious now.

I got in the shower first and adjusted the temperature. I unwrapped the soap and, as she got in the shower, she grabbed the soap and lathered up my cock with it. He petite little hand was stroking back and forth. I pulled her close so that her tits were touching my chest; I placed at finger at her opening and inserted it a bit. I was relieved to feel her moisture already.

We massaged one another with soapy water in the awkward fashion showering people do. She knew how hard I was and I liked her soft whimpers. When I reached about her backside I slid one finger into her inviting asshole. She seemed to enjoy that.

After we got out of the shower and dried off, I pulled down the bed covers and law on my back. “How do you want me?” Jen said.

“Lower your sweet pussy down on my face and take my cock in your mouth baby” I asked.

As amazing as her pussy looked it, the taste of her juices was next level up. As she sat on my tongue and lips, she began to swivel around. Her moaning was light and getting a bit louder. I shifted a bit so I could go back and forth between tonguing her pussy and nibbling on her clit. That sent her to her first orgasm as I felt her juices release around and in my mouth Her sweetness ran down my chin and onto my chest. My tongue was not done yet so I again repositioned myself so I could get access to that Goddess-like asshole. It seemed to set her off again as my tongue hit her rosebud. As amazing as her hole looked, the taste was a heavenly baked mixture of tanginess and sweetness.

After she came a second time, I asked her to turn around and lower herself onto my cock. I hadn’t come in her mouth as I wanted to save my loads for her pussy and asshole.

As she slowly impaled herself on me, it took a bit till I was all the way in. I asked her to hold still for a bit as I didn’t want to erupt too soon. After a bit she began sliding up and down and increased in intensity and speed. Her pussy felt like warm velvet, very wet warm velvet. To my regret, I told her I was close, her response was to go faster and harder until I shot a huge load. Middle aged guys are supposed to shoot like that, but I did.

She rolled off me and lay by my side. Her head was on my chest while I recovered. I rubbed her hair and back as we rubbed by chest. We may have both fallen asleep for a bit, I know I did.

It was maybe 45 minutes to an hour later that I awoke to her taking me in her mouth. I hadn’t cleaned my come or her juices off myself, didn’t seem to matter to her though.

“That is nice Jen.” Is all I could say.

She looked at me, held up the tube of KY, and winked, “we haven’t opened the KY yet.”

In a moment I had her on her tummy with a pillow elevating her hips. “Spread your cheeks, Jen”

As she reached back and spread open her muscular tight butt cheeks, I again placed my tongue on her tight little hole and went at it … for a while.

“You going to fuck my asshole or not?” Jen implored.

Lubing up my middle index finger, I slowed worked it inside her. She said it felt Ok so I followed it with a second, then a third. I was soon rotating all three fingers around her loosening sphincter ring.

“Doing ok Jen?”

“Yea feels kinda Ok, let’s keep going.”

I managed so squirt a large helping of lube into her ass cavity and I generously lathered mine with lube.

“Ready Jen?”

“Yes, get it in there.”

The initial push met some resistance. Her ass was clearly tight, I hadn’t asked her if she’d been ass fucked before, but I thought not.

Soon I was able to open up her sphincter, slid in about an inch and held still.

“Tell me when t move Jen.”

“Just go slow.”

I did go slowly, at first, but as I pistoned back and forth I went deeper and faster. I’d been with a handful of women in my life and did anal with a few, but this was the most glorious feeling me and my dick have ever had.

I know I was close and asked her how she wanted my cum. “Squirt it in me!” Jen cried.

And I did. Boy did I.

Even thought I have filled her pussy about an hour before, I still had a lot to fill her again.

As I would down, my cock softened and eventually slid out of her.

I asked if she were Ok and she smiled and moaned. I got up to shower real quick and when I came out of the bathroom she was asleep on the bed. Still on her belly, still with a pillow under her hips, and I could see me running out of her pussy and asshole.

I quietly took another $500 from my wallet and laid it on the nightstand. I wasn’t gonna leave without saying anything so I gently nudged her awake. I told her she was amazing and to stay the night of she pleased. I told her I somehow hoped out paths would cross again.

Jen looked up at me and said “That was the best ever Daddy, do you think when I give me next month’s allowance we can involve Mom?”

“Sure baby, see you at home later”