Saturday morning reared its ugly head, flooding me with anxiety, and anticipation on the unknown. Up to this point the oldest female I've ever dated, was a sophomore collage girl, who was my escort to the Senior Prom.

My anxiety wasn't based on fear, but the idea that this was trial and air situation. I looked at profiles of other dudes on the site; they averaged between 22, and 36, so that made me the youngest validated member. It's a good thing, which enticed a lot of Cougars to contact me, but still left me unsure how to interact.

We were heading to Dallas, a few hours to my place then another 3 hour drive to our destination. Dorothy insisted picking me up at my apartment, then driving the reminder of the way. I'm waiting out front, when she pulls up around 5pm very prompt she gets out informing she needs to use the restroom.

This is what I really wanted to avoid, my 1st apartment sparsely furnished with 3rd hand furniture from a second hand store. In my apt. she uses the word "This is Quaint" Then ever so sweetly asked "Is that what you're wearing?" Irritation rear its ugly head, but was able swallowed it down. She was wearing jeans, and a light blue low cut sweater. It showed the wonderful flow of cleavage, but I was expecting a bra-less dress showing lots of flesh; now she was concerned with what I was wearing. The last one to use them terms was mom, so found it a little creepy.

Describing myself honestly I'm 5'9" eating heathy, run and workout with weights, I'm no bodybuilder, but my cuts emphasized with a slender frame. Using a scale of one to ten, I conceder myself around 6, a touch above average.

Dorothy asked if had any jeans that were tighter, then felt my bisects, went into my bedroom to look for a different shirt. Not knowing how to respond just followed her. While I was changing jeans she started digging for shirts, finding 6 she like, saying she'll decide later on which one; after approval of my jeans.

Arriving in Dallas Dorothy pulled into the drive of the Rosewood Mansion, I cringed, my budget being more on the line of Motel6, and started thinking how long was going to be paying on my credit-card. A valet rushed out to open her door, another materialized from thin air, with a cart to ship belongings. Tips? Had a little cash, but now started wondering where an ATM was located.

Once we past the threshold of the hotel, her demeanor changed, it was kind of disarming in a good way. She took me by the arm pressing close, as we walked to the registry desk giving her name, saying we had a reservation. Dorothy signed the required papers, I pulled out my wallet, smiling she kissed my cheek saying "Isn't he so cute" then informing me it was already taken care of. I'll admit did get a little embarrassed.

In the room wanted to have sex right then and there, I believe she knows that, looking at her phone, calmly states after we have dinner, and we'll be late for the party. Dorothy took a small travel case heading into the bathroom, saying over her shoulder "The garment bag holds a few outfits pick the one I like."

Once the door closed, I jumped out of the chair like a kid heading to the tree on Christmas. Inside was 4 dresses, arranged carefully everything included down to panties.

The 1st was a red Swede halter top, with matching long skirt that had a split up the side; nice but...... to much pantie! Next one a pink tube top mini, matching pink thongs, OK but.... On to a dark blue halter mini-dress, short and sweet, completed with lacey G-string panties. This was defiantly what I thought was what Cougars should wear; my dick was hard imaging her in it. I had pretty much made my mind up until saw the last dress; it was something from the promise land. Black short and thin, not what you'd call transparent, but close. I learned later it was called a drape dress, with gathering sides to draw it up. I looked in the bag searching, but didn't find the missing panties.

The door opened Dorothy was wrapped in a towel smiling at my request, later after a little wine, she confessed to manipulating me with panties; so I never really had a choice. Waiting for her return was agonizing! When she next appeared, the sight of her made me think; I could die, and leave a happy man, well almost.

Dorothy's breast had just a little sag, nipples still pointing up, but the way the dress draped over them emphasized their size, the top of her naval was peeking out as she moved. She had drawn the stings up creating a small v on both sides. When she spun for my inspection you could see little flashes of nipple. It was backless save for tiny silver ringlets to keep her ass from being exposed. Jewelry was kept simple, large silver hoops in the ears being accented with her dark auburn hair. Around her neck was this silver wisp of a neckless, with a small delicate pendant in the image of a Cougar paw. Dorothy had bright red lipstick on, her eyes were done it a fashion of Cleopatra asked if "Is your Cougar slutty enough" Then her actions distressed me again.

Walking up to me, she pressed her fingers against me, slowly unbuttoning my shirt to the waist, untucking the tails from my jeans. Her hand lingered on my chest, with a small sigh, just up and stopped wanting me to let her see which shirt she wanted. She encouraged me to wear the blue muscle shirt.

I'm now living the dream; events become surreal like I'm participating in a movie watching each frame unfold. Dorothy seemed to make a radical metamorphosis, into this woman completely different woman I met in the coffee shop. Her voice took on a husky quality, over laid by that sugary sound.

In the restaurant everyone stared as we walked hand in hand, when I pulled her chair out, I'll admit my fingers lingered a bit too long on her bare back, which she seemed not to mind. She ordered wine for herself and a coke for me, then looked me over the rim with Egyptian styled eyes. Every now and a breast would fall free, and Dorothy without haste confined it once more. At one point during the meal, she slipped her shoe off tracing my dick with her toe. I almost choked on the food being chewing.

Dorothy talked about the couples around us, who was getting some, and naturally who wasn't. She continued that most men in here uses the little blue pill, that's why most the women are staring, and many of the men wish their wives tits would pop out now and then.

One thing I owe to mom is; she instilled me with gentlemanly etiquette. When Dorothy informed me she needs to powder her nose, it cloaked me in a state of conflict, being aroused. She sat calmly waiting knowing eventually I'd rise out of the chair with great embarrassment to help her up. She looked at my crotch, in that husky voice said "Someone's excited" making matters worse, gave me and the table next to us a pussy shot. Hurrying back to my seat watched her move to the restroom not a care in the world. The thing that struck me most was watching the peoples following her movement, a few men receiving frosty stares from their companions. What surprised me the most is, I received a few nots of approval.

Leaving the restaurant, eyes burning into my back, she whispered "You drive"