That night Ivan carried me to Kay's Dermatology. I gave him an envelope with a thousand dollars cash. I said, "Here, this is to help you and Kiko with expenses. She called me about the poker party. I appreciate this, and I don't want to be a freeloader on you two. At least where money is involved. Please make sure she takes what she needs for expenses and let me know when you need more."
"Thank you, ma'am."
"I am going to get a cooking lesson this week also. I am taking your rules to heart. My rules at work, your rules at your place."
"Yes ma'am."
It took the dermatologist a lot longer than I thought to do the first of several treatments to remove body hair. The dermatologist assured me that in a week I would be healed, and each would be easier and take less time. She gave me a cream to apply for the week and told me to leave the area alone, including staying out of the sun for a week. She wanted me to come back the next week if it wasn't as smooth as the rest of me by then. The dermatologist had stayed late for me, spent a lot of time and I gave her a huge tip.
When I got into the car, Ivan asked, "How did it go?"
"I think good. I will know for sure in a week."
"Did it hurt much?"
"Not compared to other things I have done. Thanks for asking, Ivan."
Ivan smiled at me in the mirror and nodded.
The next day at lunch I got a prescription for clear light blue contacts from an optometrist. He said they could be picked up on Friday.
Later that week, Sally and I had lunch together. I told her about my past weekend with Ivan and Kiko and my upcoming adventure.
She said, "I must admit I am envious. It sounds like you are beginning to enjoy your life."
"I really am. I'm not looking for anything permanent. I just want to have fun. Speaking of that I want to find out something."
Sally smiled, "Anything I can help you with."
"How did you take Henry in your ass like that? Doesn't it hurt?"
Sally smiled, "It does initially but with some practice it makes for intense experiences. The key is not to fight it. Just let it happen. You need to get your asshole accustomed to having something in it. Once you get used to it, a man's penis shoved in feels really nice. For me it intensifies my orgasms. There is also a feeling that you are doing something special for your man or men."
"Really! How do you get used to it?"
"Go get varying sized anal plugs and put them in periodically. Make sure you use lots of lube. Start small and work up. Some women like them even if they aren't going to have a man do it. Try using one when you masturbate. You will find that you can program yourself to have orgasms with something in your ass."
"So, you really enjoy it?"
"I do. Henry and I mix it in as a curve from normal sex. Whatever that is."
Sally and I were becoming really good friends. I felt like we could discuss anything. It also seemed to me that she was getting more comfortable letting me in on the most intimate parts of her life. I had never had a friend like this and I liked it very much. I felt good to be a part of her life and discussing my feelings. I realized I had been keeping them submerged for most if not all of my life. It felt good to open up with Sally.
As Ivan drove me home Friday night, Ivan gave me a package from Kiko. When I got home I opened it. There was a note from Kiko, "See how you like this. I just wanted you to have an idea what I thought a hard-up cougar would wear. Up to you, you may find something you like better. See you next Saturday. Can't wait."
I laid out the outfit. There were three pieces. Panties, well very little bity panties, bra and what looked like a long pink tee shirt. I got naked, looked in the mirror. My pussy was healing nicely. Most of the redness was gone and, in its place was nice smooth white skin. If you looked closely you could still see little bumps and a dark shadow. I had a feeling with each treatment, there would be less dark shadow. I spread my legs and for the first time really saw what my pussy looked like. It was fat, with protruding labia. It looked like it could take a tree trunk. It was almost the opposite of Kiko that had no folds just a small thin slit that was all white with a thin line in it.
I decided that maybe some men would like this. I put on the panties. I guess you would call it a thong as it barely covered my labia, my fat pussy oozed out either side of the gusset and slipped in the crack of my ass. It felt funny. This would take some getting used to. I had always worn full sized panties. Then the bra. It had black translucent cups that barely covered the bottom half of my breasts with a black lace strip that ran just above my areolas and attached to thin black lace straps. There was a seam providing a little extra support. But my big puffy pink areolas were clearly visible, and my nubs were barely contained.
Then the dress or tee shirt. It fit very tight, I could barely get into it. The short-sleeved top just covered the bra straps and cup, leaving a lot of breasts showing. It was very tight across my broad hips. I was sure that Kiko had guessed the size incorrectly. If I pulled it down it hit me mid-thigh but any movement the tight skirt rode up.
I texted Kiko:
Me: 'Thanks for outfit but the dress is very tight.'
Kiko: 'That is the way cougar wear it.'
Me: 'Really. Okay.'
I try out the cougar outfit
On Saturday, I worked at the office then went shopping. I rarely shop. Usually I had other people shop for me. I bought a blonde wig. I wore it to an adult store and bought a package of three anal plugs and lube. I then went to the mall, again something I rarely did. I decided the average cougar wouldn't shop at my normal stores. I bought a couple of outfits I thought looked good on me and would pass as a cougar outfit.
After I had dinner at home, I tried on my new outfit. I wore a red bra that wrapped around the waist and pushed my breasts up and in. The red dress plunged in back to my waist and had a deep V in front that didn't cover the red bra when I sat down. The jagged hemline hit just above mid-thigh. I also put on a pair of thigh-high stockings, whose top was visible at the hem and a pair of red high heels.
I then put in the blue contacts and the blonde wig. Looking in the mirror, I thought this was how a cougar would look. I wondered how the boys next week would like it. Then like any good technologist, I decided I needed a trial run. I promised Proctor not to do the thing I had done with Mort. And I couldn't because my dermatologist told me to leave my pussy alone until Tuesday. So, I decided to go to a bar and see if someone would try to pick me up, but I wouldn't leave the bar with them. Remember my goal was to test the new outfit.
I went to an upscale hotel bar down town. I thought this would be safe. I got there a little after eight. I sat on a stool at the bar. The bartender served me a glass of wine. He then asked, "Are you looking for some action?"
I took this as a good sign that my cougar outfit was authentic looking. "Not right now. Thanks for asking."
I sat at the bar for about fifteen minutes when the first guy approached me. He said, "Hey beautiful. Want some company?"
I didn't like his looks. There was something that made me uneasy. I said, "No thanks, I am waiting for someone."
He said, "Well, screw you. I was willing to pay you good money."
I took this again as a good sign but wanted nothing to do with this guy. I flipped into Mercedes mode, "Get away from me! You have made a mistake."
He walked away without saying anything else.
I sat for another fifteen minutes, had almost finished my glass of wine. I decided that I would call it a night with enough evidence that my outfit was right. Just as I finished the last swallow I heard, "Are you waiting for someone? If you aren't I could really use some company."
The man was about my height and age and had a very pleasant face. He wasn't handsome, bald and a little heavy, but he looked like a sweet guy who did need some company.
I gave him my now much more practiced pleasant smile. "I'm not waiting on anyone and would love some company."
He smiled back and said, "Can I buy you another glass of wine?"
"That sounds good." The bartender was listening and placed the wine on the bar. He said, "It might be easier to talk at a table."
"Okay."
