Jan's Evolution Ch. 05

I can barely contain myself. My life is changing and moving so fast. It's not that I'm overwhelmed with a job or heavy responsibilities. It's just that I've made decisions that involve taking risks, making commitments, and going in directions that are beyond where I've been before. Yes, I've flirted with the edge and I've done things that I had never dreamed of doing in my past life. Now some of those elements have become my new norm, and I'm feeling the urge to push the envelope even further.

I was a bored and unhappy mom for almost two decades. Married to a doctor and raising two sons, it was a seemingly idyllic life. But the doctor was cheating on me and the boys knew it, as much as we all tried to ignore it. Finally it was too much to bear any longer. I filed for divorce and began the year long process of ending one life and beginning a new one. A new life that was here to for unknown. Alone and desperate I reached out to my estranged younger brother. That proved to be the catalyst that changed everything. He came to Cleveland with his long time best girlfriend Sue, at his wife Trish's urging, and literally changed my life as they rescued me and encouraged me to move to Arizona where they lived.

They taught me to be open to new options and experiences. Much of which involved a sexual transition. I moved beyond my conservative strict traditional morals. I allowed myself to experience and enjoy pleasures that I always thought were limited to pornographic films and fantasies. My brother Rob and his wife are nudists, and while they are totally in love and dedicated to each other, they have a marriage that is open, in that they enjoy sex with other people, including Trish's daughters and a circle of close friends. And they allow themselves to include new partners if and when they feel it's appropriate.

They are beautiful people in so many ways. Rob is handsome and fit and comfortably wealthy. Trish is a living doll. She makes heads turn where ever she goes. But it's their loving hearts that make their beauty shine brightest. I've never heard a cross or angry word from either of them, and that extends to the people they meet and encounter. Once you meet them you just want to stay around them. And I'm so blessed that they have welcomed me as an integral part of their family and I now live in their home. I have my private bedroom and luxuriously appointed bathroom, and we share the rest of the house, including live in help. Trish and I have become best friends. She has a small business as a hair stylist. She doesn't need to work, but she enjoys the interaction with her clients and they appreciate her services. But when she's not working, we spend most of our time together socially. It might be at home living a most relaxing life in their large well planned and designed home, or out and about in the natural beauty of Sedona.

Trish has two adult daughters, Tracy and Teri, who are both very successful in their chosen business endeavors. The sexual openness has always included her girls. As a result, they mirror the love and the warmth that Trish has taught them all of their lives. It's not so much incestuous as it is simply loving and caring for each other in ways that go beyond traditional norms.

I have two adult sons, just a few years younger than their cousins. They chose to follow me to Arizona and have both acclimated and found success on their own. They live locally and close enough that they can visit when they have the time. Initially they were naturally shy about accepting the open lifestyle that I've embraced, but gradually they've at least accepted that it's my choice and it keeps me happy. I've been envious of Trish and the relationship she has with Tracy and Teri, but I recognized that it's unique and just not for everybody.

However, that has recently changed in big ways. Thanks to Tracy, she convinced my younger son Andrew to participate in a sexual encounter with me, his mother. It happened in the presence of the entire family. He was reluctant as one might expect, but after it happened he realized that it was exciting and pleasing and something that he wanted to do again, and again and... We've become lovers but with a bit of a twist. Obviously I'm 20 years older than he is, so when we are out together we attract attention as a bit of an oddity. We complicate it by being open in the ways we interact and demonstrate our love for each other. Public displays of affection happen constantly, and he refers to me as his Cougar. The title thrills me to no end. Because I am. I'm in my forties but I've kept my figure and I believe I'm attractive enough to pass for ten years less than the reality of my age. Andrew reaffirms that for me whenever we are together. I have more sexual experiences than he does, but his youth and stamina make up for any shortcomings that might exist. And he's not afraid to try anything now that he understands my willingness to be open as well. As my relations with Andrew evolved, it was only natural that I longed for a similar relationship with my older son Billy. He's a successful restauranteur and a hard worker. Like Andrew he was shy and reluctant at first. But when I made my intentions known he became more open and accepting and embraced me as his MILF. Like the cougar designation, I took MILF as a huge compliment and together we have developed a deeper love and an openness to taking it further. We all try to be discreet in our hometown, but if we get away, even just to another nearby town, we freely demonstrate our love for each other.

As part of these radical changes I've been going through, getting away has become a little easier. Billy and Andrew both ride Harley Davidson motorcycles as their primary transportation and also for sport and pleasure. I love to ride, though I pretty much gave it up to raise my family. But recently I've caught the bug again, and I made the leap and bought a Harley for myself. It's introduced a whole new dynamic in our lives and even allowed me to take more risks and become a person I never was before. And I'm loving it.

Investing in the Harley and related gear and accessories was an experience in itself. My sales person proved to be a pretty and affable woman, about my age; and on the day of delivery, we actually expanded the relationship with a most enjoyable sexual encounter. We promised to become riding partners when our schedules permitted, and our first big ride is coming up this weekend. Wanda will arrive at my home in Sedona on Saturday evening and we will ride on Sunday and Monday.

I plan for us to spend a night at a casino resort in Prescott so I had to shop for a dress. We don't have big box or department stores here. We have smaller boutique style vendors. Typically forward thinking though limited by space, budget and market to more unique, often hand made or specialty products. I have a place I've found that often has fun and sexy evening wear. Dressing up in Sedona is limited to polishing your boots. Anyway, I headed there on a mission. I need an evening outfit that I can pack in the saddlebag on my Harley. For over 20 years I've packed in a full set of Louis Vuitton luggage. Sizing down is a challenge. It helps that I'm mostly a nudist, only wear underwear with some clothes, and even my swimwear is barely permitted in most public or resort pools. But I do like to take it to the edge and I'm not shy at all. That's a trait that I acquired from Trish and her daughters, not to mention my brother Rob.

I chatted with Naomi, the store owner, told her my challenge, and prayed that she could help.

"You're not the only customer I serve who rides motorcycles." She said, "You're just entering a new world. I've learned to pack 2 weeks of fashion into a single saddle bag, including toiletries. Check these out."

She showed me a rack with about a dozen dresses and two piece sets. They were all short and mildly revealing. My eyes went immediately to a green spandex tank dress. I held it up and guessed it might fit, but told Naomi I needed to try it on. I took a moment just to see if there was anything else that I wanted to try. Nope.

I stepped behind the loose curtain for the only changing room and stripped out of my jeans and tshirt. I was the only customer in the store at the moment and I've been dressed by Naomi before, so I left the curtain mostly open. Naked, I held the dress in front of me in the mirror. Naomi was watching. I took the dress off the hanger and slipped it over my head and pulled it down. It slid down easily but hugged my figure. It was like green and black glitter. I pulled the top down and pinched my nipple to firm it up. Yes, I could almost see it through the dress. I turned and showed it to my owner friend. She would never tell me she didn't like something on me, but she'd be honest enough to suggest something else.

"Wow Jan! That's made for you, or you were made for that dress." She reached and stroked the bodice of the dress, feeling my 34Bs (that still stay up by themselves), my ribs, my waist, my hips and my rear. I let her touch me where ever she wants.

"I'll take it. You don't know how perfect this will be." I told her about my green obsession, Emeralda, leathers with green fringe, and the best of all, I pulled the bottom of the dress up to remove it and I turned and bent over enough to reveal my emerald green butt plug. Naomi shamelessly reached out and touched it. I shivered.

"What did I do?" She asked.

"That's the power of this butt plug."

"You're kidding."

This when it got weird. She pulled up her skirt, reached down behind and bent forward, and removed her own anal tool. She held it up for me. It looked like the old Christmas light bulbs. Smooth and simple. "Is it different from this? "

How could I explain? It's like a screw. But the best way to explain was to compare. So I followed her lead, bent over and removed mine. It made me quake again.

I held it beside hers and the difference was apparent.

"Wow girlfriend. Where did you get that?"

" I have a source in the Valley, but the company owner resides in Sedona and we are part of her test market. We often get new products to try."

I didn't tell her that my source is my niece, Teri.

"I'd love to try one. Can you get one for me. I'll pay retail or we can trade. I assume you're buying the dress. Do you know the price? I'll just take it off the dress."

"That sounds good, but I honestly don't know how much they are. I'll pay the full price today and you can just give me a credit for the next time I come here. You know I'll be back."

"That sounds even better!"

"Do you have a favorite color?"

"Yes I like turquoise and purple."

"I'll talk to my friend today. And I'll bring it to you as soon as I have it."

All this time I was standing naked in the shop, with my soon to be new dress draped over my arm. Naomi licked her metal tool and bent over so I could observe the reinsertion. I couldn't resist rubbing my hand over her compact butt cheek. She sighed and moaned as the bulb slipped inside. She gave it a final push and then reached farther down to her dampened pink hole and inserted her finger, moaned again and then pulled it out, stood up and held her hand to my face. I instinctively licked her slick finger and held my butt screw up.

"Would you assist me?"

I handed her the dress and the dildo. She put the dress aside as I bent over. Naomi used her finger to gather my natural lube and spread it on the screw. She wasted no time in pressing the tip to my clean wrinkled hole and slowly twisting it in. I began to feel the thrill. By the time she got it all the way in, I was cumming. As I stood up I felt her hands on my tits. Softly massaging.

"I hope you don't mind. I think we're already past this."

I put my hands over hers and increased the pressure.

"I've always loved shopping with you. Did you say that you ride motorcycles? "

"Thanks and yes I do. Usually with two or three friends."

"You'll have to tell me your favorite rides and destinations."

"I'll do better than that. I ll take you. I'll let you know when and where we're going and if you want to join us, we would welcome your company. I think you'll like my friends too. By the way, I love your ink. Someday you'll share the story behind them."

I hugged her and she held me longer than a quick hug.

"I look forward to seeing you again soon. I'll bring the toy and I'll tell you all about this weekend's trip."

"Are you riding alone?"

"I'm actually riding with the sales person I met at the Harley store last week. We hit it off and made plans."

"Wanda?"

"Yes. How did you know?"

"She's part of our extended group. I've ridden with her twice. Tell her I said hello. I'm pretty sure she will remember me. Obviously she networks with a lot of motorcycle enthusiasts. She knows a lot of people. Good people. She's special."

"Now you've really got me excited."

I paid with cash. It's one way I can maximize my support of local businesses and small business owners.

"Thanks for everything. I'll see you next week."

"Thank you Jan. It's always good to see you."

I left and headed out. Riding back home I was feeling better than ever. I was getting lots of smiles and thumbs up.

I guess I'm finally finding my path to stardom.