Shopping is a Drag

They hadn't met at a burlesque club or drag show. This chance encounter was unpredicted and unanticipated, yet a delightful surprise. Jeannie came out- Lewis smiled to himself at the double entendre'- the day prior with his 'old lady' in his store, as Lewis had studied Jeannie in total anonymity as he admired Lewis' prized dresses and gowns. (The ones he put on display weren't the full extent; no, the true cream of the crop were nestled away in another room near his office. These various outfits, he felt, were perhaps a bit too extreme for the general public in a small town. They consisted of highly bedecked corsets and dresses on to the most flamboyant one piece body stockings, all in a multitude of materials and accents, but all completely glamorous. Lewis was considering how Jeannie would respond to this truly special exhibit- IF he let Jeannie even see it.)

Lewis knew that he could have Jeannie on his knees with some fairly simple ploys, suggestions and demands. But to what end? That act of submission would be quick, shallow and fruitless. Jeannie would explore and realize even more about himself, Lewis suspected, but he would most likely then go into hiding and denial. That conclusion would be meaningless to Lewis and unwanted confusion for Jeannie.

What to do? A dozen options and potential outcomes raced through Lewis' mind. Lewis was well aware of risks and probabilities, of thrills and arousal, domination and submission, and at this point in his life, joys and sadness.

He liked Jeannie alot. He saw in Jeannie a bit of himself from (many) years' prior- a bit of daring, a smidge of softness, a hint of feminine allure, all which wanted to be blended together into one's own unique, sexy, pretty mystique. Lewis had his own 'ole what's her name' in his life; his was a friend who remained friends, but they both realized was true to each other on a platonic level. Lucky for Lewis, this revelation coincided with another life choice which he pursued and turned into a business profession coupling glamour, a variety of fetishes and the wanton indulgences of the rich and famous. That many in this niche circle ached for the pleasures that the vast masses enjoyed without fear of exposure, his newly discovered client base had no issue with the fees to have their desires fulfilled in private splendor.

Lewis was amazed at how powerful the mind was, how what seemed like a lifetime of events had washed across him in mere seconds. The lingering images of glam shows, world pageants, week long theme parties focused on wicked debauchery drenched him while also building visions of his own erotic pleasures- a feeling that he realized had translated into a quite visible erection in his tight, pastel green slacks.

Lewis eyed me with anticipation as I sat before him. Back in focus, he realized he had asked me a very challenging question and our mutual brief pause gave us both time to consider the potential pleasures and probable stress that could evolve. I looked up at Lewis and knew I had to make a decision. I had never met anyone like him before- someone assertive and engaging, worldly yet so open and warm, flamboyant yet so able at disabling 'whats her name's' cold exterior.

O my- I thought of Yvette in the same way that Lewis does! I owed Lewis an answer almost as much as I owed one to myself. I inhaled deeply as I looked upwards at Lewis. Maybe I could just tell him I'm not ready to answer him; maybe he would still accept my interests and curiosity. Maybe he would accept a response deferred to 'later'- after our get together this evening?

Lewis broke the tension as he reached for my hand and changed the subject, ever so slightly. "Hon, though your little slip on shoes are cute, I have a suggestion which I KNOW you'll love. Take those off as well as your shorty socks" he ordered. I did as told.

"Now, stand up" he continued, as he took my hands to lift me up.

"I have just the thing to help complete your look, at least for now," he said. Lewis went to an armoire that occupied one-third of the wall and extracted a pair of black open-toe sandals with 4" heels. "Try these on, Jeannie," he said as he handed them to me.

I slid them on, a bit awkward and definitely a bit stressful. They actually fit perfectly and I took a few steps in them and then engaged in a small pirouette to show off. Lewis smiled with approval.

"Wait- one more thing. You just can NOT wear those without your toes looking presentable. Let's paint your toes!" he said, a devilish smile on his face. He saw the stress on my face. Nail polish is not temporary; what would Yvette say? What a question!

"Just something subtle," he whispered, "for now". And Lewis extracted a bottle of soft pink nail polish from one of the many drawers in the armoire. "Come on, Jeannie. Don't be afraid," he said in a convincing, non-threatening manner. "She won't notice, trust me!"

I stood before him. If I put it on, what was the harm? I could easily remove it, after all. And the color was pretty much similar to my skin tone. I bet she wouldn't even notice is right! I smiled at Lewis and nodded OK.

He gestured for me to sit back down and to put my feet up on his desk. A few minutes later, the fast drying polish was applied to every toe nail and Lewis gently blew on my toes and then tickled them. I wiggled but he kept a firm grip on my legs.

"One more thing, I think," he said. I then saw that he had also brought a lipstick over to his desk and he motioned for me my upper body closer to him. I moved my bottom to the edge of the chair and leaned forward. A few motions and I felt the creamy product applied to my lips.

"So, now, let's get you back up," Lewis directed as he again took my hands to help me up in my heels.

I felt the lipstick on my lips, the tightness of my women's leggings, the change in my posture and presence as I stood before him in heels, and I couldn't deny it all was so arousing. I then saw that Lewis also noticed how I felt.

"Honey, it's called cupping, and you'll need to remember that from now on if you want to have that perfect front view," Lewis said as he reached down to caress my encapsulated but very visible erection. I closed my eyes; I had never been touched by a man and it had been quite some time since Yvette had touched me, as well.

Lewis then reached inside my tight leggings as he said "Here, let me show you." Moments later, standing before him, Lewis was caressing my cock, an even more feeling of pleasure, coupled with the satiny material. I was in heaven. "I'm trying to tuck you down, Jeannie, but, my goodness, it looks like it's going to take some effort on my part." He continued to caress and stroke me, and as I opened my eyes, he pressed against me and kissed my lips.

I was in sheer ecstasy and moaned softly. Lewis knew I was beyond the 'point of return'. His kiss became more forceful and erotic as he slid his tongue into my mouth. My lips, wet and creamy, melted to his and I was overwhelmed, wanting more, so much more. After several minutes of deep, French kissing, Lewis pressed my back ever so slightly. With both hands, he began to slide my leggings down, and then my panties, as well.

Looking at me, he pulled my top off, exposing my budding breasts. He squeezed both nipples and then cupped my ass cheeks as he moved down to begin kissing and sucking my cock. If my effort to recall the last time Yvette had kissed me was a challenge, then trying to remember the last time she gave me oral pleasure was near impossible. Regardless, she never did it the way Lewis was; there was no comparison.

Lewis reached up to fondle my one nipple while his other hand massaged and caressed my round ass. I tried to make this moment last, to selfishly hold off so that I would be gifted minutes and minutes of erotic pleasure. I tried but it was useless. Lewis slid his mouth over the length of my 6" and I erupted with unfathomable intensity. My muscles froze, my body shivered and I felt my 'clitty' throbbing for sheer life.

Lewis and I looked at each other as my climax finally subsided. Then, with delicate flair, he stood, his one hand still fondling my nipple, and leaned forward. His lips met mine and I had nowhere to move. A moment later, his mouth open and pressed to mine, we shared my cum as our tongues danced together.