My Brother's Erotic Confession Ch. 02

After a day at the Bella Pella spa getting manicures, pedicures, a complete body waxing, eyebrow shaping, hairstyling and proper fitting of his blonde wig, a lash lift, and beautiful makeup I had to admit my younger brother Paul had become a gorgeous young woman the name she chose was Emma.

I took Emma shopping on North Michigan Avenue, Chicago's magnificent mile, with 450 retailers, including flagship experiences, major department stores, and international designers and boutiques. Going from store to store we purchased everything a lady needs to be sexy, heels and pumps, nylons, a padded bra, dress, skirts and most important gaff panties a special type of compression underwear, the main purpose of a gaff is to help minimize the appearance of a crotch bulge helping transfeminine women to achieve a smoother, more affirming appearance, I put it all on my American Express black card.

Emma was a six foot tall blonde bombshell in four inch black fuck me heels, a black mini skirt, nylons over her smooth legs, with the padded bra her breast were as big has mine. We walked down the busy downtown Chicago streets men turning to stare as they passed. Emma loving every minute talking and giggling as we walked I was teaching her to make her voice come from her throat instead of her chest, to sound more feminine, I listened as she transformed her voice changing the pitch, volume, resonance, articulation, and melodic intonation into a sexy sultry voice.

A tall dark handsome man held the door for us as we entered La Scarola a Italian restaurant a small, cozy neighborhood place with framed photos covering the walls serving classic Italian comfort food. It always gives me the feeling Grandma is going to walk out of the kitchen and pinch my cheeks. A wonderful old school storefront restaurant a terrific little hideaway with amazing food and great service.

The maitre d greeted us, "table for two? Ladies," a moment I'm sure Emma will always remember. Sitting us at a table by the window we order red wine and perused the menu we both order chicken parmesan as I watched Emma smile and flirt with the waiter.

We had a wonderful time in my favorite Italian restaurant when I asked the for the check the waiter he said mister Moretti paid your bill as he pointed to the dark handsome man sitting at a table across the room, the same man who held the door for us when we entered La Scarola. Raising our glasses toasting to him he smiled and raised his glass to toast with us.

"Does that happen to you a lot?" Emma asked me. I just giggled what a fun day and evening I was having with my sister. As we walked through Pilsen one of my favorite downtown neighborhoods that overflows with music, art, culinary tradition, and nightlife. It's home to award-winning restaurants, iconic music venues, and sensational murals as far as the eye can see.

We walked into Radius an old steel factory the marvelous space has been transformed into a modern artistic venue, showcasing mural work by local and international artists, equipped with stunning light fixtures which highlight the uniqueness of the venue. Radius utilized the open floor plan of the building to produce an interactive exploratory experience for guests, where people can flow between the various areas or change the viewpoint by ascending up to the mezzanine level. Radius has been in a process of evolution for the last four years or so, progressing through multiple concepts and structures before finally solidifying into a multipurpose venue focused on elevating the East Pilsen area of Chicago.

We walked around looking at the different murals sipping more wine along our way.

"Hey Cheryle," turning to look behind me where the voice was coming from, "hi Eric small world," I responded. Eric and Ryan are two junior attorneys at my law firm, I introduced Emma to them, and we stood there making small talk Emma touching Eric's arm as they talked she was flirting with him so cute my little sister flirting.

We all walk through the beautiful space together Ryan and I walking behind Emma and Eric. I watched like a mother hen the two seemed really into each other. Eric was a handsome man a recent graduate of law school tall maybe an inch taller then Emma in heels. Breaking my trance Ryan asked if I wanted another glass of wine, I did, so we told Eric and Emma we were going to the bar. They said they wait there for us, as we walked away I glanced back with amazement seeing Eric lean in kissing Emma I almost spilled my drink. My eyes transfixed on the scene playing out in front of me has their tongues dance in each others mouths.

"They're cute together," Ryan said to me, "Don't worry Eric's a gentleman."

With that we continue on to the bar, when we returned they were gone, wondering where they got off too I walked toward the bathroom looking for my little sister, Leaving Ryan there in case they returned. After checking the bathroom with no luck, I walked around some more looking for them. Finally I passed a dark hallway that led to a storage room stacked with liquor boxes and empty kegs I saw a blonde woman on her knees cock in her mouth sucking away, mesmerized by the scene I was frozen, she was really getting into to it. Devouring a large cock, squeezing the balls, working the shaft.

Wait that's Eric the reality slowly dawning on me that was sweet Emma on her knees sucking Eric's cock. Walking back to were I left Ryan waiting telling him I had no luck finding them and we should just wait here.

Emma and Eric finally returned holding hands, I whispered in her ear, "you have a little cum on your chin honey" handing her my drink napkin to wipe her chin. She giggled whispering back, "Thank you for a great day, sis."