My Brothers Erotic Confession

Dress-up play is a safe way to explore gender identities that differ from a persons assigned gender. When people choose costumes and characters, they are able to examine and try on the gender identities and the behaviors of those characters. Please enjoy todays story and thank you for reading my works as I work through my journey of learning about people and my new sexual discoveries. Reader feedback is always welcome and is very helpful. My name is Cheryle "Cheri" I am from an Irish Catholic family, I am an Attorney a thirty year old five-foot two bi-sexual woman with long red hair, blue eyes, single,💋XOXO

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My younger brother, Paul, was staying with me for a long week-end. He had just turned eighteen and was coming to stay with me to visit universities in the Chicago area, a six foot tall young man with delicate features like mine being twelve years older then him I felt more like his Mother then older sister.

I showered in the morning shaving my legs and underarms preparing for a long day in court then a meeting with the partners, I applied my make-up, making sure it was just right. I stood before my large closet for a long time, the outfit had to be perfect, business slutty. Choosing a Giovanna red suit covering my Dream Angels Victoria Secret rad lace panties and bra set and matching red heels.

My brother arrived at my apartment while I was getting ready to go in to court, he sent a text to tell me he had arrived and I sent one back telling him to make himself comfortable in my apartment I would be home around six. I had left the key with the doorman for him so he could let himself in.

Opposing counsel approach me his client was ready to make a settlement offer. My client and I discussed the offer an a settlement was reach in a matter of minutes. We informed the judge of the settlement and called the office to inform the senior partners.

He was very pleased and with no court proceedings my day was suddenly free. Excited by the turn of events I hurried home to spend the day with my little brother. I arrived at my apartment building riding up the elevator to my tenth floor apartment.

Standing outside my door I could hear loud music from inside. I smiled at the unexpected free day to spend with my little brother. Opening the door I realized the loud music was coming from my bedroom. Laughing, I thought how I had told him to make himself comfortable.

Walking to my bedroom I looked in the open door there was a blonde woman with long curly hair dancing in baby doll pink chemise with matching panties. I just stood there leering at the sexy thing her back to me her tight ass gyrating to the beat of the music and her smooth long legs moving in an erotic dance.

What had I walked in on? My mind racing trying to figure out who this was and where was my little brother. She spun toward me our eyes meeting as shock washed over me the sexy thing was my little brother! I realized that was my Avidlove baby doll chemise and panty set and the blonde wig I had bought for Halloween a couple years ago.

Paul ran past me into the bathroom slamming the door as I was still processing what I saw. Knocking lightly on the door I offered words of comfort telling him it was OK, everyone gets curious, that I wasn't mad at his experimenting with my under garments.

Finally he opened the door tears trickling down his face I held him my arms just like I had when he was a small boy. Reiterating everyone experiments a person sexuality is not set in stone how it is fun to see how the other half lives. I admit I was rambling still processing the situation but sincerely trying to comfort him.

We walked to the living room and sat on the sofa. A surreal event playing out in real time as we talked. I asked questions in a none probing way using my lawyering skills. He admitted this was not the first time he wore woman's under things but never nothing as nice as the my designer things.

I ask if he enjoyed wearing pretty things and when the desire started. He shared with me how it all started one night at his friends Kevin's house the were drinking and smoking pot in Kevin's basement room watching porn clips on the computer.

Kevin complained at how hard the videos were making him and he needed release. I listen intently to Paul relaying the night to me picturing it in my head. Paul explained how his best friend Kevin ask him to help him and how he refused but then Kevin said Paul could pretend to be the sexy slut in the video it wouldn't be him he could become her.

Paul explained this logic made sense to his stoned brain but he told Kevin he would need sexy underwear like hers thinking that would be the end of Kevin's game. I was on the edge of my seat listening to his strange tale feeling excited wondering where the story would go.

He continued talking in a low tone almost a whisper explaining Kevin went in to the laundry room adjacent to his bedroom and returned with a black lace panties and teddy set which must of been his sisters. Kevin threw the sexy underwear to him saying what's your excuse now calling Paul's bluff.

Paul said they went back and forth Paul telling him you can't be serious, Kevin saying you said you do it if you had sexy underwear like the slut in the video. Paul said he looked at the panties then Kevin and asked him you really want me to put this on and pretend to be a sexy slut and act out the video. Kevin said yes it is just a game like we played as kids pretending to be soldiers or cowboys.

Paul said he went to the bathroom and undressed he slid the lace panties up his legs adjusting them and tucking his penis to hide the bulge then sliding the teddy over his head he looked in the mirror he explained he did look and feel sexy.

My panties growing wet at his erotic transformation tale as my eyes admired how sexy he looked in the blonde wig and my Avidlove baby doll chemise and panty set a little make up and a manicure and pedicure he would be gorgeous. listening intently as he continued with how he returned to the bedroom finding Kevin naked on his bed stroking his hard cock.

How Kevin said you look gorgeous baby when he entered how wonderful that felt how he felt alive being a sexy slut. How he crawled into the bed like the slut in the video licking Kevin's balls with his tongue teasing his cock head before sucking him into is mouth. How wonderful it felt sucking his cock being a slut for Kevin.

Amazed and excited by his erotic confession he said he and Kevin continue playing the game ordering sexy things online adding nylons and heels until Kevin left for Cal Tech. Paul said he hasn't dressed this way since Kevin left but seeing all my sexy things inspired him and when he saw the wig he had to see how it looked.

My body was on fire with a sexual heat hearing him convey this to me and I expressed my feelings to my new sister, "Honey let's have a girly day of beauty, shaving, waxing, manipedis, dress shopping, I'll do your make-up for a night on the town."

Kissing her cheek I called my friend at Bella Pella Salon & Spa to see if she could get us in today. Bella Pella Salon & Spa offers manicures, pedicures, body waxing, eyebrow shaping, hairstyling, lash lift, and makeup services, if my brother wanted to play dress up we were going to do it right.