Halloween with Kym

My first ever story based on a fantasy that will most likely never happen… (All characters of are Adult age).

I am a cross-dresser, who while I had custody of my Daughter Kym, stopped dressing. The characters are real, (names have been changed to protect the innocent), the locations are real. Only the events are made up. Should they ever actually happen, I would be very, very happy.

After Kym moved away, I started wearing my pantyhose again under my pants and with a robe around the house, this was the most my wife (Kym’s step mom ) could accept. I spent most of my time dreaming about dressing again. I was soon to find an exciting and forbidden release for my desires.

Halloween was fast approaching when Kym sent an e-mail asking me if I had plans for Halloween night. Telling her I didn’t, she asked if I would like to go out with her on the town that night. After I told her “yes”, She asked if I would dress in costume with her I said “Sure, Is there anything specific that you would like me to wear?” “Yes” She said. “ I want us to go out as Mother and Daughter”. “What”? I asked. “I want you to dress up like a woman, and be my mom for a night. I want us to both wear dresses and drive around town.” I was so taken aback I didn’t know how to respond at first. After a few moments I said, “ Only if you help me with my make-up and wig. What kind of dress do you have in mind”? She replied,” How about the blouse and Short Skirt you had hidden in the garage when I lived there”. I never knew she had seen that suitcase, I had it hidden in the back of the pile and I had forgotten about it for so long. It was only then that I remembered the photo of me dressed up with the clothes that I knew she had found out about my fetish.
She told me she wanted me to meet me at her house at 11am on Halloween. After I pulled into the drive she meet me at the door and gave me a big hug just like always. I grabbed my suitcase with my ‘old outfits’ out of the trunk and took it in with me. I went into her restroom to change and she slid a packet of Sheer-to-the-waist pantyhose under the door and said, “Dad, when you change, I want you to wear these and no panties, just like in the pictures I saw”. I was beginning to understand she had plans beyond what I first imagined. After dressing, I was wearing the pantyhose, short slip, a white blouse, a short floral skirt, and a pair of black 3” heels. I came out of the restroom and Kym had me sit at the table to get ready for my make-up and wig.
She was wearing a pleated schoolgirl skirt, White blouse, and the same pantyhose she gave me to wear. She also had on a pair of Mary-Jane shoes. Kym had me sit in a chair against the wall next to the table, She straddled my lap and sat on my lap as she faced me and began applying my make-up. I reached behind her and clasped my hands behind her soft ass and held her on my lap. After about fifteen minutes she told me she was done and got the wig and placed it on my head. She then put her hands between her legs and on my now swollen cock and rubbed it through my skirt for just a moment.
Then she stood up, bent over and kissed me lightly on the mouth, said “I Love you Mom”. And pulled my hands off her and stepped back. “Get up Mom and look at your self in the mirror” she said. I looked and I could have passed for her mother any day had it not been for the tent I was making under the skirt I wore.
“Lets go Mom” Kym said and started for the door and my car. “I am going to call you Jackie if anyone wants to know your name today”. Out we went, she got in the passenger door and I got behind the wheel and I started to drive. “Where to?” I asked. I want you to drive into downtown Denver and just drive up and down the streets. I want everyone to see you dressed like this, You look so HOT MOM.” she said.
As I got onto Buckley Rd. I started heading North to I-70 and got on the freeway into town. At Colorado Blvd. She told me to get off and go down to Colfax to get into town. As soon as I got on Colfax she reached over and grabbed my hand and put it on her knee. “Mom, my leg hurts and I need you to rub it”. I began to gently rub her leg and thigh, Kym scooted down in her seat and spread her legs further apart. “Higher Mom”, I slid my hand under the hem of her skirt and she scooted down further, as I slowly moved up her leg I reached the gusset of her pantyhose, I stroked her cunt through the hose as I drove down the street. I started to reach up to get under her pantyhose when she stopped me and said, “No Mom, Not yet”. She sat up in her seat and pulled her skirt back down.
At this point my own skirt had a bulge poking strait up in the middle. My Pantyhose were no match for my throbbing cock. Kym reached over and lightly stroked my bulge through my skirt. The silk from my slip and the Pantyhose felt so smooth, I was in ecstasy and I wanted to cum right then and there, but Kym stopped.
“Mom, I want you to go up to Federal and go up to I-76. But, stop and get gas in the car before you get on the Highway, I want to get something for us to drink, and I want you to show off your legs to the people at the gas station”. God I was so horny by this point. My own Daughter was driving me crazy. I wanted to Fuck her, and Fuck her good. My girl the slut. I pulled into the gas station and got out to pump the gas. I was having a hard time hiding my hard-on as I pumped the gas. Kym went in and bought a six pack of Cola and came out and got back in the car. Just as I was about to get in, Kym said, “Mom, pull up your skirt and let me see your pussy.” I reached down and lifted the front of my skirt and gave her her first view of my now swollen cock. I dropped the skirt back down hoping no one saw what I did and got into the car. Kym just sat there and smiled as we pulled back onto Federal and onto the Eastbound lanes of I-76.
No sooner had we merged onto the freeway and Kym opened up a cola, reclined her seat slightly and grabbed my hand again putting it on the gusset of her pantyhose. She then reached over and flipped my skirt up exposing my cock to any one in a truck that might drive by. I began to finger her little nylon covered slit as we drove. “Mom, that feels soooo good, don’t stop”. After about two miles I felt her legs squeeze down on my hand as she started moaning louder and louder. Suddenly she shook from head to toe as she had her first orgasm of the afternoon. “Crap Mom, I have been dreaming about that since I first found out about your secret”. “Take the road into Brighton and stop at the park by the river”. She pulled her skirt and reached over and lowered mine again as I took the fork into Brighton.
It was just starting to get dark as I pulled into the park and took my parking place. “Lets go for a walk”, Kym said. We both got out of the car, and Kym handed me a soda and we began to stroll down the bike path along the river. As soon as we were out of the lights from the road Kym turned to me and said. “I want to give you a kiss”. I leaned over and she put her hands behind my head and softly kissed me on the mouth. She kissed me again and I parted my lips and soon we were giving tongue to each other. “I love you Kym”, I said. I love you to Dad, ere I mean Mom”, was her reply.
Suddenly, She placed her hands on my legs just below the hem of my skirt. She lowered her head and placed it under my skirt. This was not too hard as her 5’3” frame was so much smaller than my 6’1”. I felt her lips begin to kiss my cock through my pantyhose. Suddenly, she grabbed my cock, adjusted my hose around it, and stuck it all in her mouth. She was sucking my cock through my pantyhose right on the bike path of the park. “Kym, I’m going to come!” She just continued to suck as I came in her mouth and she drank my nylon filtered juice with such enthusiasm. She stood up again grabbed my hand and lead me to a picnic table. She sat on the table and had me sit on the bench.
She reached under her skirt and poked her finger through the nylon in her pantyhose and exposed her pussy to me for the first time. She had shaved herself bare. ‘Eat me, Mom”. Who was I to say no. My tongue traced her clit, and lapped up the juices that flowed from her. Suddenly, her legs felt like a vice grip on my head, She groaned as she came in my mouth. “Keep your mouth there , I need to do one more thing”. Before I could react, She started to Piss in my mouth. At first I was repulsed but as I got used to the taste, It became very arousing to me. Having to piss myself, I reached under my skirt, freed my cock, and pissed on the ground as I sat there taking my own daughters piss in my mouth.
“Mom, lets go back to the car now, I need to fix your make-up”. As she took a towel and wiped my face, she grabbed her purse and started to re-apply my face. When she was done, she told me to take her home, she had one last surprise for me.
Walking in her front door she pulled out a kitchen chair and had me sit in it. She lifted my skirt, pulled my cock out of the pantyhose, straddled me and lowered herself onto me. We Fucked there in the chair, embraced and kissing as we both shared three more orgasms. “I love you Dad”, She said. “I Love you too, Kym”……(Part two Kym’s roadtrip – ‘Home to Nevada’ with her new Momdad. Cumming soon…)