First Experience

Best Experience

There have been so many for me and my wife of 27 years.

Before we were married, my wife and I lived together for 6 years and we traveled a lot. There was one road trip to Kansas City in the late 80's where she packed for us and I got home from work and we drove there. KC was a frequent destinations for our road trips and had been there 6 times together by now.

By this time in our relationship, I wore panties every day and on cooler days, I wore camisoles or short full slips or chemises under my thicker shirts or under a sweater vest or something to concealed my straps and pantyhose or thigh highs under my slacks to work. So, on this day, all I was wearing under my khakis and button-down shirt and sweater vest were my soft blue VF nylon bikini style panties, lace top thigh-hi hose and my wide strap plain white nylon camisole and the matching short half-slip.

So, I got home at 2pm after fueling the car and checking all the levels of the car and picked up "Cindy" (not her real name) and we hit I-35 North. After eating at one of our favorite restaurants, we got to the Embassy Suites in KC around 9:30 and after unloading the car and unpacking our bags we took a nice jacuzzi bath together, and we shaved each other's legs and crotch areas. We got out, dried off and put lotion on our skin then slipped into our matching satin gowns and robe, smoked a joint and we painted each other's toe nails. This made us horny so we made love and went to sleep after a long day.

Cindy was up first to get ready and I bummed around in my gown and matching robe, smoking a joint and having coffee when she came out of the bathroom/shower area in her gown and matching robe and smiled and joined me on the couch for a while, relaxing, smoking and drinking coffee, our favorite morning activity. I started to get horny and was stroking her tits in her satin robe watching harden but wouldn't let me go down on her since she didn't want to shower again but she did open my robe, pulled my gown up and sucked me off and we shared a lover's kiss.

We had plans on going to a big flea market we have been to before and we were deciding on what to wear and take with us and I told her to pick out what we were wearing under our clothes while I shower. I hung my gown and robe on the hook on the back of the door and when I got out of the shower, Cindy had hung her gown and robe there also and put the lingerie she wanted me to wear, me knowing she will be wearing the same; Victoria's Secret 2nd Skin Satin matching pink bra and hi cut panties, white garter belt with beige stockings and a short white full slip with lace around the bust and hem.

I got hard again thinking about our day while putting on my lingerie.

When I went to the room, Cindy was wearing her new dress she bought the week before that I told her she looked so pretty in.

I questioned her about the lingerie I was wearing and she told me because it will feel marvelously sensuous and look sexy under what I bought you to wear. So, before you argue, I know you have wanted to do this so now is your chance to be my girlfriend for the day. She took the dress from the bed and pulled it over my head and down my body it went. It fit perfect except for the extra material in front that should accommodate breasts.

The hem of the dress fell a few inches from the bottom of my slip and since I do not tuck, it hid my bulge just right. I told her that I loved everything she has planned but I still looked like a man in a dress.

Cindy told me to give her a few minutes to work a bit of magic and then then I can decide. As she worked on my face, she was telling me that we are in a place where no one will know us or give us a second look. If people looked at us, they will see 2 women that are into each other having a great time laughing and enjoying life. This logic relaxed me telling me not to look as she pulled a brunette wig that she had already brushed out and fixed it on my head and when she finished my face and I saw the subtle yet pleasing make-over she gave me and I couldn't say no to her. Cindy inserted 2 foam breast forms in my bra cups to give me some shape, clip on earrings, necklace, bracelet and a few rings.

I was speechless and she saw how nervous I was. She stood me up and we looked at each other standing side by side in the mirror and she took me in a gentle hug, running her hands over the dress, feeling all the layers of the lingerie gliding over my body then she kissed me, told me she loved me and wanted to do this for me and her. She can live out a bit of lesbian tendency she has and she will not let anything bad happen to me. It was getting on in the day and we were hungry so Cindy gave me a spare purse for my stuff and a tube of lipstick and blush and to touch up along the way. I put on a pair of beige 1″ heel, open toe sandals and we grabbed our jean jackets and hats to wear will in the sun and never looked back.

We looked like 2 girlfriends who were very much into each other and we had a great, adventure filled day. We did get a few disapproving looks and I was outed a few times but didn't care because I would never see those people again. Cindy looked out for me nicely.

We walked around this flea market for most of the afternoon, buying a few things along the way and when we left, we stopped for a small dinner at a local Greek restaurant and reflected on my first outing in fem. I thanked her for letting me do this and she said we can do it again when I am ready.

We stopped by a liquor store for a bottle of wine and went back to the hotel to relax the rest of the evening in our hotel suite and basked in the luxury of our satin gown and robes and made the sweetest love to Cindy.