She Wanted Me to Have Fun...

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A first time CD experience.
1.5k words
4.15
33.3k
11

Part 1 of the 2 part series

Updated 06/07/2023
Created 12/02/2015
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I was alone last night. Lynn had gone out to bring a friend to the airport and told me to have fun and be comfortable while I waited for her to return. I knew that her trip would take at least 2 hours and I was free to do anything. Lynn called thirty minutes after leaving, telling me that she'd be late. December is a lousy time to travel and the departure was delayed 2 hours.

She and I were about the same size and I was curious about how it would feel to have silky and soft clothes against my skin. I dug out the old camcorder and tripod and set it up in the corner of the room. My first find is a pair of her laciest panties with a matching bra and slipped into them. I looked into our full-length mirror and admired my new "look." "Not bad," I thought and my aroused cock seemed to agree based on its standing at attention. I knew that I needed some padding up top. Socks were stuffed into the cups of the lacy bra but no matter what I did, they just didn't look like a real set of tits. Ok Dave, let's think about what we can do to make them look good. Brainstorm...zippered, food storage bags with water? Balloons? Water balloons from our last outdoor battle? Ooh! That's it. Water balloons will give a nice bounce and have a natural shape.

I stepped over to her walk in closet to decide on my next selection. Blouse and skirt, little black dress or the slinky wrap dress she wore to the club last week? I say fuck it; I'll try all three! First I try the pink blouse with the black skirt and nude hose and a pair of 1 ½ inch slingbacks. I look like I'm ready to take steno at the office if only I knew steno!

Out of the officewear I slip and return them to the hangers and take the little black dress off the hanger. I pull it over my head; adjust the hemline and slip into the 3-inch heels. The feeling is great and I love the look but I just need to try the clubwear! The dress goes back to the hanger and out comes the slinky number. It goes on like it was made for me. My exploits are being recorded on the old video machine and I review the footage thinking that the footage isn't bad. Women have so many great choices of clothes while us men are stuck with pants and a shirt for almost every occasion.

The clothes go back into their respective places and the camera is put back in the closet. She comes home shortly after and asks what I'd been doing to occupy myself for the last four hours. I reply, "nothing...really. Just trying out some ideas I'd had." A smile came across her face and she told me that she had some ideas, too.

We settled in to watch a movie on cable and started chatting about our deep dark desires. My couchmate told me that she always wanted to have a sister to spend time with but since she was the baby of the family and her siblings were much older she never had such a luxury. She never had a shoulder on which to cry, a confidante, a pal with whom to go shopping. It was my turn to reveal my fantasy. I was wanted to be her mall wench.

The desire to be able to dress in something other than jeans and a oxford was what I desired. She asked if I'd ever tried dressing up and I asked if she was serious. The beans were spilled, my adventure from earlier that evening and how I felt when looking in the mirror were shared. I brought out the videocam and connected it to the widescreen. We sat on the couch giggling. A long hug and smiles were shared as we realized that each of us could have our needs fulfilled.

We bounded up the stairs and raced to the bed to see who would be undressed first.

A night of passion ensued.

I was the first one awake in the morning and proceeded to make a breakfast of bacon, eggs and toast, which was served, to my beautiful wife while still in bed. We spoke of our plans for the day. It would be a day at the shops but she wanted to know if I was serious about what I'd said last night. Indeed, I was serious and had hoped to be able to fulfill each of our desires. She told me that if I wanted to do this, I'd be able to borrow some clothes but it would only be for one time. I have to get my own. We looked in the closets for the right look and laid them out on the bed. I was eager to start dressing but was admonished that if I was going to do this I couldn't look like a hairy legged spider. We took my trimmer to my legs and chest then took a razor and shaving crème to smooth out the skin. I had never had my body shaved and the feeling of my own smooth skin was totally foreign and amazing. We moved back to the bedroom to start getting me dressed for my big day.

On went the same lace panties and matching bra from last night. Next was the nude pantyhose and I had been reminded that a "nice girl always wears a slip" under her skirt. Into the office girl outfit and I chose the daring three inch heels. Styled hair, some foundation, blush, eyeliner, mascara and pink lipstick completed the look. She got dressed in a similar business casual look. Down the staircase, out the door to the car and away we go!

The mall is a vast paradise of shops and kiosks geared toward the latest fashions and haute couture. I was nervous about the fact that I was dressed as a woman and about to go in to a place frequented by "gangs" of teenagers who may not be accepting of a guy in woman's clothing but my wife reassured me that if I was uncomfortable in any way, we would be out of there in a flash.

We browsed through some of the smaller shops and made mental notes of things we liked. Off to Macy's for their lingerie department and some fancies. We pick 5 matching bras and panties, one full slip and two half slips. Next stop is one of the smaller stores where we had found a nice little black dress, cut oh so short. Off to the shoe store to see if we could find some flats, heels and a pair of sandals. We were about to leave and I was reminded that a guy's wallet will never work if I wanted to have the correct look, so we went to the accessories department and found a wallet and small purse to carry. We'd been at the mall for hours and we both heard the call of nature, we got to our respective doorways and she grabbed me. Out of habit, I was heading toward the men's room but duh... I did not look the part. I'd never been in the ladies room so I remembered to sit to maintain decorum. We did a quick touch up of our makeup and headed toward the food court. I had to be conscious and not eat like a ravenous wolf. As we were eating, my wife noticed one of her friends across the way. I begged her to not do anything to raise Charlotte's attention but it was too late. Charlotte came over and I was introduced as an old friend "Dee" from back east. Lynn and Charlotte chatted for about fifteen minutes and then Charlotte's phone rang. Her husband was ready and would meet her at the Sears entrance. We said our good-byes and Charlotte disappeared into the mall. I told Lynn that I wasn't ready to be revealed in my new wardrobe.

Just one more stop to make. We were off to Victoria's for some sleepware. A red teddy, a robe and a lace and satin full length gown for the look. As we were heading out, my eye caught the white fur-trimmed, red satin set. I had to have it! The Mrs. Claus look is so cute. It had been a long day and since it was my first time in heels, my dogs were barking. Lynn asked if I'd be interested in trying to drive in heels. It was interesting! Just the way your foot had to be in a different position and the angles my foot hit the pedals, what an experience!

Home again. We head upstairs and I put on my Mrs. Claus outfit. It is so soft and warm, she gets into her flannel jammies, cuddles with me and we talk about our experiences from the day. I told Lynn that I have never had so much fun at the mall and she was happy to have a "girl's day out."

I am so looking forward to our next adventure!

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6 Comments
SabrinaGLangtonSabrinaGLangtonover 2 years ago

Very nice story, how did I miss this. Get's a little Christmassy at the end too... Thanks

AnonymousAnonymousover 3 years ago
First Timer

It was now or nothing fully dressed in my slutty out fit i now am weighting for my first cock.In full make up wig and bright red lips hoping to find a cock.Red corset red thong red fish net stockings red thigh high 6'' boots and the tightest shortest skirt and red sheer blouse with red stocking gloves.Now all i need is a hard cock to play with.I knew were to find all the cock i wanted and more.I went a all black club and found more cock then i wanted but took it all.

AnonymousAnonymousover 8 years ago
If Only

Your story got me thinking about how wonderful it would be to do that very same adventure with my wife. I dress almost everyday and feel so very comfortable when I look like a woman. I too love the feel of the soft fabrics on my skin, the snugness of my bra, the sensuous feel of pantyhose and the alluring sound of my heels. I sincerely hope you continue this story. BTW, when I am dressed as a woman, I feel like a woman and want to have sex as a woman.

Jaye

BrendaNWBrendaNWover 8 years ago
loved it

I only wish that I was in a relationship like that... it would be living a dream of mine.. please continue I would like to hear more about their adventures as girlfriends and spouses

AnonymousAnonymousover 8 years ago
nice story

I would love to hear what Charlotte's husband thought when he saw you from across the mall!

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