She Wanted Me to Have Fun... Pt. 02

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The next day brings more adventures.
2.2k words
4.32
17.5k
4

Part 2 of the 2 part series

Updated 06/07/2023
Created 12/02/2015
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Sunday morning comes and the two of us are deciding how to spend our day. I suggest some skating at the old millpond, a hayride and we might attend the town's tree lighting. She is intrigued by the idea and suggests I go en-femme. She offers one of her woolen skirts, a cable knit sweater and warm tights. I tell her that if I'm going in drag...then she is too. I dig out one of my old tweed blazers, woolen cap and shit-kicker boots for her to wear. We both giggle at the thought of what we'll look like.

We pick one of my new matching bra and panty sets and a half slip, pink tights from Lynn's drawer to go with her plaid wool skirt and sweater. For Lynn we find a pair of my Levi's, flannel shirt and blazer. Lynn binds her boobs to look her part and dresses in my clothes. After putting on the skirt and sweater Lynn does my hair is styled and make-up is applied. She puts on the shit-kickers and I borrow a pair of her Ugg boots, grab the skates, a thermos of coffee and head downstairs to the car.

As we're driving to the edge of town we start talking about how passable I am. I know that I need to work on my voice and Lynn says if I try to speak in hushed tones my voice isn't obviously male. I concentrate and reply in a bit of a squeak and remind her that she's dressed as a man and to speak in a lower octave.

Along the way, we pass the mall again and Lynn says that most of today's girls have their ears pierced and asks, "Would you consider doing it?" I said that I'd not really thought about it but what the heck, men and women have pierced ears so why not.

We head into the mall and look at the directory to find Claire's and make a beeline like giddy schoolgirls. We're browsing and the clerk with a badge identifying her as Barb approaches. I think to myself that it is ironic that her name is Barb and she'll be putting "barbed metal studs" into my ears. Lynn goes to the other side of the store looking at the little storage boxes. I walk up to Barb and tell her that I'd like my ears pierced. She asks, "how many holes in each side? The store is having a special and each additional piercing is half price" I never considered more than one but decided to be a bit daring and go for 3 in each side. I pick the type of stud, titanium with a clear CZ stone. She tells me it hurts a bit more for each hole higher up the ear and I'm ok with that. I sign the book for the legal release mumbo jumbo and take a seat in the chair, under all those lights. Lynn comes over and sees that I'm ready and watches as Barb starts the prep, marks the 6 spots and pulls out the gun.

I'm ready for this, aren't I? I ponder the choice I've made and say to myself "let's go!" Lynn comes back and sees the 6 ink spots on my ears. With a devilish grin, she says to me in her "husky" voice that she likes what she sees. Barb finishes hole number six and gives me the bottle of after care cleaning solution, a photocopy of care and cleaning instructions and tells me to keep the studs in for six weeks. We're all paid up and on our way to the mall exit and she says we need to make a piss stop. She really is enjoying her new role! We head to the heads again and this time we split up. She tells me that the men's room is in desperate need of a cleaning and I say that's why we stand to pee. Non-contact is the best way to use a public men's room.

Back in the car, we are talking about how long I've wanted to dress up. When I was a about 5 or 6, my sister had gotten a bodysuit for some school activity and I remember being so envious and asking my Mom why I couldn't get one, too. Mom's reply was that they're only for girls and I felt so disappointed. A couple years later, I wish I could remember more of the details but when I was about eight, my Mom let me wear her old dance costume from when she was a kid for Halloween. I do remember our family going to the town's Halloween Rag Shag event. My Dad stopped at a gas station and my sister told me to "bat my eyelashes" at the attendant. Afterward we may have gone to my grandparent's house. When I was in my teens, Mom would go out shopping and I'd be alone in the house. I would poke around in Mom's dresser and would try on her bra and nylons. I cannot explain what compelled me to do this but it felt so good to wear those things.

I do know that I was jealous of the range of clothes available to girls. A boy wears pants and a shirt for every occasion; in the summer he could wear shorts and a tee shirt or tank top or no top at all. Girls could never be topless like a boy without causing an uproar since their exposed boobies would cause the world to spin backward. I guess guys are lucky in that way but...girls had so many options in the way they could be dressed. Jeans and a tee shirt, blouse and skirt, tank top and miniskirt, dresses, bikini tops, thongs, tube tops, sun dresses, sweater dresses, bustiers, halter tops, knee socks, tights, fancy underwear, shape wear, garter belts. So many options for the women while guys had hardly any choices. I had always wanted to experience the feel of silky material on my skin. Even with sleepwear, guys have something like four sleepwear options: flannel or cotton pajamas, boxers and tee, maybe one of those old time nightshirts or union suits and of course there is always sleeping in the nude.

After we married, I had the luxury of you enjoying sexy nightwear and I got a contact high when you would cuddle in bed with me. Luckily you knew that I liked how you looked in it and you enjoyed that it made our lovemaking more passionate. Lynn said that she'd never thought of it that way and agreed that guys never had as many options for clothes.

The frozen millpond has some skaters, a few young couples and one family with small kids. A path to the ice in the snow is pretty well defined. The wooden bench sits beside the path and we sit to put on our skates. She takes my mitten clad hand like a true gentleman and leads me to the ice. We're holding hands like a couple of teens on a first date and gliding across the ice. I tell Lynn that I want to take her photo and pull out the camera. She mugs a few goofy faces for me then tells me it's my turn to be the subject. Wait, what? I don't know if I want to have photos of me in drag and she says not to worry. They're just for us and won't be shared with anyone. I skate out about 25 feet and lose my balance and land on my butt. One of the young couples skates over to me and the gentleman offers his hand to get me back on my skates. I smile and say thanks. The three of us skate off to Lynn where they introduce themselves as Paul and Toni from the next city over and we tell them that I'm Dee and Lynn is Larry. Paul sees Lynn's camera and asks if we want a few photos of the two of us skating. Sure, we reply and we skate out toward the center of the pond. Arm in arm, making circles and figure 8's on the ice like the true lovers that we are. Back to the edge of the pond, we tell them that we'd been there for a while and were planning on leaving. They suggest we all go to a diner up the road a bit. I look at Lynn desperately. I was hoping to spend the day alone with her but her devilish grin comes back and says we'd love to go for a bite.

In the car I'm a bit miffed but she says that right now she's the man and I'm the woman so we're doing this. I think to myself, "Hmmm, this is interesting. I wonder where this is leading. Lynn has never acted like this."

At the diner, Paul tells us that he's a sales rep for an auto parts manufacturer and Toni's a writer for the local newspaper. Lynn and I hadn't really devised a back-story but I'm alarmed when Lynn tells makes up a story about me being a hairstylist and shared her real job, which is a rep at the state's DMV office. I gasped a bit when she shared the tidbits. I don't know anything about hair styling and what if Toni wanted me to offer advice! (In my mind, using the worst falsetto I think. "Oh, darling that color is just not you and that cut! It only works on a poodle!") I fear having too much conversation time with these people, as I don't really want to be exposed for fear of what could happen. Again I look desperately at Lynn. She sees my glance and smiles. We finish our coffee and Lynn tells Toni and Paul that we still have other things on our agenda and that we're heading out. Lynn gives Toni her phone number and says that we like them; maybe we'd go out some night for dinner and dancing. We say our good-byes and head to the car.

"Lynn, I don't know how I feel about some of these things you told Paul and Toni. I don't know them and don't want to put us in danger."

"Dee, as long as we're together we are safe. Nobody is going to take advantage of us. Just because you're dressed up doesn't mean you cannot throw a punch and I can wallop an attacker if necessary. Let's not dwell on things that could happen and enjoy ourselves. We'll be ok, I promise. I won't put us into a situation that is risky but you have to admit that we had fun at the pond and diner, right?"

I couldn't deny it. "It was a great adventure and we still are going to the other places, yes?"

"You bet we are!"

The parking lot for hayride was a couple hundred yards from the ticket shack. Packed snow gets a bit slick and we were careful with our steps. We buy our tickets and get into the queue. The wagon master helps me into the hay wagon and Lynn climbs in unassisted; we take our places on the rearmost bale. She pulls out the camera so we can snap photos of the dairy cows, a few sheep and goats dot the landscape. Lynn's paternal grandparents had a farm and she spent childhood summers there with her cousins. Cows were always her favorite animals and this place had plenty. Photo after photo of Holstein, Brown Swiss cows and a couple of goats were taken for her scrapbook. The wagon was driven between the rows of Spruce and Douglas fir and apple trees. We cuddled under our fleece blankets and enjoyed the rest of our ride. After bouncing over the trails we were more than ready to get back to the warmth of the car.

Our last stop was the town's big event of the season; The Christmas tree lighting on the town green followed by caroling. The pine tree on the green was surrounded by the townspeople, anxious to see thousands of lights and the silver star atop light up. The Mayor and other dignitaries read their speeches while the kids ran around the tree. The P/A announcer started the countdown... 3, 2, 1 LIGHT IT UP! Cheers, oohs and aahs as if it were the Fourth of July. We were led in a few choruses of the standard carols finishing with "Jingle Bells."

Our day had been quite the adventure, Hell the whole weekend was awesome. It is like something new clicked between us and it opened a path to a brand new world. For years, I've been wishing spend an entire day en-femme. The reality was even better than the dream. I had spent a Saturday at the mall buying my own "special" clothes and today I am dressed up and sharing time with my stunning wife (dressed currently as Larry) freezing my cute (not-so) little ass off but loving every minute. I enjoyed knowing that I am able to go out into the world as I please, knowing that we're enjoying ourselves and able to dress as I please.

Where will this all go, neither of us knows but we will enjoy the ride.

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AnonymousAnonymousover 4 years ago
A good pair pf stories.

I was reading an author, named Slightly Rude, when I came across your comment about Michelle. Out of curiosity I touched your name and found that you are an author also. You stories are great and hopefully you will continue to write.

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