Several years ago I had an opportunity to go out of town with my 'work wife' over the Valentine's Day week. Both of us had been experiencing rough times with our spouses, despite our best efforts, and neither of us had sex in many months.
When we arrived in Minnesota for our class, I realized I had forgotten to pack underwear. Gina was delighted to help me shop for some boxer shorts, and we also wound up buying each other some fun Valentine's Day underwear. A little modelling for each other led to some hot and passionate sex for the rest of the week.
We discarded the evidence of the holiday underwear and went back to our separate lives. We still worked closely together, and we tried to live by 'what happens out of town, stays out of town'. But every time I saw Gina, I was reliving our sexy week together, and from her sly comments and glances, I knew she was too.
Now, eight months later, Gina needed to go to a conference in a Chicago suburb the week before Halloween. She brought it up to me, smiling and suggesting I might want to attend as well. I thought it over a lot. The conference was about things that were my responsibility at work, and I had attended a similar one five years ago. I mentioned it to my boss, and he agreed it would be good for me to attend too.
We rented a car and drove to the conference on Sunday afternoon. The air was full of sexual tension, with neither of us coming right out and saying anything about sex. It was a long ride.
We got to the hotel and went to our rooms. I did remember to pack underwear this time, and brought along the boxers that Gina had helped me pick out. We met up a few minutes later to go out to dinner. We found a nice place for dinner, and along with some wine, loosened up quite a bit. We reminisced about our last trip out of town together.
"I'm wearing boxers you helped me pick out last time. Guess which ones."
"Hmmm, the white with green stripes?"
"Lucky guess! What are you wearing underneath?"
"You'll just have to be a good boy tonight and maybe you'll find out...", she replied coyly.
We had intended to see a movie after dinner, as the 'date nights' that we had done in February. However, the week before Halloween, all that was playing were slasher flicks or children's movies. As we left the restaurant, we drove past a used clothing thrift store, with a big sign, 'Your Halloween Headquarters'.
"Hey, do you want to stop here and walk around? I like looking through the costumes around Halloween."
"Sure, sounds like fun."
We pulled into the parking lot and went inside. They had several long rows of wild clothes, some official costumes, and others just weird donated clothes. We had fun walking around and pointing out different costumes.
I held up a doctor's long white coat and leered, "Hey, want to play doctor?"
Gina laughed, and replied, "Are you a full-service doctor? It's been a long time since I've had a thorough examination."
"Why, yes, Mrs. Wilson, I'd be glad to offer my services."
"Well then, Dr. Miller, I had better find a nice outfit to wear to my appointment."
I kept the doctor coat, and we walked around looking at the other clothes. I added a patterened hospital gown, and Gina found a 1950's-era floral house dress. "This looks just like something June Cleaver would wear!" It was bluish, with a collar and buttons on top, down to a pleated skirt on the botton. June would wear this with pearls while preparing dinner for Wally and the Beaver. "I think I'll take it. I better find some accessories."
Gina found some a cheap necklace with big blue plastic beads. "How retro is this? Let's see what else will complete the outfit."
We walked around the store, and Gina found some matching shoes, then stopped by the lingerie section. There were lots of old-fashioned bras. She picked up a big one with stiff material and pointed breast cups, and laughed, "I'll bet this is what the well-dressed woman wore in the 50's."
I always thought that old-fashioned lingerie was unattractive, but with the 50's role-play we were starting, it suddenly seemed sexy. "Don't forget the granny panties", I joked.
"Always the panties with you. You know, women just call them underwear."
The store had several individual panties hanging from the racks, but nothing that wasn't too used, or in her size. On the end of the aisle, I spotted several packages of clearance panties, and pointed them out to Gina. She came over and found a three-pack of nylon full-cut underwear, in light blue, pink and yellow. "I can just imagine June wearing these too! Now, Dr. Miller, we need to find the rest of your outfit."
"What do you mean, men wear almost the same styles today."
"Oh, you guys don't know anything! If we are going to look the part, we have to find the right clothes."
Gina walked me through the mens section and found some ugly tan polyester pants. "Now these look like 50's style pants!" After a little more searching, she found an old white long-sleeve dress shirt and an old-fashioned tie. "There, Dr. Miller, you'll look like a proper 1950's doctor. Now for the final touches."
Gina walked over to a small section of men's underwear, and held up a pair of red and white striped boxer shorts with a yoke front and grippers. "My dad used to wear underwear just like these. Are they your size?" They were, so I added them to my pile of clothes. We couldn't find any vintage a-shirts, but Gina agreed that my a-shirts and socks would have to do.
We checked out and drove back to the hotel. "That was really fun! I've never shopped for vintage clothes like that before."
"Yeah, Dr. Miller, you're fun to shop with. Now we have to get into character for my appointment."
We went to our separate rooms to change into our costumes. I pulled off all of the store tags and took off my clothes. I left on my a-shirt and black dress socks, but swapped my boxers with the retro yoke boxers. I put on the tan pants, white shirt and vintage necktie. My black dress shoes and the long white doctor coat completed my outfit.
I cleaned up the room a bit and brushed my teeth, waiting for my next 'appointment'.
A short while later, there was a knock on my door. I opened it to see Gina looking stunning in her floral dress, matching shoes and blue bead necklace.
"Hello, Mrs. Wilson, come on in."
