Several years ago I had an opportunity to go out of town with my 'work wife'. She was a woman in my department that I was very close to, and we spent a lot of time together on projects. We always playfully flirted and joked, but there was never a hint of any type of deeper involvement.
Then she was supposed to go to Minnesota for a week-long computer class with another guy in my department. At the last minute, he had a family conflict, and my boss asked if I could go in his place.
It was over Valentine's Day week, but that wasn't a very big deal with my wife. We had been gradually drifting apart, with her spending all of her time with our kids and her part time job, she wasn't interested in me except as a friend. We hadn't had sex in over a year, and despite my best efforts, she really didn't seem to care.
My wife said to have fun, and didn't really even ask who I was going with. So I quickly packed a suitcase for a week, and on Sunday morning I left to pick up Gina for the 6 hour drive to Minnesota.
Gina's husband Frank didn't mind that she would be gone over Valentine's Day either. They had been cool in the bedroom for a very long time, each focusing on their own lives.
We had a fun drive, listening to music and just chatting about all kinds of things that we usually didn't get to do at work.
We got to the hotel, a nice 3-story building in the industrial park near where our class was to be held. We checked in and went to our rooms to freshen up before going out for dinner that night. I hung up my pants and dress shirts in the closet, and noticed that I had not packed any underwear. I specifically remember taking a week's worth out of my dresser drawer, but in the rush to pack, I must have left them on top of the dresser.
I called Gina and said I was going to run over to the nearby Target store to pick up a few things, and would call her as soon as I got done. She said she wanted to come along to get a chance to walk around after the long ride. I was hoping to go alone, but thought I could still be discrete.
We got to the store and I suggested we split up and meet back in the front of the store in 10 minutes. Gina was puzzled as to why I was being so evasive.
"Are you picking up something personal like hemorrhoid cream or something?" she teased.
"No," I laughed, "I forgot to bring underwear."
Gina thought that was pretty funny. "What's the big deal? I have seen men's underwear before. I buy it for Frank all the time. Come on, I'll help you pick something out"
She led me to the men' department.
"What kind do you like to wear? Don't tell me you're a tighty-whitey guy? That's all Frank will wear. I've tried buying him more modern styles, but he won't wear them."
"I usually wear boxers. Mary buys me white or blue. Hanes or Fruit of the Loom or whatever is on sale."
"Hmmm, boxers are sexy, but we have to spice up your wardrobe a bit. Let's see if we can find something more fun than plain colors."
Gina started looking through the packages in my size. She dug around and pulled out a 3-pack or boxers with bright colors in circles and triangles. Here, how about these? They look modern."
"Hmmm...when Mary sees them, she'll know I didn't pick them out."
"Who cares? You're a grown man -- you can pick out your own underwear. Maybe that's all the store had, or maybe you want to try something new?"
"Yeah, you're right. It's time for me to be a little bolder. Pick out another package, I have to get enough for all week."
Gina found another 3-pack with bright stripes and other designs.
"Now when I see you all week, I'm going to wonder which pair you're wearing. I'll guess and you can tell me if I'm right," she suggested.
As we walked to the checkout, we came across an end display of Valentine underwear. They had men's briefs and boxers in various reds and whites.
"Hey, look at this! You have to get a pair of these!" Gina held up a pair of white boxers with little red hearts all over them. "These would look so cute on you!"
"I definitely can't buy those! Mary would never believe that I bought them. Besides, I already have 6 pairs of new boxers, why would I pay more for a single pair?"
"Ugh! You men are so cheap sometimes... I'll buy the for you as a Valentine's Day present, You just have to promise me that you'll wear them on Tuesday. You can throw them away instead of taking them home after that if you want."
"Well, I don't know..."
"Come on! You just said you want to be a little bolder. Besides, I'd like to imagine you wearing these on Tuesday."
"Oh, all right. You win. Just like my wife. You know, she calls you my 'work wife', because I talk about you a lot at home."
Gina grabbed the heart boxers and we started walking to the checkout.
"That's funny. As your 'work wife', are you going to buy me any flowers or candy for Valentine's Day?"
"Maybe I should buy you some sexy lingerie? It's been a long time since I've bought anything like that."
Gina laughed, "It's been a very long time since I've worn anything like that!"
We were approaching the women's department, so I called her bluff, and turned in by the bras, looking for sexy underthings. There was an end display with bras, panties and camisoles.
"Hey, look at these! I think I should buy you something here. What size do you wear?"
"Oh no, I'm not sharing my clothes size with you. I'll look through and see if they have anything in my size."
"How about one of those silky red camisoles? That would look sexy on you!"
Gina looked through the rack. "You're in luck, they have one left."
"I'll buy it for you. See if they having matching red panties, too"
"Why do you guys call them panties? Women just call them underwear."
I grinned, "Panties just sound so naughty..."
Gina laughed, and looked through the rack. "Yup, they have the 'panties' in my size too."
"Good, I'll take them. Let's go."
We walked through the checkout. The clerk was very friendly, and chatted a bit about our purchases, assuming we were married. Gina was a little embarrassed, but played along.
When we got outside, we burst out laughing.
"Well, that was fun, Mr. Miller!"
"Yes, thanks for going shopping with me, Mrs. Miller! Let's go somewhere to eat, I'm starved."
We found a nearby sports bar, and had a few beers and a sandwich. It was really fun flirting away from the gang at the office, and we talked about all kinds of things.
"You know whenever I see you now, I'm going to wonder which boxers you're wearing...."
I grinned. "and I'm going to imagine you in that red outfit!"
We finished the meal and went back to the hotel. We said goodnight, and went to our rooms. I opened the shopping bag and looked through the boxers. I was surprised to notice that I had a hard-on from all of the flirting and underwear talk. I opened the packages and tried on the white ones with red hearts. The new material felt great on my throbbing dick. I took them off to save them for Tuesday, and lay down on the bed and jacked off, thinking of Gina in that red silky camisole and panties.
***
Monday morning, Gina and I met in the lobby for a quick breakfast at the hotel buffet. We grabbed a table and sat down.