My work wife and I were spending the week before Halloween at a conference in a Chicago suburb. We were both lonely and unhappy in our marriages, and had hooked up around Valentine's Day before this conference came up.
We were feeling horny, and had stopped at a thrift store on a whim and bought some vintage clothes to dress up and role play a doctor/patient in our hotel room last night. It was such an exciting and arousing game that we both felt so alive.
After showering, we slept naked in each other's arms all night, then had another brief round in the morning before we had to get ready for the day's events. Gina threw on her old clothes and was getting ready to go back to her room for a shower and clean clothes when she came up to me holding a pair of the pink granny panties we had bought last night for our role play.
"I think you should wear these under your dress clothes today, " she purred. "I want to imagine you in them all day, and maybe you can model them for me tonight."
I smiled. "Sure. I've never worn panties before, but it sounds like fun. Maybe you can wear something of mine under your clothes? I have some tighty whities or boxer shorts."
I walked over to my suitcase, and rummaged around to pull out my clean underwear. "Here, any of these interest you?"
Gina looked through my stack of underwear, and held up a pair of white boxers with little geometric shapes. "I think I'll wear these under my skirt, " she giggled. "Ok, off to shower and get dressed. I'll meet you for breakfast downstairs in an hour."
She left and I showered and shaved. I put on the pink nylon granny panties and instantly got a hardon. The silky material felt so good on my cock and balls, and didn't provide much support as I made a huge tent in the loose material. It was going to be interesting to keep my cock tucked in all day in my dress pants.
I met up with Gina for breakfast and we discussed our day's activities, as we were going to split up to attend different events. "I am so looking forward to being with you tonight," Gina told me. "We'll have to think up another game to play."
All through the morning, as I attended various presentations, my mind was wandering and fantasizing about our role play last night and what might happen tonight. Of course, my cock was throbbing as it tried to escape the nylon material, and I had to walk with my handouts in front of my crotch to hide the constant tent.
We met up for lunch, and Gina whispered to me, "I am so wet right now. Your boxers feel so open on my pussy that it almost feels like I'm not wearing anything under this skirt."
I grinned. "What do you want to do tonight?"
"Um..." she hesitated.
"What?"
"No, it's ok..."
"No really, tell me. Now I'm curious," I smiled.
Gina blushed and hesitated again. Then she seemed to make up her mind, and she leaned in to whisper to me, "I want to be a man. These boxers got me thinking. I want to dress up as a man and make love to you. Is that weird?"
I was surprised, but replied, "No. I think that is really hot, and would be fun to play with you."
"Really? I have one more idea. My husband would never want to try new things, but I always wanted to wear a strap-on. Is that too kinky?" She looked away quickly.
Wow! I didn't expect that. "Um...well, I guess not. I've never seen one personally, but they seem pretty popular." I thought it over. "Sure, let's see if we can go shopping again tonight." I grinned at her.
Gina seemed embarrassed, but laughed and said, "It's a date! You take me to the nicest places!"
We laughed, and split up for the afternoon sessions. I was harder than before thinking about Gina in a strap-on. I guess that meant I was going to explore some new adventures too. I wasn't sure how I felt about that, but everything with Gina was intimate and open, and I trusted her to be discrete and safe.
We met up again for dinner, and Gina told me she had searched an internet kiosk on break and found an adult toy store on the edge of town. We decided to drive past it on the way to find a restaurant and check it out. The store didn't look too bad, so we stopped at a restaurant for dinner and to get our courage up.
Throughout dinner we danced around the idea, and flirted quite a bit and I found myself getting very hard again.
"I am so wet, " Gina shared. "I think your boxers are soaked." She glanced around the restaurant, and since we were relatively secluded, she lifted her skirt and showed me. Gina was wearing my white boxers with little geometric designs, and I could see how the crotch area was slightly darker and glistening from all of her juices.
"I am so hard, " I whispered. "These panties keep rubbing against my cock and driving me wild!"
"You and your panties! You do know we just call them underwear, right?" she smiled.
We paid the bill and drove to the adult store. The store was brightly lit and looked relatively new. They had a lot of DVDs and magazines, as well as toys and lingerie. There were two other people browsing, a guy by the gay movies, and a woman by the bachelorette party favors.
We wandered around until we came to the strap-ons and dildos. "Wow, how about this?" Gina asked, as she pointed to a huge 16" black dildo called the Exxxtreme Dong.
"That looks like a pain in the ass, " I countered.
"I'm kidding!" she replied. "I was thinking of starting small..."
"Well if you want to put it where I think you do, I hope we can start small..."
"This was my fantasy, but are you sure you're ok with it? I don't want to hurt you. You just get me so horny and hot. If you want, we can just play around and don't have to do any penetration..." Gina trailed off.
"To be honest, I don't know what to expect. But it makes me excited seeing you get excited, so if we play slow and gently, I am up for trying new stuff with you. But I'd recommend starting small and using lots of lube, " I whispered.
Gina agreed, and we looked around until we found a 6" rubber strap-on cock that didn't look too thick. We had to find compatible lube, and weren't sure what to look for. Gina's newfound courage took over, and she asked the clerk for her advice, who recommended a brand. The clerk told Gina, "Be sure to let him know who's the boss", and gestured toward me. I blushed, and they both laughed.
We drove back to the hotel, and Gina had fun stroking the tent in my pants along the way. "I can't wait to play with this guy!"
We went back to my room, and Gina said "Let's get you ready." She undressed me, leaving on the pink nylon panties. Then she helped me put on the old-fashioned pointy white bra that she wore last night, as well as the June Cleaver dress and necklace we picked up at the thrift store. I was a little bigger than Gina, but the dress fit good enough. She took out her lipstick and put some on me, then a little other makeup and exclaimed, "You are so pretty!"
"Is that ok if I wear some of your clothes?"
"Sure, help yourself."
Gina took my dress pants and shirt, and got some clean boxers, an a-shirt and dress socks out of my suitcase. "I need some dry boxers - I'm afraid the ones I'm wearing are all wet now." She winked at me.
Gina went into the bathroom and changed clothes. She came out a little while later, smiling and walking a little funny, as I noticed a tent in the dress pants. She was wearing the strap-on under the pants.
"Hey, little lady!" Gina exclaimed. "You're looking mighty fine. Why don't you come over here and sit on my lap, and we'll talk about the first thing that comes up?"
She sat on the couch, and I laughed and walked over by her. "Yes sir, " I blushed.
I say across her lap, and she leaned in to kiss me. This was strangely arousing, and I kissed back, getting into more character.
We made out for a while, then Gina ran her hand across my breast, feeling the bra under the dress. "Those are some nice titties you have!"
I looked shyly away. "Would you like to see them?"
"Yes I would!" Gina reached around and unzipped the dress, and helped pull the top down to my waist, exposing the old-fashioned bra. She ran her hands across my breasts and sides, then slid the left strap off my shoulder and peeled the bra cup down to expose my nipple.
