Christie left for two weeks on the Monday before Thanksgiving, so I’d been on my own for a few days. She still texted or called every day. She’s on the east coast, so she could message me in the morning, and when I got up a few hours later, I could read it. Of course, she sent me a note every morning, telling me what pair of panties and bra to wear, so we would always be wearing matching lingerie.
So on Wednesday, she instructed me to wear the white bra and thong set she’d given me. I knew that it would be a casual day at work, so I put on some women’s trouser socks, jeans, and a dark blue dress shirt. I grabbed a casual black blazer jacket, too, to make sure the bra wasn’t visible.
I spent most of the day at work in the warehouse, doing inventory, so I swapped the jacket for a hoodie with the company logo on it. There weren’t many people working, and just after lunch, word came around that a group was planning on going to a local pizza place for happy hour after work. I had no other plans, so I thought I’d drop in.
The pizza place has a large outdoor patio that they had set aside for us. It has a few heaters, and a roof, so it was comfortable. I decided to stick with the hoodie. I got there, looked around for people I knew, and saw my co-worker Lauren waving me over. We work in different departments, but you may remember from earlier posts that we’d traveled together to a conference once, and she knew about my dressing. I got to the table, where she and a few women from her department were sitting. I knew a couple of them. Lauren gave me a hug, and left one hand lingering on my back, kind of rubbing my back where my bra was, as she introduced me to her co-workers.
I had just sat down with them, when our waitress came over and asked, “what can I get you ladies?” Two of the women looked at me and giggled, but I made a gesture to Lauren as if to say ‘you go first’ and the moment passed. She took orders around the table, and got to me.
“And for you, miss?” she asked. Everyone giggled, so I tried to smile. The woman before me had ordered a beer, so I just said “I’ll have the same, please.”
The evening went on uneventfully. Whenever the waitress returned, she’d check if anyone needed refills on drinks, usually calling me “honey.” Lauren occasionally put her hand on my back as she told her friends about the last time we went out. (She left out that I had been wearing a skirt and heels.) Eventually, people started to leave, and Lauren and I were the last at the table.
“What are you up to for Thanksgiving,” she asked. I told her that I didn’t really have any plans this year. “I don’t either,” she replied. “I’m not crazy about turkey dinner, but I hate to just sit at home. Do you want to go out for dinner?” I didn’t really like the idea of sitting at home, either, so I said yes. Lauren said she’d find some place for us to go, and let me know. We walked out of the pizza place, among the last to leave.
A few hours later, my phone rang. It was Lauren. “How about Roy’s?” she asked. Roy’s is a Hawaiian fusion restaurant nearby. I was surprised that they were doing a turkey dinner, but it sounded like a good place to go. It has a nice bar, and great service. Lauren hesitated, then told me that she wanted us to both dress up for dinner. She must have sensed my hesitation, because she said “please?” in that way that someone does when they really, really want something. I couldn’t refuse. Lauren said she’d make the arrangements.
Of course, I texted Christy to let her know. She was excited about me going out with Lauren again. She suggested that I wear her dark green cocktail dress and the short jacket that goes with it.
The next day, as I was getting ready, I got another call from Christy. I could tell she was trying to give me a little boost of courage before going out. She decided I should wear the black padded bra, along with my “special” gaff. She also had me wear a pair of black, lace top stockings, the style that stay up on their own. She had gotten me a pair in size tall, so they were tall enough to stay hidden beneath the hem of the dress. Christy also helped me with some makeup choices.
After showering and shaving everything carefully, I sat down and did my nails, using a dark maroon color that went nicely with the lip gloss Christy had chosen. When my nails dried, I did my makeup and hair, and got dressed. I put on the gaff, tucking my male parts securely away. I put on the bra and silicone breast enhancers. The dress Christy loaned me had a v-style neckline, so I managed to tug my chest together to create a bit of cleavage. I put on the stockings and a pair of black platform pumps.
Lauren made the reservations for 7:30, but wanted to meet at 6:30 for a drink. I checked to see if any neighbors were out and about, and when I was satisfied the way was clear, I headed out to my car and to the restaurant. I found parking right away – it didn’t seem as though many people were out. I walked to the restaurant and went in. The hostess looked up and greeted me, but before I had to say anything, I could see Lauren at the bar. She waved me over, and we hugged. She looked great, in a black satin and velvet dress. Lauren complimented me on how I looked. Our bartender, a very attractive woman with a mass of wavy red hair, came over. Lauren introduced us, and she and took our drink order. It was happy hour, so we ordered “Hawaiian” martini’s with vodka and pineapple juice, which turned out to be frighteningly easy to drink.
Lauren and I started talking, and before long, we were reordering drinks. When the hostess came over to seat us, Lauren looked at me and said “let’s just stay here.” Our bartender, Catherine was her name, told us that would be fine – the restaurant wasn’t busy, and we were welcome to sit at the bar and make a meal of the appetizers on happy hour special.
As we sat, I realized that Lauren and I were both getting a little giggly. She was sitting very close to me, our legs and shoulders touching. Every now and then, to emphasize something she said, she would either pat my thigh or put her hand on my forearm.
At one point, Lauren excused herself to the ladies’ room. Catherine came over to me. “Your friend is really into you, babe,” she said. “You both look fantastic.” She checked our drinks. “Everything still good, here?”
“Everything is fine, I think. This is a lot more fun than dinner.” I said. We chatted about the holiday. Catherine, it seemed, volunteered to work because she wasn’t all that excited about Thanksgiving, either.
We stayed for another round or two of drinks and some dessert, before saying goodnight to Catherine. As we walked out, we both realized we were in no shape to drive, so as we passed a taxi stand outside the restaurant, Lauren grabbed us a cab. We decided to go to my place, since it was pretty close.
We got back to my apartment and went in, and collapsed on the couch. We both kicked our heels off, and Lauren brought her knees up next to her. She hugged me, leaned near my face, and told me what a wonderful time she had. I put my arm around her, and we cuddled. “Tonight was really special for me,” I told her. “I can’t believe I felt so comfortable the whole night.” Lauren kissed me and leaned onto my shoulder.
At some point, late, we decided it was time to sleep. I found some extra pajamas for Lauren, and we undressed each other. I was pretty nervous about where things were going, until I realized that we both had quite a bit to drink. We were asleep in seconds.
The next morning, I woke up, and as quietly as I could, went to the kitchen and started coffee. I was wearing a pair of flannel pajamas with pretty short bottoms. Lauren came out a minute later, insisted that I didn’t wake her up, and very happy about the coffee.
We talked some more about what a wonderful night we both had, and made a plan to go get our cars. I loaned Lauren a pair of leggings and a sweatshirt (her heels from last night were the only shoes she had, but made the outfit look pretty sexy). I took a little longer to get ready, having to shave and put on a little makeup, before putting on a pair of leggings (mine had those cute sheer panels on the calves and thighs), a beige bra and a white hoodie. Lauren got an Uber to take us back to the restaurant, where we found our cars not too far apart. We kissed goodbye and went our separate ways.
My heart was pounding from excitement. I couldn’t wait to tell Christy about our adventure when she got back.