My First Time

I was still in my first year at the company when my boss John asked me to go to a yearly convention with him. I was a bit surprised. Outside of my interview, I hadn't really interacted too much with him at work. But he told me I had potential and that this would be a great learning experience for our industry. I felt I couldn't say no. Although it was only a state away, he informed me we'd be flying out tomorrow(Tuesday) and wouldn't be back until Sunday. We shook hands and he went back to his office. I sat at my desk, excited that he asked me to go, but also nervous and anxious. But, I figured if it would be a good learning experience and a good way to get to know my boss a little better.

I went home that night to pack. It's important to note now, that at that time I was a very closeted cross dresser. I had begun in high school and it continued off and on into my mid 20's(when this takes place). I was single and lived alone. So every night when I got home from work, I would transform from Brian to Brianna. I didn't go "all out" all the time. Most nights it was panties, stockings, lingerie, etc. But some nights I would do make up, wig the whole 9. Social media was in its infant stages at that point, so I mostly chatted on stuff like AOL messenger, chat rooms etc. I was Brianna when I was online. A 20 something blonde girl. Internet porn was also just poking its head out. And that is when I first became VERY bi-curious. The point of all this is, is that I was excited to be able to dress up in a new place. A nice hotel room, plush linens, a robe, etc. I made sure I packed my favorite stuff. For some reason, I felt like a kid of Christmas. I could barely sleep!

I met John at the airport the next morning. He chuckled at me as I had dressed for work. Him? Jeans a t-shirt. "Sorry sir, I didnt-" "Hey, it's OK." He said cutting me off. "No need to be so formal all the time. And hey, call me John." We boarded the plane and he was going over things with me. I wasn't really listening though. All I could think about now was becoming her. I was even contemplating getting on the local Craigslist(before apps) and finding a guy. I had only ever done that once. He was older. I met him in an empty parking lot after dark and sucked his cock. He wasn't overly long, but was pretty thick. I was fully dressed. It felt great. I knew I wanted more, but, we almost got caught and that scared me away from doing something like that again. But, I'd have my own hotel room now.

We landed and headed for the hotel. When we went to check in the receptionist informed us that we had only booked 1 room. John apologized and said that Sandra(his assistant) must have not realized I was joining. He tried to book another room but the hotel was full. The receptionist said they would try to get a cot up there ASAP. "Well, looks like we're roommates" he said to me. My heart sank. He talked some more on the elevator up, but much like the plane it was in one ear and out the other. I decided on the way up that I would at least wear panties under my clothes all weekend. If it's all I could do, then so be it. I don't usually wear them to work, so it would be exciting and a change for me. I was attempting to be more brave.

So now we fast forward. We went to the hotel bar for dinner and drinks. I actually got to know John pretty well. He's not really a hard ass at work or anything, just very focused and professional. But outside of work he's very laid back and relaxed. He's funny and charming and seems to have a story about everything. The bar was closing down. He told me he had a ritual he did every year of this thing on the first night and asked if I wanted to join him. I of course asked what it was. He said it was just simply a drink and a cigar on the balcony to end the first night(he said he also repeated it on the last night, just as a way to start and end the trip on a good note). I told him I didn't smoke, but would give it a shot. I was buzzed, having fun, and wanted to keep it going. We got back to the room and I told him I wanted to toss my gym shorts on, just to be more comfortable. He said he'd meet me on the balcony. When I took my pants off, I was reminded I had been wearing a thong all night. I was having so much fun that it slipped my mind. I became excited. What a rush! I thought. I had been wearing these and no one knew! I was going to take them off but decided not to. I just pulled my shorts up and smiled in the mirror(I was pretty damn buzzed haha). I pushed the curtain aside and went to tell him that I didn't mind taking the couch when I froze in my tracks. There he was. Sitting in a chair on the balcony. Sipping a scotch and smoking a cigar......completely naked.