I couldn't help but feel very self-conscious. It had been nearly two and a half years since I had been out in public dressed as Jenni. I walked through the lobby of the hotel with far less confidence than I had when I was out walking the streets looking for a trick. I tried to dress down but couldn't help but think all eyes were on me, thinking I was some cheap, ugly hooker going to meet up with her date. The hotel itself was a far cry from the motels I had been conducting my business. This was a four-star hotel with a spacious and well-decorated lobby. To me though, everything seemed just a little off.
I felt a sense of relief once I made it to the elevator and even more so when the doors opened. I quickly entered the empty car and pressed the button for the seventh floor. As the doors started to shut I took a deep breath until of course a gentleman dressed in business casual attire and newspaper in hand snuck in between the doors. My instinct was to press the "door open" as I mentally screamed to myself "wrong button" as I did.
"Thank you very much," he said kindly.
I gave him a polite smile in return, afraid to verbally engage him.
"Oh look at that, we're going to the same floor," he said making uncomfortable small talk. My heart was racing and I could feel myself sweating. What the fuck was wrong with me?
"How about that," was all I could awkwardly muster in return.
The elevator reached the seventh floor relatively quickly and my fellow passenger offered politely for me to exit first. Ladies first. I said thank you with a smile and stepped off, quickly trying to figure out which direction I should be heading without breaking stride. Room 717 was to the left and I was able to turn and start to walk down the hall without hesitation. My elevator friend followed me. I stopped in front of the door and paused before knocking to take a deep breath and make sure I looked okay.
"You look great! Let me get this for you."
The man from the elevator stepped in front of me with a key and unlocked the door. He held the door and offered for me to come in. Fuck me!
"I don't bite. Come on in."
I walked in cautiously and asked, "So you are Brad?"
"In the flesh. And I'm really hoping you are Jenni or I just made a really big mistake."
The upside was that Brad was even more attractive in person than he was online. I had met Brad in an America Online chat room called BiCuriousMM. We had been chatting online for the better part of five months before he mentioned that he would be coming to my area on business. He lived and worked in Baltimore but his traveling took him to several cities in the Midwest and Southeast.
The downside was that there was always a chance that this wasn't Brad and that I had just walked into a bad situation. I quickly surveyed the room. The desk had papers and a few file folders. There were a few suits and dress slacks hanging in the closet. It was a good sized suite with a living space and a separate bedroom. It certainly fit the bill for a seemingly important business person.
“I knew it was you from the description you gave me. Long black skirt, black boots, white top, and a denim jacket.”
I was relieved to know this was in fact Brad but still, I stood in the short hallway of his hotel, trying to find the right thing to say.
I had gone over a year after school without even thinking about dressing. I immediately recognized that living at home would be terribly constraining and had all but given up on Jenni. Then out of the blue, the woman who I shared my office with asked me if I ever wore women's panties. The question was asked as a joke until I quickly answer that as a matter of fact, I had. Deanna was a nosey office gal so naturally, she progressed through a checklist of clothing items, and after confirming that I had in fact worn each and every one of the items on her list she admitted she was a little turned on.
A week later there was a small gift box on my deck from Deanna with a card that read, "I dare you to wear these tomorrow." I unwrapped the box to find a matching blue floral print bra and panties. Like a recovering addict afraid to touch the drink, I just stared down into the box. I thought to myself, if you do it, there is no turning back. I ran through a million scenarios in my head, none of them resulting in me being able to do this just one time.
I picked up the satin panties and held them for a minute before picking up the matching bra. I held them both in my hands for a moment before getting up, placing both items in my pocket. I made a short walk to the restroom down the hall. I went into a stall, dropped my slacks, removed my boxers, and slid into the silky panties. They felt amazing under my pants. I could feel myself getting hard. I followed suit removing my shirt and put on the bra. It was a little snug but it fit well enough for me to keep it on. I buttoned my shirt back up, tucked it in, and took a deep breath. I walked back to my office and sat down.
Deanna arrived about twenty minutes later and asked if I received her present. I confirmed that I had and that they were so cute, I couldn't wait for the next day to put them on. She leaned against the threshold of the door.
"You have no idea how turned on I am right now," she said fanning herself with her hand. "Can you show me?"
We closed and locked the main door to our two office suites. I quickly undid my pants and gave her a quick peek. After pulling them back up, I unbuttoned the top half of my dress shirt to show her the bra. As flush and turned on as she was, I could feel my cock getting hard as well. I buttoned back up and told her to open the door so no one would be suspicious. She sat down in the chair across from my desk.
"OK. What the fuck?" she asked. "I was kind of joking around about things but you are fucking serious aren't you? You really have worn all the things you said. I mean you put those on without hesitation."
"Absolutely. In fact, you would be shocked at some of the things I've done dressed as a girl. I'm a different person altogether. Half the time I don't know what the fuck I'm doing. And then I do it and I can't get enough."
A little over a year after that conversation, I was standing in front of a handsome stranger named Brad, wondering that same question that always seemed to haunt me. What the fuck am I doing?
The conversation with Brad online had started relatively innocently at first. It was the third or fourth time we connected that the topic of meeting in person was brought up. There were several more that followed, each getting a little more flirtatious, a little more detailed, and finally very upfront. Brad was looking for a very discrete relationship with a younger male, who was willing to dress like a girl, that he could treat as a girlfriend when he traveled. He was in fact very bi-curious. Brad admitted that it was not from a lack of sex at home. He was quite adamant that he and his wife regularly had sex. He just wanted something different. Different was me.