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.

"So Jenni, please come in and sit down. Can I get you a cup of coffee or anything, maybe water?"

I thanked him and took him up on his offer for a water. I was nervous. I wandered over to the window to see the view from the window. I had sized Brad up enough to know that I was more than willing to give him the blow job I had promised. Brad was handsome and very fit. I found it hard to believe he was fifty-three years old, thirty years my senior. But, for fifty-three he was in great shape. He tapped me on my should and handed me the bottle of water.

"So let me say this Jenni," as he touched me on the arm. "You are even more amazing than I imagined you would be. But, you seem really uncomfortable and if you would rather just go, I totally understand."

And he was sympathetic and understanding.

"It's actually just the opposite, Brad. I would love to stay, suck your cock, kiss your lips, and let you fuck me all day. But, I know that's probably not in the cards."

We both laughed. Then he leaned in toward me. His lips softly kissed mine for a brief moment before moving his face away from mine.

"That was nice," I said softly as I stepped toward him, planting my lips back on his. In a heartbeat we made out, within seconds we were on the couch, and only a few minutes after that I found myself undoing the belt and working his pants down over his rock-hard cock. As I did, I saw the outline of his cock pressing the tight-fitting fabric of his red briefs. It didn't take much for his underwear to come off after his pants, fully exposing his cock for my taking.

I slid to the floor, kneeling in front of him, eyeing his hard-on. I realized how much I longed to have a cock in my mouth but I took a moment first to take it in my hand and stroke it. I loved the feel of his soft skin up and down his shaft and how my fingers slid over the head. My other hand took his very nicely groomed ball sac and started to fondle them. His balls were enormous. I put my lips against the head of his cock and slowly allowed his cock to fill my mouth and throat. I stopped and let my tongue lick around his rock-hard shaft before sucking back to the top, dragging my tongue up the center of his dick. I softly kiss the very tip of his cock and was already tasting a little precum. Brad moaned in delight.

I looked up at him to find his head tilted back, eyes closed, and thoroughly enjoying things. I took his cock back in my mouth, slowly sucking up and down the shaft. I licked up and around every inch of this beautiful cock. I was enjoying it as much as he was. I licked down his shaft, eyeing his ball sack. They were so big, but I couldn't resist. I took his first nut in my mouth and then the second, sucking on each of them for a few moments. I struggled but was able to fit them both in my wide-open mouth. I let my tongue enjoy these two huge nuts before returning to the massive hard-on in front of me. I licked back up to the head and moved my mouth over his cock before taking it all in my mouth and into my throat, gagging as I did. I firmly attached my lips to his shaft as I sucked up and down. I felt it stiffening and start to pulsate as I quickened my movements. Brad moaned even louder.

While I knew he was close, the first shot of cum in my mouth caught me off guard, but as its sweet taste hit my tongue I was ready for more. Wave after wave of his cum filled my mouth and throat, barely allowing me any time to swallow before I was filled up again. I had never experienced drinking in so much cum in my life. I licked up the few drops that I felt on my lips before looking up at Brad's smiling face showing him my empty mouth.

"That was incredible," he said with a great deal of enthusiasm as I joined him on the couch. He reached for his underwear but I shook my head.

"Well thank you but don't put those on just yet. What's the hurry?" I asked taking his softening cock in my hand. "I just want to touch it and hold it for a moment just in case we never see each other again."

I gently squeezed a little more cum out of the tip, licking it clean.

"I have to make sure you're cleaned up before you head off to your important meeting or whatever it is you're all dressed up for," I said with a wink.

"Oh you are a very good girl aren't you? I would definitely like to see you again. I fly out tonight though so it will have to be next time I'm back. It'll be about three weeks."

"You're going to make me wait three weeks for that cock? I guess it's worth the wait."

"It will be baby. Watching you so willingly swallow every drop of cum I gave you was incredible. And I would love to stay here all day and explore each other a little more. But, I really need to go."

"I know, I know," I said with a sad puppy dog eye face. "You have to go. But, can I just freshen up quickly before I go?"

"I'll tell you what," Brad responded. "I seriously have to go, but as a sign of trust, you can take whatever time you need and just leave when you're done. I'd like to see you again when I come back."

"It's a deal. I promise I won't be long at all," I said standing up and picking up his pants off the floor. "Let's get you out the door first."

Watching Brad get dressed was a turn on itself. As I helped him with his jacket, I saw myself in the mirror. I didn't think I looked nearly as good as I did before but for the first time back out, I was passable. And Brad seemed to like me. I rubbed my hands down his chest and looked up at him. He grabbed his bag, put his arm around me, and kissed me.

"I loved today. I'm sorry it was so short and that I have to leave. I'd really like to see you again. Let's connect online again online and make sure we can meet again, OK?"

I kissed him back on the lips and replied that it all sounded good to me. I wiped the lipstick mark off his lips and off he went. I spent a few minutes touching up a few things in the bathroom. Before leaving his room, I stopped to look myself over. I had a weird feeling that there would be another time with Brad but I couldn't help but feel sadness as I turned to leave.

As confident as I was in his room, as soon as I hit the hallway, it was lost. I walked in the opposite direction of a couple approaching me and chose to walk down seven flights of stairs instead of taking the elevator. I found a side door out of the hotel and walked well out of my way to get to my car. While I was taking steps in the right direction, and I definitely wanted more of Brad, I would have to wait and see what today would lead to.