Traveling Has Its Rewards

It was probably one of my longest trips ever. Not in terms of just distance, but in terms of time. There were two connecting flights, but I'm used to that. But due to strong head winds, my westbound flight was delayed and I missed my scheduled connections.

I never liked flying to Oregon, but now sitting around an airport for 4 extra hours in the middle of nowhere waiting for the next flight out only made it worse. I called the rental car agency and hotel to tell them I'd be late and they said no problem. They were used to it too.

The next connection was another wait, but only three hours. So leaving Miami at 8AM and arriving at 11PM was just a long, long day. The plane was packed because of the combination of flights due to the delays, but I was happy to finally be on the last leg. When I landed, I was exhausted.

Oregon's 11PM time was my time 2AM time. I quickly grabbed my two bags and headed out to pick up the rental car. At least things were now moving along.

Fortunately there were no problems at the rental car agency and I drove to the nearest fast food place that was still open, grabbed a burger and then headed to the hotel. My company booked me into one of those hotel suite type places so at least I felt like there was a little more room for me this week.

It was past midnight by the time I actually checked into my room. I guess it was now officially Sunday. What a long day. Somehow the travel didn't bother me that much when I was in my twenties, but having just hit 40, I was now getting tired of being on the road 3-4 months each year.

At least my Sunday schedule was easy. My plan was once I awoke, I was going to do a little sightseeing then start arranging some of my notes for the week's presentations. But being as tired as I was, I doubted very little of the sightseeing would take place. I really needed a good night's sleep. That was my first priority.

I placed my work bag near the closet area and tossed my personal suitcase on the bed. When I did, I noticed a new dent on the bottom. Terrific. Not only were the airlines delayed but they dented my relatively new suitcase. Idiots.

As I popped the latches open I saw a note inside saying Inspected by TSA. That figures. They probably even stole some stuff as well. That's all I needed. But then, as I looked inside, this was not even my bag. It was my brand, my color, my shape, but not my bag. The suitcase had come out on the carousel right along with my business case so I just grabbed them both and left.

I immediately called the airlines and got a recorded message. I left my details and decided to call it a night. But curiosity got the better of me and I went back to check out the bag. On top were two sweaters and a pair of jeans, but underneath I could see, and now smell, that this was a woman's suitcase.

She must have been packed for a week and was now returning home. Carefully, I unpacked the top of the bag so I could repack it in order later. As I did, I had real mixed emotions. Should I forget it and just leave it closed, or should I see what was in it?

Oh heck, she has my bag and is probably doing the same thing. As I went through it I was enthralled. Though worn, everything was so nicely packed. And her lingerie selection...nothing spectacular or sexy, but all very nice.

My guess is she was in her mid 30's and had a relatively nice job. She was definitely not small and had a nice figure, but not buxom.

I then put everything back exactly the way it was and moved it over to the couch. It was so late now that I really needed some rest so headed to bed.

Not having anything to change into, I just crawled into bed in my underwear. But as tired as I was, I tossed and turned thinking about her clothes and quite honestly, I just couldn't go to sleep.

Finally I got up, opened up the suitcase and looked again. I carefully slid out her nighties and held each one up. These weren't the tiny little babydolls like in catalogs, but rather modest ones. Not frilly, but very soft with that nice modal fabric and some subtle lace on the neckline and sleeves. Actually, real class.

I picked up the soft pink one and carefully slid it on. Ah, it fit so nicely. I ran my hands down the outside of the nightie and loved the soft feel of it and he light fragrance. I could sense my nipples getting hard and saw them pressing against the soft fabric in the mirror.

I then found a pair of pink panties and slid them on as well. This got me even more excited. I walked into the bathroom and in the full mirror I could see myself in this elegant nightie and I loved it.

I hadn't done this in years since I was a teenager. Back then, my mom's stuff was nowhere near as nice as this. This brought back such nice memories.

By now, my slight arousal was turning into a raging hard on. I reached over and grabbed some of that free lotion from the hotel vanity and within minutes, I had the nightie hiked up above my waist and I started masturbating.

I watched as my nipples got harder and harder through the soft fabric. This felt so good. This was so much better than even at my place with some porn magazines. I kept stroking my cock as I rubbed my nipples and then I exploded with a load like I had never experienced before. This was so good. It was amazing!

Maybe it was because of my sleep deprivation and then the masturbating, but this was like an out of body experience. As I stood there dazed, this warm feeling came over me. As my senses returned, I realized I needed to clean up very carefully. I did not want to get anything on these items.

Once I cleaned up, I debated on whether or not I should return the nightie to her bag, but I quickly decided against it. I made my way back to the bed in her nightie and panties and fell fast asleep.

At 10AM, I was awakened from my sleep by my cell phone. It was the airline acknowledging my dilemma. They said they were trying to track down my suitcase and would have it resolved today. It seemed like a lot of suitcases went missing on that flight because of the various flight delays. They admitted it could even be at another airport.

As I continued listening, I realized I was l sitting on the edge of the bed in this wonderful pink nightie. This was so strange at first, but I really loved the feel of it. I never have done anything like this before when I traveled, but I could really get used to this.

I was still groggy and was tempted to crawl back in bed, but I remembered the night clerk said breakfast was being served only until 10:30 so I needed to move it if I wanted to eat anything. I started changing and realized the short sleeved polo shirt I arrived in was first, in bad shape from traveling, and second, it was really cold up here in Oregon. Then I remembered there were sweaters in her suitcase.

I tossed the suitcase up on the bed and looked at the two sweaters on top. The burgundy one with the cute flowers was not going to work for me, but maybe the navy blue crew neck one would. Sure enough, I tried it on and it fit. Plus, it was so non-descript that no one would know. I loved the thrill of just putting it on and the very light scent of a woman made me excited all over again.

I looked a little deeper in the bag and carefully pulled out a black lacy camisole and black panties. Wow, she had nice stuff. I took the sweater off, and I tried these on thinking, why not? I could easily replace them right after breakfast.

I loved the look of being dressed in her black camisole and black panties. I could feel myself getting harder as looked at myself in the full length mirror. But time was ticking away and I had to move. I watched myself in the mirror as I slowly pulled up my jeans, covering the black panties. It was like in slow motion.

I had to tuck my cock between my legs just to calm it down. Can't walk into breakfast with an erection. Wearing these clothes was powerful stuff. I then pulled the navy blue sweater over my head, checked myself out one more time, and then headed down for breakfast.

Breakfast buffet was quite a spread and the place was just full of activity. I hit the buffet and then secured a small table. I had no sooner sat down and began eating when a very pleasant woman stopped by and asked if she could join me after she picked up her breakfast. There were literally no tables left. Being a nice guy, I said certainly. This was already turning into a better day than I hoped.

I played with my breakfast a bit so I could enjoy some time with her. And then the reality of my wearing the sweater hit me and I got a little nervous about it. I hoped nothing would show.

She finally returned, sat down and introduced herself as Abbie. "Hi, I'm Nick."

"Thank you so much for letting me sit here. This place is busy this morning."

"Actually I'm glad to have the company. Morning breakfasts by yourself get boring after a while. You can only look at messages on your cell phone so many times."

"I totally understand. You're here for business then?" she asked.

"Yes, I'm here for a week. I do engineering consulting so I have a number of meetings and presentations."

"Well besides being unseasonably cold today, it's supposed to be a good week weather wise. Hope you get to enjoy a little bit of our city."

"I plan on it. I have a few spots mapped out to see."

"Speaking of cold, it's a good thing you brought a sweater."

I laughed and said, "Yeah, it is."

I paused for a second and then added, "Funny story about this sweater. I actually didn't bring it."

She looked at me strangely.

"I arrived last night around 1AM and found I somehow got the wrong bag at the airport. There were delays, mix-ups and just plain travel exhaustion. I had no clothes other than what I was wearing. This sweater was in the suitcase I grabbed by mistake. I tossed it on just so I could eat and then I'm going to head to the mall right after this to buy some warm clothes just for today."

"Wow, that's so strange. But lucky for you that it fits."

"Right. All I had was my polo shirt from when I left Florida and it was 80 degrees. The weather here is much colder than I thought. But I really need my suitcase. I have meetings Monday and I would hate to have to go shopping for all new things."

"Well, I love that color on you if that helps."

"Thanks, it was either this one or the burgundy one with flowers, but I still feel awkward about it." I laughed awkwardly realizing what I had just said.

She laughed and said wryly, "You chose wisely then."

We chatted a little more and when we were done with breakfast she said,

"Before we leave, I have a little confession to make. I was the one who took your bag by mistake."

That quieted me right down and I started getting red.

"When I walked in, the man at the desk pointed you out and then I spotted my sweater. I was a little upset when I first saw you wearing it, but now that I know the story, it makes a lot more sense."

I got even redder and was not sure what to say next.

"Oh, don't be embarrassed. I probably would have done the same thing if I was you."

"How did you even know I was here?"

"When I got home last night I did the same thing as you. I called the airport and left a message. Not hearing back from them, I went through your bag and inside your suit jacket pocket was a stack of your business cards. I called two of the better hotels in town this morning and lucked out. You were staying here."

"Good thinking. I guess we both lose a little privacy when suitcases get swapped," I replied.

"Well it's nice to see some men still have a nice taste in clothes. You dress quite well."

"Uh...and so do you. May I ask, what do you do?"

"I'm a manufacturer's sales rep and I have this northwest region. Lots of travel."

Our conversation continued and then started to die off. Abbie then said nicely, "Nick, I don't want to take up any more of your time. How about we swap suitcases and I will be on my way?"

"Sure, let me change out of this sweater up in my room and I'll bring it right down."

"Oh, you don't have to. Do you want to keep the sweater for a few days? It actually looks quite nice on you."

I got red again and said, "No, that's OK, I packed a fleece pullover with me."

"Yes I know," she said with a smile.

Then she then asked..."Or keep the black camisole?"

I replied with a "Huh?"

"It's showing underneath the sweater in the back. I can see the straps and the little bumps in the back from the straps."

I got red all over again.

"Let me guess...you didn't have any under clothes to wear so you tossed on my black lace camisole as well?"

I felt like everyone at breakfast was now watching me. I had no response.

"Look, you seem like a real nice guy, and a professional as well. And my thoughts are you don't usually go around wearing women's clothes. I noticed there were no bras or panties secretly stashed in your suitcase. Plus an experienced crossdresser would wear a nude colored camisole under a sweater to make the color blend better in a public setting."

Now people were turning around and listening. The word crossdresser certainly caught everyone's attention.

Sensing the awkwardness she said, "Tell you what, let me follow you up to your room and we can continue the conversation there."

The short 3 floor elevator ride was painful. As I approached the room I remembered that her suitcase was still open and the nightie was lying on the bed along with her panties I wore last night. I paused at the door trying to think of something to say but she said, "Don't worry, I'm expecting the worse."

As I entered the room, at least everything looked neat and clean. But smack in the middle of the bed was her suitcase with her nightie and panties folded neatly beside it.

I went to place the nightie in the suitcase and she said, "Look. Keep the nightie. It's not one of my favorites anyway."

I was befuddled. That was not what I expected to hear.

After a few painful seconds of quietness, she said with a cute, sexy smile, "Would it make you feel any better if I told you I wore your boxers and your Penn State Tshirt to bed last night?"

With that she showed me a selfie she took of herself. She had to have taken about 5 different pictures. She actually looked pretty hot in them. She then said, "I guess we both did a little exploring."

"Nick, the way I look at this is that none of this would have ever happened if I hadn't taken your bag. It's not all your fault...and I actually think it's kind of cute. Plus, like I said, you seem like a real nice guy."

Quietly I stood there and had little to say. It was awkward and she sensed it.

She broke the silence by saying, "How about this? Now that we how a little more about each other, how about you shower and change, and I take you out for a little sightseeing tour of the area. I think I owe you that. We won't waste time on dumb places, but see some of the better ones."

Quietly I just stood there and then said, "OK, but you really don't have to."

That was about all I could come up with. Maybe I was just too embarrassed to think straight.

"Nick, I insist. It'll be fun," Abbie said.

I just stood there and nodded. "Well, OK. I'll be done showering in a few minutes then."

"And I'll just sit her in this massive living room over here and watch TV. This is quite the place."

I opened up my own bag and grabbed some items out of it and headed to the bathroom.

Once inside the bathroom, I took off the sweater and camisole and shouted through the bathroom door, "Abbie, I forgot to tell you, I also borrowed a pair of your panties as well."

"I expected as much...which color?"

"The black ones."

"Good choice...keep them." I then heard the TV go on so I knew she was still there.

As I finally exited the shower dressed in my own clothes I asked, "I was thinking. Fair's fair. Do you want to keep my boxers and Tshirt?"

She paused for a moment as said, "Normally I'd say no, but in this case I'll make an exception."

As we left the hotel, my boxers and T shirt tucked away in her suitcase and we continued our conversation.

Abbie was a lot cooler than I thought. She wasn't your typical hot babe but a real nice middle aged woman, in her 30's as I expected. Her looks were so average that she would never stand out in a crowd either way. I actually liked that. That fit my profile as well.

As we started visiting some tourist sites, she told me more and more about herself. She played sports in college and never minded playing on both teams as it turned out. She said she even had this great collection of guy clothes in her apartment. She actually knew more about men's clothes and designers than I did. Up here in the Northwest, no one seemed to care what anyone wore.

It was about 3PM when we stopped and grabbed some coffee. It was cold up here and getting colder. The coffee warmed us up. Her conversation drifted back to me wearing women's clothing.

I really had trouble convincing her that I really never crossdressed as she kept pressing the issue. She just would not believe it. She kept asking me all kinds of questions about it and I just kept telling her this was really my first time except as a young kid, and even then only on occasion.

"But you wanted to wear my clothes to bed and then to breakfast in a public setting though. Interesting. Maybe you're going through a change in life."

"I don't know, maybe getting older does have something to do with it. Or maybe just being overtired last night. I really don't know."

"Nick, who knows, but while this door is open just a little up here, let's head over to a store I know and get you a couple of things. The people there are great and they are such fun."

"What kind of store?"

"You'll see."

We finished up the coffee and went to the Factory Outlet mall. We headed right into the Maidenform store and the clerk greeted her with, "Hi Abbie! What brings you in today?"

"Hi Meg, just needing a few things for my new friend from Florida...his name is Nick."

"Hi Nick from Florida. Give me a shout if you need a hand."

Abbie turned to me and asked..."Are you OK with this?"

I really didn't have much of a choice but readily agreed. Abbie walked right over to where the bras were and selected five different bra styles for me. "Let's start here and see if any of these styles work for you."

She came right into the dressing room with me and said, "Off with your shirt." As I was doing that, she adjusted each bra for me and helped me slide each one on. She was all business and that actually made the experience less awkward.

From the five bras we found two styles that really seemed to fit me well. I had no idea there were different styles. We then went for color and decided on a black and pink one.

With the two bras in hand, I tossed my shirt back on and Abbie and I then headed to the panties area and got their 5 for $25 special. She suggested I get mostly the hipster panties because they are more practical. "But", she said, "toss in a thong for fun."

Holding up the panties to the bras to get the right color was fun. "These will go nicely together...don't you think?" she would ask. She was enjoying this more than me.

Within a few minutes we were over at the nightie and camisole area and selected a few of each. We made our way back to the fitting area. Abbie was so comfortable with this it was amazing. Of the three nighties, I loved the long black one with a cute slit in the front and Abbie agreed. She also like how it was a soft lace bodice and not scratchy.

As she was looking at the fit she stared at my nipples and asked, "Do your nipples always get this hard? You're worse than me."

I had no comebacks for her and was just loving this experience.

She then showed me how one camisole had slightly larger shoulder straps and could be discretely worn under a shirt or sweater. I got two of those and then two cute ones with spaghetti straps to match the black and pink bra. And just before we left she grabbed a wrap jersey skirt for $9.99 and tied it around me right there in the store and said, "And this would be perfect for around the hotel room. Get this as well."