A Trip to Remember Ch. 01

I live in Los Angeles and don't get much of a chance to practice my hobby of cross dressing. Once per year however, my company sends me to an industrial convention and I take full advantage of the opportunity. This year I was to travel to San Antonio, Texas, to attend a conference at a large hotel located on the River Walk.

I packed two bags, one with my business clothes and one with my sexy clothes. I kissed my wife goodbye and went off to the LAX airport. Checking my bags is an added thrill, since I do have the chance of my bags being inspected by the TSA examiners.

I have never had my hobby bag inspected but I have had my "normal" bag inspected (go figure). The TSA leaves a card saying that they have inspected this bag. I have heard of a case where a dildo was attached to the outside of a bag that had been inspected by the TSA. The same could happen to me were my bags examined. Up to this point my luck has held.

Landing at SAT airport I acquired my bags (with no adornments) and picked up my rental car. I traversed my way to a hotel located around one mile from the conference hotel. This hotel is within walking distance of my conference hotel but far enough away to reduce the potential of me running into someone that I knew. I wanted to be singular and had no need for "friends" enjoying my company. These friends would just take time away from my true desire.

I checked into my hotel, got lucky and received an upgraded room on the 7th floor. I went to my room and I arranged my clothing and toys. My male and female clothes were hung in the closet. My female underwear was carefully placed in one drawer. My sexual toys were place in a second drawer. My makeup, handbags and silicone breasts were in the third drawer. All of my other male stuff was tossed into the fourth drawer.

I got a wicked feeling about this, knowing that the maid could open a drawer or open the closet and see female clothes or sex toys in a room occupied by a man. I sometimes fantasized that a maid would go out of her way to look at the kind of man who used these items for his pleasure.

It was late in the afternoon and I wanted to get started immediately, but I still needed to eat dinner. I checked the restaurant guide and found that there was a nice steak restaurant a short way down the River Walk. It was still daylight but I thought I would be daring and dress in woman's clothing. Not a skirt, blouse, heels and leather skirt as I would really like, but a manly blouse, woman's tight jeans, girl shoes and a full complement of female underthings. When I returned to my room I would then change into my sexiest clothes.

I took a bath adding copious amounts of the French Lavender and Honey bubble bath that I had brought with me. The bottle says that it is scented with a romantic bouquet of French lavender, nectarine de Provence and Sun-kissed honey. It made voluminous amounts of bubbles and it smelled good enough to eat. I knew that after the bath I would also smell good enough to eat.

I drained the bath, toweled off my body and filled my bulb enema with warm water. I sat on the toilet and squeezed the water into my rectum. I waited a few minutes and then released the contents into the toilet. I repeated this procedure two more times and then finished with a final douche which contained a relaxing anal lubricant.

I know that you are thinking that the relaxing lubricant would relax my sphincter muscle and cause me to poop in my pants. Well my friend this is a well thought out process. My liberal douching has minimized the amount of fecal matter in my rectum. But, to seal (pun intended) the deal I used a combination cock ring and anal plug. A metal rod separates the ring and the ball. Instructions come with the device but essentially the ball goes up your ass and then your dick and balls go through the ring. Nothing comes out of your ass until the ball comes out. The ball doesn't come out until your dick and balls are out of the ring. I lubricated the ball, pushed the ball into my ass and then maneuvered my cock and balls through the rubber ring.

I then lubed up the inside of a small plastic bag and placed the bag into my Holy Trainer chastity device making sure that a part of the end of the bag extended through the pee hole. I pushed my cock and balls through the ring of the trainer and adjusted the ring atop the ring holding the ball up my ass. I then placed the bag and cage over my penis and pulled the bag through the piss hole which pulled my penis completely into the Holy Trainer cock cage. I turned the key which effectively locked both the chastity cage and my rectal ball in place.

I then put on my blue Genevieve garter and matching panty set from Hommemystere. I even put on the matching Genevieve Bra. I like to wear this bra because of the satin cups caress my tits and the bra produces minimal telltale lines. I didn't add any falsies to the bra, since I didn't want to attract undue attention.

I was finally going to be able to try on my Belle Maison stockings. If you haven't heard these are Japanese made stockings that have individual toes. The stocking toes fit over your toes just like a glove fits over your fingers. The unique thing about the stockings is the inclusion of pre-painted toenails. The stocking makes it look like you have had an expensive pedicure.

The designs are stylish and the colors are vibrant. I chose dark blue opaque stockings with a blue and white checkered motif adorning each toe. The combination is a little weird because you wouldn't normally see an actual toenail design through opaque stocking, but they let me purchase the combination so I did. I then carefully fit the stocking toes over my real toes and pulled up the stocking and attached the three garter belt tabs to each of the stockings.

I put on a blue and white plaid button down blouse. I purchased the blouse in a large size to minimize the effect that a bra would have on the blouse. The blouse has long sleeves, snap buttons down the front and pockets over each breast. Deliciously my blouse matched my toenails.

I buttoned up the blouse and stood in front of the mirror, twisting to see if you could see any evidence that I was wearing a bra. The blue and white plaid camouflaged the blue bra and I didn't see any strap bumps or a bump from the clasp along the back. Of course if I twisted wrong someone (a woman) might notice the uncommon protrusions and would realize that I was wearing women's undergarments. I would be found out. That potential was part of the excitement.

Next I put on a pair of size 12 Gloria Vanderbilt classic tapered jeans. I purchased these at Costco, took home a pair of size 16 jeans, returned them for a size 14, returned them and finally settled on the size 12.

The jeans were certainly tighter than I would normally wear. While my ass was smaller than your average womanly ass, the mirror showed that in these stretch pants my ass fit like a glove. I looked closely and didn't see clear evidence of my chastity device. I thought that I looked fine.

I added a light blue Cowgirl Rhinstone Belt which has a beautiful oval rhinestone buckle. I wore my blouse out of my pants to cover the fem belt. My outfit was coming together.

A pair of blue cowgirl boots would have been divine but a little over the top. As would the blue purse that I yearned to wear with this outfit. Instead of boots I decided to wear my pair of Faded Glory ballet flats. The shoes originally came with a bow detail on the toe but I cut off the bow to make the style less obviously feminine. If she paid attention, a woman would recognize the small heel and the large foot opening as woman's shoes.

I placed the shoes on my feet assuring myself that my "pedicure" could not be seen. My pants length just touched the back of my shoes. Thus the need for my dark blue opaque stockings, otherwise my hairy ankles and the tops of me feet would show. I expected that my shoes and stockings would sort of blend together.

I have always been surprised at how small the pockets are in women's jeans. Women carry all of their necessities in their purse, with the possible exception of their phone which they sometimes tuck into the rear pocket of their jeans. There is just no room in the side pockets.

Thankfully, I didn't have to carry much. No cosmetics, no tampons or super absorbent pads, no hair brush. I needed my room key (a plastic credit card), my real credit card, my license and two $20 dollar bills. I would pay for my food with the credit card, I might need my license for proof of identity and the money was for emergency or necessary purchases. This all fit easily in my side pocket. I would also take along my sudoku book to kill time at the restaurant.

Before I left the room I took my wallet and my car keys and the key for my chastity device, the key for a pair of handcuffs and the key for a pair of heels that I can lock on my feet and placed this entire collection in the room safe.

I took my IPad and turned on a program that displayes a picture for 10 second then randomly selected another picture for display. These pictures were all of me and there were over 400 of them. Any one of the pictures would embarrass me to death.

Would you like to see a picture of me wearing stockings, high heels, a bra with fake tits, on my knees sucking on a plastic penis that was suction cup attached to a full length mirror? Look at picture 233. How about me dressed in a maids' uniform, head on with me holding up my skirt so you could see my cock in chastity? That would be picture 118. See me tied up with a dildo in my ass and one in my mouth as I'm squirting cum? Try picture 18. No, I had no desire for anyone to see these pictures.

I set the iPad in the safe arranging the computer so you would see the screen as soon as you opened the safe. I then set the lock on the safe. The lock required 4 numbers and I pushed the number 1 button twice, hearing a beep after each push. I then took a pencil and closed my eyes and randomly poked at two other buttons with the end of the pencil. After hearing two more beeps I covered the display with my hand, opened my eyes and pressed the lock button and heard the lock engage.

My plan was to return to my room, change into a sexy black dress that has a back zipper. I would then add my locking high heels. I would lock my wrists in front of me using my hand cuffs, and then try 4 digit combinations until the safe unlocked.

There is a penalty timer built into the safe. When I got the wrong combination three times in a row, a 15 minute timer would start. The timer prevented me from trying any more combinations until the penalty time expired. Thus I might have to wait up to 8 hours to open the safe. The iPad slide show and my state of dress prevented me from calling in the hotel security to open the safe. I couldn't remove my shoes because of the locks. I couldn't remove my dress because I couldn't reach the zipper with my hands locked in front of me.

I would usually drink some scotch during the intervening periods. Sometimes I would punish myself by standing in the corner for the waiting period or spend the time on my knees practicing my fellatio technique on a penis secured with a suction cup against a full length mirror.

I have a camera that can take time delayed pictures and I usually set the camera up to take more compromising pictures of me for my iPad collection. I am thus continuously stimulated yet unable to obtain sexual release due to the chastity. When I finally open the safe I will normally quickly jerk off then shed my clothes and drop off into a wonderful night of sleep. I love traveling.

I have left hotel rooms before dressed in woman's clothing, but never in daylight. I have rented rooms where you can park right in front of the door. A few times I have left my room wearing a skirt or a dress and a wig and quickly gotten into my car to drive around. This has always happened in the dead of night. Not this time.

Now I was going out knowing that I wasn't wearing a stich of men's clothing. It was still light outside. I knew the psychology of the situation. I had to walk and act in a normal manner so as not to call attention to myself. I took a deep breath and left the safety of the room.

My penis would have pointed the way if it weren't secured at an uncomfortable angle. I went down the hall to the stairs. I walked down the stairs and opened the door and moved down the hallway towards the building exit.

I encountered three men coming directly towards me. They paid me little mind. That was my first test but that test was easy. Men don't usually notice other average men. They do notice women, but I wasn't a woman so who cares.

I left the building and saw the crowds walking along the River Walk. I hesitated slightly but then persevered. I took the path to the Walk and turned left knowing that my restaurant was a quarter of a mile away. I was doing fine walking past people and walking on the right hand side with a long line of people. I then saw 5 teenage girls standing off to the side and talking and giggling and fooling with their smart phones.

I knew this was the acid test. No one is more critical of a person's clothes than teenage girls. I tried not to look at them and proceeded along at a normal pace. I thankfully heard no comments and when I was around 10 steps beyond the girls I subtly looked back in their direction. One of the girls was looking in my direction but she hadn't sounded an alarm to the other girls so I was at best safe and at worst questionable which was good enough for me. I proceeded with renewed confidence.

I reached the restaurant and I could see that a line extended out of the door. I asked the check in girl how long of a wait I would have and she said "Without a reservation, around 1 hour, but we could seat you immediately at the bar and you can order right off of the menu." Seconds later I was seated at the bar.

I was eating on an expense account so I knew that I would have a good meal. I ordered an old fashioned and then looked over the menu. I ordered a filet with a baked potato and started on a sudoku puzzle.

As I was working my puzzle a woman came by, touched me on the shoulder and asked me if anyone was sitting on the barstool next to me. I told her the seat was open and that she was welcome to sit there. She fussed with her phone and muttered a few words as I was trying to do my puzzle. She then started a conversation with me.

"Are you here for a conference?" she asked. I said I was going to the water conference and asked if she was also attending. She indicated she was attending an emergency responder's conference. I found that interesting and we talked about her work.

She ordered a drink and some food and we continued our conversation. She told me that it was difficult being a woman working in a field dominated by men. I acknowledged the difficulty in her position and she began telling me of her trials and tribulations. I sympathized with her telling her that it must be very difficult.

Our food came and we continued our conversation. She told me that I was nice and that she really didn't need to be anywhere in the next few hours and did I have any idea how we could kill that time.

At this point I realized that she was hitting on me. She was younger than I and looked pretty fit and I'm sure we could have some fun together in her room or my room. Unfortunately, I was sitting there with my cock in a cage and a ball up my ass and I couldn't remove either of them, not to mention my other embellishments.

I kind of sputtered and told her that I had work to do and I really couldn't get out of it. This embarrassed her and she stood up and made some excuse about having to go to the bathroom.

I felt like crap but I could see no alternative. I swung around on my stool when I saw her return and began to apologize to her. As she was walking by saying "Oh don't worry about it, I understand" she hit my foot with her leg and my shoe flew off.

She apologized and got the shoe and looked at it kind of funny and then looked at my foot with my painted toenails. I tried to grab my shoe but she held it behind her back and asked the waiter if we could move to a booth in the bar that had just opened up. He agreed and she ordered us two appletinis and pointed to the booth.

I again tried for my shoe but she kept it away from me and said "OK princess, just get in the booth." I did as I was told and she followed me in the bench seat, blocking my exit. She had me sit up against the wall and told me to put my leg up on the seat. She felt my stocking covered foot and commented on my decorated toes.

The waitress brought over the drinks and she told the waitress to put the drinks on my bill. Her actual words were "You can put the drinks on Cinderella's bill," pointing at me. The waitress gave us a "Sure whatever" and walked back to the bar.

She handed me back my shoe saying "Nice shoes. I have a pair just like them, but I sure don't have stockings like you have, where did you get them?" We discussed my footwear and stockings at length, and I was thankful that we were in a secluded part of the bar.

She then said "I'm sorry, I didn't know that you wanted to pick up a guy, I thought you were just a normal person, I didn't realize that you were queer." I objected to that statement and told her that I wasn't looking to pick up anyone.

"What about the shoes and the stockings?"

I put my shoe on and placed both feet on the ground as I replied "I just did that for fun. I'm traveling and it was just a way for me to pass the time. It was just a fun thing to do. Actually I have never done anything like this before."

She replied "So this is your first time going out wearing woman's clothing? So the first time you decide to wear woman's shoes and you get specially made stockings? It looks to me like you went to a lot of trouble just to pass the time. I think this is more than a spur of the moment decision."

At this point she had her hand on my knee and worked her hand up my leg to the top of my stocking. It was obvious to both of us that she had just determined that I was wearing a garter belt.

Her next statement was "Well this just gets more and more interesting. You know what else I noticed? I noticed that your shirt buttons on the same side that my blouse buttons on."

She then reached over and tugged at the center of my shirt, popping 5 of the buttons on my blouse. These were snap buttons so I quickly attached them but not before she had her hand on my chest and she was feeling my bra.

"Oh my god, this is too much. Are you like transitioning or something because if you are you should really do something about your chest hair, and your head hair for that matter."

I denied everything. She then moved her hand up my leg and onto my crotch saying "Have you been fixed or and what the hell do you have down there?"

I said "Look, just let me leave. I'm sorry you don't want to get involved with me. I'm just a jerk and I shouldn't have come here. I'm sorry."

She told me that I had nothing to be sorry about. She was the aggressor. She was just looking for some non-judgmental sexual action. She told me that she has had sex with both men and women and that I shouldn't be offended by her comments. In fact I was the most interesting thing that she had seen in a long time. She then asked where my room was.

We paid our bills and walked back to my hotel. She had her hand around my waist and then slipped her hand into one of my back pockets. She told me her name was Judy and I lied and told her my name was Joe. I tried to dissuade her from going to my room but she was committed. I told her that I was obviously all screwed up and that she should just go back to her hotel.

Her answer, "I really want to see just how screwed up you are. You are going to be my best story from this trip. You already are and I know it's just going to get better."