I arrived at my hotel and got checked in around 1 in the afternoon. Another trip to NY, this time for a softball tourney. 4 days with no work worries. Just relax and play a few games. The hotel staff might look at me a bit funny but I was here for a gay softball tournament so I could get away with dressing as I pleased, even if that meant being mostly in drag. I really didn't care what most people thought.
I don't play until tomorrow afternoon so there is plenty of time for me to enjoy the city. First a shower and close shave. Some nice comfortable clothes should do. A lightly padded bra and a snug little thong to act as a gaff. A pair of stretch pants. You know the type the lady's wear, a soft gray with a pink stripe down the sides. A cute t-shirt that my bra will probably show through and a comfortable pair of peep to flats. I emptied my suitcase, hanging what needed to be hung and put my lingerie and stuff in the drawers. I left a couple diapers and plastic pants on the dresser (always like to leave a little something around to confuse the housekeeping staff). A pair of earrings and a light pink lip gloss, and I was ready for the city. I grabbed my oversize bag and threw what I needed into it including a diaper and plastic panties, my flip flops and the new nail polish my wife asked me to use.
(Okay a little clarification here. I have a weak bladder and have used diapers at night for years. I love walking around NYC and sometimes you can't find a bathroom. I figured I would get a chance later to slip it on and avoid the worry. Plus I love the humiliation of knowing it shows beneath my stretch pants if people bother to look. In fact over the years I have come to believe that I am totally invisible when walking around this city. There are just too many beautiful people and sights to look at to pay attention to me.)
My wife knew I loved to have my nails done when in the city and this day was no exception. Out of the hotel and just a few blocks to my favorite nail salon. I would get a mani & pedi and end up with pretty feet and nails. Nothing better than a nice pedicure. I recommend them to everyone. I got to the salon and told the Lady what I wanted and she showed me to a pedi station. There were women on both sides of me getting there nails done. One pretended not to notice the cross-dresser climbing into the chair next to her and the other, a lovely looking lady of about 50 yrs grinned warmly at me and winked. I loved this salon because they had great massage chairs and the staff actually spoke English. I started soaking my feet while Angie got her tools together. I handed her the polish and she smiled and complimented me on the pretty stylish pink color.
As she was finishing massaging my feet my phone rang. It was my wife Sarah. I told her I was at the salon and the girl loved the color she picked. She asked me if they did designs on nails and I told her I would ask. Angie told me they did and for an extra five bucks she could put pretty flowers on my big toes.
I told my wife what she said and she told me to ask her if she could write words instead. When I asked Angie she said she could but it would depend on what I wanted.
Sara said to ask her if she would write baby girl with one word on each big toe. I told Sara that I didn't want that and she said I could have 3 choices then, and Angie could decide which to use. I said I would write them down for her to choose because I didn't want the women around me to hear what I had to ask. This Idea was firmly shot down by Sara threatening to have it on my fingers too if I didn't obey.
She said to ask her know and make sure it was loud and clear.
I said to Angie that my wife wanted her to choose what to write from 3 choice. I noticed that the lady's next to me were listening in at this point and told Angie directly that the choices are “Baby Girl”, “Sissy Baby” or “Baby Brenda” (Brenda being my wife's sissy name for me. With Sara listening on the phone Angie said for all to hear “what do you think lady's. The gal on my right pretended not to hear but Gail, the 50 something said I love “Sissy Baby” you really should use that. Why just look at him um her it fits perfectly”.
Angie said she agreed and said that she would do it. Sara said she heard the whole thing and I should be on my best (i.e. most obedient) behavior and do what I was told. I was to send her a picture when they were done. She then hung up. Before starting the polish Angie asked if I had brought my slip-ons. And I said they were in my bag. She went to get them form the bag and out fell the diaper and pink plastic panties, right between me and Gail in the next chair. I turned beet red as Angie slowly put them back in the bag. I know Gail had to see them too. Angie slipped them on my feet and wrapped cotton between my toes spreading them out for the polish.
Gail asked me why my wife wanted that on my toes and I explained that I was her sissy and must always submit to her and will and be obedient to all woman'. Also that I can't hide that I am sissy and they will look pretty when we go to the beach next week. We chatted about what I was doing in the city and I explained what I was here for and that I hoped to be dressed all weekend. She seemed quite interested and offered to help. I told her that might be nice.
Angie was almost done and I now had pretty pink nails with sissy baby written in black with silver highlights and a little heart on them. They really looked pretty as I headed to the manicure station. Gail was also finishing and getting her hands done too. While our fingers were being done Gail asked me to join her later for dinner and whatever and I said I would bee glad to join her.
My nails ended up looking as pretty as my toes but without the wording. As I was heading to the dryers I saw Angie and Gail taking. Angie said I was to follow her to the back as they decided I needed my brows trimmed a bit and it was a treat from Gail. I started to protest but a sweet “please, for me” from Gail had me following Angie to the waxing station. I laid back on the couch and explained to Angie that I couldn't have too much take off as I still had to work at a guy job. She told me to hush as she knew what she was doing and that my glasses hide them anyway.
She spread the wax, applied a cloth and pulled. I thought my whole brow was coming off. She then did it across the top of the brow and then the other eye the same. She looked at them a bit and grabbed a tweezers and tiny scissors and started plucking and trimming. I tried to get her not to go too far but she said this was a gift from Gail and I should be grateful for it. When she was done she finally handed me a mirror. I was shocked. They weren't fully arched but tapered up high to the outside and were about a 3rd of what they were before. I would never be able to hide them now.
When Gail saw them she smiled wide.”they are so perfect” she exclaimed. “You look so pretty” I tried to tell her that they took too much off. Gail told me to look at my toes and tell her what they said. “Sissy Baby” I replied to Gail. Then she grabbed me by the chin and looked me in the eyes and said” Yes you are and you are not to complain when a grown woman tells you to do something.Is that understood “Sissy Baby”?
Yes Miss Gail I replied.
“Good then here is your bag. Go in the bathroom and put your diaper on and get back out here now.”
All I could say was yes Miss Gail.
In less than 5 minutes I was dressed as told and standing before Gail and Angie in the middle of the salon. They both took pictures of me and my toes. Gail made me give her my wife's phone # and sent her a copy. She said it was cute the way the diaper showed through my pants and that they at least made my hips look a little fuller. We have to make a stop before dinner she said and we left the salon and headed down 2nd ave. She led me into a hair salon next and talked to the receptionist and then the stylist, occasionally glancing at me. Gail gave me a card. “This is my address, you will meet me there at 5:30 that gives you an hour and a half. Give me your hotel key so I know you will show up. I started to balk but she grabbed my bag and said that a sissy doesn't make decisions, just obey. She left me in the salon and the stylist led me to her station.
“ Well Sissy, what kind of cut would you like. You have very pretty hair and its quite long for a male, its like 4 inches past your shoulders we could do something nice.
“ I just want a little trim” I said not wanting to hurt her feelings. “That's okay Gail and I already discussed it so just sit back an leave it to me.” I knew it would be best to be quiet as she said “ Gail said that the more you whine the sissier it's going to look so just be good.”
“Yes Miss” was all I could say. I was planning to cut it all off soon anyways.
The stylist said she would give me a nice wash and wear cut that would hold its shape perfectly until I was ready for another haircut. I should last at least 4 weeks she stated. She washed and rinsed it and sectioned it off and started cutting.
An hour later she had finished and it had what could only be described as a little girls haircut. She reminded me that it would keep its shape beautifully and I should be happy it was so pretty. I thanked her and asked to use the potty but she said no and giving me a knowing slap on the bottom said I best be off if I didn't want to be late to Gail's.
It was about 12 blocks to Gail's apt and I would have to walk quickly to get there on time. I was about 4 blocks away when I felt myself wetting my diaper. I finally reached her and rang the bell.
To be continued.