Sightseeing with the Practice Man

Sightseeing with the Practice Man

By Sabrina G. Langton

***

Finally alone.

Foundation, eye makeup, lipstick.

Brushes, tubes, cotton balls, eyelash curlers.

Long nails, varnish. Wig, pictures.

Finished.

***

I loved putting on makeup, it was my favorite thing about being a crossdresser, my favorite thing about trying to be a woman. I could change from an average guy in the neighborhood to a beautiful model in forty minutes. It used to take over two hours.

I lived with my mother in Secaucus, New Jersey in a fourth-floor apartment with a great view of New York City. The skyline is only six point three miles away. I had a huge picture window with this view, my mother had a view of the Rutherford Football Stadiums. 'Ka sara sara.' We have been here for over two years. Mother sold our house in South Jersey, and now we live in a luxury two-bedroom apartment closer to her sister.

In my head and mirror, I was a fashionista, an influencer named Giselle. A stately blonde model visiting the states to show off her outfits and grace. Turning the world onto fashion and beauty and food. In reality, I was a twenty-two-year-old college graduate with a good job, a hybrid car, and a local girlfriend.

My mother, of course, knew nothing of my girlie asperations. She worked at the corporate office of a major international clothing chain. She was quite busy and she loved her job, though the hours were 4:00 PM to 2:00 AM, Tuesday through Thursday. She was then gone most weekends to visit her sister nearby in Montclair. I usually had the place to myself all weekend. That's why my makeup and dressing up were always on point. All the practice.

Thursday was my favorite night. I get home from work around three in the afternoon, say goodbye to Mom, and head into my sanctuary. My room with two closets and a queen-size bed. I have an old roll-down desk that came with the apartment. It had a lock on it. Once it rolled up it revealed all my Maybelline, Chanel, Ulta, and Dollar store amenities. I then would put a long door mirror sideways onto the top of the desk and get to work on my face and outfit for the night.

Tonight I was wearing a white mini dress with a high neckline. My C cup breast forms safely hidden. I had on a white thong, nude pantyhose, and a corset underneath. I was 5'8" in flats, which I never wore, and my body was nicely proportioned. I was at the gym constantly working on my legs and tight stomach. Even my ass looked nice and round. I was all girl when dressed up. I had on my long strawberry blonde wig that matched my hair color perfectly. I would love to grow my own but my girlfriend didn't like me with long hair, I wonder if she would like me in a short skirt?

I put on my red press-on nails, nice and long, and my toes were already painted the same color. I slipped into my three-inch red heels and put on a white matching cover-up, it was a little chilly this October. A little spray of my Chanel and picked up my red bag. I was out the door, heading to the nearby retail outlets. My regular weekly outing.

There were four other apartment doors on this floor and I was happy that they were usually very quiet, even at seven on a Thursday night. Mom and I were also the closest to the stairs in 4A, only eight feet away. I was getting ready to traipse down the four flights when the door to the stairs opened and two dogs ran to me, their leashes in their wake. I spun around as they grazed my nyloned legs and ran past.

"Grab them!" I heard a call from the door. In ran Luna Hammond, the woman who had the furthest apartment from the stairs. "They are crazy tonight." She told me as the two of us chased the dogs around the landing.

I was forgetting I was all dressed up until I almost tripped on my heels. I bent down, grabbed one of the leashes and the little white Maltese jumped into my arms, trying to lick my face. I put my foot on the other leash just as the other one was going to take off back to the stairwell. It pulled me about twelve inches, but I stood my ground.

Luna picked up the leash tangled in my legs. "Shit, these dogs are so hyper, but they love you." She laughed and shook her head as she moved toward her door. "Come on in, thank you for being so quick."

I didn't really want to go in, I wasn't used to talking to anyone who wasn't working behind a register when I was all dressed up. It was the first time I was ever in anyone else's apartment since we have been living here. Luna closed the door and took off the dog's leashes.

"Wow, that was fun, no?" Both dogs hung around me and finally laid at my feet. I was very popular tonight. Luna looked down and laughed since they were now relaxing like completely different animals.

I smiled at her, she was probably seven or eight years older than me and she was married to an even older man. She was beautiful with long dark hair, dark skin, and a curvaceous body. I had noticed her a number of times and my male self would say hello to her and her dogs.

"I better go," I said in my almost perfect female voice.

"Thank you again, um I have seen you before but I don't know your name." She held out her hand and took mine.

"Giselle," I told her, afraid that my name was too exotic for Secaucus. Just as exotic as hers.

"Giselle, beautiful name, you are such a beautiful girl. I'm Luna. Do you live with the Morrison's?"

Shit, I was thinking. The Morrison's, my Mom and me. Did I live there, who was I, what should I tell her? I knew I was probably going to see her again. She said she saw me before. How could you miss a tall blond in heels?

"Um, kinda. I'm just visiting Aunt Linda." I decided I could be a cousin, a close relative, that wasn't too far-fetched.

She smiled. "You know, I was just thinking." She squished her face up in deep thought, she was a very pretty woman. "My husband's son, Marc, is coming in for a visit from London. I was going to take him to the city tomorrow, do the tourist thing, but I wonder, maybe you would like to go with him? I'm sure he would rather be with a pretty girl than his step-mom."

She went over to the table and picked up her phone. "He is very handsome," She winked at me, "Just like his father." She then showed me his picture. He was standing between them, he was tall, with dark hair, he was quite good-looking. I think. When I am dressed up I find men totally attractive. When I'm not I am a heterosexual male, as a girl, I didn't really know.

"Well? It's just for a couple of days, he and my husband have meetings in the mornings, then he will be gone. I will miss him all over again."

I didn't know what to say, what if my mother, or Keira my girlfriend found out? I decided to play it cool like I was really a sophisticated socialite. "When does he arrive?"

"Tonight, a couple of hours, his plane lands at midnight." She grabbed my hand again. "Please? He would love you. He would love me even more for finding you. I would get so many step-mommy points, ha."

"What are step-mommy points?" I asked.

"You know, points you get, when you overcompensate, for not being a real mommy, haha." She laughed, I laughed with her. I was enjoying her company very much, I never had a friend as my female self.

"Okay," I told her, it fell out of my mouth. My hand went immediately to my lips when I said it. Okay? what the hell was I thinking, I wouldn't know the first thing about going out with a man and I still didn't know if my mother was going to Montclair. If she was out of the house all weekend this would be fun, but if she wasn't...

"Really, oh my god, great. You two are going to have so much fun. Let's get a picture to show him." She then took a couple of snaps of me in my white dress. We then took a couple of pictures with the two of us. She sent them to me and we looked at them together. "We look like a couple of besties, haha. Marc is going to be thrilled."

***

I was slightly shaking when I left her and the dogs. My bracelets were rattling. I had a date tomorrow, I might have dates all weekend. I snuck downstairs into the parking garage and sat in my Honda Accord trying to catch my breath. How could I of agreed to this?

I first texted Keira. I always smiled when I typed with my long nails, and told her I was going to be busy all weekend, she was quite disappointed, that was what she lived for. She worked hard all week and couldn't wait for me to take her out, otherwise she didn't leave the house.

I could use a weekend off.

I then texted my mother, but she didn't give me a definite answer either way. If she was home it was going to be impossible for me to walk out in heels.

I went to the outlets, but now I had a mission. I needed something to wear to sightsee, I needed something comfortable and sexy. I needed something to keep up the interest of a young man, a handsome one. Asking the girls in the stores for outfit ideas was so much fun and a little exciting. I would tell them I had a date. I was now a woman who had a date, I felt incredible. Date, date, date.

In a couple of hours, I was shopped out. Not only did I find everything and more that I was looking for, but I also smiled at everyone. I wanted everyone to know I was a satisfied woman shopping to make her 'boyfriend' happy. It was a marvelous little fantasy running through my mind, and it was pretty close to reality. I would even make eye contact with men checking out my legs, 'cause usually, I walked with my eyes down to the ground. I was coming to these outlets for almost two years and now I was flirting more than usual and playing with my hair. Two men actually struck up conversations with me, something was happening and I was loving it. The confidence I felt was overpowering and my panties were drenched when I got back in the car.

***

I stayed up until late after getting back to the apartment. I was still all girl and I wanted to try and catch Luna's step-son as he got here from the airport. It was all I could think about. About forty-five minutes after his plane landed there was a little bit of commotion out on the landing. I heard Luna's dogs barking. I peered out and tried to catch a glimpse out of the peephole but there was nothing but shadows.

A couple of seconds later I heard a scratching at the door.

I looked out again it was Luna holding one of the dogs. After a light rap, I took a deep breath and opened it. I was now in a new dress and black pumps. I might wear this on one of our dates this weekend, I was hoping he liked me in it.

"I'm so sorry Giselle, the dogs wanted to see you again. They came right for the door. Hah."

I pet the one she was holding as the other ran into my apartment. They were sniffing me like crazy, one under my palm and the other now making my ankles wet.

"Since you are up come out and meet Marc and my husband, I made drinks." I was glad that my mother was still at work, I had another hour and a half until she returned. I had on a short denim dress with a belt tied around my waist and a striped shirt underneath. I was wearing three-inch black pumps and trying to silently click over to Luna's apartment. I was hoping the other neighbors didn't open their doors or look out of their peepholes.

The one dog was almost attached to me as I made my way over, I had to bend down and pick him up. I walked into the apartment with my hands full, hoping my makeup still looked okay from hours before.

There were glasses on the table and Mr. Hammond was pouring a red liquid from a pitcher. Both he and Marc turned around at the same time as I entered. Marc's eye's lit up.

I put down the dog, I was suddenly nervous, a man never looked at me like that before. I felt a little tense. The two men watched as I stood up in my heels.

"Ah, another guest." Mr. Hammond said as he handed me a drink. "Luna made Negronis. I'm Phillip, this is my son Marc."

We clinked our glasses and I drank the bitter liquid, I loved it right away. "Mmm," I said, I was afraid to talk.

"Giselle. A beautiful woman named after a beautiful ballet." Marc said in a sexy English accent, as he moved closer to me. "Luna sending me pictures of you two made my flight so long with anticipation. But now... " We clinked glasses again. "We're here." His smile was making me all warm inside, though that might have been the drink. I never felt like this, I had never been so studied or fussed about before. Even the dogs were still showering me with attention.

"Manny and Birmy love Giselle, they can't keep their noses off of her," Luna said.

"They must know something," Marc then came close to me, his face near my long hair. "Mmm, whatever that scent is I'm a fan too, haha." He sat back down and I had a tingling sensation in my panties. I was glad I was tucked and tight. I sat at the table and crossed my legs just in case.

The next hour flew by, I kept on glancing at the microwave's clock to make sure it wasn't getting too close to two fifteen when my mother would get home. I was loving being one of two girls at the table, this was so much better than sitting in front of my mirror or shopping on my own. This is what I wanted... drinks and company.

I found out that Marc was twenty-seven, three years younger than Luna, but only five years older than me. I asked Luna, "When Did you and Philip meet?"

"Mmm." She looked towards Philip. "It must be five, six years ago. I was a temp, and Philip's company hired me to organize some new employees."

"She was so good at it," Philip told me. "I married her."

"Yeah, two years later." She hit him playfully on the shoulder. "Then we moved here. I wanted to be close to the city and my family."

"And you work together?" I asked.

"Sometimes, Philip and Marc are trying to get a new venture off the ground. Once that gets started, I might help out a little." She smiled at Marc, I could tell he liked his stepmother very much.

I glanced at the clock, it was after two, and then told them I had to go and get up early. Marc walked me to the front door. He was so much taller than me, at least three or four inches and I was in heels. Then he was walking me to MY door. I was in the hallway dressed as a woman and a man had his hand on my hip. I had never spent so much time on the landing, usually, I just rushed down the stairs to the safety of my car.

"I can't wait for tomorrow." Marc was moving closer to me as we stood together. "Maybe we can start early I only have one meeting about noon. How about three?"

"That sounds great." I smiled, he was too close to me. I was getting all types of turned on.

"Three great, we'll do dinner and some sights, it will be fun." He then kissed my hand slowly. "Goodnight Giselle."

My heart was racing, I could feel it pounding against my fake breasts. "Goodnight... Marc."

I was in the door fast and now I was leaning against it. I lifted my denim dress and brought down my panties. I was so hard. I still heard their voices before they closed their door. "Oh my god, Marc... I can't wait until three..." I played with myself while rubbing my breast with the other hand. My little 'clit' was peering over my small panties as I rubbed. I didn't have to try too hard and suddenly I started cumming, I was trying not to make any noise, but I was so excited. Being so close to a man was making me crazy. I never would have imagined that I would have such a strong reaction under a man's gaze and presence, plus hanging around in a dress in front of people was a dream come true. I caught all my sperm in my hand and leaned back against the door. My eyes were closed, my orgasm was so intense, it had been building up all day.

I don't know why but I brought my hand up to my lipsticked mouth, I licked it clean. That was a first. "Thank you, you taste wonderful." I giggled and walked into my room. I didn't want my mother finding a horny woman in the apartment, blocking the door.

***

I was asleep by the time my mother got home, I had definitely had too many Negroni's, and I didn't want to get up the next morning. I had worn one of my only nightgowns to go with my breast forms and sometime in the middle of the night a man slipped into my imagination and made all kinds of love to me. This is the second pair of panties I would have to soak.

***

I stayed in my room the entire time my mother was cleaning and getting ready to leave. I had my breast forms and lingerie on the whole time, I didn't want to take them off.

She yelled through the door, "I'm leavin'!" And then she knocked. "Make sure you get out of bed."

"Okay," I said in my male voice, which is almost impossible while wearing a lace bra.

I had until three to get ready, plenty of time. I could try on every outfit again like I did last night and take more pictures.

After exhausting every combination I could try with the new clothes I decided on a long black dress with little flowers on it. The hem ended right below my knees, but it was buttoned upfront from my chest to my thigh leaving me with a perfect slit showing off my legs. My legs were perfect, shaved, and toned. I was constantly waxing and lotioning them. I hit the gym four times a week. They were my best female feature, I never wore shorts as a boy because of them.

Underneath I had on a corset and my black underwire bra. It gave me such nice cleavage, I decided no forms today, just filets. I put on four-inch sandals, so I decided to not wear pantyhose. I wanted to show off my toenails. I painted my nails pink to match, no extensions this time, and then put on pink lipstick. Big gold earrings and my thin watch were my only jewelry. Lastly, I put on a straw hat and paired it with a round straw bag. Everything was new and I was dressed perfectly for sightseeing.

I took a few pictures and read the text's from Luna and Marc that came through. Luna thanked me for taking care of her stepson and Marc thanked me for going out with him. He sent me a few shots that he took last night, I didn't even notice he was taking pictures of me. I do remember the shot of the four of us. Marc set up the timer on his phone and took five shots in a row, they were all terrible but one. It was my favorite photo of me ever. I looked incredibly happy surrounded by people.

It was getting closer to three and I was distracted trying to decide what perfume to use when I heard my mother's voice outside the door.

"What the hell," I mumbled. I looked at my phone, she texted me and asked if I wanted Indian food a half-hour ago. "Shit." I should have been checking more.

Marc would be here in a couple of minutes, I was completely dressed up and waiting for him. He was going to love me in this outfit.

I heard my mother again, "Put that over here."

"Okay, Mrs. Morrison." Shit, shit, shit. The only person who calls my mother Mrs. Morrison was Kiera. The two of them were out in the kitchen I heard clinks and clangs, they were getting ready to eat.

I texted Marc. 'So so sorry something came up, I can't get out of it. Can I call you later?'

It was too late I heard the bell. Ring. I watched it on my phone, I heard and saw the door open. It was Marc, the women let him in.

"Hi, I'm Marc, I'm here to pick up Giselle." He told them. I heard his wonderful British accent, I started to sob. I had to get undressed. "I'm the Hammond's son..."

"Giselle?"

"Yes, We are going sightseeing?" He sounded excited, I hated letting him down.

"Who?" I heard my mother say. There was some movement and talking outside I didn't know what was going on. I was taking off my heels and dress.

"She's beautiful, I don't think I know her," Keira told him. They must be looking at the pictures from last night on his phone. "She lives here?"

It got a little quiet. I was dying.

"Ohh wait, that's Giselle, we call her Jill, I haven't called her Giselle since she was born. Haha."

I heard my mother say to them. Jill?

"Maybe something happened, I'll find her and have her call you, you know if you are going out, Keira will be more than happy to go with you, right dear."