The Restart Pt. 03

After leaving Becky's I struggled to sleep that night. My mind was wandering about Becky, what was her end game with dressing me up etc. I didn't want to get outed at work, but if she did, then it violated HR policy.

Monday I arrived at work in full men's attire, no panties or nylons. I didn't know what direction this was going with Becky.

During her first break, Becky came into my office. She was wearing black dress pants, a purple blouse, black heels and black nylons. She looked amazing as usual.

"How is your day going today?" She smiled and asked. As she asked me she slid her nylon covered foot out of her heel. She definitely knew how to flirt.

I replied "Very well and yourself?"

She replied "It's awesome, I love coming to work now." as she winked at me.

Becky said "Maybe we can hang out this week, let me know what day works for you."

I looked at her and said "I definitely will."

That night I went home and worked out, ate and showered. I got out of the shower and walked over to my dresser. I instinctively slid on a pair of tan sheer to waist pantyhose, my shaper and black panties. I logged onto my yahoo. There were no messages from Justin. I scanned through my groups and all of a sudden a message popped up. The Screen name was TNTfun

"What's up, hot stuff?"

I replied "Just chilling out and you?"

"Just scrolling through Groups and I saw you were online. Tell me about yourself."

I replied and I asked the same question.

TNTfun responded "Have you ever been a bartender or worked in the food industry?"

I replied "I had, I was a waiter in college."

TNTfun responded - "We are looking for Crossdressers/Drag Queens to work at our Restaurant/Wine Distillery on weekends. Our place is about 35 miles south of where you live. We have found out that it is more appealing to females to come to our events if we have Drag Queens/Crossdressers work it. We are very LGTB friendly, but also want a traditional clientele.. Are you interested?"

I replied "Maybe, depending on the pay."

They replied "You will get a flat $150.00 plus tips. The events are usually from 9 am to 1 pm. We would need to meet to see how you look. Do you have time tonight?"

My cock was 3/4 hard in my pantyhose thinking about being dressed in full female attire and waiting on people. The financial side of me thought it could be good money to put away for a house.

I typed back "What time and where?"

They replied "9:00, the place is called "Rumors, you don't need to show up dressed. We can make you up. But bring your heels and a dress with you. "

I grabbed a duffle bag and grabbed my black dress and my black strappy heels. I put on some jeans and a sweatshirt. I left on my pantyhose and panties and drove to the bar.

It was closed and I knocked on the door. A tall in shape white male answered. He was wearing a black t-shirt, khakis and deck shoes. He looked and said "from yahoo?" I nodded and he invited me in.

He pointed to a table and said "Take a seat, do you want anything to drink?"

I replied "I will have a gin and tonic."

He nodded as I sat down.

He introduced himself "I am Trent, you are?"

I replied "Chris"

Trent replied "My partner will be here in a second."

It was a smaller place. It featured wine, and had a dining area and was very clean and well kept. It was odd I had never heard about it.

Trent brought me my drink and began to tell me about the position.

"You will dress fully in drag or female attire. Entertain, and take food/drink orders. We had an agency bring us drag queens a month ago, we promoted it as a Drunch and our Saturday morning was off the charts. We are looking to do this weekend. Do you have clothing?"

I nodded and Trent continued. " You can show up in male persona, and make yourself up here. We have a locker room in the basement."

The door opened and a female in her late 50's walked in. Trent stood up and said "This is Tonya, my wife."

Tonya was 5'6 in good shape. She wore black jeans, a gray top and black boots. Her make up was heavy, her hair dyed Auburn. She was attractive, well maintained.

I stood up and shook her hand "Chris"

Tonya replied "Nice to meet you."

Tonya quickly interjected herself into the interview.

"I need to see if you can serve in heels, darling. Let's put on your heels and your dress."

She took me to an office and said "You can change here, come out to the bar when you are done."

I took off my jeans and sweatshirt. I slid on my dress. I slid the heels on and nervously walked back out to the bar.

Tonya smiled "Look Trent, he already was wearing pantyhose as well, he was well prepared."

Tonya filled up 5 glasses with water. She pointed at a table across the restaurant and said "Bring those over there, one hand balancing the drinks."

I put the glasses on a tray. I brought the tray to my shoulder, bending my right arm. I walked across the restaurant in my high heels, pantyhose and dress. I put the drinks on the table with no spillage.

Tonya clapped and said "You are hired, my only concern is you make sure you don't get too excited doing this. I noticed a little bulge in front of your dress."

I blushed and Tonya handed me paperwork. "Bring this by Saturday, when you come. We open at 9 am, you should be here around 8. You can have fun with the clients, they might buy you drinks, but be responsible. We have a bouncer here in case someone gets out of hand. Trent will show you where to change etc. It was very nice to meet you."

Tonya left and Trent took me to the kitchen, supply room and then turned on a light. "The changing room is down here." I followed him down and below was an office and then a locker room type of room with showers, recliner etc.

"I renovated this a year ago. I try to make employees comfortable down here, seeing it can be stressful. How long have you dressed?"

"A few years," I replied. I was kind of overwhelmed with what was going on.

Trent nodded and said "What got you into it?"

I replied, "I tried on a pair of my girlfriend's pantyhose, and got caught."

Trent laughed and said "It seems like a common theme, you have amazing legs by the way."

I replied "Thank you" as I felt uneasy at the current circumstances, dressed in front of Trent after his wife dressed me to make sure I could serve in heels.

Trent said "Let's go back upstairs and you can get going."

I started to go up the stairs with Trent following me. I climbed the stairs carefully, being in heels. Towards the top I slipped and almost fell, Trent grabbed me by the hips to make sure I didn't fall. "Are you okay? I know these steps are slippery with heels on."

He put his hand on my hips and guided me as I got to the top of the stairs. I got to the top and his hands moved to my ass.

I turned around and Trent looked at me and said "you were looking for cock on Yahoo tonight weren't you?"

I stood there speechless. He grabbed my hand and took me back to the office where I changed. He spun me around and began to grind on me as he bearhugged me. His hands roamed to my thighs and he rubbed them up to my ass. I could feel his bulge against my ass.

He guided me to the ground, and I was on my knees. It was awkward, but I wanted this. I wanted to be a sissy slut in a dress, pantyhose and heels.

My face was at his crotch, he unbuttoned his khakis and pulled them down with his boxers. Out popped a nice thick 6 inch cock, shaved. He was hard already and slid my lips around the tip. My addiction to cock while dressed in nylons and heels was overcoming my judgment.

Trent moaned and began to talk as I sucked his cock. "I can't wait to see you prance around in your dress and nylons on Saturday. Those legs are going to make me so horny."

My cock was hard under my panties and pantyhose, I slid my hand between them and stroked my cock through my pantyhose. I was close to cumming.

Trent put his hand on the back of my head and held it in place. He began to fuck my mouth with pace, cumming suddenly as I felt his cum fill up my mouth. He pulled away and sighed.

I swallowed it down and rubbed my cock, until I came right in my pantyhose and panties. I stayed on my knees for a while and regained my composure.

Trent pulled his pants back up and said "Sometimes we have a theme for you to dress up to. I will text you and let you know what the theme is."

I changed back into my jeans and headed home. I couldn't believe how my life was turning.

Tuesday night I went to Walgreens and bought makeup. Wednesday and Thursday I practiced my makeup skills, trying to look more feminine. I was dressed in panties and nylons while I did it. I was so excited for Saturday I masturbated 7 times. The excitement of being in full feminine persona in front of a lot of people excited me.

Thursday night Becky called me. "Did you want to hang out tomorrow after work?' I agreed and figured I would dress under my clothes tomorrow for Becky.

Friday morning, I showered and put on red panties and tan pantyhose. I wore jeans with a blue button shirt and brown boots.

Friday Becky came into my office after lunch. She looked amazing. She had on a pair of gray jeans, with a black top. She had on 3 inch black heels with black nylons.

"We have a drink and dinner after work? Does that sound good?" I nodded and she said "I will see you then, meet at Gibby's"? I nodded and she left my office.

Meanwhile Trent emailed me "Tomorrow's theme will be Cowgirl attire. If you have shorts or denim skirts, wear them. Boots or heels will work as well. See you tomorrow!"

I met Becky at Gibby's, I just enjoyed her so much. I sat down at the bar and she dropped her lipstick. She bent down to get it and her hand slid under my jean cuff. She felt my nylon covered ankle and smiled.

"I knew you would wear nylons for me tonight, I love it." she giggled.

I replied "I knew you would wear them for me as well." and I rubbed her nylon covered ankle.

We had a few drinks and an appetizer. Becky leaned in and said "Let's go to your place and you can lick my pussy."

We paid the bill and headed to my apartment. As soon as we walked in, Becky pulled me to her and kissed me feverishly. She unbuckled my pants and slid them down leaving me in the panties and pantyhose. I slid my boots off and unbuckled her pants. She had thigh high nylons on, she slid off her heels we made out and headed to the bedroom.

I slid off her panties and fingered her pussy as my cock tented in my pantyhose and panties. I slid down and began to lick her pussy. I worked it with my tongue and soon she began to buck her hips. She moaned and shook as she orgasmed.

She looked at me and said "Fuck me Chrissy, fuck me hard." I slid my panties off and ripped a hole in my pantyhose exposing my rock hard cock.

I slid my cock into her and began to fuck her missionary style. She brought her sexy nylon feet to my face and I licked the souls of her stocking feet as I fucked her. All the excitement of the week overtook me and I came within 5 minutes.

Becky looked at me "You were as horny as I was, that's awesome. Clean me out with your tongue Chrissy."

I licked my cum out of her pussy. She got up and went into my bathroom. She came out and said "Experimenting with makeup I see?" I turned red and she laughed. "I bet you look like a complete tart made up. Those legs will get you in trouble.:

I laughed. Becky put one of my T-shirts and I put my panties back and with a shirt and my ripped pantyhose. We sat on the couch and watched TV. I put in a frozen pizza and we ate that.

Becky looked at me and said "Do you mind if I spend the night?"

I replied "Of course you can, but I have to get up early. I have a job tomorrow morning."

Becky looked at me and said "What are you doing?"

I replied "Waiting tables, to make some extra money."

Becky replied "Good for you, where too? I didn't know you were looking for a second job."

I replied "Just some place about 30 minutes from here."

Becky nodded and continued "It doesn't have a name, gotcha. So why the makeup in your bathroom? When did you decide you wanted to practice makeup?"

I replied "I was in one of those moods, just experimenting."

Becky and I sat on the couch as we ate our pizza, she brought her sexy nylon feet to my panties and rubbed my cock. She knew my weaknesses.

She looked at me "When do you plan on going out in full Fem attire?"

I replied, "I really haven't thought about it."

She pulled her foot away and blurted out "I know something is going on Chrissy, the makeup, you having to work tomorrow and not telling me where. What if I wanted to see you after?"

She walked over and took my plate away. She straddled me on the couch, leaned over and whispered in my ear"Tell me now, I want to know. Or I will never,ever allow you to touch my nylons again"

Her sexual prowess was intoxicating. I caved.

I softly replied "I am working at Rumors tomorrow, I am dressing in Drag and waiting tables."

Becky smiled from ear to ear. "I have heard about that place, how did this become a reality for you."

I explained the story. Becky had her finger in her mouth listening. I could tell she was horny again.

I finished and Becky laughed. "You blew the husband of the wife you are working for? God you are a slut when you dress, I love it. What if she finds out? You could have a catfight with her."

I replied, "I know, he made a move on me, and I should've pushed him away."

We ended up having sex again and falling asleep.

My alarm went off at 6:30. I slid off my panties and hose and showered. I shaved extra close. I was going to change there, but put on my shaper, a pair of black control top pantyhose over pink panties. I needed to control my bulge. I packed a denim skirt, a white blouse, a red wig, headband and my black ankle boots.

Becky woke up and smiled. "Good Morning sunshine. Let me help with the makeup, please"

I grabbed a chair and took it into the bathroom. Becky began to apply my makeup. The more she did, the hotter I looked. After 30 minutes she completed my look.

She smiled and said "you are going to be one hot tart today Chrissy." and kissed me on the lips.

I dressed in a pair of jeans and a sweatshirt and drove to Rumors.

I walked in and Tonya greeted me. She gave me a hug and said "Your Makeup looks amazing." She was wearing jean shorts with tan pantyhose, cowboy boots and a ruffled shirt.

She continued "It will be you, myself and one more Girl" She brought up her hands to signify "Girl" with quote marks.

I went downstairs with my bag and changed. Tonya wanted to meet at 8:30 to go over everything. I slid on my skirt, white blouse, wig and headband. I was fixing my wig when the other server came in. Vanessa was a drag queen, she was tall and had a body to die for. She had big blonde hair and was wearing white shorts with tan pantyhose, brown ankle boots, a denim shirt and white vest. She looked amazing.

We exchanged introductions, Vanessa was very nice and said "I am excited to work with you today, you have amazing legs. It's going to be a ton of fun!!"

I replied "Likewise." and we both headed upstairs. Tonya assigned areas of the dining, she would seat people and take a small portion of the dining. Trent would be the bartender. Trent wasn't there yet, which was good for me after I blew him on Tuesday. I was already very nervous. Tonya urged us to be efficient and friendly.

I studied the menu and waited for my first public appearance as a Crossdresser.

Tonya opened the doors at 9 am. A few people trickled in, Trent came in as well and worked the bar. Tonya seated 2 couples in my section and they all ordered drinks. I brought the drinks to Trent and smiled at me. Trent said "you look amazing, great makeup today!"

I replied "thank you." and continued.

By 10:00 am, the place was packed. I was flying around, my feet were starting to hurt a bit. A few guys tried to flirt with me, but I didn't have time to flirt.

It was exhilarating to be fully dressed and working. I was really enjoying it. My cock was trying to harden but the Control Top pantyhose kept my cock in check. Vanessa slapped me on the butt a few times when we were crossing paths, encouraging me to "Keep it moving hot stuff."

Around 11 am, Tonya came up to me and said, "A few guests requested your section." she pointed to the table and it was Becky and a couple. I nervously walked over, now feeling outed by Becky.

She smiled and said "Hey hot stuff, these are my friends Lindsay and Dan. Lindsay, Dan this is Chris, or Chrissy today."

Dane nodded and Lindsay said "Wow, Becky made you look amazing.. So natural."

They ordered drinks and I brought them to them. They ordered a few rounds and Becky was pretty drunk. She tried to smack me on the ass, and I had to tell the bouncer not to kick her out.

The crowd began to slow down and soon it was 1:00 pm. Dan said he was "bringing Becky back to my place to sober up."

I agreed and went downstairs. Vanessa was sitting downstairs with her boots off. She smiled and said "Great day today Chrissy, I think we killed it." Vanessa's nylon covered feet were sexy for a "male" Her toes were painted a dark blue, she had reinforced toes on her pantyhose. I couldn't keep my eyes off of them.

I slid my boots off and sat for a second. My feet were killing me.

My cock did leak precum from my shift. The excitement of being in front of people was hot. The wives and girlfriends loved it I am sure, being served by Drag Queens, I am sure some of the men thought we were hot. I enjoyed it. I was becoming more and more comfortable dressing in female attire.

Vanessa asked me "What did you think?"

I rubbed my nylon covered feet and said "It was exhilarating, I started to crossdress out of curiosity and I've grown to enjoy dressing. The taboo feeling of dressing turns me on, and being in front of complete strangers today was hot. Add in the music and energy of the Drunch. It was awesome."

Vanessa nodded and said "It is empowering, you have to be careful with the clients. Sometimes they assume that because you are dressed as a lady, you are there for sex."

I nodded and Vanessa said "Let's go upstairs and have a drink while Tonya splits up the tips."

I got up and Vanessa stopped me at the stairs "Although meeting someone hot to have sex isn't a bad thing as well." She winked at me.

We went up the stairs, both of us in our stocking feet. Vanessa went behind the bar and poured us each a drink. I sipped the drink and relaxed a bit. Vanessa caught me looking at her feet a few times and said "You like nylon feet, don't you?" I nodded and she asked me to rub her feet, if I wanted. I nodded and she put them on my lap.

I rubbed her sexy feet while we chatted for a bit, talked about dressing, our lives etc. Tonya came out of her office with our tips and gave us each an envelope. I finished my drink and went downstairs to change.

I slid off my blouse and my skirt. I was standing in my pantyhose and shaper when Vanessa came downstairs.

She looked at me and said "Damn, you have a nice body"

I replied "Thank you, same to you, as I grabbed my jeans to put on."

Vanessa smiled and said "I should probably change as well" as she reached into her backpack. She grabbed a pair of cargo pants and slid off her jean shorts. She was wearing control top pantyhose as well. I glanced over and saw the biggest cock I had seen in person. It had to be 9 inches long.

Vanessa looked at me and said "You obviously are checking out my cock, I was wondering if you were bi-sexual. I did see your girlfriend there."

I meekly replied "I am bi, she knows it."

Vanessa walked over to the door and shut it and locked it. She walked back over to me and grabbed my hand and put it on her pantyhose covered cock. She leaned in and kissed me.