Dorm Days: Week 1- Jennifer

Week 1- Jennifer

“Alright, alright. Settle down class. We got some work to do. But first, I have an announcement to make. As you all know, Charlie, Jason and I own the drag club down on Peatchtree Street.”

Several cheers and hollers echoed through the auditorium.

“Alright,” he laughed. “Calm down folks. Anyways, we need three new waitresses for the club. We don’t need to you to perform. We just need you to act. And considering how this class is very hard to get into, I would hope some of you would be capable of this. I’m going to leave a sign-up sheet at the door. You have three days to sign- up. The pay is hard to beat and getting in the good graces with your drama, dance and vocal instructors is never a bad thing. Anyways, on to the play we have at the end of the month…”

Jeff could have used the money for the job, but there was no way he was going to dress up like a girl if there was even a remote chance his buddy’s could recognize him. Professor Theo’s bar was great and Charlie and Jeff were both great guys, but he couldn’t bring himself to do it. At least that was before Thursday rolled around.

“Alright class dismissed, see you guys Friday.” Theo said.

Jeff got up to go but Theo yelled for him. Jeff turned around walked towards Theo and followed him as he gestured for him to come into his office.

“Haven’t gotten to talk to you in a while Jeff. How did your summer go?”

“Not bad sir. I stayed on campus and took summer classes and got my core requirements out of the way.”

“Smart kid.” He chuckled. “Listen Jeff. You are one of the best performers we have at this school. You played Lady Macbeth magnificently. That is why I was so surprised when you didn’t sign up for the club interviews.”

Jeff broke eye contact and began to stammer. “Well… you know I’m busy and stuff…”

“Bullshit Jeff. You don’t have another job and you would be perfect for this. You have a dainty figure, no offense. You can do the best women’s voice that I have ever heard. And at most you are 5’6. You would be perfect for this.”

“I’m gonna be straight with you sir. I could not handle the ridicule if any of my friends caught me working there. I would die of shame.”

“You would be ridiculed at an all-boy’s school for liberal arts?”

Jeff thought about it and realized it was silly but he just couldn’t bring himself to say yes.

“All right Jeff,” Theo said as he began to dig around his desk drawers. “I know it won’t be a big deal so I’m only doing this to expand your horizons. You remember that Christmas Party Charlie hosted last year that we all went to.”

“Oh, Sweet Jesus, no…” Jeff thought.

Theo pulled out a picture from his desk. Jake was mortified. He had been very drunk that night and was convinced to dress up in a white babydoll with black stockings and open-toed, leopard themed heels.

“Now, all I ask is you let us try you out for a few weeks and then you can stay or go. Your choice. Do that and this picture goes away forever.”

Jeff did the only thing he could: say yes.

Jeff left the office with a feeling of dread hanging over him. Theo said to meet him at the club in a week so they could teach him everything he needed to know.

Jeff arrived at the club when he was told to. He resigned himself to his situation.

“I just need to do this for a few weeks and then I’m off the hook.” He thought to himself.

He entered and found the place was swarming with people running around doing construction.

He was looking around for Theo when a young, black haired beauty waved him over to her.

She was sitting by herself in the corner.

“Hey Jeff, I’m April,” she said in a sexy, feminine voice. He shook her dainty hand and looked her over. She had on a short, dark blue dress on and jet-black hair that matched her stockings. She was beautiful. 

“Pleasure to meet you,” he said with a big smile.

“I’m gonna be dressing you up today, sweetie. Let’s go play dress up”, she laughed.

She grabbed him by the hand and led him behind the stage. He relished the feel of her soft hand on his.

“How did you end up here?” Jeff asked as she led him through a winding hallway. 

“I’m one of the new waitresses. I’m in your acting class with you, silly”, she said.

Jeff looked at her face. He gave it a really good look over, but was still confused.

“Wait, so that mean’s…” he said as het let go of her hand.

“Theo told me you were gonna be difficult,” she sighed.

April grabbed her hair and, to Jeff’s surprise, just lifted it straight up.

“I’m Alex,” she said in a different, less feminine tone. 

“Charlie asked me to sign-up and I actually enjoy cross-dressing so why not get paid to do it?”

“But why do you act so different? Why didn’t you tell me you were Alex from the start?”

“Because I’m not Alex,” she said as her voice returned to her feminine, singsong tone. “April and Alex are two very different people honey. Now, come on. I have a lot to teach you to help you get in touch with your feminine side.”

She fixed her wig and locked her arm around Jeff’s as she led him into a new room. She sat him down in front of a mirror. He looked around and saw a room filled with clothing and make-up in front of him along with a vanity mirror.

April quickly got to work on Jeff. She taught him how to use foundation, blush eye shadow, everything under the sun.

“Now, that you know the basics, I’m going to doll you up so you can see how gorgeous your other self is.” April went on as she started applying make-up. She applied a layer of foundation that matched Jeff’s skin, penciled on some eye shadow, extended and darkened her eyelashes, and applied red lipstick to Jeff. After she was done, she left Jeff and came back with a blonde wig. She slowly lowered it onto his head. The feeling was strange for Jeff. He looked in the mirror and saw a beautiful woman. His body betrayed him as he squirmed to avoid any further social embarrassment.

“Now, Theo said since I helped create the new you, I get to name you. I am going to keep it simple. How does Jennifer sound?” she giggled with excitement.

“It’s as good a name as any,” he sighed.

“Now, don’t be such a sour puss,” she said as she rubbed her hands on his shoulders.

“You look great Jeff. Just get in touch with your feminine side. It is just like playing any other role you have done. Except this time you get to write your own part.”

“I guess. But this is just a temporary thing. I am just doing this for a few weeks and then Theo said I could quit. “

“Sure, sure,” she said sarcastically.

“I am serious,”

“Sure, sure” she laughed. 

Thanks for reading. A little short, but the next installment for  the next waitress will be much longer. Any comments are appreciated.