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The Women's Job - It's Confidential - Chapter Three
🕑 Added 2022-08-29 14:10:39 +0000 UTCOTHER CHAPTERS | ALL STORY LIST
They sat together at a bar a few blocks from Tess’s office. Lisa closed her cell phone.
“Tess will be here shortly,” said Lisa.
“What about, Jackie?” asked Dana as she picked up her glass and took a sip of her Cosmopolitan.
Lisa shook her head. “She’s off to be with her boyfriend, Chris.”
“Wow, that’s strong, do you drink these often?” asked Dana.
“They can take the edge off a long day,” said Lisa, as she took a drink of her own drink.
“So, you worked with Jackie before being hired by Tess?” asked Dana.
“Yes. We worked together,” replied Lisa. “We didn’t know each other that well as we spent much of our time in cubicles. I got to know her as she started her transition. We sort of bonded, and then she introduced me to Tess; the rest you can say is history.”
“That’s incredible,” said Dana. “Any regrets over leaving the corporate world?”
“None at all,” replied Lisa. “I like this job a lot more, and the money is much better. I also don’t have to deal with the office BS. Do you want to work in an office your whole life?”
“No, I’m due to move out of sales soon, maybe even after this job, and then I’ll be assigned to an engineering department,” replied Dana.
“Oooh, engineering, that’s so exciting,” said Lisa sarcastically.
“It is, I plan on modeling my career after Wally,” added Dana, referring to the Dilbert character.
“Good choice,” replied Lisa with a laugh.
“Seriously, I enjoy designing things. I love the problem-solving aspects of the job,” said Dana.
“What about other things? I mean, do you, is there someone else in your life?” asked Lisa.
“No, not right now, which is probably good. It makes things less complicated,” replied Dana.
“I see,” replied Lisa. “Well, just so you know, work isn’t everything.”
“I know, but I still have a lot of loans to pay off from college. This job could be just what my finances needed.”
“What else do you want?” asked Lisa.
“Damn, you’re nosey,” replied Dana with a smile.
“Yep, it’s one of my many flaws,” replied Lisa.
“I don’t plan on spending my whole life in an office, and work isn’t the only important thing in my life,” replied Dana. She took another sip of her drink.
“Okay, that was sufficiently vague,” said Lisa. She winked at Dana.
“Point taken, I guess haven’t planned out my life too much so far.”
“That’s good, because if you plan out things too far in advance, you may miss some interesting opportunities that life throws at you. I mean, look at me; this wasn’t what I thought I’d be doing,” said Lisa.
Tess walked over and took the stool next to Lisa. She picked up one of the near-empty glasses and examined the contents. “Well, I see you two have been busy.”
“I’m teaching Dana how to drink like a businesswoman,” explained Lisa.
Tess laughed. “Well, do you want another round?”
Dana and Lisa nodded.
Twenty minutes later, a group of businessmen walked into the bar. One of them looked over at Lisa and smiled.
“I’ll be damned. What are you up to, Lisa?” he asked.
“Hi, Mark, how’re things at Chambers?” asked Lisa.
“Hectic as always,” he replied. “So where do you work now? We were surprised you left; I mean, we all thought you were on the fast track to the top.”
Mark was in his late twenties and had dark brown hair. He was in good shape and had a rather high opinion of himself when it came to women. He had asked Lisa out several times, and after she kept turning him down he assumed she was a lesbian, although he never would say this to her face. Lisa always thought of him as being slightly annoying, but harmless.
“I got a better offer; I now work for a personal consulting firm,” she replied. “I like the more flexible hours.”
Tess turned to Dana and winked. Dana did her best not to giggle.
“Well, that sounds interesting,” replied Mark. He looked over at Tess and Dana. “So, how about introducing me to your friends?”
Lisa made the introductions, introducing Dana as a friend from out of town.
Dana couldn’t help but notice the way he ran his eyes over her. “Pleased to meet you; so where are you from?”
“Detroit,” Dana lied.
“So what brings you out here?” he asked as he moved closer to her.
“I have some business up in Seattle. I came down here to have dinner with Lisa and Tess,” answered Dana.
“Oh… well, maybe if you’re free another night, we can do dinner; would you like that?” he asked. He handed her his business card. “Here’s my number.”
She took the card and stared at it. “Thanks, but I have a rather full agenda this week,” replied Dana. She felt that strange feeling runs through her body again. It was the same feeling she had felt when Pete had looked at her the previous night.
“Well, you can’t blame a guy for asking,” he replied with a grin on his face. “Well, good seeing you again, Lisa. Nice meeting you, Tess, and, Dana, if you change your mind, give me a call.”
He then walked over to join his friends. He glanced over at Dana again and shrugged his shoulders; why did the good-looking businesswomen always turn out to be lesbians? he thought. He figured that any woman who turned him down had to be a lesbian.
Lisa and Tess leaned over towards a much relieved Dana.
“You passed another test with flying colors, I must say,” stated Tess.
“Yes, you passed on the ‘blowing off the sexist jerk in a bar’ test,” added Lisa. She held up her glass in a toast.
“Was he really trying to pick up on me?” whispered Dana.
“Oh, yes,” answered Lisa nodding. “He’s not that bad, but he’s not my type.”
“Nor mine!” interjected Dana. “Hey, I’m all for trying new things, but not that!” She lifted up her glass and touched those of Tess and Lisa and took a long sip.
“It’s okay, Dana, it happens a lot to our clients,” continued Lisa. “Consider it a sign that you’re doing a great job.”
Back at her apartment, Dana thought about the encounter at the bar. She looked at herself in the mirror and could see that she was really a male, but could others? Was Mark really fooled, and did he see her as a woman?
This was becoming more complicated than she had ever thought it could be. She knew that there had been no chance that she would have accepted Mark’s offer, but what if something like this happened on the trip?
She thought about that Halloween night back at college. When it had happened, she had convinced herself that it was just a one-time thing, that she had been drunk, and that it would never happen again. Yet, she had felt those, those feelings, twice since she had become Dana, and neither time was she drunk. She knew that she would have to be on guard at all times from now on.
Meanwhile, Lisa and Tess were discussing Dana over dinner at Lisa’s house. It was takeout Chinese, and they were sitting on the couch passing around the boxes.
“I agree with you, Tess; this can’t be the first time that Dana’s dressed,” said Lisa. “If it is, she’s the most relaxed client that we’ll ever have.”
“Did you see the way she reacted to Mark back in the bar?” asked Tess.
“Yes,” replied Lisa. “She’s definitely fighting some feelings.”
“I’m torn right now, Lisa. I don’t like to interject my feelings about clients without them first bringing it up, but it’s obvious that Dana is dealing with some gender issues,” said Tess. “Don’t get me wrong; as you know, I have nothing against her if she is transgendered, but I hate to see someone in denial.”
“I know. Granted, I don’t have as much experience in these sorts of things, but if Dana is a straight male who’s content with his gender, then I’m June Cleaver.”
Tess smiled. “No one would ever confuse you with her in a million years. By the way, when are you going to let me teach you how to use chopsticks? I hate to see you use a fork.”
Lisa laughed. She had a bit of a wild side and had shared some of her adventures with her co-workers.
“I’ve tried before and usually end up with more food on my lap than in my mouth,” replied Lisa.
Tess then reached into her bowl with her chopsticks and pulled out a small piece of Kung Pao chicken, held it out in front of her, and then ate it.
“Show off! Well, maybe we should have Jackie join us some night; maybe if Dana talked with her, she’d be more likely to open up. What do you think?” asked Lisa.
“Maybe,” replied Tess. “I just don’t want her to get hurt. I mean, this is different than one of our usual clients. Dana didn’t come to us on her own accord; she was picked by her boss because of her experience and body shape. It’s different when we get a crossdresser who turns out to be a transsexual.”
“That’s true,” said Lisa.
“A couple of years ago, we had another Wade salesperson named Larry Hill; I had the same feelings about him,” stated Tess.
“What happened to him?”
“She’s still working for Wade as Leslie Hill. She wrote me last year when she was recovering from her SRS. Mr. Wade told me that she’s now a VP,” explained Tess.
“As long as she’s happy, what does it matter?” asked Lisa.
“Hey, you don’t have to convince me, but I hate to see someone struggle with their identity. What if I’m wrong and say something to Dana?”
“Do you really think you’re wrong?” asked Lisa.
Tess shook her head as she ate. “I have something I want to try.”
The next couple of days passed quickly. Under Tess and Lisa’s watchful gaze, Dana practiced her dressing and makeup.
“I’d like to take you out to dinner Friday evening. It’ll give you an opportunity to dress up and practice your evening makeup,” said Tess.
“That sounds good,” replied Dana. “Will it just be us?”
“Yes, Lisa has a date that evening,” replied Tess. “Now, you’ll be on your own for the weekend, but Monday, I’m going to have Jackie go out with you.”
“Sure, that sounds okay,” replied Dana. “I have to study this weekend anyway. I want my presentation to be perfect.”
“Don’t overstudy,” said Tess. “Try to relax too.”
“I was thinking of going to the movies one night,” said Dana.
“Good. Now, do you want to meet her, or do you want me to pick you up this evening?” asked Tess.
“Why don’t you come by my place? That way, you can grade my appearance before we go out, and also make any corrections,” said Dana.
“I want you to wear the black dress tonight; let’s keep it simple,” said Tess.
Dana then discussed accessories to go with the outfit. Tess was impressed.
“You’ve been studying,” said Tess.
“Well, you told me to look at other women, and I have. I also have those fashion magazines that Lisa gave me,” said Dana.
“I can see why you were picked for this job,” said Tess.
Dana smiled back. “Thanks.”
“I want you to try wearing stockings tonight,” said Tess. “It’ll be a good learning experience for you.”
Dana sat on the edge of her bed and slowly pulled a stocking up her left leg. She had already ruined one and was determined not to repeat the mistake. When it was near the top, she stood up and attached the garters. In some ways, she was sort of surprised that women still wore stockings. Most of the women that Dana had dated as Dylan wore pantyhose.
She stood up and examined herself in the mirror. The stocking looked straight, and then she noticed a mistake, she had her panties on under the garters. That would make going to the bathroom rather difficult, she thought.
It took her a few minutes to correct this error. Dana smiled and knew she’d have to tell Tess of the mistake. She then finished getting dressed.
Her dress was a simple short, black sleeveless number with a matching jacket. Dana remembered how Tess and Lisa had told her how it could be easily adapted to look either formal or casual.
A short time later, Dana was applying her makeup. Eyeliner was still a problem, as Dana either used too much or not enough. However, this evening she seemed to apply just enough.
Pleased with this, she worked on her mascara. It also looked pretty good. Dana shook her head at the fact that she was becoming pretty proficient at putting on makeup.
Dana finished just a few minutes before Tess arrived.
After she let Tess in, Dana stood in front of her and smiled. “Well?”
Tess ran her eyes over her student and nodded. “Very good, Dana. You’re definitely the fastest learning pupil that I’ve had in a long time.”
Tess was also wearing a black dress.
“Okay, one last thing, you need to put on some perfume,” explained Tess. “Now at work, you should be careful about using scents, as too much can be really annoying to others, but for an evening you can be more creative,” said Tess. “Here’s a scent that I think will suit you.”
Dana sniffed the bottle and nodded. “Not too bad.”
“Now, don’t soak yourself in it, just a few drops will do,” explained Tess.
Dana did as she was told. “How’s that?”
“Perfect, now let’s go out,” said Tess.
They arrived at the restaurant and were shown immediately to their table. It was an upscale place that was rated as one of the best in the area.
“How’d you get reservations for this place? I tried once for a date and was told it would be a three-week wait, and that was just for a weeknight,” whispered Dana.
Tess glanced around and then motioned Dana to lean closer. “The head chef is a client.”
Dana cocked her head. “You’re kidding, right?”
Tess shook her head. “I only use our relationship for very special events.”
“I’m honored,” replied Dana.
“Well, you’ve done so well this week, I figured you could use a little celebrating,” replied Tess. “Besides, I love the lamb here.”
Dana laughed.
“I also want you to know that I now consider you a friend,” continued Tess.
“Thank you, I really appreciate that,” said Dana.
“I don’t do this for all my clients. Granted, I get to pick and choose who I help, so I can afford to drop the ones that creep me out, but I’ve also made some wonderful friends through my job.”
“Like Lisa and Jackie,” said Dana.
“Exactly. You’ll be spending a lot of time with Jackie next week, and I just know that you’ll get along famously. I’m a good judge of character,” stated Tess as she began to scan the menu.
Dana picked up her menu. “I’ve only talked to her a few times, but she seems really nice.”
“She’s very sweet. I brought her in initially to be my receptionist and assistant, but I want to move her up to working with clients too,” said Tess.
“From what Lisa said, Jackie was on the fast track at her old company. I’m surprised that she’d take a position as a receptionist,” said Dana.
“Jackie needed a big change. She had been hiding her feelings for so long, and when they came out, there was no way she could have stayed at her old job, even though her boss was supportive. She needed a position with less stress, as she had enough to deal with her transition.”
“But I thought her transition was going smoothly,” said Dana.
“Oh, it is, but there’s no such thing as an easy transition, even when you know it’s the right thing to do. I’m just happy to provide her with a job that allows her to bloom,” said Tess.
Dana nodded.
During dinner, Dana didn’t say much, as if she was lost in her thoughts.
“Is everything okay?’ asked Tess.
“Oh, my halibut is wonderful,” replied Dana.
“Then what’s up?” asked Tess.
Dana sighed. “May I talk to you after dinner about it?”
Tess nodded.
“Thank you,” replied Dana.
They drove back to Dana’s place after dinner.
“Would you like some coffee or tea?” asked Dana.
“What are you having?” asked Tess.
“Brandy,” replied Dana.
“That sounds good,” replied Tess as she sat down.
Dana poured two glasses and handed one to Tess. She then sat down next to Tess and took a sip.
“I don’t know where to start,” said Dana.
“How about wherever you feel comfortable?” replied Tess.
“Okay,” said Dana. “I feel really comfortable as Dana. I never really thought about this sort of thing, but the last week I’ve felt so relaxed.”
“I’ve noticed,” replied Tess as she took a drink. “Ohhh, this is really nice.”
Dana nodded. “I lied when I said that I never actually dressed before, I did it twice before.”
“Tell me about it,” said Tess.
“The first time was in high school. I dressed up for a costume party; actually, my sisters dressed me up.”
“Did you even think about dressing up in women’s clothes?”
“A few times, it was very confusing, and I did my best to fight off the feelings,” confessed Dana. “I was expected to excel in school, and being different wasn’t part of the program.”
“I see, so you were an overachiever?” asked Tess.
“I graduated from Purdue in less than four years; what does that tell you?” asked Dana as she took another sip of her brandy.
“Point taken, let’s get back to Halloween, what did you wear?”
“My sister’s cheerleader uniform,” replied Dana. “I looked really good, almost too good. My sisters kidded me that I should try out for the team the following year. At the party, I fooled a lot of people. I ended up winning the top prize.”
“So, it was their idea?” asked Tess.
“Yes, but I didn’t put up much of an argument. They had been kidding me for years that I would make a cute girl, and when they suggested that they turn me into a cheerleader, I readily agreed.”
“Anything else happens?”
Dana shook her head. “Well, that’s not true; I got a date with one of the cheerleaders out of the deal.”
Tess laughed.
A smile broke out on Dana’s face. “It turned out that I lost my virginity to her.”
“Can I ask you a question about that?” asked Tess.
Dana nodded.
“How did it happen? I mean who instigated it?”
Dana cocked her head, and then it hit it. “She did. Wow, I never really thought about that, but she took charge.”
“Did she dress you up; I mean, in girl’s clothes?”
Dana looked shocked. “How, how did you know?”
“It’s not that uncommon,” replied Tess.
“She just put a bra and panties on me. Oh, she also put lipstick on me,” said Dana. “Wow, I totally forgot about that.”
“What about the next time?”
Dana took another long sip and almost emptied her glass.
Tess reached over and put her hand on Dana’s shoulder. “You don’t have to tell me.”
Dana shook her head. “No, I want to, I need to.” She reached over and picked up the bottle of brandy and refilled her glass. “It happened in college. I had just broken up with my girlfriend, and it was Halloween. My roommate and his girlfriend talked me into going to a big party they were going to. I didn’t have a costume, and the party was that night, so Cathy, my roommate Bob’s girlfriend, suggested that I go as a girl.”
“I see,” said Tess as she reached for the bottle.
“She dressed me up in a short spandex dress, and she sort of made me up as a hooker,” continued Dana. “She dressed sort of risqué too, and we were the same size. Bob thought I looked hot.”
“So what happened at the party?”
“I knew maybe half the people at the party, and I fooled most of them. Cathy told everyone I was her cousin from South Bend,” replied Dana. “Anyway, it was a college party, and there was plenty of alcohol and pot. I got a little wasted. I soon found that Bob and Cathy had left the party.”
“What happened to them?”
“They headed over to her place to have sex. They called on my cell phone after they left, I told them that I could get home on my own,” replied Dana.
“I see,” said Tess.
“Anyway, I was sitting on a couch trying to clear my head when a guy sat next to me.”
“Did you know him? asked Tess.
Dana nodded. “Yes, his name was Jim. We weren’t exactly friends, but we’d had some classes together in the past. He was a couple of years ahead of me. Anyway, he told me that I made a pretty convincing chick.”
Tess just nodded.
“He went on to say that it was amazing how I’d manage to fool most of the people at the party. He then said that the party seemed to be dying out and asked me if I wanted to go to another party he knew about. I wasn’t exactly thinking straight, so I said sure.”
“Was he in costume?”
Dana shook her head. “I should have noticed that, but like I said I was a little wasted. The other party wasn’t a costume party, and he passed me off as an old girlfriend.”
“What did you do?” asked Tess.
“I played along. It was fun fooling them,” replied Dana. “Granted, they were all a little wasted too.”
“What happened next?” asked Tess.
“Jim had his arm around me and I played along. Soon I was sitting on his lap, and he began to kiss me.” Dana took another long sip.
“What did you do?”
“I kissed him back. It felt so right. I felt tingles all through my body as he caressed me. He may have started it, but I didn’t resist,” said Dana.
“Did it end there?”
Dana shook her head again. “We went into one of the bedrooms and began to make out more. He told me that I was his bitch and things like that.”
“I get the picture,” said Tess.
“I couldn’t stop, and soon I was on my knees in front of him giving him oral. I was thrilled that he loved it. It was as if I was a different person. I had never had a homosexual thought in my life, but that night it felt so good.”
“I wouldn’t exactly call it homosexual; I doubt you saw yourself as male,” said Tess.
“That’s true. I saw myself as a woman. I was able to rationalize it by telling myself that I wasn’t a guy. I did the same thing when he fucked me,” confessed Dana. She wiped a tear away from her right eye.
“It’s okay, Dana,” said Tess, as she leaned over to hug her.
Tess refilled their glasses. Dana nodded and picked up her glass.
“I’m glad I’m not working tomorrow,” said Dana. “Anyway, he took me home and thanked me for a wonderful evening. I took a long shower before going to bed. He never contacted me again, and this is the first time that I’ve dressed up since.”
“Did you get the urge to?” asked Tess.
Dana nodded. “I blocked it out and threw myself into my studies. I never told anyone about it; well; I did get an HIV test a few months after it all happened.”
“And how are you doing now?”
“I’ve had some strange feelings,” she said. She then told Tess about Paul and Mark. “I didn’t do anything and was in control, but both encounters awoke those feelings I had with Jim.”
“I wish I had known earlier,” said Tess.
“There’s nothing I can do about it; it’s too late to back out now. Besides, those feelings are real; eventually, I would have to deal with them,” said Dana.
“I see,” replied Tess.
“I like the way I look now; I don’t know if I can go back,” continued Dana.
“Well, let’s not make any decisions right now,” said Tess.
“I know. Tess, I’m an engineer at heart; we’re not exactly spontaneous people,” said Dana with a slight laugh.
“Um, sleeping with what’s his name, Jim; that was pretty spontaneous, even if you were drinking,” said Tess.
Dana signed. “You’re right, hell, even I don’t believe it. So what now?”
“We move on and continue to prepare you for your sales mission. However, I think when this is all done; you need to start seeing a therapist. I know a very good one who deals with gender issues, and if it makes you feel better, Jackie is seeing her,” said Tess.
“Okay, that sounds good,” stated Dana as she yawned. She was struggling to keep her eyes open. “It’s amazing how exhausting spilling your soul can be.”
Tess laughed. “Let’s get you to bed; we can talk more over the weekend.” She stood up and began to help Dana up.
“I thought you were busy this weekend?” asked Dana.
“I’m business busy, but I always have time for a friend,” said Tess.
