As Steve finds help and begins to accept his truth, a challenge is set to spread his wings. Someone might be too enthusiastic.

Chapter 7

Steve returned to college for his junior year and that was when he met Kathy. Amy knew Kathy from high school and convinced her transfer to their school. Kathy was unlike any woman Steve had ever met. She smart, sexy with a sarcastic wit and before he knew it, he had fallen head over heels for her. As he thought back, perhaps it was just lust. Whatever it was, he didn’t think long on how it might affect his friendship with Amy and Sue. After Sue’s comments the previous year he was determined to make this relationship work.

Everything was great until the Halloween party.

Doctor Johnson started the next session with a tough question, “Was the first time you dressed as a woman that night with Kathy?”

Steve hesitated.

She broke in, “I can’t help you Steve if you don’t tell me the truth.

“Not really.”

“What do you mean by not really?”

“Well I experimented a little before that.”

“How’d it make you feel?”

“Bad.”

“Why do you think you did it?”

“I don’t know. I just did.”

“Did you masturbate when you were wearing makeup before you met Kathy?”

Steve’s face turned a deep crimson color. “No! Why would you ask that?”

“Are you telling the truth?”

“Yes. Of course.”

“OK. Let’s move talk about after you and Kathy broke up. How does it feel when you wear women’s clothing?”

“I really can’t describe it. I just feel comfortable.”

“Do you get aroused?”

Steve hesitated, “Sometimes.”

“And you’ve masturbated a few times haven’t you.”

“Yes.”

“What do you think about during?”

“I don’t know.”

“Think about it.”

“It’s embarrassing.”

“I can’t help you if you don’t tell me the truth.”

Tears streamed down Steve’s face, “I think about being a girl! Is that what you want to hear?”

Angie answered, “Only if it’s the truth.”

“Why would anyone say that if it weren’t true.”

Doctor Johnson continued, “What do you think about after you are done?”

The question surprised Steve, “Huh?”

“After you are finished masturbating. What do you think about?”

“Ummm … I don’t know. Not much. I can’t remember.”

“Do you change back into your “normal” clothes afterwards?”

“No. I pretty much spend my nights and weekend dressed in women’s clothes.”

Angie wrote on her notepad. “You spend all your spare time in women’s clothes?”

Steve nodded.

“What do your friends think of this?”

“My friends don’t know.”

Doctor Johnson looked from her notepad. “How can your friends not know if you are always dressed up?”

“It’s because I’ve become antisocial since Kathy and I broke up. I pretty much spend all my time alone in my apartment dressed in women’s clothing.”

“No one visits you?”

“Nope.”

“How is that possible? It sounded like you had a pretty active social life before you dated Kathy.”

“I did but over the last two years I started to spend all my time with Kathy’s friends. When we broke up, it was too awkward to continue to meet and we lost touch.”

“What about old friends or people you meet in class?”

“I’ve found that if you say no enough times, people will eventually stop asking you to go out.”

Dr. Johnson wrote on her notepad then said, “OK.” She glanced at the clock. ”We are about out of time but I want to touch on one thing before you leave. It worries me that you have pushed all your friends away. You don’t have to tell them anything but I really think it would be a good idea for you to get out of your apartment.”

Steve shrugged, “I guess I could talk to my gay friend Tim. He’d understand if anyone would.”

Doctor Johnson shook her head, “Your gay friend Tim? You do realize how bad that sounds?”

“Sorry.”

“What’s your friend’s last name if you don’t mind me asking?”

“Donelson. Tim Donelson”

Steve saw a hint of a smile cross Dr. Johnson’s face, “Ok, meet with your friend Tim and I’ll see you back here next week.

“Thanks Doc.”

Chapter 8

As Steve got home he changed into what he thought of as his “comfortable clothes”. He found the process of putting on makeup to be relaxing and as he started his routine, he thought back to the first night he went completely en femme. Sue and Amy had a huge Halloween party and Kathy suggested that they turn the apartment into a brothel as that year’s theme. Steve would be their pimp and they would be his girls. Sue liked the idea but added her own twist.

“Did we ever tell you the story about Steve’s last birthday? I’m thinking Steve should work for you instead.” Kathy loved the idea.

Before Steve knew it, the girls had planned everything. Sue and Amy were in charge of the costumes and alcohol. Kathy and Steve were in charge of the decorations and food. When the big day arrived and he finished the decorations, Amy and Sue took over.

Amy ordered him into the bathroom to shower and shave. As he was just about finished, Sue knocked on the door, “When you are done put these on. I think you can figure it out.”

She had handed him a pair of underwear but they weren’t like any underwear he’d ever seen before. He put them on and as he pulled them up he realized they were much tighter in certain areas and pulled his penis down and back between his legs. He had a little trouble pulling them tight until he realized he needed to push his testicles up into his body. He still remembered the shiver of that feeling as he tightened the gaff. It wasn’t pain as it didn’t really hurt. Emasculated was close but not quite right either. As he rubbed his hand over his groin and felt nothing there, he got a thrill he hadn’t expected. As he posed in the mirror, he remembered being aroused by the look. He even strutted around the room but stopped as his arousal was making it uncomfortable to walk.

When he exited, Sue and Amy burst into laughter, “That has to hurt.”

He answered, “It ain’t exactly comfortable.”

When they stopped laughing, they ordered him to sit in the chair, “Hurry, we need to get ready too.”

It wasn’t long before they started commenting on his looks.

Sue said, “I never realized you had such high cheekbones. This base really brings that out.”

Amy added, “And I’ve always been jealous of your pouty lips. This lipstick will help them stand out more.”

Steve endured these comments and more as they pushed and pulled his body in unfamiliar ways. They applied all sorts of crèmes and colors until they were finished.

“Done! Kathy come out and tell us what you think.”

Kathy walked into the room and said in a shout. “Wow Sue you were right.”

Sue answered, “Just wait until we get the dress, wig and the other surprises.” The girls laughed.

Steve grew suspicious at the last comment but knew he was at their mercy, “Other surprises?”

Sue’s face took an angry demeanor, “Just sit there and be quiet, bitch. I’m your pimp momma tonight and you are just one of my ho’s.”

Kathy laughed, “Someone is getting into character a bit early.”

Next came the panty hose, which weren’t too bad considering the underwear had already done the tough part. Pulling them up and feeling nothing as the fabric tightened against his front was definitely a new sensation. Next came the padded pants which reminded him a little of the pads he wore to protect his tailbone and hipbone in football. After that a corset was applied which they tied as tight as they could around his waist. Sue explained that the goal according to the salesperson that sold them the items was to give the appearance of wider hips but a small waist.

Next came the bra. Steve had never worn a bra though admittedly the thought had crossed his mind a few times. Sue and Amy had gone overboard on this too as it was a special bra with foam padding to mimic real breasts. As they fastened the clasp Steve looked in the mirror and once again felt himself start to be aroused. Luckily, the gaff held everything in place. The pressure from the bra felt like it actually improved his posture as it forced his shoulders back and his “boobs” out.

“This feels really odd.” Everyone stared back nodding their approval.

Sue and Amy each took a hand and applied extra-long press-on nails to each of his fingers. They were painted deep black and he remembered telling them, “You sure put a lot of thought into this.”

Amy and Sue started to laugh hysterically and Steve started to feel self-conscious. The only thing that remained was the leather miniskirt and matching leather top. After that, they strapped him into a pair of black 3-inch heels and as he tried to stand, he fell back into the chair. He’d never worn high heels before and they were certainly a learned experience. As Sue called for Kathy to see the final product, she handed him the leather whip that matched the outfit.

Steve asked, “Where’s the ball gag?”

Steve remembered the response as something like “We ran out of money.”

He was never completely sure Sue was joking. When Kathy came out, he swore he thought her jaw was going to hit the floor. He felt the same way when he looked in the mirror. It was strange. He knew he was looking at himself but he felt different. It was almost like his dreams had come true. He even felt like a different person, freer somehow.

The party itself was funny as no one paid him any attention until someone mentioned they were surprised Steve wasn’t at the party. When Sue stopped laughing, she spilled the beans. By that time the alcohol was flowing and Steve’s memory wasn’t perfect but he did remember being happy.

The party died down around 1am and went Steve into Kathy’s room to change into something more comfortable. The combination of long nails and alcohol made that impossible. As he sat on the bed trying to take off his heels, a silhouette appeared in the doorframe the whip in hand.

The crack of the whip got his attention and Kathy ordered, “What do you think you are doing?”

“I was taking…”

She cracked the whip again, “No talking or there will be punishments! There is no Steve only Sara.”

Steve smiled as he saw where Kathy was going. “Sara is yours to command.”

The next hour was a blur and Steve couldn’t remember a more pleasurable evening in his life. He was never entirely sure of Kathy’s thoughts as they never discussed it afterward. When Kathy excused herself to go outside for a cigarette, Steve followed. When she lit hers Steve asked for one and Kathy laughed, “Since when did you start smoking?”

“Sara’s always smoked.”

Kathy shook her head at the comment and handed him one. He clumsily put it in his mouth and she lit it for him. After nearly choking after the first try Kathy helped him take his first steps to becoming a smoker. He remembered getting a buzz from the nicotine that bordered on nausea. His last memory of the night was kissing Kathy softly on the forehead and telling her for the first time that he loved her. She said she loved him too.

It seemed like things would be that way forever but it only took another few months before it was over.

Why couldn’t he make it work with Kathy? She was pretty much everything he’d ever wanted. Why did he screw it up? His actions that led to their breakup played constantly in his mind like a bad movie. On the bad nights, it always led to more drinking until he passed out in front of the television.

His college career was almost over and turning out to be a major disappointment. His grades had never been great and now with his recent troubles since he broke up with Kathy, he was dangerously close to flunking out entirely. The conversations with Dr. Johnson helped but he still spent every night alone in his apartment. Maybe meeting with Tim would help. He’d pushed Tim away but he’d always been forgiving.

Steve worked up the courage to call him the next day. “Hey Tim. It’s Steve. How’s it going?

“Not bad. You?”

“Well … that’s why I’m calling. Do you have some time to meet?”

“Sure thing… Student Union?”

Steve took a deep breath, “I was thinking that perhaps you could you come over to my place?”

Tim laughed, “This isn’t some elaborate plot to seduce me is it Steve?”

“If that were the case Tim I’d just say it. You always were a slut.”

Tim said. “And I see you are still the charmer. How about tonight at 7?”

“Sounds great.”

“See you then.”

Steve started to get ready for the evening and he thought about what he’d say to Tim. Meeting at a restaurant would be nice but they wouldn’t have any privacy. It also would have been too easy to avoid the difficult subjects. He decided to invite Tim to dinner at his apartment and spent extra time getting ready. As he looked in the mirror, Steve was reasonably happy with the results but mattered little. Tim would be shocked no matter how good his makeup looked. Steve finished up some homework and heard a knock on the door at 6:55 PM.

”Here goes nothing...,” and Steve opened the door.

Tim stood speechless and a strange look came over his face, “Steve?”

“Yeah.”

“I barely recognized you … err um … nice outfit.”

“Yeah, yeah. Come in and I will explain.”

Tim sat on the couch without a word while Steve grabbed two glasses and a wine bottle. As he poured, Steve tried to ignore Tim’s stares.

“Please stop that.”

“Stop what?”

“Stop staring so much.”

“I’m sorry Steve but this is a shock. I really didn’t recognize you.”

Steve lit a cigarette, “Well, you are the first person that has seen me like this.”

Tim said, “I didn’t know you smoked.”

“It’s another bad habit I picked up recently.”

“You should quit.”

“Yep, I should.” Steve took another drag and blew smoke in the opposite direction.

The room grew quiet. Tim sat without speaking for a few moments then asked, “So what do you want?”

Steve felt like he was about to cry but forced himself to speak. “Dammit I don’t know. I just figured I could talk to you.”

“Because I’m gay? ”

“Kinda.”

“Don’t you think that’s a bit insulting. I’m probably as messed up as anyone. I hope you don’t think I have any answers.”

“I guess I just figured that you would understand if anyone did. I know you went through a lot freshman year and thought you might be able to help.”

“Yeah that was a tough year. I remember a particular bigoted hick that made my life hell the first semester.”

Steve looked away, “Yeah, I know. I was stupid. I didn’t know any better. Didn’t we become friends after that?”

“Yeah once you took the time to get to know me. I’m over it now but I didn’t like you much at the time.”

“That’s one of the things I’m worried about. I mean I know personally how mean-spirited people can be. I just needed someone I can trust to talk to that I thought might understand. That’s why I called you.”

“I guess that’s fair. I’m no expert though.”

“I appreciate it. You see here’s the thing … I’m so fucking confused. Every night, I get home and I dress like this. I don’t dare let anyone see me so I’m always alone. I wake up the next morning and can barely look at myself in the mirror but as the day progresses, I can’t wait to get home and change again. It’s to the point I feel more comfortable dressed like this but I can’t go outside and it is making me miserable.”

“I’m sorry Steve but I’m really not comfortable talking about this.”

Steve lost control and felt the tears rolling down his cheeks. “I just need a friend dammit!” He looked down as the tears hit his blouse.

Tim put his arm around his shoulder, “I’m here. I just don’t know what to say.” Tim grabbed a towel and wiped the tears from Steve’s face. “But I’m here.”

Steve lowered his head and put it on Tim’s shoulder. No one said a word until the timer on the oven went off. Steve didn’t say a word and went into the kitchen.

Tim asked, “What’s for dinner?”

“Nothing fancy. Just a pasta dish I like to make.”

“It smells fantastic.”

Steve took the food to the dining table and Tim brought the wine. They both ate silently until Tim asked, “How’s the job hunt going?”

“Not great. I’ve let my grades slip and most companies won’t even talk to me. How about you?”

“I’ve got interviews with a few schools so I’m pretty hopeful.”

Steve responded, “That sounds great.”

Tim smiled. “Things sure have changed since freshman year”.

“What do you mean?” Steve said defensively.

Tim said, “I don’t mean anything by it it’s just that I was so sure of everything when I was a freshman. I had all the answer to life’s questions. Now I’m constantly questioning myself. ”

Steve looked down at his outfit and laughed. “Are you trying to say something?”

“Yes and no. Hear me out for a second. I mean I thought I really understood what I wanted from life but things aren’t that simple. I thought all I had to do was to get away from home, get away from mom and dad and everything would be better. I’ve always heard that the toughest part of being gay was coming out. Don’t’ get me wrong it was tough. Telling my parents was the toughest thing I’ve ever had to do and the aftermath wasn’t much better as they kicked me out of the house. We’ve mended our relationship gradually and we have come to an understanding. They don’t ask and I don’t tell but the problems don’t stop with your parents. Every day I meet new people and I swear I can almost feel the whispers. It’s getting better but people are so damned judgmental. It’s like I have to come out every day and it can be exhausting.”

Steve repeated his question, “Are you trying to tell me something?”

“A little but I guess I told you that because I really wanted to ask a question. What’s your point of meeting me dressed like this?”

“I really don’t know. It started last year. Actually, it’s actually been going on longer but that’s beside the point.” Steve took a deep breath and looked at the ceiling. “I really like dressing in women’s clothing. I’m not sure why but I think it is part of who I am. It’s hard to describe but when I’m dressed like this it feels … right. It’s to the point that I’m always dressed as a woman whenever I’m home. I’ve been doing it for so long that I really look forward to Friday’s when I can be myself for the whole weekend.”

“Two whole days? I thought you said I was the only one that has seen you like this.”

“For the last two months I’ve pretty much ignored anyone that wants to do anything. I shut myself in here and watch TV and smoke a lot of cigarettes.”

“That doesn’t sound healthy Steve. When did you start smoking anyway? I remember you as being an anti-smoking fanatic as a freshman.”

“I was and I am. I know that sounds odd from someone holding a cigarette but it’s just a bad habit I picked up from my ex and I haven’t been able to stop. It’s honestly to the point that I think cigarettes are the only thing keeping me sane and I know that is crazy.”

Tim laughed. “So you are a chain smoking shut-in?”

“I’d put it nicer than that but it’s about right. Every Sunday night I get depressed thinking of Monday. The next day I put on my ‘regular’ clothes and go to class but they don’t feel right anymore.”

“Have you ever thought of going out dressed as a woman?”

“Are you kidding me!?!?!?”

“No. If it is so important to you that you are depressed when you aren’t dressed like that then why not?”

“I just can’t. People will stare. Then they will make comments. Eventually I’m sure someone I know will find out and I just can’t deal with that.”

“Yeah? So fuck ‘em if they can’t handle it.”

“I can’t handle it.”

Tim shook his head, “I know from personal experience there will always be haters. Did you ever go to a therapist like I suggested?”

“Actually I did.”

“And?”

“She’s pretty cool. She was the one who told me I should reach out to a friend.”

“And you thought of me? I guess I feel a little honored.”

“You are the most open minded person I know.”

Tim changed the subject, “I’m glad to hear you are seeing someone. It has helped me a lot.”

“You go to counseling too?”

“That’s why I suggested it. Everyone goes through things they need to talk about. It’s really nice to get another person’s opinion to help through things I can’t work out. Angie has really helped me.”

Steve laughed, “Doctor Johnson???”

“Yeah she’s my therapist. She’s great.”

Steve doubled over in laughter, “Yeah … I know. That’s who I’ve been seeing too.”

“You’re kidding. Seriously? “

Steve nodded, “Yeah, I’ve only seen her for about three weeks but she’s helped me. I told her I was thinking about talking to you.”

“I bet she thought that was funny.”

“Probably. Now she gets to hear about tonight from both of us.”

Tim put his hands on his hips in mock anger, “What makes you think I want to waste my time with the doc talking about your lame ass. I got serious issues to discuss!”

Steve shook his head but he was smiling, “Whatever Tim, do you wanna watch a DVD?”

“Are you changing the subject?”

Steve looked at Tim and didn’t say much for a few seconds. “Yes, and I really appreciate you coming over here.”

“You’re welcome Steve. It is still Steve right.” Tim laughed.

Steve answered, “Oh fuck you. That’s cold.”

Tim said, “I could say a thousand things like that and we still wouldn’t be even for freshman year.”

Steve answered, “Yeah you’re right, sorry about that.”

Tim was smiling. “Water under the bridge man. You just need to learn how to take a joke or you will never make it.”

“Well … I am feeling kind of gay right now so I guess that’s a start.” Steve started the DVD.

Tim said, “If that was an attempt to hit on me, I’m sorry but I’m not into girls.”

Steve turned down the lights and answered, “That’s good because I’m still not into men either”.

The two friends laughed and sat to watch the opening credits. Steve found himself looking at Tim and knew he was lucky to have a friend like him. A mental image of kissing Tim popped into Steve’s head and he forced it out.

When Steve arrived at Doc Johnson office the next week he noticed she was dressed in jeans and a sweatshirt and had a big smile on her face.

“Tim told you.”

“I can’t talk about a session with another patient.”

“Bullshit.”

“We’re on a real fine line here and I will confirm that Tim is a patient of mine and has been for a few years. “

“I can’t believe he has been seeing a therapist. He’s always seemed so sure of himself.”

“Most people hide their true feelings. Speaking of which, I heard through the grapevine that you had dinner with a friend last week dressed in women’s clothing. That’s progress.”

“Yeah. I decided if I was going to meet with Tim, it was time to share my secret.”

“That’s really great. I think you will find having a friend will be very important.

“For what?”

“We really haven’t talked much about why you called the university counseling center in the first place.”

“You never asked.”

“I wasn’t sure if you were really ready to answer it but I think you are now. Do you know why you called?”

“I think it is pretty obvious since I’ve been shut up in my apartment for almost 2 months.”

“That’s not why you called, that’s just a symptom of why you called. Why did you call?”

“Because I was depressed.”

“I’m sure there was more to it than that.”

“Honestly Doc I’m not sure what you mean. If you think I was going to kill myself I can’t say the thought didn’t cross my mind but I don’t think it was a serious thought.”

“So why did you call?

“I don’t know. Perhaps it’s because I look in the mirror and don’t know who I am anymore.”

“Did you ever?”

“I don’t know. I guess I didn’t.”

“You mentioned last time you thought you were gay. Why do you think that?”

Steve was getting angry, “Have you been listening to me!?!?”

Doctor Johnson smiled. “Do you have feelings for men?”

The mental image of kissing Tim popped into his head, “I don’t think I do but I’m a bit of a mess these days.”

“At the risk of sounding like a professor I want to tell you few things. I personally don’t like the term gay because a person’s sexuality is much more complex than one word can possibly describe. Not everyone agrees but I personally like to think that sexuality is made up of four things – genetic sex, gender identity, social identity, and sexual orientation.”

“That made no sense.”

Doctor Johnson laughed, “I didn’t think it would but I wanted to introduce the concepts. Next week is Thanksgiving so we won’t be able to have our normal Thursday meeting but I’d like you to check out a few books from this list at the library. They will give you a much better understanding.”

“That’ll work out since I’m planning on spending the whole time in my room.”

“Aren’t you going home to be with your family?”

“Yeah, I meant my room at my parent’s house.”

“Part of the reason I wanted you to go out with Tim was to get you out of the house. That didn’t work exactly as I expected so now I’d really like it if you made an effort to socialize with some of your friends back home.”

“I’ll try.”

“That’s all I can ask. I’d also like you to tell your parents about your smoking.”

“What? Why?”

“Let me ask you … Did you smoke over the summer?”

“Yeah but I only did it when they weren’t around.”

“It wouldn’t surprise me if they already knew especially if your mom still does your laundry. Things like that are hard to keep a secret. Honesty is usually your best option and you really should tell them. None of us are perfect and the main reason parents get disappointed is they don’t like to see their kids repeat their own mistakes. They will adjust in time.”

“I’m not sure I can.”

“How do you expect to ever figure out who you are if you are always lying about yourself to others?”

“All right doc, I’ll think about it.”

Doctor Johnson looked at Steve and it felt like she was trying to read his thoughts. “It’s a start.”

“OK.”

“We are almost out of time but I have to ask one last thing.”

Steve nodded.

“I have a colleague that is doing testing for a research project and I think you might be a perfect candidate. He’s got an opening the Monday after Thanksgiving and I’d like you to see him. His research will be helpful with our discussions and I hope to have the results at our next meeting.”

“Sure, whatever.”

“You don’t sound sure.”

“Sorry, this has been a tiring session and your earlier comments have me worried about my trip home.”

“Are you nervous?”

“A little.“

“That’s normal. You’ve got a lot on your mind and you really need to relax. That’s why I gave you homework.”

“If you say so. I’ll try.”

That’s all I ask. See you in two weeks.”

“See ya doc.”

Tim called a few days later and after gossiping about their separate meetings with Dr. Johnson, Steve realized that Angie had asked Tim to follow up. It was great to hear from him and they agreed to meet for drinks the next night.

Tim saw Steve across the bar and sat down at his table, “Oh hey Steve. I almost didn’t recognize you without your mascara and lipstick.”

Steve looked around to see if anyone heard.

Tim looked apologetic. “Sorry Steve but I wasn’t kidding when I said you need to learn to not be so sensitive if you ever plan to go public. It was a hard lesson for me and some people aren’t as accepting as others.”

“Are you ever going to let me forget that? Sorry. I was a jerk.”

“That’s not what I am saying. After you got to know me we became friends but there are many ignorant people in the world that aren’t that open-minded. You can’t let them get you down.”

Steve changed the subject, “Hey speaking of my issues….” He smiled and pointed under the table. Steve had pulled up a pants leg to reveal he was wearing a pair of stockings under his pants. “I thought I’d try it out. Honestly it’s feels great.”

“That’s great. Small steps.”

“I never considered looking forward to cold weather but I’m already thinking of all the different things I will be able to try once it’s sweater season.”

Tim shook his head, “Oh my god, I’ve created a monster!”

They chatted aimlessly for hours like any good friend then said their goodbyes. As Steve walked home, he felt great. It had always bothered him how badly he’d treated Tim when they first met. He’d said some really stupid things but Tim never held a grudge. If Tim were vindictive, he now had all the ammunition he needed to get back at him but Steve trusted Tim. He was pretty sure people in their situations couldn’t afford to lose true friends.