I looked in the mirror and tried to remember all the steps I would need to make this work. First, I got some bronze make-up and put a bit on my cheekbones and temples to create greater contour. I then put eye shadow on my forehead, around my eyes, and on the sides of my nose. I took out a highlighter and worked my cheekbones, jawline, and around my brow. I then took a brow pencil and a brow liner to make my eyebrows slightly bigger and thicker. For my face, I knew that make-up wouldn't cut it. I needed to look like a man not just from a distance but really close up as well. When Natalie kissed me, she would need to see me as a man for this work.

So, I used artificial hair and glued patches of them on my face to give me a beard and mustache. Once I was done with the face, I placed a wavy wig on my head. If I had cut my hair short, Nate would go ballistic on me and it would still look feminine. For this, only a wig would do. For my chest, I put on a binder tank-top I had ordered online to make my B-cup breasts flatter, put on a bulky sweatshirt, and then put on male jeans that were a little too big for me. I placed pads around my waist to equalize my hips giving me a square body-shape. To add to the look, I gave myself a belt but kept it loose. To hide my feminine hands, I put on black gloves. As it was winter, I would be able to get away with it without looking weird. On my feet were black-and-white generic tennis shoes that Nate actually wore. He actually bought tennis shoes that were a few sizes too big for him and then put tissue paper at the toe-end of the shoe. This gave everyone the appearance he wore a size eleven when he actually wore a size eight. Finally, to cover my lack of adam's apple, I put a scarf around my neck.

I finally exited my room and found Natalie watching TV in the living room. She eyed me with surprise and then started to scrutinize my appearance. She stared at me long and hard and then circled around me. "Okay," she said.

It was not the endorsement I had hoped after working on myself for thirty minutes. Still, we were off to the movie theater. I paid for everything in cash to avoid having to be carded and then went with Natalie to sit through a romantic chick flick. She seemed fully engrossed in the movie as she drank coke and ate popcorn. She would occasionally hand the popcorn over to me forcing me to take off my gloves.

"You can get closer," she invited me.

I looked around to see if anyone was giving us an odd look. So far, I had been able to pass in public. I put my arm around her and she got closer to me. This entire exercise had been for Natalie to entertain her fantasy, not that she had any romantic interest in me, personally. For her, I was just some random male date. After painfully watching two hours of ridiculous drama, I held Natalie's hand out of the theater and around town. After some window shopping, we came to a seafood restaurant. When the waiter came by, Natalie ordered for the both of us, so I would have to use my voice.

As we sat across from each other, she stared at me as if wondering what to make of my appearance. She nodded as if I had passed inspection and then prattled on about the movie while I remained silent. After dinner, I paid in cash and then we headed back home. I looked at my watch to see how much time I had left as I drove back. Natalie smirked at how I looked.

"You did well. I had fun," she said pleased.

As per her orders, I remained silent and gave her a thumbs up. As agreed upon, I wasn't to say one word or else the fantasy would be ruined. I was the silent, mysterious, man in this fantasy. Back inside the apartment, I didn't expect anything else to happen. My good deed had been accomplished. That's when Natalie came up to me and kissed me, cautiously at first, and then more passionately as she got used to my fake facial hair. She grabbed ahold of my bulky shoulders and put her tongue in my mouth. She placed her hand on my stomach careful not to touch my breasts and caressed me.

"Now, I want you to fuck me," Natalie said as she caught her breath. She gave me lustful eyes that told me she wasn't joking around.

I simply nodded and took her to my bedroom. I went into the bathroom, dropped my jeans only a little, and placed a realistic fake penis strap-on on myself. I then exited still fully clothed but with my jeans down a few inches. Natalie felt my fake cock and then smiled mischievously. "Get me ready for it," she ordered.

I obliged, feeling up her skirt and finding she had already taken her panties off. I expertly felt around and then moved her to the desk. She got herself on the desk and let me finger herself some more to prepare her for what was to come. I gave her a look as if to ask her if she was ready. She simply nodded. "Do it."

I placed my fake cock at her entrance and pushed in. Getting closer to her hips, I opened her legs and placed my hands around her hips. "Just like that," Natalie said as she thrust her hips into my fake cock. Her breathing was heavy and I could tell she was excited. I never asked her about her sexual history. I knew she wasn't a virgin but due to her deal with Nate, never truly explored her sexuality. She seemed inexperienced barely able to keep her balance on the desk. She held my face and kissed me every so often imagining I was someone else. As she became more-and-more lost in her fantasy, she began to moan and encourage me.

After some slow sex, I knew it was time to pick up the pace. She closed her eyes, hissed, and started to squirm on the desk until she finally felt her orgasm. "Holy shit, that was great," she said as she came down from her high.

I lowered her from the desk and guided her to the bed. She continued to make out with me and caress my body careful not to touch any area that would disturb her fantasy. After she had gotten everything out of her system, she smiled at me as we remained in a cuddle position. "Is it okay if we do more of this?" she asked hopefully.

"Yeah," I said softly.

---

Since Natalie never slept, I washed my face, took off the wig and clothes, and cleaned off my fake cock. I took a shower and then had a nap. When I woke up, I found Nate in the living room looking pissed-off as if he had waited hours to chew me out. "How was your date with Natalie?" he asked antagonistically.

"It went well. No one noticed," I said.

"You going to grow a beard for real and cut off your breasts?" he asked.

"Don't be fucking stupid," I scolded. "I merely did it for her."

"You don't date Natalie. You date me," he corrected me. "This is cheating."

"You're the same person," I said incredulously.

"We're no different than Siamese twins. Just because you fuck one doesn't mean you get the fuck the other," he said.

"But...why?" I wondered.

He seemed a bit stumped by that. "Look, Natalie and I made a deal. Don't you realize that every day I am stuck in this weak baby-making body that is constantly delivering estrogen to my brain? I can't look and dress the way I want to be. For over twenty fucking years, people treated me like a girl. The boys never took me seriously or they just wanted to fuck me and the girls would never think to be with me. The only romantic option I had were Lesbians and, of them, only a very few were even good-looking. I've had to put up with a lot of shit and if not for Natalie, I would be transitioning to become a man, right now," he said.

"You can look and dress like a man without needing hormones or surgery. I just did it," I said dismissively.

He scoffed at me. "Could you talk like a man? Could you run, lift weights, and fight like a man? Can you walk around the beach shirtless?" he asked.

"Well, no," I said obviously. "But you can both love who you want and present how you want. It doesn't have to be a competition between you."

"Who are you to question what we have agreed to? Do you know how weird it is for me to dream about you screwing Natalie?" he asked.

"Natalie just wanted a romantic evening and if you have a problem with that, you're an asshole," I told him bluntly.

He stormed off to his room refusing to talk to me for the rest of his term.

---

Natalie and I continued to date with me cross-dressing as a man. With each date, she started to evolve her fantasy to allow me to use my real voice when no one else was paying attention. She would experiment with my clothes making me wear a black leather jacket, sunglasses, ball caps, cowboy boots, and so forth. She would have me clean-shaven occasionally even if it did make my appearance look more feminine.

"Nate's pissed off with this," I remarked one day outside a coffee shop.

"He acts like he has it so bad. For me, being able to love who you want is more important than appearances," she said.

"Would you be willing to transition into a man if you could be with a man?" I asked.

She seemed uncomfortable with the question. "I suggested it to Nate before, but he's a bit homophobic. I think...there was a time when we could have been together with Josh as his girlfriend but Nate refused."

"What about a transman? Nate gets his vagina and you get the man you want?" I suggested.

She smiled amused at that. "Just how many transmen are there in this town for us to choose from?" she asked rhetorically. "And how many transmen are willing to date a woman and be a bottom for that woman? How many would be willing to deal with our psychology?"

"I think I can be with you both just like this," I said.

"When I kiss you, when I hold you, when I have sex with you, I think of you as someone else. I'm not in love with you and I doubt I ever will be. All of this is an unhealthy fantasy of mine but it will never be fulfilling. You will never have the shape of a man, the voice of a man, the mind of a man, the...cock of a man. You'll never get me pregnant and be the father of my children. You're the Diet Coke of a man," she said as she drank a Diet Coke in front of me.

Her comment stung but I couldn't deny it. "You're just going to have to live with my unhappiness," Natalie told me.

---

Not long afterward, Nate insisted we go skiing. He had made all the arrangements apparently had rented a cabin for us. I didn't double-check his reservation or ask him too many questions. He was generally in a bad mood with me hanging out with Natalie, and I just wanted to make it up to him. Due to his athletic build, he was faster, able to get through tougher courses, and able to get back up easier than me. He expected me to go with him down every single slope and immaturely mocked me if he got down the hill faster which was every single time. I was no slouch though. I was able to somewhat keep up with him throughout the day.

Completely exhausted, Nate took me to our cabin only to discover there was no cell phone reception. He had also intentionally not taken his phone charger and had drained the battery down to zero during the day. I had simply forgotten to take mine but wouldn't need it until tomorrow. I then realized a slight complication as the switch happened. She looked at her dead phone, checked her pockets, and simply gave me a stare.

"That bastard," she shook her head dismayed.

"What's wrong?" I asked concernedly.

"What the fuck am I supposed to do for eight hours?" she asked herself.

It suddenly dawned on me that Natalie never slept and had no electronic device to entertain herself with. Nor could she go outside and walk around for any real length of time. She was stuck in a cabin, unable to sleep, and having nothing to do. "Take my phone," I offered quickly.

She glanced at my cheap phone unimpressed. She would be forced to play candy crush until my phone went dead. "Thanks," she said taking it from me. "You should get some sleep. You look exhausted," she noted.

"Do you feel tired?" I asked.

"I feel a little sore but I'm always alert. Imagine sleeping for eight hours and only having to stay awake for eight hours. You would stay alert, wouldn't you?" she said.

"Maybe we could talk to pass the time?" I suggested.

"For eight hours? Get real," she shook her head.

"I'm willing to offer my body and mind to you for as long as I can," I said sincerely.

She simply stared at me and then at her surroundings. "You find my body attractive, don't you?" she asked.

"You're beautiful and feminine. You're like a dream come true," I said honestly.

"It must be frustrating to have me turn you down half the time," she remarked.

"Some Lesbian couples I know are barely affectionate, go months without sex. Nate can be an asshole at times, but I know he loves me and wants me. And you make up for his shortcomings," I complimented.

"Doesn't it bother you that you're living with someone who sees themself as a man?" she questioned.

"I guess I live in a fantasy where that's not the case. I see his body, I hear his voice, I can smell the perfume you make him wear, and I feel his curves, and I can even taste him, and it makes me forget what's really going on. That, and the alternative is what I was doing before which...sucked," I said.

"Is Nate experienced enough for you?" Natalie asked.

"Wow, you're kind of making me feel like I'm a whore," I laughed. "I didn't date a whole lot of women before Nate. I could tell this was his first sexual relationship, but he knew his stuff. He was confident in his ignorance, but he just got better-and-better."

"When did you know you were gay?" she asked.

"Maybe thirteen," I guessed.

"Nate kissed a girl during summer camp and got us both expelled. Before puberty started, we were so alike," Natalie recalled. "The way Nate would look at my female classmates, it made them wary of me. So, I didn't have many friends. Nate was also a complete ass to any boy who held an interest in me. It's hard to explain to people why you're one person one day and a completely different person the next," Natalie said.

"I can't imagine," I said sympathetically.

"Could be worse. Instead of two, I could have had a dozen personalities," Natalie said dryly.

"What caused this to happen to you?" I asked curiously.

"No one knows. Some people think it's genetic, others think I had a traumatic event in my childhood, and some even have the balls to say I'm making it up," she said. "It hasn't been without its advantages. Without sleep, I am so much more efficient. It makes me feel like an alien."

"Tell me the truth, do you think I'm stupid in comparison?" I asked.

"Yes," she said bluntly. "But you have your sanity. Sometimes, I wish Nate was dead and I was the only personality in this body. How fucked up is that? But I do envy people that are of one mind, especially...now," she said annoyed.

"I can stay up with you and talk for as long as I can," I said even as I fought to stay awake.

"What if I don't want to talk?" she asked coyly.

"Well, we can...I don't know, stare at each other," I suggested jokingly.

"Fuck, this was his whole plan," she realized. "I don't think I'm going to be really into this, but it will kill time. So...you want to have sex?" she asked finally.

I gawked at her. "But, I don't have any toys and I'm not dressed up for it," I said.

"I know that. I know that you like this body but I don't want to presume you will want to do this with me," she said awkwardly.

"No, we can do whatever you want," I offered.

"I don't care what you do to me. It's better than staring at wood," she said referring to the cabin.

"So, does this mean you're...," I wondered.

"Gay? No. I'm just bored, and I know you're interested. If we were both straight, I wouldn't even suggest it," she clarified.

"You can't get me all riled up and then shut me down," I told her.

"I'll be a good sport," she promised me.

I decided it was worth the risk. "Okay," I agreed.

Despite the cold outside, it was warm and toasty inside the cabin. We both took off our pants and allowed our legs to brush past each other. I took the lead, kissing her while she lay on the bed. I took a dominant role on top of her as I kissed her lips and neck. I took a slow pace wanting to ease Natalie into it and also wanting to give her all the time she needed to back out if she felt uncomfortable.

Normally, in this situation, my girlfriend would be caressing my back or trying to aggressively lower my underwear off my hips. Natalie, however, was a cold fish and didn't do anything. She had her hands to her sides and just went along with it. With both of us still wearing our sweaters, I caressed her breasts as I ground my crotch into her. We did dry humped each other for a little while, and I felt fortunate to even get this far with her.

"Okay, let's have you on your stomach," I said gently.

She complied rolling over. I got on top of her and ground my crotch with her lower back. My breasts rubbed against her shoulder blades. I reached underneath her arms and continued to caress her breasts while kissing her neck. "Is it okay if I touch you down there?" I asked.

"Just do whatever you want and I'll tell you to stop," she said.

I took two fingers and gently rubbed her clit from behind. At first, she didn't seem to notice but then she started pushing her hips against my fingers. Maybe she was fantasying I was a man behind her. At this point, it really didn't matter. Natalie was starting to get into it. I would rub her a few strokes, go back to dry humping, and then back to rubbing her again.

"Go to your back," I said after a long while.

Once she got back on her back, I escalated a little. I kissed her navel to see if she would resist me. When she didn't, I started putting my hands underneath her sweater and caressing her breasts skin-to-skin under her bra. Still, she seemed interested but not overly enthusiastic. She seemed merely curious as if she were a student in some exotic sex class. I kissed her more passionately this time to see how far I could go. I put my tongue in her mouth and kept it up. She kissed me back but her eyes were closed as if she were thinking of someone else. I kissed her as passionately as I could while caressing her breasts and she did not protest.

At this moment, a real Lesbian lover would have already pulled my sweater off but Natalie didn't have that initiative, so I did it myself exposing my breasts to her. I then worked to get her own sweater off and unclasp her breasts. After massaging them for a good while, I went low on her. "Just go underneath my underwear. Don't take it off," she said.

I complied sweeping my hand inside her underwear and rubbing her. I had seen her vagina plenty of times while with Nate but I had to respect Natalie's wishes if I wanted to ease her into this. She sighed a bit but remained fairly unenthusiastic. "Do you want me to go in?" I asked her.

"Just rub," she permitted.

She eyed me as I worked on her and after what seemed like a long time, she had me stop. "Okay, I think that's good," she said.

"You don't want to do anything else?" I asked hopefully.

"You should get some sleep," she said dismissively and then put her bra and sweater back on.

I hid my disappointment, wiped my hand with a baby wipe, and tried to get to sleep. Thinking of her and what could be kept me up though making it difficult for me to eventually fall asleep. I couldn't help but feel Natalie would rather stare at the ceiling than be romantic with me and it kind of stung.

---

The next morning, Nate woke me up. "Let's get moving," he said wide awake and chipper.

I got out of bed feeling sleep deprived. "You're an asshole. Was this all your brilliant plan?" I accused.

"Look, if we both like you, it's a win-win. I just set the conditions to make it possible," he said as if it were nothing.

"But she doesn't like me, and she'll never like me," I pointed out.

"Just give it some time," he said.

"You didn't even ask how I felt about it," I said scornfully.

He gave me a blank look. "Wouldn't you want to be with Natalie if you could?" he asked confused.

"That's not the point. We're supposed to be on the same page," I said.

"If I told you what I was up to, Natalie would then know about it in her dreams," he said obviously.

"She rejected me and I couldn't get much sleep so thanks for that," I said angrily.

"Well, you can either sulk in here or get out on those slopes," he said simply.

---

After a full day of skiing, I was exhausted and beat. Natalie drove us back to the apartment. "We were set up by Nate. I'm sorry. I wasn't in the loop about it," I said awkwardly.

"I know," she said.

"Why do you let him get away with this kind of shit?" I asked.

"What am I supposed to do? Ruin his life and mine at the same time? The thing he desires and cherishes the most in this world is...you. And I'm not going to punish him by pushing you away. It's not fair to either of you," she said.

"I can't but feel a little insulted. I mean, I know you're straight and I would never presume to turn you gay. It's just...you had nothing better to do," I said unable to articulate myself.

"Would you cut yourself or burn yourself if you had nothing better to do?" she asked rhetorically.

"Are you saying having sex with me is the same as cutting or burning yourself?" I asked.

She hesitated to reply. "If I'm with you, for serious, then I abandon all hope I'll be with a man. Even if it's just a fantasy, it's a fantasy I want to hold onto. I can't fantasize about being with a man when I'm supposed to be intimate with you," she said.

"I see," I said dumbfounded.

"Look, if you want someone to shop with, I'm your girl. But I can't give you what you seek. It's either Nate or nothing," she said.

She was driving a hard bargain and it made me suspect she wanted Nate to end his relationship with me, so she could convince him to be with a man of her choosing. It was fucked up, but I had to entertain it as a possibility.

---

It wasn't long before Nate went out for the evening while I was supposed to be asleep. He would do this every so often since he never slept. I decided to follow him to a club he often went to. It was around midnight when I arrived. As I suspected, Josh was there on the dance floor nodding his head and enjoying himself. In front of him were two girls dancing, grinding, and even kissing each other in front of them. One of the girls was Nate.

"Oh, shit," Josh realized as I came up.

"Natalie, let's talk," I ordered.

I brought Nate outside to chew him out. "What the fuck are you doing?" I demanded of him.

"Look, I'm just giving Josh a good time. I wasn't serious with that girl," he said obviously.

"You were mocking Lesbian sexuality to get your friend aroused," I said.

"You act like Lesbians never tease men," he said dismissively.

"It's still cheating. How many times do you go out with Josh?" I asked.

"Is this about the random girl or Josh?" he asked confused.

"It's both," I clarified.

"Look, it's no different than a straight woman in a lesbian porn video. It's just acting," he said.

"Why do you want to get Josh aroused?" I asked.

"It's just fun," he said defensively. "You're not even supposed to be here. It's way past your bedtime."

"What's that supposed to mean?" I asked pissed off.

"Emily, I'm not perfect, alright, but I am everything you could wish for. I look gorgeous and perfectly feminine. I'm in great shape. People who look like me are not Lesbians if you know what I mean. On top of that, I give you plenty of affection. I'm also brilliant. As far as I am concerned, you hit the jackpot so why are you acting so ungrateful?" he asked.

"What am I? Some pity case? You're fucked up in the head. No one else in the entire world would deal with your shit," I pointed out.

"I'm the next Einstein. I could be a celebrity if I wanted to and have anyone in the whole world, but I'm with you so be appreciative," he said arrogantly.

"No, because Natalie would stop you. She doesn't want that life," I said.

"You think you can divide us? Natalie will throw you under the bus before she would ever think to undermine me because we're the same person in the same body," he said and then walked back into the club.

"Fuck," I said disappointed and exasperated.

---

For some time afterward, I became jealous and frustrated with Nate's relationship with Josh. Everything they did was under the guise of "guy" stuff, but I was never invited to. At the same time, Natalie was being overly compensating for Nate's behavior. I felt like I was being emotionally manipulated and there was no one to talk to about this odd situation. I also contemplated my own sexuality and how I felt when wearing male clothing. If Nate's strategy was to be an asshole to push me towards Natalie, it was working. I began to see Natalie as a more ideal partner for me. However, she wanted nothing to do with women and it wasn't enough to dress like a man. I had to do something more drastic to gain her affection and my own sense of being was called into question.

Maybe the reason all my relationships failed was that I was never meant to date lesbians and be one. Maybe, I was meant to be with a straight woman like Natalie where I could take charge, express my confidence, and be held in high esteem by men. I looked at my naked body in the mirror and wondered if any of it was really beneficial or advantageous to me. Did breasts do anything for me other than be a nuisance, a sex object for men, and something to hide away in public? Did my vagina do anything for me other than the threat of STDs, pregnancy, periods, rape, and a source of criticism for how it looked? At that moment, I became self-loathing and feeling like I change needed to be made.

Without a doctor's prescription or advice, I decided to do a social experiment on myself. I took a package delivered to my doorstep, opened it, and placed the testosterone pills inside a book I knew neither Nate nor Natalie would bother to open.