Rosie Comes Out

Rosie Comes Out

Carmen was a beautiful lady with Hispanic roots and temperament. She was just 22 years old, just like myself, and had graduated in social studies from a good college. She had a full figure with well-developed breasts. She had a great smile. I had been to college where I studied Economics. She worked as an assistant in a medical clinic. I worked for a multinational as a junior salesperson. I had met Carmen by accident through her sister Miranda, who worked in our office. Carmen was waiting for Miranda in the parking lot for a ride home. Fortunately for me, Miranda's car and mine were not parked so far away from each other and I was introduced to her beautiful sister. It was brief but Miranda suggested we get together for a drink and I eagerly said 'yes'. Miranda was a few years older and had a steady boyfriend.

A week later we met for a drink and it seemed that Miranda's matchmaking was working. Carmen was single and had a great personality. I was surprised she had no boyfriend. We did hit it off, laughed a lot and decided to meet later that week alone. Over several months we spent several nights a week together and over the last few weeks, Carmen spent from Friday through Sunday at my small apartment. We were both inexperienced and loved our attempts to get the other excited using hands, mouth and sexual organs. I looked forward to our weekends as did Carmen.

There was one part of me that I had experimented with but kept a secret: cross-dressing. I had seen a program on television with drag queens and couldn't believe how attractive these "girls" were. Ordinary men could become beautiful girls. So, I visited some second-hand shops and bought a few items online. I had dared to buy a small makeup kit online and experimented with many looks. Since before Carmen I had neither a social nor sexual life, it seemed a good way to spend time. I hurt nobody and could do this in the space of my small apartment. Of course, I had fantasies of looking beautiful and having an equally beautiful girlfriend who understood and even helped. Fantasies would also drift to attracting males and then teasing them and even taking some home. With my increasing attraction to Carmen, all these thoughts were suppressed and clothes, wig, rubber forms and shoes went to a corner of my small cupboard in the bedroom.

The previous weekend had been similar. We had gone eating, then on Saturday night, we went to a bar which had some comedians and also a small dance floor. Neither of us was a good dancer but it gave me the opportunity to press myself against Carmen whatever music was played. She didn't seem to mind as her arms went around my neck and held me close. Of course, she spent the night in my bed and we had nothing planned for Sunday.

Carmen was as inexperienced as I. She wasn't imaginative but accepted my lead in the relationship. I had encouraged her to suck my cock which she did. But she ensured I was in her before I erupted. I, on the other hand, didn't mind tasting her till her fluids streamed. But she wouldn't kiss me after that. She never let me finish in her mouth but she was always ready for me to enter her.

We got up late and I went to put the kettle on to make coffee. I had invested in a small 2-cup coffee maker and enjoyed this luxury at the weekend. Whilst I rummaged around to look for some breakfast items, Carmen was awake but still in bed. I went into the small bathroom and took a long shower. As I luxuriated in the warm water wondering if Carmen would join me in the small shower, I heard a door bang. Perhaps Carmen was going to get some bread or pastries I thought and leisurely dried myself and shaved. With a towel wrapped around my waist, I entered the bedroom.

Disaster! Carmen had left and the bed was littered with the clothes, wig and shoes from my "girl time". I immediately dialed her number wanting to explain but it rang off the hook. She was not responding. Carmen lived with her single mother and I didn't think that 10 AM on a Sunday would be a good time to call or visit her. I had met her mother only once. Miranda was her elder sister and a colleague of mine. Would she have gone to her? Perhaps, but Miranda lived not far away, had a boyfriend and I knew she would have spent the night at her or his apartment. I cursed my own stupidity but had no reason to believe that Carmen would delve into my cupboard.

I desperately needed to explain to her but wasn't sure where to find her. At this early hour on a Sunday, it wouldn't do to disturb the only two people who might know where she might be. I kept dialing her numbers and sent her several messages with a plea to call me. I could explain. Of course, she didn't reply or pick up. I tried calling Miranda around 2 pm and got no answer. Every thirty minutes or so I kept trying both numbers without success.

Finally, around 4.30 Miranda picked up the phone. Even though she knew my number her voice asked":

"Who is this?"

"Miranda, it's Russ. I really need to speak to Carmen. Do you know where she is? Is she with you? She is not answering," I asked desperation in my voice

"Why do you want to talk to her?" the voice was cold and I assumed either Carmen was there or had called her.

"Look, she left the apartment this morning in a hurry and I need to explain something to her."

"What?" Miranda asked still in that cold voice.

"It's something personal. I'd like to talk to her. Please? "

"Carmen spoke to me, she was really upset and am quite sure she doesn't want to see or talk to you.

"Miranda, please. I can explain all. I am sure she will understand." I was pleading now.

"Look, there is nothing to be gained by confronting her now. Leave it and perhaps she will talk to you or even meet. You need to give her time."

"Miranda, if I don't explain to her right away she will continue to think the worst of me. Please can you talk to her?"

"Look, Russ, this is nothing to do with me. But you clearly upset her. I don't know what you said or did, but she was incoherent. So, give her some space and try tomorrow."

"Pleases, Miranda, please," I whined close to tears. "I didn't want the relationship to end this way."

There was a long pause but I knew Miranda was still there. I waited. "OK, come on over. If you are not honest, then forget Carmen and our friendship." Miranda's voice was stern but I didn't hear it. I was pleased that she was willing to listen.

"OK. I'm on my way. And thanks," I managed to stutter. I decided to make a quick stop and buy a bottle of wine. It was a small gesture. I hoped that Carmen would be there but couldn't be sure.

I drove carefully wondering how I should approach the subject. I could lie and say it was from an old girlfriend. But why would I keep the stuff of an old girlfriend in a plastic bag in my cupboard? That was bound to raise even more questions. Should I tell Miranda of my alter ego? That might shock her and kill our relationship. She might think of me as some pervert, certainly not a suitable companion for her younger sister, and so might even spread the word in the office. Where would I find another job quickly? All these thoughts raced through my mind as I drove to Miranda's apartment complex.

I had dropped Miranda off sometimes when she needed a ride but had never been inside her apartment. I parked the car, grabbed the wine and made my way up the stairs to her apartment. I knocked and she opened the door quickly. I walked in unsure if I would meet Carmen and how I would greet her. Certainly, no deep kiss on the lips as was our normal greeting.

"Come in," Miranda said coldly as I entered. The apartment had a corridor that led to the bathroom at the other end of the hallway. Two rooms on the left had closed doors. On the right was a small lounge area and next to it was a small kitchen. I handed her the bottle of wine which she took. "Thanks," she said and led me into the lounge. Carmen wasn't there.

I looked at Miranda expectantly but she had gone to the kitchen and I heard the cork pop. She returned quickly with the open bottle and two glasses. She poured out the wine and took a sip.

"Carmen doesn't want to see you just yet," Miranda said looking directly at me. "She was really hurt and upset. Not sure what you did." Miranda took a sip. "Carmen is in the bedroom and doesn't want to see you. She wants you to tell me exactly what you want and I will relay messages to and from her. If then she wants to meet you, you guys can take a walk or do whatever. If you don't want that, then drink your wine and leave."

I took a small sip of wine laced with a dilemma. It was a struggle to have to explain to Carmen what I had hidden in the bag; it was even more embarrassing if that were possible to explain to Miranda how I had this stash. Yet, I knew Miranda was smart, knew me enough to decide if I was lying or not. It would be embarrassing as hell but I was here now. If I walked out, I would not see Carmen again and quite possibly lose Miranda's friendship and my job. There was no guarantee that Carmen and Miranda would accept the truth but then I wouldn't be guessing for the rest of my life why I had lost Carmen.

"Mirandas, this is not easy. So please be patient. It will sound strange perhaps but I swear it's the truth." I spoke slowly and took a big gulp of wine.

"We have known each other in the office and chatted a little but we have never met socially." I paused for a sip and saw Miranda stare at me waiting for me to continue. "I grew up in a family without a father. Just my mother, sister and me. We were OK but I was shy and my sister was four years older and couldn't spend much time on me. My mother worked so I was left alone a lot. I did chores around the house and for some reason, got interested in my sister's clothes. To cut a long story short I used to amuse myself by dressing in some of her things." I paused to see Miranda's reaction. There was none. She sat passively and hadn't touched her glass again. So I continued.

"So, I went to a local college, studied and started to work at JP Holdings in sales. This meant I had some money finally and as I had not yet any friends, was able to visit thrift shops and buy some girl's stuff cheaply. Also online. So, sometimes, not every day, I dress up and like to look at myself. I studied YouTube videos of drag queens, makeup tutorials and other crossdressers. I spent more time at the weekend doing this until I met Carmen." I paused, gulped down my wine and poured myself a rather large glass. Miranda had taken just a few sips and still had plenty.

"I was so happy when I met Carmen. She was fun, laughed with me and we generally hung out. Soon we became.. quite close and she would spend the weekend in my apartment. After I met her, I stopped doing that. I lost all interest and stuffed all my things away in a bag in my cupboard. I never thought about it until this morning. So, what I am telling you is that those clothes Carmen found in the cupboard are mine. I never meant Carmen to find out and never once thought about dressing after I met her, I swear." I gulped down a big slug of wine and looked at Carmen. "I guess she must have looked in the cupboard for a T-shirt or something and found my stash. When I came out of the shower, all that stuff was on the bed and she had left." Carmen had listened to me without a question. Her face was impassive.

After a long silence, carmen took a sip of wine still staring at me. "So, you said you don't dress up anymore?"

"No, I swear I haven't since I met Carmen," I said.

"And you don't want to do it again? Never got tempted with Carmen's things around?"

"Never. I was happy I found her and even when we didn't meet in the week, we talked on the phone. I didn't need to."

Again the piercing stare with those large dark eyes. "So, if she broke up with you, would you dress again?"

I looked at Miranda, unsure how to answer. "I honestly don't know," I said finally. "I am really sorry I hurt her but it isn't some other girl's stuff. Just my stupidity."

Miranda looked at me and a small smile appeared. I hoped it was a smile. "I wish I could have seen you in a dress and makeup. I can see you in a different light now. OK. Take another drink slowly. I don't want you drunk here. I'll go talk to Carmen. Don't move."

This one-sided conversation had taken time and I guess Carmen was in the bedroom alone. Carmen got up, went to the kitchen and came back with a glass. She poured out some wine and took it with her. "Carmen only has water, I'll say you brought this."

I couldn't hear any voices, so I looked at my phone and scrolled through the text messages Carmen and I had exchanged. Most of them were about meeting at a location or with a time. Some were of ideas and my memory went back to the happy times Carmen and I had shared.

I am not sure how long Miranda was gone. My mind was racing as to how Carmen would take that news, how she would react and would she be so pissed at me she would tell me to go to hell. I also wondered how Miranda felt. She had sat silently hearing my confession. She hadn't expressed criticism or judgment. I would be sorry to lose her friendship.

Miranda reappeared and sat down. I looked at her to see what my fate was. "Look, Russ, Carmen didn't have a lot to say. She listened quietly. But she did ask whether you had gone out of the house and met any friends or had people come to the house?"

"No, no, no, I swear I never did," said vehemently. "I would never do that."

"Why not? There are plenty of men who dress like women. We see them on the street or in bars sometimes." Miranda kept that stare as if this was a normal conversation with a naughty child.

"I never did. I never wanted to. Besides, I don't think I would have gone five yards before people laughed at me. Please, can I talk to Carmen?" I asked pleadingly.

Miranda took another sip of her wine. "She doesn't want to see you yet. She is angry you didn't tell her."

"But, Miranda, there was nothing to say? I forgot all about it when I met Carmen,": I protested.

"Listen Russ. You guys should be talking with each other, not through me. But Carmen doesn't want that. Let me go back and tell her what you said." Carmen rose and left the room leaving me to my thoughts again.

Miranda came back after a much shorter time, sat down and sipped her wine. She then smiled and I thought things would be OK.

"So, as I said, Carmen is still upset. I did tell her she shouldn't have opened the bag but that didn't help." Miranda smiled. "She asked if you were serious about getting back with her."

"Of course," I interrupted Miranda. "Of course. I'll apologize to her and promise no more secrets."

"Carmen thought you might say that. So she asked you to do something for her."

"Anything," I interrupted Miranda again.

"Russ, calm down and please listen without interrupting." Miranda's voice became stern. "She is willing to meet with you but has some conditions."

"What? Anything," I repeated.

"Just wait till you hear it. She will meet you next Friday around 7 pm at the Fiesta Tavern. You guys have been there it seems. But," Miranda held up her hand as she saw I was about to interrupt her again, "she wants you to dress like the girl you want to be - the full works, and you both will go out together. She wants you to get it out of your system. She said she would be happy to have a drink with her 'girlfriend'. If you are serious about getting together with her, she will meet you but only on those terms." Miranda paused. "She means you will have to look pretty convincing and be ready to meet the world. If you look bad or she sees you haven't taken the time and the trouble to do this, she thinks you are not serious about her and she will walk away. Understand?" Miranda paused and took a sip of her drink. "She said that if you do this, she'll forgive you completely and you two can go back to being a couple. She wants that too."

"Oh God," I uttered totally defeated. It was an impossible task. I did want to be with Carmen but those terms? Even if I took the trouble to do it, she could think I didn't try and walk away leaving me dressed like that.

"I told her that this was not easy for you and you would need to think about it. So I said you can tell me tomorrow in the office and I will communicate with Carmen. She doesn't want to see or hear from you before then. Agree? No discussion."

I sat there totally dejected. I had hoped that my admission would at least get her to see me and talk to me. But Miranda was adamant. Carmen had set out her terms and I would agree implicitly or walk away from her.

"You have a lot to think about. Carmen seemed quite adamant. I couldn't talk her out of it. So please leave and think about it. You can tell me tomorrow at lunch." Carmen got up, corked the half bottle of wine and gave it to me. "You might need this tonight," she said. My time was up. She kissed me briefly on the cheek and pushed me out of the door.

I drove slowly to my apartment. My mind was a whirl. I couldn't understand why Carmen demanded this. If she had dug deeper into the bag she would have seen no girl would have bundled her clothes like that. Also, she would have seen the cut-out stockings filled with coon wool which I used for breast pads. If I went through with this, I was sure I would look like a fool, then would embarrass her and then she would dump me. Did I really want that? The trouble? Humiliation? And after everything to go out in public? I could perhaps risk dressing in private but I had never been out and this was a step too far.

I spent a restless night. I didn't drink the rest of the wine as I am a poor drinker. Also, I hadn't eaten much and it would go to my head quicker. I still had no idea what I should do. Miranda would expect a decision, but I was no further. I almost burst into tears several times, angry at my stupidity in not discarding those items and my own weakness in wanting to dress up.

Miranda sent me a message and said we could have lunch at a cafeteria nearby so we could talk. I agreed. I still had not decided on what to do as I walked the half-block to the cafeteria. I saw that Miranda had found a small table under an umbrella. She already had a sandwich and coffee. She waved for me to go inside and get something before joining her.

"So, Russ, how are you?" Miranda asked as I sat down with my sandwich and coffee.

I looked at Miranda to see if this was a joke but she seemed serious enough.

"I'm OK, thanks," I replied biting into my sandwich. We continued chewing. Miranda was obviously waiting for my answer. I still had no idea what to do.

"So, Russ, what are you going to do? I'm sorry Carmen put you in this position but she is really upset even after your explanation," Miranda asked sipping her coffee.

I looked at Miranda and thought I saw some sympathy. Normally, Carmen would have wanted nothing to do with me or accepted my explanation. But she had a request that I had no idea how to satisfy and keep my dignity. Was the relationship worth my humiliation?

"I do want to be with Carmen," I replied slowly. "But I don't want to be humiliated. I have no idea how to do what she wants. She'll laugh at me and then dump me."

Miranda was thoughtful. "Yes, it is a strange request and I don't know what is driving her. I know she likes you very much. You are the first boyfriend she has spent the night with. But I know that she is disappointed and hurt."

"I really don't know what to do," I said. It probably sounded like a whine.

Miranda looked at me. "Look, it does seem strange to me but Carmen hasn't had many boyfriends. You are the second I think. You are the first too that she has spent the night with. I know her and she wouldn't have done that for fun. She likes you a lot."

"Miranda, I really want to be with Carmen. We had a good time together but this is.. I just don't know. I don't mind doing it to win her back but I'm afraid she'll laugh at me and it'll be over."