In Over My Head - Supplement

Author's note: This entry is not an extension of the series In Over my Head but rather something that I wanted to do as more or less an add on. Mostly to discuss situations like cross dressing and how a dress loving person like me relates to it all. This is not at all really erotica. Just for fun.

I looked in the mirror and poked my face. It was looking a lot better but that spot still hurt and my nose did seem to have a different bend in it. Damn that woman could punch.

I hadn't been out of the apartment for 10 days as I was healing. I was allowed to take vacation days to heal up. My boss asked why, so I showed her. She said, "I need you to be more careful with your silly games, but I can't say much because you haven't taken any time off in almost a year. Take a couple of weeks off and heal up, silly boy."

It had been ages since I had gone out and I was going crazy and with makeup I didn't look too bad so I put on panties and a nice pair of slacks topped off with a light blue polo shirt. I went out to the coffee shop and it felt good. On a beautiful spring day it felt great.

I found an out of the way little spot and settled in with my tea and blueberry scone. Content to be alone in a crowd as people happily chatted away with friends and families. I had neither and sat alone as usual.

Since my tea was just a bit too hot to drink I tore off a piece of the scone and was about to pop that tasty morsel into my mouth when someone abruptly sat at the table with me. Damn, is she wearing the same clothes she wore when she......

What women wear is noticed by cross dressers. They like women's clothing and they tend to pay attention. And it did seem like she was wearing the exact same thing as when she had punched my face in. I said nothing about it. Didn't dare to.

"Looks like you are healing," she said casually and then she broke that off and started apologizing again. "Again, I am sorry. I lost it and took it out on you."

"Mostly you took it out on my face," I answered with a shrug. "Sissies get beat up. I have seen it happen so I suppose I was long over due."

"You could have at least put up a fight or defended yourself," she said as she tried sipping her coffee that was still too hot to drink. "You just stood there and let me punch you."

"I was taught not to hit a girl," I lied because for some reason no one taught me that directly. Even though it probably should be a thing. "Besides which, you probably would have beat me senseless had I tried to fight back. I saw it as a lost cause."

"Then don't fucking get up you moron."

"Sadly I saw a trans-girl get massively walked on because she didn't get up," I replied. "Seriously, just leave it. It is over and done."

She nodded and I watched her open her bag and take out a muffin. Damn she was a big girl. You are lucky she didn't fucking kill you sweet heart.

"How did you,,,,,," I started to say, feeling the conversation was lagging.

"I brought you home, fucking moron," she said holding her palms out. "Remember, or were you concussed?"

I nodded, yeah she did didn't she.

"All you had was that bloody dress to wear and I didn't want to see you get your ass kicked again trying to get home," she continued. "Did you get your car?"

"I am here aren't I, fucking moron," I said regretting the words as they were leaving my mouth.

She just laughed and said, "Yeah, I deserved that."

I looked over at her and studied her as she drank her coffee. She was really a very attractive woman. She was wearing makeup but very natural shades and did little to cover the freckles that were scattered across her cheeks and nose. I felt awkward as I wanted to keep looking at her because I could not tell if her eyes were hazel or more a greenish gray. They seemed to change depending on how the light hit them.

She had an entirely different demeanor that morning. Last time I had seen her she was openly hostle, followed by complete ambivalence then a moment of great rage. Then on the ride home was the interminably long lecture about how very sad my life was.

We had a very nice conversation and for some reason she didn't continue grilling me about my love of women's clothing and dressing up. But that string was broken when she looked under the table and asked, "Are you wearing......"

"Yes, I only wear women's clothing now," I said almost triumphantly. "They have come to accept that at work. But slacks and blouses that I wear do have a more androgynous look."

"How come you never asked about me," she said gingerly drinking her coffee.

"I figured that is your business and none of mine," I said honestly. "My boss always wanted to be a man but I think she gave up trying. I think the understanding that we are somewhat alike but in opposing directions gives us a bond of a sort."

"I never wanted to be a fucking man," she said giving me a look of irritation. "I am ok being a woman. More than ok. I just don't like dresses and skirts. I think they are demeaning. And given your personality that is probably why you wear them because you also think wearing a dress diminishes you."

"No, I pretty much always wanted to be a girl and I love the way dresses and skirts feel."

"Girls are awesome," she said, almost as an aside. "I love girls."

"I never would have guessed," I responded with a wink. "Can I ask why you said that your friends would be laughing at me? Because they seemed pretty nice to me that night."

She moved herself to get more comfortable in her seat and then looked at me. She seemed to be contemplating her response.

Finally she spoke and said, "Firstly, not really friends. At least not now. Not even sure we were then, although those four were very close in school. Don't think so much now. Those sisters are very nice and all but deep into Jesus, massively so, and they can get annoying. Jannell, she was heavy into girls but now I think she is trying to "cure" herself of that curse.

"Mostly we were teammates and we had a bond. I was always the 5th wheel and seen as a loner to that group because I came to school to play basketball but that was a fail because I couldn't shoot. In high school I was always enough bigger that I could bully my way to the net. Didn't work out so well in college. They transferred me to volleyball and I liked it."

"Yes that is all good but you didn't answer the question," I said pushing her a bit.

"Why do you want to know? You seemed to be having fun so you should just let it go. But they were making comments behind your back. How they reacted to you surprised me. You being you has to be some sort of Jesus violation for the Jackson twins and those other two, they were always kind of stuck up back in school. But people change I suppose."

We talked and got another tea and coffee and talked some more and then came soup. We talked on and on about many things and it was amazing fun for me. I had never had a girlfriend before. And no, not a girlfriend but a friend that is a girl. She was very intuitive and had a deep sensitive and caring side which I did not get the night we had first met. I found out that she sold medical insurance. Not like a person would buy but she represented a large insurance company and worked with agents.

As the conversation raged on we got back to the subject of me and she asked if I was going to transition and change into a girl.

"First, people don't change into a girl or a boy," I said. "They are born a girl or boy but in some cases they feel that is wrong. The mind tells them one thing but the physical is something else. They feel out of place."

"Is that how you felt," she asked reaching out and holding my hand. "Lost and confused and wanting to be something else?"

"Always lost and frequently confused and definitely wanting to be a girl," I answered. "But, years of therapy have taught me that I am not really that and not really a t-girl. So while I would love to be a girl because I love everything about them, if I am honest with myself I am not a transsexual. Also I am not sure I have the will to see it through.

"Trust, it took years of therapy and self appraisal to realize that. I tried to push my way in and found a doctor that prescribed the treatment drugs that have changed me physically but I found a guy now that has me on the right track. If all this is the right track for anyone. He is the only one that wasn't hell bent on "fixing" me. He just worked on helping me cope."

"I firmly believe that a lot of this whole gender dyslexia thing is a part of our stereotyping of genders that has been burned into us over centuries. If as a kid I like wearing dresses and playing dolls does that make me a girl? If you like wearing pants and cars and like working on cars does that make you a boy? Why can't I like dolls and be a boy and you be a girl that is a mechanic?"

She leaned forward and poked a finger at me, "First off I only see a fucking car as a necessity and an expensive one at that. More importantly I would hate to have to actually fix the fucking things. But I see your point. I doubt it is very popular in the LGBTQ community though."

She moved back to her coffee and took a longer drink. She gave me an understanding smile as our eyes touched. "I do wish I knew you better, yanno, before I beat the shit outta you."

"Yeah, that would have been nice. Or at least helpful. But sadly that is what happens more often than not. No one really knows or understands the people they want to hate. Or have been programmed to think they hate."

"But you still dress up like a girl and act like a girl," she responded leaning forward again.

"I am still a cross dresser and always will be," I told her. "I like it. No I love it and see no reason to change that. It is a big part of my life and I simply love the feeling. I still take the drugs because they have altered my look and made me look more feminine but other than that....."

"You do look sort of fem," she agreed. "I guess my first reaction to you, or at least one of them was that of jealousy. I felt you were prettier than me. Soooooo, what does a cross dresser do for porn, if you don't mind me asking. Vogue or Elle magazine, W perhaps?"

"You know about W," I said with a smile. She gave me the finger in return. "Yes those are good and catalogues are fun as well. But to be honest I love the many fashion blogs there on the internet. The women are more real. Most men when they see a picture in those magazines want to rip the dress off them. I can see the same picture and can love seeing a nice looking woman but also think, damn, what a pretty dress. So I can enjoy looking at them both."

"So you are keeping the boy parts," she asked seeming to want to change the subject from women's catalogues and fashion mags.

"Yes I am keeping the balls and this useless little penis," I said with a shrug. "No sense going through all of that. Besides having them adds greatly to my other hobbies. The only physical thing I have done is to have laser treatments to remove facial hair. That was great fun I can tell you."

"When you say act like a girl, do you do stuff other than just wearing the clothes," she queried?

"Yes, I put on make up and wear lipstick and of course shave the necessary parts," I said. "Sit to pee as often as I can and many other things. So I always try my best to do and act as I feel a girl would. I am in fact wearing a neutral natural shade of lipstick now."

"But, do you get off on being in a dress," she asked leaning forward to get a closer look at my lips? "Or is it just fun?"

"As a kid it did get me off and make it easy to masturbate," I agreed. "I always felt so wrong. Wrong for wearing my mothers clothes. Wrong for liking the way they fit on me and the way they felt. Wrong for masturbation. Just wrong. I had a loving and good family as a kid but I was always so disappointing. My mother hated that I wore her clothes. Not so much that they were HER clothes in particular but women;s clothes in general. So I always felt like a failure.

"I did continue to dress and a part of that was the humiliation side of it I guess. Being that I got off wearing a bra and panties sort of meant getting off on being humiliated. I like to think I always wear women's clothing because of the look and feel but if I am honest the humiliation part of it is still there. One woman analyst I had said that I dressed because I actually saw women as inferior so dressing like a woman made me feel inferior. I thought that was bull shit."

"I suppose that is always an option," she said agreeing with that doctor's opinion. "Although to be fair you don't seem abusive toward women. Then again I don't know you all that well so maybe you have your mother in your freezer at home."

"I have no freezer." I thought aloud as I protested that opinion.

"I love women and want to emulate women and would never hurt one on purpose. Sure they can be irritating but all people can be that. My biggest issue is that I am easily intimidated by a woman. Always have. I have never actually had a real date or even kissed a girl or woman. If a girl talked to me in school I would turn to jelly."

"So you have never had sex then," she prodded giving me a little wink. "You are a little dress wearing virgin."

She teased me with a little laugh but I nodded yes. I was what I was. And damn she had a beautiful smile.

She leaned back in her chair and shook her head, "Shit, girl, even I have been fucked once or twice. Yanno, by an actual human cock, not just artificial appendages. And I am totally lez."

"I know, I know, so pathetic," I answered defensively.

"Is ok, someone has to thin out the herd," she said openly laughing at me. Then she leaned forward again and took my hand and patted it. "Sorry I am teasing. But I guess that is something people do not like being teased about."

"I am good, I have accepted who and what I am. Embraced it actually."

"So if I said let's go to your place and fuck you wouldn't do it," she asked almost incredulously. And when I hesitated she glared at me and said, "Shit, that is sad, and in a way fucking insulting."

"What is that line, 'it isn't you it's me?' that is very applicable in this case," I said. "You would most definitely be disappointed. IF such an unlikely occurrence were to actually happen, which is doubtful, I would rather be given the chance to use my mouth to orally stimulate you."

"And then have me sit hard on your face so I could squirt all over it," she laughed. "Right, right? Tell me I am wrong."

My bright red blushing face was a beacon light of affirmation or her assumption.

"If you were more of a woman, or possibly more of a man, which I doubt, I might take you up on that," she said as she rose from the table. She moved over and stood above me, She bent over and grabbed my head and gave me a deep long kiss. She parted my lips with her tongue and rammed it into my mouth. I thought she as done but she kept kissing me.

She finally pulled away from me and stood. Before walking away she gave me a playful little smile and a wink and said in an embarrassingly loud voice smacking of conquest, "At least now you can't claim to have never been properly kissed."

And just as fast as she walked in she was gone. I continued sitting there and could not get her out of my mind because that was a first for me. Seriously. Almost 30 and that had to be a first for me. Not only having the privilege of sitting with a nice looking woman but having an actual conversation where I was not frozen in fear and anxiety.

And she had just walked out of my life. More than likely forever. Oh well.