Why I Prefer Sex Work to Dating

First off I want to apologize for not posting anything. Emily and I are working on the next chapter of her story and I still have it on my desk to finish the "Our Secrets" series. So hopefully you'll have something new to read soon. In the mean time I wanted to get this out there.

So it is the morning after Christmas when I started this and I am feeling so very introspective. I thought I would take a few minutes and share some things about my life and my family. This isn't really erotic, maybe more philosophical. I want to write it anyway for my own sake and will share with my audience on Literotica because I am not sure who else would be interested in reading it.

I'll start with something a little dirty for the hell of it anyway, just to titillate the reader. Let's say the cut in scene in this little slice of my life film starts with stark white letters across the screen "Christmas Eve Day 2016". The camera pans across an overcast morning in my city. The view pans from the sky to descend through the roof of the building where I have my massage space. The music fades out to reveal the background audio of skin slapping on skin and moans.

"Uh mmm uhh uhh uhh, yes baby give it me."

I am wearing a "Sexy Santa" outfit, which consists of black leather knee high boots, a ridiculously short red skirt with white fake fur trim and an equally revealing red band of a top and of course a Santa Claus hat on my dark curly hair.

My skirt is hiked up around my waist and the top is pulled up over my small breasts, which are currently bouncing back and forth. I am bent over my massage table as a distinguished older gentleman rams his cock into my ass with much more force than usual.

My body is covered in a sheen of sweat, we've been going hard for nearly an hour and I am surprised to find myself working up to a second orgasm. His unusual passion this session had made me cum quickly. I have rarely ever cum twice with a client before. I am about to now.

"Ohhhhh fuuuuck I am gonna cum again!"

"Oh fuck yeah do it!" He yells, grabbing my hair in one hand, gripping my hip with the other and pounding me even harder. My little cock explodes as ropes of hot sticky cum shoot all over the table below me. Just then he groans loudly and I feel his cock pulsing in my ass. Wow.

I hadn't planned on having any appointments today, though now I am glad I did accept the call. Greg is a regular client and a really nice guy. When he called in the morning I could feel his anxiety. A lot of people experience anxiety around the holidays and I'm no exception. This hot intense fuck is just what both of us needed. I can see it in his face as we pull apart. He's much more relaxed. So am I.

After we shower and hold each other with the affection of long time lovers. We kiss and caress each other's naked soapy bodies. Later as we dress he tells me about his wife and how there is just so much pressure to be happy during the holidays; he thanks me for being there for him. Greg pays me well as he always does, always nice to have a few extra bucks for the holidays.

OK, for those of you who are only interested in the sex stuff, now would be a good time to get off the Tammy train. I am going to just riff a bit on what life is like for me as a passable Trans woman.

First off, if for some reason you've never read my stuff before, I am a proud transgender woman. That means I look like a woman but I have a nice little cock and balls between my legs. I am rather fond of this part of me as it both gives me immense pleasure and makes me unique. I am what we call in the Trans world "Passable"

Passable means that when I go out in public what people see is a young woman, not a "guy in a dress". Some Trans people are not passable at all and to be honest they get the ugliest side of society thrown at them. I have friends like this and I empathize strongly with their struggles. I am not complaining at all about being passable, I am just going to describe some of the unique challenges associated with being that way as a Trans person.

So after Gregg left I put on some not so ridiculous clothes. It is cold outside so I dressed accordingly with a cute burgundy skirt over some warm tights and these really cute black suede wedge boots and a matching cable knit sweater. After I got myself all public presentable I headed off to the mall for exactly two things I needed to get for Christmas. One was for my Mom and the other for my best friend and roommate Emily. I am a terrible procrastinator and I really have no excuse for not already having these things.

So some last minute Christmas shopping, pretty much like any other person might if they were procrastinators like me.

That is where the similarity ends. As I walk into the mall I catch the eye of a super cute guy, probably in his late 20's. He's big and has a beard and a nice open and honest looking face. He's the kind of guy most girls would want, handsome and well dressed. He seems well put together all around, probably has a good job and seems like the kind of guy a woman might want to someday marry. I divert my eyes immediately and pick up my pace, I can tell he's interested and I don't want any part of all that, more about this guy later.

I was talking recently to someone I met in passing. She was a friend of a friend kind of thing and we ended up having coffee. She asked if I had a boyfriend or girlfriend. I told her no, I don't date.

"Don't date?" she asked incredulously.

"Yes" I replied nonchalantly.

"Like ever?" her jaw was practically on the floor as I just nodded.

"But it's so sad not to have someone for the holidays?"

Funny, I thought to myself, I don't feel sad. I actually feel pretty fulfilled. It isn't that I have never dated. I have had a few boyfriends and a couple of girlfriends in my life. Given my profession and my biology I find it to be more trouble than it is worth.

For those who don't know me I am also a sex worker. I use my massage business as a cover for what amounts to prostitution. My more trusted clients pay me to have sex with them. I have been doing this a fairly long time and I have never been to jail or contracted an STD.

OK so back to the guy in the mall. I have always been curious what it is like to be a real woman in that I could just let this guy approach me and ask me out. I could decide if I liked him and go from there. It is not like that for me and others like me. In fact this situation is fraught with potential danger.

Let's say I react differently. He smiles, I smile back. He comes up and introduces himself. Now let's imagine he's a perfect gentleman. He asks me out. Now I have a choice. I can string him along, maybe even for a few dates, some kissing and potentially even give him head without him ever knowing I am Trans. Some Trans girls I know do this. It is very dangerous, because eventually they will find out. A lot of Trans girls get murdered because of that. I don't like victim blaming, but I am not condoning it either, it does happen. Besides it is dishonest in my opinion and that is just not me.

Instead what I am left with is a confession. I say this advisedly. Being a person outside of the mainstream people expect me to be exactly what I appear to be, a young genetic woman. Telling people that you are not always comes across as a weird sort of apology. I try to phrase it positively but it still comes out like that.

So instead, if I wanted to try I would I tell him that I am Trans. I a lot of men get really upset upon hearing this, some to the point of violence and other foolish sorts of behavior. Some people just hate finding out that a person that they are attracted to has the same equipment as them. It's ridiculous but it is the world we live in.

At this point he may get angry and storm off. He may take out his conflicted feelings about his attraction on me. He may do that through teasing me, calling me names, attempting to hit me. I have seen all of these reactions in men. If you have read my other stories you know the intensity of the assault I endured.

There is also the possibility that he's a great guy, open minded and still game for a date or even just saying "Oh wow, cool, not my thing but have a good day shopping." would be great.

Even if I get this far, up comes the next hurdle.

"What do you do for a living?" Mall guy asks of dinner and drinks.

"Oh well I'm a massage therapist and well most of my income comes from sex work."

"Sex work?" he asks, almost spitting his drink, "You mean like prostitution?"

"Yeah, pretty much." I reply.

Most people are not OK with this in someone they want to date. Even if he gets over the initial shock, well then there is the idea that he may try to fix me. I am not broken, I have been down this road and it pisses me off. He may try to get me to quit, say he'll support me. I like what I do and I like my independence. I am not cut out to be some guy's Suzie Homemaker. I'm just not.

So instead of going through this on the off chance this cute guy would still be interested and emotionally mature enough to handle all of that, I duck my head and rush to my shopping. Of course I don't rush so fast that my walk isn't sexy. I do want him to be attracted and I get a little private smile on my face as I hope he's looking at my ass and I hope he likes it enough to think about me the next time he masturbates. I may even think about him the next time I do.

Here is where people might say that my life seems sad to them. To a degree they are right. No one should have to go through life fearing that if people knew about them that they might be assaulted or murdered. There are whole countries where just being like me (atheist, trans and bisexual) would get me beheaded or thrown from the nearest roof.

For the most part those people who might pity me are wrong though. I meet all of my sexual needs, and even some of my emotional needs with clients. I am going to my Mom's for dinner tonight with my best friend Emily. There I will have a home cooked meal and exchange gifts with the two people I love most in life. I will feel the deepest love I can imagine. As we laugh together and hug intimately to show that love I will be so happy that I may cry as I am right now just writing about it.

My life is good as it is and I am so very happy despite all the challenges. No matter who you are or what you face in life, please find what makes you happy and hold on to it with everything you have. Don't ever let someone else tell you how you should feel.

Kisses,

Tammy