It’s a weird feeling. I used to do this job and I was bloody good at it too. I made a decent living and had a lot of freedom. I mostly did domination stuff, so it worked quite well for me. Understandably, I was a genius with a strap on. Now, here I am, and I am nervous as hell.
I’m six months post-surgery. I could have had sex before and I thought I would, but my girlfriend couldn’t handle my transition. She said that she’s always been a lesbian and now that I have a penis, she simply can’t be with me anymore. I sort of understand, but I really thought she was in love with me and not my vagina. Never mind. I’ve moved on.
Being newly trans, I’ve been a little bit anxious about going out, socialising and dating. I fancy women. Always have. But I’m still not sure if my new dick will actually work at all and I’m certainly very aware that it doesn’t look like a real one. That doesn’t bother me too much. After working as an escort, myself for three years, I learned that penises come in all shapes and sizes. Nevertheless, I’m new to having one and I’m not even 100% sure how to use it properly. I mean, in my head, I’m all man and absolutely capable, but I feel a bit awkward.
And how do I talk to women about it anyway? I’m going to have to work all of this out, but for now, I need to practise. I need to be with a woman. I’m sick of waiting. I mean I didn’t go through all of this for nothing. I’m ready as I’ll ever be.
A friend of mine had worked for Cleopatra Escorts and said it was a very open minded service with experienced and friendly women working for them. Even so, I didn’t really want to tell them about my situation up front. I didn’t know how they’d react, so I just arranged a date with a very beautiful, slightly older escort, who seemed to be experienced, was bisexual and had a lot of reviews saying she was super patient. I booked an outcall because I wanted to at least be somewhere, I didn’t have to leave, if I freaked out. I live alone in a nice part of the city, so it isn’t a problem for me.
She turned up just on time and, when I opened the door, I was more than pleasantly surprised to see that her photos didn’t do her justice. She was very good looking and dressed casually in jeans and a leather jacket. I have a thing for leather, so that worked. A good start for sure. I’m sure she could tell that I was worried because she took my hand, gently kissed me on the cheek, walked through the door past me and pulled me back into my own flat. The way she did it was so sweet and confident, it put me right at ease.
I offered her a drink and poured us both a whiskey. We made small talk and I couldn’t build up the courage to sit next to her on the settee. She seemed pretty chilled, so I didn’t feel pressured. I just leaned up against the breakfast bar and tried to check her out surreptitiously. She definitely worked out or did pilates or something. She was wearing a camisole under her jacket and when she took it off, I could see her arms were well defined. Her tits were unbelievable, and I had a hard time focusing on anything else to be honest. She was braless, so it was delightfully distracting.
Finally, I took a deep breath. I mean, I’m paying for her time and I’m also feeling horny. I say to her ‘I have something personal I need to share with you before we go any further.’ She looks at me and smiles gently, encouraging me to continue. ‘I..um…I…’. This is the first time I’ve talked about this to a strange woman. I pull myself together and blurt it out. ‘I’m transgender’. She tilts her head to the side and looks at me, a little bit confused. She giggles and says, ‘I don’t mean to sound stupid, but you don’t look like you want to be a lady, so I’m guessing you’re a man now.’ I exhaled with relief. No judgement and she seems to get it.
I smile broadly and say, ‘You got it and guess who is the lucky woman who is going to pop my male cherry.’ She burst out laughing, but not at me, just really warmly and honestly and said ‘Well, it’s my privilege then. This will be a first for me too. Come over here and let me help you relax young man.’ And that’s how it all started.
We had a shit load of fun. She was gentle and took her time to make sure that I was OK with everything we did. She also made sure that I was satisfied, and more than once. I think she got a kick out of being my first and took some pride in making it memorable. It most certainly was. In fact, I’ve decided to have a few more dates with her until I can master my technique and gain more confidence. I’m so glad I did it and I tip my hat to all the wonderful women out there who are helping guys like me, for all sorts of reasons. Everyone deserves pleasure in their lives. Seems like I’ve been making some good decisions in my life recently. One of them was most definitely to trust Cleopatra Escorts and their amazing women.