I've caved. It's been 8 months since I've last had sex. I've probably masturbated every day since, sometimes multiple times a day, which I know is probably not any amazing feat but it was a sad little bit of context I thought I would throw in there. It's been a while since I've been touched by anyone other than my own hands.
The only problem was that I needed to find someone else as the previous sex worker I had went to see a few times has gone on indefinite hiatus. In all I saw her three times, once in February, again in April and then in August (which I strangely didn't write about even though she kind of pegged me and promised to actually fuck my ass with a strap-on the next time). I had found out as I was going to schedule another appointment with her in October that she had decided to leave the field. I was disappointed, but was happy for her. She was the perfect type of woman to introduce me to seeing a sex worker as she was extremely friendly and sweet.
Actually a couple of months ago I did schedule an appointment with another sex worker, someone who was going to be local which would be very convenient. There was a problem right from the start though, and I never ended up getting to see her.
I did my research and she had positive reviews and she was a real provider with a presence on social media so I reached out and set something up a few weeks out in early February. As time got closer to our meeting I would check out her social media posts and she had more of a you owe me attitude than the previous provider I had seen, the sweet girl who essentially retired. I didn't mind it though, just figuring it was the persona she was playing.
As it turned out I wasn't able to see her on our scheduled day. I had let her know a few days in advance that it I wasn't going to be able to make it. I had something similar happen with the sweet retired provider on our second meeting, I had caught a cold and was coughing a lot and asked to cancel. She said that was perfectly fine and my deposit could be forwarded to a future appointment, which ended up being in April. This new girl did not have the same approach.
When I messaged her and said I would not be able to make the appointment due to personal issues I thought she would say something similar. At this point I had also sent her a deposit and I was willing to lose it if she had never come to my area again, but was hoping to just reschedule. Instead she said that her coming to my area, which is rural, was based on demand and I would need to send her the full amount of the appointment.
No mention of it being a hold or reservation for a future appoinment.
No mention of anything beyond the implication of pay me what you owe.
It was a huge turn off, but I paid it. This might be seen as pathetic (yeah) and now I'm a fucking loser who paid a woman he didn't even meet to not have sex with him (absolutely). Did I go overboard to make sure a woman who, from the perfectly placed angles in her social media posts, seemed attractive wasn't upset with me? 100% percent. She was coming to my area before I reached out to her so I don't see how my scheduling an appointment with her had anything to do with demand if she didn't know I was going to see her prior to scheduling it. Anyways, not the point of the post.
It was two months since then when I finally decided to cave and reach out to travel to see a sex worker I was attracted to based on looks and personality. I should say perceived personality because I can only see what they post online but after contacting her she still seems sweet via text and is very punctual with her replies as well, so I've got a good feeling about it.
So, this new girl, I had been following her on Twitter for a while and she's got a great body and seems really sweet. The only reason I haven't seen her sooner is because she's about an hour drive away, which is a bit of time for what is, essentially, an expensive booty call. But I wanted to do it, the opportunity had come up to do it and I'm getting to that point where I've gone too long without being touched by another person and I'm starting to feel an extreme need of intimacy.
What makes me have a very good feeling about this and wishing I could schedule it sooner even was, when we were messaging, she told me what she had offered and I had pushed through my nervousness and apprehension of not wanting to seem like a creep and told her what I was looking for, which was this:
Do you like my hand pussy? (Make me say “yes I like your hand pussy”)
Do you want me to stop? Are you sure?
Ask me if I like your panties.
Ask me if I want to wear them on my face.
Tell me I better warn you when I’m going to “make cummies” because only you get to decide when I “make cummies”
As you’re slowly stroking ask me if I want to cum. Over and over, in between, anything else you say, in a sweet and kind voice ask “do you want to cum?” And when I say yes just ask again, and again, and again,
Comment on how small and cute my penis is and how it doesn’t deserve real pussy so it only gets hand pussy and maybe foot pussy if I’m good.
Tell me you want me to go pussy-free for you and then you’ll let me make cummies. Make me say it, that I’ll be pussy-free for you. When I do you take my hand and put it on my penis and tell me to make cummies now while you kiss my ear and whisper heavily to make cummies for you. I cum all over my stomach (or in a condom if it always needs to be contained) and you caress me and call me a good boy and tell me what a good job I did with soft caressing and kisses.
Of course it doesn’t need to be exactly that, I love the idea of you pressing your feet into my face while I stroke or teasing my penis with your feet. Spontaneity is always welcomed, but that’s the kind of thing I would love to experience with someone. Make me feel vulnerable but “cared for” if that makes any sense.
I do enjoy the thought of a sensual massage as well, leading up or after if I finish quickly. Whichever you prefer really as I’m sure you can make me finish quite quickly ☺️
I really like to lay on either back or front and have your fingertips graze/flutter/tickle over my skin. Especially between legs and thighs and over genitals. Just a tease. When you graze over a sensitive spot I shiver and it feels so incredible.
She had a simple response, basically telling me all of that sounded good and she was looking forward to hearing from me to confirm date and time. Me being me was hoping for a little more interaction and critique or excitement or anything while what she gave me was a simple one line response. I figure it was because, for one she's busy, two she has a life and doesn't want to entertain a random person she's seeing for the first time, and three I can imagine some men would message with kink and fetish stuff and try to get the providers to play along and talk about it so they could jerk off to the responses, but when the orgasm or fetish entertaining is what is being paid for why would she give it away for free?
So I booked her. In just over three weeks I'll have seen my second sex worker, and hopefully have had a very satisfying appointment. From what I could tell she didn't offer penetration, which is perfectly fine with me. Yes, I'd love to be able to fuck her, but I'm wondering if its a first time thing meeting someone thing, and even if she doesn't ever I'll save judging until after I've met her and had some time with her. Seeing as how during my favorite appointment with the first sex worker I met was when she was jerking me off and asking me if I wanted to cum over and over until I shot a load all over myself, I think not fucking her would be fine.
All I'm hoping to get out of it is an orgasm, a beautiful woman running her hands all over my body, a hand job and some kissing. Everything and anything else is bonus. From there I can do what I was hoping to with the now retired sex worker, play out some of my sexual fantasies and fetishes while also feeling more comfortable expressing what I want.
I'd like to have her refer to herself in third person as Mommy.
I'd like to have a foot job.
I'd like to cum on her feet and have her tell me to clean it off with my tongue.
I'd like to have her stroke me while calling me a faggot and gay (although I think it will take a long time to ask for this one and as its a little bit harsh and I don't know how comfortable she would be saying it)
If she's got a strap on and it's on her menu I'd love to be pegged by her.
There are so many things I'd like but it all starts with the first meeting and seeing how compatible we are, in both directions.
There is another provider I'm interested in as well. She recently posted a blurry face picture of herself and I liked it on my main, non-sex related account and she followed me back. She's got a very nice body and what appears to be a venus tummy, which I would worship until the end of time. Her bio describes her as friendly with a bubbly personality, which aligns her to my first sex worker who I adored. So, all in all, I've got options.
I'm excited to meet my new provider. I really need to think up names to go along with them and while I'm sure they might not mind having a little advertisement I'm also being a bit honest of my thoughts and feelings and I don't want to hurt anyone with something that might be seen as a negative or to get too specific about something that happens in the bedroom so I'll just keep it anonymous for now but maybe I'll use some letters or something to differentiate if I'm going to get too involved in the sex worker world.
For now the retired provider is N, the one who I paid but never saw is D and the new one I've got an appointment with is B. Loved N and hope she's doing wonderful with her new endeavors. Didn't get to meet D and probably never will. Really excited to see B.
That's the update. Now I'm going to see if I can spend an hour doing some creative writing and adding to the massive bucks I just earned in March from Amazon ($1.58!) and/or building up my website post library.