Apparently I’m not T-Pain.  Okay, that's misleading because the woman who I’m referring to isn’t a stripper so maybe I can still be T-pain (referring to the song “I fell in love with a stripper y’all” for those who might be unaware).  I had my meeting.  My get-together.  My appointment.  I did not fall in love.

That’s a good thing though.  The alternative being that I met this woman and she made me feel incredible beyond belief and then I became obsessed.  How far would I take the obsession?  Bi-weekly meetings?  (They would be weekly but she seems to do an every-other-week thing between here and the city).  It would have been an interesting turn of events, however I’m much happier being in the non-obsessed realm and a firm grip on reality.

I’m not saying the experience was bad though.  It was great.  I’d give it an 82 out of 100.  (please note that I am a notoriously tough grader.  You should see my Letterboxd reviews).  I do hold some blame for it not being higher as I was nervous and a bit shy in saying what I wanted.  I got what I wanted, because, as mentioned from before, I wanted everything all at once and, therefore, didn’t know what I wanted to happen in this particular instance.

I orgasmed.

I was touched seductively.

I was able to touch her.

I sucked on her breasts.

She ran her fingers along my body.

She made me shiver.

She even grazed my feet a couple of times, which made my entire body shiver.

I couldn’t have asked for a much better experience for a first time endeavor.  She was great and did everything wonderfully based on what I gave her as clues and tips.  I would imagine, the more she gets to know a person, she would be able to know what they like and tailor the experience towards that.  With a first time guest she’s got to test the waters.

One thing that didn’t happen, and this has no bearing in the overall grade of 82, is vaginal intercourse.  What, you say?  Exasperation?  Surprise?  Dumbfoundedness?  How in the fuck do you pay for a sex worker and not actually fuck her?  Pretty easily actually.  

Going into it I had an inkling of a suspicion that I wouldn’t actually make it to have my dick enter her pussy.  My first thought was because I figured I would cum nearly the second she started jerking me off, and if she had joined me in the shower I very well may have not even made it to the bed before I spurted all over the shower and had it drain down with the soapy suds. 

Thankfully that didn’t happen.

My second thought was that I’d orgasm from her hand.  The way I had my ideal scenario set up in my head was that I would nurse at her breasts (okay, suck not nurse.  There was no milk or anything but its my kink and I’ll call the terms what I want) and she would give me the slowest, most sensual handjob I would ever experience.  She would tickle her fingers along my stomach, chest, hips, testicles, cock and up my back before starting over again by wrapping her fingers delicately around my shaft and pumping slowly while moaning extremely softly and whispering gentle encouragement.

“You’re doing so good, baby.”

“Mmm, just like that.”

“It’s okay if you want to cum.  Just let it all out.”

“There you go, good boy.”

“Nice, big, deep sucks.”

“Do you like that?  Moan for me if you like that.”

It would all be even more intense if she referred to herself as “Mommy” but it’s a little early to introduce that level of kink, even if you’re paying someone to fuck you.

All of these words breathed softly down to me as she teases me over and over again.  I would whimper and whine as my breathing grew heavy and eventually drop my lips from her nipples and moan until she strokes me and I cum all over myself.  Then, as an extra bit to finish it off, she would wipe her hand on me to clean it off from any cum that got on her.  It’s something my ex wife used to do and it gave the entire experience a bit of submissive spice where she’s saying, “ugh, gross.  That’s all you’re getting,” but without saying it.

That didn’t happen either, even if it would have been the preferred way for it all to go and probably would have had me give her close to 100 if not an actual 100 if it went exactly as my mind had imagined it.

What actually happened, you ask?  Well, to put it in stale words, she put a condom over my dick and gave me a blowjob until I orgasmed.  I did not have that on the bingo card because I didn’t even imagine I would ask for a blowjob.  It’s not that I have anything against them, but I’ve had such lackluster blowjobs throughout my life that they’re kind of ruined for me in a way.    Now, this woman gave an incredible blowjob, even if it was while I was wearing a condom.  There was a while where I didn’t think I was going to finish, but I also felt like I was purposely holding back.  Once I decided to accept it and try to just let it happen she was able to make me cum so intensely.  

She used her hands to tease my balls in the most perfect way.  It was so gentle but it made me shiver and quake in her hands.  I spread my legs apart to give her better access, I didn’t want it to stop and I let her do what she’s good at.  

What felt the best about the orgasm was how I could let go with it.  I didn’t have to hide any of my reaction or subdue my moan so I wasn’t too loud or too vulgar sounding.  I just groaned out, let a nice “fuck” bellow out at the peak and then laid back panting, and what she did next was the best part, not of the entire experience but just made me feel so incredibly satisfied.  She told me that I could just lay back and enjoy the feeling while she went and got a warm cloth to clean me up.

That is what I was searching for the most, and what made me go through with it despite the doubt that kept coming up, that maybe I should cancel the meeting.  But I wanted to have something that was for me and treated me.  I got to experience the benefit and revel in it.  The only way that moment would have been better was if I could have rolled over on my side and went to sleep.

That wasn’t everything.  It was actually only half the time.  The rest of the time she gave me a massage and lotioned my body.  Overall it was okay, the massage part.  She lotioned herself up and slid up and down my back, which was my least favorite part of the entire experience.  It wasn’t that the feeling was off-putting or I was uncomfortable or anything like that, it’s just that I’ve always found it dumb and I never understood why anyone did it whether it was in porn or in real life.  

What I’ve mostly taken from the entire experience, now two days removed from it taking place, is that I don’t think I’m a sex obsessed person despite my brain always (seemingly) thinking about it.  I write bad erotica and keep a sex blog but it’s not something that consumes me so much that I need to have it all the time.  Either that or maybe casual sex isn’t for me.  

That last part is the one that hit home the most because I had always thought casual sex was the perfect form of existence.  Fuck whoever you want, as long as you’re not hurting anyone.  New experiences.  New people.  Apparently not?

This woman was great at her job.  She made me feel comfortable and relaxed.  She did everything she needed to do.  82 is not a bad grade, it’s above average, which is why I keep coming back to me being part of the reason the grade isn’t higher.  I don’t think it’s something I’m going to need to do frequently.  I may reach out to her again in a few months, but prior to meeting her I was flush with thoughts of when I would get to see her next.  

Now?

I’m wondering how long I can go without seeing her and not have it seem like I didn’t like my experience.  I’ve sat contemplating if I should send her a thank you gift so she knows how great she was and when I don’t contact her for an immediate get together she won’t think I was unhappy with the service.

And then, overall, what I’m feeling now is very similar to how I felt after meeting with a man I met on Grindr (I’ll have to add a post about him, among many other things.  I had written about him on my old blog but it’s been exploded).  I met a man on Grindr who was gay and he invited me over to his house for sex.  We had a pretty good time all around, aside from a few things that didn’t go as well as I wanted and one thing that turned me off, but all together it was a positive experience.

But afterwards I had this same feeling of I don’t need this.  I ended up deleting Grindr and, well, not necessarily ghosting the guy but ghosting the app.  I did tell him before I deleted the app that I had an amazing time and it was exactly what I needed.  He was a great kisser and he had a very big cock (at least compared to mine).  

So now I’m stuck with that eerily similar feeling of, “I liked her, but I’m not sure I need to do that again anytime soon.”

Is it the casual sex I didn’t take to?

Is it that I just don’t need sex that often?

Is my libido shot?

Or do I just need someone I actually care about for it to mean something?  I know, how saccharine.  The guy who writes erotica about women who turn into sex cows and leak milk from their tits wants to find a girl he loves before he can care about sex.  I’m starting to think this is the one that wins out.  

I can write about sex when it's something that turns me on.  I can get turned on about something and get hyped up about something I go looking for.  But then when the experience happens and there’s nothing there but the sex it doesn’t hold me.  It’s the same when I meet someone and we talk and have a good enough time but after a few separate conversations I realize they’re kind of boring (or, maybe that’s mean.  Maybe they just aren’t for me).  I need something else that keeps me there.  

Maybe if she played up to a hyper specific kink?  Yeah, that would have been enough to keep me wanting more, at least until it got played out.  That’s just it though, there has to be more than just sex with someone.  I always feel that there are so many men out there that just need to have sex and cum and that's enough for them, but I’ve never been like that.  It turns out I’ve always been right, I’m not like that.  I need another layer.  I need another factor to get me to want it again.

So, yes, I will most likely go see her again.  But that will only be because I wouldn’t have had sex in a while and I would be hungry for someone to touch me.  I’m sure it will be just as good as the first time, if not better because I’ll be a bit less shy/nervous.  I think she’ll serve an important purpose because it will allow me to not be worried about meeting someone because I miss sex and miss someone touching me.  I’ll be able to hold out and meet someone I like and find attractive both physically and mentally because I’ve already had that touch need met.  

In the meantime I’ll see if the well hasn’t dried up.  I’ll try to finish that damn sissy story I’ve been working on for so long and then maybe start something new or continue something I’ve got a little bit of work done.  This was a great experience and it’s funny how it all turned out, not nearly as I would have expected.  Always pluses for growth and finding things out about yourself you didn’t know though.