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6:35 PM - Sat 6.18.16
Coming & Going

Coming & Going

(WARNING: This entry's gonna be pretty much entirely about my second-and-final - at least for now - visit to an escort this past Monday. If you're squeamish when it comes to this stuff - and I'm certainly squeamish writing about it, believe me! - you should probably bail right now.)

Since I saw Ryan for the second time on Monday evening, I've spent the rest of the week, when I'm not thinking about other weighty matters, trying to figure out what to make of the experience (While comparing-and-contrasting it to our "maiden voyage" on Memorial Day).

One thing that was a little strange - In between our two sessions, I'd gotten a cold sore (right under my bottom lip, on the left-hand side).

Once I realized it was a cold-sore (And not an ingrown-hair), I agonized over it - "Do I text her to cancel? Do I medicate and hope it clears up in time? Is she gonna be mad if I wait till Sunday and then cancel? What should I do?".

On Sunday, when it had dried to just a little scab under my lip, I thought, "Do I just go and hope she doesn't notice, or doesn't care?".

I didn't want to postpone (after the first time, I had a full head-of-steam about having a second time ASAP), but I also didn't want to go and have her say, "Dude, you come in with that on your face and didn't have the common courtesy to warn me? WTF?".

But since I'm (basically) a decent guy, and neurotic as fuck, I texted her - complete with a picture of the affected area - and asked what she thought (Postpone? Proceed? Proceed while wearing Haz-Mat suits?).

And she said "I get cold sores myself, so it's no big deal. Don't worry about it. I even have some good medicine I'll bring when I see you" (While the Ryan of my neurotic fears is kind of a bitch, the real thing is clearly a sweetheart).

The funny thing about all this?

When we got together, she looked over my lips, gave me the medicine she'd talked about (A white pill - an antiviral, I guess?), and in spite of the dried-up cold sore being "no big deal" in her text, she was definitely more tentative about the kissing...which was now, to my way-of-thinking, just perfect (If you remember, I wasn't nuts about the kissing the first time - there was a lot of porn-star like tongue - cause I felt like it was just "too much").

But I've gotten a little ahead of myself...

One thing I keep thinking is that it was both "better" and "worse" than our first time on Memorial Day.

The first time, it was at a Holiday Inn Express less than three miles from my apartment, which I loved (Whether it's an audition or a visit to an escort - In LA, I really like when getting wherever-it-is is a breeze).

But this time, she was in West LA, so there was more of a drive, and during rush-hour (I was meeting her at 6:00 pm). So there was some driving stress mixed-in with the sexual excitement.

I overestimated how long it would take - didn't want to make her wait - so I got there 20 minutes early (Texted her, but it was over 10 minutes before she responded - somewhat tersely and confusingly - and a couple more minutes before she told me her room number - Not a big deal, really, but it started things off a little off-kilter in my mind).

Last time, she'd come down to the lobby and gotten me - Not sure why, but I preferred that to just going up to the room (Though part of that might have been the initial excitement/trepidation of meeting her the first time. Or maybe some weird thrill of being "naughty", because the desk clerk might see the both of us together? Who knows?).

The awkward, "off-kilter" feeling continued when I went up to her room - our chit-chat felt more strained than the first time, a little more "pro-forma", perhaps? Hard to put my finger on what the "issue" was, but things just felt...strained (I know she'd intended to shoot a video for her website earlier, and the person flaked on her, so maybe she was in a bad mood because of that? Distracted? I'm not sure).

She was already down to a shirt, heels, and underthings (It's a seriously good "look" for her), and I saw a glass of wine or champagne on the end-table (Which made the bottle of champagne I'd brought - a pricier bottle than the first time - seem somewhat superfluous).

But it wasn't too long before we started to recapture the fun vibe we'd had the first time, with a lot of laughter and joking, maybe starting when she was running my credit card (As I felt myself starting to respond to her sexually, I began faux-talking-to-myself - "Jim, let the pretty lady finish what she's doing before you grab her, okay?").

Speaking of the monetary part of the program - She'd said she was going to give me a discount due to the nice review I'd written for her on an adult website, so she asked, "Would $XXXX be okay?".

It was a substantial break from the last time, which had already been a discount from her regular 2-hour rate...but it wasn't nearly as much as the "June special" she had on her website's blog (Where a returning client would get 50% off what they paid their first time).

But I so didn't want to haggle over rates and "specials" while I was literally in the room ("Gee, that's a nice offer, and I really appreciate it..but can you do any better?") - beyond it feeling super-awkward, it just didn't seem the way to insure having "the best experience" - so inwardly, I decidedly to just "take the hit", and said "Sounds great! Thanks!".

(Yikes! Re-reading what I've written so far, and it doesn't sound so good, huh? Well, let me just say, "But wait! There's more...!")

One change from before was that, instead of her doing her dance like last time, our initial "foreplay" involved kissing as we were both standing up next to the bed, and getting undressed from there. I really liked it - the dance had been nice the first time, but the fact is, no one I'd ever had sex with previously had done a "couch-dance" for me before we did the deed, so this felt more "real", and not like some kind of erotic Kabuki theater.

Speaking of "real" tantalizing thing Ryan had texted me after we arranged a 2nd get-together was "I'm going to cross a personal boundary for you...".

And that "personal boundary" turned out to be "a blowjob with no condom".

(I don't think I said it out loud, but inwardly, when I realized what was about to happen, I was like, "YAY!".)

This was head-and-shoulders better than the first time, which had done next-to-nothing for me - It just felt better, first-off, but it was also more erotic (It's pretty deflating - literally! - to watch someone doing something to you sexually, like sucking your dick when you've got a condom on, and thinking "Jeez...that can't be much fun...".

As she started, she said, "If you're gonna come, let me know, okay?" And if it had gone on for awhile - I don't know exactly how long "awhile" is, but...awhile - I think that would have been in the realm of possibility.

And if-I'd-known-then-what-I-know now, I might have relaxed and let that happen, if it was gonna happen...but in the moment (And this was early on), I thought how there were specific things I wanted to do (doggy-style, reverse-cowgirl, from behind standing up), and things I wanted to see more of (like her back and ass, clearly). And I really had my heart set on having an orgasm, if I was going to have one, during sex.

So I cut that part of the program short. Which feels stupid now because it was really good.

I went down on her again, this time not being nearly as tentative, but also taking pains to make sure I didn't get too aggressive, like the clients she complained about the first time.

And it seemed like she liked it - Without my asking, she said, with a great deal of enthusiasm, that it was better than the first time.

And at one point, she started "moving around" under my tongue, which I found exciting (That was where I thought - rightly or wrongly - that we were, at least for the moment, having a mutual erotic experience. And again, rightly or wrongly, just the idea that I was actually "doing something for her" sexually, to whatever degree, was very sexy).

And she invited me, once again, to lick her ass (I'd been kind of kissing and stroking her in that neighborhood, so she said "You can get right in there - I'm very clean", which I found both very funny, and very hot (I was, again, definitely less "tentative" about it than the first time. The first time was arousing just because I was doing something I'd only thought about before, while this time was more like, "Yeah...I can admit it now - I seriously like this...!").

(The ass-licking is one thing that makes me ponder my "sexual wiring" - Do I like it because it's "dirty"? Does it have an appealing air of "subservience" or "subjugation"? What's going on there, exactly? - but if I wanna do it and can find women with nice asses who like it/will let me do it, who cares really?)

We did missionary, we did her on top, and we got in the positions that gave me the "visuals" I'd wanted - reverse-cowgirl, along with a couple variations of "from behind" (At one point, I was looking around the room, as if I'd suddenly spy a chandelier or something that we could swing from) and much of the time, whatever-it-was felt great - but no matter what we did, I couldn't quite "get there".

At one point, I did something I'd done "in practice", between visits, that had gotten me off (Well, it was either "practice" or just "masturbating while fantasizing about her". I'm not really sure which. But I really was trying to masturbate less, and make it more..."sex-like", so I'd have a better time the next time we saw each other).

(And here's where I now get really embarrassed...)

I told Ryan, as I was on top of her, "I'm going to say some stuff - It might be a little weird...".

I imagine she thought I'd start cursing and calling her a bitch and what-have-you, but that wasn't what I had in mind - Instead, as I thrust inside her, I held her close and...started telling her how much I loved her ("Oh God...Oh Ryan, I love you...I love you so much!")

Pathetic? Sad? Kind of sweet? "Oh, the poor guy really just wants to be in love...!"

Whatever it was, it almost worked. It might have been play-acting, it might have been real "in the moment", it might have been me having a sense-memory of sex with someone who used to love me half a lifetime ago, but whatever it was, it almost got me "over the hump", so to speak.

But I didn't get off.

Nothing got me off, however good it felt (And one thing was disappointing - The "reverse cowgirl", while offering spectacular visuals, was probably the worst position we did in terms of how things felt, because it put things at an awkward angle. I probably would have done better with her on top facing me, with some well-placed mirrors for my viewing pleasure).

Part of the general problem was mechanics - I hadn't thought about this in decades, but one problem I'd had with sex (back when I was having sex), was that, although I'm tall, my legs are really short. Which means certain positions - like the things I'd wanted to do with Ryan because the visuals aroused me - don't work very well because parts don't line up right (It's the kind of thing I imagine can be worked out in a committed relationship - "If we put some pillows here, and you climb half-way up this ladder, then I swing down from the could work" - but it's hard to do on the fly with someone you've basically just met, particularly when there's a "time element" involved).

Another problem is that I'm just fucking old now, and even though I've been Zumba-ing these past months, I'm still a guy who hasn't had sex for the majority of his adult life, who typically gets himself off in minutes masturbating to porn - So my "sex muscles" are not in shape, and there was an issue being able to thrust hard enough/long enough/fast enough to get off (I just can't move my hips as fast as I can move my right hand, dammit!).

But the main culprit here?

The fucking condom.

She'd brought Magnums for me, so the "fit" wasn't an issue this time out, but I do think the reduced sensation made things just hard enough that I couldn't get past it.

(I feel pretty certain, any other issues aside, that if I hadn't had that condom on, there were a number of times I was aroused enough that that would have made the difference. But anyway...)

Here's the least happy part of the experience - I'm not sure the exact moment it started (I think maybe after she'd thought I came after the "Missionary position"/profession-of-love portion of the program...but it turned out I hadn't), but Ryan clearly started "losing interest".

She never sounded mad, exactly, but at one point she asked if I was "trying not to come" (I wasn't), and at another point, if I "wanted to come", or, again, was "holding off, looking to create 'memories'" (Don't remember what I said, but the answer was kinda "Yes" - I was definitely invested in coming, particularly since I hadn't the last time, and was't trying to "hold off" my orgasm...but since this was the last time we would be together and I was paying dearly for the privilege, I was looking to get the most possible out of our time. I would have been kind of horrified if I'd had an orgasm 10 minutes into my time, for example).

There were a few other comments (Like a comically rueful, rhetorical "What is it with men not being able to come?"), and internally, it "brought the whole edifice down" for me (Not terribly sexy or great for the self-esteem when the message from a woman you're having sex with, that you think you're having a nice time with, becomes "Damn Man, would you fucking come already?") - We had time left, and I wasn't ready to give up, but for her, the "us having sex" part of things was clearly over.

And really, she was probably right - if I'd hopped on her and pumped away for another fruitless 15 or 20 minutes without getting off, that would have been tough for me to deal with as I drove back home. And who knows? Maybe for her too, a little bit. But anyway...

Like last time, she threw out the option of watching her play with herself (I had the feeling that that's what she ends up having to do with a lot of guys - She said "a lot of men can't come with a condom on"...which made me want to say, "If you know that, why were you giving me shit about intentionally trying not to come?, like I was doing it just to frustrate you?".

So, kind of begrudgingly, I said, "Yeah, let's do that".

So she masturbated with the dildo/vibrator/whatever, as I stood behind her, jerking myself off (She started doing it from the top, and I asked her to do it from underneath, so I could see better).

It was exactly the scenario from the last time, where I'd said, "It was nice, but kinda not-the-point, to be masturbating to live-action porn".

Except last time, I'd already given up on the idea of getting off at that point.

But this was the end of my big "sexual adventure" - I wanted to come, I wanted "someone to be in the room" when I did, and "any port in a storm"...

And after an an hour-and-a-half or so of sexual stimulation, and being pent-up from not having gotten off in almost three days, with my faithful right hand leading the charge, and Ryan providing very stimulating "live- action porn" I came within minutes.

The two of us had a celebratory few moments - I was certainly relieved, and I think she was too (She laughed and said "Yay!" as I hugged her from behind) - then as she went to shower (My "relief" had landed on her back and ass), I crashed harder-and-faster than I have in quite some time.

Part of it was disappointment - powerful orgasm aside - that things still hadn't gone the way I'd wanted them to. Ultimately, I felt like I hadn't "had sex", I'd masturbated, something I already know I'm really good at.

I had the right condoms. I had 50 mgs of Viagra in my system. I'd worked to "retrain-my-body" (Granted, trying to make up for 25 years in two weeks, but still...). I had a very sexually attractive partner.

And it still didn't go the way I'd wanted it to.

Beyond that, I was just really sad that the whole thing was over - What would just be "paying for sex" for some people was an epic adventure for me, that had started before Memorial Day and was going to, inevitably, be a pretty brief affair. It was exciting and scary, and gave me something to look forward to (And something to write about)...and now it was all over.

But suddenly we're moving toward 3:00 am on Monday morning...

That was the experience, but I'm going to have to save the wrap-up and post-mortem for next time...

(Hey, this might be the last time I have sex for the foreseeable future - I've gotta "stretch it out" for as long as possible, before I'm back to writing about how acting isn't going as well as I'd like and I'm afraid of death, and all that horseshit...)


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