12:55 pm - Weds 06.01.16
Jim's Big Memorial Day Adventure - The Not-Quite Climactic Conclusion

Before I get to "Part II" of my story...

Nice surprise today- While working at Weight Watchers (I'm in Santa Monica on Wednesdays), got a text for one of those "audition" things I used to do back-in-the-day (I kid, but my last audition was almost a month ago, and it feels ever longer).

It was another dancing thing, for a commercial, but this time, I was actively encouraged not to try to be "goofy", but to dance to the best of my ability (Which, as you might remember, is something I like to do).

(I thought it went very well. Callbacks are supposed to be Monday - Wish me luck!)

Now, where did I leave off yesterday...?

On Sunday - I'm not sure what time (But I feel like it was early evening)- I made a date to see "Ryan" ( i.e. The woman from the website), at 3 pm on Memorial Day.

(I put her name in quotes because it's clearly her "nom de escort"...but it's the name I know her by, so from here on out, when I mention her by name, it'll be quote-free.)

Remember how I said my original plan had been to make a reservation for a couple weeks down the road, so I'd have time to "think about it" and maybe back out?

Well, apparently potential clients "flaking" is a big occupational hazard for escorts - as a good salesperson, she moved me to a commitment very quickly, and after we set the time (3 pm), she made me agree we were "beyond cancelling at this point, right?", and told me she'd re-confirm with me again in the morning.

On one level, all this made me more nervous - in a "this is all happening so fast...!" sense - but I totally "got it" (She's a professional, she's coming from out-of-town, and she doesn't want her time and energy wasted), and I felt reassured by her "professionalism" (If she didn't want me to "flake", she wasn't going to "flake" on me either).

And after all, it wasn't like she was pushing me into something I didn't want to do.

The next morning, I got up, had breakfast, messed around on the Internet, and picked up around the place a little.

But as you might imagine, it all just felt like killing time (Well, everything I do these days feels like "Killing time"...but in this case, even more so!)

Speaking of "picking up around the place" - In a blog post on her site she'd written about possible "adjustable rates" for the gentleman of more modest means - so I brought it up (I said something like, "I'm a working actor, but not a famous one"), she offered to come to my place, for substantially less.

(I thought about it for an instant, then declined, thinking I'd have enough to be self-conscious about when the time came without being embarrassed about my crappy apartment and shitty housekeeping.)

Late morning, Ryan texted me, confirming that we were still on, and asking if we could push things to 4:00 (I think she'd told me by that point where we would be meeting, at a Holiday Inn downtown, just a few miles from my place).

She texted again in the afternoon, saying traffic was heavier than she'd planned and she might be running late, and reminded me what I needed to bring with me (ID, my credit card - she'd prefers cash, but I didn't want to take that much out of of my checking - and a bottle of champagne).

She texted again - She was at the hotel, on time (actually, early I think), but having some trouble with the reservation, so suggested I arrive at 4:15, so she could have time to set up (I think she'd already given me the room # at that point, and had told me to let her know when I got there, then come on up).

Eventually, the time came - I showered more thoroughly than I have in years, and drove to the place (Driving right by it initially - It was one of those "Holiday Inn Lite" places, and I'd been looking for a stand-alone sign, when it just had "Holiday Inn" on the building).

I, parked, texted Ryan I was there, took a deep breath, thought "Oh my God, I'm really doing this...!", and walked in.

(Warning: Okay, I'm writing about my first experience with an escort - Do I really have to warn you at this point that things are gonna get a bit...graphic?)

Feeling slightly paranoid, I didn't want to ask the desk clerk where the elevators where, so I was looking around when I heard a voice - "Jim?"

I turned...and there she was.

And I thought she was perfect.

She didn't look like a hooker, she didn't look like a supermodel, she looked like a very attractive, friendly, put-together, real woman. Streaked, maybe collar-length blonde hair, slim-but-not-skinny, maybe 5'8" or 5'9" in heels (Like some of the other people who had "reviewed" her - on her website, and on Adultsearch.com - I thought she actually looked better than her pictures. And I'd been nervous about her appearance - "What if I see her, and I'm disappointed?" - but I was so not-disappointed).

We went up in the elevator - joking about "technology" when she had a little difficulty with the key card (which was needed for the elevator as well as the room - that's why she had to come down to get me) - and into the room.

Soft music was playing, and I think maybe just the table lamps were on (I'm going to be a not-completely reliable narrator here - I'd be a lousy eye-witness - but I'll do my best).

She'd looked at me and said "You're cute!" in the elevator, and said it again when we got in the room, "You are really cute!" (She said it a number of times throughout our time together. And "cute" was nice. "Cute" I could buy - If she'd said "You're so handsome" or "You're so sexy", I would've wanted to say "Cut the bullshit, okay?").

For my part, I told her she looked even better than her pictures, and periodically as we chatted (I was paying for two hours), I would literally lose track of what I was saying when I'd look at her, and tell her, "I'm sorry...I just can't get over how good you look!". And I meant it.

We had to get the "business" out of the way first... she apologized that it was taking some time to do the credit card, then she had me sign a "waiver" (I guess that I agreed that the fee was the fee, whatever happened, and I wouldn't try to cancel the charge). She asked me where I wanted her to send the receipt - phone or email - and I said "phone", and the "business" part was done (More on that later...).

She opened the champagne I'd brought, and poured us each a glass, and we chatted - I was nervous, as you'd imagine, and did what I do when I'm nervous with any new person, which was to turn on my "funny/charming actor" persona.

But I was also quite honest, and on some level, not trying to put on a front - I said pretty early on, "This is not just my first time with you. This is my first time with anyone, in a very long time".

(Cause really, what was I gonna do, try to act like I knew what I was doing?)

We talked about what we do for a living - and, amusingly, kind of "bonded" over the story of my Shameless nakedness (She said, almost like we were fellow erotic dancers, "The first time is really hard...", and I said, "Yeah, but at least when you got naked, people went 'Yay! She's NAKED!'", which made her laugh).

Then, at some point that seemed quite natural, she excused herself, went into the bathroom for a bit, and came out with just a shirt on over her bra and panties.

She got me down to my underwear (I'd opted for black for the occasion), and said, "I used to be a dancer, so I like to start things with a little dance. would that be okay?".

I said, "Uh...sure!".

So it was basically like a couch dance at a strip club, except I was lying on the bed in my underwear (It was so much like a couch dance - the only experience I've ever had with this sort of thing till now - that it took me a few moments to realize I didn't have to keep my hands limp at my sides: "Jim, you can actually touch the really pretty lady!").

She took her bra off, and I think I might have actually laughed with delight, because she laughed happily along with me and said "Boobies!" (There was a lot of laughter in general during our time together, which I thought was fun).

At one point, I don't remember if it was when she was feeling my penis through my underwear or when she'd actually taken my underwear off (I think it was the latter), she exclaimed loudly, "You have a big dick...!

I don't remember my exact response, but the tone was basically "Oh come on! You don't have to say that...!".

And she was basically like, "What, I wouldn't know?", and went on about how one thing that was interesting to her with what she does is how you can't ever tell what a guy's got going in his pants by his body type - "It's always a surprise", she said.

(But more on "my big dick" later, because it figures into the story...)

From there, we...did stuff.

Early on, she said, "I just have two rules - No fingers in the butt..." - which I could live without...but which probably would have happened at some point if she hadn't said anything - "...and condoms are a must".

One thing I think she got a kick out of - beyond my kid-in-a-candy-store happiness over her and her body - was that I was like, "Can I do this?", "Is this okay?" (I went in wanting to have fun, but also with the idea that I didn't want to be a client she'd have to "grit her teeth" through - For whatever reason, I have an obsession with employing a sex worker, then becoming her horrible comic anecdote after-the-fact).

At one point, I told her, "True Confessions"-style, "I feel bad for every woman I performed oral sex on when I was younger, cause I don't think I was very good at it (I think I spent all my time licking their vaginas, and never got anywhere near their clits)...can I 'give it a try' with you, and see if I have the right idea now?".

To my recollection, I've never been with someone who was shaved "down there" (Wasn't the "style" back when I was sexually active), and I loved it - One reason I grew reticent over time about going down on women was the fear that I just wasn't good at it, but another was that, with a lot of hair down there, you can't see what you're doing, you end up with a mouth full of pubic hair, and sometimes the smell and taste were... not so great.

But this? She looked good, she smelled good, she tasted good,and I could have stayed there a long time, happily licking away, if I wasn't "on borrowed time", so to speak... and didn't think it was a little silly of me to think I could give my new friend, the professional sex worker, an orgasm (Taking note of my happy noises during the act, Ryan said, laughing, "Oh, you're a giver...!". And for the record, she gave me good marks, complimenting me on my gentleness. She said "Most guys just get in there and go-to-town, and it's kinda painful". So then I imitated her having to deal with that - "Oh, that's so good...(ow!)you're the best...(Ouch!)" - and she laughed again.

I also got to do something I've never done before, because I could never get up the nerve to ask a woman in my personal life, and (I'm embarrassed to say this) licked her ass.

(And, once again - Looked good, tasted good, would have happily done that for quite awhile.)

Suffice it to say, things were going pretty well - The only thing I wasn't nuts about at that point was the way she kissed (It was pretty fake "porn-star" stuff, with WAY more tongue than I like - I like to "start small and move up", not immediately go at each other like we're trying to eat each other's faces. In addition, my mouth is actually kind of small, and I have a condition where I don't really have the space I'm supposed to for my teeth and tongue and uvula, so my own tongue feels too-big-for-my-mouth a lot of the time (Meaning, while I'm game for a tongue sword-fight when kissing, if my tongue is in my mouth, and your tongue is completely pushing into my mouth, I find that...unpleasant, almost a "choking hazard").

But it felt awkward to say, "I don't like what you're doing, do it like this..." (Oddly, commenting on how someone kisses feels...too "personal" to me, while asking for what I want sexually, on the other hand, just indicates I like this or that sexual "thing", or need a particular kind of stimulation to get off - but I'm sure she would have adjusted if I'd simply asked. So I feel like that's on me.)

So, lots of fun...but my "Sexual Waterloo" was the mandatory condom (for oral sex and for intercourse).

She got me completely hard at one point, using some lube, and put the condom on with her mouth (I don't think anyone's done that to me/with me before - I was impressed).

But condoms have always felt bad to me - Not so much because of the "reduced sensation" (That I can deal with), but because I feel "squeezed in".

In a word, I can get hard, but with that pinched/restricted feeling, I can't stay hard. And once I start to lose it, it's difficult-bordering-on-impossible to get it back (And let's remember - I'm also a 55-year-old man who hasn't has sex in a good 25 years, who's messed up his sexual wiring by masturbating pretty much daily, often as briskly as possible).

So oral didn't really work - in addition to my "condom situation", it just seemed unpleasant on Ryan's end, to be mouthing a lubed-up condom, and that wasn't very sexy to me - and intercourse only worked a little better - We did missionary, and her on top, and we'd start okay (Just being inside a woman was pretty great), but eventually, I just ended up mushing myself into her half-erect.

She asked me if I'd like to watch her masturbate or use a dildo, and I said, "Yes please!".

And that was nice - I particularly enjoyed the latter - but kind of not-the-point, to masturbate to "live-action porn". I really wanted to have actual sex (Besides, to get off at that point, I would have needed to take off the condom, and wash off the half-dried lube, and by that point, my time would have been pretty much up - I was kind of amazed how quickly the time went by, considering I went in thinking "What the heck are we gonna do for two hours?").

The two of us talked for a bit afterward - I told her exactly how long it had been since I'd last had sex, and that I went into the session not really knowing what was going to happen for me sexually (I thought I might come in my pants the first time she touched me - fairly unlikely but possible - and I thought...what ended up happening might happen).

The idea that I was going to go from "zero" to "successful sex", with the "condom issue", my age, how long it's been, my "bad sexual wiring", etc...well, as I told Ryan, when she expressed disappointment that she hadn't made it happen for me, "That was a big pretty mountain to climb".

Speaking of "big" - here "my big dick" comes back into play - at that point, Ryan said something that might seriously change the course of my life:

"You need to buy Magnums" (a brand of condom for guys with bigger equipment).

I'm still marveling over this - I've had bad experiences with condoms throughout my entire, albeit truncated, sex life, because they were "cutting off my circulation".

And my answer to this dilemma, instead of "buy larger condoms", was to basically give up on sex (That wasn't the only reason my sex life died half a lifetime ago...but it was definitely a factor).

Because I just didn't think of myself as being "big" (I've always defined myself as solidly "average" in that department). I defined "big" as "having a cock like a porn star", and I'm not particularly "long", just "hefty"...but "hefty" is the entire fucking issue here!

(And yes, I've seen the videos where women put a condom on a cucumber, to rebut complaints from men that "condoms are too small". And my "rebuttal to the rebuttal" would be, "My cock is not a fucking cucumber!")

So if nothing else, having a professional escort say "You need to buy big condoms" (And no one else ever has - I guess other women I failed with while wearing a condom just thought I was impotent), that alone made the experience worthwhile, to the point of being potentially life-changing.

(Yesterday I did indeed buy a box of Magnums, and in the evening, I "took myself on a test drive" with one - fit like a glove, I could stay up, could even let myself "calm down" and "build myself back up" again - though I needed more lube than the condom itself provides - and, most important, could get off. Jesus, do I ever wish I'd realized I had "a big dick" sooner!)

But beyond the "condom thing", which is huge (Pun noticed...but not intended), this experience was tremendously worthwhile to me.

I am a sexual being who hasn't been sexual for most of his life. And here I am these days, afraid nothing new is going to happen for me, that I'm just "marking time" till death, having practically gotten used to the idea that no one is ever going to touch me sexually again.

Monday made a normal process - sex - seem normal again, even if I was paying someone for the privilege. I was naked with a woman (a very attractive one), and it was fun, and I wasn't embarrassed, and it seemed like something that could be "normal", that could happen someday in a normal context (Cause while I've gotten kind of "used" to being alone and unloved...that ain't "normal").

(Writing the above just almost made me cry...)

So I was afraid to do it, it felt extravagant-bordering-on-crazy to do it (I've never spent this much money on making myself feel good before...ever. Just before this, I was feeling guilty because I spent $70 on a ticket to see Louis CK in July), but I'm really glad I did it.

And, under the circumstances, I have to do it at least one more time...

I have to.

(PS I forgot something - When I got home, and looked at the receipt for the charge for our session...I saw that Ryan had given me the cheaper rate we had discussed earlier. It might sound funny to say, but I was...moved by that.)

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