I don't know what the hell just happened, but one of the most awkward sessions ever was also one of the best sessions I've ever had. Of course, memory is a fickle thing, so I may be giving too much credit to more recent dreams, but...
The girl herself? She looks around 29ish (according to AMP standards, meaning she could be anywhere from 29 to 40). She has an average to pretty face. Average to pretty body. Average to okay personality (not very talkative or friendly). Everything was average separately, but it was one of those sum of all parts is greater than the whole things. The total package was better than average.
Anyhow, I don't know what came over me or her or what, but somehow while she was giving me a CBJ, we went through the whole gamut of upselling and negotiation through some really excruciatingly awkward conversation due to the sensitive subject matter (I've been yelled at and pseudo-banned from one place, pseudo meaning it doesn't matter because the mamasan changed).
Me: ..can I ask you something?
Her: What?
Me: If I ask, you're not going to get mad, right?
Her: What?
Me: You're not going to get mad, right? Don't yell at me?
Her: You're weird. Just ask.
Me: If I give you $100, can you do it with your mouth without the condom?
Her: What? Just do mouth?
Me: And sex.
Her: Mouth? No-condom? Then sex? Condom?
Me: Yes. I'll give you $100. Can you do it with your mouth without the condom?
Her: Of course, for $100, I have to!
She then whipped off the condom and proceeded to give me a BBBJ. I've had plenty of BBBJ's before (from personal life to AMPs to escorts), but hers has to be one of the best in my opinion. Just wet enough to be warm and enjoyable, but not too sloppy (I hate it when girls give a BJ with too much spit). She was also able to take it all the way without any teeth scraping, which is something I really hate.
Once again, proof that I have not learned from previous mistakes.
Me: How about down there?
Her: No.
Me: Not even for $100 more?
Her: No. How do you know I don't have a disease. I don't even do that with my boyfriend.
Me: Okay.
Her: Never.
Some more BBBJ. This went on for a while before another awkward conversation came up.
Her: Ready? (for sex)
Me: Does that mean you won't do it with your mouth again? (unsure because the bbbj is so good)
Her: What?
Me: I mean, if I put it in you, will you not do it with your mouth again?
Her: Huh? What do you want?
Me: Will you still suck me after we do it for a little bit?
Her: Huh. Okay. Let me get more towel.
She went out and brought more towels, but my dick died. So she just gave me some more BBBJ to cheer me up. But since now I knew she would give me more BBBJ after penetration, I asked her to stop. So she put on the condom and on she went. She did some nice cowgirl but she stopped entirely too fast and told me to get on top, but I wasn't going to complain.
While banging away, I dove in for some kissing. She did not evade. I doubt she was wooed by my ugly mug so it's definitely because of the tip she knew was going to ensue. Stuck my tongue into her mouth and we kissed pretty passionately.
I was about to cum way too fast so I pulled out.
Me: Shit.. I'm about to cum already.
Her: Haha. You know, us girls' goal is to make customer cum fast.
Me: Well not me. It's expensive.
Her: Haha. That is true.
Me: Shit.
She just waited patiently and did not put up a fuss, once again most likely due to the ensuing tip. Then I stuck it back in her for some more pumping and began kissing her again. And once again more awkward conversation.
Me: Where am I allowed to cum?
Her: Where do you want to?
Me: Everywhere.
Her: Everywhere is fine except for neck up.
Me: Even for $100 more?
Her: No! If it gets in my eye, I might get a disease.
Me: Oh, okay.
Some more banging. More kissing.
Me: How about in your mouth?
Her: Are you crazy! For $100! $300 total! ($100 standard tip + $100 for bbbj + $100 for cim)
Me: Eh.
More banging. She then started to make some noise. She was acting, but at least she was giving effort in her acting.
Me: How about for $50?
Her: Okay.
Me: Okay, do it now.
Off I go and she takes off the condom, wipes me down with a hot towel, and starts giving me more of that deep, wet but not too wet BBBJ. I'm in heaven.
Now let me preface this with: I HATE DATY. Licking the pussy of girlfriends in my personal life disgusts me, and licking the pussy of a working girl disgusts me even more. Not to mention she had already lubed herself up when we went for the sex.
But for some reason, I spun her around and just dove into her pussy. Now, I'm not a DATY expert, and I think this is maybe the third time I've ever done it, but her pussy tasted sweet. She must've used some sort of flavored lube.
Anyway, after a couple of minutes of this, I realized I hated DATY and raised her ass and watched her just pumping my cock with her throat. I used my arms to raise and lower her lower back to guide the pace and then I blew. She sucked it all up before getting up briskly and spitting it all into a towel.
She then took another towel and wiped my mouth off.
I don't know if I'm just remembering wrong or not, but this was honestly the second time I've ever felt that my dick was truly drained. The first time being when I lost my virginity. You know how you feel after you take the perfect deep shit that doesn't tear your anus. Or how you feel after you drink some cold water after playing some basketball on a hot day. Or how you feel after a good Thanksgiving meal.
It was like that. My dick was truly content and satisfied.
So while I popped out my wallet and gave her $250 (Plus $60 = $310 total... Ouch.), another conversation came up.
Me: You're going to talk bad about me after I leave, right?
Her: No! How can I? None of the other girls can know or they'll talk bad about me.
Me: Okay.
Her: If you ever do this again... With another girl... Don't talk about me? Okay? Don't say that I did it.
Me: Okay.
If you've seen my posts, you know I do BBBJ, facials, and BBFS. But this was truly my most satisfying experience and I don't even regret the huge hit my wallet took for a 40-minute AMP visit.
Anyhow, I then went home and jerked off to some porn that had finished downloading while I was at the AMP. Then I went to spend the night with my AMP mistress where before we went to sleep, I had her give me a blowjob and some deep rimming before she sucked and swallowed every last drop of my cum, though I have to admit I did not really squirt that much (normally she spits, and by normally, I mean she only swallowed my cum once before when I begged her to). Then we fell asleep.
Speaking of which, I want to add on that I had anal sex for the first time (it was also her first time) with my older AMP mistress during the month of December. Took a while and a lot of lube but once I got it in there, it felt good, but definitely not for her. She was trembling with fear and her face looked to be in a lot of pain.
I did not do a lot of thrusting as it was tight enough and just some wiggling was enough to get me off. Had anal sex with her just once more and some more of the same. This time I filmed it but she deleted it saying that everything looked good except her face since she was scared/hurting.
Oh well, next time.