juliagarwood: Part II

Continued from Part I.

The Second Date

I showed up to the hotel with plenty of time to spare, and checked in. Somehow the reservation got messed up so that I wasn’t in the nicer room, they’d given me a standard one. I told the woman at the front desk that I thought I’d booked a nicer room, so she upgraded me on the spot. (I’m forgetting the terminology this hotel uses for “nicer” vs. “standard” rooms, so I’m just making it generic.) I went up to the room, dropped off my bag, and texted her to let her know I was there, so she could come any time. I then headed back down to the lobby, so I’d be there when she arrived.

I sat there for quite a while before she got there. (It was probably only around 15 minutes, but it felt longer¹⁵.) When she did arrive, she was wearing a brown coat over a short black dress (as we’d agreed beforehand). I obviously couldn’t see underneath it, but I knew that she’d be wearing a black bra and panties (as we’d agreed beforehand). I brought her to the front desk, so she could give them her license plate for the parking, and then we headed to the lounge for a drink (as we’d agreed beforehand).

Drinks

She looked good, very sexy, but she kept pulling down the bottom of her dress, in that way women have when they feel their dress or skirt is too short, and she confirmed verbally that, yes, it was too short for her taste. She’d promised to wear black for me, but when she’d looked in her closet that morning the only black dress she could find was this one, so she’d worn it. Frankly, it wasn’t that short, so I don’t think she needed to be self conscious, but her feelings about the dress were just a manifestation of a larger problem: she wasn’t comfortable in general. I did what I could to try and make her feel at ease, including a herculean effort to find the right level of physical contact, so that she’d have that comforting touch without getting spooked and running madly out the front door from me pawing her.

She kept commenting that, “This is weird!” And let’s be honest: she was right. Meeting someone you barely know at a hotel for the purpose of having sex with them is weird. I’m way more used to it than she was, so it wasn’t as weird for me as it was for her, but even I have to admit that it is weird. So she sipped her Long Island Iced Tea, and I sipped my white wine, and we made small talk in the lounge for a while as she tried to get used to the situation, before heading up to the room.

The Room

But we eventually did go upstairs, and on the way there we alternated between linking arms and holding hands (as we’d agreed beforehand). When we got there she looked around the room – as anyone would do, upon entering a hotel room for the first time – then she went out on the balcony to look around. She was obviously stalling, which was fine. We had hours together; we didn't need to rip our clothes off the second we entered the room. We stood on the balcony for a few minutes, with my arm around her, and enjoyed the view and talked about how “weird” it was, before heading back inside.

She sat on the bed, so I sat beside her and struggled with how far and how fast to push her. Do I start kissing her right away, and risk spooking her? Do I give her time and space to get used to things, and risk having nothing happen because she needs that final push? I think I got it about right, in that my initial caresses were more about providing comfort than about giving way to lust. However, as I have proven time and time again, once I start kissing a woman, it starts to get passionate very fast, and to my relief it happened in this case as well.

Making Out

The scene played out pretty much as I’d have expected it to. Kissing grew more passionate, clothing was discarded bit by bit, hands roamed. I don’t know if it makes me seem less manly, but to me the “making out” part of a meeting is almost as good as the sex – sometimes better. When I’m in sync with a woman and our kisses match each other in intensity, it’s otherworldly.

Before too long we were down to underthings, and I was sliding a finger into her pussy, continuing to kiss her all the while. My intent had been to stimulate her clit, but she wanted my finger inside her, so that’s where I went¹⁶. And then, to her surprise, a second finger followed, and I don’t think she was sure what to do about that.

It’s probably worth pausing here to note that she was a stereotypical Asian girl when it comes to sex¹⁷, in that her body simply didn’t know how to respond to pleasure, alternating between pushing me away because it’s too much and pulling me in for more. The reaction I sometimes see from Asian girls is one in which it’s hard to tell if they’re in the throes of an orgasm or crying out in pain and humiliation. (“Why would you do this to me? Please don’t stop doing this to me!!!”) So when I inserted a second finger, she initially reacted by trying to reject it (closing her legs and whatnot) – but only slightly more than she’d done when the first finger went in, and she was the one who wanted the first one there in the first place! So I decided to keep going, until she came.

Sex

There was a slight, almost-awkward pause at this point, as the rest of our clothes came off and we prepared ourselves for penile insertion¹⁸. The reason it was verging on awkward is that I was [over]-thinking it again: was she ready to take this final step? Up until this point she would have had reason to feel guilty, yes, but once we fucked there was no question left on the matter – no nuance, no way for her to get around it, no more loopholes: she would have cheated on her husband. Any thinking person would argue that she’d already cheated on him, by cumming on my fingers, by kissing me, by ever meeting me in the first place (even on our first date), by logging onto Ashley Madison and messaging men, but however many lines one chooses to draw, she was about to cross the one that anyone would call absolute. Even the most liberal definitions of faithfulness, which would have allowed kissing and making out and even oral sex, would have to admit that yes, fucking is cheating. So I hesitated a moment longer, giving her a chance to indicate that she wasn’t ready to go through with it

But she was, so I was soon inside her. (She had to guide me in. Sometimes, on rare occasions, I’m able to get myself in – just like a porn star! – but usually the woman needs to guide me, and this was one of those times¹⁹.)

I was having trouble gauging her reaction, so it was difficult to get in exactly the right rhythm. I think we fit together very well, and were quite compatible, but I also think she was on the verge a couple of times without ever crossing the precipice. (Or maybe she came over and over? Every woman looks, acts, and sounds different when she has an orgasm.)

Unfortunately, I was starting to get hot. As in literally hot, starting to sweat and whatnot. I’d started off by doing my best to make sure I didn’t cum before she did, I wanted to make sure she got off, but then I had to change my approach and go for it, and eventually I was… well, I wasn’t pushing rope, but I wasn’t as hard as I should have been, either. So I faked an orgasm (thank god for condoms), and enjoyed the “afterglow.” (Which wasn’t real afterglow, because I hadn’t cum, but it was still nice.)

She gently nudged me down below, and I eagerly took the hint, letting my tongue find and caress her clit. I worked a finger inside her, and then, like before, sent a second one in there after it. As before, she squirmed and tried to get away from that second finger; as before, I didn’t let her get away, and began to fuck her with both while keeping my tongue at work on her clit. I think she was expecting, again, that my tongue would snake inside her, but wasn’t counting on the clitoral stimulation. So she was getting unexpected pleasure on a number of fronts (two fingers instead of one, and a persistent pleasuring of her clit). As she would ride closer to the crest, she would often squirm in such a way that my tongue had to leave her clit, so I started to improvise by replacing it with my thumb, such that I had two fingers inside her pussy and the thumb on her clit, and it drove her wild. After a while I stopped even bothering to try and get my tongue in there, I just finger-fucked her and kissed and licked around her thighs.

Post-Coital… Bliss?

Once she’d climaxed for me, and I’d slowed my finger-fucking to bring her down gently, I eventually came back up beside her, to kiss and hold her and enjoy the post-coital intimacy that I love so much. She asked me how I was feeling, and I told her I was feeling quite good.

And then she started to cry.

I comforted her as best I could, but in reality there wasn’t much I could do other than hold her and stroke her hair and kiss her forehead. I initially assumed she was overcome with guilt, but no, she was sad because she couldn’t understand why her husband didn’t want this with her. Why did a near stranger want her so badly, and enjoy being in a bed kissing and cuddling her, when her husband didn’t? She had often told me that I always know the right thing to say, but in this case all I could say was, “I don’t know.”

She eventually stopped crying, of course, and we continued to talk, and enjoy the intimacy of lying naked in bed together, until we ended up making out some more, and the next thing I knew I was inside her for Round 2.

Round 2

This time there was no holding back, I wanted to cum, so I just fucked her this time and didn’t pay as much attention to trying to hold off for her sake. I don’t know if she came, but I definitely did²⁰. There was still time for cuddling, again, but not much, because it was getting time for her to go. We got cleaned up, and then spent a few more minutes in the room while she talked to her husband. I did my best not to listen, but I think he was trying to plan a vacation, and wanting her opinion on things.

She was kind enough to drive me to a subway station, which saved me having to get a taxi, and I was amused to find out that she’s… not a great driver. (Another Asian stereotype!)

So… What Now?

All of this took place on a Friday, and unfortunately I had a funeral on the Saturday, and then family stuff for the rest of the weekend, so I couldn’t text her much. We exchanged a few messages, but no long conversations. Just enough for her to tell me, Friday night, that she felt less guilty after she ate dinner. Considering that her level of guilt was of primary concern to me this was good to hear; considering that it didn’t make any sense (why would a full stomach make you feel less guilty?), my fears weren’t fully alleviated.

So when I got back to the office on Monday, with more time to chat, Job #1 was to determine how she felt. Was she feeling guilty? Would she want to continue seeing me? Would she want to just be friends? Unfortunately, her answer was less than effusive. She asked me how I felt, and I was happy to tell her. She asked me (in her own words) if I was pleased with her – especially whether I was pleased with her appearance, since she’s had two kids – and I was happy to tell her that yes, she’s sexy, she’s good in bed, and I was looking forward to seeing her again. (Hint! Hint!) She told me that she needed to think things through, to know how to articulate it.

Which she never really did. She didn’t ever articulate to me how she was feeling, whether she was interested (and/or able) to continue seeing me, or anything else. I probed her a couple of times on it – after a while it was more of a playful game than anything, because I’d stopped expecting a straightforward answer – but never any clarification.

On the other hand, her sense of humour was ramped up about 25%, and our conversations were much looser and more playful. All in all, it seemed like she was okay with the situation, and wanting more hotel time with me, she just didn’t want to explicitly state it.

The End

So the week had started out tentatively, and built fairly quickly to get almost back to normal. Maybe even better than normal, because her sense of humour seemed to have expanded, and our conversations were now much looser.

And then on Friday, right at the very end of the workday, she cried again. She had once again started querying me on why I was interested in seeing her, and did I really think she was pretty, and did I really enjoy talking to her? And I said… well, really, I said more of the usual. I told her once more that she was sexy, and told her once more that I wouldn’t be chatting with her if I didn’t enjoy chatting with her. And based on this, she told me that she’d shed some more tears, for the same reason she’d cried the previous Friday: Why wasn’t she able to get this kind of attention from her husband? Why could she get a stranger to tell her she’s sexy when her own husband wouldn’t²¹?

I had to leave shortly after that, and I didn’t talk to her on Saturday. I did, however, spend some time on A-M, because I’d been neglecting it, though I didn’t send out very many messages.

And then, late Saturday afternoon (I’m not sure what time), she removed me from her B-B-M list. Based on the nature of our communications, it’s all in her hands; I can’t re-add her to B-B-M, because I don’t have her PIN, and I can’t contact her on A-M because she removed her profile. If she ever wants to re-add me to B-B-M, hopefully she remembers my PIN; otherwise, we’re disconnected permanently. So once again, I’m left in the dark, not sure why a woman removed me from her life, and all I have are theories with no information as to which (if any) might be true:

• Did she get caught by her husband, and have to delete everything?
• Did she decide that this cheating thing is not for her, and that she had to end it for her own sake?
• Did she see that I was still active on A-M (through some other account she created), and get pissed off at me for “cheating” on her?
• Did she remove me accidentally (or have to reinstall B-B-M or reset her phone or something), and then immediately freak out that she’d lost contact with me and couldn’t get it back? Perhaps the email address where I’d sent her my B-B-M PIN got deleted along with her A-M account, and she couldn’t find it again?
• Did she just not enjoy being in bed with me, and couldn’t bring herself to say so?

If she ever connects with me again, I might find the answer to these questions. If she doesn’t, I’ll never have anything but theories. Some of the theories involve her losing contact by accident, and not being able to re-add me simply because she didn’t have my PIN, but if that was really the case, it was her own fault. A) for not keeping the thing written down somewhere, and B) for being so secretive in the first place – I have no way of finding her or getting back in touch, it’s all on her, so if she can’t re-initiate contact, then that’s it.

But if she purposely disconnected because she was pissed at me, then I guess she’s right where she wants to be.

Footnotes

• ¹⁵ Ever sat in a hotel lobby, waiting for a near stranger to show up, so you could have adulterous sex with them? It’s a long wait. Plus, every other man standing around in the lobby starts to look like her husband; what if he found out, somehow, and is waiting to find the man who’s banging his wife so he can shoot them both?!? ↺
• ¹⁶ It’s possible this was due to her inexperience. Some women don’t understand that clitoral stimulation is even more important than penetration, they’re too influenced by porn (and men’s preferences – which is what porn is based on). Later on, we’ll come back to clitoral stimulation... ↺
• ¹⁷ This is probably racist, but I’m leaving it in here. I’m hyper sensitive to racism, but on this one, it’s something I’ve noticed on numerous occasions. Let’s just chalk it up to conditioning: Asian girls are told to act like this during sex, so some of them do. ↺
• ¹⁸ I couldn’t help but phrase this in the least sexy way possible... ↺
• ¹⁹ I don’t know why I felt the need to include that overly intimate detail. Perhaps I just want to make my readers as uncomfortable as possible. ↺
• ²⁰ Not something to brag about, by any means, but given how things had played out the first time I was just happy to have gotten rid of some sperm... ↺
• ²¹ This is actually pretty straightforward human nature, but I didn’t say that to her. ↺