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Harder! - Part II

After my first date with Angelina we exchanged a couple of messages. Apparently she somehow got the impression that I wasn't really into her, so I had to assure her that I was (even if she did like to kick small animals). I tried to arrange a second date, but I didn't get any further response.

Finally I got an instant message from her: "Can I see your kinky profile?"

"I thought you'd never ask! :)" I replied, and sent her the link.

She seemed to like what she saw, and some back and forth ensued. She told me that she had made her own flogger and asked if I wanted to see it. Of course I said yes. The texted picture of the flogger excited me. The fact that it was draped over her bare ass in the image definitely helped.

Trying to arrange a second date still proved a challenge though. Many of my messages went unanswered for long periods, and I may have overdone the sex banter to try and attract her attention. After describing how I’d like to have her chained to my bed so I could work multiple orgasms out of her with my hands, she accused me of regarding her as an object and said she was reluctant to meet because she didn't think I respected her. Slightly perplexed by the change in tone, I assured her I did respect her, and I thought I was just playing the part I was supposed to play in the game I thought we were playing…

Confused and frustrated, I gave up the chase. Then a month or so later I got a message from her out of the blue. "Hey" it read. Not much to go on there so I ignored it. A while later I got a wordier message and we started talking again, but now the roles were reversed and she was pushing to meet me.

Eventually a Saturday came around when we were both free and a second date was set. Well, except it turned out she wasn't quite free. She actually had some friends in town but wanted me to come meet her anyway. It was never really clear to me what her plan was, but we found ourselves at the same union square Mexican place where we landed on our first date. She still had a friend with her but I thought I did a good job of dealing with this extra company and engaged them both in friendly conversation. Her friend then pointed out that Angelina and I were both being really awkward, and that we should stop being awkward.

Angelina informed me she had been out of touch partly because she had been busy dating a couple. She didn't seem to rate the experience positively, reporting that it had gotten weird when the guy seemed to be more into her than he was into his girlfriend. I didn't get a clear impression of what the couple was actually like from Angelina's polarized statements, but reportedly the guy was a muscle bound sports obsessed douche, and the girl was a psycho control freak.

Having successfully sowed discord in that relationship, Angelina had abandoned ship and now found herself back on the singles wagon, hanging out with me... and her friend.

"You look different to when I last saw you," she said.

"Really?" I guess I've had a haircut at some point.

"Do you think I look different?"

"Not really."

"You don't think that I look fat? I've put on a bit of weight."

I do not follow many rules when it comes to talking to women, but one I try to stick by solidly is to never ever ever be drawn into a conversation about their weight. That way madness lies. Talking about weight and body shape in the abstract is dangerous enough, but a conversation with someone about their actual body can quickly become a lose-lose situation. If you offer too much reassurance you risk sounding insincere and they might get angry at you. If you don't offer enough reassurance then they might think that you secretly think they're fat, and get angry at you. It's like walking along a knife edge, which actually is a knife edge. You can't stand on a knife edge. You'll just end up being like: "Ow! Why do my feet hurt?!... Ow! Why am I now cut in half?!"

It is possible that some part of my brain had already observed that Angelina looked a tiny bit sturdier than she did when we first met, but not in a way that had compromised her looks. My brain had filed this observation under “information not to bring up at any cost, even if asked about it directly”.

"No, you look good," I said, "you've dyed your hair right? It looks redder."

See what I did there? See how I masterfully deflected the conversation at a critical moment to avoid a spiral into doom and despair? I know. I'm quite surprised at how suavely I pulled that off.

The three of us had been making what I thought was perfectly natural conversation for a while, but eventually her friend decided it was too unbearably awkward, and she left to go and catch up with her other friends who were in town.

Tiring of our Mexican locale Angelina and I wandered south into Greenwich Village. Now she was over 21, I used my lovely smart phone to guide us to a cool hipsterish place called V-bar south of Washington Square Park. A guy with a dense frizzy beard served Angelina a glass of red wine and myself a hoppy beer. We sat at the bar. After chatting about her friends a little bit Angelina turned to me and asked: "Am I freaking you out?"

"No. Why?" I said. This question confused me, I imagine I pulled a confused expression in response. Apparently this looked like a freaked out face.

"You look freaked out. I'm freaking you out aren't I?"

"No.… I’m good.”

"You just look like you can't deal with this crazy bitch you're on a date with."

"Errr, no. That’s not what I'm thinking, though I'm not really sure how to deal with this particular conversation. What makes me look freaked out?"

"You just look nervous… like I'm making you nervous."

"No I don't feel nervous. I mean I don't feel like throwing up, which is normally a good indicator of when I’m nervous!"

"Still, I think you're a bit freaked out by me..."

If my confused face still looked like a freaked out face, then it probably wasn't reassuring her at that point.

"Well I'm not, but I don't know how I can demonstrate that to you"

"I don't know," she said.

There was a pause.

An idea occurred to me.

"Actually, I have an idea," I said, putting down my beer.

I leaned out of my bar stool towards her, ran my hand up through her hair, and bringing her head towards mine I kissed her. Angelina didn’t hold back engulfing my face in her lips, and somewhere behind the bar I got the feeling that a beard was judging me.

'Well that seemed to do the trick!' I thought. ‘Thank god she’s finally shut up about how I’m freaked out by her.’

We spent a while longer in that bar and Angelina said that some of her friends might come and join us, so we found some space at one of the tables. It began to get busy and loud. Kissing Angelina occasionally seemed to do a good job of keeping any awkward conversations at bay, and we chatted about hopes/dreams/TV/movies/art/dating/family/etc. After a couple of drinks it seemed like her friends weren't going to show up and that maybe I should be moving this date along somehow.

"Do you want to get another drink here? Or I have wine back at my place if your friends aren't coming?"

"Would you have me in your place?" she asked, sounding surprisingly sincere.

"Of course! Why wouldn’t I?" I replied.

We walked back through Washington Square Park. Evening had not yet become night and various dark figures were still moving around its curving paths. Sometimes they were silhouetted against the park's great marble arch, which was lit up like the grand white doorway of a giant invisible house.


Not long after we had got into my apartment and I had handed Angelina a glass of wine she asked:

"Do you mind if I take my pants off?"

"No, that's fine by me!"

"I just feel more comfortable without them on."


It seems like a good sign when your date is taking their pants off of their own accord…

(To be concluded HERE)

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