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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)

Harder! - part I

For the start of this chapter we’re going to have to go back in time to January, because that is when I first began chatting to a cute-bisexual-artist-student-Puerto-Rican-girl named Angelina[1]. We talked a bit about art and artists, and discussed the possibility of going to checkout MoMa together. She had messaged my normal profile, but her Okcupid personality-o-meter gave her a very strong ‘kinkiness’ rating, which seemed promising… so I gave her my number.

One Saturday morning I got a text:

"Hey, I'm on the train headed back to the city, what you doing?"

My afternoon was free so I agreed to meet up, but unable to decide what part of town we should rendezvous in I said that I'd come meet her outside Grand Central when her train arrived. I figured there must be somewhere good for a drink around there... "Let’s be spontaneous! :-)" I texted.

I waited by the front entrance to Grand Central station. There were an innumerable variety of travellers coming and going through the station’s doors. Unlike most public buildings that endure heavy foot traffic, this hub of American rail transport did not have efficient automatic door opening systems. It just had big heavy swinging wooden doors with shiny brass finishings that the Saturday travellers were having to battle with while towing their luggage.

Watching this war of Americans vs. doors provided sufficient entertainment while I waited for Angelina to arrive. The best bits were when two hapless folks would try and take on the same door simultaneously from both sides. They would then either neutralise each other’s efforts, or propel the door with unexpected velocity towards the individual who decided to pull... This all happened despite the presence of large windows through which the assault-on-door could be easily coordinated, if only they had a little more awareness. I could probably reflect for several more paragraphs on New York door etiquette (or lack thereof), and its implications for social decline. However we all have places to be and my date is meant to be turning up at some point in this story, so let’s get back to her.

After a couple of texts to confirm which door I was waiting by, Angelina appeared, walking across the street. She was shorter than I expected and her nose and lip piercings seemed to assume more prominence than they had in her profile photos. Perhaps they were enhanced in real life by her bad-ass leather jacket. Still, I thought it was a hot look.

"Hi! How’s it going?" I asked.

"Fine thanks," she said, while we hugged a greeting, "some homeless lady just told me I looked sexy... I always get come on to by homeless people for some reason."

"Ha, well I guess it's still a compliment. So do you feel like getting a drink somewhere?"

"Sure. Where's good around here?"

"I have no idea. This isn't a part of town I hang out in much. I'm sure we can find somewhere though. I figured we could give being spontaneous a try."

Sadly, as this date took place back in January, I did not have a smartphone on me as it was still somewhere in the postal system. Smart phones are very helpful to the process of being spontaneous as at the very least they give you suggestions for the best directions to be spontaneous in.

"Let’s try down there," I said, pointing to a street running alongside Grand Central, "I have a good feeling about that street!"

"Sure," she replied.

A few minutes later we were staring at blocks of lifeless concrete and glass that mostly comprised office and parking entrances and stretched off into the distance, devoid of all personality, and, more importantly, devoid of anywhere that looked like it might serve drinks.

"Well this is a shit street. Whose idea was it to come down here!" I said.

She laughed.

We retraced our steps a little way, then I said "Ok this is the last time I try being spontaneous… Erm... over there is a tacky looking Mexican place we could try?" I pointed.

"Do you think that just because I'm Hispanic you should take me to a Mexican place? Huh?" She said, in what I hoped was a joking tone.

"Ha, no just seems like the only place on this street that might serve beer! Shall we try it?"

"Whatever. I don't mind."

"Let’s take a look."

We entered the tacky Mexican place with neon margaritas in the window. The inside of the tacky Mexican place was also tacky. There were no other customers. We were immediately set upon by an enthusiastic waiter who hustled us into some seats and gave us menus before we could protest.

"So this place is... Erm... something?" I said

"Yeah, it seems pretty terrible," she said.

"Do you want to try somewhere else?"


While the waiter's back was turned, we put down the menus and scuttled for the door.

"Well, being spontaneous isn't working out as well as I'd hoped!" I said, even though the humour of that comment seemed exhausted.

"I know this place down by Union Square. Do you want to head down there?" She suggested.

I was more than happy to let her take control of this so-far-disastrous date.

"Sure," I replied.

A short subway ride later we were jostling through Union Square towards what turned out to be a less tacky Mexican place. Maintaining conversation on the way there came easily enough, even if it mostly consisted of complaining about New York.

This Mexican place didn't have waiters. You just ordered food from a counter, or drinks from the bar. Having got some guacamole and chips we sat at a two person table by the window.

"Shall we get something to drink?" I asked, gesturing towards the bar.

"Actually I'm not technically old enough to drink yet. I turn 21 in March."

"Oh shit, sorry! I forget how crazy this country is about that. The legal age is 18 in England[2]!"

"Yeah it's 18 in Puerto Rico too, which is why I don't have a fake ID, but I drink all the time though."

I'm not sure if I could get in trouble for writing about whether I bought beer for someone just under 21 in an anonymous dating book... but fortunately this is only a hypothetical question as I then purchased two non-alcoholic (but surprisingly beer like) beverages for us to drink instead.

We chatted over our drinks that totally weren't beer. I told her about my research and she talked about art school and print making. She found it frustrating not being able to just 'do her own thing', and believed that her art teacher had some kind of mild vendetta against her. I asked her what she liked to make prints of and she said a series of words that made no sense to me, then she clarified: "'s like they're about imagined historical situations, but that never actually happened... and sometimes combining fictional characters..."

"Uh huh... I've not heard of that," I replied.

"Like for example I'm working on this piece right now where Malcolm X is being tortured by Hannibal Lecter at the battle of Gettysburg. I can show you if you like."


She showed me a picture on her iPhone.

"Cool! That's interesting!" is what I said.

'My god that is comically terrible,' Is what I thought.

The picture consisted of squiggly lines that were barely recognisable as humans, let alone Hannibal Lecter or Malcolm X. However, despite never reading the dating rule book, I guessed that telling a date their artwork looks comically terrible is considered a faux pas... and maybe I just didn’t ‘get it’.

Some more rambling conversation later and we arrived at the topic of her piercings.

"Do you think my lip piercing is ugly?" she asked.

"No, not at all,” I said, staring at it, “although does it not get uncomfortable? Like, doesn't it catch it on your food? Or does it get in the way if you're kissing someone?"

"No, not at all."

"Fair enough. I don't think I'll get one though," I said, smiling.

“Do you have any tattoos?" she asked.

"No, although I wouldn't rule out getting one... I'm just not sure I could decide on anything I'd want to have permanently drawn on me. How about you?"

 "Yeah I've got a couple, there's this one..."

She pulled up her sleeve and showed me a wilted rose on her upper arm.

"...and this one..."

She tilted her head to show me a beetle hidden on the back of her neck under her hair.

"... and then there's a big one on my thigh that my tattoo artist friend is still working on. It's going to be of my old cat sitting on his favourite chair. Here I'll show you."

She shifted in her seat, presenting her thigh to me, and then raised her skirt up to a slightly scandalous height in order to show me the large half-finished picture of cat and chair. I resisted the urge to look around to see if we’d attracted anyone’s attention. It definitely would have been obvious that this girl was nearly showing me her ass in public.

Part of me hoped someone was looking.

After she lowered her skirt, a conversation about pets ensued. At some point I complained:

"There are so many people with annoyingly small ratty dogs in this city. They always seem to run out in front of my feet as if they're begging me to accidentally kick them!"

"Yeah sometimes I kick them deliberately," she said

"Wait… What?! Seriously?!"

"Well only like once... I was drunk!"

"Haha! That's... amazing?... If slightly scary..."

"I didn't kick it that hard... It was just in my way!... Although it did yelp a little though."

"Did its owner not get mad at you?"

"She was looking the other way, but she did give me an angry look afterwards. But whatever!"

"Wow... I'm glad I now know that you like to kick small dogs!" I said with a smile.

"I don't! Shut up. Whatever."

Weird as this date was, there was a pleasant transparency to it. As evidenced by her dog kicking story, Angelina had this unreserved honesty about her, combined with a certain amount of bad-ass aggression and perhaps some thinly veiled vulnerability; all of which made her easy to talk to. I told her about my occasional nausea attacks on dates, and the second sex profile I'd recently started on Okcupid. We related over our vaguely traumatic experiences in Catholic school and we discussed BDSM a bit as well, although we didn't go into our personal interests at that point. She also described an abusive relationship she had been in back in Puerto Rico. This seemed like a fairly amazing amount of sharing for a first date, but I found it hard not to respect her openness.

We both had friends in town to meet that evening, so as it started to get dark outside we agreed that it was probably time to head out. Angelina took the remaining chips and guacamole with us: "In case I can give them to some homeless guy," she said, and sure enough within a block there was some shabbily dressed chap sitting on the pavement who accepted her offering with an uninterruptable grunt.

We exchanged a firm hug by the union square subway stop, and then with a smile she disappeared down into the concrete guts of the city.

We stayed sporadically in touch after that, but the messages exchanged over the next month or so became a somewhat tricky balancing act for me... It was a balancing act in which I seemed to repeatedly fall off the tight rope, hit the net face first, and then give up completely... Only to find myself unexpectedly wobbling along the rope again.

However for details on that you'll have to wait until.... YOU CLICK HERE...

[1] This message came before I had even got laid in New York yet, but this is a story that played out slowly and reached its ‘conclusion’ shortly after I met Josie, so that’s why I am only telling it now.

[2] I also thought her Okcupid profile said she was older, but I decided not to say "Oh I thought you were older!" in case that sounded insulting somehow.