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Chapter 1: The Shy Boy


When my primary partner and I opened up our relationship and adopted a polyamorous lifestyle this year, we both joined an online dating site, OKCupid.

SIDENOTE: I’ll do a post about how and why we adopted this lifestyle at some point in the near future, but for now I am focussing on my most recent experiences.

Apart from the occasional “Nice boobs” and “How about some naked pics?” messages, I have actually met quite a few nice people through the site. One person in particular – let’s call him Scott – really caught my eye. His photos were appealing, but the conversation was remarkably stimulating, and as we began to converse with more frequency I gave him my Facebook address and then my cell phone number. Now this is not something I do very often, I would rather not every person I meet online have access to a bazillion photos of me, my family, friends and – many many of my cats – and all my personal information. But I felt a true friendship growing with Scott, and so I felt comfortable doing so. In fact, I have been using OKCupid for about 4 months now, and Scott is the only person I have given my Facebook and cell number to, so there was obviously something special I was seeing in him.

Scott, 2 years younger than me, started calling me his “Magic Eight Ball” because I was so open to talking about very personal subjects, and would answer his questions, such as “So do girls watch a lot of porn?” and other things relating to the workings of the female mind and sexuality. I am guessing most of the females he knows aren’t as open and forward as I am in talking about such things.

One morning he spoke of how he was feeling emotionally sensitive and fragile, as he had made out with and stayed over with a girl the night before (no sex, just cuddling: he made a point of telling me). He said he didn’t really have feelings for her, but that her friend had suggested he do it as it was her birthday, and now he wasn’t sure what was going to happen, as she is someone that he sees a lot through University. He also referred to his heart as being “made of chocolate”, referring to his sensitive nature. I realised as we had this conversation that I felt a twinge of jealousy towards this girl he had hooked up with, and realised how attracted I was to his online persona.

So I decided I wanted to travel to his city (about a 13 hour bus trip away) to meet him. (Let’s call this city: Place by the Sea). Due to studies and some personal issues my travel plans kept having to be pushed back. At one point I told him “It’s strange to be attracted to someone so much when you haven’t actually met them” to which he responded “I don’t know why you are, I think I must come accross as a sad and lonely boy.” This was the only time I spoke of being attracted to him, afraid of scaring him off. He lamented that he was only attracted to the most physically appealing girls, the “real stunners” as he put them, and that they all always have boyfriends.

Due to a whole huge heap of drama in the town where I live (there will most certainly be a post about this, The Great Fallout of September 2012, at a later stage), let’s call it Horribly Incestuous Town, and my own exhaustion from working on my half-thesis, I decided I needed to get the hell out of dodge, and decided this would be a perfect excuse to go and stay with my brother in Place by the Sea, unwind a bit, and most awesomely, meet Scott in person.

Scott seemed excited at the prospect of my arrival, offering to show me around his University and take me out to show me a few hangout spots. As I am finishing my degree at the end of this year, I have been considering moving to Place by the Sea, so he specifically offered to take me to some hangouts in the area I would be hoping to move to.

I arrived in Place by the Sea last week Wednesday evening, exhausted from a 13 hour trip, and not keen to do anything, so Scott and I agreed that we would hang out the next day. Unfortunately my brother lives on the opposite side of town, about a 40 minute drive from Scott. Neither of them were willing to make the drive, and since I don’t have a car or even a license for that matter (I know, I fail), we agreed to meet at a halfway point, where I was dropped off and Scott picked me up. I was actually a bit offended that Scott was unwilling to make the drive. I know that it’s a long way, but I mean, come on, I came 13 hours on a bus to meet him, put in a little effort here.


I had debated about what to wear for this meeting. I was hoping to look sexy, but not too “eager” so I opted for a tight fitting dress, but no cleavage, and a belt to give me an hour glass figure. It’s always difficult to know if someone will look like their photos, so I was hoping I would still find him attractive in real life. But I had no idea what would happen, as we had not talked about it really. We flirted all the time, but flirting and fucking are two very different things. I found a bookstore to wait in, lucky enough to find the fantasy novel I am currently reading on the shelf, and found somewhere to sit and read my book while I waited. I chose the book shop because I was hoping it would make me look 1. Smart and intellectual, and 2. Nonchalant: “Hey, look how un nervous I am about this meeting, I can just sit here relaxed and read a book”. It also meant he could see me first, and come over to me without me having to see him, which would avoid the awkward making eye contact and then walking towards eachother vibe, unsure of how long to maintain eye contact etc etc. So, yes, I put a lot of thought into the whole thing. I obviously wanted him to find me attractive.

I was extremely nervous sitting there actually, I could barely focus on my book, and I felt my legs going numb (this happens to me a lot for 2 reasons: Nerves and anxiety, and really good orgasms). Alas this numbness was due to the former. Anyway, the moment finally arrived and he wandered over to me and we finally met in person. I realised that my fears of him not being as attractive in person was totally unfounded as I discovered that he is actually unbelievably cute. I have always found the shy, smart type very attractive, you know the one, the shy smile, cute glasses. Well he certainly fit that archetype. Amazingly, it wasn’t at all awkward meeting, and as we went to his car and drove off to find a bar, we fell into conversation very easily.

I’m gonna skip ahead most of the evening out, because the juicy bits are what happened when we got to his place, but this is the basic summary: Lady Taylor went into Extreme Flirt Mode which involves the following: Lots of eye contact, lots of laughing, a little bit of casual bodily contact here and there which could be brushed off as accidental but could also be seen as purposeful, and an attempt to come across as both intelligent and funny. Those are the two attributes I find most attractive in others, so I try to come across that way myself. My look has often been described as a kind of sexy school teacher or librarian, and so I try to make the most of it. After the bar, he took me to a club where everyone wore lots of black and scowled a lot, and yet they were playing Katy Perry music, so the vibe was a bit confusing. I wasn’t sure yet if he was into me, so I decided to bite the bullet and do the unthinkable to most people: I just asked him. I know I am forward, I’m told I am all the time, and I know many people find that intimidating, but I would like to think that it means I am usually more likely to get what I want if people know what it is I want from them. So I said, “Are you attracted to me?”. He looked a bit stunned, and then smiled and said “Yes. Are you attracted to me?”. I nodded and said “Yes, very” and then before it could get awkward I went for it and kissed him. He had obviously shaved right before coming to meet me, his skin was smooth and he smelt amazing. I am extremely turned on by smell, and I instantly knew I wanted to fuck him. I had actually started to develop real feelings for the boy though, so that was also strongly influential. Not taking him for the sex in the bathroom type, I decided to restrain myself. We made out on and off in the corner, intermittently standing in long lines for drinks and chatting. After about an hour I decided it was time to leave and see what would happen…


Did I mention Scott still lives with his parents? Ahem. Yes. Yes he does. He has a section of the house to himself thankfully, but it attaches to an open plan kitchen they all share, so I started off whispering when we came in. He told me I didn’t need to, and I tried not to let the fact that his parents were so nearby bother me. To be honest, I was so horny at this point in time I didn’t really care. Scott has a small scruffy looking dog which hated me on site, clearly smelling my female pheremones, and my lust for her owner. I love animals, but I avoided her, not wanting to lose any digits. He went off somewhere in the rest of the house, so I took the opportunity to brush my teeth and change into my pajamas – yes, I had brought these in case I needed to stay over at his place because it was too far to drive me home, or for any other, more fun reasons 😛

He came back, and went into the bathroom to do the same, and when he emerged he said, “You can sleep in the spare room if you like, or if you want you can sleep here with me.”
I have no idea if he was really oblivious or trying to be gentlemanly and show me nothing was expected of me, but I just laughed and got into his bed…

To be continued…

In Chapter 1 part 2: The Sex, The Morning After and Oh God the Awkward.


Lady Taylor