Greg is Dating

Once upon a time, I have forgotten where or when, I read a piece about the fate of blogs. It was half-humorously claiming that most blogs end up updated once every 6 months or so, and even this one post simply contains an apology from the blogger for not writing for so long and promises to update more frequently in the future. 

And that is where this blog has ended up. I realize I have dropped off the face of the earth lately, and the thought I have abandoned my writing and the handful of faithful readers I accumulated bothers me regularly. But, unlike what the introduction would suggest, I am not going to apologize for it, because the reason for my disappearance is an important one: I am happy.

For those of you who still remember my last few posts, I was describing how I started going out with the dance instructor from my gym, Andrea. Well, Andrea is now my girlfriend. After around 8 months with her, I can confidently say we are in a very good place in our relationship. We now see each other regularly, or at least as regularly as our busy lives and obligations will allow us (remember, Andrea has a 5-year old daughter to take care of, as well as holding down two jobs). We enjoy a lot of the same things, we love each other’s company, and I dare say that I have never felt so adulated, appreciated and well-looked after in any of my previous longer-term relationships. And then, there is the sex.

Last time I wrote about sex with Andrea, I had something like this to say:

“It would be great if I could now write that what followed was a night of unparalleled passion where we both fulfilled each other’s deepest fantasies. Alas, life does not always work like [that]…”

Except, sometimes it does. Nowadays, every night Andrea and I spend together is a night of unparalleled passion. Deepest fantasies are fulfilled left and right. I have no hesitation to say that sex with her is by far the best sexual experience of my life. What is even better, that last sentence wouldn’t even begin to describe what Andrea’s opinion is on the matter. Far be it from me to toot my own horn, so let’s just say that adjectives like “amazing”, “mind-blowing” and “breathtaking” are in regular use in my bedroom.

Not everything is perfect in our relationship of course. We still struggle to find all the time we would like to spend together. I have no issues with Andrea having a child, but this fact does create some problems, since her daughter’s father is still in the picture. And my status as a visitor in the USA means that at some point we will have to worry about what happens next: either we call it quits, or we will both have to make some very serious, life-altering decisions about our future.

But we try not to worry about crossing that bridge until we come to it. For now, we enjoy the time we have together and try to make the best of it. Most of the time, we seem to be managing pretty well. Which means that, after a year on a personal journey filled with new experiences, inward reflections, exciting adventures and bitter disappointments, Greg is no longer dating. I have found someone, and with her, some balance and respite. The cynic in me reminds me to treasure it. Who knows how long it will last?

When I started this blog, my main motivation was to vent my frustrations with dating. From that point of view, now that I am in a relationship and no longer dating, the reason for the existence of the blog has disappeared. Even though Greg is Dating has given me the right motivation to focus my energies on my writing (which is something I have always loved and was good at), there is nothing more to write about. At least, not here. Logically, this brings us to the end of this blog.

But not yet. Not quite. There are still stories left untold. Two stories that happened very shortly after I started seeing Andrea. So here we go. Two more stories to write. And boy, are they good!

Stay tuned.

(to read all about how I met Andrea, click here)

Two weeks after our salsa evening, I was getting ready to meet with Andrea again. Like the day of our first kiss, this was not a traditional date. Rather, Andrea had invited me on a night out with her colleagues and friends.

The venue was a large bar with pool tables and a huge dance floor. I arrived very early, and the bar was still almost empty, but Andrea was already there with one of her friends. At first, as is natural, there was a bit of nervousness between us after not seeing each other for two weeks. Several glasses of scotch and the constant stream of introductions because of the new arrivals to the group soon took care of that. As the evening progressed, more and more of Andrea’s colleagues kept showing up. I thought it was a bit curious that she had invited me out to such an event, but as I have since found out, this is simply Andrea’s way: she does not hide much from the people in her life, be they family, friends or colleagues. There was no effort to keep our growing infatuation with each other out of the public eye either; we kept touching and kissing throughout the evening.

              

But that was nothing compared to when we got up to dance. As one of Andrea’s friends later would describe it, “we were practically doing it on the dance floor”. She was right too, which is why after less than an hour of suggestive and titillating dancing, I leaned closer to Andrea and simply whispered in her ear: “Let’s go home”.

That was all the motivation Andrea needed. We stormed out of the bar, jumped in her car, and drove to my place as quickly as we could. Once there, our clothes disappeared in seconds and we were in bed before we knew it. Before our date, I had a pretty good sense that we would end up in bed, and Andrea expected so too. The anticipation, for both of us, was off the charts. But especially for Andrea. From her confessions to me in our previous meetings, and from what I had pieced together, she had barely had any sex for a year, and she had been fantasizing about us for quite a while.

It would be great if I could now write that what followed was a night of unparalleled passion where we both fulfilled each other’s deepest fantasies. Alas, life does not always work like in a romantic novel. Sometimes, you can know too much for your own good. My knowledge of Andrea’s anticipation and expectations; the whiskey I had inside me from earlier in the evening; my intimidation by the fact that I was in bed for the first time with such a fit and attractive woman; some deep seated insecurities caused by my debacle with Lily; all of this conspired against me. And as every man knows, once problems appear and you start worrying, things can only go downhill from there. To avoid beating around the bush: I didn’t really show up for the main event that night.

We did have sex in the end. Andrea was very understanding and helped me overcome my anxiety. She also did not seem to be disappointed at all; my guess is that she was already so into me that she was more than happy with spending the evening together and getting to the physical level of our relationship. But I was upset by my performance. Meeting expectations (either set by others or by myself) is something I take seriously. I felt like I had something to prove after that night.

Luckily, that was not the last time I saw Andrea. Not by a long shot.

(click here for the first part)

It was getting late. I was in bed in my hotel room. Texts were flying back and forth between Ruby and me. Of course, it wasn’t long before our exchange started heating up.

“I have to confess something. I am getting pretty turned on”, I wrote.

“You are late to the party then”, Ruby replied.

“I wish I was there with you. I would certainly show you a party”.

“Are you talking dirty to me Greg?”

“Ruby, when I talk dirty to you, you will know it!”

I kept pushing the boundaries. I’ve never done this before; certainly not with a girl I just met and never been intimate with. But this night, it didn’t seem to matter. I could do no wrong.

“I am so horny right now!”

I hesitated for a minute. This was an escalation point. Should I go for it?

“Are you touching yourself?”

Silence. For a few minutes I thought I went too far. Then:

“Maybe”

Another escalation. By now I was all in.

“Here’s what I want you to do then. Run your fingers on your lips, then rub your clit, and tell me how it feels”

Another silence.

“It feels good”

“That’s what I thought. By the way: NOW I am talking dirty to you.”

I proceeded to describe to Ruby what I would do to her next time I saw her.
I have no way of knowing of course, but based on her feedback she seemed to really enjoy it. She told me that she came hard that night.

We kept in touch for the remainder of my time away. And about a week later, it was finally time for our next date. I took Ruby to a speakeasy-style restaurant. The food was very good, and the drinks even better. All in all, a great time was had. After dinner, we took a walk and bought some ice-cream. But we both knew that this was just the first course of the date. We got in Ruby’s car, and drove around town for a while. After some temporary hesitation, Ruby drove us back to her place.

We had a quick walk around the house, but the anticipation was too great to resist for long. Soon, we were in bed undressing each other. Ruby is a quite attractive girl, with an exotic beauty due to her Vietnamese heritage, and since our first meeting we seemed to share an innate attraction. In addition, we had been looking forward to this moment for a few weeks by now. Things were getting very hot in her bedroom.

“Do you have condoms with you?”

“No. You don’t have any here?”

This was a face-palm moment. I should have brought some condoms with me of course, but in my defence, this was in the middle of the summer, I was only wearing a T-shirt and it’s difficult to carry much more than a phone, keys and some money in your pants’ pockets. I figured that either Ruby would have some condoms at home, or that we could just buy some on our way there, but I never got around to it.

Under the circumstances, I volunteered to go buy us some. I got dressed, borrowed Ruby’s car and drove to the nearest gas station. I made it back in under 20 minutes. It was late, and we were starting to feel tired, so we got straight to business.

We had sex twice before we both passed out. Four hours later, we woke up and had sex twice more, before starting our morning. I can say that I pleasantly surprised Ruby with my… performance, but no more than I surprised myself. I hadn’t had sex for a while, and Ruby really knew what she was doing, so I can only take partial credit for that night’s prowess.

I had been very excited about the way it was going with Ruby, and she seemed to also have a great interest in me, which I appreciated a lot. But sometimes, it is just not meant to be. The day after I spent the night with Ruby, I went out with Lady Dance. This was not exactly a date; she was out with friends, I was out with friends, we simply agreed to meet since we were going to the same place. But once there, things took a different and unexpected route and I ended up being completely smitten with her. But this is a story for another time.

I did not want to lead Ruby or anyone else on. I was planning to let her know that it was not going to work out between us as soon as I saw her next. I have to say, I was really not looking forward to it. We kept in touch as often as ever for another week. Then, she suddenly stopped texting. Maybe she sensed that something was wrong, or maybe she had her own reasons. I never found out. I felt like the right thing to do was to confront her and tell her the truth about what happened, but on the other hand it seemed to me that it would be cruel and stupid to contact her out of the blue and ask her to meet just to break up with her. As the days went by, I figured that if it was important enough for her she would get back to me, otherwise maybe she also had her reason for the break down of communication.

One last thing about Ruby: I more or less knew after our one night together that it wasn’t going to work out between us, because she was such a huge dog person. I have nothing against dogs, and I have realized some time ago that on the West Coast of the USA practically everybody and their mother owns a dog, so I’d better get used to it. But I do draw the line with dogs in the bed I am sleeping in. Ruby clearly often sleeps with her dog in her bed, and as a result the dog felt comfortable to jump into it, even while we were having sex. There are a lot of things I keep an open mind about when it comes to sex, but a dog licking me while I am doing it, is certainly not one of them. If I stayed with Ruby, it would have to be the dog or me, and I have a distinct feeling it wasn’t going to be the dog!

The summer, traveling and work have gotten in the way of my updates. That is how it is in August. Greg comes back today with a retro story. Enjoy.

I once got the girl by hitting her with a pebble. True story.

It was the first summer of the millennium, and I was chilling on a beach with friends. Felix was there. Gus was there. Michael was there. So were some others. We were all waiting for a buddy to meet us, and he was ridiculously late. When he finally arrived, he called us a few times to ask exactly where we were on the beach. We could see him standing just a few meters away, and we were waving at him, but he was still completely clueless as to where we were. Frustrated, I did something stupid: I picked up a small pebble and threw it at him. I missed him, but I did hit the kneecap of the girl that was with him and was standing behind him.

Pebble Girl was exactly my age; she had just graduated medical school, and she was the doctor of a remote health center in a small, seaside village, not too far from where we were enjoying the beach. Since “Pebble Girl” is a terrible nickname, let’s just agree to call her the Doctor, shall we? The Doctor was furious with me. For about 5 minutes that is, because somehow we soon hit it off, and spent the rest of the afternoon together in the sea or lounging on the beach.

    

I have to make this point here: the Doctor had the most. Amazing. Ass. Ever. I say this without much reservation, and knowing that it makes me sound like… well, an ass, but it’s just a fact: this girl had the best formed behind I have ever seen, and what’s more she knew it full well and was very proud of it.

The next week flew by, and when the weekend was almost upon us, my friends and I had a decision to make as to where we would spend it. I am going to give you one guess what my vote was for. Have you guessed it yet? That’s right, I twisted everybody’s arm and we decided on the same small, seaside village, where the Doctor was working.

We spent the day on a popular beach, and I texted the Doctor (who was on duty) that she could meet us there when she was done with work. Later in the afternoon, she showed up and it was painfully obvious to everyone that it was on between us. We couldn’t keep our hands off each other. On a couple of occasions, our friends told us to get a room. As it turned out, we never got around to that. On our way out of the beach, we started making out and we barely made it to my car. We got inside, the Doctor got on top of me, and our swimming gear disappeared in a flash. Another second later, I was inside her, and we were having sex for the first time right in the middle of the parking lot, which, I should add, was extremely busy at this time of the afternoon. So busy that we started to become a bit of a spectacle as more and more people were leaving the beach. This was a problem for the Doctor who was by her position a known member of the local community. She covered her face with her long, blond hair in embarrassment every time someone would walk by. But she never stopped, until she came.

And it went on from there. We spent the weekend in bed most of the time, except for a few breaks when we decided to visit a beach to take advantage of the summer sun and the sea. We picked remote beaches to avoid repeating the show of the first day. And we generally enjoyed each other’s company and bodies. I ended up staying an extra two days with the Doctor when my friends left, and they were good days.

But the non-stop sex, the unusual locations, and her perfect bottom are not even the things I remember most vividly about the Doctor. How do I put this? Well, to quote one of my favorite TV series: “Do you know how rare it is to find a girl who genuinely, honest to God, absolutely loves it up the arse?” (By the way, if you know the source of the quote, you are my new favorite person on the tumblrverse!). What I am trying to say is that the Doctor just loved anal.

Back then, I was relatively inexperienced, and I certainly had not even gotten close to having anal sex before. Despite my inexperience, the fact that she was into bum sex was clearer than daylight. My younger self wasn’t going to pass up the opportunity to try something new, and early on I broached the subject with the Doctor, who confirmed my impressions and guided me through my first experience with anal. We repeated it a few times in the following days, but obviously I didn’t really know what I was doing; I could tell that my performance left a lot to be desired. Nevertheless, thanks to the Doctor’s initiation, anal sex was added to my sexual awareness, and I have gotten much better at it since then.

I visited the Doctor two weeks later for another weekend of wanton sexual pleasures and frolicking on the beach and in the sea. Again, we had a great time together. The week after that, I returned to the UK, where I was living at the time. And that was it for this adventure. I never heard from the Doctor again.

In my blog, I tell the stories of my dating adventures. The key element is that these are my stories, from my point of view, influenced by my morality and my perception of reality. Invariably, I come off looking like the good guy (or so I hope). I am certain that if one were to ask the women that appear in my posts though, they would have a different story to tell. Still, I want to be as accurate, honest and truthful as possible when I write, and at the very least I know that I am trying to be a good and fair person, and treat people the way I would like to be treated myself.

This story is about the one time that I acted like a real dick.

We had just finished college, and my friends Felix and Gus and I were doing our best to enjoy ourselves. At the end of that summer, we knew that our paths would lead us apart. Felix and I were starting our post-graduate studies, him in the USA, and I in the UK. And Gus was off to the Czech Republic to study medicine. We were off for the weekend, just the three of us, to a remote village by the sea, where we rented a room at a bed and breakfast. We were hanging out in our room, relaxing, talking, laughing and slowly getting ready for our night out.

It was the summer, and it was very hot, so all doors and windows to the place were wide open. I had just taken a shower, and I was standing in the middle of our living room, with only a tiny towel rapped around my waste. That’s when the girls who were renting the room next door walked by on their way out. There were three of them, and it was as if they had just walked out of stereotype land: there was the sexy and mysterious one, who was dressed in black, the loud and sassy one, who was dressed in white, and the fat and silent one, who was dressed in a tent.

(I know, I know, that was terrible. I apologize profusely. But man, that girl was big…)

I don’t want to brag too much about this, but at the time I was in the best shape of my life. I have always been a fit person, but that summer I had all the free time in the world for exercising and taking care of myself, and I looked like it. Which was clearly what the girls thought, since they noticeably did a double take, walked past, then came back for more.

“Excuse us, boys”, asked the one in white, taking a few steps into our room “do you happen to know where people go for a drink in these parts?”.

Gus immediately took over. “There are a few places. But we were just on our way to the Red Mill. If you give us a few minutes, we could walk there together”.

They did give us a few minutes, I put on something more than a towel and on the way to the Red Mill we got introduced. The girls were a couple years younger than us, students at the same college as we were, and were also there for a short vacation after the term finals. The girl in white’s name was Bonita, and it was clear that I had caught her eye in particular. We had a few drinks with the next-door trio, but soon called it a night (we had to meet some friends somewhere else), arranging to meet the next day on the beach.

This is where this story interjects an older one: as it happens, that was the day I bumped into Cate on the beach. Cate invited me to a party that night, so I ended up ignoring Bonita and her friends. Of course, to my eternal amazement, this worked to my benefit. When I was finally back from the party, Bonita was all over me. Why are women always attracted to men who treat them terribly? (And why do I never learn from that? Damn my mother and her gentlemanly upbringing!).

Once we were back in the city, Bonita and I started dating on a regular basis. We were both off school, it was the summer, we were young… it was the perfect storm. We went out often, we had all kinds of fun, and it wasn’t long before we also started sleeping together. For me, sex with Bonita was great mainly for two reasons: first, she was a strange combination of being very into sex, but also very naive about it, which gave me a sense of both adventure and control. Second, she had huge breasts. That is such a guy thing to say, but bear with me for a second: I tend to go for the athletic type, which means that the women I sleep with are almost always small or flat chested. My point is, Bonita’s physique was a new experience for me.

As for her, she also seemed to be very much into our sexual activities, because, well… she only had crappy lovers before me, I guess. That’s the best explanation I have for some of the things she expressed enthusiasm about during sex, like the fact I would touch her clitoris (I don’t think my younger self really knew what to do with it back then, but yeah, at least I knew where it was. Sometimes reading loads of books does help!), or the experience of simultaneous orgasms (I remember thinking, “I’m 24! Most of the time I am trying really hard NOT to come! You could give me a countdown from 5 and I could come on cue, this shit is easy!”).

And this is where I acted like a dick. We were having a great time with Bonita, and pretty soon I could tell that she was developing feelings for me. But I might have neglected mentioning one crucial detail to her: I was moving to a different country in September. Which by now was less than a month away. I really have no excuse for what I did. In all honesty, when I met her I thought that if I told her about my impending departure, she wouldn’t sleep with me. And later it became too difficult to bring it up, so I didn’t. As we hang out more and more together, friends would bring this up casually in conversation, congratulating me or wishing me well. When Bonita would ask what they meant, I evaded or ignored the question. Finally, at a friend’s birthday party, the fact that I was leaving in 3 weeks sunk in for her. Bonita left the party in tears, and soon after I started freezing her out. I never really broke up with her, she just kind of blended into the background.

I know. Apparently, I was an asshole back then.

My relationship with Bonita was the first time I thought I might be any good in this sex business. Before her, I was either too inexperienced or too ignorant to even think about such things. But sleeping with Bonita made me think about how sex can be an amazing shared experience, and that one doesn’t need to be superhumanly talented or gifted to do it well, all it takes is caring about the other person and doing some basic things. I have been trying to be a good lover to my partner ever since.