Re-Post: Zen and the Art of Online Dating

Like many people in my generation, I met my husband through online dating. However, unlike many of my friends, I preferred online dating to meeting dates in person. The men I met online were carefully selected and vetted, unlike the ones I met in bars or at parties. I felt like I worked out the […]

via Love Notes: Zen and the Art of Online Dating — the syntax of things

A First Time Story

Shortly after my 16th birthday, my girlfriend of about 6 months invited me over for the day.

We had up until that time been sexually active in every way except for actual intercourse. We had traded pictures, I had fingered her, eaten her out, received head, as well as hand jobs but neither of us had really broached the subject of sex.

In retrospect I probably should have pushed the subject a little more, but in all honesty had been fine as long as I came. So it didn’t matter as long as she was the one to provide it, for it did heighten the experience to have another do it instead of oneself. I saw sex just as another form of this and nothing more.

Anyway the day I went over her mom was out at work and we had the place to ourselves, so naturally as we had done many times before we began playing truth or dare. Each dare getting a little bit raunchier. The excitement was building; each of us had been pushing our boundaries and feeling one another out. Finally she told me that she had wanted to have sex for awhile and had specifically chosen for me to come over that day because her mom was out. So we went into the bedroom, all of our earlier excitement and energy having faded we undressed, and got into bed.

She got on top of me, put a condom on, and pulled the covers over us. I slid in and we began slowly to rise up and down. She grimaced a bit and we took it slow; it ended up lasting about 10 minutes. I remember thinking I would rather get head than this as it provides a lot more pleasure; because it was so tight it hurt her so we went really slow.

But we ended up doing it a second and a third time and a fourth time and jesus christ did I like it after the initial hesitation.

—M.O, male, 21 years old

Personal Sexperience & Life Lessons

My first time wasn’t very glamorous. I was 15 years old and had been dating my boyfriend (we’ll call him Justin) for about a month. He was the first one to ever get past first base – in fact we rocketed from first base to third without much preamble. I liked him, I trusted him, but I didn’t love him. We had fun and we cared about each other, but I didn’t love him.

One day we were getting hot and heavy and our clothes ended up strewn all over the floor. He was hard, I was wet, and we were grinding against each other. Then somehow it just ended up inside me (I should mention here that I accidentally broke my hymen when I was 8 due to a gymnastics mishap). We both looked at each other, wide-eyed and unsure, before lust overcame us both and we just went with it.

I didn’t particularly enjoy it – I was caught up in how weird the sensation felt. Once Justin was spent inside me (we didn’t use a condom), we kind of lay there together not speaking. It wasn’t awkward or uncomfortable, we just had no idea what to say. We hadn’t discussed sex, nor had we planned for anything to happen. It was accidental sex.

I’d had opportunities before but they never seemed like ideal situations. I wasn’t someone who expected roses and candles for my first time, but I trusted my instincts. I wasn’t mad, sad, or upset in any way that my first time wasn’t special. I felt different afterward. It took me a good two days to really process what had happened, and get used to the idea of no longer being a virgin.

Now, with 20 years of hindsight, I have much more perspective on things.

I don’t regret dating Justin, nor do I regret that we were intimate. I do wish I had waited to have actual sex, because 6 months later I could have shared that gift with my first real love. Justin and I will always have that connection of being each other’s first. Although we remained friends on and off for another ten years, we are no longer in contact; I can’t help but wish I’d given that gift to someone special. It is an incredibly personal thing to give someone your virginity.

I’m also incredibly grateful that the lack of condom didn’t lead to pregnancy. I was VERY lucky in that regard.

Some people say giving yourself at any time is special, whether it’s the first or not. Some hold sex as a sacred thing to be shared only when truly in love. I’ve even met someone who couldn’t physically be with someone unless there were strong feelings between them. I personally don’t subscribe to that philosophy.

The best sex you can have is with someone you love, that much I won’t debate. Being able to fully trust someone and let go in a supportive environment makes everything that much more potent. Sex is at its finest when you know your partner is genuinely interested in pleasing you.

But you can still have a lot of fun without an emotional connection. It won’t be the same level of deep satisfaction – it may get you off, but it won’t fulfill you to the core. And sometimes that’s okay! I think having mediocre or less satisfying sex is good, in a way, because it helps us to appreciate the good stuff even more by comparison. And being able to fulfill your particularly lewd/kinky fantasies is immensely pleasurable. Most of us have a sexual bucketlist, and not all items can be fulfilled while in a relationship. Experimenting is great, expanding your horizons can be fun, and experience helps us fine tune our technique as we learn from others. Sex is awesome.

In the 20 years since Justin, I have had a full spectrum of amazing and horrifying experiences. I have learned a lot and tried many things, pushed my limits and pursued challenges. And I have gained a lot of perspective about sex, relationships, and everything in between.

Here is a list of conclusions I’ve drawn from my experiences:

  • Unless you know with absolute certainty that your relationship is monogamous without cheating, always use a condom. ALWAYS. STIs are common and very annoying. Most of them are easily treated but they’re a huge hassle. It’s a good idea to keep condoms with you at all times in case you need one.
  • NO MEANS NO. Never let someone talk you into something that makes you uncomfortable. If they try, get up and walk away. There are plenty of other people who will be respectful of your limits.
  • The best lovers are those who want to please you more than they want to be pleased. Someone who genuinely enjoys giving pleasure, and even gets off on doing it, is usually great at what they do. ALWAYS reciprocate the attention they give you.
  • Sex is only good when there’s communication. Don’t be afraid to say if something hurts, or if they’re doing it wrong. Talk about your needs, desires, and hot spots. Everyone is different and most people want to learn how to please you. If they’re unreceptive, walk away.
  • Similarly, let your partner know when they’re doing well. Moans and groans go a long way.
  • TRUST YOUR INSTINCTS. If a situation/person/activity makes you hesitate, then get out of it. Your subconscious brain can pick up on subtle cues that the conscious brain often ignores or minimizes. Your gut always knows best.
  • NEVER openly criticize someone’s body. You’re lucky you get to see it at all. If you think there’s something to be concerned about for health reasons, be tactful and respectful in mentioning it.
  • Try not to compare different partners. Everyone is unique and no two experiences, even with the same person, will be exactly alike. Comparisons don’t serve any purpose except to make us critical and judgemental.
  • Penis size matters a lot less than most people think. I’d rather be with a man who’s smaller but talented than with some hung idiot.
  • As long as they’re legal, safe, and consensual, explore your fetishes! Don’t feel guilty for having them – no one has to know but you and the person you play with.
  • The number of partners someone has had does not reflect who they are or their level of skill. Someone can have 100 partners under their belt and still be a terrible lover. Also, just because someone has had lots of partners, it doesn’t mean they don’t have standards. Numbers don’t really mean a whole lot in the bigger picture.
  • The brain is the largest erogenous zone. Example: I find a hearty philosophical debate more of a turn-on than dick pics. Stimulate the mind, then stimulate the body.
  • There are many different types of sex. Each has an appropriate time and place.
  • NEVER CHEAT ON YOUR PARTNER. They will always find out one way or another. The satisfaction you get from a night of passion isn’t worth the heartache you cause someone you care about. If you’re tempted to stray, sit down and figure out why that is. Cheating is often reflective of a deeper issue in the relationship, which isn’t necessarily about sex.
  • It’s a fact that you will be rejected far more than you will succeed; learn to shake it off.

Different Types of Relationships: An Analytical Approach


There are so many different ways to organize a relationship between two (or more) people. Each situation is unique, dynamic, and fluid, and will likely evolve over time. Here I have taken an analytical and generalized approach to relationships. In my mind there are two major types: romantic and sexual. Often they overlap, sometimes they don’t.

With all these different types of relationships, sometimes the line between faithfulness and cheating can get blurred. That usually happens when the rules/limits/expectations are not fully discussed ahead of time. Essentially cheating can be defined as any sexual contact which violates the parameters of the relationship, and it can happen in any arrangement.

I HIGHLY recommend an open and frank discussion about what’s allowed and what isn’t when engaging in a new relationship. Write it down if necessary, like a kind of contract, to minimize heartbreak. And don’t be afraid to revise the terms and conditions of this contract at any time.

Read on, and feel free to comment with any additions of your own!

Romantic/lifestyle relationships

The Default: Monogamy

When you’re a teenager and someone wants to be your boyfriend/girlfriend, there’s an undiscussed understanding that you will be in a monogamous relationship. That means no flirting, exchanging naughty pics, or engaging in sexual contact with anyone but your partner. It’s become the social default: unless otherwise specified, you are in a monogamous relationship with one person.


The Frowned-upon: Polygamy

Polygamy actually breaks down into two sub-categories: polygyny and polyandry. The first refers to a man who has multiple girlfriends/wives, while his partners are faithful to him. The second is the same thing for a woman with multiple husbands/boyfriends. Often these arrangements have some kind of religious context, but they can also be cultural. A sultan with a harem, for instance, is practicing a polygamous lifestyle.


The New: Polyamory

There are many different ways this sort of relationship can be arranged into multiple sub-categories. At its most fundamental level, polyamory is where each person has multiple monogamous partners with full disclosure. So person A has 3 boyfriends, and is only intimate with those three partners, and each partner knows about the other. These men may also have multiple partners of their own. This arrangement is not just about sex – it’s real intimacy between individuals at different times, kind of like a time share.

Usually combined with monogamy.


The Complicated: Triads et al.

Sometimes there are groups of people who co-habitate together and consider themselves all part of one relationship. This is usually limited to three people but in theory the number can be infinite. They may or may not have sexual contact all at the same time, but they are committed to each person equally.

Usually combined with monogamy. Can be combined with group sex.


The Hierarchy: Primary & Secondary

Some polyamorists categorize their relationships as “primary” and “secondary.” A woman who is married and living with her husband fulltime would consider that her primary relationship, while any others she engages in are considered secondary. It’s a way of prioritizing relationships; if she’s uncomfortable with being open about polyamory with outsiders, she can introduce her primary as her husband. It also minimizes complications with things like property ownership and children – generally things only shared between primaries. Despite the inherent hierarchy of the language of “primary” vs. “secondary,” each relationship is an emotional investment and has a lot of meaning attached to it.

Usually combined with monogamy.


The Challenging: Ethical Non-Monogamy

This is otherwise known as the “open relationship.” Like polyamory, this arrangement has a lot of variables to consider. There are dozens, if not hundreds of ways to personalize this type of relationship. At its core, essentially it means person A is involved with one person romantically, with potentially infinite casual hookups on the side. There is a clear compartmentalization of sex and emotions, with only their partner getting love and romance.

Can be combined with friends with benefits, fuck buddies, one night stands, swinging, power exchange, and group sex.



The Specialist: Power Exchange

I will not go into great detail about this type of relationship because it could have books written about this category alone. Suffice to say some people enjoy being dominant – that is, having power and control over the pleasure of others, while those who enjoy giving up control are submissive.

There are varying degrees of control one person can have/give up. Some go into it as a total lifestyle where every aspect of their lives is micromanaged by another – sexual, social, and financial. Most adopt this lifestyle only on weekends as an escape from their usual routine or to provide balance (those who are dominant in real life are often, though not always, sexually submissive).

It’s important to note that being dominant or submissive does not necessarily involve a romantic attachment, nor does it always involve whips and chains. Romantic attachment (ie: love and emotional fulfillment) can be present between a dom/sub, or the relationship can be strictly sexual in nature. Doms may choose to have only one sub at a time, or multiple, but subs typically only have one dom.

I will write more details about this in a later post since it’s a topic that deserves more attention.

Can be combined with any other category.

Sexual Relationships


The Uncommon: Cuckolds

This rare arrangement is largely sex-based. It’s where one partner, usually a man (called a cuck), allows his wife/girlfriend to have sexual contact with another man only while he watches. The outside man is called the “bull” and is usually chosen because he is very well endowed. There is no romantic attachment to the bull whatsoever. In some cases, the cuck is taunted and teased by either the bull or the wife for being an inadequate lover. This is all done with prior knowledge and consent of all parties.

Usually combined with power exchange and ethical non-monogamy, can be combined with friends with benefits, fuck buddies, or one night stands.


The Thrilling: Swinging

Swinging is actually a type of ethical non-monogamy where the only sexual contact outside the relationship takes place by both partners at the same time. Essentially this is where two couples swap partners for an evening of sexual contact, with full consent and knowledge of what the others are doing. They may or may not be in the same room but are usually in the same abode when this happens. This is becoming increasingly common as people try to spice up their sex lives while minimizing the potential for jealousy. Because the sexual activities are done together at the same time, some people consider this a monogamous arrangement.

Can be combined with monogamy, ethical non-monogamy, group sex, and power exchange.


The Coveted: Friends With Benefits

This is a very popular arrangement for many, as you get the best of many worlds: regular sex, great company, and no commitment. It is highly sought after by both sexes, as there are no limitations to the amount of FWB you can have at once. People who are practicing ethical non-monogamy may have FWB in addition to their committed partner, or FWB can be single and not looking for any attachments.

Can be combined with ethical non-monogamy and power exchange.


The Common: Fuck Buddies

Similar to Friends with Benefits, but lacking in friendship. Fuck buddies are just that: acquaintances who have sex every now and then. The relationship is entirely about physical pleasure. Whereas FWB may have a real friendship that is not entirely based on sex, where they can spend time together platonically, fuck buddies generally have no interest in spending time together outside the bedroom. Again, those practicing non-monogamy may have one or more fuck buddies in addition to FWB and one committed partner.

Can be combined with ethical non-monogamy and power exchange.


The Singular: One Night Stands

This is fairly self-explanatory. It’s one night of sex that does not result in a relationship, friendship, or any contact whatsoever. By definition it is an act performed between strangers or new acquaintances.

Can be combined with ethical non-monogamy and power exchange.


The Multiple: Group Sex

This is pretty straightforward: when three or more people are engaged in sexual activities at the same time, it’s considered group sex. This includes threesomes (three partners), orgies (four or more partners), gangbangs (one recipient with multiple givers), bukkake (multiple loads of ejaculate aimed at one person), and could even include swingers.

Can be combined with ethical non-monogamy and power exchange.