Sex

How to: Casual Sex

My last post on relationships / cheating / communication was the most popular in the last five posts or so.  I know, you want juicy stuff as opposed to pictures of fantastic food (though I maintain that tasty food is one the great joys in this life.)  I think you’ll find that communication (and a lack thereof) remains a major theme in many of these posts as it directly affects the success of probably 90% of human social interaction.

It's tough.  He understands.

It’s tough. He understands.

Anyway, as you’ve read a few times now I’ve been single for right about eight years now (I’m literally within a week or so of the anniversary of the breakup.)  Post relationship I spent a lot of time focusing on myself and rebuilding, and then a few years later I started looking around for somebody who could be “the one”.  Well, the bad news is I haven’t found her yet.  The good news is I’ve gotten pretty good at this bachelor thing.  I’ve had a fair amount of forward movement professionally,  I’m improving my financial status daily, I’ve got some pretty strong bonds with friends of mine personally and (sometimes related) I’ve generally been pretty successful sexually (As in, women have regularly found me desirable enough to share themselves with me in that manner…)  So if I can’t have the one, this is a pretty awesome close second.

What blows my mind when I talk about this with some people is why they (or more often their “partners”) really suck at this casual sex thing.  It’s like they took something they saw in a movie and expected real life to be like that (thanks Hollywood.)  While I understand the male need to “alpha” (ugh) and the female desire to not be a “slut” (really ugh) you need to understand that those terms, and even those concepts are fucking ridiculous ideas created by insecure morons who were likely trying to manipulate you in order to keep you “in your place”.  Men must be physical, unrelenting, dominant, stupid cave men, and women must be weak, blindly dedicated, subservient nurturers.  Obviously… NO.    Now don’t get me wrong, this sort of role-play in the bedroom as playtime is all fine and well and healthy if that’s what you’re into, but as a standard of operation in the real world it’s narrow-minded and limiting for both genders.

So, whether you’re in-between serious relationships, getting a little on the side (legitimately.. or not..), indefinitely single by choice or you’re like me and are holding out for “the one”, here’s a few guideline “Dos and Do Nots” that have worked very well for me and I think are pretty universal (but is nowhere CLOSE to a complete list.)

First, DO:

Honesty at work.

Honesty at work.

1. Be Honest.  If there is one thing that will ruin a potentially good situation and make it ugly, it’s you spouting a bunch of bullshit.  It’s not “the game”.  It’s real adult life, so act like it.  Be straight up about what you want (and even how you want it…) in the beginning, even if it’s tough to let somebody who was hoping for more down.  It’s true, this might damage your chances of getting busy in the short term, but think of it as an investment.  The worst thing that happens is they respect you for being straight up with them and move on.  Sometimes though, they become friends, and sometimes that comes with benefits.  More than a few times I’ve been told I’m a good choice for that sort of thing because they know where I stand and don’t have to worry about complications.  Honesty keeps it simple.  When things are simple we can do our thing and get on with our lives.

2. Be Respectful.  This is huge.  Did you know that when somebody feels like you respect them, they are much more likely to let you see them naked?  It’s not rocket science.  This means eliminating words like “slut, whore, etc” from your dictionary as those are basically misogynistic double standards created to shame women (and albeit far less often, men.)  Newsflash: If you make people feel bad about being sexual, they are a lot less likely to be sexual with you.  This is ironic because people will often put down somebody’s sexual activity/history with others and then turn around and try to make something happen. You’re not going to make them feel okay about hooking up with you if you berate them for hooking up with others.

flirty-just-friends3. Be A Friend.  So a big part of functioning as a friend with benefits, is (wait for it) being an actual friend.  I’m not saying you need to pour your soul out to them and spend a bunch of time with them, but communicate, relate and hang out without any expectations periodically.  You’ll find some people become important to you and others stay very casual, but as long as there’s not false expectations, things stay pretty light.  When the benefits DO kick in, it depends on the person, but they might be wanting to play every time they see you anyway.  Sometimes that really IS the core of your “friendship” (gee darn.)  But the danger is in assuming.  So be cool, be a friend, keep it light, and fun.  The more fun and flirty (if accepted / appropriate) you are, the more likely at some point you’ll hit that moment when you know something is about to go down.

4. Be Patient.  If there is any one major secret to my sexual success, it is that I know when to be patient.  Often times people are not in the mindset / position to hook up (or, maybe just not hook up with you) when you first meet.  But that doesn’t mean they won’t always be. If you were honest (see step 1) and told them what you were about in regards to them, and then you were respectful (see step 2) then you will probably have some level of interaction with them on a friends basis (see step 3.)  So long as you’re not overbearing about it, if they thought of you sexually at some point in the past, odds are somewhere deep down it crosses their mind from time to time IF you’ve been fun and easy to be around.  Then if you’re lucky, they’ll let you know when they feel like acting on those thoughts.

Possibly overkill....

Possibly overkill….

5. Be Smart.  Sometimes I tell my friends stories of people I know that have literally slept with over a hundred people.  To this day they are healthy and happy and obviously know how to attract attention.  On the flip side I have personally witnessed somebody in a Frat House years ago who had been with probably five people in their life at most, hook up with three different people consecutively in a drunken rampage that didn’t appear to include protection.  That, to me, is a stupid, sad story.  (For the record, there was no visible rape involved… this person was literally seeking the people out and they were very happy to receive them…)  Point being, both sound pretty scary right?  Yes and no. There’s something to be said about numbers, as number of partners can indeed affect your chances of contracting an STI.  But the point of my example is that the first person knows what they are doing, is protected and communicates openly with their partners.  The second… not so much (obviously.)  Who’s the bigger risk for you to hook up with?  Call me traditional (see that whole friendship thing) but I kinda like to get to know my partners and even moreso communicate with them.  Does this mean I haven’t hooked up randomly at a party before…?  Well, no.  But I was protected and though I left the next morning, I left my information (which she was super surprised by), we became friends, had some great sex and her and I have hooked up a few times in between her boyfriends since then. Regardless my point is:  Learn about your potential partner by communicating with them, use protection, get tested.  It’s all fun and games until you start screwing around with somebody’s health (including your own.)

Next: DO NOT:

1. Have expectations.  This isn’t just about friends with benefits, this is about dating in general.  Numerous times have my friends told me the person they were out with made some offhanded remarks like “Oh man you’re going to be so amazing when we finally sleep together…”  What?!  I can’t even make up something that ridiculous.  Needless to say that sort of attitude is a very quick way to screw your chances (no pun intended…) and possibly damage the friendship.  Having expectations also leads to inevitable disappointment if they happen to not feel like hooking up at that point.  This can cause you act out in stupid ways and damage your chances in the future too.  So play it cool, show your interest (casually!) and don’t count on something happening the first, second or any time.  To be honest I’m not certain of the science behind it but I very often end up getting busy when I am pretty sure something won’t happen going into the evening for whatever reason.  It’s nice to be surprised!

What.. are.. you?!

What.. are.. you?!

2. Try too hard.  I’ve done it, you’ve done it, we’ve all gotten to the point where we got really really excited about a potential date/hookup/girlfriend/boyfriend/etc.  We got super nervous, put on too much smelly stuff, forced the conversation and likely drank entirely too much in the process.  Where did it get you?  Lot’s of places, but not in bed with the person you wanted.  Both genders have a sense for when the other is trying too hard, and it comes off as desperation, which in most cases is a huge turn-off.  Sometimes they may have totally planned to hook up with you, and the sort of erratic behavior that comes from nervousness and irritating passive-aggressive pushiness convinces them it might be a bad idea.  It’s good to seem interested, but keep your cool because desperation will scare most people off.    

Don't Judge. :D

Don’t Judge. 😀

3. Judge.  I’m going to be straight with you here, your opportunities for casual sexual encounters will come from all kinds of unexpected places (I mean.. they have websites for this stuff.. and no, for the record, I’ve never used Ashley Madison.)  Anyway, the point is regardless of circumstance, judging the other person for their choices will (obviously) screw up any chance you have of hooking up with them.  I’m not just talking about those fooling around on their spouse either.  You want to take the moral high ground?  That’s your business.  But otherwise people are in totally honest, open, polyamorous or even mostly monogamous relationships that might, for some reason with to include you and/or legitimately see you outside of it.  Maybe the idea of multiple people weirds you out? Well that’s fine!  But judging others about their activities outside of their involvement with you is not.  At the very least, it’s really hypocritical being that you’re trying to make yourself a part of those decisions.

4. Be Possessive.  This happens all the time, and women get the bad rap for it despite the fact then men very often get emotionally attached and fall into this trap.  “No Strings Attached” means no strings attached. (Like “no means no” with more words.)  Do not come into a situation claiming your ability to remain unattached and keep it casual and then expect it to magically change (thanks again Hollywood.)  If you begin to feel differently, you’re gonna have to talk about it.  The whole point of the benefits behind casual sex is that it’s casual.  You can get together, have a good time, maybe grab a bite to eat, and get on with your lives without having to take it with you.  It’s like going to the gym: you might be sore from it the next day, but otherwise it has no effect on your outside life other than making you feel better about things.  I realize that for some the emotional separation is difficult, and it’s easy to attach to somebody that is both a good friend and fantastic in the sack, but once you start feeling like you can tell them not to see anyone else, or go on dates, or even how often they need to see you, you’ve crossed the line from casual to trying to control them, and that’s not okay.  If you find this happening you need to talk about it, and it may be best if you downgrade to regular friendship.  If by chance you’re both wanting to take it to the next level?  That’s wonderful!  But very rare, so don’t hold your breath.

1332453942295_473877If you keep you head in the right place and your emotions in check, you can have a really great time and take care of those urges without hurting anyone.  I think that’s the best thing: when everyone knows what they want, they get it, and everyone walks away happy.  But this is only going to happen if you’re willing to be honest and communicate about your situations.

I could go on about this forever, I even considered dividing it into two posts.  But I liked how it flowed, and I felt it was related enough it warranted a long post.  Last week was the longest post yet until this one and it was very popular so perhaps you don’t mind a lot of words as long as I can keep it interesting (or maybe just sexy.)  Regardless, expect more on this, we’re just getting started.

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(In)fidelity

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Worth Reading!

I recently finished Paulo Coelho’s newest book titled “Adultery”. The subject is exactly as the title states and involves a woman’s journey from marriage to the temptations of an extra-marital affair and the ultimate resolution/consequences . I won’t give too many details as I don’t wish to spoil it for you, but I will say that thought the middle of the book got a little bit far-fetched, the overall story, thought processes and moral dilemma presented were solid and realistic. (Do note that “realistic “ is often not necessarily a happy ending.)

As you know, during my recent trip to my Seattle, I had the opportunity to discuss this (and many other) subjects with an old high school friend of mine, and contrast my lifestyle to hers. As a regular reader of my blog, she followed up with me and was interested in elaborating her views while asking me to write about mine. Since I really enjoy answering questions and providing feedback I ‘ll all to happy to oblige, especially because this is a subject that comes up a lot.

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You know who you are. Get on it!

My friend is the portrait of what many people see as the ideal relationship / marriage. She has been with her high school sweetheart for some seventeen years now and still very happy in her marriage. I haven’t seen or spoken to this man since high school, but he was good-natured and devoted to her then, so I have a feeling he is much the same now (judging especially from the photos and what-not I see on Facebook.) They have a house, two adorable children, and if they don’t have a white picket fence, I’m going to suggest she get one. Her marriage is one of two I can think of that have the chance to be that rare, older (not even “elderly” really) adorable couple celebrating their fiftieth anniversary.

At some point during our conversations in Seattle, my friend(s) and I got to talking about relationships and those that sometimes decide to include a third party (or more) in their sex life.  I’ve been involved in situations like that in the past (both as inviter and invitee) and I mentioned I’ve observed it bringing a new element into the bedroom and sometimes reviving a situation that may have become routine or mundane.  Later, my friend commented that she believed that if that happens with your partner, they may not be the right person for you.  She said: “I believe that when you are with the right person, sex should only get better and I don’t think that you need to add additional parties to make this happen.”  Further in the conversation she elaborated that every couple has problems, and the key was to attack those problems when they are small.  She gave an example of a friend of hers who is married but hasn’t had sex with her husband in (literally) years.  She hit the nail on the head when she said the solution was communication, and should’ve happened a long time ago.  The years (or even months barring medical conditions…) without sex are abnormal and destructive to the marriage.  I agreed that it was a total communication breakdown at it’s core, but where her and I may differ is that I actually believe that such communication is MORE important even than basic monogamy.

Wise man. (I can't believe that's a legit quote...)

Wise man. (I can’t believe that’s a legit quote…)

Allow me to explain: I often wish / fantasize about having the sort of situation that my friend has.  I won’t say everyone does, as times are changing and the “ideal” relationship can differ very much depending on the individual.  But many people (including me) still dream of finding “the one” on some level and living happily ever after.  However, finding that person is difficult and as my friend pointed out, even the  “perfect” marriage goes through dry spells and requires effort on both parties to continue to be a giving situation for both.  So, when things go wrong you encounter one of two scenarios:
 

1.  This is a problem we need to work out, but we’ll get past it and get stronger.

-or-

2.  One or both of us is no longer the right person for this relationship.  Either we weren’t from the beginning, or things have changed and instead of growing together, we have grown apart.

There’s nothing “wrong” with either of these situations.  Sometimes things simply are what they are and no amount of good faith effort will fix them.  But let’s focus on situation one, because once you’re in situation two, it’s just a matter of admitting and accepting it (which unfortunately can take a number of years anyway… and I can blog about that in the future…)

Cute/Funny but...

Cute/Funny but…


When a problem grows into an otherwise great, loving relationship, the vast majority of the time is the lack of honest communication.  When almost any issue is addressed straightforwardly, constructively and honestly, the majority of the time it can be resolved.  If they cannot, there’s a good chance you fall into situation two above.  VERY often I hear a primary issue of long-time couples is a stale or near nonexistent sex life.  I can tell you now that even as a 35 year old bachelor I don’t have the obsessive drive I had in my mid twenties, but I’m talking a couple of days off as opposed to weeks, months or years.  Why does this happen?  Routine? Insecurity? Too busy?  All of the above?  It happens because one or both parties is no longer excited about the prospect, it’s not longer turning them on.  Then, the situation becomes one-sided and turns into “work” instead of “play” for one or both parties.  Situations like this are what lead to people finding alternatives: Porn (individually.. and I’m not saying this is necessarily bad as it can excite one of both partners..) Toys (again, CAN be a good thing, all about how they are used…) and eventually other people (my friend doesn’t agree, but this can also end up a positive situation.)

The solution again is wide open communication.  But what get in the way is that people are afraid to tell their partners what they want.  After years, they worry about damaging their ego, being judged for something different they are craving, or coming across too needy or unreasonable for being wanted.  But I believe there’s nothing wrong with wanting something else or having expectations of your spouse on a sexual level.  If this is an ideal “forever” pairing, a partnership, both have to try to give the other what they need.  So many people are brought up on the outdated belief that love and sex have to be exclusive (and if that’s your preference more power to you), but it’s scientifically proven that this is simply not the case.  But instead of talking to their partner and being wide open about their deepest, darkest desires, they bottle it up, feel ashamed and tell themselves they are “wrong” for wanting these things. Then they try to pretend they are okay with the routine they have, but lying to yourself like that never ends well, and the all too common feeling of feeling “trapped” sets in.

Oh jesus.. THAT guy..

Oh jesus.. THAT guy..

One day, they come across somebody who is flirty and seems interested in them superficially.  Normally they probably wouldn’t even give the possibility a second thought, but two things come into play: 1. Human nature magnifies the feeling of wanting something when you feel you can’t have it (the initial desire has to be there first though.) and 2. Compared to their spouse, this person is not connected to their “real life” and is for all intents an purposes, a toy.  There is no marriage, no children and no responsibility to be an ideal spouse in this situation.  The opportunity arises to be fun, flirty, desired and greedy.  They get to demand what they want and if the person doesn’t like it, they are more or less discardable without issue.  The freedom is a huge turn-on, especially for somebody that has gotten into the habit of having to repress themselves.  I hate to bring Disney into this conversation, but this is the chance for them to “Let it go.”  Sometimes it’s a fling and nothing comes of it, others they are found out, or can’t handle the guilt and the world comes crashing down.  But it’s only a temporary solution either way, eventually the problem marriage still exists, or it’s been destroyed.

So, how do you avoid a situation like this?  I keep mentioning communication, but on a whole different level.  I’m talking about a soul-bearing, demon revealing, perverse, fucked up, this might hurt your feeling but you need to know this, holy shit this is scary but only you are worthy of this level of communication.  This is supposed to be your life partner, so you have to be willing to tell your deepest, darkest secrets and show them all the sides they signed up for before you end up feeling like you need to show that to somebody else.  Once the communication is on that level, you can figure out how to work it out (or not.  As it’s possible they simply can’t handle what you have to say, at which point I would be more likely to say you fall into option two above.)

Problem... solved?

Problem… solved?

Regardless sometimes that communication alone will solve the problem through new activities (red room anyone?)  But where I disagree with my friend I mentioned earlier though, is that when this communication takes place, it’s possible that another person, or even some other people might be discussed.  As far as I’m concerned, that’s ok.  It doesn’t necessarily mean you’re with the wrong person.  As long as the relationship has a totally open and honest level of communication, including potential feelings of pride, jealousy and inadequacy, and they are addressed respectfully with a constructive solution sought, then I don’t believe infidelity has occurred regardless of who does what with who.  The bond between two people who love each other is not merely based on the physical, and to say that somebody being involved with a different person negates a legendary bond of love is just ridiculous.  What matters is the trust.  If that is intact, so too should be the bond.

Oh son of a…

When I have these conversations, people try to flip it on me.  They say: “Well that’s very ideal, but what if the love of your life came to you and told you she wanted to be with somebody else sexually, or that she already had but she still loved you!  Could you really still be with her?”  Short answer: Yes, probably.  Longer answer:  If she had already done so, I would be pretty upset, pissed even to the point I might need some time.  But would I end it right away?  No.  I would try for the level of communication I mentioned above.  I would need to understand why she needed it, and what the solution was.  If I was satisfied with it, and I felt I could trust her based on that communication, I could stay.  In fact, once, a long time ago I already did.  But then many years later when I was similarly tested, I couldn’t open up and be that honest, I couldn’t bear my soul and make myself vulnerable, and so, I lost.  Rarely is it the actions that will kill a real relationship, but the reasons behind them that are locked away and never addressed.

When love and trust and that level of communication exist, I believe the right people for each other can overcome almost anything.  Then again, that’s awfully romantic of me… what do I know?