I was recently SnapChatting with a friend and former colleague of mine when the subject of sex came up. The fact that the conversation went that direction is not really much of a surprise. She and I have a flirtatious history and many people (including us) thought that we would hook up at some point. But, alas, circumstances never really matched up for us bang but we remain good friends (and still occasionally sext).
As we discussed whether we would eventually hook up (I think it is likely) we talked about whether it would be good or not and, in particular, what would happen to our friendship if the sex was bad. I don’t think it would be bad… we are both friendly, generous, fun-loving people… but if it was bad I don’t think that would be a big deal. A bad sexual experience is something that we would just laugh about because our self-confidence isn’t based on something with so many unknown variables like a great sexual experience. A friendship that can’t handle bad sex or the awkwardness that comes from getting naked together isn’t a very strong friendship.
Besides, it probably wouldn’t be bad. Realistically, I don’t think it would be mind-blowingly great either. People (at least in my experience) are generally kind of awkward and weird the first time they hook up. There is an excitement in exploring a new body and new sensations, but there is also a lack of knowledge about what will pleasure the person. There is a learning curve that doesn’t exist with a regular partner. I think sex with my partner is amazing and I wouldn’t trade it for a new experience (luckily, I don’t have to) but new experiences also bring variety and a fresh perspective.
The truth is, if/when she and I hook up it’ll probably be “pretty good”. Our minds tend to live in extremes, everything will be absolutely terrible or absolutely wonderful, but reality is kind of mediocre. We put special events like sex, weddings, and vacations on this pedestal that can’t help but be a bit of a letdown when our fantasies collide with reality. And we assume certain terrible things will destroy our lives, whether that be the death of a family member, losing your job, becoming paralyzed, etc. but we actually recover quickly if we allow ourselves too. That is part of why I have found so much strength in mindfulness meditation and the Stoic philosophy, they allow me to live in the moment and see reality for what it is, and to only worry about what is under my control.
But, maybe the sex would suck. Maybe it would be terrible. Maybe neither of us feel a lick of pleasure or joy or satisfaction. Instead, we fumble around uncomfortably and lose all sexual desire for each other. Well, that would be okay. She is a dear friend and I’m not keeping in touch with her as a sort of investment where I expect sex later. Nobody is a sexual Roth IRA that you plug time into monthly and expect to withdraw an orgasmic payoff down the road. If the sex is bad, we will laugh about it, drink a beer, and go about our lives with one less thing to be curious about. It is better to have a few bad experiences than spend your short life wondering “what if”.
Hey! I’m always looking for things to write about. Have you got a question or comment for me? Feel free to submit anonymously to my SurveyMonkey (www.surveymonkey.com/r/XYRDXHH). No subject is off limits (just see some of my previous questions here to get a feel for what people ask about… it is mostly sex)
This post is in response to anonymous questions and comments that I receive via a SurveyMonkey form I set up. If you’d like to send me a question or comment just fill out the form at this website (www.surveymonkey.com/r/XYRDXHH). I’m sorry for the delay on some of these, I received more responses than I expected and am answering as quickly as I can (without burning myself out). If you are willing to give up the anonymity and provide contact information then I will respond directly to you before (or instead of) blogging.
- What are your top three pet peeve things people say to you? (I want to know how to not piss you off)
To be honest, this was actually a really difficult question for me and I never really came up with three things that people say to me. Being late is a pet peeve of mine, but I usually am more annoyed when I’m late than when other people are late.
It does frustrate me when people give me unsolicited advice publicly, particularly when it comes to nutrition and exercise. When people comment on an Instagram photo or a news article with advice for me it feels disingenuous, instead of trying to help me it feels like they are just trying to brag about their knowledge. I also feel like people are that I’m stupid or something when they do this (I admit that my perception is my own fault, but isn’t that what all pet peeves are? A reflection of our own issues?). I’d much rather someone contact me privately with a bit of humbleness instead of slinging advice around that I didn’t ask for.
I also really hate when people don’t give each other a little respect during discussions or debates. It seems all too often that people assume their opponents are dumb or naïve or haven’t thought their position through. Both sides of every argument spend all their time attacking what they perceive their opponents to believe instead of actually listening to what someone believes. I’ve come to believe that most people are doing the best they can, that I would probably see the world the way they do if I had a similar life experience as them, and every issue is incredibly complex.
I know it is easier to say, “Abortion is murder!” than to say, “I believe abortion is a complex issue. Not only do we need to determine when a fetus gains human rights, but we need to determine if those rights take precedence over the rights of the mother. Each situation is likely very different and nuanced and we should treat this issue with love and compassion.” (All sides of the political spectrum do this, we dehumanize and simplify our opponents while pretending we have the moral and intellectually superior position)
So… that didn’t really answer your question ☹
- When having a sexual experience with more than one person, what’s been the most awkward situation? What’s been the most fun situation?
Hmm, I’m not sure if this is asking for specific stories or just generalizations. I’ll answer both I guess.
Awkward: My first threesome was pretty awkward. Actually, “terrible” would be a better word than “awkward”, but there was certainly some awkwardness involved. It was with a college friend of mine and a woman he knew. We all knew that the threesome was going to happen, which was kind of rare (see below). It started out just fine, but throughout the whole thing my friend (who was a guy) was being very vocal in kind of an awkward way. He kept saying, “Yeah! Fuck my best friend!!” and similar stuff. It was kind of uncomfortable for me to hear that type of verbalization, especially since I wasn’t his best friend. We were buddies, but it really wasn’t a close friendship. Then, at one point I was having sex with her doggy style while she was going down on him and she threw up on him. She cleaned up and we kept going (probably a mistake), then when she was going down on me and having sex with him she shit all over him. At that point, I exited the situation and spent a good part of the night hiding under blankets on the couch re-evaluating my views on sex. I almost became monogamous that night.
As far as general awkwardness goes, I think the lead up to the event is the most awkward part. It would be nice if we lived in a society where you could say, “Hey, you two are attractive, do you want to fool around?” and nobody would get offended or anything by the question or the answer. But, we don’t live in a society like that. We kind of dance around asking for anything sexual, especially if it doesn’t fall into a very narrow definition of what is acceptable. The world is filled with missed orgasms and experiences. because sex is such a taboo subject. (Related: I would much, much, much rather someone ask my partner and I if they want to hook up than not ask us out of a concern that we will think they are freaks or something. There are many reasons why we might say no, but there are many reasons why we would say yes too. There is literally nothing sexual involving consenting adults that you could ask us that would be offensive or make us think less of you.)
Fun: Figuring out a specific fun situation is a little bit difficult. I’ve had a few experiences that stand out but ranking them is difficult. I guess I would say a threesome at a festival would be classified as the most fun. It was just a grand time of people exploring each other’s bodies, laughing, and learning from each other. That actually kind of sums up the parts about having more partners that is the most fun, you get to get lost in the moment and introducing new people brings about surprises. It is so easy to become sexually efficient with our partners, we know how to use our hands, mouths, and other body parts to bring the most pleasure is the quickest time. That is awesome, but it can also lead to ruts. Familiarity leads to boredom.
When you bring in new people they have moves and tools and preferences that they default to that may not be something you have thought about before. I think that is why I really love having new sexual experiences, it isn’t about being horny, it is about my insatiable curiosity. Seeing new areolas, tasting new genitals, spanking new asses, watching others bang is just a lot of fun. Sex doesn’t need to be taken any more seriously than that. Some of the most fun I’ve had didn’t even involve me touching people other than my partner, just being in the same room with your friends while they are enjoying each other is a blast. I think same-room sex with others is something more people should explore and can really cement friendships. Hell, at this point I don’t even need to be super attracted to someone to be curious about those things and have a desire to experience the unique desires and techniques that they bring to the bedroom. Sometimes sexual stimulation isn’t about sex, it is about exploration, friendship, and living in the moment.
3. Did you enjoy working for SFL (Students For Liberty) or did it get on your nerves a lot?
I loved working for SFL and I would probably still work for them today (or maybe somewhere similar in the liberty movement) if they weren’t based out of Washington DC. I loved SFL, I hated DC. I don’t know if I would feel the same way about SFL now though. This is going to make me sound old and bitter but, back in my day SFL only had three staff members and we were crammed in a tiny office in the Cato Annex. We hosted about 10 conferences a year and the CC class was only 28 people. We slept in airports and on dorm floors, we couldn’t afford staff computers, and our pay was low… but there was a purity of mission about it. We worked our butts off and reached to the left and the right to forge alliances. It was difficult and exhausting, but we didn’t worry about donors or money or get into squabbles about stupid shit. We focused on getting resources to the students, and that was about it. I don’t know if SFL has changed much since I left in 2012, to be honest I kind of stopped paying attention after I received hateful emails from “friends” when I voiced some of my concerns to the Executive Board. I realized that if they are unwilling to even have a conversation then it was time for me to move on. I look fondly at my time at SFL, but it is part of my past and I don’t see that changing.
That’s it for today, if you have a question or comment, please fill out this form 🙂