Oh, Benjamin.

May 6, 2013 12:49 PM

"And here's to you, Mrs. Robinson..."Can you help me become a more effective sexual mentor?

We are an early thirties woman and twenty-something man forging ahead into a casual sexual relationship under the explicit understanding that the much more sexually experienced woman would help guide a shy guy with limited sexual experience (not a virgin, just a few partners). Absolutely no strings attached, however great conversation has already taken place and one night together thus far, so far so good, we're very comfortable with each other as two human beings.

We've talked about giving feedback (during and afterwards), things we'd both like to explore, STIs/protection, etc. but I've searched far and wide for information helping me be a better teacher, no luck with the web or Dan Savagesque resources. The basic premise of this project being more experience for him with what he likes and what a woman (n=1) likes, increased confidence in his performance and well, a mutually satisfying continued sexual relationship for both of us.

I realize this is very broad, but how can I take on this role more effectively? I'm super excited about it, and would love to learn how to be good at this kind of mentoring.

posted by anonymous to Human Relations (10 answers total)

Praise on the spot, criticize later (obviously, not counting if he's hurting you (and you're not into that)). And rather than saying, "You did this wrong," tell him, "[That] had [effect], which I suspect/hope you were not going for. Perhaps if you were to try [this] instead."
posted by Etrigan at 12:55 PM on May 6, 2013 [3 favorites]

Oh, and also, don't be afraid to stretch your boundaries during this tutelage. In your early 30s, there is a distinct chance that A) you've not done everything that anyone finds hawt, or 2) he would be better at things you haven't previously enjoyed than the people with whom you didn't enjoy them.
posted by Etrigan at 1:01 PM on May 6, 2013 [2 favorites]

Although I can't suggest any specific techniques to use to achieve this, I'd think the most useful thing you can help him learn is how to be comfortable talking about what he and you both like *in the moment* in a way that doesn't feel awkward or that breaks the flow or pulls one of you too far out of that moment.

(I was thinking about this just last night, and how a former partner and I never seemed to figure out how to communicate in such a way that I didn't feel like I needed to completely leave my body and engage the analytical part of my brain so that I could give him specific feedback; when I did, and he would try something else that sometimes wasn't quite it, I could see/feel his problem-solver brain take over and sex became more about following a set of directions to achieve a desired end state - and frustration if that didn't happen - rather than just a flowing experience that allowed for physical, verbal, mental and emotional to all cruise along together happily.)

I wish I knew how to tell you the right words/tone/approach to use but I don't; if I did I might still be hooked up with this other guy... Good luck!
posted by hapax_legomenon at 1:20 PM on May 6, 2013 [1 favorite]

Oh, and also, don't be afraid to stretch your boundaries during this tutelage.

Yea, this. I'm in my late 30s and when faced with a similar situation, was surprised at how very little it felt like The Graduate. We were on mostly equal footing, as it turns out, for the reasons that Etrigan mentions and more. We are learning alot together, through good communication and consideration for each other.
posted by cabingirl at 1:52 PM on May 6, 2013 [2 favorites]

The copy cat game is great for teaching how to kiss, for instance. Another game is taking turns asking, "where do you want to be touched?"

In any event, the take away lesson needs to be with regards to the interaction and not to the mechanics. Every woman is different, so your tutelage, while saintly and incredibly hot, is only applicable to young Benjamin's future if he learns the meta lesson about communication instead of the direct lesson, "What does Mrs. Robinson like?"

A trip to one of those couple friendly pleasure shops may be in order. Letting him watch you take care of yourself and vice versa is another good mind opener. I don't have much else to say because you don't point out if Benjamin has any particular areas of growth. Heck, I'm in my 30s and have had the same number if parners as this young fellow. Odds are pretty good that the tutelege is just a handy, dandy excuse to get it on for him -- and more power to that, because, in my humble opinion, all relationships should be framed under the question, "what can I learn from and grow on here?"

Oh yeah, the in's and outs of emergency contraception and what to do when Plan A fails are always a good chat to have.
posted by Skwirl at 1:56 PM on May 6, 2013 [1 favorite]

In any event, the take away lesson needs to be with regards to the interaction and not to the mechanics. Every woman is different, so your tutelage is only applicable to young Benjamin's future if he learns the meta lesson about communication instead of the direct lesson, "What does Mrs. Robinson like?"

I think this is a very important point. At several points in my life, I've been in social circles where several friends have dated the same person at different times. It's been shockingly common for one friend to say that they had a great sex life with that person, while the other friend will say that it was terrible for them and didn't work at all.
posted by cairdeas at 2:12 PM on May 6, 2013 [3 favorites]

You could get books like "Joy of sex" and "More joy of sex" and read them together. Some things that will be meaningful to him will be things you didn't think of as significant. You have more experience. Just spending time together, talking, and being intimate will expose him to new knowledge and attitudes. For me, time spent with older men was valuable more for soaking up their more relaxed sexual attitude than anything else. Yes, I learned other things too. But those mostly mattered less to me than that emotional piece.
posted by Michele in California at 2:14 PM on May 6, 2013

I suggest focusing on relaxation, emotional vulnerability, open speaking and listening, integrating sex and sensual / indulgent pleasure activity (massage, saunas, picnics, cuddling), connecting fantasy life and social identity, etc.

You talk about acts and performance, but I think young inexperienced men in our culture are likely too preoccupied with that -- sex as bodily performance -- and have the most to gain from reconsidering it in more mutual, social and emotional terms.
posted by ead at 2:50 PM on May 6, 2013 [11 favorites]

ead said: "You talk about acts and performance, but I think young inexperienced men in our culture are likely too preoccupied with that -- sex as bodily performance -- and have the most to gain from reconsidering it in more mutual, social and emotional terms."

Oh. Muh. Gawd. THIS. And more of this. To hell with technique. Enjoy him and tell him you just want him to enjoy you.

Once upon a time, I was a terribly shy guy. I was on a date. We ended up back at my place and we got stuck at the moment where she was hoping I'd make a move and I was too shy to do it. I offered her another drink and she said "That sounds nice, but honestly? I'd kind of like to fuck your brains out, so you can either pour me another glass or you can take me to your bed." Yeah, so when we got to my bed she told me to lie down. She took my clothes off and had her way with me. She was in total control and it was awesome.

By the second time, the sex was pretty much a 50/50 give & take thing. But that first time, it was all her, and it took away any nervousness on my part. I was pretty nervous even though I wasn't a virgin. I guess I was worried I'd disappoint her? Or something? I asked if there was anything she wanted me to do and she said "Nope. Just lie back and enjoy the show." And with that, my nervousness pretty much disappeared.

A lot of the nervousness is about being afraid of doing something wrong. If you take control the first time, he won't have to worry about doing anything wrong since there won't be anything for him to do but enjoy. And, believe me, he will.

Treat the first time you two have sex as if it's a gift you're giving him. After that, figure it all out as you go.

Good luck! It sounds like he's a lucky guy :)
posted by 2oh1 at 4:55 PM on May 6, 2013 [1 favorite]

Positive to negative feedback ratio should be like 70/30.

Add a specific suggestion after a negative: "I don't think I'm into having my nipples pulled so hard, but I love it when you lick them slowly like you did last night."

Be sexy when you give feedback, like, "Can you feel how wet it makes me when you do xyz?" (while you move his hand to feel...)

Be playful and light when possible.

"Want to try xyz?"

Just show him how hot he is. Look at him with the lust you feel. Tell him when he looks especially sexy. All the feedback doesn't need to be about specific technique.

Have fun!
posted by latkes at 7:42 PM on May 6, 2013