A regular reader e-mailed me the following:

It appears from reading your accounts that you’ve had the experience several times in the past year of being someone’s First – first extramarital event, first swing, first 3-or-moresome, first girl-girl.

Any thoughts on the care and feeding of beginners? How did these firsts come about – your idea or theirs? How much pre-planning and advance discussion? How did you deal with nerves on their part or yours?

Some of this might be useful not only for others in your position but for anyone leading anyone into new outside-the-comfort-zone experiences.

If you think about it, we’ve all been beginners at some time. For Veronica and I, SwingerWife was a valuable source of advice and support as we started to explore the lifestyle.  [Sadly her blog is gone, so there's nothing to link to.]  The longer we’ve been playing, obviously the frequency of “firsts” declines and we became the experienced couple.  Looking back, while we suspect that several of the couples we’ve played with were relative newbies, that was something we figured out afterward.  Case in point are Ned and Ann, just click on “The Tale of Ned and Ann” at the top of this page for the full story of that disaster.

Times when we have knowingly been a “first” for someone else have almost been exclusively with blog friends, people that we’re already friends with.  A good example is The Dirty Side of Us.  We’ve known her and her family through her mommy blog for almost as long as we’ve been blogging.  Last fall she came to visit us for a long weekend, for what was originally planned as a purely vanilla/non-sex visit.  As the date approached, knowing that we find her attractive, she let us know that she was interested in possibly playing with us.  She had never had any 3some or girl-girl experience and wanted to explore, with the full knowledge and consent of her hubby.

The details are not important, but to answer the readers question, knowing that she was interested in playing with us gave us the opportunity to have several open and honest discussions about it.  We talked about boundaries, desires, fantasies she wanted to fulfill, and she had the chance to talk about all of this with her husband, who knew all along what we were planning.

I hope that no one should be surprised that it comes back to communication, before, during and especially after we play with someone who is exploring something new.  I say especially after because we want to make sure that our friend didn’t have any regrets, that it was a positive experience for them.  Obviously we’d have clues during that would tell us that she’s enjoying herself (multiple orgasms and enthusiastic pussy eating kinda give it away!), but a quick “hey, did you have fun last night? And it’s all good with hubby?” is still important.

Veronica: At the risk of being repetitive it really does come down to communication.  Communicating with the person or couple before, during and after the sex, even if its a quick email or text is important.  Also I think with a newbie in a 3some situation it is good to put them at the center of attention, so to speak.  Whether or not you have to be more assertive depends on the couple.  I do find though that when I have sex with a woman who is new to girl sex that I do need to take the lead a little bit.  However, I find that once they get into the sex that they become more assertive.

I also find that when I have sex with a woman who is having her first threesome experience I always let her know that I would not be offended if she did not want to reciprocate on the oral end of things.  She might get cold feet and I want her to know that it’s okay to change her mind.  A few women have said to us “I’m not sure I’ll know what to do!” and I’ve told them that the best way is to do the things that you like having done to you or to imitate  what the person who had gone down on you just did as people will often fall back onto how they like things  until they know exactly how you like it.

Hubman and I do not avoid newbies nor do we seek them  out.  In the beginning we had  actually been told by some more experienced couples to avoid people who prefer newbies as they often have some issue they are trying to hide and feel that they can best hide it with an inexperienced couple. Now of course we are not newbies so that is no longer an issue.

For an additional perspective this week, here’s The Dirty Side (did we ever come up with an alias for her?) with her take on being the newbie joining the “experienced” couple:

From our point of view I would also say that communication played a huge part in me coming up there and the fun that we had. If my husband would have been uncomfortable or did not want me to play I would have NOT. We talked about all the boundaries and the do’s and don’ts of it all way ahead of time and even on the day of me leaving. My hubby had their address and phone numbers in case I felt uncomfortable with any situation.

It all comes back to the communication and it is SO important on every ones part!  I felt extremely and let me say extremely comfortable meeting them and being with them.

I kind of in a way choose them to be my first. I had read both of their blogs for a long while and had some communication prior to all this happening. I knew they were good people from the talks on the phone and emails I had with them. I want some one who was still kind of new and yet had also done this and knew the ropes {sorta speak}. I liked Veronica from the very first time I read her blog and did feel a connection so I knew that her and I would hit it off.

I also knew that these two were very attractive people. So I was not my any means going into this blind.
Even thou I/we have not done this again {not for lack of not having fun, because I sure did} I would seek these two out again for a first! They were both awesome and kind.

I know I hope to make a trip soon to see them again