Expert: Guycurious - 1/29/2012

Question
My girlfriend and I have been dating for 5 years now, I am 25 and she is 21. Recently the topic of swinging has come up between us. I feel that I have a pretty strong grasp on the topic, however extra insight is always a benefit. I would love your views and advice on the topic.

To begin "Kitliana" (my girlfriend) has never had full intercourse with anyone but myself. No female experience and very little male experience. I however have had much more experience and had enjoyable threesomes in past relationships. I always have wanted to give her the chance to experience sex with another partner, male of female. I believe that healthy sex experience is an integral part of growth and development. Giving her this opportunity is important to her becoming a strong woman. She was opposed to this idea and I knew that pushing her into it would not help her grow, and left the idea alone. Every 5-6 months I would bring it up to see if her views had changed.

Recently she displayed a growing interest in a female friend of ours that we mutually find attractive ("Crystal"). Crystal has been dating a friend of ours named "Josh" for a few years. Multiple years of friendship has been built between us all, 9 or more in the case between my girlfriend and Josh. We aren't all the closest, but we all have deep friendships and memories.

I have lusted after Crystal for years before this relationship, and its well known. However, my first instinct is to give my girlfriend the chance to experiment sexually, and let her explore her sexual desires. This looks to start as an encounter between the ladies, progress to swaps, and possibly a foursome later if all participants enjoy the festivities. I have opened the lines of communication and found that the couple has an open relationship, has threesome experience and seems interested.

I began my methodical checklist to begin healthy connections between both couples. The men talked recently and have had a good discussion. The ladies are set to talk in the near future by themselves. Then as a group we plan to meet for dinner at a restaurant, followed by meeting at their house to talk more openly  couple to couple. Then if all parties agree, the females would have an encounter by themselves to see how they enjoyed and handled.

The other couple has their boundaries set and know their limits. I need to still sort though the minor details with my girlfriend, though we have had multiple talks at length on boundaries and such. We plan to write everything down so that we know what the limits of comfort are and can reference and alter if need be as a couple. I know that communication and honesty are the two most important things to healthy swinging. We have plenty of time before any encounters would happen to fine tune all communication issues.

My concerns begin here.
(1) With me being Kitliana's first lover, are there any steps I can take outside of the normal to help her find her comfort zone? I understand I cannot make her be comfortable, I can only help guide her there.

(2)Both the women are have self image issues. Kitliana is slightly overweight and Crystal usually has sex in the dark or dim light because she is shy. Any way to help them circumvent these issues and let all parties enjoy the experience.

(3)We will most likely attempt a full swap at one point. With both Josh and my girlfriend being close friends, are their any steps to take to help break the stigma of "this is my close friend". They already both admit that they are sexually attracted to each other.

(4)What else am I missing to help give her a healthy and enjoyable experience? Always nice to have extra eyes and advice.

Answer
I must admit your depth of research and planning on this topic at your age is remarkable.  I'm very impressed.  

Onto your questions.  Kitliana will find her comfort level with her Crystal and Crystal will do the same.  Maybe if the experience is enjoyable for both a second encounter will be more relaxed, maybe even with the lights on !

Sexual exploration at your ages is normal and I encourage it.  Life is too short to sit back and wonder, "What if...."  You've already discussed the ground rules as partners and I'm assuming said ground rules will be discussed as a group.  

There is nothing you can do to break the stigma of "this is my close friend".  That is the reality of the situation.  There may be some awkwardness immediately afterward but I feel it will quickly fade.  

Have fun, be safe and I wish you the best.