A: Your attitude here is very important. It may be helpful for you to remind yourself that most of us were frightened the first time. Accept and respect his fear. Also consider it an honor to be his teacher - the one to invite him into the incredibly wonderful world of sexuality and sensual pleasure. Take your time, and explore a great deal of foreplay over several sessions before moving into penetration practices. Create a sacred space with candles, flowers, incense, sensual music etc. Dress in something beautiful and sexy. Dress him.
Teach him how to pleasure you and thank him profusely, reassuring him that you are very much enjoying each step of the way. That could be one session unto itself. Then explore pleasuring him slowly and with great attention to detail and lots of communication and appreciation. Massage his belly and pelvic area to release tension. Then create a session to arouse each other before putting his lingam inside you. Give him positive, encouraging feedback no matter what happens. Emphasize the positive and give suggestions about how it could be different next time. Suggest that it's like learning anything else - improvement surely will follow. There are excellent workshops that can help the two of you move through this much faster and easier, if he would be willing (and courageous) enough to attend. Typically they're in California or Hawaii. Check the Teacher Section on the website for referals.
