A: Greetings,

First, it's wonderful that you are putting some serious thought into this delicate situation. My ability to respond is also limited because there are some questions that are important to know, like are you two just friends? Have you talked about having a relationships, or sexual relationship before? Or is this a silent longing you have had that he is completely unaware of?

Given the information you have provided, I would say you have a few choices. It depends on your comfort level.

Choice one) Have an honest conversation with him to establish what his thoughts are. In the initial conversation, you don't have to reveal to him that you are interested in a sexual relationship. If the conversation is going well and he confirms, that he would be interested in sex, it would be a good time to express yourself or agree, you would be interested as well.

Choice two) This one involves more finesse. This all hinges on whether or not you already know that he is also interested in you too. If you already know that he is interested but are uncomfortable with being frank about wanting to have sex, you can plan a romantic evening. Go dancing and/or have a nice romantic dinner. If you go dancing, choose a nice club, preferably one with live jazz or some other type of smooth groove music. And do dance with him. ;) This is the perfect opportunity for you get into the vibe. Your body language can be more powerful than you verbally telling him what you want. This is a good way to ease into a sexual situation with few if any awkward moments. You may want to do this more than once before you take it to the sexual level but it's really up to you. It's nice to welcome him into a more intimate space. It will also let him know you are serious and the vibe is strong.

Your first time) It may hurt, it may not. First, He HAS to be gentle and this should be established before you start. Also, if you are well lubricated and relaxed, that can ease or eliminate the pain. The amount of pain you have may also depend on your body as well. You really don't have to worry about it though. And please don't let it keep you from doing what you want to do. It may hurt at 22 and it will still hurt at 28... So waiting won't eliminate the possibility of pain.As you get more relaxed AND if he is gentle, the pain won't last at all. And trust me, once it starts getting good, that will be so far from you mind!

Sincerely,
Tressa!