First time

[AppleGeek]

Ok so I need to give you some background info. My first time having sex was with my ex, (we will call him: joe) I trusted Joe so we did it. But I had to be the bottom. I wanted to be the top but he said I would like it. So I trusted him but I hated it. (He was big down there) and I havnt had anal since.

Ok so I have this best friend, we will call him Andrew. We are such great friends that we dated. But we decieded to be friends instead. We were better that way. But we still hook up. A lot. We could be sitting on the couch playing a game then we start making out and the blowing. I told him I didn't want to have sex because Andrew is a top and I would have to be the bottom and my only expirence being a bottom went terrible. Andrew said it was fine and he coudnt care less about anal, but I really want to bottom for him. I don't know why I feel like this. He's just so attractive. I'm just afraid what happened with Joe would happen with Andrew...ugg. And If I do have anal with Andrew what do I do to make myself feel pleasure. (Sorry if this is long or too discriptive. I tried to be as basic as possible. I'm new here. If I did something wrong ill take it down lol)

[AppleGeek]

anything :/

[sheffield]

You want it with Andrew, and that makes a big difference. I think a big part of enjoying being a bottom is wanting it and being horny about it. If you don't really want it, you probably won't enjoy the physical stuff either, even when there's nothing actually wrong. You can discuss it with Andrew, I'm sure he understands and he probably knows how to be extra careful in sex. Remember to warm up enough, and you can be on the top so you can control the penetration.

[Samdabisa]

You want it with Andrew, and that makes a big difference. I think a big part of enjoying being a bottom is wanting it and being horny about it. If you don't really want it, you probably won't enjoy the physical stuff either, even when there's nothing actually wrong. You can discuss it with Andrew, I'm sure he understands and he probably knows how to be extra careful in sex. Remember to warm up enough, and you can be on the top so you can control the penetration.

agreed. The first time I bottomed, I was not into it because the guy was a creeper in a way and only was worried about his pleasure. As long as you both consider each other's pleasure, you should be fine IF and WHEN you want to do it.

[Bowyn Aerrow]

Most of sex takes place in the brain not the bottom/crotch.

Thus your desire to be with this guy this way may make the whole experience better.

Also consider that you are a virgin (basically) down in that area. I would suggest that you start fingering yourself to adapt and get used to the idea of having something go in.

Also use lots of lube. One of the better positions for entry is on the side, spooning your partner behind you. He basically lays there and you do the 'work' of getting in there. You will have more control, be able to take your time. The whole being in control of how fast insertion takes place usually leads to a guy relaxing a lot more than laying there and having the other guy 'guess' how fast to go.

The whole chemistry thing seems to be at work here. There is far much more to the act of sex than just the sex. Personalities have to mesh, there has to be some amount of trust.

Apparently you trust him with this and maybe he is even a bit more dominate than you and it comforts you emotionally. This a good thing.

IF he treats you like a virgin, goes slowly, uses lots of lube you should do fine.

If he is more than average in endowments you two may want to use toys to get you used to having something 'up there'.

Fingering can work, start with one finger, work it a while, move up to two fingers, work it a while longer, then three - however many are needed.

Fingernails should be cut very short and filed smooth - Just an FYI.

[ObnoxiousKid]

not sure why the names need to be kept anonymous lol not like anyone knows you or them

[boi4studs]

Make sure he gives you lots of foreplay before fucking you. Like at least 20 minutes worth of playing with your hole.