[sarahcar]

I'm planning to have sex with a guy I've been seeing. It would be the first time for me, although he has had a couple of previous partners. I think the best time to switch to initiate penetrative sex would be when he is going down on me but before I climax. That way, I'd be at the peak of arousal and lubrication already...

I'd like to have your opinion on the best way to do this. Is this transition a common thing to do? And what exactly should I say or do to make him switch mid-way from performing oral to fetching a condom for sex? He is a generous partner and, from what I've gathered so far, likes to be told what to do. So, I don't mind communicating my needs, but I want to pick the right words, to make sure he wants it as well, and also not to sound too crass.

Thanks in advance!

(In case you care about this: He doesn't know it would be my first time. I'm 21 and I haven't felt the need to tell him and make a big deal out of it. because it really shouldn't be. Plus, my hymen is pretty stretched and torn through the insertion of tampons, fingers and toys.)

[Element]

My personal opinion; they guy needs to know it's your first time. He needs to know he needs to be gentler, kinder, move a bit slower with a virgin. Everything is going to be new to you. If the man truly cares for you; he's going to want to do something to make your first time special. You're giving him a gift and if he is a respectable man; he's going to take that gift with care and respect.

As for your initial question; I like to take my man's face in both of my hands, look him in the eyes and tell him "Come here. I want you."

There is also the issue of; if your man is well endowed, it doesn't matter if you believe your hymen is stretched. First time penetration can't be like every day normal sex. He needs to know to not go in like a jack hammer. He needs to know how to enter a virgin with care.

[a_dub]

There is also the issue of; if your man is well endowed, it doesn't matter if you believe your hymen is stretched. First time penetration can't be like every day normal sex. He needs to know to not go in like a jack hammer. He needs to know how to enter a virgin with care.

I'm only 5 inches...definitely not "well endowed"...so I can go like a jack hammer! Yay!

Do all virgin girls require gentle sex with large men the first time or is it a personal choice that varies from girl to girl?

[DreamP346]

Telling a guy if its your first time is your choice you don't have to tell him anything about your past. You can always ask him to go gental regardless of its your first time and 100th time. However, open sexual communication in a relationship is very important. Is this a relationship that you plan on continuing? If so, why hide the facts. Be truthful.

The best way to transition is actually to have an orgasm from oral and then have intercourse. This way you are completely relaxed. Also, many women don't orgasm from intercourse alone, especially the first time. So unless he is going to give you oral after he has cum, it is better to get your orgasm before intercourse.

If he can maintain an erection while giving you oral, its better to start off with condoms already on. If not, there is nothing wrong with putting the condom on after you have an orgasm. There are many ways you can keep it sexy. Here is something you could do. Once you cum, you switch places with him lying down and you on top. Keep the condom handy (under the pillow before you start so its easy to get). Tell him you are now going to take care of him and seductively kiss him down the chest. Slip on the condom and then get on top of him. This way you will also be able to control the level of penetration and how fast you go.

The language you use really depends on your guys. Some people like to talk dirty and use super vulgar language with each others. Others will use more romantic words like "I really need you". It all depends on you. There is no right answer, words or language. Whatever makes you feel comfortable.

[sarahcar]

Telling a guy if its your first time is your choice you don't have to tell him anything about your past. You can always ask him to go gental regardless of its your first time and 100th time. However, open sexual communication in a relationship is very important. Is this a relationship that you plan on continuing? If so, why hide the facts. Be truthful.

The best way to transition is actually to have an orgasm from oral and then have intercourse. This way you are completely relaxed. Also, many women don't orgasm from intercourse alone, especially the first time. So unless he is going to give you oral after he has cum, it is better to get your orgasm before intercourse.

If he can maintain an erection while giving you oral, its better to start off with condoms already on. If not, there is nothing wrong with putting the condom on after you have an orgasm. There are many ways you can keep it sexy. Here is something you could do. Once you cum, you switch places with him lying down and you on top. Keep the condom handy (under the pillow before you start so its easy to get). Tell him you are now going to take care of him and seductively kiss him down the chest. Slip on the condom and then get on top of him. This way you will also be able to control the level of penetration and how fast you go.

The language you use really depends on your guys. Some people like to talk dirty and use super vulgar language with each others. Others will use more romantic words like "I really need you". It all depends on you. There is no right answer, words or language. Whatever makes you feel comfortable.

Thank you! Your response was very thorough! I appreciate your advice regarding language and condom use. But I'm a little unclear on your suggestion of having an orgasm first and then going for intercourse. I have only been able to have clitoral orgasms so far; vaginal vibrators haven't ever brought me to the edge by themselves. So, I see your point that I might not actually be able to have an orgasm through penetrative sex. But would I want him in me once I have already climaxed? And even if I didn't mind, wouldn't my vaginal muscles start going back to their normal (tighter) state, rather than the more expanded state that comes with sexual arousal?

[DreamP346]

Thank you! Your response was very thorough! I appreciate your advice regarding language and condom use. But I'm a little unclear on your suggestion of having an orgasm first and then going for intercourse. I have only been able to have clitoral orgasms so far; vaginal vibrators haven't ever brought me to the edge by themselves. So, I see your point that I might not actually be able to have an orgasm through penetrative sex. But would I want him in me once I have already climaxed? And even if I didn't mind, wouldn't my vaginal muscles start going back to their normal (tighter) state, rather than the more expanded state that comes with sexual arousal?

After an orgasm, your muscles will be all relaxed. Its not going to tighten up immediately. This is a very common practice among heterosexual couples - man provides oral to woman and reaches female orgasm, and then they have intercourse. Each person is different so I don't know if you will want your partner inside of you right after an orgasm, but for the majority of women, its not an issue at all.

Because its your first time, you just have to experiment to figure things out. That is why it may be a good idea to tell your partner that its your first time.

A large percent of women cannot have vaginal orgasm and having one on your first try is very unlikely. Also, vaginal orgasms are usually percipitated by rubbing the G-spot. The G-spot vibrators don't do the job for the majority. You may be able to have a vaginal orgasm from a dildo, but its not the norm. A real penis will be very different since it doesn't vibrate, but also the position of your body (since you will now have a partner) will make the whole experience very different than a toy. Don't go into it expecting it to be anything like with a toy. There will be a lot of awkard moments trying to figure out what position works best for you, where to put your legs, how to move (or not move), etc.

as you say your partner is very generous, he will most likely be very patient as well. You may want to discuss things with him before hand about what things you want to try, etc. I know it doesn't sound as romantic to plan the night's activities, but it can make things a lot less awkard.