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Being prepared for the first time

My girlfriend and I are both virgins and it college. We've been dating for nearly a year now and it feels that we might be going to have sex in near future so I'm looking for some advice.

Shortly after I started masturbating when I was a teenager I would always try to last long during most sessions trying to stay on the edge. Although its not regular I've trained myself enough so I can actually orgasm without ejaculation but I always finish otherwise I get sore. I actually got a fleshlight back when I was 17 by using a supermarket prepaid cc online (yes I was a minor and its illegal so sue me) Anyways I understand it won't be even close to the same but hopefully it was worth the investment. Of course I understand that this might all be for naught since when everything is new there could be sensory overload so I might blow my load early. On the other hand I might get nervous and be unable to finish.

You could say I've preparing for this day since I was a teenager. I've been reading guides on how to pleasure women for years (yeah nerdy I know) of course that might do little good since I have never practiced what I've studied. I understand the importance of foreplay and that its best that my partner orgasms before I enter her however since it would be my 1st time I'm not sure if everything will go as planned so to say. As well as the need to take our time. My girlfriend is a virgin but I'm not sure if her hymen is still intact. She has mentioned that she's used vibrators/dildos but I've heard many women pleasure themselves by clitoral stimulation so it could be intact. This brings up another concern about possibly helping her with pain during.

I have protection ready of course when the time comes and I know to use a fresh one every time so no need to remind me of that. There is also the concern of how sex can change a relationship but I guess I'll just have to deal with that when the time comes.

Thank you for those who read this and on whatever advice you people can provide.

OK, you have protection and that is good. She should also have vaginal spermicide - jelly, foam, suppository. If you are that close to sex, you are close enough to discuss the benefits of adding spermicide in her to a condom on you.

You are over thinking the whole thing too much. Just relax and have fun with it. Sex will only get better the more you do it. The first time you do it you will both be lousy. Its like anything in life. Practise makes you better. You cant just pick up a guitar and be instanty awesome. You must practise.

As brandye has said make sure that fun/practice is safe though.

Thank you to those who responded so far.

@Brandye

My girlfriend is on the pill to help regulate her period so we're not worried about any unwanted pregnancies. We're going to use condoms just in case and even though we're both virgins it doesn't mean we might not be infected from something we don't know about such as yeast infection or something along those lines. So its more a less something we'll use whenever we start having sex until we feel comfortable with just the pill.

My main concerns are her pain, being able to satisfy her and if I'll be able to last long enough despite my the preparation I've done. Of course I know I shouldn't set my expectation too high since things don't go as planned in life. However I want our first time and following encounters to be the best that they can be.

@Syryon

I understand things probably won't go as well as I want it to but you can't blame a guy for being prepared and at least trying to make it as good of an experience as possible.

The best way to assure that you satisfy her is to pay attention to her cues and follow them. Watch for body language, listen for sounds/words, and do as those things tell you to do. Also, provide her similar feedback so she has some idea how to assure she satisfies you.

Also, don't be alarmed if she gets emotional afterward--she may, she may not, don't be surprised either way, just cuddle her through it if she does. I've cried post-play twice. The first time a guy ever brought me to orgasm, and one time my now-husband and I had to stop because I felt an insulin reaction (I'm diabetic) coming on. I think the fast, unexpected stop and "come down" were too much.

Extend the foreplay and outercourse as this will help ease, if not erase, the pain of first entry. An orgasm before entry is for the NEXT time, not this time. You want her on the brink of orgasming. Understand?

Afterwards, relax for a bit, cuddle and since an orgasm isn't all that likely the first time, try it all again from the beginning, this time deliberately seeking her orgasm..

HwT,

Welcome to the SI101 Board and its Forums. I hope you will enjoy participating. Please begin by familiarizing yourself with the FAQs, the Posting Guidelines, and especially the Index, all found at the top of the main screen. The Index contains links to helpful informative insightful, as well as how-to information that discuss the most common questions and concerns people ask about. In addition, if you click on the site's Home Page you will find even more information.

I recommend that the two of you read every article listed in the Index, discuss what you have read, and add the information to what each of you already know. Knowledge is empowering.

> My girlfriend is on the pill to help regulate her period so we're not worried about any unwanted pregnancies.

You should be. It is naive to believe that one form of birth control is all that is required. Contraceptives are not 100% guaranteed, and if a woman forgets to take a pill--well.... If you read around the site you will find many references to the following: If a girl/woman does not want to become an unwed mother she should look out for and protect A#1--herself. If a boy/man does not want to become a father, he should look out for and protect A#1--himself. In addition, a third line of protection should be used such as a spermicide. Never ever rely upon the other person for your protection!

> We're going to use condoms just in case

Good, now add #3, also in order to be extra safe than sorry.

> even though we're both virgins it doesn't mean we might not be infected from something we don't know about such as yeast infection or something along those lines.

True enough, yet a yeast infection is the least of your concerns, and, it manifests itself noticeably.

> My main concerns are her pain, being able to satisfy her and if I'll be able to last long enough despite my the preparation I've done.

All this is covered in some articles on first time intercourse listed in the Index.

It is common for fellas to be concerned about first time performance issues. Just understand that rarely does first time intercourse go as planned. There is also an article about "experience" and I urge you to read this even though your experience is equal at this point.

When it comes time for intercourse, plan on using the Woman Superior/Cowgirl position. This places the woman in control. She knows where P & V are and can deftly bring the two together. She can control the placement of the penis, the pressure, speed, and depth of insertion, the return stroke and rate of stroking. This saves you some angst and performance anxiety.

As for the likelihood of climaxing too quickly, know that PE can happen with the initial insertion, pull out, or within the first few strokes. If it happens after a couple of minutes it is simply an untimely event. There is a post on what to do to help out.

> My main concerns are her pain, being able to satisfy her

There may or may not be any initial discomfort. If there is it is rarely that bad, yet you must expect it as a matter of what happens due either to rough handling or the fact that the hymen is still (partially) intact.

> Women can be satisfied by simply cuddling with her lover and enjoying herself and you. This is all you need concern yourself about.

As for orgasms, as noted, she most likely will not have one due to first time intercourse due to a lot of reasons, discomfort being one, distractions being another. Female orgasms are much more elusive than the male's.

If she does not yet masturbate then do not expect that she will climax. Each of us male or female is responsible for our own orgasms. We do not give them away. All any of us can hope to accomplish is to help each other achieve them. If she has yet to cross this bridge, then she must learn to connect the dots so to speak. Once she can climax regularly and consistently she can then take your fingers in her hand and show you what is required. There is an article on all this, also.

> Of course I know I shouldn't set my expectation too high since things don't go as planned in life. However I want our first time and following encounters to be the best that they can be.

Set your expectations on entertaining each other and simply enjoying the moment. Know this: Making love is not what we do to each other; rather, what we do with and for each other in partnership. Explore and learn together.

> I understand things probably won't go as well as I want it to but you can't blame a guy for being prepared and at least trying to make it as good of an experience as possible.

Asked and answered, above.
-doc

Dear HWT,
My first question to you would be; how far have you two come together so far in the sexual realms?

I'd say that you may like to very much explore eachothers' bodies together before even thinking about penetration. If you have experienced sexuality together on just about every aspect but penetration, both she and you will know exactly what stimulates and pleases her (and what pleases you :)). You will know exactly how to read her bodylanguage and she yours. Iow; I'd consider such experience a good remedy against any fear of hurting her or not pleasing her. Very likely, with such extended sexual experience together, you will both know what stimulates her to orgasm. Let's say: about 75% chance, since only a quarter of women report to never orgasm.

The only thing you shouldn't be surprised about is that she may not be capable of orgasm through penetration. Due to her first time. But also because of the simple fact that only about a quarter of all women frequently reach orgasm through penetration and thrusting.

If she's ready for actual penetration; I'd suggest you'd hand her the wheel. While on top, it gives her all the control over the situation she needs. Even if she gets scared or hurt; she can switch the angle or stop the movement within a fraction of a second. And you are right there to help her. Allow me to quote DD2 on this:
[QUOTE=dancingdoc2;269491]First time intercourse is best accomplished using the Woman Superior/Cowgirl position. This places the woman in control.
A) she knows where P & V are and deftly bring the two together
+ this saves the man some anxious moments and avoids fumbling
B) if she has a (partial) hymen, she can position the tip of the
penis between the rim of the hymen and vaginal wall which will
permit the penis to slip in and not necessarily poke against the
membrane perhaps causing some discomfort
C) she can apply just the right amount of pressure when trying
to insert your penis
D) she can go as deep as desired and then...
E) begin stroking at a rate and depth that suits her
F) you can lay on your back and enjoy the ride, and...
+ support her breasts so that they do not bounce
+ caress them
+ raise your hips up to meet her movements

Although her movements will be up and down (the length of your penis), this does not necessarily mean they have to be straight up and down, vertically; she can also "ride you" by positioning herself on her hands or her forearms above your chest and move back and forth on that axis. Whatever works for her in the moment.[/QUOTE]

Now, on another realm: there are thoroughly 4 psychological mechanisms about expectations. Please read on, it gets to practical advice in a minute :)
1) Some say you shouldn't expect too much, because it will only lead to disappointment. There lies truth in that; we all know it does. Your mind becomes much unsatisfied when the situation becomes other than expected. The exception being when reality is somehow considered more positive, which we call: surprise!
2) There is however another system at work. Whatever you expect to feel, is more likely to be experienced. If you fear pain, it is more likely to be felt. If you expect pleasure, it is more likely to be felt. You can test this theory at home by holding something very cold and pretending it is either warm and pleasant or cold and painful. You will see your experience shapes itself to your thinking.
3) And there's even a mechanism that expectations influences your actions. If you fear to fall down, it is more likely that you'll fall. Your body is preparing itself for it, just because you expect it. It is worthwhile noting that your mind and body respond to positive commands better than negative. Your mind has a tendency to skip the "don'ts". So instead of "don't hurt her", think: "please her".
4) As you now see how influential the mind is; you may see how it tends to not fully process your sensory input at times, because your simply too busy processing thoughts and what-if's inside your head. This can easily be reversed. Allow yourself to be in the moment. This does not mean; losing your head. It means; focusing on the here and now. On what you feel and on eachother.

Which is why I'd say when it comes to first times: don't expect rainbows, but do expect pleasure. And let yourself "be" in the present moment; flowing with it. You'll get the best of all psychological mechanisms!

Btw: My first time preceded months of exploring eachother. I had several orgasms prior to penetration. I was in charge of the penetration. I didn't expect pain, but pleasure. My expectations were exceeded by the experience; absolutely wonderful would be the term :)

I hope this post is somehow helpful to both you and your gf (as you may have noticed; I've incorporated advice for you, her and both of you, since you'll be undertaking this journey together :)). If you need clarification on anything, please let me know!

Thank you for all the responses. Especially for the time effort from RedRoses and dancingdoc2. I'll take everything you've said into consideration.

sorry for not responding earlier as I've been away. My girlfriend and I have been petting for some time and just this weekend we started experimenting with oral sex. I'm proud to say that after a bit of guidance I was able to bring her to orgasm this way especially since I hear many women find it difficult to orgasm from penetration alone. When she gave me oral it felt amazing but I found it difficult to orgasm and we actually took a break where she tried again and I was able to ejaculate. I reassured her that it was great though. Is this weird that I had difficulties having an orgasm from oral? I've heard most guys find it especially stimulating. Could I have been more nervous then I realized and that this was the issue?

I really appreciate the help here especially since we could be having sex as soon as a few days.

RedRoses you mention that it would be best for our first time if she is on top. Just wondering do you mean just standard female superior? Would this be a good position to give clitoral stimulation to her as well to make it more likely she'll orgasm from intercourse. I understand that women are less like to orgasm this way but it's worth a try. Plus I gotta admit there is an ego thing of being a man and giving your girl an orgasm with your penis in her. Would I just lay back and let her take her time until we're done? I want to be doing something for her.

I know I had something else to say but I forgot. Guess I'll just add it when I remember.

> I'm proud to say that after a bit of guidance I was able to bring her to orgasm

Bravo and Kudos!, although keep in mind that each person is responsible for his/her own orgasms. All any of us can do is to help our partner achieve them.** It sounds like you did quite well. Keep the lines of communications open and provide each other with feedback on how you are responding to kisses and caresses and for what you need now/next.

> When she gave me oral it felt amazing but I found it difficult to orgasm and we actually took a break

Yup! true enough. You'll find an article listed in the Index that discusses this problem, also.

> Is this weird that I had difficulties having an orgasm from oral? I've heard most guys find it especially stimulating.

It is not weird at all when you understand why. Soon after learning how to masturbate we quickly settle into a routine that while pretty much the same for every other male, each of us adds some variation to the theme that is unique to us. The sensations we receive from oral stimulation are indeed intense yet more than likely not what we need and rely upon to build ourselves to the brink of an orgasm by hand. So, as explained in the article, the thing to do is to enjoy the intensity for as long as desired, then slide back down your arousal curve and go about rebuilding your arousal much as you would do as if home alone.

> do you mean just standard female superior?

Yes, although some variation on angles like sitting astride and stroking vertically vs. semi-reclined and stroking up and down the length of your penis while moving more or less along your torso.

> Would this be a good position to give clitoral stimulation to her as well to make it more likely she'll orgasm from intercourse.

Here is a Golden Rule for you two to learn: Help your partner to enjoy the first and last orgasm of the session as well as any quantity in between as she desires. This means you can help her enjoy an orgasm before engaging in intercourse! :D There is no rule that says every orgasm has to be the result of intercourse.

For the first few sessions and until you begin to become comfortable with each other I would not strive to have orgasms. If they happen--GREAT, otherwise know and understand that even without orgasms, women can have a rockin' good time. (There is an article on this, also.) There are enough distractions going on that will probably squelch any build up that would result in an orgasm. Please her in other ways, primarily.

> **I gotta admit there is an ego thing of being a man and giving your girl an orgasm with your penis in her.

There is more to making love and expressing the love each has for the other than an orgasm. Orgasms are nice, yet they are not the be all end all for making love. You have much to learn and I suggest, again, that the two of you read every article listed in the Index, especially if you want to become a world class lover. Drop the ego and direct it where it really is important--pleasuring her and being attentive to her in other ways, first.

> Would I just lay back and let her take her time until we're done? I want to be doing something for her.

* While reclining you can steady the motion of her breasts
* While reclining you can cup her breasts and stimulate the nipples and areolas
* While reclining, you can continue to kiss and caress her body
+ understand that when aroused the skin is the largest most sensitive sex organ
* While reclining, you can continue to provide feedback on how you are
responding to what she is doing and for what you need now/next
* While reclining, you can be whispering sweet nothings
* While reclining, you can thrust upward in response to her movements
+ plus the strain will help trigger your orgasm when you are nearing your peak

These should keep you occupied....

> Would I just lay back and let her take her time until we're done?

As you gain experience you will discover that there are many things you can do in response. Didn't I mention somewhere in this thread that making love is not what we do to each other; rather, what we do with and for each other in partnership? Your contribution is required unless you are tied UP or down and even then you can do something....

Lastly, drop your focus about orgasms and just do what you can do to enjoy the "ride". It's not all about orgasms.

> I want to be doing something for her.

Concentrate on making love to her mind, soul, and psyche.

-doc

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