[QUOTE=Buddy;260512][COLOR="blue">Well I am 15 years old and there is this girl who is 14 and we have flirted and now we want to do sexual stuff with each other. She has done anal intercourse multiple times and vaginal intercourse once. I have done nothing sexual at all. We have also never dated.[/COLOR]

Ahh, the hormones are flying! From your description, above, it sounds like the two of you are mainly interested in having orgasms and feeling good, rather than having any sort of emotional relationship. This is OK because if this is what both of you are after; however, it is important for both of you to understand that with an emotional connection comes better sex more often than not.

[COLOR="blue">Now she just wants to do anal which I am ok with. I just need help with the process and some positions. I have read some articles on this site and they just don't give me that personal advice that I need.[/COLOR]

Why so much emphasis on anal intercourse and not vaginal? **
(I agree that for a young girl, this interest in anal stimulation is downright creepy.)

The potential problems associated with anal stimulation are:
* Passing of STDs and other social diseases
* Damaging the sensitive membranes and tissues in and around the anus
* Pain and discomfort when not done with care and consideration
* Condoms are more apt to brake
* Repetitive anal sex leads to weakening of the anal sphincter, which leads the feces to escape involuntarily.

[COLOR="blue">I want to know how to properly insert myself into her anus, and how do I know if I am going in at the right angle. [/COLOR]

Please read this article listed in the Index:

Playing Ball" and How To Tips for Prostate Massage
This is also an excellent tutorial for people interested in and concerned about the how-to of Anal stimulation as well as play.

Dangers of anal penetration-Part 1

Dangers of anal penetration illustrated-Part 2

[COLOR="blue">Also I would like to know what are some great positions for beginners to anal sex. I have a 6 and a half inch penis if that helps with the advice giving.

Thank You. :)[/COLOR][/QUOTE]

Please refer to the site's Home Page and review the many illustrated animated sexual positions. Beginner or experienced, positions are varied and numerous. I'd suggest starting with either the Cowgirl/Woman Superior where the man reclines with the woman straddling him above. Another good one is with the woman on her knees and forearms with the man either kneeling behind or standing behind.

As for angles, consider that every penis has a different slant or list. Some bend up sharply, some not so much; some point straight ahead; some list a bit to the left or to the right. What is important is that the penis penetrate the anus straight and level.

** If the two of you are intrigued with anal stimulation, then I strongly suggest that you limit this activity because of the inherent dangers associated with the practice.

If the two of you want to do this as an alternative to vaginal intercourse because of the chances for pregnancy, then I strongly suggest that you rethink this strategy. If the two of you want to indulge in what is considered adult behavior and activities, then you have to be adult about the responsibilities and potential consequences.

Ideally, three forms of contraception should be used. Hers, yours, ours {backup). She should use some form of highly reliable form of birth control. Perhaps at her young age this is not practical. The next best protection is for you to use a condom and the two of you use a spermicide inside of her as backup.

I understand the curiosity and pleasures associated with seeing each other nude, and, pleasuring each other physically; however, as a person much more experienced, I'm here to tell you that for all the fun of intercourse, orgasms derived from foreplay activities {hand job/oral/both together) will produce much more intense orgasms. Think about this.

If your girlfriend has not yet learned how to masturbate, then in all likelihood, you will be the only one enjoying orgasms. For more on this, please read the articles that discuss this matter, listed in the Index.

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 section, 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 discusses 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, as noted.

I hope this is of help. Got questions? (Please see my follow up reply, below.)

You might want to just ask her what to do if she has that much experience with anal sex.
There's plenty of information on it on the forums, just look around the sticky posts.

I'm no expert but it may help if she guides you as to how to insert your penis,and check out sex positions part of site as there may be some anal ones there to look at.And by the way wear a condom!!!

There are several threads considering anal play/sex with tons of info. Hope this helps answering your question:
-http://www.sexinfo101.com/forum/pleasing-him/11220-anal-101-a-25.html with pages of opinions
-http://www.sexinfo101.com/forum/pleasing-him/19950-playing-ball-how-tips... tutorial for people interested in and concerned about the how-to of Anal stimulation as well as play (not just for men)
-http://www.sexinfo101.com/forum/sex-toys-products/28800-dildos-human-anu... on the risk of anal penetration

I did some reading on anal sex myself lately (interesting subject). And I found [url=http://sexsecretsblog.com/which-anal-sex-positions-are-best-for-beginner... blog to be quite informative, also about positions :) And if you're really interested; there appears to be a book about it! "The anal sex positions Guide" by Tristan Taormino; an award-winning author, columnist, editor, and sex educator. Also the author of: "The Ultimate Guide to Anal Sex for Women". Haven't read it myself, but I will give you reviews when I have ;)

Like the others, I'd also advice: let her guide you! You leave her in control (that's actually a tip on many sites; not only for the advanced, but also considering beginners) She pushes a little and inserts the penis. She moves when comfortable and will ask you to move when she's ready.

If your gonna have anal sex with her, please do use a condon for protection. It is very important to use a condom.ok? And have a lubricant at hand. With regards to positioning, you might just ask her since she's done it already. As what they are saying here, let her guide you. Just relax and be patient.

As for your free hand, you might wanna use it on her tits or in her vagina.

There's something very CREEPY about a 14 year old girl being 'experienced' at anal sex.

[QUOTE=Buddy;260523][COLOR="Blue">I was just wondering about lube. Now seeing we are young, we do not have access to actual lube(I don't think we are using a condom for this reason too). Will spit from a quick session or oral sex on me be good enough? [/COLOR][/quote]

Buddy, Buddy, Buddy!~

[COLOR="red">[SIZE="5">STOP![/SIZE][/COLOR] [COLOR="Orange">Please slow down....
[/COLOR]
The two of you need much more insight and information than you now possess.

Lubricants, spermicides, and, condoms are available straight off the shelf of most supermarkets, drug stores, and, pharmacies. No prescription required. Even if you are too embarrassed to walk up to a checkout counter with each of these in hand, then talk to an older person to intercede on your behalf. Now, think about this: Young boys are naturally inquisitive when it comes to their body and sex. Cashiers are wiser, and male clerks have been there done that when it comes to masturbation and experimentation. That said, they know that horny guys are going to be curious about condoms and will buy them. They also know that they are curious about lubes and how the solution enhances our pleasure when applied to the penis. So, suck it up and do not be afraid to walk in pick up these items and present them to the cashier along with your payment.

It is utterly [COLOR="Red">dangerous[/COLOR] and [COLOR="Red">irresponsible[/COLOR] not to practice "safe sex". Always wear a condom. Especially wear a condom when engaging in anal intercourse. If you are unwilling to look out for her safety as well as yours and do what is necessary, then do not have sex. As mentioned, elsewhere in my reply, you can enjoy much more intense orgasms from foreplay activities! If you are not going to be responsible, then the two of you better have a plan in place for when she announces to all concerned that she is pregnant!, or worse, has contracted a social disease. Then there is you: if you do not look out for A#1, and do not want the future course of your life forever changed, then do not have intercourse {anal and/or vaginal) without a condom, and, a spermicide in her vagina.

Each of us, male and female, is responsible for our own orgasms. We do not give them away. All any of us can hope to accomplish is to help our partner achieve them. For her, this requires that she knows how to masturbate (something a lot of girls do not learn until much older, if at all) and can regularly and consistently orgasm. Only after she can do this can she show you how to mimic her technique. The same goes for you. Show her how you masturbate, then help her to mimic your technique for best most satisfying results. In all cases, give each other feedback on how you are responding to each other's caresses.

"Spit"? Saliva, is totally inadequate. Anal penetration requires copious amounts of lubrication in order to be safe and effective.

As for what to do with your free hand, I suggest before proceeding any further as a partnership, that the two of you read each and every article listed in the Index. Knowledge is empowering and right now you know just enough to be dangerous. I applaud you for asking questions. This is good. Don't stop. The articles will answer your questions, as well as a few you have not yet thought of!

As for what to do with your free hand, well, consider what you do with your penis. A clitoris is a miniature penis, even though the shaft is buried beneath a layer of skin. The small inner lips (labia) is akin to the scrotum and just as sensitive. This said, the clitoris is much more sensitive than a penis, so reading the articles will give the two of you much more information and insight on what and how to pleasure each other.

[quote=][COLOR="Blue">Is it also possible for me to get her to reach orgasm by pure anal sex? Any suggestions on what I should do with my free hands?[/COLOR][/QUOTE]

Not likely. Intercourse, either place, generally requires that the man reach around and stimulate her clitoris {tip and shaft) and/or labia in addition. That said, remember that we do not give orgasms away. She has to be able to climax on her own before a man can help her achieve them. This requires that she learn to masturbate successfully, something guys do automatically during puberty; not so with girls, generally. Until she can do this, and then show you how to mimic her technique, she will not climax. On the other hand, this does not mean that all this activity will not be pleasurable and satisfying. If you know what to do and do it carefully and skillfully, a woman will be happy. Having orgasms is a biological imperative for the male of the species, not so for the gentler gender. This is why learning all about making out and placing emphasis on the emotional aspects of this are so important.

My second recommendation is to turn your emphasis on sex around. Right now you have the proverbial cart before the horse with all your concerns about penetrative sex. Better for all concerned to learn how to turn each other on, first and foremost (women require much more time and effort than guys). Please read about fooling around and making out and the several stages involved. After each of you have read the articles, please discuss what you have read. Doing so will help make for much more rewarding and satisfying times together. (hint hint)

OK, sexual experience in a 14 yo woman is not unknown. I am exhibit number one for that. BUT, some few 14 yo men and women make themselves fairly knowledgeable; other "just do it." This latter group assumes much unnecessary risk. Are you aware that anal sex CAN, and sometimes does, lead to pregnancy? Are you aware of the risks to the penis going in there as well as to the anus being penetrated? A simple hook-up as you describe with a woman who has had multiple partners has greater risk of disease than dealing with with someone you have known a bit.

As doc points out, there are many ways for the two of you to experience sexual gratification, and learn a lot about sex, with very little risk.

It is time for you to back off; learn a bit and find a woman, in a few years, not willing to spread her cheeks for casual friends.

[QUOTE=EvilEvilKitten;260528]There's something very CREEPY about a 14 year old girl being 'experienced' at anal sex.[/QUOTE]

[color=green]i agree....and prefers anal over vaginal......interesting[/color]

As always, some super advice here. I too am just a bit gob-smacked at a 14/15 year-old being bedazzled with anal sex. Sensible of you it is to seek the opinions of the professionals. However, at your age I was still enjoying the miracles of masturbation and the occasional hand up the jumper of some obliging female.
Ahh, the joys of youth.
But good luck!

[QUOTE=Buddy;260584][COLOR="blue">Thank you for the advice. [/COLOR]

As for my part--you're welcome!

[COLOR="blue">Everything went great. We got a condom and instead of doing anal intercourse we did vaginal intercourse.[/COLOR]

Just curious, did you purchase the condom or get one from a friend? ;)

[COLOR="blue">I was kind of nervous at first but she helped a lot by guiding me in.[/COLOR]

Being nervous is completely understandable! (Who wouldn't be? Who hasn't been? BTW, there is an article on this that discusses having different levels of experience.)

She helped? How wonderful! She is a knowledgeable partner.

[COLOR="blue">She said it was the best pleasure she has ever had too. It lasted for about 15 minutes and we orgasmed at around the same time. I honestly thought I was only going to last 3 minutes but I was surprised at how long I lasted. [/COLOR]

Whether actually true or said simply to bolster your confidence, I would never question the statement. She seems wise beyond her years.

If your curious on the positions we did, we did missionary, and cow girl. She loves it when I play with her boobs too.

Some of us regularly promote the use of the Cowgirl/Woman Superior position for first time intercourse because a woman knows where P and V are and can deftly bring the two together; she knows how much pressure to apply and where, she knows where to position the penis should the hymen be intact.

You can play with her breasts most anytime; although, involving an Areola and nipple when she is very aroused will intensify her level of arousal.

[COLOR="blue">We are planning on doing it again sometime soon too.[/COLOR] :)[/QUOTE]

No doubt, really? :D :cool:

In the meantime, please read the articles, either separately or together, then discuss what you have learned. Add all this to what you each of you already knows. Knowledge is empowering.

i agree with them u are soo not ready. and 2 me a 14 year old girl that expernced is a
little creepy

Don’t have too-high expectations in first time sex. Sex generally improves as you get to know someone and become more comfortable with each other’s bodies. First-time sex can be tense and nerve-wracking, not to mention painful sometimes. Taking long, deep breaths can help you relax and let go.