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Thread: Guy losing virginity to experienced woman--help

  1. #1
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    Default Guy losing virginity to experienced woman--help


    Hi,

    Iím new here and I need some objective information, so I hope someone here can
    help.

    Iím a guy whoís a late bloomer, 22-year old virgin--I have always tended to be
    extremely shy and lack self-confidence around women. But my girlfriend and I are
    very serious--Iíve been with her for 6 months and Iím ready to take the plunge.

    The problem is that my girlfriend (whose 23) isnít a virgin. Sheís had two other
    partners with whom she got a good bit of sexual experience (one of them in
    particular). This makes me very self conscious and worried about the fact that I
    wonít know what to do and wonít measure up. I find her beautiful sexy, and
    exciting, so I donít have trouble getting excited with her, but the fact that
    sheís experienced is very intimidating for me. These guys have been out of her
    life for some time--the last time she had sex was two years ago--but I still
    feel intimidated and inadequate. Iíve told her how I feel, and she has been very
    reassuring that she loves me and doesnít think about those guys any more, but
    she still knows what to do and I donít. Since Iím just starting out, Iím sure I
    wonít be able to excite her as much as her past partners.

    Also, sheís on the pill, and she wants my/our first time to be special. Sheís
    tested and is disease free, and since Iím a virgin whose never done drugs or
    anything Iím sure Iím clean, but I worry about how effective the pill is (Iíve
    never needed to know this stuff before--the stats on line look pretty good but
    Iíd like to hear it from real people). Plus I have heard that a condom can keep
    me from climaxing too fast the first time.

    So I guess I can use some advice as to the pill, condoms (yes or no), and
    generally how to go about losing my virginity with my girlfriend in this
    situation. Any details would be appreciated. Thanks!

  2. #2
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    My experience with guys who have not had sex before tend to go way too fast and want to be inside me after only a few minutes of foreplay. Experienced guys with the right intentions go a lot slower and wait until the girl is fully aroused. So go slow, and let her step the pace. She'll let you know when fully aroused.

    Kinda surprised you've been together 6 months and only now are consider sex. I'd wonder how strong of sexual chemistry a couple has if takes that long. I don't jump into bed with just any guy, or do it right away, but if I really like a guy and he likes me, even a couple of months would be a long trial period to see if we like each other enough to have sex.
    Last edited by LisaW1991; 04-08-2013 at 01:00 AM.

  3. #3
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    Boys are different, first time isn't always special or great for us, it might be interesting though. So what I suggest is don't fuss about it too much, take the plunge, feel great, if you're both disease free and she's on the pill, first do it without the condom and if your stamina is good, use a condom when you get an orgasm.

    Take care

    Quote Originally Posted by Brad90 View Post
    Hi,

    Iím new here and I need some objective information, so I hope someone here can
    help.

    Iím a guy whoís a late bloomer, 22-year old virgin--I have always tended to be
    extremely shy and lack self-confidence around women. But my girlfriend and I are
    very serious--Iíve been with her for 6 months and Iím ready to take the plunge.

    The problem is that my girlfriend (whose 23) isnít a virgin. Sheís had two other
    partners with whom she got a good bit of sexual experience (one of them in
    particular). This makes me very self conscious and worried about the fact that I
    wonít know what to do and wonít measure up. I find her beautiful sexy, and
    exciting, so I donít have trouble getting excited with her, but the fact that
    sheís experienced is very intimidating for me. These guys have been out of her
    life for some time--the last time she had sex was two years ago--but I still
    feel intimidated and inadequate. Iíve told her how I feel, and she has been very
    reassuring that she loves me and doesnít think about those guys any more, but
    she still knows what to do and I donít. Since Iím just starting out, Iím sure I
    wonít be able to excite her as much as her past partners.

    Also, sheís on the pill, and she wants my/our first time to be special. Sheís
    tested and is disease free, and since Iím a virgin whose never done drugs or
    anything Iím sure Iím clean, but I worry about how effective the pill is (Iíve
    never needed to know this stuff before--the stats on line look pretty good but
    Iíd like to hear it from real people). Plus I have heard that a condom can keep
    me from climaxing too fast the first time.

    So I guess I can use some advice as to the pill, condoms (yes or no), and
    generally how to go about losing my virginity with my girlfriend in this
    situation. Any details would be appreciated. Thanks!

  4. #4
    Silver Contributor 100+ Posts Array Harmony's Avatar
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    Congratulations. At least you've been brave enough to come here and ask for help/advice/reassurance. Many men wouldn't for a variety of reasons. I wish I'd had somewhere like this to go when I was younger. If I'd had it would have been me asking questions like yours instead of me trying to pass on what little pieces of knowledge I managed to glean through trial and error over the past few years as I muddled my way through my teens and early twenties.

    I was with my first GF for 3 months before we had sex, and she, like your GF was sexually experienced already. So I understand your position (no pun intended). I was 19 and a half the first time we had sex and she was 18. Previous sexual experience doesn't guarantee that she had an amazing sex life prior to meeting you, but what this results in for a man, is that as men we're quite competitive by nature, and subsequently you now feel like a competition exists (though it probably only exists in your head) between you and these other men (her previous lovers) and you need to prove yourself to be 'better' than them and you're worried that with the handicap of having no previous sexual experience you will not be able to.

    This is all very normal. And if you don't think it is, seek comfort from the fact that I felt like you when I was younger.

    Lisa is correct in my opinion; though remember that all experienced men started out inexperienced, and it is not where you start, it is where you end up that counts.

    It is also normal for women to be more sexually experienced than boys their own age, and start having sex from a younger age than boys, at least that's the impression I got. When I was at school I can remember the girls maturing a lot faster than the boys.

    Rather than going on to much I'll just try and bullet point some do's and don'ts that I think will help you.

    DO NOT
    1) Ask your GF if your penis is bigger than her ex lover/s. If you have, never ask again.

    2) Expect to take her to the peak of sexual ecstasy once you start having sex. I'm all about not being a selfish lover, and while I've never had sex with a virgin I would go out on a limb and say that at least the first few times you have sex will be all about you. By that I mea that there shouldn't really be any expectations on you to make her climax. So do your best to take the pressure off of yourself. The first (maybe few) attempts at sex may well be clumsy and unsuccessful and the first few times (at least) will likely be very brief/quick, which is to say (without sounding like a ********************************k) you'll probably prematurely ejaculate. Just try and enjoy yourself.

    3) Ask/grill/interrogate your GF for details (sexual and/or non-sexual) about her ex's. It's not attractive and nothing good can come from it.

    4) be resentful she has had sex/sexual partners/relationships and you haven't. As a man I can attest that on one hand it is quite humiliating/awkward/embarrassing and paradoxically emasculating losing your virginity to a sexual experienced woman but be grateful she's sharing this experience with YOU. You're essentially going to be deriving a benefit from her and her ex's. In retrospect I'm glad I did it the way you are now.

    5) put a time scale/deadline on this and think stuff like, 'I HAVE to have had sex with her by the end of the week'. Just keep fooling around and it will happen. Trust me.

    6) Try too hard to please her sexually and put pressure on her to climax.

    7) beat yourself up or get upset if you experience any teething problems. You'll probably just get too excited at first and cum too quickly, which is very normal with less experienced men. Fortunately there are plenty of ways to deal with that which we'll get onto later.

    8) be ashamed of being a virgin, 22 is late in my opinion (and that is only my opinion for what it's worth) but late doesn't mean bad. All it does in my opinion is typically raise problems regarding an unequal balance in sexual experience since the 'late' partner (like I was) will typically find themselves with some catching up to do. While the insecurity will probably be equally balanced for late starting boys and girls problems are usually more manifest for the boys as they're the ones who control how long sex lasts. For this reason late starting/inexperienced men usually feel more pressure and experience more difficulties initially than late starting women.

    This also highlights something else which is very interesting (which will be the topic of conversation in the next thread I start) regarding pre-conceived ideas about gender. Society in general does (unfortunately) view female sexual activity with more moral criticism than male sexual activity. Women get called/labelled ****s for promiscuity while men get a proverbial (or literal) pat on the back.

    But while women (rightfully) lobby for equality for women and the absence of gender discrimination (the absence of gender discrimination needs to work both ways for it to be absent) we often forget that many expectations still rest upon men to conform to particular standards and to have the innate ability to fulfill certain roles. This is made even worse by the fact that many, many, men now have grown up without a father figure (and are often raised by a single mother who had no father figure either) and yet the pressure is as still as great as ever.

    As men we tend to make it worse for each other by not be supportive too, so we bring some of it on ourselves.

    Different women will have different expectations of a man but how does society view a woman who confesses to having trouble climaxing? This is a slightly taboo subject but would a woman seeking counsel in her pursuit of multiple orgasms be viewed as inferior, as un-feminine? I doubt it, but a man the same age who admits he cannot stop himself cumming will definitely be more reluctant and embarrassed when considering looking for help, and will likely be subject to ridicule and embarrassment from his peers.

    Another example is the way women demand equality in the workplace and the right to work in traditionally male dominated roles, yet have they considered the prejudice with which they view men who wish to do the same and work as nursery nurses, nannys, or hairdressers? As women begin to occupy job roles traditionally filled by men that leaves one more man looking for a job and one more vacancy a women may have filled.



    DO:
    1) Enjoy yourself, don't feel ashamed of your circumstances

    2) LEARN, and strive to learn more. Read,
    the barefoot doctors handbook for modern lovers
    the couples guide to getting it on (read this last)
    the multi orgasmic couple (this book details the exercises which will help you control your orgasms and last longer. Do these religiously and don't when you feel them working. Don;t expect them to work straight away and don't try the sperm retention techniques; at this stage it is only controlling orgasms you to concern yourself with.)
    how to give her absolute pleasure
    she cums first

    3) 'listen' to her body. when you fool around gauge her responses when you caress and touch different parts of her body and look out for the 'hot spots' (you'll be paying extra attention to these in the boudoir) lower back, neck, and insides and backs of thighs are a good starting point.

    4) Be open to the idea of using sex toys in the bedroom - it doesn't make you 'inferior' using a vibrator or dildo to make your GF climax. What does (or can) make you inferior is closing your mind to the concept of creativity in the bedroom. I bought my first GF an 8" sex toy and she loved it. When I'd cum too quickly for her (most of the time) I'd sit there and watch and masturbate while she finished herself off with it (while wearing her nurses outfit).

    5) Appreciate your GF for who she is, and that includes any sexual experience she's acquired on her journey through the thoroughfare of life. This has helped shape her into the woman who who've fallen in love with. If those ex's - and they are ex's now, and for a reason - hadn't screwed up somewhere along the line you would have never got your chance with her.

    6) be open about your feelings and communicate. COMMUNICATE-COMMUNICATE-COMMUNICATE. I'll say it one more time: communicate. If there is a problem and you don't acknowledge it, discuss it and tackle it head on it will affect the relationship and after failed attempts to deal with it she will become frustrated and eventually give up.

    By reading the threads on here you'll see that actually, sexual problems like erectile dysfunction, premature ejaculation and whatever else - while they are problems - the women who come here looking for help are doing it because their partners wont. The real issue and cause of problems becomes the man's refusal to tackle the problem head on: his lack of communication and reluctance/fear of the humiliation of dealing with it. Never be like this.
    Don't give her ear damage but be open about your feelings, what you enjoy, what you want to try and what she wants you to do. Be an attentive and caring lover and partner.

    I searched online once for advice for boys about losing their virginity and I'd never seen so much bunk in all my life, I mean it actually hurt my eyes. The lack of support and resources available for men, and their innate reluctance to ask for help, compounded by societal attitudes has the obvious and insidious effect of causing an immeasurable number of problems in society in my opinion.

    Good luck
    LisaW1991 likes this.
    No matter how objective we try to be, we all see through our own eyes...

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    Thanks for all the replies (especially Harmony). Lisa, there's definitely a lot of chemistry. We have already done a bunch of stuff, and I've learned a lot about her body and her responses already, which has helped me loosen up. I will be sure not to go too fast and wait until she lets me know she is ready for me to penetrate her. Harmony, you're right about the sense of competition--I worry that when we have sex for the first time she will be doing things she learned with other guys and I'll feel like a newb and won't be able to satisfy her. But I will work on not dwelling on it and I think your advice will help.

    So any thoughts on the Pill? she is on her off week right now and we will probably have sex once her period is over. Is she safe even during the off week?

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    If she is on the pill, sex at anytime should be OK. Nothing is 100%, even condoms, but the pill is practically as safe at preventing pregnancy as the condoms. Technically speaking a girl can only get pregnant a few days each month even when she's not using any kind of protection, often called the "Rythm method". Condoms are important for sex with partners who have had sex with multiple people and could have a STD. Kinda sounds like you've got that covered already, so need to get into those details.

    Sex without a condom is more enjoyable, but sense you don't now any different, then its not like you're going to noticed the difference. She might. I personally don't like condoms in terms of pleasure, I like the feeling when a guy peaks and has his release while still inside me. Maybe its the biological drive to get pregnant, I can't explain for certain, just prefer he stays inside.

    I'll say when I was 15 I had sex with a guy in his 20s that never had sex before. I was kinda surprised and did not find out until we were in bed about to have sex. He never actually told me until later, but it was clear when we were having sex that he was unfamiliar with the sexual details of a girl's body. I had suggest he go slower and later when I was fully aroused, I had to guide his erection to my vagina opening because he was aiming at a little too high, he thought my opening was near the top of my pubic area. We had a nice time for couple of hours, but it was a little weird for me to be showing\explaining to a man the basics of how to have good sex. If I had known he had never had sex before, I probably would have taken things slower with him. I had only know him for a couple of weeks and assumed he had plenty of sexual experience, so there was no reason to go slower. He as a quick learner though and it really didn't take more than a few times to get beyond the basics. He really was a sweet guy, and I enjoyed having sex with him.

    see ya

    Lisa

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    As long as she starts her next pack on time then she's covered. If you are worried, then just wear a condom. It's the best way to protect yourself and make sure you don't end up a father before you're ready for a little tot with your eyes.

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    A Few comments here..

    Thats strange bc most men like being with virgin women.

    Women also like being a mans first too. I see u keep notches on your belt like a man does.

    Maybe u can tell us how u pounded penises into smaller sizes. Lol
    Super, I'm sorry to ask this, but are you experienced in New Relationships and being a Virgin, whether Male or Female ?

    You comment (Above ) to Emily, to me,and I did not even post it, was Offensive to say the least .
    Women don't always like Being the First to a Man and many Men don't like Being with a Virgin .

    This young man is asking questions to make his First time be Special , not only for himself, but for the Woman who is willing to Teach him .. Sexual Pleasures. I doubt she is going to take " Pride " in taking his Virginity, It sounds more like she really Cares for him and it's Not all about Sex . That she wants to help him become Sexual and Sensual in their Relationship.

    Emily, was sharing, as the others have, her Experiences, this was to help Brad. I see nowhere that She says keeps notches on her belt or Pounds Penises into smaller Sizes. I see no humor in your comment, I do see Immaturity and lack of Respect for those who are trying to help this Young Man .

    On your other comment ( this again is to super )
    Btw it may bother u later that she was on the pill with a guy before u. If this wont bother u go ahead and take the plunge. Otherwise u may want to wait for another virgin.
    Why would it bother him that she was on the Pill ? Why would it bother him that she has has sexual activity before him ? He knows this, this is why he is asking US for Help !
    She is Being Mature and Responsible, by being on the Pill to Start with .

    He is a bit nervous about his first time,he has a Willing Teacher, he is no different than a Woman coming here and asking for advise of her First time.

    Brad .. I'm very proud of you for coming here and asking. I hope your first time is Awesome for you .. Even if things aren't " Perfect " Relax, Enjoy and do what feels best. Then the next time, Enjoy even more..

    Practice makes Perfect.

    Lisa, Element, Harmony & Eugene .. Excellent Advise and I'm Sure that Brad appreciates it .



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    Quote Originally Posted by Sooper View Post
    If women want to brag about sleeping around... Guess what. Its not the same as a man. Mainly because a womans vagina gets bigger the more sex she has. A mans penis does not change
    This is not true, even even a little bit. Its one of those urban legends that has no truth to it. And guess what? ...only guys believe it.

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    Hey guys, deleting your posts to Sooper

    Sooper won't be responding.
    PUT A LITTLE 'LIKE' IN MY SOUL!

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