Women and Virginity: Preparing for the First Time

bedside-candleMost of my blogs over the years have been written for people who are already sexually active and have experience with pivi (penis-in-vagina intercourse). Today I’m going to address young (and perhaps not-so-young) women who are interested in losing their virginity. (I hope guys will read this as well—virgins or not.)

Losing your virginity is not a topic that most of us bandy around in casual conversation. But I’ve been privileged over the years to hear thousands of descriptions, most of them about experiences that were awkward, clumsy, and sometimes painful. It doesn’t need to be that way.

I heartily recommend that your first sexual partner be someone who is gentle and kind, with a good sense of humor. And please, please, please don’t be drunk or high your first time. Take it from me: Couples who do it sober have a happier and safer experience!

Losing your virginity with your sweetheart and soulmate would be a lovely option, but most of us no-longer-virgins are not even in touch with the person we did it with for the first time. One of the keys to having wonderful sex is knowing your own body.

Regular readers may have read comments recently from older women who are enjoying sex more and more the older they become. One reader celebrates post-menopause as a time when she knows her body well enough to say yea or nay in ways that her lover can truly understand. Another writes about discovering new delights about her body as she ages. Whatever your age, consider yourself at the start of a fascinating journey!

If you masturbate, you have an advantage in this department. If you haven’t explored your body this way yet, not to worry. I suggest you try for a time when you have 30 minutes to yourself or when you’re tucked under the covers for bed. First, wash your hands, then moisten your fingers. (I mistyped “finders” here—how perfect!) Let your fingers “find” pleasing places on your body—everywhere except your genitals.

Relax, breathe, and allow yourself to spend at least 10 minutes exploring up and down your body. You might want to imagine that your lover’s fingers/finders are discovering erogenous zones that you weren’t aware of before. Then, let your focus shift to the area between your legs, with your fingers gliding up and down and around your vulva, the outside part of what’s between your legs, as opposed to the vagina, where tampons and penises (sometimes) go.

Next, get your finger extremely wet (saliva works fine) so you can venture inside. Slowly inch your finger inside, allowing yourself to feel what your finger is “finding” inside as well as what your vagina might be feeling. Some women may want to explore more deeply, while others might feel quite nervous and hesitant. If you’re in this camp, this might be a good place to stop for now. Congratulate yourself for taking this important step and consider venturing a bit farther the next time.

If you’re eager to press on, let your finger keep going. Remember to breathe, and continue to ask yourself what your vagina is feeling and experiencing. You might want to consider adding a second finger, especially if you anticipate pivi.

I highly recommend a wonderful book by my colleague Lonnie Barbach, called For Yourself, about masturbation. Female virgins and nonvirgins alike may benefit from carving out pleasurable time “for themselves.”

If all of this seems too overwhelming, maybe it’s not the right time in your life to be losing your virginity. Millions of lesbians will attest that there are numerous ways that you and a partner can enjoy one another sexually without a penis going into your vagina!

© Copyright 2013 GoodTherapy.org. All rights reserved. Permission to publish granted by Jill Denton, LMFT, CSAT, CCS, therapist in Los Osos, California

The preceding article was solely written by the author named above. Any views and opinions expressed are not necessarily shared by GoodTherapy.org. Questions or concerns about the preceding article can be directed to the author or posted as a comment below.

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  • laura

    laura

    August 20th, 2013 at 8:43 PM

    still remember the day I lost my virginity.was 17 and no it was not a great experience.was not used to masturbating so that did play a role there.later when I started to masturbate I identified and understood my body and the pleasure points.enjoyed sex much much better after these discoveries.

    so I’d suggest all young women out there to discover their own pleasure points and to know there own body better.it definitely helps your sex life!

  • Catey

    Catey

    March 11th, 2017 at 11:03 PM

    My boyfriend and I have been dating for 7 months and he’s been trying to get in my pants but I’m nervous because I’m a virgin…………. I’m so scared

  • Jennifer

    Jennifer

    August 21st, 2013 at 4:01 AM

    Well that was a lot more to that article than I thought that there was going to be!
    I’m okay with that but kind of makes me glad that there wasn’t so much build up to my first time, just did it and got it over with!

  • Rhonda F

    Rhonda F

    August 22nd, 2013 at 4:01 AM

    It was not until I was an adult that I began to take control of my own body and masturbate and learn what I liked and didn’t. When I actually lost my virginity I knew nothing about that, I was just concerned at that point about keeping my boyfriend around. It makes me sad but I think that a lot of women of my generation probably lost their bvirginity for the same reasons, not because they were really ready but because it just felt like the right time and they were just ready to get it over with.
    If I had known more then I would have waited a lot longer and would have honestly been able to give more instruction about what felt better to me. I guess I can’t go back now, but I can instruct lovers today and have better experiences now than in the past.

  • Anonymous

    Anonymous

    September 29th, 2013 at 1:16 PM

    I was 31.
    Kept waiting for feelings of attraction, lust, desire, interest, anything, to bubble up. They never did. So I finally just picked a guy at work; a few week later it was over.
    Why so late? Your guess is as good as mine. No one ever showed any interest.

  • Autumn

    Autumn

    April 24th, 2015 at 10:49 PM

    Losing it tonight. Woo hoo!!

  • Michael

    Michael

    December 29th, 2016 at 12:53 PM

    Good for you and your lovers

  • Val

    Val

    July 31st, 2015 at 10:49 PM

    I just turned twenty on the 5th on July 2015. Not only am I still a virgin but I haven’t even kissed anyone yet. (I know, I’m lame) In six days I am meeting my boyfriend for the first time, in person. We’ve been in a long distance relationship for 2 months now. I am so nervous, anxious and excited about my first kiss and losing my virginity. He knows I’m a virgin so he does know to be careful, but how can I calm the nervousness?

  • Jill Denton

    Jill Denton

    August 2nd, 2015 at 12:39 PM

    Hi Val, I’m glad you found my blog so recently and I can imagine how nervous you feel about meeting your new boyfriend. I think the most important thing I can suggest is that you let go attachment to outcome!! You’re scared, I think, because you’re assuming that this first meeting will mean that you MUST “lose your virginity!” This need not happen, and it might be much better if it doesn’t! I’m reachable by text or phone via my website which is JillSexTherapist.com. Feel free to contact me if you’d like!

  • Val

    Val

    August 10th, 2015 at 8:11 PM

    Hi Jill, its Val again. I lost my virginity and had my first kiss on Thursday (8-6-15). I was nervous but in the moment it felt so right. I wanted to thank you for writing this blog post so I felt like I had a safe place to address my concerns.

  • tina

    tina

    November 25th, 2016 at 11:31 PM

    hi Jill, I’m 22 years old virgin. the reason that i still didn’t have a sex because of feeling scared on pains. the question i want to ask you is it painful???

  • shelby

    shelby

    July 1st, 2019 at 9:56 PM

    so im 18 and me and this guy have been together since we were freshmen in highschool and im still a virgin at times he wanted to get in my pants but i told him i didnt feel comfortable yet so we waited and waited next thing i know its my 18th birthday so he calls me and begs me to do it and still i said no and im ready but the reason why i keep saying no is because im afraid its going to hurt when me and him have sex plus i have a fear of getting pregnant but i know he loves me and i love him

  • Kate123

    Kate123

    August 10th, 2015 at 7:48 PM

    Hi Jill,
    I am about to turn 20, and I have never felt so ready to lose my virginity. I’ve dated many guys and had the chance to, but I never felt ready. I always felt it was just something far away. But now, I know I’m ready to take the next step in my sexual life, if you will. The thing is, I’ve always wanted to lose it to someone I’m dating, someone I am deeply in love with. But I am no where close to being deeply in love or in any committed relationship. This idea popped into my mind and I cant stop pondering this. Let me know what you think. Maybe it doesn’t matter the type of relationship you have with the person, but more how much you care about and trust them. Maybe it’s better to lose it to someone you know you’ll always be friends with, even if that is just your guy friend you’ve known your entire life and will always love. I was close to losing it with an old boyfriend, but I didn’t because in the moment part of me deep down knew he was going to drop me when he was done with me. And then I’d regret it and look back on my first time in sadness and regret and hate. But if I made my first memory of it with a friend, and guy I’ve known longer than anyone I can think of, maybe it’d logically be a good idea. Maybe it’d still be meaningful and I could look back on it like yep I lost my virginity to my bestfriend I love unconditionally and will never leave me, so I didn’t have to stress about losing it to someone who won’t matter in a year. Am I delusional, would I regret this, or would going with my heart be a smart decision?

  • Jill Denton

    Jill Denton

    August 11th, 2015 at 2:23 PM

    First to Val – you’re welcome! Now Kate….tough question which I can’t really answer because I don’t know you OR certainly your best friend! You also haven’t mentioned how HE feels about this! Sex often brings lots of complicated feelings and it often changes the form of relationships. I hope other blog readers will add their thoughts. And Kate I also invite you to contact me if you’d like to explore this in more depth. I left instructions on Aug. 2 in post to Val.

  • Erin

    Erin

    August 11th, 2015 at 3:46 PM

    @Kate: Only you know your relationship with your friend, but I can tell you that my experience was great with a casual guy friend! I was 21 and totally desperate to lose my virginity, but didn’t much care about finding total love or having a long-lasting relationship. I deeply cared for my friend, and he for me, but there were no expectations.

    Does your friend know you are a virgin? If not, I want to urge you to tell your friend and to be completely honest about your level of experience… but that would make me a hypocrite. I lied and had an alibi for when I “lost my virginity,” so my friend didn’t know. It haunted me for years until I recently told him (he’s still my best friend). He understood why I kept it secret and was not hurt by my lie, but I still feel strongly (especially moving forward in my intimate relationships) that such dishonesty is no basis for any type of romance, even a fling. If you do choose to keep it secret, I’d highly recommend doing a lot of… erm… *exploration* on your own beforehand, if you haven’t already—just as Jill advises in the article. Actually, I’d recommend that anyway. My first time was not painful because I had been fairly adventurous by myself :) It makes the experience a whole lot easier.

    Finally, be aware that even if you don’t have feelings for your friend, and even if you don’t develop feelings for him, you will probably want to have sex more after you lose your virginity. And unless it’s totally awful (unlikely, if your connection with your friend is as deep as it sounds), you’re probably going to want to do it again with that same friend. So just stay in constant communication about whether you or he intend to continue a friends-with-benefits situation, or have it just be a one-time event to get the actual virginity-taking over with, or what.

  • Kate123

    Kate123

    August 17th, 2015 at 6:10 PM

    Thanks guys for the advice. I’m still thinking about it. We’ll see what happens😁

  • Danielle

    Danielle

    August 25th, 2015 at 6:17 AM

    Hi Jill,
    My name is Danielle and I am 15 years old. I feel as if I’m ready to take my relationship to the next step and have sex with my boyfriend. I need advice.

  • Dessie

    Dessie

    August 30th, 2015 at 1:24 AM

    Okay so I’m 19…I’m a virgin. I do masturbate but I have never reached an orgasm. I go and then I get sore and can’t go on. Is that normal? How can I reach that peak?

  • Jessie

    Jessie

    September 29th, 2015 at 4:15 PM

    It was a well written article but sadly it didn’t hold any information I don’t already know, nor did it ease my fears.
    Meeting my boyfriend in person for the first time in our 6, nearly 7 years together. I’m a virgin and he knows this, we’ve had many long discussions on it. I’m still not sure I’m ready for this but after so many years I don’t think I can say no to him.

  • Tasha

    Tasha

    November 14th, 2015 at 12:38 PM

    Worst advice ever!!!!! The question is how to prepare for sex with your partner…. Not prepare for sex with your self… Fingering your self is sex.

  • Tasha

    Tasha

    November 14th, 2015 at 12:44 PM

    I am 22 and a virgin. I will have sex the first time on my wedding night. We have been together 6 years… It is very much possible to save your self if your not ready. Regardless when you have sex just makes sure your ready and it with someone worth wild. Because once you have sex you can never get a do over for your first time.

  • Hailey

    Hailey

    December 17th, 2015 at 7:56 PM

    My name is Hailey and I’m 18 years old. I’m a Virgin and one thing I really need to know is how to prepare ‘down there’. Should I shave/wax it or keep it hairy/trimmed? Which do boys like more? I really need help with this

  • Jill Denton

    Jill Denton

    December 20th, 2015 at 5:46 PM

    Hi Hailey – what’s most important is what feels comfortable for you. Worrying about what guys might like will keep you nervous and focused on them.

  • Kait

    Kait

    January 17th, 2016 at 8:50 PM

    Allright.
    Well what you ladies need to know is a clear definition of sex.

    It is a sexual orgin inserted into an orafice.
    What’s that? A hole.
    Whether its your mouth butt of ear.
    Its technically sex.

  • Lorine

    Lorine

    February 28th, 2016 at 9:14 AM

    Hi! I am in search of a dating coach for my niece. She’s a 40 year old Virginia. She’s hesitate with online dating and believes that she may need virgin group therapy. I do not know how to help her. Please assist! Thank you in advance.

  • Jill Denton

    Jill Denton

    July 14th, 2016 at 2:24 PM

    Lorine it’s wonderful that you want to help your niece. And I’m sorry I didn’t get to see you query sooner! Please contact me if you’re still looking so I can learn more about your situation. Or better yet have your niece contact me! JillSexTherapist.com

  • Noname

    Noname

    April 24th, 2016 at 5:27 AM

    M 30 yer old straight guy… Hd lot of opportunity to score (my frnds abbreviations)… I nvr did it… M kind of sensitive, worried n fr d reason I’ve been dumpd by gals many a tyms.. I usually gt things in my mind lyk Wat if it effects my partners emotional status… Currently m in a relationship… N my partner is on to me fr it… M kind of worried it shd nt turn into a regret… Fr both of us… Fr me sex is nt jst pleasure principle…. Dnt knw m lyk… Nooooooo…. Any help…! Her!?

  • Anonymous

    Anonymous

    July 10th, 2016 at 11:43 PM

    Hi! I am planning on losing my virginity in just a few days. I am excited / nervous because it’s not going to be with a boyfriend… I don’t have one. He is my “friend” but we don’t hang out often. He knows we’re going to have sex because we talked about it. I am still in highschool but I feel like I am ready. I am nervous that it will hurt/or bleed. I don’t know what to expect. Do all first timers feel pain? Also, I heard coconut oil is sake to use down there… Is it? Thanks!

  • lana

    lana

    July 14th, 2016 at 2:03 AM

    so I’m a 14 year old, and a virgin, my best friend is trying to “hook me up” with this guy. I’m all for it but she wants me to have sex with him, and I really don’t mind losing my virginity but I’m afraid it will hurt or I’ll bleed or I’ll make a complete fool myself. I feel like I’m young but I really don’t care about my virginity all that much, gonna lose it anyway, why not lose it to a cute guy?

  • Jill Denton

    Jill Denton

    July 14th, 2016 at 2:28 PM

    Iana I also want to reply to your more recent question by strongly suggesting that you say “no thanks” to your bf who wants you to have sex with this guy – even if he’s cute! You’ll have a much better first experience if it’s with someone you kow well and trust. Give yourself some time!

  • Kayla

    Kayla

    August 9th, 2016 at 7:11 AM

    I’m ready for sex but I don’t know how to prepare for it with my body and I have tried to masturbate but its not really working it just starts to hurt and I know I’m young but I’ve been with him for a year now and I feel its time. What should I do?

  • Jill Denton

    Jill Denton

    August 9th, 2016 at 2:51 PM

    Hi Kayla – I invite you to reread my blog piece above about how to begin exploring your own body, which can help you learn how to pleasure yourself or masturbate. If you’re touching yourself in ways that hurt, you’re probably going way too fast!

  • Nikki

    Nikki

    September 20th, 2016 at 2:05 PM

    Hi, Jill. I’m 22 and had my first sexual experience a few days ago. His penis was getting a bit painful for me, so he decided to give me oral sex… where I bled all over his face and into his mouth. Needless to say, I was mortified and he was traumatized. I guess what I’m asking is what’s the next step here? Will it hurt less next time? Will I bleed again? Did I do something wrong that I need to fix (maybe more lube?)? Is there more preparation I need?

  • Jill Denton

    Jill Denton

    September 20th, 2016 at 3:38 PM

    Dear Nikki – Some women do experience bleeding the first time they have penis in vagina intercourse – it’s totally natural and nothing to be ashamed or mortified about. Neither of you did anything wrong, and I would suggest you consult with your gynecologist so they can check you out and allay any fears you have about what happened physically. Counseling may help if your partner if someone that you want to stay with!

  • Nikki

    Nikki

    September 20th, 2016 at 4:41 PM

    Thank you for responding! Is there some way to prevent bleeding next time? I just want it to feel good some time soon.

  • Jill Denton

    Jill Denton

    September 21st, 2016 at 2:06 PM

    You’re welcome…and this is truly a physiological question that only your MD can speak to! All the best…

  • Cori

    Cori

    November 19th, 2016 at 4:07 AM

    Hi Jill,
    I am a 23 year old virgin. I am sure that i want to lose my virginity, but i feel strongly only for this one guy (mr.c) who is miles away (in another country). Like i have known him for almost 4 years now and i know i can trust Mr.C to keep it between us, to be gentle and to stop if i cant take it.
    But there is another guy in my life (Mr.J) who is understanding, gentle and works with me, so known him for the past 2 months or so.He is interested in me and has made the moves.
    But the questions are:
    1) do you think i should just get it done with Mr. J?
    Or wait for Mr. C?
    2) should i masturbate so its less painful? If yes then what would you recommend?
    3) what is best/ least painful position ?

  • tina

    tina

    November 25th, 2016 at 11:26 PM

    hi cori, we have the same a story and we also have same age i’m 22 and virgin. so i understand you well , the person you have to choose is Mr.J because what if Mr.C don’t came !

  • Cassie

    Cassie

    January 4th, 2017 at 12:39 PM

    Hi Jill,
    I was molested by my stepdad the summer of my 7th grade year and every since then, I have been addicted to masturbating and I have been basically wanting to have sex because that door has been opened for me and I don’t know how to close It. What do I do? I’m scared that it is wrong for me to masturbate and I want to have sex but I can’t. I’m scared. I’m lost. Where do I go and what do I do?

  • Jill Denton

    Jill Denton

    January 4th, 2017 at 3:45 PM

    Hi Cassie, You don’t mention how old you are and that certainly effects my response to your questions. If you’re in Middle School or High School there should probably be a counselor on campus that you could talk to. Self pleasuring (masturbation) is not wrong, but the experience of molestation is creating all kinds of confusion and fears for you. Please reach out and get help! You were victimized as a young teen and support is available. Another good option would be a local rape crisis center near your home. You’re courageous to leave this note and I wish you the best.

  • Cassie

    Cassie

    February 3rd, 2017 at 11:50 AM

    I am 17. I will be 18 in like 50 days. I am going to a therapist to get help, but I just fell like it’s not really helping. What other options are there?

  • Hoss

    Hoss

    February 3rd, 2017 at 12:21 AM

    I am in my eighteen years and I have black boss ( he is twenty five ) who wants to break my virginity so badly but I am afraid I might not be able to take his all inside what can I do to enjoy it instead hate it please help me love to hear from you soon.soon he is

  • Hoss

    Hoss

    February 3rd, 2017 at 12:22 AM

    need your suggestion soon thanks so much

  • Miranda

    Miranda

    February 5th, 2017 at 7:37 AM

    Hey it’s Miranda I am 17 yrs old and I have the best boyfriend ever. I have masterbated before. I want to have sex with my boyfriend he knows that I am a virgin. He said that we will take it easy for my first time but I’m still scared. Is there a way to prevent it from hurting. I’m also cause that I will bleed. I need help!!

  • Khaya

    Khaya

    March 2nd, 2017 at 12:06 PM

    How does it feels like?

  • Crystal

    Crystal

    June 6th, 2017 at 12:44 PM

    I’m 16 and I lost my virginity 1 week ago. I have been with my boyfriend 3 months and it felt like the right time. We didn’t use any protection and I’m happy to say I’m not pregnant. I feel like I know my body, so I could give him instruction on what I like.

  • Lucie

    Lucie

    October 3rd, 2017 at 4:24 AM

    Hi Jill,
    My boyfriend and I have been together for a long time and he’s not a Virgin and I am. I’m ready to lose it, I feel comfortable I just don’t know exactly what to do or what to expect.

  • Livvy

    Livvy

    May 15th, 2018 at 11:24 PM

    I need help. I have a best guy friend and we are really close, we just aren’t ready to date yet. He lives in NJ and I live in CO. We plan on meeting each other for the first time in 4 years. We talk about cuddling and kissing, but once he said he has a surprise for me for when we meet. That is more then kissing. I have a strong idea, but I’m so nervous. I don’t like my body. We’ve skyped before and he says all these wonderful comments. I’m scared he won’t like my body… But then again its in 4 years. Any advice? And I might want to lose my virginity to him. He’s a virgin too..

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