My girlfriend and I have been together for about a year and 2 months. We are each other’s first time in everything. I have tried my best to get her to cum, but everything I have done does not seem to do anything. I have told her I am willing to get taught what she likes and stuff. She had recently brought up that she just feels insecure when having sex. I have tried telling her how much I love her and her body. Calling her body perfect in every way possible to maybe help a little. She recently told me that she used to get pleasure from riding her pillow. I did not mind her telling me this, but what hurt was when she told me that it was better than our sex. Now I feel like my efforts are not enough. I am getting beat by a pillow. What can I do to get her to enjoy herself more with me? note that she has never finished in her life.

46 comments
  1. Keep doing what you’re doing. Then as you approach your climax, ask her to ride on the pillow in a way that makes her climax and then you can finish standing up in front of her. Or on the bed beside her. It’s my opinion that sex is flexible and 2 people can do whatever they need to do to adapt so that everyone gets the most out of it. Point of the story, don’t be intimated by the pillow, learn how to incorporate it.

  2. Have her ride the pillow as a part of it. Watch her and jerk off, telling her how beautiful and perfect she looks doing it. Encourage her to cum as she rides it.

  3. Focus on her learning to cum with a partner before you worry about whether you’re the physical reason she cums. You’re putting additional pressure on her when the goal should be simply to help facilitate her orgasm in any way you can so that she’s more comfortable. Whether you get yours or not, you should be focused on helping her.

  4. My wife and I both enjoy masterbating and sometimes cum from piv sex. Sometimes we don’t. I always encourage my wife to masterbate before sex, it makes her extra creamy/lubed and helps her orgasm. Foreplay is big for us, I do a lot of fingering and we both find it relaxing. You both need to find what works for you. Try to throw your insecurities out the window and take this as a fun challenge. The beauty of sex is that there are a lot of ways to do it.

  5. Is she on any kind of medication?
    ADHD, anxiety/depression medication, and pain killers can both decrease sexual desire and make it significantly harder to orgasm.

  6. I come like your GF, I’m a pillow rider. It’s really hard to replicate with a partner, the closer I’ve come is grinding on my partner’s thigh or, when it was a woman, her pussy or ass (ass is uncomfortable for erect penis owners).

    My current BF is the only one to make me come differently, mind you I’m 32 and I’ve been having sex for 15 years. He found a way to masturbate me manually that allows me to come, if I think of the right things. There’s a few positions (me on top mostly) where I’m able to grind on him while he’s in me, but I need total control, I’m moving he’s waiting for me to come. But I wouldn’t have had the courage to do this when I was younger.

    Just love your girlfriend, accept her coming is not in your control, make some suggestions and see what she’s comfortable with. She might also not know what she likes and be able to tell you what she wants done/to do, so try stuff, as much as possible.

    I’m sorry she said it’s better than your sex, she shouldn’t have said that, it must have hurt a lot.

  7. you are making a big mistake. I have several ex boyfriends like you and they always beat themselves up for something that was out of both our control. She probably loves having sex with you, because emotional connection and the intimacy, but physically, she responds better to other things. The sex is not just about the end goal, it is about the process of being together and build up. For women, every woman is different in what she responds to but most of us want to have sex for the emotional connection. Sex is very physically rewarding for men, but sex does not get women off. It’s a small proportion of women, 20%, who are capable of an orgasm from penetration alone. In addition to that your gf does not know what an orgasm is like, that’s more rare but I’ve heard of it before. She either doesn’t know that she’s already orgasmed from masturbaiting or she can only reach climax from using toys and hasn’t found a toy that will do that to her. Nothing can replace sex with you, but you’ve got to stop feeling like you are in competition with whatever turns her on. Thats probably why she hasn’t come yet, because you are discouraging anything that will get her there. If she likes pillows, get her to ride a pillow in front of you. Get her a vibrator. Get her dildos. It doesn’t matter, because as long as you are experiencing it together, it builds intimacy.

  8. If she hasn’t had a orgasm from masturbating then really, you need to start there. She has to be comfortable and know what turns her on. It’s more mental for women. You git to get in her head and talk about what turns her on.

  9. It’s not your fault she can’t cum. She told you she’s insecure…her lack of orgasms isn’t due to your inadequacy so stop focusing on that. Your mission should be to find ways to help your gf become more comfortable and get past the mental hangups she has about sex.

  10. As others have said, majority of women don’t cum from PIV.

    The amount of pressure you have put on your girlfriend having an orgasm is also not helping the situation.

    You say it’s for the benefit of her pleasure but from your comments it is also very much to help your self esteem. You have made this situation about you.

    She can ride your leg like she rides her pillow. You can try a vibrating cock ring and she can grind on that while on top.

    But guess what? It’s not the end of the world if she doesn’t cum. And you putting stipulations on how she is “supposed” or how you’d prefer her to cum is problematic.

    I am proud of her for not faking it.

  11. My advice would be to let her get comfortable cumming in front of you first – let her ride her pillow to cum if that’s what she wants. The whole thing with riding a pillow (from a woman’s perspective) is that it stimulates the clit. Once she’s able to actually cum in front of you, have her try rubbing herself during sex / you do it.
    Not saying you are (but it sounds like it) don’t put pressure on her to cum during PIV because many women don’t and the pressure will make her feel worse. Other than that, keep trying and getting to know her body and be patient. Good luck!

  12. You gotta hit those spots man, start with kissing and touching things that aren’t her private parts, but close to them, kiss her neck, her earlobes, her collar bone, kiss down her stomach, around her bellybutton, inside of her thighs and so on, make sure you cut your finger nails and finger her like you telling someone to “come here” with two fingers curling up twords the ceiling if she’s on her back, rubbing the top wall inside her v, not too deep, slowly feel the top wall, you will find an area that’s kinda like feeling little ridges, that’s her g spot, watch her for her reaction, she will show you when you are in the right spot if you pay attention, once you find that, go down on her with your tounge or use your other hand on her clit at the same time you are rubbing the g spot. Experiment with different speeds and spots while watching her reaction. Get her off at least once this way before you even think about sticking your dick in, once she finishes that way, it’s way easier to get her to finish again on your dick. Try all that and you shouldn’t have a problem getting anyone off again.

  13. Maybe try letting her grind on part of your body even if you just lay your arm on the bed, maybe over time it can be turned into something else Many men can only cum from masterbating they know exactly how to do it to get off

  14. The love of my life almost never came from PIV without a vibrator. You can’t take that shit personally. We were together for 6 years and 99% of the time she used a vibrator. If you let that shit deflate your ego, then you’re going to fuck things up. Some women can, some women can’t. Let it go.

  15. Imo watching porn SHE likes or even letting her watch it solo and masturbate is helpful in letting her build the confidence to cum regularly which is what she needs if she’s ever going to come from PIV.

    Let her really explore the kind of porn that she likes instead of just generic stuff you expect porn to be.

    Often I like to watch amateur porn because it just has this feel of like realism to it that I feel that other kinds of porn lack.

    I also think that you should keep options open to like sexy gifs and pictures… these things exist and can be highly erotic.

    Sometimes erotic fiction coupled with roleplaying is also helpful.

    Don’t overthink these things just try to enjoy being with your girlfriend in these sexy moments.

    My recommendation if you prefer missionary make the experience more about her than your dick being inside her.

    If she’s a pillowrider will probably have more luck with cowgirl in cumming.

    But the reason she finds pillow so pleasurable I believe is because of the gentle intimate contact with all parts of her pussy and not just the inside of it. I believe if you can replicate that she will cum and having your dick inside her will just enhance the orgasm.

    Enjoy

  16. This is not at all unusual. Don’t be discouraged. She has had a long time to perfect her pillow technique.

    You might ask her if she like to use toys or would like to bring her pillow into the session if your ego can stand the competition.

    I also suggest consulting a sex therapist.

  17. Ok, here’s my spiel – Look up the following. She’s not just about the sex, this podcast is pretty cool with other couples talking about their experiences.
    Check this woman out on YouTube or Spotify or IG. She has so many life lessons, advise for men, women, couples, etc. She talks about your sexuality and enjoying your full potential, etc.
    Kim Anami- Orgasmic Enlightenment

    Edit- adding – we as humans over think. Enjoy each other in every aspect, communicating and being honest.

  18. There is also a website called OMGYes that focuses on women’s orgasms. It costs money because the research costs money but there are amazing insights, videos, interactive games that will help normalize sex for her and teach you both a lot!!!

  19. Could tell her to us ur face as a pillow… just saying… she likes to grind… so she probably needs to be on top riding and grinding… can u handle it… once she accomplished this, it will be easier for both of u to read each other’s signs to achieve orgasm… she still may been more fore play to warm up before piv… toys can help, but there are unique cock sleeves that offer a grind plate to better stimulate the clit while grinding

    https://darquepath.com.au/products/gluttony-wearable-sleeve

  20. Assuming you like sex and trying things out. Let her know that you would like to play with her. Obviously let her know you just want to do your thing and don’t worry about an orgasm. Lube, a vibrator, tongue, fingers and plenty of time are your friend. Leisurely relaxed afternoon of playing with her clit and g-spot will likely get you what you’re looking for. Had a fuck buddy awhile back with the same story. Sex was pretty awesome but it was annoying she would call to hookup and always say but don’t worry….. she always waved me off on oral. We finally met up with an overnight. Yet again she waves me off. I let her know that I would like to go down on her and didn’t care if she cums. (Very competitive guy… I did care) In the end she let’s me know she would enjoy it but didn’t want to disappoint me. My response was along the lines I just wanted to have some fun doing my thing and she was welcome to watch TV or play with her phone. I went into it with a 3 hour plan…. settled in with the lube and constant stimulation to her g-spot and clit. Whatever got a reaction i kept doing and stitched all of them together. Only took half hour. Later she let me know what finally got her off was the realization that I was enjoying myself and it wasn’t going to stop.

  21. You may have the intention of putting her pleasure before your own, which I commend you for, but I can tell you are not. That’s ok, here are some ways to put her pleasure first, which is essential if you want her to come for the first time:

    – Take all of the pressure off. Let go of any end goal other than her enjoying herself in the moment. Don’t let her feel any of your frustration or insecurity (don’t justify or explain why it’s hard to make her come, don’t compare other experiences etc.), that’s yours to deal with, not hers.
    – State your intentions clearly. Let her know how much you love her, how important her pleasure is to you, how much you enjoy watching her feel good no matter the outcome, that there are no conditions on this, you’ve got all the time in the world to please her.
    – Encourage her to take ownership of her pleasure and learn to come on her own first. It for sure doesn’t matter who or what gets her off, don’t let your ego or insecurities get in the way of that. Tell her you’d love to watch her hump that pillow, show her how interested you are in anything that turns her on or makes her feel good.
    – Put PIV to rest for a bit and work on her whole body, mind and soul instead. Basically make love to every part of her. Explore and find her buttons, whisper words of praise and encouragement in her ear. Let her know this is enough for you, that in this moment you don’t care about jerking off, you just want to pleasure her.
    – Don’t over stimulate. If you’re going down on her/fingering her, it’s really easy to numb her clit until she’s past the possibility of orgasm. Go slow, be real sensitive to her body language or encourage her to verbalise when you need to press lighter/go faster/switch movements etc.

    This may seem overly selfless or unachievable but you’ve absolutely got this. You’ll be doing yourself a favour in the long run because sex just is so much more fun when both of you are getting off.

  22. Why don’t u pretend you are the pillow with small cushions around your cock and she can ride all she wants on it!!

  23. If the issue is her psychology, I’m not sure how to help here. Maybe pot? It can seriously help. Good toys, a peaceful welcoming environment, candles, and self- touch. If the insecurities are deeper, she might need to talk to someone.

    Technique, however, can be taught. The first thing is to accept that most women don’t cum from penetration. Accept it, get over it. Foreplay, then, isn’t just to turn someone on. Your fingers and tongue are the main event.

    Set the mood, create the right environment, and get to know her body. Be patient, loving, open, and enjoy yourself. If she’s uncomfortable with her body, you need to show her that going down on her is the most amazing thing in the world. Love is a verb. Don’t just tell her you love her body, actively do it.

    Three tips:

    Fingers: crook your fingers towards yourself, like a gentle hook. Above the inside of her vagina you’ll feel a kind of spongy, firm ball, almost. Apply firm, rhythmic pressure to this spot. Don’t be violent, be loving. This isn’t porn. This spot is your best find

    Rhythm: put on a good soundtrack and follow it. This is a dance, and you’re both more likely to let go if you find a great Rhythm.

    Listen: this is 90% of good sex. Pay attention to her. The way she breathes, the way she moves, the way her body feels. I mean it when I say it’s a dance. Lead the dance by feeling what she’s experiencing. When she likes something, keep going, stay on Rhythm, but build and fall in intensity based on her reactions.

    A couple of books

    For her: Come as You Are

    For you: She Comes First.

  24. >note that she has never finished in her life.

    Like never had an orgasm in her life?

    First step is her being able to reach orgasm herself

  25. why are you putting so much pressure on her to orgasm? does it even bother her that she isn’t or are you making this into your own problem?

  26. If you guys are off the legal age maybe have a few glasses of wine to loosen up and explore each other’s bodies without having sex ex: teasing, fingering, oral, licking, grinding
    Don’t feel rushed to finish and just have the goal be to make each other feel good

  27. Not necessarily you. I wasn’t able to truly cum the first few years of having sex. Some women’s bodies take a while to sort it out. I was having a blast…some twitches, but not a true orgasm. (Lost virginity at 15…I was 19ish before it randomly happened.) And ESPECIALLY when people are new at sex, their masturbation efforts are likely more pleasurable. It’s instant feedback when you do it yourself. You don’t have to translate what you’re feeling into words. You don’t have to worry about hurting someone else’s feelings. You aren’t dealing with any self conscious feelings at all. All of that can make masturbating a bit more pleasurable until partners work out each other’s “buttons” so to speak.

  28. Hey, definitely keep complimenting her and showing her that you love and admire her mind, body and spirit. Don’t forget that for play begins outside the bedroom. Maybe try and do things that show you love her body, without expecting sex from it.
    Have you heard of the 5 love languages? That could be a quiz you two complete together and learn how to love each other in that partner’s language.
    Ex. words of affirmation- you telling her you love her smile, problem solving skills, her body is banging
    Physical touch- have her lay her head in your lap while watching a show and just play with her hair/ rub her scalp, massaging her feet
    Acts of service- hey, I saw your tank was low, so I filled you up, or hey, don’t worry about dinner, I want to make us something
    Quality time- having a game night, going to a restaurant you both have mentioned wanting to try, going to the store together, getting a pedicure together, having a picnic on your living room floor with a list of fun questions to ask each other
    Gifts- flowers, something sexy you want her to wear, tickets to a comedian she likes, a gift card for coffee/ her go to fast food place. If money is tight then a homemade coupon book for her to use whenever (A back/ foot massage that doesn’t or does include a happy ending at her request. Vacuuming/ washing her car. A voucher for you to do the laundry naked or with something funny)

    Since she mentioned that riding the pillow helped her get there, watch this video and see if she will be interested in trying a position? Would she be more comfortable with the lights off, candles, a t shirt? Let her know that you care and want to to help her be more comfortable with a little pressure as possible.

    https://youtu.be/n1Ab7wQiQSY

    I’m sorry this was long, but I hope this helps.

  29. Being someone who was in this scenario it just takes patience.

    -When you have sex don’t make orgasm for her the goal just make sure everyone has a good time.

    For my girlfriend she just needed to continue to get comfortable and confident with what she liked.

    -Just keep at it

    -Focus on her and don’t be disappointed if there is no orgasm.

    -Make sure she is telling you what she likes.

    -Try to keep any pressure off.

    -Try different positions and techniques.

    -Have fun. Sex can be good without orgasm.

    Good luck my friend. It gets better and that first time she does orgasm is the best feeling in the whole world!

  30. Don’t take this personally at all, women’s bodies are much different than men’s and harder to figure out, even for the women owner themselves.

    I did not have an orgasm until after my fourth partner. Don’t know why. Can’t say one guy was better than the other . I think time passed, I felt more comfortable, I had more experience with my body and different men’s bodies.

  31. you suck at foreplay probably or you need to make her comfortable first.. tensed body or things on mind fuck up whole orgasms… do what she likes before getting on with it… try kissing her all over her body and don’t just jump to piv… ask her and make her a part of it not to full fill your satisfaction…

  32. Tons of comments here so this may not get any traction, but have you had her try grinding on you? Does she use the pillow with or without underwear on? Depending on which, maybe try having her straddle your lap (with or without an erection) and have her grind against you. My wife and I do this sometimes as part of foreplay, I’ll pull her on top of me and she grinds her pussy against my dick while we make out. It’s pretty nice, then we move on to other things.

  33. Okay. If she rides her pillow, she likes clitoral play. Do your best to research what you think she likes. Pick up on her reaction and stay the same during that time. Women are people of emotion, she may like it a different way from the way she’s telling you and might be shy about it. Try other ways as well and see if it makes her feel better. Don’t call her beautiful just outside of sex but also while you have it. She her how much you love her, and tell her as well.

  34. Have you gone down on her? You know most women do not orgasm from PIV right? Like the majority do not. Focus on the clit dude cuz that is how most women get off.

  35. You sound like you’re both really young so here’s a big lesson.

    The brain is the biggest sexual organ in the body.

    No matter how much you try to do for her physically, if her head is not in the game for whatever reason, it’s a no go. It just won’t work at all.

    Not your fault.

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