Hey! I have two dilemmas. So basically, I've been sleeping with my fuck buddy for about a year now and I've never orgasmed but he cums every time we have sex. The sex is amazing, the best I've ever had. He's older than me and far more experienced than me and he puts in a lot of effort to make sure it feels good. In certain positions he'll rub my clit and focuses mostly on the clit when he's fingering me and giving me oral but even so it never happens. I recently bought a vibrator and had my first ever orgasm at the age of 22, so I know what it's supposed to feel like but recently ever time I use it I struggle to reach orgasm. The feelings get too intense and I struggle to hold my vibrator to continue the sensation which is very frustrating. Do you have any advice how I can overcome both of these issues?
Hey! I have great news for you; you actually only have one dilemma and it’s a totally fixable one.
But before I get into it, I just want to address that in your original email you said your boyfriend would “run” on your clit, I assumed it was a typo of rub, but JUST in case it wasn't, I would definitely advise he stops running on your clit because I don’t think that works for anyone.
Okay, so the predicament is simply that you’re having a hard time reaching orgasm overall. I am so sorry you had to wait 22 years to experience an orgasm, and now that you know what it is, I’m so sorry you’re struggling to find it again. But fear not, because it’s a completely typical situation, and working through it is gonna be really fun.
If you’re struggling to orgasm when you’re on your own, you’re absolutely not going to have more luck with a partner. You really need to know how to get there by yourself before you can instruct your boyfriend on how to make it happen. So you’re going to have to experiment with your masturbatory techniques and have a long overdue journey of discovering your personal erotic response. Once you’ve nailed making yourself orgasm, you’ll be more than ready to find out how you can orgasm with your boyfriend.
Although it may feel counterintuitive at first, it can help to completely take the goal of orgasm off the table for a little bit. Sometimes the conscious quest for orgasm can actually be what gets in the way. If you instead focus on increasing pleasurable sensations, and exploring what feels good, you may find that you accidentally cum anyway.
Clitoral stimulation is key for the majority of women to reach orgasm, and many require simultaneous penetration and clit touching. It sounds like your fuck buddy is aware of this, and so has been directing some attention there - but he's going to need more specific instruction.
I think your vibrator may be a little too intense for your clitoris, the sensation you describe is a super common. It appears that clits can vary A LOT in their sensitivity. While some require very powerful and direct vibration to reach climax, others respond to just a light feather touch. If you do have a more sensitive clit, one solution could be investing in a new vibrator that offers a range of intensities; so you can turn it all the way down and slowly increase the speed or strength of vibrations as needed. I REALLY recommend FUN FACTORYs LAYASPOT for an introduction to clitoral vibrations.
Alternatively (or also for best results) you can try out some different masturbatory techniques. E.g. use only your hands, use penetrative toys (if your clit isn't enjoying vibrations - definitely try a g-spot stimulator such as the great GIGI 2 by LELO), try running water pressure, or try just humping and grinding on something sanitary. Loads of women employ a very specific and personalised masturbatory routine to ensure they reach orgasm, but they have usually honed this technique through trial and error, or stumbled across it by surprise! You could check out OMGyes for some clear examples and inspiration (or even have a peek at some solo female porn).
If you struggle to keep your hands in place while you're reaching orgasm, then don't use your hands! Position your sex toy in a way that you can work hands free - using your hips and thighs to grind your way to orgasm.
If you’re still having trouble you should consider any psychological barriers that may be preventing you from feeling relaxed enough in order to orgasm. It might be that you prefer a specific context or setting, that you need a long warm up, or that you need to be fantasising about something particular. Whatever it is, whatever it takes, be generous and patient with yourself until you are confident you know what you want and need.
THEN when it comes to the partner, start off with some DIY clitoral stimulation. Have him observe what you do, then hold his hand and make it do what you want it to do, and eventually he will learn through your direction what gets you there. Try also cowgirl/reverse cowgirl and other positions where you can really control the speed and rhythm of the fucking and the position and angle of your junk. If using a toy is your preferred method to reach orgasm, then whip it out and show him how to use it!
TL;DR masturbate a ton