Scarleteen

I'm 29F and something bothers me up to this day. At 27, I attempted sex for the first time and it was generally unpleasant. I was peer pressured into it and out of pity, tried to have sex with a friend. I did my best to get aroused and get wet enough for what's to come. All prior knowledge about sex has just been internet and porn tutorial videos (which is kind of dorky...). I decided to go through with the sex despite knowing I don't like my friend that way and despite having only masturbate and get aroused via non-penetrative stimulation.

I thought I would be able to penetrate myself finally with the help of my friend, but I realize after he tries to enter, how tight it feels. I didn't even feel pain. Just that there is a struggle to even get past my opening... he proceeded to air hump me for 30 mins. I was getting drier by the second and he was falling asleep while doing so. Lame night overall.

After that, I thought to myself that maybe I should try penetration myself first. And I get aroused and even wet, then use lube - but when I insert the toy, it reaches about 1/2" or 3/4" of the way before I feel the tightness and the pain. Like I can't push it deeper. I haven't tried finger too as I don't know but the fear of scratching my inside with my nails is what bothers me. Maybe it's not a real worry tho.

I am a little bit insecure about it, as I've never been in a serious relationship before and I have fears of putting a foreign object inside me. I wanna be able to enjoy myself. But I don't know how. Please help... I want to feel pleasure.

Hi there AngelMads! There's a lot to cover here, but first I want to say that I'm sorry this is making you feel insecure and stressed out. What you're describing is very common and it doesn't mean that you won't be able to enjoy yourself or experience pleasure in the future.

First, let's talk about the sexual experience you had with your friend. I'm so sorry that it was so unpleasant! Given everything you've described about the situation (you felt pressured, you don't like your friend that way, the sex wasn't fun or pleasurable, etc.) it is not surprising at all that your body didn't react the way you expected. I would even go so far as to say that this is an example of your body working to protect you, like it was saying "nope, this is not the way I want to have sex, this is not happening!" Feeling safe, comfortable, and relaxed are BIG parts of what allows our bodies to become aroused and as you say, arousal is necessary for trying to insert anything.

Now, on to the masturbation piece. To start with, there could be a similar thing going on here: like you said, you have some fear about inserting the toy or fingers, and it sounds like it also might be all tangled up with some negative emotions like feeling insecure or worried about whether you'll be able to have pleasurable sex in the future. Those negative feelings can make your body tense up and lessen your arousal. But there could be some other things going on too. This article is framed around intercourse with a partner, but all the information absolutely also applies to masturbation too: From OW! to WOW! Demystifying Painful Intercourse As it mentions, there could be a medical issue involved, like vaginismus, that a gynecologist could be able to help you with. Or, if the issue is more about your fear and your memories of your previous bad experience, a therapist could be helpful to untangle some of that. Or, it could just be that you need more time to explore by yourself in a low pressure, relaxed, and comfortable way or with a good, safe partner in the future, and you'll find that there's no problem at all! This article isn't about insertion specifically, but I love what it has to say about how to create an environment that is about just exploring pleasure during masturbation: Take a Self-Love Road Trip: Let Curiosity Guide Your Masturbation.

The last thing I want to say is that although I'm pretty confident you'll be able to figure out how to have intercourse in the future, the ability to insert something in your vagina is NOT the same as your ability to have pleasurable and enjoyable sex. There is so much pleasure to be found in sexual activities that don't involve inserting anything at all, both in masturbation and partnered sex. I always think it's a good idea for everyone to explore all kinds of sexual pleasure, for one because our bodies are all different and respond to things in different ways, but also for two because the more options you have for pleasure, the richer and more flexible and varied your sex life can be. This article talks specifically about why it can be good to explore other kinds of sex besides intercourse, especially if intercourse is not very pleasurable at the moment: Yield for Pleasure.

I hope some of that is helpful!