Hi! First of all, thank you for having such an amazing site. I’ve been reading for a while just to get to know things, since I find it really interesting.

Now, for the advice I want to ask. I’m almost 100% sure I’m never going to have sex with a man. I’m 28-years-old and never had a boyfriend…

I’ve had cybersex, obviously I masturbate on occasions but it’s only clitoral. I’m seriously considering “deflowering” myself so here’s where my concern comes in. How should I do this? Is it necessary to go all the way or can I just like use my fingers and maybe not be able to break the hymen but just reach enough to be able to pleasure myself? I’d like to not have to buy any sex toys to do this.

I’m just generally scared of doing this by myself but I really don’t have any other choice. It’s gotten to the point I actually dream about fingering myself. Yes, I do watch porn.

Anyway, thanks in advance and I do hope I get some advice.




Thanks so much for writing in. I’m so glad that you felt the desire to reach out to us, as our founder designed the site in such a way to make it a safe place for people seeking answers to deeper questions like you.

First off, I want to empathize with you and tell you I’m sorry you’re having so much trouble. It can be difficult to feel as if things will ever be different when you’ve been stuck in one place for so long. As I don’t know your history, I know I don’t know the whole story. However, I’d like to say this. For some, religious and cultural reasons keep them from having an intimate relationship. But… if the reason that you believe you will never have a boyfriend is because you are unworthy or unlovable, think again.

You are worthy. You are lovable. There is someone out there who wants to love you, but they cannot find you if you are bogged down by the belief that you can never have it so you may as well give up. This is not positive thinking, and it is not useful to you or your growth as an individual. Plenty of people do not find love or make love with someone for a long time. It is easy to look around and compare oneself to others, when the only person you have control of is yourself. Don’t compare yourself. You’re perfect as you are, and if you want to find someone, you can!


As far as masturbation and losing your virginity goes, it is totally, completely and utterly okay that you watch porn and that you engage in cyber sex. Breaking the hymen is not necessarily a symbol of “losing one’s virginity.” Some people with vaginas are born without a hymen, and some break their hymens doing completely ordinary, non-sexual things, like horseback riding, cleaning, playing sports and walking. Thus, the pain that is experienced by many with vaginas when they lose their virginity oftentimes doesn’t have anything to do with breaking hymens.

Secondly, there is no one way to have sex. Many people have sex in many different ways. Masturbating by yourself, even when there is penetration, is not considered “losing one’s virginity”, as it is not with a partner. Most definitions of sex involve a partner, and it doesn’t always include penetration. The conventional view of sex and ‘losing one’s virginity’ is penetrative penis-in-vagina sex, but this is a very narrow definition. Anal sex is also a form of sex and can count for “losing one’s virginity.” In fact, due to the highly intimate nature of oral play, experts are starting to consider it as “losing one’s virginity” and refute claims that you can be a “virgin” but have oral sex.

If you’re wondering about penetrative sex, it is possible to penetrate yourself. It is completely normal, healthy, and pleasurable. It is not dangerous, shameful, or “deflowering”. It is okay to use your fingers, toys, or something else – in fact, we’d recommend doing it solo first rather than with a partner, so you can completely control the speed, depth, and sensation. Go slow, enjoy the sensations, and explore what feels good to you.

Have you ever orgasmed with your clitoral stimulation? If you have, I would definitely wait to penetrate yourself until after you have orgasmed from clitoral stimulation. Your vaginal muscles will be much more relaxed and your body will generally be more open to your fingers (or a toy, if you choose to use that) coming inside.

When you do penetrate yourself, I would make sure your hands were clean and would definitely recommend a good water-based lubricant. My favorite is Almost Naked Personal Lubricant, but any water-based lube will do. Put the lube on your fingers and gently move your hand down from your clitoris to your vaginal opening and stick your finger (first one, then more) slowly inside. You can play with pressure and speed. Your vagina also has the ability to expand, and so you can play with adding more fingers as you get more comfortable.

As you get in touch with your body, I would recommend a good quality vibrating toy. There some amazing, body friendly toys that are made with clean materials and cool vibration patterns. Also, there is only so far a hand can reach when you’re playing with yourself, so adding a toy in the mix can leave your other hand free to play with your clit while your toy is inside you. If you’re looking for some good quality beginners toys, we love the We-Vibe Tango for clitoral stimulation. If you’re looking for something inexpensive, Adam & Eve’s Velvet Kiss is a great beginner toy.

I want to commend you for asking questions and for your willingness to explore. Exploring your body so well is definitely a gift in and of itself, as when you do find a partner, you will know what you like and what gets you off. However, I would highly recommend exploring your beliefs about why you don’t think you’ll ever find a loving, caring partner. Know that there is absolutely nothing wrong with asking for help from a licensed therapist or professional in helping you sort out these beliefs that are keeping you from having sex with a person that deeply cares about you.

I sincerely believe that in your case, the best thing you can do for yourself is to seek the help of a licensed, educated professional. We at Slutty Girl Problems absolutely adore the work that the professionals of the American Association of Sexuality Educators Counselors and Therapists (AASECT) do nationwide and I would strongly encourage you to seek out a professional in your area.

As far as professional level resources and books you can read to further educate yourself, I highly recommend the work of Tammy Nelson, Ian Kerner, and Stanley Siegel. Siegel’s book Your Brain On Sex changed my life and really helped me do some deep therapeutic work. I think it’s a worthwhile read for anyone asking the bigger questions.



As you go on this journey, remember that the answers you seek are out there, but that they might not be the answers you think you’re seeking. Journeys of self discovery don’t often follow the straight and narrow path and it is okay to ask for help on a path like your own.

We here at Slutty Girl Problems wish you the best of luck. Know this: You are worthy and lovable and you will find the answers you seek if you have the courage to look for them inside you.



 Questions are considered anonymous, and identifying information such as names and email addresses will not be posted, in accordance with our Privacy Policy. Personal information such as age and location may be changed to keep submitting parties anonymous. Submitting a question does not guarantee a response. Questions may be edited for spelling and grammar. By submitting, you agree to our Terms and Conditions.

Note: Some links are affiliate links, which help support the site. All opinions are 100% honest and my own. I only recommend things I would use myself! Read more about our affiliate links.