I'm 35 and still a virgin - will first time sex hurt?

Hi Aunt Vadge,

I may end up writing a novel here.

So I have two questions regarding sex and fellatio blowjob.

My first is I am a 35-year-old virgin. Sometimes I wonder, who am I waiting for?! I don’t think I’m waiting for marriage, but someone decent. I had a bf for 5 months, and he gave me oral for the first time. It felt great.

I broke up with him, but I’m contemplating getting back together to have sex. Before I go on, I am BRCA1 positive and found at age 24. I spent 10 grand freezing my eggs so I can use them with IVF and get them genetically tested. I’m paying a storage fee annually.

While I was freezing them, I was doing abdominal ultrasounds. On my first appointment, my reproductive endocrinologist suggested a transvaginal ultrasound.

My mother agreed since it would be easier to see my eggs, ovarian reserve, etc. I remember she started to stick the probe in, and I yelled in pain for her to get out of it.

I was traumatised because I thought sex will feel like that. Ever since my surgery, since they had to use a TVS to get my eggs out, I am able endure a transvaginal exam. I feel pressure, and it is a bit uncomfortable, but I deal with it

I also have been masturbating since I was 16, and my hymen may have been broken during the retrieval, but I’m not sure.

I’m just nervous about having sex for the first time and if it will hurt, etc. The doctors do recommend a salpingo-oophorectomy at age 35 to 40 with HRT so I don’t go into surgical menopause.

I just wanted to know if it can be a pleasurable experience, if not the first time, but eventually? When I watch porn, there is a sense of total enjoyment, sensuality and freedom of being in the moment and just keep thrusting without end… I want that feeling.

Also, I wanted to know if I get back together with my ex, is it safe to give him a BJ without a condom since we both got tested? I personally would want him to wear a flavored condom, and I don’t want cum in my mouth.

Thanks.
Sorry for being too graphic or writing a novel.

Yours sincerely,
Curious
Age 35, USA

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First and foremost, Curious, thank you for trusting me with your thoughts and concerns. It’s absolutely fine that you’ve shared a lot with me – it helps to understand your situation better. Let’s tackle your questions one at a time.

Your first time

Regarding your first question about having sex for the first time. It’s important to understand that everyone’s experience with sex is unique, and it can certainly be a pleasurable experience, even the first time.

However, it’s not uncommon for the first time to be a mix of emotions and sensations, including discomfort.

What is seen in pornography is often not representative of real-life sex – it’s a performance that doesn’t account for the nuances of individual experience, intimacy, and connection. It’s completely normal not to experience the kind of non-stop pleasure that’s portrayed in porn, especially not initially.

To help make your first experience more pleasurable, communication with your partner is key. Make sure to tell them what feels good, what doesn’t, and if you want to stop or take a break.

Using plenty of lubrication can help make things more comfortable, and finding a position that allows you to control the depth and speed of penetration might also be beneficial.

If you’re concerned about pain or discomfort, discussing this with a gynaecologist can also provide you reassurance, and they may also be able to offer tips specific to your situation.

Fellatio safety

Moving on to your question about fellatio and safety. If both you and your partner have been tested and are clear of sexually transmitted infections (STIs), the risk would be lower, but remember that some STIs are not regularly screened for and can be asymptomatic.

If you or your ex have had other partners since being tested, it’s a good idea to be tested again.

It’s great that you’re considering using condoms during oral sex – flavoured condoms can be a good compromise if you’re not comfortable with ejaculate in your mouth, and they can reduce the risk of transmitting any infections that might not have been tested for.

Again, communication with your partner is essential to ensure that both your boundaries and health are respected.

I think you’ll like sex! But first…

Since you’ve been masturbating for so long, you know what you like and what gives you pleasure, which is a huge bonus. I get the impression that once you get started with sex, there’ll be no stopping you!

To help quell some of the anxiety about penetration and pain, my advice would be to start trying masturbation with a penis-shaped dildo. This way, you are in control of the whole thing and can experiment with what feels good and what doesn’t. Slowly and gently, try penetration on yourself.

The main advice here is to go slow, use plenty of lube, and make sure you are good and turned on before you penetrate your vagina, as it’ll be much more ready to receive the toy, and it’ll be much more pleasurable.

Learn how big the clitoris is and how it also needs to be ‘erect’ like a penis for penetration to feel good for you. This is the difference between the discomfort of the ultrasound and exam versus hot sex or a good self-love sesh. Your huge clitoral structures are what make penetration feel good when they are engorged. Otherwise, sex feels like a pelvic exam – uncomfortable and uninspiring.

Experiment with positions with the dildo. Using pillows, you can hold it in place on a bed, use it from behind, or use it from the front. I recommend you try everything! I recommend a very high-quality dildo, so get a really nice finish (not hard plastic) in a modest size (you can always upsize or buy more than one).

Find a very upmarket dildo shop, and go in-store if you’re brave enough and speak to the shop assistant, who you can explain what you’re after, and they will give you advice. Or, find something that looks beautiful online from such a shop and start trying it out.

Then, when you feel less worried about penetration – and in fact, look forward to the ‘thrusting without end’ – then give your ex a call. You will know what you’re in for in terms of penetration. I promise it won’t feel like an intravaginal ultrasound OR a vaginal exam!

If it hurts, stop and try something else or try another time. Remember, your comfort and pleasure in sexual experiences is paramount. Make sure to take your time, communicate openly with your partner, and don’t do anything you’re uncomfortable with. It’s your body, your choice, and your right to enjoy sex on your own terms.

Please reach out if you have more questions or need further clarification – I’m here to help.

Happy lusting!
Aunt Vadge