The ultimate guide to the first time sex with another woman

Dating tips
February 12, 2020

It’s hard to calm down before having first-time sex with another woman. You don’t know how it will feel to have love with someone with boobs and vagina, and you don’t know how to make it all flow naturally. In reality, many bisexual and lesbian women found that having sex with women is much easier than with men.

Still, you want to be ready for the exploration before you embark on the journey. You wouldn’t want to find yourself holding your partner’s boobs awkwardly with absolutely no idea what to do. So, here are the best tips for a woman having sex with another woman for the first time.

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When you have sex with a woman for the first time, it’s natural to be stressed

Tips for first-time lesbian sex

You only have one shot at having lesbian sex for the first time. Naturally, you want to get it right. In my experience, several factors can be make-or-break — everything else is optional. So, let’s cut to the chase.

Start with communication

For any good sex, straight and gay, communication is the only way to make sure both partners will be safe and comfortable during the process. If you are having sex for the first time with another woman, talking things out is especially important. Don’t be scared to ask where she’s going to put her fingers and how exactly she’ll move them, how far will the penetration go, what are the rules on boob play.

Masturbate to get experience

Lesbian women have an immense advantage — you have an excellent training ground with you. Masturbation is the best way to explore sexual techniques and understand the way your body responds to various kinds of stimulation. I encourage you to experience different types of technique — clitoral stimulation, G-spot orgasms, squirting, and anal penetration.

Naturally, the body of your partner will feel different from your own, mainly because the anatomy of each woman differs and because you get no feedback on your action. Still, knowing what goes where on your skin is a good way to get started. Plus, you can tell her what techniques get it on for you the most.

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Talk to your partner about her previous experiences before having sex

Practice nipple play

Even if you are nipple masturbation pro on your own, you can get confused with an unfamiliar pair. At first, you’ll be confused about how it feels to hold booиs — and that’s just to being with. You can also feel insecure about your interactions — a lot of women worry that they will hurt their partners.

My advice here is to avoid painful experiences and rough stimulation. If you decided to go there, at least, practice the techniques on yourself at first. Also, remember the advice on communication.

Get good at clitoral stimulation

The most common way for lesbian couples to get to orgasms is by clitoral stimulation. You insert your fingers into her vagina and start massaging her clitoris or the deeper sections of the vulva. You can even use fingers for G-spot stimulation, although it’s easier for women with longer fingers.

If your fingers aren’t too long, experiment with sex toys. For clitoral stimulation, you’ll be fine with your hands, but if you are aiming at G-spot, a practice combining hand play with sex toys. Again, try new things out on your body before trying anything funny with your partner.

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Whatever penetration you choose, don’t forget about kisses and hugs

Discuss the optimal penetration

Deeper isn’t always better. For the best first-time lesbian sex, it’s better to discuss how deep you want to go before you go in. Some women prefer G-spot vibrators for deep penetration instead of fingers while others find sex toys too rough.

Either way, if you choose to go in deep, don’t forget to lubricate. Also, take good care of your fingers — use creams and lotions to smoothen the skin and trim nails.

Use accessories

Lesbian sex also requires protection. Otherwise, you risk the transmission of HPV, bacterial infections, hepatitis, and other diseases. To protect yourself, use dental dams — small accessories that are attached to the vagina. For fingering, use latex gloves.

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Dental dams are easy to apply and you will not lose sensitivity

Go oral

If you feel more confident during your first-time sex, you can lick her clit and labia. It’s a subtle stimulation that excites female erogenous zones in seconds. Oral sex is one of the shortest ways to get her excited, and it doesn’t take much practice. Remember to not slack off on protection, though.

Best positions for first-time lesbian sex

If you are experienced in having sex, just not the lesbian one, you can easily pull off the most common lesbian positions. If this is your first time having sex with another woman, it’s best to not experiment with anything right away. For those who have already been in the game, I made a list of most impressive positions for first-time lesbian sex.

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It’s an ideal first-time position for oral sex

The Lean In

Your partner should lie at her back while you sit on your knees, facing her vagina. Kneel and penetrate her vagina, or start with gentle clitoral fingering. The angle is suitable for deep penetration because her vagina will be facing you directly. Use this one for oral sex too — you’ll be in a perfect position to lick her labia.

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It’s a gentle position that doesn’t require much strength or practice

The Laconic Lounger

This is a simple and gentle position, perfect for beginners. The partner lies on the bed on her back. You kneel between her knees and use one hand for clitoral stimulation. Make round motions with your fingers, while the other one will massage her boobs. You’ll be facing each other, so a perfect one for passionate kisses, too.

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You might want to do some ab workouts before trying out this one

The Olympic Gymnast

This position isn’t easy to pull off — it requires strong core and leg muscles, but if you do, it’s rewarding. Lie on your back and put your legs in the air as if you are exercising lower abs. The partner puts her face between your legs and stimulates your clitoris with fingers or lips. The angle is perfect for G-spot stimulation and oral sex.

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This position puts your vagina and anus in the closest proximity to each other

Twisted Scissor

Both partners should spread their legs and straddle the partner with one of them. Legs intertwine, forming a shape of twisted scissors. This position requires a lot of space, so you can do it on the floor, using cushions and blankets for support. Your clits will be rubbing each other, providing seamless stimulation.

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Lesbian doggy style isn’t much different from the straight one

Doggy Style

Doggy style is a classic position for a reason. The only difference is that lesbian couples use their fingers or sex toys for penetration. The basics are the same: one partner gets on her knees and hands while another kneels, facing the partner’s rear. It’s a rough position, so don’t slack off on lubrication.

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Her stomach should face your back, leaving both of your hands free

Standing Shower Sex

This position doesn’t require much space and is perfect for showers and small rooms. Your partner goes behind, hugging you from the back. Your butt is facing your vagina, leaving your hands free for clitoral fingering and boob plays.

What lesbians say about their first times

What’s the better source of learning materials if not real-life reviews. I scoured YouTube, forums, and Reddit to get advice from fellow-lesbians.

Don’t use your teeth

If you want to stimulate her with your mouth, limit to licking and sucking. Any grinding or binding can end in the injury, and she won’t enjoy this. Also, if you don’t have lubes, use your pit as a natural lubricant.

The foreplay is your friend

Don’t rush the sex, especially if you have rough positions in mind. My best experience was after at least 20-minute long cuddle sessions. If you also add a dirty talk to the mix, you will enjoy the process much more. Also, don’t limit yourself only to her vagina. Pay some attention to her hips, neck, ear lobes, back, and tummy.

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Start with dirty talks and gentle cuddles

Keep eye contact

When you are entering her vagina or anus, be sure to look at the partner the whole time. Start orally. You can lick labia and clit to get used to the sensation. If you want to pull something funny, ask her beforehand. Generally, always ask. Don’t worry, it won’t kill the spontaneity — certainly not as bad as an injury would.

Experiment with the speed

When you are in, don’t get stuck in one tempo. Whether you use fingers, sex toys, or your tongue, switch it up from time to time. Vary the intensity from very slow to a fast one. If you are rocking her on different sides of the spectrum, she will surely enjoy your spontaneity. Just make sure not to overdo it.

Get positive energy running

My first time was terrible. I am not sure if she felt the same way, but let’s just say, I didn’t feel anything expect of stress. However, I got a precious lesson from that. The second time around, I was just as inexperienced, but I decided to go with it, tried to crack jokes, and experimented with sex talk (although some of that was cringe). Still, she loved it, and we both had a wild ride. The change in energy made everything much better. Even now, when I am not confident, I try the same sex with another woman for the first time story — it makes partners much more careful.

Start on one

Don’t make the mistake of thinking that exploring a female body will be easier in a threesome. You’ll be distracted by the third person — and it doesn’t matter whether it’s a man or woman. The communication options are limited, and you won’t be feeling as comfortable. I know that many girls have the temptation to invite girls into their straight hookups, but honestly, that’s not the best way to get introduced to lesbian sex.

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How was your first lesbian experience?

The first lesbian experience is not your ultimate time. Don’t expect it to the best version of sexual chemistry with a partner. If you don’t enjoy it, don’t give up or beat yourself up. Even if you do all the tips mentioned, you’ll get a decent experience. Keep exploring yourself and your partner, and practice different techniques during masturbation.

At what age is appropriate to have the first lesbian sex?

If you are not 18 yet, make sure to educate yourself on the safe sex and make sure that the partner understands what to do. If you are older and worried about the lack of experience, don’t feel pressured. In my experience, the bisexual and lesbian community is friendly. If you warn your partner about the lack of experience, she’ll likely walk you through the process in detail.

What to do if I have no experience in lesbian sex?

Start with masturbation. Exploring yourself with different techniques of clitoral stimulation, G-spot orgasms, and experimenting with sex toys is the easiest way to get familiar with what makes women cum. You won’t be able to try oral, but that’s the easiest part of lesbian sex. Also, I wouldn’t watch lesbian porn — it’s not one bit realistic.

How to start having sex with women?

You can start by registering on the dating app that’s friendly to the LGBT community. My favorites are Pure, OkCupid, and Her. You don’t have to rush getting into a serious relationship — for some, it’s easier to start with casual hookups whee you have no responsibilities. But, since it’s your first time, I recommend avoid getting drunk — you want to keep a clear mind and remember what’s going on for future experiences.

What are the possible challenges of having sex with a woman for the first time?

You can be confused with clitoral stimulation and boob play. A lot of women at first don’t feel comfortable with their hands. Also, you need to focus on lubrication, hand hygiene, and buy special accessories like dental cams for protection.

A short film about first-time lesbian sex


Getting to good lesbian sex requires patience. Women take longer to orgasm, so you’ll need to try multiple techniques and foreplay. If you expect the immediate effect, you’ll be disappointed again. Don’t set orgasms as the only end goal — a lot of women enjoy lesbian sex even if they didn’t orgasm. If you take your time and don’t stress, you’ll most likely cum even on your first try.

The key to success is communication and eye contact. As long as you are aware of how she feels and she knows what you think, you are both good.

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