Chapter 9: Penetration for Pros - Expert Tips & Sex Positions

Let’s get it on! We’ve already discussed several kinds of sex — oral, anal, and masturbation (aka: solo sex). Now it’s time to talk about penetration.

Most of us learn that “Real Sex” is vaginal penetration or intercourse. When we lose our virginity, this is what the social script is referencing. While this social understanding of sex may be popular, in my professional opinion, it couldn't be more incorrect.

When we define “sex” as just vaginal penetration, it leaves out countless couples who cannot engage in this activity because they don't have a heterosexual, man/woman, able-bodied configuration. Or perhaps you are a hetero, able-bodied couple, but simply don't find penetration to be the gold standard of sexual stimulation. Whoever you are, and whatever your relationship configuration, the current sexual script is, and always has been, all about “performing intercourse.” This narrative minimizes sex to just genital act, versus a whole body, pleasure-forward experience.

So, rather than define “Real Sex” as the act of penetration where genitals enter an orifice for the end result of orgasm, let's try on a different definition.

I like to define “Real Sex” as any erotic activity that results in sensual or sexual pleasure. Real sex can include manual play, oral sex, anal sex, solo sex, tribadism, frotting, and yes, vaginal intercourse as well. Sometimes we have an orgasm; sometimes we don't. Sometimes we have penetration; sometimes we don't. Sometimes we are alone; sometimes we are with another. There is so much space and permission to explore the diversity of what turns us on when we change the definition of “Real Sex” to be inclusive and comprehensive.

Cheesecake of Pleasure

Changing the definition of “Real Sex” is a change in mindset. Therefore, I want to introduce you to my favorite sex therapy invention: The Cheesecake of Pleasure. Imagine having “sex” like you might eat cheesecake from the grocery store. Have you seen those cheesecake platters that have a diversity of flavors? Each flavor can symbolize a different sensual or sexual activity — from kissing or sexy showers to oral sex and anal sex. Flavors can include naked cuddling, light bondage, vaginal intercourse, and mutual masturbation with sex toys. Every couple's cheesecake will be unique to them based on the activities to which they both agree.

However, my number one ground-rule is the same no matter the flavors you choose: The Goal is Pleasure. (I did not say the goal was vaginal intercourse or even orgasm.) The Goal is Pleasure. If you have vaginal intercourse as a flavor, then have a good time! If you have an orgasm because the flavor you choose is so delectable and pleasurable, then congratulations! But these are by-products of the goal. When we take the performance out of sex and make pleasure the goal instead, everything opens up, making “sex” liberating, inclusive, and exciting.

There is one more suggestion around this concept. Some flavors may generate a high dose of pleasure for one person in the relationship, while the other person may experience a medium or lower dose of pleasure. We don't need to be experiencing the same amount of pleasure at the same time. We just need to agree that we like all flavors we mutually choose, and therefore, they get to go on the Cheesecake List.

Also, as a side note on virginity — rather than “lose our virginity” as if this treasured part of us must be inevitably and permanently “lost” to feel successful in the world, perhaps we could consider this an opportunity to “share our virginity!”

Communication is Lubrication

“Communication is lubrication” is a common cliché in the sex therapy arena, but that's because the metaphor could not be more apt. Communication can ensure an exciting and safe experience. When we can express our needs and wants, as well as fears and boundaries, then sex isn't carried out mysteriously. When things are a mystery, we make up a story in the absence of knowledge. Typically, the story is usually worse than the truth! “I think she liked the way I touched her.” “I think that was enough foreplay before I penetrated.” “I think he wants the lights off with sex.” And so it goes!

Talking in bed is easier when we practice talking about sex (and about all our fav cheesecake flavors) outside the bedroom. When that feels comfortable, bringing the conversation into the bedroom is the next step. Though so many young people are eager to have penetration (and “share virginity”), my professional advice is typically that if you can talk about sex in and out of the bedroom – your wants, needs, fears, and boundaries — then you are emotionally ready for penetration.

So, what does this discussion look like? Ideally there is enough safety to express whatever you need, openly and honestly.

“I need you to know that I really like to be tied up and spanked to get me turned on.”

“I want you to understand that I need to go slow with penetration because I have a history of pain with intercourse.”

“I'd like for us to both use condoms until we get tested for STIs.”

“I want to share my fantasy about threesomes with you. I don't need to have one, but just sharing is exciting and turns me on.”

“I like to be kissed on my neck and have my earlobes nibbled.”

“Because of menopause, I need to use extra lube and have extra foreplay.”

“Because of cancer, I need to use extra lube and have extra foreplay.”

“Because I'm human, I need to use extra lube and have extra foreplay.”

Learning to map your partner's body and their non-verbal cues will also score you big points in the bedroom (or wherever you play). Some people moan, groan, or even wince in pleasure. Others gyrate their hips or rock their pelvis in pleasure. Some people don't have a lot of movement or sound and can always be given permission for that freedom of expression. If you are unsure or confused by the non-verbal cues you are receiving, just ask your lover, “How is this feeling?” and “Any changes you'd like me to make?” Just because we are mapping the body and learning non-verbal cues doesn't mean we are meant to be mind-readers. Verbal communication to clear up any assumptions will ultimately cultivate the most clarity and success for your sex life and general relationship.

Expert Tips on Vaginal Penetration

When it comes to vaginal penetration, the media makes it seem straightforward. Genital A (typically a penis) inserts into Genital B (typically a vagina). Some thrusting occurs. The hips rock and roll. After a little bit of time, the friction of the two genitals manifests in an orgasmic climax!

Sorry folks, this is a gross simplification, on so many levels.

As we've learned from the “Cheesecake of Pleasure,” sex is not just penetration. It's a whole category of sensual and sexual activities that generate pleasure for both partners.

When “sex” is just simplified to the dance of the genitals, we leave out the whole body and mind connection, aka the intimacy and/or eroticism.

When it comes to penetration, we need so much more behind the scenes to ensure an enjoyable time, for the long run. Yes, I said the long run. Penetration can be super easy for new couples who are lubricated with all the new relationship energy hormones, like dopamine and adrenaline. When the newness fades, we must ensure we have enough real lubrication and extraordinary foreplay. We should also have some effective sex toys on hand to support a clitoral orgasm as 75% of women cannot have an orgasm from penetration alone.

Let's not forget that as humans, some women might have pain during penetration at some point due to childbirth and/or a drier vaginal canal after menopause. Men might have an elusive erection where the penis decides not to be part of the party or decides to ejaculate more quickly than desired. We might encounter an illness or a huge life stressor, either of which leaves “the penetration narrative” dull and lifeless.

Penetration for Pros is about being flexible to abandon the narrative you see in the media and find a flow with your words and your body that works for you. You might look like the movies. But you might not! You might thrust deep and hard, or your partner may feel more comfortable with shallow and slow. You might change positions four times, or you might defer to your tried-and-true place because it feels the most intimate and offers the most sensation and pleasure.

If you are totally new to penetration or feel like the movements you've engaged in just don't work, I want to introduce a new method I call Vulva Painting. Yes, penetration is about painting first. Imagine the vulva as a canvas and the penis as a paintbrush. If you are a same-sex relationship, or a trans-relationship, the configuration changes just slightly. The canvas and paintbrush for penis-on-penis (also known as frotting), or vulva-on-vulva (also known as tribadism), can be interchangeably exchanged in this exercise. For intersex, trans, and/or gender-fluid genital configurations, partners can play around with canvas and paintbrush roles.

For the sake of explaining this exercise, I'll use a penis-vulva configuration. After full-body foreplay (see Chapter 6 as a reminder), it's time for a focus on the genitals. The penis can be flaccid or erect, but flaccid is softer for painting. Apply lube to the tip of the penis and begin softly painting the outer and inner lips of the vulva. The vulva should be aroused from foreplay, but if not, this exercise can most certainly include some clit painting too! Once the vulva canvas is super excited, and I mean aroused at a high level like 7 out of 10, then penetration can begin. I don't recommend penetration before the vulva is at an aroused level of 7 because it can be internally uncomfortable and unprepared. A prepared and excited vulva makes for a more open and receiving vagina.

From here, penetrate one inch. Just. One. Inch. Check in. Is she begging for more or is she tense? You get to tease her while also making sure she wants the whole member. Then a second inch. Check in. A third inch. Until the vagina has capacity and excitement to take in the whole penis. Go slow at first. Remember those three Ss? Slow, soft, subtle. You can always go harder and faster as you build momentum. Rushing in and immediately thrusting fast is not going to accomplish the desired results for either partner. The penis may ejaculate too quickly that way, and the vagina may be overwhelmed.

Some partners may want to stay in the slow zone the whole time. Others may want to play with speed, depth, angles, and positions. Some partners stop and change activities because there is a loss of erection, pain with penetration, or to hold off on ejaculation. Think about that cheesecake again. You can go to the fridge and eat a different flavor, then come back to penetration if you want. No, this won't look like the Hollywood or Netflix script of sex, but we aren't measuring ourselves by that barometer anyway. It's just a set-up for failure.

If you return to penetration after a slice of another cheesecake, you can apply the same modality above, or if both partners are strongly aroused, slide your penis fully inside the vagina with slightly more speed. Again, check in with your partner. Immediate speed and depth are not always the desired effect. You have plenty of time to build towards that. Unless, of course, this is a quickie. In which case, try Penetration for Pros with the best sex toy you have to ensure you get that vaginal arousal up to a level 7 or more!

Popular Sex Positions & Your Pleasure

The guidelines above can be mastered in any sexual position. That said, sexual mastery is not about how many positions you do or how complicated and advanced you can get with your positions. Many couples tell me they just wish for more positions to spice things up. Then, they add more positions and still feel in a rut. The rut is not broken by more positions. It's broken by more pleasure. As we learned about in the Cheesecake Model — pleasure is subjective and unique to each person and couple.

Of course, it can be very fun to have a portfolio of positions from which to draw. Some positions might be great for accessing and stimulating the clit and/or G-Spot. Other positions might be good for deeper penetration. Some are great for controlling speed and depth to support more comfortable penetration and/or lasting longer. All the positions can be accessed whether you have a penis-vagina combinations, penis-anus, dildo-vagina, vulva-to-vulva rubbing, or penis-penis rubbing. No matter your genital configuration or gender identity, these positions work for all of us.

Missionary

Sometimes we just love the time-tested classic missionary position. This one provides plenty of full-body contact and eye gazing should you desire. There is space to nibble on the neck of your lover, as well as relax into the pleasure experienced. If this is your go-to, and it works, don't feel like you need to accomplish crazy feats of physicality and gymnastics to “perform” all the other positions.

Cowgirl

This woman-on-top position is the ultimate position for any couple. The woman (or top partner) straddles the man (or bottom partner) who is lying down. Here, she can maintain control of speed and depth of penetration, while also having her clit touched and tickled by herself or her partner. As she stretches her torso or arms to the ceiling, she can access a goddess type energy. This can be arousing for her, as well as for the partner lying down and gazing up at her. Yes, this position is amazing for intimate and/or lusty eye contact. Best of all, cowgirl can be accomplished with a penis, a dildo, or even two vulvas rubbing together without the penetration component.

Doggystyle

The media has given this position a lot of airtime, making it one of the most popular. This is because the man (or partner) from behind can look down at his partner's sexy behind, while also penetrating with far more depth and speed – if the couple wishes this. The woman (or kneeling partner) can really surrender to the pleasure she is experiencing, while also enjoying breast play or spanking, should she like either of these. This position is also great for penis-vagina combinations, penis-anus, dildo-vagina, or vulva-to-vulva rubbing.

For the woman bent over, consider hugging a pillow for extra support and/or having a pillow under the knees to prevent joint pain. The partner who is penetrating can kneel (again on a pillow if he wishes), or even stand up if his partner is bent over a bed or countertop. I really like this position in front of a full-length mirror (like in a closet or bathroom), so that the receiving partner can gaze in the mirror at the full body of her penetrating partner and make intimate and/or lusty eye contact. Then again, she might just want to wear a fun blindfold!

Spooning

This position is perfect for the couple that loves to cuddle! With its large amount of skin contact, spooning is another sex position that can offer a lot of intimacy. This is also great for anyone who needs a more relaxed position when supporting injuries or managing illness. Both partners can lie down on their sides, with knees slightly bent. The person penetrating is behind and can wrap their arms around their partner's waist. This position gives access to two key erogenous zones — the neck for nibbling and the breasts for stimulation. The shallower aspect of penetration here allows this position to be slow and sensual.

Advanced Sex Positions

The following positions are slightly more complex and physical. They are still easily accessible for many people but do require more flexibility and strength than the positions in the previous section.

Eagle

If you are the receiving partner, lay on your back, legs toward the ceiling. You can wrap your legs around your lover's neck or rest them on their shoulders. If your lover has a smaller penis, you can cross your ankles around your lover's neck, tightening the vagina (or anus) around the penis (or dildo). If you are the penetrating partner, you can kneel or stand at the edge of the bed. This position is great for depth of penetration or G-Spot access.

Straddling Tree

Lack of sufficient clitoral stimulation is one of the biggest challenges of cowgirl and reverse cowgirl. This version addresses that with a little old-fashioned grinding. The man, or penetrating partner, begins by lying flat on his back and one leg bent at the knee. The woman then climbs on top and straddles his bent leg, leaving their legs locked together. This allows her to rock back and forth in his lap while grinding her clit against his leg for additional stimulation. If she gets tired, she can lean against his leg for some extra support. This is also an excellent position for two women or partners with two vulvas.

Bended Knees

This is the passion position that comes straight from the pages of the Kama Sutra. Partners basically embrace in “leg-locking” by kneeling as they face each other. The penetrating partner lifts his right leg up and bends his knee, leaving him kneeling on his left knee. The receiving partner mirrors his actions, arching her left leg over his right one. This allows both of you to have eye contact and embrace each other while engaging in penetration or just good old grinding. If knees are cranky, drop a pillow for comfort. Again, this one is good for all combinations of couples.

Crouching Lion

Hear the roar with this progressive partner-on-top position! It starts with the penetrating partner lying on his back, with knees bent at a 90-degree angle. The receiving partner slips between him, positioning her torso between his legs. By planting her feet on the outside of his hips, she has leverage for her ideal speed and depth of thrusting. This position is also great for grinding as well as anal penetration.

The Dome

This gymnastic, yoga-style position will leave you and your lover seeing stars — literally! The receiving partner basically engages in a backbend (also known as a full bridge yoga pose), while her lover slides between her legs on his knees to penetrate. If a backbend is too aggressive, then she can do a hip thrust or yoga half bridge. He can grab her by the hips or butt for support. The backbend nature of this pose may create a head rush, which can accelerate arousal for some lovers.

Yab Yum

This is the ultimate position for all lovers—no matter your age, size, ability, sexual orientation, or gender. Though this position doesn't allow for intense and fast thrusting, it's the go-to for sensuality. The penetrating partner sits on the floor or bed, legs either straight out or crossed. The receiving partner sits on top, straddling the bottom person and wrapping her legs around his abdomen. The receiving partner can place a pillow under her butt for extra elevation and support. She can lean back on her hands or reach forward and wrap her arms around his neck. Lovers can have eye contact and place hands on hearts or move their energy and stimulation in multiple directions by moving their torsos toward and away from one another.

Remember, sex is not a performance. It's an activity of pleasure. If you want to try out some other positions for fun, go for it. If you want this position, just remember to include at least 20 minutes of excellent foreplay and perhaps a capable collection of sex toys!

Penetration & Genital Connection for Queer Couples

When it comes to queer sex for LGBTQI couples, the mechanics of genital contact and penetration are sometimes the same and sometimes different.

Vulva-to-vulva contact for lesbian, bisexual, and/or genderqueer couples is often marked by oral sex, fingering, tribbing, and use of strap-on toys. When it comes to penetration, strap-on harnesses and dildos are excellent options for the queer couple looking for thicker and deeper vaginal penetration. (Hetero woman can and do use them as well, typically for pegging their male partner. Some strap-ons are even hollow so they can be used by men with erectile dysfunction.) Strap-on harnesses feature a sturdy belt along with some extra straps for support. The harness typically features a rubber O-ring in the front that can be used to hold a special, strap-on dildo in place. This allows anyone wearing the harness to “use” the dildo on their partner like it was a penis.

Eve’s Strap On Playset is particularly popular. This playset comes with a fully adjustable harness to fit a wide range of body types as well as three different dildos. The dildos vary in size and shape, so you can experiment with multiple sensations depending on your experience and comfort levels.

Face Sitting for Oral Pleasure

This position is a favorite among many lesbian and bisexual couples but can be enjoyed by absolutely anyone. One woman simply lies down, while the other literally sits on her face. The bottom partner can then lick and kiss the genitals, as the top partner sits back and enjoys!

Tribbing

This is a woman-on-woman version of scissoring whereby the couple rubs their clits together for mutual stimulation. Start by sitting down, facing your partner with your legs spread slightly open. Slide closer to your lover, interlocking your legs with hers and enjoy the grinding. For extra sensation, you can add a finger, a clit vibe, or a double dildo into the works. The Crystal Jellies 12” Double Dildo features an extra-long and super-flexible shaft that makes it easy to share. Both ends feature a tapered tip for easy insertion. For clit stimulation, try the Joystick Rechargeable Wand!

Penis-to-penis contact for gay, bisexual, and gender queer couples includes handjobs, blowjobs, frotting, and penetration. The penetration positions are similar to those for hetero couples, with the main difference being the exclusive use of the anus and some name changes. For instance, the Cowgirl position turns into the Cowboy. If you’re interested in learning more about anal sex, then feel free to skip ahead to the next chapter, which is all about the backdoor.

Frotting

Frotting is the rubbing of two (or more) penises together for stimulation. Both men can kneel down while facing each other. From here, press your penises together and start stroking them simultaneously. Since the tip is the most sensitive part of the penis, make sure to rub your tip with your partner’s. You can mix it up by rubbing your own penis, then your partner's, and then back to yours.

Penetration for transgender people or intersex people, as well as for their partners, typically requires a good deal of communication to know how to navigate the body. Some trans folks have had surgery, some have not. For example, a trans-woman who has elected not to have surgery or is waiting to do so may have a penis and may love to penetrate a vagina or anus with her penis. A different trans-woman may have complicated feelings about her penis and may prefer to receive anal penetration or do other erotic activities instead. Some pre-op trans-men have a lot of sensation in their breasts and want it part of their sexual play, even if they bind their breasts in public. Others bind almost all the time and prefer not to include the breasts. Advocating for your body is key to discovering the pleasure possible.

As for those who are intersex, the genitals can vary greatly. Sometimes the vagina is too shallow for comfortable penetration, or it might be larger but not large enough to fully penetrate. There is no need to change or modify the genitals! The genitals of an intersex person can enjoy just as much pleasure as anyone else's genitals. If you or your partner want to explore options that seem beyond reach, sex toys can be fabulous for filling in any gaps.

Never forget — penetration need not be the gold standard of sex. No matter what our genitals look like; no matter how they function; no matter the gender we feel aligns with our genitals — we are still humans with an abundance of delicious and erotically capable nerve endings capable and deserving of pleasure.

Adult Toys for Everyone

Adam & Eve offers a wide range of sex toys and other items for hetero & LGBTQI couples that love playing together.

With over 375,000 sold, the Big O Multi-Stage Vibrating Penis Ring is one of their most popular vibrators for couples. This ring fits snugly around the shaft of his penis, keeping blood in his shaft. This has the dual benefit of slightly boosting his size and making it easier to maintain his erection. A small, powerful vibrator rubs against her clit or his taint with every thrust to help enhance their pleasure too. No wonder penis rings are often called the ultimate sex toy for hetero and gay couples!

Another great option is the Couple’s Enhancer Ring. This sex toy features two loops – one that hugs his shaft, while the other fits around his balls to help him last longer. It’s also covered with dozens of soft, flexible ticklers for added pleasure.

If your partner’s a little too sensitive for vibrations, Adam & Eve has plenty of non-vibrating rings from which to choose. I recommend getting a multi-pack like the Triple Erection System or the Ultra Sweller Penis Rings. Each comes with multiple rings in different sizes so you can experiment to see which works best for you.

While penis rings are intended primarily for men, it’s possible for two women to use them as well. Simply slip the ring around your favorite dildo (strap on or regular) to turn it into a rabbit vibe!

Another great vibrator for couples is the We-Vibe Match Couples Massager. The Match is shaped like the letter ‘C.’ One arm presses against her clit, while the other slips inside her vagina. It’s specially shaped so she can wear it while having sex to stimulate her and her partner at the same time. If the We-Vibe version is a little too pricey for your budget, the Satisfyer Partner Plus works the same way. It just has fewer bells and whistles, so it’s much more affordable.

Sex furniture is incredible for couples with physical limitations, and/or for the more adventurous couple. These pieces provide the extra support for tackling the more complex positions that we mentioned above.

With an average rating of 4.7 out of 5, the Liberator Ramp & Wedge Combo is one of the highest rated items on AdamEve.com. This versatile position aid consists of two pieces, a large ramp and smaller wedge. This makes it extremely easy to experiment with deeper penetration and new angles of entry. It also allows extra comfort while you try out a variety of new positions.

The Fetish Fantasy Spinning Swing is for the daring couple that desires to dangle in mid-air for a weightless feeling. It’s just as much fun during foreplay or oral.