5 Ways to Pleasure a Penis

A naked athletic man in white underwear sits freely and confidently on the couch.

Helping someone have an orgasm is one thing. Making it memorable is another. 

If your partner has a penis and you want to show them a great time, that’s wonderful. But I find that the people really skillful at this know how to elongate their partner’s pleasure. They know how to create a lot of build-up, and how to use body / hands / mouth / toys etc. in such a way that their partner is practically begging for an orgasm. 

Because the sexual nerve endings of a penis sit close to the surface of the skin though, there’s an art to this build-up. You don’t necessarily want to help your partner get off right away, but rather let them enjoy the journey in the most amazing way possible. So, how do you find that balance? Here are 5 techniques that create a sexy build-up to an incredible orgasm. 

1. Tease Wisely

When it’s time for foreplay, resist the urge to strip off your clothes and theirs immediately. 

Instead, let your body language telegraph what’s to come by using your hands: grab their ass, pull their body to yours, run your fingers up their inner thighs. And yes…I would call this “dry humping,” something you might associate with adolescence. But remember, this is likely the place you started building your sexual repertoire, and this is the zone that builds a ton of arousal! Aka blood flow to the genitals, aka helping them get an erection, which puts their sexual response into gear. 

Try: Making out on the edge of a bed or chair with them sitting down, clothes on. Sit in their lap and straddle them, a la Lotus Position. Start mimicking the movements of sex: pushing into them, light grinding on the penis. Kiss their neck, run your hands underneath their shirt, squeeze their nipples (an erogenous zone on everyone). Apply increasing pressure on their penis by pushing your pelvis deeper into their lap. Depending on your angle, this puts pressure on the head – the most sensitive part of the penis – and should feel really good to them.

2. Give An Upgraded Handjob

A lot of the time, the shaft (the long part of the penis) gets outsized focus in a handjob. Ask anyone with a penis: stimulating the shaft is awesome! But there’s more you can do during the handjob to make it extra stimulating.

Here are two parts that often get neglected in the handjob: the frenulum and the testicles. The frenulum is a small patch of skin on the underside of the head, connecting to the shaft, and containing Pacinian pleasure receptors. It responds to deep pressure (more on that in a moment), while your best bet for the testicles is light pressure. The testicles not only produce sperm, they are jam-packed with nerve endings – making them extremely sensitive. For most people testicle stimulation feels pleasurable, the trick is to be more gentle here than other parts of the penis. 

Try: Making your handjob two-handed. The frenulum responds to vibration and deep pressure, so apply lube (bonus points for one that tastes and smells delish), wrap your fingers around the shaft, and start moving it up and down the shaft. Meanwhile, use your other thumb to press into the frenulum while your other hand does its thing. Vary between that and cupping the testicles, all while keeping your shaft movement going. The net-net is waaay more sexual nerve endings getting stimulated.

3. Try a Kinky Blowjob 

I say “kinky” because you’re going to introduce some power dynamics. But in the spirit of all kink, it’s important to remember that this is play, and you should only do what you truly want! On that note, the two main concepts I want to talk about here are deep-throating and orgasm denial, while you give oral sex. 

Do you have to deep-throat? Of course you don’t. And truly, you should only do this with a partner you trust – prolonged gagging on a penis isn’t safe or something I would recommend. But if it’s something you legitimately want to do with a partner, there’s a taboo element that could feel exciting for you both. 

With orgasm denial, the power is in your hands literally and figuratively. The key is to attune closely to your partner’s arousal and body language, backing off when they’re getting close to orgasm. It’s a sexy form of edging, which I have a whole guide on here.

Try: Making eye contact during your blowjob. Whether it’s after deep-throating, after orgasm denial, or just little sexy pauses between sucking and licking the shaft, eye contact always feels intimate. On top of that, it’s incredibly arousing to our nervous system. This study proves what we knew already…that eye contact is pretty much a universal turn-on. 

4. Use a Vibrating Penis Ring 

While penis rings are traditionally used to keep the wearer hard, vibrating penis rings act like a sex toy. They stimulate the base of their penis (away from the most sensitive parts), but when worn during intercourse, they feel incredible on the other person.

If you’ve got a vulva, the vibrations of a penis ring will stimulate your clitoris during sex – it’s *chef’s kiss* for mutual orgasms. And even if your partner doesn’t “need” a penis ring to stay hard, the extra engorgement to the shaft will light up more of their sexual nerve endings, making intercourse feel deliciously sensitive. 

Try: The TOR 3 from LELO: the gold standard of vibrating penis rings, with a generous surface area on top for broad stimulation. It’s also completely waterproof, so very fun to use in the shower or hot tub. Just don’t forget lube!: water washes away natural lubrication, so a silicone lube is best. 

5. Give Prostate Massage

If your partner has a penis, they have a prostate: a sensitive, walnut-shaped gland located about two inches inside the anus. And it feels very good when stimulated directly. 

A prostate or “P-spot” orgasm is often compared to a G-spot orgasm on those with a vulva. It feels deeply internal and very powerful – almost a full-body orgasm. Plus, your partner doesn’t need to be erect to have one! So even if they’ve already had an orgasm, this is a nice trick to have up your sleeve if sexual contact is still going. 

Try: With a very well-lubed (and optionally, gloved) finger, gently and mindfully insert it into the anus. This is obviously a time for tons of communication, so frequent check-ins apply as you increase depth. Try inserting up to the second knuckle. You’re feeling for a soft, padded gland that you can either pulse back and forth on with the pad of your finger, or apply a circling motion. I’ve got a full how-to on prostate massage here if you’d like to get all the intel.

If your partner has a penis, I hope these ideas inspire you for your next sex sesh! Which ones do you love, and which ones are new to you? Come find me on Instagram @sexwithemily and let’s talk.

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