How to Put a Condom on a Soft Penis — With Your Mouth

Those of us in our 50-80+-year-old age group who are dating or in non-exclusive relationships need to take safer sex seriously. Yet how often do we face the challenge that the penis owner in our bed loses his erection (or thinks that he will, or doesn’t have one in the first place) when we want him to don a condom? We can have plenty of sexy fun with or without his erection, but what do we do about barrier protection?In honor of STD Awareness Month, I’d like to share with you an easy and sexy way to put a condom on a soft penis — using your mouth. With the help of the delightful Kendra Holliday (who told me, “I’ve never done this before!), the perfectly flaccid Sailor Soft Pack from Good Vibrations, and an expired condom (don’t we all have those?), I presented this demo during my “25 Tips for Sexy Aging” presentation at CatalystCon Midwest.  Here are the step-by-step instructions. (Practice on a dildo, soft packer, or consenting vegetable first.)

1. Start to unroll the condom, just enough so that you’re sure of the direction it unrolls. Squeeze out any air in the tip. (That doesn’t matter for the demo, but it’s important when you do it in real life.)

2. Perch the condom on top of the head of the penis and roll it down just a little, keeping it in place with your fingers. If the penis is soft, the condom won’t go down much — that doesn’t matter. You’re just getting it in position

3. Put your mouth over the tip of the condom-clad penis head, leaving the rim of the condom outside your mouth. Use your fingers to keep the rim in place. Start to suck.

4. Keep sucking gently. Use your fingers to assist the condom to roll down over the penis, which is disappearing into your mouth, much to the enjoyment of its owner. As you continue to suck and the penis gets pulled into your mouth, the condom will continue to unroll over it — magic!

5. Keep going until the condom is fully unrolled. Keep it in place with your hand as you remove your mouth — if indeed you want to remove your mouth — from the well-clad penis.

Doesn’t that sound like fun? Oh, it is! Thank you to the lover whom I will not name who first introduced me to this trick.

Many thanks to Kendra Holliday for her willingness to learn this method in front of an audience. Kendra is a sex surrogate in St. Louis and co-leader of SEX+STL (Sex Positive St. Louis). She blogs as The Beautiful Kind.

Thanks also to Randy Austin-Cardona for photographing this process, and to CatalystCon for inviting me to give my “25 Tips for Sexy Aging” at this conference.

Note to meeting planners who were considering hiring me to speak until they read this — don’t worry, this demo is optional! As always, my talks are personalized for your audience and your needs and preferences. 

Condom, Lube Giveaways from Lucky Bloke

Update: Although the contest is closed now, I hope you’ll read the interesting info below, including how to choose the right size condom!

What do you do to make safer sex sexier? How does it enhance your sexual enjoyment rather than interfere with it? What is your safer sex policy with new lovers or with non-exclusive partners?

Answer any of these questions and you can win free condoms or lube and dental dams!

I’m teaming together with Lucky Bloke, a condom subscription service offering more options than you thought possible, to find out what you think about safer sex and to reward two lucky people age 50+ with gift samplers of condoms or lubes! 

Here’s what you can win:

Condom Sampler: An assortment of 12 different brands of condoms. Some will be familiar; others new to you. If you have a size preference, let me know whether you’d small, medium, or large. Use this Size Test if you don’t know:

An empty toilet paper roll easily measures the erect penis of your choice. Click here.


• if there’s extra room = SMALLER / MORE TAILORED FIT CONDOMS  (best fit for 35% of men) 

• just enough room = MEDIUM / STANDARD FIT CONDOMS  (best fit for 50% of men)

• if it’s too tight = LARGER / GENEROUS FIT CONDOMS  (best fit for 15% of men)

Lube Sampler: I’m often asked which lubricant is best. I have my favorites, but it really depends on you and what feels good to you. This sampler lets you try 12 different lubes so you can figure out your favorite.

Whichever contest you’re entering, if you’d like some dental dams for safe cunnilingus, let me know that you’d like those included if you win one of the prizes. Dental dams aren’t just for the dentist’s office — they are latex squares large enough to fit over a woman’s entire genital area with room to spare so that there’s no exchange of body fluids during cunnilingus. I know, they look funny, but they feel fine and don’t interfere at all with the pleasure–take my word for it!

Here’s how you enter:

1. Be age 50 or over.

2. Email Joan the following:

In 50-80 words, answer one or more of these questions:

  • What makes safer sex (including condoms/ dental dams/ non-penetrative sex) sexy as well as smart at our age?
  • How do you make barrier protection sexier, more fun, and an enhancement of hot sex?  
  • What is your personal safer sex policy with new lovers or with non-exclusive partners, and why? 

3. In your email, include your name, age, email, and mailing address (does not have to be in the US!), and tell me whether you want the condom sampler or the lube sampler and whether you’d like dental dams included if you win.

The best two responses will receive samplers directly from Lucky Bloke, sponsors of this contest, and will be published here and in  The Ultimate Guide to Sex after Fifty, to be published by Cleis Press early in 2015. At Joan’s discretion, more of your comments may be used in the book, as well.

You may enter by commenting here, but please also email me the info above (#3) so I can notify you if you win. 
By entering this contest or posting a comment here, you’re giving me permission to publish excerpts in my book. I won’t identify you in any way. Thank you for participating!

Contest is closed, thank you!

Note from Lucky Bloke to you:

Discretion and ethical business practices are paramount at Lucky Bloke. We only use our customer’s information for shipping their orders. Everything is shipped discretely and personal information is never shared or made public anywhere.