Dear Sasha,

I am 18 years old and still a virgin. I realize there are a lot of people older then me who are still virgins, but it is still quite hard for me to handle the pressure. I do believe I am ready; I am just mostly scared of the pain.

That’s because it hurts me to even put a tampon in. Is there anything I can do to prepare myself? Or at least make it hurt less when the time comes? I also have never had an orgasm, so I wonder if there’s something weird about that. I often engage in other sexual activities, but never the real thing, and I usually get bored after a while because it never feels that great. Could you please tell me what is wrong with me?

Confused and Worried

The first thing I would suggest you do is to get yourself a gynecologist with whom you feel comfortable discussing your sexuality. I have found that free sexual health clinics are best equipped to deal with these matters, since part of their mandate is, of course, offering unbiased advice on sexual health concerns. A pelvic exam will reveal some possible issues, one of which may be a robust hymen. In the meantime, you might want to research something called vaginismus, a word for painful intercourse, including the inability to insert tampons without pain.

First-time sex does hurt for some (did for me) and can continue to be painful until your vaginal canal becomes more receptive. This is not unusual. Some women who experience painful intercourse will prepare themselves with dilators, also known as stents. This is a course also followed by post-op transsexual women. You can read about it at Zen And The Art Of Post-Operative Maintenance.

As for tampon insertion, perhaps it’s a simple matter of lubrication. Try greasing it up with a little water-based lube before insertion and see if that helps.

There is nothing weird about not having an orgasm yet. I was 18 before I had my first orgasm during partner sex, and I’d been having penetrative sex since I was 16 and had been fooling around with people since I was 14. There’s so much going on when you first begin these kinds of adventures (am I doing it right? how do I look? is this going to hurt? why am I thinking about Catherine Bach while I’m sucking your cock? etc, etc) that it’s a wonder you can relax at all.

If you haven’t been masturbating, I would certainly recommend giving it a go. When I first began, I found using my hand a little intense, so I used the faucet in the bathtub. A nice steady stream of warm water can sure conjure up some agreeable feelings, let me tell you.

Or try purchasing a vibrator. A few websites that give good descriptions and reviews are comeasyouare.com, goodforher.com and goodvibes.com. I would also recommend Heather Corinna’s book S.E.X.: The All-You-Need-To-Know Progressive Sexuality Guide To Get You Through High School And College (De Capo).

He Shoots, He Bores

Dear Sasha,

I am a healthy male just a few months short of my 60th birthday. I am single at present but recently ended a year-long relationship. Despite my age, I am highly sexual and masturbate often (20 times a month). Over the last few years, the quantity of semen I produce has diminished to a drop or two, and sometimes I have a dry orgasm. My ability to “launch” it has all but disappeared. I have not had a vasectomy, and wonder if there is a way to increase my semen production. My girlfriends and I have enjoyed the messy kind of sex that copious amounts of semen offers. Any suggestions would be appreciated.

Dry But Still Pumping

I’ll implore you (as a woman who falls for anti-aging face creams and miracle hair products on a regular basis) not to buy into any of these wonder pills hawked by porn stars who are famously copious ejaculators. At one point, Peter “The Cumshot Legend” North was selling them on his personal website, but appears to no longer be; you can see his rather flaccid endorsement of others here.

As I’ve said before, the greatest effect North’s pills seem to have had is on the fleet of luxury cars he owns.

As we age, our muscles get a bit soggy, including the ones in the genital area. Women who find themselves peeing a little after they sneeze or laugh are encouraged to strengthen their PC muscles, and I would suggest you try the same. You can find directions (apologies for the bowmp-chika-bowmp music) at kegelexercisesformen.com. This won’t necessarily improve your load, but it will help keep your erections and general man area in firmer shape, which helps with a more impressive launch.

Your situation could also be related to a prostate issue, so it’s a good idea to have a check-up with your doc. He may then recommend you see a urologist.

On the website Kinsey Confidential, Debby Herbenick says, “It’s also worth noting that some research has suggested that body fat distribution may be related to the volume of semen. If you have gained a considerable amount of weight in recent years, it is possible that the weight gain is related to your volume of ejaculate. This is something you can also discuss with your health care provider.”

Herbenick recommends the book The New Male Sexuality (Bantam), by Bernie Zilbergeld, as one of interest.

Another way to increase your load, I’m sorry to say, is to refrain from ejaculating, meaning you may want to cut back on your masturbation regime.

And, hey, messy sex doesn’t always have to involve your semen. Many women ejaculate themselves, and you can also create the same effect artificially. The lubricant Liquid Silk mimics the texture and colour of semen very well. You’re getting on, bud, and your body’s changing. Respecting and working with what you’ve got with some humour and ingenuity goes a long way.

This column was originally published in NOW Magazine. Ask Sasha: [email protected]

Sasha Van Bon Bon

Sasha is a nationally syndicated sex columnist whose work has appeared in a variety of Canadian weeklies and online magazines for over 15 years. Her column appears weekly in NOW magazine. She is also...