The De-Virginizer

By Kendra Holliday | November 16, 2012

Note: This article was originally published here.

Adult male virgins often feel shame and anxiety

Not every woman in their late 30s can say they devirginized four men in one year. I can. Over the course of several months, I spent intimate time with four adult male virgins, from 24 to 38 years of age. Two had overwhelmingly positive outcomes, and two did not.

The Good

As a sex surrogate and sexplorer, I have a philosophy when it comes to people, places and things: Leave them better than you found them. That is always my goal. When I’m in bed with someone, I want them to feel amazing and very special. Despite my best intentions, however, it doesn’t always work out that way.

Virgin #1 was a 38-year-old man with a dismal track record in the bedroom. He went to bars to “pick up chicks,” but would shut down as soon as he got them home. He’d give them oral sex, all the while sweating bullets as he feared letting them down, which in his mind, he did. He counted on alcohol to cloud the evening, mumbling about “whiskey dick” as he sheepishly showed them the door. Finally, he decided enough was enough, and he sought professional help.

I spent a couple hours talking with him about his issues, which was one key to solving them. Having it all out in the open was a relief to him—it was good to be on the same page instead of hiding his insecurities like porn under the mattress.

We then spent a couple hours in a very open and honest setting—he felt safe and understood by me, which was such a contrast to his past experiences. He was getting to the point where he was feeling like women were adversaries, to be feared.

He had successful intercourse with me for the very first time. He was amazed—it felt so right and spectacular. “I can’t believe I’m doing it!” he kept muttering incredulously in my ear as he pushed awkwardly in and out of me.

The sessions he had with me were a breakthrough with him. He found that women are not scary creatures, and went out into the dating world with newfound confidence.

Virgin #2 was a charming 25-year-old with a perfectly charismatic personality. He was pursuing a career in politics, and wanted to be sure the time he spent with me remained under wraps, as he was very conscious of the potential for future scandals.

#2 had never kissed a girl. I was his first on all fronts—first kiss, first oral, first everything. He was so sweet, I asked him how this came to be, and he told me it was due to lack of opportunity, but that he had his eye on a special girl, and wanted to make sure he would be prepared for courtship.

It’s a good thing he went this route, as he was a terrible kisser. I patiently showed him how to relax his mouth and take his time. He went down on me and remarked, “I’ve always heard a woman tastes like fish, but that’s not true at all! You taste wonderful!” He completely freaked when I put my mouth on his penis, saying, “Okay, I’ve always heard a blowjob feels incredible, and that is absolutely true!” The cutest moment was when he got on top of me and started having sex with me.

“I had NO IDEA how much work sex is!” he huffed and puffed. He used pelvic muscles he never realized he had! It felt so great, TOO great; it took him forever to orgasm. He finally resorted to a more familiar method—masturbation as I quietly lay next to him.

Luckily, he started dating the girl of his dreams a month after our session, and he couldn’t thank me enough for giving him a great head start.

My goal is to leave people better than I find them

The Bad

Virgin #3 was a 30-year-old man who had also never kissed a woman. He was completely handsome and stylish, but very socially awkward. We went on three dates before doing the deed, and he was by far the most talented lover out of all of them. As we made love, he was simultaneously thrilled and horrified at how incredible sex felt. I was riding him, my hair streaming down my breasts, and he lamented mid-thrust, “I can’t believe I’ve been missing out on this for TWENTY YEARS!” Such a bittersweet moment.

I was so happy for him, and was glad to help prime his pump so he could go out and knock ’em dead. But afterward, he started asking me out on more dates and even proposed a camping trip. I gently but firmly reminded him of the boundaries set in place ahead of time, and he was crushed. It’s been a year, and he still hasn’t dated or been with anyone but me.

Virgin #4 was a 24-year-old man who was painfully shy and inexperienced. Incredibly naïve, he had had his heart broken by more than one catty cyberchick, and he needed some TLC.

I gave it to him. We got together a few times, took baby steps, and finally consummated the relationship. He was like a deer in headlights, stunned at the feelings he had never tapped into before. He found partnersex to be overwhelming, and couldn’t orgasm with me. He got ME to come though, perfecting his oral skills and being an apt pupil indeed. Have you ever been licked by a young, handsome virgin? I highly recommend it. And then he became attached to me.

When I let him know that our time together had run its course, he became very bitter and felt slighted. He even accused me of using him. A couple months later, he started dating a girl more his age, and that went well for about four months until she completely shattered him by cheating on him and then dumping him for the next shiny new guy.

The Ugly (Truth)

There are consequences to your actions. The men who slept with me and I knew the risks involved with getting too intimate. We are all grown people, and we all have emotions. Despite our best efforts, some feelings were hurt instead of helped. I cautioned each of them ahead of time to be prepared for the unexpected. I feel terrible for those who left with a bad taste in their mouth.

But that’s the price you pay when you play with others—for every amazing sensation, there’s a chance for disappointment. For every euphoric moment, there’s heartache around the corner. Pride, regret, guilt, joy… It’s all these feelings that make us humans, and I wouldn’t want it any other way.


UPDATE: Tune in Monday for a heartwarming update that involves Virgin #3!


Jenny 2012-11-16 10:29:56

Wow! LOVE THIS!! Just found your blog 🙂 thanks for sharing!!


Jem 2012-11-20 13:17:29

I’ve devirginized two guys: my future husband when he was nineteen, and a twenty-eight year old just a few years ago, so I’d have been about forty. So I don’t think I have enough data to come up with any patterns, but both times:

1. I was expecting it to be quick, but it wasn’t. Both times, they were keen, perhaps a little shy, but not squeamish. Tender, very vanilla, missionary. Very sweet first dates beforehand, where they were plucking up the courage to ask if I wanted to hold hands and I was secretly plotting filthy ways to take their innocence.

2. They needed a lot more guidance ‘down there’ than I’d have thought. Their first guesses about where they were going were not very accurate at all.

3. I came.

4. They were ready for their *second* time really, really quickly. They had their breath back before I did. They were very quick learners.

5. I felt a real sense of responsibility, during and especially afterwards. Whatever else happened, I’d always be their first. I was very lucky my first time, and I wanted theirs to be special, too. Afterwards, I felt a little territorial, a little like I was responsible for them. I still feel a bond.


Jem 2012-11-20 14:16:34

And now I’m thinking about the terms. If you pop a guy’s cherry, someone needs to call an ambulance because something just went badly wrong, but can you ‘deflower’ a guy?

And that age-old question: when does it count as devirginizing for guys?


Amanda Marcotte 2013-01-29 04:09:00

I think men who pay for sex are the scum of the Earth. They are just perverts, creep and misogynist who want to abuse women in bed.

If men have RESPECKT for women, they would be getting sex so much easily.


    Kendra Holliday 2013-01-29 12:40:29

    Do you know many men who pay for sex? I’ve met and know many and they are not scum, they are for the most part lovely humans and there is mutual respect present. And hey I’m a pervert!


    Nat 2016-01-18 12:30:09

    hahahaha that was an ignorant comment. I know some guys who are wonderful, sensitive intellectuals who, for the life of them, can’t get girlfriends. Like me, they are college-aged males looking for a relationship that includes sex as a major facet. They have tried every medium of communication (dating apps, in-person communication, and vacations to other places), employing every appropriate rhetorical tact to no avail. The fact is that some guys just don’t have luck with romantic affairs. It is not a matter of being rude or slimy, like you foolishly suggested. Most men biologically NEED sex, unlike some women who could go years without having a sexual partner and not feel any shame or regret. So, with all of that being considered, some of the aforementioned gentlemen told me that at some point they may pay for sex, and I think no less of them. They wouldn’t doing it to work out some weird, misogynistic fantasy.


Steve 2013-09-15 19:00:15

Good Article. I am a 38 year old male virgin. This last year I have had about 4 opportunities to have sex but turned down 3 of the women because I wasn’t attracted to them and one was 18 yrs old and was she said she would graduate high school in 2 months so I had to turn her down because of her age but she was cute and I really wanted to have sex with her but it would be wrong. Some women started getting interested in me the last 3 months don’t know watch changed other than my haircut, clothes, and some female friends I guess help some.

To be honest I am just average looking, honest, nice, have a good career, non drug user, working part time on a masters degree, do some volunteer work, but I guess women in general just found me too nice, the nice guy syndrome and I have approach anxiety with women. If I don’t find a women attractive or she is married then I have no problem talking to them. So I need to find a way to break through the gap to date women I attracted towards.

My approach anxiety got so bad around February this year that after 1 successful group date with woman I liked that I almost killed myself when the 2nd date went bad. The woman got drunk tried to sleep with 4 different men and gave me backhanded compliments, which made no sense when the 1st date was so successful. The first date we ended the night with a kiss and was flirting all night and dancing so it must have been good. Also something happened to the woman I liked after that night she never went out dancing again, never drank, and only stays home. I guess we both hurt each emotional which is unfortunate because I still have a lot of feelings for her.

When I held the gun to my head and cocked trigger I was thinking I am good enough for any women, how can I be a better person, will I always feel emotional pain when I don’t have someone to share my life with. I then realized that there are a lot of people that care about me that would be really hurt. I never have shared this my close friends don’t know how they would have reacted and I don’t want to hurt them.

Sometimes it is selfish but I imagine how good it would feel if there was some beautiful woman out there felt the emotional pain of losing me and wishing they had the chance to know me when I was around. I guess some sort of weird romantic notions, I guess the strict religious beliefs that I was raised on ruined my ability to be honest with my desires to have sex with attractive women so I am rarely direct when asking out women which makes it really hard to get dates.

I stumbled onto your blog from DoctorNerdLove website article on older virgins. It was a good article and logical but still the emotions of being an old virgin hurts because it feels like everyone since the age of 12 has had sex and I am left alone.

The one thing I can say is that from your picture kind and beautiful. Your article shows that you really care for people and doing it in your way. I only wish that I could find a woman like you where I live. To be honest because you are so attractive if I saw you in bookstore or grocery store I would never have the courage to approach you.

Life is a struggle and it will be interesting to see how I choose to live it, short or long with passion or without pain. All I know is that life it too short when you have someone you love to share it with and too long when you are alone.


Augustus Gloop 2018-12-20 14:19:37

47, still have my flower. I’ve never felt that it was the right time to sleep with someone. Most of the time, some strong part of me says ‘NO!’ and then I think about a load of excuses to avoid women. The weaker part of me is becoming more interested but I don’t know if I’ll ever ‘take the plunge’. There’s always some problem in my mind, like I don’t want to hurt women or get hurt myself, both of which could happen all too easily. I am capable of causing great offense and my manner is generally off-putting. I give up quickly when I feel that I’ve done something wrong, no matter how minor. I’ve had crushes a few times but they come to nothing because the women are unavailable. I just have to be strong and keep living. Perhaps it’s my destiny to be celibate for life. I find it very difficult to sustain interest in a woman beyond a few minutes. I feel like a failure but then anyone is a failure in one way or another. We all have strengths and weaknesses. At least I have other pleasures, especially creative writing. Exploring new ideas is more interesting to me than dealing with women.


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