By Kendra Holliday | November 16, 2012
Note: This article was originally published here.
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.
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.
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!