February 22, 2010

Diary of a Sex Surrogate: The Devirginizer

by The Beautiful Kind

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 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. Both 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.