I understand that it is a common practice in many cultures--and yes, even in the U.S.--for a father to hire a prostitute for his son's "first" experience. It is also traditional in some societies around the world for an older woman to introduce a young man into the mysteries and pleasures of sex, and this sometimes includes teaching him to be a good lover to his future partners. Well, I never exactly imagined myself in this position, but a few nights ago, it did happen. Most often, when a potential client tells me that "this is my first time," he means in "hiring an escort." It became clear to me the other night that the young man who had availed himself of my services meant literally HIS FIRST TIME--EVER!!! So there was a moment when I thought: "Yikes--I have a whole new job description!," and I was a bit taken aback at first, but it actually went very well, and I feel now that I was an essential part of an important rite of passage for this young man. Pablo (not his real name, of course) came out to meet me at my car. He is an extremely affable, sincere, handsome, and somewhat shy man in his late 20s, who for various reasons related to professional responsibilities and due to the repressive culture into which he was born, had just not yet had a sexual encounter with a woman. I was immediately impressed by his matter-of-fact attitude, his openness, his willingness to learn, and his natural talents in bed. I loved that Pablo was so very practical, and just decided to hire someone like me himself! I can definitely understand how a relatively introverted young man from another culture would feel very lost in the American dating scene, with all of its mixed signals and the mine-field of stereotypes, expectations, and assumptions which of course plague us all. How much more difficult for a genuinely shy, sensitive and sincere young male to try to navigate this tricky course? I was just in admiration that he decided on a very reasonable solution: hire an escort for a night of lessons and pleasure, and the most important thing: To NOT be a virgin anymore!!! We talked about many things, not just the mechanics of sex itself. He wanted general advice on dating, and I had to rack my brain and draw on my vast experiences along those lines to think of what to say to him. Again, I have never been with a virgin (that I know of) in my personal dating life or at work, so it was a bit disorienting at first. Normally, I am hired to be a companion and playmate for an hour or two for a man who knows what he wants (for the most part). Sometimes clients are shy or nervous, but they are not usually "newbies" to the whole act itself. What was really surprising was how difficult it was for me to advise him on how to behave with a new woman he was dating. There must be so much pressure on a young man, I would guess, to be a "gentleman," and yet to also make all the first moves and to be the aggressor when it comes to getting physical. I found myself encouraging him over and over again to be himself, to be honest, to communicate, and to ask his date what she enjoys, etc. Then I had to explain in rather convoluted terms that often a young woman will crave sex as much as a guy, but her mind will tell her that it's "not right," or whatever. How to describe to a very earnest young man who has hardly ever dated that relationships can be full of "Mixed Messages from Hell"?!! This was probably the most challenging part of my job that night. I think the best advice I could give him was to find someone with whom he was comfortable, and with whom he had good communication, and that these two qualities in a relationship could go a long way towards helping to deal with any other difficulties that might arise. He had done his homework by watching porn and studying up somewhat on the matter of human sexuality in general, and so he was well prepared--and very willing! He had also practiced with a condom. It was just so amazing to me how he had it all planned out: "I am going to prepare myself, and YOU are going to teach me"! I quickly analyzed in my mind what are the normal "steps" a guy usually takes when he wants to show a woman that he likes her, and that he is interested in becoming intimate. "Touch her gently on the shoulder, on the leg while you are chatting with her;" "If you are sitting next to her on a bench or in a movie theater, try to hold her hand or put your arm around her shoulder;" "Watch her body language to see if she is receptive," etc., etc. There really is quite a fairly well set-out sequence of events if you take the time to break it all down. I think young men are probably running these steps through their heads all the time! After talking for awhile, we finally went to bed, and I was actually a bit nervous--but not as much as him--he was shaking! But he has a very good sense of humor, and I am told that I put people at ease, so we got through the slight anxiety. I thought he was really quite brave, and so down-to-earth about the whole thing. I had to think about what a guy "usually" does first in bed. I again reminded him that "everyone is different," and to "ask your partner what she likes," etc. I taught him how to French kiss, how to touch me all over very sensually--pointing out that this is the way I like to be touched, but that it may very well be somewhat universal to all women in general. I shared with him the maxim that I heard from a client one time, and that I believe to be true in many ways: "If you want to make a man feel good, worship his cock; if you want to make a woman feel good, worship her whole body." Pablo is really quite a good kisser, and has a very sensual touch--especially for a man who has never done either with a woman before! He was quite eager and willing to kiss and play with my breasts, which he did very well. It was so funny--I actually found myself being "first time" nervous when it got to the point when he was going to explore my private parts. I don't know if I was picking up on his anxiety, or if it was my own, based on not knowing how he might react to the whole situation. Well, he was a champ. He kissed my vulva right off the bat, and explored the whole area with his tongue and finger. I think he even succeeded in finding my G-spot! Then I really started enjoying the fun of it all: I was INITIATING this young man into one of the most important experiences of his whole life. I was his teacher, and he was an extremely willing and enthusiastic student. We also both saw the humor in the whole situation, and were able to be light-hearted about it. It still makes me chuckle when I think about it--that I didn't know what role I was going to be stepping into that night! I'm actually glad that I didn't know ahead of time that it was going to be my job to "de-virginize" him, or I might have put unnecessary pressure on myself beforehand. This is one of the things I love most about this work: The Adventure of it All. Being the New Age Escort, of course I perceived the sacred element in this experience for the both of us, and I said a little prayer as he entered me. I was again impressed by his demeanor once we got to the intercourse. He is just a naturally talented and sensual lover, and he had some very nice moves on his own without me saying anything. I have often heard that when a guy has his first time, he usually comes in a matter of seconds. I was on top at first, and showed him various permutations of the "female superior" position, and why many people think it "superior" to the perennially favorite but perhaps overrated "missionary position." He actually held off his orgasm very nicely and was a true gentleman. Then when I got on the bottom, it was all over in a matter of seconds, because we were focusing on him finally, and he was able to relax and let go. He breathed a metaphorical sigh of relief that he had finally gotten his "first time" behind him. He was very grateful and thanked me very much, and told me that his next time would be with a real girlfriend. It was an extremely delightful and life-affirming experience for me, if unexpected, and I am deeply grateful that I could assist him. I wish there wasn't the age difference between us, because I would like to date him myself! Just for fun--and partly to "research" this entry--I watched The 40 Year-Old Virgin, which I had recorded previously but hadn't yet watched. I found it to be a surprisingly sweet, funny, and endearing film, with a rather clear message: Everyone is on his or her own path, and their sexual "status" really has very little to do with who they are as a person or what kind of lover they might be. It also reminded me of an article I saw long ago entitled "Why nerdy geeks make the best boyfriends." The film is perhaps a not-so-subtle reminder to "Not judge a book by its cover," and to give ourselves time to get to know someone before deciding anything about them. People can surprise us. I believe that Pablo, just like the character in the movie, will make some woman very happy someday on many different levels. I wish him all the best! | 
