Monday, June 8, 2009

Client #16 - a boy to break your heart

I have finally seen a new client! After I put my latest ad up I wasn't sure if I wanted to actually take any bookings or if I was just mucking around. So I took the passive aggressive way out and replied with such inflated rates and strict requirements I thought I'd get no takers. Instead, a gorgeous, young, polite boy replied and booked me for two hours! A combination of the stupid amount of money, plus his great photo and writing and I was super keen to see him.

He'd requested me dress in business attire ,and since I felt like giving him the time of his life I actually went out to the sales and bought a black skirt and ruffled, stripped business shirt. It was great fun buying corporate wear after so long out of a corporate office. Quite funny that my wardrobe is totally casual - except for the sexy costumes and fetish wear I use with clients. Nothing in between. I admit it did give me a bit of thrill too - knowing I'd be wearing it later that night in my "double life" as such. The day just seems to have so much more spark to it when I'm about to visit someone.

I was a little nervous about visiting him at home, since he was way, way, deep in the suburbs. But I gave Bell all of his info, even his photo, and did the usual safety stuff like insisting on seeing every room of his house before we exchanged money etc etc - there were no football players hiding in cupboards or anything. Whew.

Now...onto the details. The boy was tall. 22 years old. Geeky. Overweight - a BHM I guess you'd say. But since I quite like my guys cuddly I thought he was near perfect. Dark horn-rimmed glasses and a passion for sci-fi? Jackpot.

The trouble was though he was just too nervous. And self-conscious about his weight, and lack of experience. It reminded me of myself at a similar age. I tried my very best to be sexy and reassuring, and take the lead - but it was just terrible. You know how when two people with Tourettes get together they can make each other's ticks and cussing worse? Well, two fat, sci fi geeks together just seemed to throw me back to his age and I lost a lot of my sexual vibe. I tried and tried and tried to get him to relax and open up. In the end I did convince him to masturbate so he would cum. And I masturbated for him.

Then we fell into conversation. And he revealed probably far too much for his own comfort. Lack of girlfriends, lack of experience, lack of confidence, suicide attempts, despair at the stupidity of the world. I thought he had a marvellously black sense of humour and suspect he is super, super smart. I just held him at let him talk. In return I revealed far too much about my awkward young adult years too - very similar stories, minus the suicide attempts for me.

I think the similarities are what is making him so hard to forget. His loneliness and isolation. I tried to just spoon with him and stroke him and say all of the things I wish I could have said to a younger self. That life gets better, that everybody is lovable no matter their shape, and that it will work out in the end. It was just heart wrenching.

After more talking than sex, he let me go a little early so I would make it home before it was too late at night. And he walked me to my car and kissed me at the door to make sure I left safely since it was a slightly seedy neighbourhood. So thoughtful - I just know he's a perfect match for some lovely, chubby, girl somewhere.

Four days later and I'm still mulling over the experience. Even sent him a quick email reinforcing some of the stuff I'd said, including that I was glad he hadn't succeeded in the the suicide attempt, for the world would be a poorer place without him. He replied thanking me for being so kind.

I take a couple of life lessons from it all. The main one being that unless you can convince your self you're okay, then you won't be. It's totally perception and no one can change it for you. I've also learnt that men suffer just as much as women with the whole size and body issue thing. And it's no less painful to be an overweight guy than a fat girl. That was eye-opening.

Oh...and I also figure there is some truth in the stereotype of the whore with the heart of gold. This guy really did affect me, and I truly hope I've helped him at least a little - even if it was just a few hours of comfort on a cold Friday night.


  1. With guys, some of us hit a groove when we hit our mid to late 30's. Up to that point, the pressure is on to be a "stud." Once we realize how stupid it is to try to be a "stud", we can then be ourselves, which is usually what women want anyway.

    A few lucky guys figure this out early in life. I wish I had.

  2. I hear ya The Toy. I didn't hit my groove until I hit my mid 30's. It is fairly true that if I knew then what I know now I would have been a much better young man. I think you don't pick up a certain confidence until you are comfortable in your own skin... sometimes that takes awhile (or never I would imagine). That's common among both sexes....

  3. This story was just heartwrenching! I'm happy you were so kind to him!

  4. It's amazing what you are learning and sharing with us... you should consider writing a book. I'd certainly read it! :)

  5. Oh, my, he sounds like precisely the sort of boy I'd have fallen hard for - and still might.

  6. You are a nice person, CG. :-)

    I'm new here. I think I'll be visiting again.