Dianne

One of my very first sugar babies. I met her through an ad in the Village Voice. She advertised as nubian beauty with model build. I went for it and we met at a Caribean bar/restaurant.

She really liked sex without any protection. I found that very disturbing to say the least. How can someone do that this day and age with all the accesss to medical information is beyond me! But she wanted it:
the first time we had sex she was on top of me fooling around, and then she begins riding me. Luckily I had some CD's with me so we used them. I think she was a pro, with a serious family issue. I just wish she finds peace and a stable relationship she craves.

We met on and off for about 4 years. Reason we broke it off: a disagreement over a girl friend of hers: we met her at the same carribean bar we used to hang out (Baby Bo's on 23rd street, a great casual hang out kind of bar). Purpose was to meet and explore the possibility of a 3 some. Anyway, conversation is going great and there is obviously attraction between me and the friend who is a mixed race chinese and east indian from Guyana (i forget her name unfortunately). The friend really digs me and we all go back to her place. Had a couple of drinks, and then the doorbell rings. This Jamaican guy (her son's godfather, and also a part time drug dealer) walks in, started drinking, and we can't get rid of him! An hour later he finally leaves, and we all start making out. The friend gets totally naked and performs a dance right in front of me. Very seductive. Then she starts blowing me whille Diana plays with my balls from behind. Great time was had by all. A few months later her picture graced the inside cover of 'Time Out New York' magazine!
The next day, Diana calls me to wish me happy holidays, and, being pretty insensitive, I tell her I would like to see her friend again. She starts yelling at me and that was the last time we spoke. I sincerely hope she is well, and that she is a good mother to her young daughter.
A few years later I read a book written by one of her friends (we almost had a 3 some with her too, but that's another story), called 'Bird on a wire'. In this book she outlined Dianne's problems with drinking and bad family life. I feel bad for her.

Janice

Here I am in a hotel on Manhattan's west side, sitting on the bed across from a blond with a great set of eyes. I met her at Shaan, a fancy Indian restaurant (that has turned into a steakhouse: just what NYC needs, another steakhouse!). We are talking and obviously we both know why we are there, she is divorced and misses sexual activity, and I am the convenient stranger with which to engage.
David: Janice are you feeling ok?
Janice: Yes David. But I am with a strange man, in a dark hotel room. Not sure how comfortable I am with the situation.
D: How can I help?
J: I think that $300 is a fair exchange.
D: OK!
J: Let me make myself a bit more comfortable.
And with that, she goes to the bathroom and swithes into this nice little nite gown. Very sexy indeed. And its amazing that $300 was able to get her past the fact she had just met me an hour ago over Indian food and Taj Mahal beers!