Double trouble: Cali and her daughter part 2

About 30 minutes later the door knocked and the daughter walked in. I told the mother that she looked left out and it was my duty as a gentleman to serve her every whim. 'Let me talk to her' momma Cali says. Jaimie took a shower and then wrapped herself in a bath towel. She had a quiet talk with momma, whom I could see through the mirror of the bathroom, the door being half open. At one point, the daughter gave the mother the finger! Not sure what that was all about. I think the mother wanted to make sure the daughter doesn't get a better deal, and the daughter told her to get lost. I say that because on her way out of the room the mother warned me: 'Make sure her's doesn't last longer than mine!'

Anyway, the daughter literally jumps on the bed with a big smile, surprising me, still with the towel around her, and me being totally naked. She pulls my hair back and starts nibbling on my neck which was very enjoyable, but I was afraid she was going to leave a mark. I discovered that both her and her mother had a Harley bolt shape tatooed on their hips. Nice piece of work they do in Fresno.

Momma comes back, and exhausted we all go to sleep, in the same bed, with me in the middle. I turned around and slept cuddling the daughter. She was soooo cute. I felt like those times in college when I slept cuddling against my then girlfriend, whom I later married. Of course all this cuddling was interrupted by the insatiable mother, while the daughter was (or pretending to be) asleep.

Next morning I had to leave. So the daughter said, 'Are you afraid to party with Cali?' so I politely asked the mother to go downstairs and check to see if there are any messages for me. Then I take the daughter and threw her playfully on the bed, she obligingly stripped and the act was consummated once again. Of course, her hair was messed up so she had to spend another half hour fixing it up. These two were hair maniacs. We parted ways, and I told Jaimie that I would love to be her long distance SD, and she would be welcome to fly back here if her mommy lets her, all expenses paid. She has not taken me up on the offer, to this date.

And after that I had arranged for another sugar date at one of my favorite hotels on the east side. Walking down there I was thinking to myself that I had finally mastered the art of serial Sugar dating, a goal that had eluded me since I was 25 years old.

Anyway. One more for the SD David diaries...

Double trouble: Cali and her daughter

A classic one, and I guess every man's wet dream. I suppose I am one of the fortunate ones?

****Editors Note: I found some of these posting in my old notebook, so the next few entries are not in chronological order. One day I will go back and put them in the beginning of the blog. But for the time being, here it goes ****

'Hi Dave, we found your ad on Craigslist. You don't know us but my daughter and I will be visiting New York for the weekend. So we were thinking that we may need a tour guide'.

When I read this, my immediate reaction was :'YES!' But I decided to play it cool, as to not show too much excitement. So I told her that I would love to be a tour guide, not too busy the coming weekend, everyone is visiting friends Upstate, so as luck would have it I am all alone. We exchanged pictures, just to make sure there is mutual attraction, and we kept communicating via email or text throughout the week.

The big day came, and she asked me if I found a friend for her 22 year daughter, 'She is hot'. I said 'No, but don't worry, I will take care of both of you, I aim to please'. She laughed at that and said 'You think you can handle two nasty Cali girls?'. I said 'Don't worry about me I'll be fine'. As I was walking toward the hotel she texted me (obviously to psych me out) 'Are you nervous?. 'No, why would I be?' I texted back.

So I met her downstairs at their hotel bar,and we started talking like two old buddies. We discussed her interest in motorcycles and dragster racing, and she showed me some pictures of her in her purple racing suit. She raced professionally sometimes, and looked really hot in that suit. The daughter, Jaimie, finally arrives, and she was a sweet looking, recently turned 22 year old hottie. Quiet, but the kind of quiet that you know can spell trouble.

She really wanted me to find a Harley store for her. I didn't think that one even existed in Manhattan but it did and we found it. Both mother and daughter tried on some hats and black motorcycle tank tops, that made the blond daughter look really hot. At this point I was really starting to eye the daughter, by the way.

We went to the Oyster Bar at Grand Central as they liked seafood. Not my favorite, but they were the honored guests, so what the heck. After dinner, they presented me with a free pass to New York Babes, so we headed down there. There, the mother proudly announced that Jaimie, a college student in pre-med, is putting herself through college by part-time striping. She even showed me several pictures of her in a thong climbing the pole. If there were any doubts in my mind that I was lusting after the daughter, there were dispelled at this point. She wanted to try out as a guest stripper (only topless in NY) at the Babes but there was a waiting list !! I didn't realize this was a competitive sport. The talent there was mediocre, so I am sure that Jaimie would have blown them to bits. Was able to discreetly get one of the strippers phone number right under the eyes of the supervisor by giving her 22 dollars as a tip, and asking for a $1 in change with her phone number (without her name of course) written on it. That's the topic of another blog entry, however.

After that adventure, we headed back to the hotel bar, where we caught up with Santino (?!) a gay looking Australian air steward whom they had met earlier. Great laughs were had by all, but now it was getting around midnight so it was the moment we had all been waiting for.

We went upstairs to their room and the mother tried on that great fishnet dress she had brought with her. The daughter went to catch up on emails at the Wi-Fi lounge downstairs, while Davey boy and momma got better acquainted. She would just do anything to please, as long as I asked nicely. This was a real life date sprinkled with sugar. I was somewhat confused that they never ever mentioned anything about sugar. But being the good host that I am, I volunteered and they were very happy, and they emailed me afterwards calling me a 'sweet man, and lots of fun'.

SB virgin

Now that I am retired from the SD business, old memories are coming back and I want to write them down before I get too old and senile. I remember 21 year old Natasha. I was in fact quite surprised when she told me she was nervous to meet me and that I was the first person she had met from that site. I never met a SB virgin before.

We had arranged to meet at a 'surf' bar in Brooklyn. I showed up at the appointed time, decided to take a seat at a table inside, chatted a bit with the bartender, and waited. And waited...She had texted me she would be there in just a minute. But after she was 20 minutes late I texted her 'If you don't show up in 5 minutes I am leaving'. No response, so I left. I was not angry, just surprised that someone would confirm their arrival, and then change their mind literally 2 minutes before the meeting took place.

The next day I texted her 'So what's your excuse?'. Just a few seconds later she replied 'Actually I don't have one. I just got really nervous before I met you, at the last minute'. I was taken aback by her immediate honesty and any irritation I had disappeared. I responded 'I know sweetie, I was a college student once. I won't bite you. It's just a simple drink among friends. Come meet me tonight at 6:30 at Lanza's, a low key and old fashioned Italian on the lower east side, and a favorite of mine. I will call you before hand to make sure you are not scared'. 'OK, I promise I won't get scared' she said.

We finally met at the restaurant and sat down next to each other and we talked in a relaxed way. She paid me several compliments during the night, 'you are cute', or 'I am attracted to you', 'If we get along I will take down my profile from match dot com' etc. All very flattering. She was pretty good company for someone who seemed totally out of place and nervous. And I really liked the fact that she wasn't scared to do a couple of shots of Sambuca with me.

The subject of 'sugar' came up and she said she would prefer to be with someone that she likes as a person first, and then other stuff happens. I said that I was in total agreement with her. She asked me if I could help her on that night. I sent her away with $$$ on account that she was flat out broke and in the process of being evicted. I never got anything in return, other than a promise that next time 'we will have fun when you come to see me in Brooklyn'. Did that ever happen? Let me dust off my old yellow paged notebook....

There was something awkward about her, due to her young age and total inexperience. She was inexperienced in both the sugar life, but possibly even the real dating life as well, so you could say this was a double whammy. Did I find that cute in any shape of form? Not really, because it got in the way of things. It's always better when the lady has some experience at least, and all (or some) kinks have already been worked out by another man. This way, this man, SD David, can reap some more benefits. Incidentally, that is exactly why I used to lust over older women, whilst in my twenties. Warmth, maturity, and most of all, experience.