All in all I have had 4 Sugar Daddies total. The first two are of very little interest so I will keep it brief. The third was a broken hearted soul, and the last ahh the last. My Alexander, I would become his mistress and in many ways he would save me.
I found myself sitting outside a Starbucks off the 15 on Aero drive. It was my first Sugar Daddy interview. My hair was down and flat ironed, and I had donned a black blazer and skinny jeans with heels. Looking back I wondered if I thought I was going on a business interview. Through my scavenging on www.sugardaddy.com I found a man who I thought might be acceptable. I was getting lost in thought when a fleshy man hesitantly walked up to my table, his eyes searching, scanning me for recognition. He was a business owner, and married. He had a long term Mistress for over 4 years that he had broken up with about 6 month past (she went away to school) and was looking for someone to fill the void. We spent the next couple of weeks talking, getting to know each other over dinner and drinks. I would be paid a monthly allowance of $2000 a month, for my secrecy, discretion, companionship and of course sex.
It was a short-lived affair, and only lasted for about a month after those first few weeks of getting to know each other. I can still remember the first time we had sex. We kept it local and had an overnighter at the Westin in Downtown San Diego.
We had gone to dinner first, and I wore a teal blue negligee under my dress. I am a natural 34 D with a tiny waist and my lingerie of choice always accents each delicious curve. I had made sure to take a picture of myself, as I was getting ready. My phone was resting in my lap; I was poised and ready to send the picture to him. I clicked the send button as I lifted my glass of wine to my mouth and took a sip. I looked at him, devilishly with one eyebrow lifted and suggested he check his phone. I remember him turning red, and stuttering like a little schoolboy.
“That…that’s what you’re wearing under that?” Smiling I nodded.
He took me back to the hotel shortly there after and as we walked through the bedroom door he could barely contain himself. He ripped my dress off over my head and ordered me to stand in the middle of the room so he could inspect me. I swung my hips from side to side and my boobs gave a slight jiggle as he came forward to stroke them. Then he pushed me back on to the bed and spread my legs. He continued to go down on me, it wasn’t the best pussy eating I’ve ever had.
I thought we were going to get to the sex-he however had other ideas. Rolling over he continued to order ice cream to be brought up. Then he sat back in a chair flipped on his laptop and continued to do work. Now, the first time you have sex with someone is always awkward, but this I was not expecting. You have a woman waiting there posed for you and you work? 15 minutes of silence passed and we heard the knock of room service. He looked up and said answer the door. I looked at him, but did what I was told.
The doorman all but had a heart attack as I opened it with only thin lace holding in my lady parts. My beau on the other hand was more then happy with the spectacle. He was not an obese man, but he definitely had an extra layer of fluff on him. He looked as though he could have been quite handsome in his younger years, but age and bad diet had not served him well. It was written all over his face he was enjoying having a hot piece of ass at his disposal in front of this strapping young man who delivered our ice cream.
I wish I could say the rest of the night was as exciting, but in reality it was quite a dud. I didn’t even get off, which is really sad for a multiply orgasmic girl. He fucked me missionary style, my head kept hitting the headboard, he got off rolled over and went to sleep. The end. We saw each other for about a month after that, in the end however he ended up getting in a drunken car accident-no surprise, and called it quits.
After that I started a SB relationship with a dashing Indian man who was actually quite attractive, but unfortunately had mommy issues. We dated for months under the same negotiation of $2000 a month. I was his companion for dates, work events and weekly lunches. We never however had sex, not even oral sex. Strange I know. I felt more of a therapist in those months and less like a “girlfriend”. He would come over for lunch once a week, which I would either order in for us or make. He would then continue to unload all of his deep seeded personal issues, then bend me over and stick his face in my ass cheeks while massaging them. There wasn’t even any tongue action in the butthole. Then he would go off to work like nothing happened. The irony.
In the end his mother found a nice Indian girl for him to marry so we ceased seeing each other, and I was back on the prowl. This is when I would come across Sebastian, my brokenhearted lover who I will always have a soft spot for. He is also the one who began my sexual revolution into the beautiful world of BDSM.