Down the Rabbit Hole…

Hello, yes I am back and its time to play. Let me apologize for my silence, I have been traveling with my boss and sharing a hotel room. Which does not leave a lot of private time for more intimate writing, and then I came down quite ill. I am better now and ready for action….Now where were we? Oh yes, Sebastian, the magician of my heart…

We met on a blustery day at the Hotel Del in Coronado. They have a delicious Sunday brunch special and the grounds are gorgeous. He met me out front, I was not sure what to expect. He had a kind smile and offered me his arm to escort me inside. He was tall, over 6 feet, a shaved head that you could see if grown out would make a ring of grey. He was solid, and you could tell he would have been quite the athlete in his younger days. But for his features he was distinguished and very attractive, however paired with my youth the onlooker could instantly tell what was happening.

I don’t remember what we ate that day, but I do remember being fully entertained the whole time. We recounted our lives, loves and history. He was a neurosurgeon and was originally from the East Coast-sans accent. He had been married previously, over a decade ago to a frigid woman who refused to fuck him and who almost took him for all he had. In the battle he had lost his children whom which he still has a lingering relationship with that holds on by a thread.  Growing up he had a love for magic and card tricks; he owned every trick from his local magic shop and would practice tirelessly for hours. His father however prevailed and insisted he become a doctor-so he did.

I was coy, a little shy and sweetly innocent yet perversely sexy. My hand fluttered over his at the right moments, my head tilted so a strand of hair fell in my face, I looked at him with my big blue eye over the rim of my mimosa glass as a slight smile played my lips. I was good at seduction, it was in me, and I didn’t even have to try or force it. It ran through my veins, I was told once my body was built for sin. When he pulled out a dollar bill and continued to fold me an origami elephant I lit up the room. This was over two years ago…I still have the elephant.

We left like two lovers high on life and went back to his place on the beautiful San Diego coastline. It was like walking into a dream especially for a history major like myself. Or should I say like walking into a museum. His five-story house was beautifully appointed in the finest garbs of all the ancient civilizations. Bronze metal hung on brightly colored paint next to bows and arrows. Ancient deities lined the walls their faces masked in horror over the crystal gems and mad scientist tools that cluttered the tables. Every space was claimed with parchments and pen, Tibetan incense holders and tribal masks. I walked around like a child in wonder, gently stroking each item as if it would turn to dust beneath my fingers. Every heirloom had a story behind it, an adventure of how he had claimed it. I felt him come behind me and reach through my hair, grasping my jaw line to turn my face up at him. He told me he had never had anyone react in such appreciation to his house how I just had. I licked my lips and looked at him and replied who could resist such wonders of mankind through the ages. That was when he kissed me for the first time. A furtive kiss, hard and wanting.

We somehow found our way over to the kitchen where he poured me a drink; he only had cheap vodka and bad mixers but somehow managed to make me an acceptable cocktail. We also lit up a blunt and began to smoke as he pulled out his magic box. No kinky innuendos here, it was truly a box of magic.

He was showing me his digs when something dawned on him and he turned to me and asked—

“How is it that your divorced, who would ever want to lose you?”

I had never uttered the truth to a soul in my life. I don’t know why I told him, and truth be told I did not tell him much. My answers were fleeting as my heart pounded in my chest and my head swam with bud and liquor—

“My husband used to beat me…he used to tell me I would never find anyone like him….my father was an alcoholic who emotionally beat me down for a decade until I ran away with my husband to get away from it….It took me six years to finally leave my ex-husband.”

That was it, he looked at me with those eyes and stroked my hand and asked if I would like to see my future. I blinked away tears that were threatening to sting my eyes and told him of course and clanged my glass to his in a salute. He spent the next hour putting on a spectacular magic show and weaving me the tale of my future. Until we managed to stumble up the five flights to his bedroom…

Sugar on my Spoon…

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.

 

 

And so it begins…

I had to go to work and I stripped down to change into my work clothes. I caught a glimpse of myself in the mirror. I stopped to look, turning to the side and sucking my stomach in. I have never been petite; I always fought my hourglass figure. I have boobs, full hips and a bubble butt that could start to take over the rest of me if I didn’t keep it in check. Red haired, and bright blue eyes that were usually my most noticeable feature (after the butt). My skin was peaches and cream with light freckles over my nose, I was always trying to tan it. My girlfriend Amber had beautiful honey skin, I was always so jealous. I turned red, and my tan was her normal skin color. Sighing I wondered if I was skinny enough to be a sugar babe. What was I even thinking, I didn’t even know if I would do this?

I spent the next week looking through listings while refusing to respond or commit to anything. I wanted to talk to someone about it-someone impartial. I had spoken about it to some of my gay guy friends, but it was an all to common cultural acceptance for them to have daddys. I lived with a gay man in the heart of San Diego’s gay neighborhood Hillcrest. It was a hip and trendy part of town where you could go out at any given moment and people watch. My favorite was at La Fuenta at 2am after Riches closed and all the trannys and goes go dancers came out. My roommate albeit gay-was the one person who would never approve of this for me. I knew it would lower me in his eyes in the beginning. He had mentioned to me on occasion that I was different- one of the few good honest girls left. I decided to get out and clear my head so I headed to one of my favorite spots in SD, Cowles Mountain.

It was one of the highest points in San Diego with a beautiful view and was a moderate climb. Maybe it was the heat that had baked my brains, or dehydration was making me loony, but half way up I decided to call my mother. I stopped panting, and sat down on a boulder with my iphone pressed into my face.

I heard her “hello”. “Hi Mom” she responded with her typical “hi honey whattsup”.

“So, Mom, what would you think of your daughter being a high-priced sugar babe?” There was a silence on the phone-I’m assuming this was the point where she either decides that I am still her daughter or not.  Now let me back peddle here, my mom is a cool chick but I was not expecting this answer.

“Well you know Tim at work has one and they seem ok, I mean you wouldn’t have to have sex right away, and as long as they are not into anything perverted.” I think at that point I had started to laugh hysterically. My mother and I had not always been close. We had gone through a “stage”. But since I had divorced my husband- a story for a later time, we had become very close. I had come to rely on her as my moral compass. So I went on to tell her about the Sugar Daddy site. She was completely intrigued by the idea, but did go through the-well I guess in this case it would not be typical mother behavior. She wanted background checks ran on each potential, the times and locations of each date and if I could get their license plate numbers even better.

That night I sat in front of my computer screen, the humming of my computer tower and  a glass of wine in front of me. I began looking through messages…

A tantalizing prelude…

My back arched and lifted off the bed as my head tilted back. I could feel the waves of my orgasm wash over me, I was helpless, defenseless. He had my legs pinned back behind my head and was pushing himself in and out of me. It was like something broke in me and I could not control it. I did not want to cum but he forced me to. My body shook as the last of it drained out of me. He was heavy on top of me, smothering; I grew still and gently pushed him off of me. I curled my legs up to my chest and breathed heavy as sweat beaded down my neck. He sat up and looked up at me with those eyes and I wondered what was I doing. It was so wrong, it should not be this good. Fishnet stockings, condom wrappers and a hash pipe littered floor. I toed my way around them and found my dress, silently pulling it back on and adjusting myself. I smelled like him, like our sex, such a distinct smell. I turned around and he was on the edge of the bed sipping a glass of water. I leaned over and kissed the top of his head then made my way to the bathroom. My feet padded silently on the cold marble floor and I sat down to pee. Such a cold and barren bathroom I thought, looking around. Everything in its rightful home, every towel perfectly folded, every item intricately put in its place.  Just like him, nothing ever out of sorts. I left that night with an envelope full of money, and as I pulled myself in my car I stopped to count it like I do every time. It never changes, $500. I slide the envelope in my purse and start my car; the cool air of the AC blows over me. Driving home half lit, half dazed I wonder how I got there. It is a short drive, and I force myself into the shower. I never go to sleep smelling like him, I wash myself clean. Like it can somehow clean away the dirty deeds that I have done. It doesn’t, but I don’t feel regret either. I am a San Diego Sugar Baby, they are my dirty deeds and I own them.

I never thought I would tout the name Sugar Baby. In fact I did not really know anything about being one, until one of my gay guy friends mentioned it to me. I had just gotten out of a bad break up and was going through the typical man hating faze, you know the one-post one pint of Ben and Jerry’s and pre-becoming a lesbian. I was shopping at a high-end boutique and luckily had no shortage on Hillcrest’s finest gay men as support. I was complaining that all I really wanted at this point was for someone to take me out and take care of me, when Charles my best sidekick turned to me and said in his best Naomi Cambell voice, “Ohh girl, what you need is a suga daddy!” Baffled I gave him a blank stare, he threw down the shirt he was admiring pressed up against his chest in the mirror and said “You have never considered a Daddy?” Apparently these “Daddies” are all the rage this season. He raised an eyebrow and continued, “I have one that I see on the regular, and he gives me $900 a session.” My eyes must have given away my disbelief, or perhaps it could have been I jaw was dropped so low you could have fit, …well you get the idea. Charles sauntered up to me with his best catwalk swag and said “look-just check out Sugar Daddy.com. You don’t have to get paid for anything, but if you are looking for a man to take care of you-while you make up the rules. That is your place.” That night I stared at the blank screen of my computer as I contemplated if I could pull this off. It couldn’t hurt just to look right? I pressed the power button on my old PC tower, and it slowly hummed to life. I clicked intern explorer, and slowly typed in http://www.sugardaddy.com. The browser flashed and up came a scene of a handsome man with silver hair and the blonde babe smiling in front of him, jet in the background with palm trees lining the screen. I didn’t have to commit to anything, right, I could just peruse the listings. See what is out there, it could be quite interesting from a sociological standpoint. I entered in my info, and it asked all the typical stuff- how much you make, what are you looking for, what do you look like. Here goes- 5’9, red hair, blue eyes, busty. What do I like…..now here was the golden question. I spun around in my chair tapping a pen to my mouth. I didn’t even know what I wanted out of this. I pulled myself forward and stared at the screen, likes: “outdoor fitness activities, movie, wine nights, and high heels.” That should do for now I thought; give them a little taste without being too over the top.

I started to scan through the listings, which you could tailor to your own search parameters. The listings were enormous, and there were so many men looking for different things, wives, hookups, and dirty little secrets. Pretty soon I had killed an hour just pilfering through peoples profiles. It was too much, my mind felt bogged down by all the information. I switched off my screen and wondered at my own demise- what the hell was I doing?