At 52 years old I'd been thinking a lot about what I want my sex life to look like here on out. I was engaged in my mid 30's to a gorgeous young lady that had a 1 year old daughter. I looked forward to becoming a family with her before she abruptly called things off without an reason and left town never to be seen or heard from again. I'm not gonna lie, my heart was broken.
At that point I decided that women weren't worth my dedication and just used and abused them at will. Being an above average looking guy with a very large bank account I never had an empty bed unless by choice. I would fuck random ladies I picked up at a bar, hire high priced call girls, and even get some off of one of those fetish sites when I wanted to get extra wild. This went on for years.
About four years ago I started seeing a woman named Sarah who was into swinging. Sarah was a curvy mid 40's blonde with huge tits and an insatiable sexual appetite to match mine. Needless to say it was an adventurous time filled with 3somes, voyeurism, exhibitionism, and fetishes galore.
However, at some point I feel like a light bulb went off in my head. I wanted a sugar baby. The thought of a young hot sex toy that was available for me to date, fuck, and even spoil really appealed to me. So I broke things off with Sarah and placed an ad on a sugar daddy website in hopes of securing my prize.
I received a couple dozen responses the first week but was quickly able to weed out some of the more obvious red flags. One woman wanted an immediate $5k per week allowance. One said she was 16 but "won't tell anyone." Many seemed like bots and many others like psychos. I did get 2 responses that were intriguing.
Jennifer (I love the classic names) was 19, a student at the local university studying nursing, and asked for a reasonable allowance based on both our wants/needs. That seemed fair to me. She was also quite attractive although her tits are on the small side (I like for curvy girls). Overall a definite consideration.
Hailey was 18, lived at home with her parents, worked at a dentist office, but made it clear that she desires to play the role of trad-wife for an older man. She wants to cook, clean, take care of the home, and of course fuck her sugar daddy as often as he likes. She claims her sex drive is high but her body count was low. "My hope is to be the property of one sexy older man" the final line of her bio read. Hailey has a great body as well. Curvy but in shape, gorgeous green eyes, auburn hair, and probably DD titties.
"If she's sane I think I've found my sugar baby!" I thought to myself about Hailey.
I requested a date with Hailey for the following night to meet at an expensive restaurant with the possibility of a night cap. Told her to take an Uber which I'd pay for so she can leave with me if we click.
I received her response "I look forward to meeting you David. Thank you for the transport. May I request some additional funds so that I can wear something special for you? Maybe say...$500?"
"Done." I answered and immediately sent her the cash through an app.
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"A bottle of Chateau Lafite and two glasses please." I told the waiter.
"Right away sir. And I believe your 'daughter' has arrived sir." He said as he stepped behind the chair opposite me and slid it out.
I stood up and looked over my shoulder to see Hailey approaching in an absolutely stunning form fitting black halter dress that accentuated her heavenly body. Her auburn hair was down on her shoulders and her make up was subtle enough to show her natural beauty. Her legs (and sexy ankles) were perched on a sexy pair of black high heels. This young lady was destined to be some guy's queen.
"Hello beautiful!" I said as I kissed her on the cheek. "You look incredible." As if my facial expression hadn't told her my thoughts before this.
"Thank you. I'm glad you like the dress you bought!" She giggled. "You're very handsome yourself. Rugged. Manly." She complimented me while feeling my broad shoulders. "You look much younger in person as well."
After sitting down, Hailey and I talked, drank wine, ate, and talked some more. She is a very mature young lady. We talked about her upbringing, my business success, her brief sex life, my desires in a sugar baby, her specific kinks that she is dying to try, etc. Two and a half hours after meeting I was ready to "sign the deal" as they say. And she seemed fairly enamored as well.
"Would you like to go back to my place? Or a hotel if you prefer?" I offered her. "Or would you like to discuss our arrangement first?"
"Can we talk business tomorrow and just have some fun tonight?" She asked. "Lets see if we're sexually compatible."
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The entire drive to my house Hailey was rubbing my cock through my pants. I simply lightly scratched her back knowing I was going to get her fully once we got home.
Once home we barely got into the door and we were kissing passionately while undressing one another. Hailey was down to a black lacy thong by the time we reached my bedroom. I asked her to keep it on as I finished undressing.
I laid her back on my bed and spread her legs so I could lay between them and kiss her sweet pussy through her panties. Her fingers weaved into my hair. I squeezed her ass as I lifted her pelvis into my face. I had told her at dinner that I'm a very oral man so I'm sure she expected me to dive right in.
