The Sugar Dick Daddy Ch. 02

Work, work work.... sleep! Repeat! I didn't really appreciate how much physical labor goes into operating a retail drugstore until a dear friend told me to give it a try. He had the same college degree as me and thought I might be a good fit. I was leaving a budding career in fitness club management because I had topped out with my salary and got passed over for the next promotion. Only one week in and my lower back was killing me. The glamorous part of retail is the holiday sales, but what most people don't realize is that most of those sale items arrive months before the event and make it hard to move around our stockrooms for weekly and daily items. One evening, I decided that I needed some physical pampering and scrolled through my phone for a local massage spot with good prices and immediate availability. In no time, I located one in a neighboring town only 15 minutes away. I was approximately 32 by then and was a solid 200 lbs. I was relatively fit and took care of myself and family.

As I rolled up to the address, I discovered that the actual massage parlor address was a former small drugstore as well. I rang the bell and was quickly invited in by a bouncy voluptuous vixen. She appeared to be in her late 60's and very fit. She must have been a knockout in her 20's... but she's a stunner now. I was shocked into reality by her firm grip around my hand as she led me inside and to our massage room. She told me her name was Diana and wanted to know what I was interested in today. I was too shy to admit what I was really interested in, once I saw her firm ass as she bent over to pick up sheets and towels for the massage table. My mouth was dry at the idea of what those thick globes of comfort would feel like bouncing on my thighs. I began to undress fully in front of her while she got the table set up. As she finished, her eyes caught her first sight of my thick, veiny hunk of meat. I finally answered..."whatever you feel is best!"

She smiled, lifted the sheet and motioned for me to climb onto the table and lay on my front with my arms out over the side. My face was positioned in the center of a face cushion with a hole in the middle, which allowed me to not only breathe, but actually see her shapely legs, up to the tops of her thighs. She dimmed the lights, lit some candles and warmed the massage oil as we got acquainted. We made small talk as she got the light spa music going. Diana told me that she used to be a Call Girl out in Vegas, but she moved back here when she retired so she could help her aging parents, who had both passed a couple of years back. They left her the money to start her own spa and she jumped at the chance to get back into an environment that she felt most comfortable in. She worked out every morning, ate healthy and loved to walk on the naughty side when the right opportunity presents itself. I smiled at that comment because as she said it, not only did I hear her pouring massage oil into her hands, but as her robe hit the floor, I knew she was was rubbing that oil on her perky tits. The moment her hands touched my shoulders, the heady aroma of her pussy wafted across my nose from just beyond my sight. This was going to be worth every penny!

Diana moved around the table with the prowess of a feline. And eventually, she climbed on the table, straddled my back and dragged her hard nipples across my skin. Long, slow movements at first, followed by tight circles around my shoulder blades gave rise to sporadic breathing from her. Diana was really into this. Before she could take herself over the edge, I had had enough teasing and I was ready for some real fun as well. I quickly rolled over onto my back, while she still straddled my hips, and grazed her dripping warm entrance with the massive tip of my throbbing dick. Diana then decided to take advantage of the opportunity which had presented itself. She reached behind her, got more massage oil and liberally coated my shaft, including my balls. The anticipation of feeling desired by a woman of her stature was intoxicating.

Slowly, Diana eased herself down onto my shaft. She was unbelievably tight. I asked her how long..."Years!" was all she could manage as I filled up her warm depths. Diana took a moment to welcome me inside. "You're a big one!", she said as she recovered her breath. I told her that I wanted her to use me. I wanted her to let out all the pain and frustration of all the years past out on this fat dick. I gently caressed her firm abs and cupped her juicy breasts, careful to apply just the right amount of pressure to her rock hard nipples. Diana knew what she wanted. She leaned forward and asked me to take her... from behind. It took a little effort because of the height difference, but she placed a small stool in front of the table, climbed up and bent over for me. This was exactly the scenario I had running through my head earlier. I took my time to drag the tip of my shaft up and down her dripping slit before easing all my inches inside her. I only stopped as I felt my balls graze her clit. I grabbed her well-toned hips and gave her long, slow deep strokes and I just listened. First it was just her rapid breathing, then came the sighs. Then she whimpered. At this point, I knew she was ready for some real hard fucking. I spread my legs apart, slightly, then grabbed her wrists for support, so I could pull her back onto me as I thrust away inside her. Now, she was going to experience total and complete release. The only sound louder than Diana's cries of pleasure was the rhythmic clapping of her ass cheeks against my thighs. She came over and over as my heavy balls slammed against her sensitive clit. My dick head pounded relentlessly against her G-Spot. The carpet beneath us was soaked in her pussy juice.

Diana tapped out in under ten minutes. I still had 40 minutes left in my massage and I was still hard because I wanted to make sure Diana had enough of what she needed. She dismounted both me and the table to grab towels for us and bottles of water. Both her breathing and legs were shaky after that vigorous fucking. We took a moment to drink and recover. In the dark, I could still see Diana lazily stroking her clit while she drank her water. She was staring at my throbbing dick the whole time. I caught her gaze and smiled. She smiled back, almost in disbelief at what we just did.

She motioned for me to climb back onto the table, where she mounted me again. Once I was fully inside her warm wetness, she leaned all the way forward until my face was covered in her curly red hair with her mouth next to my ear. Softly, she whispered that she wanted to feel me cum inside her. She explained that she is well past menopause but still missed the feeling of being pumped full of cum from a throbbing warm-blooded dick and mine was perfect. She started with slow undulations at first. Next she added gyrations while absolutely filthy words flowed from her lips to my ears. In nearly no time, I was gripping her ass and pounding into her with the same intensity as before. When she asked me to finger her ass, I lost all control and almost fully released inside her pussy. But as she realised what was happening, she reached back and shoved my spurting dick all the way inside her asshole. She sat up to not only ensure I was fully embedded deep in her rear but she massaged my balls to ensure that I was fully emptying inside her.

Diana was full of surprises... and my cum. She sat there, on top of me, while she continued my massage. She added more oil to her hands and lovingly massaged my head, neck, shoulders, arms, chest and torso all while patiently milking my throbbing dick in her asshole. When it was time to massage my legs, she simply rotated herself, with me still lodged deep inside her, and continued the massage. The view of my dick slowly being fucked by this Sex Goddess quickly became too much for me to much resist. I pulled Diana's back against my chest and wrapped my left arm around her breasts and massaged her clit with my right while I pounded her bottom from underneath. This drove her crazy. Our sexual chemistry was ridiculous! In minutes, we were both shooting cum all over the place. Mine was dumped in her ass, but hers shot onto the walls and snuffed out one of her candles. We took that as our que to stop fucking and finish up my massage. We toweled down again and with great satisfaction, managed to get through the last of my services.

Diana has been my lover and friend for nine years now. She knows all my kinks and knows how to get them out of me. The years have been very kind to Diana, as she still looks better than many women half her age and I'm glad she decided to take advantage of the situation I created by booking her so many years ago!

Stay tuned for the next episode!