My Year as a Sugar Baby Pt. 1: The Massage [MF]

I’ve always been turned on by age play. Whether a man is much older than me, or much younger (legal of course), the sex based on their respective life experience adds an extra layer of taboo that drives me wild.

In my 20s, I worked as a waitress or bartender. There was no shortage of older men that’d shoot their shot at a young, thick, big titted latina like me when I served them drinks. I knew how to work the bar and flirt to maximize my tips, but I’d never gone home with anyone or dated a customer.

That was until I met Damon. A software salesman in his mid-50s, I noted that Damon was a couple years older than my Dad. He had beautiful green eyes and thick, full lips surrounded by a well kempt silverfox beard. His head was shaved and he had a natural tan from his long jogs outdoors. His slim runners build looked trim in his suit, and his deep voice would make my knees weak when he’d address me.

One rainy and slow Friday night, Damon came in looking particularly upbeat. He ordered a top shelf whiskey and asked if I’d have one with him. We were a couple hours from closing, and my last few guests were wrapping up. I served his drink, while sneaking mine into a kids plastic cup which is what staff drank out of.

“So what’s the occasion, hun?” I asked.

“I just closed a major deal, comes with a really nice bonus.” he elated.

I tried my best to be happy for Damon, but it was difficult standing on the other side of the bar, knowing I’d be walking home with less than $100 for the night. We both finished our drinks quick and Damon insisted I have one more. I wasn’t closing that night so I accepted, gulped my drink, wrapped up my tables, and checked out for the night.

On my way out, Damon asked if I’d like to join him for more drinks as he helped me with my jacket.

“On me!” He offered, smiling kindly as he put his own jacket on.

I felt like I could use the drinks and accepted the invitation. We sat in a quiet booth and Damon made great conversation with me, I could tell why he made so much money as a salesman. He asked how my night at the bar was. I said “slow, and of course right before rent is do”, taking a big sip of my drink to emphasize the hard times.

Damon smiled, and in a joking tone said “if only you had a sugar daddy.”

Before I could catch myself I blurted “Jeez I’d love that.”

Damon looked me in my eyes, interested, and asked “Really? What would that entail for you?”

My heart was racing as he leaned in, I took a deep breath, smelling his cologne.

“I don’t know” I said, placing my hand on his thigh “that would depend on the guy”.

I leaned in and initiated a kiss. Half because I was turned on, the other because I wanted to prove how serious I was.

My hand crept up Damon’s thigh and I could feel his already semi-hard cock growing further in his pants. He broke our kiss and said “Wow. Want to go back to my place and discuss further?”

We paid our check and began the drive to Damon’s house, which was a short 10 minute trip away. Damon asked if I enjoyed massages and I said “of course.”

He asked if I’d be interested in him giving me a massage, no sex, we’d both be nude, and he’d write a check to my landlord paying the remaining portion of my rent ($300) for the experience. I thought I heard him wrong and clarified “YOU give ME the massage?” He confirmed that to be the case. “I mean.” I took a second to pretend like I was actually mulling it over “sure, if it’s just a massage”, trying my best to sound innocent.

He smiled to himself and we pulled into the driveway of his beautiful house on a lake. I commented on the gorgeous reflection of the moon on the water and he smiled at me, looking as handsome as ever, the sliver light from the sky accentuating his gray hair.

Damon lead me to the bedroom and played a romantic record from his impressive vinyl collection. He kept the lights off but lit some candles. He started to strip down to his boxers and I got fully naked.

I asked if I could take a shower since I was fresh off work and he provided me a towel. His bathroom had heated tile floors and dual shower heads. He joined me in the shower and requested to wash me. It was such a turn on to be in the shower with a man more than twice my age, him running the wash cloth over my most intimate parts while commenting on how beautiful I am. Damon told me to bend forward and put my hands on the shower wall. I did as I was told and he proceeded to spread my ass and wash me from behind.

When we dried up and returned to the bedroom, I laid on his king size mattress, facing up at the ceiling as he approached with a small container of coconut oil.

“Is there anything I can get for you before we begin?” He sincerely asked.

“Just some water please. And um, do you mind if I smoke?” I produced a joint from my purse. He insisted I light up and do whatever I needed to get comfortable. He slid his glass door open to let the smoke out and left to get my drink. I smoked half my joint, staring at the water outside, in disbelief of the scenario I found myself in.

Damon returned and I relieved my cotton mouth with the ice water before laying on my back, facing up at him. I closed my eyes, floating on cloud 9 as soft kisses were planted on my neck. I moaned and Damon felt encouraged, sucking some of my flesh into his mouth. He continued down to my nipples and spent quiet some time alternating from teasing with the tip of his tongue, to lightly sucking both my nipples, to filling his whole mouth with as much of my DDD breast as he could fit while simultaneously rubbing his tongue all over my areola roughly, removing his mouth with a loud pop.

No one had ever teased me like that before and I begged him to touch my clit. He smiled and said “not yet”.

I turned over, per his request, and laid on my stomach. He covered his palms in coconut oil and took a seat on my ass. I felt his balls and dick rest between my butt cheeks as he started to rub my neck and back with his skilled hands.

“You’re really good at this”, I sighed.

“I took some massage classes in college. Never worked in the field but always stayed interested”. He said, continuing to work my lower back. I could feel his cock stiffening against my ass; I pressed back and wiggled against it, trying to tease him a bit.

Damon finished my back and hopped off my ass to reposition himself. I took a moment to take in Damon’s naked body. He was in great shape, with a 6pack and tight pecs. His dick looked a little over 6 inches with nice thickness, nothing overwhelming.

Damon continued my massage by rubbing my thighs, seeming to take great care to get as close as possible to my aching pussy but never touching it. Damon worked down to my toes and wrapped up the first part of my massage, washing his hands after.

He returned from the bathroom with another bottle. “Grapeseed oil” he said.

I was still laying on my stomach now, with my legs spread in a v-shape, in order to give him access to anything he wanted. Damon poured some of the warm oil on my ass, and I felt it run between my thick cheeks, down passed my asshole to my already wet pussy. I felt his strong but soft hands work my ass cheeks, he made sure to spread them wide every now and then to give himself a close up view of my tight holes. He slid his hands between my round ass cheeks and started to play with my asshole. He pushed his index finger right passed my tight ring in one motion and I let out satisfied sigh. He was pleased that I enjoyed it. He continued to finger my butt while I grunted and squealed.

I was asked to turn over and lay on my back. Damon’s head dipped between my legs and he started to kiss and nibble on my inner thighs. I squealed in delight and because it tickled a bit. He made his way to my pussy and gave my slit a few kisses before covering my it with his open mouth and running his tongue flatly from the bottom of my clit to the top of its hood. He did this repeatedly, purposefully, taking his time to savor the rush of wetness my pussy would provide with each wave of pleasure that’d wash from the tip of my toes to my head.

Damon lifted my leg, bending it and placing my heel on his back, further exposing my asshole to him while he continued to lick my clit. He put two fingers in my juicy pussy and started to press up towards my belly button. I’d never felt a sensation like that before and let out a shocked but obviously pleased “aaah”.

His fingers kept a steady rhythm and I was gyrating uncontrollably as he increased pressure, tapping my gspot a slightly harder now. At this point, Damon was sucking my little clit like he was my nipple earlier and I felt a deep buildup of euphoria as my orgasm approached. Damon must have sensed this because he increased speed with his fingers inside me. He took his free hand and started slowly penetrating my ass with his finger.

This drove me over the edge and I came hard against his tongue while his pointer finger was doing small circles deep in my butt. I was a moaning and screaming mess as my legs flailed wildly and my tits bounced around because my world shattering orgasm. “Fuck Damon! What are you doing to me” is all I could manage to say.

As if he were skillfully landing a plane, Damon brought me down from my peak. He reduced the pressure on my gspot and clit but didn’t completely stop sucking me. He just layed his tongue flat on my clit and barely vibrated it.

I couldn’t believe I came that hard from oral alone and sang Damon’s praises and he beamed back proudly. I reached towards his hard cock to return the favor but he took my hands to his lips, kissed them and said, “another time”.

I couldn’t believe what I was hearing, and must have appeared to have my feelings hurt. He whispered reassuringly, “I just want tonight, this first time, to be only about you”. He hopped off the bed and returned with the $300 check for my landlord like we agreed on and left it on the nightstand.

I was feeling conflicted, but also very satisfied and special that I was pleased without having to do anything in return.

I thanked Damon and started to get dressed. He mentioned he was having a party the following weekend and that he could use a bartender for the private event. “The tips should be decent”, he encouraged.

I accepted the job and we exchanged numbers. He kissed me on my forehead as the cab he called for me pulled up.

I drove home feeling like a princess and kept wondering where this new relationship with Damon would lead, and what kind of party he was going to throw…

Source: reddit.com/r/gonewildstories/comments/yv91qs/my_year_as_a_sugar_baby_pt_1_the_massage_mf