Back in my college days going to a university in a very expensive city led me to look for alternative ways of acquiring enough money to pay down my ridiculous debts as well as fuel my hedonistic lifestyle. I had a fairly wide circle of friends at varying levels of ratchet, and eventually came in contact with a guy who was deep into Seeking Arrangements. He told me stories about how he would spend his nights with the rich elite of the city, men and women, and getting showered with gifts, allowances, and attention during our pillow talk post-sex.
Being a fit college-aged bisexual male with a cute baby face courtesy of my Asian genes apparently made me a very good fit for the sugar baby lifestyle and he quickly got my set up and talking to potential SDs and SMs (heavily skewed towards SDs for anyone interested).
I’ve decided to recount a few of my more memorable tales from back then here on gonewildstories mostly for my own archival purposes, but figured sharing with an audience is also a nice benefit/turn on as well.
This particular story involves Mary, my unicorn sugar momma. Not only was she a drop dead gorgeous MILF with a tight body and a natural tear drop C cup rack capped with smooth areolas and eraser nipples, but she was also witty, intelligent, and best of all kind-hearted. She really made me feel like someone special whenever we spent time together. Honestly looking back I was in love with her for a stretch, which eventually led to the demise of our relationship, but that’s a story for another time.
Mary and I had been seeing each other for close to a year at the point of this story. We’d meet about 2 to 3 times a month, with a pretty standard routine. She’d take me to dinner at a wonderful restaurant where she’d treat me like the eye-candy I was, occasionally inviting some of her girlfriends out with us to show me off. She would literally scroll through nudes she’d taken of me on her phone, showing her friends while I sat there burning up in embarrassment. After dinner though we would always go straight to her home and spend the rest of the night in intimacy.
We had begun to explore some kinks she had never attempted with her ex-husband starting with the more vanilla stuff: light bondage, spanking, anal, etc. But she quickly amped up the intensity knowing that I was game for anything: double-penetration with a dildo, clamps and whips, and pegging just to name a few. On the menu for this night (as you might have guessed from the title) was CNC.
Now I did not have that much experience at the time with CNC, and to be honest the idea of it made me uncomfortable. After a fair amount of research online however, I began to understand it better and we made sure to overcommunicate to make sure we were both on the same page when it came to starting the exploration of our soon-to-be new favorite kink.
We established a safe word (was actually a safe tune that could be hummed since we planned to involve a ball gag) and set an exact time period where we would be in the CNC space for our first foray (this later turned into a permanent situation where I had a key to her place and could use her anytime within a 2 day time-frame). Other than that she let me know that she didn’t want to place any hard limits on what could occur in order to fully immerse herself in the experience, however Mary and I had so much sexual chemistry that we weren’t concerned as much about crossing any lines. I went into the first encounter knowing exactly what I would be doing and making sure it was all within things that Mary and I had already done with consent.
—– sex starts here —–
The night of, I made my way straight to Mary’s house where the front door had been left unlocked. I was wearing a gray suit with a matching tie and quietly stepped into her foyer, turning the doorknob as I closed the door silently while pulling a ski mask out of my weekend bag and slipping it on.
Taking off my shoes, I crept down the hallway, making as little noise as possible. From upstairs I could hear Mary watching TV in her bedroom as we had discussed. My cock hardened in anticipation as I climbed the stairs, slowly approaching her bedroom door.
Just before entering, I grabbed two short braided lengths of rope with loops already tied onto the ends and a ball gag out of my bag. I knew I would have to move quick as Mary was not the type to sit back and let things happen.
I opened the door quickly, letting it slam against the wall as I rushed to jump on top of Mary, lying on her King size bed. She let out a scream as I pressed my weight down on her, quickly isolating her left arm as she struggled beneath me. Wrapping the first rope around her wrist I cinched the knot tight and used my left knee to pin her flailing right arm to the bed as I pulled the rope up to her bed post and secured the second loop around the top of the post.
As she struggled against her restraint her screams devolved into breathless begging, pleading with me not to do this, that she could pay me and that she wouldn’t tell anyone. I gave her a quick backhand across the face which stunned her into silence, giving me the opportunity to secure her right arm to the opposite bedpost.
Mary’s arms now secured I brushed Mary’s hair back from her face and stared into her eyes as I shushed her whimpers, stroking her cheek as I dangled the ball gag above her face. Fear crept into her eyes as she immersed herself in the fantasy of the situation and I shoved the gag into her mouth, fastening it behind her head.
Mary was wearing a pink silk nightie that had ridden up her thighs, exposing her satin panties completely soaked through at this point. I trailed a finger up her milky thighs, applying pressure as my index slid down over her hardened clit. A moan escaped her gag as I started to roll my finger back and forth across her clit. Abruptly I stopped as she began to buck her hips into my hand.
I chastised her for being a horny slut as I walked to my bag, deposited on the floor by the door. Reaching inside I brought out our first toy for the night, a black leather riding crop.
With a flick of my wrist the crop slapped across her cheek with a stinging blow. Tears welled up in her eyes and another muffled moan escaped from her mouth.
“The more noise you make the rougher this will be.”
Her moans of uncertainty faded back into whimpers of fear.
“Good girl, you learn quickly.”
I brought the crop down directly onto her mound, causing her to buck her hips again, but she contained her reaction to the lightest of groans. Stroking her hair, I let Mary know I approved of her quick obedience before sliding down and pulling her panties down her legs.
I slowly slid my index and middle fingers into her lubricated hole, glistening with her arousal, and a moan of extreme pleasure escaped her as I filled her up, pressing down into her pelvis. I quickly bring the crop down onto her right breast with my other hand in retaliation for her moan and immediately extracting my fingers, leaving a glistening drool of her wetness that shined in the light of the streetlamps coming through the windows. Straightening up and I roughly grab her right breast, slowly twisting it counterclockwise. The pain caused Mary to roll her eyes, its contrast to the pleasure of my
fingers bringing a fresh gush of lubrication which began to leak onto her thighs.
After a few seconds, I let go, telling Mary, “I’ll give you one more chance before tonight goes a very different direction.”
Unzipping my slacks, I pulled out my engorged cock, stiff and standing at attention, with precum dripping from the circumcised head. About 7″ in length, with a gentle upward curve and about as thick as her wrist, she had never failed to tell me how much she loved my cock, but the look in her eyes now was one of dread as I lifted her knees to her chest, lining myself up.
The wetness between her legs was now leaving a small pool on the sheets below her. Slapping my shaft against her pussy a few times I enjoyed watching the pleasure of my actions battle the fear she was experiencing, completely helpless to stop what was coming. I continued to rub my shaft between her lips, coating my cock in a mix of precum and her juices.
Grabbing the headboard, I leaned forward, inserting my throbbing member between her plump lips. The first thing I felt was the absolute vice like grip her vagina had on my cock, the ludicrous amount of lubrication making the insertion smooth as I bottomed out on the first agonizingly slow stroke.
——
This is getting to be quite lengthy so I will pause it here for now. Would love to hear if anyone would like to have this story continued and also love hearing others’ experiences with CNC!
Source: reddit.com/r/gonewildstories/comments/navc9j/mf_helping_21my_sugar_momma_explore_her_newly