Slave Southwindingroad

The Side of the Road Incident, my First BDSM Experience

Part 5

I obeyed my Mistress’ instructions crawling to the edge of the queen bed where she took a seat. I got on my knees and was inspected and was praised for being able to maintain my posture for such a long period of time during my previous task (a feat that was only possible for me due to the time I had recently spent as a collegiate athlete). After a healthy dose of additional teasing, she indulged what was my ultimate fantasy, being forced (consensually) to pleasure her between her legs with my tongue. She gripped my hair, guided my face, told me when to lick, when to stop, when to continue, and used me to her satisfaction just like in my wildest dreams- in those moments I was in heaven. I continued as she commanded until she was satisfied and I profusely offered thanks. I was rewarded with praise and was given an invitation to serve again. Unfortunately, because of my financial situation as an underemployed student I was never able to see her again.

I would not reprise the role of a submissive for a professional domme for another 8 years- at which point I had thoroughly explored my kinky interests and gained a better understanding of D/S dynamics. I sometimes think about that bright-eyed, bushy-tailed young man barely starting to explore beyond his vanilla sexuality and am thankful for the patience, compassion, guidance, and attention that Mistress blessed me with that day. But only a really, really dumb slut would forget to check their gas before going to a session.

The End

The Side of the Road Incident, my First BDSM Experience

Part 4

An attractive blonde woman, no taller than 5’6”, answered the door and welcomed me in to the room. My heart was beating out of my chest as I stepped inside. I remember wore a dark outfit, the material it was made out of has faded from my memory. I was instructed to place my tribute on the round seating table in the corner of the room where she took a seat. She acknowledged that my struggle that evening and told me that she did not believe my story until she heard the sound of the cars whizzing past me on the freeway. The moment I she told me that, I could feel tension release from my body and my mind slow down; the feeling of panicked desperation eased and nervous excitement remained.

My Mistress proceeded to rip through scratchers tickets at the table and asked me about my experience (I had none) and my kinks (I was just starting to explore). I expressed interest was in following general orders and being physically made to be used pleasure. Her first command was for me to dress down to my underwear and stand up against the wall, holding up my arms off of the wall in a cactus shape as still as I could. I remained positioned there without a good sense of how fast time was passing. As my muscles started to tire, she produced a flogger and used it lightly all over my body. She verbally teased me about how hard I was struggling as my arms started to twitch and shake- but I did not fail her and after what felt like a painful eternity she released me from my position on the wall and brought me to my hands and knees on the floor.

To be continued..

The Side of the Road Incident, my First BDSM Experience

Part 3

I had a quiver in my voice when I spoke up to explain my situation that I was stranded and would be late to the rendezvous. Mistress was furious and doubted my story immediately and began interrogating me about my exact location and what I was doing to remedy the situation. I was mortified, beyond embarrassed and folded under the pressure of my failure was blubbering through my words on the phone. After a few moments, unexpectedly, her tone softened- she demanded I proceed as best I could and keep her updated on my progress via text.

After another 30 or more minutes of waiting, Kevin arrived in his sedan with the red gas can. We had a laugh about my situation, I did not tell him what I was explicitly up to- but I implied I was up to no good and that was enough to sate his curiosity for the time being. With a gallon of gas in the tank, I made my way to a gas station and then along I-10 to the other side of town where I finally arrived at my destination almost an hour late. I reported my status as commanded and was directed to the door. My nerves and embarrassment were at their peak as I knocked at the door and it began to open.

To be continued..

The Side of the Road Incident, my First BDSM Experience

Part 2

As I made my way down State Route 143 in a borrowed minivan, my mind continued to race and my entire body tingled with anticipation. Keeping an eye on the clock to ensure I would comply with the instructions I had been given: acquire a specific tribute of various items, arrive at the appointed time, await further instructions, the car is slowing down- I pushed the pedal down to the floor but it was no use. I coasted to a stop on the shoulder of the highway as panic set in. I immediately called my roommate, let’s call him Kevin, and explained that I was stranded on the side of the highway in the middle of the night. He agreed to go to a gas station to get a can of gas to save me. After I hung up, I immediately made a phone call to my perspective Mistress for the evening. She answered with a “Hello?” and was none too pleased as I made an effort to explain the situation I was in.

To be continued..

The Side of the Road Incident, my First BDSM Experience

Part 1

This is another story that started on Craigslist in the mid-2010’s. I stumbled upon an ad posted by a domme who was in town for a short amount of time. Light/gentle female domination had become a sexual interests and I was lucky to get a response and made an appointment for sometime around midnight across town.

I was beyond excited- I was frenzied and visions of domination danced in my head. As I got ready I fantasized about receiving orders, being used, and submitting completely all for the first time. I was so caught up in my excitement I lost the attention to detail that a submissive should maintain when honoring their commitments. I diligently polished my hygiene, precisely prepared my tribute, and continuously monitored my timing and progress. While I was focusing on the major components of my commitment, I neglected to notice the fuel gauge already reading empty.

To be continued..

Storytime: The Craigslist Cuck Incident, Double-Trouble

Part 3

The second man came into the house wearing an unassuming white shirt and shorts. After a few words he disrobed and joined us on the mattress. His cock was comparable to mine, a bit bigger, but we made a good team. We took turns spit-roasting the shy little redhead while her husband filmed. I remember being hard as a rock and having fun placing her in different compromising positions. After maybe an hour, the husband had a suggestion- he asked if we would be down to try double penetration. I think I might have looked at the other participants to see what they would say before I accepted the offer. I wasn’t nervous about trying it, but it also wasn’t anything I had ever contemplated before.. so when we entered her together and started thrusting, I was not mentally ready for how clearly I would be able to feel another throbbing cock rubbing against mine. I tried for a few minutes- but it was no use, the shock of the new sensation drained all the blood from my penis and I was down for the count. I apologized, but there were no hard feelings and the moment wound down. The other guy decided he was going to leave at the same time I was and we walked out together. I remember he had a big smile on his face as we walked awkwardly to the sidewalk where we shook hands, laughed, and agreed it was fun before parting ways. All these years later, I still wish I could watch the tape.

The End

Storytime: The Craigslist Cuck Incident, Double-Trouble

Part 2

Arriving at the house I had become more nervous than excited, but I steeled myself and knocked on the door. I was welcomed in by a stout, bearded man. I wore shorts and a dark T-shirt that was stretched tight by his protruding belly. The front door of the house opened up into a mostly enclosed living room lined with two couches and Americana furnishings. In the center of the room, a matress with a fitted sheet laid in conspicuously on the floor. A diminutive redheaded woman sat on the couch on the leftmost wall, she smiled shyly and rose to greet me with a soft hug and a “nice to meet you.” I could feel she was also nervous, which was comforting, however, the husband spoke up and confessed the dilemma of the evening- they had double-booked with another man who was arriving soon.

I was taken aback by this new information- my natural inclination in my life is to have a plan and stick to it, but I agreed to stay for a group event. We didn’t wait up for the other guest to arrive, the wife and I both got naked on the mattress and she started sucking my cock- it felt incredible to me. I was enjoying it so much I didn’t think twice when the husband started filming on a comically old camcorder- I was finally getting the wild sex I wanted. And then the knock came at the door.

To be continued..

I decided it could be exciting to share some of my past experiences on here. Not all of them feature me in a submissive role- but they are all true stories that I think will be fun to share!

Storytime: The Craigslist Cuck Incident, Double-Trouble

Part 1

I started attending university in the fall of 2009. Many nights were consumed by hyper-sexual manic episodes and sexual frustration. For a time, I got in the habit of scouring craigslist personals for a hookup or a new experience. The hours were long and the success rate low, but I walked away unscathed and with breadth of experiences- some fond, a few traumatic, but mostly satisfying. One experience in particular remains a special memory that still amuses me. 

Once upon a time, I replied to a personals ad posted by a married couple looking for a man to come over and have sex with the wife while the husband watched. It was early days in my sexual journey, cuckolding was not a kink I spent time thinking about in any aspect.. Even so, I was hungry for new experiences and for pussy, so I replied as soon as I read the ad with a note and flattering picture. I eventually received a response with an address, I quickly confirmed and frantically scurried out the door.

To be continued..