A pivotal event that led to my obsession with spanking occurred in the spring of my senior year of high school. My friend, Steve, and I were playing homage to Ferris Bueller and spent a fine spring Wednesday skipping school. In the afternoon, about the time school let out, Steve was showing-off his new dirt bike. I took a brief lap of the neighborhood and clumsily took the turn into our drive too wide and ran right through our neighbor’s flower bed that lay on the border of our properties.

“Ms Evans is gonna be pissed,” Steve observed, looking towards our neighbor’s house. I hoped that she was at work and I might have time to tidy-up the tire tracks and broken plants but she suddenly emerged from her front door. She crooked her finger at us and Steve offered, “See ya,” and roared away. I ambled over to a visibly upset neighbor. She was a thirty-something divorcee with an incredible figures and frankly a fairly common factor in my sexual fantasies. Steve and I had often discussed her feminine shape - particularly her very generous breasts - arguing whether they were real or fake but deciding finally that provenance was irrelevant we just wanted to see and touch them.

“Skipping school?” she guessed. “You’ve made quite a mess of my garden!”

“Sorry, miss,” I attempted.

“I’m thinking your parents should be made aware of your hijinks,” she continued.

“Please don’t,” I begged.

“You deserved to be disciplined. If you want me to remain silent about this, you need to come inside and accept your punishment,” she demanded. I wasn’t sure where she was intending but I desperately wanted to keep my parents from knowing about the day’s adventure.

I looked over at our house and then followed Ms Evans inside her front door. Both of my parents were away for a few days but our live-in housekeeper would be home soon. My folks traveled a fair bit for work and Mona had been managing household affairs for a few years now. During the school day she was often away, at the market, taking classes relating to her various hobbies, attending yoga classes and such. She had a full life in addition to taking care of our house and me. As with my parents, I needed to keep Mona from discovering anything was amiss.

Ms Evans led me to her living room and had me wait there for a few moments. She returned with a paddle that immediately caught my attention and immediately conveyed the sort of discipline she had in mind. “If you want me to keep quiet about you and your friend playing hooky and tearing up my flowers, you’ll accept ten swats,” she announced. I nodded meekly, not yet dawning on me why a single woman might have such an implement at the ready. “Turn around, lower your pants and bend over - hands on your knees,” she ordered. I complied, having been spanked in similar poses before but never by a buxom neighbor that I found incredibly desirable. She tapped the plank against my bare buns and gave me a hard swat. I cried out and stood up in response. “Count these, and if you break position again, that swat does not count and will be repeated. Understood?” she added.

“One,” I moaned. In less than a minute, my ass was ablaze and my cock rock-hard with arousal.

“Put yourself back together,” she instructed and a few moments later let me out.

I returned home to find that Mona had arrived in the meantime and was preparing dinner. She greeted me affably and set the lid on a simmering pan. “How was school today,” she asked with an unusual expression.

“Fine?” I replied.

“You might as well end the charade,” Mona replied. “My friend works in the front office and noticed you were out today. She texted me asking if you were sick.” I nodded my admission. “Go get your mother’s brush,” Mona ordered. I trudged off to fetch the implement that both my mom and Mona favored. I tried to wish my erection away. After leaving Ms Evans with a raging boner, I had planned on heading straight to my room to resolve the tension. I returned to the kitchen with the tool that had heated my backside countless times. Mona had pulled a chair from the table to face the room and reached out to take the brush. I dutifully approached her right side, undid my belt and slid my jeans and boxers down. “Oh, my,” Mona remarked seeing my very turgid penis. Nevertheless, she guided me over her knee. “Looks like somebody has already warmed your backside recently,” she noted.

“I got caught give Steve answers to the math quiz and we both got swats,” I lied. Corporal punishment was routine at our school and the idea that miscreants would be paddled for infractions - usually on-the-spot in front of the rest of the class - was completely ordinary.

“Well, I’m gonna make that seem like a walk in the park,” Mona announced and began to spank. I had been over Mona’s knee innumerable times and never received a spanking this hard or long. It seemed to last forever and the fire in my cheeks grew and grew. On the front side, the assault on my ass cheeks only intensified my arousal. To my horror I felt climax quickly approaching and then the unstoppable spasms of ejaculation. Mona felt it, too, paused the spanking and prompted me to stand. My cock was twitching, still leaking the last remnants and her thighs were soaked with semen. She stood and reviewed the scene including a puddle on the floor. “Bend over,” she ordered, pulling my belt from my pants. She resumed the punishment, blistering my already red-hot ass with the heavy leather strap. “Clean-up yourself and that mess,” she commanded and stalked off. I complied and a few minutes later we were at the table eating her stew in the awkward aftermath of the action that had just occurred.

The next day, I dropped by Ms Evans and apologized for wrecking her flowers, then awkwardly approached the topic that had been in my head since yesterday’s events. The spankings by her and Mona had triggered something new. “Would you be willing to spank me again - maybe routinely?” I asked.

She considered her answer for a moment. “You would definitely benefit from regular, routine discipline,” she noted and then suggested, “Come over every Wednesday after school.” I nodded my agreement and left. I could have easily made a similar request from Mona but sensed she approached spanking my bottom as part of her duties whereas I felt that Ms Evan truly enjoyed it and yearned to give spankings like I seemed to crave receiving them. Like clockwork, I stopped at Ms Evans after school on Wednesdays for the rest of the semester. I would leave content with a fiery ass and a stiff cock. When the semester ended, we maintained our Wednesday ritual until I left for college.

That Wednesday event seemed to also change the dynamic between Mona and me. Spankings seemed to be the answer even the most minor missteps, but the scene was typically my bedroom. Perhaps a few times a week, she would decree something like, “You’ve done it now, mister. Go to your room to await your punishment.” She would usually not keep me waiting long, entering with the chosen implement that day, and her taking a seat at the end of my bed. She seemed to take great satisfaction at lowering my pants, seeing my growing erection and guiding me over her lap. While I never performed an encore - ejaculating on her lap - her clothing was frequently dotted with wet spots of pre-cum. She would often suggest I recline on the bed and pleasure myself while she watched, “You should take care of that,” was a frequent post-spanking instruction, gazing intently until release. It was a vivid fantasy for me, as well. I welcomed the frequent trips over her knee but also frustrated by her lack of participation in the finale. I dreamt of her stroking or sucking me to fruition and then joining me in the post-ejaculation clean-up, her round form fully naked with with me in the shower.

After leaving for college, my sessions with Ms Evans continued as possible on weekends home. They never had the sexual overtone of Mona’s spankings but were so very gratifying. At winter break, Ms Evan put me over her knee as was a usual starting point. She paddled my ass with a bath brush and when she paused, had me stand. “I’ve taken a new job and will be moving away. I’m afraid this is our last session together,” she announced. I was disappointed by the news but then the scene took an unexpected turn as she pulled off her top and unfastened her bra. I finally saw her magnificent breasts. “It’s ok. You can touch them,” she allowed. I fondled them for a few moments and then she sank to her knees. She took me in her mouth and the her oral stimulation was highly effective, bringing me to climax far too soon. She took the first jet into her mouth but the remainder she directed onto those perfect breasts and then rubbed the sticky concoction over them.

After I went to college, Mona took another job and our very quirky spanking connection was also lost. I look back at those few months as nirvana. I’ve remained very obsessed with spanking, looking for opportunities to give and receive as often as possible, but nothing yet has come close to the intensity and delight those two women provided.

Today, I find myself sitting in the office of the head of HR. I have just started a new job and was a bit surprised at the email that summoned me to this meeting. “Go ahead and have a seat in her her office,” the executive’s admin had offered. I was looking around the room and heard footsteps behind me and the door close.

“So, less that a week on the job and already in trouble,” I heard a familiar voice scold. I turned to see my old nemesis, Ms Evans smiling at me. “You know - at this company- the response for failing to fill out your timesheet correctly is corporal punishment.” I nodded agreement with her premise. “Stand-up, drop those pants and bend over my desk,” she ordered. I eagerly complied as she drew a paddle - a match to the one she had first used upon me - from a cabinet. A dozen swats left my as ablaze and my cock rock-hard. She tapped my erection with the paddle and handed me a card, “Let’s take care of THAT after work.” I turned over her business card with an address jotted on the back. I exited her office and her admin gave me a knowing smile, seeing the obvious bulge in my pants and full-well knowing my ass cheeks were aglow.