This is a story about how my most embarrassing moment turned into the best luck I ever had. Her name was Lexi — or as I secretly referred to her in my inner-most thoughts, Sexy Lexi. And she was sexy in the best possible way: a shy, modest dresser who didn’t need anything more than a pair of blue jeans and a t-shirt to show off an unimposing, yet curvy, athletic figure. She had brown curly hair and haunting hazel eyes. I knew her from church, which I realize might be a strange place to begin a sex story, but hey, that’s just how it all…or should I say, I, went down.
Lexi and I sang in the choir together on Sundays and we both had a habit of wandering out of service once we were finished with singing. We talked here and there, sometimes cordially, at other times we were awkwardly flirtatious. Then came the fateful day during service when we crossed paths walking down the hallway and I put my foot in my mouth in the worst possible way.
“Hey there, sexy Lexi!” I said, casual as ever. That is, until I realized what had just exited my mouth.
She stopped. Her eyes went wide and my face turned red as a turnip. She burst into laughter and put her hand over her mouth. “Oh my God, I am so sorry! I did not mean to say that out loud!” I said.
“Wow!” she said as her face turned its own shade of red.
“Um, I’m gonna shut up and go crawl in a hole now,” I said as I started to turn toward the opposite direction that she had been walking.
“You may proceed,” she said, making an old-fashioned bowing gesture with a wave of her hand. I avoided her for the rest of the service and left as quietly and quickly as I could once it was over.
The next week when I saw Lexi her shyness had given way to coquettish teasing with a few not so furtive glances in my direction during rehearsal. I think she might have winked at me but I’m not entirely sure. I was young and filled with enough testosterone to let that little bit of encouragement fill me with a dangerous amount of self-confidence. I thought I’d break the tension between us with a little joke. So I sauntered up to her during service after the music was finished and started a conversation. I found her again in the foyer where fortunately we were the only ones around.
“Hey, sorry about last week,” I said with a casual smile. “I didn’t mean for you to hear about your secret nickname.” She blushed just a little.
“That’s ok, Kevin. I’ll just have to think of one for you now.”
“Fair enough,” I said. “What are you doing after service?”
“I don’t have any plans,” she said as her face lit up slightly.
“Well, then…what do you say we get out here…and do a little…missionary activity??” I said with a cheesy wink.
Her blushing intensified. She gasped slightly and looked down at her shoes trying not to laugh. Then she looked up at me and shook her head in disappointment. “You are soooo bad!” she said, still trying not to laugh.
“Am I?” was all I would think of in response.
She smirked and paused for a moment. “Yes. Yes you are,” she said. Her voice took on a playful, maternal tone and she wagged her index finger toward my nose. “You are a very bad boy! I should wash your mouth out with soap!”
“Well, if that’s what you’re into,” I quipped.
Lexi burst into laughter as the tension between us finally broke. I laughed in return. What happened next took me completely by surprise. She reached up, grabbed my ear, and began pulling me toward down the hall toward the offices. “Come with me!” she commanded.
“Yes ma’am!” I replied.
She took me through a door, down another corridor, all the way to the end of a row of office doors. My ear was killing me but I was way too turned on to care. She turned us to the left and took me into the last office. The lights were off and as the door shut we were suddenly in complete darkness.
“Is this where bad boys go to get punished?” I teased.
“I’d keep your mouth shut if I were you,” she said, giggling. She grabbed me by the shoulders and pushed me toward the back of the room. I couldn’t tell where I was going exactly but in a few seconds, I found my nose in a corner.
“Stay right there, Kevin. You’re in time out. I’ll be back to deal with you after service.”
“Ummm…Lexi? What if someone comes in?”
“No one comes in here until Monday morning. And I have a key. So just do what you’re told and if you’re a good boy for me I might just come back and show how sexy Lexi can be.”
Well, that had me sold. “Yes, ma’am!” I said. The door opened and shut. I was alone in the dark with no idea of what would happen next.
When Lexi returned she found me seated at the desk with my feet up, holding a ruler I had found in the top drawer. She seemed all too delighted to catch me disobeying her commands. She smiled in mock horror and put her hands on her hips. “What do you think you’re doing, Kevin? I told you to stay in the corner and I definitely didn’t give you permission to turn on the lights.”
“Oh sorry, I forgot,” I said in the most cavalier tone I could muster. “Are you gonna punish me?”
She froze in a stiff sort of way. She didn’t seem to know quite what to do but I could tell she was thinking hard to form her next words. I reached across the desk and handed her the ruler. The look that dawned on her face once I did told me everything I needed to know. She took it and began to slap it against her palm. I stood to my feet and faced her.
“Oh, are you gonna spank me with the ruler?”
She seemed to gain her composure and gave me a stern, confident look. “Well, that’s a stupid question isn’t it?” she said, placing one hand on my back. She pushed me down until my torso was right up against the desk. “Of course I’m going to spank you with the ruler. Now bend over the desk!”
I offered no resistance. Thankfully the desk was clear of everything except an old desktop computer on one side. I felt the ruler smack up against my butt three times, not hard enough to cause any pain, but more than hard enough to bring my arousal to a whole new level. I know just what to do, I thought.
“Oh Lexi… you spank like a girl!”
“Ohhhh, is that a fact?” she said, sounding quite confident now. “Stand up and turn around!”
I stood to my feet and faced her. She looked as if the words were on the tip of her tongue, she only lacked the courage to say them. Then, to my utter astonishment, she took a deep breath and looked me square in the eyes. “Drop your pants, Kevin.”
I reached down, unbuckled my belt, and undid my black slacks. They fell to my ankles, revealing my gray boxers which were sticking out like a tent. Lexi’s eyes darted down repeatedly as we stood there, facing each other. She pointed at the desk with her index finger. I bent over and put my elbows on the desk.
“I think we should take these boxers down. I don’t think you’re gonna learn your lesson otherwise,” she said.
“You’re the boss, sexy Lexi.” And with that, I felt my underwear make their way to my ankles and the sting of the ruler came immediately after.
“I did not give you permission to call me that!” she snapped as she gave me three sharp spanks. “You should be ashamed of yourself, lusting after a woman in church!” The ruler came down harder several more times. I closed my eyes for a second, trying not to look like a total sissy by crying out or moving out of position. I suddenly felt the most welcome sensation of her soft, dainty fingers massaging my manhood.
“Aaaand what’s this we have here?” she said, pinching ever so gently around the base of my shaft. She moved upwards toward the top and then down again in an expert-like fashion. I began to pant like a dog. “Well, you’re certainly bigger than I thought you would be…”
“I don’t think I’ve ever been quite this big before!” I said, almost losing my breath. The gentle massaging continued as the ruler smacked my bottom several more times. The combination of spanking and her hand around my shaft was a little more than I could handle. “Ohhh Lexi!” I panted. “I’m gonna make a mess!”
She giggled and continued spanking. “Ohhh my, we’re sensitive aren’t we?”
I nodded. “It feels soooo good.”
Her hand left my dick and the spanking stopped. She began pulling my underwear back up. I thought maybe she had decided to stop but then once my boxers were back in place she pulled the back of them down just enough to bare my ass. Her hand gripped full around my erection and she began to stroke over my boxers just as the ruler smacked my bottom harder than ever. I closed my eyes but I could still hear her smile as she taunted me.
“You realize you’re gonna go straight to hell if you come in church right?”
“Ohhhh, it’s worth it!” I exclaimed beneath my breath.
She began to stroke me more aggressively as she continued spanking me. “Oh my gosh! You are such a naughty boy Kevin!!”
It was only a few more strokes and spanks before I felt the blood rush to my head. My hands were starting to tremble and I cried out. “Ohhhhh, Lexi!!” She rubbed even harder and faster, this time spanking me over and over again in the same exact spot, taunting me beneath her breath. “That’s right Kevin, come for me. Show me how naughty you can…ohhhhh, Kevin!”
There was something about hearing her say my name and feeling that ruler against my bottom harder than ever that pushed me right over the edge. The first two spurts went straight through my boxers and onto the desk. The rest made a mess from the inside. I was so overcome with the exhilaration of orgasming in front of real woman — the woman of my naughtiest fantasies, no less — that I collapsed to my knees and hyperventilated for more than a minute. Lexi ran her fingers through my hair and smiled at me while I regained my composure.
“Thank you!” I said look up at her, still out of breath. “Is there something I can do for you?”
She reached for the box of tissues on the desk and handed me one. “You can start by cleaning up after yourself. I don’t appreciate having my desk soiled.”
I stood to my feet and did as I was told. It was a type of humiliation that spoke to me in a way that was deeply erotic, and strangely satisfying. “Wait, your desk?” I said, sounding puzzled.
“Yup, I got promoted. I’m now assistant music director and you are in my new office!” she said with a twirl of her hand.
“Ohhh, that’s why you had a key. So that means…”
“I’m your new boss!”
“I’m not gonna lie, that’s kind of a turn on,” I said with an embarrassed smile. “Well, my butt is very tender. So I’d say your team management skills are coming along nicely.”
Lexi stepped forward and rubbed my bottom. “Then I take it you learned your lesson and you won’t be calling me by objectifying names any more?”
“I don’t know, boss. I think I might need some more one-on-one coaching.”
“Well..I guess I’ll be seeing you in here next week then. I just hope you realize that I will be the one orgasming next time. And if that doesn’t happen, you will be very sorry.”
“Yes, ma’am!” I said.
“Good,” she said with a big smile that suddenly turned into a stern expression. “Now pull up your pants and get your naughty butt out of my office!”
I did exactly as I was told, but not before receiving one last smack with the ruler on my way out.