*Sadly, this is a very true story from my life before I gained confidence. Names have been changed to protect the recipients of my awkwardness.*
*Apologies in advance if this goes against the themes covered by this sub. Even though this story is full of sexual frustration, Kimmie is still someone I enjoy thinking about from time to time when I’m alone. There’s still time to top it, but she’s by far the sexiest woman I’ve blown it with.*
———
Kimmie was an impossible to ignore 18 year-old force of nature. With her long brunette hair, she was almost six feet tall (most of that were her thin but shapely legs) with a model’s figure to match and the demeanor of a girl who had been the most striking one in the room for many years. When we would walk together, it was amusing to see the cascading whipping heads from the boys aligned along the edges of the hallway.
We became acquainted when her parents insisted she join the debate team. I (also 18) was the team captain and instructed all the new members on the basics of debate. Her father was a successful lawyer and knew it was a great way for Kimmie to get some of the early skills that could come in useful if she chose to go down that career path.
After a few of our meetings, she would seek me out in the hallways or at lunch. I did not understand what was going on. When she would stroke my shoulder or want to walk arm-in-arm, I was convinced she was messing with me. Kimmie wasn’t known to be big flirt, but she was sending me all the signs: playing with her hair, rubbing my hand or arm, laughing too loudly at my jokes. When she started asking me what I thought of her, I stumbled coming up with a response. I entertained no other possibility other than this was heading towards some epic embarrassment she had planned for me.
One aspect of Kimmie I had trouble reconciling was her bimbo aura. She acted the part well; a little too well, by my estimation. I was convinced it was done to facilitate her social life, but every once in awhile she’d do or say something that would betray something deeper within her. By my rationale, if she was capable of that pretty effective deception then she must be playing with me as well.
A few days before the events below, Kimmie’s good friend Janet (also gorgeous) approached me at my locker. “Um, look Alex–I don’t know what your problem is, but Kimmie is, like, really into you. I mean, I’m not sure what game you’re playing, but you are, like, being a total idiot right now.”
I laughed and gave a sarcastic nod. “Right Janet. She’s super into me. Got it.”
I heard an exasperated “Whatever!” as I headed towards class.
Looking back, I was being a total idiot.
In my defense, I did not understand back then that to some girls intelligence can be more attractive than physical traits. I fell in the middle of the road in terms of looks, but I was one of the smarter kids in school. File that in the “Things That Would Have Been Good To Know Back Then” folder.
Later that week, we had a tournament about an hour away so we were able to get an activity bus to take us there. On the ride up, Kimmie sat in the seat in front of me and we talked most of the way. I remember I kept making her laugh, so much so her mascara ran a little bit and she begged me to stop. I guess that was what we should call the tipping point.
Once we arrived at the school hosting the tournament, Kimmie no longer restrained herself. As we got off the bus, she grabbed my hand. I saw some girls I knew from a previous tournament and they waved at me. Kimmie narrowed her eyes, almost comically, and shouted, “He’s mine, ladies.”
To my fellow male debate nerds, I must have seemed a god that day.
I had this statuesque beauty attached to me, her large breasts bouncing slightly as she marched down the hall with me and her high heels clicking to announce our presence to those who had not already gawked at her. I swear to you, my thinking at this time was still that she was putting on an act and was waiting for the moment that I would believe this deception to humiliate me.
(Thanks Mom!)
She reluctantly let me go when we needed to get to our separate rooms for the matches. I felt relieved to focus on the relatively simple matter of universal healthcare plans and the related esoterica of policy debate.
After the matches were finished, we reconvened in the school auditorium. Apparently, absence had made her heart grow fonder. Kimmie sat next to me and began an ill-fated seduction that still haunts me to this day.
She began by rubbing my bicep and then moved down to my thigh. She took my lack of reaction as a challenge and pulled up her skirt enough so her long leg in black hose could be draped over my leg and perilously close to my crotch. She proceeded to rub her leg back and forth as she lightly moaned in my ear.
I was in agony. At this point, my body comprehended what my brain would not and I realized any further stimulation was going to lead to an unmistakable announcement of my interest in her activity.
Then fate intervened.
“Kimmie! Alex! Cut it out right now!” Our team adviser was glaring at us. Kimmie immediately put a totally innocent look on her face (see–she was so damn good at faking things!) and said, “Sorry, Miss Lawson. I had a cramp and Alex was just making sure I didn’t hurt myself.”
The rest of the team in the row behind us snickered. When Miss Lawson moved away, one of them whispered, “Get a room you two!” Kimmie turned around and stared. “Believe me, I would like that very much!”
After we were discovered, Miss Lawson never strayed far, so Kimmie was mostly limited to holding onto my arm through the trophy presentations. When she thought she wasn’t being watched, she would put her head on my shoulder. I could smell her sweet teen perfume on me and I wanted to explode.
It was time to leave. As the sun was going down, we headed onto the bus and Kimmie was about to sit next to me when Miss Lawson intervened. “No, no, no, no. Kimmie, you will be at least two seats away.” Kimmie gave me her best puppy dog eyes and slunk towards the front of the bus.
This time apart gave me some time to analyze what had just happened. Had I been misreading this situation the whole time or is she the most evil of social pranksters? I looked around and it was unmistakable: everyone was looking at me differently now.
Wouldn’t this be the perfect time for Kimmie to spring the trap?
About 30 minutes into the ride home, we stopped at a fast food place to grab some dinner. Kimmie took advantage of the chaos of 20 hungry high school kids descending upon the counter to check in with me. “Miss me?,” she asked with a sweet smile.
We talked a little while in line and after we picked up our food she leaned in. “Look, Miss Lawson is totally going to fall asleep after this. I’m going to sneak back to see you when she does. Don’t sit next to anyone else, okay?” I nodded.
As she predicted, Miss Lawson was out within 10 minutes of our return to the road. Kimmie practically crawled back to my seat and gave me a hug. Everything was okay for about a minute and then things got weird. She started what seemed to be hyperventilating and her eyes teared up.
I was totally confused. “Kimmie, are you alright?”
“Oh my god, Alex. I’m in so much trouble!”
“What? What in the world is wrong all of a sudden?”
“I ate a chicken nugget.”
“Uh, okay…”
“I gave those up for Lent! Alex, I could go to Hell over this!”
I was not very knowledgeable about Lent or the stakes involved, but being hit with eternal damnation over a chicken nugget seemed a little bizarre. “Kimmie, I’m sure it’s not a big deal. Can’t you just confess or something and then go back to not eating them?”
She didn’t answer. She just started sobbing and then she thrust her head facedown into my lap. Yes, just like that. This began my most confusing situation of close female contact.
As she laid her head on my lap, Kimmie continued to sob. Her motions related to the sobbing combined with the motions of the bus let to multiple contacts with my cock. When she went to wipe her eyes, she rubbed it. When she put both hands under her head, they laid right on it. And finally when she wiped her mascara-running eyes on my crotch, her lips brushed it.
My confusion was so strong that I somehow managed not to get hard through all this. Considering the hair-trigger that is the 18 year-old penis, I still am impressed in a way by this act of willpower.
However, as she lifted her head and she gave me a cold look, I realized the crying had been a ruse to do something much more fun and I had ruined the chance in epic fashion. I had blown it to a degree that she would no longer be pursuing me because I had actually dented her ego.
Kimmie let out a big sigh and shook her head. “I need to go over there and calm down before we get home.”
When the bus arrived, Kimmie left without saying a word. I got in my car to drive home and as the shock wore off, the terrible error I had made began to really sink in. I sped home, ran to my room, threw my shirt and mascara-stained pants on the floor, and jerked off furiously still smelling of Kimmie’s perfume.
The next morning, my dad had a chuckle when he saw me putting my pants in the washer. “Fun night, son?” Oh Dad, if you only knew how it really went.
I arrived at school and I was getting some odd looks. One of my friends grabbed me and said, “Dude, you’re gay? How could you not tell me?”
“What? What are you talking about?”
“Janet is going around telling people that you are gay. She said she has proof.”
“Oh sweet Jesus…”
I tracked Janet down. She laughed when she saw me. “Now, it all makes sense.”
“Janet, I am not gay. It’s been very confusing with Kimmie.”
“Oh, I bet it was confusing.”
“No, seriously. I thought she had been messing with me this whole time. And I can see why Kimmie might come to the conclusion that I’m gay, but I really do like girls. I just was overthinking everything.”
Janet made a face. “She’s super pissed, Alex. She’s never been rejected like that.”
“I bet, but I wasn’t trying to reject her. I will talk to her–just please stop with the revenge campaign.” Janet agreed to back off provided I made things right.
And I did talk to Kimmie. We were able to laugh about it eventually, but the magic was gone. She was never going to see me the same way after that. Although, I did get a long kiss on the cheek from her at graduation. She got one last laugh out of leaving her lipstick on me while everyone stared at the beautiful girl kissing the nerdy boy, so I guess there was still part of her that liked to make me and others squirm.
Source: reddit.com/r/sexystories/comments/73bpry/the_master_debater_mf_humor_nonfiction_frustration