Education of a Scoundrel

In life it is of vital importance to have a goal. One year in college my goal was Candy, a blonde dance major with a habit of letting her egregious breasts fall out of her top in dance class. None of my friends knew much about her, just that she hung out with a few artsy theatre types and her nerdy brother who rented a house with her. But once again eavesdropping served me well.

I was sitting in my usual booth in the school cafeteria when her brother Jake and his buddy Bob ensconced themselves in the booth next to mine. I was bent over a book reading so I don’t think they even saw the top of my head. I knew Jake from one of my classes and talked to him a couple of times but didn’t really know his friend. Jake started talking about life with his sister. “Man, I don’t know how to handle living with my sis. Do you know how she’s paying for our place?” Bob replied “Isn’t she waitressing?” I heard Jake groan then reply “No, that was last year. Dude, she’s working as a dominatrix. She spanks businessmen and makes them suck her toes for a living. Our house is full of bondage gear; she turned her bedroom into a dungeon. Yesterday I went home and found a guy in an Armani suit that looked like it cost more than my car eating out of my dog Max’s bowl while he waited for her.” Bob was gobsmacked, “Holy shit, what did you do?” Jake sighed, “What could I do? I filled the water bowl and went to my room to study.”

By now I was sprung. Then things turned really interesting. “Yeah, her birthday is in two months, she’s planning a huge blowout, told me to invite everyone I know to the house. But some of her new friends are just plain freaks, not sure what’ll happen when my crowd collides with hers. Want to come?” Bob took a moment then accepted, “That sounds like the least boring party of the year, count me in.” As they left I had a new goal for my life brewing in my mind like something in a witch’s kettle. Goals are important and this was going to be big.

When launching any campaign you need a strategy that is workable and easily changed as circumstances evolve. The first rule is “know your enemy”. So that next week in class I made sure I was in the same study group as Jake and talked him up about non-school things to get to know him. When I found out he and his friends played Dungeons & Dragons, I knew that was my ace in the hole.

The next Saturday I was at his house with his buddies, pretending to be a devilish rogue (yes, I know, it was intentionally ironic) stalking an aristocrat to steal his magic ring and plying Jake and his friends with cold beer to make it easier for us to socialize. Over the next couple of weekends I made sure I became leader of the adventuring party then leader of Jake’s friends outside of the weekly D&D sessions. When we went out anywhere I was the one who made the plans and got things moving, calling the guys to get them out of their respective ruts. If there was a party, I was the life of it.

Now, very few men like seeing their female relatives being pursued and nonchalance opens more doors than eagerness because nobody likes the stench of desperation, so when Jake invited me to his sister’s party after a marathon D&D session one Sunday afternoon I played it cool, quizzing him on her taste in music and friends then asking him what kind of beer and snacks would be on hand before finally accepting the invitation. Not wanting to telegraph my interest in his sister’s breas-, er, dancing, I just acted like her party was one more item on my social calendar. I told Jake I’d let him know later if I was going to be there then waited till after class the following Tuesday to confirm.

The party was on Saturday night, starting at seven o’clock. I got there an hour later in a leisurely fashion, in no particular hurry. I was wearing the same generic jeans and t-shirt as every other guy but had a pink feather boa that smelled of stripper and a smudge of lipstick on my neck. As soon as I walked in people began pointing and whispering, wondering where I had been before the party. Jake got me a beer and showed me around, introducing me to his sister and some of their friends. I ignored her comment about my boa and flirted with one of her friends, Gina, a geeky theatre major with black hair and lots of tats. She gave me a confused look and headed to the dance floor in the middle of the spacious living room.

Nothing makes you an alpha male like leading the pack, so after I sipped my drink and chatted with a few people, enjoying the music and noshing on some pizza, I rounded up the D&Ders for a big “Huzzah!” cheer and a toast to the birthday girl in the middle of the room to make sure Candy’s friends knew who the leader was. Once again Candy stared at me, but this time with more interest.

The band of gamers drifted away and a girl in a red dress passed through my peripheral vision, her bosom preceding her by a foot. She came up behind me and sniffed my cologne then pressed her silicone enhanced chest against my back. I could tell by her breath she was more than a little tipsy so it was no surprise when she started licking my neck and slid a hand in my pants. When she grabbed my Johnson and let her fingers do the walking I told her she had exactly three hours to stop that. She giggled and stuck her tongue in my ear.

I had no reason to object to this treatment, so I was letting her have her way with me. I could feel her nipples getting stiff and my whole body was standing at attention. Then I noticed something strange. Something was pressing against my bum. Was that her hand? She had one hand inside my pants. Her other hand was squeezing my chest. I felt something twitch behind me. OH. MY. GOD. That’s not a hand! My jaw dropped then so did my cup of beer, spilling on the floor. I heard her giggle louder. “Oh, damn, I dropped my drink!” I blurted out, pulling her hand out of my pants. “So sorry, I need a drink, nice meeting you...” I said as I hurried away, holding my butt cheeks together as I walked. I grabbed another beer and stood against a wall so my posterior was covered. Just then Jake walked by and told me too late, “Hey, Sam, watch out for my sister’s tranny friend Helga, she’s got a dick like a baseball bat...” NOW he tells me! Suffice it to say it took me a little while to get my composure back.

I had some more pizza after a few minutes then returned to the chase, looking around for Candy. She was dancing with a football player I recognized as one of Jake’s non-gamer friends, Dave from Ohio. Dave was about twice my size, very drunk, and had his hands all over Candy. I needed a diversion. I saw Helga dancing with Gina and hit upon a plan. I danced my way over to Helga and Gina and whispered in Helga’s ear, “You took me by surprise, I don’t go that way. But if you do me a quick favour I’ll owe you big time.” Helga looked at me with a raised eyebrow. I pointed at Dave and told her I need him out of my way. She looked at Dave then Candy and giggled again. My plan was coming together.

Helga started dancing with Candy and Dave and after a couple of songs managed to split them up, leading Dave upstairs to an uncertain fate. That was my queue. I ambled over to Candy who was now sitting on a couch having a drink and said “You’re pretty cute, want to dance?” Candy was used to being told how hot she was, it was her due, being told she was “pretty cute” was tantamount to being called a dog. She gasped “Cute?! Did you just call me cute? How dare you? Look at this body, men pay me to...” I cut her short, “Okay, you’re not cute. I want to dance with you anyway...” She was in shock. Nobody, especially not a guy, ever talked to her like that. While her mouth hung open I lassoed her with my boa to pull her on the dance floor. “Close your mouth before you swallow a fly...” I told her. Dancing mixed with similar teasing followed, during which I made a point to prick her ego often and told her about why I didn’t like heights and other tales of my misdeeds. Eventually we ended up back on the couch making out with her straddling my lap and me sliding my hands inside her shirt to finally feel those breasts I had been dreaming about. A strong woman needs a strong man to tell her where her place is so she can feel secure and safe. I let her know her place was on my lap with her tongue in my mouth.

Things were going well. Candy thought I was the alpha male of my group and responded accordingly once I got the competition to go another way and got some time with her. A few funny pricks to her ego disarmed her, making her drop her shields long enough to get to know me, and setting her back on her heels when she tried to give me attitude let her know who was in charge. Then it happened...

...Out of nowhere there was a horrible scream. “Aaaaaaaaauuuuugggghhh!” Then Dave, buck naked, came falling down the stairs having tripped while trying to pull up his underwear, and landed in the middle of the living room face first, breaking his nose. He was covered in lipstick marks and hickies. Then Helga, still pulling on her dress, came down walking down the stairs. Dave leapt up and point at her. “SHE PEES STANDING UP!” he screamed, and ran out of the house in his boxers to disappear into the night. Helga sheepishly replied, “I’ve been a bad girl...” The crowd broke into cheers and laughter and Dave’s friends ran out to find him.

Taken aback by what had just happened I unwittingly said aloud what I was thinking. “Gee, I didn’t think THAT would happen...” Candy overheard my ruminations and glared at me. “What did you do?!” she snapped at me. “Um...” I replied eloquently. She grabbed my nipple and twisted, sending pain shooting through me and proceeded to annunciate the question more emphatically. “What. Did. You. Do!?” I confessed, “I just asked her to distract him so I could dance with you...” She twisted harder, “That boy is going to be traumatized for life! You are a bad, BAD boy!” I cringed and confessed, “Yes, it was wrong, I should be punished...” Her eyes lit up and she grinned evilly. “You are SO getting it!” She jumped off my lap and pulled me up by my ear, making me yelp in pain. Still as cocky as ever I replied, “Promises, promises...” which made her dig her nails into my flesh. “Oh,” she said, “I deliver, don’t worry.” Then she dragged me up the stairs to her bedroom/dungeon.

Once in her room she threw me down on her bed and yanked off my pants. I sprang to attention, hitting her in the eye. “Brat!” she yelped then slapped a cock-ring around my junk and smacked my balls. I tried to get up and grab her but she cuffed my hands and attached my cuffs to a chain from the ceiling and hoisted me onto my feet by my hair before I knew what was happening. This girl worked fast. She slid a Trojan on me and started sucking me down her throat till I thought I was going to burst, then “thwack!” she hit me with a riding crop across my bare ass. The sting made me wince but it also made my cock twitch.

That was the pattern, some pleasure followed by a jolt of pain. She kissed me, licked me, then tortured me. The arousal just built until the pleasure became a form of torture too, with no way for me to gain release. The feel of her body against mine, the scent of her own arousal, the sting of her whip, her nails digging into my skin all blended together. She teased me with the scent of her pussy, made me go down on her over and over, but would not let me penetrate her or pleasure myself. Finally I was near weeping, begging for release. “Okay,” she sighed “you have been punished enough, you little punk. Let this be a lesson to you!” then removed the cock-ring and squeezed my cock between her soft breasts. Within seconds I came all over them, at last gaining the release I needed. I was drained.

It was G-d only knows how late at this point, we were both tired, so Candy told me to go sleep it off in one of the guest rooms. “No, no, no! You’re not getting any more of me till you learn to behave yourself!” she told me. So I toddled off to find a bed for the night. Now, what I found when I did is a whole other story, one with more sex and less whipping, but lots of lessons on bad behaviour. But to recap, first, you need goals in life, both long and short term, that make you push yourself forward. Next, you need a plan that has some room for improvisation and a strategy for getting what you want. Standing out of the crowd is good; don’t be afraid to be a little outrageous and get people talking. Being talked about is almost always better than being overlooked. Women want you to be a man, not a boy, so be a leader and take charge. Don’t be afraid to ask for help from strangers, they may help you in unexpected ways. Finally, it is better to ask for forgiveness than for permission, so don’t hesitate to go after what you want even if a few toes get stepped on along the way.