On Friday I made out with a virgin... Saturday she was duct tape
One day, after waking up surrounded by empty Pabst cans to the sound of my roommate screaming at his World of Warcraft guild, I walked over to my computer and saw that I'd had a few friend requests, which I accepted all of - at least the females (I was a shitty dude). By the time I finished my shower, shave, and breakfast of cold pizza I returned to my computer to a new message from Kate.
Kate was extremely attractive... in the exact opposite ways that I tend to prefer(ed). I liked extremely thin or chubby pale art majors with shitty attitudes, my age or older, black or colorful hair, dressed punk as fuck, and enjoyed going to basement punk shows & goth fetish nights. She wasn't thin or chubby - I think the kids today would call her thicc - with a giant ass on her relatively slim 5' frame. She was two years my junior. She regularly tanned, kept her hair in line with mainstream trends, was bubbly and cheerful. I had no idea why she wanted to talk to me (my initial thought was that I was going to be asked to stop corrupting one of her friends), but I didn't have to work until that evening, so I was game to talk.
Over the course of a few days, I'd learned that Kate was a bit deeper than her outward appearance. She'd initially found me via a local music community I owned, and we actually shared a good deal in common (at least in late teen/early 20s terms - music, movies, binge drinking, and hormones). Our conversation seemed to gel really nicely, and we'd decided to make plans to meet the following Friday night, she'd stay at a friend's house, then we'd go to a concert together the next night.
She lived in the dorms of a rural university about two hours from me and I was the big shot adult with my own (shared) apartment in the big city, so we decided that she'd come over and we'd "watch some movies," which was 2003 for "Netflix and Chill."
That Friday morning I woke up (likely again surrounded by Pabst cans) to a few Myspace messages from Kate from the middle of the night. They were obviously written while drunk, and while I don't have the memory to recite them verbatim, the gist of her concerns were that she was a virgin, that she was incredibly embarrassed about that, and was totally cool if I wanted to cancel our plans. I responded that I was really interested in meeting her (which was increasingly true - this girl had a quick wit) and that movies can just mean movies, and that I'd see her at 8. As a serial monogamist, I had a bit of a Grease fantasy rolling around in the back of my head... minus the L. Ron Hubbard.
I quickly cleaned my apartment, gave my roommate $50 to be somewhere else for the night, put on my best Myspace Scene Boy outfit and fast forwarded two thirds of the way through Fight Club, so I could appear to just casually be watching it when she'd arrive.
Fifteen minutes late, my doorbell rang and in walked Kate - as attractive as she appeared online and exactly as... normal? She wore a yellow flowered sundress, painted red lips, and had clearly tanned recently. She wore something vanilla, which I'd later find to be from Victoria's Secret. We made some small talk, where I learned she had a heavy southern accent - which was exotic and hot to me at the time. I showed her to my DVD collection and asked her to pick something out while I made us a drink.
Now up until this point, the majority of my dating history has been made up of punk rock girls from the city. They don't smell like vanilla, they smell like human. They're not stereotypically southern in their politeness or their colloquialisms... they'll spit and tell you to fuck off. They'll slam a PBR pounder faster than I can. What the fuck was I going to make for this delicate college girl? I dumped about half of a shot of vodka into some lemonade for her and made myself a tall glass of Jaegermeister.
I returned from my kitchen with our drinks she had chosen a movie (Don't Be a Menace to South Central While Drinking Your Juice in the Hood - which I consider to be my generation's Citizen Kane) and we settled in with our drinks to watch. About three minutes into the film, Kate takes a sip of her drink, then another.
"Well, it's obvious you're not trying to get me drunk and take advantage of me," she teased as she snatched my drink from my hand and slammed half of it down, pausing briefly to give me a look that said, "told you so," before downing the other half. I was impressed at both her drinking ability and her confidence. My dick strained against my jeans (which SUCKED if you were a dude who wore women's jeans), because while this girl wasn't traditionally my type, she was fun and she was hot.
And she was a virgin.
The thought ran through my head as she walked over to my refrigerator, my eyes glued to her legs and ass as she poured two shots of vodka and returned, handing me one and sitting on my lap, silently toasting a few times (until I got the point to join her), and we both downed our shots. From that point until we passed out drunk around 4am we made out to the point where my lips were swollen. I'd gotten handfuls of her ass and breasts, but all over clothes, and any suggestion about going further were politely shut down. Fuck it, I thought. Making out is fun.
I was pretty poor at the time and I slept on an air mattress, so any bit of movement could be pretty jarring. This had always been an issue when a partner would get up to use the restroom in the middle of the night. I wouldn't have thought much of it, if Kate weren't still laying next to me. I kept my eyes closed and listened for a few minutes and the sounds and movements next to me were unmistakable - Kate was masturbating in my bed while she thought I was sleeping.
I laid there, completely unsure what to do. Should I help her out? What if I'm misreading the situation? Why am I overthinking this? I should just pretend to sleep. These thoughts and more ran through my head when I felt Kate shudder hard, sigh heavily, and then go still.
"Good morning." I blurted out after what felt like an hour, but was more like a minute later, and Kate sat up quickly, looking at me. Her eyes went from startled to terrified as she realized that I knew what had just happened. Her tanned skin turned bright red as she tried to stammer through an explanation while desperately seeking her purse and making a rushed exit to get to her friend's house.
So, it's 8:30 in the morning, I'm still drunk from the night before, after making out for hours with this really hot girl with an exotic (to me) accent and a great ass, awakened by the sounds of that same girl masturbating with me laying mere inches away... and I didn't make a move.
Embarrassed by my complete lack of game and not wanting to make her feel any more embarrassed, I went back to sleep without calling her. I figured that I'd never see her again, and it would just have been a fun little weird story.
Fast forward to 8pm that night. I'm standing off to the side of the stage at a concert venue watching an opening band when I feel a tap on my shoulder. It's Kate, who takes me by the hand and pulls me over to a quieter part of the club, telling me that she'd like to talk about this morning. We find a quiet place and she's almost instantly standing on her toes, wrapping her arms around my neck, and kissing me passionately.
The rest of the concert is a bit of a blur... we left before the headliner finished their set and sat in her car making out. I'd noticed she was a bit more aggressive than the previous night, moving my hands to her breasts and ass, and rubbing my cock over my jeans. We decided that we should go back to my place.
During the 20 minute drive, she'd explained to me that she was indeed a virgin, though she'd wanted to lose it, and was simply waiting to make a decent enough connection with someone that it didn't feel wasted. I told her that I was happy just to make out all night again.
We got back to my place, and it was clear tonight was going to go differently. As soon as my bedroom door closed, she stripped down to her underwear and posed on my bed with her giant ass in the air, looking at me seductively and saying, "I was bad this morning, you should punish me."
At this point in my life, I'd had limited experience with dom/sub interactions, had no idea what I was doing, but I played along, playfully slapping her ass, which only seemed to frustrate her. "Harder" she exclaimed in an almost mocking tone. I slap her ass again, this time more forcefully, making a loud smacking noise and stinging my hand. She moaned, but still appeared dissatisfied.
She stood up and began looking around my room. I asked what she was looking for, and she told me to go make us drinks. I was happy to oblige. While in my kitchen, I heard Kate rummaging around my room, I assume looking for sex toys or my porn collection. I returned to her holding a roll of duct tape and a wooden ruler. I'm thoroughly confused and totally excited.
"Here are the rules," Kate said, as she took a gulp of the Jack & Coke I'd given her. "Under no circumstances are we having sex tonight. I want you to tape me up and I want you to touch me. I want you to spank me with this ruler, and I want you to leave marks."
Holy. Fucking. Shit.
She laid flat on my mattress. I started with her ankles. Knowing that we wouldn't be having sex, I took a length of the silver tape bound her ankles together. I places a few pillows under her stomach, elevating her ass. I stretched her arms over her head and bound them together at the wrists. I checked to ensure she was bound to her satisfaction. I walked over to my dresser and pulled out a sleeping mask that was left behind by an ex-girlfriend to function as a blindfold, placing it over her eyes. Then I grabbed the ruler.
I took my time with Kate. I'd start by running the ruler up the backs of her thighs lightly touching her ass or grazing her pussy over her underwear, building her anticipation (and mine). When my teasing had her squirming uncontrollably, I took the ruler and slapped her ass, hard. She squealed and I took a step back, thinking that I'd hit her too hard... for about two seconds when she started begging me for more.
I slapped the thick wooden ruler across her ass dozens of times, all the while it was still covered in her cotton panties. I ached to see the marks I was leaving. I stopped for a minute to get a glass of water and Kate begged me to un-tape her so that she could touch herself... I slapped her ass hard with the ruler.
"You got to touch yourself this morning... and you made yourself cum. You aren't allowed to cum again until I do," I said with a hint of frustration in my voice as I slapped her ass again... to which she responded, "please cum."
I removed the tape from her wrists and placed her on the floor on her knees, still blindfolded and bound at the ankles. I placed her hands behind her back and taped them together. At that point I stood in front of her and rubbed my cock, just inches from her lips. She'd stick out her tongue and I'd pull away. She'd lean in and I'd use my free hand to pull her away by her hair.
As I got closer to cumming, I wanted to see her face. I removed it to get a good look. Here was this completely normal girl, the type who usually doesn't notice that I exist, makeup smeared and ass bruised looking up at me and saying, "please cum on my tits."
That was it. I exploded from the base of my spine leaving ropes of cum all over her chest and neck, some hitting her in the chin. At that point, she looked like a cross between the girl next door and a depraved cumslut. As I untaped her hands, she collected my cum and rubbed it into her skin.