Page 10 of Roll For Initiative


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20 Minutes Prior

Ileave her in the bath, hoping the warm water helps sober her up. I couldn’t be in there anymore. The thought of her naked body just below the surface was wearing thin on my restraint. When I get to the front room, I can hear her phone going off in her bag.

*Ding* *Ding*

Another 2 messages, what the fuck. Who would be blowing up her phone at midnight. Hopefully, no one is dying. I grab her bag to check to make sure no one is actually dying. Her lock code has always been the same, 51999, Her favorite movie Star Wars Episode 1: Phantom menace came out on May 19th, 1999. She is such a nerd. Swiping down on the notifications there is a message from an unknown number. Fuck it, curiosity gets the better of me.

Unknown Number-*hey it’s Alec. From the bar. *

Unknown Number-*I really enjoyed talking to you tonight. You are absolutely stunning, sweet, funny, and to top it off, you're a nerd. You are literally the perfect woman. ^_^*

Unknown Number-*I can’t stop thinking about you. Are you free Friday night? Maybe dinner and a movie? I hear they are playing some older movies at the skylight theater. Might be fun. *

Fuck off, Alec. I know it’s wrong, but I can’t stand by and watch her get involved with this fucker.

-Blocked- Delete Number - Empty deleted texts folder-

There, it’s like he never existed. No harm, no foul. She will think he blew her off and all will be fine. A little possessive of me, but oh well. I need to figure out what I want, though. I set her phone down on the coffee table and debated what to do.

Fuck it. I think I’m just going to crash for a few hours, then I’ll Uber home, or maybe she can give me a ride home in the morning. She is probably just going to crawl into bed after her bath anyway, so I might as well get comfortable. I slide off my jeans and socks; I can’t sleep in jeans; it is so uncomfortable. I relax on the couch, laying my head on the armrest. I decide against my better judgement to pick back up her phone. I’m curious about what kind of apps she has here. Sure, that’s my only reasoning, I try to convince myself.

5E, Tinder, TikTok, Discord, D&D Beyond, KNKI... What the fuck is KNKI? I open the app, and I am completely stunned. It’s a sex app. Well, kind of. It seems like it is basically kinkier tinder. Makes sense with the name. Cassie must have downloaded this by mistake. I click “My Profile” and there in a black lace corset and a matching thong and garters is Cassie. Female, 24, Sexual Partner Preference: Open. What. The. Fuck. This is not the same Cassie I have known for the last 15 years. Cassie blushed at blow job jokes and waited till 18 to lose her virginity. Hell, the girl still dresses like she is stuck in high school. She is not the same as this black lace and leather Goddess spread out on the screen in front of me. I’m dumbfounded.

My mind goes back to earlier. She said Sir more than once, and she was so obedient in her room when I told her to sit up. She sat like a true sub, hands folded on her lap and everything. There is no way! Is she a submissive? There is a tab for Assessment Results. Assessment? What kind of assessment.

These results are based on your answers to our personal assessment. Please do not treat these answers as finite, but more as pathways for you to explore. Please, do more research into the different categories that align with your personality type. Be sure to use safe words and have fun.

I click on her results. Submissive/ Brat. I knew it! I have always known she was a brat, but I guess she is also a sub, based on her answers. I find this interesting, and apparently so does my cock because he is stirring to life again at the thought of Cassie in that corset and thong in the photo. I go back to her profile and snoop through it more. Below her interests, she has bondage, impact play, roll playing, gags, harnesses, clamps, worship, Dom/Sub, degradation, whips, group play, and CNC. Jesus Christ, she is into a lot of the same shit I am. I can’t stop myself as I start snooping through her phone more.

Immediately I go to her gallery. If that was her profile photo, what other stuff does she have photos of? I scroll through her albums, there are tons. So many memories of us through the years are flying across the screen. Some memories I had completely forgotten about. For example, in the summer after 9th grade, Cassie had just gotten her braces off, and we went to a carnival. She got a caramel apple because she hadn’t had anything with caramel in over 5 years. Her mother would never allow her to have something that would damage the braces. Cassie’s mom has always been about appearances. Even though Cassie’s teeth weren’t bad, her mother insisted on her having them to make her teeth perfectly straight. When she sunk her teeth into that caramel apple she had the biggest grin on her face. The pic she has is a selfie of us each holding a caramel apple and clashing the apples together. God, I miss being a stupid teen, we always had fun, and we were always together.

Scrolling down further, I see a black square thumbnail for an album named “X.” Hmm, I wonder what this could be. Iclick it, but it is password protected. I try her lock screen code. Incorrect. Hmm. 6969? Bingo! Opening the album, my breath is completely lost. There are so many photos. Who is this woman, she looks like Cassie, but it’s like it is a completely different person. She radiates such confidence in her photos. She may be submissive, but her eyes exude power. God she is beautiful. Why hasn’t she ever shown this side of her. Could this be what she meant when she changed since Mark broke her heart. There’s no way she has hidden this side of her from me for long.

As I keep scrolling I come across a pic of her, it looks like it was taken by someone or maybe using a tripod. It is stunning. Black and white, she is on her knees in a leather harness, barely covering her nipples and a thong with knee high boots. Her arms are bound behind her using the diamond arm binder technique. Her partner must be skilled in Shibari because that tie is very tricky, I had tried and failed a lot before I perfected my technique. I am almost so entranced by the photo that I almost forget there is a male sitting in front of her. You can’t see his face, only his body. He is reaching down and cupping her chin. The look she is giving him is pure lust. It makes my jaw clench and tick with frustration. I move past the photo, needing to see what else this X album holds.

Flipping through the album is like having access to my own private Cassie porno magazine. She has taken photos in so many different positions, with different toys. Everything about her is sexy as fuck right now and it is only making me harder. I start to palm my hard cock over top of my boxers, maybe I’ll just quickly take care of this before I go to sleep. I stop for a moment, needing to make sure I don’t hear her coming out here. The apartment is dead silent, she must already be asleep. I close down all the apps I opened and put the phone back on the coffee table just in case she does come out here. The mental images that are burned into my memory are all I need.

I pull my shirt up a bit, then reach into my boxers, gripping my hardening length in slow firm strokes. I close my eyes and start thinking of all the photos I seen tonight, and all I learned about my sweet, not so innocent anymore, Cassie. My mind slips into another fantasy involving her. This time though, we are in one of the rooms at FoxDen.

We are in one of the main VIP rooms, the one with my favorite device, the St. Andrews Cross. She is dressed in the corset, thong, and garters from that profile pic. I press her up against the cross, taking my time to attach each wrist lock firmly in place. After each wrist, I trail kisses down her arm and across her chest. I can practically hear the sounds of her panting from how turned on she is getting.

I can’t help the moan that slips past my lips thinking of this. This is now twice in the last 12 hours I have masturbated to the thought of Cassie. Never before has she consumed my mind like she has now.

I capture her mouth with mine, pressing myself between her unshackled legs. Pushing my growing erection against her. I can picture her moaning, silenced as my tongue tangles with hers. I suck her tongue into my mouth and bite, not hard enough to draw blood, but hard enough to cause her to whimper. I begin to kiss down her neck, nipping her sensitive skin and causing goosebumps to ripple across her entire body.

I start to thrust my hips with each stroke, coaxing my cock closer and closer to release.

I trail the kisses down over her warm breasts, gripping them tight as I take her swollen nipple into my mouth. Teasing it in circles with my tongue. She arches her back, pressing her nipple harder against my tongue. I lean away, just enough to strike her across the tit. Her beautiful pale skin starts to turn crimson. The moan she lets out is delicious and has my cock twitching. My good girl loves pain.

I start to stroke my cock faster. My breathing is becoming more rapid.

I kiss her down her stomach and then kneel before her. I sink my teeth into the soft flesh of her hip. She moans my name. I lift each of her thighs over my shoulders, lifting her off the ground. I lock eyes with her as I trail my tongue up her inner thigh. Her eyes shine with desire. I know exactly what she wants. The scent of her arousal wraps around me. I rip her panties off in one quick motion then crash my mouth against her warm pussy. Licking and sucking like a man starved for days. She bucks her hips, fucking my face. “Such a good girl, take your pleasure. Ride my face like you would ride my cock.”

Another moan slips past my lips. I pause for a moment. I still haven’t heard the door open, but I could have sworn I just heard a moan. It must be my imagination. These boxer shorts are too restraining, so I pull them down slightly, releasing my cock. I begin to stroke it faster, picking up speed as I thrust my hips.

I tease her clit with my tongue and pinch it between my teeth. Sending a full shutter through her body. Her thighs clench my head. If I had to choose a way to die, it would be between her thighs as she rode my face, chasing her orgasm. I slip my middle and pointer finger into her pussy. Thrusting them in and out of her wet cunt while I nibble on her sensitive clit.

I’m so close; my whole body is starting to tense.