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Anal Roll Roulette

Before you can begin, choose some settings (click to activate, use before first roll):

Bad luck? Rerolls? Watersports? Oral tasks? Exposure? Achievements? Roll all now?

Getting into the mood

In order to get yourself ready, watch some inspirational videos... You should stay hard during the duration (30 min - 60 min) and you can play with your member, but don't you dare to cum! You should also insert a small to medium sized buttplug to prepare your hole, it is also recommended to insert the anal spreader after some time, to prepare your fuckhole as good as possible. Oh, if you try for a prostate orgasm, don't cum for 7 days prior to this roulette.

Category Subject Act Edge
Hardcore Amateur Gangbang 1 time
BDSM Virgin Anal 1 time
Fetish Ebony Creampie 2 times
Gay MILF Bondage 1 time
Taboo Teen Orgy 2 times
Femdom Big Tits Cowgirl 2 times
Weird BBW Blowjob 3 times
Lesbian Hentai Sex 2 times
Solo Asian Fingering 3 times
Sissy Latina Strapon 4 times

OR roll a pornstar

Ethnicity Age Cup Size Who
All 18-50+ All First from right (any row)
Asian 20-50+ A Second from right (any row)
Black 30-50+ B First two rows
All 40-50+ All First three rows
Indian 30-40 C First 10
Latin 20-30 D First 5
All 18-20 All First from left (any row)
Mid East 18-40 E Second from left (any row)
White 18-30 F First one
Pick one You choose Pick one You choose

Cleaning the behind

In order for this experiment to not be a dirty mess, get up now. Collect you enema equipment (or shower head) and some lube. Go into the bathroom (or bathtub), get comfortable and insert it. Let the warm water flow in until you feel full and after some time (couple of minutes), push it into the toilet. If you feel like it, you can repeat this step to get extra clean.


Lube up

Make sure to have some lube handy, you will need alot of it for the next tasks. Cover your index finger with a lot of lube and tease your hole. Slowly try to insert your finger and make sure to spread the lube. And if you intend to cum after this, you might want to collect two spoons of precum.


Starting small or opening up

One-Three Fingers means, in the first round, use one finger, then two and in the final round use three fingers (if you can, you can use more in the last round). (1x) means you have to do this task once, for the rolled duration and in the rolled position, (2x) means doing the task twice for the rolled duration each and in the rolled position.

Instruments: mini buttplug, small buttplug, glass dildo, finger

Instruction Duration Position
One Finger (1x) 2 min Doggy
One Finger (1x), mini/small buttplug (1x) 3 min Ass up, face down
One-two Fingers (2x), mini/small buttplug (1x) 4 min Laying on side
One-three Fingers (3x), mini/small buttplug (1x) 5 min On knees
One Finger (1x), mini/small buttplug (1x), glass dildo (1x) 6 min Sitting
One-two Fingers (2x), mini/small buttplug (1x), glass dildo (1x) 4 min Laying on side
One-three Fingers (3x), mini/small buttplug (2x), glass dildo (1x) 5 min Doggy
One-two Fingers (2x), mini/small buttplug (2x), glass dildo (1x) 6 min Ass up, face down
One-two Fingers (2x), mini/small buttplug (2x), glass dildo (2x) 7 min Sitting
One-three Fingers (3x), mini/small buttplug (3x), glass dildo (3x) 8 min You choose

Keeping the mood

After you played a little bit with your boypussy, it is important to stay in the mood. What should you watch during your anal adventure? Let me help you. Search for a compilation or a very long video. During that, do the tease tasks.

Subject Act Tease
Amateur Gangbang 200 light strokes
Virgin Anal Play with your frenulum
Ebony Blowjob Play with your frenulum, do another task
MILF Pounding 400 light strokes
Teen Hardcore Play with your penis head
BBW Facefuck Play with your penis head, do another task
Big tits Double penetration 600 light strokes
Hentai Spitroast With your hand make a ring, caress head
Asian Orgy Masturbate fast for 5 min
Latina Strapon Fuck fleshlight for 5 min

Working your way up

Try to insert the instrument as deep as possible, without creating too much discomfort.

Instruments: Anal beads 1, anal beads 2, realistic dildo, vibrator, medium buttplug

Instruction Duration Position
Anal beads 1 (1x), medium buttplug (1x), realistic dildo (1x) 4 min Doggy
Anal beads 2 (1x), vibrator (1x, medium), realistic dildo (1x) 5 min Ass up, face down
Medium buttplug (1x), vibrator (1x, medium), realistic dildo (1x) 6 min Laying on side
Anal beads 1 & 2 (1x), medium buttplug (1x), realistic dildo (1x) 7 min Doggy
Anal beads 1 & 2 (2x), realistic dildo (2x) 8 min Ass up, face down
Anal beads 1 & 2 (2x), medium buttplug (2x), vibrator (1x) 6 min Sitting
Anal beads 1 & 2 (2x), medium buttplug (1x), realistic dildo (2x) 7 min Cowgirl
Anal beads 1 & 2 (1x), medium buttplug (1x), vibrator (1x, high), realistic dildo (1x) 8 min Squad
Anal beads 1 & 2 (1x), medium buttplug (1x), vibrator (1x, medium), realistic dildo (2x) 9 min Cowgirl
Anal beads 1 & 2 (2x), medium buttplug (1x), vibrator (1x, high), realistic dildo (2x) 10 min You choose

Vibrations and edges

In this section you get the chance to use your vibrating toys and to edge a couple of times, to build up that yummy juice.

Instruments: Vibrating anal beads, vibrating glans stimulator

Instruction Thrusts Number of edges
Vibrating glans stimulator 50 Edge once
Vibrating anal beads (1x) 60 Edge once
Vibrating glans stimulator, Vibrating anal beads (1x) 70 Edge twice
Vibrating glans stimulator, Vibrating anal beads (1x) 80 Edge twice
Vibrating glans stimulator, Vibrating anal beads (2x) 90 Edge thrice
Vibrating glans stimulator, Vibrating anal beads (2x) 70 Edge four times
Vibrating glans stimulator, Vibrating anal beads (1x) 80 Edge four times
Vibrating glans stimulator, Vibrating anal beads (2x) 90 Edge six times
Vibrating glans stimulator, Vibrating anal beads (3x) 100 Edge eight times
Vibrating glans stimulator, Vibrating anal beads (3x) 120 Edge ten times

Challenging size

This part is very challenging and if you already had problems with Working your way up, then this chapter is not for you. Come back once you have trained your hole to accept bigger instruments. Really though, these instruments are huge. If you are up to the challenge, try first to insert just the tip and then work your way deeper inside.

Instruments: Huge black dildo, huge pink dildo, big buttplug, anal beads 3, big pink dildo

Instruction Duration Position
Big buttplug (1x), anal beads 3 (1x) 5 min Doggy
Big buttplug (1x), anal beads 3 (1x), big pink dildo (1x) 6 min Ass up, face down
Big buttplug (2x), anal beads 3 (1x), big pink dildo (1x) 7 min Laying on side
Big buttplug (2x), anal beads 3 (2x), big pink dildo (1x) 8 min Doggy
Big buttplug (2x), anal beads 3 (2x), big pink dildo (2x) 9 min Ass up, face down
Big buttplug (2x), anal beads 3 (2x), big pink dildo (1x), huge black dildo (1x) 7 min Sitting
Big buttplug (2x), anal beads 3 (2x), big pink dildo (2x), huge black dildo (1x) 8 min Cowgirl
Big buttplug (2x), anal beads 3 (2x), big pink dildo (1x), huge black dildo (1x), huge pink dildo (1x) 9 min Squad
Big buttplug (2x), anal beads 3 (2x), big pink dildo (2x), huge black dildo (1x), huge pink dildo (1x) 10 min Cowgirl
Big buttplug (2x), anal beads 3 (2x), big pink dildo (2x), huge black dildo (2x), huge pink dildo (2x) 11 min You choose

Reaching climax

If you want to cum the usual way, you first have to eat at least two spoons full of precum! Swirl the precum around in your mouth for 1 minute, gargle and then swallow it all! All the precum that leaks during this time, you have to eat as well before cumming. There is the option to come from anal only or another cum play section below if you love to play with your cum.

Ass play Cum
Nothing Just cum
Finger in ass On floor
Mini Buttplug In cup (reuse later)
Small buttplug In hands, use as lube and cum again
Vibrator (medium) Taste some
Medium buttplug On toy, lick clean (later)
Vibrator (high) On toy, fuck your ass with it
Big buttplug Cum in glass, snowball (swallow later)
Riding realistic dildo Cum into mouth, spit
Riding big pink dildo Cum into mouth, swallow (later)

OR (try to) cum from anal

Wow, nice you have chosen to cum from anal without stimulating your dick. First of all, make sure you are horny and hard for at least 2 hours, then edge once or twice. After that use the prostate massager and try to stimulate your prostate until your dick starts leaking or cumming.

More Cumplay

If you are still in the mood to play with that yummy semen of yours, you can do the tasks below. Choose whether to do them cummulatively or just one task. If you want to play with your cum but are not in the mood right now, just save it in a glass and come back in 15 min when you are horny again.

Cumplay
Cum is in a glass, swirl you tongue around in it
Cum is in a glass, swirl you tongue around in it, empty in mouth and then back in glass
Pour cum onto floor, lick it up
Pour cum onto dildo, fuck your ass with it, no swallowing for you
Gargle cum in mouth, scoop some out and rub over lips
Pour cum onto floor, lick it up, drool it back onto floor and lick it up again, then drool into glass
Pour into mouth, and swirl it around for 5 min before drinking it
Do the first task, pour into mouth, then swirl it around for 5 min before drinking it
Do the second task, pour into mouth, then swirl it around for 5 min before drinking it
Do three of the tasks above

Achievements?! Achievements!

You are an achievement-whore and therefore you want to try and complete all the challenges in this section.

Completed Name Description
achievement1 Look mom, I can gape! You can gape! Finally some fresh air.
achievement2 Two at a time! You can fit at least the realistic dildo and the vibrator in your ass at the same time!
achievement3 No way THAT is going in there! You can fist your hole! More than enough space here.
achievement4 Found the spot! You can finally come from prostate stimulation only.
achievement7 Sword Smith! You succesfully sharpened (edged) your tool at least 20 times.
achievement8 Still horny! Even after cumming you are horny enough to play with your semen.