A quiet room. A relaxing bath beforehand. Lube. More lube. Maybe a finger first. Is today the day? Two fingers. Now three. Yes, this might happen today.
Put a towel down. Get it out of the box. Put it next to you, in sight at all times.
Three still easing in. You grab a toy. Nothing special. six inches, fairly fat. the kind of thing you could risk being found without too much embarrassment. The kind of dildo your aunty has. Or your mum. Or your boss.
Sick with lube, it slides up easily. Meh. Vanilla.
After a few minutes, you crawl over to your box of 'special stuff', little dildo still poking out, and break- out the big guns
First a big plug. placing it on the floor, you squat over it, letting just the end push into your anus at first. Then more. Then more. At it's widest the plug is 4 inches in diameter. After seven agonising minutes, and maybe a little too much clit rubbing, you feel your ass close over the edge of the cone.
You lean forward on all fours, and admire yourself in the mirror. Pushing hard, you eject the plug. Your anus gapes a little, leaks a little blob of lube, then slowly closes back up.
You look across at your latest purchase. No, not yet. Savour the anticipation.
Next you reach for a big dildo. Shaped like a cock, but really thick, with a 12" shaft and huge balls, this is always a challenge to relish. You smear the head, under the glans and the shaft with lube, put the base on the towel, kneel down, and sit back. The girth is not as much as the buttplug, but this is long. Really long. slowly, agonisingly, you sit further and further back. every so often sliding forward again to ease the pressure in your bowel, feeling the shaft drag slightly as it comes back out.
After what feels like hours, you have worked the whole thing up yourself, and your buttocks are resting on the big plastic balls. Gripping the base between your feet, you lean forward, slowly letting the entire length slip out of your ass. With a sloppy 'pop' the glans exits, along with a little trapped air.
A sip of red wine from the glass you poured earlier, perhaps to steady your nerves. You look at your new idol. Yes, now it is time. You have already stretched as far as you can usually, but now it's time to take the next step. You grab a handful of lube and ease it up and around your anus, your fingers and even your whole hand easily passing your anus as you stare lustfully at it, almost salivating.
It is frankly massive. The head alone is bigger than the plug from earlier, and then there are all manner of lumps and bumps to stretch you in all kinds of ways. You lube it up, and notice how the lube collects in certain places.
Again, you place the base on the towel, and holding onto the windowsill, you squat onto the tip of it. You are quickly at your limit. You sit back a little more, all of your weight bearing down on the acorn- shaped head.
You cannot go any wider. the stretch is overwhelming, you feel like you are going to split. You frantically rub at your clit, you need to orgasm more than ever. the feeling builds, then all too soon you come.
Lying on your side on the towel, surrounded by the musky smell of your sweat, lubricant and ass, you close your eyes and concentrate on the burning between your cheeks, and vow to not be beaten next time.