The Anal Prober

About 6 weeks ago, I ordered this. A nice little jelly toy that was specifically meant for playing with one’s anus. I didn’t fancy running the risk of “stuffus interruptus” (as coined by Cherrie) and this toy is rather unlikely to become a permanent resident in my colon as I doubt I could ever stretch my anus to get the rather wide middle section in me (nor do I wish to stretch my anus that wide).

When I first got it, the first thing I did was to size it up, the beaded end seemed inviting enough, the first bead was only as wide as my fingertip and it got a little wider. The other end, I thought it would be a good while before I got that end inserted in my ass as it seemed rather large to me!

So come the first night I decided to play with the toy. I’m undressed, resting on my comfy bed with a towel underneath me, my legs bent with my feet on the floor as I lay on my back. I grab some lube and dispense a few drops onto my fingertip so I can gently rub my asshole. Getting more lube, I lube up my index finger of my left hand and continue to rub my asshole before slowly pressing it against the sphincter and it progressively lets me in. Slowly stroking my finger in my ass for a little while before trying two fingers in my ass.. uhh.. nope my asshole wasn’t up to it, only one finger it is….

Out comes the Anal Prober, heavy with the scent of jelly toys as I hold it by the wider end, and squirt some lube over the beads, spreading it around with my finger as I brace myself for some proper penetration. The first bead practically slipped in without me noticing.. same goes for the 2nd bead. I only noticed the 3rd and 4th bead gently stretching my ass hole as I moved the prober gently back and forth in my bum. Thinking about topspeedloader’s comment, I resisted the temptation to jerk myself off but I wasn’t really getting anywhere and I fell asleep a little frustrated.. (though not with the toy in my ass)

That being said, I have fallen asleep with the toy in my ass quite deliberately and I did manage to get the wider end of the prober inside me, and it does feel nice, and when you push it in deep, it feels hot as my asshole gets stretched as it rides up on the extremely thick middle section, and it feels cool as you withdraw it. I didn’t manage to find the pleasure I was seeking until a few weeks ago.. when I was chatting with my ‘Kindred Spirit’. Some of the details have been altered along with her name and I’ve got her permission to publish this here. The conversation is after the jump.

Sweet Chilli: do you get turned on by FF, MFM, FMF, MM etc?
Kyma: the first three, oh definitely…
Sweet Chilli: not MM then
Kyma: nope… not wired that way.
Sweet Chilli: you don’t have to be gay – FF gets me horny but I am definitely not lesbian
Sweet Chilli: Just the fact that another woman completely understands what to do
Kyma: still don’t find MM arousing…
Sweet Chilli: She knows what she likes and how it feels
Sweet Chilli: ok
Kyma: even though I have the inclination to stick things up my bum
Sweet Chilli: done any of that recently?
Kyma: nope.
Sweet Chilli: I’ve got an FF scenario stuck in my head..
Kyma: ooooh….
Sweet Chilli: With ****’s girl, and him watching
Kyma:
Sweet Chilli: My hard nipples brushing against hers
Sweet Chilli: Gently kissing each other
Sweet Chilli: Lightly flicking her nipple with my tongue
Sweet Chilli: Sucking it
Kyma: mmmmm
Sweet Chilli: Her nipple getting harder
Sweet Chilli: She’s moved her hand to my ass
Sweet Chilli: She’s caressing me
Sweet Chilli: I begin to massage her other breast
Sweet Chilli: We can feel the tension heightening
Sweet Chilli: I feel myself slowly dripping
Sweet Chilli: Still sucking her breast
Sweet Chilli: She tentatively moves her hand from my ass to my pussy lips
Kyma: oooh, you’re making me feel wet now….
Sweet Chilli: stroking my lips from back to front
Sweet Chilli: I gasp at the pleasure
Sweet Chilli: Her touch so soft and gentle, she knows exactly what to do
Sweet Chilli: She pulls away from me, looks me in the eyes and begins to move down my body
Sweet Chilli: Holding my gaze she licks my stomach
Sweet Chilli: then trails her tongue further down
Sweet Chilli: Still looking me deep in the eyes
Sweet Chilli: until she reaches my swollen and engorged clit
Sweet Chilli: She gently flicks it with her tongue
Sweet Chilli: A sigh of pleasure escapes my mouth
Sweet Chilli: She begins to lick and suck, whilst stroking my inner thighs
Kyma: mmmmm
Sweet Chilli: I begin to sigh and moan at the sheer pleasure she is inflicting upon me
Sweet Chilli: Oh so slowly she strokes from my thigh to my pussy lips
Sweet Chilli: A gentle touch sending chill down my spine
Sweet Chilli: All the while sucking at my clit with determined fervour
Sweet Chilli: Slowly she inserts a finger into my wetness
Sweet Chilli: Slicking up my nectar and covering my pussy
Sweet Chilli: She puts her finger to her mouth and licks my honey from it
Sweet Chilli: Tasting me, she sighs
Sweet Chilli: With one swift movement she moves her tongue and licks my hole
Sweet Chilli: Drinking me up
Sweet Chilli: She inserts her tongue into me
Sweet Chilli: I loud moan escapes my mouth
Sweet Chilli: She starts to stroke herself while seeking out my spot with her tongue
Kyma: oooooh
Sweet Chilli: The wriggling and to-ing and fro-ing of her tongue bringing me ever closer to cumming
Sweet Chilli: She finds the elusive spot and massages it with a force
Sweet Chilli: She rubs my clit with one hand and finger fucks herself with the other
Sweet Chilli: I begin to massage my breasts and pull at my nipples
Sweet Chilli: Both of us are so close to cumming
Sweet Chilli: Our stroking, licking, massaging and moaning all in synchronicity
Sweet Chilli: Soon we are both cumming with a force
Sweet Chilli: Echoing each others cries of pleasure
Kyma: mmmmmmm
Sweet Chilli: As I cum I gush into her hungry mouth
Sweet Chilli: Her own wetness dripping to the floor
Sweet Chilli: As we come down from the high of orgasm we kiss and stroke each other
Sweet Chilli: Stroke of the cheek, flicking of tongues
Sweet Chilli: Lick of the breast, nibbling of the neck
Sweet Chilli: Our legs locked tightly together so our pussies are touching
Sweet Chilli: We rock against each other rubbing our clits
Kyma: mmmmmm… I can’t help but touch myself as you tell me this, my tip sooo wet…
Sweet Chilli: Kissing and fondling in our post-cum bliss
Sweet Chilli: Was that hot enough for you?
Kyma: that was very very hot…
Kyma: much better than the few lesbian/girl on girl scenes I’ve seen
Kyma: I’m so aroused I want to put the anal prober in my ass…
Sweet Chilli: I didn’t even put much effort in! I thought you’d think it was amateurish
Sweet Chilli: Oh please do that
Sweet Chilli: We can try and make you cum with it
Kyma: oh perhaps even better, we start with the anal prober and then maybe a bit later on, we try and get the Aneros in me…
Sweet Chilli: oh yes
Kyma: oh okay… I’ll be back in a bit.. need to prep myself before I get the toys and lube out.
Sweet Chilli: sure
Kyma: back…
Sweet Chilli: you still nice and hard?
Sweet Chilli: ass primed?
Kyma: kind of lost the hardness (easily fixed)… just lubing my hole
Sweet Chilli: Just think of me and a girl getting deep down and dirrrrrty!
Kyma: mmmmmm
Sweet Chilli: so how do you wanna do this?
Kyma: just gonna shoot a little bit of lube up my hole and then lube the prober and insert the wider end in me and we’ll take it from there… (ass has already been fingered)
Sweet Chilli: okely dokely
Kyma: just shot the lube up…
Kyma: covering the wider end with lots of lube
Sweet Chilli: ok
Kyma: here we go…
Sweet Chilli: easing it in gently?
Kyma: uh huh
Sweet Chilli: stroke yourself at the same time – get completely relaxed
Kyma: it’s in…
Sweet Chilli: how does it feel?
Kyma: hard to describe
Kyma: I just feel it within
Kyma: not stroking my ass yet
Sweet Chilli: I’ll help you
Kyma: okies
Sweet Chilli: I’d like to be pleasured by two guys at the same time
Kyma: all their attention on you
Sweet Chilli: yeah, completely, undivided, their sole purpose to make me cum over and over and over…
Kyma: mmmm
Kyma: (I’m slowly stroking my cock and ass)
Sweet Chilli: mmm
Sweet Chilli: One guy would be fucking me hard from behind
Sweet Chilli: The other sucking my clit
Kyma: and fondling your breasts
Sweet Chilli: yeah, pulling my nipples into hard points
Sweet Chilli: my breasts becoming full
Kyma: mmmmmmm
Sweet Chilli: How is it feeling?
Kyma: nicer
Sweet Chilli: My full leaden breasts be licked and sucked
Sweet Chilli: My throbbing engorged clit being sucked
Sweet Chilli: Then a finger in my pussy
Sweet Chilli: Then another
Sweet Chilli: in
Sweet Chilli: out
Sweet Chilli: in
Sweet Chilli: out
Sweet Chilli: in
Sweet Chilli: out
Sweet Chilli: lick
Sweet Chilli: suck
Sweet Chilli: lick
Sweet Chilli: suck
Kyma: mmmmm
Sweet Chilli: three fingers now…
Sweet Chilli: Pussy juices soaking his hand and my thighs
<interlude>
Sweet Chilli: hey, you know I wanna try a vibrator? Well, I got a new phone so today I used the vibrate on the old one…
Kyma: mmmmmm
Sweet Chilli: Against my clit
Sweet Chilli: It was great
Sweet Chilli: Vibration in my clit and finger fucking myself – soooo good!
Kyma: mmmmmmmmmmmm
Kyma: you need a little finger vibe
Sweet Chilli: There is an Ann Summers near me…might get one tomorrow…
Kyma: good idea
Sweet Chilli: oh I just remembered…they installed “fun” vending machines in the loos at a bar I go to.
Sweet Chilli: they sell finger vibes…
Kyma: lol
Sweet Chilli: and rubber cocks
Kyma:
Sweet Chilli: anyway, that is a diversion…how is your cock?
Kyma: those toys must be manna from heaven for a horny girl like you
Kyma: hard…… nice and hard
Sweet Chilli: having pleasurable feelings?
Kyma: mmmm yes, but still need your help
Sweet Chilli: I have gone blank – fuck!
Kyma: touch me….
Sweet Chilli: I’d rather touch myself! – I’m feeling greedy today!
Sweet Chilli: Ok I know…
Sweet Chilli: I’ve bought a vibe..
Sweet Chilli: I’m teasing my clit with it
Kyma: mmmmmm
Sweet Chilli: Slicking the vibe in my kitten honey
Sweet Chilli: The vibrations coursing through my pussy…
Kyma: I’ve just cum….
Kyma: mmmmmm
Sweet Chilli: YES!!!!!!!
Sweet Chilli: Wooopeee!
Sweet Chilli: how is your ass?
Kyma: mmmmm
Sweet Chilli: Is this better than other times you’ve tried?
Kyma: oh yes.. it was different too….
Kyma: at first, some clear fluid leaked from my cock.. then some cum.. and then I spurted.. It felt soo good
Sweet Chilli: oh wow! sounds good (for you – still not my thing)
Kyma: