Sandy's Story - Anal Sex

As you know if you've been following along, a lovely young couple, Sandy and Tom, have been receiving some coaching from me on how to get vanilla Tom to satisfy spanko Sandy's cravings. I knew from the start that Sandy was very anal erotic, and we had an exercise that included some OTK fingering of Sandy's bum by Tom. She took one finger ok, but had trouble with two. Nonetheless, Sandy still fantasizes about receiving rough anal sex from Tom.

After our last exercise, as told in Sandy's Story - Implements Exercise, I prefaced the instructions as follows.

You're almost ready for me to kick you out of the nest! But let's make sure Tom knows how to safely play with implements before then.

Then Sandy, at the end of her email recounting the outcome, wrote,

P.S. Tom and I do not want to be kicked out of the nest, though we understand if you have to. Can you give us another exercise? Maybe something around, oh gosh, bum fucking?

I published that post very soon after I received the email, finally catching up to the present. I thought I would tease Sandy a bit about the bum fucking. I deliberately made little comments, and posted some images/gifs/movies of rough bum fuckings tagging Sandy in my post Thoughts on Sexy Images. For example,

Speaking to Sandy here.
Is this what you really want from Tom young lady?
You'll look and act just like her, you know.

Some friends of the blog helped that along as well, such as Tanky who responded to small-dick-david recounting how he once bought a riding crop at a country tack shop.

The bridal range is much more affordable and varied than in inner-city stores as well, and most women prefer it to being held by the ears.

Sorry, bridle range! Damn auto-correct...

(That was a pun in case you missed it. He was talking about the product range of horse bridles available at a rural tack shop, and punned 'bridle' with 'bridal' deliberately - Sandy seemed to enjoy the two images Tanky immediately brought to her mind, and no doubt blushed at the marriage reference as well, seeing as how she and Tom are as yet unwed).

[By the way, Tanky recently posted a fun/odd story on his blog about me that is half-created by an AI! See A PERVERT ROBOT HELPED ME WRITE STRICY JULIE FANFIC!]

I kept the kids waiting for a while to make sure I could blog this one in "real time". Eventually, Sandy grew impatient and sent me a pleading sort of email:

Hi Julie,

Despite all your efforts to scare me off, I am still eager to try anal with Tom (and have it done by him a bit more dominantly).

We could obviously try it ourselves, but we both think we really need you to guide us through this process of taking my anal virginity.

Would you please? Pretty please. You can blog about it. We'll do it however you say.

Thank you,

Sandy (with Tom)

Isn't that the sweetest (and most desperate) sort of thing you've ever seen? How can I not? So let's see if we can't fully satisfy that greedy little asshole of yours, young lady 😈.

I decided how I wanted them to proceed and wrote up a long and detailed reply. It will be a difficult session for Sandy, but I know she's up to it.

In the below, some of the images I included in the email, and others I'm adding in now.

All right, guys, if that's what you want, Sandy...

Seriously, of course I was teasing. Anal sex can be almost completely pain free if you are properly prepared. And the preparation itself is half the kinky fun. Let's make sure we do that first, and discover your sensitivity. Later on, if you want it, Sandy, you can skip steps in the prep and make it a bit more "challenging" for yourself.

A little basic anatomy first.

The anus has two sets of muscles: the voluntary ones (the external anal sphincter) and the involuntary ones (the internal anal sphincter). They both have to relax. You can control the external ones (like when you're trying to hold it in, or trying to poop), but the internal ones have a mind of their own and need coaxing. But as long as the external ones are clenched, the internal ones won't release either. There's a lot of musculature there, and there's no way to safely pry it open. It needs to be coaxed.

Once you're passed the anal sphincter there's a big empty cavity. And then, maybe around 4" in, right at the very tip of a finger, there are more structures called the "transverse folds", or the "rectal valves".

They can squeeze the rectum shut to support the weight of the poop before it descends into the anal cavity at which point you really 'gotta go! These are purely involuntary muscles and need to be coaxed to relax as well. It's about 6" or so up to the sigmoid colon where it bends, but it's all pretty stretchy, so people do push past that but it may feel impossible, so don't push it.

Ok, onto the deeds.

First, we need to make sure you are very properly cleaned out. I want Tom to give you a good, embarrassing, enema.

Tom - enemas are very closely adjacent to the spanko kink, and are with Sandy. In some spanking novels, the girl is "punished" with an enema by her mother.

We'll make Sandy's enema a bit of a punishment.

Sandy, you need to acquire the necessary gear. Here's a picture and a link on amazon:

https://www.amazon.ca/dp/B08ZXV6DWV

If a similar thing is available at your local pharmacy, you should absolutely buy it there, Sandy, and checkout with your favourite lady. You need not say even a word. She'll know right away! Add a little tub of Vaseline as well and have some water-based lube handy.

You also need to acquire a set of training butt plugs. Here is one I found online with a link to give you the idea.

LINK

In this set, the smallest is only 1" wide at its widest, which should be tolerable to start.

If you could also get one with a vibrating function, you should get that also. Something like this:

LINK

The vibrations are great for loosening Sandy up even more prior to taking the penis.

Finally, it would also be useful to acquire a couple of penis-shaped dildos. One noticeably smaller than Tom, and one approximately the same size (not bigger).

It would be fun if you have a nearby sex shop you can go to and explain to the shop attendant exactly what you are up to and what you are looking for.

Ok, training day, let's get going kids!

Tom - pile a few pillows on the bathroom floor and put a big towel or two to cover them up. Sandy will be kneeling across those, supporting her own weight on her hands and knees, and may collapse a bit onto the pillows as she wishes.

First, Sandy, make sure you are as cleaned out behind there as possible using regular means.

Tom, fill the enema bag with a mixture of a mild, natural liquid soap (just a tiny squirt will do) and warm water. Give it a good shake. Close it off and attach the hose clamping it shut using the included clamp. Put the longer attachment on the end (the one with the multiple little holes). Hang it up nice and high using a bent wire hanger. Then unclamp it and let it flow into the tub or shower until it flows freely. Experiment with how much flow you get at various clamping settings. Clamp it shut again.

Sandy should strip and kneel across the pillows with her head low and her bum high.

Tom, coat Sandy's anal entrance and a little bit inside the hole with Vaseline.

Sometimes what comes out can be a bit burny ("ring of fire" sort of thing) and this will protect her. While you're at it, use one finger to loosen her up a bit as you did before. In and out. Rotations. Finger fucking.

Then coat the nozzle with the water-based lube. We don't want a lot of Vaseline on the nozzle as it will clog the little holes up. Insert it very gently all the way in. Don't force it any point. If there is resistance it's because it's misaligned. Experiment with different angles until it slides in freely.

Sometimes some "inadvertent" genital touching is unavoidable

Now unclamp it so it flows freely. At a certain point Sandy will cramp up a bit. Stop the flow completely and let it settle. You can rub her low belly gently, and also a little pussy play helps in my experience. Once it's settled down, let it flow again. Experiment with half-settings on the clamp, monitoring how full the bag is to make sure it's emptying. Stop it completely whenever Sandy asks and settle her down again. But try hard, Sandy, to take the full bag.

This is the same position you will be in, Sandy.
Nice and submissive.

Once it's all in, Tom, slowly remove the nozzle. Be careful as Sandy may spurt out her bum. Sandy, clamp yourself shut tightly. Tom, take the smallest butt plug, coat it with lube, and insert it into her bum.

Now, Sandy, stand up and hold the butt plug in with your hand. Tom, you need to be the enforcer here. Make sure Sandy holds it in for FIVE full minutes. This will be difficult for Sandy. Expect complaints and a little poopy dance in front of the toilet. Sandy, I need you to be submissive here. You may not go potty until Tom allows it. You will not be injured by this, despite the discomfort. Tom, you be the judge. Either five minutes or when the begging and crying and pleading becomes intolerable.

Then Sandy should sit on the toilet and release the enema. Expect it be very smelly and very disgusting! Sandy, make a few "courtesy flushes" along the way. Decide amongst yourselves if Tom should be present to watch (extra embarrassment and intimacy), or wait outside the bathroom. As you sit on the toilet, it will come dribbling out for quite some time.

When is mostly done, repeat the whole procedure twice more with warm water rinsing enemas. Tom, make sure all the soap is rinsed out of the enema bag. Also clean her bum and reapply Vaseline.

If the water coming out is clear at the end, you are done. If not, administer as many rinsing half-bag-enemas until it comes out clear.

Sandy will then need at least 30 minutes of recovery time lying on the bed with a towel under her (or an adult diaper or puppy pad if you want to go there).

Sandy may need a shower. And Tom, you should do a final soap and water cleaning of Sandy's anal-genital area.

That anus should be clean enough to eat off of now! Tom, if you ever wanted to try rimming Sandy with your tongue, now is the time (and highly encouraged to get her in the mood).

Let's now get into the stretching portion. Use lots of lube on Sandy's hole and the toy both, and insert the smallest plug. Once it's in there Sandy should clench and relax, clench and relax, around it to tire out those muscles. Leave it in for a good five minutes, then, Tom, give her a gentle little fucking with that plug, taking it all the way out and all the way back in again. Make sure there is always plenty of lube.

Patience is key here. Don't go on until Sandy wants to.

Then go on to the next size up plug and repeat it. It will be a bit tight getting the thickest part of the plug past the anal ring. Sandy, just breathe deeply, don't clench, and make like you're going potty. Nothing will come out as you are so clean up there. Let it sit in there a bit longer.

If the vibrating plug is the same or a bit bigger than the middle plug, use the vibrating plug now. Get it up in there and turn it up to max and just leave it there for 10 minutes or so.

Then do the largest butt plug and let it get comfortable inside of Sandy. Have Sandy gently sit on it to work it up deeper.

These butt plugs can be used for many exciting things going forward. Sometimes the plugs are used as punishment themselves. 

Tom, it's very embarrassing for a girl to be plugged like this as punishment. You can have Sandy do corner time while a plug is inserted. If she gives you any "lip", there's always the bigger plug. Or plug her, sit her down naked on a hard wooden stool with her feet off the ground, and have her write lines. Or maybe her punishment will be to step out with you for shopping, a movie, or a restaurant, while the plug is still inserted.

Once all that is done, use the smaller dildo and give her a fucking with it using your hand, Tom. Study the angle it goes in easiest. You will remember that later when you use your cock.

Then use the larger dildo that is Tom-sized. I think Sandy, by now, will be able to take it easily. Important psychologically, a real penis is way easier to take than a harder dildo of the same diameter. So if Sandy is taking this, taking the cock will be easy by comparison.

And remember Tom, Sandy is a spanko, so be a bit dominant throughout this whole thing, and Sandy you can beg and complain. But respect yellow and red safewords! A few spanks along the way will be welcome. If her butt is rosy or even red by the end, that's totally acceptable.

Time for the real thing!

Sandy, your job is to make sure Tom is rock hard for you. You do whatever it takes, girl.

I would recommend a spooning position for a first time. Most control for both of you. No accidental release of weight possible.

Tom, arrange Sandy at the right height (possibly using a pillow if needed). Then adjust her upper body and thighs to the correct anal entry angle relative to your cock that you studied earlier. Use your fingers and plenty of lube to re-loosen her ass. Two fingers now should be no problem. Then lube your cock liberally, and her anus, and line up your tip with her bumhole.

Sandy, reach back with your top hand and spread your cheek open, nice and wide. It's both a help to Tom, and also psychologically makes you a part of your own ass fucking.

A little gentle pressure, and a little wriggling from Sandy. And Sandy, you relax and make to go potty, and the tip will slip in. There we go. That's the hardest part done! Let it sit there for a bit.

Now, Tom, go in no more than an inch in and out at first. Sandy, you help by being an active participant and pushing back into Tom.

Gently work up until Tom is legitimately fucking you in the ass. Sandy, I think a little appreciation is called for now. Moan loudly and tell Tom very explicitly, with your words, how much you love his cock in your ass. Lie if you have to. The pleasure you are receiving is giving Tom the pleasure of fucking your hot, tight, little asshole. Tom, my husband tells me it's the best feeling fucking such a tight little hole on a willing and eager woman. Sandy, I rub myself with my fingers during an ass fucking and can get off. Try that if Tom allows it. Ask permission first.

Ideally, Tom should have a good, healthy, cum, deep up inside of your asshole, Sandy, to end it.

I DO NOT recommend oral right after an ass fucking. Obvious, possible health issues, but Sandy, you can show your appreciation by cleaning him off with a washcloth.

In future sessions, you can forgo the enemas, and the graduated stretching. However, I always appreciate a stretch with a toy or two before anal, even though I have had my bum fucked many times by now. We have also played with me taking it straight, without a pre-stretch, as a "punishment", but I find that very painful and intense. If it's a punishment scene, after a spanking Tom can plug you while you're still across his knee, and then stand you, plugged, for a few minutes in the corner. Then out comes the plug and in comes the cock for a doggy-style "punishment" fuck to "teach you your place".

We may be creating a monster here, Sandy. Once you've given your man license to take you like this, it might happen considerably more often than you are counting on. It did in my case! After a spanking, I am now often "taught my place" with an ass fucking.

Have fun, kids. Write me with any questions and definitely give us the usual blow-by-blow after all is said and done.

As soon as you respond with the "got it and will do" email, I'll post this immediately to see if readers have any additional suggestions or ideas for you. Let's make your first bum fucking a communal event, Sandy!

Good luck!

Julie

I received my reply back quickly from the kids.

Wow! Thank you so much, Julie. I knew we were right to wait on your wise counsel. Your step-by-step guide is going to be really helpful and takes all the guesswork out of it. It's a pretty exciting read, actually. It will take us a few days to gather everything up, and then this seems to be an almost full day Saturday activity. So very interested in any additional comments and suggestions from your readers in the meantime. Thank you in advance, everybody. Let's get me ass fucked.

Sandy and Tom

Finally caught right up. The kids are preparing this now. Any comments and suggestions, please let them know!