I’m quite fond of the njoy line of steel sex toys, but they are certainly not cheap; $120 for a butt plug.
https://shop.njoytoys.com/products/pure-plug-2

If you’re looking for a less expensive option, Williams Sonoma has you covered; $29.95, including an optional “BDSM mode”.
https://www.williams-sonoma.com/products/reversible-meat-tenderizer/

“Tenderizer” indeed.

Like most women I know, my girlfriend’s prior experiences with anal sex were loathsome. There was no prior discussion or negotiation, and when it happened there was a great deal of difficulty and pain. The result was a resolve of “Nope, not for me. Never again.” that lasted for years.

When I raised the topic some months ago, S was very frank about her past experience and the overwhelmingly negative impressions it had left. Given how much trust she had in our relationship and the successes of our on-going sexual explorations, she wasn’t completely closed to the idea, but she was open about her apprehension and skepticism.

With her explicit permission, I began a very gradual process of simple, classical conditioning. I’m going to describe that in some graphic, and not always sexy, detail.

In the beginning, I just wanted to make her aware of her asshole, in the context of actions she already enjoyed. For instance, while I was going down on her, I would simply rest an oiled finger on her puckered sphincter. There was no attempt to penetrate, in fact there was only the very lightest of stroking. I just wanted her to be aware of her asshole while I was licking her pussy and bringing her to orgasm. This was a sporadic and occasional association for some weeks, but gradually became more of a regular thing; while giving her head I would lightly pet her asshole.

Once she seemed fully at ease with that pairing, and even enjoying it, I raised the stakes. After a particularly vigorous bout of pussy licking, once she was completely aroused and engaged, after several orgasms already, I asked her to roll over onto her belly. I pushed one arm under her and started stroking her engorged clit with my fingers, swiftly bringing her back to the brink of orgasm. When she was right on the cusp, I started gently lapping at her asshole with my tongue. She stiffened with surprise, I increased the speed and pressure of my fingers slightly, and she came quite loudly and enthusiastically. I reinforced that association several times, bringing her to orgasm with my fingers while my tongue licked and swirled against her sphincter.

Again, licking S’s asshole while fingering her clit and pussy was an occasional thing at first. Over the course of some weeks, it gradually became a more regular part of our sexual repertoire. Additionally, I became a little more vigorous with my tongue, licking her asshole more firmly, and even worming the tip of my tongue just a tiny bit into her sphincter.

Over time, it became quite apparent that S was deeply enjoying having her asshole licked. I began to experiment with stroking her clit and fingering her pussy a little less, keeping her just below the threshold of orgasm, and then using the licking of her sphincter as the tiny bit of additional stimulation that would push her over the edge of climax. That worked better and better over some time. The day finally came when I rolled S onto her belly and started licking her asshole intently, with no other stimulation whatsoever. It took a little time, but she finally reached a frantic orgasm from no other stimulation than having my tongue on her ass.

From there, things accelerated a bit. I started giving S head by having her sit on my face, with the tip of my pinky finger on her asshole, as I licked and sucked at her clit and labia. Slowly, with a lot of lube, I started sliding my finger inside her ass. I listened carefully for sounds of discomfort, pulled back when needed, and focused on making sure she was cumming so much from the cunnilingus that she wasn’t too distracted by what was happening to her ass. I probably didn’t get more than the first knuckle of my pinky inside her the first time, and that was just fine. Over the course of weeks, that position became a more common activity, very slowly working my finger a little deeper, and gradually moving to larger fingers. As with having her sphincter licked, eventually having her asshole fingered became a source of pleasure for her, all by itself.

From there, it was only a matter of time before we were both in the right headspace to try putting my cock in her asshole. I’ll tell that story in a little more detail later, but first stop here and stress some of the major guidelines of all this:

– Consent: Embarking on this journey was explicitly discussed and freely agreed to. There was a tremendous amount of trust involved and my primary goal all along was to make sure S never had a reason to regret that trust.

– Association: I always started with an activity S already greatly enjoyed and looked for ways to add very small forms of anal stimulation to that activity. Gradually, she began to associate the anal play with the pleasure she was experiencing. Over time, the repeated reinforcements of that association meant the anal play was pleasurable on its own, without the associated pussy play.

– Patience: This process happened over a span of six months or more. It was very important to me that every step of the journey be enjoyable and pleasurable, so that S would be enthusiastic about continuing. I let S’s reactions guide how fast and how far we progressed, focusing on being patient. The last thing I wanted was to push too hard too fast and cause a negative reaction, undoing all of the previous progress. I stayed intent on simply enjoying where we were at any given moment, being ready to back off at the first sign of discomfort.

– Hygiene: We take some very simple precautions. Make sure our recent diet is respectable, with a minimum of greasy foods. If there’s been a bowel movement since her last shower, maybe it’s time to shower again. Don’t be shy about using plenty of hot water and a soapy wash cloth to wipe at the sphincter. That minimum amount of preparation has worked fine for us; I’ve never felt like an enema was a necessary part of the process. Mostly, I refuse to worry about it. If I’m doing it right, sex is messy; I regularly end up smeared with spit, cum, lube, and pussy juice. I just don’t obsess over it; I’m too busy having fun. Thus far, there have been no messy accidents that have led me to regret those guidelines.

That has been our process, and it has worked very well. No doubt, a lot of that has less to do with the process and more to do with my extraordinary partner.

My first serious experiences with BDSM were with a former partner, M. A couple of years into the relationship, I bound her arms over her head (standing) and engaged in some sensation play, tickling, and mild spanking. Although it seemed to go well for awhile, she soon had a major meltdown, scene over, lots of aftercare. The experience pushed enough major buttons with her that we avoided that territory assiduously for a great many years after.

Over a decade later (I tend towards pretty long-term relationships), M and I made plans to go to Burning Man as part of a sex-positive theme camp we recalled from our previous Burn. Apparently we only vaguely, sorta, kinda remembered the camp, because “sex-positive” was too vague by half. Once we arrived on playa and started assisting with erecting the camp (phrasing!), we discovered that the camp founders described the camp as “the biggest, baddest BDSM play space on playa”. Both of us worked shifts as “Dungeon Monitors”, helping supervise the public play space. I also attended a “make your own flogger” class on playa and came away with my very first flogger.

Those experiences brought the topic back to the table for M and me, and we explored it with cautious enthusiasm. I was a tentative top, M was my bottom. There was some role playing, bondage, sensation play, spanking (bare handed and with a strap), flogging, anal play, and dominance/submission.

The play was enjoyable and rewarding, but it was also complicated. I didn’t know it at the time, but the relationship with M was on its last legs; she left our home and the relationship three months after that Burn, and hasn’t spoken to me in over two years. So our renewed explorations of BDSM happened in the context of some relationship strife, communication challenges, and more emotional turmoil than usual. Additionally, M and I were both strong believers in a guideline regarding open relationships, “Don’t embark on this journey when your relationship isn’t already pretty solid. Trying this isn’t going to fix your relationship, and in fact might hasten an already-looming demise.”

As such, experimenting with BDSM was something M and I did only when the conditions were just right. She had to be in the right mood, I had to be in the right mood, there couldn’t be any overt drama or communication issues hanging in the air, we had to have a serious chunk of free time available for the scene and ample aftercare. It felt like the stars had to be aligned just so before we were willing to “go there”, and the conditions were unfavorable far more often than they were favorable.

Of course, the picture was further clouded by how new we both were in this space. I was a tentative top, still getting my bearings in this landscape. M was an anxious bottom who really struggled with trusting and letting go. It was a challenging learning process. Then the relationship crumbled to pieces from under me. I have speculated more than once about whether our foray into BDSM contributed straw to our camel’s over-burdened back. Given the lack of subsequent communication between us, I can’t really say.

Regardless, the experience reinforced my belief that BDSM was only viable in the context of a rock-solid relationship, between people who were (separately and together) in a very secure emotional landscape. That belief was soon challenged. Look for Part 2 of this story.

As is obvious from my previous post, S and I have been exploring anal play a bit more. This is something I’ve enjoyed with a few previous partners, but only very occasionally. S’ past experiences receiving anal have been pretty dreadful, so we’re moving slowly, carefully, and trying to build a wealth of positive associations for her before getting too ambitious.

There’s a school of thought out there that says if you expect something from your partner, you better be willing to go there yourself. More specifically, if you’re all hot and bothered to have your partner take something up their ass, it’s only fair that you be willing to do the same. “Don’t dish it out if you can’t take it.”

My personal belief is that this is more of a general guideline, rather than a hard-and-fast rule. Trying too hard to maintain a strict symmetry in relationships can backfire. Sometimes a person only likes one end of the equation, not the other, and as long as both partners are consenting and cool with that, no harm, no foul.

But, you know me; I’m in this to learn, to experience new things, to broaden my horizons. I really do want to know more about receiving anal play, so that I can be better, more informed, more considerate about how to give anal pleasure to someone else. Besides, the prostate, right?! Men have this enormous erogenous zone in their ass; how sad would it be to ignore that and the pleasure it might be able to provide?

So, there has been some fooling around with my ass lately. For a while now, I’ve known I like having my perineum stimulated. And if I’m feeling relaxed, confidently clean, and very comfortable with my partner, I enjoy getting rimmed. But I haven’t had a lot of experience being penetrated. I’ve fooled around with an Aneros prostate toy and haven’t gotten much out of it. I have an ex- with extensive medical training, and she attempted to stimulate my prostate a couple of times, with a fair bit of confusion and no fireworks. Bummer. (No pun intended.)

By contrast, S has a fair bit of experience playing with the ass of previous partners, and feels very confident in playing with the prostate. She and I have tried that a couple of times, with some minor success, but nothing earth shaking.

Yesterday, I was in the mood to up the ante. We spent a solid three hours in the “Fuck Treehouse” and tried a variety of toys: hard, soft, vibrating, static, fast, slow, gentle and rough. Without further ado, here are the toys that were up my ass yesterday:

From left to right:
First is a slender silicon butt plug, with a wee little vibrator threaded through the base. I kinda liked that. I don’t think it would have made me cum, and the vibrations were subtle, but if I did a clench and release pattern with my ass cheeks, it felt nice.

Next is a slightly girthier butt plug, with considerably stronger vibrations. Same as with the previous toy; that wasn’t enough to get me off, but I enjoyed the sensations.

Then a glass dildo, thicker still. I felt kind of “meh” about that. Glass has a frictionless glide (when well oiled) that made insertion easy, but otherwise it was uninspiring.

Then a double-ended dildo that S wore in a harness for fucking me. The cliched position for having your ass fucked is doggy style, but I’m taller than S and I couldn’t seem to get low enough for her to reach me in that position. And, of course, the curve of that dildo meant I needed to be face up for it to stimulate my prostate. That was enjoyable, primarily because of the interactivity. Watching S get off from the end of the dildo inside her, egging her on to push harder or deeper, that was fun. In hindsight (again, no pun intended), I’m surprised I handled the girth of that dildo as well as I did. Of course, there had been some extensive warm up prior to that toy.

Lastly, there is the silicon dildo attachment for the Sybian. Finding the right position to ride the Sybian was a challenge. If I really wanted the vibration to focus on my prostate (can I just start calling it the “p-spot”?), I couldn’t be resting on my knees as is traditional for a woman on the Sybian. Instead I got my feet under me and leaned backwards considerably, bracing my arms on a padded bench placed just behind the Sybian. Effective, but it was putting a strain on my arms holding myself up that way. At the end, I had S lying in front of me, sucking my cock while I perched on the Sybian. The sensation was delicious, intense, and overwhelming, but I still didn’t manage to cum. Maybe it was from the strain of holding myself, maybe I didn’t have the stimulation in quite the right spot, maybe I wasn’t psychologically ready to let go. Dunno. I enjoyed it, but no release.

Overall, I had a good time, and when I finally laid back and masturbated afterwards, the force and quantity of my ejaculation was staggering. I’d try any of the toys again, but I suspect I might need to do some shopping for the kind of sharply curved toys specifically intended for prostate stimulation.

Most importantly, the experience gave me some insights into how to improve my technique when I’m playing with someone else’s anus and rectum, and how to do that in a way that feels safe, reassuring, and (hopefully) rewarding.

Late on a quiet Sunday afternoon, I was lounging on the sofa and S was reading in the bedroom. From the other room she called out, “Do we have talcum powder?” “Nope, don’t think so.”, I replied. After a moment of silence, S came back with, “How about corn starch?” “Sure. In the cupboard, in a round, blue and gold can.” Without responding, she padded barefoot into the kitchen and then returned to the bedroom.

Intrigued, I asked from the couch, “Why do you ask?” In a matter-of-fact voice she said, “Because I was lightly stroking my clit, and I wondered what it would feel like totally dry and buttery soft, like with talcum powder. You know, instead of all wet and oily.”

Can you see why I adore this woman?

Within a bare few minutes, I could resist no longer. I got off the couch, went to the bedroom and laid down beside her on the bed, where she was idly playing with a pussy liberally dusted with white powder. With her welcome blessing, I joined in the experience, and found it was quite lovely. The powder made the skin contact soft and smooth, and the lack of oil meant I could feel every little crease and fold and all the subtle differences in the skin texture. It was extraordinary!

Despite S’ appetite for overwhelming sensations and rough play, an excruciatingly light and fairly slow touch is the surest way to get her off. With my powdered finger feathering up and down the shaft of her clit, she was ready to come in very little time. I teased her for a while, denying her that first orgasm until she begged and pleaded and offered me anything I wanted (like that’s anything new) before I allowed her to have that first shuddering orgasm. Once the dam broke, I continued stimulating her and brought her off several more times before giving her a break and letting her breathe. It was a delightful experience, and one I enthusiastically recommend.

After, her eyes twinkled and she asked hopefully, “What would you like to do next?” I did not have to think very long. “Friday night you talked about wanting to squirt again. Let’s go up to the attic and do that.” S did not need her arm twisted. “Okay!”

I hasten to point out that she hopped in the shower to briefly rinse off the corn starch; we weren’t trying to make a roux here!

In the redwood paneled attic that a friend called our “Fuck Treehouse”, we put down the “sex blanket” (a Liberator Throw) to catch any fluids, got out the NJoy Pure Wand, and brought the jar of coconut oil into easy reach. As aroused as S already was, getting her to squirt took surprisingly little time. Her ejaculate was copious and decidedly milky white. I still haven’t found the knack of making her squirt with my fingers, but the heavy steel barbell does the trick pretty reliably. As I was using the barbell on her, I provided some auxiliary stimulation by playing with her clit, then later very shallowly fingering her asshole. She soaked the blanket quite thoroughly and noisily (and happily, the mattress below stayed entirely dry).

We have gradually been exploring more ass play between the two of us, and this seemed like a good time to push that envelope a bit. (“I’d push her envelope, I tell you whut.”) We took some time to examine in a clinical fashion what she liked and what wasn’t as good. With not even one knuckle fully inserted, I demonstrated lightly jostling and bouncing my finger (her favorite), working my finger in and out without actually stroking the skin (I can demonstrate that better than I know how to describe it), and then stroking my finger in and out a way that actually stroked the skin (which was a little too intense for her).

Equipped with a better idea of what was working for her, I asked her to get on hands and knees. I inserted the narrow end of the NJoy into her pussy and played with that in the usual fashion, soon getting her to squirt a bit more. After a while I bent forward and started lapping at the puckered pink rosebud of her asshole. She groaned deeply, her face and shoulders dropped to the bed and her ass arched towards the sky. We played with that for quite a while, with explosive results. I have become familiar with how fast and how often S can orgasm, in rolling waves one right on top of the other. This was several steps beyond that. She was thrashing side to side, screaming gutturally into the pillow, utterly incoherent, one step away from a grand mal seizure. When that went on long enough that I thought she might hurt herself, I backed off slightly, stopped lapping at her asshole, let her gather her wits, and then resumed the intensity, this time stroking her clit as well. And whoosh, there she goes again. I played through several variations of that, until she begged for a break to have a drink of water.

After the briefest of respites, we decided to very carefully try to narrow end of the NJoy wand in her ass. Still in the “face down, ass up” pose, I held the wand very still and let her gradually work it inside her ass. With me holding the wand still, she could be in control of the speed and depth of the action, pausing to get used to the size and sensation as needed, then working deeper, then waiting, then again. Ultimately, she took the ball end of the wand and perhaps an inch of shaft, and that seemed to be a happy place for her. With the slightest rocking motion of the wand, I started stroking her clit, bringing her to a couple of very happy orgasms with the wand inside her. Emboldened, I slipped two fingers inside her pussy and started playing with her g-spot while the wand was still in her ass. The wall separating the rectum from the vaginal canal is rather thin, and I could clearly feel the hard ball of the wand against my fingers as I stroked her g-spot. She had several more orgasms this way, rather louder and more enthusiastically. On a hunch, I removed my fingers and just played with the wand in her ass, hoping it would tap in a diffuse way against her g-spot. It seemed successful, and she had two solid orgasms with no stimulation aside from the wand in her ass (albeit, stimulating her g-spot indirectly).

When her ass finally reached its limit, I held the wand steady and let her ease forward until the bulbous end plopped free. I reassured her that I saw no sign at all of any tearing, nor any slight bleeding, and frankly, no messy “santorum” either. I gave her well-used asshole a friendly and comforting lap or two, set the wand aside, and fell on the bed beside her as she exclaimed a tired but joyful “Wow!” Then she noticed my cock, which was rather happily erect, and perhaps even a bit larger than usual.

She attempted some profound deep throating, and found the extra smidge of length too much for her throat. She asked me to fuck her instead, and I did so with great abandon. In all honesty, I was so crazy aroused by this time that I didn’t last very long, but it was still enough to give her three or so more orgasms before I reached my own shuddering, groaning climax.

Goddamn. Is it any wonder we so rarely leave the house?

Note: Wow, I threw around a couple of brand names in this post. I want to rush to reassure readers (all two of them) that I have no connection with the companies cited and there’s no compensation whatsoever. I only mention the brands with such specificity in case someone reading thinks to themselves “That sounds nifty! I wonder where I could find one of those.”