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.
