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.

Summer 1983

During the Summer session at my town’s art college, my highschool girlfriend’s mother taught art classes on the campus to local elementary school students. Occasionally, Paula and I would go to the classes with her, ostensibly to help, for a very loose definition of the word. Paula and I had just started having sex a couple of months prior, and were going at it like we had invented it.

On one such occasion, we snuck away to a bathroom near the classroom, locked the door behind us, and had a frantic, urgent quickie. We fucked with the kind of brevity only teenagers can manage, then composed ourselves, and snuck back into the bustling classroom with what we imagined was smooth subtlety. And not even a half hour later, we repeated the trick. And again. And… Before the day was over, I’m sure we visited that bathroom over ten times. Hey, we were teenagers! At the time, we thought we were being terribly discreet, but in hindsight I cannot imagine it was not blatantly obvious to her mother. I can only imagine what she must have thought. Later that same day, Paula and I wandered off to stroll through a nearby art museum, where I seem to recall finding a quiet nook and enthusiastically fingering her. I am truly fortunate that my first serious girlfriend was easily as sex-crazed as I was. Those were some good times.

Fall 2017

Though I left town over 30 years ago, my family still lives in the same area and I return occasionally to see them. On the latest visit, I brought my current partner with me. Melody is an amateur artist, so one morning when we had no other plans, I took her to that same art museum to spend a couple of hours looking at paintings and sculptures. As luck would have it, the museum was very lightly attended that morning, and when a suitable opportunity presented itself, I slipped my hand under Melody’s dress, pushed her panties to the side, and stroked her clit attentively for several minutes while she pushed back against my hand and stifled her moans. After a furtive but enthusiastic orgasm, she composed herself and we resumed our art appreciation. We left the museum with some time to spare, and so… I led her to the nearby college of art. As we headed that way, I told her the story of my teenage adventures with Paula at that site. We spent some time admiring an exhibit of student art in the atrium, then wandered upstairs and found a bathroom much like the one Paula and I used (perhaps the exact one). We entered, locked the door behind us, and I fucked her from behind with all due enthusiasm. The facility was as tiny and grotty as I remembered it, though it had been updated with automatic sensors for flushing the toilet and dispensing paper towels. We managed to accidentally trigger a release of paper towels at a climactic moment, to some laughter.

Again, I am truly fortunate to have a girlfriend who is easily as sex-crazed as I am. These are some very good times.

M was not gone from my life very long when I took up a relationship with S. She was a long-time friend and confidant, a member of my logical family for some years. We had even had sex a handful of times, quite enjoyably, but neither of us were in a place to pursue that more frequently or more intentionally, until M left.

Three things came together in a quite unexpected fashion when S and I embarked on a more serious relationship.

First, we started incorporating BDSM into our sex play from the outset. I had long known S was a self-described sensation junkie, with a very high pain threshold. She also had some challenges reaching climax during the early renewal of our relationship, so rougher play and BDSM were a way of reaching some of those intensely transcendent moments during sex without orgasm.

The second major factor was that I took the occasion of deepening our relationship to ask S for some details regarding her past and childhood. Most specifically, I wanted to hear the full story of several years of childhood sexual abuse she endured. This was a fraught process. S had spent a great deal of her adult life trying not to think about that part of her past, had internalized a significant amount of shame and blame about the event, and had never before shared the entire story with anyone. Thankfully, she felt like she could trust me, and we spent long hours over several different meetings going through all of the horrific details.

So there we were. Meeting once a month at the start, very soon moving to once every two weeks, and shortly after that to weekly. Talking very intensely about her childhood sexual abuse. Engaging in some fairly rough sex play and BDSM. Quite unintentionally, the two began to overlap in some unexpected ways. After rough sessions of flogging and spanking, we would take time for aftercare, soothing her skin with oil, reassuring her that she was in a safe space with someone who loved her and cared for her deeply. During those times, she would often flash back to our conversations of her abuse. On some occasions, she flashed back to specific events and details with graphic clarity. Other times she would break down sobbing over the guilt she felt over “letting” the abuse happen. I categorically reject the assertion that a seven-year-old has any agency in sexual abuse inflicted upon them and I started making that case with increasing vigor and firmness. As incredible as it seems to me, this was the first time S had gotten validation that her childhood abuse wasn’t her fault. It took a lot of time, reassurance, and discussion for that idea to begin to take root within her.

The third major factor (remember, up above, I said there were three parts?) was that all of this elevated BDSM activity motivated me to get much more serious about the practice. I spent some considerable time thinking about my own internal ethics and the moral implications of striking a woman, repeatedly and quite hard. Growing up as a good Southern boy with lessons of “you don’t ever hit a woman, ever, for any reason” left its imprint on me and I had to really think deeply about how these new sexual behaviors integrated into that. There are some past posts in this blog where I wrote about that issue at some length. I also did a bunch of research and reading in the neurological science behind pain play and why that “works” so dramatically for some people. The BDSM sessions I planned and executed for S started to follow more specific and intentional patterns, based on that research. Over the course of ten minutes I would gradually escalate a pattern of stimulation, building within S a reservoir of endorphins, ending in a climactic rush of stimulation/pain to dump those into her bloodstream. Then the next ten-minute session would immediately begin and the cycle would be repeated. We would get three or four of those cycles completed before S was effectively “tripping balls” on her own internally-produced endorphin rush.

There was one particularly note-worthy moment that brought all three of these factors together. We were in the midst of an intense BDSM scene. S was standing, arms restrained by padded wrist cuffs. I was behind her with an array of floggers and leather straps, escalating the activity towards another endorphin release. She was at a particularly vulnerable moment, the flogging was really getting to her, there were tears flowing. To this day, I don’t know quite what prompted me to do this, but as I was flogging her, I started asking her, roughly, angrily, “Whose fault was it?”

The first couple of times, she was silent and didn’t answer.

“Whose fault was it?” Thwack!
“Whose fault was it?” Thwack!
Eventually, she responded, breaking down sobbing in the process.
“It was my fault!”, tears rolling down her cheeks.
“Whose fault was it?” Thwack!
“It was my fault,” she answered, more tentatively this time.
“Whose fault was it?” Thwack!
“Whose fault was it?” Thwack!
“His fault?”, this came nervously, tentatively, like she was trying it on for size in her head.
“Whose fault was it?” Thwack!
“It wasn’t my fault.”, this came more firmly, like she was finding sure footing.
“Whose fault was it?” Thwack!
“It wasn’t my fault!” This came out stronger still. She also stood a little taller, and did not shrink from flogger blows.
“Whose fault was it?” Thwack!
“It wasn’t my fault!” This came out as an angry shout, defiant, solid. She flared her back and shoulders, daring me to do my worst. I put my back into it and swung hard.
“Whose fault was it?” Thwack!
“It wasn’t my fault!”
“Whose fault was it?” Thwack!
“It wasn’t my fault!”
“Whose fault was it?” Thwack!

When I released her, the aftercare was especially long, and there was a great deal of crying. However, these weren’t the hot tears of shame and violation, but the cleansing tears of release. For the first time, S was really coming to terms with releasing the responsibility she had been trying to carry.

This experience shaped much of our subsequent BDSM play. Over much time and discussion we would identify issues where she was “stuck” mentally or emotionally and look for ways to bring them to the surface during an intense scene. In the process, her confidence grew and emotional weight she had been carrying for virtually her entire life began to fall off her. She was reframing her memory of the experience, from something that defined her, into something that “merely” happened to her.

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.”

01. July 2017 · Write a comment · Categories: Uncategorized · Tags:

I’ve lately been revisiting Armistead Maupin’s “Tales of the City” series on audiobooks. As Melody and I made our way through the series, we had a conversation about AIDS and the ways it touched our personal lives.

Though Melody is only 18 months older than me, our experiences couldn’t have been more different.

She vividly remembers getting her first test and waiting the interminable two weeks for the results, she lost dear friends to the disease, and nursed loved ones as they succumbed to it.

My first several partners were all long-term relationships, virgins when I met them. Despite being in open/poly relationships from my very first serious girlfriend, and being in a threesome for several years across high school and college, I was… this feels really hard to confess… I was 30 before I had sex with someone who had previous sexual partners. Said another way, I was 30 before I had sex with someone whose virginity I had not “taken”. As I look back and say that out loud, it seems unfathomable to me.

As such, I didn’t worry about possibly contracting HIV until long after the horrific shock of the plague had passed and people resigned themselves to the possibility as a tragically real risk of our era.

It’s scarcely believable that a journey started like that has led me to where I am today.

20. June 2017 · Write a comment · Categories: Uncategorized · Tags:

Perhaps you’ve had the experience of visiting the home of someone who has too many pets, and/or pets with insufficient hygiene. Everyone who visits the house instantly recognizes the problem, except the people who live there. They have been surrounded by the smell for too long and have lost the ability to recognize it.

In that spirit, I’m asking for some radical honesty. Please, tell me straight up; I can take it. Does my house smell like sex?

Over the last two weeks, S and I have had two dates with a new person in our lives, E. There have been a dozen delightful aspects to the experience; glorious conversations that swoop from the silly to the sublime to the serious, learning each others’ stories and histories, the seemingly instant rapport S and E developed, the easy way the three of us collaborate and play in the kitchen while making pasta and salad, deep-and-real conversations basking in the hot tub, and (lest you forget who you’re talking to) there has been a considerable quantity and quality of amazing sex. Fucking awesome (and awesome fucking)!

There’s one aspect of the experience that I have found especially gratifying and would like to describe.

The first evening the three of us hung out together, we reached a threshold where it was clear we were going to be fooling around. We had been talking about sex all night, her experiences, our experiences, where our individual journeys have taken us. Eventually we ended up in the sex treehouse and she saw the Sybian and the bed up there and we all looked at each other, grinned, and effectively said, “You wanna?” (Oh hell yeah!)

So, clothes were doffed, we cuddled on the bed together, and there was that brief awkward pause of “Okay, how are we gonna do this? How does this work?”

It feels like there is never a good sexy time to have the STD talk, there’s only more and less awkward. But this felt like about the best window we were going to find. So I seized the conversational bull by the horns, “Hey, before we get started, let’s have the terribly unsexy and awkward STD talk.” We explicitly reviewed when we had been tested last, what issues there were to consider, possible risks to be mindful of. Once we felt like we had all potential issues on the table and a shared understanding, we took a moment to acknowledge how that can be a challenging topic, but we were all three so glad we had discussed it before anything juicy had happened.

Since we were in that space already, I then dove into explicit topic number two. “Let’s talk about boundaries for a minute. It’s super important to me that we’re only doing things that you’re really enthusiastic about. If you’ve got any hard boundaries that you already know about, I want to hear them. At the same time, if you find your boundaries shift as we’re fooling around and something that you thought would be awesome is making you uncomfortable, it’s important to me that you are able to speak up and let us know. Does that work for you? Can you do that, can you explicitly own your boundaries like that?” She could and did. We laid down a couple of hard lines and enthusiastically agreed that any one of us could pause the action at any time to add to that list with no drama, no hurt feelings.

I thought we were about ready to start and then E paused for a moment with a thoughtful expression and spoke again. “I need to say… I know you two enjoy some pretty enthusiastic BDSM play, and I feel like I need to say… that’s not really my thing. I like a little bit of light hair pulling in just the right moments, but that’s about it. I just don’t have the same relationship with pain that you do. I hope that’s not a huge downer.” We rushed to reassure her; I think my answer was something like, “Oh hon, I have zero agenda except making your brain turn to mush with pleasure! Especially while we’re getting started and learning about each other, I’m not trying to push your boundaries or do anything that you feel uncertain about. I want you to end this night feeling supremely blissed out and completely comfortable.”

With those conversations done, we turned to slathering each other with oil, getting a little familiar with each others’ bodies, and… epic amounts of fun ensued. I could write full-on porn about the experience, but here’s the thing that really stood out for me. Having had those conversations, we then proceeded to have one of the most uninhibited and least self-conscious threesomes I’ve ever had. There seemed to be the least amount of anxiety and fretting that I have ever had with a new partner. Everyone seemed to be fully comfortable in their own skin, overflowing with praise about how stunningly gorgeous the other two were, and deeply committed to spreading around as much pleasure as we possibly could. I don’t think I have ever felt as nakedly exposed and vulnerable in front of a new partner, nor have I ever been as well rewarded for being so open. Everyone took a prolonged turn as the center of attention, combinations and permutations were explored with glee and abandon, the differences in our bodies and preferences were explored with wonder and delight and a complete lack of judgement. And I was really pleased to find out that E did indeed feel safe and secure enough to say once or twice, “That’s not really working for me; can we have less of this and maybe more of that?” Knowing that your partner(s) have that ability to own their own boundaries does a considerable amount to quiet that inner voice that frets about, “She seems like she’s having fun, but is she really enjoying that? What’s the furrow on her brow mean? Hell, is that person feeling left out? Am I doing too much of this and not enough that?” Being able to let go of that and trust my partners was an enormous gift and tremendously liberating.

Last night was the second date with E, and I am so happy to report the first time was not a fluke. Again we discussed our boundaries, where our heads were, what we needed. We started in one place and twice when it seemed like things were about to escalate I checked in explicitly, “Can I do this, would you enjoy this?” and received clear and honest answers. It was a magical experience, ran rather later than any of us expected, and included several (welcome) firsts for E.

I feel profoundly fortunate to have had that experience with partners who are so extraordinarily generous with their affection, trust, and intention. I can’t tell you how eager and excited I am about the prospect of more forthcoming.

For several months, S and I have been having some deep and real conversations about sexuality with her friend J. J comes from a conservative and religious background, and her marriage is rewarding in a great number of ways, but not always sexually. So we’ve been talking to her about the sexual reawakening S experienced two years ago, talking about kink and BDSM, and talking about open relationships. Not evangelizing, not even trying to talk her into anything, but just sharing our experiences, the journeys we’ve taken, the mistakes we’ve made, and the rewards we’ve found.

Last night, J came over for dinner and talking. Which turned into hot tubbing. Which turned into taking a shower together. Which turned into playing in bed. Followed by more tubbing, more showering, and finally, reluctantly, going to sleep for the night.

Some images that are stuck in my head:

Washing J’s hair in the shower, while my erect cock slid against her ample and luscious backside.

Watching S and J kiss, and kiss, and kiss.

S sucking one of J’s nipples, while I sucked the other, doing our best to drive her out of her mind.

S licking J’s pussy for the first time. “I’ve been waiting to do that for 20 years!”

Fucking S from behind while she licked J’s pussy.

J on her hands and knees, ass high in the air and her head low, whilst I licked and fingered her from behind, giving J her first ever g-spot orgasm and making her squirt a tiny bit.

S fingering J, gradually adding one finger after another until S was fucking J with her entire fist; this was the first time I witnessed fisting first-hand.*

S hanging her head off the side of the bed, me filling her throat with my cock whilst J kissed and sucked S’s pussy.

Fucking S in the sex swing whilst J petted S’s clit and stroked my balls.

J on her back, S lying face down on top of her, me fucking S from behind whilst I held J’s legs high in the air; it almost felt like a pantomime of fucking J.

Giving J a series of especially strong orgasms, making her scream and shake, and finally withdrawing. The powerful, shuddering, after-shock orgasms J would have as much as a minute later from stimulus as simple as licking her nipple.

All in all, it was an amazing, wonderful, delightful night. So much trust, so few inhibitions, such rampant enthusiasm. It’s not quite my birthday yet, but this was one of the best celebrations I could have imagined.

* Pun unintended, but now that I’ve said it, I’m cheerfully taking credit for it.