My attitude towards anal sex is what I have referred to in the past as a love/hate relationship. Many of you that are familiar with my stories may be somewhat surprised by that because of the role that anal sex plays in many of my stories. I would explain that as being the result of my change in attitude over the years. Anal sex was not something I have always enjoyed. This story is intended to document and explain that change, and describe how it came about over the years.

I, like many women of my generation, based my attitude on anal sex on what I can only describe as traumatic early experiences. As I look back now, I recognize that these experiences were with mostly inept, insensitive, and inexperienced lovers. Mostly, they were young men that had no clue as to the techniques required for successfully making love to my rear passage. Many looked at a woman’s ass as an alternative vagina. Furthermore, they were even less knowledgeable when it came to the female psychology of anal sex.

While I find it easy to blame these young men, I have also learned to assume some share of the responsibility as well. I guess you can say this is part of my maturation as a woman. I have learned to accept the fact that I allowed this to happen to me and that I was just as ignorant as my lovers. Of course, this was at a time before the internet and readily available printed materials on the subject, like those that exist today. Anal sex was like most other sexual activities, we simply learned by trial and error. However, in this case, the errors almost entirely overwhelmed the successes.

Over the years, I had discussed this with many other women and a few male lovers. What I learned was that I was not unique in this regard. Many women have shared their horror stories as well. Many were similar, and some even more traumatic than my own. The common thread that ran through them was the same inexperience and insensitivity that I have now learned to recognize.

Surprisingly, I discovered that porn, both written and video, had a large part to play in the attitude and approach that many men had towards anal eroticism. I can’t really say that proper technique plays a large role in any depiction of anal sex in most porn genres, even today in a time that I like to think of as more sexually “enlightened.” I still read stories here on Literotica, that, at their best, can be best described as “improbable,” and at worst are simply scary.

I have posted in the Lit forum about the fact that I feel writers have an obligation to depict sexuality in a form that is accurate and believable. Often, while writing, I have put myself in the shoes of a young man or woman that are reading my stories, and felt the need to portray sex in a way that has some accuracy and educational content. For better or worse, our society lacks any effective form of sex education. Erotica, unfortunately, fills that void to some degree. I was shocked to see that many writers did not share this belief, and some that were plainly hostile to it. The response by other authors to my forum posts was filled with language such as “it’s just a fantasy” and “the need to suspend disbelief.”

I have a hard time with those concepts because I somehow doubt that many readers, especially the young and inexperienced, are able to differentiate “fantasy” and real life. I suppose that largely depends on how outlandish the fantasy. Sometimes a fantasy can go to such an extreme that even the most naïve reader can appreciate that this is not real life. The problem comes with stories that are more subtle with their “fantasy” aspects.

I won’t go into my early anal sex history very much, other than to say it was painful and brief. The fact that my lovers during this period often thought that anal sex was something appropriate to “surprise me” with certainly didn’t help. Anal sex, as I alluded to earlier, was lacking in lube, sensitivity, preparation, and skill by both my lovers and myself. These early experiences were when I was in college and my attitudes towards anal sex were largely dominated by concerns over pain, hygiene, and social taboos.

Many years passed during which anal sex was largely non-existent in my sex life. There was an occasional finger or tongue used to try to please me, but my conditioning had made me reject much more than that. For the most part, I didn’t get much in the way of pleasure from these occasional forays. There were occasional lovers, both male and female, that attempted to go beyond these attempts but I always made it clear that my ass was a “no go zone” and simply not part of my sexual repertoire.

I suppose you could say that my attitude towards anal sex began to change after I met and began to live with Judy. My relationship with Judy was primarily as a roommate, and secondarily as occasional lovers. We were each other’s “bootie call” friend during dry times in our love lives. Judy was, for lack of a better term, a vocal advocate and aficionado of anal sex. Anal sex, simply put, was her “thing.” I can still recall frequent occasions spent lying in my bed listening to her through the thin walls of our apartment, as she encouraged her male lover, and occasional female lover, to even greater heights of anal eroticism. She was extremely vocal in this regard and needless to say, very uninhibited as well.

I do admit that listening to her was a huge turn on and usually left me masturbating in my bed as I listened to her and her lover. Even though my mind was having a hard time consciously accepting anal sex, my body, and sub-conscious mind, was not. Some of my most memorable self-induced orgasms were accompanied by the sounds and mental images of Judy’s anal extravaganzas.

As time went on, and as I became more comfortable with her as a lover, her encouragement was expanded to include me. I discovered that she enjoyed nothing more than my lubed fingers (or dildo or vibe) buried in her ass and my tongue on her clit. This combination never failed to bring her to large, and sometimes several, body jolting orgasms.

Her love of anal sex was not simply limited to receiving. She was an enthusiastic giver as well. At first, my inhibitions were sufficient to limit her to the occasional use of a single finger or an occasional tongue in or on my bottom. I was always up tight about the whole cleanliness thing, even if she was not. Judy ultimately accepted my hang-ups and anal exploration was never more than a minor part of our foreplay or the build up towards what I thought of as “normal sex.” Perhaps this fact was the reason why our relationship, if you can call it that, never progressed beyond that of “fuck buddies.”

The topic of anal sex, and Judy’s attitude and enjoyment of it, was eventually discussed during a pillow talk session after a particularly heated sexual encounter. My eyes were opened by this discussion, and for the first time, I started to re-consider my own attitudes. This was certainly not the first time I had discussed anal sex with another women, but it was the first time that I had met someone that didn’t share my own negative impressions about it. Judy was, is nothing else, a huge advocate and cheerleader for the joys of anal sex.

First, I realized that the pain issue was something akin to a self-fulfilling prophecy. My early experiences had all be painful and as a result I was not able to relax enough for it to be anything other than painful. If I couldn’t relax my anal sphincter, any attempt at penetration was going to be nothing short of rape. My mind simply would not allow my ass to do anything except tighten up in anticipation of what my mind was convinced was sure to be a painful experience.

Second, she explained that hygiene was not the major issue that I had thought it to be. She explained that the rectum was usually largely empty most of the time. Yes, there were some nasty germs there, but as long as a lover didn’t switch back to your pussy after being in your ass, that wasn’t really a big issue. Besides, you can always use a condom. She further described how she had started including enemas as part of her pre-date preparation and how much that had helped her overcome her own hygiene concerns. She even said that she had come to the point that she got some enjoyment from the ritual of cleaning her ass and preparing it for sex.

Lastly, she told me how she had had similar issues with the taboo nature of anal sex. She described how a wonderful lover had helped her overcome that and open herself to the possibilities for pleasure in that part of her body. She said she was eternally grateful to that lover for his assistance in her discovery process. Besides, she explained, anal sex was a lot more “main stream” now that a lot of women were allowing themselves to explore their sexuality.

That point really got me thinking. I had always prided myself on my ability to be open to sexual exploration and how in touch I was with my sexuality. I realized that to some degree, I had kept a firm lock on that possibility and there was some hypocrisy in my attitude. I eventually came to the conclusion that I had perhaps never really given anal sex a fair shake.

Unfortunately, my employer promoted me and transferred me out of state a few weeks after this conversation. I did get with Judy once more before I left and I allowed myself to open up to some limited anal exploration. Our discussion and some later follow up chats, were far from forgotten, and I often referred back to them in my mind. If nothing else, Judy was successful in that I was at least allowing myself to start considering the possibilities.

Anal eroticism slowly began to establish a foothold, at least to a limited degree, in my sex and fantasy life. When I say my sex life, I am primarily referring to a few exploratory experiences during my more enthusiastic masturbation sessions. It was definitely not something I was ready to share with a lover at that point. Besides, as a result of my re-location, I was out of the social scene for a while, and mostly celibate.

My lack of a social life was greatly exacerbated by the fact that my new position required a lot of business travel. The result of all this was that I had a lot of free time on my hands, much of it spent in a hotel room in towns I knew little about. I was never the type to become a hotel “lounge lizard” and was more likely to spend free time in my room with a bottle of wine and a good book or watching TV.

The lack of a social life had one immediate impact. I had always been a devotee of masturbation, even when I was in a relationship. However, it now became my sexual mainstay. Masturbation for me was always a long drawn out affair and I certainly had the time to devote to it. During this period, it developed into an art form. Much of my reading material was of an erotic nature. I rarely passed through an airport without picking up a copy of Penthouse Forum, Variations, or something similar. I had a couple of trusty vibrators that were part of my travel kit. Many evenings were spent reading erotic stories and bringing myself to wonderful, full body orgasms. Needless to say, I spent a lot of money on batteries during this period and spares were also part of my travel kit.

My job change forced me to start reconsidering a lot of aspects in my life, professionally and eventually personally. I spent a lot of the time in the hotels devoted to this reconsideration. I think this period was when I first became truly comfortable with my sexuality. A lot of that had to do with acceptance and finally flushing a lot of societal conventions from my brain. I had finally rid myself of a lot of the “good girl” notions about sexuality that my family and society in general had force fed me. I came away with an attitude that could be mainly described as “if it feels good, do it.”

Anal sex was not left out of this sexual rejuvenation. I have always been what some may describe as a goal oriented, type A personality. Anal sex, or rather my exploration and eventual enjoyment of it, became one of those goals. I can even remember sitting in a hotel room, one stormy night in Tulsa, jotting down incremental goals and the steps needed to achieve them. Admittedly, I was honest enough with myself that I realized all these goals might not be necessarily achievable and the entire project may end in failure. However, I was not going to give up without a sincere effort. For several months afterwards, I referred to this as “the project” whenever I thought about it. The rest of that week was devoted to refining the plan. By the time I got home that weekend, I was ready to begin.

This was in the mid 90’s and by then the early form of the web had taken shape. It certainly wasn’t as expansive as it is now, but I decided to do some searches on the topic of anal sex and see what was available. Online porn was in its infancy and I found more than a little porn devoted to anal sex. I dismissed most of it and focused on sites that were more oriented to “how to” and tutorials. There was certainly not a lot, but enough that I got some good ideas and information from them.

With my background research complete, I made a trip to the drugstore for step two. I did so late at night at a 24-hour store so that no one I knew would see me, or at least I hoped so. I stocked up with a couple of different types of lube and enema products. I got some Fleet disposable enemas, as well as an enema/douche bag. I decided to try both and see which I preferred for both at home and when I was on the road. Lube was limited to KY and I seem to recall that Astroglide had just become available in drug stores, and I got both. I also got a box of condoms. Luckily, I got one of those clerks that didn’t even notice what I was buying. She looked tired and half-asleep and my embarrassment was minimized.

Later that weekend I made a trip across town for my first visit to an adult bookstore. This was before the large adult megaplexs and online shopping was still very sparse. I had been told by a friend that this store was “the best.” I didn’t really know what to expect. The few vibrators that I owned had either been a gift from a lover or purchased at a lingerie store or in the “novelty” section of a store like Spenser’s Gifts. I knew that neither a lingerie store, nor Spenser’s was going to have the “specialty” products that I was looking for.

I’m not sure what my friend’s opinion of what “best” implied, but I thought the place looked seedy. I can say that it did seem to be clean. I went early in the morning in the hope that the “perverts” wouldn’t be there yet. Actually, it was almost empty. There was one couple in the main shop area with me and they were over looking at videos. I assume the rest of the few cars in the parking lot belonged to people that were in the back in the video booths.

I quickly found the toy section and spent a few minutes looking over the selection. There wasn’t a lot, but enough that I found a few things that were along the lines of what I was searching for. I grabbed them and beat a hasty retreat from the store. The clerk seemed bored and other than asking me if I needed extra batteries, we had little in the way of conversation. I paid and was driving home within a few minutes.

The rest of the weekend was spent on errands, laundry, paying bills, and preparing for my next trip. I didn’t have the time available to devote to the drawn out session I was planning and I decided to wait until the following week while I was on the road. I packed up all my supplies in the bottom of a small bag and covered them with toiletries.

I went into the office on Monday and worked until late. My flight was a late morning flight on Tuesday. I got in and out of the airport and through the rental car agency with no problems. By late afternoon I was settling into my hotel room and making phone calls to confirm my appointments for the week. I ordered a salad from room service and after I finished eating, I began to plan the rest of my evening.

I began by drawing a hot bath. I soaked for a while and shaved my pits, legs, and trimmed my pussy. I decided to try out the Fleets enema first and I retrieved it from the bottom of my overnight bag. I carefully read the directions and had to go retrieve the lube to apply to the applicator tip on the Fleets container. I did this while letting the Fleets warm in the sink that I had filled with hot water. Following the directions, I prepared a second Fleets for a final rinse while I was getting everything else ready.

When everything was ready, I got on my knees on the floor and tried to push the applicator into my ass. The lube didn’t help because the tip kept sliding around. After a minute or so, I finally got it positioned correctly and started to slowly slide it in while forcing myself to relax. It felt odd, but not much different from a finger. It definitely wasn’t entirely uncomfortable.

The flood of fluid that followed was definitely something I wasn’t used to or prepared for and the feeling of liquid in my bowels was something I associated with something a lot less pleasant. I realized that association was largely mental, and not a physical reaction. I lay on the towel on the floor for several minutes, absorbing the feeling of the liquid seeping deeper into my colon and doing its job. Finally, I moved to the toilet and released the fluid. I then repeated the process with a fresh Fleet’s for a final rinse.

Now that I was all clean and “fresh,” I moved to the bedroom and prepared to continue my experiment. I had laid out a few toys and brought the bottle of lube with me from the bathroom. I put a towel over the bedding before climbing into bed.

For that first time, I limited myself to inserting first one, then later a second finger in my ass. While I generally found the sensation enjoyable, I noted a couple of things. First, my short arms made reaching my ass a little difficult and limited me to the positions I could be in. Second, the positions I was limited to made my other favorite masturbatory accompaniments, such as reading erotic stories, almost impossible. While it was a good first attempt, it had its limitations.

I quickly recognized that I needed to move on to small toys that would “extend” my reach. Having gained confidence in my ability to accept two fingers I next tried a small vibrator that was about the same diameter as my fingers. I made sure to wipe the lube off my fingers because the vibe didn’t have a base that would prevent it from getting “lost” inside me. Besides, I was more interested in determining my ability to handle the girth of the toy than the depth.