Background: I have a story to tell. It’s a story about body image, porn, sexuality and relationships. Its main characters are myself; my aunt; the internet; its technological cohorts; and D, J, and M – three men I have, for lack of a better term, dated – in that order. Stories told in chronological order are nice, but I don’t want to tell this story starting from the beginning and proceeding to the present. I need to tell it in bits and pieces, not necessarily in order, with breaks in-between for essays on related topics that aren’t at the heart of my (our?) story, yet are topics that also compel me to write. Hopefully, the collection of these vignettes about my lovers, cybersex/porn and the deceased aunt I miss – hopefully, they will form some sort of coherent whole.
We were naked, in D’s bed, in his tiny studio apartment, on a Saturday morning. I was on one of my cross-country visits to see him for several days. I was stroking his cock, and sucking it, but he was not getting erect.
“We have a problem. I can’t seem to get hard with you.”
This wasn’t new territory for us. Intermingled with our frequent and painful arguments about the attractiveness … or lack thereof … of my breasts—a subject I’m sure to return to in future posts—we had also had some fairly open and thoughtful exchanges about his erections … or lack thereof. I thought we had succeeded in making ourselves feel comfortable and unpressured about sexual performance the first time we were together—five hours of intense exploration of each other’s bodies culminated in incredible fucking. He also liked my belief in the sex-positive feminist definition of “sex” as all forms of sex … for example, oral, finger-fucking, mutual masturbation … all valid, full-fledged sex. He agreed that sex is not just the old in-out, not just penis in vagina. As he put it, his penis didn’t work a lot of the time, so he liked to leave it out of things and concentrate on using his hands and mouth on his lovers. He also had described the change in his sexual response with age – easily getting and staying hard in his 20’s, erections becoming more difficult to come by in his 30’s.
I had thought he had a healthy attitude about it, so it took me by surprise when he called it a problem and implied that it was specific to me and … well …. my fault? I had known better than to turn it into a problem by regarding it as one—I wanted to give him sexual pleasure, more than anything, but he didn’t need to be a porn star to capture my erotic imagination. Apparently, in order to capture his, I did.
He admitted that he had been abstaining from masturbating to porn for about a month in an effort to get his easy erections back. He thought that perhaps he had grown used to a specific type of stimulation – not just the feel of his own hand, but the visual stimulation. I was skeptical that porn was to blame because I suspected other factors: his heavy drinking, his hang-ups about sex in general, run-of-the-mill performance anxiety, but he explained that he deals with not being attracted to the way his lovers look, by trying to concentrate on how it feels. I was still somewhat skeptical, but I was also hurt, especially in light of what I already knew about his gaze. In the context of our arguments about my breasts leading to his refusal to take my bra off during sex, any implication that my looks were responsible for his soft cock was yet another blow to my sexual ego. I was some combination of humiliated, angry, sympathetic and realistic. I said, “I’m not unrealistic about these things. I know that men like younger women. I have my own turn-ons and preferences in looks. I like men who are tall.” He said, “I like younger women.”
He liked younger women – not a huge revelation. In fact, something I can relate to. I kinda like younger guys, and for that matter, I kinda like younger women, too. But I feared he was a 30-something man unable to function sexually with me, a 30-something woman, because he was only truly turned on by the way 18-year-olds looked. Trouble was … he and his very real, very average body, showing all the signs of his age, was a huge visual turn-on for me. His gut, his pale doughy skin, his bald spot, his slight double chin, his back hair – I totally dug it all. Why wasn’t he the same? What the hell was I doing in his bed if he wasn’t enthusiastic about me the way I was about him?
I also suspected that laying off the porn might be the completely wrong strategy. The porn might be the key to me finding his turn-on – the key to getting in deep and rocking his world – the key to fulfilling his deepest desires, and by so doing, fulfilling my own deepest sexually submissive desires. I wanted to know what kind of porn he liked – I wanted to know what his turn-ons really were – I asked. Big awkward silence. There were always lots of pauses and silences during our conversations, even on the most innocuous of subjects. But this one was heavier. Finally, he sighed and blurted out, “I like anal, o.k.?”
“Why wouldn’t you just tell me that?”
“I don’t know. I’m shy.”
It was as if I had dragged this extremely personal and embarrASSing information out of him … which was odd because he was always trying to stick his fingers in my ass. It’s not like the revelation shocked me. I guess he didn’t like having to say it out loud.
Before D, there’d only been one guy who had tried fingering me anally. I was in my early 20’s, and the guy who tried it said that in his and his friends’ experience, anal stimulation was really pleasurable for women. They joked that the way to a woman’s soul was through her ass. They’d started referring to anal as “taking a woman’s soul.” But that guy didn’t reach my depths. His big finger just hurt, and I made him take it out almost as soon as he had put it in. And although I had experienced some intense pleasure from D fooling around on the surface without penetrating, it generally hurt when D tried to stick his finger in my ass, too.
I asked D whether he had ever done anal intercourse. No.
I asked whether he fingered other girls’ asses. Yes, but I was the only one to complain so much. I suggested that maybe I needed him to use more lube – it seemed like he always tried to put in a pretty dry finger, and I liked lots and lots of lube in my pussy, so lots of lube might be just the trick in my ass.
He took over then, confidently. He got the lube out. He laid back down on his back. He ordered me to straddle his chest, facing away from him. He had me bend over his cock and start stroking it. The position put my asshole right there at his fingertips. His well-lubed finger went in. Then out completely.
“Um, I think you need to go to the bathroom.”
I was mortified.
It was my turn to blurt out what had been extremely personal and much more embarrASSing information that I’d been avoiding sharing with him. I had been trying to convince him to let me have time alone in his apartment, but I had been evasive about why. He didn’t trust girls to be unsupervised in his space, and early on in our seeing each other, in a moment of honesty about my character flaws, I made the mistake of admitting that I had a tendency to snoop. But really, I didn’t want to snoop while he was gone. I wanted to do something tha
t rhymes with snoop!
Red-faced, I explained the situation … travelling cross-country, dehydration on the plane, nerves, the lack of privacy. He readily agreed to give me time alone in the apartment. Unfortunately, my alone time didn’t pan out the way we wanted. He left me alone by grabbing a book and heading up to the rooftop of his building, before we would be going to dinner that night. He said to just come get him when I was done.
Come get him when I was done??? Too. Much. Performance. Anxiety.
…
At the time, I considered myself relatively inexperienced with looking at and watching porn. Actually, I still consider myself relatively inexperienced with looking at and watching porn. I’m female. Looking at porn is not something I do much of, at least not the way a guy does. I have masturbated to porn on rare occasions, but if I want to jack off, I tend to go into myself, into my fantasies. And so, I was curious … pretty much as curious as I was at 14, the first time I was alone in a guy’s room, taking a few furtive peeks into the Playboy I spied under his nightstand … feeling fascinated with, turned on by and inadequate compared to the images … asking the questions women often ask themselves in secret about discovered porn that looks nothing like them: Is this what he wants? Is this what men want?
That night I suggested to D that we look at porn together. I told him I hadn’t seen much internet porn, that it wasn’t really something I did.
He sat in his big office chair at the computer. I sat on the couch just behind his chair. He walked me through his process – stuff I didn’t follow about turning off cookies – something about how the site we were going to was a compilation of thousands of free images that other users of the site had liked in their porn searches that day. The link to each set of images was displayed as a thumbnail, resulting in a full page of little images of different women. He proposed we take turns picking girls. He picked one first. Young, tall, thin, pretty, her pictures started off in skimpy shorts and a top and ended with her naked—nothing particularly interesting, nothing I felt I hadn’t seen a lot of actually—standard porn fare. I picked one—more standard porn fare—young, tall, thin, pretty. His next pick … professional photos of a young curvy plus-size woman with glasses, wearing a woman’s suit in the initial pictures and ending up naked by the end of the photo set. She intrigued me. She was something I hadn’t seen in my rare Playboy flip-throughs and my one marathon night of watching XXX-rated movies when I happened to be staying in a motel room with free porn access. She looked like I did before I had lost weight – she looked like a brunette version of me at 70 pounds heavier. I thought she looked rather scrumptious. But I was guarded. I didn’t comment. I just asked D what he thought of her. I guess I was hopeful that his picking her indicated he really liked her. He said flatly, “She’s fuckable,” as if he’d resigned himself to settling for the likes of her. Well, that didn’t feel very good.
This all really wasn’t what I had in mind or what I expected. This wasn’t good and fun like I expected it. This was bad, and it got worse. But I couldn’t articulate why or how or what I had, in fact, had in mind. I had some generalized idea that looking at porn together would be sexy and turn us on. This, so far, was not sexy, not at all.
I picked one. Amateur snapshots of a type of woman I had never really seen naked and on display for sex before. In her 40’s? 50’s? Thin, in great shape, her skin betrayed decades of being a happy sun-lover – mottled skin covered her chest and arms – her face had plenty of laugh and smile lines. D was sour, “She’s terrible!” He almost hissed it. This made me feel bad, just as bad as the fuckable comment about the cute fat girl. Why was that? This older woman looked nothing like me. Was it that someday I might look like that and I’d like to think that at that point in time, men would still like to look at me naked? And that D, specifically, would still be attracted to me? Was it that it was unnecessarily mean and disrespectful to women? Was it that he sounded so immature hurtling out insults about something as shallow as a woman’s age and looks?
It was also fascinating. These non-standard women—old and fat chicks looking sultry for the camera, getting topless, spreading their legs—they were a beautiful sight, in my opinion. And then there was the insight. Insight into this man’s gaze and its relationship to porn. That’s something that women commonly aren’t privy to. I hadn’t expected this weird combination of pain and fascination in hearing his reactions to other women’s nudie pictures. I hadn’t expected this meat market evaluation of them, but I was willing to roll with it, and then I couldn’t help it. I had to ask the obvious question.
“D? … Will you tell me whether I look like anyone on here?” I hadn’t thought that we had run across my nude double yet, but I thought we might, and we were already into such risky territory trampling on the edges of my body image. Why not just get right to the heart of the questions that were still unclear to me? How did he really see my body? How did my body actually look, in reality? I thought it might fix it all, too. I thought it could turn out to be interesting and affirming … and well, hot … to see a girl who looked like me up there amongst this collection of the favorite porn of the day.
D got angry and shut down the porn viewing. He said that was a trap. He said he had been having “danger, danger” thoughts the whole time we were looking at the porn. He said he didn’t want to talk to me about my body. I felt awful, confused. He went to sleep. Like most nights I spent with him, I was unable to sleep until late into the night—my brain, hashing and re-hashing his anger at me, trying to figure out what the fuck just happened, wouldn’t shut down.
By the next morning … I had figured it out. I told D, “That wasn’t what I wanted. When you planted yourself in the chair and put me over here on the couch and set us up to look at the porn all cool and rational and observational, I couldn’t help but go to an intellectual place of really honestly wondering: among this group of women, who, if any, do I look like? What I actually had wanted was for us to look at porn together while being sexual with each other. I had wanted it to be a sexual experience.”
Communicating with D was so hard, but there were these moments when I’d get through and he would get it and get my needs like no one else had before. He took over again, confidently. He had me bend over the computer, facing it. He sat on the couch right behind me, again setting us up so that my ass would be right at his fingertips. He typed in a URL from memory: www.teachmyass.com.
All we looked at were galleries on the main page … two examples:
My eyes were wide. I was looking at hardcore sex acts I’d never seen before – girls’ pink little assholes stretched so wide you could see up into the dark of their colons. Fingers, weird objects, whole hands, dicks – all in a place I had never fully appreciated that fingers, weird objects, whole hands and dicks could truly be inserted like that.
This site and the dynamic D had set up by planting me in front of him contained the k
ey I was looking for. It was not just that his favorite sex acts were on full display before me, giving me what I thought would be useful information about his turn-ons and showing me fantasy women that I could possibly emulate. It was also that, even though I had never been into anal before, my turn-ons were on full display before us. These fantasy girls were anal virgins. So was I. These fantasy girls needed to be taught how to do and enjoy something quite perverted. So did I. These fantasy girls desperately desired to learn from the fantasy male sex expert, so much so they were willing to pay the dude to violate, stretch and fuck their assholes. I was desperately seeking something erotic from D, something I couldn’t quite put my finger on, but something that compelled me to keep going out there to visit him even though I was sacrificing my self-respect and my values by going to bed with someone who wasn’t just insensitive about the effects of the male gaze, and his gaze, on his lovers but crossed the line into being downright cruel about it. Yet he had me set up in front of him the same way these beautiful young girls were set up before the camera – their sweet heart-shaped asses completely objectified. My sweet heart-shaped ass was naked, too, and about to be the object of D’s attention.
I felt incredibly submissive and extremely turned on. I felt like I was a beautiful young anal virgin needing a lesson. I started pointing out the pictures I liked – the ones in which the girls were being fingered, the ones with small dainty-looking butt plugs, the ones with the girls’ ass cheeks being spread by the guy’s big hands to give us all a real good look at her most intimate parts, the ones where the guy’s dick was sliding in – my voice was shy and girlish, “I like that one. I want you to do that to me.” I also pointed out the ones that freaked me out – the enema kit was freaky number one. At the time, I didn’t even understand … what in the world were those tubes going in her, making her look like some sort of cyborg or something? D chuckled, almost contentedly, when I covered it up with my hands and whispered, “I don’t like that one. It’s weird.”
D started doing things to me. Touching my pussy. Fingering my pussy. Stroking his fingers across my asshole. Using lots of lube, making me all slippery. I was deep into the fantasy of having my ass taught. I had my first pleasurable anal experience that Sunday morning—by the end of it, D had me on all fours, lengthwise, on the couch, with my back arched as much as possible, doing things to me that I couldn’t even decipher what exactly was happening. Were his fingers in my pussy? In my ass? Both? Was it one finger? Two? Three? My whole pelvic area, the entire length from my clit to my ass was like one mass of quivering sensation. I had lost myself in his double fingering me, taking me over with his hands. Any inhibitions I had, any self-doubt, all my worries about whether D was turned on by my body and our sex, all the awkward weirdness between me and D – those were all gone, at least temporarily.
These things came back, of course, with a vengeance. Afterwards, in the bathroom, him washing his hands and advising me to clean myself up carefully to avoid contaminating my pussy with fecal matter, I was firmly back to reality. And the reality was that I had still not pooped. It had been in there the whole time. Ugh. I asked him whether it was gross. Yes. I asked him why he did it. Because I was enjoying it so much.
Well, I had definitely not achieved fantasy girl status. Poopy girl was not his thing. But apparently, I showed promise. Later that day, as we walked to the subway that would take me to the airport, he said, sounding very satisfied with himself, “You had two fingers in you. Well, actually, you had four fingers in you. Two in your pussy and two in your ass. If it weren’t for the stuff, I would have gone even deeper in you.” The fact that I had been enthusiastically talking about how I was going to buy a book to learn how to receive, not just anal fingering, but anal intercourse seemed to please him.
I didn’t lose my anal virginity with D. I bought and read the book, I bought and learned how to use an enema kit, I really wanted to do it, and I flew across the country one more time, hoping he would be the one to take it, hoping he’d get to experience anal intercourse for the first time, too. We made a go at it, too, but we couldn’t even get his fingers in without pain, and his dick was determinedly limp that weekend for good reason. Our last weekend together was an emotional roller coaster for me, an uncomfortable drag for him—a weekend primarily spent fighting about his gaze, my body, and my unhappiness with the way things were between us—all a subject for a future post and not the main subject of this post. I actually didn’t lose my anal virginity until 2 years later. During those two years, my ass periodically pined for D’s skill, my heart periodically pined for him to take my anal virginity like we had planned, and my fingers, on rare occasions, typed teachmyass.com into my browser’s address bar and rubbed my clit to multiple orgasms.
