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.

When he called and told me I had an hour to get over to his condo, I thought we would be alone. But there were two other guys in the living room. One kicked back on the couch drinking a beer. The other looked slightly bored while flipping through some porn on M’s computer.

M told me to take my overnight bag upstairs to the bedroom, and then come back downstairs for a drink. His voice and his body language was upbeat, warm, just like I’d remembered. And he flashed me one of his easy smiles. That smile had made me feel giddy yet calm the few times I’d seen M in person. But it wasn’t quite working this time. I felt really nervous and a little upset while walking upstairs. The first time he agrees to see me in 4 months, and there’s two guys I’d never met! And that one of the guys was looking at porn—that added to my nerves. Porn makes me feel uncomfortable, prudish, jealous and inadequate as often as it turns me on. My lingering worries about whether M would ever be pleased with me as a submissive—whether I could please him as much as the porn models do, despite my refusal to get any implants, despite my problem with being, as he put it, rude—those worries had also set me on edge about this visit.

All this was bad enough, but joining them for a drink? I thought I had told M that I don’t drink. Didn’t he remember? Would he try to make me drink with them? There were so many things I had either resisted or outright refused to do for him—would he put up with another boundary? Would I put up with it, if I felt like he was pushing another boundary? And drinking was yet another issue I felt self-conscious but adamant about, just like I felt about breast implants. I’m really not interested in drinking, but when I find myself in social situations involving alcohol, it can be a bit awkward to be the 32-year-old who has never had even a beer or a sip of wine. I sometimes feel like a child among adults.

I tip-toed back downstairs and poked my head around the corner of the stairs. M was sitting on the bottom steps, saying something about how “they’ve both been hard to train. Sometimes I want to slap them silly, they frustrate me so much.”

M looked up at me, smiling warmly again, “Go sit on the couch next to Jeff.”

I glanced up at Jeff and then the guy at the computer as I sidled past M and across the living room. The guy at the computer was looking me up and down with the same bored facial expression he’d been giving the images on the screen.

As soon as I sat down, M piped up again, a little smirk in place of his warm smile, “What would you like to drink, Marilyn?”

I flushed bright red and stammered, “Um, I don’t drink. Could I just have some water?”

M chuckled a bit, “You can have some water, but I think you need to drink something more substantial, too. Something that will relax you. Something that will make you feel good.” Jeff and the guy at the computer smiled, too, wolfish little grins that simultaneously scared me and made my pussy tingle.

M got up and went to the small kitchen off of the living room. After I declined his offer of ice, we watched him run a glass of tap water, get an empty wine glass out of the cupboard, and then two opaque bottles out of the fridge.

He sat the four items down on the coffee table in front of me. It occurred to me then that the table looked really clean, and before I could stop myself, I blurted out, “Hey, the coffee table is all clear. It was really messy the last time I was here.” I meant to sound sweet and impressed because I was—I didn’t keep my house so clean. But M shot me a look.

Jeff spoke up, “Dude, cut her some slack. She’s right, and it’s not like you’ve been cleaning up around here. You’re letting Amy do that, aren’t ya?”

Amy? Who’s Amy? The other sub he’d been seeing?

“That’s not the point. Marilyn has a real problem with being rude, and I’m not letting it slide.” He looked straight at me, stern but forgiving, “You’ll make up for that smart-alec remark later. But right now, we’re going to give you a treat and show off some of your new skills to my friends.” He paused, “You’re a smart sub, Marilyn. What’s in the bottles? It’s not alcohol.”

I knew now what he’d served me. I’d been so resistant to the idea when he first asked me. I thought it was totally disgusting. I said as much when I said I would never do it. That was my first rude comment back in the beginning, back when M really liked me and hadn’t decided I was rude and took too long to cum. But the idea started to intrigue me, and soon, I was back-pedaling on my “never.” Fuck, soon I was masturbating to the idea. No wonder he pushed my boundaries—I wasn’t very consistent about this one.

I thought about all this as I replied, “Cum?”

“Yup, good girl…smart little sub…smart-alec little sub. The grey bottle is the cum from when Amy jerks me off. Do you want to try some of that first?”

I nodded slowly. I was excited, but I was also jealous that this Amy had gotten to jerk him off enough times to fill up a whole bottle with his cum, while I had only gotten to suck his cock and fuck him once. And I was still nervous. The idea of drinking his cum out of a glass had become a hot fantasy, but what if the reality was more like my initial gut reaction: totally gross?

“Pour yourself half a glass.”

I uncapped the bottle and poured some, thick and viscous, into the wine glass. I’d never drunk any actual wine out of a wine glass, but I was about to drink cold sperm out of one. Was I a childish abstainer or just a hardcore sex fiend at heart, preferring perverted adult pleasures like cum shots over standard adult pleasures like fine wines?

I glanced up at the guy at the computer. He looked interested in me now … he’d unzipped his pants and was stroking himself. The sight of his rock hard cock—that made me feel the calm that M’s smile normally made me feel. I knew M would like it that I was turning on his friend. I knew then that M would be rock hard, too, and that Jeff was probably hard as well. That was a good thing—M always said that hard-ons are a submissive’s only responsibility.

“Marilyn, you’re going to drink my cum in 8 sips. The last one might be more of a big swig than a sip,” he smiled. Then he added, “Every time you swallow, you’re going to come.”

I nodded slowly again, “Yes, sir. But…?” I hesitated, torn between the risk and the rew
ard of what I was about to do.

“Oh, I know what you’re wondering you little worrywart. I was tested 3 weeks ago, and Amy was tested last week. My friends may want to add a shot to your glass, so I made them go see the doctor, too. We are all clear. This is as risk-free as you’re going to get without sticking to a safe little latexed and monogamous sex life, Marilyn. Are you prepared to risk it?”

I was. I lifted the glass and smelled it. God, it smelled good. M’s cum. How I had longed for months to taste it.

First sip … it was thick and salty in my mouth, still cold from the fridge. That was oddly refreshing. Cum was normally warm when I tasted it. It wasn’t gross at all like I’d feared—I savored the salty flavor.

The guy at the computer stroked himself harder, marveling, “She likes it. No wonder you keep the little bitch around, M. That ain’t an easy thing to find, a chick who digs cum like that.”

And then I swallowed. The orgasm overtook me. It was small but immediate. I cooed and shivered slightly.

“Good girl. Very good girl. Next orgasm will be harder.”

Second sip … I noticed a subtle flavor I hadn’t detected in the first sip. A tang you don’t appreciate when going through the motions of swallowing after a standard blow job. God, I know I sound a bit like some of those pretentious wine buffs that bore me and make me feel dumb at parties, but what can I say? I was developing my palate for cum. M was turning me into a cum connoisseur.

I swallowed again. The second orgasm went through my body in strong waves. I moaned. I felt light-headed.

Third, fourth and fifth sips went by in a blur of orgasmic contractions. I was no longer savoring the flavor as much as I was enjoying feeling intoxicated … drunk on M’s cum and the multiple orgasms he could force out of me by mere suggestion.

Before my sixth …well, I was swigging the stuff more than sipping it by that point, so before my sixth swig, the guy at the computer couldn’t control himself anymore. “Girlie, you’ve got another shot you’re gonna have to do. Bring that wine glass over here and finish me off.” I jerked him off into the cup, which was really exciting but I wondered when I’d get to stroke M’s cock.

Picture from spermcocktail.com

The nameless guy came, grunting and snorting a bit as his warm cum dripped into M’s cold cum, and then he watched me intently. M sure was succeeding at turning me into quite the slut, jerking off some guy whose name I didn’t even know. But I felt like I had gained some upper hand over anonymous guy, or maybe the intoxicated feeling made me cocky. At any rate, I had his full attention, and it seemed appropriate to milk it. I took my finger and stirred his cum into M’s. Slowly. Deliberately. And then, just as slowly and deliberately, I licked my finger. Oh, but being so cocky about it was foolish. I was so focused on trying to impress him that I forgot to set the glass down before I swallowed. As soon as I swallowed, I came hard, harder than before because the mix of two guy’s ejaculate was even more powerful. I almost dropped the glass as I writhed around, shaking all over my body. After I was done cumming, M took the glass from me and pointed out some of their cum spilt on the carpet.

“You’re not going to let that go to waste, are you?”

God, I was out of control. I dropped to my elbows and knees and licked their cum off the floor, doubling over with lengthy orgasmic contractions spreading out from my pussy to the tips of my toes and up to my face.

M pulled me up onto his lap, stroking my hair and squeezing one of my tits as he told me how good I was doing, showing off my talents and his training to his friends, how orgasmic I had become from months of practice at his orders, showing him how devoted I was to pleasing him by developing a hunger for cum.

“You’ve got one more sip left. Can you handle it?”

“Yes, I can.”

“Tonight’s been a big night for you so far. We’ll give you a break after this, but we’re not done yet, ok? We’ve got another bottle filled with something extra special, and you still need to make up for that rude comment.”

“OK. I’ll do my best.”

“Good girl. Your dedication is why I’ve kept you around. You always show improvement. That pleases me.”

He held the glass up to my mouth, and I slurped up the remaining cum. His pep talk and lecture had brought me back down to earth a bit, enough for me to enjoy the taste again. Tangy. Salty. M’s cum with a hint of the anonymous guy’s mixed in.

I swallowed, and it seemed like the cumming went on forever. I was wrapped up in M’s lap. He continued to squeeze my tit, making my nipple get hard before squeezing the other. As the orgasm died off, I still felt the pleasure in my nipples as he played with my tits, and my pussy kept on throbbing as I went limp in his arms.

“Good girl. We’ll let you take a break. Go sit back on the couch.”

The anonymous guy stood up, shaking hands and thanking M, saying how he wished he could get Becky to drink his cum like that and he wished he could stay to watch me drink the second bottle. I guess whatever was next, it would just be with M and Jeff…

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.

I’ve been bound with leather belts once … like the ones straight off someone’s pants. One belt bound my wrists above my head. One bound my breasts. If I said “I liked it,” it wouldn’t do justice to how it made me feel … powerful, free, throbbing, special, girlish, beautiful, owned, ready to worship at his feet or perhaps elsewhere on his body. We didn’t go farther than getting topless and doing a little heavy petting over the pants – second seems like it would be the right base to claim – but the experience was a more intense, meaningful and important romantic and sexual first than was losing my virginity. It was something like losing my real virginity.

I believe my ex-friend/ex-top/ex-boyfriend, J, would feel something similar about our sexual experiences with each other … if not this particular time at second base, probably the first time we slid into home. “Coming-of-age” was the phrase he used to describe the date on which we actually fucked for the first time – the date on which he bought twine at the hardware store on the way to meeting me, and then tied my arms behind my back. The thin scratchy twine cut into my elbows dangerously but thrust my chest out in the most lovely way. The danger to the nerves that run through my elbows was something we learned about the next day, over breakfast with my kinky rope-bondage-loving friends – it certainly explained why it had hurt like hell when he tried laying me on my back while he had me tied like that.

But the belts at second base – the belts are most vivid in my mind. I had felt submissive a few times before with other lovers, including the anal experience with D which I’ve already written about. But the belts with J – that was my first real-life BDSM experience. It was his second. Especially given our ages at the time (him 28, me 31), our mutual inexperience with our core kinky identities is certainly a powerful and romantic part of the story in this vignette – a powerful aspect of our entire relationship in fact – we were each other’s first real BDSM partners. Yet there was another kind of inexperience making the hour with the belts worth describing – and appropriate in my broader story of male gazes, body image, and sexuality – it was only J’s third experience with naked tits.

J was 28, but he had the maturity and sexual experience of a 14-year-old. And so … even though he was wildly attracted to me, I feared the inexperience of his gaze more than anything. I feared a gaze that had been so thoroughly steeped in almost nothing but porn for a good 10 years longer than the average man. I feared a gaze and a mentality that not only paid for a subscription to Maxim magazine but also took the rag seriously. I also feared his lack of any sort of filtering of what came out of his mouth. He had said things about women’s bodies that were glaring red flags. There was the time he had made just about the cheapest, unfunniest shot possible at a party, blurting out “You can say that again,” in response to an un-self-conscious big girl cheerfully asking a guy to scooch his chair in because, as she put it, she was “too fat” to get past. There was the time I had asked him about recent dating prospects, and he described how his attraction to a girl ended when she got up from the table she was sitting at, revealing wide hips in the process. Ultimately, I was right to fear his gaze, and I should have feared it more than I did because, in the end, he hurt me terribly with it. But that day – that first bondage experience for me, that third naked-tits experience for him – his gaze and his introducing me to breast bondage gave me a temporary freedom from my worries about these things, a freedom that left me able to focus on the pleasure of submitting, a freedom to appreciate the experience of a deep need being plainly and enthusiastically fulfilled for real, for the first time – it was like gasping for air after holding my breath during the years of my youth.

For months prior to our first date, there had been extreme mutual attraction between me and J. Although it’s not necessary that I describe anything about those months in order to write up a vignette about our first time getting partially naked and doing some bondage together, I feel it’s only fair to talk about that attraction because it occurred under circumstances that were probably unfair and at times humiliating for J. I don’t want to write anything more about J without some context about the initial tough and embarrassing crush he had on me, which I couldn’t help but encourage because I was totally crushed out on him, too.

J was my boyfriend’s roommate. In fact, J was my geeky and brainy boyfriend’s even geekier, perhaps brainier, and most definitely – completely – totally – obnoxious and rude roommate. And yet … J was also hip, really hip. My best and most concise description of J:

A cross between …

Max Fischer, the genius prep school teenager, played by Jason Schwartzman, from Wes Anderson’s Rushmore …

one of the guys off of Jackass … perhaps this one:

and Michael Scott, the boss played by Steve Carell, in The Office …

Let’s take a moment and reiterate that last one – when I watch The Office, I get eerie flashbacks to J acting just like Michael Scott. Anyone who has watched The Office may find it hard to bel
ieve any woman would be into someone who literally behaved like that character, but I was – I was totally into him.

J’s life imitating pop culture doesn’t end for me there, though. If we use the traditional definition of first-time vaginal intercourse, J had lost his virginity at age 28, only a few weeks before meeting me, and his sum total sexual experience prior to that was a single blow job and a few French kisses. So there were also some strong similarities to another character Steve Carell has played – The 40-Year-Old Virgin:

The upshot was that J desperately needed to grow up in a lot of ways, sexually being just one. As for me, a 31-year-old who had had the adjective “mature” applied to me in its non-porn sense by various family members, teachers and friends since a very young age, I had a need to be less mature and have more of the fun I felt I had missed out on in my teens and 20’s. We were in for a dizzying train wreck.

My intentions were mostly good in initially trying to channel my attraction to J into friendship – trying to be a confidant, mentor and cheerleader about dating, women and sex. I had also worked hard to be honest and open with both my boyfriend and J about my attraction to J, as well as my loyalty to my boyfriend, so that no one felt misled. I don’t think I did anything truly wrong or dishonest under the circumstances – it’s not like I went looking for J. I had a good thing with and was wildly attracted to the vanilla boyfriend myself, and I didn’t want to mess things up with him. But before I write anything more about J and his ADD gaze – immature and porn-addled to the point of cruelty one minute, deliciously objectifying and accepting of my real body the next minute – it’s important that I confess to my own girlish immaturity during these months before J moved, and my boyfriend gave me – his polyamorous (and married) girlfriend (have I mentioned I’m happily married?) – permission and rules under which J and I could pursue our mutual attraction physically. (Whew – did you get all that? ADD gaze, affirming and immaturely cruel. My own immaturity, about to be revealed. My boyfriend saying J and I could date and fool around, after J moved out of their house. And yes, I’m married.)

Before my boyfriend relaxed his rule against J, during the time J and I were dangerously flirtatious “friends,” I found the love triangle terribly exciting. I was as giddy about the two of them as your average 16-year-old just discovering lust-love. I flirted with J pretty shamelessly, sometimes in front of my boyfriend, sometimes when my boyfriend wasn’t there, sometimes over email, sometimes in front of my boyfriend and all their friends. In my defense, J needed my flirting bad. I also loved it when J flirted with me, something he took every opportunity to engage in. It gets worse, though … J’s room was right above my boyfriend’s room, and I was loud when my boyfriend fucked me. Sometimes I was even louder because wanting J, too, led to my wanting him to hear me and think about having sex with me, and all of that made me that much more turned on and loud. And I was the one to suggest going on walks together, when my boyfriend was too sleepy or lazy to join me excercising. J and I would talk about sex and dating on these walks, under the guise of friendship. But in actuality, our talking about sex and dating relieved and fed my desire for some sort of sexual interaction with him, without crossing any boundaries of physical intimacy. Well … except for the time he lamented his thick curly Jewish fro hair, and shocked at his self-hatred of a physical trait I found really sexy about him, I reached over and stroked my hand through it, telling him how much I liked his hair, discovering how good it felt in addition to how good it looked; his head nuzzled into my hand, hungry for being touched. And well … there was also the time he hopped behind me and deftly maneuvered me to a sitting position on the ground with his arm around me, before I even knew what hit me. I sat there for a minute feeling a mixture of excitement and guilt about encouraging him and toying with our flirting like this, behind my boyfriend’s back. That particular interaction prompted one of my open talks with my boyfriend, again making clear to him I was attracted to J but hadn’t crossed any lines he found important (no kissing J, no sex with J) and wouldn’t cross those lines without permission.

J’s desperate needy attraction to me was revealed in plain and sometimes explicit detail on these walks – J was into me for sure – but he also really really needed sex, something he’d only experienced four times. He was somewhat willing to take any female that came along, having lost his virginity with a girl he really didn’t find attractive. My thorough attraction to him was revealed in plain detail on these walks, as well – I oozed with compliments on his looks, his brains, his coolness – I laughed and gushed at his jokes and his teasing me – he made me laugh in that way that instantaneously turns a girl’s clit into a throbbing drain on the blood in her brain. His thorough potential for being an insensitive thoughtless prick about women’s bodies was revealed on these walks, too, as was his related talent for the type of objectification I adored: a lewd yet clever remark about staring at my tits; my favorite kind of compliment – one I’d never heard before – directed at my shoulders, their cuteness, and how effectively I communicated and flirted with them; telling me about my boyfriends’ buddies at the gym the week after they all met me – they discussed my nice, big, full, round, perky tits. The picture he painted was one of approval, admiration, wonder, envy. The approval, admiration and wonder was intended for my tits. The envy was for my boyfriend. I reveled in his tale of me being objectified, and I smiled at the implication that the perception of my tits made my boyfriend more of a man in their eyes. I loved and admired my boyfriend and felt he deserved the kind of envy that comes from having a sexy girlfriend. At the time, I felt no need for it to be known, nor guilt nor shame, that any approval, admiration and wonder was actually for my bra, since my tits were only round, full and perky when corralled in one. In fact, it filled me with pride at my ability to pick out great-supporting bras and fool them dudes with what appeared to be eye-popping perky tits.

But most importantly, my and J’s mutual desires for and inexperience in BDSM were revealed explicitly on these walks. I do believe our top-bottom dynamic was there from the very first time we met, though. I left the take-out teriyaki place, at which I met my boyfriend’s friends, indelibly marked and intrigued by what felt like hostility yet desire from J. My perception of hostility/desire made all the more sense when my boyfriend later told me about J having only had intercourse for the first time a few weeks before – a virgin at 28, he must have had a lot of resentment towards women. The hostility/desire made even more sense on the walk in which I confessed to identifying as submissive and J confessed to the type of porn he liked – bondage – in particular, rope bondage.

We didn’t have any rope at second base, though. We only had his two leather belts … and lots of anticipation …

Lots of anticipation.

A few hours after our actual fooling around with the belts, I wrote him an email about the sexual fantasy I had been having about him for months. The fantasy was inspired by our friends-only predicament, my tendency towards fantasizing about forced sex, and his mentioning the way he had used the belts off of his pants to do some bondage with that first girl he fucked a few weeks
before we met. I wrote:

Being with you today was intensely good. I lack adequate words for it.

My fantasy about belts and silence:
We’re still not supposed to be doing anything beyond friendship, so I’m settling for friendship. I want to help you with the whole sex/girls issue. I want to learn more about BDSM myself. I want to do things like go to munches and meet other BDSM types for talking and learning…community. I want to see your BDSM porn. I’m curious about your having tied Shelly up with belts, hands behind her back, ankles together. I don’t understand how you would get belts to do that…do they have special notches way in close so that they’ll be tight around the wrists and ankles, which are much smaller than anyone’s waist? I’m curious about how the belts would feel. Would I like it? Should I put BDSM higher on my sex to do list? I’m visiting you, we’re in your room, I ask you to tie me up with the belts like you did to Shelly. My conditions are the belts will only stay on for a few minutes and I don’t want to be facing you–I don’t want you to see my face–if the belts cause me to feel sexual, it won’t count as cheating if you don’t see my reaction–and I’m embarrassed at the thought of you seeing me react anyways. I’m kneeling. I’m in front of your bed. You belt my wrists, then my ankles. You let me experience the feel of it for a few minutes. Then you come up behind me and cover my mouth…press yourself against me…grab at my tits. I feel scared. violated. wanted. not responsible. at your mercy. dumb/naive. You pull up my shirt. You undo my pants, pull them down. You bend me over the bed. You fuck me with one hand over my mouth and one hand holding me down, sometimes on my shoulder, sometimes my neck, sometimes my hip, sometimes the small of my back. Big, strong, hands.

J wrote me back:

Missy,

I’m a little confused… did you write this before today? “We’re still not supposed to be doing anything beyond friendship, so I’m settling for friendship.” Or is this just a part of the fantasy? Because it’s part of my fantasy. I won’t tell you exactly what is involved, should it ruin the surprise… but it starts with us doing something “friendly” like watching a movie on a couch. We have agreed previously that it’s not ok for us to be sexual and that we’re just going to be friends for the time. At some point in the movie I clap my hand over your mouth and tell you that if you don’t do what I ask you to I’ll hurt you. I use my other hand to feel over your chest, slowly circling in to your crotch…

Anyway there’s more, but the general “thrust” of things is that you’re being violated, taken against your will. It’s very similar to your fantasy I think. I love to see that we’re so aligned.

Mmmmm, yeah. We found it terribly romantic that unbeknownst to each other, we’d both been independently having fantasies about him “raping” me for months. Like I said, lots of anticipation.

The story of this second-base date is even more wild, though, and I’ve debated about whether to include these details because I’m not going to explore them in a meaningful way and they may further distract from the parts of the experience I most want to emphasize – the gaze, the bondage freeing me from my worries about the gaze. But the fact is the whole polyamorous married thing is a fundamental aspect of our first date. J and I were actually on this date with my husband. My husband and I had picked J up from the train station the night before, and then the three of us had gone out to dinner, with J playing footsie with me, and me playing footsie with my husband under the table. We all went to a party. J and I stole away from the party and made out in the backseat of our car at one point. That first kiss, the opportunity to run my hands through his hair freely, was incredibly intense after 6 months of flirting. We stayed the night at a friend’s – my husband and me in one room, J in his own room. In the morning, I asked my husband if I could go to J’s room for a while after we fooled around, and my fooling around with J occurred during my husband’s post-BJ-slumber. As if that isn’t enough outrageous but earnest polyamorousness, there’s more – I had a visit planned with my boyfriend immediately after my three-way date between me, J and my husband. I timed J’s and my boyfriend’s train departure and arrivals to avoid the two of them meeting awkwardly at the train station, and I confess, I liked it … I liked it a lot that they were passing each other on opposite trains for me … the official start of the four months during which I dated two guys in addition to my husband was incredibly exciting, and scandalous, no? Perhaps I’ll write more sometime about carrying on with three relationships at once (and why I won’t ever try that again), but as I’ve said, today is about belts, gaze, and freedom in restraints; today is not about maintaining sexual restraint.

While still in the room with my husband the morning after the three-way dinner, the party, and the making out in the back seat, I heard J get up and go to the bathroom. After it sounded like he’d returned to his room, I opened the door of our room and saw that J’s door was cracked. I tiptoed across the hall and peaked through the crack. J was lying in bed, apparently dozing again. I pushed my way in, and closed the door behind me. He perked up and said that it looked like I had accepted his invitation – he had cracked his door open expecting me – hoping for me. He lifted the covers. I slid in beside him. We pressed against one another. I felt him hard through his thin pajama pants. I felt his hard naked hairy chest. We made out. He felt me up over my top and bra.

And then, it was time. It was time for my top and my bra to come off.

But, of course …

Of course, I was reluctant.

I was reluctant to share my body, especially my tits, with J. It wasn’t just the red flags of J’s words about other women’s bodies making me suspect that he would not appreciate my body. It wasn’t just that I could no longer be so carefree about his and his friends’ misplaced praise for my full round perky tits in fact being praise for the bra I’d have to take off if I was to share my real body and my real self with J. It was also that my history with D had me scared – I didn’t want to expose myself to another guy with an insensitive, cruel, youth-obsessed gaze intent on some ideal I didn’t fit – I didn’t want to share myself with someone who didn’t appreciate the beauty and uniqueness of my natural breasts. I expressed some of these things to J, less eloquently of course, and I remember his response distinctly. I was lying on my back. He was laying next to me, over me. He said, “I’ll see your flaws. That’s cool.”

I sort of liked that comment and sort of didn’t. D identified my breasts as utter total ugly flaws – flaws being a word we argued about extensively – so I winced at the mention of flaws at the same time that, “That’s cool,” put such a different spin on it.

J did some more coaxing, saying that it was a shame that my experiences with D were affecting our experience together – because he wasn’t D – D was an asshole – J was a nice guy – and J needed this with me. He appealed to my desire to correct what I saw as the injustice of J’s lack of sex, love and attention from women in his life.

Persuaded, I decided to take control of my exposure. I decided to take my top and my bra off in a way and in a position that I felt effectively presented the loveliness of my naked breasts. I sat up opposite of him, kneeling on the bed, strong proud posture, but obviously vulnerable. I looked at him. He looked back at me. I took my top off over my head. I unhooked my bra in the back. And then I took my bra off the same way I’d taken off my top – over my head, lifting my arms, lifting my breasts.

Perhaps he was be
ing kind. Perhaps he was fooled by my posturing and positioning. Perhaps he was lost in the moment and had lost his true gaze in the process. Perhaps he was just desperate and willing to settle for my saggy tits. But I think in reality, he really believed and felt what he said at the time, and his change in attitude later – a year later, when he berated my body – was his ADD gaze and temperament at work.

After my bra came off, and I was sitting in front of him topless, waiting for his reaction, he didn’t skip a beat … he said, “They’re beautiful. I don’t see how you could think I’d think otherwise.”

I was so relieved. I felt safe.

He perked up again – delighting in an idea – remembering something he’d brought for us to play with. He got out of bed and went searching for his pants in a heap of clothes he had taken off before going to bed and piling them on the floor. He fished out the pants and then pulled the belt out of them, tossing it onto the bed and the pants back into the pile. Then he went to his bag and got out a second belt. He uncoiled the belt and pulled it taught, teasing me, “Why would I need two belts on an overnight trip? They’re not even different colors.”

I learned how a belt would bind my narrow wrists – no notches close in like I had envisioned – no, he wound and wound the belt around my wrists, which I had placed out in front of me, offering them to his control, and then he secured it in one of its regular notches, one of the notches he used when wearing it around his own waist.

I learned how it felt – tight, secure, safe. There was such pleasure in him laying on top of me, our naked chests pressed against each other, as he hooked his thumb in the belt and used his strength to stretch my arms far overhead – conveying a feeling that I was his to toy with.

He talked about the sounds the leather makes. “Don’t you love those noises?” I did. The leather creaked from being stretched taught and rubbing against itself in its coils around my wrists.

Then he told me about how much he loves breast bondage, and he asked whether he should bind my breasts. I readily agreed, eager for the experience, eager to please.

Before he bound my breasts, during the time he only had my wrists bound, I had been enjoying it immensely, buuut … I was also mindful of being close to a position I tried hard to avoid, even with guys whose gazes I completely trusted. I confess: I don’t particularly like the shape of my tits when I lay flat on my back and they flop to the side. With my arms overhead instead of pressed against the sides of my chest, I couldn’t do what I’ve always done while lying on my back, whether naked with a guy today, or alone at age 13, examining what my tits did and how they compared to my concept of what breasts were supposed to do when I laid on my back. With my arms overhead, I couldn’t push my arms under my boobs to prop them up and make them into round mounds beneath nipples that point straight up towards the ceiling. I had to settle on a compromise position – twisting my torso a bit, balancing my right breast so that it appeared large and full on my chest – only the left breast sagged and flopped to the side, and even that particular flopping and sagging was in a shape that was rather pleasing to me, as opposed to the flat flopping that occurs when I’m flat on my back. Eagerly anticipating the breast bondage, I was unaware that it would free me from these worries about the shape of my breasts. I also presume J remained unaware that binding my breasts let me drop my guard about twisting my torso just so.

J had me lift my torso up so that he could slip the belt underneath me. He wrapped the belt around my breasts, right across my nipples – the leather was cool and smooth against them – and once he tightened the belt, I enjoyed the feeling of pressure permeating through my tits, my whole chest in fact, giving me the sensation that he controlled one of the most sensitive erogenous zones on my body. But something else happened once he tightened the belt: my tits stood up straight against gravity – they bulged and strained against the tight leather, just the way those fantasy tits I lacked would bulge and strain.

Freedom, I do say. Freedom to lay flat and relaxed on my back. Freedom to enjoy a perky shape without destroying my natural shape with surgery or implants. I like belts as much as I like bras, maybe even more.

Bras are incredible works of fashion technology, aren’t they? I really love them. I love the way a pretty bra looks, decked out in lace and ribbon, or eyelets and scalloped edging, or simple satin. I love the way a good-fitting bra feels, too. Tight around my torso, lifting and cradling my breasts in one place, holding them still and close, and then, the feeling of release and relaxation when I take it off after a long day. In 7th or 8th grade, my boobs were perky for about five minutes before they gave under the pressure of their size and decided to hang a good five pencils below the passing grade for the you-don’t-need-a-bra test. They still hang like that today:

Since I’ve failed the pencil test ever since I got breasts, I have taken full advantage of the wonders of bra engineering. I have to say that I am quite satisfied with the comfort and support they have provided me for the past 20 years. Bras have allowed me to live an active life – running to catch buses, dancing for hours on end, hiking up mountains, jumping up and down in triumph and glee, doing somersaults and cartwheels on green lawns well past my flat-chested childhood. These things would be painful without a good bra keeping things from bouncing too much.

The bra I burned for my Feminist Pornographer header is my favorite of all time. It’s pretty. It’s comfortable. It gives me great support. My boobs look hot in it under a variety of tops and dresses. I originally owned three of them, but now, I’m down to one because the one I burned for my header is the second one that’s gone up in flames. I’d like to write about Dan Savage burning the first one for me sometime. But I figure if George Lucas could release the 4th episode in the Star Wars series first, I should be able to write about Bra Burning II before I write about Bra Burning I.

The bra in my Feminist Pornographer header didn’t actually go up in flames completely—I stopped about here:

I would have liked to display this charred and half-burned bra somewhere in my house. But I was already concerned about having inhaled too many dioxins during the burn itself, and the half-destroyed bra still smelled like burnt plastic, even after sitting outside to air out for a couple days. So it went into the trash.

My burnt bras were Warner’s Sheer Heavan Underwire Bras – Style #1502 – size 34D. I know these details because I wrote them down to be able to order more of them. Alas, the style was discontinued in February of 2007, and I didn’t figure that out until after I burned them. I have to confess that if I had known I wouldn’t be able to buy more to replace the ones that went up in flames, I might have thought twice about destroying two of them. A good bra is hard to find, and this bra has additional merits that my other styles don’t possess. Because it is see-through and nude-colored, wearing it may be the closest approximation of the classical nude breast I can create on my own body, without surgery. I like that. I like that I can enjoy a mimic of the perky look without destroying my natural shape or risking loss of sensation. I like the way I can use it to show off and present my nipples to a lover if I so choose – if I feel safe with a guy – if I am confident his gaze and his hands enjoy my unsupported naked breast, too.

But the useful qualities of this bra for sex and fun and fashion have also made it a symbol of pain for me. You see, this bra was one of several that I bought specifically for the purposes of wearing in bed with D. Our arguments about the attractiveness of my breasts led to me wearing bras during sex, and his ultimate refusal to take my bra off, even when I wanted him to, was … how should I put it? … fucked up. I like erotic humiliation, but my earnest shopping for bras and tops in order to please him but also, somewhat subconsciously, deny him the privilege of the tits he had insulted; my focus on choosing styles and fabrics I thought he, in particular, would like; my hope that he would back down, that he would change his mind and get me completely naked because he wanted me as I was; my hope that he would understand how much I needed to be naked with him; his consistently and contentedly taking off every other stitch of clothing on my body besides my bra, over and over again – that wasn’t erotically humiliating – it was just plain humiliating. But this particular bra gets even better as a symbol of pain and male gaze assholery for me – it’s the same bra I was wearing when J – having been enthusiastic about my boobs for months and having known my history with D – did an about face and, like D, wanted me to keep my bra on during sex.

Just as I want to post about my first bra burning some other Sunday, I also want to write about these experiences with D and J in more detail, in the future. There are nuances in the he-said-she-said of our arguments and actions I want to explore at length, but for now … this week … I am distracted by writing about something else … the glow of flames, the heat of combustion, the discovery of my inner pyromaniac.

It was fun to burn this bra.

Really. Fun.

I’ve never been particularly into fires. I’ve enjoyed plenty of nice ones that someone else has built in a fireplace or campground, but I’ve never desired fire enough to make one myself, or prioritize living in a house with a fireplace. I was never tempted to play with matches as a kid. And although I liked fireworks on the 4th of July at times, more often than not, they scared me. I took adult warnings about the dangers of fire very seriously. But I’m an adult now, and I really … really … enjoyed setting my bra ablaze.

To get the shot of me in the bra, the shots of the bra in flames, and the post-burn braless shot, I set up my digital camera on its tripod, planning to shoot in its movie mode and then extract still shots from the movies on my computer. During the shoot, I had my blinds open to get good light. I live on a busy street, so I was counting on the glare from the sun on the windows to prevent people from seeing in. I’d estimate that 100 people drove or walked by, while I was standing nude and able to see them clearly and head on, outside the window I was standing opposite of. There were plenty of times that I ducked down worried that they’d see through the glare and I’d offend someone with my blatant nakedness, but no one seemed to notice me from what I could tell. I played around a lot with the placement and angle of the camera. I did a bunch of practice shots, holding the bra out at different distances and angles from my body. I had to strike a balance – framing the bra within the shot and framing my body with the bra, on the one hand – and on the other hand, maintaining what felt like a safe distance between my body and a fabric whose flammable properties were unknown to me. If I held it too close, I feared burning myself, especially if the burning bra got out of control. But if I held it out too far, part of the bra would be cut off in the shot.

When I thought I had the angles right … when I had practiced holding still in my protester’s pose, and keeping my face plain and serious, and covering my pussy with my hands to emphasize the nudity of my breasts, and holding the bra out so it was fully in the shot and not blocking the view of my breasts and not twisted or folded … when I was finally ready to light it on fire, I put 3 big pans and tupperwares full of water on the floor, underneath where I would be holding the blazing bra. I envisioned lowering the bra into the water to put out the flames if they got too big, and having the water right there to squelch the flames was, in fact, useful and necessary. But I didn’t anticipate the other purpose the pans of water served in protecting me and my house from fire – it surprised me when pieces of the bra, still aflame, fell off of it, hit the water, and hissed as the water extinguished them:

It was all thrilling. It was hard to keep my face plain and serious for the protester look I was going for. The movies caught giddy smiles on my face each time the flames got too big and I relaxed from my pose in order to lower the bra to the water.

When I first put up Feminist Pornographer, I had a different version of the bra burning header – a more extended version, filling the width of my blog. At least it filled the width when I viewed it on my computer. This was before I figured out how to code the layout in my header the way I really wanted it. I like the simplicity of the three-panel header and how it draws more attention to the statement I intend it to make (which is something like: You want ‘em perky? Fuck that. I’m staying saggy). But the extended version has its merits, too – more variety of flames, a display of the progression of the burn. It was hard to choose the winning bra-on-fire picture to go in the three-panel version. I like each of the pictures in the more extended version:

Does my header picture communicate? It probably does most of the time, but I rejected an anonymous comment on my “Feminist Posing” collage from a few weeks ago because the commenter really didn’t get it. The comment was: “on this pictures you look much more better as on the ‘blog headline picture’. keep it up” … Dude doesn’t get it – dude gets his comment rejected. Although today, that’s changed to dude doesn’t get it – dude gets his comment written about. Perhaps the anonymous commenter is not a native English speaker. At any rate, I presume he has not read anything I’ve written on here, just as I presume he’s a guy. Or perhaps he has, and he doesn’t understand it. Or maaaybe, the dude totally gets it – maybe his comment was intended to get under my skin – that would … impress me. At any rate, I realize – in fact, I even hope for – the irony and pathetic-ness in my putting up pictures and essays intended to counter and comment on his type of attitude and then finding myself the object of his type of attitude – perhaps he or others will post more comments describing exactly why I look much more better posing with the backlighting: because it minimizes my cellulite? because I look thinner? I also realize the backlit pictures of me posing in the mirror with sex appeal in mind are more likely to be beaten off to – and that’s fine – I intended them to be presenting my body for sex … for consumption. And although it wouldn’t surprise me if they’ve inspired some beating off, too, I intended the header pictures to present my body for a different kind of admiration – thought, art, principle, independence. So don’t get me wrong – I like the backlighting and the posing, too – and I appreciate compliments on the sex appeal of any of my pictures. But really, I look much more better in the header – straight on, in full daylight, plain and simple; wearing nothing but my painful, comfortable bra – an icon of femininity, a false presentation of my most feminine features; and then taking it off and letting it burn, admiring the glow of its symbolism … the slight upturn in my mouth. I could barely keep that smile off my face because I felt free.

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.