Additional Author’s Notes
I think most people get very turned on by the things I described in the author’s note but don’t appreciate them because a cultural obsession with shock value and ejaculation, shaped by the most commercial forms of pop porn and obsessed with monetary gain but never female pleasure, has created an artificial kink-“vanilla” divide which serves (and services) nobody.
The background is a little meandering but helps see my unique perspective; as a pop culture student, I have renamed the three women in these episodes after a classic Elvis Costello ballad, a silver screen sex symbol gone too soon, and a classic Stones smash. See if you can see why the names are apt; the subtitles are honestly just takeoffs on media and ad tropes one finds traversing this great information superhighway, magical creatures of the Internet that I have found IRL.
Prologue
Where did it begin? Why did I come to want encounters now deemed “vanilla” with curvaceous women so bad? Nobody ever fully knows, but three major factors emerged quite early. First, a large slice of my childhood was spent in Europe, specifically an area where touch is more a part of everyday interaction and in a pre-social-media era when attitudes toward sex and nudity were freer than in my native United States; ever since, having lived there has intrigued American women I come across due to the romance of that part of the world, my ace in the hole. (No pun intended.)
Second, deprivation in the dating game of deception where I lacked the guile and physical coordination to play and win in my teens and twenties, especially once I was forced to start over around a mid-sized Midwestern city far from the suburbs of a large one I’d come to know. My intimacy thus was cut off more or less by this and my lack of a driver’s license (crucial to Midwestern rites of passage) until after university/college, limited until my twenties to requests for dates that didn’t fit millennial culture with a protective (perhaps over) mother preventing the kind of unsupervised hangouts where couples actually bonded and formed.
Third and finally, as far as my preferences, Freudian forces may have played a role in my enjoying voluptuous figures more and more as I got older; my mother struggled with a modest weight issue and the underwear catalogs that I discovered before becoming Internet-savvy were Lane Bryant rather than Victoria’s Secret. The BBW niche appealed to me, but I gradually came to see most gonzo pornography as good for laughs and little else, preferring romantic scenarios and amateur couples’ vids that made love rather than just fucking.
My twenties coming to an end and my growing income after the recession threw me and my mother into rentals got me to think that the pipe dream could come true again, essentially starting from scratch since efforts to convert on real-life friendships had never panned out.
I had the misfortune to be starting out on online dating with no sexual experience past puberty right around the late 2010s, when the industry was shifting from personals with first name and pictures to social-media addiction farming based on rapid swiping. I looked decent but struggled with a height of 5 foot 6 and a belly I never flattened completely but tried my best with mostly walking aerobics but occasional reps, plus, my hobbies in photography and a dream of pop culture writing/blogging helped round out my life of underemployment.
Considering the odds I was working with starting at twenty-nine as the above, my first steps weren’t so bad, mainly because I took the sliver of matches I got and made a serious effort to get to know each one. Most were either very inexperienced women my age or older women who were more interested online than off in becoming intimate. My first multiple-date pairing was two hours away but seemed to make things worthwhile by sexting extensively, only to marry the next partner she announced on social media I could see; a couple women roughly five years older were the first I kissed on the lips since high school, but the pattern of next partners “sticking,” perhaps due to age, held for a while.
Getting off a series of meds, catching COVID, and moving into an apartment (still at home given housing costs and some life skills issues admittedly, but with the occasional sound of bedsprings and muffled moans that motivated me to go for the real thing) in 2022 set the stage for the episodes below, as fantasy started to collide with real life with women two to five years younger than me.
Episode I: Allison, the Manic Pixie Dream Girl
Taken advantage of but determined to decorate this drab world, Allison rolled into town with little to her name and a yen to start over. She started out in the same multi-city area as my first relationship four years earlier, dreaming of working in handicrafts. Like many bipolar women, she was vulnerable to love-bombing while manic and succumbed to a physically and emotionally abusive fellow who impregnated her with three children. Never marrying, he would beat her when dissatisfied with her depressive state, which she tolerated perhaps to feel alive even as he set problematic examples for their children, also turning to tobacco as her seemingly only vice.
Allison was accepted into a supportive shelter for battered women but struggled once placed in independent housing with rude neighbors, including one particularly nasty lady on meth that sometimes threatened the little dog that was intended as protection. Admiring my support for my mother after my parents’ separation and feeling safe with my quiet personality grounding her manic phase, she allowed me into her apartment and world for a few months of that winter and spring. Delicate but somewhat rounded from her pregnancies, she charmed me from the start as the sort of classic eccentric artist I had long wanted to date in my hipster phase, though the baggage gave me pause as it would anyone.
I went on a lovely first date with Allison, bouncing from the art museum to the library to the apartment she was already making her own, where she cooked me eggs. A kiss goodnight and some help moving around furniture from the last tenant were the extent of our intimacy, but the next time would beckon more.
The next Saturday, Allison had gotten a movie (on RedBox I believe), Lars and the Real Girl, odd date choice focusing on a fellow and his love doll he gradually untangles his trauma and leaves behind, and after a coffee date where she held me and kissed the side of me to the point where the owner would later recall her as “my wife,” we went to her place per her plans to cuddle and watch said film.
I had accepted her wish to take things slow, something some previous partners in town had been more rude about (including one quite fond of a certain TV personality-cum-President whose following I never joined thus endearing me to that side of the growing political gender gap). Fully clothed, I kissed her from time to time. She Frenched me and I returned the favor, proceeding a few times off and on as we enjoyed each others’ warmth on a cold February day. I once told her “You’re so beautiful,” sincerely believing her mix of emo and neo-Bohemian fashions to be some of the most striking I’d ever seen, only to be told in the same whisper, “No, I’m not.”
Wanting to prove Allison wrong and feeling my loins begin to stir, I asked her if she was interested in getting a bit adventurous. She said things were fine staying like this for now, noted my disappointment, and appreciated my respect for her consent.
One of our last kisses, perhaps testing this boundary, I moved down from her mouth via her neck to her upper breast. Taking care not to touch anything overly intimate (her nipple was fully covered in her shirt), I pulled back as I saw her twitch her legs back and forth looking somewhere else, somewhere blissful, in her striking eyes. She got up, told the cute puppy, “Mommy got a little excited,” and excused herself to the bathroom, returning after a few minutes with a smile on her face; only much later did I realize that I had likely brought her to climax, thus missing the opportunity to go into the bathroom myself to use it while sniffing the first panties I had ever soaked.
Allison promised me as we parted that she would be worth the wait and looked forward to being together fully, saying she had “techniques” in which she was excelled. Her next suggestion piqued my interest, making me spaghetti at her place a Friday night before Valentine’s Day. Buying a chocolate set from a local confectioner, I was all set to join her for what I had every reason to expect was a third date of passionate escalation, only for her to cancel at the last minute. First feigning illness, she told me she was “too broken” and had returned to her abusive partner.
Accepting this as par for the course, I was surprised to see Allison return come April as her manic state had returned. This time we hit another cafe after she had cat-sit for a bit of a hoarder in the neighborhood, leading to some odors that were not the most pleasant. She took a great photo of me, let me open and close her doors as a gentleman, and stopped by a thrift store to get some items including a dress. I picked at her insistence among the slinkier of the numbers, which she offered to model at her apartment. It was more of a nightgown as it turned out, so she told me she wished she’d worn sexier underwear (her black panties framed her heart-shaped ass perfectly, as I told her). Time pressed us but we agreed to meet again.
I did not feel comfortable bringing Allison into my move to the new apartment, with which she offered to help, and after some lost contact she informed me a few months later that she had been assaulted by the meth addict neighbor’s boyfriend and ended up leaving with her dog to live elsewhere. She moved further away from the ex, gained custody of her kids, and is now with a mild-mannered man who reminds me of myself in some ways; still keeping in touch now and then, she has made enormous progress in controlling her challenges, and opened my heart to the struggles of so many I had hitherto read about in books and news articles. I am very proud of having shown her she could expect more from a man than the cruelties she had known.
Episode II: Marilyn, the Single Mom in My Area Who Wanted to Fuck Tonight
As I progressed from woman to woman, they became more locally rooted and less experienced with life; perhaps it is simply that I see more with my own growing experience behind the “face value” in those who have not decided to take that fateful initiative to become the pursuer. Marilyn may be the first BBW in this list; her shapely rear and modest but sensitive breasts, along with hair with an ever-so-slight kink, betrayed a very different background from Allison. I guessed her to be perhaps Hispanic or among the many Micronesians to settle the area, but she revealed herself to be biracial (Black / white) during our courtship, one of five scions of a local farmer’s daughter and an African American fellow who seemed relatively accepted in a suburb of the small college town half an hour away where she lived despite very problematic unspoken racial dynamics in this part of the country at times.
An ambitious go-getter rising up in her hospitality field, Marilyn shared custody of two children with a man she told me was her only prior lover since high school, all white like myself (I’m half Jewish and half Scotch-Irish/Norwegian, he was probably more of the latter) judging by the kids’ straighter hair. She had stretch marks and some self-consciousness about her body, but once I made it clear I accepted her things proceeded beyond my wildest dreams, and perhaps beyond what she wanted as someone looking for “something beyond friends with benefits” but not a boyfriend just yet.
Over September as I settled into fall at the new place, I and Marilyn chatted. I cancelled our first meeting as an opportunity came up in a different town the same distance away; that woman had some drug problems in her recent past, and while she was pleasant enough, there were too many echoes of the difficulties I had with Allison to proceed further. Perhaps I inadvertently ratcheted up the tension with Marilyn this way, as she let slip that she “hoped I like her” when we meet.
Naturally chuffed at the eagerness of this single mom to see me, I settled into my usual pattern. I had found some videos of women resembling her in action, and they gave me great inspiration, so I had admittedly indulged in several rounds of self-pleasure before our date. Perhaps I expected the old saw about being relaxed to be true, and perhaps I was proven right, though the costs would be apparent as well. We met at the local pizzeria and had to eat at the more unassuming bar next door; I rolled with it and on our lovely fall date of fertile conversation, this woman noted her kids being with the ex and offered several next steps beyond dinner, including the fateful option of “my place.” So it began.
Rolling in to public parking in the town’s complex system, I followed Marilyn to her humble apartment. We proceeded to watch some random entertainment, believe it or not the Bob’s Burgers movie was what ended up being the bill of fare. I didn’t care and have never been very decisive on this sort of thing, rolling with it and holding her hand after she hadn’t necessarily been much of a hugger or kisser.
Fifteen minutes in or so, she did and said something that will be burned into my memory forever: clasping my hand under her shirt to her bare breast, she said, “You’re so shy.”
The touch barrier broken at last, my hand on her intimate area, I began to rub her and this time closed in for the kiss successfully. After she asked if I was comfortable with more, I asked to see more of her and was rewarded with her sports bra coming off entirely.
Caressing her soft back and belly, I asked Marilyn and heard a glorious “Yes” if she wanted me to lick her breasts, so I proceeded from experience to tease her areolas and was rewarded by her soft moans under her breath. Still having my undershirt and skinny jeans on (we’re millennials, don’t judge lol), I let her straddle me in lap dance position, and we made out and petted as her desire grew. She began to paw at my now somewhat turgid member, and I began to slip my fingers into the waistband of her leggings to rub the soft cheeks of her bubble butt. Finally, I asked her if she wanted to have sex, and she agreed and led me by the hand up the stairs to the bedroom of her suite.
The details of my first time are vivid as I’m sure they always are. Marilyn was too horny for a full striptease, so it was not long after her black leggings dropped to the floor that her purple briefs joined them. I asked if I could go down on her and she spread-eagled with her eyes closed, exposing to me the most beautiful thing I had ever seen. In full bloom and open to pleasure, her clitoris beckoned me.
I was not prepared for some of the smells and in retrospect could have and perhaps should have spent more time down there, but it thrilled me to hear her breaths quicken as my tongue massaged the folds in the garden that had brought two children into this world. Rising up to kiss her, I positioned myself between her legs, and after sliding the magnum that seemed like all that could accommodate my six-inch girth (equal to length) onto my cock, she guided me into the depths her ex-husband alone had plumbed. Her body heat radiated through me and I felt the first twitches of her muscles exquisitely wrap me within; as I struggled with the rhythm and with maintaining hardness (which I attributed to being over-masturbated in the prior 36 hours), I revealed to her that she was my first lover.
Marilyn took pride in this and told me she wished she’d been able to prepare me better, but I told her the anxiety might have made it worse and that the magic of the night was what I needed (not telling her the perhaps unnecessary detail that most men fear the stigma of revealing this, especially at an age like thirty-three). To make me harder, she got down on the floor and gave me my first blowjob, expertly sucking on the whole member between occasional licks at my balls. She tried to ride me with another brand of condom, but though my nether regions throbbed with warm stimulation and she enjoyed my alternation between kisses and breast play, we could never square the circle and get me balls deep or cumming.
At first unsure whether I loved her appearance (“Maybe you just don’t find my body attractive,” she said to the breaking of my heart), I reassured her about her body type being my fantasy (no lies there). She even offered to take me raw, claiming to be tested and on birth control with only her ex as a prior partner and obviously none for me, but I declined given my discomfort with this for our first encounter.
I had a great discussion with Marilyn afterwards, where I disclosed diagnoses, things about my past, etc., that I might never have with a woman I had not penetrated. She was glad to see me again and we exchanged numbers, though I ironically never got suggestive pictures like I did with other women (including one trying to get me to subscribe to her OnlyFans) uninterested in flesh-and-blood activity.
A couple hours later that night, I masturbated to erection and completion to the memory, implying that all was not lost in this department.
While we went on another date and got along well enjoying our mutual hobby of walking/hiking, she was unwilling to hold hands at the café we stopped at for a sandwich lunch, perhaps a sign she did not wish for a relationship. Perhaps I came off a bit immature mentioning possibilities for more (I joked we could get clean before we get dirty or vice versa, a true lead balloon if ever there was one), since she found out shortly after getting home that her ex had picked up the kids from school early with an illness.
Unsure whether I could keep being her sneaky link, I took her stated unwillingness for anything deeper as a sign our sexual partnership was over, but we kept in touch now and then. Perhaps I was spoiled, as intimacy seldom came as early as it did with her, but Foreplay 101 was invaluable and a part of me will always be hot for teacher. In the end, I concluded, she was on the rebound and wanted to know that once more she could desire and touch, be desired and touched, once again, and I was lucky enough to be at the right place and time to be her partner for a moment.
Episode III: Angie, the Innocent Virgin Girl Next Door
After a year and a half dry spell, next up was a true Midwestern dish. Angie was a lily-white school functionary from a long-time bartending family (on her mother’s side) and a transplant from elsewhere in state on her father’s side. She lived in her own home unlike the last two apartment-dwellers, only around five minutes’ drive away in ideal conditions. We had little interests in common, save for trying to make the relationship work and perhaps caring about young people. As a behaviorist and part of a tight-knit family that gathered in numbers beyond what I was accustomed to, she had a keen awareness of the perceptions of others and hesitated to dress or conduct herself outside her home in ways that might get to kids who grew up rough and would not respect “a ho.”
Much more than even Marilyn, Angie was a BBW, but her relationship to her body was more complicated, even leading into the pros and cons of the new semaglutides that have challenged the era of body positivity that thrills me so today. I grew up with millennial women whose self-esteem was wrecked by heroin chic and whale-tail fashions of the mean aughts that were unflattering on bigger ladies, but I was still vaguely aware of a more open attitude to showing skin among bohemian elites or artist types like Allison (the Lena Dunham look) and women who were working-class and/or of color (Marilyn).
Angie’s middle-class attitude and need to keep the schoolmarm look (and a wholesome example for the nieces she helped raise) for public consumption led her to be very leery of showing skin or wearing anything form-fitting. I would see beneath soon enough, when the warm heat of the spring brought her flower out into the open.
I’ll spare the pleasantries of my first few dates with Angie, but they did blow past my record at around five by the time we first saw each others’ bodies in full. Nervous about sharing even headless pictures beyond the fringe of some underwear, Angie finally invited me to some dinner, board games, yada yada at her place. Watching bland pop culture documentaries by my generation’s iron law of Netflix and chill as the evening wound down, she took off her glasses and began to straddle me on her couch as we made out on a warm late April to early May evening, the picture of corn-fed American femininity in a tee and jean shorts like something out of John Mellencamp. Our lips searched each other inexpertly and our tongues danced with electric pleasure as we enjoyed the closeness, then she shared with me where she stood.
The furthest a man had gone with Angie was “second base,” such were her insecurities and her family’s sexual conservatism (toward their daughters per the usual double standard, I should add, as her brother was involved for a decade out of wedlock until marrying and having the nieces for whom she cared, were the father still around perhaps it would have been far more nerve-wracking). To my delight, she was open to breaking out of these norms at her own pace and giving me her firsts, and soon I rightly recognized the potential for wet jeans and shirts and was down to my boxer briefs as her shirt came off.
I boldly told her the bra was in the way, and so she invited me to take off my first one. Experimenting gently with the nipples as she closed her eyes to enjoy it, she soon shucked off the shorts to be naked save for pastel cotton underpants that teased me delightfully with the trimmed hair and flesh of her fupa. Her undulating form was so much more beautiful without than with the layers under which she hid, and though she was unready to go all the way, her inexperienced hands caressed my nervous member as we switched to a kind of outside missionary, teasing her soft mound with my testicles as I humped her belly and licked her breasts.
Wanting more privacy, Angie and I moved the proceedings from the living room to her bedroom and got a towel at my recommendation. She told me she was ready for more intimate touching, and after some consideration of cunnilingus, she walked me through finding her clit and providing her first release at the hands (well fingers) of a man. The flushed skin, the soft moans, the quivers of her ample flesh, most of all the moisture of her slick passage tightening around my digit all belied the lack of a rock-hard dick; my mind was erect and focused on the mission of satisfying her, and she and I both remembered it as a magical night. Among my last words after she came down from the mountain was how beautiful I found her body, which she sincerely thanked me for like I had answered a forgotten prayer.
By the next and final time we were intimate, a kind of debut among my friends at a local supper club buffet spot, Angie’s desires and comfort level had grown. We held hands in public and had gotten back to her place, where she showed that she had obtained condoms she hoped would perhaps lessen any effect on my sensitivity, bought a toy to entertain herself, gotten lube, basically accepted that were going to be a sexually active couple. Now the experiment was on! She wore a sexy red number she had teased me with by sext (off of her) and said she would rather spit then swallow, so we started some oral, even a little titfuck that wasn’t bad for a beginner. My member stirred some and I tried to return the favor, though I began to struggle some with the odor and the logistics of having my head there. Ultimately, I did more manual stimulation and we kissed some on her queen bed, but I felt I would be ready with some light penetration to be stimulated by the event itself.
The missionary I dreamed of was tried by me and Angie, but we had trouble lining up the spots, ditto when she mounted me. Finally, this once-shy vixen took up my offer to help smooth penetration by reaching her deepest recesses in doggy style. Glistening folds beckoned me and my thrusts soon beat a primal tattoo against her clit, exciting her to moans once again; alas, once more the spirit was willing and the flesh weak (a urologist visit to check for the likes of Peyronie’s and varicocele came up empty-handed, so perhaps we just both didn’t know what we were doing enough, certainly it was hard to imagine me as a blue pill candidate when I could get morning wood and use imagery and text alone). I saw to her orgasm as I had before, with fingers working their magic.
Wanting to let her know how much I reveled in her, I invited Angie to shower with me at her place before I returned home for the afternoon, an intimate pleasure that she of course had also never experienced like everything else we did in her bedroom. We made plans, had laughs, and just overall felt like a couple that had been together for years and not months, enjoying the thrill of discovering each others’ bodies, what they could do, and how we could use them to express and fill our deepest needs and hungers.
Between the technical issues, which I suspect could be long COVID given some of the other possibilities’ unlikelihood and my being much harder with Allison before catching the virus, and my basic life skills deficits, things eventually came to an amicable but real impasse. Angie never truly got over my turning down an invitation to a best friend’s wedding, and she envisioned marriage and kids in the short run despite some difficulties potentially conceiving them given that her life, family duties, and job revolved around offspring. I was more looking for dual-income no kids and unsure I wanted to bring children into the chaos of this world. We chat now and then, appreciative of one another and the milestones we helped each other reach.
Though my mother’s health, my job, and the world’s economy and politics remain embroiled in chaos at the moment, I keep hoping for another moment soon where I get to truly worship the body of Woman at her ripest and most sensual, breasts and hips and labia and smiles that make me want to forget the world’s troubles and just share a moment with the most wondrous creatures on this Earth. Perhaps that is my calling in life: to be a strange Peter Pan unable to conquer women but able to fulfill their innermost desires for a night or two of no-strings-attached pleasure, one soft, warm, round, cooing goddess of love at a time.