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TRUE CONFESSIONS- Losing My Virginity to Kinky Sex

I'd had an anal fixation for attractive females since childhood (beginning at around 6 or 7), but I'd patiently waited until the age of 32 before I finally found out what it was like to insert my erection into the body of a woman. Was it nasty and perverted that I chose a woman's anus instead of her vagina? Absolutely!

To explain... At 32, I had long given up on my ideal, on my dream of finding the perfect romance with the right girl, and making love to my bride on our honeymoon. Along the bumpy road that was my humble life, complex circumstances seemed to conspire, and a normal life-- well-- whatever normal is-- that just wasn't going to happen for me. I resigned myself to that difficult and disappointing truth. So, it became my self-indulgent quest to find sexual gratification instead of love. If or when love ever came along, it would have to wait in line. Exploring my nasty kinks was pushed to the top of my agenda. First up: Anal Sex. After a lifetime of staring mesmerized at beautiful girls in tight pants, their sexy butts on tantalizing display, nothing excited me more than the prospect of a woman slowly pulling her panties down, and bending over to let me sniff, lick, finger, and stuff my face up her ass right before fucking it. Such base objectification of women became the center of my addiction to porn. Masturbating to anal sex videos was an escapist fantasy for me, but I increasingly wondered what the reality must be like. Although I was and remain a gentleman, holding women in high esteem, this kink was my single vice, discreetly kept.

Barbara called me out of the blue that fateful night, and I barely remembered who she was, and how she obtained my phone number. Ah! It came back to me a few seconds later. A month or so earlier, we'd met for the first time when she flirted with me in the "Electronics" section at Target department store. She had unnerved me a bit with her sudden approach, walking straight up to me. Most mature women did not behave that way in public with strangers, and this lady totally had a wholesome look and a totally cheerful vibe about her. With her very short brown hairdo showing flecks of gray, and her friendly demeanor, she could have been someone's kindly grandmother, particularly with those half-moon spectacles perched on the tip of her nose, and linked by a thin chain draping around the back of her neck. Even though she wasn't my type by any stretch, mostly due to her age, she was reasonably pretty, with a pudgy mid-section beneath a very large bust. Despite the relative modesty of her blouse, its plunging neckline revealed an impressive amount of cleavage that was impossible to ignore. Barbara said that she liked to give hugs to tall men. I presumed that, with her height being around 5'7", this made her feel small and secure, and that she was probably projecting fond memories of some father figure onto me. As I watched her walk away, pushing her red shopping cart, I wondered if this might be one of those singular opportunities which I would forever regret failing to pursue. I had zero social life, and no prospects at all on the horizon. So, why not give this a peek? Spurred into action, I searched the store in hopes of finding the old woman. Once I spotted her in "Small Electric Appliances," I forced myself to calmly approach and turn on my charm. I had zero experience at this, but I thought I did all right. We exchanged names in introduction, and I mentioned that I was an illustrator, which impressed her. Barbara said that she wasn't married, but that she was still living with her ex-boyfriend, an arrangement which was coming to an end. Hmm... A complication. Well, just in case, for the future, I gave this middle-aged white woman my number, joking about going over to visit sometime when her situation changed, and I would show her my etchings. And that was it. I didn't really expect anything to happen, but I reveled in my sudden surge in confidence. Shy guy that I was, this was the first female with whom I had flirted since my late teens, back in high school. But those were teenage girls, and Barbara was a grown woman, an older white woman. This stirred my interracial desires big-time.

But as the weeks passed, I'd started to forget about it. Barbara's phone call was a pleasant surprise. She happily informed me that she had moved into a small cottage to the rear of her ex-boyfriend's property. It was a small move, and in one of her first acts of new independence, she wanted to hold me to my offer of visiting her to-- show her my etchings. I was flattered that she remembered me in such detail, down to my flippant flirtatious remark. Nevertheless, I was very nervous, having second thoughts about the whole thing. Still, my rigid erection was a vote for me to embark on this naughty adventure, a quest to surrender my virtue in a very exciting and unorthodox way. But were we on the same page? Was this about casual sex? Well, this was a much older woman being bold enough to call me. Just as she had done in the department store, Barbara was aggressively making the first move. And the fact that she was inviting me directly over to her place instead of coaxing me to take her out on a date had to be interpreted as purely sexual. All polite pretenses aside, she wanted my young black dick. Did I really want to give it to her? Time to put up, or shut up.

I was partially in a daze as I headed over to her place that night. Since I worked from home as a freelancer, I was without a car. So, I rode my bicycle over the relatively short distance across town. I was extremely nervous, but I at least remembered to bring my art portfolio along to show her, as promised, in an effort to break the ice. Leaving my bike propped off the side of the dark, narrow walkway, I knocked on the door to Barbara's little one-room cottage. The door opened, and there was the kind face with the beaming smile matching my refreshed recollection. As I stepped inside, Barbara continued to appraise me in gleeful wonder while shutting the front door behind me. Once again, she remarked on how tall I was, and how much that delighted her. This time, however, she got the hug she had craved from the beginning. The warm greeting was followed by some awkward and breezy small talk. She was dressed casually, although her top once again sported a plunging neckline, something common among very busty women, so proud of their assets. All I accepted to drink was a glass of ice water, my usual beverage of choice. There wasn't space for much furniture in this one-room cottage. In lieu of a couch, we simply sat together on Barbara's bed while she happily reviewed my art portfolio. She took her time examining every illustration, gushing with praise and awe. I answered her questions and told the stories behind those drawings which fascinated her most. Finishing the book, I set it aside on the nightstand, next to my glass of water. I became aware of the quiet there in the cottage, as well as in the sleepy neighborhood outside. It was nearly bedtime for most decent folks hereabouts. What was I doing there? What was I thinking? Barbara filled the awkward silence by flirting again, complimenting my looks while lightly caressing the side of my neck. This much older lady had sent tingles through me with that teasing touch, and my penis stirred to life again in my pants. She had made the first move once more, taking that pressure off of my shoulders.

Steadily, I relaxed, and I summoned the nerve to lightly fondle her large breasts while we started french-kissing. Outside of being smooshed in a loving embrace from one of my great aunts as a kid, I'd never been that close to tits of such magnitude before. Each mound of flesh more than filled my hand, and the substantial weight stunned me! I found that I liked the taste of her tongue, and the feel of her warm breath on my cheek. It had been so long since I'd kissed anyone that way. Still, I was never more mindful that this woman was 20 years older than me, and that she was the first white woman with whom I had ever shared such intimacy. Interracial intimacy is so supremely erotic. And now I was learning how erotic Age Gap intimacy could also be. In my mind, I marveled that she was already 2 years out of high school by the time I was born. Peeking out of one eye, I noted the pearl earring adorning her earlobe, the strands of gray in her close-cropped brown hair, and the fine smile lines radiating outward from the corner of her own eye. An undeniable spell was being cast, and I opened my mouth in fuller acceptance of Barbara's probing tongue.

It was a fact that Barbara wasn't at all shy. She'd proven that in the department store. So, when I felt her hand sliding down into my lap, my reflex action was to spread my thighs to better accommodate her shameless groping. It was her place, and she was comfortable taking the lead in this encounter. In my position as a nervous virgin with a much more experienced older woman, I preferred this. This felt right. She groped and squeezed the bulge she found there. Deftly, she undid my pants while still kissing me. The soft clinking of my belt buckle was loud in the quiet room, as was the sound of my zipper opening. Tingles of delight overloaded my brain's pleasure center once I felt Barbara's hand reach into my underwear to take hold of my engorged penis. I paused our kissing to look down, appreciating the stark contrast of her older, creamy-white hand wrapped around my younger chocolate dick. Only one other person in my life had ever touched me there, in that way, and that was my high school girlfriend so many years before. That occurred in the back rows of darkened movie theaters, in the thick bushes of Central Park, and any other secluded places we found to make out, and touch one another's young bodies. Susan was first-generation Chinese, one of the brightest students in our graduating class. And she was a sexual freak. She taught me how to kiss. And she gave me my first blow-job, something I actually fought against at the time, being so naive and so prudish. That amusing story can be found elsewhere in my Writings. However, fellatio was as far as any of those escapades went, never further. Back then, I resolved to obey my faith, and preserve my virginity until marriage. But, I digress. Back to our tale...

I watched as Barbara stood up to undress, so full of girlish glee as she removed her 44 DDD bra, allowing her huge breasts to spill out. Barbara was pleasingly plump around the middle, not the hourglass figure which was my ideal. Still, this was no deal-breaker for me as a sex-starved young man on the verge of finally solving the mystery of sex. She stood between my legs to let me play with them, and suck on her nipples. As she hastily removed her shorts and panties, I reached down to also play with the mound of hair around her pussy before inserting a finger inside to note her wetness. I was familiar with the complexity of a woman's vagina from playing with Susan's so long ago, and from studying way too much porn. I knew to stimulate the clitoris, and at last, I was sending tingles through Barbara's body now. Part of me still refused to believe this was all really happening. These reality checks seemed to come in waves every 5 minutes or so.

Taking my turn to strip naked, I enjoyed the exhibitionist rush of slowly sliding down the waistband of my underwear until my erection sprang free. My penis dangled and jiggled, now fully exposed in Barbara's sight as I stepped out of the last of my clothes, standing as nude as she in the cozy lamplight. What an odd pair we made! What winding roads in our respective lives had led us to this point together? She was my first woman, let alone my first Caucasian woman. Was I her first black man? Considering all the years of history she saw before I was born, what did she think of those heroic African-Americans fighting and dying for Civil Rights? What did she know about Emmett Till, the 14 year-old black boy who was brutally murdered in the Deep South of Mississippi just for wolf-whistling at the white wife of a town merchant? And there we were, white woman and black man engaging in taboo foreplay, preparing to have sex. As much as the world had changed, much of it still remained the same. The sight of me with Barbara would have shocked and offended lots of folks, and enraged some.

Taking a seat on the bed again, she reached out to place her hands on my hips. Leaning closer, she engulfed my dick with her mouth, and proceeded to suck. Yes, that's what this feels like, I remembered. The wet warmth of my penis being bathed in her saliva was so pleasing. The tight seal of her lips, the lively activity of her tongue, bathing my organ in her saliva... I even enjoyed the occasional scr*pe of her teeth along my shaft as a solid reminder that my penis was indeed inside her mouth. I reflected again on all the racist history Barbara must have been aware of back in her youth. That added so much more excitement and significance to this moment, to immerse myself in the ecstasy of this old white woman sucking on my black dong. No white superiority in that little cottage. Suck my black dick, white woman. Suck it. I pushed my pelvis forward, and I gently caressed her back and shoulders, stroking her short hair while glancing around the small room to distract myself from the extreme pleasure. Her hands came up to clutch and squeeze my tight, round "ghetto booty." It all felt so magical and so kinky. But I had no stamina. I was a virgin. I knew I was going to climax prematurely if I didn't do something fast, and I might never get the chance to try what I hoped. Awkwardly moving away from her, I candidly asked Barbara-- ifIcouldfuckheruptheass. Haha! I figured I could get it out if I blurted it as fast as I could.

Immediately, Barbara expressed a concern that I was gay. Uhh-- no. I confidently assured her that I was indeed straight as straight can be. I explained that I had an anal fetish for girls from a very early age, and I was desperate to finally know what it was like to experience anal sex most of all, and with her, if she didn't mind. She would be my first. This satisfied Barbara, and even flattered her. After giving the matter another moment's thought, she told me, "Ohh, well, I haven't had time to-- you know--" "That's okay! I don't mind." I told the truth. My mounting excitement overrode everything else. No doubt, Barbara had showered earlier that day, and perhaps shortly before my arrival at her cottage. But even if she'd planned for us to meet that evening, I'm sure she'd gone through her ordinary routine the rest of the day, never thinking she'd have to prepare for what I was requesting. And that made it a spontaneous opportunity to experience anal sex as naturally as possible. That's exactly what I wanted.

The next thing I remember was climbing up to crouch behind Barbara in the middle of the bed. Doggy position was so aptly named, being so animal and so undignified for two human beings. Barbara was face-down, ass-up, her spine arched so seductively as she waited for me. My vision was filled with this old woman's pale, wide buttocks, flatter than it was round, a sparse sprinkling of freckles dotting each massive cheek. Being a Butt-Lover for so long, I'd seen my fair share of gorgeous female asses in porn magazines and videos. This was not that. Barbara had an old white lady's butt, nothing spectacular. It was a bit square, not pear-shaped, nor apple-bottomed, and definitely not a bubble butt. What made it so intensely appealing was that it was Barbara's butt, now being graciously surrendered to me for my kinky experimentation. Her butt was to be my wild frontier of fun, and deep within the tight, very private space beyond that puckered aperture was where I would shed my virginity at last, and "officially" become a man. Under these considerations, Barbara's ass was the most beautiful ass in the world to me in that moment.

Astutely, Barbara liberally applied moisture from her pussy to her anus before giving her hips a little wiggle. Watching her do that was the perfect opening act to this deliriously nasty stage in my life. Still nervous as hell, I gradually unleashed my inner pervert. Taking my time, I used my dick to wipe up and down the length of Barbara's butt-crack several times before pressing the tip of my glans firmly against the puckered gateway of her sphincter. It slowly yielded to the pressure, and with an inaudible "pop," it swallowed up the mushroom head of my penis. Just like that, I was on the threshold of fantasy fulfillment. Leaning into it, I watched as the entire length of my dong disappeared in a smooth plunge straight up Barbara's asshole. She responded with an, "OHHhhhhh!" It was all at once an obscene and beautiful sight, an indescribably transformative sensation. I went motionless, soaking in the moment of my first sexual connection with a woman's body. Not her mouth. And not her pussy; that would come later. No, again, I wanted my first penetration to be in the place where women had teased me for a lifetime. All the bouncing, and jiggling, and sashaying... all the skin-tight jeans, the bikini bottoms, and the sexy little panty wedgies... Female ASS. It had fascinated me to the point of obsession, never failing to get my dick rock-hard. And now, I reveled in the euphoria of having my rock-hard erection stuffed completely up inside this old white woman's tight shit-chute, a woman with whom I was barely acquainted. No dating. No courtship. Just a booty-call in the most literal sense of the term, and as I designed it for us. The interracial contrast provided the unparalleled eroticism. The Age Gap provided the dark racial history as an added element to the taboo. A young black man fucking an old white woman right up the ass? It was perfect. Relaxing more of my weight down on her, my dick sank into Barbara's snug anus, to my balls.

Okay, for the most part, our sexual education is clinical. We're taught what goes where, and how the coital process works in general. Maybe some of us inspect photos and crudely-drawn diagrams, and some of us even watch safe, artfully-crafted films. But beyond all that basic information, no one can teach us the actual physical practice as youngsters. The interaction of our bodies comes naturally, the positioning, the opening of our legs, the thrusting of our hips... I was a virgin, but my body knew how to move as I proceeded to anally sodomize Barbara. Auto-pilot was engaged on the mental level, so to speak. Physically, my body entered Hump Mode, and, to a voyeur, the scene must have closely conjured the image of one dog humping another in the street. All of a sudden, I felt the power transfer from her to me. In fucking Barbara up her ass, I was suddenly in the Dominant position, and she the submissive. This additional psychological layer thoroughly spiked the kinky splendor. I took a more possessive grasp of Barbara's waist as I started fucking her loudly enough for the slap-slap-slapping of our colliding flesh to doubtlessly be heard over in the neighboring backyard.

My vigorous energy unbalanced Barbara, and we toppled forward in a heap onto the bed. Adjusting instantly, still inserted, I continued to hump her from that prone position, sliding my hands beneath her body to grasp both her massive breasts. I laid the side of my face atop hers, and she giggled to listen to my ragged breaths. My uneven breathing betrayed the intensity of my arousal, like hearing the irregular breathing of someone masturbating. I was slightly embarrassed that she noticed this lack of cool composure on my part. But this was about my first time, and I was finally gettin' some ass. Using my knees, I coaxed Barbara to spread her thighs wide upon the bed sheets, and to arch her spine into me, granting easier access. The tightness of her rectum had eased considerably in accommodating my anal invasion, and the relentless penetration of my penis. She felt loose now, and this aroused me even more. The pace of my merciless thrusting increased, and I hit my peak. Explosive eruption. Barbara reacted with a moan as she must have felt my dick throbbing and pulsing within her chute. I pumped a full and massive load of semen like gushing lava into her colon. Gazing down at the back of Barbara's head during my convulsing orgasm, I also felt a wave of affection and gratitude. I was no longer a virgin. I had shared my essence with her as my chosen first. This was very special amid all the kinky specifics. Hers was the first body into which I had ejaculated my sperm. Yes, I'm a sentimental guy. This wasn't how I had hoped it would be, experiencing one of life's greatest pleasures, its greatest manifestation of amorous love. It was what I got, and it was wonderful in its own way. Sweaty and panting heavily, I pulled out. My flaccid penis exited Barbara's asshole with a soft kissing sound, little sticky strands stretching out to maintain our bodily connection.

Joy and rapture? Alas, not for long. I was immediately consumed with guilt as the reality of what I'd done returned to torment me. I had committed fornication, and I was ashamed. Barbara tried to offer comfort as I explained about my strict religious background. And it was that confession and her empathy that began building the foundation of what would become a friendship lasting nearly a year. Coping with my guilt, I returned often to visit Barbara, exploring all the sexual kinks that fascinated me. And yes, we had lots more anal sex.