Standing at five feet nine inches and 175 pounds, I was a nineteen-year-old fetishizable force to be reckoned with. I had long red hair that I kept in a French braid concealing my sensuality and confirming my naiveté. My breasts were large and dense, decorated by crater-like pasty pink nipples. My ivory skin was a translucent shell encasing a voluptuous body decorated with bright blue veins that were roadmaps to where I wanted be teased and tortured. No longer a young, twig-like teen, I was a woman by any measurable standard, and I wanted to be fucked.
But I was a virgin. I was not the typical repressed high schooler that moved on to college without letting myself get fucked, though that’s what many assumed. Rather, I never had an interest in having sex with my male peers. I often crushed on my professors, teachers, and older male role models, but never had the confidence or desire to approach them. By my Junior year of college, though, I had had enough.
I had a vigorous sex life with myself. Uninterested in high school and college boys, I developed an interest in older men and wanted to fuck desperately, but didn’t know where to start. On top of this, I was ambivalent. As a perfectionist, I didn’t want to attempt something that I didn’t already know a great deal about, even if that something was as seemingly intuitive as sex. I spent weeks browsing the reddit AskMen section for advice on how to conceal my virginity. Should I break my hymen with a dildo before so I won’t bleed with him? What if I bleed anyway?!?. What if I say something weird when I’m getting off? What if I freak out and can’t do it? Thoughts like this plagued my apprehensive mind for weeks. But I knew I had to address this sooner rather than later. So, I downloaded Tinder and made a profile. What should I say in my bio? Perhaps something quirky but endearing would pull the crowd I was trying to attract. “Just a cute Jew, how ‘bout you?”. Yeah, that’ll work. I saved the profile and started swiping.
Knowing I had an affinity for older men, I set my age preferences to between 35 and 45. Probably not grey, but could be my dad in some parts of the country. Perfect. I swiped through the plethora of aging frat bros, divorced suburban dads, and aging dirty hippies. I was not having any luck, and even those that I matched with were not that enticing to my teenage desires.
Then I saw /u/seedickthrowaway. I recognized him from my previous escapades in Tinder. We had talked briefly the year prior, but I got flighty and left the conversation. I remembered him being forward, insisting that I come over the same day, or maybe the next day if I must. He was just as attractive as I had remembered. In the year prior, I had wanted to meet up with him, to finally let myself go and let him pleasure me. But at the time, I was a year into almost a two-year long depressive episode and couldn’t will myself to get ready to go see him. So I stayed in bed and imagined what he might do to me if I had gone. I regretted staying in and not pouncing on the opportunity, but knew it wasn’t the right time. But a year later, my libido had my nerves in a headlock, and I wanted nothing more than for an experienced older man to fuck my overly-analytical and nervous brains out.
He was a 35-year-old engineer with olive skin, dark curly hair, and a perfectly-groomed beard that was made to juxtapose my alabaster thighs. Hello, darkness, my old friend. I had found the man for the task, I just hoped that he would still want me.
A day had passed, and I was sitting on my bed stroking my pussy in the middle of the day between classes when I got a notification. “/u/seedickthrowaway sent you a message” it read. It was a Monday. “I believe that I am also a cute Jew, yes?” he wrote. It was a smirky quip that showed he had looked at my bio, but was also pretty self-impressed. After exchanging messages for about a half an hour, I was taken aback by his candor.
“On metro, reading your profile.
Rock hard.
Drinks tonight?”
“Does this mean he thinks I’m attractive?” I naively thought. I said that I had homework and studying to do throughout the week, but could see him on Friday. He agreed, and I started to panic. Was this really going to happen? I was partly relieved, but mostly out of denial. I knew I wasn’t ready, but decided that I had to be. /u/seedickthrowaway asked me to message him if I became free earlier in the week, and I agreed.
Friday came, and I planned to meet him after work. Conveniently, he lived just two blocks from my work. I dressed inappropriately for work, covering a very revealing fuchsia blouse with an oversized men’s Levi’s jacket, buttoned up to the collar. “I can do this. I’m ready for this,” I said to myself in the bathroom mirror before exiting my apartment.
Work that afternoon was the longest few hours of my life. I could barely contain my nervousness, pacing, tapping my foot, and reapplying my lipstick. I thought about leaving early, but it didn’t make sense. I had to meet him at 6:15, so there was no sense leaving early. The clock finally struck 6, and I could feel my heart racing. But, like always, my emotions were contained in 300 feet of hemp rope, gimp hooded and ball gagged. I walked confidently in the direction of his apartment complex. He buzzed me in, and I swallowed. It was happening.
I entered the building and took the elevator up to the third floor. I exited the elevator, turned to the right and walked down the long hallway, realizing that his unit was at the very end. Once at the front door, I paused and doubled checked the unit number. I was in the right place. There was no backing out now.
I gave my standard three-beat knock on his front door. Moments later, it veered open at a speed comparable to that of expired molasses. At the end of the painfully long moment, he stood before me, even more statuesque and exquisite than I had imagined. His espresso-colored eyes pierced into my sapphire blues, and the beard I so badly wanted in my pussy was adorned with a few grey hairs. Fuck yes. I had come to the right place.
“Shabbat shalom,” I exclaimed, awkwardly. “Shabbat shalom,” he replied, surprised. He guided me back to the kitchen of his one-bedroom apartment on Denny Way. It was a perfect June evening, and the sun was just beginning to set over the Space Needle, which was in perfect view from his kitchen window. I took off my jacket to reveal what I had been hiding at work: two succulent, plump breasts cradled in a push up bra beneath a revealing pink top. “Look at you with your titties hanging out,” he quipped. He made himself a martini, and had me pour my own gin and tonic. Splendid. I was in control of how much alcohol I’d drink, and wouldn’t get into too much trouble.
We talked for quite some time and covered the usual topics: college, hometowns, work. At one point I noticed that he was stroking his cock, but didn’t know if it was meant to be sexual or if that was just something that guys did. He asked me how I came to be so accomplished academically at such a young age. I had a response that dismissed the compliment. He paused, suddenly. “Could you take your top of for me?” he asked, seemingly out of nowhere. Not knowing whether I should tell him to fuck off or just go along with it, I paused, looked at him, and reluctantly agreed. My fuchsia surplice top came off to reveal my tender, plush breasts, embellished with blue veins that were throbbing with arousal. I only hoped that he was feeling the same way.
He stood up in front of me and asked me to suck his cock. I immediately said no, surprised and offended. “How long have I even been here?” I questioned. “An hour,” he insisted. “Please?” he implored. I sat silently, shocked and uncertain. “When was the last time you sucked a cock?” he asked. My voice started to crack before I could even get out a word and I couldn’t maintain eye contact with him anymore. “Never?” he questioned. I looked at him with an innocent stare that could have only conveyed inexperience. “Come with me,” he said.
I followed him into his room and laid next to him on his bed. The straw-colored linen sheets accented an otherwise minimalist tidy room. He pulled at my black lace bra to uncover my breasts. He sucked on my nipples and bit down. Hard. I winced, and he pulled back. He started taking off his black Levi’s 511s to reveal a near perfect cock. I stared at it like a portrait in a gallery, in awe of its beauty, but afraid of touching it.
“Do you want me to teach you?” he inquired. I took him with my eyes and with my gaze, the desire was confirmed. “Spit in your hand,” he commanded. I nervously tried to cough something up, when he grabbed my hand and spat in it. I felt simultaneously degraded and aroused.
His greedy hands braced my face and guided me onto him. “This is not the first dick you’ve ever sucked,” he remarked, incredulously. Splaying his legs open, I grabbed the backs of his thighs and stuck my ass in the air as if I were eating pussy like a Portland bulldyke. I denied his claims, somewhat flattered. “I just watch a lot of porn.” I planted my face into his basket and sucked his cock as if I was licking the world’s last creamsicle on an apocalyptic hot summer day. What I lacked in experience I made up for in enthusiasm. I pursed my lips and ran them all along the sides of his shaft and swirled my tongue around the head. In need of a breath, I let up and smacked a hard kiss right on the tip.
I lifted my face off his cock, wiped my jaw, and looked up at him like a scared fawn. With a fistful of sheet in each hand, he relented. “No more.”
He stopped me before he came, and told me to stand at the edge of the bed. My shins pressed into the frame, and I could feel an uncomfortable stretch down the back of my legs. He shimmied my pants down to reveal a pair of lacey black panties my mom bought me in a 3-pack from Costco. He slid his hand into them and slowly stroked my dripping pussy from clit to taint with this middle finger. He pushed me onto my hands and knees as his greedy hands caressed my milky white ass with the tenderness of a lover and the intentions of a sadist. The caress was rough but sensual. It made me know that I was wanted, but that I was ultimately his fucktoy for the evening. The caresses slowed, and his hand was steadied, leaving just his thumb circling in one place. He was hesitating, and I thought I had done or said something wrong.
I felt the warmth of his hand lift off of me, vanishing, and was almost instantaneously met with a sting. He had pulled his hand back to plant it on me firmly. My skin was pulsing with a humming vibration from his palm, and I let out a sound that was somewhere between a wince and a moan. His hand was buzzing. He put his hands on my hips and pulled himself into me and teased the lips of my pussy with the head of his cock. They were already so plump and wet. The teasing had puffed my lips up and and covered them with my own cum. There I stood, ready. My young pussy was pink and sweet, just like the plumerias on the desk of my femininely-decorated dorm room.
I lost control, moaning and flinching as if I were the victim of an exorcism. He wasn’t even inside of me yet. It was the most satisfying and overwhelming sensation I had ever felt. I started thrashing my head around and moaning uncontrollably. “Do you have a condom?” I asked, panicked. “I’m just rubbing,” he reassured. He retrieved a condom from the aluminum Durex box on the side of his bed. I heard him rip it open and roll it onto his hard pulsing cock. He pulled my Costco panties down from between the middle of my thick thighs down to my ankles with his toes. He knelt down, momentarily, and kissed my right asscheek, only to stand up and smack it twice as hard as he had the first time. My shoulders lunged forward and down into the bed deeper.
He grabbed my wide hips and pulled them into him. He slipped into me, and I gasped, as if I had just been saved from drowning. It was euphoric. Even with a condom I could feel him in me. He flipped me over, and I couldn’t help but look at him. He was so beautiful. I ran my hands down his back and onto his ass, which could have been carved out stone. His dark and devious eyes looked into mine sweetly, and he caressed my face. “Do you like the way Daddy feels inside you, you slutty little girl?” he asked. I whimpered, eagerly. “That’s what I like to hear.” He spat in my face, the humiliation reminding me of my place and evolution at the same time.
He came, and I was at peace. It was over. I wasn’t a virgin anymore. I was laying next to him, stroking his chest, feeling his warmth. Always feeling fallible, I asked if I had been too wet. He reassured me that I hadn’t. But I still felt that I had failed him. He sent me home, and I felt confused. My virginity was no longer an issue, but another soon replaced it. My sexual archetype became that of a man that wasn’t available to me. Like a pup following a wolf, I was infatuated with his being and wanted nothing more than to please him. But to him, I was just another pup: a young, wandering, directionless, naive creature to be molded, and then turned loose to the rest of the world.
Source: reddit.com/r/gonewildstories/comments/bj9ubj/i_lost_my_virginity_to_a_kinky_older_man_on
Goddamn
You did a great job with this story.