This incident has been on my mind lately. Seeing as I’m currently on my third glass of whiskey, I thought why hell not post it. This requires a ~~little~~ lot of backstory, so settle in. Maybe pour yourself a drink. A large one.
I wasn’t what you’d call popular in high school. I was (still am, in point of fact) an enormous nerd. Tall, scrawny, face like a bird, socially awkward, introverted, more interested in reading or my science classes than talking to people, more inclined to remember Shel Silverstein poems (the greatest American poet, fuck you, fight me) than the lyrics to whatever sing was popular. I was a walking stereotype. My love and sex life was nothing to write home about, unless you were scripting a cringe comedy. The less said about that period, the better.
College was a little kinder and less painful, as I found a slightly wider circle of friends, discovered D&D and Warhammer (yes, I was *amazingly* cool, thanks for noticing), and discovered that other people did more than tolerate my company. My prowess with women, however, was the stuff of cautionary tales. I can count all of my college dates on one hand and went the entirety of my college career without a girlfriend. I did, however, join an online text roleplaying game. The game was about 8 or so players (I was the only guy, weirdly enough). It reawakened a creative writing instinct that I had thought high school literature classes had killed.
It was here in the realm of cyberspace that I met Nina (not her real name). We clicked pretty quickly on a platonic level, even though she was about five or six years older than me. She liked my writing, even going so far as to give me a few requests for specific things. Writing short stories for the game was a fun little diversion to pass the time.
In a move that surprised everyone, including me, I enlisted in the army after graduating. While most people join the army and then go to college, I decided to do things backwards apparently. What can I say? I told you I was weird.
Basic training did two things. One, I learned how to get along with people. Basic forces you to learn how to interact with people, if by no other means than forcing you to be in the same area as 39 other idiots who were also dumb enough to join. Two, I packed on about 25 pounds of muscle. I wasn’t sporting a six-pack but my shoulders were definitely broader.
When I got to my first duty station, I got back in touch with the game group and started writing again. Nina was still there, always commenting whenever I posted a new piece. We eventually exchanged chat information and would occasionally have a quick conversation online. When I deployed, we became pen pals. At Christmas, she baked enough cookies for my entire unit and even made a special batch just for me.
Still with me? Here, have another finger of whiskey.
Things started heating up when I got back. We had more frequent chats, until one night our normal banter turned into innuendos and double entendres. Then a week or so later, we had a similar chat. A week after that, we dropped the pretense and I employed my creative writing abilities to start painting a rather risque picture of her and I in a hotel room.
(I need to pause and emphasize “creative” in that last sentence, because I was, at this point, still a virgin and a pretty green one at that. I had seen one set of real-life boobs. The closest I had gotten to sex was frottage from a female college friend who abruptly ceased and told me to go home and finish myself off and call her the next day. She then attempted to set me up with her roommate the next evening. It was very confusing. Anyway, I’m rabbit-ing. Back to the story.)
For a moment Nina stopped responding to my chat and I thought I had crossed a line. After an agonizing few minutes, she told me to keep writing, that she was only typing with one hand. Puzzled, I started to ask why when it dawned on me what she meant. Well, okay, then, it’s like that. Let’s boogie. Drawing on every sex scene I had ever read, I painted her a word picture of hot steamy sensual coupling, until she typed out (slowly, I might add) that she was almost there. A few minutes later she typed a smiley face, called me a silver-tongued devil, and thanked me for a pleasurable evening. She abruptly signed off, leaving me both baffled and hard as a rock. I chalked it up to a one-off event, jerked myself off, and went to bed.
Nina didn’t say anything about our little round of cybersex and I didn’t press the issue. About a month later though, I casually mentioned I was trying to figure out where to go on my upcoming four-day weekend.
“Have you thought about X?” Nina asked.
“Not really. Anything there you think I should see?” I replied.
“Not sure. Google Maps says it’s about the halfway point between me and you. We could find out together.” Nina responded and my heart rate hit the roof.
“Well, I’ve never been to X. Seems like as good a time as any.” I said, frantically trying to find a hotel at a decent price.
I lit out for X early Friday morning and had a lovely drive. I thought long and hard about where I wanted the weekend to go. While I wasn’t particularly religious at the time, I had been raised religious with all the associated baggage. Did I want to do this?*That bell can’t be unrung* said the voice of every pastor ever in my head. Nina had already checked in to our hotel room about an hour earlier, when I pulled up. I sat in the truck for about 10 minutes staring at her car and made up my mind. We’d have a wonderful weekend and maybe fool around but I wouldn’t have sex with her. I got out, grabbed my duffel, and headed to the room. I knocked. She opened.
I pause again for a brief description of our protagonists. I, at this point in life, am tall, blue-eyed, brown-haired with a trim athlete’s build. I didn’t have a six-pack, but I did have the beginnings of what Nina later told me were Adonis lines. My cock, like my face, is average. Nothing anyone would write home about, but nothing anyone would mock either. Nina is shorter than I am, somewhere south of BBW but north of “thicc” (as the youngins say). Big round ass, enormous chest, reddish-blonde hair, smile that will light up a pitch-black room. Resume tape.
We both said hi and then stood there awkwardly for a second. “I baked you something.” she said, breaking the painful silence and retreated inside. From her suitcase, she produces a plastic container filled with molasses. My favorite. A woman I had never met before in real life not only suggested we meet up for a potentially dirty weekend, she had brought my favorite baked good on the planet. I shut the door behind me, took the cookies from her hands, placed them back on her suitcase, and then kissed her for all I was worth.
Have another finger of whiskey. This is where it gets spicy.
After a moment of initial shock, she met my mouth hungrily. We stood like that, arms around each other, me towering over her, kissing like our lives depended on it. When we came up for air, Nina grinned from ear-to-ear. “Well hello to you too.” She pulled me down for another kiss.
My hands wandered lower resting just above the swell of her hip. Her hands went straight to my ass and squeezed. I felt myself growing hard. She giggled as I tried to adjust myself to keep my erection from pressing up against her and revealing just how hard I was. (I had some hangups, okay?)
“Happy to see me?”
“I’m just here for the cookies.”
“That says otherwise.” She motioned towards the obvious hard-on straining against my jeans.
I sat down on the bed, took a deep breath, and explained what I’d decided on the drive up. She sat down next to me and nodded. “It’s fine. That kiss took me by surprise, but only whatever you’re comfortable with. You can definitely kiss me again.” I smiled, relieved. She smiled at me, fondly. We kissed again, less frantically this time, but still just as hungrily. She slowly leaned back, pulling me on top of her. We stayed like that for a while, me in top of her, kissing like long-separates lovers.
Eventually, I tugged at the top button of her shirt. “What’s under here?”
“Why don’t you take it off and find out?”
Grinning, I rolled over and sat up, pulling Nina into a seated position. I unbuttoned her shirt and she shrugged it off, revealing a pair of exquisite breasts barely encased in a black lace bra. I stared. She flushed. I took one in my hand, savoring the weight and gently squeezed. She moaned under her breath. My cock twitched. I squeezed the other one. She moaned again, louder. Lightning shot down my spine. I popped one out of the cup and kissed the nipple gently. Nina hissed and I pulled away sharply.
“No” she said, smiling shly. “That felt really good. You can do it again.”
I accepted her gracious invitation, alternately fondling her breasts and nibbling on her nipples. At some point the bra disappeared and I kissed up her chest to her throat then over her collar bone. It was then we both discovered she had an unusual erogenous zone around her collarbone. Whenever I kissed there it was like lightning went through her body and she would whimper as she shivered.
Soon, we were both naked and staring at each other. Me, in wide-eyed wonder. Her, with the “come hither” eyes that only true lust can make possible. I felt like a million bucks.
We lay down next to each other. Her hand reached out and lightly grazed my cock. It twitched and a little drop of pre-cum leaked out. “That may not be a good idea. I might make a mess.” I said, sheepishly. She smiled kindly. “That’s alright. We have all weekend.”
I reached out and rubbed her lightly, my hand making it’s way towards her pussy. She spread her legs a little and my fingers found her wetness. I teased her slightly, light slow strokes. She closed her eyes and moaned loudly in appreciation. Encouraged, I increased my efforts and she rocked her hips forward into my palm. I let her build the friction for a while and then removed my hand. “Spread your legs for me.” I said. “It was a long drive and I’m hungry.”
Nina shook her head, rolling her eyes at my ridiculous line but did as I asked. As I repositioned my head between her thighs, I looked up and said “This is my first time doing this, so you may have to give me some instructions.” She ruffled my hair and rocked her hips up at me, indicating there were better uses for my mouth.
In every hero’s story, there is a point where he or she discovers their special talent that lets them win the day. Luke was force-sensitive. Steve Rogers never quit. Indiana Jones had panache. Hercules was a demigod. Apparently I have an inborn talent for cunilinguis. I assumed Nina was just sensitive but women later down the line would also confirm me to be a silver-tongued devil.
I licked, gently at first, then more rapidly. She tasted like heaven. I toyed at her with my tongue; flicks, licks, probes. Exploring her with my tongue, I found her clit and her thighs tightened around my head. Grinning internally, I tongued at her clit, feeling her body shift and writhe. Nina’s moans got louder and more urgent. Having found patterns that seemed to be working, I continued my merciless assault. I heard her grab a spare pillow to muffle her screams. Then suddenly, with a loud, muffled wail, she convulsed and her thighs nearly crushed my head. I would have died happy.
She relaxed and sighed happily. “Jesus Christ, where did you learn to do that?”
“First time.” I reminded her.
“Bullshit.” She said. “Now kiss me.”
As I kissed her, my hands wandered down to her pussy again.
She made a noise that was half protest, half begging. I teased her entrance with my finger before inserting it into her. The sound that escaped her lips was pure pleasure. I began fingering her, exploring her, understanding what motions made her convulse. Soon I had two fingers in her very tight pussy and she came with another noisy wail. This time I didn’t let up and fingered her straight through her orgasm. “Slow down, slow down, slo- Oh God, keep going don’t stop.”
I fingered Nina through multiple orgasms until her hand clamped down hard on my wrist and begged me to stop. “I haven’t had sex in a while” she said, trying to catch her breath. “My hips need a break. Goddamn.”
I pulled my fingers out of her and licked them clean. Nina smiled and snuggled up to me, her head in the crook of my shoulder, her breasts pressed against my ribcage. I will always remember the warmth of her body, the softness of her skin, and the light scent of whatever lotion or bodywash she had used that day. We lay like that for a while, utterly silent, Nina’s eyes half-closed in contentment, until she recovered. Finally she sat up.
“Okay, wonder boy. Time for me to repay the favor.” She lightly stroked my cock and my eyes almost rolled back in my head.
“Uh, that’s on a hair trigger so….”
“Shut up.” Nina said, stroking me. I nodded meekly and 30 seconds later splattered everywhere. I lay there, eyes closed, mortified at my brevity, when I felt Nina’s tongue on my stomach. I looked down to see her licking the cum from my belly. She tasted it and nodded. “I’m not normally a swallower but you taste pretty good.” She grinned. “Think you have another one for me?” She then proceeded to clean my stomach and chest with her tongue while I lay there, feeling my cock quickly recharge.
When I was clean (ish) and hard again Nina pulled her hair back into a ponytail bun and kissed my cock. She took me in her mouth and I flexed my hips needily. I stroked her hair lightly as she performed her ministrations; sucking, licking, teasing my slit with her tongue, fondling my balls. I would occasionally thrust my hips up reflexively and have to force myself back down to keep her from gagging. All the while, Nina would make noises of encouragement in her throat. I’m not sure how long it took before I was on the edge. I whimpered (in a totally manly way, swear) that I was close. Nina’s mouth left my cock with a loud pop and she stroked me, tossing in some encouraging words. (She later told me she enjoyed watching her partners face during orgasm. “I want to see your eyes burn” was her exact phrase.) I came with a loud grunt and a whole-body shudder. “Clean up, aisle you”, she giggled and once again, licked up the cum from my body.
The rest of the weekend was variations on the same: fellatio, cunnilinguis, fingering, frottage, titty-fucking. (Did I mention Nina had a rack to murder for? ‘Cause… spectacular.) We left for meals and to get some fresh air but after a few hours we inevitably found ourselves back in the room, ready for another round. Nina swallowed as much cum as I could produce, licking it off my body or, very memorably, her breasts and nipples. I ate her pussy like it was my last meal. The room smelled like sex. I’m sure housekeeping was either disgusted or jealous. Maybe both.
Our last morning rolled around and found me on top of her, teasing her entrance with the head of my cock. I wasn’t planning on penetrating her, we just enjoyed the teasing sensations. Nina was sopping wet, in one of her pre-orgasm hazy trances. I was reveling in my newfound abilities to reduce the beautiful, intelligent woman in my bed into a creature of unbridled lust. (Ladies, you have no idea how much watching that transformation turns a man on.) I was propped up, shifting my hips when she bucked. I slid forward…into her.
We froze.
“Am I…” I said.
Nina stared at me wide-eyed. “…yes”
We stared at each other for what seemed like forever. I could feel my heart pounding in my chest. Nina seemed to relax a little.
“Are you okay?” She asked quietly.
“I don’t know. I’m a little concerned that if I move, I’ll cum.” I said.
Nina giggled in spite of herself and recovered quickly. “It’s okay, take your time. Decide what you want to do.”
I have no idea how long I thought about this. My mind was a blank and on fire all at the same time. Mental white noise is a thing, apparently. I was hard as a rock, halfway inside her, trying to figure out whether what my body was screaming at me to do was a good idea.
“Are you sure you’re okay with me…” I trailed off.
Nina’s face and eyes suddenly got very serious. She reached a hand up and touched my cheek. “Sweetie, I would be honored.” She leaned up and kissed me very gently. I nodded slowly and swallowed.
I’d like to say that I am a natural talent, that I rocked Nina’s world on my first time. I am not and I did not. The memory of a first time isn’t so much the event itself, but the emotional weight we attach to the transition point as a society, the passing from boy to man, in the frankly sexist parlance of earlier times.
With a slow thrust, I pushed myself all the way in. I exhaled. Nina sighed with pleasure. I pulled back and pushed forward again, slowly. I was aware of my breath, of my heartbeat, of Nina’s unrelenting gaze and her hands on my hips gently urging me to let myself go. Another stroke, slightly faster, my balls tightening and my cock beginning the first twitch of climax. I exhaled slowly.
“I will not be long. Where do you want me to finish?” I asked through a ragged breath.
“Inside me is fine.” Nina said in a low voice.
I needed no more urging. I picked up the pace and maybe 20 seconds later exploded inside her with a loud grunt. I kept pumping emptying myself into her. I was aware of her squeezing herself around my cock and her quiet urgings of “Yes, yes, that’s it.” With a final shuddering stroke, I emptied the last of myself into her. Sensing I was finished, she gently pulled me down on top of her and kissed me. I lay there, my erection slowly shrinking inside her, my head on her soft enormous breasts trying to collect my wits. Finally, I pulled out and rolled over. Nina snuggled up to me.
“Are you okay?”
Nina stroked my chest softly. I lay there, staring at the ceiling, processing. “I think so? I’m not sure. My brain is scrambled. I mean, I wasn’t planning to do that, but I guess I was playing with fire but then again…” I rambled for a few minutes. Nina let me, listening patiently. In the end, I decided I was okay with it. Nothing ever quite turns out like we planned. Sometimes, we just do shit and see what happens and play the hand as it’s dealt to us. I conveyed all this in what I’d like to think were eloquent terms, but were more than likely the ramblings of a hormone-soaked brain dealing with post-nut clarity. Nina smiled and kissed my cheek.
“I enjoyed it.” she said, sitting up and stretching. “But I need to get a shower and clean up so I can start driving back.”
My eyes raked over her, taking in the glory of her nude body one last time. “It’s been a hell of a weekend.”
“Mmmhmm”, she purred, happily. “I have a lot more to teach you the next time we do one of these.”
Source: reddit.com/r/gonewildstories/comments/nl6i7b/a_virgins_dirty_weekend_mf
The best bit: “smile that will light up a pitch-black room.”