Signing back up for Reddit combined with quarantine time to get nostalgic has me fondly recalling memories of nights (and mornings) past. Let’s be honest too, we’re all fucking horny right now.
As a creative outlet and a meager attempt to contribute to Sexy Reddit of which I’m so fond, going to post some formative stories along my personal sexual journey starting from the start – as explained below. Hope at least a few of you enjoy!!
I start the tales at the opening of my eyes to all that sexuality would one day mean to me.
I led a happy and sexual adolescence but it wasn’t until 21 years old that things got interesting. In art school and loving life, I had been dating Emmy (also 21 years old) for a few months.
She was beautiful – Lebanese, average height, long curly hair, perky C cups, a firm but large handful of a butt, and a deep and thoughtful smile that combined with piercings eyes to melt any heart. Emmy had a tough and wise exterior – as friends before we dated she was quick to talk about a previous relationship with a professor – but beneath the protective shell, she was a sensitive, deeply curious girl whose experience with sex was limited to a few flings with older men and little in the way of making love or any sort of relationship with real trust and connection.
And make love we did – often and repeatedly – long into many nights. After about a month we both got tested and she excitedly announced she had gone to the campus health center for birth control. Sex turned even more intimate and sloppy and hungry as everything was now possible and natural.
And so we pick things up a couple of months into things. By that point it wasn’t unusual for us to have sex three or four times in a day but things had up to then been relatively vanilla – I was addicted to her sensual blowjobs, we would fuck in missionary or cowgirl, and I would try and make her cum – oftentimes unsuccessfully – with my mouth as she laid on her back and tried to focus.
Then all that changed one magical afternoon.
I had been on a trip home for a couple of days. It was the first time we had been apart since we starting dating. We talked constantly while I was gone and stayed up late into the night texting each other stories of what we planned to do upon our reunion – punctuated by her sending a photo of her legs spread, glistening clit front and center, with the caption, “I need you here now.”
Needless to say, I rushed straight from the airport to her apartment.
When I opened the door, she was waiting for me in the entrance way in only a thin white crop top and a long flowing skirt. We immediately melded into each other’s arms, making out with the hunger that comes from sexting over a few days apart. Lips open, tongues hungrily intertwined, I pushed her up against the wall as my hand teasingly grazed her bare stomach before reaching underneath her shirt for a handful of her breast. As she gasped with the satisfaction of my hands reunion with its favorite spot, I rolled her nipple in between my fingers, eliciting a sharp inhale against our still connected mouths. My other hand reached down at this point, pulling up her skirt, and reached around to firmly grab her ass. My already hardening cock jumped at her lack of underwear as I pulled her in against me so our hips urgently met.
Feeling me against her – separated only by my jeans and her thin skirt, she pulled her head from mine and smiled knowingly before – eye to eye – telling me she had a lot of time to think over the past few days and she has plans for me.
Barely having had time to register what she meant, she spun me around and now pinned me against the wall. She kissed me once more before pulling my shirt over my head and then sliding down to her knees where she hastily unbuttoned and pulled down my jeans and underwear.
Smiling up at me, she told me she wanted to get any too-quick orgasm out of the way so we could focus. Now turning her attention back to my dick, bobbing longingly in front of me, she swallowed me in a nearly single motion while using her hands to keep my hips firmly against the wall. She then put her all into a deep throat blowjob that I’m not ashamed to admit was so mind blowing my effective that it was over in a memorable and explosive minute or so (and that might be generous). She then stood up, smiling with cum still on her lips and opened her mouth to show how full it was before pausing – devilish smile and all. She then grabbed my hair and pulled me in to kiss her – going out of her way to push some of my cum into my mouth. After a moment she paused our renewed making out to tell me that if she was going to swallow it, I should too.
Turned on and excited for this new woman I found myself naked in front of, I pulled her back in and continued kissing her until I felt two hands on my shoulder pushing me down onto my knees. Not knowing what she wanted but eager to please, I complied and knelt in front of her as she then lifted her skirt with one hand and grabbed my hair with the other.
“It’s time we focused on my getting off as much as you do. Let’s think of it as your having a debt to make up for in all of the extra orgasms you’ve had.”
With that, she pulled my selfish, untrained twenty one year old face in to her already swollen and wet push where I started to lap away.
After just a few months of that, she grew a bit frustrated and told me to get up and follow her into the bedroom.
Once in the bedroom, I started to kiss her again, wanting to regain the romance of my arrival but she had other plans. Pushing me away, she told me with no room for debate to lay down on the bed with my head on a pillow. As I crawled over there, she undressed and followed me – crawling up my body but instead of stopping at our usual cowgirl, she continued, eventually scooting on her knees so that her pussy was right in front of my chin.
As is perhaps obvious given the context, this was the first time any woman had ever sat on my chest or face and I sadly hadn’t even considered the possibility. Nonetheless, instinct and a love of pussy took over and like the young inexperience man I was, I started trying to fuck her with my tongue.
That’s when everything changed. With a tough love kind of firmness, she pulled my head away.
“Stop. That doesn’t work. I need you to pay attention. What I need is focus and consistency. Lick my clit.”
Head now back in place, I went to a trick I had read at some point about “drawing” the alphabet with your tongue.
“Stop. I can’t focus if you keep changing. Pick a speed and pressure and stay with it.”
Now back with my nose up against her pubic mound and my mouth on her clit, I started out gently with consistency. And then it started to really click. I felt it first in her thighs – a low vibration building to a squeeze. Now with sound muffled as her thighs gripped my ears, she started to moan louder and louder. I felt my chin grow more and more wet as she responded to my attention and then her hands gripped my hair. Not to change anything this time but to pull me in, hold me there lest I interrupt her building orgasm. As that wave of pleasure crashed over her, she screamed out. It was a primal scream at a volume I never heard from her – accompanied by her grinding her pussy into my face briefly and then sort of ejecting away from me as she came down and grew sensitive.
She laid down on my legs, still shaking and vibrating with the after shocks of what she would later say was the most powerful orgasm of her life to date.
Meanwhile, I was forever hooked. That sense of pride and satisfaction and utility and intimacy was one I was addicted to instantly. For the first time, I felt I had the power of pleasing my partner in my hands and I couldn’t wait to do it again.
Brain reeling from this shift, I was brought back to the current moment by her saying she was curious about something.
“Are you curious about butt play?” She asked.
My heart started to beat a bit faster at mentoring of a sort of (at the time) kinky holy grail.
Playing it cool – or at least trying to, I replied, “Sure, I guess so.”
“Ok, I want to feel what it’s like for you to play with me down there but I’m too sensitive still. You go first.”
Confused at first, she explained to me that some men enjoyed having their ass fingered and if I was going to finger her, she gets to finger me.
While my mind wrestled with all the homophobia of high school years, she casually leaned over and too my semi-hard dick in her mouth and began to lick circles around the head while looking up at me, waiting for my answer.
As hormones began to flood into me once more, I agreed. She wasted no time in pushing my hips so I was laying on my side. She then grabbed a condom from the drawer and spooned me from behind, one hand reaching around to hold my chest and the other teasing it’s way down my side and towards my butt.
I shivered pleasure and anticipation as she stroked my cheek and, despite myself, my cock grew uncomfortably hard. As she started to kiss and suck on the back of my neck, her fingers started to stroke up and down my crack, pressing in just a bit firmer with each stroke until finally she rested a condom covered finger on top of my hole. To this day I can still feel the moment – her mouth on my neck, her hard nipples pressing into my back, her finger and even her nail, in my most intimate spot. She started to press down and I anxiously suggested she add more lube.
As her hand drew away, I was surprised to feel a tinge of regret and longing – wishing she hadn’t pulled away even if just momentarily. As she lubed up her finger, she said she had read that I should push down to make it easier. Not quite understanding what she meant, I unthinkingly pushed my whole body back against her now returned finger – eager to feel what was to come. She gently pressed her finger past the hole and then deeper as I felt the pressure and her finger nail with each stage. Once in she asked how it was.
Still too shy to admit how much I enjoyed it, I just nodded it was fine and she started to move her finger around like her other hand reached around to grab my cock. To my surprise the combination of the moment, her finger at my prostate, and my enjoyment of her previous orgasm all conspired to force me to instantly tell her to stop as I was too sensitive and close.
I’m sure she smiled behind me as she said “really!? Then maybe it should be my turn.”
With that she abruptly pulled her finger out before I could even protest or ask for me and she flipped over onto her other side, pushing her butt out to spoon me with purpose. Already facing away from me, she handed me to lube and, having watched enough porn to think I knew, I liberally slathered it onto my hand.
Without having yet really learned the fun of teasing and eager to feel into her new frontier, I brought my finger right to her butthole. I massaged it a bit to her instant and deep moaning.
“Wow. Oh my god that feels good.”
Encouraged, I continued to massage her hole with my finger, lightly at first but more firmly as she moaned and pushed back against my finger. Eventually she kept pushing and i took my cue to press deeper into her, slipping in more easily that I might have imagined and now started to fuck my finger in and out of her incredibly tight hole.
After a time of this sexy, intimate, and new frontier, she grew sheepish for the first time since I had walked through the door.
“Would you want to try?”
“Try what?”
“To be inside… there? This feels amazing and I want to feel you.”
I doubt I answered so much as excitedly mumbled. Kneeling up quickly and enthusiastically, probably keen to get it going before she changed her mind, I straddled her legs as she laid down on her stomach, gorgeous ass propped up in the air. She grabbed a pillow for under her hips and then implored me to used the whole bottle of lube.
At this point I was all for her directions and I slathered that bottle onto her and my now eager cock. Covered in lube I leaned forward in my knees and hands and rubbed my Dick over her butt crack a few times at which point she reached back and started to position me.
“Slowly. Very slowly. Ok, ok, push a bit mor.. wait! Ok. Now push again. Uh, ok, push again. Mmmm”
And just like that, the head of my cock was in my girlfriends ass. We both paused, waiting for some other shoe to drop in this dirty act. After a moment and my growing confidence the excitement wouldn’t just lead to my cuming instantly,
“Ok, this feels amazing. Would you start to fuck me?”
With that I started to pull in and out of her, slowly and gently, short strokes growing longer until she said she preferred short and small movements.
Bliss doesn’t begin to describe the moment, tight doesn’t begin to describe the sensations, and eventually she could feel my slowing down and growing tentative in my movements as I felt my orgasm creeping into focus.
“I don’t know how much longer this will feel good. I want you to cum in my ass. Don’t hold back.”
With that I laid my chest down on her back so we were skin to skin, connected in this most intimate of ways as I whispered in her ear how much I cared for her and how amazing it felt. Her moans mixed in with mine as I started to cum deep into her ass, instinct and pleasure pushing me to drive as deep as I could into her to deposit my cum.
We both laid there afterwards, sweaty, in love, and blissful as my cock grew soft while still in her butt. We fell asleep that way, piled on top of each other, having opened up whole new worlds of connection, pleasure, and exploration.
Source: reddit.com/r/gonewildstories/comments/hvqmfw/mf_my_college_girlfriend_and_i_open_new_horizons
I love when dudes learn prostrate stimulation. Makes shit so much more fun.
Great story!