Growing up I was extremely shy and was far too nervous to talk to girls. I had one girlfriend in my early 20s but after we broke up I didn’t really date very much and I didn’t have sex again for four years, until I was 26. The girlfriend wasn’t my first sexual experience but she was my first love and we had a very active sex life and became very good at what we were into. Following the end of that, however, I reverted to my natural introversion and social anxiety and thought this was it for life. That is, until this first casual encounter. After that it was like the floodgates opened, and I made up for a lot of lost time, and while I’d always had a very very high sex drive I’ve since then also developed my tastes, interests, and kinks. I’m in my early 30s now, male, and in Australia, and I’ve dated, had short flings, had ongoing friends-with-benefits, had fuck buddies (less friends than FWB I think), had one night stands, and had a small number of BDSM focussed relations. But this is the story of the first casual encounter and the one that really got my confidence up.
Dan was an acquaintance I met through a kind of professional organisation, and while we were friendly, we didn’t always have a whole lot to talk about. So I was somewhat surprised to have been invited to his 21st birthday party. And it wasn’t just a Facebook invite – it was a personalised invite. And while at 26 I was beginning to feel the age gap of being just out of the loop of late teens-to-early 20s references and culture I went along anyway because I thought it was nice of him to invite me and he was a nice guy.
What transpired, however, was that I was feeling even more out of place than expected. It was a great party – at his family’s home in the suburbs of a major Australian city. Nice big house, well catered, plenty of alcohol, and a very nice family. It was a pretty average middle class suburb – not a regional area or anything. And yet it must have been a very insular suburb. Because it seemed just about every other attendee at the party was from Dan’s high school year group. And not only that, a lot of them had known each other since primary school (elementary school for our US readers). And not only that, I had driven to that party and I was on antibiotics at the time, so I wasn’t drinking.
I tried to mingle, but it didn’t work very well for an anxious introvert surrounded by increasingly drunk younger people. People were nice enough and I got through it, but I was extremely glad when speeches and cake cutting came.
During the birthday boy’s speech I found myself catching the eye of the girl next to me. She was about half a foot shorter than me, a little mousy, a thin face with brown eyes, tousled light brown hair that went to her shoulders, a tight blouse and a tight skirt that went to her knees. She had low sensible heels and a vintage handbag-purse. Someone was talking to her during the speech, someone drunk, and she was trying to politely shush him. We exchanged looks and seemed to pick up that we were both completely sober.
When the speeches were done she and I started talking, first out of general politeness, then out of genuine interest. It wasn’t like we had all that much in common – I think it was more we were both relieved to have someone to talk to, although I didn’t actually ask or find out why she wasn’t drinking. She was also part of the same school year group so she was presumably around 21. When I mentioned I was about to leave even though it was quite early she asked how I was getting home, and I told her I was driving. We lived fairly close by, which I knew from our conversation, and since she’d taken a ride with friends to get there, friends who were now drunk, she very gladly accepted a ride home. We kind of said goodbye to people, kind of didn’t need to worry about it as everyone else was pretty hammered by that point.
In the car it was pretty quiet. We’d exhausted most conversation topics, just to the edge of politeness, at the party. And after four long years of celibacy on my part and nothing of the party spirit having caught on from the party we were just at, taking anything further with this girl was not even remotely on my mind. I didn’t even know how to pick up signs.
So when we pulled up at her house and she reached over to kiss me on the cheek I didn’t know what to think when she put her hand on my thigh for balance. I was just utterly bewildered. What then happened was kind of a blur – she kissed me on the cheek, but as she pulled away we made eye contact. And suddenly we were making out. I probably wasn’t any good, but things kept progressing. We kept making out. She kept moving her hands over my legs. She got to my crotch. And I absolutely could not believe it when she started to unzip my pants and pulled my cock out.
I doubly couldn’t believe it when she started licking the underside of my length from balls to tip and then taking all of me in her mouth. This was fricking amazing! I held her hair up for her and started to really enjoy it. So did she, it seemed. When I put a hand on the back of her head she sighed in satisfaction.
She settled into a rhythm, sucking my length until I hit the back of her mouth – not the back of her throat, but the back of her mouth, so that she was only making it about half way down my cock. I’d always struggled to finish from head alone, and after a while she seemed to sense I wasn’t going to finish. So she licked up as much spit as she could and sat back in her seat.
In a moment of bold inspiration I said something tried and true that I’d learnt from pop culture was exactly the thing to say in such moments.
‘Would you like to come back to my place for a cup of tea?’ I said it with a grin – I could still hardly believe what was happening, and I’d grown more confident than I could remember.
‘Tea would be great right about now,’ she replied with a grin of her own.
So I made the short drive back to mine, and we went in, and I made a show of going to the kitchen to boil some water, when she put her hands around my waist from behind. I quickly spun around and we made out, and I led us to my room. I led her to the bed, backed her up against it, and she helped me take her blouse off and unzip her skirt, until she was in panties and lying back on my bed. I tried to run my fingers down her thighs as sexily as I could, and when I got to her crotch the muscle memory of some years before returned and I remembered, I hoped, what to do. I played with her over her panties, then put my hand inside and played with her some more. I took them off and played with her clit, testing her reaction to making tiny circles compared to rubbing up and down, before fingering her with one finger and then two.
And then she simply said ‘Just fuck me already. Condom on.’
I was wondering how this could be happening and thanking my lucky stairs that some time ago – about a year and a half, or possibly two years before – I had bought a box of condoms in anticipation that things would soon be getting frisky. That didn’t end up happening as I’d hoped. It only took years later for it to finally come true. But in that moment I rolled a condom on and got to it.
And it was glorious. Feeling the inside of a pussy again was like nothing else. Feeling the inside of a pussy of a girl I’d just met that night while we continued to kiss was like life could not get any better. We kept at missionary for a while, after which I lifted myself up and rested on my knees so I could hold her legs in the air. After a bit I tried to rub her clit but my rhythm became a little clumsy, and she pushed my hand away and took over rubbing her clit herself.
But I knew what I really wanted to save myself for. I pulled out and motioned for her to get on her hands and knees. Doggy is without doubt one of the best things you can do on this earth. I’m an ass man besides, and there is no better way to appreciate one than gripping onto it with both hands and thrusting your full length into the pussy below it. This was it.
She was kind of lopsided on my bed – propping herself up on one elbow on one side, down on her shoulder on the other as her hand snaked under herself to play with her clit. She was beginning to moan with each thrust, and each thrust was coming harder and faster.
I lasted only minutes longer. And it was the best orgasm, without doubt, I’d had in years. I kept gripping her ass as she furiously rubbed her clit and came hard. Her pussy squeezed my softening cock briefly, then she collapsed forward gasping for air. I was guessing I hadn’t embarrassed myself when she seemed to read my mind.
‘Needed that. Fuck that was good,’ she said as she rolled over.
I lowered myself and settled into a snuggle. She gently stroked my hair and I gently stroked her back as we lay tangled on our sides, not talking but occasionally kissing. After a bit the kissing intensified, and I snaked my hand back down to her crotch to feel she was soaking wet, either still or again I wasn’t sure.
She pushed me onto my back and made her way down to my cock and began blowing me in a way that has since become my favourite, possible because of that night. Blowjobs are extremely important to me and I enjoy them and need them in equal part to PIV, and I think that night was partly responsible. She had this technique of sucking, with varying degrees of intensity, while rubbing her tongue on the underside of my cock. I’ve since tutored many more women in that technique, and I’ve also since learned that she was really quite skilled and quite intuitive as well.
I was rock hard and after a bit she got another condom and began to put it on me, but it didn’t really work so I ended up putting it on. She got on top and started riding for a bit. We somehow both sensed, however, that we wanted something else, so she got on her hands and knees again.
What followed was a bit of a blur. It was the perfect combination of young guy with massive stamina, having let off the edge with a first orgasm, and a girl who enjoyed bringing herself to clitoral orgasm while being pounded from behind. At the time I hadn’t learnt my now favourite techniques of hair pulling, spanking, and light choking, so basically just stuck with jackhammering and moving my hands between holding onto her hips and massaging her ass. I wasn’t sure how many times she came but when I finally did she was an incoherent mess, and we both collapsed.
After a bit of a cuddle I drove her home. She lived with her parents and couldn’t stay over, and I probably wasn’t comfortable with that happening anyway. We had sex two more times but it’s that first time that really sticks with me. I knew we weren’t compatible in any way other than in bed – we had literally zero in common – but I was a bit surprised when contact from her dwindled. Finally she let me know that she’d been talking to someone and wanted to date him, so that made sense.
Source: reddit.com/r/gonewildstories/comments/qbsce4/mf_how_being_the_sober_one_led_to_my_m26_first