My unusual [f]irst ti[m]e

I think high school is a time where you either get laid a fair bit, or not at all – and unfortunately for me, it was the latter. You see I had a bit of a reputation for being a bit geeky, a bit too smart for my own good. You know the type… seemingly more into games than girls. I knew this, and I had the insecure acceptance of this reality that just compounded the problem. As such, I didn't get any action in high school and am what you would call 'a late bloomer.'

In college I came into my own alot more. Intelligence was more highly valued, more common and a sharp wit more appreciated. In turn I received more attention from the opposite sex. But, having the stunted beginning I still had trouble turning this into anything more than a few drunken hookups. Not that I was bad looking. I am 6'0, have jet black hair, and have a medium build – I'd say average or slightly above.

I still spent way too much time in front of the screen, chatting, gaming and… lets face it – jerking off to huge amounts of porn. I preferred chatting to friends and women via msn or yahoo chat where the pressure was off and the conversation flowed at a steady pace. Sometimes when no one was online, I would trawl msn profiles, or myspace for new friends. I say friends, but I only ever contacted women so I will leave you to judge. That's where I met Amanda. She had this little anime cat-woman as her profile pic sort of like this, which seemed almost sexual in nature.

Amanda was 22 at the time, a few years older than me, and was in her final year of occupational therapy at a different university. We chatted for a few hours, about uni, life, likes/dislikes – the conversation flowed smoothly and I liked her. She soon asked for photos of myself, which I sent. When I asked for some back she said "The only ones I have on this computer aren't really 'appropriate' so my profile pic will have to do for now ;)." That should have been my first hint of something good, but it blew right past me.

Amanda was about 5'3, with lovely flowing dark brown hair, smooth pale skin and small but perky B cup breasts. Her smile, despite slightly crooked teeth seemed to betray something devious about her. She had gone to an all girls catholic high school years ago and had found it to be a difficult place with that 'strict code of behavior.' I'd soon find out that this had manifested itself later in her life as a love of things taboo and a little unusual. Excellent for me, as I was and still am a bit unusual.

I was chatting to her about my love of pool / snooker soon after we had begun talking and mentioned I had one at my share house. She said something like 'oooh… I love pool tables, but I'm not sure you'd call what I do on them playing.' I took the safer route on this and assumed she meant she played poorly and I offered to give her a few lessons. When she replied '… sure, I'd love a lesson or two on your pool table,' I finally got the hint and started flirting back – albeit not as overtly as her. It became a game where she would try and push me and get me riled up with obvious innuendo and I would play back by replying in a way where it was ambiguous if I realized or not.

Looking back, she must have been really confused because the conversation would constantly turn to sex, and we had wound up sexting a few times, but I had yet to suggest a meet. She would frequently respond to questions like 'Hey how are you?' with 'Good, but I am really really horny.' I'd deflect – playing hard to get perhaps, or just being inexperienced. Of course had not told her I was a virgin and had no intention of doing so.

She had started to trickle-feed me the inappropriate photos of herself about a fortnight after we started chatting. I have since lost them all when a hard drive crashed, but I remember one of her sitting on her bed, curled with her ass facing the camera. Her left arm ran over her left thigh and her entire hand was stuffed into her pussy. She was obviously moaning, and her face, as well as her chest was flushed red. I cant tell you how many times I jerked off to that.

We continued to chat daily for over a month before we decided to to meet – very soon after she sent the previously mentioned photo. We lived only an hour apart – not very far and I probably should have made the trip sooner.

We had dinner at a little place near her student accommodation and laughed about how long it had taken us to meet. We had a little wine, paid the bill and walked through a nice park on the way back to my car. We jumped on the kids play equipment there, and she sat down on the top of this short ladder that brought her head to my height. Naturally I leaned in and kissed her, and she responded enthusiastically, twirling her tongue into mine and intermittently sucking my top lip. I was instantly ragingly hard, having not jerked off in a few days, but from her perch she couldn't see.

After about 20 minutes or so of kissing, then horsing around on the park slides and play equipment in the semi-darkness, I said it was time we got her back home. She pouted, but then agreed and I drove her back. She said 'you should come in and see my room! but you do have uni tomorrow.' She gave me the out but I agreed to come inside of course.

Her flatmates were out and we had the place to ourselves, but we headed straight for her room where she had a little tv set up. She slides off her jeans, revealing a pair of plain black panties. 'Come on,' she said, jumping straight under her covers 'watch a movie with me.' It was summertime and I have no idea why she had a comforter on her bed, but we were under that sweating away. We kissed and then I slid into the big spoon position as we faced the tv. I still didn't have the 'this is it' thought until she said, 'sorry, its really hot in here, but I like the weight of the comforter – I usually just lie under here naked, would that bother you?' The jackpot noises start going off in my head as I concentrate and respond… 'no not at all.' With that, she rummages under the sheets, and off comes her top, and bra. Behind her, I fiddle with my jeans and manage to shimmy out of them and soon am in just my underwear.

I go back to spooning Amanda, laying my hand on her side and gliding it up and down her gently. On one of my many trips down I notice she has kept her very thin panties on. I wondered if this meant she didn't want me to go too far… But resumed tracing my fingers over her side and shoulder. Her body would respond in such an amazing way, undulating and moving to increase the contact of my fingers. She made little 'uh' and 'mmh' noises as went over the sides of her breasts or over the tops of her shoulders.

I knew from our conversations she liked to be bitten, on the shoulder and collar bone. She loved breath in her ears, and her nipples to be treated roughly. I kept up the steady touching for some time, absentmindedly watching the movie. When she started making noises, I breathily asked in her ears 'does that feel good?' and she bucked her hips into my groin as a response, rubbing against my hardness. Slowly my hands ventured further across her side, edging closer to her nipple. She had stopped watching the movie and I could see over the side of her face she had closed her eyes. Her body made needy movements when I edged towards her nipples, arching at my hand. I finally relented and allowed myself the pleasure of exploring her nipples. They were erect, almost twice the width of a pencil and rock solid. I dived in and squeezed, eliciting a moan that sounded both of relief and frustration.

I was having an extremely hard time concentrating with her ass periodically bucking back and rubbing my cock through my underwear. It was like I practically had a cheat sheet to a final exam. I knew so many of her little ticks and quirks that got her off. I pressed onward, biting her shoulder and feeling her convulse. I slipped my hands round her and ran them between her legs, avoiding directly above her pussy. She was practically frantic with frustration, and kept saying 'ohh god, touch me please.' I relented eventually, sliding over her panties, which were absolutely sodden. Her juices had seeped completely through, her panties as slippery as if I was directly touching her.

We had talked about how it 'had been a while' for me and that I was worried about going the distance – little did she know how long it had actually been. Amanda just said 'Please. Please just fuck me. Don't worry about lasting. Just cum in me and we'll fuck again later.' I am pretty restrained but even I had my limits. I peeled her dripping panties off her and slid them down her legs, removing my own underwear as well before resuming my position behind her.

She reached back to grab my cock and sighed 'god its so big and thick.' I didn't think I had a particularly big cock but apparently just under 7" and thick is quite a bit above average. She wiggled back and rubbed the head of my cock, slick with precum already, against her sex. I grabbed her hips and pulled her back while she also pushed back. She was so excited her silky smooth pussy enveloped me in one stroke resulting in a deep mutual groan.

I started pumping, almost fully withdrawing on each stroke before sliding back in slowly. Amanda was moaning almost constantly, and I reached around her, placing a hand around her neck to press another one of her buttons – choking. She grabbed my other hand, which had been under her body since we started fucking and drew it up to her mouth, jamming a few fingers in. This turned me on immensely and I picked up the pace, thrusting faster into her pussy which she had angled to give me better access. Each stroke was punctuated with wet 'mummph' and 'eeecck' noises, seemingly based on how hard I rammed it into her.

It had barely been three minutes before I felt that sensation that the dam was breaking. I tried to concentrate, make it last longer, but her squeals and moans, her drenched pussy and the sucking on my fingers made it impossible. I said something like 'Urghhh fuck,' which Amanda noticed, and then began thrusting her body back against me. My body clenched and she made one final thrust against me, holding me deep inside her as my hot load spurted into her. She expertly wiggled her body around, slightly coming off me and back on in time with each jet of cum.

We lay like that, still, before bursting into laughter – almost surprised at the sexual chemistry. She slid off me, and immediately slid her hand down to her pussy, sliding her fingers through our mutual juices before tasting it. 'Mmmmm your cum tastes so good' she said, quickly turning around and popping my cock into her mouth before I knew what was happening. She bobbed up and down a few times before briefly looking at me, 'next time you definitely have to cum in my mouth.'

I didn't have to wait long for next time. This was one of the few occasions in my life where I stayed completely hard and was ready for more almost instantly. Look… maybe it wasn't that unusual for a first time, but it sure started off some crazy sex adventures.

Source: reddit.com/r/gonewildstories/comments/3m2htw/my_unusual_first_time