Inexperienced teenage fling with an older guy [FM]

This won’t be the most over the top orgy-filled story you’ve ever read here, but it’s a big memory for me and a big influence on my sexuality, and something I feel the urge to tell anonymous horny people on the internet about.

When I was 19, I’d just had a horrible breakup with my first proper boyfriend – the guy I’d lost my virginity to and was madly in love with. We had a lot of firsts together, and I was addicted to him, so I took the break up hard. Until that point I’d been pretty shy about all things sexual, and pretty shy in general actually. At school I was very focused on academic stuff and was the typical well behaved quiet girl more likely to be found in the library than anywhere else. While I absolutely loved to please my boyfriend, I wasn’t confident enough to do things with him that seem tame to me today – I’m now 28 and a lot more open-minded. In general I was a pretty naive teenager who didn’t know as much about sex as my peers, and while I enjoyed it, I wasn’t exactly adventurous. We never did it doggystyle – now my favourite position – because I felt very self-conscious about my bum, which is disproportionately large – something it has taken me a long time to realise is a plus point for a lot of guys. I blew him, but I never swallowed. He was not the most adventurous himself and went down on me maybe twice ever. In fact he was quite selfish, but I got used to and got turned on by the idea that sex was mostly about his pleasure, so I was happy when he took the lead.

I won’t go into details about the break up, which was initiated by him, but that summer, which was university holidays, I got a temping job with a company of about 50 employees. I was one of the youngest there and was put to work doing all kinds of admin tasks. I was quiet and shy as always but made myself popular by being helpful and competent, so got on quite well with some of the others, and before long was invited out for drinks on a Friday by a group who used to go to the pub together after work. One of these was a guy of 34 – attractive, grown-up, well-rounded, and not my usual ‘type’, or the sort of person it would have occurred to me might feel any attraction to me.

After a few of these nights out, him and me were sitting together and everyone else was up dancing or at the bar or whatever, and we got talking one on one. We weren’t even being that flirty, and I’ll never forget how taken aback I felt when he just calmly said “you know you are incredibly sexy?” I was tongue-tied and blushing and just didn’t know what to say next, and he just gave this confident laugh, like he knew what a shock this was to me to hear something like that.

The next day I woke up hung over with all this playing over and over in my head. I wondered if he was joking, I wondered whether I was attracted to him, because I’d just never thought of him that way, I wondered whether I could have anything with him given how raw I felt about the guy I was still in love with, and just didn’t know what to do. But later he texted me and asked if I wanted to meet up that night, just me and him. What got me wide eyed was that rather than make this at a pub or a restaurant or somewhere, it was at his flat. I went over feeling apprehensive but kind of knowing I was going to let this guy fuck me.

We had a really nice evening, he had cooked us a meal, and I felt really comfortable with him. Again he was so confident, and started telling me how he’d noticed me as soon as I started working with him, he said I seemed to be both innocent and dirty at the same time, in a way he couldn’t resist, and he admitted to checking out my arse when I walked around the office. I had never had anyone speak to me like this or be so confident in blatantly trying to seduce me without making an idiot of themselves. I was getting more and more turned on and found myself asking about him, the kinds of women he was into, the relationships he’d had, and just everything I could find out about him. I told him all about my ex, and he told me about long term relationships, fuckbuddies, one night stands, all things I was yet to experience at that age.

By the time he leant in to kiss me I’d had loads of wine and just knew he was going all the way with me. I was shaking but loved it, and kept telling him not to stop as he kissed my neck and undressed me. He started whispering in my ear that he always knew I was gagging for sex and he always knew he was going to fuck me. He was cocky and aggressive, and most arousing to me of all at that point, way older and more experienced than me. I felt like a teenager being taken advantage of by a grown man, and loved it. When he first put it in me I was on my side on his sofa, and he spooned me and grabbed my arse. Pretty soon we were on the floor, and I felt ridiculously dirty because the lights were on, my arse was in the air and I was letting this guy from work have his wicked way with me, like some kind of slut, when I had never done anything remotely slutty.

In the morning I woke up naked in his bed still thinking “what the fuck has got into me?”, and half expecting him to regret it and want me out of the house. Instead he went down on me, against my protests because I was sweaty and sticky and gross from the night before, but he just didn’t seem to care about that or have any of the inhibitions and hang-ups I’d been used to in my previous relationship.

I probably don’t need to say that we kept this up and I kept going over to see him over the next few weeks. He always took charge during sex and got me doing things I’d never have thought I’d be comfortable with. He was the first guy whose cum I swallowed, the first guy I masturbated in front of, with a dildo he bought me that I still have today, the first guy I rimmed, the first guy I let in my arsehole, the first guy I allowed to tie me up and make me beg.

Throughout all this we both absolutely loved the age gap between us, and it was a major factor in how our relationship was so sexual. The memory of this is what made me want to post this story here. He couldn’t believe his luck that he was fucking the nerdy student girl in the office. He would tell me what a filthy teenager I was to let him do the things he was doing to me, how he was ruining me for other guys, how my parents would kill him if they knew what he could talk their daughter into, all that stuff. I never called him daddy because that word has just never appealed to me in a sexual context, but when I read DDlg experiences I identify with a lot of the mindset of the women involved. I totally played up the whole innocent girl thing with him, and I know he used to boast to his friends that he was fucking me, and possibly showed them pictures.

We stopped seeing each other when I moved away at the end of the summer, and kept in touch a little as friends. We never had an exclusive arrangement, and I think while we were seeing each other he may have had one or two other encounters, while I was his alone. I’ve had a lot of hot sex since, but I always look back to that summer as the one where I was brought out of my shell by a confident, dominant guy, who shared my interest in feeling depraved about our age gap.

So… not the hottest piece of erotica, but I wanted to get it off my chest, and I’ll talk more about it in the comment thread if anyone is interested in particular parts of the story.

Source: reddit.com/r/gonewildstories/comments/5h5in0/inexperienced_teenage_fling_with_an_older_guy_fm