This is a new chapter in the saga I started here: https://old.reddit.com/r/gonewildstories/comments/u33z2w/f_i_f45_had_a_secret_affair_for_8_months_it/, but it’s pretty different now, less a story than a dive into various memories.
Ali was my first real boyfriend and my first fuck. My first most things, actually. We were eighteen, late bloomers. Before we were together I had made out with a few boys at dances and parties, “dated” a few for a few weeks and that’s about it. I’d say I made out with more guys than most of my friends, and I was pretty into the idea of sex, but whenever I was with someone I was quickly turned off. There was a lot of clumsy boob-handling and fingering,but it was always too fast, fumbling, frantic, and fogged up with insecurity.
I felt sorry for these guys and acted like I was having a ball, but most of them didn’t make me cum or even feel good. I had to convince the two or three guys who agreed to go down on me, and I liked that better, but they would always stop after 30 seconds, long before I was ready to stop. The furthest I’d gone with anyone before Ali was giving a few blowjobs. It’s not that I particularly liked giving head, but I enjoyed giving pleasure. And it was so easy! But I didn’t truly like doing it until Ali.
Then Ali and I hooked up at one of those insane parties at someone’s house when their parents are away for the month…. It makes me shudder to imagine it, now that I’m a mom. Anyway, it was probably early October but it was unseasonably warm. Everyone was drunk, swimming, breaking stuff. I was not especially wild, more mellow. I hung out with the hippies and grunge kids, smoking weed and chatting instead of doing shots and getting rowdy. This night I was with the usual crew around a bonfire. There was some singing and guitars, all very calm and cool compared with the mayhem going on inside. I remember singing “Unknown Legend,” which had just come out; that’ll give you a sense of the mood.
There were some folks there from another school at the party, and some of them hung out with us. Ali was one of them. You could see the interest around the firepit as soon as he showed up. Ali was good looking. Clean-cut and a bit nerdy compared to our more ragtag look, but definitely good looking. His profile was incredible. What a perfect nose, and these incredibly long eyelashes. It was hard to tell in the dark, but I would later see the feature that had girls swooning over him, that rare combination of black hair, caramel skin and green eyes. Oof! Everyone was looking at him, and when he borrowed a guitar and sang, with a voice that seemed endearingly wobbly, it was like all the girls were melting on the spot. I was pretty stoked that he had sat down next to me.
When I sucked on the joint he passed my way, I felt all wet knowing his saliva was on the paper I was now putting on my lips. It was like a long distance kiss. Soon after he passed the guitar back to its owner, we were holding hands. Soon after that, we were making out in the pool house. He kissed for ages while he squeezed my tits and sucked on my nipples, just like every other boy would have, but the difference is he was doing it slowly, and well. Really well. It was like he knew what my body wanted, or maybe he knew how to make my body want what he did next.
But when he started pulling tentatively at my shorts, I stopped him. I wanted him, but I didn’t want to go further in a mouldy poolhouse when someone could just walk in. He understood and didn’t push it further. We made out more. I didn’t mind him sliding his hands down the back of my shorts and squeezing my butt. I was so tempted to do more, but there wasn’t any obvious place to go. I wanted to go down on him, but I didn’t know how to ask, usually guys told me when they wanted me to. Ali was obviously turned on, I could feel his hard on through his shorts when he was grinding against me, but he didn’t steer things. He let me take the reins, and I was weirdly too shy to take initiative.
We grinded hard, and to my complete shock the friction of his boner through his swimming trunks suddenly made me cum. Once the immediate flood of pleasure had passed, my reaction was to laugh uncontrollably while Ali rearranged his clothes, looking confused. Later, he told me that he’d cum too, in his trunks, and he actually thought I was laughing at him because of it. I didn’t know that, I just thought he was having second thoughts. I was a bit hurt, not knowing that he was embarrassed. Oh, high school! All that insecurity and awkwardness. When he went home soon afterward, without either of us saying anything about seeing each other again or trading phone numbers, I figured that was that.
Luckily we had friends in common, and soon one of my friends passed me Ali’s number, which she’d got from one of his friends. Like I said: high school. I waffled for days, and finally my friend called Ali for me, with me blushing and cringing in the corner while she talked. She said I wanted to see him again and could he meet me outside our school on Friday? I knew he’d said yes before she hung up.
So Ali and I started “going out.” Mostly, at first, we went out with other friends, in big groups of teenagers, and so apart from more kissing and pawing at each other, nothing much happened for a while. But eventually I invited him over for dinner, and my parents loved him. He was polite and articulate, and he laughed at my parents’ groan-worthy jokes, and really that’s all it took. It also helped that he was pretty clean cut compared with my other friends. I found out that my parents were pretty relaxed about me having a boy over. We would disappear into my room for hours, and they never bothered us. Finally we had time and privacy, and we started making the most of it.
It was in my bedroom that I first saw a guy fully naked, and that a guy saw me fully naked too. You have to remember (or imagine) that this was a time before people had easy access to porn, so most people didn’t really get to know what other bodies looked like, let alone close up and personal. We explored each other with a curiosity and interest that I feel I’ve been trying to recapture ever since. We took turns lying without moving on our backs while the other just looked, though it was allowable to move the motionless person’s body for a more intimate view. I remember Ali working my thighs apart and peering down between my legs, so close I could feel his breath against my pussy, and getting so aroused knowing what he could see and how much he wanted to taste me. But tasting was not allowed during that part of the game.
He really, really enjoyed oral, so for the first few months we were together, as often as not, one or both of us was going down on the other. I found out how easily I could cum–it only took the slightest bit of skill and patience, something none of the other guys had had. And I discovered that I loved, loved, loved giving blowjobs. Or, to be accurate, I loved giving blowjobs to Ali.
He got so much joy out of them, and his dick was very, very pretty. He had a habit of telling me what he’d do to me after I made him cum that got me incredibly horny. No one had ever talked to me about sex, and here was this gorgeous guy telling me how he would suck my clit and tongue my vagina once he had ejaculated in my mouth. For someone who was new at this, it was an incredibly erotic but also mind-expanding experience. Sex could be not only fun and pleasurable, but also good for my self-image.
One weekend my parents rented a place by the beach and let me bring Ali along. We had separate bedrooms, but more for appearances than anything. No one checked on us, and that was the first time I slept in the same bed as a boy. On the Saturday we rented bikes and rode far out of the town into a field, where we hid in a small wooded area and made out. I had given Ali handjobs before, but it was always in the dark, or at least sneaking under covers or clothing. This time, I was able to watch the whole thing–not only my hand working Ali’s cock into a full erection, but also his facial expression as I brought him closer and closer to orgasm. The best part, though, was seeing him cum. This was totally new to me, I was fascinating to see the spurt out of him in little jets. I had always thought it oozed out passively, like sweat or snot (I know, that’s an awful comparison, but I didn’t know what else to compare that image to). I wiped it off my hands in some grass, and told him I wanted to try having sex.
Ali’s response was strangely muted. I had expected that there was nothing he would want more. I asked him if he was against sex before marriage or something (it wasn’t impossible: his parents were pretty traditional), but it wasn’t that. He admitted that he’’d already had sex with two girls before me. I wasn’t jealous, in fact I was relieved. I figured it would be better if one of us wasn’t totally inexperienced. But also it meant that he wasn’t against sex. It turned out that he hadn’t particularly enjoyed intercourse, that he preferred oral by a long shot. I said I still wanted to try, maybe it’d be better with me. Even it wasn’t the best, surely it’d still be fun.
Source: reddit.com/r/gonewildstories/comments/uvn57w/f_portraits_of_my_f46_past_lovers_part_xii_ali