[M]y [f]irst time – Part Two

Back by the popular demand of literally one user (stonefio55), I proudly present to you – Part Two.

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Stone – in case you needed a recap, here’s [Part One](https://www.reddit.com/r/gonewildstories/comments/ohtc1m/my_first_time/).

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As mentioned in the conclusion of Part One, Ellen and I parted ways in 2005. Apart from the odd Facebook message in 2011 (I was lonely in Hong Kong, and wondered if she had any good travel tips), we lost touch completely. Completely, that is, until the summer of 2015 – my brother’s wedding. And that’s where Part Two picks up.

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At the time, I was living and working in Asia. I was both nervous and excited to hop on a plane and head back home for my brother’s wedding. I hadn’t been back in over a year, and it would be the perfect vacation to see some familiar places and faces again. Who doesn’t appreciate a bit of the old nostalgia. But on the other hand, I was a nervous wreck. My brother had made me his best man, and of course, I had to get up in front of everyone and give a speech. To this day, I detest public speaking. I detest public speaking as much as I enjoy sex (which I’ll get to in a moment, I promise), but I couldn’t let my big bruva down. Not on his big bruva day. So much like I’m doing now, I opened a note on my iPhone, and started writing.

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The ballroom was filled with applause and cheering, as I returned to my seat after delivering the speech. To say it went surprisingly well would have been an understatement. At least four people came up to me and said it was the funniest best man speech they’ve ever heard. And I knew they were telling the truth, because I had also played the guitar during the ceremony, and no one had complimented or said shit about that. Fueled by their genuine compliments, my ego went through the roof. I looked around, and saw many of my brother’s old high school friends, some of whom I knew myself. I recognised one girl at the high school reunion table – it was Anna, and she looked smoking hot that night. I had a crush on her in high school, and since she was two years older I had never had the chance to speak to her.

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Fuck it, I affirmed to myself. As everyone was mingling and drinking, I went for an empty seat beside Anna. She looked at me “That was a hilarious speech, – (I almost typed out my name here).” I smiled at her, “Thanks, I had a huge crush on you in high school.” I said, intoxicatedly. She laughed it off, and we started talking about high school and old friends, and before I knew it my tongue was in her pussy. Kidding. I had seen on Instagram that she was friends with Ellen, so I thought I’d ask how Ellen was doing, as she was somewhat of a mutual friend. “Oh yea, we do hang out from time to time. Didn’t you guys date for a bit? Actually, she’s in town right now!” A slightly more suggestive friend adjacent to Anna chimed in, “Yea, and she’s single now too. Her boyfriend cheated on her, so she left him and moved back here”. Apparently, she had just gotten out of a ten year relationship – it was one of the guys she was “three-timing” in Part One. Suggestive Friend chimed in some more, “I can message her and ask her to come here if you want – we were actually going to hang out after the wedding.” Uhh, yes please. And then after what couldn’t have been more than 20 minutes, Ellen stepped into the ballroom with some other friends.

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To be honest, during the 10 year gap, I had stalked Ellen’s social media on several occasions; in fact, more times that I’d like to admit. But don’t we all do that? Look up people we used to get frisky with, fill in details with our memory, and fap to their social media pics? Maybe that’s just me. Feel free to share your stance on this matter. And as always, don’t forget to rate, comment and subscribe. On her Instagram account, I was particularly drawn to a picture she had taken at what seemed to be a horse racing track. She had on a pair of black leather boots, a black skirt, some sort of black shirt or blouse (tbh, I don’t even know what a blouse exactly is) that showed off her toned abdomen and belly button, and a black jacket over that. Her shoulder length hair was straight and black with dyed streaks of blonde (apparently that was still in). When Ellen walked into the ballroom that night, I kid you not, she was wearing that exact outfit (minus the boots maybe). When I saw her, I was actually manoeuvring my way through the crowd trying to get to the bathroom, when a familiar scent of sweet grapefruit and chicken nuggets caught my nose’s attention. I physically bumped into her. Concealing my eagerness, I say hi, and continued to the bathroom, where I formulated my plan.

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As I was only in town for the week, I was staying with my parents. My parents had since moved, and did not have a spare room for me, so I actually just slept on an old, green twin-sized sofa bed that I pulled out each night. If the end goal for that evening was to take Ellen to bed, there was no way in hell it was going to be that bed. I had found out that Ellen had also just gotten back, and was sharing a queen-sized bed with a girlfriend. Better, but still not ideal. However, what I also learned was that my brother and his new wife, along with my parents, would be spending the night at the hotel. That left two options: my brother’s apartment or my parents’ bed. I imagined the worst case scenario where the owner of said bed would walk in on Ellen and me. After some contemplation (I was still sitting on the toilet by the way), I chose my parents’ bed, which was in a house. A house has multiple exits to sneak out of (as we had experienced ten years prior), while an apartment only had the one.

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I hung out with Ellen and her friends for a couple hours in the hotel casino and bar. But quite frankly, from the moment we saw each other, we both had a mutual understanding of what was to come. I guess we were just trying to dilute the experience to not make it seem like she was a mere booty call. And she wasn’t. I was genuinely excited and happy (but mostly horny) to see her again after all these years. In addition, I would like to remind you that we had never actually fucked. To be very honest, she didn’t even see me naked in high school. I guess I was scared or something, or was just content from fingering and kissing her. I was curious as to see how we’d grown and will “perform” after all these years. At one point, apparently noticing how absent I was, one of her friends just came out and asked the group “hey, do you want to take Ellen home?” “Uh, yes, very much so,” I said, so we hopped in a cab.

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We had a nice time catching up in the cab – we touched on past relationships, work, and each others’ genitalia. As we almost reached my parents’ place, I realized I didn’t have a condom. “Hey, I don’t have a condom”. She gave me a startled look. “Hi excuse me, do you mind if we pull over at a gas station to pick up some condoms”. I picked up two 3-condom packets: one regular blue one, and one “extra thin”, in case I wanted to live dangerously that night. I got back into the cab, and before I knew it, we were in the front door with the house to ourselves.

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This time was very different from our first time. There was no need to sneak around or use a Japanese exchange student’s room. So what did I do? After closing the front door, I immediately started to strip off my tuxedo. Not in a sexy way either – I had that thing on for almost 17 hours at that point. But somehow, as she was an old friend, I was very comfortable around Ellen. When I was down to just my shirt and tighty whities, I grabbed her and kissed her with ten years worth of pent up horniness and jerking off to her social media pics. As before, she closed her eyes when she kissed me, while I stared at her face. I kissed her lips, neck, ears, and even blew into her mouth for old times’ sake. I grabbed her ass through her skirt and squeezed her against my chest. As we continue making out for a few minutes (still beside the front door), she pulled away and went “I’m on my period.” As I was more experienced at this point, I asked the only logical question that could follow that statement: “Which day?” To which she replied “Second.” Fuck me. The Second Day. Or as I like to call it – Sweet Sweet Niagara Falls Day.

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I could see the horniness in her eyes, and clearly she implied that we were going to have period sex. But I had a different concern on my mind – like a horny Dexter, I had to ensure that a single drop of her blood was not left behind. In the cab, I was fantasizing about how we would start stripping at the front door, move to the couch, fuck in the kitchen, and finish in bed. Instead, I went to grab the thickest, largest, and oldest towel I could find, and neatly laid it down on my parents bed. With her lying down, carefully in the centre of the towel, I straddled on top of her and continued making out with her. I stripped off her jacket, then the ambiguous blouse, and then the skirt.

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I felt the crotch of her black panties, unsure if the wetness was pussy juice or blood, and slowly pulled them off. Bingo, not blood. I fingered her a bit. Still, no blood. “Hey it’s actually not that bad”, I said aloud. I took off my shirt, and continued kissing her ecstatically, grinding my tighty whitied package against her pussy. I took off her bra, and squeezed her nipples while we continued to kiss. We must have made out like that for at least 10 minutes. She looked up at me and whispered “I missed you,”, which was definitely a horny lie, but I accepted it nonetheless. I took it slow and tried to savour each moment, knowing full well this would likely be our last time. I stopped rubbing my crotch against her pussy. I reached down and started massaging her pussy, then her clit, then full on fingering her with three fingers.

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She was loud. Our teeth rattled against each other, as I continued to try kissing her while her moans turned to screams. As she indicated she was about to climax, I pulled out and a stream of bloody squirt sprayed all over my parents’ bed and wall. Kidding (I know those liquids come out of different holes…). However, what did happen was at that moment, a distinct smell hit my nostrils (no she didn’t shit herself) – a whaft of metallic, irony blood. I looked down. To my horror, my fingers and palm were soaked in her period juices, and my tighty whities had become tighty reddies. I got up and checked the bed for any stains – 100% of the blood was on me. Thank goodness. So I shrugged, and continued.

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Eventually, I asked her if I could eat her pussy. I hadn’t done this with her back in high school, due to my firm belief that oral sex immediately resulted in AIDS. She was slightly reluctant, not because of her period, but because her boyfriend of ten years never did this for her. In fact, no one had ever done it for her. Fuck yea. The feeling of being the first at something never fails to turn you on. Even if it meant getting a blood moustache along the way. I went down on her, licking her clit and then inside her pussy. Surprisingly, I think I had gotten all the blood with my underwear and hand. I swung around, 69 style, so she could suck my cock and balls.

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I like 69ing on top because it provides more control; if she forgot about the balls (which she did), I could easily adjust. Bring the balls – to her, as I always say. I reached over and grabbed the two packs of condoms, and asked which she preferred. “Do you and your ex usually use the thin ones?” “Actually, we never used condoms. He just pulled out”. I considered it for a second, but then concluded I was only “extra thin” kind of dangerous, not “she’s on her period so she probably won’t get pregnant anyway but my hands are too bloody to google this right now” kind of dangerous.I slipped on the condom and went in her missionary style. I’m not very big (pics available upon request), but she was definitely the tightest I’ve ever felt to this day. After a few minutes of missionary, I did her from behind (as she had alluded to this as her favourite in the cab). Then we switched to my favourite position: she’s on top, but you’re hugging her body in, and her head is beside yours. My nails dug into her back as I pumped as hard and fast as I possibly could.

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At this point, I wanted to cum badly. So in attempts to make her cum (again?), I thought I would transition into my fool-proof-make-a-girl-cum position. There’s probably a name for this, but essentially: she’s on her back, with one leg resting on the bed, and the other raised up on your shoulder. With both arms, you grab onto her raised leg (like hugging a tree trunk), and basically penetrate her in a scissoring like position as hard and fast as possible. Grinding works too. In my experience this is the deepest penetrating position I have ever mustered – she would say things like “Ah, you’re so deep” or “Ah fuck, so deep so deep.” That’s why I have aptly named it the So Deep So Deep position.

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However, I never got the chance to SDSD her. She said “I want to do this” and did the one thing that makes me cum almost immediately – cowgirl grinding. She got on top of me, sat on my dick, and smothered the life out of it – and indeed a lifeless penis it was.

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I need to go meet my brother now, so I’ll give this a quick proofread and post it. Hope you enjoyed fapping to this, stonefio55 (do you fap to these stories? or just read them on the bus or something?)

Source: reddit.com/r/gonewildstories/comments/oil7xv/my_first_time_part_two