*note: this story alternates between intimacy and pre-intimacy. I have separated the “flashbacks” by three asterisks (***) so you can get to the good stuff if you want it. Enjoy.
***
You know you shouldn’t be doing this. You know that you shouldn’t have her hand around your cock while you lean over her, even though she makes it feel just like that summer after high school. Even though she’s wearing the same perfume she used to wear. You could have stopped this a long time ago. Then you wouldn’t be in her honeymoon suite the night before her wedding, getting jerked off by her and kissing her neck, thinking about whether she is still a virgin.
***
You could have stopped this a long time ago. You were back in your hometown to celebrate your younger brother’s graduation. Your wife couldn’t make it, since it’s two plane rides away and she has to work long hours at the hospital, and you were saving up vacation days so you could go on that honeymoon she’s been planning for so long. You decided to go for a run, just for old time’s sake, down the trail by her house.
“I just like the trail more than the roads,” you told your parents when you took their car to drive there. Maybe it was to relive the memories you and she used to have on the trail. Back when she was your long term high school girlfriend, star of the cross country team, and you two used to run together because that was the only time she had to spend with you, and because it was the easiest way to get her out of her very religious home.
The trail had a lot of hills and dense woods. You might sneak up to the top of one, far from view of anyone else, and pull her hips close to you. She was a little sweaty, and so were you. This is where she blew you for the first time. She got on her knees and slowly pulled your shorts down. Your cock was already hard from the making out, but now it was as long as it had ever been. You pulled as much of her long, blonde, curly hair back in a makeshift ponytail as she kissed the head and started bobbing on it. You’d been asking her for it for three months, and finally, she got on her knees and gave you your first blowjob. She kept bobbing, and you told her to stroke the shaft, so she did.
It wasn’t great at the time, but she got better, with you telling her more and more what you liked. Even after two and a half years, you never got further than that, though. She was trying to save herself for marriage. Even fingers inside of her were off limits. She had a scholarship to a school a few states away, and you were going to school out in California, so you two mutually broke up, basically on good terms.
So you went for that run. You were hoping that she might be out on a run too – and she was. You saw her from a ways away. Even though she hadn’t run for the college team in two years she was still in great shape. If anything, she was a little more curvy, and her boobs were more than bee stings through her sports bra. She said “hi!”, and you said “hi!” back, and you tried to catch up. You pretended not to know that she was engaged, and “wow your wedding is in two days?” even though you checked her social media religiously.
She asked to run with you for a while, and you “accidentally” ran her past the spot where she used to blow you. You tease her a little: “wow, you’re almost in as good of shape as when you were running with the team!” Later, when you’re stretching on a cool down, she feels up your arm muscles. She tells you her bachelorette plans, from dinner to the route of the bar crawl. You don’t commit to seeing her again as you run back home.
You text some old friends the next night. The night before her wedding. The night she’s going to be at Paddy’s, then the District, and then her hotel. “Hey, what do you guys think about going out tonight? I came back last minute for my brother’s graduation.” You guys pregame, and then go out, and make it to District before ten. Your friends are making plans to bail and go home, and you’ve just about given up hope around eleven. But then she comes in with her party. It’s just her and a couple of her friends. Now your friends are ready to stay. You let her find you. “Wow! What are you doing here?!” She asks with a wink. “I got dragged here by these two,” you explain.
You dance on the floor, but only with her friends. She’s getting married, after all, and you don’t want to look like you’re doing anything untoward in front of your friends and hers. Finally, her friends get tired. She’s looking sweaty. She leans in to you and looks up at you, like she used to. “Hey now… Where is… Where is she?” she asks, referring to your wife. “Couldn’t make it” you respond. Is it ironic that you’re married before she is?
***
You should have stopped it back there. But now she’s moaning your name. When you kiss her, she’s still got a little bit of sweat from the dance floor, and her hips are grinding up against your leg. Through her jeans you think she might be getting wet. She’s stroking your cock rapidly now. “Oh fuck… you’re still so good at this” you say. You reach behind her and undo her bra and push it out of the way.
***
Her friends’ ubers have arrived. You’re still talking to her about her husband – a similarly religious guy, from a few towns over, who happens to look a lot like you – and follow her into her uber. She doesn’t protest. You’re both in the back and she sits in the middle seat so that she’s leaning up against you. She tells you that she has something to show you, back in her room. “But what about…” you ask. “Oh he’s at home. We’re staying separate until the wedding night. Come on!” Staying separate?
Her hotel room is the bridal suite. She’s a little tipsy from the alcohol. The room has a cute calendar on it that she brought it. While she’s going to get something, you take a closer look at it. Some dates are marked in red, some in green, and the week around the wedding date is highlighted – “ovu week!” it says. She planned her wedding date to coincide with her cycle. According to the calendar, she is ovulating right now.
“Here… here’s my dress!” She says, holding it up. It’s a darker white with lots of poofy components. She wanted to show you her wedding dress. “Say, why are you getting married so fast?” you ask. “You’ve only known this guy for like, what, seven months?” She explains that the timing was “just right” and “when you know, you know!”. “Yeah, right, it’s probably because he wants to have sex with you!” you blurt out.
It gets very, very quiet. She asks you a question. “Why… why do you think sex before marriage is OK?” You tell her about your own experience. With your now wife. It was a way of embracing each other. It was a way of becoming more vulnerable. It felt fucking good, and it was wrong to deny the pleasure that could come from sex. “Didn’t it feel good, making out, all those years ago?” She looks at you with doe eyes. “Imagine that, but… times 100. That’s what sex is like. And it only gets better.” She’s really looking at you now.
“Look, figuring out what you like and how to please your partner… that’s part of a healthy relationship. For instance, when I’m with my wife, I know where her spots are, because we’ve explored that. It makes it so much better. I wish that we could have had that.” She’s leaning in to you. “I wish that I could have had my first time with you,” you say, and lean in to kiss her. But you still could have stopped.
***
But now you’re nibbling her ear, and she’s unbuttoning her pants. “I… I have to tell you something…” she says. “I’m… still…” “Shh, it’s OK… we don’t have to do anything you don’t want to do.” You reassure her. As if. “Ok… just… only things we’ve already done before, OK?” If that’s all she wanted, why is she unbuttoning her pants? You roll over to your back, and she’s on top of you, starting to bob her head on your cock.
“Oh… fuck… Oh…” you moan her name. “You know… you should really…. Really know yourself…” you say. She’s coy. “It would just be, you know, exterior, so you can find your clit…” You just know that she’s never even thought about masturbating. She’s definitely not on birth control – that wouldn’t be allowed either by her family.
She rolls on to her back, now totally topless, with her wedding dress laying on the bed next to her. You get on top of her and start to trace her outlines. “Now, no… nothing… Oh wow…” she says as you start to trace the inside of her legs, to her outer labia, getting closer and closer to her clit. She’s swelling out of her white panties. Every time you get close to it she jerks like it’s too much. She’s probably never even had it stimulated. “So does your fiance do anything like this?” you ask. She’s shaking her head no.
“Wow. It’s a good thing you get to be around me tonight, otherwise you’ll probably never know this stuff, because God knows [he] won’t know how to do this.” Your hand is down by her crotch and she’s starting to grind onto it. You use your right thumb to play with her clit and make circular motions with the palm of your hand. Your middle and ring finger are tracing the outline of her hole.
“Just, just one…” she says,putting her hand on yours to push your middle finger in to her virgin pussy, just down to two knuckles. She is so tight. “Did that hurt?” you ask. “Nng.. just a little…” she says. You grab some lotion from the bedside table as lube and start to finger her. “Just think of this as making you a little more welcoming, you know” You say. You ask her what’s feeling good and she wants more on her clit.
You rearrange yourself, down between her legs, and start to kiss and then suck her clit. She is getting so wet now, the tightness is not as restrictive. You add another finger. “Is that OK?” You ask. She nods in between panting. You continue to gently suck on her clit and get both fingers in all the way down. Every time you add a little more, there’s a little cry of resistance, but she keeps moaning your name. You get on top of her to kiss her, with your cockhead on her belly button, a few strings of pre cum dabbing her belly.
She reaches down to your cock. This is the point of no return. She plays with herself with it, pushing it in just a millimeter, then pushing her clit, and pushing it another millimeter. “You can do it” You say. “Oh, I want you so bad…” She says. “Do you have a condom?” As if she would have a condom in her wedding suite that she booked the week that she is ovulating. “No… ok, you just have to promise to pull out, OK?” You promise.
You push through her as slow as possible. You’ve never been raw, not even in your wife, since she is worried about pregnancy. The feeling is almost too much. You let out a low groan, and she lets out a tiny cry, like she is feeling pain. She is so tight and so wet. You check that she’s OK. Yes, she says, and she wants more of you. Finally you get down to balls deep inside of her. Missionnary style. You gently thrust into her, each time she moans a little more for you. Her legs are around yours and she is kissing your neck.
“Oh… you should get on top…” you tell her. You’ll last longer that way and have more control to pull out of her. She does so and gets on top, riding you slowly. She puts one of her breasts in your mouth and you suckle it. Her body is getting so sweaty that she slides on top of you effortlessly, like an ice cube skidding on a warm floor.
“Let me show you something” you tell her. You lay on your back and she lays on you with her back, so that her breasts are up, like a reverse doggy style. You guide your cock back in. From this position, you can kiss her, play with her nipple, and rub her clit at the same time. She can’t handle it anymore and cums on you, arching her back, flexing her abs, and pushing her ass into you. You apply firm pressure to her clit and kiss her neck to make her orgasm more intense.
“I want to go back to missionary” she says, and you get back on top of her. She’s laying on her wedding dress now. You put a pillow underneath her ass to get even deeper.
“Oh God… where do you want me to cum?” you ask, feeling yourself getting close. Your cock is starting to swell even more as it prepares to shoot a load into her. She’s in ecstasy. “Did you know… I’ve never come in anyone before…” you say. “I want…” she says, starting to lift her hips up, “you to…” her legs are now lifted, allowing you to get all the way inside of her, brushing up against her cervix with your cockhead, “come in me…” she says, pulling her legs around your hips so you can’t escape. You release your hot, warm load into her and feel her pulsating abs and pussy, orgasming as well, pullng your cum even deeper into her vagina. You keep thrusting and thrusting, leaning all the way into her and pulling her ass up for your hips, feeling complete connection to her. Nothing has ever felt so good.
***
Eventually you get her cleaned up, you help her put new sheets on the bed, and set up her wedding dress. You tell her you’ll text her tomorrow, and she says not to bother. You get an uber back home and in the morning you tell your parents that you had a great time catching up with your old friends.
A few months later and she makes a big post, announcing a few things. First, she’s finally posted the professional pictures from her wedding. But there’s one detail that you notice, something that looks out of place. On her wedding dress, the off-white dress with the poofy sections, there’s a few small off-color dots on the center section. A few dots that are just a little more white than the rest of the dress. I wonder how those got there? The second announcement is that she is pregnant, and she and her husband are ready to welcome another soul into the world. You give the post a like and comment “Congratulations!”.
Source: reddit.com/r/eroticliterature/comments/izp1mp/your_exgirlfriend_the_night_before_her_wedding