[MF] The Saga of Sally – Cum-Stained Jeans

Hi, you might remember me as [the guy who fucked his stepmom, Ana, on vacation](https://old.reddit.com/r/gonewildstories/comments/hragsd/my_vacation_fling_with_my_stepmom_part_1_mf/). But that was around 20 years ago and I have had a life full of other sexual escapades. Several of you wanted me to keep writing about them so here I am. And here I am with the first part of what will probably take weeks or more to write: the Saga of Sally. This post might have a little bit of build up just to set everything up but I hope it’s worth it. I will also be calling myself “Mark” from now on.

If my stepmom Ana was my foundational, the very first, sexual experience of my life, then Sally is the definitive sexual relationship of my lifetime. We fooled around, fucked, and loved on-off for a long time. I’m going to tackle our sexual escapades chronologically. There will be some one-off parts that didn’t involve Sally too, moments where we weren’t exclusive and I had some crazy sexual experiences. But we’ll get to that later. First Sally.

Throughout my first year and a half at college I had gotten a bit of a reputation for chasing after a specific type of girl. Basically, it was Ana. I wanted leggy, toned, slim girls with tanned skin, and if they came with an accent all the better but I was happy to live with American girls who fitted the bill. I had a few serious, short relationships but mostly I just fucked around. One of those serious relationships was with Marie though. She was from an Italian-American family and to a college boy, Italian-American and Spanish might as well have been the same thing. I don’t have any great stories from Marie because it was all missionary quickies in my dorm whenever we had the time, her skirt hitched up around her waist, her panties hanging off an ankle. She had a great body though and she kept herself so tight and toned by playing a lot of sport, mostly volleyball and soccer. Another member of that team was Sally.

Sally and I got along like a house on fire. I wouldn’t necessarily call her a tomboy, she liked make-up and dressing up every now and then but she definitely had a tomboyish streak. She loved soccer. She was incredibly funny. She even did a few pretty successful open-mic nights before deciding she couldn’t handle the nerves. We also had a lot of similar tastes in books, movies and television: kind of dorky but not full blown nerd. It didn’t take long for us to become best friends. Part of this was because she was just fucking cool to hang out with. Part of it was that while I lived in a cold, gross dorm with gross, messy boys, she still lived at home since she was local and her parents were rich: their house was much better to spend my time at than in my dorm. But mostly it was because she was cool. Now Marie got jealous. She didn’t like how much time Sally and I spent together and we eventually broke it up. I thought Marie was so fucking dumb. Didn’t she realize that Sally wasn’t my type?

Everyone knew I liked tall, leggy, darker skin, petite, toned, tight, black haired women. That was my type. And Sally? Sally wasn’t any of those things. She was a pocket rocket, not much taller than 5 feet. She was pale with bright red hair. Sally and I would argue over exactly how curvy (or thick if we were at college now) she was. She said she wasn’t *that curvy* and it was because she was short it was an illusion. I’m telling you she was fucking curvy. She had at least D cup breasts that had to be supported by an industrial bra from the Soviet Union when she played soccer. Her waistline was small, but her hips flared out. She had that hourglass figure. And her ass? Jesus Christ, her ass was round and thick. I know I said she wasn’t my type but every so often I found myself staring at her backside. It was like my dick was smarter than my brain and had figured out I was attracted to this pocket rocket, redheaded vixen. I know some of you asked for photos of someone who looked like Ana last time and I couldn’t really think of anyone but considering Sally will be making many reappearances I went hunting for an equivalent photo and [she looked a bit like this](https://preview.redd.it/kzllfuq6o2o21.jpg?width=640&crop=smart&auto=webp&s=3d17bf59ce6d2dfba8691510ebcfaa5aff68bca5) but without the tattoos.

So that was Sally and me. We were both in our second year of college. We were 19 or 20. And for about six months we were inseparable platonic best friends. Y’all can see where this is going. Like I said I spent a lot of time around her fancy house and her parents didn’t mind. She was an only child and a bit spoiled. Her father liked me because I shared a lot of his interests and I was studying a “grown up” degree compared to his daughter doing English and Art. Her mother liked her because at 19, when I wanted to be, I was a fucking charming polite motherfucker. Sally used to joke that I was trying to get into her mother’s pants, not realizing that I had prior experience at such activities with my own stepmom. Either way. Her parents liked me. And had no concern about the two of us being home alone. If anything I think they were more worried that we weren’t fucking.

One day I go to Sally’s house after class in the middle of the afternoon. I can’t remember why. I think there may have been a sport game or something we watched together. But we eventually get to bullshitting and having a beer and enjoying each other’s company sitting upstairs in her bedroom. I honestly don’t have a fucking clue what Sally was wearing above the waist. That memory is gone to time. But I do remember she was wearing track shorts that hugged her ample butt. Sally was the type of girl that no matter how baggy her bottoms were, her ass was being framed by them. At one point Sally is once again teasing me about my taste in women. It was a favorite pastime of hers. We were both liberal students and she liked to tease me about being a conservative who just wanted to get myself a latina housewife to bang. And then she does something she had never done before. She brings up her own body. “I would say you’re just after that J-Lo booty, but I have a better ass than every girl you’ve ever dated.” I laugh and say “Sally, you’re not really my type.” That was the red flag to this shortstack bull. She started going on about how I wouldn’t be able to handle her. That she would break me in minutes. I keep laughing which only makes her more passionate and she says the words that will change our entire lives: “I bet I could make you cum in just five minutes only with my hand.”

I laugh again but this time a little sheepishly. She sounds like she means it. She pushes me in the chest. “Oh yeah, you don’t think I can?” she says and I’m now fucking stuck. What the fuck do you say to that? What do you say to your best friend saying she can jerk you off in five minutes? I stammer something saying that I don’t think she can and our fates are sealed. We’re competitive. We won’t let this stand. And so I’m sitting dumbstruck on the edge of the bed as Sally unzips my jeans and fishes out my semi-hard cock. It sits there rather lonely, jutting out from my pants as Sally sits next to me. “What are you waiting for?” I say in a voice a little too squeaky and quiet. Sally rolls her eyes and point to the alarm clock. She’s waiting until it turns to 3:47 so that we know exactly how long five minutes is. Envy your ability to have a stopwatch on your phone now.

Now I think I have this bet. My short fuse with Ana has disappeared now and my stamina is decent. Also it’s Sally. It’s my best friend, fully dressed, who isn’t even my type. It’s not like it’s Ana with a soapy handjob in the shower. I can last five minutes. My confidence isn’t even dented by the sight of Sally licking her palm, getting it slick with saliva. I can handle this. The clock hits 3:47 and Sally grabs my cock and starts to pump it with enthusiasm. Okay. Her grip is just right and her arm is a blur, but she can’t keep this speed up. I’m fine. And then that fucking tiny bitch unleashes her secret plan.

She puts her mouth to my ear, all the while still jerking me off and says: “You know Marie told me about you?” I blurt out a ‘what’. “Yeah. About how you’re fucking obsessed with anal. About how you were always asking to shove your cock in her ass but she never would.” That pocket rocket bitch. That cunning fucking shortstack. Sally continues to pump me as she starts to purr dirty poison into my ear. She tells me about how Marie would look so hot with my cock in her ass. About the faces she’d pull. About how good her tanned ass would look with my cum all over it. I look at the clock. How the fuck is it only 3:48?!?! I swallow. I can do this. I can do this.

“Do you want to hear a secret, Mark?” Sally whispers. I don’t say anything. I’m going for the stoic silence plan. Don’t negotiate with terrorists. “I fucking love it in my butt. It feels so good. My round ass getting fucked by a hard cock. And your cock is really nice. I think it would look so good pushing in between my thick asscheeks.” She keeps on talking. Keeps on saying these words but I lose focus. Because now I’m thinking about one thing only. Fucking my best friend in her plump, round ass. I’m throbbing. She laughs, she can feel me losing it. “Oooh. Do you want to fuck me in my ass, Mark?” I hate her. I fucking hate this minx. I look at the clock. 3:49. Jesus Christ. I’m done for. Then she shifts her body, still jerking me off, but her mouth is now hovering above the tip of my cock. I can feel her hot breath on my skin.

“I thought it was hands only!” I gasp. She replies: “it is but we don’t want a mess do we?”

I realize I’m about to cum inside my best friend’s mouth. More, now that she’s leaning over my lap, her shorts-clad ass is in the air. I don’t have a great view, more an outline of it, but the idea of being behind it, being inside it, sends me over the edge. “Oh God, Sal” I moan as I fall back on her bed, my balls churning. I look up at the ceiling in pleasure, waiting for that moment of her warm, wet lips wrapping around my cock. They never do. Instead that fucking tiny redheaded bitch pulls her face away as she jerks me to my climax. I realize what is about to happen but my balls are beyond control and my cock is an erupting volcano. My jeans are soon covered in my cum, my spunk splattering against the denim, my own cock and balls, and Sally’s hand.

“Not even four minutes” she laughs triumphantly. I catch a sight of her licking her hand clean. That should have made me ready for round 2 but I was too preoccupied with my fucking jeans. I quickly grab her pajamas top and try to wipe up the mess, much to her complaining, but it’s no use. While the streaks of cum have been wiped away, there’s clear splotchy white stains. “Sally, I have to catch the bus home!” I yell at her, calling her a bitch straight to her face. She laughs and points out I should probably get out of her house before her parents are home. I stare at her, wide-eyed, realizing she’s going to make me get home in this state. I quickly gather up my things, try to make myself as presentable as possible with cum-stained jeans on and head off. Before I do I stop at the front door. “Did you mean what you said? About -” I can’t finish the sentence. About fucking her ass. She looks me dead in the eye, very serious, and then says “I’m sorry Mark, you’re not my type” and closes the door on my face.

And that’s how I then had to catch the bus home in clearly sex-stained pants. An old woman looked at me for most of the ride home, and not in a good way. More in a “deciding if she’s going to tell the entire bus” way. I hurry out at my stop and rush back to my dorm. I get several stares but no one says anything. Fortunately my roommate isn’t home and I can change and sulk in peace. You see I’m very angry. Incredibly angry. Not because of the mess on my jeans. Because I’ve just realized I’m incredibly sexually attracted to my best friend Sally.

Source: reddit.com/r/gonewildstories/comments/hsqikr/mf_the_saga_of_sally_cumstained_jeans