My [29F] First Confession: my bf’s [29M] high school crush [32?F] came into town [FFM]

So this is my first post here after a couple years of lurking. I love reading about all (OK, some) of your sexcapades, and overall I really love how supportive and positive this community *can* be. Over the past couple years my bf and I have been trying to consume more ethical porn/erotica (both of us are typical millennial porn addicts), and written/amateur stuff often feels the most authentic and least exploitative. I decided it might be time for me to contribute to a community that has made me cum at least, like, eleven times. πŸ₯°

About me: I really, really love threesomes (usually ffm but have done both), casual sex with my friends (men and women!), watching porn, mutual masturbation, and both giving/receiving oral (with anyone!). I love sneaking around (not cheating!), meeting couples with open relationships, and watching my bf with other women. I love stripping (watching and doing!), lap dances, sexy parties, and seeing my friends feeling confident in their sexiest outfits. Light BDSM can be really fun too! Most of all I love having sexy discussions with sexy friends, and I am pretty much always in at least one ongoing sext convo (usually just words, I’m kinda paranoid about sending/posting pics).

I’m really not into any incest/step-family stuff, nor am I into anything that leans into non-con or abusive territory. Cuts down on what I can read/watch on this and most other subreddits, but oh well. Ngl, I know most of you out there are gross horny boys πŸ™ƒ, but what excites me about posting is the idea of my fellow women (and femme presenting! and enbies!) getting themselves off reading about me and my experiences/fantasies! Ok, maybe I’m happy to get some of you guys off, too (or maybe not 😈).

I’m open to DMs (no dick pics!) as long as you keep it classy and don’t take it personally if I don’t respond.

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So this is a (mostly) true story about my bf James and his high school crush Stella (fake names, obviously). I have changed some details for anonymity and while some particulars might be a little embellished (deliberately or from the natural shortcomings of human memory), I swear to you, pretty much all of this REALLY happened. If you can’t trust an e-girl’s burner reddit account, who can you trust??? (But, no, really, I did this shit and I’m dying for you to read about it. πŸ˜‰)

James and Elena went to the same high school, but she was a junior (I think?) when he was a freshman. She had a boyfriend all through high school, although their relationship didn’t seem very healthy, but James had a huge crush on her from being in the same Shakespeare play (freakin drama nerds, right?). They stayed friends even after she graduated and while nothing ever happened between them, I know (from talking through it with them since) that they both felt chemistry, although they never acknowledged it until I came along.

Stella lived across the the country after college but James went from high school straight to work in his/our hometown and never left (I mean, he’s traveled a bunch, but he’s never moved to another city). She told me later that her high school boyfriend got jealous that James and Stella had this (very innocuous) long-distance friendship/correspondence, and he forbade Stella from talking to James anymore. Apparently that was the final straw in their relationship, and Stella finally broke things off with the only person she ever seriously dated. James never knew this until years later.

Fast forward the better part of a decade. James and I have been dating for about a year and a half (covid partners, naturally). We had already talked about opening things up in our relationship, and I knew that sharing another woman was his number one fantasy (basic male fantasy, but luckily also one of mine). James is a total slut, he doesn’t seem to know exactly how many people he’s fucked, but he thinks between 40-50. We have both had several threesomes and group experiences before we met, something we bonded over early in our relationship (probably such an alluring shared fantasy because covid lockdown made it untenable!).

James is not possessive at all, and had encouraged me to feel free to pursue a separate sexual relationship if I wanted, although by the time I met Stella, I had never taken him up on it and had never extended the same offer to him. He’s a great communicator and very respectful of my boundaries (something I value so much), and our sex life started incredible and has only gotten better. We’d already begun regularly talking during sex about sharing a hypothetical female partner, and I was very intrigued one night when (as he absolutely railed me with his gorgeous cock 😈) he whispered into my ear that he wanted to see his friend Stella eat my pussy. Whoah! Later, after we wrapped up (I don’t remember if we both came, but it’s not uncommon for neither of us to quite get there due to respective prescriptions) I asked him to remind me who Stella was, and he got a little embarrassed.

“I mentioned her name because I wanted you to ask,” James confessed. I knew it. Boys are so predictable. I shifted around in bed so we were side by side, and I adopted an exaggerated pouty sexy voice and asked him, “Will you show me her picture, daddy?” He instantly knew he wasn’t in trouble (sometimes he forgets that his gf is a horny freak), and pulled her page up. He reminded me about their friendship and I remembered that when he had told me about her before, I really enjoyed imagining his cute younger self pining for this sexy older woman. As we lay beside each other, he pulled up her pic and I felt his cock getting hard against my thigh. I loooove feeling his cock press against my body, and he knows it.

I looked over at his phone and gasped, because Stella was sooo beautiful. She was petite, with thick, wavy black hair styled into a cute pixie cut with a streak of neon blue. She had big, soft brown doe eyes, and a cute little button nose. Fuuuck me, I’m in love, I thought. “Oh, you like her, huh?” James said slyly, as he looked sideways through his long, beautiful, enviable (damn him!) eyelashes. “How could you tell?” I asked as I began grinding my still naked and recently fucked body against his. His cock (which is so pretty! and feels so nice! in my mouth and in my pussy! and I literally have no idea what size it is! like 7 inches? is that a lot? who cares, literally only boys care about measuring dicks!) was rock hard and I looked hungrily back and forth from it and the phone in his hand showing Stella’s selfie.

He put his tongue on my ear, nibbled, and responded “Because your pussy left a wet spot on my thigh when you rolled over.” I wanted to respond that we literally were just fucking and that of course my pussy was wet and how could you tell anyway, we’re both damp all over with each other’s sweat and spit and cum but instead I just made a pathetic moan while he kissed my neck and slid three fingers into my soaking cunt. Cheap point!

He dropped the phone on the bed and started rapidly sliding his fingers in and out of me while using his thumb to rub my clit. With his other hand, he grabbed his big, hard, pretty cock, not stroking himself, but just holding it and lightly squeezing the base. I love watching him touch himself and I love looking at the base of his cock, nestled in his soft bush. He knew exactly what he was doing with his hand, and within a minute, I threw my head back (accidentally bumping it on our headboard, but I didn’t care) let out all the uncontrollable moans and cries that had been building up, and tensed my legs up as I felt a euphoric release and began squirting. I had never done that with a partner before I started dating James, and only a couple times by myself. Within a week of the first time we fucked, he had figured out how to make me squirt any time with his hand. Within a month, he could do it with his mouth. By six months, he could make me squirt just by pulling out of me and slapping his hard, dripping cock on my clit at the exact right speed. Now we have to change the sheets like 3 times a week. What a keeper. 🀀

So I’m moaning, my body is shaking, and I’m squirting all over James’s hand, and then I’m squirting all over his cock, because like lightning, he’s hopped up onto his knees, spread my dripping legs, and thrust his beautiful cock into my drenched pussy. At this point I’m just lost in the sensation and seeing stars, so I have no idea how many thrusts I take before he suddenly pulls out, leans forward over me, grabs the headboard with one hand and begins to furiously pump his cock with the other. I obediently scooch down the bed, still on my back, until his cock (dripping! with MY juicey squirt!) is directly over my face. He loves this part. I flash him my sexiest eyes and open my mouth with my tongue out, and I reach up and begin squeezing and pinching my nipple. “Call me by her name, James,” I beg in my pouty voice. Oh yeah, that’ll get him.

He barely manages to mutter “Oh fuck! Fuck! Stella!” before his body goes tense and his giant, pretty, delicious, dripping, shining cock explodes, and hot white cum streaks over my tits and my face and into my mouth (and in my hair and in my eye and on the sheets, we’re a bit of a mess). In a daze, he keeps pumping his cock as I sit up on my knees, and spin around (James’s warm cum now running down my breasts, onto my stomach, and dripping down my chin) and take his delicious cock in my mouth as it makes it’s final pulses. I taste my own pussy all over his shaft and then feel his warm cum shoot through my mouth and down my throat. I nearly gag but I save myself and pull him out of me. An absolutely disgusting/delicious mix of our fluids is dripping out of my mouth. I definitely need to take a shower. James is looking at me like I’m a literal goddess. “You wanna cum on her like you just came on me?” I ask him, “Because I’d really like to see that… I’d really like to clean her up with my tongue afterwards.” I swish my mouth a little to gather up a mix of cum and spit, and then I stick my tongue out, and let the sticky white mix slowly drip down onto my bare thighs. I’m just teasing him now! But the truth is, I am really turned on and Stella looks so sweet on James’s phone, shoved to the edge of the mattress, sitting in the middle of a veritable puddle one or both of us.

“Why don’t you tell me about the time you could have fucked her but didn’t?” I ask him, still facing him, streaked with his cum, watching him slowly stroke his now half-erect cock, a nearly invisible spider’s thread of cum still stretching from the tip of his cock to the inside of his own thigh. Fuck, how hot would it be to watch him facefuck Stella, and watch him make her face and body get so wet and sticky and marked with meandering shiny streaks across her perfect soft skin – and then suddenly, he’s pushed me on my back and spread my legs and in his hand is his vibrating cock ring (my favorite!), his fingers threaded through the ring and the vibrating rabbit ears gently grazing the exact right spot. I lay back and close my eyes. It’s not often I can cum with a partner, but tonight feels special.

“At a cast party sIeepover once,” (freakin theater nerds!), “a bunch of our friends had smoked some weed, changed into pajamas, and started playing truth or dare…” he began to tell me, as I kept my eyes closed and concentrated on his voice and the incredible, torturous vibration against my clit. “Everyone was feeling frisky and we’d taken turns daring each other to make out. I had kissed like three girls, but not Stella. Then, our friend Ashley, who was barely wearing anything, clearly the horniest, blurted out, ‘Should I dare someone to let us watch them give head?’ I expected everyone to freak out, but those of us left awake were all pretty good friends and super slutty, so people started laughing and saying stuff like ‘that would be so crazy! but also really fucking hot!’ I didn’t say anything, and neither did Stella, but we looked each other dead in the eyes, and I remember seeing her mouth open just slightly and then she looked down and her eyes got wide and she smiled and I realized that she was looking at the growing bulge in my briefs…” He trailed off as I finally, FINALLY came, and he stared down at my spasming body with a look of accomplishment.

“Don’t stop, tell me the rest of the story!” I told him as soon as I caught my breath and pulled the filthy, damp sheet up over our suddenly cold bodies.

“Well, to tell the truth, that story didn’t even happen. Or it didn’t happen that way, Stella wasn’t even there at the party,” he said with a laugh as we wiped ourselves (somewhat) clean and settled back into bed next to each other.

“What a dirty imagination…” I cooed as I scooped up his phone and started casually scrolling Stella’s timeline. “I was literally just imagining watching her suck your dick when you started telling your little story. Which I assume ended with her sucking you off in front of your slutty drama friends?”

“Haha, how did you know where I was going?” James is so predictable. I love it. “Well it’s funny that I just happened to mention my old high school crush during sex,” he said with mock sincerity. I playfully jabbed him in the ribs as he said the words I knew he’d been planning to say to me this whole evening. “Because, Stella is gonna be in town next week visiting her family and I thought it might be fun to invite her over for a.. date night.” Bingo.

I pursed my lips and looked into his pretty perfect eyes and purred with all sincerity, “I’d absolutely love that, baby. Just make sure you don’t accidentally call her by my name when you cum on her. ” I jumped out of bed and bounced over to the shower, glancing back at him, looking at his crush’s selfies while reclining in our wet, dirty bed, his beautiful cock resting against his thigh – fuck, I’m so happy. And horny. “Give her a call. Tell her I think she looks… lovely. And I’m excited to meet her. And let’s go ahead and invite her for a sleepover.”

James was giving me that dumbfounded, worshipful look when I stepped through the door of the shower. “I love sleepovers!” he shouted after me. I know.

πŸ’‹

Source: reddit.com/r/gonewildstories/comments/udwb4l/my_29f_first_confession_my_bfs_29m_high_school