To give some insight he was my first ever boyfriend, my first kiss as well. He was a shy blonde kid and I was too. We’d been dating for Max 4 months in middle school; he’d given me what I thought was a love letter on Valentine’s Day and I’d given him about a 100$ worth of gifts. I was thinking when everyone stared at us it was because we were a cute couple.. nope, he’d read this letter to everyone before giving it to me. It was a four page breakup letter, I was traumatized.
Fast forward to senior year 18[f] (me), I’d started maturing more but still hated him for what he had done. I was getting hit on more frequently by most of the guys in my small town, including my ex who’d humiliated me. So of course I flirted back to waste his time, until I saw his brother in quick add his brother was 26, he’d constantly be down from college hanging out with both my ex & and his best friend so I’d seen him. He’s physically the same as my ex but more mature and has about a foot on him.
I’d added his brother on Snapchat & was responded to quickly. “I remember you, you used to come by the house when you were younger” I was surprised he’d remembered the shy awkward girl who’d come over. I said something dumb like “haha yea that’s right” there was some small talk but It kinda stayed at that.…. until I’d posted a post workout pic on my story, It was a pic of me in blue leggings & a black mesh bra that was see through with Calvin Klein lettering on it. He’d said “WOW someone’s grown 😉” I’d read that and got extremely excited. I snapped him a sweaty pic of me just smiling with my nipples definitely showing through the top.
We’d lightly flirted back & forth until he’d asked me what I was doing and if I wanted to come chill with him and Jackson (ex’s best friend); that they were going to a field to go smoke and drink. I said yes with kinda fear cause he was an older guy, and I’d never gotten drunk or high before! After about an hour of getting ready he’d picked me up, and my awkward self is sitting against the truck door thinking bout the texts & snaps we’d exchanged. Honestly getting excited but lost in thought, he’d told me to move closer and I had he grabbed my knee right kinda to where it tickles and hurts which got me extremely wet.
After an awkward car ride we’d gotten to his house the same one I’d been to when I was younger. He and his brother used to share the guest house bunk beds. It was a talk metal bed frame with the mattress above and one below. I’d awkwardly sat on the edge of the bed and he’d instantly started kissing me I felt my face go red & I was so warm from the excitement. Knowing what I was doing was kinda wrong but it was so hot!
He’d grabbed my Jean shorts and threw me back onto the bed on my back and started grinding on top of me. I could feel it and was fairly satisfied with what was pressing up against me; until the door had flown open to Jackson w a case of beer. His brother keeps kissing me like it’s nothing and I’m quick to push him back cause I was embarrassed. Jackson tosses him a drink and me as well after we’d both sat up.
They both acted like nothing happened!! I was so confused by it, I’m drinking acting like it doesn’t taste like straight piss, but I chugged it and felt warm. Id been focusing on just listening and drinking but realized his brothers hand was on my thigh he was rubbing his fingers up my shorts and Jackson is kinda watching. I didn’t mind it and grabbed a second beer, I was wet and I think he knew when he’d touched. My panties beneath my shorts cause he’d moved closer to me. Grabbing my thighs and occasionally kissing me he pushed me onto my back again while Jackson went out to smoke.
Within maybe a minute my shorts are gone and he’d pulled my bra off beneath my tank top. He’s kissing and biting my neck and I am on fire, I feel my body just tingling and I’m so turned on. I’m grabbing him and kissing him, but of course Jackson comes back, but instead of sitting up we just continue and I’m sure I looked shocked I’m just looking at Jackson who’s just watching, drinking, and smirking. I’m smiling a little when my tank top is lifted up and my tits are being bitten on. I’m moaning and trying to stay quite, Jackson says something like “come on guys” when my (e.b) says “dude come here” Jackson awkwardly grabs my tit and I just smile lightly hoping for more than that. (e.b) slides down and pulls out his dick and begins teasing my clit, spits on it and just rubs it back and forth; Jackson leans over and is biting and squeezing my tits hard and holy fuck was it great.
I feel (e.b) slide his dick into me deep and is fucking me slowly. I reach over and unzip Jackson’s jeans he stands up and asks if I can handle 9. I’m scared tbh but said “I can try I’ve never taken that much”
Jackson on his knees by the bed with my head hanging off is slowly teasing my lips and entering my mouth. I’m super excited, extremely wet and feel (e.b) fucking me harder to see if he can thrust my lips further down Jackson’s huge dick. I’m choking but trying my best to handle it occasionally pressing my tongue out to get it deeper. Jackson pulls his dick out and turns Me around, (e.b) is laying on his back so I put my mouth around his dick tasting my cum all over it.
Jackson’s view is my ass in the air and my head bobbing on (e.b)s dick I lifted my head quickly feeling Jackson thrust his huge dick into me without any restraint. I’m holding back tears due to him absolutely pounding into me with a steady beat.
I tried hard to focus on sucking on (e.b)s dick until he’s trusting up into my throat. I’m being viscously fucked; and it is the most amazing experience I’ve ever had. Jackson presses his thumb into my ass and I gag at the shock but press my Hips further Agains him feeling him push his thumb go in and out. Jackson tells (e.b) “damn she’s a little freak” like they weren’t both fucking me at the same time.
(e.b) pulls out and then lays me on my side where he then slowly presses his dick into my ass. I broke into tears and they’d asked me “if I need to stop”.
I’m shaking and crying but I beg them to keep fucking me.
(e.b) is quick to bust and fills my ass with cum; Jackson continued to fuck me even harder pounding my insides. I tell (e.b) to come back to my mouth when I see He’s still plenty hard and I suck on his creamy dick.
Jackson quickly pulls out and shoves me down onto my knees, forcing his dick down my throat feeling it twitch as his hot cum shoots into my mouth and goes down my throat. He’d wiped his dick across my lips before we’d all gotten to catch our breath.
Was the greatest night I’d ever had and have still been unable to top it.
Source: reddit.com/r/eroticliterature/comments/ttg430/how_i_fucked_my_boyfriends_brother_his_best_friend
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