Her name was Sondra, like Sandra, but with an o, I think. I never asked.
It was a wedding, or rather, the aftermath. We were all the same hotel- me, most of my friends, their significant others, and mine too. The place was a country estate, a few separate buildings with a dozen or so rooms in each, some lovely nature and fuck all else.
It was full, overfull, and as such we’d had to move from room to room, building to building, over the three nights we were there. That inconvenience led to my superior geographic knowledge of the place.
That knowledge is what led my tipsy girlfriend to suggest I help Sondra find her room while she went to our room to change. Not an issue, just tour guide duty. Easy. I was drunk, because it was a wedding, but still… easy.
So Sondra, friend of the bride, a bit of a socialite, clearly spoilt, pretty bit not stunning. Five seven, dark hair and a button nose, tanned like she went on holiday every week. Lovely eyes. Not much cleavage, perky ass. I barely knew her, but just like all the other bridesmaids, I had noticed her. By noticed, I mean I’d undressed her with my eyes.
So my girlfriend stumbled away and Sondra asked me to lead the way and I laughed at the irony of the drunk leading the sober, but I knew where to go and soon enough we got there.
Simple.
She unlocked her door and I said goodnight and turned away, hoping to get back to my room before the girlfriend was asleep. Post-wedding hotel sex. I had my dirty plan.
“Seriously, you’re not even going to try?”
“Try?” I was genuinely confused. Again, I was drunk. Open bar drunk.
“I thought we could have a cheeky shag”
“Oh.. fuck.. no… I’m… flattered…but…”
“Don’t be. I’d do anything with a cock at this point”
“Charming…”
She grabbed my hand and pulled me into the room, a tiny little thing with a single bed and a sloped roof, closing the door behind me. I was in a state of drunken shock. I could’ve left if I really wanted to, but I like to think I had no choice. It numbs a bit of the guilt.
“We’ll be quick…”
I probably could’ve stopped her unbuckling me. I went as far as to stammer something like “we shouldn’t…”. I didn’t say no. I suppose I could’ve stopped her pushing me on to the bed. I went down easy. Resistance was futile.
“I won’t tell…”
She hiked up her dress and straddled me, her bony fingers wrapping around my shaft, guiding me. I should’ve said something about a condom but all I managed was an “ Ohh fuck” as I was engulfed by a lovely, wet warmth.
“There we go…”
Her bunched up dress deprived me of a view but it didn’t matter, the sight of a bridesmaid writhing about on top of me was good enough. I reached for her breasts, pulling her dress down, scooping her little nipples out, rolling and pinching and tugging them. Now I was complicit.
The writhing turned to riding as she leaned back, depriving me of her nipples, her hands resting on my knees. I hoisted the dress up, folds of fucking silk and lace, craning my neck, finally getting a look. Barely a sliver of pubes, dark lips and a swollen clit that my thumb started to rub.
“Yes… Do that…”
Approval. Now I was involved. Participating. Struggling to hold that fucking dress up, attempting to ignore her sexy whimpers. Rubbing, strumming, whimpers becoming moans. I was good at it.
“Don’t stop”
She was trying to get that fucking dress off, pulling it up, struggling, the skirt over her face, her arms stuck. It was pretty entertaining. She started to lose her balance so I sat up which didn’t help at all. She fell back with a soft thud, the dress still over her face, my cock still inside her, an unrestricted view of all the good bits.
“Don’t you dare stop”
I was sitting upright, her crotch in my lap, watching her struggle, my thumb on her clit, watching her ride me, watching her little breasts jiggle, a lovely, faceless body. It was inexplicably hot. She couldn’t see me but I could see most of her and I loved it. No expression to interpret, no eyes judging me as I ogled.
It was like wrestling. Writhing and twisting, freeing an arm, a foot on my chest, rolling onto her side as she tugged the dress over her head, her thighs drawing together, crushing my hand. I hoisted a leg over her and she was on her stomach, prone, my cock still inside her, her legs clasped firmly together. Tighter. Finally naked. Dangling over the edge of the little bed. Wriggling her hips and pressing back, her buttocks jiggling in my hands as I pulled them apart.
It was primal. She pressed back hard, climbing back onto the bed, arching her back, hoisting herself up, somehow managing to get on her hands and knees. Good old fashioned doggy. My phone rang. Dread, fear and guilt.
“Almost there” she whimpered.
My phone kept ringing and I started thrusting out of desperation and terror. Hard and fast, making the little bed thump against the wall.
“Yes… yes… don’t fucking stop.. I’m coming… don’t stop…”
I fucked her as she came, thrusting and grunting as she spasmed and shuddered, watching her asshole clench and her lips grip my creamy shaft. My phone stopped ringing. She went limp.
“Cum on my bum…”
I pulled out and stroked my creamy cock, sliding my tip along her crack as she wriggled. Prodding gently enough to feign innocence as it brushed over her asshole, firmly enough to demonstrate intent. Investigating possibilities. Getting closer.
“Cheeky boy…”
Intent demonstrated. Instead of retreating or objecting she pressed back, taking me by surprise, taking me, my tip in her ass, a whimper and a giggle and a squeeze, evicting me as quickly as she’d welcomed me.
Anal. If I’d blinked I would’ve missed it. But it was anal, unsheathed and unexpected and most definitely unwise. It was my undoing. I unloaded, a rope splaying across her back, attempting to poke it back in as I gushed, failing, oozing, deflating, until I was a limp sticky mess, just like her.
Anal. Fuck yes.
“Fuck yes”
She giggled. My phone rang. I cleaned up and she just lay there, naked and sticky. I could’ve had another go but I didn’t. Guilt, but mostly fear.
The girlfriend was nowhere to be found. Turns out she hooked up with two groomsmen and was calling me to make some kind of excuse. I should’ve stayed for another go.
Source: reddit.com/r/gonewildstories/comments/egstbx/the_bridesmaid_who_shagged_me_mf
Well written dude!
Beautiful. Epic. Tragic.
Sweet story! Almost seems like Sondra and your girlfriend were In cahoots…
Yes. You should have stayed with the lady who let you put the tip in her asshole.
Idiot.