His loss, my gain

Our story begins after a night out a few years back Connor, Amber and I ended up back at their house. Our whole group had known each other since high school and we liked to go out for drinks occasionally, we’d slowed down now that we were all in our late 20s but we still drank a far bit. After the night was over we caught a cab, which dropped us off at Amber and Connor’s tiny one bedroom apartment. We plopped down onto the couch. I looked over at Amber to see her rolling her eyes, as her drunk boyfriend Connor jokingly pawed at her.
“Ughh you are so fucking drunk babe!” She screeched and pushed him away from her. “Just let him rest Amber, it’s been a long night for all of us” I replied with a shrug.
She stuck her tongue out at him one final time before scooting around to look at me. We had been friends since high school and had adopted an almost brother/sister relationship at this point, lots of back and forth and teasing and shoulder punching. She was a tiny little thing, just 5’2” and 120 pounds, pale skin more suited for Siberia’s winters than warm California. Her defining attribute was her long blonde hair, and her almost comically bratty personality.
Especially when she got drunk, she would whine and yell at Connor to eat her pussy or fuck her harder regardless of the guest in her living room. I always wondered if she got off on that, or if she knew that I would jerk off listening to them. I could tell she wanted to get manhandled and he wasn’t into it like her. I would often fantasize about pulling her soft cream colored ass cheeks apart and stretching her out the way she needed.
“Earth to Mark!!!” Amber droned, annoyed I wasn’t paying attention. I snapped out of my reverie and looked up at her apologizing. “Will you help me with him? He’s too big for me to carry” she motioned towards Connor and me being 6’7” I had to oblige. I managed to get him into bed and walked to the couch. Usually at this point she’d berate him into coaxing a couple orgasms out of her and go to sleep. Far from being sad I was excited, I loved these live jerk sessions. This time she sat right next to me and really turned the vocal fry to eleven.
“Soooooo, I got a new tattoo” she smirked, her voice cartoonishly similar to Paris Hilton “Wow, lemme guess a tramp stamp” I responded jovially, not wanting to seem too eager. “Noooouh” she cooed in return.
“It’s right here! You like it?” Putting on her best high pitched baby voice she loved to do when she was drunk. She clumsily dragged her top down to reveal a mandala stretching between her breasts. I couldn’t help but stare as her right breast fell out of her top completely.
“That’s awesome, I love the line work, and the nipple aint bad either” I chuckled, desperately holding back the need to put her stiff pink nipple in my mouth.
“Thank you! So I’ve been meaning to ask you, why don’t you ever hit on me?” The baby voice was gone now and she was actually serious.
“What!? Because you have a boyfriend, he’s in the next room!” I said my voice trembling as my cock rapidly stiffened in my pants.
“Yeah but I just showed you my tit, most guys would want to suck on it” pausing at tit and suck for emphasis and twirling her hair as she dragged a vape.
“Well I don’t see you that way” I lied, poorly. Immediately she stood up, strode over and in one smooth motion pulled both her breasts out, inches from my face.
“So you don’t want to suck on these” she almost purred into my ear as she wiggled her impossibly perky tear shaped breasts in my face, begging me to suck them. I had imagined this so many times I couldn’t believe it was real. I was so surprised I couldn’t do a thing, but she grabbed my head and pushed it in between her tits and shook them. Then immediately sat down and put on a big adorable, smize, squeezing her tits together while she explained.
“I know you, and I know you want to cum on these don’t you” I nodded slowly
“You want to make a big mess on my tits huh” demanding attention and never breaking eye contact she slid over and started massaging my hard cock through my pants.
“Here’s what’s going to happen Mark, my boyfriend will stay asleep in our room” she started unzipping my pants and kissing my neck
“Connor, the friend you’ve had since grade school? Yeah he’s gonna stay asleep, and lucky for you, he decided he wanted to send a dick pic to his ex” she rooted around in my pants and fished her wish, her small, deft hands dragging me out into the open air. I felt a tongue in my ear and a quiet giggle.
I suddenly felt that unmistakable hedonistic scream of pleasure that can only be an eager mouth sucking your cock. I looked down to see her nose on my stomach and the biggest puppy dog eyes perched over my cock, looking up for approval. I brushed her hair out of her face and she gently slid me out of her mouth and began licking up and down my shaft, sometimes popping my balls into her mouth.
“I, I can’t do this Amber, he’s right there and he’s my friend” I tried to protest, shit even I didn’t believe it. But I had to say something. As if to answer, she spit out one of my balls with a pop, and looked up at me, manufacturing a look of excitement and innocence, as if she had no idea how this cock had gotten above her. I could feel the heat of her breath wash over my cock as she announced
“I want to sit on your cock, and I want to feel your cum in my ass when I get in bed next to Connor, and you’re going to give me that cum aren’t you”
Then she slowly stuffed every inch of my cock down her throat, her intricate eye makeup wide around her eyes as she gagged on it, it was only 6 inches so she was playing it up, but I loved it. I decided then and there if I was going to make this choice, I was gonna give her the fucking she deserved.
“Ok you little slut, you want this cock, I’ll give you as much as you can handle” I pulled out of her mouth and lifted her up completely, putting her back on the couch and kneeling in front. I spit on my hand and rubbed it on her pink, tight, hole. Then I pushed both her legs back to her neck so her asshole puckered open just slightly. I had imagined this sight dozens of times and I wanted to soak it all in. Pale and fragile, the curves and hollows of her body wrapping in on themselves waiting to be gripped. She began to whine, an urgent, soft whisper “unnnnnh” I knew she was whining for me to push myself into her ass, but I wanted to savor this. I gripped under her ass and gently pulled it apart, coaxing my sticky dick head into the opening.
I pushed my body against hers, feeling her tits press into me and whispered directly into her ear
“Is this better my good little whore?” She nodded vigorously and whined for my cock.
I pulled slowly and evenly on her hips feeling more of myself disappear into her tightness. Only letting go once I knew I wouldn’t fall out and ran my fingers across her face and into her hair.
“This is so fucking hot” I whispered and simultaneously pushed my mouth onto hers, firmly pushing my manhood into her an inch at a time. As her moans escaped into my mouth I could taste the vodka and cigarettes she was so fond of. I put my arms around her hips and pinned her to the couch, working every last millimeter of dick inside her. Never breaking eye contact, once I was all the way in I let out a huge sigh of relief. Finally I was exactly where I wanted to be. I could feel her clenching and unclenching her ass around me and we both smiled for the first time in awhile,
“God that feels so fucking good, stretch my tiny little ass” she demanded, pulling me into her and squirming onto me. I then began to warm her asshole up by taking my dick all the way out until just the tip is in, then gripping her neck and holding her in place while I go all the way back in. Whenever I would crest in she would clench her ass nice and tight and release and I would go out. This slow dance continued, each stroke giving her a surprised face as it stretched her out over and over.
“Is this what you wanted Amber? Did you want me to come over and let me use your tight little ass as my fuck toy?” I whispered slowly, slipping out of her and sitting on the couch.
“Yes, I need it, I need it baby” she squatted over me and sat down on my cock getting my balls even more sticky with her juices. I think to this day it’s the hottest thing I’ve ever seen, this girl who I thought I could never fuck, squatting over me and spreading herself open, staring at me with a look of sadistic delight, desperate to see my reaction to her body opening up and swallowing me whole. She had to cover my mouth when she fully sat on me, and then I had to cover hers when I grabbed both of her tits, twisted them and then held her shoulders down while I pounded upwards.
She started cumming so hard she just went limp, I had to hold her upright to keep fucking her as she squirted, the warm liquid gushing out onto me, the couch and my clothes. Then she crumpled onto me, writhing with pleasure and surprise. I pushed her face up to look in her eyes and then let it go inside her. As the first rope of cum shot into her ass, she jumped a little and then smiled a huge smile, nuzzling into me as I shot another, and another into her ass. She would moan a deep “nhhhhn” with every shot until I was spent.
“Hun, I need you to do one last thing for me” she was back to normal after her orgasm now and looked up at me, her eye makeup all smeared
“I need you to clean me up and suck up your last little treat”
“Mhmmm how could I forget”
She jostled her ass until my cock slipped out and carefully sucked, nibbled, and drained all the cum, asshole juice, and squirt fluid off my cock and balls, making sure to show me how she swallowed it all. After she was done, she got up, said goodnight and turned the light off. We ended up blaming the squirt on one of the dogs peeing, and I remember her giving him a big tongue kiss in the morning, then looking over at me with an evil grin. Was it worth it? Maybe, maybe not but try to say no when you’re watching a perfect unreasonably tight, pink, little asshole slowly stretch around the head of your cock.

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