Hello friends. It is a good day for anyone born north of the Mason-Dixon line of Chicago baseball fandom. Even though I wouldn’t consider myself a die-hard fan, it was pretty awesome watching the Cubs win the World Series last night. But that wasn’t the only enjoyable thing that happened last night!
DC is the most transient town in America, so it’s easy to find a ton of other folks from your hometown. And since this town is tight as hell when it comes to socializing (politician, lobbyist, government worker or journalist, we all love booze, food and sex in some order). So when I decided to host a get together for Game 7 with other Cubs loyalists, it didn’t take long to fill my small apartment. Most of the people were guys and gals I’d met working here, but there was one old friend I reached out to.
Rebecca grew up two streets down from me and we were in school together from K through high school. I had a pretty big crush on her starting in fifth or sixth grade. Petite, sarcastic and pretty, she comfortably floated between the popular cliques in high school, including the clique I was in (nerdy athletes?). Our senior year we were the co-editors of the high school rag, which gave me tons of time with her. Come prom time, we were both single, so I mustered up the courage to ask her to prom. Unsurprisingly, she turned me down, although gently (“blah blah blah we are too good of friends blah blah blah don’t want to lose that blah blah blah”…you know how it goes). I ended up taking another girl but Rebecca went stag with some friends. At the after party, with my date passed out drunk somewhere else, Rebecca and I had a real heart to heart and we ended up drunkenly making out a little, although she stopped things before they went much past some kissing. Seeing my obvious disappointment, she cracked, “how about I owe you a BJ when the Cubs win the World Series?” in the hope that would lighten the mood. As that’s the Chicago equivalent of a politician promising to actually give a shit about his constituents, I let it drop and we graduated and moved on with our lives.
We re-connected four years ago, when Rebecca called me out of the blue to ask my help in quashing a story that would put her then-boss (a mediocre Senator well-known around DC for playing grab ass with his hot staffers) in some trouble back in his home state. A quid pro quo that met the approval of my bosses at the network was hammered out where Rebecca and her boss gave us some insider info, and aside from both of our careers getting a nice little boost, we also became friendly again, hanging out, texting often, and participating in the great DC tradition of trading political favors for access and vice versa.
So it goes without saying that I invited Rebecca to my get-together. And since I had 100% remembered her “promise”, there was even a little part of me that thought maybe she did too and would pay up if the Cubs won (as if I needed another reason to cheer for the boys in blue). She showed up a little bit late, in the 2nd or 3rd inning, when the booze was flowing freely and the two 6 foot subs I had bought were well on their way to getting demolished. No surprise, she looked amazing. Sometime after high school, she had thinned out a bit, highlighting her long chin and cheekbones, dyed her hair blonde and had paid good money to upgrade her small tits to very respectable C or D cups. Last night she was wearing a tight Cubs t-shirt and black leggings, and I know I wasn’t the only one staring at her hard ass when she bent over to grab some food off my coffee table after she said her hellos.
I worked the room, chatting with Rebecca a bit, and watching her pound the tequila, and found myself next to her when the Cubs scored twice in the 10th inning. Hugs and high fives all around…and was it my half-drunk mind or did Rebecca really grind her crotch into me while we hugged? I was pretty distracted and sporting a half-chub until the final out, when I was rewarded with another long, tight hug from Rebecca, those hard tits of hers feeling wonderful against my ribs, and even a kiss on the cheek.
The crowd thinned quickly–it was approaching 1 AM–but Rebecca offered to stick around to help me clean up until it was just the two of us in the apartment (my roommate, thankfully, has been covering the Senate races and I’ve only seen him for a few days the past three months).
“So,” I said with all the wit and cleverness I’ve accrued over the years, as we leaned against the living room wall next to the kitchen pass-through finishing the dregs of the tequila. I’m happy I could get that much out, as all I could think was how to bring up a conversation from 11 years ago in a totally casual and not desperate way and gain a shot at seeing her
Rebecca’s hazel eyes sparkled as she looked at me over her cup. “Remember prom night?”
I felt a jolt go through my whole body. Was she about to bring it up? Holy shit! “When you told me you’d give me a blowjob when the Cubs won the World Series?” I blurted out.
Rebecca’s eyes widened in shock and she stared at me. “I–what?”
Oh shit oh shit oh shit. “I mean, I do remember prom night. What about it?” I rushed, my hands shaking, my face reddening.
Rebecca’s mouth tightened and she started to turn away as if she was going to leave when she stopped and spun back. “Holy shit, I did say that, didn’t I?” she said with a laugh. “At the lake house party afterwards?” She grinned at me. “Did you just remember that because the Cubs won, or have you been holding out hope for a decade?”
I sputtered and got redder and cursed the delicious wonderful alcohol that was clearly to blame for my verbal diarrhea.
Rebecca stepped closer to me and reached out and began stroking my hard cock through my pants. “Hmm…I’m guessing the latter, isn’t it?”
As her slender fingers rubbed me, I wasn’t sure what was going to happened first, cumming in my pants or dying of embarrassment. “What did you mean then about remembering from prom?” I asked lamely.
Rebecca ignored my question. She put her cup down on the pass-through counter and leaned in and licked me, her tongue running from the bottom of my substantial cleft to just below my lip. “Hmmm,” she purred and I shuddered with pleasure. She grabbed my cock full and I leaned into her and we started to kiss. I got my drink down and wrapped my arm around her, pulling her close. But she wriggled out of my grasp and with a smile, grabbed my hand and led me to the loveseat and pushed me down. I sat obediently and she pushed my legs apart and got down on her knees between them. I tugged at her shirt but she waggled a finger at me. “I owe you a blowjob, I didn’t promise you sex, right?”
I nodded dumbly, excited but also more than a little disappointed that I wasn’t going to get to see those fabulous tits of her. Rebecca pulled her hair back with a hair elastic of some sort and unsnapped my pants. I lifted my butt off the sofa and allowed her to tug down my pants and boxers, my little guy bounding out for air. Once they were removed and tossed to the side, she leaned over and took my erection in her mouth, swirling her tongue over the head, causing me to shudder again and groan.
I watched her head go up and down on my cock, lightly massaging my balls with her right hand. I put a hand on her head to feel the movement and banished the thought that she had gotten so good at this from blowing her old boss, the distinguished senator. The alcohol dulled the horny edge that would have made me cum right away, and I enjoyed a good five or ten minutes of amazing head before I felt an orgasm coming.
“I’m gonna blow,” I gasped, but Rebecca noticed too. She took my cock out of her mouth, gave my shaft one long lick and then moved off to my left, jerking me off until cum spurted out, splashing onto the rug and coffee table. She kept jerking until I stopped spurting, and then leaned over and sucked the cum remaining on my dick off. She smacked her lips and gave my softening cock head a light kiss. I shuddered again.
“Shit, that was amazing.” I groaned.
“Lived up to a decade of build up?” she laughed. She was probably making fun of me, but I just nodded contently.
Rebecca stood up and grabbed her purse. She turned, her ass still sticking out towards me and I briefly wondered if I got hard again if she’d want to fuck for real, my brain trying to build some construct where she’d want to come back over and ride me. “What did you mean about prom?” I stalled.
She smiled. “I was going to ask if you remembered at prom when we talked about changing the world and here we both are working in DC.”
Honestly, I didn’t really remember anything else about our prom night conversation besides her blowjob promise, nor did I think her work as a lobbyist now nor mine as a news producer was changing the world much but I just nodded.
Rebecca laughed at me and head for the door. “Liar,” she said, as she blew me a kiss and left. I sat on my sofa, pantsless, and cheered the fact that at least I could cross getting a BJ from a high school crush off the ol’ bucket list. Oh and seeing the Cubs win the World Series…
Source: reddit.com/r/gonewildstories/comments/5azecv/cubs_win_and_so_did_i_mf_oral