Part 1
The music at the bar was kind of loud for my taste, but it was the only place nearby that my roommate could get into. Everywhere else walkable checked ID at the door and she was only 19. After bailing on college upstate she had moved to the city about six months ago. I think this is the only bar she's ever even been to. Boyfriend and I hadn't lived here long either, so Emma was really my only close friend. I'm only a few years older, but way more experienced with drinking, guys, life, the whole nine yards.
I escaped NYC along with boyfriend last year for something more affordable, which is nice. The downside is that I left all my friends (and side guys) behind. Back in NY I had a few good things going on. Boyfriend and I have an open relationship, where we date pretty much whoever we please. Close friends and the like are off limits (mostly). It works out well because while boyfriend is great, sometimes a girl just needs a little... more. Jealousy happens but we deal. Also sometimes jealousy is hot.
Boyfriend is a social butterfly so he's been dating and already has a pretty good group of friends. He and a few of his coworkers were in the corner throwing darts. I'm not sure they even knew the rules.
"Yo watch yourselves!" the bartender yelled, as two of them raced to the board to grab their darts. They ignored him, like drunk dudes do, and wrestled over who got to throw next. Elbows flew and boyfriend knocked over a beer on some innocent bystander.
The bartender was on them fast (or maybe it seemed that way because I was fairly drunk too)! He was a tall older guy, prolly in his 40s. He'd been there other nights but I never got his name because honestly he struck me as kind of a jerk.
"Alright kids! Out!" He was always talking down to people like that. Boyfriend and his buddies were out of line I guess, but he really didn't need to throw them out.
I followed outside. Boyfriend wanted me to bar hop with them but I wasn't about to abandon Emma. Needless to say words were exchanged. When I went back in I was in an awful mood.
"Oooo look though. For us!" Em had clearly ready my mind and handed me a shot.
"Oh tequila... I make a lot of mistakes with tequila."
"Sorry lady. I didn't pick. They were an apology from Jack."
"Jack?" The bartender waved and walked over.
"Jack." He extended his hand. I shook it and gave a half smile.
"Nice hands," interjected Emma as she leaned in. She was definitely drunk. He did have nice hands though and to be fair it was good tequila. Jack poured us all another shot and did one too. I'm pretty sure we didn't pay for another drink that night.
It was Thursday so the bar thinned out pretty fast. After some small talk, "I've seen you around, live in the area, sorry about your boyfriend, blah blah," more booze and some harmless flirting I needed to pee desperately.
I took care of business and was looking in the mirror. My tomboy game was on point. I had one of boyfriend's plaid shirts buttoned all the way up to the collar, short hair perfectly quaffed, new black frame glasses and a sports bra keeping me all in place. My boobs are pretty big, C cups, but they look huge on my tiny frame so I squeezed them into a tight sports bra that night for a more andro look. While admiring myself and putting on some lipstick for a femme touch, my phone blew up. I had a text from an unknown number.
::COME BACK:: with a goofy picture of Jack and Emma behind the bar. When I walked out she was swatting his chest. I was surprised at how much smaller than him she looked. He was easily over six feet. We all giggled some more and Emma went outside to smoke while I finished my drink and said goodbye.
"She's trashed I should tuck her in."
"Stay a while. She's a big girl. She can handle getting home."
I was more tempted than I expected, but it was getting late.
"Sorry but boyfriend is pissed at me as is. I should talk to him before bed."
Jack smirked, turned away and started moving some glasses. He didn't say goodbye, just kind of went back to work as if we hadn't spent the night laughing and flirting. Jerk.
I practically carried Emma home. When I changed and looked at my phone I had a bunch of drunk texts from boyfriend. He was at his place and in bed. There was also one from Jack's number.
::Your bf was only mad because he's got a small dick::
I was outraged! Boyfriend does not have a small dick. I mean... It's not big, but it does the trick... usually. I think he's even above average.
::Fuck off! You prolly have a small dick!::
It wasn't my most eloquent reply, but whatever. My blood was up.
He was def prepared for me though. Within seconds my phone was buzzing. I was ready for a fight, but all I got was a picture of his junk. Instantly all that rage turned into something very different. It was a mirror pic, just torso down. He definitely had a right to be cocky. That thing was not small. When I looked back later I noticed he was in surprisingly good shape for an older guy. You could see the faint outline of a six pack, light hair leading down to his nicely trimmed package. The main event distracted from all of that though. The one thing I think about in that moment was how heavy it looked, long, thickand so heavy. It was standing straight up and reached past his belly button.
I was examining the beautiful veins and the bulge right in the middle. My pussy was getting wet, so sitting right on the couch I reached down to feel. As I ran my finger over the lips I felt how smooth I was. I pushed on my clit and started making little circles. I was just starting to get into it when another text came in.
::What's your address?::
Without thinking I replied.
I tore through my room looking for something to wear. I didn't wanna look like I had gotten dressed up, but my nipples were poking out hard through the worn out v-neck I was wearing. You could easily see I had one pierced and the other wasn't being quiet either. The little boyshorts I had on didn't leave too much to the imagination either. Before I could find something just lacy or just tiny enough to still look effortless the bell rang.
Shit! I raced to the door so he wouldn't ring again and wake up Em.
"Hey," I managed to get out.
Damn he looked good. Better in this light, or better now that I know he's packing? Unclear. Either way he had some of his slicked back grey hairs out of place. I reached up to fix them and he caught my wrist. Without even speaking he led me inside.
I was feeling very exposed and a little awkward so I tried to make small talk. He turned around to face me without replying. We were standing very close together. He was still holding my wrist securely in one hand with the other on my waist. Not knowing what to do, I started to get up on my toes to try to kiss him, but was held firmly in place on the floor. Jack twisted the arm he was holding behind my back and I gasped. He pulled down the v-neck and glared in at my exposed tits.
"Very nice. Where were you hiding these?"
It was the first thing he said to me and I couldn't quite come up with an answer I was so worked up. He smiled a bit at my obviously flustered state. Then he pulled me in close. I could feel him semi-hard against my stomach as he groped my ass.
I allowed him to explore my body with his free hand, not wanting to interrupt again. His hand easily covered my ass and I knew his finger tips could feel how wet I was through my panties. After a few seconds he released me.
"Take this off," he nodded and flicked the edge of my shirt. I inhaled hard and pulled it off. I could feel his eyes on me though his expression didn't change at all.
"Keep going." He pointed to my little shorts.
I couldn't even think so I just did as I was told. I was completely exposed and could feel it. My heart raced. I was standing completely naked in front of this fully clothed older man.
He held a finger down and spun it in a circle indication that I should do the same.
"Slowly."
Holy shit! What was I doing? A few hours ago I was cutting this guy dagger stares as he tossed my drunk boyfriend out on the street. Now I'm putting myself on display for him. I loved it.
I finished my little circle. He was undoing his belt. All I wanted was to please him. I'm not sure if I was taking initiative again or just weak in my knees but I dropped down in front of him.
How his cock could look even bigger in person I'm not sure, but god damn it was impressive. He pulled it all the way out and lowered his jeans a bit. His meaty shaft was amazing but it was his balls that really shocked me. I guess I couldn't see them well in the picture but now they were hanging there and I couldn't help but reach not and touch.
I grabbed his cock in one hand. I couldn't even close my fist around it. At the thickest part it must have been the size of a beer can. My other hand went to his huge balls. They were at least double the size of boyfriend's maybe more. His junk was so heavy and his cock wasn't even all the way hard yet.
Jack nodded and placed in hand on my head. I opened my mouth to take the tip of his cock. I was really worried I wouldn't be able to do much with him. My mouth isn't all that big. I swallowed the head and reached out my tongue. Saliva was leaking from the edge of my mouth as I tried to bob a little.
He wasn't all that interested in my slow start. His free hand gripped the back of my neck digging his finger tips in. I was startled, but his other hand running through my hair comforted me a bit. My pace quickened. Well it was his pace now as he started thrusting in and out. I tried my best to massage his balls in one hand but I actually needed both to contain them. Slowly but surely he was pushing into me. I couldn't help but gag.
I'm not sure if Jack didn't notice my discomfort or didn't care because his pace kept quickening. He grabbed my short hair tightly and pushed deeper into me. I could feel him pass my mouth and into my throat. Tears streamed down my face and spit dribbled steadily out of my mouth onto my tits. He pulled out for a moment to let me catch my breath, but quickly jammed himself back in, back into my throat. My body resisted. All the muscles in my throat and my stomach convulsed to push him out but he was so strong, so dominant. He took my face like he owned it.
