Lucy and the Bartender

Jack had just left from another one of his late night visits. Most times he would come by after closing the bar around 3 or 4, fuck me stupid then leave. Once in awhile though he'd been spending the night. Those were the nights boyfriend would get most jealous I think. Last time he wanted to get breakfast, but i missed all of his texts because I spent the morning getting fucked into the floor! He even came to the door and rung the bell a bunch. That fight was almost as big as when I first told him about Jack. I handled that argument in exactly the same manner. I simply reminded him that he was free to fuck who he pleased, just like I was. That had always been our arrangement. So what if who I pleased happened to be the older stud bartender who threw him out last month? He had no comeback, but I offered to tell him every single detail if that helped. His cock had been half stiff the entire conversation, so I knew it would work.

I whispered into his ear about how huge Jack's cock was. How big and powerful everything about him was and how I just couldn't resist. There was no one in the room and I have no issues discussing sex aloud, but leaning in like that let him feel my breath on his neck and let me lick his ear a little at the best parts. I had barely finished describing the intense face fucking Jack game me when he whimpered a little. I laid my hand on the bulge in his pants.

"Should I continue?"

He didn't have an answer, only heavy breathing and a pleading look on his face. I could see that I had won, so I unzipped his fly and said, "Go on..."

He had his dick out and in hand within seconds. I probably shouldn't have, but seeing pull on his dick like that made me giggle, especially having just spent hours with Jack, who would never allow me to take charge like that. Boyfriend is handsome and sweet. He's even above average downstair at about 6 inches. Most girls I'm told would be happy with that. Jack stood over a foot taller than me. He was strong and dominant. I had never measured him but his cock had to be almost a foot long. I was definitely bigger than the 10 in that had previously been my record. Compared to Jack, boyfriend was... well a boy. He's lucky I love him.

"It felt like a baseball bat in my stomach." I'm pretty sure that was the line that put him over the edge that first time.

Boyfriend was easy enough to make happy, so I wasn't really concerned. As I walked down the hallway from the shower thinking about the rough fucking I had just gotten, feeling very content and very sore, was something Jack had said started to make me nervous. He often asked about Emma, my roommate, and joked about how he wanted to fuck her. She was my best friend and pretty much always there with me when I'd see him at the bar. All the guys had crushes on Emma. She had big round doe eyes and one of those cutesy faces that made her look confused all the time (In truth she was only confused most of the time). Boyfriend has had a hardon for her since the day she moved in and had seen her doing yoga in the living room.

"I'm going to fuck her with or without you," Jack said to me with a nonchalant shrug. "You can help or listen from the next room. Your call."

I tried to slap his chest, but he caught my wrist and twisted my arm around my back. It the pain was sharp and abrupt so i gasped. He forced me down and i followed obediently. I licked and sucked his cock for almost an hour after that. I could never tell with Jack if he was joking or not. Being put down like that had me so turned on though. I came twice while blowing him and then once again in the shower with only my fingers.

I was toweling off and walking down the hall thinking, "I'm sure glad I keep my hair really short. It would have been impossible to get all that cum out otherwise!" When I passed Emma's room, I heard a buzzing sound coming from inside. She had been listening to us fuck all morning and now was getting herself off! I'm not sure why I was so shocked. It wasn't the first time I'd heard her in there.

The door was cracked enough that me bursting in without knocking wasn't weird. Emma immediately sat up and yanked the covers to her waist. Her hard nipples showed through the loose tank top she was wearing. I tried my best to hide my little smile as I hopped into bed and cuddled up next to her. Emma's body was curvier than mine. While my big tits stood out because of my tiny frame, hers fit her body perfectly. She would always borrow my bras saying we're the same size and then spill over the top. I could feel her panting and her heart racing as I lay my head on her chest. I reached up and ran my fingers through her bleach blond hair.

"Oh hey... uum good morning?" Emma said everything like a question.

"I had a hard night, Em!" I pouted at her. I'm not sure what came over me, but she was getting off to the sounds of me gagging, moaning and having my head banged against the wall. If she was gonna hide it, I was gonna make it difficult!

"I heard," she giggled shifting her body a bit.

"It's just like every time I think about Jack, I come to the conclusion that I'm remembering wrong. I'm not though. His dick is really just that fucking big. Now I'm SO sore! What's the biggest you've had?" This happened to be a question I knew the answer to. Emma and I have had many long in-depth conversations about sex. They were mostly me talking about sex and her listening attentively. When I'd get to the good parts she would always screw up her mouth and furrow her brow like she was thinking really hard about it. But maybe she was actually just getting super hot and bothered. Emma had only been with two guys, her high school boyfriend, who she blew on his prom night, and fucked and four or five times when she visited him at college, and a one night stand with one of boyfriends buddies, David.

"David was kinda big, like maybe 8 inches."

I giggled a little, knowing it was a lie. Boyfriends buddies all went to the gym together, and I once made him describe all their bodies for me in great detail while I stroked his cock. I didn't let him cum until he's given me permission to fuck them all. I never actually did, but he really got off to that shit.

"Oh my god! Eight inches in and I'm like losing my mind, but then it just keeps going and I dunno I'm just some place else. Like all my thoughts and inhibitions slip away and I'm some kind of animal." It was sort of like teasing boyfriend. He was humiliated hearing about me and Jack though. This was different. Emma was intrigued. She was living vicariously... but maybe we could fix that.

We had both slid down into the bed, laying on our backs with one shoulder touching and our heads tilted in against each other. I ran through all three fuck sessions from the night into the morning. It might have been four, but I lost track at some point. During our shifting around Emma lost track of the vibrator that she was hiding under the blankets.

I felt the cold plastic against my leg and quickly snatched it up. Jumping out of bed and waving it, I told her, "You know I've got much better toys than this."

Emma looked like she'd seen a ghost. She reached out and tried to follow me, but realizing she had no bottoms on she grabbed the sheets around her and retreated.

"What the fuuuck! Give that back!"

I just cocked my head and raced off to my room. I could hear her pounding her fists on the bed and calling my name. "Not funny, Lus!"

I came back right away to see her sitting in bed pouting with her arms crossed. The angry look faded slowly into shock and maybe awe when she saw me. I had dropped my towel. In one hand I had a thick black dildo and in the other I was twirling nipple clamps on a chain like a lifeguard's whistle.

"I'm happy to share."

MY heart was throbbing in my chest. She wants this right? She does. Does she??

It felt like an eternity and she didn't move just sort of cocked her head and looked up and down me. I giggled I think to break the tension and she laughed back. I jumped on the bed and pushed her over. She called me a jerk and pounded my chest. I grabbed her wrists and we rolled around laughing until she felt one of my hands on her thigh.

Emma froze in place. She looked in my eyes and asked, "For real?"

"For real." All the tension in the room broke. She exhaled as I slid my hand up and brushed her lips. She was still wet from playing with herself. I tried pushing two fingers into her. She was dripping down her leg but it was still a tight squeeze. Kneeling next to her and slowly fingering her cunt I started in with Emma's vibrator. After just a minute or so she was thrusting her hips into my hand. Always self conscious about her tits, Emma had one arm pressing them against her chest, I assumed to keep them from smacking her in the face. Fuck I wanted to see those massive things bounce around! I reached up, grabbed the front of her tank top and yanked it down. Her eyes had been clamped shut and at that moment shop open. My fingers were deep in her cunt. I held them there. Emma's arm had come down to grab my hand as I exposed her pale tits. Her eyes went from her naked body to me. I smiled approvingly and took one of her light pale nipples in my mouth. Again Emma relaxed her body and started pumping her hips. The harder I bit down the more frantic her breathing became and the harder she ground against me. I sat up and pushed the vibrator inside her. Emma quickly grabbed her own nipples and pinched them while I fucked her with it. I could tell she was close to cumming and I wanted to see that so badly, but I stopped. I pulled out and watched her buck two or three times before she could stop herself...

A light whimper was all she could manage.

"Not yet."

Emma opened her mouth to protest two or three times but couldn't think of any words. I climbed over her body, so my knees were at her hips and I was facing her. I took her hands off her tits and replaced them with the clamps I had brought.

"I had a feeling you'd like these." She nodded her head, but then winced and bit down on her lower lip as I tightened each just a little more than she expected. Emma started working on her clit with her vibrator, but I snatched it away.

"Now you said you'd had an 8 inch cock before right?"

Emma gripped the sheets next to her and ground her ass into the bed. It was pretty tempting, but I was enjoying the power game too much to fall for that. I took the vibrator, at about 5 or 6 inches in one hand and my 8 inch dildo in the other and said, "Because I don't think you have."

She nodded her head insisting she had. "Cmon Luuus I'm real close!"

"Was it more like this little one? Because that's not 8 inches. Or was it more like this one!"

I ran the head of my fat rubber cock across her clit and slid it up her body catching the chain the linked her nipples together. Emma jerked a bit forward at the pain.

"Tell the truth."

"GRRRRR mmm Lus! It was like the little one!"

I giggled and pressed the head of my toy against her. She ground her teeth together and pushed back but the thing wouldn't budge. I hadn't thought to bring lube so I started giving the thing a tongue bath.

"Holy shit!" Emma groaned, as she saw me take most of it down my throat (I was just showing off there).

I pulled on the chain so she'd sit up and offered the cock for her to suck too. She kept her eyes on me and her little tongue poking out of her mouth as she tried to take it in her throat. Her gag reflex kicked in almost immediately but she was clearly getting off on it, pushing it as far as she could each time.

Watching her tear up and hack spit all over my toy got me going again and I started working my own clit. Emma saw and a switch went off. She realized that she had been hogging all the attention and reached over to help.

"Gentle," I warned, because I was still super sore. She rubbed my clit a little and I let her feel my gaping pussy.

"Oh wow... Jack did that to you. Like... just nooow?"

"Mmmmmmhm and you're next."

I pushed the cock against her again. She twisted up her body cried out loudly for the first time. The head popped inside. I'm pretty sure I could hear it even. Emma let out a guttural moan and I held it there, her hips raised in the air. I grabbed the chain connecting her tits and shoved it between her teeth. It pulled her tits up by the nipples and made Emma squeak. I ran my fingers through her sparse blond pubic hair and slowly lowered her to bed.

"What's the biggest thing you've ever had in you?"

Emma looked at me with pleading eyes. Her face was still red from gagging herself. She tried to speak with the chain in her mouth. She tried to beg me to fuck her.

"Hhhhhooh shuuck eeee... uuuck me..."

"What's the biggest? Is it David's cock or mine?"

I pushed. At that moment Emma lost all control. Her jaw dropped and the chain fell loose. She reached down and gripped my hands tightly squeezing her fat tits up and together between her arms.

"Fuck Lus! It's yours! Yours is the biggest! FUCK ME FUUUUUUCK!"

She couldn't take more than half for a good 10 minutes or so, but by her second orgasm she had most of it in her. It took a while before she released my hands and let me really beat her insides up with it though. I guess it takes a minute before you can trust your roommate not to break your pussy.

I'm not sure how long we went at it. I even had a few small orgasms with the vibe while Emma licked me. Eventually we collapsed and passed out together. I realized later that I probably should have invited her to join me Jack while we were all worked up, but I was too absorbed in the moment. When I brought up in the morning she was super timid again.

"I dunno Lus. That was reeeal intense and you said he's bigger."

"Well maybe instead of listening in next time," I tossed her vibrator towards her, "you could watch at the door."

Emma's eyes lit up for a second then she clammed up realizing how excited she had just looked. I laughed and tugged on her hair a bit.

"Then if you like what you see..."

I enjoyed the idea of us plotting together, like I had a partner in crime. Over the next week or so not much changed at home. Emma and I had always been pretty close, pretty cuddly as friends go. We spent a few nights sleeping in the same bed and fooled around a little, nothing major (practice is key). So when I told her Jack had texted me, that he was coming over after his shift tomorrow, the mood shifted. I expected her to be scared, but she seemed more intrigued than anything else. It was like all those times we had laid in bed talking. She hung on my every word. She even helped me angle some furniture differently so she could get a good view from her room.

I felt very prepared for our little deception. All that went out the window though when Jack showed up that night instead. I didn't have the outfit I had planned on. I didn't even know if Emma was home!

Jack pushed right past me when I answered the door. He smirked and laughed under his breath. I'm guessing he could read the confusion and surprise on my face. I scurried to the kitchen to get him a drink like I had planned. I could still get this back on track. "This could still work!" I thought.

I fumbled with the bottle of whisky a bit. The cap was harder to get off than I thought. I kept trying to glance down the hallway to see if Emma was watching, but I couldn't get a good view from the kitchen. When I walked out, Jack was sitting in the wrong place. I had forgotten to lead him to the chair. I had no idea what the view from that spot was like! I wasn't going to let it phase me though. I walked over to the couch, handed him his drink, pulled my shirt off over my head and dropped to my knees. I might not have my fancy new bra on, but my D cups squished into this sports bra would have to do.

Kneeling from below Jack looked so big. His greying hair was all out of place after working all night. He smelled like cigarettes and spilled booze. He leaned back with his drink and motioned for me to go on. I usually don't get to take the lead with him, but maybe since I was doing all of the right things I was getting a pass.

I undid Jack's pants and guided his monster cock out of his boxer briefs. It was so wide my fingers weren't even close to touching as I stroked him hard. Licking my lips, I studied every inch of it. The thick veins, the slight bulge in the middle, I was dripping wet. I didn't have anything on under my sweatpants, so I felt it down my leg as I started licking it from base to tip. I kept glancing past his shoulder to see if I could get a good view of Emma. I could see her door, but not her! My lips stretched to the max getting his head in my mouth. I had to get up off my knees a bit to get over the top and get good angle. In that moment Jack changed. His hand had been stroking my hair gently. He grabbed it tight and yanked down the front of my bra. I felt the stretchy material underneath pushing my boobs up and together.

With both hands on my head, Jack started bouncing me off his dick. He didn't thrust, just jerked himself with my mouth. I could feel him hitting the back of my mouth hard again and again until he just held it there. He waited a few seconds before pushing at my throat. I'm not sure why I wasn't ready for this, but I started to panic. I grabbed at his legs and at the couch, and twisted away a bit. No matter how hard I squirmed, Jacks big hands around my head just kept pushing my mouth down on him, pushing past my mouth and into my throat. I had forgotten Emma for a moment, but tried again to look over. It was impossible to see much. My eyes were all watering and Jack had really started working me hard and fast. I usually love getting my face smashed like that, but all I could think in that moment was that I'm sure Emma would be scared away if she was watching this.

When Jack let me go he'd had about half of his cock jammed down my throat. I was a mess. My face was red, mascara dripping down my cheeks. I was covered in spit and phlegm. My nose was running any my hair was all over the place. I fell back on the floor panting. In that moment Emma came running to my side. She knelt next to me and started licking my face, cleaning all the drool off of my face and tits. She was wearing the matching lacy thong and bralette we had picked out for her (little bitch had all the time in the world to get ready while I was getting abused).

Jack simply watched smirking, his whisky in one hand, his massive tool in the other. He didn't seem surprised at all. Maybe I had given us up by glancing at Emma's door so much. Maybe he just knew that I'd bring her to him eventually.

After regained my composure a bit, I started kissing Emma back. My spit was all over her face now too. We stopped immediately as Jack leaned forward offering two fingers to Emma. She tentatively tried to suck on them, but he lifted them to the roof of her mouth and guided her up. He held her there by the roof of her mouth just too high to kneel, but too low to comfortably stand and pulled her forward to a position in front of him.

With his fingers till pressed against the roof of her mouth, Jack informed her, "This is where we start. Every time." He still has his cock in the other hand.

"Do you understand?"

Emma's eyes were wide as she nodded. SLAP

"Excuse me?"

Unable to close her mouth she replied, "Yessh." SLAP "Yesh, shhir?!"

"Let's have a look at you." He stood up and lifted her by her mouth to full height. She rose wobbling awkwardly a bit. Her breathing was shaky and I could tell she was on the verge of crying, not tearing up from gagging, but really crying. I had hoped that knowing how inexperienced Em was he'd take it slow, but this was the opposite of that. I think he was being more harsh than ever!