It all started one day a few years back I was having a conversation with the IT girl Emily. I had known her for a bit. Her father used to work in the office as a boss before he retired. Emily and I use to walk in to work together since we parked our cars in the same lot and we both had to be in work by 8am. Emily was 5’1 with brown hair that fell just below the shoulders. She was slightly curvy but in all the right places. She had brown eyes and wore thin framed glasses. She would normally wear outfits to work that would hide her body. It seemed she was a bit self conscious about her body since she went from super thin to heavyset and back to a more toned athletic body.
Even though Emily was very pretty I always just treated her like one of the guys at work. Plus I wasn’t the heartthrob that I like to pretend I am. I’m only 5’7 180lbs short brown hair with blue eyes. I don’t have 6 pack abs but I do have a flat stomach.
On our walks into work we would talk football since she was a Jets fan and I a Steelers fan. We were both in different Fantasy football leagues so we use to compare teams. One day I decided to create my own league with the guys from work. I had filled all the teams but one and was having a hard time finding a person to fill it.
The next day on the walk in to work I asked Emily if she would help me out
“Sure. I don’t know why you didn’t ask earlier. You must have been scared I would win it all” she said it with a playful smile.
I said to her “You’re talking to a champion you’re going to have your hands full when you face me.” She laughed and we parted on our way to our own offices.
After the season started we would talk more and more each day about our teams. Every morning I saw her she would always bat her eyes and put on a cute face and say “Good morning Commissioner” I would always smile. We started to get close to each other she would talk to me about bad dates she had. I had told her how since I’m a shy guy I didn’t date much. I had been in a relationship for 4 years but had broken up about 8 months prior.
As the season went on Emily had been doing very well by week 7 she was 6-1. I had an undefeated record going at that point.
One morning I ran into Emily
“Hey Commish if you don’t have plans tonight swing by the Alley. I’m bartending till 10.”
“Me at go to the bar, well since you’re twisting my arm I be there after I hit the gym.”
After work I hit the gym and finished up at about 8. I headed home and took a long shower since my muscles were sore. After the shower I almost forgot about stopping by to see Emily at her side job.
At 8:50pm she texted me
“you didn’t forget about me did you?”
I quickly threw on some jeans and a light blue polo shirt and headed for the bar. I got to the bar at 9:15pm I had really hustled to get there since it’s 3 towns away from my house. When I walked in I expected to see at least a half filled bar since it was a Friday night. As I looked around no one was there except Emily. I said to Emily
“I know this place isn’t a main stream bar but where is every one?”
Emily was wiping down the bottles behind the bar. She was wearing dark Blue jeans a grey shirt with a V-neck that went down to the middle of her ribs and she wasn’t wearing a bra.
“That’s a very good question. I almost thought you weren’t going to show up.”
“Is everything ok?“
“I know I always seem like everything is great but the truth is I’m struggling paying bills.”
“I’m sorry I didn’t know”.
“There are cutback rumors at the office for the IT department. I am lucky that I get paid here at the bar weather it’s busy or not but the tips are what help me get by.”
“Don’t worry about the rumors sometimes they are just that.”
Emily then came around the bar and sat on the stool next to me.
“I’m sorry I didn’t mean to put my troubles on you.”
“Don’t worry that’s what friends do they help each other.”
I tried to lighten the mood and change the subject. I shouted “Two shots of jack for this year’s champion”
“I can’t drink while working”. She quipped back at me.
I smiled and gave her a hug and told her everything will work out. Emily went back behind the bar and poured the two shots.
“It would be rude for you to let me drink alone”
I slid the second shot toward her. After we took our shot she took the glasses to clean them. While her back was to me I paid my tab and left her $100 tip and headed home.
The next morning Emily was waiting for me in the parking lot. When I got out of my car she ran over to me and gave me a huge hug. I could feel her pressing her whole body against me. As she pulled away she gave me a kiss on the cheek.
“You didn’t have to leave me such a big tip that wasn’t why I asked you to the bar.”
“I know but, I’m sure the money would get better use with you than me.”
She hugged me again and we then walked in to work and went our separate ways.
During that day I don’t know why but I couldn’t stop thinking about Emily and how she looked last night at the bar. And then I thought about the full body hug she had given me in the morning. She had never hugged me like that before.
Finally the work day came to an end and Emily met me at the elevators to leave.
Emily started talking Fantasy football but for the first time I couldn’t focus on that l was staring at her. She was wearing a white button down shirt and a black skirt that went just past the knee but was form fitting with black high heals on.
All of a sudden I realized she had asked a question “... so what do you think?”
All I could say was “well you have to do what is best for you.”
She gave me a puzzled look then laughed and said “you didn’t hear a word I said did you?” I said I’m sorry my head was somewhere else.
“I was asking if you wanted to watch the games together this week since we will be facing each other?”
“What bar do you want to go to?”
“Ugh I work at a bar 5 nights a week I would rather not go to a bar. Didn’t you mention to the guys your sports room has a 75 inch tv? Why don’t we watch it there?”
“Ok I’ll see you Monday at my place at 7:30pm. You don’t have to bring anything.”
Monday came and Emily showed up at 7:30 on the dot. She was wearing a jets jersey but she had it tied up showing off her flat tan stomach and her breast filled out the top of the jersey. She also had on black sweat pants that were so tight it curved perfectly around her toned legs and ass. She had her hair up in a bun and was wearing her thin framed black glasses.
I was taken back I had never seen Emily dressed like this before. I couldn’t help but stare at her standing there.
“Are you going to invite me in or are we watching the game on the porch?”
She had a bag of chips in one hand and a bottle of jack in the other. I regained my sense and said “come on in.”
“Thank you. I figured since we were staying in for the games I would wear comfy clothes hope it doesn’t bother you.”
“Not at all make yourself as comfortable as you want.” She smirked as she walked past me.
I followed her to the kitchen.
“Want to make the games a bit more interesting?”
“I don’t want to take your money.”
“Who said you were gonna win? And besides I had more interesting wagers if you’re up for it.”
“I hope your team is ready because I’m bringing my A game this week”.
“My team is too much for you to handle”.
“You must have forgotten what my D can do”.
She paused and looked at my crotch with a devilish grin.
“That’s a lot of talk. So how about those wagers?”
“What did you have in mind?”
“If I win you have to cover my league fee and if you win we can really see if I can handle your D.”
I stood there for a second with my mouth slightly open.
“Are you sure about this?”
“I never make a bet I won’t honor. But if you’re scared it’s ok.”
“OK it’s a bet.”
Our matchup was in the final minutes of the game. I was winning by 10 and a bit smug faced. Emily had been sitting right next to me the whole game with our legs touching.
I had trouble focusing on the game because of what she was wearing. No matter what was happening I was rock hard looking at her body. The final play her receiver catches a pass Emily jumps up and is cheering until she see him get tackled at the goal line ending the game and Emily loses by 1. I sat there quiet to see what she was gonna do. She was still facing the TV as she dropped to her knees in defeat.Emily turned around at me and a smirk came across her face.
“I guess I get to see how big your D really is.”
She gets up and walks over to me. She pushes me back against the couch running her hands down my chest. Her eyes locked on mine. She drops down to her knees but this time with a smile. With one hand undoing my belt she takes her other hand and starts rubbing my hard cock through my jeans. She unzips my pants and pulls them down to my ankles.
Her eyes light up as she see the outline of my hard 8 inch cock through my boxer briefs. She rubs the shaft through the briefs with her face inches away. She leans back and takes off the jersey exposing her black lace bra. It wasn’t until now I could truly admire her size 34D breast.
As I go to put my hands on her breast I get a quick feel before she pushes me back on the couch. She lowers her bra’s shoulder straps she leans in and starts rubbing my shaft again this time a bit harder.
She licks my hard cock through the briefs slowly then continues rubbing with one hand. She takes her other hand and unhooks her bra from the back and lets the bra fall to the floor.
She pulls down my briefs and grabs my hard cock with enthusiasm and starts stroking it up and down every so often licking the head.
As she moves her hand to play with my balls she puts my cock deep in her mouth. I can feel her tongue against the shaft as she goes up and down. She starts to increase her pace and I feel like I can’t last much longer. She can tell so she takes both of her hands and hold onto my ass pulling me deeper into her mouth as I pump load after load of warm cum down her throat. She gags for a moment but then licks up every last drop.
Using her fingers to get the excess off her lips and back in her mouth. She leans back and says
“Congratulations Commissioner I‘m looking forward to our next match up” with a smile she stands up gets dressed and heads home. I think to myself I can’t wait till we face each other again...