Cassie and I were friends from college. Newly graduated, we both ended up in the Chicago area for work. Cassie lived in a tiny studio apartment on the lake, and I lived out in the burbs because my office was in Schaumburg. We tried to meet up every couple of months or so, but it ended up being more often during the Bears season. We were hanging onto the old college “Sunday Funday” tradition the best we could post college. We were much more tame now as college grads, but one Sunday took a particularly interesting turn that brought me back to being a coed.
I decided to drive down to the city Sunday morning to meet Cass at her place, where we could walk to the bars from. Her apartment was in the best location, but parking was always a mess. I decided to suck it up, and pulled into a small nearby garage, and paid the astronomical fee. The attendant motioned for me to pull into a spot, and then I gathered my things, hopped out, and handed him the $30 fee in cash.
I walked out into the cold wind on Clark St. and headed to Cassie’s building. I was filled with excitement to spend the day drinking with my college friend. I headed into her building, buzzed her, and then went up the elevator and down the hall, where she greeted me in her robe with a big smile and hug.
I was the prettier of the two, but Cassie was cute in her own way. She had shoulder-length brown hair, perky B cups, and some thickness around the tummy, booty, and hips. She wasn’t fat, but she was curvy and she enjoyed eating and drinking. I, on the other hand, was tanned and toned in those days. My blonde hair came down my back to just above my waist, and my narrow, fit hips were paired with a round, muscular butt and defined legs. But my best feature had to be my 34DD tits. They were big, dense, and perky, and capped off with nipples that were seemingly always hard and sticking out. This could have been because they were sensitive and I loved the attention they got me.
Cassie wasn’t as into fashion or makeup as I was, but for Sunday Funday, we kept things casual anyway. After all, it wasn’t even 10 am yet! I took off my coat to reveal my sexy but sporty outfit. I was wearing leggings, Ugg boots, and a grey zip-front Bears hoodie with it unzipped to reveal a cropped white cotton cami and no bra. The cami wasn’t sheer, but you could see a hint of my dark pink areolas and of course my nips poking out clear as day. Knowing Cassie had noticed them made them stiffen even more. I just loved when they were the star of the show!
Cassie was still deciding what to wear, while she sipped on a beer she had cracked open. We ended up agreeing that she should wear a Bears T-shirt that she had cut a wider neckline on, paired with a cute orange bra peeking out. She tied it in the back to make it a crop top and revealed her belly button piercing and rose tattoo on her hip. Her ultra-low-rise jeans hugged her wide hips and accentuated the look.
“Nikki, you look so hot!! I can’t wait for you to meet the guys who work down the hall from my office. They’ll be at Stanley’s today too!” Cassie squealed as we admired ourselves in the full-length mirror on the back of her door. Stanley’s was the bar we were headed to that offered bottomless mimosas and a breakfast buffet to kick off game day.
We finished off the beer and threw our coats on over our outfits. The bar was just a five-minute walk and while it was cold, it wasn’t nearly as bad as some Chicago late fall days can be. We chatted about work and what we’d been up to since our last hangout, but we hurried and rushed into the warm bar in record time.
Stanley’s was already packed. The crowd was mostly men in their thirties, a bit old for us twenty-two-year-olds, but I figured as the day went on, the demographic could change. A man in his fifties caught sight of Cass and waved her over.
“Oh, John! There you are. This is my friend Nikki from college,” Cassie exclaimed as she introduced me to this man that she explained was the manager of the insurance business located on the same floor as her marketing firm in the Loop.
He was sitting with a group of four other men who seemed to be in their late thirties, in a big U-shaped booth tucked away in a private corner. She climbed in next to John, and I went to the opposite side and introduced myself to a very plain-looking man with a greying goatee named Dan. We got a round of jaeger bombs and mimosas for Cassie and I to get the day started. The shot went down easy followed by a big swig of mimosa.
We all made small talk and kept the drinks flowing for a while. I was feeling a little flirty and uninhibited, and Dan was enjoying it. I usually wasn’t into plain-looking men who were almost forty, but the attention felt great. I could tell he felt like he’d scored the jackpot having a couple of sexy recent college grads at the table.
He had his arm around me and was rubbing my waistband of my leggings and inching his hand higher on my rib cage every chance he got. I made sure to turn towards him and use my arms to press my cleavage up into plain view for him. He kept stealing glances, and I could feel my nipples doing their thing rubbing against the thin, stretchy cami that was barely containing them. I let the hoodie slip down off my shoulders and toyed with the spaghetti strap of the tank as he talked to me. This had him unable to look away. I leaned in close while we chatted and let my hard nip graze the back of his hand holding his cocktail.
The excitement was building so I decided it was time to hit the ladies’ room with Cassie and catch my breath. Once we closed the door to the ladies’ room, I could see it on Cassie’s face that she was loving the attention of these older men too. She adjusted her top in the mirror so more of her bra was peeking out, and turned to me, and reached to pull the neckline of my tank lower than it already was. I responded by pinching and tugging at my nipples to make them stand on end, the perfect accessory to my tiny white cami.
“Nikki! You little slut! What are you doing?!” Cassie exclaimed.
I just smiled at her, kept rolling my nipples between fingers through the shirt, and said, “I thought we were here to have fun!”
With that, Cassie rolled her eyes, giggled, and pulled me out of the ladies’ room. As we walked back up to the table, Dan was standing at the end with his back to me. I decided to slide in between where he was and another older man named Bill was sitting.
Bill stared right at my tits and said, “Well, what do we have here??” This attention made my stomach flip flop, but I loved it. I pressed my chest out proudly and responded, “What does it look like?”
Bill took that as an invitation to pull the middle of the neckline down with his pointer finger, freeing my perky tits with a bounce. I squeezed them even closer together with my arms, and Bill called over to John.
“Hey John, get a look at these knockers!” Bill half shouted across the table. He had taken one breast in his hand, and gave it a good shake. John and Cassie looked over wide-eyed. Something inside me stirred, and I pulled on my nipples while looking right at Bill. If they weren’t sticking out over an inch from my tit before, they were now.
Dan had sat back down at the edge of the booth, creating a little more privacy, as he went in to play with my nipples with one hand. I noticed his other hand was in his pocket, doing it’s best to work his cock through his pants.
I looked over and noticed John and Cass had started to make out, and I could tell it wasn’t the first time. He was glancing at my tits while kissing her. That slut never told me she was hooking up with this old guy, but I wasn’t surprised, knowing her track record in college. John came up for air, and told all of us to follow him.
As it turned out, John knew the owner of the bar and knew that there was a basement party room that wasn’t in use. He opened a door and we all followed him down the stairs, which opened up to a room lined with booths that looked like a fifties diner.
Bill lifted me so I was sitting on top of the table of one of the booths, and immediately pulled my tits back out and started sucking aggressively, switching from one rock-hard nipple to the other, pulling each one with his mouth and letting them pop from his lips. I’m able to orgasm from nipple play alone, and this was sending me to another planet.
Dan was sitting in the booth with a couple of the other guys, watching this all go down and reaching to fondle the breast that wasn’t in Bill’s mouth. He’d undone his pants and was slowly tugging on his hard cock underneath the tabletop.
I looked over and noticed that John and Cassie were passionately making out, but fully clothed. John caught my eye and told us that he didn’t want to take advantage of his friend who owned the place and we couldn’t have a full-on orgy down there. The guys chuckled but looked bummed. I was breathing hard while my tits heaved up and down on my chest with my inhales, my nipples still rock hard and buzzing from all the licking, sucking, and tweaking.
“Cassie and I are going to head back to my place for some alone time. Why don’t you guys calm down, head to over Duffy’s for a few drinks, and after Cassie and I have had our privacy, you guys can all come up to my condo and pick this back up?” John said.
Reluctantly, we all agreed. Without John at Stanley’s, the bouncer or bartender would surely discover us and throw us out. We all threw our coats on and headed back out into the cold.
Soon to be continued in part 2
