Anne was a pretty woman how must have just touched 40 years old when we hooked up. She was definitely a very bangable milf who had a few kids and was going through a hard time. I met her son when I was playing on the travel hockey team. We weren't great friends and didn't really talk, but I had his number in my phone and we were in the some mutual group chats. We hung out in the same group until I went off to prep school for hockey and eventually college.
I took a year in boarding school, then did a year in the ECHL and eventually the AHL before going to my local university. I lived on campus for my first year even though it was my hometown and my parents lived 10 minutes away. I wasn't eligible to play there, but I joined the club team and wanted to get a degree while hooking up with as many girls as possible. Needless to say I was one of the older freshmen in the class so I was cleaning up. The guys liked that I could buy booze and the girls loved that I was older, more experienced, and much more confident.
It was like shooting fish in a barrel. As I progressed, I moved off campus and everyone loved to come to my apartment before hitting the bars downtown. It was called "the pitstop." Eventually I got bored and started to venture off campus a bit I would meet people at the local Applebees and building a network of friends outside of college. I skipped lectures and revision, but always had a 30 rack ready to go.
I first met Anne in the summer before my sr year. We flirted a little at the bar once or twice. It was always in a joking way. She was wearing a ring, but was always with her girl friends drinking. It sounded like she was pretty shy and reserved but I thought she was an easy target. I'm a bit of a taller and stronger looking guy since I played sports. It honestly felt like college or school to me, the girls would almost always be looking for a fun loving jock to entertain them for the night.
One night we got pretty drunk, mostly my fault for supplying the booze.
"Anne, you've got solid knockers." I said pretty matter of factly to her while looking at her boobs. I said it in a way that wasn't aggressive, just a casual acknowledgment.
"Thanks. Pretty direct of you, I must say." She replied with a sarcastic tone to show that she was taken aback by it.
Her thick, dark, curly hair framed her face in a way that made me think about pulling on it.
"Try not to blush too much." I added as a jab while nudging her arm with my forearm.
"I'm not blushing." She said with a pretend annoyance that was cute. She karate chopped my arm playfully. I was flexing and so we shared a look. Her look of surprise that it was hard and my look of "yeah, that's right, I work out" type of thing.
"Look right there, I said as I poked her cheek." Trying to break down the physical touch barrier even more.
"No those are my dimples." She replied while looking away trying to minimize our interaction. I knew I had to say something shocking again to get her attention.
"They say that dimples are just a sign that your parents had sex when you were in the belly. Your dad's dick pokes you in the cheek as he's pumping your mom while your facial muscles are developing." I said as I put my arm around her pulling her close and saying it in her ear in a friendly way. The type of way that indicates this bar is loud and I just wanted you to hear me, rather than pulling her in close in a creepy way.
To my surprise, she stayed in my body space and stood on her tip toes. She grabbed my shirt and leaned to my ear since the bar was loud and said, "no surprise my kids don't have dimples."
"Are you saying your husband has a small weiner and it couldn't reach." Again, purposefully being provocative to keep her attention and move the topic to something sexual. I also love the benefit of putting her husband down too so she would inadvertently think I have a bigger one.
"We just didn't have sex while I was pregnant." She said correcting my assumption with her explanation. I knew I had her.
"So he's got a small peepee and doesn't bend you over regularly." I said again pushing the limits. Then I cut her off when she was going to protest, "or at all. He doesn't bend you over at all." Then I trailed off and said away from her direction almost talking to myself, for comedic purpose, "that man is either gay or has the self control of a monk."
As I kept staring away I could see her pursed lip smile and head tilt. She opened her mouth to say something and I just raised my eyebrows in a questioning manner and she shut it and gave me that pouty smile again.
"Look, I like sex, it's just hard to find time with kids, career, pregnancy, and all that stuff. Not something I would expect you to know about since your like a kid yourself." Anne said trying to sound like we're bantering, but I had her right where I wanted her. She was trying to prove something to me and herself and I struck a nerve.
"Well, you look like you could use another..." I trailed off hoping to get her irritated again.
"No, I don't need any other penises in my life. I've got plenty. Thank you very much." She said sound strong and independent.
"I was going to say another drink. To loosen up. Sheesh. Now I know you NEED another drink." I said to her trying to be funny. I gave the bartend a head nod and held up two fingers. Over she came with 2 more drinks.
"I don't need this. I don't need someone to buy me a drink. I thought you were just trying to say I needed some penis or something else along those lines." She was trying to say, but I stood tall and pretended not to hear her in the loud bar.
I leaned down and told her, "I think I'm getting under your skin a bit, let me buy this a peace offering." Looking defeated and a bit hurt that some random guy her kids age could have this power over her, she submitted and relented to drinking it. That itself was not a sip of alcohol, but a sip of defeat.
