MILF Happy Hour
Alex and Jenn were best friends in high school. Alex came from a broken home, and her mother worked multiple jobs to keep her kids in some semblance of a normal life. Jenn had an extended family with mom, dad, sisters, aunts, uncles and cousins. They welcomed all who came, and Alex easily fit in with their loud, fun, barely-controlled chaos.
They were twin daughters of different mothers. They were about the same height, had the same color hair, and similar taste in clothes, shoes, makeup, and style. The biggest noticeable difference was that Jenn had fuller lips and chest. They were both extremely attractive, had no problem getting dates, and often dated best friends. They both made drill team their freshmen year, and it controlled their social agendas through their senior years.
After graduation Alex went away to college while Jenn worked full time and attended junior college in the evenings. There was less time for them to hang out, but Jenn did occasionally visit Alex at school, stayed in an apartment with no parental supervision, went to college parties, and even took trips together. But as often happens to best friends, they graduated, got jobs, got married, and they drifted apart. They only saw each other at reunions or when they bumped in to each other at random local events.
At their 25th reunion they found each other and found a table. They talked about careers, their kids being married or away at college, and for the first time in years it seemed they had time for lunch or drinks. Phone calls were more frequent, and dinners with their husbands were added to their agendas. Jenn invited Alex to join her teaching friends at a girls' weekend that included two nights in a suite at a high-end hotel with a Pink concert in between. For each of them, it was the first time in too many years that they could concentrate on being women instead of having to be moms or wives.
The week after the Pink concert Alex and Jenn met for happy hour. Even though she lived 30 minutes away, Alex's company had put her up at a hotel in the Arts district while she attended meetings with a potential client. She met Jenn for drinks on the patio of a trendy Tex/Mex restaurant less than a block away.
When they arrived at the restaurant they were dressed alike - similar $200 haircuts, $300 sandles, $150 mani/pedis, and the latest comfortable MILF summer ware. It was like high school only better - they both married comfortably, had good jobs, nice homes, and had aged extremely well. In many ways, they were even sexier than when they ran together 'back in the day'.
They ordered a round of swirls, and before dinner arrived they were already feeling the effects of the alcohol. Alex had so much she wanted to talk about and didn't waste any time.
"I had a great time last week. Thanks for including me."
"It was an awesome weekend," Jenn answered. "Those girls get crazy!"
"I thought they were great. I hope we can do it again sometime," Alex answered. After a slight pause, she continued her thought.
"So are you and Kasey... uh... 'close'?"
Jenn noticed a slight emphasis on the word 'close' and was curious what Alex meant.
"We worked together for five years, then we were pregnant at the same time. Our kids were pretty close growing up. I guess we're kinda close, but you and I were much better friends in high school. I've never had a closer friend than you were back then."
"Oh, that's so sweet! I feel the same way!," Alex answered. "The two of you seemed so close, they way she would put her hand on your leg, or when you guys hugged."
"Oh, well..." Jenn wasn't sure if Alex was drunk enough for the rest of the story, but she really wanted to tell her. "...we were pretty close before she got married."
Alex was pretty drunk, but she definitely noticed the emphasis Jenn put on 'pretty'. She hoped Jenn would say more, but she didn't.
"OK, I understand if you don't want to talk about it..."
"I don't mind talking about it - I just don't want to say anything that will make you think less of me. We haven't been as close since the kids, and I've changed. We've both changed."
"How have you changed?!" Alex asked somewhat-loudly as she put her hand on Jenn's leg. After two swirls, she was getting a little loud.
Jenn put her hand on Alex's and gave it a little squeeze.
"Remember in high school where Kimmy was the wild one, I was the innocent one, and you were somewhere in between?"
Alex shook her head 'yes' as she tried to focus on Jenn's suddenly-serious face. Jenn squeezed her friend's hand again for effect before continuing.
"That may not be the case anymore...". She held Alex's hand even tighter and moved her face a little closer to her friend's face. She looked deep into Alex's eyes as she let a little smile replace the serious look she temporarily wore.
Alex never blinked and never let Jenn's short serious spell phase her. She just continued to smile and ask questions.
"So how are you so different?"
"I'm not as innocent as I was in the day..." Jenn paused as she thought about how much to share. She decided to keep their discussion PG. "You know, marriage, being a Mom, and... other stuff."
Alex still looked confused, then asked "Other stuff? Like kinky PTA meetings, or sex-toy sales person, or..."
"You're getting warmer..." Jenn said with a very mischievous grin. Since they started hanging out together again after the reunion, she and her husband, Mark, often fantasized about her getting together with Alex. Jenn was even more motivated after seeing Alex bounce around the suite in barely-there pajamas during the concert weekend. When she left home that afternoon, she wasn't sure if this would be a weekend she could try, but this seemed like a perfect opportunity.
"Before the kids were born Mark and I had a threesome with Kasey one night after a happy hour." (Teacher Happy Hour, Pt. 1, 2 and 3, June 2018 and August 2020 in Literotica)
Alex looked a little surprised but also excitedly smiled as she responded.
"Really?! That's so hot. Who would've ever thought the innocent one in our group would get so wild. Good for you! So that's why you guys are so close..." Alex replied.
"Yeah, it tends to bring you together when you've seen your 'hair down there' in another woman's mouth... And then had her's in your mouth!"
Jenn was relieved that Alex hadn't freaked out or gotten judgemental over her revelation. She and Kasey had drifted apart after Kasey moved to a new job, and Jenn's current teacher friends weren't as outgoing. She hadn't talked to anyone about intimate secrets in years so it was pretty hot to do it with someone she'd known for so long. Alex hadn't shared anything yet so she decided to ask.
"So how about you? Any secrets you wanna share?"
"Oh, I DEFINITELY have some secrets," Alex answered between long drinks. "Nothing as cool as a threesome, but I've done some things," she added staring into Jenn's hazel eyes.
"Really? Do tell - and I want to hear everything!" Jenn purred sensuously.
"Remember when you, Kimmy, and I were in Jamaica, and I came in to talk to you while you were in the shower?"
"Yeah, you said said Kimmy had met some guy on the beach and needed some alone time."
"We went to his room for drinks, but then they started making out. I thought about leaving, but it was kinda hot being there. They would occasionally look at me to see if I was watching or if I was going to leave. When I didn't leave they would get a little more into it. Soon they were naked, and then he was fucking her. She was watching me for my reaction, then reached her hand out to me like she wanted me to join in. I was so horny that I was tempted, but I didn't know this guy at all. So I watched a little more then left."
