MILF Happy Hour

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."

"Oh my gawd," Jenn said. "I was so naive back then I'm not sure what I would have done."

"I wasn't naive," Alex responded. "I had some experience, and watching them was so sexy. But I'd never done a 1-night stand or had casual sex or been in a threesome so I was nervous. I came back to our room but didn't see you. I heard the shower and just busted in to have someone to talk to. Then you were naked in the shower and I was still so horny. For a second I thought of getting in with you and seeing what would happen. But then I remembered you were a lot more innocent than us, so I didn't do it..."

Jenn knew parts of this story from a few years after they graduated, but this was the first time she'd heard the intimate details. She wasn't surprised at Kimmy - she was definitely the wildest of their group and was never afraid to have random sex. She remembered that night that Alex came in while she was showering and appeared a little flustered. She didn't know why but wasn't surprised when her best friend walked in and hung out. In drill team they dressed together, showered together, hung out all the time, and had very few secrets. She'd heard rumors of some of the girls hooking up, but she never imagined she was almost one of them. She and Alex were incredibly close, and there was a type of very-close, trusting love between them. And at 21 when they took that trip she was a developed woman whose family had used guilt to keep her from trying the supposedly-forbidden joys of sex. But after high school it had gotten harder to fully adhere to the guilt-filled philosophy, and she was extremely curious about intimacy. If Alex had joined her, she probably would have welcomed her.

But that was years ago.

"I never knew the full story," Jenn responded. "Just the part about Kimmy. So you're a voyeur, and I'm bi. We all have secrets. But that was a long time ago."

Alex smiled, took another drink, then looked like she had something else to say.

"Is there something else?" Jenn asked.

"Yeah, I'm a voyeur... And a slut."

This time she dropped her eyes down so she didn't make eye contact.

"Really?" Jenn responded. "Do tell!"

"A few years ago at Mitch's Christmas party I gave one of his friends a blow job," she said partly excited and partly ashamed.

This time Jenn looked shocked but intrigued.

"Really?! Why?"

"I hadn't been laid in so long, and this guy was flirting with me. Mitch was talking work to a group of guys, and I was looking hot..."

"I bet you were looking SOOOO hot," Jenn offered, encouraging Alex to keep talking.

"You know I was!" Alex agreed before getting back to her story. "...and we were walking, then I noticed we were in the parking lot between a bunch of cars and no one was around. So I gave him a quick kiss while rubbing his cock. He didn't object so I unzipped his pants and he was in my mouth. For a second I felt guilty and stopped. But then I remembered how long it had been since Mitch had touched me, and how many times he told me 'no', so I finished."

"Finished? As in, you let him..."

Before Jenn could finish, Alex completed her sentence for her.

"Yep, I let him cum in my mouth. Then I went back inside and told Mitch I was ready to go home. I tried to get him to do me, but he again said 'no'. So for the first time ever I got out my vibrator and masturbated beside him. He objected for a second, but the look on my face told him to get away. I had a great orgasm right next to him!"

"Wow, that is so hot. So I guess Mitch never found out?"

Alex shook her head 'no' while taking another icy drink.

"Did you ever see the guy again?" Jenn asked.

"I did, but just at occasional events Mitch's office had. We never hooked up or anything like that. But sometimes we'd make eye contact, and the look on his face told me he was open to it. Kept me pretty horny for a while."

Alex looked at Jenn during a temporary break in the conversation. She hoped Jenn wasn't too shocked learning her BFF was a slut and was relieved when she saw Jenn open her mouth to speak.

"I never masturbated until Mark and I had been married over a year," Jenn responded in an almost-embarrassed tone. "After we'd been married a while, he asked me to do it for his birthday. I didn't even know how, but we sat in front of this mirror and he guided my hand. He made me put a finger inside. I was pretty sure I was going to hell, but it felt really good. After a few minutes he got me to make myself cum. Now I love it and do it all the time!"

"Wow," Alex responded. "You were probably the only drill team girl who didn't do it."

Alex took another drink then started another story.

"A few months after I blew Mitch's friend, I was on a business trip to New York. During dinner one night a guy I worked with was very attentive, and I was very horny. We ended up fucking that night, and I didn't even feel guilty. I decided that night I was never going without sex again."

"Seriously!?" Jenn asked, mildly shocked. "How was it? SOOO HOT!"

"It was very hot. Intense. Naughty. Forbidden. Sexy. Multi-orgasmic. Sex like you have when you first meet someone and are desperate to feel them inside you. New relationship sex... I didn't feel guilty then, but I did a little later when I got home. But Mitch still barely touches me, so no more guilt. Never again."

Alex paused for a second but was then on to her next topic.

"Speaking of hot, I think that guy sitting alone over there is pretty hot. And I've heard rumors about..."

"Black guys?" Jenn responded as she turned and followed Alex's stare to a handsome, late-30's guy eating alone a few tables away.

"Yeah, about how huge they are..." she said with a very naughty grin.

"I've heard that, too," Jenn answered.

"So let's find out," Alex said, almost pleading with Jenn.

"What... go over and ask him if he has a big dick?"

"No," Alex replied sweetly. "But..."

"You mean pick him up?" Jenn asked, barely surprised.

"Yeah, will you help me?" Alex

"Help you pick him up? Girl you're so hot you won't need any help getting in his pants!"

"No, not pick him up. If I do pick him up, will you come up to the room with me? I've met up with guys a few times, but they were someone I'd already met or at least talked to. I've never just randomly picked up a guy at a bar. But, DANG he's hot. And I've always fantasized about being with a black guy. Especially after watching some videos. They are HUGE!"

"So you want me to go up to the room with the two of you?!"

Alex shook her head 'yes' while smiling as seductively as she could.

"And do what?" Jenn asked.

"Make me feel safe and comfortable, and of course watch. And maybe you could even help out a little, and then..."

"Then what?"

"Well maybe he's fucking amazing, and amazing at fucking, and you might want to..."

Jenn had never heard Alex cuss before, and as images of her bestie riding a huge black cock to orgasm swirled through her head the dirty talk gave her a slight tingling between her legs. She picked up her phone and dialed Mark.

Alex heard half the conversation between Jenn and her husband, Mark. She only half-listened to their conversation as she mentally undressed the stranger. As she snapped out of the fantasy and rejoined the present, she heard Jenn talking.

"Really? All the way up?"

When Alex heard Jenn talking she turned to watch her friend to see if she could judge how it was going. By her smile, she was pretty sure that it was going well.

"Of Alex?"

Jenn cut her eyes toward Alex as she continued talking with Mark.

"OK, I'll see what I can do."

Jenn watched Alex who is watching the guy she wanted to pick-up.

"Me? Would that bother you?"

Alex was again watching Jenn, and if it was possible her smile was getting even bigger.

"OK, sounds good sweetheart. I love you! I'll call you from the hotel if it all works out."

Jenn was beaming ear-to-ear as she hung up the phone. Alex couldn't wait to hear Mark's response.

"So?" she asked impatiently.

"He said I should put my hand on your thigh when the Prey is watching. He called him 'Prey' because with two cougars hunting the poor guy doesn't have a chance. Then when we know he's looking I should lean in close, pretend to whisper in your ear, then nibble on your ear as I move my hand ALL the way up your leg."

"All the way up..." Alex asked not sure what Jenn meant.

"Yeah, you know... make sure he sees me touch you 'there'".

"There? You mean my..." Alex said not sure what word to use.

"Yeah, your 'pussy'," Jenn whispered enthusiastically, leaning in close so no one around would hear. "is that going to bother you?"

"No, it won't bother me - as long as he thinks it will work." Alex replied

"He has no idea if it will work. But he said he would have fun playing alone while he thought of me touching you there," Jenn said busting out laughing.

Jenn got up from her chair, checked her shorts and top to make sure she still looked as hot as she had earlier, then started to walk away.

"Time to earn my wing man wings," she said.

"Where are you go..." Alex stammered as Jenn walked toward the stranger. Jenn ignored her as she put on her most seductive smile and approached the stranger. This new, bold Jenn was new to Alex, but she she was pretty sure she knew what her friend was doing. She watched Jenn shake his hand, and as they talked she flirted like a professional. She sat next to him, smiled, then laughed, then put a hand on his knee while laughing at something he said. She could only imagine what Jenn was saying, but when she got a serious look and leaned in closer she was pretty sure she knew what the conversation was about. The stranger looked toward Alex with a huge smile, then turned back and smiled at Jenn. Jenn stood up, grabbed his hand and headed back to their table.

"Alex, this is Charles. He DOES have a huge dick, and he would LOVE to fuck you," she said with all the confidence of an experienced player. "And he's even OK if I watch!"

Alex tried not to look too shocked as she shook his hand. She never imagined it would happen like this, with her sitting calmly enjoying a drink while her BFF picked up her first BBC. But as soon as she felt his large, warm hand clasp hers, she knew she would cum fast and often.

There was no need for small talk, and all three of them were ready to get the sexual adventure started. Alex and Jenn asked Charles to give them a 15 minute head start and hurried to Alex's hotel room.

"What do you think I should be wearing when he shows up?" Alex tentatively asked as they hurried toward the hotel.

"Nothing! You need to be totally naked when he gets here!" Jenn responded.

"Really?! Naked?" Alex replied.

"Yeah, can't be shy now - not one stitch on. We already seduced him at the restaurant, so no need putting on something revealing to try to seduce him again. He's showing up because he wants to fuck, and you want to get fucked. You could waste time with small talk and underwear, or you can get down to business and get that itch between your legs scratched. Besides, I want him to get naked, too, so we can see if he's as huge as he says he is. You want me to watch, and every minute you spend flirting is a minute I don't get to see you getting fucked."

"Oh, Ok - I guess that sounds good. I'm definitely ready," Alex replied. "What will you be doing?"

"I'm going to be sitting in the chair next to the bed, sipping a glass of wine, and waiting on the show to start. Maybe cheer a little, make a few requests - generally getting REALLY horny. When I don't think I can take it any more, I may make myself cum or maybe just get naked and join you," Jenn enthusiastically answered.

"Heck YEAH!" Alex responded as she imagined her friend sliding her had between her legs while sitting just inches away. "That sounds perfect!"

The final minutes of their walk were silent as they anticipated the rest of the evening. When they got to the room, there was only seven minutes left in the 15 minute head start they asked Charles to give them. Alex went to the vanity and touched up her hair and make-up while Jenn poured them two glasses of wine. With four minutes left Alex headed to the restroom.