An Unexpectedly Erotic Date Night

If you haven't already, check out the previous stories in mine and Maddie's stories beginning with a steamy vacation (Slowly opening up on vacation Ch 1 to 6) and then continuing since we got back in "A birthday to remember." This story doesn't really require the prereading but it definitely enhances the effect that I'm trying to achieve.

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An Unexpectedly Erotic Date Night

The night started out like every other date night. We went to dinner at a cool new restaurant where we enjoyed a few more drinks that we normally would. It was the first weekend of the summer break for Maddie and she wanted to cut loose a bit to celebrate her time off. It was only 630 PM and we were both fairly intoxicated already. Maddie as she sometimes did when she was feeling playful, she started flirting with the waiter who seemed to taking every opportunity to come by and engage with her. It was pushing 40 degrees Celsius (about 100 Fahrenheit) so Maddie had taken the opportunity to wear a short summer dress that was fairly low cut even with all the buttons done up. I noticed after she went to the bathroom, she came back having undone one of the buttons, revealing another few inches of her delicious cleavage. It did not go unnoticed by our waiter either as he was visibly struggling to prevent his eyes from drifting while he was talking to Maddie.

"So... Jordan," Maddie said while looking at his name tag then back to him. "Do you go to school in town here?"

"Uhhh yeah, I'm at the university," He replied.

"Ooo, what are you taking?" Maddie asked.

"Kinesiology, I'm in my first year," he said.

"You can't be more than 19 then! You could almost one of my high school students. Learning all that anatomy must be how you have these muscles," Maddie said, tracing her hand up his forearm. "I bet the girls are all over you."

"Don't embarrass the kid, I'm sure he does fine with the ladies," I interjected.

"Actually, not so much, I'm still getting to know people and I take it pretty serious so outside of school and work I don't have a ton of free time," he added.

"Sounds like you have a bright future, I can tell being a teacher and all," Maddie said.

"Thanks, wish I had you as a teacher in high school. I probably would have paid attention more," Jordan said playfully, while his eyes dropped to her cleavage.

Maddie saw his eyes shift and decided to play along. She leaned forward and beckoned him closer with her finger so that his face was next to hers and allowed him an even better look down her cleavage. "I would have got your attention, but it wouldn't be on your school work," Maddie whispered in his ear before leaning back.

He stood back up with a dumb smirk on his face knowing it was true.

"I'll be right back with your drinks," he said feeling the tension in the air.

"Can you get the cheque too, we have a show to catch," I called out as he was leaving.

We paid our bill, finished our drinks and headed down the street to the venue hosting the comedy show we planned to go to.

We were running a bit late as the show was about to start were lucky that they still had tickets at the door when we arrived. Lucky for us there were some good seats left which we grabbed. We were sharing a table with another couple who at first glance seemed oddly matched. She seemed noticeably order than him which is not a combination you see very often.

The show started off great with the first few opening acts performing good sets that made everyone at our table laugh hysterically. Some of the jokes really pushed some boundaries so we figured since the other couple were laughing at the same jokes, they were cool people. They had a break before the last opening act and we got to talking with the other couple. Our suspicions were correct as David was 23 and Mary was 33, but they seemed like a great couple so who were we to judge. We ordered a few rounds of drinks and got to know them a bit.

"So how did you guys meet, I bet there's a story there," Maddie said, trying to dance around their age gap.

"Tinder, actually. I know what you're going to say but its so hard to meet people these days," Mary said.

"Cool, I have a girlfriend who met their partner on there. Did you suck him in with sexy photos in your profile like my girlfriend did?" Maddie said, laughing.

"You know I did! Wanna see? I think it is still active," Mary said pulling out her phone.

Maddie scooted in and they went through the photos.

"Wow, you're so confident in these, no wonder he matched with you, I would have too." Maddie said genuinely impressed with how bold she was in the pictures.

Mary wasn't anywhere near as hot as Maddie, she was about 40 lbs heavier and a fair bit rounder but had larger breasts and seemed quite confident. David on the other hand was shy and very skinny but they probably balanced out each other's personalities. I talked to him while Maddie and Mary were busy talking about tinder and such and found out that he's an IT specialist and mostly works from home. We didn't have much in common but did manage to find a show we both liked and discussed that a bit. I found out it was actually his birthday and first comedy show so I ordered a round of shots to celebrate.

The show resumed and as expected the main event was even funnier than the opening acts. We laughed so much the comedian even heckled us, causing us to laugh even more. By the end we were all in tears from the jokes and when they turned the lights on, we checked the time and it was only 10 PM. Having had such a great time with them it would have been a shame for the night to end so early.

"Seeing as it's David's birthday, would you guys like to go out somewhere after this?" Mary asked. "There's a dive bar just up the block that has pool tables that a friend recommended a while back."

"Sure, that sounds great. Its way too early to call it a night," Maddie said.

We let them lead the way and we walked the block and a half to this old looking bar that had a couple pool tables in the corner and a few older regulars hanging around the bar. I went to the bartender and ordered everyone a drink and got some change for the pool tables. I got back in the middle of Mary replaying a joke from the show and somehow it made us laugh almost as much as it did an hour ago. Maddie and I are not good pool players to begin with but being as drunk as we were made us hilariously bad at it. Mary was just as bad but David was a little better than us but not by a lot so it made for long games.

There was rock music playing in the bar which was a welcome change from the super loud club music that most bars played nowadays and it made for a nice atmosphere. The older regulars looked like they were from the classic rock generation and seemed to match the decorum. At one point, either out of frustration of watching us play such terrible pool or because they just wanted to have some fun, the regulars came up to the table and challenged us to a game.

"I can't watch you guys embarrass yourselves in front of these pretty women anymore, me and Joe will play you too next game," he said.

They introduced himself to us quickly as Hank and Joe before going directly to Maddie and Mary to get to know them better.

"Your boyfriends are terrible at pool, but we'll teach them how its done, don't worry Maddie," Hank said as he nudged her with his elbow.

"I don't know these guys may not look like much but they get the job done," Mary said winking at David.

"Oh, is that so? Then why don't we bet on it then?" Hank said. "We'll but you guys a round of drinks if we lose, but if we win, you guys have to dance with us for a couple songs while these guys watch."

"You're on," Mary said immediately from behind Maddie.

They hung around until the current game ended, mostly talking to Maddie and playfully making fun of how we held the cues.

As Maddie was lining up the last shot Hank came up behind her to 'help' her out.

"No no no, Maddie. You have to have a firm grip, and get down nice and low," Hank said from behind Maddie while he forced her to lean over the table. He wrapped himself around her and pressed into her ass at the same time as he placed a hand over hers holding the cue. All the while Joe and David stood across the table looking down Maddie's shirt.

"That's it," he growled as they moved together and sank the last shot.

Maddie stood up, rubbing her ass into Hank in the process and turned around and high fived him in celebration as she and I had finally won a game. She came around the table and kissed me and as she was near she whispered to me, "Hank was totally feeling me up there." As if to motivate me to win the game.

"Now go kick their ass," Maddie said aloud.

We decided to play best two out of three just in case the game was close. The first game went pretty much as you would have expected with them winning in only 5 turns and us only having sunk half our balls.

"George, get the song ready these fine women are about to get this place going," Hank shouted.

Maddie and Mary looked on with a fake disappointed smile as they probably knew we didn't stand a chance.

"What kind of music do you ladies like?" Hank taunted.

The next game started off a bit better as we got some lucky shots and they missed a few easy ones mostly due to being distracted by Mary and Maddie. Maddie at some point had undone another button and the top of her lace bra became visible when she leaned over the table as Hank was trying to shoot. Their efforts were in vain though as when it came down to the final ball, I sank the cue ball along with it so we lost again.

I apologized to David for being so bad and he didn't seem to care much that his girl was about to dance with these two old guys. I obviously didn't mind either, after all we had been through, this would be considered tame but I couldn't expect the other couple to have the same tolerance so I was impressed with his reaction.

The two men went over to our girls right after the win and took them by the hand to the middle of the mostly deserted bar. The bartender turned the music up and played a slower country song that allowed them to dance. Hank paired with Maddie and Joe with Mary and they started it off innocently enough just holding one hand and another at their low back. Both of these guys wore button up shirts, cowboy boots and jeans that were befitting of men their age. Maddie and Hank, unlike the others seemed to be talking the whole time they danced and she was laughing at his jokes as they did. He seemed like he was really laying on the charm and I was intrigued by what he would try in this scenario. By the end of the first song, he had placed both hands on her back and Maddie had her arms around his neck. She caught him multiple times peering down her dress but she didn't stop him from staring, in fact she later told me she enjoyed it.

The second song played and like the first one, Maddie and Hank's position changed a bit so that her legs were inter twined with his and they slowly rocked back and fourth to the song. About halfway through one of his hands had slid down and was placed on her ass with only the thin material of her dress in the way. She didn't stop him so he got a bit bolder and started to kiss her neck by the end of the song. When it ended Maddie gave him a kiss on the cheek and came back to me with a mischievous smile on her face.

Maddie leaned in close to me and whispered, "I'm so wet right now."

"I wonder what would have happened if you stayed for another song?" I teased.

Maddie gave a dangerous grin and said, "lets, find out shall we?" She said as she turned, catching up to Hank on his way to his stool and whispered something to him. The she slowly took him by the hand to the center of the bar and the next song started to play. She wrapped her arms around the back of his neck and he pulled her in tight by her hips. His one hand found her ass immediately and Maddie didn't finch, in fact she tilted her neck back a little seemingly in enjoyment. This gave him a very nice view of her cleavage and I noticed his other hand trace up her side coming to rest on her upper back.

Maddie noticed he was staring down her shirt and reached up to undo one of the buttons of her dress. Her already revealing top now showed a dangerous amount of cleavage and it had Hank practically drooling. Pushing it even further she placed a hand at either side of her breasts and squeezed them together. His hand drifted from her side and was now over top of hers but with it being much larger than hers, his finger tips were touching the side of her tit. She slid her hand from under his, allowing his palm to cup the side of her breast while she undid another button.

The dress was now open to the strip of fabric connecting the cups of her bra and holding on by the thin straps over her shoulders. Hank's hand drifted further up to Maddie's shoulder and while making eye contact with her, he slowly slid the strap off the end of her shoulder. She was going along with everything he wanted and it was driving me crazy, her body was intoxicating and he was setting it free. The next song started and they continued slowly dancing as he nestled into her neck, planting slow sensual kisses. She was eating it all up, completely entranced by what they were doing. She moved her hands from the back of his neck, to his shoulder and then to the top of his chest, feeling his weathered body. Sliding her hand down further to his stomach and to the top of his pants. He stopped moving in anticipation of her next move. Her hand grasped his button and expertly undid with a single motion, looking up at him as she moved.

"I bet you've got a nice big cock for me, don't you?" Maddy whispered to him. She turned around and bent at the waist, grinding hard into his crotch as she felt his hands grip her hips. She felt him thrust his crotch into her ass several times, her tits almost bouncing out of her top in the process. After a few more thrusts she stood back up and turned to face him. She looked down and she could see his head covered only by his underwear peeping out the top of his pants, a small wet spot permeating the thin fabric. She slowly began tracing her hand down from his neck to his chest and further down to the middle of his stomach. The path her hand was taking would eventually lead to the only thing on his mind, in mere seconds she would be playing with his dick. That is she would have if she hadn't looked back up to him as she licked her lips and slowly began backing away, smiling widely until she was close to me and turned. He stood there dumbfounded by what had just transpired with a mix of pleasure and confusion before slowly going back to the bar to join the other regulars.

Mary had gone over to David who seemed to have enjoyed the show. Mary hadn't gone as far as Maddie but she still flirted quite a bit with Joe. A few seconds later Hank and Joe came over with a tray full of shots for us and we all did them. It was whiskey which none of us expected and all hated except for Hank and Joe. They went back to the bar and we contemplated what our next move was. Maddie was clearly horny as hell and I wouldn't have minded taking cab home then to bring her home and fuck her brains out. Mary and David were a few feet away and talking, I assumed they had similar plans given that they were as drunk and affectionate as us.

I was just thinking of a polite way to tell them we were going to leave when Mary said, "we don't really do this kind of thing and we've only ever just toyed with the idea of it anyway. Buuut ... since it's David's birthday and we really like you guys, we were wondering if you guys would be down to swing?"

I was very surprised, but impressed with how direct Mary was. She wasn't conventionally hot but her confidence was very attractive and she had the look of someone who knows what they were doing.

Maddie's first reaction was to smile so I figured I knew what her answer was but we hadn't had sex with anyone else, just the occasional handjob. This would really be expanding our boundaries and honestly, I would have gone along with whatever Maddie wanted to do.

"Whatever you want to do, I'm down," I whispered to Maddie.

She stool there contemplating for a while before finally saying to all of us," well we were just talking about getting out of here so we could fuck when we got home. We haven't really gone that far before and I don't think we're going to tonight."

"That's ok, it was just a crazy thought we ...," Mary said a little disappointed as she was cut off by Maddie.

"But since it's your birthday, meet us in the bathroom in a minute and I can give you a little present," Maddie said.

Maddie took me by the hand and I followed her around the corner into the bathroom. We closed the door behind it and she immediately started kissing me passionately.

Between kisses she said," You're going to love what's about to happen."

David and Mary walked into the bathroom and Maddie went by and locked the door behind them. It was a bit of cramped space with the 4 of us in there and it wasn't the cleanest washroom either. Mary and David looked a bit nervous compared to Maddie and I who were pretty relaxed with me just planning to enjoy the show.

"So have you guys ever done anything like this before" Maddie asked playfully as she drifted closer to the couple.

"No, but we've talked about it a lot," Mary said.

"Oh really?" Maddie said, now right in front of Mary.

She leaned forward and kissed her, placing a hand behind her head. David stood to the side and enjoyed the show with me. They made out for a minute and let their hands wander each other's bodies, putting on a very sexy display. Maddie kissed along her neck and up to her hear and whispered, "I'm going to suck your boyfriends cock, is that ok?"

"Mhmm," Mary nodded while Maddie kissed her neck.

"Does he have nice, big balls to empty all over me?" Maddie continuing to whisper.

"Yeah, he does," Mary said shakily.

Maddie kissed her once more on the lips and then turned to David and kissed him. Mary came over beside me to watch Maddie make out with her boyfriend before what she planned next. As Maddie kissed David, his hand found its way to her breast causing her to moan in his mouth. She slid the straps off her shoulders and let her dress fall to the ground revealing her matching set of sheer lace bra and panties. She reached behind her back and undid the clasp of her bra and that too fell to the floor. Both hands now found their way to Maddie's tits and he squeezed and pinched her nipples to Maddie's pleasure. He broke their kiss and leaned down to put his mouth over her left nipple and began to suck it. Maddie threw her head back in response to his mouth on her and traced her hands down his body until she felt his belt. She continued down and could felt the outline of a decent sized cock from behind his pants. She ran her hands up and down it a few times before unbuckling his belt and reaching her hand down into his pants. She found his shaft and gripped it tightly to judge its thickness and it was to her liking as it brought a big smile to her face.

I could tell Mary was enjoying the show as she was leaning against the wall beside me, breathing heavily and squeezing her breast through her dress. I couldn't blame her; David almost certainly will never be able to hook up with a woman of Maddie's calibre. I think Mary might not have minded having Maddie to herself after her reaction to their kiss and I wouldn't have minded seeing it either.

Maddie was now moving her hand up and down in his pants as he continued to suck on her nipples, he could not get enough of those perfect, perky tits. She withdrew her hand and found the band of his underwear and pulled them down in the same motion as she lowered herself to her knees in front of him. An average sized cock sprang free but with one caveat, he was uncut. Maddie had never handled one before and had admitted to me that she was very curious about them. She took it in her hand and jerked it back and forth, transfixed on how his foreskin moved. As she just held it in front of her only the tiniest bit of the head peeked out of the skin and she stuck her tongue out and lightly flicked the exposed head. It had a salty taste like that of precum as she withdrew her tongue to taste it and lick her lips. She kissed the whole tip next then lifted it up and kissed all the way down the underside to the base. Maddie started kissing further down to his balls while she slowly jerked him. She drug her tongue further down to the underside of his balls, letting them on her nose. Pausing there to lick the border of his taint and sac as she looked up into his eyes. This was something she never even did with me and I so turned on and a bit jealous that he was the one to experience it first. She was in a spot that if she moved even an inch further down she would be licking the rim of his hole and I didn't even know if she was into that.