This story takes place four months after our transformative Mexico vacation where my wife Maddie and I really explored our sexual boundaries.
When we got home, we made the decision that we would not be doing too much sexual exploration around where we lived. Maddie's job could be jeopardized if it were to come out that she was to be discovered acting lewdly in public in any manner so we saved our adventures for days we were out of town. That was what made this event all the more surprising.
It was my birthday weekend and we went out to a bar for drinks with friends until after midnight and got very drunk in the process. Maddie, as a treat to me, wore a crop top with a sexy black lace bra underneath. She looked uncredible and I couldn't take my eyes off her all night, but neither could our friends. She got compliments on her outfit all night from them, both the guys and girls. I could tell she was loving the attention as she was absolutely beaming with confidence. This brought back visions of her on our last trip where she was the focal point of every room she stepped in. I discovered she felt the same when we were dancing and she took her turn to do a little performance in a circle that had formed on the dance floor. She shook her ass, swayed her hips and moved in a way that had everyone watching cheering her on.
She had single guys offering to buy her drinks and dance with her all night which I loved to see. She even divulged a few of them for a few minutes after receiving the drink, feeling like she owed them a little bit. My friends at one point were a little confused why I let these random nineteen-year-old looking guys dance with her. So, I just told them I didn't feel like dancing too much and Maddie was really looking forward to getting the chance to since she hadn't in months. They seemed to buy it with a little hesitation but still found it was a bit strange. Since the place was quite loud and crowded, we couldn't see all that much from our booth at the side anyways so we just hung out while she was out there.
Our pregnant friend Josie and her husband Greg who left around 10PM offered us a ride but with it being the first time going out in a while we wanted to make the most of it by staying out. Our other friends Luke and Simon stayed out with us the whole night with the latter taking his turn dancing with Maddie on a few occasions. Luke had his wife stay home sick but Simon was our shy friend who didn't have much luck with girls so Maddie always tried her best to make sure he wasn't left out. One of her favorite things to do when we were out together was to play wingman to Simon and try to get him laid. On this night she wasn't successful and as a consolation prize she danced several songs with him.
As 12:30 came around most of us were spent and we called for a ride to get home. Luke caught a taxi on his own as he lived on the other end of town and Simon would be joining us as we all went in the same direction home. This was when Maddie's second surprise was revealed as who showed up to drive us but our old friend Gurpreet.
He stepped out of his car to greet Maddie who gave him a big hug and we shook hands. I helped Simon who could barely stand up in his drunken state to the back seat and Maddie joined us in the back with her sitting in the middle seat. As we took off towards home, Simon was in a state somewhere between awake and asleep and intermittently kept falling asleep on Maddie' shoulder.
About 10 minutes into the ride, he got really chatty and said, "I'm so jealous of you Jack. You get to take your hot wife home and probably have sex all night but when I go home, I'm going to be pants down in front of my laptop looking at porn, jerking off."
Maddie and I burst out laughing that our normally shy friend who never reveals anything about his sex life just told us he's going home to masturbate. After our laughter had subsided, which Simon himself took part in, Maddie looked over to me with a mischievous look I haven't seen since our trip.
"Well Simon, if we're sending you home to jerk off, why don't I give you something to think about," Maddie said in a sultry tone. Without thinking, she crossed her arms grasping the bottom of her top and pulled it over her head and then expertly reached behind her back and unclasped her bra, allowing it to fall in her lap, exposing her perfect, perky tits. I was a bit shocked as I had not anticipated our night to take a turn like this. The absolute confidence she showed as she removed her crop top and bra was a testament to the wonderful shift in our relationship as she didn't hesitate at all.
I leaned forward to gauge Simon's reaction to seeing her exposed like this for the first time and to my disappointment he was completely asleep, snoring against the window. He hadn't even caught a glimpse of what would have surely made his whole night but someone else did.
As Maddie was putting her bra back on Gurpreet chimed in, "Ohh those are as lovely as I remember, Maddie. You truly are my favorite customer."
"Oh thanks, Gurpreet," Maddie replied, once again dropping her bra to cup each breast in her hand and giggle them for him.
"I think this is your friend's house," Gurpreet said, pulling into the condo parking lot.
Maddie hurriedly put her bra and top back on and I got out to go to the other side of the car to help our friend. I caught him as he almost fell out of the car when I opened the door despite Maddie trying to wake him up. As I helped him to his feet, I let him take a few steps before I saw him start to wobble a bit and decided I better take him up to his door to make sure he makes it home. I put his shoulder behind my neck and we walked together to the lobby on the way gesturing to Maddie that I had it under control.
After we struggled with his keys at the front entrance, we stumbled down the hall to the elevator and pressed the button to go up to the 13th floor where he lived. In the elevator, which was really slow given how old the building was, we got to talking since he was semi awake.
"I hope you had a good birthday man, sorry I got so drunk, it's been a while since I've seen you and I just wanted everyone to have a good time," Simon said, slurring his speech.
"Thanks, I had a great time, I'm glad you waited until the uber to pass out or our night would have ended a lot earlier," I replied.
"Don't mention it, and hey I hope you don't mind me dancing with Maddie, she's so great," Simon said, very slowly talking with his eyes shut.
"Don't sweat it, she loves to dance and I know she loves hanging out with you in the bar. It lets her live vicariously, you know," I said.
"Yeah, she's the best," Simon added. "I hope its not weird to say but I've always had a bit of a crush on her, and I appreciate you both so I'd never try anything you know. She's just so cool and I wish I could find what you guys have together."
"Well thanks for saying that, I know she really cares about you and we really value your friendship man," I said, fully believing he's just saying things because he's drunk.
I let him talk so he'd stay awake and I wouldn't have to carry him all the way down the hall to his room and drop him in his bed. The elevator opened and we stumble to his door and after I made sure he was ok I head back to the elevator and back to the car.
When I got back to the vehicle, I opened the back door and discovered Maddie had once again taken off her top and was sitting there in just her bra. The bra was pretty sheer and you could clearly make out her nipples behind it.
"Well, if you're going to just sit there wearing only that you might as well just take it off," I said, teasing her.
"Why not," she replied, taking her bra off. "Gurpreet was just offering to take us by his house to collect the bra I left in here a few months back."
"If its not too far out of the way," I said, not wanting too be out all night but curious where Maddie was taking this.
"Not to worry Jack, I live only a few kilometers from your house," he said reassuringly while still staring at Maddie's chest. He started driving again, constantly looking into the backseat at Maddie who made sure to stay in the Middle seat to allow Gurpreet an easy view. "You are a very curious husband to allow such a beautiful wife to show off like this. I am very happy I met you both."
I didn't hear all of what he said as I was busy making out with my wife. Maddie was really getting into it too as she allowed me to unbutton her pants and slip a hand down into her panties. I quickly found her clit and started to massage it but was having trouble with how tight her pants were.
"Sit up so I can take theses off," I said to her and she obliged my request. I pulled them down her legs and helped her step out of them, allowing me much better access to her pussy. I pulled them to the side with one hand and started to slowly run my fingers along her slit, pausing at her clit to apply more pressure. I went up and down her tight pussy slowly several times before slipping my index finger halfway into her entrance that caused Maddie to moan silently. I pushed in the rest of the way and curled my finger to feel her G spot. When I reached it, her hips twitched forward a bit and her mouth shot open in an OH motion. I withdrew most of my finger, applying pressure as it went up and drove it back in, with my palm making contact with her clit at the bottom. I kept repeating this motion at a steady pace and It seemed like she was about to cum in short order.
While she was really getting into it that was unfortunately when we pulled into Gurpreet's driveway. We had unknowingly ventured into a rougher part of town and didn't know exactly where we were. His house was an older duplex that was definitely in need of some repair on the outside at least. Gurpreet put the car in park and turned around to watch me finger Maddie. There we were, a young stunning brunette babe having her pussy played with by her husband while an old fat man watched from the front seat.
"I need to cum so bad, Jack," Maddie said in between heavy breaths.
I thought I would up the ante a bit and pulled my pants down, allowing my rock-hard cock to spring out. I knelt on the seat and had her lay down over the middle seat and replaced my fingers with my dick that slit easily into her drenched pussy.
"Oh fuck, Jack. You're fucking me right in front of our driver, oh my god," Maddie moaned as I bottomed out into her.
That's when I saw it for the first time. Gurpreet had also pulled his pants down and was stroking himself to the scene and to say he had a very unique penis would be putting it lightly. It was a bit dark and he couldn't have been more than 3 or 4 inches long but it was uncommonly thick, atleast the diameter of a soda can. His motions were short and his hand didn't fit all the way around it as he moved it along his shaft. I all of a sudden got curious what it would look like in Maddie's hand and I knew he would want to know as well.
I didn't think Maddie could see it so I said, "why don't you come back here and join us so Maddie can see."
He smiled and quickly obliged, making his way to the back seat surprisingly fast. We soon found out there wouldn't be enough room for him to sit with Maddie splayed over the seats so we slid further towards the door and he stayed there only inches from Maddie's head. The streetlight gave us both a better view of his odd but impressive cock that he stroked very quickly in Maddie's direction. Not only was his cock impossibly thick, his balls matched and were easily 50% bigger than mine. As soon as she saw his package, she couldn't take her eyes off of it and reached out and cupped his large balls as he continued to jerk it towards her.
As I kept thrusting into her, his leather seats were a bit slippery and I was inadvertently pushing her closer and closer to his cock. He hadn't moved closer but she was now positioned underneath the end of his cock while some precum had started to form at the tip. As he continued his short motions the bead became bigger before finally dripping and landing right above Maddie's eye. She felt exhilarated by the warm liquid and migrated her hand up to his shaft and grabbed in like a door handle and resumed the jerking motion. My prediction was right, she could only fit her hand around half of the impressive cock and the visual of her hands on it sent me over the edge and I started to fill her pussy.
