Wedding Date 4

My name is Nathan and I'm married to my wife Jill and we have 2 kids. Jill is originally from Washington which is where we met in College. We now live in Colorado in a rural area and have a small acreage 15 minutes from our town where the kids go to school. This summer we had planned a trip back to visit her parents. I had booked the flights back in March but in April I had received an invite to a wedding near the end of our 2 week vacation.

The wedding was for a guy named Darren who had worked for a tech company I have used for work over the years. Darren is only 25 compared to my 40 but we had gotten along really well when he worked there so I was quite humbled he would invite Jill and I. Jill made the suggestion that I just fly home a few days early and attend. Jill is super easy going so I knew I wouldn't be in trouble if I left her with the kids as they are now 10 and 13.

July had rolled around and we were having a good time at the in laws but it was now the Friday before I was set to fly home for the wedding. Jill was driving me to the airport when she said "I got you a date for the wedding tomorrow!" I figured she was kidding and would suggest I take our dog Ginger.

"Who? Ginger I'm guessing."

"No, very funny, Cassie is gonna go with you. I texted her this morning and since John is still away working she would have something to do Saturday night."

Cassie and her husband John are friends of ours. They have kids near the same age as us and we have hung out often. Cassie is in her late 30's but she is a real stunner. Maybe 5'6", brunette without an ounce of fat and a real nice set of fake breasts that John bought her after their last child. They have an above ground pool and hot tub which we have been in a handful of times. She's never been shy to wear a bikini while in the water. Having Cassie come with me was quite appealing as going stag wouldn't be much fun at all.

"Huh, that will be much better than going alone for sure. You sure you are ok with me dating?" I laughed.

"You bet, but behave yourself at the wedding." she warned.

When I got home Friday night I texted Cassie and said I would pick her up at 230. The wedding was at 4 and it was only 35 minutes to Darren's parents farm at which the wedding was being held.

I arrived promptly at 230 and knocked on the door while opening it to announce that I was here for my date. Cassie called back that she needed 5 more minutes but to come on in. I let myself in and waited in the porch. Eventually Cassie came around the corner in a dark blue strapless dress. It was the type that wasn't tight fitting but the dress was primarily held up by her boobs as there must be some sort of an elastic on the top that kept it from sliding down. It was an appropriate dress for a wedding especially since it was extremely hot out and it was an outdoor wedding the dress looked light and airy.

"Do you have something against the bride?" I asked.

"No, why would I? I've never met her." she questioned me.

"Well it's so supposed to be her day and I think all eyes will be on you! You look incredible!" I replied.

"Haha, now I know how you got Jill, Mr. Charmer."

We hoped in my SUV and headed to the wedding. It was a nice but long ceremony and with the heat it was becoming a sweatshop among the guests. Soon enough it was over and we headed to the white tent and found our assigned seats. We were with 2 other couples who were the parents of 2 of the groomsmen. They were likely in their mid 50's. We both got along well with the others at our table as the women were quite friendly with Jill and they were all heavy into the red wine early on. I had to drive so I had only had a beer with the supper and just sipped water during the speeches. Eventually the couple had their first dance and soon the guests were out dancing. I took the opportunity to find Darren and his wife to congratulate them.

When I returned, one of the groomsmen was seated at our table chatting with Cassie. When I got there she introduced me as her date and myself to Matt, the groomsmen.

"Do you mind if I ask your wife to dance?" he asked me.

"Well, that's up to her as she's not my wife." I laughed.

Cassie said why not and off they headed to the dance floor. The music was fast and Matt was grinding up on Cassie fairly hard and had his hands all over her. Soon there was a group of guys and a few women joining Matt and Cassie. After a few more songs a slow one came on and that's when Matt grabbed Cassie's right hand and pulled her close as they danced intimately. I couldn't help but think John would get a kick out of this young guy trying to pick up his wife.

Matt was whispering in Cassie's ear as they danced but she then pulled back from him with a bit of a shocked look on her face and said something back. The song ended shortly and she headed back over to the table. When she arrived and sat down I leaned in and asked if she was ok.

"Oh I'm fine. Forgot how ballsy young boys can be." she said

I asked what he said to her and her initial reaction was of shock in my opinion.

"He leaned and said that I know you are not wearing a bra cause I can feel your nipples but I'm really curious if you have on any panties and maybe you'd like to show me" she replied with a bit of a laugh.

"Are you ok? Want me to confront him?" I said with some gusto in my voice.

"Oh no, it was harmless. I told him my husband would be the one to find out".

I could tell Cassie wasn't freaked out about it as she has likely been hit on lots and she too is quite easy going.

"I could take a pic for John and text him if you want?" I said sarcastically.

"How bout a selfie of us instead?" Cassie replied.

I grabbed my phone and turned it on us and snapped a pic. I took the liberty of sending the pic to Jill, John and Cassie in a group text with the caption 'Hot Date!'

Jill texted back and said "Looking good you guys, take care of my man Cass!"

John eventually replied to with "Wow, you are a lucky guy. Have fun!"

Our table continued to have a good time as the guys discussed baseball, especially the Rockies while the girls continued with their red wine. The older ladies were quite drunk by 10 pm and I think Cassie had a heavy buzz on while I nursed my 2nd beer. Around 11 pm the crowd started to thin and I asked Cassie if she was ready to head home and she did. We said our goodbyes to the table and made our way to Darren and his wife to say congrats again and then goodbye.

Cassie said she wanted to use the washroom before we left and so did I. We headed to the line of port-o-potty's and when we arrived there was 3 ahead of me on the men's side and only one in the stall for Cassie. Just as Cassie was about to enter I noticed Matt was exiting the mens. Eventually she came out and she said she would meet me at my vehicle and she headed towards the parked cars.

When I finished and was heading over I could see Matt was beside my SUV talking to Cassie again. This time however he kept his distance and when I approached everything seemed fine. Matt shook my hand and said "You are a lucky man!" and walked off.

I was already in the SUV when I heard Cassie yell to Matt "Do you still wanna know?" In one swift motion she reached up under her dress, shimmied her body a bit and soon had her dark panties in her hand and started to twirl them on her index finger. It was a bit of a 'suck on them apples' move as Matt was standing there with his jaw on the ground watching Cassie twirl her panties. With that she jumped in and threw her panties on the dash in one smooth motion. I put it in drive and tried to keep my own jaw off the steering wheel.

Cassie then let out a laugh and said "That should give the young buck something to dream about tonight!"

"He's not the only one who's gonna be dreaming. That was some sexy move Cassie!" I said excitedly.

She laughed again in response and we headed out onto pavement towards home. The conversation swayed away from the evenings event and over to kids, work etc. Soon I was pulling down her lane towards their country home shortly before midnight. Cassie then asked if I wanted to come in for drinks as now I only had a few miles of backroads to get home. I took her offer and tried to stay quiet in an attempt to not wake the kids.

"Don't worry, they are at my moms." she loudly said. "Let's head to the pool deck, its still so warm out!"

I followed her through the house to the back sliding doors and stood by some pool chairs while Cassie headed to the bar fridge for a couple beers. She handed me my beer, clanked bottles, said cheers and sat down beside each other but facing the pool.

Cassie then put her panties, that were crumpled in her hand, on the small glass table between us. She was slouched in the chair and had kicked her shoes off to the side. I couldn't help but think about the fact she wasn't wearing anything under her dress while she sat mere feet beside me. We were quietly sipping our beer while the water from the pool pump made noise in the background. I then grabbed her panties and twirled them with my own index finger and said "So... you're going commando?"

Cassie smiled and said "Ya, this dress doesn't really work with a bra and well...you have the rest in your hand!"

"Commando is actually one of my all time favourite turn ons." I replied. "Nothing more sexy than wondering whats under the a layer of clothes!"

"Oh really? Big Nate likes commando does he. What else turns you on?"

I was a bit offended by her big Nate comment. I was 6'2" and although I wasn't in great shape I didn't think I was big per say.

"Big Nate! C'mon Cassie, I know I'm not in college any more but I'd like to think I'm not big." I replied with some defence in my tone.

"I don't mean fat, I mean big down there. Jill told me about your Willy! You don't think you got her based on your personality did ya?" Cassie responded sarcastically.

I was no longer offended by her comment but now I was blushing. I didn't know Jill had discussed my penis size with her. Although I know I'm no porn star I'm pretty sure I'm above average in length and girth.

Cassie could obviously tell I was feeling awkward and she tried to help by adding "Don't be embarrassed, you should feel lucky. I know Jill is lucky to have it. So now that I've got you beet red what else turns you on?"

I figured what the hell, she was obviously buzzed and having fun. I may as well tell some more.

"I love skinny dipping! That's why I'm always suggesting a pool to Jill." I responded.

"Kinky!! I never knew you guys were exhibitionists." said Cassie.

I laughed hard "Jill would never go skinny dipping even if we had our own pool. That's just on my dream list!"

"Well be me guest, my pool can be your Disney. Let your dreams come true." Cassie exclaimed while gesturing her hand towards the pool.

At first I thought she had to be joking but then I got the sense she wasn't kidding and she was suggesting I go for a midnight dip. I thought I'd see how far this game would go so I stood up to unbutton my shirt and loosened my tie and pulled it off my neck. I was now shirtless and when she continued to sip on her beer I unbuckled and pulled off my pants as well as my socks so I was just left standing in my boxer briefs beside her.

"Go ahead, take em off and jump in!"

I was now buzzed from the beers we had been drinking since arriving that I was feeling brave. I walked the few feet to the edge of the pool and hesitantly pulled off my briefs and jumped in. When I emerged Cassie was laughing and cheering. "How does it feel? Great doesn't it? I love going at night when the kids are asleep."

"The water is super warm and ya it does feel nice." I enthusiastically replied. Thankfully the patio didn't have great lighting and since the water was at least a few inches above my hips I was fairly confident I wasn't exposed to Cassie. The only problem was I found it to be quite exciting to be naked in front of another woman and I was sporting a healthy hard on. The woman also happen to be going commando and was gorgeous on top of that.

Cassie stood up and was headed towards the bar fridge again to which I assumed was to get another beer. I was correct as she grabbed 2 but just as she closed the fridge she reached towards the wall and flicked a switch. That switch turned on 4 underwater lights in the oval shaped pool. I was busy looking at the lights and noticing how colourful it made the water that I didn't noticed Cassie was now at the edge of the pool with her hand stretched out offering me another beer. I took the beer and took a sip while Cassie leered into the water in front of me and nodded while adding "Jill was right! You are big!"

I immediately put my free hand in front of my crotch and said "Sorry."

"Don't be sorry about that. Most men would be thrilled to be packing that!"

My mind was spinning now. I've always found Cassie to very good looking but I had never felt an attraction to her in any way before. Now I was definitely looking at her in a different way tonight. It became very apparent that I was thinking with the wrong head as I said something that I shouldn't have. "Why don't you jump in too, the water is so refreshing!"

Cassie looked at me, looked down, looked at me again and then kinda smiled. She took a few steps towards the edge of the pool. She bent down to set her beer near the edge and then straightened back up and paused. The pause seemed to be a full minute of silence as it seemed as if Cassie was contemplating if she should or not. Then it happened, she brought her hands up the top of her dress, hooked her fingers in the material and pushed it down to the ground and kicked it over to the chairs. The figure in front of me was breathtaking. Like I said earlier, I had seen her many times in a bikini but seeing her in the flesh was hard to describe. Her breasts were extremely perky and round and her vagina was completely shaved. I had always wondered how much she shaved as her bikinis were small enough that she would have to do some. Now I knew.

After standing there for a slight pause she jumped in and went right under the water. When she emerges she slicked her hair back with her hands which gave me another eyeful of her fake tits. Jill has natural 36C breasts but after 2 kids and nursing they didn't sit like Cassie's did. Cassie waded through the water towards the edge and grabbed her beer. She took a big sip and then turned towards me. The water was right around chest level for Cassie in that about half her breasts were in the water.

"So?" she said "You're officially skinny dipping, how does it feel?"

"Exciting! But I'm having a hard time not ogling! You are quite the sight! Wow, those are nice!" I said while nodding at her breasts.

She then took her free hand and gave them a squeeze right in front of me. "Ya, I'm real happy with them."

"Jesus Christ. Don't do that in front of me, I'm gonna end up blowing my top if you don't quit." I responded.

With that Cassie began to pinch her nipples and squeeze her breasts but she did it in an almost comical manner possibly to make me more uncomfortable. She even put her beer back on the edge so she could use both hands.

"It's funny watching you squirm Nate. What more do I gotta do to make you really squirm?" she said.

I never like to be in a situation where I don't have the upper hand and at the moment she was controlling me. I decided to turn the tables and began walking towards her in the pool. This seemed to catch her off guard as she stopped and with a shocked look she stopped feeling herself. I reached for the edge and put my beer down as well and continued towards her.

"What are you doing?" she quizzed.

With a stern look on my face I responded with "My turn to make you squirm!"

I dove at her and she turned to try and run away towards the ladder of the pool. She was just ascending up the steps when I grabbed her around the waist, picked her up and dunked her gently into the water. When she emerged she was laughing and smiling but that stopped quickly as she tried to jump up and push my head down with her hands. The only thing that accomplished was putting her breasts at eye level and mere inches from my face.

When she couldn't dunk me I once again grabbed her by the waist and picked her up and out of the water. I cradled her high up in my arms and begin to walk as fast as I could in an attempt to pick up speed for when I was gonna throw her under again. Cassie must've sensed what I was planning and wrapped her arms around my neck and the began squirming in my arms. Her feistiness was impressive as she somehow got out of my grip and was now wrapped around me but high enough that her crotch was wrapped around my stomach but that put her chest right in my face. Her breasts were undoubtedly firm to the touch and her nipples erect. I then stopped my forward motion and stood still. Cassie eased up her grip on my head and fell back a bit so her breasts were no longer touching my face.

I looked up and laughed while Cassie too looked down with a smile. I eased off on my grip and let her slide down my body so she was touching with her feet. During the motion my now rock hard penis had come in brief contact with her vagina and it was now poking into her stomach. Cassie reached into the water and gave my penis a few slow strokes. We had officially crossed the line at that point. Although I knew the stuff leading up to this moment would not be accepted by neither my wife or John.

She continued to slowly stroke me and then looked up and said "Wanna get in the hot tub?"

I replied with a frog in my throat "Suuure."

She lead the way towards the ladder, out of the pool and towards the hot tub which was about 15 feet from the pool along the wall of the house. "Can you take the cover off and I'll grab more beer?". I just nodded and took off the cover and stepped down into the tub and sat so I was facing the fridge. I watched with great pleasure as she bent down and grabbed 2 cans of beer as from my view point the bottles were gone. She turned and walked back with a can in each hand. My erection had lessened while I had removed the cover and got in the tub but now as I watched Cassie walk towards me dripping wet, I was back to full blown hard on.

Cassie handed me the beer and stepped in and right beside me in the tub. My arms were planted, spread out and back along the top of the tub. When she sat beside me my one arm was around her head so she was nuzzled in nice and close. She drank with her left hand and me with my right. After a few sips of our drinks I felt her move slightly and then felt her hand on my rigid penis. She slowly stroked the entire length of my shaft and even lightly stroked the head with her fingertips before heading back down my shaft. I was wide eyed as she stroked me and continued to take sips of my beer as did she.

The slow stroking continued for several minutes and not a word was said. Because she was so gentle with her actions I wasn't fearful of cumming any time soon although I was very much enjoying the stimulation. Cassie either finished her beer or had had enough as she placed it up on the deck and put her other hand back in the water. Next I felt her move slightly away from me but then I realized why. She now had both hands fondling my private area as her other hand was cupping my balls. I slouched down a bit so I was near the edge of the seat and spread my legs to give her better access. She seemed to agree as she let out a soft moan.

After a few more minutes of slow stroking Cassie again shifted in the tub and positioned herself so she was almost facing me. The stroking continued but with a more aggressive attack. I reached my own hand out and now was massaging her right breast. Cassie began to moan quietly but she continued her actions under the water. Easily 10 minutes had gone by since the handjob had started and still not a word had been said. I felt I needed to say something but in my aroused state I couldn't think of anything other than to moan myself.