Date Night 52

My wife, Michelle, and I have had a wonderful marriage with great kids. As we approached our late-30s we were feeling like things were getting stagnant for us. We have always like watching adult videos together and with the internet they are so easy to find and the content so vast that we easily found ideas to spice things up for us. This is how we got into swinging.

On one of the adult video sites we were watching we noticed there was a chat area. Michelle logged in to see what it was all about. Well, the guys in there must not be used to a woman chatting there because she was inundated with requests to chat. I encouraged her to pick someone she thought would be worthwhile. After a number of tries chatting with guys who were way too quick to get her to talk dirty, we found a young guy (or so he said) who seemed to be pretty respectful. I enjoyed as Michelle chatted with this man, Alex. The conversation did turn sexual and Michelle was really getting into it, touching herself and telling Alex what she was doing as she masturbated. Alex was doing the same and he said he shot a huge load of cum while Michelle was orgasming herself.

Over the next few weeks Michelle and Alex chatted more and had more cybersex. I was there for some of the encounters (which I found incredibly hot) and was not there for others. Michelle told me she found both ways to be hot - with me there watching and doing it alone. Michelle told Alex that I was watching her and he was okay with that. He said he liked the idea. After 3 or 4 weeks we exchanged email addresses and pictures. During this emailing back and forth we learned that we only live about 4 hours from each other.

Alex is 25, about 6'0" tall with a great, muscular build - I guess he played college football at a small school. He has short blonde hair and the steel gray eyes. Michelle kept looking at his pic when they would chat and she masturbated herself to cum.

Michelle sent a couple "regular" pics to Alex, as well as a couple of racy ones. Michelle is a stunner - always has been. She is 38, but could easily pass for early-30s. She is about 5'5" tall with shoulder length dark brown hair, which is pretty straight. She has large brown eyes that I can stare into for hours. She weighs about 140 pounds, so she is in decent shape - not like athlete shape, but extremely sexy because she has curves in the right places - 34C bust and nice hips. She walks a whole lot, so she has great legs. I love a lovely lady in heels and stockings or pantyhose - I guess that's my fetish. Michelle sent Alex some sexy pics of her teasing in some revealing outfits while in stockings and different types of high heels and boots. I guess it turns out that Alex is also an aficionado of legs and heels.

After a period of time on email and chat we decided to try the phone sex route with Alex. We quickly found out how hot that could be escalated to the idea of meeting Alex.

We laid down some ground rules first. This was to be a date. I was going to be going with Michelle and escorting them on the date until she and I both felt comfortable with how things were going. If things went well, the date my progress into intimacy - but we would have to see. Alex was all gung-ho for this possibility.

We made arrangements for two weeks later. Michelle was constantly talking about it, asking me about it - what to wear, how she should act, if she should get wild with him if she likes him, etc. Michelle went shopping for a new outfit for the date - but she wouldn't let me see the outfit until the night of the date.

Two weeks later came and we had made arrangements for the kids to stay by Michelle's sister and her family. We chose to meet somewhere midway between where we and Alex live. We booked the hotel room and told him that we would pay for that, if he would pay for the food and drink. Michelle packed a few different outfits - of varying sexiness and kinkiness as well as throwing in a few of her favorite toys we had purchased over the years.

We got to the hotel early in the afternoon - much earlier than we told Alex we would be there. We parked on the opposite side, so Alex would be much less likely to follow or stalk us if we found out he was a bad match. We checked in and Michelle changed into an outfit I had seen her in many times. She told me she was saving the new outfit for the date, after we met with Alex to see if he was worth it. She put on a red silk blouse, short black skirt, and red stiletto pumps. Under the outfit was a red lace bra and matching thong. She was bare legged in this outfit. She re-did her makeup and we went to the hotel lounge and called Alex. He was just pulling in and met us in the lounge. He was the consummate gentleman. Michelle was swept off her feet and I must say that I was very impressed with him, as well. Michelle gave me a nod so I explained to him how this was going to work, since Michelle wanted to go through with the date. He was to bring his luggage to the hotel room I rented for him - which adjoined ours. He was then to meet me back in the lounge. During this time Michelle was going to change into her outfit for the date. We would then take a cab or the hotel shuttle somewhere for dinner, dancing, and drinks. Alex was agreeable to all of this.

He and went to his car to get his luggage while Michelle went to change. He and I were back in the lounge having a drink when Michelle called that she would meet us in the lobby in 5 minutes. She came off the elevator and my eyes about fell out of my head. Alex's jaw hit the floor and he smiled broadly. Michelle was wearing a red, sleeveless dress with a deep V neckline. She must had a push-up bra on as her breasts looked like there were going to explode out of the top. The dress was so short and tight that when she sat, you could see the lacy tops of the black stockings. She also was wearing a new pair of red, knee-high boots with four inch spiked heels. She definitely spent well on this outfit!

Michelle came over and basically ignored me. She took Alex by the arm and kissed his cheek. I followed out to the cab. I asked the cabbie if he would let me ride in front and take occasional video. He didn't like the idea until I offered him and extra $50. As we drove to the restaurant, I recorded on my phone. Michelle's hand was on his thigh and then his crotch. I could see the bulge in his pants expanding and expanding. He looked quite large from my angle. Michelle only teased him on the way to the restaurant.

Once inside we had a nice dinner. Michelle sat between the two of us and kept teasing us with her foot encased in those sexy boots. I could see Alex kept looking down her dress at her gorgeous breasts. My wife had gone all out for this guy. I was aroused by all of this and couldn't wait for what was coming next.

We went to a nearby bar rather than a dance club, to have some drinks. Michelle sat up on a tall bar chair and crossed her legs as she sat between the two of us. She drew plenty of looks from both men and women in the bar. She kept teasing us with her foot and eventually put her foot in Alex's lap and poked at his big hardon with the heel of her boot as she giggled.

After a few drinks and feeling good we called for a cab back to the hotel. I again tipped extra to ride in front and record the backseat action. This time they were making out. Michelle's breasts were being mauled by Alex's big hands as they kissed hungrily and tongues danced together. Michelle kept rubbing Alex's cock through his pants until I could see a little amount of pre-cum leaking through them.

Back in the hotel they walked calmly through the lobby, hand in hand. Once in the elevator they were back to making out and this time his hand was going under her dress. Michelle was moaning loudly as the elevator door opened to our floor. I opened the door for them as they entered our room. I then opened the adjoining door for Alex's room in case we needed in there. Michelle pointed me to sit in the chair by the desk in the room and told me to record this on the ipad we had brought with.

Michelle excused herself to the bathroom and told Alex to undress. He was standing there with a massive erection. He must have been close to nine inches and very thick. I admit I was jealous, as I am just average in the cock department, but am long lasting. Michelle had re-applied her lipstick and came out twirling her thong panties around her finger, smiling. She tossed them at me. I sniffed them and felt their wetness. Michelle knelt down in her boots and began stroking Alex's cock with her skilled hands. She mercilessly teased the head with her long nails, scratching it. She then kissed the head and licked the long shaft from base to tip before inhaling most of it into her mouth. Michelle has always been a deepthroat queen, but with my cock it had to be much easier than with Alex's monster dick.

Michelle looked up at him and told him that she wanted to deepthroat him but would need his help and told him to "skull fuck" her. Alex started thrusting his hips as he held my wife's head. She gagged a little but adjusted with the thrusts until her mouth was touching the hair at the base of his cock and his cum-filled balls. Michelle pulled off his cock and licked her lover's cock and smiled. Alex said he had never had a woman do that to him before. She just smiled and winked.

With that she stood up and turned to have Alex unzip her dress. My sexy wife was standing there in a black push up bra, black stockings and slutty red boots. Alex walked over to her and kissed her and grabbed those lovely breasts. He lifted each out of the cups of the bra and sucked each of them before licking and pinching them. She told him to bite them so he took a nipple between his teeth gently and pulled it out as far as he could before he let it slip from his bite - she was moaning and throwing her head back as he did this.

Michelle declared that it was now time to fuck! She pushed him back on the bed and straddled Alex. She mounted him and slid her horny, wet pussy down on his big cock. She moaned as she took all of him inside her and sat with him fully enclosed inside her. She ground against him and rocked before she got into a rhythm of sliding up and down on his pole, moaning as he would thrust up and she slammed down on him. Alex's hands went to her tits to play with them while Michelle rode - her hands in her hair, eyes closed, and unintelligible sounds coming from her mouth. I could tell that Michelle was close to an huge orgasm and I told Alex to hold on for dear life as she started to cum, writhing, and thrashing about on top of him. Suddenly I could see his body stiffen as he groaned loudly and Michelle squealed as he filled her pussy with so much cum that it started spewing out of her pussy around the base of his cock.

After they both came down from that earth-shattering cum, Michelle slid off and started licking their cum juices from the base of his cock and working her way back up to the tip. Smiling at him the whole time. I smiled at Michelle and she smiled back at me. We started laughing and both said, at the same time, that the date was a success.