My Second Chance at Happiness

This story may contain:

M/F, F/F, M/M, THREESOMES, GROUP, SWINGING

ALL characters are clean and safe

Prologue -

It's been several years since my lovely wife passed. I have been able to survive but lately my mind keeps going back to the love we shared, as well as the great sex we had. This story is how I got a second chance at happiness...

I don't know why but I was bored and as a lark I put an ad in the local personals for a mature, attractive woman, 40 - 60, to man scape my privates, something my wife did religiously every week and after she did me, I did her private area. It was something we enjoyed doing as husband and wife, especially when we were going to visit a clothing optional resort or have special company over.

Two weeks went by before I surprisingly got a response...

The Story -

I got an email from a woman named Connie. She said she found my ad interesting. She even sent a picture of herself. From her picture I was guessing she.just be in her late 40's with dirty blonde hair. As I read further, She said she was 50 and she also said she might be interested in helping me out and if I was serious to send her more details.

I was surprised at first but I quickly replied, "Connie, first I want to thank you for your reply. I also want to thank you for your picture. You certainly are very attractive.

My name is John. I am 60 years old, 5'8", 170, s/p brown hair, hazel eyes, and am a widower. My late wife and I always trimmed our privates...it was something we enjoyed doing together and lately I have missed it more and more. So, I was hoping I could find a woman who would help me so I can again visit clothing optional resorts like my wife and I used to.

Please let me know if you are interested.

I have enclosed a picture of myself.

Thanks, John"

That night I got a reply from Connie. "John, Thank you for your reply. I thought about your request and I would consider helping you out but first we would have to meet to see if we are compatible. You see, I have been a widow for a few years and feel it's now time for me to experience life again. By the way, I liked your picture. 🙂

Hope that helps.

Connie"

I replied that same night. "Connie, I understand you completely. If you like, we can go out to dinner one night, my treat of course. Please let me know if you have a favorite restaurant. I like Italian, seafood and steak. Also, I live near the Empire City Casino. I am free whatever day you choose...just let me know

John"

It was almost midnight when I got her reply. "John, I like the same as you. How about we go to the steakhouse near you for dinner tomorrow night, say 6:00 p.m.?

Connie"

I replied, "Connie, Sounds great. We can meet inside. I will be wearing jeans, sport shirt and a tan jacket.

John"

"John, okay. I'll be wearing jeans and a black blouse. See you tomorrow.

Connie"

Wow! That night I could barely sleep. I was nervous as all hell. I think I just about got an hours sleep. It was about 7:30 a.m. when I got out of bed. I showered and laid out what I was going to wear that night, nothing fancy for sure. During the day I ran some errands and got home in time to shave and take another shower.

Since the restaurant was close by, I left my house at 5:30 p.m. and arrived at 5:45 p.m. I went inside and asked for a booth. I told the hostess I was waiting for a female friend whom I described and then went to the booth. I sat facing the restaurant's entrance do I could spot Connie when she came in.

At six on the dot I saw Connie enter. The hostess brought her over to me. I got up and introduced myself as she introduced herself and then we both sat down. I ordered some wine and I started the conversation.

"Connie, you are more beautiful in person."

"Thank you John. And, thanks for your picture. So tell me all about yourself, good and bad." As she laughed.

"Well, you know I am a widower and that I'm 60. My wife and I used to go to clothing optional resorts as often as we could. We made some good friends at the resorts."

"How good?"

"Do you really want to know?"

"Yes. Tell me everything."

"Ok. My wife and I, from the day we were married we agreed to experience as much in life as possible and that included sex. We loved each other immensely but when it came to sex, we agreed to enjoy it all, without any regrets or judgement. So, that being said, if we met someone or a couple, and we got along, we would have sex with them, together or one on one."

"So, you and your wife were swingers?"

"Not exactly, but we did enjoy others and became good friends with some of them. Does that shock you?"

"Not really. You see, I must confess that my husband and I were swingers and that is one of the things that I miss the most...we loved sex, probably as much as you and your wife. Does that shock you?"

"Well, it does a little, but it is a pleasant surprise. To be perfectly honest, I would love to take you to a clothing optional resort some time. I think you would enjoy it."

"I might take you up on that. Now, getting back to your ad...What did you want, specifically?"

"I was looking for a woman to come to my house and man scape my cock, balls and pubic area, maybe on a regular basis."

"That's a possibility, but what do I get out of it?"

"What do you have in mind?"

"Hmmm. Would it be too forward of me to ask for a good fucking once I finished trimming your privates?"

"I think that could be arranged. Let's finish our dinner first." I said laughing "Oh, by the way, I love your blouse."

She looked down and noticed her nipples were pushing out and that I could see the outlines.

She smiled and said, "Thank you. I was going to wear my white blouse but I didn't want to be too forward." And she laughed.

We finally finished our dinner and I asked Connie if she wanted to come to my house and she said yes. She followed me in her car and when we got to my house and I put my car in the garage and she parked in the driveway. We went into the house and I gave her a quick tour. She sat in the den as I poured us some wine.

We talked some more and she finally said, "John, why not show me what I have to work with?"

I got up from the sofa and, not being shy, undressed until my cock and balls were out for her to see By now my cock was semi erect.

"Mmmm, it looks like I will have some work to do. You have a nice package. Shall we get started?"

I took her to my bedroom where I had all that she would need to do her job. I got on the bed as she directed and waited for her to start. Just as she was ready to start, she smiled and started removing her jeans and blouse then her thong. She was completely naked now. It was them that I saw that she was completely smooth.

Then she smiled and said, "I feel more relaxed if I were naked like you while I'm trimming you. That ok?"

"It sure is. Boy, you are beautiful."

For about an hour she trimmed and cut and smoothed every inch of my pubic area until my balls and shaft were completely smooth and the hair around my cock was short and trim which made my cock look much bigger.

When she finished, she cleaned up everything and I was as proud as could be. I got up and hugged and kissed and thanked her.

She smiled and said, "Ok. Now fuck me."

We got on the bed and she wasted no time in spreading her legs. My hard cock easily slipped into her wet cunt and my cock went in as far as it would go.

"Fuck me John. Fuck me hard. It's been a long."

I wasted no time and fucked her as fast and as hard as I could when I finally shot my cum into her cunt. As I was still cumming in her she was still bucking her hips trying to get more cum out of me. After awhile we both calmed down as we hugged and kissed.

"John, that was terrific. I would love to make this a regular thing, if you want?"

"How about tomorrow night? You can come for dinner and we can get to know each other."

"That sounds good. What time?"

"How about 6:00?"

"That's ok with me."

We fucked again before she had to leave.

The next day I went shopping for dinner. I was going to make a small roast and even bake a pie for dessert.

I had everything ready..the roast was in the oven, the pie was cooling and the table set and wine chilled.

Finally, the doorbell rang and it was Connie. I gave her a hug and a light kiss and we sat in the kitchen so I could watch over my dinner cooking.

"I'm glad you came Connie. I was looking forward to tonight."

"Me too, John. Everything smells so good."

We had some time before dinner so we chatted. We found that we had a lot in common besides sex.

"So John, do you still ever meet with your special friends?"

"No, not really. Things changed after my wife passed. What about you? You don't swing anymore?"

"To tell you the truth John, I do miss it. After last night I think I want to get back into it."

"Hmmmm. Look, I have an idea. I wouldn't mind getting into it as well. Maybe we can team up? Would you be interested?"

Smiling, she said, "John, that's all I was thinking about after I left you last night. I'm interested and was hoping you would be too."

"Connie, let me make some calls to some of my special friends to see if we could connect and you could do the same."

"Ok, I'll make some calls as soon as I can. By the way, I would like to go to a clothing optional resort with you. I want to show off the work I did on you yesterday." She laughed.

"How about tomorrow. The ride is only an hour away. We could stay the weekend and maybe we can connect. Oh, one other thing, I have videos on my phone of some of the encounters my wife and I did if you care to see them."

"I would love to see them right after we have your delicious dinner "

Dinner was ready and it came out terrific.

We finished and I cleaned up while Connie watched my videos.

Soon, we were on the couch together.

"John, the videos were terrific. Your wife was beautiful and so sexy. You should be so proud of her. There was one video that was amazing though...the guy with a huge cock fucking her. I could watch your wife fucking him all day. "

"Yeah, that was a great night. I just watched as he got his huge cock in her and fucked her. That was my friend Tom. We still talk to each other every now and then. Did you want to meet him?" I said laughing.

"I'm glad you have his number." As she laughed.

I then leaned over and kissed her. My hands roaming over her clothed body. Our tongues entwined. Her hand rubbing my hard cock through my jeans. Suddenly she started undoing my pants until my erect cock sprang out. She wasted no time in devouring my cock with her mouth, sucking and licking my entire shaft.

"Easy baby or I'll cum."

She looked up at me and smiled and said, "Let me taste your cum now."

A few more sucks and my cock exploded and my cum spurted I to her mouth until I was drained. She quickly kissed me, sharing my cum.

"Why don't we go to my bedroom Connie?"

We got up and both got completely naked and got on the bed. We just cuddled together, feeling our warm nakedness.

"I'm sure glad you answered my ad Connie."

"Not as glad as I am for you placing it. I can't believe how much I missed all this and am really looking forward to moving on with you."

"Same here Connie. The one thing I loved more than anything was watching my wife taking another guys cock in her cunt. Watching a strangers cock sliding in and out of her cunt and then filling it with his cum was indescribable. All of which she did knowing how much I loved seeing her doing it."

"Yes, I know what you mean. I loved watching my husband fucking another woman and cumming in her. Do you think we will get lucky tomorrow?"

I laughed and said, "I'll see what I could do. Now let's fuck."

And fuck we did. I lost track of the number of times my cock was in her cunt throughout the night.

The morning came and after we woke up, fucked then headed to the shower and finally had breakfast.

It was mid morning when we headed to the resort. An hours drive later we were there. We checked in and went to our cabin and got undressed and started walking the trails.

"So Connie, how do you feel?"

"This is terrific. I love the freedom of no clothes and the looks I am getting. I hope we can connect."

I laughed as we walked. We eventually wound up at the pool which wasn't crowded. We found a couple of lounges and laid down. Connie got a lot of looks by passersby, some saying hello to us. There was one woman, an attractive red head who stopped in front of us.

"Hi, my name is Ronda. My husband and I live here at the resort. Are you new here?"

"Hello. My name is John and this is Connie. We are up here for the weekend. This is Connie's first time at a clothing optional resort."

"Oh, how wonderful. Connie, you will love it here. If you two aren't doing anything for dinner, we would love to have you join me and my husband.

I looked at Connie and she smiled and I replied, "It looks like we will accept your generous offer. Thank you "

"Our place is down the next street on the right, number 10. Come around 5 so we can chat before dinner. See you later."

Connie looked at me and said, "What do you think?"

"It's a possibility but who knows...we will see."

A short time later we left the pool and headed back to the cabin we rented for the weekend. Connie was all over me and we fucked. We then showered and headed over to Ronda's place. We rang the bell and Ronda let us in. She introduced us to her husband, Mike and he welcomed us inside.

As we sat I figured that they were in their forties or early fifties. Ronda was about 5'6", maybe 125, nice full tits and big nipples. Mike had to be about 5'9", maybe 180 or 190, nice big cock and balls. He was perfectly smooth. Ronda had a red landing strip.

We chatted and then Mike said, "Connie, I like your smoothness. I have asked Ronda to go smooth but she likes to show off her red patch." As we all laughed.

Mike then got up and he brought in some steaks from the grill which we thoroughly enjoyed.

After dinner, we again chatted and this time it was Ronda who said, "I just wanted to say that as soon as I saw you two, I knew there might be a connection between us. Look, if you are not interested, we understand, but we were hoping you might be."

I looked at Connie and replied, "One of the reasons we came up here today was to see if we could connect with a couple. You see, we were swingers but have been inactive for awhile and we wanted to get back into it."

Mike stopped me and said, "If you want to swing, that's terrific. We have some friends here that swing, like us. We could introduce you to them and maybe we can get together for a nice time, if you want "

"We would like that."

Ronda excused herself and came back a few minutes later and said, "I made some calls but none of our friends are able to come over now. But one couple can come over tomorrow."

I looked at Connie and she smiled.

Then I saw Mike get closer to Connie. I watched as Mike started kissing Connie and Connie returning his kisses. His hands roamed all over her body. Her hands moved down to his erect cock, fondling it. She started jerking him off when Ronda came to me and sat besides me and kissed me. Her hands quickly found my hard cock. From the corner of my eye I saw Connie look over at me and smiled as she moved her mouth down to Mike's cock. I watched as she sucked his hard cock.

As Connie was busy with Mike, Ronda and I got on the shaggy rug and I mounted her. She grabbed my cock and practically shoved it into her cunt, moaning as it slipped in. "Mike, Mike, his cock feels so nice in me."

Mike answered, "Make him cum in you baby do I can suck his cum from your cunt."

A few hard strokes and I shot my cum into Ronda's cunt. As soon as I came Mike moved his mouth to her cunt and lapped up my cum. He then quickly moved his mouth to Connie's mouth and kissed her, sharing my cum with her. When he finished, he laid Connie on the floor next to Ronda and quickly got his cock in her cunt and started fucking her.

It wasn't long before I watched Connie's body arching up with every one of Mike's thrusts. Soon Mike yelled out that he was going to cum. I could see his body tensing up and his balls ready to explode and then he shot his cum into her cunt. They both laid there exhausted with his cum oozing out her cunt.

I said, "Hey guys, that was amazing. You two are terrific."

Ronda replied, "You and Connie were terrific. Weren't they Mike?"

"Yes, they were. I must say to Connie that she was a great fuck and I would love to fuck her forever."

Ronda said, "John, why don't you and Connie stay over tonight?"

I looked at Connie and she replied, "I am sure John and I would love to stay over."

I smiled and shook my head yes and smiled.

We all rested awhile and had some wine. As we sipped our wine, Ronda came over to Connie and whispered something in her ear. I saw Connie smile as Ronda sat besides her. In seconds they were locked in an embrace and kissing. Their tits pressed together...their hands all over each other. Mike and I watched them and then I could feel Mike's hands on my cock and balls. I looked at him and spread my legs a bit and he moved his mouth to my cock. In seconds my cock was in his mouth. I automatically moved my hand to his cock and started jerking it off.

Suddenly the girls were kneeling in front of us. Ronda started sucking my cock as Connie started sucking Mike's cock. Then they kept switching over to each of our cocks. In a short time Mike and I were both ready to cum and then our cocks spurted out or cum all over their faces and tits. I lapped up Mike's cum from Connie and Mike lapped up my cum from Ronda.

We all laughed and rested.

That night we all fucked and sucked each other and by morning we were all covered in dried cum and juices. I woke up to see Connie on all fours with Mike's cock in her ass and Ronda underneath Connie eating her out. I watched her tits swaying with each of his thrusts. It was amazing to watch. Then Connie noticed I was watching and gave me a big smile and then she started moaning as he filled her ass with his cum. with my cock still in Ronda's cunt.

Eventually we got up and continued where we left off. After our morning fuck session, we showered, me and Ronda and Mike and Connie, then we had breakfast.

We discussed last night and Ronda asked, "So, are you two glad you got back into swinging?"

I responded, "To be honest, yes. I really missed all that fun."

Connie added, "Yes. And I am so glad that Ronda found us. That was the best time I've had in a long fucking time."

Then Ronda said, "Our friends are coming over later this afternoon.They are Carol and David. They are in their 30's and boy can they fuck."

Ronda then said, "If you guys want we can spend time by the pool or we can take a walk around the resort...your choice."

Connie replied, "If it's ok with you guys, I would like to spend time at the pool."

So we agreed on going to the pool.

We cleaned up and headed to the pool.

We found four lounges and Mike and Connie sat next to each other and Ronda sat next to me.

People passing by would say hello or some would stop by and talk to Mike or Ronda.

One middle aged couple who was passing by said, "Ronda, Are your friends swingers?"

Ronda replied, "Yes, they are. Why, do you want to fuck them?"

"We wouldn't mind." Then they went on their way.

Connie and I just laughed.

I then said, "It seems like people know you guys."

Mike said, "Yes. We don't hide it that we are swingers. We should be going soon. Our friends will be over soon and we should get ready.

I said, "I'm looking forward to it."

Connie smiled and said, "Me too and I want to thank John and you guys for the greatest time I've had in a long time and can't wait to continue swinging."