I’ve been posting several of my stories which I decided to share after I found them in my journal. Having written them a while ago and having taken place over several years, I had to clean them up a bit and try to make sense of them. It is different writing for a personal journal than it is for people to read. The funny thing is that half the time I couldn’t remember these situations and half way through the memories were coming like a tidal wave. Just remember that they aren’t all in the chronological order of which they occurred.
During the summer Cindy, my wife, would go to the beach as often as she could. I on the other hand was not a fan of the heat, sun, and did I mention heat. During these days she would usually go with her friends and I would do my own things … work, play, rest.
One Saturday after a long day of watching TV and channel surfing, Cindy came home from the beach one of the guys who went, a friend of a friend, was making passes at her and trying to be touchy and flirtatious in the water.
She could see that I was anxious and I asked her if anything happened. She looked at me and said she. We talked about how our days went so far and she confessed that wouldn’t let anything happen unless we talked about it. At that moment I wasn’t sure how to bring up the fact that I would have loved her to have done something without me knowing and then telling me about it … but it would defeat the purpose if I told her to do it. Later that evening I brought up the subject about the guy again and she ended up asking me if I would have been upset had something happened. I tried to play it down by saying it might have bothered me but at the same time it would have been exciting.
A few weeks later she was invited with some of her friends from work out on a boat. I knew most of the people going … Karen & Andy, Paula & Jorge, and another guy named Jorge. The only one I didn’t know was the owner of the boat Ralph which I found out was the guy who was flirting with her at the beach. My mind was racing with possibilities.
I knew that Karen and Paula were close friends of Cindy and they spent most of their time at Happy Hours and hitting on other men despite both of them being married. They are both in their mid to upper 40’s and their husbands slightly older. Jorge M. was a single man in his early 50’s, recently divorced and going through a late mid-life crisis. He is actually a very nice guy but we always suspected he was gay. The last guy, Ralph, was also in his late 40’s but looked older. He was Paula’s friend. Out of all of them, Cindy was by far the youngest at a recently turned 25.
I also knew that Paula and Karen always tried to set Cindy up with other guys even while we were engaged telling her that it wasn’t done until she said ‘I do’ and then she had to just be extra careful. You get the idea. Of course Cindy never shared with them that she had already been with other guys with my approval.
Anyways, I told Cindy it would be fun and to let them know we would go. When Saturday came around I put on my best ‘sick’ performance to date. I kept running to the bathroom throughout the night and in the morning told her I just couldn’t go but told her to go ahead since everyone was expecting us. She made sure I had everything I needed and even went so far as to call her sister to check up on me later.
Off she went ….
As the day went on I must have played with myself half a dozen times in anticipation but in all honesty expecting nothing to happen. I’ve been through these situations a few other time and they always proved more wishful thinking than reality … but a man can dream can’t he.
The phone rang around 6pm and it was Cindy. They had just dropped Karen and Andy at home and now they were headed to Paula’s house to pick up her car and head home. I talked to her briefly about how everyone enjoyed it and all she could talk about was how nice the boat was. Some women love cards … mine really loves boats.
It was now 8pm she wasn’t home yet but I figured they were probably all just chatting away so I decided to give her a call … no answer. I tried again a few minutes later and still no answer.
By 8:45pm I gave her cell phone another try. I looked up Paula’s phone and called the house but no one answered. In all honesty I’m one of those worry warts that always imagines the worst and I was beginning down that road. I even called Karen and she said that they were dropped off quite a bit ago and that Cindy and the rest were headed to Paula’s house.
I jumped in the car and left to make sure she wasn’t in an accident. Paula doesn’t live more than 15 minutes away. I followed the path Cindy would’ve taken and when I arrived at Paula’s house I saw everyone’s cars in the front. At that point my anxiety peaked and a rush of adrenaline and excitement coursed through me. ‘Could it be happening???’
I rushed home, changed, got into bed and tried to watch TV to not think about it. I couldn’t believe how excited I was getting.
Sometime after 10pm she called me on the phone and said she was sorry for not calling earlier but they ended up picking up some Mc Donald’s on the way and spent the rest of the time eating and talking. She had seen I called just now when she left but had left the cell phone in the car. My excitement was slowly waning as I realized her story made perfect sense … damn it!!
When she arrived, she walked right into the bedroom wearing only her bikini. It wasn’t one of the thong bikinis as she was fairly conservative when it came to her bathing suits, but it still made her look incredible. She walked right to the bed and laid next to me as I muted the TV and turned to give her a kiss hello. She pressed herself against me and, holding my neck and head, made out with me like we were newly weds.
She took my hand and placed it between her legs as she pulled the bikini to the side. She was so wet. I guess she must have had a great conversation with Paula and Jorge. She asked me if I wanted to fuck and I just nodded. Then she told me she ‘just did’. I didn’t catch it off the bat but as she said, ‘did it twice’ my jaw just about dropped.
I jumped on top of her ready to fuck but she pushed me off and told me that I had to wait if I wanted to know what happened. ?
After I plopped next to her she began to tell me the entire story and I kept interrupting asking for the details. Why can’t women understand that we need the details? The entire time she told me what happened she was stroking my cock and stopping just before I came and then started again. What a build up.
HER STORY ------------------------
In the morning she went to Paula’s house where Jorge was already waiting. From there the four of them went to pick up Karen and Andy. Jorge M. was going to meet them at the Marina.
Once they were out on the boat, the morning just went by. All of them were drinking and sharing stories. Paula decided to be topless to make sure she had a perfect tan. Not too long afterwards, Karen joined her and suggested for Cindy to do it but she declined. They kept telling her it was just them and it wasn’t like any of them, being doctors and therapists, hadn’t seen them before. But still she didn’t feel comfortable with the husbands, Jorge M. and Ralph there.
After lunch, Ralph started to make Margaritas for everyone. I’m not too familiar with boats but apparently this one had a small cabin down below but only room for a couple of people. It was mostly storage and one side bunk to sit or rest. Jorge M. was in the water walking on the sand bar (this is where the boat was anchored).
While everyone was doing their own thing, Paula pulled Cindy over and told her she thought Ralph liked her. Cindy laughed and said she noticed it too. Paula just laughed and winked a few times to egg her on.
While they were enjoying the Margaritas, the all began to talk about their past most embarrassing sexual moments. Then they talked about their best moments. Apparently most of them had previously experienced threesomes and exhibitionist moments. Cindy told me she was tempted to tell them about Rick and Chris but chickened out at the last moment.
Paula walked up behind Cindy and pulled her neck strap, exposing one breast to everyone. Cindy quickly covered it. Karen and Paula were both teasing her about being shy since neither of them had their tops on. Ralph made a comment about how could she just show one and not the other … he considered her a tease and laughed. Between all them joking around the few drinks in her, she ended up taking her top off. That was a first for her.
Ralph pretty much sat or laid next to her the entire time always glancing at her without being too obvious but she caught him most of the times and it made her excited.
Karen and Andy had disappeared onto the sandbar and drifted off for some privacy. Jorge M. was in the cabin taking a nap on the bunk. Paula and Jorge were at the front of the boat, laying down and making out. Cindy felt a little uncomfortable standing in the back of the boat watching those two with Ralph standing next to her watching the same thing, but neither moved.
They took off to another spot. Everyone was at the front of the boat sitting down and enjoying the wind and waves. Paula had gone to the back to get some water for her, Andy and Cindy. When she came back she had forgotten Cindy’s water and Karen said she had wanted some too. Cindy jumped up to get her water and Karen’s. *** Cindy found out later from Paula that Ralph had told her to do it to get Cindy back there. ***
Cindy got the waters from the back cooler and as she walked past Ralph he asked her if she wanted to steer for a bit. She leaped at the opportunity and quickly gave Karen her water and returned. I swear if this wasn’t such an obvious plot, I don’t know what it was. Cindy stood at the wheel and Ralph right behind her with his hands on her hands. He wasn’t being discreet about his erection at all. She said every time the boat hit a small wave he would exaggerate the bounce and push against her.
As Cindy drove the boat, Ralph began to place his hands on her sides and move them across her stomach and up the sides. From the front of the boat you could only see their shoulders, resolving Cindy’s main concern. Once he didn’t sense any resistance, he moved up and slid under her bikini top, pushing it over her breast. She was stunned at how he was just squeezing her tits as she watched everyone in the front of the boat. Every once in a while, someone would look back and just smile, oblivious to what he was doing to her.
Then he stood up against her and put her hand on his shorts and she rubbed him for a while. Supposedly he either already came or had a great deal of pre-cum because his shorts were pretty wet. At one point he pulled them down and was gyrating into her from behind.
This quickly stopped when Jorge M. started to come to the back to get a drink and ended up standing next to them to chat. Cindy left Ralph and went to the front of the boat.
The trip ended and they had just dropped off Karen and Andy when she called me. They did stop at McDonalds and ate when they got to Paula’s house. After eating, they were sitting around talking in the living room and Paula went to get some aloe. Cindy joined her. This is when Paula asked her if anything happened and told Cindy what Ralph asked her to do to get Cindy to go to the back.
Cindy had to confess at that point that they fondled each other but that was it. Paula asked her why she didn’t take advantage now to do more and Cindy smiled but nodded no. Paula kept telling her she should since this was a perfect time. Cindy pretended to be shocked by the whole thing and acted as if she felt guilty. Paula apparently didn’t care because she started telling Cindy about two of her friends who had slept with Ralph and both gave him 5 out of 5 stars (I guess their version of a little black book). Cindy laughed but didn’t say anything. Paula then told her she would have to take things into her own hands and Cindy started to get nervous about what she might do but Paula was already out the bathroom and heading down the hall.
When they returned to the living room, they all talked about stupid things. Cindy says she could see Paula whisper things into Jorge’s ear whenever no one was looking. About 8:00pm she looked at the watch and started to get up. Paula got up quickly and offered everyone some left over ice cream cake. Cindy said she had to get going and that is when everyone piped in with the usual, ‘come-on … just stay a few more minutes. Just a little ice cream.’ Paula went to the kitchen and asked Jorge to give her a hand. Cindy started to head to the kitchen too and Paula just shooed her away laughingly. Cindy sat back on the couch next to Ralph and they started to talk about his job.
Paula and Jorge brought out the ice cream. After everyone was done Cindy took the dishes to the kitchen and started to wash them when Ralph came in and asked if she needed a hand. She was almost done rinsing them and putting them in the dishwasher as he just watched. She thought he was going to make a move on her but didn’t even try. When she was done they both walked past the dining room into the living room and stood there as Paula and Jorge were both groping each other without a care.
Cindy had never seen Paula and Jorge going at it like this and the fact that Ralph was right next to her made it even stranger. They just watched as Jorge slid his shorts just low enough to let Paula reach down and stroke him. Jorge just stared at Cindy as Paula hunched over and began to give him a blow job. Then she knelt on the floor in front of him to get a better position and Jorge continued to look at Cindy and smile.
She was so fixated on Jorge and Paula, she didn’t even realize Ralph had moved behind her. That is when Cindy felt his hands on her shoulders and he began to kiss her neck. He nibbled on her ear and blew as he worked his hands around her and cupped her breasts. Her hands reached behind her and rubbed his thighs. Then she felt his fingers on the sides of her shorts slowly working them down. She didn’t move. Ralph began to caress her ass pushing the bikini bottom aside as he slid between her cheeks and reached the front. He had one hand on her ass and one on her breast.
Then he lifted her shirt off and untied the back of her bikini top exposing her breasts to Jorge. Ralph just caressed them from behind as Cindy and Jorge kept looking at each other.
She watched Jorge toss Paula on the couch and remove her shorts and bathing suit bottom as he climbed on top of her. Jorge was hovering over Paula, her legs spread around him and the entire time he was pumping her, he just looked at Cindy. Cindy said she just didn’t feel embarrassed anymore and she leaned down to remove her bikini bottom actually feeling aroused exposing herself to Jorge, who for a much older man, she said, was quite impressive.
Ralph pulled her into the dining room and against the wall. She admits that she wanted to keep watching the other two but wanted to fuck so badly she could hardly wait. Ralph didn’t waste any time. As she stood against the wall, he knelt down and began to eat her out and then finger her. She could hear the sounds from the next room … Paula’s moans. This gave her the confidence she needed to let out her own sighs and moans. (I had to get this detail out of her myself).
He took her to the floor and as she lay there, he took off his clothes.
She says his cock was average and bit thicker but never got completely hard. He got in front of her and continued to eat her out and then placed himself on top of her so she could suck his cock, the classic 69.
Then he pulled out a chair and had her kneel over it so he could doggy style her. He just started to fuck her from behind when she realized he never put on a condom. She freaked out and told him to put one on but he didn’t have one. She stopped him and said she didn’t want to without a condom … she even told him that she didn’t know him that well and apologized. He ended up fingering her for a while and having her give him a blow job.
He kept eating her out and stroking his cock against her and it was killing her. She finally caved in and walked to the living room to ask Paula for a condom. When she walked in, Paula was bent over the couch with Jorge doing her from behind. Both of them now completely naked and Paula grunting louder.
Paula turned around to look at Cindy and said, ‘having fun!!’. Cindy asked her for a condom and Jorge told her to look in his bedroom in one of his drawers. Cindy said Jorge began to thrust hard and Paula just buried her head into the couch with her hands gripping the cushions. Before she turned around, Jorge turned his head and met her eyes. He never smiled and caught her off guard because he mouthed the words, ‘I want to fuck you’ and narrowed his eyes like he was already doing it. That is when I said my little comment about, ‘no shit … you are half his age and who wouldn’t.’
She ran to the bedroom and found them. When she ran into the hallway, Ralph was there and he picked her up … kissing her and taking her to the bed. He dropped her down and Cindy ripped the condom pack, slipped it on him, and leaned back. Ralph jumped right on her and they fucked. She says they never changed positions and her kept going for a good 20 minutes. She says she kept switching between thinking of Ralph and then imagining Jorge … although she never thought of him in that way before.
When it was over, they walked to the dining room and got their clothes on. She couldn’t really hear Paula and Jorge but as they headed to the entrance of the house, she could hear sounds from the guest bedroom. As she walked past it, the happy couple were still at it … or at least at it again.
Ralph walked Cindy to her car. When she got in, he leaned down to give her a kiss they started to make out again. She said before she knew it, he was folding her breasts. He tried to pull her to get out of the car but she said no, she really had to leave … but he continued to kiss her. He started to tell her how much he wanted to have her again and she resisted insisting she really had to leave. Then he began to rub her on the outside between her legs and it didn’t take long for her to get out of the car, leaving the door wide open, and go back inside the house.
He took her to the couch and they both took their clothes off. Ralph went down on her again (which he apparently loves to do) and squeeze her ass at the edge of the couch. Half way into it she said she noticed Jorge walking into the kitchen completely naked and looking at her and Ralph … and then disappear behind the wall.
Ralph slid up on top of her and started to push into her much harder than the first time … she loved it. He turned her over and did the same from behind while pulling her towards him by the hips. He was trying as hard as he could and she wanted more. She admitted to even let out loud moans not caring who heard.
When he spun her around and was ready to go inside again, she realized through the excitement that once again, he didn’t have a condom. She almost let him continue but she said she remembered our promise and she plopped off the couch and told him to wait one second while she got another condom. He apologized and sat on the couch and said to hurry.
She walked quickly down the hall, past the guest room and peaked in. Paula was laying on the bed resting and maybe even sleeping and Jorge was softly running his fingers up and down her back. She went into the master bedroom and retrieved another condom from the drawer.
As she walked back down the corridor, Jorge walked outside the room and walked towards her. He stopped and mentioned he had to use the bathroom. He then grabbed her hand, the one with the condom, lifted it up as if to look at it and snickered. ‘I’m glad someone is putting them to use.’ Cindy smiled and said she felt a little intimidated with Jorge and her being completely naked in front of each other.
When he let go of her hand he just barely brushed his hand down her shoulder over her breast and down her waist and made a mmmm..mmmm sound. She got a little nervous and continued past him but having to brush her whole side against him he just stood there.
Back in the living room, she climbed on top of Ralph on the couch and rode him for while. The back of the couch faces the entrance to the dining room and that is where Jorge stood the entire time watching her. She actually loved it. Jorge was touching himself and mouthing some things to her but she couldn’t make them out.
Ralph even made a motion as if to change position but she kept riding faster to stay there. He finally picked her up and reversed it … her legs on his shoulder and his cock all the way inside of her. She had already cum and was just waiting for him to and finally he did. It was amazing she said and the fact that someone was watching her made it even better. Now she thinks she likes to have other people watch… hahaha.
She knew it was getting late and quickly got dressed, said goodbye to Ralph and yelled to Jorge but didn’t actually want to go to him just incase he wanted something else.
BACK AT HOME -----------------
Then she told me was sorry that Ralph didn’t use a condom most of the second time and didn’t realize it. As awful as I feel for saying it, it turned me on. She never forgot to wear one with people she didn’t know ever since, but for that one time it really raised the excitement level.
I asked her if she really thought Jorge would try something and she said she didn’t know but regardless of how ‘wild’ Paula is, she is a super jealous woman when it comes to her husband. Never makes any sense to me how she could have sex in front of others but freak out if her husband flirts.
We made love once that night that lasted quite a while and talked about her night the entire time. She never hooked up with Ralph again but it didn’t stop Paula from trying to keep setting her up with other guys. Maybe if she knew we already did, she wouldn’t try so hard.
