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Yacht Club
Summer was over and fair weather sailors were home watching football on the television. Only serious salts, including my girl and I, were still out sailing regularly. While my girl and I had been out sailing that day, I had reflected on our relationship of the last several years.
It had started with her being a valued member of my crew, which surprised many people because she only weighed a 100 pounds at most. However, she could get her job done better than the 220 pound male mussel boys. I always smiled when she would come and do a job they could not get done. I had originally noticed that even though she was more that thirty years old, she was very modest, which can be a problem in the very close quarters of a yacht. Then a little over a year ago she and I went out to dinner alone after a yacht race.
After we finished dinner that day, we ended back at her apartment and the relationship moved to a sexual stage, but did so very strangely. She turned out the lights and made me turn my back while she got in bed under the covers. Then I was allowed to undress and join her in bed. That went on about three weeks until one night when I shot a very large load of cum into her, and that sent her running to the bathroom with her hand holding her pussy. It may sound strange and even though it was dark, that was the first time actually I saw her nude.
The next morning I told her I was sorry but I had been turned on so much by her. She shyly said that was ok, but also indicated she had never had sex anywhere but in bed, in the missionary position and her partner had a rubber. I remembered having a sinking feeling about pregnancy as I commented about how much she had been missing. She said she had long fantasized about having sex in forbidden places, and even doing a striptease or being an exhibitionist. But as she said it was all in her imagination. I stood up, gave her a hug, and after a while started to undress her standing in the middle of her living room. She objected a bit but I told her to imagine.
When she was standing there naked I gave her another hug and said keep on imagining. Then I started kissing and caressing her neck, then her breasts and as I worked my way down her body I realized her legs were spread wide and she was very, very wet. I started to finger her pussy and rub her clitoris, which turned her on even more. When I started kissing her pussy and running my tongue along her lips, she objected saying “I never . . .” but words died when I took her clitoris in mouth and she shoved her pussy hard into my face. I was eating her pussy, had two fingers of my right hand in it, and playing with clitoris with the left hand when I felt her start to cum so I worked my tongue inside and she went off. It wasn’t a quiet moan like she had always done. She was pulling my hair, her whole body was in a spasm, she was exclaiming a load “oh fuck . . .” I kept on going and so did she and orgasmed again even bigger as I worked a third finger into her pussy. I still kept on working her and she keep building to her third orgasm which had her screaming “oh fuck, fuck me hard”. I stood up, bent her over a chair and I took her from behind with her breasts cupped in my hands. She came again screaming, and yet again when I shot into her what I think was the biggest load of cum that I had ever done.
After we recovered, I got a wash cloth for her pussy and we went to the bathroom for a shower. Yes, we do it in the shower where we both came again. I cleaned her pussy for her and used her dosh bag to shoot many shots of warm water into her, which she seemed to enjoy. I then soaped her anis and inserted a finger, and used her bag to shoot warm water in her ass. As I was drying her off I rimmed her. We got dressed and we went to breakfast. Over breakfast she looked deep into her coffee cup and said I have never cum so hard, never cum so many times, never had sex so many ways or in so many places, and I think we made a beautiful mess. I reached under the table and up her skirt. She raised up, letting me take her panties off, but as I slid them down her legs she said “No not here – at least not yet.”
Since then we made love in every position, and everywhere in her apartment and my apartment, in and on our the boat and our cars, in the swimming pool and hot tub, in an elevator, in a restaurant that had dr*ped booths, in several parks, on several beaches and statues, over a cannon, on the steps of a court house, and she had even asked me to do her in a department store dressing room. It had been an interesting year having sex in all kids in non-traditional and public places. She had actually worked hard at it and had become comfortable at being publicly sexual and even with other people if there are girls doing the same thing. She had even become somewhat comfortable being undressed with others present. That was also a short while before my boat race from Santa Barbara to King Harbor in 1977, which I have written about separately. Today as we were securing the boat I was remembering how her sexuality and come from total fantasy to actual reality. It pleased me greatly and made me proud. As we were finishing buttoning up the boat, she indicated that she was feeling very bold and was even a little loose.
It was almost closing time at the yacht club, but we decided to go to the clubhouse for a drink just before we went home. Besides the bartender, the only people there were two girls sitting with their boyfriends. Other than that the place was dead. As we were sitting down at the bar, my girl ask me what is that drink you sometimes have called a Dirty something or other. I said do you mean a “Dirty Sister – Boy that would be really bold of you”. I said that “It is a drink in six parts; three parts 151 rum; two parts tequila; and one part kolua”. I ask if she wanted to try it. She said I told you I was feeling very bold, so I ordered a pair from the bartender.
While we were waiting for our drinks, I noticed that both of the girls were very both big busted and shapely, and then that all of them were in their very early twenties, which made them about fifteen years younger than us. As we got our drinks I noticed that the girls were engaged in a game of teasing their boyfriends by undoing their blouse buttons and showing off the tops of their breasts, then covering back up. One girl was very gregarious but the other seemed very shy. Then shortly latter they repeating the routine. After one routine, my girl turns to me saying I can do that too....do you want a better show. She waited until the girls started the next routine and she undid two buttons on her blouse but she left them open showing the tops of her breasts and her lace bra.
Right after I noticed my girl’s show, I could not help but notice a second person, the gregarious girl. She looks my girl in the eye and, while her friend the shy girl covers up, she smiles and undoes another one of her buttons. Not to be undone, my girl undoes two more of her blouse buttons. The other girl responds by undoing three of her buttons. As I glance over at the guys it becomes apparent from their smiles that this is all good news for us guys.
As I turned back to the gregarious girl, she is undoing the last button and pulling out her blouse. It is now open and all can see her breasts in her very sexy see through bra. As I glance back to my girl, she does the same thing but in a sexy striptease manner. I note that she too is also wearing a very sexy bra that shows off her, hard and erect, nipples. During all this, the other shy girl stays totally covered and quiet, but now begins to laugh saying to my girl, Don't take this the wrong way, but its nice to see that older gals like to play around too. My girl told her that no offense was taken, and that perhaps the boys were more interested in the bodies of you and your girlfriend because you are so much younger. The girl said. I actually think my boyfriend has a fantasy about older women.
At this point everything was interrupted by the bartender, who said I have closed and locked the door so we are the only ones left here. If you don't mind me watching, you can all continue to fool around. In fact, I'll buy the girls and their respective boyfriend a drink of their choice for any piece of clothing you girls wish to take off. With that the shy gal, stands up and boldly takes off her blouse and asks for two of those Dirty-Sister drinks you gave them. She was also wearing a very sheer bra and like her girlfriend had great nipples. As the bartender was leaving to make the drinks, the gregarious girl and my girl both take off their tops, but my girl did so in a sexy stripper style as she yelled you might as well make it 6 Dirty-Sisters because that is what we are being.
After we downed our shots, the bartender turned on some music. As we were each dancing with our respective partners, the bartender turned the lights down real low. As my girl and I danced very close she whispered in my ear, that the shy girl’s boyfriend keeps looking at me. I think that the shy girl is right about her boyfriend’s older woman fantasy and I have to say I like the thought of it. In fact, it's making me hot to think I can turn on a young guy. I'm not sure how far the two girls will go, but I'm going to take the lead and find out....
The song finished, and my girl suggested to the other girls that they go to the restroom. When they departed, we guys were left alone sitting at the bar. The shy girl’s boyfriend was first to speak. If you don't mind me saying so, your girl is very attractive and has a great body. While I would never do anything, his girl’s comment about my looking at her mom is true. While not as sexy as your girl, there are times I just fantasize about her. I told him that my girl really likes the idea of a younger guy finding her attractive, so enjoy looking. He then added that what he really liked is that both of the other girls are very playful and this seems to have had an effect on his girl. She is usually shy, so I was shocked when she was the first one to take off her top. Well guys..., I said, I think that we might very well be in for an interesting evening....
As the girls returned, it was my girl in the lead giving a thumbs up showing she was in control and said, Anyone up for another drink?... We three guys almost responded in unison, Hell yes.... Without hesitation, the three girls took off their jeans and shoes and handed them to the bartender. What a great site! The girls all wore thongs, so there three equally attractive asses were on display. As we downed our Dirty-Sisters, I could not believe my ears when the gregarious girl shouted out, I need another drink!... As I glanced at my girl, and she gave me a wink and quickly turned back to the gregarious girl saying “Let me help you with that....” As my girl faced her she slid her bra straps down, moved her arms around her and undid her bra clips. Ever so slowly, my girl brought her bra forward letting it drop to the floor.
The girls reversed roles and then just as sensually began to remove my girl's bra. As the bra was brought forward, she let her hands cup my girl's breasts for a few seconds. Two down, with what I was to find out was the best to come. My girl and the gregarious girl moved behind the shy girl. They raised her arms, undid her bra clips and each reached a hand under her bra to caress her tits. Gently, they continued her tit massage making certain that they squeezed her nipples until they were red and hard.
Without removing their hands from the shy girl, my girl said So, are you boys enjoying our little show? Would you like us to continue?... Again, as if in a chorus we responded in the affirmative. My girl then said you will all need to show us what good sports you are. We want you boys to strip to your shorts, but we don't want you to take off your own clothes. By the way bartender, this includes you as well. So, boys get to it.... My girl had this planned all out beautifully.
We looked at each other a little hesitant, but after a quick huddle, we decided the benefits would far outweigh the girls’ request. We stripped each others cloths. Now it was me who spoke. Okay you girls got what you wanted, now we expect a great show.... My girl and the gregarious girl then walked the shy girl over to a post and beam by the dance floor. With her hands still over her head and wrapped in her bra, they tied her hands to the beam. My girl said One more drink bartender... as they let her bra drop to the floor. Then they removed shy girl’s thong leaving her naked, and used her thong to blindfold her. My girl then took the gregarious girl’s tong leaving her naked. Then my girl went over to the boy friend of the shy girl and did a striptease of her thong, which was all wet from her pussy. She sat in his lap rubbed her tits in his face followed by her wet thong which she then stuffed in his mouth. Then stark naked she walked over pick her bra off the floor rubbed it on her pussy and through it to him saying you may want this a souvenir too. I was not at all disappointed in the show – And I could not help but think if they had known her a year ago. My girl and the gregarious girl began rubbing their bodies against the shy girl. They continued playing with her breasts, massaged her legs, humping themselves against her thighs. The shy girl was going crazy! She was hanging there by her arms, being teased by the two gals. The gregarious girl left for a minute, returning with a vibrator she must have had in her purse. The body rubbing continuing, the gregarious girl began working the vibrator on the shy girl's clit, then slowly inserted it. Taking it out after a bit, the shy girl screamed, For Christ's sake put it back in and fuck me already.... I think we all need a drink first..., my girl said. By this time we are really feeling the very strong booze. Since we have no clothes left to trade, we'll just have to think of something else, although I am not sure we got drinks for ever peace of clothing. Bartender, is it worth a round of drinks if we let you work the vibrator on the shy girl... Without even answering, he began to fix a round of drinks, passing them out, then bringing the drink for the shy girl to her lips.
Getting down on his knees, he began working the vibrator on the shy girl. Slowly at first, then increasing his pace, he worked the vibrator. Stopping or slowing down when he sensed that shy girl was about to cum, he kept her going for a good fifteen minutes. In a scream that filled the bar, the shy girl had one of the most vocal orgasms I had ever witnessed.
As my girl and the gregarious girl untied the shy girl, she told them that she needed a drink and that it was now their turn to earn a round. My girl and the gregarious girl then flipped a coin, with my girl being the loser. So..., The shy girl said “What can my girl do to earn those drinks? Bartender, it's your bar, so you decide....”
We guys huddled again, with the shy girl’s boyfriend saying that he would love to somehow live out his older woman fantasy. Let me play with your girl.... I told him that he should go for it and that I thought that my girl might go for anything other than being actually fucked. So..., our friendly bartender said, Just how far do you think she'll go?... Well there is only one way to find out I told him, ask her....
Alright..., the bartender began, I would like to see you sit back on that sofa over there while we take turns licking your clit.... Now, I know that she likes nothing better than to be licked, but this would be her first contact with other guys since our sexual relationship began. Knowing that this would be another giant step forward in our play with others, she glanced over at me seeking my okay. I gave her a quick nod and she smiled.
They went over to my girl each taking hold of one of her hands. They escorted her over to the sofa, knelt in front of her and spread her legs. The shy girl’s boyfriend was first to have a go at it. Judging by my girl’s reaction, his tongue was definitely hitting the mark. Without saying a word, other girls joined my girl on the sofa, sitting on either side of her. As the shy girl’s boyfriend continued his licking and tongue probing the girls played with my girl's tits. With the other guy and myself left as observers, we each seemed to have the same idea of playing with our cocks while watching the show. When my girl began to shudder I knew she was cumming hard and fast. As she reached orgasm, the shy girl’s boyfriend pulled away, letting the bartender have his turn. It was not long before she was ready to cum again, but as with the vibrator on the shy girl, the bartender kept her on the edge for over fifteen minutes until she had her second orgasm of the night.
I know that once my girl has cum from having her clit being massaged, that she likes to be fucked. Since she seemed so accommodating to the shy girl’s boyfriend and the bartender, I told them to go ahead and fuck her if she seemed willing. I also told them that while they were at it, they should suck her tits. My girl again glanced over at me seeking my okay. Again I gave her a quick nod ok and she smiled and gave me a wink, and she turned back to the shy girl’s boyfriend, with her legs still spread she reached down and guided his cock into her pussy. After they had been going for a while she yelled “fuck me, fuck me harder. . .” As he thrust into her deeper and deeper and my girl seemed to be having a very good time the girls played with her tits and sucking them was the most erotic experience I have had. I was not the only one who felt this way, because before long my girl came as loud and strong as I have ever witnessed.
The shy girl’s boyfriend pulled out and the bartender moved up between my girl’s legs to take his turn. Again my girl glanced over at me seeking my okay, and I again gave her a nod and she smiled. The bartender went at her and pounded her hard – she seemed to be on her way for her fourth orgasm of the evening which came a short while later.
As my girl’s turn at play ended, we all sat at the bar having another Dirty-Sister. Once again, its was the shy girl who informed the bartender that it was now gregarious girl’s turn and that he should make the suggestion. As we guys were about to huddle again, the gregarious girl spoke up. You guys can come up with a plan for me or I can come up with my own plan. I promise that you will not be disappointed.... What the heck we thought, let's see what she has in mind.
Since I seem to be the show's finale for the evening, why don't we all get involved? She said since so far I had just observed so it was my turn. I want to 69 with him one-on-one till he cums in my mouth. After that she said we can go at it with a long complicated scorecard of pussies and asses..., which I did not care about because I had my faced buried in her nicely shaved and soaked pussy and was already licking, sucking and eating. When she finally took my cock into her mouth, she took it all the way into her throat and her tongue was not at all shy. She was also caressing my balls – This was one first class cock sucker. After a while I felt my own asshole being licked and fingered. It was my girl doing me the same way I had done her in the shower a year ago. However, 69 with the gregarious girl continued hot and heavy while I had the ecstasy of having my ass being worked. It was not long before I shot my load into the gregarious girl's mouth which she sucked up like a vacuum cleaner. At almost the same moment, I could feel her cum and her juices release.
After that each of us in turn separated and gradually took seats at the bar while the bartender poured some coffee and Baileys. All accept my girl and I. Our naked bodies were cuddled on the sofa. After awhile she said to me during the last year you have been the first to do me in so many different places and the first to do me in so many different positions – Thank you for making almost all of my fantasies into reality. However, I have a favor to ask of you. I said ok, sure. She said I want you to be the first to fuck me in the ass, and part of my first multiple penetration. I again said sure, but I think we need lubrication. She handed me the tube of lubricant.
I turned her over and started kissing and caressing her but cheeks and the crack of her ass, and rimmed her. She said to me, Tell me when you think my asshole is ready to take in your cock. I said ok but let’s not rush it. I slowly started to spread some of the love juices and cum from her pussy as well as the lubricant around and in her asshole, and began to work my middle finger slowly into her very tight hole. Slowly in and out, each time going a little deeper. When my knuckle went past her sphincter, which clamped down hard as she shied Oh! Yes . . Oh! Yes. I held my hand still and let her adjust for a moment or two. I felt the pressure relent and I continued spreading love juices, cum and lubricant deep into her asshole. I kept working my middle finger slowly in and out, and finally the hole loosened enough that I could carefully start to work in a second finger. She was also working back into me. When her asshole was loose enough to handle both fingers with ease, I did the same with the third finger. I was also as wet and lubricated as her ass, and I told her that I thought she was ready.
She motioned to the people at the bar. The shy girl brought over her boyfriend. As my girl took his dick in her mouth to finish getting him hard again, I put large amounts of lubricant on my cock. My girl then climbed onto his pole. After sliding up and down on it several times she settled firmly nestled on top of his tummy with his cock completely sheathed balls deep inside, and then she bent over onto his chest. She said to me over her shoulder “Now fuck me in the ass”. I spread her ass cheeks wide, and started to enter her ass. I could feel the boyfriend’s cock through the thin membrane of her anal canal. I finally worked my cock into her ass balls deep, and her anal ring was clasped tightly around my shaft. The three of us hit a nice rhythm of alternating in and out. My girl again motioned to the people at the bar. This time the gregarious girl brought over her boyfriend. The only person my girl had not done this evening. As my girl took his cock in her mouth balls deep and she now had penetration into every one of her holes at the same time.
All four of us adjusted to the rhythm, and my girl’s started moaning and the moans just kept getting harder and louder. She suddenly started screaming “Fuck me! Fuck me! Fuck me!” over and over. Finally she came as loud and strong as the first time that she had fucked the shy girl’s boyfriend. Right afterward he unloaded into her pussy followed by me exploded deep into her bowels. My cock went soft and I rolled over and it slipped gently out of my girl’s ass. After my girl caught her breath, she finished sucking-off the gregarious girl’s boyfriend.
My girl and I finally got some coffee and Baileys. As we sat there we noticed that all of us looked more than just a little disheveled. All of the others were making quick trips to the restrooms to tidy up and were getting dressed, we sat at the bar stark naked. As we finished our drinks, I told my girl how the whole evening went and ask her if she planned the whole thing during the short restroom break with the girls. She said No . . . I just told them what my dream was. They went with it and added some seasoning from there own dreams. It was everything I ever dreamed of, and absolutely the most and best sex I have ever had – Thank you! – Are you ok? – I love you!
At long last we decided to put some cloths on, which was not much for my girl’s because she had given all of her underwear away. As we finally departed, I noticed the whole bar had the scent of sex. I smiled and thought – This sure makes a great memory. There were hugs and smiles shared all around. An invitation from the bartender to return anytime was made and we all exchanged phone numbers and emails. Not sure if we will ever do this again, but I would like to.