Ryan's Rules

I work as a sommelier in a fancy restaurant. So I have to buy the wines for the restaurant and suggest choices matching the food to the customers. The most important organ for my profession is my nose. I like the job, but there is not a lot of money in it. My wife brings in the dough. She is a real estate agent, and business was booming. She told me she needed a break, and wanted to go on a one-week vacation. "Fine", I said, because I can essentially go on vacation when I want. I can easily teach a waiter all the bullshit I tell to the clients, like "the hint of chalk in this wine perfectly combines with the halibut". Only when the restaurant buys wines my nose is really needed.

While discussing the vacation options my wife suggested: "Why don't we ask Lillian and Owen if they want to join us". Lillian is an old friend of hers, who moved to a town a few hours driving from where we live, so we don't see them often anymore. Going together to a holiday resort seemed a nice way to get in touch again. I know Lillian well from many years ago, when she was living nearby, but two years ago she married Owen, whom I have only met a few times. Owen was not her first love by any means; she had a long string of boy friends.

We, Matteo and Madelyn, are a young couple around 30 years old. Lillian and Owen have roughly the same age as us. My wife Madelyn is a petite brunette, with a C-cup that is well-proportioned with respect to her shapely body. We have a good sex life, but a fairly ordinary one. Nothing kinky, just caressing, licking, sucking and fucking. Due to our different working hours we sometimes have to use our agendas to plan sex, but we do our best. Occasionally we have discussed getting sexually involved with other people. We found the idea exciting and were open to it, but it never happened.

Lillian is a bit taller than Madelyn, and also has bigger breasts. She is blond, but not the stereotypical dim-witted blonde. In fact she has a wonderfully naughty intelligence, and likes to say things like "a dirty mind is a joy forever." But despite all her naughty talk, it never went beyond that, not with us at least. I had never even seen either her or Owen naked. Madelyn once told me that Lillian is trying to make a living writing erotic books, but with little success. But I am not supposed to know that.

Owen works as a software engineer in a niche online book company. Antique books, I believe. He looks a few years older than his age, with some premature baldness, and a bit of superfluous belly fat. But despite his not too sexy looks, Owen is quit horny, says Madelyn, who heard that from Lillian. As Lillian put it: "We fuck like rabbits". You would never guess that if you see him. On the other hand Lillian herself looks as if she can't get enough of it, which is probably true.

I have to confess something about myself. I am a heterosexual man who has always been fascinated by penises. I am sure I am not gay, and not even bisexual. When I walk through town, only the women have my attention. My brain scans them systematically, and filters out the men. I am never attracted to men and I have no desire to have sex with men. Unlike women, I am not interested in a guy's butt. But when a guy takes off his pants, I am immediately focused on his cock, and I would very much like to play with it for a while. I would even love to suck it, but nothing beyond that. I have absolute no desire to go anal with a man. Not with a women either, but they have a more attractive hole to put my penis in. I have no problem with being like this. In fact, I would love to be truly bi-sexual, so that in principle I can enjoy sex with any human on this planet, but I am not.

My penis obsession exists only in my mind. The cocks I have actually seen are either in shower rooms or porn. The advantage of my cock fetish is that I can jack off to almost any types of porn. In particular I like the kind where a straight guy is seduced by a gay massage therapist. Videos with lines like: "Doctor, what are you doing?", to which the doctor answers: "well, I notice a lot of stress here, so I will have to see if I can release it; don't worry, I am a professional, I know what I am doing".

Then the towel covering the straight guy's ass is removed and we get a shot of his balls between his legs. He is told to turn around and we get a closeup view of the client's cock being massaged. A little later, the therapist has mysteriously lost his pants, and the client starts sucking his dick, without any explanation of the therapeutic value of this procedure. By then I have usually already shot my load, and if not, I stop the video anyway, because what follows is usually some anal penetration scenes, which make me lose my erection.

Straight men with a cock fetish are not uncommon, as I found out after a bit of googling. One theory is that it afflicts men who are worried that their cock is too small, but I am not sure that is true. Sometimes these men meet in mutual masturbation clubs. This sounds like fun, but I have never tried it. I am worried that the atmosphere may turn out to be too gay for my taste.

My fetish has a special place in my brain, where it inspires wild fantasies that will never happen. More often my fantasies are about group sex and orgies, which also never happen in my real life, or so I thought. My wife knows about my fantasies, but takes them for granted. We never talked much about it. Neither of us have any aversion to same sex interactions, or to sex with strangers; it just never happens.

My mind went on one of these fantasy trips again after we booked a week in a beach resort in Florida, where we were going to share an apartment with Lillian and Owen. Though Owen is not especially physically attractive, he has a penis, which is always enough to trigger my imagination. Perhaps I would get to see it, perhaps I would be able to touch it, lick it or suck it.

Not that I was not interested in seeing Lillian naked, but she is my wife's friend, and not likely to reveal herself to me. Surely, scenes of wild orgies involving the four of us crossed my mind, but that seemed outlandish.

But perhaps Owen and I might share the bathroom one day, so that I could see his crown jewels. My own crown jewel is unfortunately below average in size. About 5.5 inches when fully erect, though fairly thick. But I cannot complain. It performs very well and it gives my wife and me a lot of pleasure. I enjoy standing naked in front of a mirror and admiring it.

The apartment in Florida turned out to have two bedrooms with kingsize beds, and two separate bathrooms. There was also a common living room with a dining table and a coffee table with two large sofas. The separate bathrooms ruined my fantasy: no chance to catch Owen naked in the bathroom. Perhaps I could convince them to visit a nude beach? That would of course be cock paradise for me!

The day after arriving we did go to the beach, but a normal one, where clothing was not optional. I saw my friends in bathing suits. Lillian looked as good as I remembered her, and Owen looked as unspectacular as usual, except that he was wearing a speedo, which is a bit unusual for a man like him. Perhaps this was Lillian's idea, in order to make him look a bit more sexy. The speedo showed the outline of his penis, which I studied with interest. It seemed to be of substantial size. I was wearing standard swimming trunks, which hide ones manhood, unless it is monstrous in size.

I took a deep breath and inhaled some fresh sea air, and commented about how wonderful it smelled; Smell is kind of my profession, after all. Lillian said: "So you like that smell? I have more of that if you want some." Madelyn understood the sexual innuendo immediately and said with mock revulsion: "Come on Lillian; behave yourself." But I knew she liked it when Lillian talked dirty. I wish I had the presence of mind to say something lewd in reply, but my mind was too slow that day.

A good-looking couple entered the beach, and they sat down a few meters away from us. They were younger than us, I would say about 25, and later we learned that their names were Ryan and Natalie. Ryan was fairly tall, had dark hair, and the kind of body that makes women drool from their mouth and their pussy. Even I, as a man, could see that he was a good-looking guy. He had an impressive sixpack, a firm ass, and a movie star face. Unfortunately he wore swimming trunks, which revealed nothing about his cock.

But impressive as he was, Natalie was from a different planet altogether. She had the kind of angelic face that I can fall in love with on the spot. She had beautiful, long, chestnut colored hair, matching her hazel eyes perfectly. Here breasts were C-cup sized like those of my wife, and she had the perfect hour-glass figure, highlighted by a sexy yellow bikini. My sexual fantasies immediately flipped from Owen's cock to wild fucking sessions with Natalie. Madelyn and Lillian are good-looking women, but Natalie was in a different class.

We started talking to Ryan and Natalie. They moved a bit closer to us, much to my delight, and to the delight of the others, as I found out quickly. Lillian and Madelyn could not keep their eyes off Ryan, and Owen and I could not keep or eyes off Natalie. They were very charming people from the Chicago area, and we got along really well. He was a mathematician, totally in contradiction to his stunning looks, and we never found out what Natalie did apart from being devastatingly beautiful. She was a bit shy and not very talkative. Ryan did the talking, but never in a dominant way.

We decided to go for dinner together with them, to an Italian restaurant at the beach front. Three of us ordered Spaghetti alla Vongole, which Lillian referred to as "Spaghetti with Pussies". Natalie laughed out loud at that joke. She is even more irresistible when she laughs like that. We drank a bottle of "Verdicchio dei Castelli di Jesi" which I had selected. I told them that it was characterized by aromas of ripe peach, tangerine, pineapple, flowers and flint. All were impressed, except Madelyn, who already knew my theatrics. The wine went down very well, and we ordered a second bottle. We were all pleasantly drowsy when we left the restaurant, and we invited Ryan and Natalie to our place for some more drinks. On the way I overheard Lillian and Madelyn whisper something to each other. I could not quite understand everything, but they seemed to say that Ryan's appearance had made them very horny.

After a few drinks Ryan asked: what do you guys usually do in the evening? I replied that there was no fixed activity, because we were not even used to going on a vacation together. We might watch some TV, or go on a beach walk, or visit a bar. I asked him if he had any suggestions. He hesitated, then said: "I do, but I am not sure this is your kind of thing." Lillian said: "Just give it a try, and we will tell you". He said: "OK then. On several of our previous vacations with friends, we played strip poker." I glanced at my wife, who appeared interested. Lillian said: "Sounds great! Please tell us more about that."

Ryan said: "I am sure you know already that it is a game where, depending on the outcome of a draw, the participants take off pieces of clothing. There are many variations. It does not have to be poker, or even a card game. Often there are several rounds, each with a winner and a loser. Sometimes the loser must remove a piece of clothing. In other variants the winner chooses a participant and a piece of clothing they should remove. In more conservative groups the game goes on until everyone is in underwear, but more often everybody ends up naked." Madelyn said: "Well, fortunately we are not conservative. We have no issue with nudity. But who is the winner of the whole game, and what does he or she win?".

Ryan answered: "In most case, if everyone is naked except one person, that person is the winner. Their prize is seeing everyone else naked without revealing their private parts themselves. But often at that stage there is a huge buildup of excitement, and others things start happening. Often the fully dressed person will then feel more like a loser." Now Lillian started getting even more interested: "Other things? Like what?". Ryan said: "It involves using other parts of your body than just your eyes and ears. You know what I mean, right?" Lillian said: "If I understand what you mean I am definitely interested. So tell us more."

Ryan continued: "My favorite version is one where there is a winner and a loser per round, and the winner has the right to remove one piece of clothing of the loser. Usually the loser can decide which garment to remove. This leads to one-on-one physical contact, which can be quite erotic. Madelyn asked: "What kind of physical contact? Is the winner allowed to touch the loser?". Ryan said: "That depends on the group. In some cases the loser simply performs a little striptease-style dance, removing the piece of clothing. In other cases the winner removes it. In doing so some parts of the body may be touched, inadvertently or not, including some private parts. One could also agree that the winner has the right to caress any skin that is revealed. One can even agree that the winner may use their mouth to do this."

After these words there was a brief silence, and I fully expected one of us to say: "that goes much too far for me". But instead my wife said: "I think that before we start I should go to the bathroom and wash myself a bit." It was a tacit admission that she was seriously thinking of going ahead with this.

Then I brought up the question that was of my personal interest: "What happens if winner and loser have the same sex?". Ryan said: "Again, that is up to all of you. You have to define the limits that you feel comfortable with. One option is that rounds that end in same-sex interactions are simply skipped, until there is an opposite sex outcome". Lillian said: "Maybe it is more exciting to allow same sex. I would be perfectly happy to remove a women's bra and fondle her tits. Madelyn and I already have experience with that".

That was news to me, but not shocking or surprising. Madelyn had already mentioned to me that she had some lesbian experiences, but not that Lillian was one of her partners. Lillian continued: "The men may be less enthusiastic. Usually they stress out when anything "gay" is happening." My wife replied: "Those poor guys. They get to see three women naked, and there is a price to be payed for that. We get to see them suck each others cocks". She was getting terribly explicit now. Perhaps the wine was doing its work. I had never seen her like this before.

It was part of a general outbreak of open-mindedness, where nobody wanted to say that something was going too far for them. Of course I liked where this was going, because now cock-sucking was on the table, and with feigned reluctance I said "I will deal with a cock the way I see fit. I can handle it". "I would love to see you handle it", said Lillian. Owen said, jokingly(?): "I would love to suck your dick if the opportunity arises", and then blushed when he realized what he had just said.

Ryan, who seemed to take the lead of the game, said: "Wow, I thought you were all a little reserved initially, but I am pleasantly surprised. Perhaps the best plan is not to set any strict interaction rules in advance. Obviously if during the game someone goes to far with them or their partner, any one of us may say no. Then we respect those limits from then on. I am pretty uninhibited myself but not everybody is like that. If you are going to try something new, please ask it first. Otherwise we would have to make a check list of all imaginable sexual activities and approve them first. And believe me, if you forbid things in advance, you may regret it later, because this kind of game tends to push your limits as sexual tensions mount."

The number one sexual activity on my list was fucking Natalie, but I did not dare to ask explicitly if that was OK. I was sure everyone was already thinking about fucking, but nobody wanted to mention that yet. Since she had not said anything I merely asked: "Natalie, are you OK with all this?" She nodded yes, and seemed to blush a bit, but Ryan answered for her: "Don't worry about Natalie. She just loves anything that might happen. I am almost certain that her limits are way beyond yours!" That is good to know, I thought, and my cock twitched in my pants.

Ryan asked if any of us had an STD, to the best of our knowledge. And he asked if the women used contraceptives. "Just in case" he said, "but I have to bring this up now, so that we do not do anything we regret later." At this point we all understood clearly where this might end. I realized later that we took a risk here, because we only knew Ryan and Natalie for half of a day, and knew next to nothing about them. Perhaps the whole thing was a ploy to make Ryan fuck two attractive women. Perhaps Natalie was part of the complot, and served as bait for the men. Even today I still think that this is possible. Perhaps on every vacation they tried to make friends with an attractive group of people, and have sex with them. But nothing bad happened, so I don't care.

Ryan seemed to have thought the whole thing through in advance, and with mathematical rigor he started working out the last details. We established that none of us brought playing cards, but Lillian and Owen brought a board game with a pair of dice. So in each round all of us would roll the dice, and the highest and lowest numbers determined winner and loser. In case of equality, those participants would roll the dice again, until a unique winner or loser was established.

Ryan had also thought about the endgame. If someone was already naked, it was pointless for that person to be the loser, since they had nothing to lose. But they could still be a winner. So in that situation the loser was the lowest scoring person who still has some clothing. If there was just one person left with some clothing, that person automatically became the loser, and the five naked people would throw dice to determine who was given the pleasure to undress the loser.

He had also thought about clothing. Everybody should start with the same number of items. We all agreed that shoes, socks, stockings and jewelry would not count. So the women started with a shirt, a bra, a skirt and panties. Removing any of these is exciting for the men, but it is hard to come up with something equally exciting for the women. Nature has provide women with three exciting body parts, and men with only one.

We decided on shirt, pants, underpants and speedos for the men, to be removed in that order. I could borrow a speedo from Owen, but he had only one clean one left. So I gave Ryan one of my undershirts to wear under his shirt. His stripping order would then be shirt, pants, undershirt, underpants. At least in his case removing an undershirt would reveal his impressive sixpack, which the ladies loved. I my case or Owen's there was not much there to get excited about.

One by one we all went to our rooms or one of the bathrooms to change into the appropriate clothing. In retrospect it was amusing that we all went to separate rooms to change our clothing. We intuitively understood not to get changed in the living room in front of all the others. Even though all of our secrets would soon be revealed anyway, that would ruin the whole point of the game.

We also washed the relevant body parts. "Do not use heavily perfumed soap", Ryan remarked, showing once again that he thought of everything. The smell of vaginas and penises is generally under-appreciated. If you google that subject you find that it is mostly discussed as a problem, and rarely as a positive part of the sexual experience. But any animal can tell you that it is!