Sex on the Retreat Pt. 01

This story is the first part of three.

It had been a stressful summer. The stress of being alone in the store for most of the summer when my co-worker had been on vacation, while the pharmacy had lots of customers. Yes, I'm a pharmacist. I have my own little shop with almost a full range of products. In addition to the prescription drugs, there is a wide range of other products for beauty care, foot care, oral hygiene, intimate products and yes, a little bit of everything. Almost like a small variety store, I usually say. Being a pharmacist may not be the sexiest job in the world, but it requires a lot of knowledge about different preparations, how they go together with other drugs and how to take them. Doctors often prescribe new medicines without thinking about or understanding how they fit with the medicines the patient is already taking. We pharmacists have a big role here and sometimes we have to warn against combining and sometimes even go back to the doctor to give the patient a different medicine.

But most of the time it is routine. Customers come in, show their ID and tell us which medications they need, if there are several on their prescription list. The days come and go, one customer after another. But sometimes something odd happens. Like when a guy, maybe 20 years old, comes in and wants to buy condoms. He stutters a bit and looks slightly nervous. He asks which ones are good and what I can recommend. Our range is not very large, but we have a couple of different brands. He says he wants one as thin as possible. I take out a package. I ask if he wants a pack of ten or thirty. He says thirty, pays and goes out.

I have to describe myself. My name is Elise and I'm 40 years old, 168 cm tall and weigh 59 kg. I have light-colored hair that I usually wear half-length and, more often than not, down. Many people say that I am quite cute. A little bit feminine round, not big breasts, but I like them. Currently alone, after my relationship broke up before the summer. When we couldn't take a vacation together, he took a trip to Tenerife. He met a younger willing woman and had been having sex all vacation. Yeah, so my life doesn't really rock.

A little later in the afternoon, the guy who bought the condoms comes back. He blushes and says he probably doesn't know how to do it. He has tried, but only gets it on a little bit. Then he asks if there is any help, if I can show him how to do it. Is he too big to use condoms?

"I've never heard of that," I say. "What do you mean you want help?"

"Yes, well, show me how to do it," he stammers and turns bright red in the face.

"Well, we have no such service. It's usually never a problem. Don't you have anyone to ask?"

"No, no, no. I'm meeting a girl tomorrow and I want to be prepared. Can't keep fumbling around if something happens. I've never done that before. Been with a girl, that is."

The guy looks nice, and so inexperienced, it seems. What would I do? Can't ask him to pull down his pants and show him here in the store!

"I close at seven," I hear myself say. "Come just before and we'll see what the problem is."

Ohhhh, God, what am I doing? But I was both moved by his story and interested to see what was so difficult.

At five minutes to seven, he came back to the store. He had the packet of condom with him. I asked him to wait a while, had to deal with the last customer and then close and lock up.

"Come back here and we'll see what you don't think works. Try putting a condom on this dildo," I say, taking out one of the dildos we offer for sale.

He takes out a condom, opens the small package and puts it on the dildo. It goes on like a charm.

"There doesn't seem to be any problem. You do exactly the same on your penis. But make sure you are really hard first. It's hard to put it on if it's soft."

"I have tried," says the guy. "But it doesn't work. And I've wanked it up so it's hard and big."

"Mmm, what do you want us to do? Do you want to show your penis and how you do it?"

This is crazy! Am I standing here suggesting that he pull out his penis and show it to me? What am I doing? And say? The guy is now blushing even more, if possible, but starts to unbutton his pants and pulls them and his underwear down. Oh, my God, what a penis, yes cock! It's probably 18-20 cm long and looks really thick. And it now stands straight out, no problems with the erection. I don't think I've ever seen such a big glans, a bit purple. So beautiful!

He takes out a condom, opens it and tries to roll it on. Only the glans comes in. No matter how he pulls and tries to keep rolling, it doesn't work. I can't help myself, I grab the shaft and try too. It doesn't work. I get a tape measure; I have to measure how thick he is. I get it to just over 15 cm in circumference, i.e., a diameter of almost five centimeters. Now I understand his problem. We don't have any condoms in that size. My advice is that he will have to find another shop.

Meanwhile, I am standing there with his huge cock in my hands. It's so nice and without thinking about what I'm doing, I'm jerking him off slowly. In addition, I am now really horny myself and feel that my panties have become wet in the crotch. I wonder what a cock like this feels like? I haven't had sex since my partner disappeared. Here I stand with this fantastic creation and just want to feel it more, feel it inside me.

I bend down and lick the hrad lightly. I taste some salt and, actually, soap. My mouth swallows more of the cock, feeling the glans teasing my throat. Playing with my tongue, licking and sucking. He seems loaded. Doesn't want him to come in my mouth. Stops sucking.

"Sit here on the chair," I say. "If you've never been with a woman before, now is the time."

I quickly pull down my panties, unbutton my pharmacy coat and sit over him. Point the cock at my now soaking wet pussy and sink down on him. What a feeling when he comes in; how his glans makes its way into me, as I lower myself down. Ohhhh, it stops, can't get it all in; the glans is at the bottom. I start riding him, slowly, slowly. What an experience! Gets completely fulfilled by him, so wonderful. Have never had such a big thing in me before. I move on him, wanting it to never end. He starts moaning and groaning. Grabs me hard and he comes. Spraying and pumping his semen into me, three or four strong shots. And then, without warning, I come too. An orgasm that matches the size of his cock. Is there a connection? No, no, size doesn't matter! Everyone says so - but they are wrong. They have not experienced this model.

I'm still sitting on him. He is still hard and, I think, even thicker. Is it possible to ride on? I start to move a bit again. I squeeze my inner muscles and feel how he responds. Now it's really wet and sticky, from our combined fluids. The friction is a little less, but still so nice to have him there in me, experiencing how he fills me with both cock and seed. He can last longer now, we move together, enjoying the experience. For a virgin, he is a natural. After a while, we increase the pace automatically, until we reach a pace where the whole shop is sloshing and making noise. Good thing we're alone. Now I'm getting close again, wanting to have that amazing orgasm one more time. My pussy clenches and squeezes him, my legs want to close around him as I come in my second orgasm. It seems that my convulsions also make him squirt a second time. How much is in his balls? It feels like he fills me with his fluid completely, and it runs down the length of his cock, onto the chair and the floor.

Sweaty, I get off him. Get a towel and dry him off. Holding his cock which is now a little softer, but still huge. Dries him thoroughly and really gets a chance to inspect this monster. So amazing. Asks him to wipe me. Want to feel his hands on my pussy, my body.

Stunned, we stand up, look at each other. He is blushing and I have a big smile, starts laughing and he joins in. There we are half-naked and laughing!

"Thank you," he says. "That was fantastic! How did it go for you? I didn't have a condom."

"Don't worry, I take pills. Besides, I think I have to thank you for an unforgettable experience. Take care of that monster. He'll make a lot of women happy. You don't have to worry about not being able to satisfy a woman. Good luck tomorrow, and don't forget to buy large condoms."

Yes, this was an example of experience as a pharmacist. Rare but so amazing. I've been working all summer and it's time to take some time off. My colleague is back, and a newly graduated pharmacist will be working while I am away. Together they will be able to manage the business.

My mother has booked a trip to Madeira for the two of us. The idea is to spend a day in Funchal and then go to a special place, a real retreat. Just the two of us and a lot of books, sun and swimming.

When we land in Madeira, the weather is lousy. A little rain in the air, but warm and pleasant. We go to the hotel, unpack and then go out to get something to eat. Nice to just walk around in a thin summer dress. The wind caresses and embraces my legs, it is so nice to just walk and be. Feel how the wind caresses me all the way up to my panties, I actually feel it through them.

Down at the market we find a fish restaurant, it seems nice. We go in and order each a Sea Bass. Fully cooked. It comes in, the fish is fresh and good, but completely without frills. With a good wine, we feel much better. We walk back to the hotel. Have a beer in the bar and then go upstairs to bed and sleep.

Mom and I have traveled together several times before. Sometimes my dad comes along too. Regardless, we always share a bed and find it nice to just lie down and chat. Sometimes we give each other a hug or caress each other lightly. If Dad is there, it can be a bit more than just caressing. He tends to get excited when we are all naked. But with my mom, it's just close and cozy. My mother is about the same height and weight as me. A little plumper over the years, since she's 65, but still a nice figure. It's clear that the earth's gravity has made her breasts a bit saggy, but they still look nice and relatively firm. I know that they are very nice to caress and play with.

I tell her about the guy who wanted to buy condoms. I notice that my mom is interested and wants to know more details, so I try to describe what his penis was like and then what I did. She thinks I was both wrong and right at the same time. I had to show how long and thick he was and describe the feeling of being fulfilled. Yes, we have such a natural relationship that we can talk about it. So I say that he was several sizes bigger than my dad, who doesn't have a very small penis. We both have experience with it, but that's another story. Now I notice that mom is starting to masturbate. Sounds so nice, and I got a little wet just telling her. We end up lying there next to each other, rubbing our pussies and clits. Moaning in unison. Notice how the bed shakes and vibrates when mom comes. Soon after, it's my turn.

After a while we hug each other. Say good night and fall asleep.

The next day we make an excursion to one of the many levadas, and walk along the small canal that leads the water down to various farms. In the afternoon we pick up our rental car. We make a list of what we need to buy for the retreat. The small restaurant there closes at six o'clock, so we have to prepare food ourselves. It will be a long list of food and wine we want.

When we arrive there is a cable car that goes straight down about 300 meters to the beach and the houses where we will stay. The cable car also closes at six in the evening. There are no other ways to get there, except possibly by boat. Down there it is a microclimate, even with bad weather it is almost always warm and pleasant. It can rain, of course, but usually the sun is shining. There is a rocky beach, lots of banana plantations and a large garden with all kinds of plants and flowers. An oasis!

We take the cable car down with all our stuff, check in and get a small house with bedroom, living room, kitchen and a private patio, a terrace. There is even a barbecue, if we want to barbecue. The house and patio are completely private. We unpack and make ourselves at home. Then take a walk along the road to the pier, where the restaurant is also located. Sit down and buy some lunch. Think we are the only guests in the place.

After a while, a man comes walking. Says Good afternoon, orders a beer and sits down at one of the other tables. He looks at us and asks:

"Just arrived here. Are you going to live here too or just a short visit?"

"Hi," I say, "we arrived a little while ago and are staying for five days."

"I've been here for two days and will stay another five," says the man. "It's really nice to just be here. No hurry, no needs, nowhere to go, just walking the trails, sunbathing, reading and, well, just being."

Mom and I give each other meaningful looks. The man, maybe 60 years old, some gray hair. Looks well-built, nice laugh lines on his face. Maybe 175 cm and around 80 kg, we guess. He is wearing a simple tennis shirt and a pair of shorts and sandals. He looks easygoing. We start talking and inquire about the place.

"Not much to tell," he says. "What you see is what's there. Sometimes some people come and just visit the place during the day, then take the cable car up again before they close. Otherwise, it's very private and quiet. And the houses, where you live, no one is permitted except those who also live here. But even they are usually only seen here in the restaurant, or when they go for a walk."

"You have bought food with you, right? Otherwise, you can order here what you want to cook in the evening," he continues.

"Yes, we understood that. We have bought a lot, both food and wine. We'll manage, at least for a few days. In the worst case, we'll have to take the cable car up and go shopping. It only costs ten euros to go back and forth with it. The problem seems to be parking up there. We just found a spot, but then it was full."

"Yes, I know. Many people park along the road. Not allowed, I guess, but what to do? Well, now I'm going to make some lunch. Maybe we'll meet when we're out walking or here at the restaurant. There's not much else to do. But I'm mostly in my house or on the patio, sunbathing, reading or writing."

"Nice to meet you," I say, "but may I ask what you are writing?"

"Mmm, don't know. Not so proud of my writing. I've written a lot in the past, but only non-fiction and articles. But now it's something else..."

"You don't have to tell me, sorry if I was a bit too curious."

"Yes, it's true that I now live quite alone, except when I'm working. I don't meet any women, I only have myself and my imagination. A fantasy, which replaces the usual relationship."

"Well, I write short stories for the internet. Short stories that many people like to read and get a little excitement from," he says.

"What, you write erotic short stories," I exclaim.

"Yes," he replies, "nothing I really want to talk about. A little ashamed, actually."

"Why is that? Aren't they good? But if many people read them, they must be good. Would it be possible to read them? I'm sure my mom would like it too. I guess we're kind of nerds about that."

"Oh, dear. I wasn't expecting that. But you can go on the Internet and read. Feel free to tell me how you experienced them. Or I can send you a newly written one, which hasn't been published yet. I'd love to hear what you think. Where do you live?"

We tell him where the house and he say he'll come by with the story a little later. Then he goes away.

Mom and I look at each other. This could be an interesting stay. Some erotica to read in the sun. After eating, we go back to "our" house. Undress and go out on the patio. We are both naturalists and enjoy sunbathing and being naked.

There are two sunbeds. We anoint each other. It's nice to be rubbed in by warm, soft hands. I feel that my mother is rubbing a little more carefully on my breasts and thighs. Making sure that the sunscreen really covers all parts, even in the womb. Lovely. Then I lubricate mom. Just as careful when it comes to her nice breasts, stomach, thighs and pussy. Notice that she is already wet when I get to the intimate parts.

"A little horny? Is that man getting you wet?" I ask.

"Mmm, and that he writes erotica. And isn't he sexy? I wonder what he's like by the way. Maybe I can seduce him? He has no women in his life, he says. Maybe the three of us can have fun together?"

"Sounds like a plan," I say. "But we have to proceed with caution. I think he's a bit of a loner, doesn't let people in easily."

"Maybe, let's see. He'll bring the short story, then we'll see when we discuss it with him," says mom. "What would he say if we invite him and are naked?"

"Slowly on the slopes. Then we'll really scare him off. Let's take it easy."

We lie down and sunbathe. When there's a knock on the door, I put on a sundress and go to open it. There he is, now with a small stack of paper in his hand.

"Hi, do you still want to read? I can't wait to hear what you and your mom think. Maybe we can talk tomorrow?" he says.

"Oh yes, we really want to read. How exciting. We will be reading it right now. Don't you want to come and have a drink later?"

"Thanks, I'd love to, but only if you let me cook, barbeque, for you. All right if I come at six?" he says.

"We'll have a drink outside, so dress lightly."

I go back out to my mom on the terrace. She takes the first page, starts reading. Then hands it over to me. I glance at her. She reads with growing interest. She holds the pages in one hand. The other is on her thigh. I see how she slowly starts caressing herself. I start reading, after a while I get warm, my body tingles. He can really write. Makes me excited when I read. Impressions and feelings go straight into the body, from the eyes, down through the breasts, the navel and into the deepest part of the pussy. I get wet, have to take a hand and caress myself. So fantastic, an outstanding story, both action and eroticism, at the same time. Exciting, can't let go of the pages.

I see that mom doesn't just caress herself lightly, she has three fingers inside her vagina and rubs her clit with her thumb. I'm no better. We read and masturbate. Moaning and whimpering. Really good story, at least it has the intended effect on both my mother and me.

The story is about a slightly older man who picks up a woman in a hotel bar. After they have sex, the woman goes down to the bar and invites the young woman standing at the bar. Then their games continue more or less all night. A lot of sex and a lot of kinky stuff. We get red-faced, horny, wet and, eventually, satisfied as we read and masturbate. But it feels like a rather empty satisfaction after what the characters in the story experience. We need the real thing. It's not just the direct body contact, but even more the feeling of being filled with a warm, hard, veiny and pulsating cock. Imagine if we had that guy in the pharmacy right here with us!

"It's half past five. What should we offer? And we have to put something on, right? I can't meet him naked. I don't know what kind of guy he is yet. Bikini or something else?"

"Bikini, I think, we said scantily clad," mom says. "We have beer and wine, he can choose, I think. I bring out a sundress to wear if he comes fully dressed, just in case."

"Okay, I will set the table and put on the red bikini. The one that's quite boldly cut, but still quite innocent. Highlighting but not showing..."

"Then I take the blue one, a bit like yours, but perhaps a bit more respectable. I'm no longer so young."

We set the table and get dressed. Soon there's another knock on the door. Mom goes to open it. She looks great in her bikini. Just right. The man is only wearing a pair of swimming trunks. Good, then we don't have to get dressed either.