Sex tip #28: Having a holiday plan by Sana & Theo

Sex tip #28: Having a holiday plan by Sana & Theo

About Sana & Theo

If we suppose to introduce ourselves and our life, it would be a world MESS. We are both studying at university an both have quite successful startups. If you would ever ask us what our plans for the week, except for the lectures, we wouldn’t be able to say. Situations in our lives change every single moment. We plan maximally one day ahead, and that brings a lot of stress to our lives. 

How we made it up

Last week we finally had a free week just for ourselves one whole week after a heck of a long time. We dreamed of this holiday for years. Just two of us. One week at an all-inclusive beach resort. To understand our story right, we must say that we talk about sex a lot, but really having it is a way different story. We’re usually that tired after a long day that we pass away in front of Netflix. So while we were planning our perfect holiday, Theo comes up with an idea. What about to also plan our sexual activities? I’d laugh at that first, but after a while, it started to make me a sense. Without a strong plan, we wouldn’t be able to have a perfect holiday.  

How to do it  

It’s not really innovative. Just sit down and discuss what kind of sex you would like to have in the upcoming days. Maybe you think it will lose all the spontaneity but, in our opinion, for some sexual activities, it’s more than pleasant to know about it beforehand. And for some activities, it escalates the tension. So let’s see our list. 

Day #1 – Lingerie sex

THEO POV: First night, we had chosen regular vanilla sex only with little spice in the lingerie way. After dinner and shower, I was banned from the bathroom, and I suppose to wait in bed. A few minutes later, Sana stepped out from the bathroom in her new beautiful lingerie. She was wearing shiny black high heel shoes, black lace stockings finished by a suspender belt. No panties. Her pubic hair perfectly shaved into a decent triangle. No bra, so her round perky tits pointed at me and calling me over. On her hands a black satin gloves. Red highly kissable lips and over the eyes lace mask. Her hair was combed into a bun. 

I had a lot of work to stay calm down and not to ejaculate too quickly. She knows that these kinds of sets set me on fire and even more when she walks in it like a queen of the world.  

Day #2 – Only oral sex

SANA POV: I was always immodestly proud of my fellatio skills, and Theo doesn’t lag behind. So for us, oral sex is a full-fledged form of sex. To be more thrilling, we agreed that anytime during the day, when someone says now and where the other one must go and provide the best service. My “now” took place before the after-lunch nap. I come back from the shower, where I flushed salt from my body and felt awesomely fresh. Theo didn’t resist a single second and covered my body with kisses. When he reached my intimate point, he pulled the highest caliber. Girls, you probably know guys who lick pussy like if was spicy ice cream, just with the tip of the tongue (probably the bad habit learned from porn?). But this is not Theo case. When he licks he puts everything in it. He uses the whole mouth, tongue, lips, and sometimes his fingers. And he always squeezing my inner thighs when he feels I’m about to come. 

Oh, those memories … Ok, I must have a pause writing. I will be back in 5 or 10 minutes. 

Sorry, I’m back. 

Theo’s “now” was during dinner. He excused himself for the toilet. A couple of minutes later, I got a text saying: “Come to the toilets at a lobby, right behind the front desk. Nobody’s here. I felt little butterflies in my stomach as I was aroused by the danger. He already waited for me before the toilets with a foxy smirk in his face. He pulled me in one of the men’s toilets cabin pull his pants down and said: “Be a good girl and do your best”. I really appreciate that he cleaned himself before the action, so I could enjoy it at the maximum. Later, when we were sipping our drinks, we made fun of what all could happen if someone had shown up.     

Day #3 – Anal sex

SANA POV: This! This is that kind of sex you certainly wanna know about at least a day before. At least me. For me, anal is quite a big thing. I had previous bad experience with it, but Theo showed me, that there is nothing to worry about if things are done right. The whole day Theo acted like a sweetheart to me. He constantly asked if I need something, if I want a drink or if I want to smear my back with sunscreen etc. If I were a bitch, I could easily manipulate him by anal sex. Muhahaha. Just kidding, I know that anal sex is a way higher level of intimacy for him, and I feel it the same way. After the cleaning process, I got amazing back rub, then he started to rub my but cheeks and he scrutinizes deeper and deeper until he reaches the downtown. He slowly circulates there and carefully adds more lube, asked permission once more, and then slides his one finger in. I was so relaxed that I didn’t felt anything than pure pleasure. He started to rub my pussy with his second hand, and I started to subtly moan. He did so well that I didn’t even mention that he put the second finger in. It didn’t take long, and I reached my first orgasm that day. Because I was fully relaxed now, he slowly inserted his penis in my backdoor garland. I was like in heaven, just feeling that amazing pressure and release slowly changing one into each other. It was truly magical, and no one can persuade me that it wasn’t due to planning.   

Day #4 – Mutual masturbation with porn

THEO POV: Day no. 4. Time to relax. We have had planned a trip to the close-by national park for this day, so we were expecting to be tired, and we were right. We got back at 9 pm, had light dinner and went right to our room. Now the tricky part begins. Pick the right movie. “No, this guy is ugly” or “Not this one, is so unrealistic” after fifteen minutes of picking, we had chosen orgy video, so the scenes change. After a while, real porn started for me. Sana started to rub her boobs and pull her nipples. When she notices that I was watching her more than the video, she started to overplay the sensation a bit, but I loved it. She sensually licked her fingers and slowly moved them to her pussy, while her second hand still rubbed her tits. At this moment, I stroked my cock faster and faster. That little naughty whore starts to provoke me even more. “Oh, I am such a dirty girl. I can’t stop touching my hot body” or “I should be punished by my poor behavior. Wish you could fuck me senseless”. You can probably imagine it doesn’t take long to climax for me, and Sana was done a moment after. Then we felt sleep while cuddling.       

Day #5 – BDSM sex


Written with the kind permission of My Master

I already knelt beside the bed, where toys were stacked, with the hood on my face (only with the hole for my mouth). Had handcuffs on my wrists, anal plug in me and besides that, nothing. My hands held the new leather collar. I heard that the Master entered our room. “Well, well, well. Look what we got here. Look who’s looking for the attention.” he said. I didn’t say a word. He came closer, took the collar, and said: “Once I put this on you, you are my property, and I can do whatever I want with you, but trust me, everything I will do to you is only for your own good. Do you agree with this?”. “Yes, Sir” I replied. He put the collar on me and gave me a big kiss on my lips. Ordered me to stand up, joined my handcuffs together, and put my hand behind my head. “Time for the inspection, little whore” he told me in a husky voice. He knows, that I struggle with this part. While he’s doing it, I feel so degraded and longing so much for a compliment. He knows, so he touches different parts of my body and only growls like he isn’t satisfied. “Ok then, at least you fuckholes are perfectly shaved,” he said. I smiled a bit and thanked him. “I heard that you masturbated this morning in the shower, do you confess yourself, or should I get it from you?” I shook my head rapidly. “No? Ok then,” he said calmly but with a minor upset in his voice. He put nipple clamps on me, and I hissed a bit. “Bent over the bed, and I will ask again when I feel you’re ready to speak until then don’t make a sound”. This time he said it much more vigorous, so I did it without any hesitation. My knees shook a little bit with the expectation of what is going to happen next. Then the first hit of the paddle felt on my bare butt. I hiss again. He buried my face more into the pillows and continue spanking me. When I felt my bum is going to burn, and a small drop of my pussy juice falling down on my thigh, he took my head from the pillows and asked: “Are you willing to admit now that you lied to me?”. “I’m so much sorry Sir, please let me know what I can do, so I can make it up for you.” I zealously replied. “Ok, but your punishment isn’t over. Kneel and suck my cock. Take care really well, or I will have to hurt you even more.” I started to suck my Master’s cock and already felt a lot of his pre-cum as he was aroused from spanking me. That really flattered me. I heard him a bit moaning, so I speeded up. He sharply stopped me. “Where’s the rush? Don’t think you’ll get over it so quickly.” He set me up and laid me on the bed. I had a feeling that he is looking over my body a maybe masturbates a little bit. A moment later, he started to rub my pussy, and it felt so good. I tried to control myself because I didn’t receive permission to have an orgasm. Bad for me, that my Master has really dexterous fingers. I stretched like a bow and had one of the strongest orgasms of the weak. Master immediately stopped and said: “Ok, put this on your punishment diary, we will deal with it later”. Then I was blessed with his cock in my pussy for a while until he jizzed in me. He felt down on me, he caresses my cheek and said: “That’s all for now. See, you can be a good girl if you want”. And I felt like in heaven.     

Day #6 – Dirty maid fantasy

THEO POV: It was a lazy morning, we just laid by the pool and sipping the coffee. I started to fall asleep, and suddenly Sana poked into me and said: “wait for the signal” and wink on me. Now I’m not sleepy at all, I thought to myself. About 20 minutes later, I got a text from her: “Sir, there is something weird going on in your room. Please arrive immediately.” I knew, what was that weird thing that was going on. So I just covered my hard-on with a towel and hastily walked to our room. 

I opened the door and saw the maid masturbating and sniffing my shirt. I violently closed the door and vigorously ask: “What ‘s going on here? I’m not used to, that personnel of the hotel touches my personal stuff. She replied with a nervous tone in her voice: “I’m so sorry sir, I just couldn’t resist. Please don’t tell it, my manager. I will do anything. Just please don’t tell it, anyone”. “There is something that could be done” I replied. “Anything Sir, anything” she begged. I started to pull my swimsuits down. And she said: “No Sir, please, not this. I have a husband that I love”. “Ok then, let’s find a manager”. She immediately comes closer to me, kneeled down, pulled my swimsuit down, and started to eagerly suck my dick. Then I stopped her and ordered to bend over the desk. She again remonstrates, but that only made me want her more. I finished it with the jizz on her butt and said: “hope you clean this mess, so I don’t have to report it you to your manager” and walked away. When Sana come back from the room with a big smile, she teased me, where I was, that she only left for a restroom, and I was gone. I smiled too … a lot.            

Day #7 – Invite another couple/Sexy photo shooting

SANA POV: It’s been quite a while since we had sex with another couple. And we weren’t sure if we are going to be able to succeed with this task this week, and if there will be someone suitable in the resort. So we had a backup plan, sexy photo shooting. Luckily we didn’t have to approach it. 

We knew that if we wanna succeed, we must work on it since our arrival at the hotel. Immediately in the lobby, we started to scan for a suitable couple we could seduce. But we saw nothing, only families with small children or elderly couples. We’ve started to feel a bit anxious. Later, Theo admitted to me, that at this moment, he started to plan on how he wants to photoshoot me. For a few more days our situation seemed to be desperate. But on the sixth day of our vacation, this AMAZING couple showed up, let’s call them B (him) and G (her). B was tall, musculus and tan, and G was a petite blonde with nice round boobs and remarkable bum. We saw two free deck chairs near to them so we decided to lay there that day. It did not take long and we started chatting about the resort, noisy kids, etc. The word gave the word, and we had dinner with them. She was really funny, and he was so mysterious. The next day repeat, laying near each other by the pool, common meals, having fun, and the disco was planned in the evening. Lucky for us, the disco was so boring, that it wasn’t hard to convince them to continue the party in our room. A couple of drinks later, I started to make out with G, which aroused both guys. I asked them if they want more, and they both nodded. So I started to undress myself and her. She was a bit shy, but I’m sure this wasn’t her first girl on girl experience. Theo was so aroused that he pulled down his pants and started to jerk off. B’s pants followed. I whispered to G’s ear: “Look what a nice cock Theo has. Wouldn’t you like to suck it off?” She timidly looked at B and he nodded like a crazy person. I pulled her panties down and started to lick her and invite B to lick me as well. Oh, he certainly knew how to do it. Then we agreed that he will fuck me and Theo will fuck G. We stopped early in the morning, and it was probably best foursome I had ever had. 

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