I will tell you a story about what happened this summer when I went on vacation with my parents and their best friends.
It was not the first time that we were going on vacation together, we did it almost every year. This year we went to a place near Venice in Italy for 2 weeks. My parents their best friends are Alex and his wife Diane, who have been married for 16 years now. Alex looks a bit like a geek. He is 44 years old, has black hair and glasses on. His wife Diane has been my crush for a lot of years now, she is what you would call a cougar. She has long brown hair, blue eyes and a really good body, especially for a 42 year old woman.
My parents and I were meeting them at the airport on a Monday morning. We were waiting for themat the gate that our plane was leaving from, when I saw them coming towards us from a distance. “Hey look, there they are,” my mom said, while pointing at them. They were coming closer, damn, Diane looked even better then I remembered. She was wearing light blue jeans which were ripped a bit, black heels and a white t-shirt with a print on it. They were greeting my parents first, then Alex shook my hand and then Diane came up to me. She placed her right hand on my hip and I also placed my right hand on her hip, while we greeted each other with two kisses on the cheeks. “How are you Jake?” She asked me, while giving me a little hug. “I’m great. I’m really excited for going on
holiday. How are you?’ I asked her. “Yeah, I’m really excited too, it’s going to be fun again!’ Diane
replied. My parents were also talking with Alex, when we were told that we could board the plane.
On the plane I was sitting next to Alex and my father while my mom was sitting somewhere else with Diane. When we arrived at our destination, it was already evening so we looked around a little, made up our beds and went almost directly to sleep.
We were sleeping in a little house with a pool in the backyard. I was sleeping in a room upstairs, Alex and Diane were sleeping in the room next to mine and my parents were sleeping in a room
downstairs.
Day 2
When I woke up around 8 AM and walked downstairs, I could see that the table was already settled.
My dad and Alex already went to get some bread and some other groceries.
“Good morning Jake,” my mother said as I walked down the stairs.
“Morning,” I mumbled.
“Hi,” Diane said, who came from outside. I was stunned for a moment, she was only wearing her red bikini and her long brown hair was hanging over her right shoulder.
“Hi,” I stumbled. I felt my penis getting semi hard in my swimming pants, so I quickly sat down at the table to hide it. When my father and Alex came back, we ate breakfast together and talked about how everybody has been and what changed and stuff like that.
After we had breakfast and cleaned it up, we went to explore the surroundings a bit and we went shopping. When we came back it was around 5 PM and around 30 minutes later my mother and
Diane were cooking a meal together.
Diane had a white summer dress on and I could not take my eyes of her during dinner. A few times she looked back in my eyes and then I could see her beautiful blue eyes. Usually I look away when someone looks back but one time we looked in each other’s eyes for a few seconds and I could feel butterfly’s in my stomach. She was everything that I wanted on that moment. Alter the dinner, me and Diane decided to do the dishes. I was washing the dishes and she was drying them.
“Maybe we will finish faster if we first wash the dishes together or if you wash the dishes and I dry them?” I asked Diane. I asked this because she had to wait for the dishes because she dried the dishes way faster than I washed them.
“It doesn’t matter, you’re doing fine. But I can help you with it,” Diane said and she took a cup and started to wash it. A few times our hands touched in the water, even a small thing like touching her hand made me crazy. When we were done with washing and drying the dishes together, Diane took a glass and filled it with water. She drank the water at once. “A little thirsty?” I asked her. “Yeah it’s because of the heat. Do you want some?” She asked me, while filling her glass again.
“Yeah sure, wait I’ll get some ice cubes,” I said and I started to walk to the freezer.
I was looking into the freezer when Diane called my name. “Yes?” I said and I turned around.
Splash!, Diane just threw the cold water all over me, she laughed and ran outside. I was shocked for a moment but started to run after her. I ran outside and saw that my parents and Alex sitting at the table playing cards, they were laughing a bit when they saw me all wet. I was running about two meters behind Diane. She was turning right at the pool and I was coming closer. We were both laughing. She probably realized that it was not really smart to walk near the pool, so she started to run away from it. I was coming closer and grabbed her right hand. “Now I’ve got you!” I yelled and I laughed. I now lifted her legs up and started to walk to the pool. I saw that my parents and Alex were all laughing too.
“No, not the pool!” Diane screamed and she tried to get away but it did not work. I now was standing at the pool and said: “Do you want some water too?” “No thanks, haha,” she said. I put her feet back on the ground after she said that and said: “Okay, I’ll spare you for this time.” I could see that she felt relieved. “Or not,” I said and I grabbed her by the hips and jumped in the pool with her. We were both still laughing a lot and she swam closer to me and placed her hand on the top of my head and pushed my head under water. When I came up, she wanted to swim away again. Alex and my parents were still smiling at us but started to play cards again. I swam after her, dove underwater and grabbed one of her legs. She started to kick a little to get out but I started to pull her leg further underwater and got up again. We were both splashing water on each other now and she dove underwater this time. She came up right in front of me and I could feel her **** touching my chest. She had her arms around my waist and I could feel her vagina touching my erection. This was so hot and I wondered if she felt my hard ****. We looked each other in the eyes and our lips were almost touching. She smiled at me and took me underwater again. After goofing around a bit more, we decided to make peace. That evening I took a shower and Diane took one after me. We all played a few games together that night and went to bed around 11 PM.
Day 3
The next morning I was laying on a tanning bed in the backyard near the pool. My parents were sitting outside too. “Me and your mother are going to do some grocery shopping, is there anything that you want?” My father asked me. “Uhm, well maybe some sunbathing cream. I forgot mine,” I replied.
Diane just came outside when I said that, she looked amazing as always. She was wearing blue jean shorts with a red bikini top, red flip-flops and she was wearing her hair in a ponytail. “Good
morning all,” she said with her sweet and soft voice. We all greeted her and my mother asked if she needed anything from the grocery store, but she did not need anything. “Then we will get you some sunbathing cream, Jake. You can take ours in the mean while or else you might get burned,” my mother said to me, worried as always. “You can take my sunbathing cream too, it is standing on the dinner table. Wait, I will get it for you,” Diane said and she walked inside. My parents said goodbye to me and walked inside after Diane.
“Here you go,” Diane said when she came back. “Thanks,” I replied. “You want me to rub you in with it?” She asked me. I was really surprised by this and this felt kind of like a dream. “Would be great,” I said, trying to keep it cool. “Alex just woke up. He is going to take a shower,” Diane said to me. It sounded like she was telling me that Alex would not disturb us for a while and that she was giving me a hint with it, but thought to myself that I was probably just imagining things.
She shook the bottle and squeezed some cream out of it, then she started to rub in my belly, something that I could do myself but I did not mind of course. “You’ve been really working out haven’t you? You really got a great body,” Diane said while gently going up with her hand to my chest and my arms. I did not know what to say to that so I stumbled: “Thanks, I have been going to the gym a lot,” I felt pretty nervous and did not really know what to do with the flirting, was it just some innocent flirting or did she really want me to do anything? I could feel my penis was growing. She was gently rubbing my biceps and then told me to go lay on my belly, so that she could rub in my back. So I did and she lifted her right leg over me. She was now sitting on my *** and she started to rub in my back. “You’re really good in this, you should become a masseuse,” I said to her with a smile on my face. “Haha, thank you Jake. If I got guys like you on the table I would probably do it,” she said. Wow, she was now flirting with me even more obvious. I could not believe that this was happening and I started to feel a little shy. It felt amazing and my hard **** was pressing against the tanning bed. “Well, I would definitely be your best customer if you were a masseuse,” I replied.
Her hands were now slowly massaging my lower back. “Haha, you’re sweet. Turn around again, I forgot to do your face,” she said to me. I could feel her lift herself a bit up, so that I could turn around. Because I had a ***** I did not know if I should, but because of the flirting I did it anyways. She sat down on my ****, I could feel my hard **** touching her ***** through her shorts. There is no way back now, she definitely could feel that I got a *****. I was really hoping that she was really flirting with me and that she would not mind. But she did something that I did not really expect, she started to move her hips up and down and started to ride my **** very gently. I placed both my hands on her hips and she came down with her face near mine. She softly kissed me on my lips and placed her hand on my face. “I really want to do this but Alex can come down any time,” she whispered in my ear. She now took my earlobe in her mouth and started to suck on it, damn this felt so good. She was still riding my hard **** but took my earlobe out of her mouth. I grabbed her face and kissed her on the lips again, now I entered her mouth with my tong. We were now French kissing, I could feel her soft tongue gently touching mine. This was amazing. I had my left hand placed on the back of her head while we were kissing, my right hand went up from her hip slowly to her breast. I gently touched it and made circle movements with my thump on her nipple, I could see and feel that her nipples got hard, she moaned a bit in my ear. Her boobs felt amazing, probably a cup D. We suddenly heard some footsteps, it was probably Alex coming down the stairs. So we had to stop but she whispered in my ear: “We will continue this tonight, I will come to your room when everyone is asleep. At least, if you would like that?” “Yes of course I want that,” I replied and I gave her another kiss on the lips. She stood up, walked to the back door but Alex already walked out. Pff, that was close. What if we did not hear him coming down? “Hi!” He happily said to us. If he only knew what we just did and even worse what we are planning to do tonight. Me and Diane both said “Hi” back and acted like nothing happened. “Where are your parents?” He asked me. “They are doing some grocery shopping, so that we can eat lunch. They will be back soon,” I said. “Okay, I will set the table then,” Alex said and he walked inside. “I’ll help you,” Diane said. Before Diane walked in after Alex she looked at me and gave me a wink. Damn, she was making me crazy but I would get my chance. Yes tonight my fantasy would come true.
Later that day, when my parents came back, we ate lunch together and went to explore the surroundings a bit more. In the evening, we stopped at a restaurant near our holiday house to eat our supper. Nothing really happened anymore between me and Diane since that morning. We needed to hide our feelings and we needed to act like nothing happened. But we were sitting next to each other on the table, so I really had to control myself. She was still wearing her blue jean shorts but she was now wearing Adidas sneakers and a black top and her hair was no longer in a ponytail. Even in sneakers she looked very sexy.
We all had a fun time and laughed and joked a lot during the supper, my dad and Alex both drank a lot of beer, so they were both a little tipsy. Diane and my mother only drank one glass of wine.
We had just ordered our dessert, when suddenly I felt a hand on my right leg. I looked down and saw Diane’s hand with her red coloured nails on my leg and she slowly went up to my ****. It began to grow again and it was pressing against my shorts. “I need to go to the toilet, be right back.” I quickly said and I touched Diane’s leg. I wished that she would understand what I wanted. I wanted her to come with me. I had to hide my erection when I stood up, but I think they did not notice. “I’ll walk with you Jake, I need to go to,” Diane said. I was really excited that she just said that and my adrenaline started to pump. We walked to the toilets together but I pulled her inside the gents room. There was nobody inside. It was a small bathroom with only a toilet and a sink in it.
“I’m sorry, I couldn’t hold myself anymore,” Diane said and she took off my shirt. “Me neither, I was hoping that you would understand that I want you here,” I said while I opened the buttons of her shorts. I dropped her shorts on the floor. We then kissed each other and she took off her own top while I dropped my shorts on the floor. We had to work fast or else they would notice that we were gone for so long. I unhooked her bra and I looked at her beautiful big breasts. “Wow, you really are perfect aren’t you?” I asked her, after I unhooked her bra. “You’re sweet and not so bad yourself either,” she said. She looked me in the eyes and now licked her right hand, it looked incredibly sexy.
She dropped my boxers, “Well that’s a nice surprise,” she said. She took my hard **** in her right wet hand and started to ********** me. I could not hold myself anymore and after I dropped her black thong, I lifted her up and pressed her against the wall. She licked her hand again and she took my **** in her hand and leaded it into her wet, tight and bald *****. I went in with the top of my ****, it felt really good, it was warm and wet. She moaned a bit: “Ahh, hmm, **** me Jake, **** me hard and quick.”
I went in deeper and she was breathing harder near my ear. I went slowly up and down in the
beginning but I raised the tempo. She was moaning so sexy and cute in my ear, it made me even hornier. “Ah, ah, this is so good Jake,” Diane whispered in my ear. I was now ******* her fast and hard and saw her boobs bouncing up and down. I licked her right nipple while ******* her against the wall, her nipples turned hard. I kissed her on the lips while I was still ******* her, we were both gasping for breath. “Hmm, I’m about to come Jake,” she whispered in my ear. “Me to,” I whispered back. I went harder and faster and I came inside her, I felt shocks through my whole body and Diane moaned: “Ahhh,” it was maybe a bit too hard, someone could have heard her. She also shocked a bit and I went a few times up and down with my ****. “That was unbelievable,” Diane said. “Yeah, it really was,” I responded, still gasping for breath a bit. “Are we still on for tonight?” I asked her. “Hell yes,” she answered. She now went down with her face and took my **** in her mouth, there was still a little *** on it but she just licked it off. My **** was very sensitive so this felt really good. She took my boxer from the floor and lifted it back up again. “We need to hurry or else they will probably notice,” Diane said to me. So we hurried and when we came back they did not even notice, at least they did not say anything about it.
It was 11 PM when we got back at our place, first we drank something and then we went to bed.
Day 4
It was past 12PM when I went to my bed. I had 2 beds in my room, both for 1 person but I had shoved them next to each other, so that I would have a two persons bed. I was laying on my bed in the darkness wondering about a few things: Would Diane come to my room tonight? If she will come, how late will she come? Are we going to have love again? What if my parents and Alex found out?
I fell asleep after a while and woke up when I felt that someone came under my blanket, I felt a hand resting on my side.
“Jake, wake up honey,” Diane whispered in my ear. I was awake right away when I heard her say that. “Hey, I’m glad that you’re here,” I whispered back and I kissed her on the lips. Diane turned on the lamp that stood on the nightstand. The light was not very bright but bright enough to see Diane clearly now. She looked hot as always. She was only wearing a black bra and a black thong.
“I want to see you when we do this,” Diane whispered in my ear.
“I want to see you too, you look amazing,” I whispered back in her ear. With my mouth still near her ear, I sucked on her earlobe.
“Ahh,” she moaned quietly while lifting her body up a bit because she enjoyed the feeling.
I lifted my left leg over her body and laid on top of her. I placed my right hand on her cheek and whispered: “You’re so damn beautiful.” We looked in each other’s eyes and she smiled after I said that. She grabbed me by the neck with her right hand, pushed my head down to her head and we started to kiss. I felt her tongue entering my mouth and touching my tongue. We passionately French kissed for a while. While we were French kissing I lifted her back, unhooked her bra and slowly dropped the strings of her bra down her shoulders.
I gently squeezed her soft breasts and kissed her on the mouth. I slowly went down. First kissing her in the neck, then I kissed her above her belly button and then underneath. I slowly took of her thong and threw it away. I now kissed her right ankle, went up to her shin, her thigh and then kissed her clitoris. She was moaning and her *** was lifting a bit. I now started to suck on her clitoris and I was making movements with my tongue. Her ***** was getting wetter with every second and I could see that she really liked it. “Hmm, I’m already coming,” Diane whispered. Her body shocked a bit and she moaned a bit more. She squirted a bit in my face when she came.
She was breathing very fast and the only thing she said was: “Wow.” I kissed her on her lips and she placed her hands on my back and rolled me over. “Now it’s my turn,” Diane whispered. Her hand slowly went inside my boxer short and she slowly started to stroke my ****, it went hard immediately. We kissed each other and she now went down with her head, down to my ****. She took of my boxer short and stroke my **** again. She took the top of my **** in her mouth and played with it with her tongue. She was looking at me while she was sucking the top of my ****. She put her hair behind her ears so that I would see her face clearly, she gently went further down and she now had my whole **** inside her mouth. She went up and down a few times, still looking at me while doing it.
Diane stopped sucking my ****, she kissed me and whispered: “I want you inside me.” I really wanted to get inside her again so I directly rolled her over and kissed her in the neck, she moaned. I now kissed her on the lips and grabbed both her legs and lifted them up onto my shoulders. I now slowly went inside with the top of my **** and slowly went deeper, her ***** was warm and wet and it felt amazing. I went up and down and ****** her faster and faster. She was gasping for breath and I felt her nails on my back, after a few minutes I slowly took her legs of my shoulder and just laid on top of her, kissing her and still ******* her. She grabbed my neck and lowered my head next to hers, I could feel her nails and hear her moan in my ear.
“Ahh, roll over,” she whispered in my ear, I took my **** out and rolled over to my back, she started to sit on me, took my **** and inserted it into her vagina. I tried to go up and down with my **** while she went up and down with her body and moved her *** while doing it. She looked really gorgeous and I could see her boobs bounce every time she went up and down. She raised the tempo and she was trying to say that she was about to come. We went faster and faster and I rolled her on her back again and raised the tempo even more. I was about to come to and felt the *** coming out, while she moaned “Ahhhh,” near my ear. I went up and down with my **** a few more times and whispered to her: “This was perfect,” while I took my **** out of her and laid next to her on the bed. “Wow, yes it was,” Diane whispered back and she kissed me on the lips.
We laid next to each other for a while, cuddling and kissing a bit more. “I know it’s bad but I think I really have strong feelings for you,” Diane said to me after a while. “I really, really like you too.
Would you like to do this again sometime?” I asked her. “I would really like that,” Diane responded and I kissed her on the lips again.
