This is Part 2 of my sexual encounters with Lisa the businesswoman cougar. One of my best and wildest sexual experiences. You can read Part 1 here.
This story happened a few weeks later. Lisa messaged me to check how I was doing. She said she is planning a solo road trip to a nearby lake 2 hours north of our city. And asked me if I wanted to join. I was excited for sure. How can I turn down the opportunity? I immediately replied, “yes”.
She said she was going to rent a car, and we can switch driving on the way. Then we will book a room once we get there. We agreed to meet outside a mall — she would pick me up and then head to our adventure.
This was my first time I’ve been on a road trip with a woman. Most of my past sexual adventures happened in my bedroom. So I was excited to try new things.
On Saturday, I packed a small bag and headed to the mall where we were supposed to meet. I got there 20 minutes early. I wanted to get some condoms, lubes, and mints, and I did.
She met me outside at the time we decided. As I stepped into the car, she wore a red summer dress — a red top and red shorts. We hugged, and we were on our journey.
Throughout the ride, we chatted about past relationships, sexual kinks, our dating history, etc. It was an interesting chat. Occasionally, we would make a pit stop, and I would switch with her.
During our trip, we got to talk about sex. I told her, “I’ve never had bareback sex and also haven’t cum in someone”.
She laughed. I then told her, “I was a bit nervous, so I rushed and got myself tested — all clean”
She ” Relax, I get tested occasionally, and at this stage, I don’t think I can get pregnant”.
She then asked, “Did you like it?”
I “Of course, I couldn’t stop thinking about it.” “By the way, I did purchase some condoms and stuff. It’s in my bag”.
She smiled. We both smiled. She was silent for a bit.
I “You don’t want to use them, do you?”
She said, “No”.
I was getting turned on just by the thought of penetrating her raw wet pussy. I could tell that our conversation was turning her on too. A part of me just wanted to pull over and make out with her. But for some reason, I resisted and told myself to wait.
We entered the town that we had intended to visit. It was early evening. We agreed to find a nice room first, then get dinner, then go for a walk on the lake.
We found a nice room and paid for it. Next, we see a local restaurant. We park the car and head inside to eat dinner. We ordered food and spoke during our dinner—nothing sexual, just a casual chat.
Once dinner was over, we settled the bill and headed out.
As we walked to the car, there was an awkward silence, and I felt a sexual tension. She looked at me and smiled. That sly fox. She knew what she was doing, LOL.
A part of me felt the strong urge to pull her closer and kiss her right in the parking lot. But I resisted. I should have. It was a town far away from our city, and nobody knew us.
I got in my head, and I did not pull the trigger.
We got in the car and agreed to go to the room to put down our things and then head out to the lake.
We entered the room. Put down our stuff. The room was neat — two large bedrooms, a big bathroom, and big TV, and there was a sliding door that had a view of the other rooms in the hotel.
We stepped outside for a bit to take a look at the view. Our goal was to just check it out and then head out. It was a bit chilly.
We were standing close to each other, almost touching our bodies. So far, we haven’t made any physical contact. So the sexual tension was in the air. We both looked at each other and smiled.
At that point, all my nervousness died, and the sexual tension had overtaken everything. I couldn’t hold it any longer. Enough is enough. Fuck.
I pulled her for a small kiss. It started small, and then immediately, it became a wild makeout. We made out for a bit on the balcony. I held her hand and then took her inside the room. Closed the door and curtains.
We started making out passionately, holding each other tight. Soon she started to take my shirt off, and I took off her top. I then sat on the bed and placed her on my lap while kissing her neck and then sucking hard on her boobs and nipples.
I then put her on the bed. She took off my pants and underwear. She was only wearing a panty at this point. She started kissing and sucking my balls . I was hard, I mean really hard. It was hot watching her suck my penis top and down. After some time, I asked her to stop and pushed her on the bed.
I slowly removed her panties using only my teeth. But as soon as I saw her glistening wet pussy, I decided to throw the slow pace out of the window.
I immediately started kissing and sucking, and fingering her pussy. I was down there for a few minutes, then she asked me to stop and enter her.
I was more excited this time than the first time. I am going to enter her raw, and this time I wanted it badly. I have now been addicted to barebacking. I slowly rubbed my hard dick on her pussy, and then slowly entered her. I wanted to see, feel and experience every inch going inside. I put it inside all at once and took it out. I could see a little bit of her cum on my brown dick. I loved that natural lubricant.
So I kept going in this position — I was standing, and she was on the bed. We kept at this position for a while.
She then told me I got something in my bag and took it out. It was coconut oil. It was the best lube, she said. And she was right.
She then told me to lie down. Rubbed some lube on my dick and slid on top of me. We were in the cowgirl position for a while.
Then she started pounding me hard. It was kinda exciting to me. She was going up and down so hard. She loved to fuck. A couple of times, it slipped out, and once, it even hurt. LOL. So we decided to change positions.
We tried so many positions for a bit. Then she told me to come from behind – doggy style. So I did. I was pounding her from behind while squeezing her at. At this time, she started playing with her clit. She told me to slow down and go deep.
And when I hit the cervix, wait, then go out and go back all the way in again. So I slowed down while she was wildly rubbing her clit. Man, I love cougars — they know what they want :)
We then decided to try the spider position. This was the first time I have ever done it, and I thoroughly enjoyed it. We were able to see each other while enjoying each other’s genitals. This was both our favorite position, and we both seemed to enjoy it.
We tried many other positions. This was 5 years ago. I don’t remember all of it. But there were a few. At this point, we were probably 45 to 60 minutes into our sessions.
Then she wanted to try something new. She sat up on the bed with her back. I laid on the bed and was hitting her from the side at 45 degrees. I wish I could find the position online, but I can’t. I was going in and out while she was rubbing her clit.
I could tell she wanted to come. I had one hand on her boobs and the other on her thighs. I tried to make her cum first and then cum after that. But I couldn’t hold it any longer. I have been raw-dogging her for an hour now.
I couldn’t hold myself and came hard inside her while she was still masturbating. I lost control. I took my dick out and saw a stream of my cum escape her pussy. I decided not to be a selfish lover, so I decided to help her.
I put my finger in her cum soaked pussy and started fingering her. I have never done this before, so it was hot. I could feel the smell of my cum already filling the room.
I didn’t feel weird and didn’t want to ruin the moment. So I kept fingering her hard, using my cum in her pussy as the lube, and she rubbed her clit hard. Soon she came and let out a huge moan.
We then lay exhausted in bed. It was a long fuck session. And we looked outside; it was dark. So we naturally skipped the walk on the lake, lol.
We both went to the bathroom to clean ourselves up. Then we crawled into bed and cuddled. We talked for a bit. After some time, she said she needed a bit more space because the bed was small.
She asked if I minded if she went and slept on the other bed. I didn’t mind at all. After a sweaty, intense session, we both needed to get rest.
I remember falling asleep too fast. I probably slept like a baby.
In the morning, around 7 am, we were both awake. We smiled at each other from different beds. We greeted each other good morning.
Then in a moment, she jumped from her bed to mine. I was shocked but also turned on. She started stroking my balls and then sucking them.
I told her to stop because I wanted to eat her out too. I told her I needed to go brush. You know, because of morning breath.
We both went to the bathroom and brushed our teeth and then ran back to the bed.
We kissed and sucked each other off. Then we put some lube on and decided to go back to our favorite position — the spider.
We continued for a while. I was on the verge of coming. So I grabbed her and pushed her on the bed. And started going hard in the missionary position. Within some time, I came hard.
We lay in bed, both panting and heaving after the morning quickie.
Then we both took a shower, got dressed, checked out, had breakfast, and hit the road again to return home. We continued to have a good chat on the way back.
She then dropped me off at a place not far from my home. We hugged, said goodbye, and agreed to get together again soon.
If you liked this adventure with Lisa, I have other spicy ones too — once at a hotel, we booked after dinner and the other one at a sex club…
If you liked this and the last one, I am pretty sure you will enjoy the next one too.
Source: reddit.com/r/gonewildstories/comments/xwos68/mf_a_fun_weekend_road_trip_i_32m_went_on_a_with_a
Please more that!