As the title says, yes, this story involves squirting and lots of it. It was with an Italian cougar who I had met at a nightclub.
Until this memorable incident, I thought squirting wasn’t real. Pornstars faked it to get more views. Because until this moment, I never had any of the women I have slept with doing this. So I resigned to the fact that squirting was not real.
So here goes.
**The Pickup**
It was a Saturday evening, and I was going through a dry spell. No FWBs, no dates, nothing. It was a cold February night. I wanted to break the monotony — so I decided to go watch a late-night movie. The movie theatre was close by, and I had no intentions of going to a club because by the time the movie is over, it will be midnight, and I might be tired.
Anyways, I get ready to go to the movie. As I was heading out the door, for some reason, I thought I should just carry a couple of condoms with me. I didn’t know why. I just did. Maybe it was divine intervention.
I go to the movie, watch the movie. I left the movie theatre. It wasn’t that cold that night.
I decided to visit a local nightclub, only a few blocks away. I thought I will only be there for 30 minutes and then go home.
So I said, “fuck it,” and headed there. I paid the $20 cover and headed in. It was relatively packed.
I got myself a drink and started scouring the dance floor. For some reason, I was in a good mood. I noticed a few groups of women dancing, few couples, and so on. Then I saw 2 cougars dancing by themselves. It looked like they were friends.
I started dancing close to them. One of them wanted nothing to do with them. The other was slightly interested. So I took her hand, invited her to dance close to me, and started dancing. We started slow, and then we went fast, really close to each other. We continued this for like 10 minutes. I could tell we were both interested. After that, she broke it off and went with her friend to the bar to get a drink.
For the next 30 minutes, I was dancing or talking to strangers. I was just in the moment. Then I noticed that the cougar was back on the dance floor.
I inviter her to dance with me again, and this time we’re going hard. Her boobs pressed against mine, her thighs on my crotch, and my hands on her lower back. Either I was so good, or I got really lucky. Regardless, we just were having fun at the moment.
Her head was placed on my shoulders. So I lifted her head and pulled her in for a kiss. She reciprocated. There was massive sexual tension, and we needed to kiss to break the tension. First, it was a slow kiss, then it became a gigantic make-out session in the middle of the dancefloor.
We continued this for 10 minutes. And it was really loud in the dance floor. I asked her name. She said “Anna”. We both couldn’t talk. I said, “Anna, let’s find a table and sit for a bit and talk”. She agreed. I led her to an empty table at the back of the room.
As soon as we sat, Anna jumped on my lap, and we started making out. She held my head tightly and pulled me in. I took a break from her lips and started kissing her neck slowly to her revealing cleavage. I didn’t want to be a creep in the club by groping her, so I stopped there. She unbuttoned the top 2 buttons on my shirt and slid her hand in. She started feeling me. She took her other hand and slid it in my pants. Yes, she skipped the underwear and went directly to my cock. It was hot. I wanted to test the waters, so I slowly unzipped her pants and slid my hand in. I swear I didn’t go that deep, but it was wet.
At that moment, the rational part of my brain chimed in, “dude WTF, this is an open club, and everyone can see”.
I said, “Anna, we can’t do more here. People will see us”.
Either she was a bit tipsy or turned on. She pulled me and started making out.
I then said, “Anna, wait. I want to kiss you everywhere, not just your lips and neck.. everywhere”.
Anna took a moment, stared into my eyes, and then smiled. She asked me,” do you live close by?”
I said “yes.”
Anna “I am close too. I live in X. If you want we can go there”.
I said “yes”.
Wasting no time, I zipped her pants up, made sure my pants were proper, buttoned my shirt, and then led her out of there. I grabbed her hand, and she followed me.
We bumped into her friend. Anna told me to wait and then went and whispered to her friend. Her friend looked at her, a bit shocked. And then looked at me and then looked back at Anna. She signaled me over and said, “you look like a nice guy, but this is my best friend. Her safety is important”.
I told her friend “I will take good care of her. We are going to her place. Why don’t you take my phone number. You can call me tonight or tomorrow morning to check on your phone”.
Without hesitation, she took out her phone and grabbed my number. And once again, let me know “take good care of her”.
I said, “Yes I will”
We both said goodbye to her friend; we grabbed our coats and headed out.
It was still a chilly night. Anna and I held each other’s hands and walked as if we had known each other long. She asked me if I do this a lot. I asked, “What?”.
Anna “do you come to this club and pick up random women?”.
I said, “You are the first one from this club :)”.
She smiled and said, “You are smooth”. We both laughed and kept walking.
The sexual tension was so high. We would stop at various corners, make out heavily for a few moments. When we felt the cold breeze hit our necks and hands, we would stop and keep walking.
Her apartment wasn’t close by, and one of my best sexual adventures awaits me.
**The Sex Part.. Correction. (The Mind-blowing sex).**
We reach Anna’s apartment. It was a gorgeous 3-bedroom apartment with a splendid view of the city. Anna got me some water, and we headed into the living room. There were pictures of her kids and family.
She opened up and told me she was Italian, been married for 20+ years. Now divorced. Had 2 young kids who live with her, and on some weekends with her ex. We talked about this for a bit. Then she told me she and her ex-husband hadn’t had sex for 5 years. I told her that I didn’t believe that. How was it possible? She told me she was in a dead bedroom situation.
To cheer her up, I said, “Well, tonight, let’s change that. I am going to help you with that”.
She laughed “how generous. hahaha”.
We pulled towards each other and started making out. We were standing for a bit. Then I sat down on the couch and had her sit on my lap. By now, our make-outs have gotten more intense. I took off her top. She took my shirt off. I grabbed and boobs and started slowly kissing them. Then I took her nipple in my mouth and started sucking on them slow and then fast. Her moans grew louder and louder, all while she was grinding me.
It has been a while for me, and I was hungry to eat some pussy. I wanted to go for the treat. I told Anna to take me to the bedroom. We both stood up topless and walked into her room. I noticed something strange, my pant was wet. At first, I thought she peed on me, but there was no smell.
I was a bit perplexed. Did I make her so wet??
I made Anna sit on the bed and took off her pants. Then I took off my soaked pants. We were both in our underwear.
I pushed Anna on the bed. I started kissing her boobs and nipples and slowly made my way to the panty. I decided to tease her a little bit. So instead of going for the panty, I went to her thighs. I started slowly kissing and moving my tongue up and down each thigh… She kept moaning and moaning.
Then I slowly pulled down the panty using my teeth. I could finally see her wet pussy. It was glistening. I liked how it looked and smelled. I decided to play with it.
I circled my tongue around the pussy, and I took a break to see my finger in her pussy.
What happened next was shocking.
As I slid my one finger, she left out a huge moan, and then something wet hit me. And then it kept coming. Before I realized I had just been squirted on. She squirted on my forehead. I was in a state of shock and exhilaration. Is this really happening?
Before I could say anything, she looked at me “I am really sorry, this happens when I am excited”.
I said , “Anna are you kidding? This is awesome. This is so hot”.
Anna ” I get really excited, and I can’t help myself.”
I said, “Then let’s help you let loose.”
I went back to fingering her and eating her pussy. The scent, the pussy juice, and the squirt made it all exhilarating. I first went slow, then fast. She pulled my head closer to the point I was suffocating. Her legs were over my shoulders on my back.
Her pants and moans started accelerating, and then she lifted her legs and pushed my head back. She squirted again—this time not a large quantity like last time.
She lay there breathing a sigh of relief. She said, “I am sorry”. I told her not to apologize, and I liked it.
Then she pulled my head closer and started kissing me. She got up from the bed and made me lay on the bed. She pulled my boxers out and started stroking my dick. She didn’t waste time, and she would begin kissing and sucking it. It was not hard movements but rather slow. Occasionally she would look at me, smile, and then go back to sucking my dick.
She asked me how old I was. I told her I was 34. She said, “I am 48, just you know. Have you ever been with a woman this old?”
I said “No”.
She asked, “What do you think?”
I said, “Anna, this is one of the most surreal sexual experiences. Probably one of the best”
she “You are a liar.”
I ” I’ve never been squirted on twice. And you are sucking my dick amazing”.
She smiled and went back to what she was doing.
Then she asked me if I had a condom. I reached for my pant and took out one of them. That weird hunch at the beginning of the night had paid off. Who knew I needed to use a condom tonight… LOL
She slid the condom on me. Then she rubbed her pussy slowly over the tip, and she slowly slid into me (cowgirl position). It was so wet and hot. I have never felt anything this wet. Usually, I always had to put some lube on. No, Not this time.
We continued on the cowgirl position while I was squeezing her boobs. This woman knew how to enjoy herself. I thought to myself, “What type of loser husband wouldn’t have sex with this goddess every night.”
Then we switched to a missionary position. We kept going at this for a while. Her moans started increasing more and more, then at the moment, she pushed my chest to signal me to pull out. And this moment, she left out another squirt.
I asked her if she wanted a break. She said No. So I went back in.
Then I pulled her to the end of the bed and asked her to turn over. I entered her in the doggy position. We probably were in this for 15 minutes. I have never experienced something so wet. Then it happened again. This time she wanted me to feel it all. She didn’t warn me. She sprayed my dick and stomach with her juice. This time she didn’t apologize. She was enjoying it more and more.
We did a few more positions. Then we went back to missionary position. She asked me to cum. She wanted to feel my juice in her. So I held her tightly and started pounding in the missionary position. She wrapped her legs around me. I took her hands, put them on the bed, and grabbed them. She then squeezed my hands tightly. We continued this for a while, and then I came.
I let out a satisfied orgasm. We were both panting and heaving. We were also sweating a bit despite the cold night.
We both got up to go get cleaned up. We brushed our teeth and went back to bed. She said if I want I can stay over. I agreed.
When we reached the bed, I was surprised. It was soaked. It felt as if someone has poured a lot of water all over the body. I didn’t complain. Neither did she. We both seemed to enjoy laying down in a bit filled with her juices.
We talked a bit. She told me about her life and asked about mine. Then we fooled around a bit more. Then we dozed off.
In the morning, I woke up to a raging boner. I mean, how can I not. I was in bed with a hot cougar, and it was wet with her juices. I started slowly rubbing my dick on her ass and grabbing her boobs at the same time. She was awake, and she started slowly grinding me. Due to morning breath, we didn’t kiss. She reached over to her drawer, picked up a condom, and handed it over. I put it in and slid my cock in her. It wasn’t as wet as last night. She told me she was all juiced out. We continued this for a while. She asked me to come on her body.
I took my dick out. She immediately pulled out the condom and threw it out. Then she started stroking me hard. I couldn’t hold it, and it came all over my belly.
We laid there a bit exhausted. After a while, she looked at the watch and said her kids would over soon, and I needed to go.
I put on my clothes. As I was heading out, I asked her if she wanted to do this again. She agreed. So I said we should exchange numbers. She took out her phone, asked for my number, and then started at me. At this moment, I realized and laughed, “wait, you don’t know my name, do you?”.
She blushed, and I could tell she was a bit embarrassed. I told her not to worry and gave her my name and number.
I left her apartment, called an Uber, went on home, and slept like a baby. It was one of the best post-sex sleeps I have had. I had never been that satisfied until that moment.
Much to my dismay — Anna and I didn’t meet up again. She only wanted a one-night stand. I tried a few times, then stopped messaging her.
Even if it was just a one-night-stand — it was truly memorable.
Source: reddit.com/r/gonewildstories/comments/nr1yqw/mf_the_time_an_italian_cougarmilf_f48_squirted_on