I just wanted to apologize if there are any grammatical errors. I am writing this on my phone and people in this sub make it look too easy lol.
This all happened when I was 20 and had just gotten out of my first real relationship. A little about me: I grew up a very overweight child, but at the end of highschool I lost a ton of weight to play college basketball. I was now 6’3 195lbs and was told I was very attractive. Except I was still that same fat kid at heart.
Just like any newly single 20 year old guy, I took to tinder and was having a great time receiving a lot of attention. One night while I was at my apartment with my best friend I ended up changing my age settings to 35+ as a joke. To my surprise this extremely hot 40 year old blonde had her Insta on her profile, so I followed her and dm’d her. To my surprise she responded and told me she thought I was very hot and that she wanted to get to know me better. At this point I was freaking out. I had never done anything like this before and felt way out of my comfort zone.
We exchanged numbers and talked for a few hours before she invited me over to her hotel room. She traveled a lot for work and was only in town for about a week. At this point it was about midnight and I told my best friend who practically pushed me out of our apartment and locked me out just to make sure I didn’t chicken out.
When I pulled up to the hotel I let her know I was there and she said to meet her around back. I was so close to chickening out and driving away, that’s how nervous I was. She opened the back door to the stairwell and oh my god was she not only real, but was extremely hot. She looked better than her pictures and was about 5’7, had massive fake tits, and a tight body. I’m not joking she was every guys MILF dream. As soon as she hugged me I was hard as a rock. But she grabbed my hand to lead me up the stairwell and I noticed this giant bruise on her left shoulder blade. My first thought was that she was leading me up to her room where her abusive bf was waiting to mug me and steal my pants. I have no idea why I was so scared about my pants getting stolen, but I was haha. But any guy reading this knows that I wasn’t thinking with my head. I was mesmerized and was blindly following her perfect ass up those stairs.
When we got to her room I honestly tried to be slick and look behind the doorways and around quickly for that crackhead/ pants stealing bf, but he was nowhere to be found. She did however ask me if I was okay because I probably looked like an idiot. I just said that I was looking for the bathroom. (Guys it’s a hotel room there’s only two rooms… she said confused “yea it’s right there.” I just acted like I knew what I was doing and stood in there for about a minute before flushing the toilet.
After looking stupid she led me to the bed and we started out by talking. I think she could tell I was nervous so she took it slow at first. Fast forward 20 minutes, and I leaned in and kissed her. Things immediately escalated fast we were making out and had our hands all over each other’s bodies. I took her red crop top off and went straight for those amazing Tits of hers. I took her hard nipples in my mouth immediately. (I love eating pussy it turns me on so much, and leads to way better sex if you start out that way). I laid her on her back and told her that I had to take care of her first. I started out by kissing down her stomach all the way to her nearly trimmed pussy. I hovered over her lips for a few seconds so she could feel my hot breath teasing her. Then I slowly licked all the way up her wet pussy and heard her moan. I used just my tongue for a few minutes before sliding my middle finger inside to search for her g spot as I continued to taste how wet she was. I loved feeling her fingers in my hair as she was moaning. I would Wait for her to get close and stop seconds before just so I could hear her beg me to let her cum. This went on for about 30 minutes and after she came 4 times.
She looked me in the eyes and said she had to have my cock now. I laid down on my back as she ripped my pants off quickly, and took my cock in her mouth instantly. She wasn’t the best at giving head which was surprising, but I’m not one to turn down a blowjob. I wanted her pussy so badly at this point that I pulled her off my cock and threw her on her back with my cock just at the entrance of her pussy. At this point I realized I didn’t bring the condoms up from my car, but we were both so turned on she just said fuck it and grabbed my hips and pulled me inside. I wasted no time and started pounding her. She was screaming and begging for me to fuck her as hard as I could. The headboard was smashing up against the wall and I’m sure her neighbors didn’t get much sleep for the next 45 minutes. Hearing her moan my name and screaming she was cumming was the hottest thing I have experienced at this point, and I was struggling to hold back my cum. She sensed this and started begging for it, she asked me to cover her. This was all the help I needed, I pulled out and shot ropes of cum all over her stomach and Tits. I laid down next to her and we both were completely out of breath.
After a minute or two she started stroking my cock again, and asked if she could ride me. Those words to a 20 year old male were stronger than any viagra I could’ve taken that night. We went another 2 quick rounds and both of us were spent.
I drove home exhausted and drained. The next morning I woke up to nudes of her and a text that said “come fuck me again tonight.”
If you guys are interested in night number two let me know. Also I wanted to add that the bruise ended up being from a guy at work wasn’t looking where he was going and hit her with some kind of heavy pallet. She managed construction sites which is why she traveled a lot.
Source: reddit.com/r/gonewildstories/comments/x42use/my_first_hookup_was_with_a_milf