Hey, first post here! I had a lot of wild times in my 20’s. Definitely slowed down the later I got into my 30’s but I was reminded of this the other day so I thought I’d share and hopefully you will enjoy.
I was 21(M) and in the military stationed in Virginia. A friend of mine had a buddy from back home coming out to visit for the weekend so he wanted to take him out to Virginia Beach and see what kind of trouble we could get into. No plan at all except to start drinking and get a hotel room at some point in the evening so that we wouldn’t have to drive home.
First place we hit was somewhere on the beach with a back patio. It was summertime, early afternoon on a Saturday. We’re just shooting the shit and having a beer and at some point strike up a conversation with two women at the table next to us. Don’t remember what it was about but lots of jokes going on and whatnot. I don’t remember what the one woman looked like but I remember they were both attractive. The second woman, let’s call her Kate, was very pretty, slimmer, blonde hair past her shoulders, looked to be in her late 30’s. Come to find out she was a 42 year old fitness instructor.
After an hour or so they were about to leave but we tried talking them into staying and hanging out. The first woman had some sort of commitment, but Kate decided she didn’t have anything going on so she would hang out for a bit. We still needed a hotel room and wanted to get one before the night set in. These were the days before smartphones kids. Calling around wasn’t doing much good so the plan was my friend and his buddy would drive around to different hotels while Kate and I strolled the strip and tried to find the next place to hang out.
There was some sort of convention in town and the hotels were booked solid. As the hours went on I kept getting calls from them saying they were striking out. Eventually they decided they were just going to head home. Kate and I had been bar hopping for several hours at this point and I was on my way to drunktown. We drove separately so I told them not to worry and I would just sleep in my car.
Kate was awesome. Good conversationalist, sexy, classy, the whole package. I just kept thinking man, if she wasn’t so much older she would be the perfect woman. Story is already getting kinda long so I’ll spare the details of the places we went throughout the night, but she could blend into any crowd and situation.
Well at one of the places we went whilst sitting at the bar, a guy a little older than her starts talking to her while I’m talking to the bartender asking about the night life in the area. I can tell he’s hitting on her but don’t think much of it. She’s pretty hot so why wouldn’t guys hit on her? Well we leave and I can tell her mood has changed a bit. I ask if everything is ok and she’s like “that guy was hitting on me and you didn’t say anything about it”. That’s when it hit me like a ton of bricks. My new friend wasn’t just my new friend, sh wanted to fuck. All night I had just assumed I was too young for her so didn’t put the moves on her.
Fast forward to a few more drinks and we’re in the parking garage making out in the back of her car. She’s sitting on top of me, grinding on me while taking breaks from that so I can finger fuck her. We’re both going crazy and are about to seal the deal when a security guard knocks on the window and says we gotta take a hike.
Now at the peak of hornyness we decide to head out of town and hit the first hotel/motel we see (yes in retrospect we should have taken a cab but I wasn’t thinking clearly at the time and only had one thing on my mind). About 15 minutes down the road we see a place that is bigger and actually pretty nice. Lucky us, 1 room left. We get upstairs and clothes start coming off before the door shuts. She’s on her knees giving me the best head I’ve ever had in my life up until that point. We move to the bed. I eat her out until she can’t stand it anymore and begs me to fuck her. I crawl on top and start laying into her hard missionary style. She’s super wet from the anticipation and has already cum at least twice from my oral. This is my first experience with a woman that much older and I remember being amazing at how tight her kitty was inside and out.
She is vocal… and I’m loving it. I’m giving it to her hard and drunk enough that I don’t have to worry about spilling my load too early. She was a lady on the street but likes it hard and dirty in the sheets. She starts taking charge which I love. Gets on all fours and tells me to fuck her from behind and smack her ass. She’s a fitness instructor with a great body, but isn’t a twig. She has one of the best asses I’ve ever seen regardless of age. I obliged. I’m going as hard as I can, smacking that ass, pulling her hair… and then she puts a hand up to stop me. Oh no I think, I went too far. And that’s when it happens. A moment I will never forget as long as I live. She looks back over her shoulder and says “I want you to fuck me in my ass”. I couldn’t believe it. My first anal experience was with this goddess and she wants it bad. I said the only thing I could think of at that point… “I love you”. Lol. But true story. I pulled my dick out and moved it up to her hole. The juice was all the lube that was required. I pushed it in slowly as she winced just a tiny bit. I couldn’t believe it. It felt amazing.
I start out slow and get a little faster and faster as she’s on all fours pushing back on me with every thrust. Her vocals continue. I’m going deeper and faster until I just decide to push her on the bed flat so I can really dig in. I have her legs pinned down by mine and her hands held over her head so there’s no escaping, not that she wanted to. The harder and faster I go the more her vocals seem to be a mix of pain and pleasure at the same time. Eventually I’m going so hard she can’t make out words, just groans of ecstasy and orgasms. The bed is shaking and squeaking. Hell, the whole hotel probably is. I can see her eyes rolled to the back of her head. I’m fucking her ass harder than I do most pussy and she manages to let out a long intense “ohhhhh gooooddddd” and that was it for me. I go as hard as I can and shoot my load as far up her ass as humanly possible. Exhausted, we pass out.
In the morning on the way back to my car she tells me that her soon to be ex is a Navy Seal. So that’s awesome. Expecting a bullet to come flying through the window at any moment lol. She asks if I want to exchange numbers and we do. Yet neither one of us ever contacted the other. I’m not sure why to be honest. I guess I thought our experience was so perfect, why ruin the memory. Or maybe I was worried about getting my neck snapped by the ex. All I know now is that every time somebody mentions Virginia Beach it takes me back…