We fucked in her car surrounded by a crowd of people. [MF]

To understand a little better, you should read [this one](https://www.reddit.com/r/gonewildstories/comments/8rhk13/taking_an_old_friends_virginity_one_summer/?st=JINLBLFV&sh=bd875fc5) first so theres context.

Me and Heather had been at it for about a month now. She knew what she liked. I knew what she liked. At this point we had done pretty much everything minus anal. We fucked in a pool, jacuzzi, the shower, her house, my house, other peoples houses, but tonight would be new for both of us. I had a show to play. I was filling in for a friend of mine who had knee surgery so he couldn’t play drums for 6 weeks. Not my style of music, but we go back and I said I could fill in while he’s out. Heather had never seen me play live before so she asked if I mind. Of course not. I play in front of strangers all the time.

Edging, squirting, being spied on, and getting walked in on. Tiffany sex chronicles [MF] [Long]

Tiffany had a nursing thing she had to attend in Chicago. I had to meet her there because I still had a few weeks left in the Marines. I land at Ohare and she picks me up then we head to the hotel. She warned me ahead of time she had coworker sharing her room. We pull up to this pinky out monocle wearing establishment called The Peninsula Chicago. We were upstairs in their room overlooking the city and doing the meet and greet. They had a suite and her coworkers were mingling waiting on us. I see a few familiar faces from my last story and some new ones. They were all way overdressed. Here I come in khaki shorts and a Gorgoroth shirt. I fit in.

Taking an old [F]riends virginity one su[M]mer

This takes place exactly a decade ago this month. 18 year old me gets a text from Heather. Heather is a childhood best friend that I grew up with and lived around the corner from. We have a lot of history. None of it sexual until now. We just graduated high school and both turned 18 recently. Our conversation goes something along the lines of “hey. I need to ask a favor. A serious favor.” I’m typing from memory, none of this is direct quotes, just a summary.

Me – everything ok?
Heather – yeah, it’s something personal though and I don’t know how to say it.
Me – I can’t help if I don’t know what the deal is.
Heather – ok, fine. I want you to take my virginity.
Me – are you fucking with me?
Heather – I’m still at work, I’ll come by after I get off.

Now at my house…

Heather – you’re one of my oldest friends. You’ve always had my back and been good to me. I trust you and I know who you are. All of my friends have been talking about sex lately and I’m the only one that hasn’t had sex. I think about it all the time and I want to do it. I want it to be you. So?

Drunk ex gets her first anal creampie [MF]

Better to read the Hawaii story first if anybody is reading this one without knowing the story so far.

Tiffany had money. She was a seasoned nurse anesthetist. I have no idea what that means, but she made enough to live in a really nice area in San Francisco, drive a jaguar, an wear (ironically) Tiffany jewelry. She liked to spoil me. And to clarify, I never asked a dime out of her. So, a group of nurses and doctors plan a dinner party at this really upscale place called lazy bear. All fancy rich people. Yachts and Rolex’s. Way out of my league being from crime infested New Orleans. So I have to dress the part. All I have is dress blues which I’m not fucking wearing. Tiffany takes me to this tailor and gets me fitted. Shoes. Ties. Sunglasses. All that other shit that you wear with a suit. A Tag Heuer. I see all this being rung up and I had to step in.

A week well spent in Waikiki [MF] [LONG]

My last deployment had us hopping between countries for the last three months of a ten month tour. Our last port visit before we got back to Cali was Hawaii. It was the week of my birthday. Me and my squad, yes a literal squad of Marines, were tearing up the bars in Waikiki. We get a solid buzz going when we go to this one place that was pretty busy. Couldn’t tell you name. Good crowd. Good music. Good vibe.

Then, like in cheesy rom coms, I see her across the room talking to her friend. Her smile was killer. Long wavy brunette hair down to her lower back. Tan skin. Glasses over her bright blue eyes. Curvy body. She was absolutely beautiful. She had a radiant glow about her. Could’ve just been me seeing that though.

I was trying to think of something to say when she starts walking straight at me. I’m 23 years old at the time. I’ve been in combat. I’ve been wounded. Why the fuck am I nervous? It seems like she was walking at me for an hour. She was wearing a maxi dress which showed off her figure perfectly. She gets closer where I can size her up a little better. I’m 6’3, she’s almost eye level with me. 6 feet tall busty Amazon goddess, and she walks right passed me. I missed an opportunity.

Intense threesome with best friend part 2 [MFF] [LONG]

Follow up threesome to my threesome with Maddy and Bri.

So, this picks up exactly where the last one left off. I guess one of them got cold in the middle of the night because we woke up with a blanket covering the three of us. It’s about 11am. The sun is peeking through her sliding glass door right in my face. Remember, we’re in the living room. I drug a mattress from the spare room so we had plenty of space. The room looks like sex dungeon. Lube on the table. A vibrator on the sofa. Towels and baby wipes all over the ground. Maddy must’ve taken her butt plug out sometime after we all passed out.

She looked gorgeous sleeping. The sun was hitting her her naked back with a little of her ass exposed. Bri was really really drunk. I don’t even think she fell asleep. She passed out. Her plug was still in. She was laying flat on her back, dark hair covering her shoulder. Perky pink nipples standing erect. I got up quietly to go do my morning routine; brush, quick shower, reevaluate the last 15 hours, contemplate the details, etc. etc.

Intense threesome with best friends [MFF] [LONG]

A few years ago I was hooking up with this girl pretty regularly. We’ll call her M and her friend B. M was a foot shorter than me at 5”3’ but she is absolutely stacked with 36DDs. Fantastic ass and smooth legs. Former competitive cheerleader. Anyway, we’re at her house hanging out having a good time around the pool. As the sun starts setting we all hop in the hot tub. There’s about 10 of us. We’re drinking and having a genuinely great time. M is sitting in my lap with B directly across from us. Dark hair, pale skin, perky Cs staring right at me in the hot water. A few bottles go down in the heat and we’re all feeling it. Happily buzzed and laughing it up.