My friend was too scared to post this story himself so he decided to let me reap the karma. Here’s the story as he told it.
Author: NotMyDogPaul
[MF] lost my virginity to an older woman and made her cum 1.9 times.
So my last story on this sub enjoyed a bit of popularity. I decided to share the story of how I lost my virginity.
So I was a bit of a late bloomer. I was 22 at the time and the year before, I made out with an older woman and I basically found something out about myself that day. I like cougars, so naturally, I set up a cougarlife.com profile. It didn’t take long for me to connect with a much older woman. She had a gorgeous pic and we would chat all the time. We exchanged numbers and after a little while we decided to meet. She lived like 90 mins away and she decided to drive on up to see me on a weekend. We met at a local park on a Saturday and we walked around and talked. We got frozen yogurt and started talking about my favorite topic, standup comedy. We came to my place to “chill and watch Netflix.” It wasn’t lost on her. I had just gotten a new stethoscope at the time (nursing school) and she was in the field so I showed it to her. She asked to listen to my heart. “wow. It’s going so fast. Your lips just look so kissable” she said. It took what felt like an hour for me to get the courage to say “then why don’t you just kiss them?” But I did. And she did. We went to my room. I took off her bra with one hand. Still proud of that lol. Her breasts were very large and smelled like lotion, not to mention the undeniable and intoxicating scent of pheromones. We make out for a little bit and she instructed me to take her pants off and go down on her. I have poor coordination. To hit the clit with my tongue, I decided to rub it with my finger and follow my arm and hand down to my to tongue. But it did the job. She even though it was charming. She asked “how do I taste?” And I just said “like the ocean” and continued on eating. I started fingering her and remarked that “it really does feel like warm apple pie” and that made her laugh quite a bit. But I kept going. I was on a mission. I felt her pussy tighten up and I freaked out. I immediately withdrew my fingers. I didn’t expect it. She was annoyed but understanding. And momma didn’t raise no quitter so I got back on the horse and finished her off. She then started working on me, and I started making these horrendous noises like a cat immigrating its owners orgasm. She thought it was rad. I was just such a fuckijg virgin and she loved it. Then, for the next few hours I was mainly fingering her and eating her out while doing things to her nipples like sucking and rubbing. That was nice. And she had me whisper Russian poetry in her ear. Idk what that was about but that’s cool. No skin off my back. This whole time, I can’t cum. Way too nervous even though it feels incredible. I tried to put on a condom but made the mistake of unrolling it all the way and trying to stretch it over my dick. She helps me out on the other one. We start penetrative sex and she’s uh…well, let’s say cavernous. Plus the condom. No sensation. She had to keep fluffing me and it just wasn’t going anywhere. We were both really tired by then and hungry, not to mention I was in a bunch of pain. I I cooked up some hash browns from scratch and she left. Then I jerked off and turned the night sky white. We still occasional hi via text. The end.
[MFM] my two friends ask me to join them for a threesome which leads to the most awkward first time cuddling in history.
Let’s call my friends Joe and Joanne. That’s not their real names but that’s okay. This was in 2013 when I was 19 years old and still a virgin. My friend Joanne lived in Europe at the time. She came to visit me and I picked her up at the airport. She had a really long flight from Germany to California so we decided to go grab a bite to eat. We went to her favorite Chinese place from back when she lived here and we saw my friend Joe. He came over and we sat together. They hit it off like nothing I’ve ever seen. We go back to my place and he is mapping out her body with his hands like fucking Vespucci. The sexual energy was causing disruptions in the power grid. Then they said “hey NotMyDogPaul, wanna have a threewo?” Being a virgin, a storyteller and a person who has always been taught to accept something offered with an open heart with a similarly open mind, I didn’t think I was really in a position to refuse. We started talking and about how to do it because Joe and Joanne were also virgins at age 21 and 19 respectively. But after much consideration, they decided that it’d be weird if I join in, even though they’d be fine with me standing in the corner and watching and touching myself. That was a touch to much for me, though. I let them use my bed and I gave them condoms because I want to be a good host. They were really having at it. The best way to describe it was bears battling evolution. Ugly grunts and groans. I couldn’t sleep. They were too loud. Finally, I hear their night come to a crescendo. Joe had to go immediately after so they both took a sexy shower together and he left. She could see that I’m feeling awkward about the whole situation. I was excited to lose my virginity and it didn’t happen but it was my problem and I didn’t wanna make it her problem. She says to me “hey NotMyDogPaul, he fucked me but he didn’t cuddle with me. Do you wanna finish the job he couldn’t?” So I cuddled with her as she was in her underwear sporting an awkward boner as the big spoon, trying desperately to keep my hips away from hers. She then told me about her fucked up childhood for 6 hours straight as I reexamined my life choices. The end.