Once Upon a Life – Part 2 of Many [MF] – Matt’s First Night Sleeping With a Female

**Once Upon a Life**

**Part 2 of Many – Matt’s first night sleeping all night with a female.**

Here is the story of how Matt spent his first ever night with a female, a young lady.

Near the end of the summer there was an end of season picnic and awards ceremony for a summer league baseball program Matt had played in.

The season was over and all of the families and players were invited to a huge park. It was a huge pot luck, many grills were going and people were playing catch, Frisbee etc.

During the time there in the park, another ballplayer that Matt knew came up to talk to him. Matt knew of this guy and had known of him for years and years as they’d played against each other many times. But, this guy went to a different high school than Matt did, in the next town over so while he knew of him, he didn’t really know him. They didn’t hang out together off of the ballfields etc.

Once Upon a Life – Part 1 of Many [MF] – Background – Setting the Scene

**Once Upon a Life**

**Part 1 of Many – Background – Setting the scene**

The story will begin in the mid 1980’s with a young man named Matthew.

It was August and Matt was excitedly looking forward to beginning college in a few weeks. He was going to go to a large university, with many tens of thousands of students and he was looking forward to the coeds in particular of course.

Matthew was dating his high school sweetheart, a young lady named Julianna. Julianna was also going to be going to the same university as Matthew. They were both going to be living in the same dorm.

Matthew was in love with Julianna. They had dated all four years of high school, gone to prom together as juniors and seniors and they were now going off to college together.

While Matthew loved Julianna and thought he would likely marry her after they graduated from college, he wanted to have fun, experience all he could in college. In short, he wanted to have a blast in college, before the toils of adulthood hit him head on.

[Mf] Night of taboo passion between distant relatives

It was about 10 months ago during the time when my cousin was getting married. She invited extended family and everyone gathered together in one location for a weekend-long wedding. Since our families never interacted much, I [33/M] basically felt like a stranger among a sea of relatives. I said my hellos and mostly kept to myself.

Since it was a big family gathering, we had one of the hotel floors to ourselves. It was a pretty cool setup where people could congregate in the lounge and catch up or talk about old times. Again, not knowing anyone around, I mostly stayed in my room or greeted some people.

Late one night, at roughly 1 am, I felt like leaving my room to go to the lounge. As I neared the area, I heard a faint sound and was surprised that anyone would be there. I walked in slowly and saw on the couch the younger cousin of the bride, so my cousin’s cousin. I remembered being introduced to her earlier and thinking she looked really good, but then cursing myself for finding a relative attractive. She was a junior in high school, so that was doubly perverse.

[MF] Hooked up with an ex on my birthday and she gave me the blowjob of a lifetime.

One day out of the blue I get a random Friend Request from an ex I had dated for a time shortly out of high school. It was brief, but honestly the only thing I missed about her was the amazing sex. So naturally the other head got the best of me and I accepted. Almost immediately we started into small talk, just catching up. This goes on for a few days until I figure she’s just bored so I kind of lose interest in the whole thing pretty quick.

That is, until the day before my birthday. She knows it’s coming up and I told her I was kind of bummed because I had to work early the next day so I didn’t plan on doing anything special. So then she asks if I think I can get any weed so we can catch a buzz and watch a movie instead. Not on such short notice unfortunately, I tell her. Her next response was something I’ll never forget.

[MF] ~Half a Decade in the Making! [LONG]

2012. Snapchat was in full effect. A new way to connect with all my high school friends even after we graduated because we all promised too. We all know that’s not what happened though, it never ends up like that.

Fast forward into the summer of 2017, Most of us have gone off to college or something of the sort. It was a slow day at work so I decided to check out some Snapchat stories to pass the time. I notice my old friend Kara post a picture of her new dog and I couldn’t help but swipe up and comment about how cute the dang thing is. Kara thanks me and we make some small talk about how our lives are. I make a comment about how I couldn’t wait to get out of work and head to the gym to relieve some stress. Kara opens my message but replies with a picture of herself in the mirror in a sports bra and tight spandex shorts captioned “I just finished my workout.” Now I had never looked at Kara in a sexual way, last time I saw her she was short (and I mean short! 4’11”), had a larger frame, and kind of geeky. I was in shock about the picture because she was absolutely gorgeous, her body now tight and fit, her boobs were double D’s, and an ass she made sure to show off while still being 4’11”!

That moment I realised I got turned on by watching my bf with another girl [FFM]

So once I was in high school, just turned eighteen. I was one of those nerds (which at the times still meant uncool) who had the potential to be hot (really big tits, big lips, thin legs) but still refused her potential. My bf of that time (we had already been together 3 years, he was my first and only one, same for him) was kind of like me, nice features but not a man yet.
I had a best friend at that time, let’s call her Natasha, and she was everything that I wanted to be and never hoped to: confident, amazing long hair, perfect, firm round ass, elegant, witty. I had always envied her, and at the same time found her so attractive.
I know my bf felt the same towards her. He was very religious and I was very serious too, he wanted to marry me and was sure I was the one in his life. He would never, ever cheat on me. But I saw him looking at her ass a couple of times, and once I saw a pic of her in her swimming costume saved on his phone. In that moment, when I discovered the picture, I was expecting to be furiously jealous. And I was. But I was much, much more turned on by that. And I felt so guilty about it. The thought of my ex boyfriend jerking off to her picture turned me on in a way that sex never had between us in the past. So I didn’t tell him anything.
The three of us were very closed and shared the same sense of humour. She was way sexier and more attractive than me, but I had always known that someway, she was attracted by me. I think she envied my huge tits, and when giving me “girl hugs” I could always feel her rub her tits against mine a bit longer that what those hugs required. Once, during a bet in class she had kissed me on the lips and bit my lip a little bit, and then looked at me in a weird way before shrugging it off and pretending it she was doing it for the crowd. Anyways, I used to masturbate thinking about her kisses and ass a lot, during that period, but obviously never told my bf about, cause religious and being a huge homofobic and all that kind of shit.
So one night we went to an house party, the three of us. It was in a friend’s kitchen and bedroom, we were like five and constantly going in and out the room. At a certain moment I got caught in a conversation with a classmate and I see my bf going to the bedroom. I knew that Natasha was in there, but didn’t give a lot of importance to it. The bed was positioned in a way that was almost behind the door, but you could actually see a little bit if you angle it well. After ten minutes talking with this classmate and Natasha and my bf still in the room alone (presumably in the bed area, since I couldn’t see them) I started to think it was weird. My classmate went in the garden with the others and I decided to go and see what they were doing. I get closer to the door in that angle where I could see the bed and I see the two of them “playing” on the bed. They weren’t kissing or anything like that, they were kind of wrestling but while doing that I could see my boyfriend rubbing his cock on her ass. She was pretending to fight back, but she was actually enjoying the contact. I didn’t go in. Stayed outside and watched for a while. I could imagine him, his cock hard as a rock while he was innocently pretending to “wrestle”, and I got immediately wet. Like, crazy wet, I felt almost drunk the level of excitement I had. So i go back into the kitchen and call my bf. He stands up and run towards me. I can see his dick through the jeans and I’m certain.
So we stay a while and then say goodnight. I was supposed to drive both of them back home. While we were driving back home, my bf starts making jokes about how we should have sex that night. I was shy and never talked about this stuff with Natasha, so was a bit embarrassed, but he kept joking and she kept laughing, encouraging him. So then she said “well, I could take a video” to which he immediately replies, “well, you could be in it, my gf doesn’t mind, do you?”
I was speechless. This was absurd coming from him and left me without words. So I didnt say anything. He was the one deciding things for the both of us most of the times, I didn’t have a very strong personality.
So I was driving, he was sitting behind and she was sitting next to me. She goes behind with him and smiles at me. She puts an arm around his shoulder. Still, I was speechless. I was very jealous and actually a bit angry they were so insolent. But also, I could feel my pussy getting wet. So he says “[my name] come here”, like he’s talking to a dog or something, and I do that, still confused. He says “suck it a little bit” and I started sucking him but it wouldn’t get hard, like maybe the situation was too much for him. So I suck for a little but it’s still soft and I think I’m doing something wrong. Then it immediately gets hard, I look up and Natasha has just started kissing him in a slutty way. When she stopped kissing him his cock would soft, so I went up and started kissing him. Then she went down at him, and while she was sucking him he was moaning so much I couldn’t kiss him, so I just kind of stayed there looking at him, moaning and mumbling her name. So after a while he pushes my head down and we start sucking him in two, I lick the balls and she licks the top. He can’t hold it anymore, and comes in Natasha’s mouth.
We all stat quiet for a bit, and that’s when my bf suggest Natasha should kiss me to see “how it feels”. Natasha agrees and I don’t reply, so she starts kissing me, biting my lips and sucking them a bit. My panties are soaked. My bf suggests we take away are shirts and adjusts the seats so we can lie down. I feel my nipple rubbing against her small this while she kisses me, so I grab her ass. My bf has taken his cock out of the trousers and stroking it. He keeps giving us orders with a rough voice I had never heard. He says: “you should do a 69 now”. Natasha takes off her pants without any hesitation, my bf looks at me impatiently so I do it too. I’m lying down and she puts her pussy right in front of my mouth. I’d never seen (literally) a pussy that wet. It was dripping. I started kind of awkwardly slurping her clit while what she was doing with mine felt amazing. I could also see my bf jerking off and repeating “oh, good girls, like this, good girls” until he came and squirted on her ass. I came but felt so shy I tried not to show it. I don’t know about her.
After this we went home, and I never knew if they fucked again behind my back, after that night. At this point I think that’s very likely.
Anyways, that was the moment I realised I was a “cuckquean”: the thought of my bf cheating on me in front of me was a huge turn on. Still is.

Revenge on my high school bully [Mf] [oral] [masterbation] [spanking]

There’s a man looking over photos of young girls. Teens. 14 years old. Blondes and brunettes. Redheads. Girls with devoloping breast. Girls with small breast. Girls who looked like they were already 18. Finally, seeing the girl he wanted. Nicole. A cute brunette. Toned body from soccer. Nice developing breast. She likes to take selfies. Very confident girl in her photos.

“Finally, found you.” The man in the darkness says.

The next day. At the local coffee spot. It’s eleven am. Sunny and the coffee shop is bustling. Nicole is about to enter but is pushed backed by a random stranger with a hoodie on.

“Asshole.” She yells as she enters the establishment.

She hugs her friends and has some small talk then waits on line to order. She orders her extremely sugary and high caffeinated beverage. She looks for her wallet but it’s missing.

“No, I’m sorry. I have it. I swear. This can’t be happening again. No, no, no.” She panics.

The barista and the cashier look at her very sternly. This happening before.

Lost my virginity when I wasn’t expecting to [MF]

I know, the title seems hard to believe. Until I reached my early to mid twenties, I could easily miss hints and cues directed my way. That’s probably part of the reason I was still a virgin when I graduated from high school in the late 80s. I had gotten as far as French kissing a girl, but that was it.

I enlisted in the Air Force, and after Basic went to the base where I would learn my career essentials. While there, I did manage to get to 3rd base, both in the base movie theater (very stupidly risky in hindsight) and the dorm TV room. The dorm, itself, was co-ed, but the bays were not. During my stay there, there was a female I had hoped to hook up with, who was known for being generally inclined to have fun. For easy reference, I will call her “B”. Unfortunately, I never did get a chance with B while at the training base.

First Time Taking Photos [FM]

I got a ton of awesome messages of people asking me to write more about different first things, and my husband and I are having a ton of fun talking about this stuff and he loves when I write them up because I get insanely horny reliving these times, plus he loves hearing about how slutty I used to be. Someone asked about this first, but I’ll write a lot more so message me and ask.

This goes back to my last year of high school, right after graduation. I’d been in a FWB type relationship with this really fun older guy who I grew up near. We went to fancy places and parties, he was well off and paid for everything. We had been talking about having more of a relationship but he had concerns cause his youngest daughter was my age. I personally didn’t care, but she wouldn’t have liked the idea since we were friends. Anyways, he ended up getting transferred for work to the other side of the country and we had a few weeks to wrap things up because I was going to school in a totally different place.

Far Away At Willoughby Academy (Part 5) [FF][Fsub][Mast][Med][Reluc][Exh][ENF][MC][College][SciFi][AltReal]

**Far Away At Willoughby Academy (Part 5)**

Regina waited until after dinner to track down the name Miss Stevens had given her days ago. It felt like much longer, but it wasn’t even the end of the first week. She knocked at room 3035 in Turnbull Hall. At half past six, she hadn’t needed to buzz in with her bracelet. Turnbull Hall was a second-year dorm, and much quieter, since the majority of second years weren’t showing up until the weekend. Someone was playing pop music, which she didn’t recognize, but it was echoing from down the hall, making the place seem emptier. One of the things that surprised her was seeing a door for the co-ed common room when she entered the lobby. She wondered if people used it when they had to change into what Regina would only loosely term as pajamas and robes. She re-tucked her blouse and straightened her skirt, steeling herself before walking up to the third floor.