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.

A drawn out hookup with the store hottie. [MF]

Hey everyone,

Burner account for obvious reasons. This is going to be a llllooonnnggg post with lots of details – I want to do the story justice. It’s not a unique story, but it’s special to me.

About Us
***
This took place back in 2012, so both she and I have changed a bit.

Her
To protect the identity of the girl in this story, I’m changing her name to Lucy. She knows I’m posting this and will be reading the comments. So if you like the story or have any questions for her, she’ll see them. She also loves compliments so please heave those on her in the comments.

Here are some pictures of her I’m posting with her consent from my spank bank. https://imgur.com/a/ax7OJxe

I think she’s gorgeous, she has the kind of body glorified in old paintings, with a luscious head of firey red hair, hourglass body, green eyes and an incredible pair of tits. I probably jack off to her memory once a week.

Me
I’m about 6 feet, brown hair, brown eyes, scruffy. I’ve been described by the gay community as a “cub” (I’m not gay, but apparently that gives people the mental image they’re looking for). I work out, but still have some weight, so I’ve got a pretty solid dad-bod.

My girlfriend let me fuck her however I wanted for my birthday [FF]

I had a fairly good response to the first story I posted on here (plus it was really fun writing it!) so I’m going to share another story about the amazing sex I have with my girlfriend Leah.

Here’s a link to my last story for those interested: [My girlfriend surprised me by fucking my ass after a wedding [FF]](https://www.reddit.com/r/gonewildstories/comments/a2uvh6/my_gf_surprised_me_by_fucking_my_ass_after_a/)

This experience took place on my birthday last year. As the day approached I was hinting to Leah that I was expecting big things to happen in the bedroom to celebrate. She was wondering if these expectations included her fucking me or if I was thinking more of a role reversal. For context, between the two of us, Leah fucks me about 70 percent of the time, so you could say she’s the more dominant one of the two of us. With the drop of a dime though, she’ll be on her back, legs spread open, begging for me to fill her up. One of the qualities I love most about her in terms of sex is that she can make me cum five times in an hour by fucking me just the right way, but also absolutely blow my mind by taking it any way I want to give it to her. With this in mind, I decided I wanted to spend the day truly appreciating that glorious body of hers by fucking her any way I pleased.

Tales from the Candy Shop, part 4 [MF]

[Part One](https://www.reddit.com/r/gonewildstories/comments/9xdytx/tales_from_the_candy_shop_part_1_mf/?st=JPKVCVG2&sh=d8a3408e), [Part Two](https://www.reddit.com/r/gonewildstories/comments/9y8n9h/tales_from_the_candy_shop_part_2_mf/?st=JPLGJRM9&sh=111edc91), and [Part Three](https://www.reddit.com/r/gonewildstories/comments/9ze32z/tales_from_the_candy_shop_part_3_mf/?st=JPLGKNPM&sh=21695007) here

Just the other day I was browsing this and other confessional subs when I came upon one poster who admitted that he’d had sex with a girl in someone else’s apartment. Like a *Highlander* flashback or an *Assassin’s Creed* memory (yes, I’m a geek, shut up), it triggered a story and made me think “Oh yeah, I’ve totally done that!”

Back when I worked in the Candy Shop, my then-girlfriend Ann was asked to house-sit for a friend. She usually lived with her older sister and a friend from California, and this was a chance for her to have her own space for once. For me, it was a chance to get naughty.

The friend rented a studio apartment in an historic part of town. Still, the owner had made the most of the space; the bed was in the center of the room, surrounded by the kitchen area, a bookshelf, a futon, a Chinese screen and a workspace. The bathroom was in the hallway, shared with the other tenants. I’m almost positive such a thing is illegal now, but whatever. Ann’s friend also had a dog, the care of whom was her main task as house-sitter.

RAOMD [Success] [MF] Part 2 – finding our kinks

If you want to take a look at how I met “Kelli” and our first encounter, that story is here: https://www.reddit.com/r/gonewildstories/comments/a6azu2/raomd_success_mf/?st=JPPN940S&sh=541e3752

After that first time, we both decided we wanted more and we agreed to make our arrangement ongoing. One thing I left out of that story is that neither of us desired to be in a committed relationship. Thus, a kinky FWB arrangement was born. I say kinky because Kelli wasn’t satisfied with a “let’s just fuck” arrangement. She wanted to know my kinks and what got me going and wanted me to know hers. I fuckin loved this because I have always wanted a partner that was willing to explore with me sexually and have never had one. Until now….

In the weeks that followed part 1, we were both too busy to meet often. We messaged back and forth frequently though and she would often send me amazing pics of her naked body. She went out of town with family, we squeezed in a short meet for drinks, and then she was leaving on another trip the next day. I would be out of town the week after that, so essentially we wouldn’t see each other for at least 2 weeks. We decided it would be best to plan out our next meeting after those 2 weeks were done, so I made some arrangements. What happens on that rendezvous I will save for part 3.

Followed two strangers home from the club after making out with both of them and getting fingered on the dance floor [MFM]

I wanted to post a new story but it’s been awhile since I’ve had any action, so I thought why not share one of my older stories instead? I realised some of my deep fantasies because of what happened on this night that I’m about to tell you about, and it’s a memory I’ll cherish for a long time.

I was going to meet up with a friend, Carol, who I had met briefly at a previous house party. She was leaving the country for awhile so she wanted to have a night out with me before she left (she felt like I was fun to hang with, even though we only talked for an hour or so the first time we met). We agreed to meet at her friend’s house, and have pre-drinks together before heading out to the clubs. It so happened that another distant friend of mine, Frank, wanted to hang out that night too, so I brought him along at the last minute. After some cheap goon (boxed wine) and idle chats, we all left for the club.

[MF] I was kinda forced to sex (no rape or anything)

Hello Reddit,

I want to tell a story that happend 2 years ago in Germany (I’m German too so please excuse me if I make any mistakes)

I was a phd student at a big university and as such I was in charge of a lab full of undergrad students who tried to complete their first practical lab course. There was one “problematic” girl. Relatively pretty and also pretty naughty.

When the course started she attracked attention because she always made ambiguous and naughty comments when speaking with me, which got more on more sexual.

Examples:
Me: “Yeah, in an ionic bond we have only the attraction between the cations and anions. This all about attractions between different charges”
She: “Believe me, I know a lot about attraction”

Besides that she had always problems with the appropriate lab clothing. She loved to dress her sexy which included open shoes (not allowed) or skirts (not allowed).

This was going on some time until she stayed late to make more advances. I don’t speak about “Let’s drink a coffee”. She offered sex straightforward. I said that I had a girlfriend and besides that I must not sleep with one of my students. I relied on my authority and said to her, that I never want to hear any such advances by her.

Early Christmas – Twice in one night [MF][MF]

My girlfriend Ivy and I are in an open relationship. As her and my work often conspire to keep us apart. She travels a lot and I work odd hours.

While Ivy prefers to keep her flings one time things, I kind of mostly sleep with the same girl, aside from a few one night stands. I hooked up with the much younger Cassie, who works at the front desk of my office building. Cassie is very heavily tattooed and hard-drinking/partying under her proper office lady exterior.

Due to timing issues the office Christmas party was a week ago. Ivy was in town and accompanied me. It was the first time she came face to face with Cassie. I could smell something was up, when after work Ivy had me pick her up and I saw her dress. She normally wears the particular dark-blue dress, if she wants to impress.

I kind of found it funny and flattering that she dressed up, only so she could show of to Cassie. Well when we passed the front desk, Ivy clung to me, as if she had been riveted to my arm.

[MF] Introducing my husband to Amy

I have been taking baby steps with my husband, moving him closer and closer to considering making me a cuckquean.

I had another reddit user, James, message me who has a fantasy about watching his girlfriend, Amy, have sex with other men without any of the humiliation that tends to come with the cuckquean/cuckold lifestyle.

We talked a lot about our fantasies and they were very similar just flipped. He really liked my posts and would tell me that he would jerk off thinking of my husband fucking his girlfriend.

He gave me the idea of using pictures of Amy while I used the pocket pussy on my husband to get him in the mindset of fucking other women. When I saw the pictures I knew they would drive my husband crazy because she is definitely his type. Amy is very fit and has a runners body. She has a very nice round butt and large breasts for how skinny she is. She’s a very pretty woman with brown hair and blue eyes.