Author: amItrailertrash

accidental slippage [MF]

This was the year that I was going to trade school down south, and had met a girl that conveniently happened to live in said town, we met at a house party and started dating, and I moved in with her for the short time I was going to school. The relationship lasted only as long as I was in school. But this is about the night that I accidently slipped in the wrong hole one night.

Her name was Amber, she was about 5’4″, blonde hair, green eyes, c cup tits, and an ass that was made on the hockey rink.

the club that we were at was attached to a hotel, and while we were drinking and dancing, at one point we actually found an unlocked door to a board room and had a very passionate quicky before deciding to take it back to my place for the main event.

It was a drunken sloppy make out fest, followed by an equally sloppy blowjob that turned into a 69. Her pussy was wet and tight, and delicious. She was gagging and jerking me off while telling me how much she wanted me inside of her. So like the drunk gentlemen I was, I slipped on a condom and started going to town. Read more »

Sticking my dick in crazy Part 9 [M][F][F][F] the tale of 3 women

So by this point I had broken things off with Melissa, but we were still fucking from time to time. She had finally gotten a place of her own, and it was coming along nicely for her. Little did I know, she was going through some massive depression, along with alcohol and pills, her life was taking a massive turn for the worst.

At this time, I had gotten the tinder fired back up and was also seeing two other girls, Lilly, and Kim.

It was a juggling act to say the least, Kim was a single parent like myself, looking for someone to drink wine with, and talk about what a train wreck out lives had turned into since our split. While Lilly was a girl that I was just getting to know and would go on dating for over a year after I had finally made the decision that I didn’t want to be sleeping around anymore. Read more »

The time I stuck my dick in crazy Part 8, [MF][MF] the beginning of the end

“Let’s go pick my friend up.” Melissa stated, its only a 4 hour drive.

Melissa had been texting her friend back and forth, Rebecca. She had told me some pretty wild stories about how her and Rebecca had hooked up in the past, and from seeing some pics of this girl, I was pretty curious to see where the weekend would take us.

So we packed up my truck, brought along some treats for the ride, and hit the highway. The weather was shit out that day, it had just snowed a ton, roads were terrible, but I was focused on getting there to pick this girl up so they could have a “dick sucking competition.” with yours truly being the benefactor. They had both bragged that they could go deeper than the other, so I was curious to see who the winner would be.

On the way, Melissa kept flipping through the nudes that she had of Rebecca to let me know what I was in store for. Rebecca was a slightly bigger girl, big tits, decent ass, tiny coming it at only 5′ even….. And as I would later find out, crazier than Melissa. Read more »

The time I stuck my dick in crazy Part 7 [MFM] The devils three way

At this point, you as the readers should be able to see that what Melissa and I had was pretty toxic.

She had massive attachment issues, and I was in a place were the only think I should have been attached to was a therapist…… That being said, I did allow her to move in with me, it was almost a half and half thing were she shared her time between her moms and my house. She wasn’t around when my kids were (thank god) but still. it was a weird time.

My friend Jake was at my place a lot during this time as well, he was also trying to hide from his issues in a bottle, and running to my house was his release from life. We grew up together, knew each others ins and outs, and I still consider him one of my good friends. This is the night we had a devils three way with Melissa while high on mushrooms.

Melissa had gotten her hands on a 1/2 oz of zoomers, Jake was on the lounger, and Melissa and I were on the couch. We had settled on watching youtube music videos on my TV while we waited for them to kick in. All of us were pretty deep into the second 24 pack of the night, Jake having finished his bottle of vodka. Read more »

Sticking my dick in crazy Part 6 [MF] Shower fuck to cure a hangover

Melissa put my phone on speaker while my ex wife was yelling obscenities on the other end of the line, “You know he’s fucking other women don’t you?! You little coke whore, I hope you like my sloppy seconds!”

I stood in the shower listening to all the terrible things they were saying back and forth before finally stepping out and ripping my phone from Melissa’s hand, telling my ex I would call her back and hanging it up….. Not how I wanted to start a morning after the interesting night we had just had.

Melissa had a fire in her eyes, they were still a little glazed from her also apparent hangover, “that bitch can’t talk to me like that, you need to say something to her.” I wasn’t trying to defend my ex, but I did overhear Melissa say she could take my cock better than her, and that she was a loser for letting me go, but that’s besides the point. “Sure, I’ll let her know next time we talk.” Read more »

The time I stuck my dick in crazy Part 5 [FF] sit in the corner and watch my fuck your girl

First off, thanks for the comments people, I had no idea that there would be this much interest in my fucked up stories hahaha. After I wrote down the first one, it felt good to keep going, relive some of my troubled times and remind myself I’m on a better path. Melissa was a wild ride, but some things are left in the past, though at times produce good memories.

Back to the debauchery.

After the risky business in the sauna, I got a call to head out to a different job for a week south in the province, to say I was glad for the call was an understatement. At the same time, Melissa was headed off to a work training seminar in the city, so we made plans to meet up at her hotel when I was headed back, maybe go out for a nice dinner, go for drinks or dancing.

We talked throughout the week, me about working alone in the mountains, bouncing from site to site getting shit done, her about all the new people she was meeting and how well program was going for her. One night she brought up one of her co-workers, “she’s a lesbian, I really like her! We get alone great, she makes me laugh all the time, and helps me afterwards go through anything I missed.” Read more »

The time I stuck my dick in crazy Part 4 [MF] red flags, red flags everywhere

I have a little time this morning, so I figured I would write up about the time Melissa gave me a HJ in the sauna at a crowded pool….

As I said before, I was in a dark place at this point in my life, drinking daily, dabbling (okay more than dabbling) in drugs far harsher than the weed I was also smoking. Yet somehow, continued to go to the gym on a semi regular basis. Sure I would make myself presentable and be the best guy I could around my kids when I had them. But all in all, I was a fuck show….. Melissa was keeping me on just enough of the edge that I wasn’t fucking anything that moved (that came out later in the relationship).

I was still on nights, so I would be sleeping by 9am, and up at 2-3, crack a beer, make some eggs, protein shake, and then head out to the gym, which was located in the community center, so there was a pool and sauna attached to it. Read more »

The time I stuck my dick in crazy part 3 [MF] first time anal

I’m currently sitting in my camp room, so I figured I would attempt to write up a third story about Melissa.

For everyone asking, I won’t be sending pictures of her. I’m a douchebag for sure, but even I’m not that douchy to be sending out her pics without permission, and if I write up to the end of our relationship, you’ll see why we don’t talk anymore lol.

Someone asked who she looks like, after a quick google search, best I could come up with is Emma stone, with a slightly wider face lol. Oh! she also had pierced nipples, those were fun.

Melissa had a lot of kinks, I mean a lot. We chatted about each others one day driving. I’m not into kink shaming, but even I won’t piss on someone’s face, and I’m not a huge fan of forcefully slapping one across the face and spitting on them, too many dark memories. That being said, she LOVED anal.

I mentioned in my first two stories about a tongue or even finger in the ass, but I wasn’t expecting that she more often than not wanted me to take the route less taken. Read more »

sticking my dick in crazy part 2 [MFF]

So after crazy Melissa and I had be seeing each other for a couple of weeks, more and more red flags would pop up, that I was either to pussy drunk to notice, or had to much emotional shit going on in my head to care about. She messaged me one night while I was on an afternoon shift, asking if one of her friends could come over for drinks.

I rolled into my house at around 11:30pm, walked up the stairs to loud music, laughter, and 2 fairly drunk ladies at my table. Her friend (tammy), was going on about how her boyfriend wouldn’t mind if she hooked up with another girl, but didn’t know what the rules would be for another guy…… The fuck did I walk into?!

I grabbed a beer from the fridge, pounded it to start catching up, grabbed another, and sat at the table to get some more information from this curious conversation. Apparently, Melissa was heavily bisexual, and Tammy was someone who she had hooked up with in the past. My mind was racing, I’ve been with “bi” girls in the past, but from talking to one of them about it, they basically said, “just because i’m bi, doesn’t mean that I want a threesome. Read more »

The time I stuck my dick in crazy [MF] Part 1?

Hey all,

My last post went well, so I figured I would write up another one about my first “relationship” after I got divorced.

In 2019, before the world went to shit, my world was already in the trash. At 29, I had just gotten divorced, lost my house, went from seeing my children to suddenly being told when I could visit them. Needless to say, I turned to some pretty bad habits to try and get my mind off of things.

My ex had always been the jealous type (when we weren’t fucked up and she was trying to show off), and had accused me of sleeping around with a cousin of her sisters husband back when we were together. So what does any half drunk guy do after a nightshift when he’s feeling lonely?….. That’s right, message said cousin and see what I could make happen.

I thought this girl was hot, sure she was 8-9 years younger than me! But from what I could recall, she could just about outdrink me at the fires we attended, smoked, cursed, and was an all around good time. What’s the worst that could happen?! Read more »