Anna and her sisters Pt 5 [MF] [Oral] [PiV]

**Author’s Note** To all those who had been following and wondering about a new entry, sorry for the delay on this one. I’m linking the previous entries in this series in case you are a new reader, or need a catch up on where we are. A few more entries for this series will be incoming over the next couple weeks. On to the dirty story.

[Pt 1]([https://www.reddit.com/r/eroticliterature/comments/s7rrxz/anna_and_her_sisters_pt_1_mf_oral_piv_anal/](https://www.reddit.com/r/eroticliterature/comments/s7rrxz/anna_and_her_sisters_pt_1_mf_oral_piv_anal/))

[Pt 2]([https://www.reddit.com/r/eroticliterature/comments/s8ll4h/anna_and_her_sisters_pt_2_mf_oral_piv/](https://www.reddit.com/r/eroticliterature/comments/s8ll4h/anna_and_her_sisters_pt_2_mf_oral_piv/))

[Pt 3]([https://www.reddit.com/r/eroticliterature/comments/s9du2p/anna_and_her_sisters_pt_3_mf_oral_piv_dirty_talk/](https://www.reddit.com/r/eroticliterature/comments/s9du2p/anna_and_her_sisters_pt_3_mf_oral_piv_dirty_talk/))

[Pt 4]([https://www.reddit.com/r/eroticliterature/comments/sa9frx/anna_and_her_sisters_pt_4_my_night_with_chloe_mf/](https://www.reddit.com/r/eroticliterature/comments/sa9frx/anna_and_her_sisters_pt_4_my_night_with_chloe_mf/))

“What do you mean it’s not a problem. She knows I sent that picture of her sister, and not the one I’m married to.” I was pretty nervous now. Bridge is my friend and had been a decade before I started dating Anna.

“I explained everything.” She said.

“You told Bridgette you sent me to fuck Chloe?” I was a little gobsmacked.

 “Well, I kinda let it slip a little, then she pressed me about it. So I told her everything. She was shocked, but she understood.” She said.

 “Great, that’s all I need, your older sister looking at me like some kind of perv.”

“I don’t think that will be a problem, she’s actually really jealous, that I shared you with Chloe.”

[F]irst time solo anal

Recently I’ve been really curious about anal so last night I finally bit the bullet and tried experimenting with it. I had spent a good few days reading articles about how to start, how to prep, etc and by yesterday I was fully confident in trying it.

I was a little paranoid that it would hurt too much so yesterday on my way home from buying lube I got a few g’s of weed and rolled myself a small joint. After my parents went to bed I stepped out and smoked it at a park near my place and immediately came back, going straight to my room. I had already prepped for it a little so I just laid down a few towels on my bed, stripped naked, and laid down with the lube. I put a healthy amount on my asshole & fingers and just started rubbing my asshole.

I don’t know if it was the weed but even just doing that felt amazing so I got a little into it and spent what must’ve been the next ten minutes just massaging my asshole. Eventually I realized I needed to move on so I opened my laptop, put on some porn, and reapplied the lube.

Struck [M/f] [BDSM] [overstimulation] [face slapping] [spanking]

Sir’s little slut laying on the bed is something to behold. She is spread eagle, arms and legs forced open wide by the cuffs linked to each bedpost. She cannot move an inch. There is a leather belt around her waist, tied to anchors in the floor, keeping her midsection still. Like this, she is vulnerable to whatever he chooses to do.

The cuffs seem like the only thing keeping her from floating away and the belt feels like the only thing keeping her from shaking apart. Sir has let her cum three times now and the orgasms are starting to feel more like a punishment than a pleasure.

He pinches her nipples and scratches long red lines down her stomach and over her thighs. His lips are soft on hers and leave sloppy kisses down her neck and over her clit. She shudders and whines and her thighs quake. She couldn’t keep still if she tried and is grateful for the bindings that hold her in place. He brings her to an orgasm, then after she has come down from straining against her bondage, he slaps her pussy.

I fucked my first boyfriend only when he became my ex [FM]

*A warning: the lines between consent and non-consent might get blurry.*
———-

First boyfriend gave me [my first taste of cum](https://www.reddit.com/r/gonewildstories/comments/td5uj2/my_first_blowjob_or_i_swallowed_sperm_at_grandmas/), but when we dated I was not ready to go all the way. After our break up, we remained friends. At times, he flirted with me, which felt benign because he had moved to a different place and was getting plenty of quality pussy.

So, 7 years after our break up, I did not take him seriously when he said his main regret was not fucking me while we lived in the same city. I laughed it off. Well, it turns out he really did mean it, and this became a sticking point in our conversations for months. To his credit, he waited for me to break off a marriage prospect before he pounced.

“I thought he was the keeper. He would have made you a very happy wife.”

“There are some things I need to do before I commit at that level.”

“I sure hope fucking me is one of them.”

[FM] Let My Neighbour Fuck Me

I live in a condo. Small units, thin walls, you know the drill.

Over the past 2 years, I’ve been hearing my next door [M 40s] neighbour absolutely rail his wife. I’ve beard everything – the groaning, moaning, intense orgasms. I’ve heard her scream his name (let’s call him Jared), and vice versa. He’s not my type, but knowing what he’s capable of definitely made me look at him differently whenever we passed each other in the halls.

I also heard the arguments – very intense. Seems like he felt like she wasnt as invested as he was. Also seems like he wanted kids and he didn’t. They’d still have incredible sex after arguing, but it was clear there was a rift. I was working from home when he asked for them to separate and she immediately agreed. She left the next night.

I saw him a lot more after that. Passing smiles in the hallways, pleasant greetings in the elevator, casual conversation that kind of thing. One day he knocks at my door, asks me if I can help him out with some IKEA furniture. In hindsight, this was totally a line.

My [F] first one night stand [M] post break up

Heya! I’ve made a new account dedicated to this kinda thing for personal privacy reasons. I’m happy to chat with people on here but please be cool. I know I writing about my sex life, that doesn’t mean I want pictures of untidy dicks with your bathroom sink in the background.

So back in 2018 I broke up with my boyfriend of 2 years. He was in my class in University and ended up hitting it off. Pretty average relationship, decent enough sex, but there was no real passion anywhere, sexual or not. Regardless, I was pretty bummed out when I ended the relationship which led to a slight downward spiral. I began drinking more often, skipping classes due to late nights at a bar etc.

Her Second Massage [MF][Massage][MDom][FSub][Choking]

They entered his hotel room late. He followed her into the room where she turned to face him with a sly grin on her face.

“Same bed?” she asked.

“Yes…just let me pour a drink” he replied.

He moved to the table to fix himself a drink. As he mixed the rum with soda, she positioned herself on the bed, laying on her stomach, head at the foot facing him. He turned and sipped on his drink as he gazed at her body lying before him. God, how he loved the shape of her ass, he thought. He wanted her lying like this, but naked was all he could think at that moment.

Camgirl MILF gets caught [FF, mutual masturbation, camgirl]

[Read the first part here](https://www.reddit.com/r/eroticliterature/comments/tk97x8/a_49_year_old_milf_becomes_a_top_earning_camgirl/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

Mandy had been gay long before she knew what the word meant. She had heard her friends talking about wanting to kiss boys but that didn’t hold her interest at all. She would watch her friends talking and could picture herself kissing them instead. Her mother sat her down after Mandy got her first period and had “the talk.” Her mother talked about reproduction in a frank manner. Mandy was full of questions.

“Do only boys and girls kiss?” Mandy asked earnestly.

Her mom responded, “No hunny, sometimes boys will fall in love with boys and girls will fall in love with girls and that is okay.”

Feeling cautious, Mandy asked, “So it is okay that I want to kiss girls and not boys.”

Her mom smiled, “Mandy, It doesn’t surprise me at all and I am proud of you for sharing with me.”

Mandy slept her way through high school and college. She refused to settle down. She had seen her parent’s loveless marriage and wanted none of that. She had been in a bit of a forced dry spell. The lockdown due to the pandemic really hampered her love life. She realized that a lot of people were in the same position as her.

Under the covers – pt 2 (M/F)

I wake up at 6:30, slip out of bed and go out and get coffee made. I go back in to bed and find you on your stomach with your hand down your shorts. I place my hand on your butt to find the bottom of your tank top and slide it up exposing your back. Under the covers I go and begin kissing up your back.

You must be waking up, I feel your hips rise and push down hard into your hand. I kiss back down while sliding a leg of your shorts up to expose a butt cheek. I kiss it multiple times before I start to bite it gently. Your rhythm increases, you’re awake and ready for me to get in between your legs.

You spread them wide to allow me to lay in between them. I nibble, bite and kiss your ass more, down around your thigh and back up the inside and begin licking, lapping for your vagina. You lift your ass up to allow me more access to your lady parts. You’re soaked, it’s a joint effort with your fingers working your clit and my tongue working your opening and your soft ass hole.

I banged Janet’s BBW MILF BFF Connie after a cookout Part 2 [Str8] [MF] [kissing] [groping] [oral] [sex]

This is a true story. I changed the names of all and some details to disguise the identities of those in this story. The dialogues are to the best of my memory. It has been more than 45 years since this happened so I hope you will cut me some slack.

[Background: In 1978 I was involved in a hot wife/cuckold/bull relationship. Janet was the hot wife; Derek, my boss, was her cuckold husband. Our HW/C/B relationship had been on and off for more than two years. If you want to read about my experiences with Janet and Derek they are on my profile page.

This is the second of two stories focused on my initial times with Janet’s BBW MILF BFF. Part 1 told how Connie and I initially got together in her home as her husband slept off his drunk. That epistle is also on my profile page. Part1 ends with Connie not being ready to have sex with me and her sending me back to Janet with blue balls.]

**Connie and I, our second time together**