Tag: Anal

Being a Mistress at 24 to a 45 year old (true story) [PART TWO]

Damn, alright. Wasn’t expecting the response from the first one. I thought of posting because I always wanted to blog… but don’t know what about. Also, i’m SO SEXUALLY FRUSTRATED. All I have is to look back on my relationship with Jerry. Just logged on to my secret sex e-mail, and found the video and pictures I described on my previous post.

God my pussy is wet. Im craaaving dick right now.

Alright, let’s continue with my story on my affair with Jerry.

——————-

Jerry is a tender romantic. Thats what I like about him. He is obviously more mature. But he is also gentle. Though in bed… my god, he is dirty AF. As i mentioned, we eased in sex on our first meet. When we entered his studio from the balcony, I took off my sandals, and crawled onto his bed. Purposely had my ass out. He loves my ass.

I lay on my back, swaying my legs side to side. Waiting for him to come to me. He then climbs over me and kisses me. Read more »

[MF] More adventures in cross dressing

[part 1 exploring CD](https://www.reddit.com/r/gonewildstories/comments/gtya1u/fm_my_wife_is_encouraging_me_to_explore/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

We had a pretty easy Sunday on tap. We had cooked big meals on Friday and Saturday and had plenty of leftovers. There were calm seas for both of our jobs and no major hours needed to be spent in front of a computer screen.

I am the morning person in our relationship and I spent the morning hours crafting part one of this adventure (see the link above) Writing erotic stories turns me on so I was edging myself a little and taking periodic breaks to look at naughty things here on reddit.

Satisfied with my morning efforts, I turned my attention to taking a warm bath. As I sat there in a bubble bath admiring my own painted toenails I realized that, as a lifelong foot guy, seeing my feet look pretty was a genuine turn on because A) I would totally suck my own toes and B) The idea of other guys getting off on my toes adds a new layer to my well established foot kink.

I shaved my chest for the second time. Thus far I have been very fortunate with razor burn or skin irritations from my depilatory routines and I wish to continue this trend by staying regular with it. Read more »

I asked to eat her ass and it couldn’t have gone better [MF]

ever since i(m) started masturbating, I’ve always had this desire to explore a girls ass, especially with my tongue. It would turn me on the most thinking about pushing my tongue deep into a girls ass and feelings around while she moaned. I was 20 and with my first girlfriend (we took each other’s virginity) but we never did anything anal or anal related. I was too afraid to bring it up but when I did, she was really sweet about it and decided to go through with the prep work and give it a try.

It started on a saturday evening, and my girlfriend asks what we should do before sundown.

“Maybe we can do some sundown activities before sundown” I say

“What do you mean” She asks, slyly, and knowing perfectly well what I meant

“Should I show and not tell?”

“Surprise me”

Her teasing me was such a turn on and I couldn’t help but start imagining all the things we could do to each other for the night. Then I started thinking about my kink. The thing I always wanted to do but was too afraid to ask for: shoving my tongue down her asshole. I have fantasized about this before, and maybe now was the time to finally ask for it considering how horny we both were. Read more »

The Doctor’s MILF

MILF PART 3

 I continued to freely play with her pussy and feel her sensual moist pussy lips and I plunge my finger deep inside of her and enjoy the wetness inside and cant wait to have my cock inside of that hole.  I start to really concentrate on kissing and alternating with tiny bites up and down her neck.  I also continue to play with her pussy but I am now more focused on rubbing that clit of hers as like an automatic reaction everytime I rub my finger over or around her clit she sighs out with moans of pleasure.  This drives me to want to bring her to a climax just playing with her clit as I have her standing up and leaning herself into my naked body.  She tends to fall more into my chest when I really work her clit which gets my cock a cheap thrill as she inadvertently runs those oh so moist pussy lips right over my cock as she falls into and against my chest as I keep her standing upright legs spread.   Read more »

The Work Weekend, Part 1 [MF] [milf] [age gap] [female perspective] [yes they’re too damn long] [also probably too tame] [two peppers at most]

*(Note: If you’ve never listened to the comedy podcast “My Dad Wrote a Porno”, I really recommend it. They read and discuss truly absurd and anatomically impossible literature that one of their dads wrote for a series called “Belinda Blinked.” My stories in their cringier moments remind me a little bit of Belinda stories. But, I hope it’s not so silly that anyone could model a comedy podcast around it?)*

Cady had been on the road for work for fourteen of the last twenty days, and it was wearing her out. But one of the perks of her job was that she could self-approve a nice hotel for herself for this next trip — and she knew she deserved it. Friday work out of town merited a nice suite and an appointment in the hotel spa too.

When she was finally able to leave the remote office and get to the hotel, the relief at being finished for the week was exhilarating. She settled in to the suite a little, then decided to take advantage of some of the free spa time before the massage appointment. Read more »

Monster Brothel; The Witch and the Demon [fantasy][magic][foursome][anal][cum eating][monster][demon]

“Do you know what they have planned for us?” Alexa asked, twisting her vibrant red hair around her finger.

“All I know is that someone requested us specifically, they’ve more than proven that they know what we like. That squid girl was incredible and you said the Werewolf was exactly what you needed. They somehow know what it is we desire. I mean, it’s obvious there is some kind of magic at play here, they drew us in and now we can’t stay away. I trust that whoever they have for us tonight, it’s going to be special.” Jacob sat down on the edge of the bed next to his wife.

They were in a simple bedroom just like the one that Alexa had seen weeks before, a large bed in the center of the room with an iron frame bolted to the stone ceiling. The bed was covered in black bedding, satin pillows and sheets with a black lace ruffle along the bottom. The curtains were thick and black hanging over the windows on either side of the bed. The floor was grey stone tile and the walls were painted in a dusty charcoal. This room had a darker, more mysterious ambiance than the room in which Alexa had been introduced to her werewolf lover. Read more »

My [M] memories of Squishy [F] – A twitter friend who liked aggressive sex, became a sexting partner and engaged me in multiple IRL trysts. PART 4

[Part 1](https://www.reddit.com/r/gonewildstories/comments/gzy5hc/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 2](https://www.reddit.com/r/gonewildstories/comments/h01pvo/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 3](https://www.reddit.com/r/gonewildstories/comments/h02yz4/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 5](https://www.reddit.com/r/gonewildstories/comments/h03sur/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

Squishy was unusual in the respect that she didn’t keep her address a secret. She lived in a historic neighborhood with really big houses that were over a century old. Her house was her absolute pride and joy, and she tweeted a lot about how she knew she was extremely fortunate to have been able to afford her house. I think she was able to afford it because of a combination of factors. I think she came from a family with a bit of affluence, first of all. (Some of her pictures as a little kid were of her on a horse doing show-jumping) Also, she previously worked for a very large financial institution, and her (ex?) husband did as well. I’m still not clear on that situation because her first husband didn’t seem completely out of her life, but at the same time, nothing about that house seemed to indicate any kind of male presence. When I knew her she was self-employed as a freelance writer and worked from home without any set hours. She tweeted a lot about gardening, jogging, and her renovation/interior decorating projects. Read more »

New [f]riend in Vegas

I was in the train from the terminal to baggage claim when a handsome dad in a suit stands beside me. He’s sharp, clean cut, I had noticed him on my flight from Dfw, and he says hi. We chat. Both here for business. Staying at hotels across from each other on the strip.

“We should share a cab” He says. Indeed. I told him I’d never seen inside the Bellagio, where he’s staying. “Why don’t you come in? I‘ve got a great view of the fountains from my room, you should come see it”He’s smooth. Real smooth. Or maybe I’m just horny… Read more »

[M]e, My Girl[F]riend, and our roo[M]ate. Part 1

Hey all!

Some fun things have been happening in my life lately so I wanted to make this account to share.

A little backstory before we jump into it: I met my girlfriend last year over tinder, we had known each other vaguely through mutual acquaintances, but I hadn’t spoken much to her or anything. We’ll call her Clare

So anyway I met her and we hooked up and had fun so we agreed to do it again sometime, and while I was over her place I found out that the person who owned the house was an old coworker and friend of mine who I hadn’t talked to in awhile. Lets go with Tim for his name.

It was fun going over her place and hang out with Tim and hook up with Clare and generally a good time and whatnot.

So after a couple times of visiting her place Tim tells me that their other roommate, (who I didn’t know super well, she wasn’t there very often) was moving out and the room was available. I was pretty worried about moving in to the same house with with Clare since we hadn’t been hanging out for that long but I was also in desperate need of housing since my sublet was about to expire and the price was too good to pass up. Read more »

[M]y moving gift [F]rom Michelle

Apologies, this post got removed because I added a few video links to porn hub, now removed, hope you enjoy……

So this is a continuation of the me and Michelle period of my life. Following on from my first Michelle Story : [Here](https://www.reddit.com/r/gonewildstories/comments/gqtlrf/my_eventful_business_road_trip_meeting_with_a/)

A few of you have asked privately what she looked like, the only person I can think of is Victoria Roberts, who I must say, I got off too a lot many years ago : there’s some videos floating around on porn hub.

Michelle was maybe a little bit bigger than her, but facial features and pretty much everything else was damn near identical.

Back to the story at hand.

Michelle and I had grow pretty close over the next few weeks, and we get to point where we have the odd date here and there. We go through each others life stories and We fuck almost every night, and if we’re in my apartment, she’d leave to “go home”. We’re sure the office knows by now, but we keep it as professional as possible despite some slutty pictures here and there from the toilets. Read more »