Tag: Anal

[MF] Happy Birthday Sugar Baby

I have been a SD off and on for about 10 years or so. A the time of this story I had been seeing my first SB for about a year, since she graduated from my senior seminar class… read the story how it started HERE. We started our arrangement right after my birthday in May so we were coming up on both my birthday and our year anniversary. Also, I knew she was leaving over the summer for graduate school, so our meetings had become more intense for both of us as we saw the end in sight.

Anyway, baby had asked if I wanted anything special for my birthday present and honestly, she would do whatever I wanted, so I had to really think about it. Little did I know it would turn into a bit of a small obsession for me after that. I asked her to worship my cock and see how many times she could make me cum in an afternoon. We usually spent a few hours in a hotel together and I would cum once or twice. I love to make the first one last with being edged, a variety of positions and my attention to her orgasms, etc. Read more »

When me (24f) and my bf (39m) hooked up with a friend of mine (23f) during quarantine [MFF]

One of my friends (let’s call her Mo) from Israel visited us in Gold Coast before the quarantine but got stuck with the flight cancellations. Me and her had hooked up before during our trips to Europe, but this was the first time where we had a threesome with my current bf.

First time it happened, we all were very excited and it took a lot of wine to calm ourselves down. Mo and I started making out and we were too horny to move into the bedroom so she started eating me out on the living room couch. When this was going on, my bf Jerrod was masturbating while looking at our show. After some time, he joined us and started fucking Mo from behind while she was eating me.

After sometime Mo had her jaw aching, so she just put her head on top of my boobs and started licking them while getting fucked from behind. Jerrod started to switch fucking between me and Mo which felt really great for me. With all the stimulation, it was too much for me and I came. Read more »

A new Puppy! [Dd/lg] [Kitten] [Puppy] [Daddy] [MFM] [Threesome] [Anal] [Gentle]

Daddy leaned back on the couch and smiled at her. One large hand petted his thigh, and she obediently moved to lay down with her head on his lap. Immediately his hand went to her hair and stroked it tenderly.

“I got you something today,” he chuckled, “well, I got us something. But I think you’re gonna like it.”

His fingers moved through her hair gently and she closed her eyes with a contented sigh. After a moment enjoying the warm feeling of her head on his thigh he clapped sharply twice. She opened her eyes slowly and watched in fascination as a tall, lean man with caramel hair and black rimmed glasses walked shyly into the room to stand in front of the couch.

“This is our pet for this evening, do you like him?”

She couldn’t answer straight away. Instead she stared up at him with wide eyes. The sharp sound and hot sting of Daddy’s hand coming down on her bottom made her flinch and gasp.

“Yes daddy, sorry…” she tired her eyes away from their new playmate to look over her shoulder at Daddy. “He’s ours?” Read more »

We [MF] got interrupted whilst having sex

This happened when I was about 22 and my, long ago ex, girlfriend was about 19. My girlfriend used to share a house with two friends and she was very open. She would often walk around the house in various states of undress and her two (female) housemates were just used to it. She was also very experimental and open sexually, so it was a fun relationship to be in.

Due to her openness, her best friend new an awful lot about her sexual escapades and would often tease her. One birthday her friend bought my girlfriend a double ended dildo, seemingly as a joke.

My girlfriend was slim, had dark hair, with small tits and a nice round ass. She also sported quite a big bush, which I loved. She loved anal sex and we would do it often.

One day, probably in the middle of the day, we were having a really good fuck. As we were fucking, she rolled onto her side and took the double ended dildo out of her drawer. She told me that she wanted dp with the dildo in her pussy and me in her ass. She laid on her side, pushed her ass out and told me to fuck her ass. I rubbed some lube on my cock and her asshole and slowly pushed my cock inside her. Read more »

[MF] I fuck my fiance’s ass after 5 years

So, me and my fiance have been together 5 years and our sex has always been pretty damn good. She was quite timid before meeting me due to previous relationships and being used to sex where her satisfaction wasn’t considered by her partner. After a few months together she was open to more things that were new to her like spanking, choking, riding me among other things. Only recently she opened up to the idea of blow jobs, they aren’t my favourite thing but the sight of her with my cock in her mouth does it for me. The only thing that was seemingly way off the table was any form of anal play.

That was until a couple of weeks ago when after a long hot session she said she wanted to try anal. A few days passed and we got all the essentials like lube etc. When the night came we had normal vaginal sex first, my fiance is able to have multiple orgasms which seems to help relax her. After getting ourselves ready again we got down to the business of prepping her for anal. Read more »

My FWB [F] cucked me [M] for a younger boy toy.

My (I’m 29) side piece who is older (46) and married has an open relationship and she fucks a rotation of regulars. She’s really fit for her age and looks much younger too. She likes younger guys for boy toys and for a while I was the youngest. Her type is usually early 20 or late teen black and Latino dudes. Her newest addition is a 19 year old Dominican and she told me he was her new favorite because he was really long and girthy. So when I go over her place for a quick hook up and we are in bed naked making out she all of a sudden gets a text. The new kid was texting her to come over in about an hour. So she tells me I need to leave. This is the first time she’s ever acted like this. Then she asks me to just finger her but I can’t have sex with her because she wanted to make sure he didn’t get used pussy. I was denied a hand job because she didn’t make want to make her bed a mess. So I begged her for anal instead. While I’m fucking her from behind she’s sexting this guy and telling him how he hits deeper than anyone she’s had and she loves her dick. I’m completely out of the mood and actually pretty pissed at this point so it’s taking me awhile. She gets mad and tells me to just hurry up and come in her ass so she has time to get ready for him. Read more »

I [M] decide to give a Nerdy Girl a date to remember… then she surprises me by deep throating my cock on the ride home!

This is a true story that took place a few years ago, before my current relationship. I had recently ended a long-term and unhealthy ([but](https://www.reddit.com/r/gonewildstories/comments/ncsvb0/accidental_anal_with_my_exgirlfriend/) [very](https://www.reddit.com/r/gonewildstories/comments/nd1ewb/fucking_my_exgirlfriend_at_the_beach_house_while/) [sexy](https://www.reddit.com/r/gonewildstories/comments/nde7np/i_tried_to_break_up_but_my_exgirlfriend_took_off/)) relationship, and I was figuring out what kind of women I wanted to date next. I had turned to online dating, and was finding some success. This is the story of how I underestimated a girl on a date, and wound up getting the most amazing blowjob of my life.

As usual, if you like this story please comment! And if you really like it, send me a chat or a PM. I enjoy talking with folks who read my stories!

I started chatting online with a nerdy girl I’ll call Veronica. She was a bit plump, with long pink hair and pale skin. Not my usual type, but after a long relationship I was trying to branch out and try new things.

We decided to meet up for a mid-day beer in a town up the highway. The first date was alright. There weren’t too many sparks, but we connected over her nerdier interests. She talked and talked and talked about anime and video games, and I realized that this girl was far nerdier than I. Read more »

Nailing [M]y First Crossdresser- The First Date [M][M]

[Pending how this is received, I will happily provide a follow-up of the second time I got to meet Toni. I thought perhaps that a burgeoning sissy may see this and feel a bit inspired to hear about an anon meet from the other side of the equation. I’ve added a bit of narrative for effect, but 95% of it is true to the best of my (rather high) recollections. For your consideration, I present an overly-detailed account of my first time nailing a crossdresser]
***

I can still taste her tight little ass whenever I think about it. Or, more accurately, his tight ass, but when you’re fucking a cute bubble-butt thats so tight and tasty, does it really matter? To this day, the smell of coconut oil takes me back and I can still feel the faint patter of what has to be tone of the top five most intense orgasms of my entire life. Fuck, I came so hard that it makes me hard just to remember how hard I came. Read more »

The Inventor Part 1: Jack’s invention comes to life [MFF][blowjob][facial][scifi]

After years of hard work Jack had finally completed his prototype, a completely realistic sex doll with AI learning. Her name was Celest, or Cybernetic Exponentially Learning Emotive Sex Toy and she was designed to be able to alter her body shape and facial features to best suit her user. Celest was on a work table beside Jack with wires hanging out of her ear ready to be formatted for Jack’s sexual desires. All he needed to do is run the basic start up program, and the AI should do the rest. The screen in front of him flashed grids of women’s faces and body parts, his eye movements were being tracked to narrow down which traits he was most attracted to. Celest’s body contorted beside him, slowly forming into his ideal woman. Read more »

My husband won’t fuck my ass…so I stuck a finger in his and he loved it [f][m]

So if you have followed me at all,ever since a little night club adventure when a stranger fingered my ass I have been obsessed and longing for a little anal exploration.

Anyway my hubby isn’t that way inclined. And I’m okay with that. Recently though I have been exploring more with [some plugs](https://imgur.com/a/TsShq8N) and encouraging him to show a little love to my rosebud.

He does enjoy a good rimjob though. So one night while I was giving him one of my daily blowjobs I continued past his balls and gave his ass a little love with my tongue. That’s when, after lubing it up with a lot of spit I stuck my finger in. And let me tell you the stories are true. He loved it. I have never seen him cum so much or so hard.

I think we might just have added an entire new dimension to our relationship.

Stay tuned…