gonewildstories Archives — Page 3602 of 5640 — NSFW story

[MF] – Met a lovely redhead in #Nashville

Early this week, I saw a post from /u/nashflashfemale, who I will call Holly, and started a conversation while she flew at about 37 thousand feet from the west coast. Great conversation and we agree to meet on Wednesday to explore some Nashville beer. I am going to call her Holly, as I am into the holiday spirit.

Tuesday night, she calls and is upset about another date that ended in disaster. We talk. She talks to my wife. We agree to meet Wednesday. I will try to keep this brief rather than a play by play, as she has already spelled it out [in this post]( https://old.reddit.com/r/dirtyr4r/comments/e9r2zg/35_f4m_nashville_exceed_my_expectations_success/).

First impression IRL was her getting out of the Uber. Nicely dressed in a mid-length top and sweats. She has a nice hourglass figure and she does look quite young, like her pictures. Personally, I think she looks better than her pictures. We have a couple of flights and a great conversation with lots of laughing. I love she is not constrained in laughing out loud. Humor is a sign of a good relationship, me thinks. :D Read more »

I [M] fucked my transgender [M] roommate

So yeah I fucked my roommate after I knew that he was originally a girl, and while I was fucking him and he started saying fuck my tight pussy wtf I couldn’t process what was happening am I fucking a man with a vagina or a woman with beard or both lol no offense to the trans community but what is the point of transitioning from female to male and still getting fucked by men

Roadhead from My Cheerleader Crush over Christmas [MF]

There’s only so much time you can spend with your extended family before it starts to drive you nuts. I was home for Christmas from the city a few hundred miles away where I went to college. I’d had just about enough of White Christmas and playing legos with my cousins so I hopped in my truck and drove out to a roadside bar that hadn’t paid too much attention to our fake IDs when I was underage.

It was decently packed, I figured I’d run into some of the old crew so I picked an open seat at the bar, ordered a longneck and took in the room. Seemed like most of the people were in the same boat as me, escaping from too much family time to the noisy confines of a dive bar.

“Oh my god! Hi!” Lilly wrapped her arms around my neck from behind and gave me a squeeze.

“Hey stranger!” I turned to look at her. She still looked amazing. In highschool, Lilly was the bubbly cheerleader with the long string of disappointing white-trash boyfriends. She was probably 5’8″, with a toned athlete’s body, wearing cowboy boots, jeans that accentuated her perky, firm ass and a snap-button western shirt that was unbuttoned enough to show her pert b-cups. Read more »

[FM] All tied up in a stranger’s hotel room

There I was, a 24-year-old chick in the Upper Midwest, yearning for no-strings sexual attention after a breakup. And there he was, Joseph, a 35-year-old man, introducing himself in my inbox. He said he would be on a business trip in my city in a week and offered to chat and see where things go. I indulged in the conversation, keeping an open mind to what is typically an unlikely scenario. By the time he was on the plane to my city it was clear that this hookup might actually happen. Two days into his stay, we made plans for me to come to his hotel room downtown.

I’ve had experience [hooking up with a stranger in a hotel room](https://reddit.app.link/XLabkcnfo2) before, which made me less nervous, but as I’ve mentioned in most of my stories, the nerves are never nonexistent no matter how many times you’ve done this kind of thing. We texted beforehand about what we were hoping to do, our likes and dislikes, etc. The thorough communication mixed with smoking some pot beforehand made me nice and relaxed when I got to the hotel. (I did get super lost trying to find his room though. That’s the downside of getting blazed I guess.) Read more »

My daughter’s girlfriend finger fucked me. [FF]

My [F45] daughter came home for the weekend from university and brought home her girlfriend (Sara) for us to meet. She was 19, tall with a petite build and attractive face with deep brown eyes. With expertly applied makeup is was easy to find yourself staring at her.

She was chatty and confident. She could have fitted in anywhere and I was glad she felt relaxed in our home. On the Saturday night the pair of them went out and I didn’t expect them back until late.

I was ready for bed dressed in just a robe fetching a glass of water when I was surprised at their return before midnight. They were both quite drunk and Sara was helping my daughter who was using any surface within reach to steady herself. I helped them both stagger to the front room and they flopped down on the sofa.

I fetched them some water and when I returned into the room the two of them were giggling.

“Show Sara your tits Mum, she is jealous of how big they are.” Read more »

[MF] First time Anal and DP for her

Long time lurker, first time poster. I was encouraged to share this story by her. Everything that happened was consensual (talk to your partner about safe words!), but it was a surprise.

We will call her Bella, and she is 37 with perfect tits and a great ass, but her best feature is her dirty, slutty mind. She is bravely pushing her limits and reaping the multiple orgasmic benefits as a result. We have many fun stories to share, but this one is one of my favorites. Read more »

Two fairy girls getting their wings and virginities taken [FFM]

This took place at halloween. I had the house for myself, and was sitting drinking with the neighbour. He is a middle aged guy and constantly complained about problems with his wife. Late at night my sister and her friend came in. Quite tipsy, but disappointed the party they visited had been a bore. They had worked really hard on their costumes. Both girls were dressed as fairies. My sister in a green and and her friend in a blue dress, with complementary wings in the same hue. They wore some sort of glittering makeup. To top it off, they had headband wreaths with ledband lights in all kinds of blinking colours, and the same kind of lights at different places on their wings. When the lights were on, they certainly lit up the area, the point being the center of attention I guess.

So the girls were in a good mood, and were flirting freely and happily. Them getting drinks of the girly type only added to their behaviour. He must have seen something I didn’t, because when the girls were gone to the bathroom, he said he hoped I wouldn’t be mad if he had sex with my sister this night. I thought he was joking and didn’t think much of it. Read more »

Mr. H. Part 3 [FM]

I can hear him moving some things around, he walked away for a minute but he’s back now. He picks me up in his arms. I’m covered in wax and my cum. My arms still cuffed behind my back, unable to see a thing and my ass filled with a butt plug. We’re moving through the house but I’m not sure where we’ve gone to, I’m absolutely lost in my own home. I feel him put me down on our bed, he uncuffs me. As I go to take off my blindfold, his hand greets mine “Not yet, lay on your stomach”. I do as I’m told. I feel him tie my hands together with rope and attach the ends to each side of the bed. He lifts my ass up so he can have better access, I hear more rummaging. He comes back to me, and kisses my ass before he smacks it a few more times with the paddle. I feel his fingers slide inside me again as his other hand plays with my clit. I thrust against him, just wanting an orgasm or even better to feel his cock inside me. I want to cum on him. Read more »