gonewildstories Archives — Page 2739 of 5640 — NSFW story

How I [M] Ended Up Fucking My Married Cougar Occupational Therapist [F]

[TLDR Version: I (M39) ended up fucking my married older Occupational Therapist (F55) after she reached out to me by e-mail when I was no longer a client. Long.]

The garage door was open – just like she said it would be. To my right I saw that the door leading up the stairs to the living area was open slightly – just like she said it would be.

I parked my car next to hers and entered the house. As I began ascending the dark wooden stairs I called out softly, “Hello?”

A sultry reply came back from her den where soft music played in the background. “Hello,” I heard her answer. “Come on in. I made you a drink.”

She sat on the couch with her legs curled under her wearing a short black dress like I told her to since I wanted to have easy access to her pussy. Underneath, she had a classy black and white brassiere that cupped her small breasts. Under her dress she wore a pair of black lace panties that I’d told her to wear since it turned me on. Read more »

FWB Loves Anal [MF]

“Daddy, PLEASE fuck my ass!” Grace pleaded.

She and I had anal sex for the first last spring. Her last boyfriend wasn’t too interested in it, so I was really the first person she explored it with. Turns out she LOVES it! She’s tall (5’10”), skinny but with a nicely shaped ass from years of competitive swimming. Her long brown hair is usually in a ponytail. Grace has a smile that will light up a room, and eyes that are so blue you want to swim in them.

Personally I’m going for the sexy Dad next door vibe, although it feels like I forget the sexy part sometimes. I’m tall(ish), stocky, more salt than pepper in my hair these days. I’ve been told on more than one occasion that my cock is a great size for anal. Not too big at close to 6”, with a good girth. Additionally when I get hard, it’s HARD.

We were trying to ease our way back into bedroom activities after a six month break. The emphasis should be on “trying” though as we were attacking each other the way a Survivor contestant dives head first into an all you can eat buffet! I’d already spent 30-45 minutes eating her pussy; we’d gone through our favorite positions, I’d even shackled her and gave her a few licks with the whip. Read more »

I 19[M] have sex with my older brother 21[M]

Me and my brother have a long maybe toxic relationship,
We both sleep in the room, we’re our parents only childs. Almost everyday after we check that out parents are asleep we lay in the same bed and start playing with each other,
I’m usually a bottom but sometimes I’ll fuck him, somedays we only cuddle or just a quick hand/blow job
I thought I’d share my story so if you’re interested i might post some stories and how it began.
Ask my anything

The continuing adventures of me and Val [M][F]

In the beginning of our relationship, Val and I wanted to make sure we were doing things right this time. So, we weren’t in a rush to jump right into bed just yet. We had years of each other’s lives that we had to catch up on. That first taste would have to last us and we were fine with it.

She met my kids, I met her son. Her mother and my parents still remembered one another and got along. We had plenty of date nights together. We made out and groped each other constantly. We were happy with that.

We dated like this for a solid 6 months. Of course, the want was there. Text messages got more and more racy, certain pictures were exchanged. It wasn’t long before we couldn’t take it anymore.

I managed to get the whole week off for the 4th of July. She had work for the first part of the week and I had my kids, so I decided that I would throw a bbq on the fourth. She brought her mom and her son and my family came too. We all had a great time hanging out. The kids played and the adults laughed and joked. Val pulled me to the side and informed me that her mother was going to take little man for the night. When every one else went home, she was all mine. She then kissed me and ran her hand across the front of my shorts. Read more »

My first gay experience [mm]

I knew I was gay since I was very young but living in a small religious town forced me to be quiet about it, I knew college would be my chance to be myself.
I was excited when I started college because I knew it would be a chance to explore my sexuality, the only problem is that I’m shy. I had an English class and my professor ( we’ll call him John) was very attractive. He was about 5’10 with a pretty nice dad bod and in his mid 40’s. I definitely had a crush on him but I wasn’t going to hit on my teacher especially when I didn’t even know if he was gay, which lead me to this day……
One day after class John told me to meet him in his office. I was so nervous because i didn’t know why he wanted to see me. I get to his office and he got right to the point. “ when did you come out?” He asked. “ I haven’t actually come out to anyone “, I responded.
“ so you’ve never been with another man?” He asked.
“ no “
“ do you want to?”
“Yeah”
“Come here”, he said in a claim yet commanding voice. The second I walked up to him he grabbed my waist and plunged his tongue deep into my mouth. I was in complete shock I had never kissed anyone before especially not like this. His tongue swirled aggressively in my mouth and eventually I calmed down and started kissing him back. It was incredible. He was pressed against me Nd I could feel him getting hard. The next part happened so fast.
He forced me to my knees and undid his pants his cock was right in my face. It was right around 6 inches and fairly thick, it was semi erect and twitching.
“ put me in your mouth”, he said gruffly.
I was apprehensive at first but I complied. I took him completely in and started to suck.
“ don’t use your teeth, just lips and tongue “
It took me a second but eventually I figured it and got a rhythm bobbing on his now rock hard cock. I know I was doing it right because he started to moan and grabbed the back of my head slowly fucking my face. I could taste his precum as I sucked on his head and cupped his twitching balls. He gripped my head tight told me to stay still as he aggressively started fucking my mouth. I was gagging and drool was running down my mouth but I could tell he was going to cum so stayed still. Then he let out a “fuck!” As his hot sticky cum shot into the back of my throat. I almost threw up but I swallowed his salty load and stood back up.
He did his pants back up and said we had to go before we got caught but that we would get together soon.
It was an incredible experience and there’s more stories to cum. ?

[MF] I finally caved and let him use me

My ex boyfriend from high school was the first person to explore my submissive side with me, and if I’m perfectly honest, he’s never really lost that control over me. I struggle to resist him, even to this day. He’ll suddenly pop up in my DMs and I can usually stop myself for a while, just being a bitchy brat until he goes quiet. But a few weeks ago he sent me a message I couldn’t ignore.

“I’m going to be walking past your house at 10pm tomorrow night, you’d better be ready”

Fuck. This is the closest he had been in months, and I knew I wouldn’t be able to be strong this time. I tried, I really did, try to play it off, pretending I wasn’t interested. We both knew this was a lie. I spent the whole day as a bundle of excited nervousness, still unsure whether he would actually appear at my door.

At just a little after 10, my door knocked. I hadn’t made any special effort with my clothes, I just had a long t shirt and leggings on. Besides, they never stayed on very long. I took a deep breath and opened the door. Read more »

I [M] received the HJ of a lifetime (that I didn’t ask for) from a [F] Las Vegas Hooker

Last year, I had a short business trip to Las Vegas for some meetings and a big client dinner. I arrived late Wednesday night, and was flying back home to the Midwest early Friday morning with a full day of meetings and the aforementioned dinner sandwiched in between.

On Thursday, got back to the Aria at around 11pm after a loooong dinner and a couple (or maybe 9) whiskey gingers. I had an 8am flight Friday morning to make sure I arrived home early enough, with the long flight and two hour time change, to spend some time with my wife and kids.

Buzzing on adrenaline from a successful day of meetings and buzzing even more so on whiskey, I decided I would hit the blackjack tables to unwind a bit before I called it a night. Shockingly to me, the Aria actually had $10 tables available for low budget players like myself. Read more »

I was solo in a medical clinic and could entertain [MF]. Afternoon delights : )

I had been emailing K for several days. She had a profile on an adult dating site and was actually closer to me than indicated. Early 30’s, not married , no kids 5′ 4″ , average build and she looked good in her photos. She was available to visit at my office in the afternoon We went over favourite positions. I mentioned that a nice one to start was her sitting in a chair and me alternating between oral on her and penetration. When I told K, “I’m looking forward to tasting you ” , K, said “I would probably taste you first. Game on ! A date was set . But it was a winter storm day. Darn ! K came the next day. Read more »

[MFM] Finally had my first threesome!

It finally happened. Heres the story.

If you want the background, you’ll have to check my profile. I’ve got lots of stories about the events leading up to this.

In summary: I met Devaughan a couple years ago. Had amazing sex, developed a kink for creampies and older men. He introduced me to his friend Troy, who I fucked during the relationship and after Devaughan and I ended things. Troy and I reconnected during COVID, and became FWB. And then Devaughan and I fucked at Troy’s place. And it was very clear that they wanted a threesome (because they said so). Both men are in their early 40s, and I’m 28.

Things started off as they always do. Drinking, hanging out, nothing exciting. Both men are looking at me in a way that makes me kind of horny, but also a bit uncomfortable. You know the feeling. I decide it’s now or never, but I’m not the type to make the first move. Read more »