I fucked an older women at a wedding
For the record, I’m not proud of this, but it was one of the hottest experiences of my life. I am currently in a relationship.
Last week a good friend of mine got married. I (27m) was supposed to go with my gf (25F) but she had some work event to attend. Not going to lie, it was nice going on a little mini solo vacation. Sometimes just getting away is a nice reset. Anyways, the wedding was in California on the beach so it was super nice and tropical and just a good vibe all around. The dress code was also a bit lax so everyone was wearing beachy attire. I was hanging out with my group of friends most of the time. Since we were there a few days before the actual wedding we were golfing, hitting the pool, and partying it up at night with other wedding guests.
The night before the wedding, everyone was kind of doing their own thing, so I decided to head down to the bar to watch some of the games on TV. So there I am hanging out by myself when a woman probably around 45ish came and sat a... continue reading
Recently, my girlfriend (f24) and I (m24) have been playing around with the idea of her waking up to me already fucking her. The past week I’ve been waking up a little while before her, gently rubbing her pussy to get her a little wet, and slowly squeezing my cock inside her until she wakes up. She usually starts waking and moaning pretty immediately.
Today, I woke up really hard, and spent a little more time getting her ready first, and lubed up my cock so that I could slide inside her more easily. She was asleep still, lying at a slightly odd angle, but I managed to find the right spot to begin pushing my very hard cock inside her. She felt amazing. As I eased into her and began to slowly thrust, i noticed that she was still asleep, and was only just about to wake up to my cock fully inside of her for the first time.
As she woke, she began moaning deeply, and gasping with each breath. I started fucking her harder, speeding up and gripping her hips tightly to pull her further down... continue reading
Asked my boyfie to use all my holes whenever he wants
Our sex life has always been pretty good, but we didn't have sex that much (or as much as two people with big libidos should be having) usually 1-2 times a week. About 3 months ago, I started toying with the idea of switching things up.
I asked him to use me for his own pleasure, as a fuck toy whenever he wants. No matter what I'm doing, any hole he wants, no questions asked. My boyfriend is a perfect gentleman and is quite vanilla in bed, so I wasn't entirely sure he would be up for it or if he'd even give it a shot.
He agreed to try it out, but didn't immediately take advantage of my request. The first few weeks we were still having sex twice a week and nothing new had happened. But something happened for him in the third week, and I woke up to his cock down my throat in the morning before he left for work.
I was shocked at how rough he was being, I'd never seen him like that before. He has a big, thick, long cock and I've never been able to fit it all in my mout... continue reading
Drunk anal with a friend's sister
So this was years ago when I (28m) was in college.
I'd gone over to a friend's house, let's say her name is Violet, to drink and blow off some steam after a particularly rough round of midterms. We'd do this on a fairly regular basis with a whole group of friends and roommates, getting absolutely trashed and going over our classes and tests since we were in the same major.
Now, Violet and I never had a thing despite her being absolutely gorgeous. Petite blonde, nice body, funny, but I just never had any desire to have sex with her. Besides, she had a long-term boyfriend (now husband) who is an awesome dude to hang out with. Violet's sister Pink, on the other hand...
Tall, curvy, brunette, just a great body, very open, and one of the biggest flirts I've ever met. She was a year below us in college and was always present for our drunken escapades since she was living with her sister. I swear basically all the men that were ever over or in the group wanted to be with her at one point... continue reading
Admittedly, I'm pretty easy to pick up at a club. You can always find me dancing, and if you're suddenly behind me, you'll find my ass all over you in no time. So you can imagine what that says about my standards in a guy who can take me home.
A guy asked me if I would dance with him last night if he bought me a drink, so I grabbed him by his shirt and said he'd get me for the night if he bought me two. A done deal. While we were dancing, he just couldn't stay away from my ass. Constantly grabbing it, slipping a hand under my dress, the works. This didn't stop when we got back to his place.
We had some alright sex, but when he was pounding me doggystyle he was obsessed with playing with my ass. This time it was smacking it in the same place over and over until it ran red, then trying to stick fingers in my asshole. I let him get a couple fingers in there, but it was relentless. I was sure he was waiting for me to tell him to fuck my ass, but I was pretty drunk and wasn't turned on e... continue reading
Had a boyfriend some time ago who was incredibly sexually active and I had a great relationship with. (These two things usually go hand in hand for me.)
Once we had delved into the realms of kink, I found out there was a lot he had never tried. He ended up loving bondage, I already had an inkling that he was going to like mommy and pregnancy kinks and I ended up being right. However while we explored these kinks, the one he avoided entirely and had no interest in even talking about was anal.
So I avoided it for the time being, but knew it wouldn't last. It was something I had already done by myself a few times and enjoyed a lot, so I wanted to try it with a real dick very badly.
The relationship progressed without it, and eventually things started to fall apart. We became long distance when I left for school so the times we could see each other were rare, not to mention the times we could fuck. At the same time, I had developed a group of friends on campus in a physics class, all o... continue reading
Walking back to the campsite, Katie hung on my arm and laid her head on my shoulder. I was reveling in the bliss I had experienced throughout they day. It felt so freeing to be walking naked in the cool night, our walk guided by the little bit of light left from the day. It was a very intimate walk with someone who was not my wife and it was refreshing after 15 years of marriage to feel wanted by someone else.
Arriving back at the campsite Katie stops me and wraps her arms around my neck. Her body is pressed against me I can feel her hard nipples and soft skin pressing against me. My half hard cock is pushing against her small landing strip. She pressed her lips against mine and her tongue into my mouth. I wrapped my arms around her waist and grabbed her beautiful round ass pulling her closer. We shared this passionate kiss for a few moments before she broke it off, looked me straight in the eyes and said "thank you for tonight, I hope it's not the last time I get that thick cock ins... continue reading
My First Trans Experience
Before I get into the actual experience, I’ll give you some backstory on how we got there.
Growing up, I had a best friend named Brian who was also my neighbor. We met when we were 5 or 6 and both also ended up having older brothers who became friends through sports. So basically, we were together all the time, whether it was hanging out together at one of our houses or at sporting events, either our brothers’ or our own. We were essentially inseparable.
Brian’s brother was an exceptional hockey player, and even though we all played in some capacity growing up, he was miles better than anybody else in the leagues. Because of that, Brian and his family moved away when we were both 11 years old so he could pursue sports. It was tough when he moved but we still stayed in contact somewhat. This is a few years ago now so social media was still relatively new. We became friends on the various platforms and stayed in contact that way but eventually lost most contact when we entered high sc... continue reading
I had an anal threeway with my friend and her boyfriend
I had a kinky friend ask me once if I wanted to help her give her boyfriend a really hot surprise for his birthday, she asked if i would be down for letting her boyfriend fuck me and her up our asses. She said he loves anal and she had already skimmed through some of her friends on insta with him and that I was one of the ones he found really hot. I have a hard time saying no to anyone but i'm very susceptible to flattery so she got me there :)
So I said yes, and on his birthday i got myself super cleaned up and went over to their apartment and first we went out to get ice cream but then we came home and started kissing and making out (first she and I started kissing then we invited him in) then we started sucking his cock, he was like, holy shit this is an awesome birthday present, but then my friend was like, no, your present is you get to fuck our asses. He was pretty stoked about that.
We got our underwear off and I saw my friend was wearing a buttplug and I was like fuck, i wish... continue reading