16 People Dish Out The Dirty Details Of The ‘Best Sex They’ve Ever Had’


Responses originally from R/AskReddit

1. Overcuming challenges

I have a lot of insecurities when it comes to sex with guys. It’s something we’ve been working on our whole relationship. I’ve never been able to get out of my head.

But about 2 months ago, something just changed. I stayed the night, which wasn’t unusual, and we started kissing and touching each other. But this time it was just so sensual and intense. I don’t know what changed or where it came from.

He ate me out for a solid 20 minutes and by the end I was shaking uncontrollably. I sucked his dick until he came and I swallowed, which I haven’t done in a long time.

I got on top of him and rode his dick for the longest I ever have, I honestly lost track of time. I didn’t have to stop and rest, I just kept going and going. We were both drenched in sweat, making it much easier for me to grind on him.

I squirted for the first time when I was on top of him. I’ve since learned that it’s easy for me to recognize the angle that he needs to hit for me to squirt, but I can never distinguish when it’s actually happening. I honestly don’t know how many times I squirted but it was everywhere.

He pushed me off and laid me down, pulling my legs over his head. He fucked me hard for a few minutes and I squirted more- I don’t know how many times still. We couldn’t sleep on the bed that night and it was still wet when we woke up early the next afternoon.

Our sex life has vastly improved since that night, but I’ve still never squirted that many times or that much again.

2. It was enthusiastic!!!

Enthusiasm. I once hooked up with a girl who had it in spades.

When I replay that night over in my head there’s not really anything physical about her or the sex that stands out.

But, my god. This woman was enthusiastic.

She made me feel like a God damn porn star.

From the moment when she got my pants off and said “oh wow” to later when she was saying shit like “your cock is so deep inside me.”

Don’t get me wrong, I don’t consider myself to be anywhere near a sexual God our anything, but this girl sure made me feel that way.

3. Making it fun

had a short term relationship with a girl I met through some mutual friends. My girlfriend at the time approved of me having sex on the side for a little fun while she was out of the country.

This girl just had an INSANE amount of fun doing everything. She actually acted like she was not only enjoying it, but having FUN every moment of everything that was happening. She was riding me like I was a swingset, smiling the whole time. We told jokes to each other. When we were done, we talked about fun times we’d had and sex with other people. Then we fucked again.

Three weeks.

After that we moved to different states and remained great friends over Facebook. When I met her new boyfriend, we all joked about how loud she was in bed.

That was as close as I’ve ever been to a poly relationship. Being with a girl who really showed that she not only enjoyed the sex but was also having FUN was awesome.

4. It was the acid…

On the edge of a bluff that skirted a closed golf course in whangarei, New Zealand. On acid. It happened because we got turned on by the waves, crashing into the rocks below. It was a night with a full moon, and the water seemed to be made of black latex. The waves would rhythmically slam into the hard, black granite. Making a sucking, slurping sound as it drew back, leaving gentle frothy licks before suddenly plunging into the rocks for more. We simultaneously decided that we needed to fuck. Immediately. I pulled her pants off and ate her for a while, before slowly entering. It was definitely the acid… but that night, I felt like I finally understood her vagina. I could feel gestures and contractions that seemed to happen almost autonomously. We’ve been having sex for over a year and a half, but this time I felt like I was really getting to know its texture and personality. At one point, it felt like our respective parts had blended, and we were stirring a mystic soup.

Tldr: outdoor sex, foreign country, amazing acid trip and super sexy water.

5. Kill my nipples

I was lazing in bed one Sunday morning with my SO. We’re lightly fooling around and chatting about sex. I love nipple stimulation and mention how I liked them squeezed really hard. We get an idea and he nips downstairs to the kitchen and he comes back with two different types of clothes pegs. We try the wooden ones first but they hurt too much, the plastic ones still cause intense pain but I can just about take it. We’re lying next to each other and im feeling pretty good about being able to take it when I notice that I’m insanely turned on, I mention this to him and he slips his hand down there to check for wetness. I’m soaked!

He immediately gets the hardest boner ever. Feels like I can barely get my hand around it. He tries to finger me but I can’t wait. I throw him on the bed and jump on his magnificent cock. I cum almost immediately, really hard. Hard enough to push him out of me but I’m on top so I use my bodyweight to keep him in. I can feel my pussy contracting around him, he has this huge grin on his face. Almost as soon as I finish orgasming I’m aware of the clamping pain on my nipples, it sets me off again so I fuck him a bit more. It takes virtually nothing before I cum again. Over and over I repeat this cycle, I cum five times in five minutes. It’s insane, my body has become some kind of orgasm machine. I can’t take any more and ask him to take the pegs off me. Bloody hell that hurts!

I lay down to recover while he massages my poor abused titties with this dopey ear to ear grin on his face. I needed a bit of time to compose myself but then fair’s fair I suck him off until he cums (it doesn’t take long, he was so turned on). Afterwards we lay in each other’s arms wallowing in our love for each other.

6. Choke me

My girl came over with all intentions of just passing out all night. (She was working a very shitty job at the time) So she gets there and we cuddle and go to sleep, next thing I know she’s waking me up at 4 am because she’s horny.

Things get hot and heavy and we get a little rough like normal, and then out of nowhere she grabs my neck and starts squeezing and at first I freak out, but then I realize I love it, and we keep going till we both finish at the same time. And then proceed to pass out and sleep till 1 pm.

7. Fuck me in the window!

For Valentine’s Day two years ago, my SO and I decided to rent a hotel room for a day-long sex marathon. We went crazy that day, just fucking on every surface of the room. The highlight though was him tying me spread-eagle on top of one of the tables in my school girl outfit I wore for him, and opening the curtains of the room so I could be “exposed” to the high rise office building that was across from the hotel. That element of exhibitionism while he fucked me raw was absolutely amazing. It was also the first time we tried some more intense BDSM stuff like choking and gagging me with my panties. It was so incredibly amazing, and now we’ve made it a tradition to spend Valentine’s Day at a hotel every year.

8. Sex in the rain (or after it anyway)

A friend and I were spending a lot of time together one summer- cute dates (picnics, going to the zoo, movies, dinner, you name it), late nights, and long talks… we had kissed, and were rarely found not holding hands or walking arm-in-arm. One night we were at my place, watching a movie and it started to pour- an immediate torrential downpour.

She turns to me, kisses my cheek and whispers in my ear “let’s go outside”, gets up and gently tugs at my hand, pulling me outside. We run around in the rain, barefoot and soaked- after a couple of minutes, we decide we’re too cold and have to go back inside, but we stop in front of the walkway and kiss for a good long while before going inside.

Inside, we’re both sopping wet- soaked through to the bone. I suggest we change into something dry, and she coyly replies “why not just get out of it?” so… we do- our clothes left by the door, she wraps herself around me and I walk us up to my bedroom where we proceed to have the most amazing, loud, passionate sex until the sun comes up.

Afterwards, my back was positively covered in scratch marks, and we both had hickeys everywhere. We ended up going over to a friend’s house that night to swim and then drink outrageously, and we had the same sex again that night- practically the whole week was spent relaxing and going out during the day and then wildly screwing each other at night.

9. Sex on the sofa bed

Mine was very recently with my SO.

I had my fair share of partners during college etc but the first time my SO and I slept together he immediately shot to the number one spot.

So he was away for a wedding, when he got back he had a friend staying with him, his friend was sleeping in his bed, he and I were on his sofa-bed.

We were cuddling and he was buzzed and not really sleepy. He asked if I wanted to spoon I said sure, he pressed his hard cock right up on my ass. I started grinding against it. He said he didn’t want to have sex in case his friend heard us so I started licking his cock instead. He stopped me and started teasing my tits.

Usually I like kinda rough stimulation, biting my nipples HARD, but this time he just went so slowly and so gently, it drove me crazy!! After maybe 10-15 mins of having my tits teased like that I couldn’t take it anymore.

I begged him to fuck me and he obliged. As we weren’t on a proper bed or anything we could only really do missionary but it was intense and so loving and just… Wow!!

10. I came inside her and it was insane

The best sex I ever had…

It was in college with a FWB. She came over to fuck like she normally does. Making out, I went to the drawer to pull out a condom but forgot we used the last condom the last time we fucked. I told her I didn’t have a condom.

We continued making out (her on top) while she grinded her pussy on my cock. At some point, she sank down on it. We fucked for a LONG time! Against the wall. Bent her over the bed. Bent her over the desk. Missionary. In the window. Everywhere. Back to the bed with her on top I was ready to cum. I told her I was going to cum. She started riding me harder. I said again I was going to cum. She started long stroking my cock – lifting up until just the head was in her pussy then sinking down. I went to grab her hips to get her off me. She grabbed my wrists and pinned them to the sides of my head while she rode my cock. I came HARD in her pussy! It was the first time I ever came inside a woman before. It was the greatest orgasm I had to that date.

I’ve had some good ones, but this one I will remember forever.

11. “Tell me the alphabet backwards…”

Leaving the bar one night, I bump into a vague acquaintance, and a friend of theirs whom I & everyone I was with didn’t know. She very strongly resembled a brunette Scarlett Johansen. We all briefly exchanged formalities, trying to be on our ways after a long night out.

The unknown, buxom, sexy brunette and I, however, had instantly locked eyes, and walking & talking on the way to the parking garage, I’m subtly flirting but am not pressed either way because I was tired, but she says to me with a smile “you look like you’d be a great kisser”.

Immediately I’m turned on because a woman taking the initiative, in any way, is one of the most dead-sexy things imaginable. We kiss slowly & passionately, instant kissing chemistry. She says “yeah… I’m coming home with you tonight”. Away we go in my car.

Get back to my place, tear off our clothes, all while hot kissing and my hands roaming her amazing naked figure. Perfect tits, ass, and hips, just simply perfect. The type of girl whose body doesn’t lie through her clothes.

So, the 2 hottest things that made this 1 (of 2) best sexual encounters in my life so far:

We’re making out, hot naked bodies pressed together while standing, and she drops to her knees and slowly starts going down on me (I LOVE standing BJs), and she is wonderful & passionate about it, but pauses a moment and looks up at me.

“Start saying the alphabet backwards, like I’m a cop giving you a field test, or I stop”.

Holy shit, I could barely think, and letters started pouring out my mouth in a blur, every so often hearing her moan/say: “Mhm mhhmmm” (as in “no, you messed up”), and she would lightly pull away from me, as my scrambled brain begged for blood from my throbbing cock in order to formulate the next proper letters to keep her going at it.

Amazing. Which led to:

We move to the bed and she subtly, almost without me even realizing, again takes initiative to maneuver herself on top of me. Watching her gorgeous, large breasts heave, as I gently caressed her body & breasts, as she buried her gorgeous hips down onto me…

Slowly sliding & grinding her pussy all over me, and then slipping me inside of her, and riding me like an animal. Like any guy, I love a girl on top. This is one of the sexiest views imaginable, and I was lost in the euphoria. Watching her slowly thrust away, with my hands on her tits, then one on her belly with my thumb gently rubbing her clit with every thrust… watching her arch back every few humps, and her head thrown back or to the side every so often, with her mouth open in a silent gasps.

Then she started trying to talk, like typical sex stuff “you feel so good”, “it’s amazing”, etc, but almost immediately, she becomes mostly incomprehensible and I have the hugest shit-eating grin on my face as this girl rides me and literally starts speaking in tongues, half-sentences, and half-words… and then feeling her pussy quiver on my cock as she collapsed on me and we kissed.

Un-fucking-believable. I rolled her over and finished myself off, but that was just mindless fucking at that point. She herself, was amazing. Laying there in the after-sex musky, calm, haze, she says “that was amazing, when I was on top of you it was like a mini-orgasm with each thrust, you have a perfect cock”… sooo fucking hot to hear something like that. I mentioned she was talking while on top, but she claimed she had no recollection of trying to say anything. Unreal. Best one-night-stand ever. Luckily it happened a few more times.

12. Hammock Sex

My first real/serious girlfriend, we had been dating on and off for like a year and a half. We had very similar libidos and interests back then, and she liked to do it whenever we had the chance. One night, I snuck over to her house (we were both about 16 at the time, so this was a big deal.) So I worked my way over there, and she was camping out in the back yard, and they had a hammock.

I started on top but that didn’t really work out, so then she got on top and holy hell. The next 45 minutes were THE most intense minutes of sex. She just got a rhythm that perfectly rolled with the bouncing of the hammock and it was crazy. I recommend a hammock to anyone for this reason.

13. Threesome led to better twosome

I had my first threesome one night (me, SO, and friend), up until the wee hours of the morning at the friend’s place.That was awesome and mind opening and beautiful but it’s not my best. My best time was the morning after the threesome when my SO and I were alone again: it was just missionary but it was so incredibly passionate and urgent and connected that it blew my mind even more than the amazing threesome.

It was like some new, deeper connection had been made between us after that night and manifested itself as mind-exploding sex.

14. “Ran my pussy like he owned it.”

My lover and I have the best sex I have ever had, consistently. The best was the most recent.

He just ran my pussy like he owns it. Double penetrating my pussy with toys, sucking my clit multiple times. He knows I like it kinky and rough and pulled out all the stops. I have bruises all over my body and my muscles hurt (this was on Wednesday. He fisted me while using a Hitachi on me. He took pictures of me. He fucked me with my panties. As in stuffed them inside me. By the end of the night, I was in ecstasy & just begging him to fill me up and use my pussy. Absolutely mind blowing.

15. Totally dominated, totally turned on

When I was 16 I was at a house with a circle of fracquaintances. Of all the people there, I knew him the least; we had had a few conversations previous, but nothing indicated that he was into me, so to speak.

There was a general “keep up” drinking contest in which I was of course participating, so by my 4th beer inside of an hour and a half (I was about 5’2″, 130lbs. at the time), I was drunk but not too drunk. More like at that wonderfully happy, invincible stage.

I had gone downstairs for a smoke and was climbing a set of stairs to the side room where we were chilling, and he was coming down. We met about halfway, stopped, and just looked at each other.

I said hi.

He said hi.

He slams me into the wall and begins kissing me, forcefully, without any of the sloppy drunkenness or inexperience I had come to expect from my peer group (although he has 3 years on me, so that helped). We run to his room and the door slams behind me. I say something like, “You know I’m not just going to have sex with you,” and he responds with something like, “Oh I know,” and then I’m up against the wall again, wrapping my legs around him (he’s only slightly taller than me and very muscular so we had great angles for all of this), then he threw me on the bed, went down on me while wrapped around my legs so I couldn’t escape, even after I had already cum twice and was kicking like crazy. I sucked his dick to a hardness heretofore unknown to humankind. Then we fucked in multiple positions for the next hour. We were interrupted at some point by people just walking in, but continued regardless, like the troopers we are.

This particular session was my first indication that I wanted to be dominated in bed, that the last thing I wanted was someone tenderly stroking my hair and asking me if I’m okay every 5 seconds. This was hot and spontaneous and just fucking brilliant.

16. “My moans were a treasure map for her to follow.”

One night my friend and his girlfriend ask me to go bowling one night, I decide to get out of the apartment, and they invited a friend along. It was a friend of the girlfriend’s who wanted to get out of the house too, she was someone I had met I think briefly once before, but only in passing. We all went bowling, and throughout the night I kept finding myself checking out the girl’s ass when she went up there. When she’d come back I’d kinda half assed put my arm on the back of the chair kinda around her but only lightly flirted.

Fast forward to the end of bowling, we all decide to come back to my apartment to watch a movie, my friend and his girlfriend are on one end of the couch, and me and the girl were kinda near the other (not cuddling, or anything). About 20 minutes into the movie I decide what the hell and put my hand on her upper thigh, to which she covers with her hand. At this point there’s insane sparks. About 5 minutes pass and then I just turn to her, she turns to me, and we start making out like teenagers. My friend didn’t notice really, and his girlfriend was all but asleep in his lap. I whispered to the girl “want to move this to my bedroom” to which she stands up and walks right to.

I follow her with about a 5 second lag time, and when I get to the bedroom she’s already laying on her back with her pants off. She asks if I have a condom and it’s on. This girl was the most enthusiastic woman I’ve ever experienced in bed, I was throwing her into all different positions, and she was squealing with delight in every one. What made it extra special is that she was the first girl I had ever been with that had her pubic hair completely waxed, which made going down on her the most pleasurable time I’ve ever had doing that for someone.

Then we turn the tables and she decides to go down on me, which typically isn’t the easiest thing to get me off from, however she was AMAZING, my moans seemed to be a treasure map for her to follow, as she always took my breathing and grunts as cues to what was good, and what was amazing! Then it came time for me to come, at which point I informed her of this (because I had never been with a girl that swallowed before and that’s common courtesy), to my surprise, she doubled her efforts and made me come harder than I had ever come before right into her mouth which she promptly swallowed with pride.

I was astonished at this whole series of events. However while we had been going at it for a good 30-45 minutes including foreplay and penetration, she hadn’t come yet (which she seemed to be ok with). I then asked her if she’s able to come while masturbating, and she said yes. So I grabbed her hand and guided it down to her still wet slit and started helping her rub it slowly, once she started getting a rhythm going I started to also masturbate with her in sync, while also kissing her all over, caressing her magnificent breasts, and occasionally helping her rubbing. After about 5 minutes, we both came with a powerful orgasm at the same time. She turned to me and said “that was fucking hot!”. After that both of us just laid there coming down from some of the most unexpected, statically charged sex.

After that night I found out that my friend and his girlfriend had been hearing the girl’s moaning and noises, and felt pretty uncomfortable so they left. To this day, that was the hottest, and best sex of my life. And the sad part is after that night, we never saw each other again (although we’re still friends on Facebook). Thought Catalog Logo Mark

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