Whats the best moment in the history of your sex life?

[JoBYY]

The most interesting moment of my sexual life was definitely when my friends order me a prostitute to lose my virginity. I will definitely never forget that in my life.

[nerdybetty]

Probably just after I came out to my wife as trans and she confessed that she'd always sorta known and wanted to make the day rather special for me. I'm a bit of a sub and have always wanted to try out some BDSM stuff; so she no joke hired an escort, a professional dom, to show her the ropes literally and figuratively and she treated me to what was, hands down, the best sexperience of my life.

Knowing that my wife not only fully supports me, not only is she kinkier than I am, but is willing to spend £2k just to have me tied, spanked AND give me some stellar pegging sex all in the same day??! Amazing. 10/10 wife material, I'd marry her twice if I could!
I'll have to write a blog post or story or something about it, it was honestly THE most wholesome and sexiest thing i think I've ever experienced. I think I'm the luckiest specimen alive lol

[joyvenusianarts]

The best moment of my sexual history was the defloration of my anus. It was in a forest and I got fucked in the ass by the boyfriend of a male-to-female transgender woman. She watched me get fucked the whole time. The guy had a very big cock and he fucked me in such a way that since then I can't do without big cocks deep in my slutty ass. From this memorable event, I wanted to feel this first impression again. And every time I use big dildos seven centimeters wide, it's the memory of my anal deflowering that comes to mind. My little ass was tighter then, and it was this wonderful moment that was this first time that made me want to explore the magic of anal pleasure more and more deeply.

[KCallidus]

The girl I first had sex with and dated on and off again through college did two things.

First, after a night of way to much drinking, she was riding my face and intentionally peed in my mouth. It was mind blowing and I loved it.
Second, a couple of months after that, having replayed that scene a few things, she met me later at night during the summer and road my face again. This time feeding me some other dude's cum.

That blue-eyed, red headed, fair skinned, freckled Irish Catholic sexy freak fucked me up for life. I was smart enough to know to never date another red-head again.

Still friends with that minx.

[JerkForThem]

Mine was probably when i dared my wife to wear her PVC dress (images in gallery) on a night out with me to a club. Didn't think she would do it but she did! The whole night guys were staring, groping her on the dancefloor, trying to chat her up etc. I was a walking hard on all night, she knew it too.

It gets to the end of the night and I’m desperate to get her home and fuck her. She has other ideas and drags me round the back of the club, down an alleyway out of sight (or so we thought). I hitch her dress up over her ass, bend her over and slide right in. She was already soaking wet. I cum quite quickly as I've been building it for a few hours watching other guys try it on with her. She turns around to face me and it turns out we are being watched by 3 guys. She kneels down, sucks me dry then stands up, takes my hand and we walk straight past them smiling.

Only regret is that they didn't join in!

[jedjcfvenusianarts-joystardust]

The best moment of my sexual history was the defloration of my anus. It was in a forest and I got fucked in the ass by the boyfriend of a male-to-female transgender woman. She watched me get fucked the whole time. The guy had a very big cock and he fucked me in such a way that since then I can't do without big cocks deep in my slutty ass. From this memorable event, I wanted to feel this first impression again. And every time I use big dildos, it's the memory of my anal deflowering that comes to mind. My little ass was tighter then, and it was this wonderful moment that made me want to explore the magic of anal pleasure more and more deeply.

[johnnyys]

when I tried sex with hot milf. I often hook up with older women via dating site. I wasn’t even looking for a hookup at first, but the site helped me rediscover a side of myself I hadn’t tapped into in years. I matched with someone who shared my interests and my pace. We took our time chatting and getting comfortable, and when we met, everything clicked.

[Sandy_Porn_Collector]

For me it was with a woman I fucked for a year or so. She was a filthy redhead with huge tits who would do pretty much everything, she would let me fuck her face, she would swallow my cum and take it up the ass.

One evening I was out with her as it was her cousins birthday and I had plans for her in the evening. At the time I was a police officer and owned a pair of rigid handcuffs (much better than the handcuffs with a chain). We went out for the evening and after the meal we were having a drink in a pub and I was telling her what I was going to do with her, at one point I was standing against the wall and she was in front of me rubbing my hard cock through my jeans with her hand.

When I got her back to one of the bedrooms at the cousins house I put my plan into action. Firstly I placed a blindfold on her, then I placed her hands behind her back and applied the handcuffs and she was completely at my mercy, then I got her on her hands and knees and stuck my cock inside her tight arse, I then fucked her while she screamed in pleasure before I dumped a load of cum in her willing ass.

[bottomsup88]

So very long, got carried away, but thats how I am with stories
So the very very best experience #1, I cant tell you But it was by far the best sexual experience ever. For all involved
So I lost my virginity when I was early teens with my GF at the time and we fucked ALL the time. When I stopped seeing her I didnt do much for a while until senior year.
From 18 to 23ish I was a fireman, worked for Cal-Fire, I went to work there right out of high school and if there is one thing you get from doing that job is you are IN SHAPE. Fighting brush fires is to this day the most physically demanding thing I've ever done. So I looked good And according to the female friends I guess I was a good looking guy. Although I was oblivious to that fact, ugh. But I never had a problem getting girls, dates, hookups and all that.
My Dad was the Deputy Chief of the Major city fire department where we lived. At one point he was the commander of all the dispatch. So everyone knew him and all the other surrounding city Dept dispatchers knew him. (No this is not a dad son thing)
When I was 19, which was 1980 I was at home, Friday night and the phone rang, old school land line. I say hello and this gal asks for someone, she sounds cute, if thats a thing, and I say sorry wrong number, but my chick radar went off so I didnt hang up, I started talking to her, and flirting. She is 39, 20 years older than me. We lived near each other and I talked her into meeting me for a drink. (remember I'm 19) So we decide to meet at the bar in El Torito's in town.
So remember no internet or anything so this is a totally blind meet. We meetup, and we hit it off, she was really cute and sexy, great bod and fun and she was all over me. Plenty of sexual tension. As we're talking we're sharing our stuff, I'm a fireman, she just happens to be a dispatcher at the fire dept of the city we live in, which is next to the one my dad works for. So stupid me not knowing any better I said OH well you must know my dad! He's dating so n so at your dispatch, which was her co worker! She asks whos' my dad? I tell her and she about shits herself. She knows my dad really well, one through work but also through him dating her coworker, she knew all the dirt on my dads dating life from her friend LOL. Once she realized who I was, hooking up was too close to home. She understandably didnt want getting out that she hooked up with the Chiefs son who's 20 years younger than her.! So I had to do some fast talking to get her to stay which she did.

She invites me to her house, we get there, she gets us some drinks, we sit on the couch which lasted about 2 minutes, clothes are off, and it was an all out go for a good 3 hours. I was in the best shape ever and this gal twice my age gave me a run for me money. That was some of the hottest best sex I've ever had. When I left the next morning she says, this was only supposed to be a 1 time thing, ....But, she says to me, thats the best sex she's ever had in her whole life and you're coming back mister! No complaints from me! We hooked up several times after that each time as good as the first. Even though she was that "older woman" to me, I didnt really see it that way, she was just a good looking chick, we clicked and the sex was fucking HOT!

Another one, I give this girl top 2 in the best sex. I Grew up in Socal but had moved to Washington state and I had a 3 week trip back home planned. There was a group of us that grew up together (4 guys). I was the first to get married, have kids and get divorced lol. One of them married the high school sweetheart he met when she was 14 (Cathy). Had kids but they only made it about 17 yrs got a divorce. The thing was me and Cathy always got along, we were always friends., she was that girl I couldnt have. Nothing was ever said between us. But many years later after her divorce, ex out of the picture we started talking. Me in Wa, her in Cali.
We decided to go out while I was down for my trip. BUT I had also gotten on the AFF AdultFriendFinder to see if I could find someone to hookup with, go out with. I came across this profile, very pretty, long blonde hair, 5'4 100lbs and the name is "Allholes666". PERFECT! LOL I hit her up tell her my plans, and she says she's in but has a BUT. And its a big BUT... She is paralyzed in a wheel chair, she broke her neck when she was 12 diving into shallow water. Technically she says she's a quadriplegic but only because her hands dont work right. She's more like a paraplegic. Since our meetup was on the premise of sex and hooking up she goes on to explain things and how having sex works and all her limitations. Let me tell you she doesnt have many. allholes666 means what it says LOL So she sounds light a total sweetheart, sends me pictures of her, she worked for a very famous radio morning show so she was actually very well known.

I thought What the hell why not, whats the worst that can happen. So the day we met I went to her house and we were going to go to lunch, when I see her, my jaw drops, she is fucking HOT, her condition aside this girl is a 10 all day. She is smoking hot, just beautiful. So if you go anywhere with her she actually has to drive because she has one of those mini vans made special for her and her wheelchair so she can drive it. I'm thinking a chick thats a quadriplegic, in a wheel chair that can drive her car at 75 mph down the freeway is pretty bad ass in my book lol Son of a Bitch! This chick hauls ass! She's in the fast lane jammin down the road. After spending time with her, she's a pretty neat person and you forget she's in a wheelchair. So we make a plan for me to come over one night. We would have done it that night but because of her condition we had to plan it a little. She LOVES getting fucked in the ass. She has a caretaker that comes over 3 times a week and helps her empty out her bowels. Sucks, yukky process. BUT the end result is the caretaker goes the extra mile for her and does an enema. Those are the days she's all cleaned out and ready to get fucked in the ass

So I was skeptical a little initially, but she cured that in the first 3 minutes of giving me head. She tells me she's like a little rag doll, you just have to pick her up and put her wherever you want her to be, any position and she's way more flexible than a normal person Feet up behind her head, peace of cake LOL This girl does not miss out on any sex anything. I have a really big dick and she takes it like a champ, she can deep throat, loves giving head, loves hard vigorous fucking and REALLY love getting pounded hard in the ass which is just perfect for me cause thats how I like to give it.
The first night we fucked for hours, I kept coming back for more and she was game. Since she only does the cleaning thing 3 times a week, guess where I was 3 nights a week for the 3 weeks I was there. She is one of the coolest people I've ever met and the sex was AMAZING. If I were to rank it she's #2 on best sex ever.
So in the mean time I had these plans with Cathy. I've known her for 40 years. We go out, dinner, beach, motel at the beach, awesome night had a great time. Later that night we have sex. Now I've wanted to have sex with Cathy, the blonde little surfer looking girl ever since the 1st time I saw her 40 years before. The sex was fun and enjoyable BUT her sex sounds, she sounds like she's squealing like a pig. I cant explain it. I've had lots of sex with many different people, this was wtf is that. Totally distracting. It was one of those things that ruined an otherwise good time. I waited 40 years to have sex with her, man that let all the air out of the balloon. I mentioned her because she wanted more sex and more hooking up. She was calling me and I told her I have plans with "Rollergirl" and Cathy got ALL PISSED off that I wanted to spend time with Rollergirl and in the heat of the moment she says "Why! she's a cripple, how can you even have sex with her when you can have sex with me!!!"! LOL. She was totally put off that I wanted to spend time with a girl in a wheelchair than with her. I didnt have the heart to tell her how much better the sex with Rollergirl" was.
The End