What's the best sexual experience you ever had that you thought would be the worst?

[1373263]

As above, what did you reluctantly do / felt obliged to do / were forced to do that you didn't want to but really enjoyed and would do again / did do again if you got the chance?

I would say for me it was an older female flatmate, we were friendly but I wasn't interested in her in a sexual way, she was 15 years older than me and separated, quite serious and her clothes didn't flatter at all. My mate and I had discussed her at one stage and we came to the conclusion her best chance was her husband; my mate sarcastically referred to her as "your mum".
One evening she came into the kitchen, opened her blouse and held me against the bench, rubbing my chest and shushing me. She was quite persistent and eventually I went from thinking WTF was going on and how I could get away, to realising that what she was doing felt good, and her body felt good and quite different to younger women. We ended up in her bedroom and clothes came off; her figure was great, with peachy breasts and bum and a definite gap between her legs. She didn't know what to make of my cock- it grew and it was it was uncut, and she spent some time looking at how it worked before trying it for size, cowgirl style. It didn't fit- at all. She looked like she was going to cry, but when I asked her if I could eat her as a distraction she looked happier and agreed. I found that pussy lips could be very interesting- she certainly wasn't all tucked in neatly down there, and I made the most of it while she babbled and gasped- mainly gasped... and tried to drown me.
Confidence somewhat restored, she managed to work herself onto my cock- she was tight and when I was halfway in she started to get into it, feeling how far there was to go as she pushed down. Once we got going there was no stopping her and she almost seemed to suck the cum out of me when she came- it was quite incredible to me at the time how she could tighten herself in pulses.
We were both sore the next day and she was waddling around the house when I left, but being sore didn't put her off at all and within a couple of weeks she knew how to make it work.
I eventually told my mate and he went on about it for weeks, until I compared it to him seeking daddy dick...

 

[BlackBearCognac]

Probably a meetup with this Turkish guy while I was visiting Barcelona many years ago.

He wasn't really my type and our conversation over WhatsApp bored me to death.

He kept insisting on meeting up with me... and funny enough the same exact day I reluctantly agreed to meet him I had a spontaneous but successful and very hot hookup with someone else.

When he initially showed up I wasn't at all impressed. He was a super nice guy, though. Having already blown my load only ~3 hours prior, I was fine with just showing him around my hotel and talking to him.

But maybe about 15 min in he asks to go back to my room. I oblige and the moment the door shuts he gets naked and is all over me. He was only about 5'5" with a lean and very hairy body. His dick was instantly hard and maybe about 5.5". Comparatively I'm 6'2" with a very wide body with little body hair with about 7" cock.

I don't know what happened but something clicked for me... maybe it was just his raw passion and enthusiasm? It felt great to have someone be so aggressively attracted to me.

We made out, he sucked me, I ate his ass, then fucked him until I came inside of him. He then unexpectedly flipped me over and fucked me like a jackhammer for about a minute until he came. That was so hot that I actually immediately fucked him again and came a second time with probably the best orgasm I've ever had.

Great sex but with someone I wasn't even attracted to, even after the fact. Funny how that works.

 

[wvgwm52]

Thought about double penetration( 2 dicks in my ass at one time) Met couple guys and basicly was just having a threesome.. but I had mentioned to them about dp .. there I was .. guy laying under me me squatting down so he can fuck my ass .. he pulled out and his buddy went in really lubed up .. then they swapped again.. few minutes later the guy on bottom left his dick inside me and stays still as the other guy slides his dick inside me ..

I don’t know why I never did this sooner.. feeling my ass open up like it did and the pain was awesome.. I know wild saying the pain was awesome.. but I learned I loved pain years ago from another man

they kept things lined gokd.. then it was a good feeling.. on minute felt one dick shooting inside me . Then the other shoved in all the way as he could and came as well..

So if like pain trust me.. this will push you to your limits and then some..

And yes I’ve done it few more times since

 

[Lakeshore]

When I fucked an older BBW I had just met at a party. I was 25 years old and horny all the time. I thought because of her 50+ years of age her tits would be saggy, her pussy would be loose, and her overall body would be ugly. Surprise to me: Her tits were super firm, her pussy was very tight, and her body was nice. She was a good fuck.

 

[Jeffp50]

I saw this guy on Grindr, he would sometimes send me a "hi" there. I would normally ignore. From the picture of him he didn't look that good, and looked too effeminate for my taste.

One day I decided to respond him, he wanted to meet that day because that afternoon he was alone.

I was about to leave and rain started pouring, i grabbed my car, had the worse time trying to find his address since all the roads were blocked, so I thought this were not our day.

He answers the door, he is so handsome! 6'2 green eyes, his body is in between that phase of fit and chubby, stubble beard, amazing smile, and much more manly that i expected.

He just took me to his bedroom and started kissing me. Great kisser he was, his body felt really good and had trimmed hair all over. We just clicked really well. Felt it like i knew him a long time ago. We were all naked at this point but I didn't even cared to move to the next part since this part was solo good

My dick is a little bigger than his. But his is much smoother specially the head. He rimmed me, sucked me, kissed again. I'm really good at it, which I of course retribute, but I have to say how good he was it as well.

Eventually i grabbed the condom he got the gel. He was really enjoying fucking me. I was really nice to see in his face every thrust he would push inside me.

We both came, i did in his belly, which he grabbed some put in his mouth and kissed me, he did in my face, we finish with a kiss.

One of the best exp i had really awesome, the only sad part is that I had to move town. But I still have his contact so one day we will see it other again

 

[Derringer]

Not necessarily the best but a very surprisingly arousing experience when I watched a girlfriend being fucked by a guy with a far bigger cock. I had never made her cum with my tiny penis but she quite obviously enjoyed multiple orgasms when he fucked her.

 

[Aussiebottomguy]

When my ex arranged a gang bang for me with some of his friends. There were 4 of them and they all took turns fucking me, either together or one at a time.

It was very hot at the time but later I regretted some aspects as they took pictures and videos and the worst was i bumped into 2 of them sometime later and they remembered me and laughed.

 

[SeeTheDifference]

The first time I was with a guy and he convinced me to bottom. I was sure it would be painful and unsatisfying. Instead, it turned out to be one of the best sexual experiences of my life.

 

[thick4me]

Long time ago I was walking on Greenwich Ave and passed a tall..thin..muscular guy...big head of beautiful thick curly hair. I turned and walked in the next shop.. He followed me in after a quick chat we exchanged numbers...We met up the next day and took the subway to his apartment in Parkchester Bronx...We had incredible sex...His cock was huge..thick..perfect..over 9'' and thick...he was so aggressive...I loved it....meanwhile I was in a long term relationship ...I was not so much as confused as hypnotized...The next day after work he came to see me..We ended up back in Parkchester...in bed ...in the shower..on the floor..on the terrace...
I ended up going back to my boyfriend after 2 or 3 days..I regret not having stayed with him in The Bronx and left my partner for good....We ended up seeing each other a few more times...
I'm always thinking of him and wondering where he is...and what if???? Incredible magnetism...

 

[Richard Licks]

Not necessarily the best but a very surprisingly arousing experience when I watched a girlfriend being fucked by a guy with a far bigger cock. I had never made her cum with my tiny penis but she quite obviously enjoyed multiple orgasms when he fucked her.

Sounds like a cuckold situation there. Did you do that more than once?

 

[Derringer]

Sounds like a cuckold situation there. Did you do that more than once?

it became a sexual lifestyle choice. totally kickstarted by a rampant sph fetish. not only did I not engage in it only once but numerous times with that girlfriend I ended up in 2 subsequent relationships ( including my most recent one) that included cuckold activity.

 

[Daveboogie]

First time I had my ass eaten out. I was at a sleep over with lots of fiends staying in the same room. One of my friends randomly started stroking my legs and thighs before slowly pulling my undies down. Before I knew it he was spreading my cheeks and shoving his tongue into my hole, it was so ticklish but I was trying not to wake any of my other friends up. The more he licked the harder I got until I eventually squirted cum everywhere again still trying to muffle my moans and groans as not to wake any of my friends. I just lay there after it, covered in cum with my ass out and my undies by my ankles.

 

[Derringer]

First time MMF where the other guy totally outmanned me. I have a tiny cock so not really a surprise but I was very trepidacious about the humiliation factor. I however discovered I had an sph fetish as I was actually highly aroused by the situation when the hookup actually happened.

 

[theplayerking]

I was at a sex party here in New York during Pride a few years ago. Being Pride in New York there were a lot of people visiting from out of town. The party was pretty active and a lot of fun. Towards the end of the party a guy in his mid 60s who was a total top but had a small dick asked to fuck me. I’m extremely versatile and almost never get fucked without flipping unless the top is super hot (which this guy was not). However, because it was Pride and he had come all the way down from Upstate New York, I decided to let him have a go with my hole. In terms of pure physical sensation, it was the best fuck of my life. My asshole has never felt so good before or since.

I‘m more of a psychological bottom, meaning I get off more on the idea of a hot guy being inside my body rather than the physical sensation of getting fucked (which to me, always feels a bit uncomfortable). Despite not being turned on physically, this guy had amazing technique that made my hole feel amazing.

 

[notthatguy]

The first time I fucked a girl's ass. OMG was it tight.

 

[deleted690810]

I was at a sex party here in New York during Pride a few years ago. Being Pride in New York there were a lot of people visiting from out of town. The party was pretty active and a lot of fun. Towards the end of the party a guy in his mid 60s who was a total top but had a small dick asked to fuck me. I’m extremely versatile and almost never get fucked without flipping unless the top is super hot (which this guy was not). However, because it was Pride and he had come all the way down from Upstate New York, I decided to let him have a go with my hole. In terms of pure physical sensation, it was the best fuck of my life. My asshole has never felt so good before or since.

I‘m more of a psychological bottom, meaning I get off more on the idea of a hot guy being inside my body rather than the physical sensation of getting fucked (which to me, always feels a bit uncomfortable). Despite not being turned on physically, this guy had amazing technique that made my hole feel amazing.

Huh- there are many aspects of this story that I find quite interesting. The only time I can think of hooking up with someone that wasn’t really my type is when I was drunk at a bathhouse once. This guy who was not my type at all kept pursuing me. The alcohol and his persistence wore me down. It was not very memorable or I blacked out or both!

 

[deleted2780451]

I'd probably never do it again (past that phase of my hoe life lol), but the first time I got DPed went from terrible and felling like I was going to have permanent damage to incredible and wanting it daily over the course of like 2 minutes lol

 

[Richard Licks]

The first time I fucked a girl's ass. OMG was it tight.

Ass fucking a woman will always be on my "Bucket List"

 

[notthatguy]

Ass fucking a woman will always be on my "Bucket List"

In the words of Nike..... just do it!

 

[Blade-Blanco]

My second girlfriend was more experienced than me. My first girlfriend had a great ass. It looked like two muffins stuffed in jeans. The sex was always vanilla. Shit, I wasn't experienced much so what did I know. My second girlfriend also had a great ass. I was a bit nervous and probably not over my first girlfriend. So I had trouble getting hard the first time. I was quite embarrassed. I remember the second girlfriend acting like she was going to go down on me for a bj. I got super excited and then she came up saying "just kidding". Thinking back on it, I think she just wanted me to beg for it. She "reluctantly" agreed but for some reason didn't want me to watch and covered her head with a sheet. Man, she went down, grabbed my dick, and engulfed it. Basically put my first girlfriend's pseudo-bj to shame. It didn't take very long and I exploded. Then she kept stroking me off and I was quivering. After, she swallowed. Man, I was hooked.

Her mom was a nurse. So she always had this jar of condoms in her room. I enjoyed the spoils of the relationship. I thought we had it figured out. One day as we were doing it the condom had broke. Up until that time I always had sex with a condom. Oh my God! The sensation of a wet pussy without a condom was an eye opener. I erupted rather quickly. I'll never forget her and what she taught me and the sensations from our experiences.