Surprised in sex.

I've been with a few women who found themselves surprisingly aroused to hear the phrase "good girl" in bed, the way it deepened their desire. I don't use that with every woman I end up connecting with, but there are times when you intuit what will thrill them.

I've had a few liaisons with married women where, at the start, we agree to use condoms ... and eventually I find them tempting me to forgo one later on, in the heat of passion. Surprising, I suppose you could say, as the expected gender dynamic involves the woman being the more cautious one and the man begging to push boundaries.
So hot. I enjoy being called a “good boy” as I approach orgasm.
 
Random guy I met off a dating site, hockey player, his third late nite visit to my place after practice (the arena was down the street from my apartment complex) out of the blue mid fuck starts choking me, without any conversation or consent request. I remember thinking yup this is how I’m gonna die before kicking him off me and kicking him out. Not cool.
I’m not naive I know it’s de rigeur in porn these days , but he had never done it and we had never discussed it.
Put me off random hookups for several years after that.
Ugh. Sorry you experienced that.

Discussion, communication, consent.

What a fuck was that guy was. And again, sorry it happened to you.
 
I had a great girlfriend in college. There was a small crew of us who were a bit older - in our mid/late 20s.

She taught me a lot. First it takes me a long time to cum. Especially w oral. She gave me this amazing blowjob and she took me all the way till i came.

She also had a food fetish. Yes food! She loved sweets (not fat at all, just had a sweet tooth) and we got to talking how she wanted something sweet as she was cumming.

It was a little tough logistically, but once while we were fucking and she was close, she had me put a brownie in her mouth. She looooved the sweetness and the orgasm at the same time. We did it also with Ben and Jerry’s ice cream once too. Messy and challenging to do while your fucking, but SURPRISINGLY fun!!

All kinds of fun with whipped cream.

Also had a three way w her and one of her friends from our older college group. A lovely surprise.

Before I had any concept of poly (this was mid 90s), we had this wierd three way relationship. Eventually jealousy crept in and it didn’t last. But it was lovely while it did!
 
Random guy I met off a dating site, hockey player, his third late nite visit to my place after practice (the arena was down the street from my apartment complex) out of the blue mid fuck starts choking me, without any conversation or consent request. I remember thinking yup this is how I’m gonna die before kicking him off me and kicking him out. Not cool.
I’m not naive I know it’s de rigeur in porn these days , but he had never done it and we had never discussed it.
Put me off random hookups for several years after that.
That's certainly not de rigeur in any porn that I watch. Folks have to actively search for that kind of stuff. I'm not against rough sex, but I've never engaged in it. I've chatted with many women on here who are into it, but it certainly has to be consensual.
 
I have really only had two huge sexual surprises in my dating life. The first one was a woman I met in a bar. We hit it off and she took me home, both pretty drunk. Took me to her bedroom and we stripped down naked. She got out two pairs of pink plastic handcuffs and asked if she could use them on me. I had never done anything like that, but I said sure. She cuffed my wrists to her bed post, then rode me until we orgasmed together. Afterwards, after she had set me free, she was so thrilled and said she couldn't believe I let her handcuff me. I took one of the pairs of handcuffs and snapped it apart like a twig. Told her I'd never really been worried. We dated for about 6 months, then just kind of fizzled out. But she made me play beach volleyball with her and her friends. One of which I ended up marrying. The three of us stayed friends for years.
 
My wife had been out with the staff from the medical office where she worked. I got the kids in bed, watched some TV, and went to bed. I heard her come in, but didn't completely wake up until I realized she had stripped naked and pulled down the covers. She pulled out my cock and started giving me a great blow job to get me hard. Then she climbed on and fucked me hard. Total surprise! I needed to send her out with the office bunch more often.
 
My wife had been out with the staff from the medical office where she worked. I got the kids in bed, watched some TV, and went to bed. I heard her come in, but didn't completely wake up until I realized she had stripped naked and pulled down the covers. She pulled out my cock and started giving me a great blow job to get me hard. Then she climbed on and fucked me hard. Total surprise! I needed to send her out with the office bunch more often.
I swear I think of Ginger Lynn every time I see your screen name and avatar. Sounds like a great surprise!
 
Random guy I met off a dating site, hockey player, his third late nite visit to my place after practice (the arena was down the street from my apartment complex) out of the blue mid fuck starts choking me, without any conversation or consent request. I remember thinking yup this is how I’m gonna die before kicking him off me and kicking him out. Not cool.
I’m not naive I know it’s de rigeur in porn these days , but he had never done it and we had never discussed it.
Put me off random hookups for several years after that.
I hope when you were kicking him off you, you kicked him in the balls.
 
I was on a third date with a guy I had met on a dating app. We had been talking about what turned us on and I told him how much being watched excited me. We went back to his apartment after dinner and he opened all of the windows and turned on all of the lights. We started kissing and just the idea that the people in the building across from him could see us brought out the exhibitionist in me. I turned into our first time having sex but not the last time I would have sex with windows open.
How would it be, to be watched by someone a lot closer?
 
Since someone shared a negative story, I will share one of mine...

I was getting hot and heavy with a guy and he tried to go anal with any sort of prep or discussion. It was extremely painful and humiliating and it's a big reason I just can't warm up to anal sex...

On a more positive note, I shaved myself bald downstairs so I could be smooth in a bathing suit and my man went down on me. Part of me suspects he was trying to manipulate me into shaving more often (positive reinforcement), but I enjoyed myself anyway.
 
So it was the 2nd time I'd been to see this girl. Things get hot and she begins giving me a bj. After being married to a woman who refused to do this, I had no idea I was supposed to tell her I was close to cumming and I just let loose. She was surprised but not in a good way. We still fucked a few times after that then lost touch.
 
Not as exciting as a number of the replies, but a number of years ago I was dating a girl who I would later marry. We went to bed one Friday or Saturday night and several hours later I began to wake up dreaming that I was receiving a blow job.
To my surprise I was. She sucked me off till I came and then rolled me over on my side, gave me a kiss and I drifted off to sleep again. Thinking about doing this with my current wife, but maybe this time I’ll just eat her till she cums and then, roll her over give her a kiss goodnight.
 
When participating in a gangbang, which I talked about in one of the threads on the topic, one of the guys was able to cum twice without losing his erection or having to stop. It was a lot of cum too. He gave Peter North a run for his money, let me tell you. Never in my life before that or since then have I ever seen a guy shoot so much.
Yes, indeed, that is a surprise. It happened to me with the first trans girl who ever fucked me. She had just finished cuming in my ass when she told me, "Don't move. I will get hard again and cum." She was still hard enough that her cock stayed in my ass, then not even a minute later, it got good and hard and she fucked me again, cuming for a second time.
 
Ok. Today’s surprise
Text message
“When you get in shower downstairs, I will be waiting for you”

I did as instructed, walked upstairs.
hubby naked, spread on the bed with the toy box open.

“Do your worst mistress”. So I did!

Not a bad morning
 
My wife is pretty mild, so any time she pulls out something new, it's a surprise.

-She's typically very submissive within her narrow comfort zone, so her being dominant is rare. There was one night, semi-shortly after she moved in (2010ish?), that she was on top and trying to be dominant and i wasn't making it easy. I can't remember what she told me to do, but i said no and was shocked when she slapped me across the face. I think she realized she fucked up by the smile i got. Took her until very recently to try it again.

-maybe a month ago, she was playing with me and using her rabbit vibrator on herself. Out of no where she puts it on my cock and starts moving it around looking for sensitive spots. We had already been at it for awhile and my back wasn't liking being in bed anymore, so i knew next to her, took the toy and held it length wise under my shaft while sucking on her nipples. It only took about 2 minutes for me to cum, which i think intrigued her as much as delighted her.

-when we were dating, we hadn't talked much about porn. She knew i watched it occasionally, and i knew she was aware of it, but wasn't into it. We were long distance and she was visiting. She randomly asked if i had any porn that we could put on, so i put on the one dvd i had. She told me to watch it while she sucked my cock. We ended up fucking for over an hour before her pussy couldn't stay wet anymore and wouldn't let me in after we moved to the bedroom. She said later that she liked the sounds of other people having sex while we got it on. Fast forward to about 2012, and True Blood led to more than a couple of orgasms.
 
Got squirted on with old girlfriend I was hooked I loved her juices all over me and bed! Same girl I licked her ass for first time she clinched up but slowly opened up and loved it! She returned favor also it was amazing feeling !❤️❤️❤️❤️
 
This isn't very radical, but a warm memory. I was home from college and my GF, originally from Kansas but at school in upstate NY, came down to the coast for the weekend. I had a single bed in a new part of the house away from everyone else. She stayed in my brother's room who was away at school at the time. In the middle of the night, she quietly came to my room and snuggled beside me with a T-shirt and nothing else. In that tight space, she maneuvered so she was on her back, one leg up and I was on my side and slipped in. This was nothing new, it was one of her favorite positions. As we finished, she said "Don't slip out, stay in" and then she pulled her leg over and spooned, then leaned back and said "This way when you get hard in the middle of the night, you can just start moving again and give me some more". We slept and sure enough, two or three hours later I woke up hard and started moving just a little. She moaned, reached behind her, over my hip and pulled me encouragingly.
 
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