Same answer "My Wife" I met her as an uninformed young virgin who (and I can't state this enough) knew nothing about sex! Thanks to Catholic fear and shame it's still a struggle for her owning certain sexual thoughts and feelings, that said I wouldn't trade her for the world when she's in that right mood and right train of thought the sex is amazing with a woman who's warm, intelligent and beautiful in my eyes!

 

Nothing worse than when love gets in the way of some good old revenge sex.

Thinskin

P.S. The "I want you" worked then?

TS

 

Best was fucking a friend in her hair salon after she gave me a haircut and wash while she was naked. Also fucked her in a strip club VIP room where she worked.

Worst was my sis in law. Fucked her from behind in her bathroom then spun her around to grab her hair push her down and cum on her face. Only did it cause my brother in law was a douche but, his wife would fuck just about anyone. Thought for sure that was gonna be a trip to the pharmacy after I did it.

 

Most regrettable was this extremely sexy filipina who had just turned 18, she had an amazing body and a really cute face. I love eating pussy and her pussy was bitter as fuck....... So disgusting i had to use the mouthwash as soon as she left. Still i soldiered through and ate her nasty pussy for like 10 minutes (gag) .

Then we fucked and the sex was ok but when she blew me which she did for like 2 minutes she seemed disgusted and she just didn't really seem to into it.

Unfortunate because the worst woman in bed was the hottest woman i ever fucked.



most memorable? My ex girlfriends parents were out of town so we had a sex marathon while they were away. It was capped off by her riding me in a rolling office chair. It felt like a combination of a lap dance and fucking. It was incredibly hot.

 

MOST REGRETTABLE - She was a chubby native chick with bleach blonde hair, i wouldn't say she was fat but she was definitely thick, we had some mutual friends so i knew who she was but we weren't friends, she had the reputation of a huge slut, every time i saw her she was with a different guy. Normally i thought she was kinda nasty, that is until a bunch of friends went camping one weekend, she was with a group near by that we knew but as far as i know she was by her self for once, at first i didnt pay her much attention but after a few drinks she started getting flirty and being that i had been in a dry spell for a few months she started to seem alright, few more drinks later we had gone for a slight walk, she straight up asks if i want a blowjob and i gotta give her credit, she gave the most amazingly sloppy blowjob ive ever had and she didnt even miss a beat when i shot my load down her throat, we go back have a few more drinks and next thing i know im watching her ass jiggle as i lay into her from behind. When i sobered up the next morning i couldn't believe i had actually fucked her, the sad part is that thanks to a bottle of whiskey i decided to fuck her again the following night, luckily my tent was away from the others and she was only interested in dick then she went back to her own tent so no one ever saw her coming or going. I thought about bleaching my dick after that.

MOST MEMORABLE - First time bareback and nutting in a woman, i was 19 hanging out with a friend of mine in her hot tub, She was a gorgeous blonde knockout but that didn't mean much as i had known her since we had started high school so that friendship crap always got in the way. So were sitting in the hot tub having a few drinks and she starts going on bout how happy she was to be single, the only thing she didnt like was the fact she hadn't gotten laid in over a week, i laughed and said something about how it must be so hard being that she could get any guy into bed with zero effort, thats when i felt her hand on my leg and she asks "does that include you?" at first i thought she was fucking with me then that hand found my cock, we started going at it, stripped down and moved to a couch inside, she goes to mount me and i tell her to grab a condom first, she smiles and says shes just started taking the pill a couple week before and she'd rather go bareback, that was all the convincing it took, feeling that tight wet pussy was the best thing ever, so much so that i set a new personal speed record and blew my load in her in 5 minutes or less, i apologized for my quickness and told her it was my first time going bareback, thats when she told me she had only started the pill the week she broke up with her BF and that i was actually the first guy she had ever gone bareback with. She didn't seem to mind my quick performance she just wanted to know how long it would take me to get hard again. I knew i was basically just her rebound but i took full advantage of it.

 

Can't really think of any time I really regret. Once in an old hotel room waiting for the hot water to heat back up so we could shower, we fooled around a bit because there was nothing else to do. Seemed awkward and forced for both of us. I don't really regret it, it was just... awkward.

Most memorable? Too many good times to choose from.

 

Most memorably, but not the best. I was seeing a very petite woman, 5' nothing and I'm just over 6'. She loved sex and my cock but because of the size of my cock and the size of her pussy I could not get fully in, so always had to restrain myself, never really able to 'let go'. For some reason, although she obviously had them, she had very quite orgasms. One morning on the way to the office, fully suited for a business meeting, I called in to pick up my phone which I forgotten the night before, she was in the laundry room, in just her nightdress doing some washing. As she put a load of washing into the machine she decided to also wash her nightdress and stripped it off,when I saw her rounded butt and then when she turned her small but perfect breasts, her nicely rounded mound and her crease that was it, I was ready and when I dropped my pants and she saw the state of my cock so was she. I lifted her onto the washing machine and we stated fucking; I don't know if we had found the perfect height, if it was the position, or the fact her weight had unbalanced the washing machine but this time with the help of machine's juddering beneath her butt and my thrusts my cock for the first time went all the way in, balls deep, she loved it and so did I. We fuck like we never had, with the way the machine was making her body shake, her tightness transmitting it to my cock, only adding to all the sensations. Just as I was about to cum she started screaming and yelling that she was "having a big one", another first adding to my excitement, and her extra tight contraction along and around the length of my cock finished me off, her shaking and the machine's shaking squeezing out every last drop. Afterwards I think we were both in a kind of state of shock at the intensity of what had just happened, until she broke the mood by saying how funny I looked standing there, with my pants round my ankles, in a white business shirt, with a tie hanging down that matched the colour of my now hanging cock.
Most regrettable. The night a FWB, who was a really great fuck, whenever, however and as many times as I wanted, told me after I had deposited my third 'load' "hope that this time you've got me pregnant". Turned out that unknowingly I'd been used, with her husband's knowledge, as a surrogate donor. I might have been getting the goodies but that pissed me off and it was our last time; I got the last laugh because she wasn't.

 

Most regrettable had to be the first time I fucked my first wife because it led to six years in hell before I got divorced.

 

Can't say any were truly regrettable but some were a bit much. Woke up in a strange bed (I'm a sober drunk now but had many black-outs during the day). The woman next to me was a stranger and pretty homely. Out of the fog, I heard a door open and a guy shout out, "I'm home honey!" In a shot I was out of bed, dressed and out the window. After running a couple of blocks I realized I didn't know where I was and couldn't see my car. Long story short, I was 75 miles from home and it took me half an hour to find my car. Never found out who I slept with or where I met her.

Another comes to mind. I was seeing a married woman who never fucked but gave BJs. She was wonderful ... until she told her husband about me and he came after me with a loaded 45! I managed to elude him and stopped seeing his wife immediately.

Most memorable was the first time with my wife -- as others have shared.

 

Both were mistresses the most memorable was Dianne for her open honesty in a strange sexual nature and intensity! Regrettable Patty who was too immature to be the other woman!

 

Most memorable was first time with another woman. As I've mentioned in several threads. No regrettable fucks that stand out. Just some soso fucks.

 

Memorable...first time having male sex CD'd. Little black dress camasole pantys and thigh highs, short blonde wig and make up, fucking hot 19yr old.My friend dressed me and took me out, several bars, drinks and teasing being felt up. We picked ip a friend of his and went back to a hotel room to drink, coke and weed it up
I came out of the bathroom and my friend and the other guy were kissing and masturbating each otherThey got me on my knees and I sucked cock for awhilethen my friend manuvered me doggy and took my pantys around my thighs, tounged and licked my ass and stroked me while my mouth was full of cock, spanking and fingering me he slid his cock in my ass... we were doing coke so the took turns ficking me and cumming in my ass all night...

 

Ive had a few regrettable fucks and a few memorable ones too.

Letting a good fiends partner fuck me was regrettable because of the fall out after.

Getting drunk and not remembering too much other the realisation I had sex with someone I didnt even really like or fancy would be another less than stellar moment in my life.

Memorable would be being, and to misquote a well known song, wined dined and 69'd by a handsome and extremely rich man. There wasnt anything bad about the experience except I wasnt the love of his life like I thought at the time, just a very young and very impressionable girl. I wouldnt change it though I grew up a lot and the sex was terrific !

 

My most memorable was my first girl/ girl experience. That opened up a new world for me. My most regrettable was with my ex-husband. I slept with him before he got married and I thought, why did I do that? I guess it was a little payback at the time.

 

My ex girlfriends daughter. Was actually more than once and a number of times over a year. She was hot as fuck. I dont really regret fucking her but she did cause a lot of trouble which culminated in her mum becoming my ex, which is a regret.

 

I emailed this couple on Craigslist several years ago..got pics and talked for a week before meeting them in a hotel room.I get into the room to find this last fat bitch on the bed naked and legs spread.she was at least 100lb (she was about 300+lb) heavier than her picture was...she looked maybe 200 in it.

The guy was just an average guy. I sucked him off first while trying to think of a way to leave. He came so fast and unexpected. Was really salty and nasty. She sucked my dick very horribly so I sat up and just fucked her. Nasty chafed inner thighs...excess fat swinging anywhere. Her huge fat tits were flat with huge nipples. There was nothing good about her at all. I thought about a friend of mine so I could cum...came inside her..her husband proceeded to was the creampie. I went into bathroom and showered off real quick..got half dressed fast...came out and said I left phone in the car..brb...and fucking got out of dodge!! Turned off phone for the day.

I like chubby girls..but this chick was obese and I was tricked.

Most memorable...my current gf. The first time she pissed on my dick..then sat on it to fuck me, while still wet with her pee and hearing her moan and say, " omg that feels so awesome.I actually like it" we hadn't tried ws yet..that was our first time.

 

I would not call this regretable because I definitly enjoyed fucking the wife of one of our friends. Since then her personality has changed to the point that if I were to never fuck her again it would be okay with me. My most memorable has to be with a girlfriend prior to meeting my wife. My brother and I arrived at our house in the middle of the day with our respective girlfriends. My brother and his girlfriend immediatly went upstairs to the bedroom we shared. My girlfriend and I wanted to fuck and there was no way we were going to fuck in the same room with my brother and his girlfriend. We took the only other room in the house where we could close and lock the door, the bathroom. My wife, now teases me about using the bathroom to fuck my then girlfrienď and says, "How romantic, the bathroom floor." We thought it would be a pleasant afternoon fuck, but instead it was the most pleasurable the two of us ever had. I was super hard and she was extra wet, we were both eager for each other. The entry into her was pure ecstacy, unlike any I had ever experienced. She moaned and called out my name as I entered into her, she had never done that previously. We fucked each other slow and easy, and we fucked each other fast and hard. The entire time we were in the bathroom all we did was fuck, no foreplay, no oral, only fucking each other. When we finally stopped it was only after she told me that her pussy was sore. We had been fucking for at least two hours, with her cumming numerous times. When I finally did cum in her, it was unlike any that I had ever previously experienced. I felt as if the only thing that existed was my cock, her pussy, and my cock releasing a massive load of cum into that pussy.

 

To adequately describe the most memorable that springs to mind and do it justice would require Hush-like length and writing skills to match but the most regrettable may be the most recent. Like someone said... Don't fuck friends!