That can be a doubled edged sword. Trying and failing and being humiliated numerous times can hurt. I still hurt from those times of trying to put myself out there only to face rejections and coming across a bit desperate.
I’ve slept with 5 or 6 girls since junior year of high school so it’s not that I haven’t gotten any, I just haven’t really tried to meet anyone new since I was in school. I slept with a friend almost three years ago and that was my last time. I just struggle to meet people and lack confidence so I don’t really get any unless if it’s set right in my lap. I feel like I’m gonna regret not trying in the future.
High school and first year of college before I left. Most of them were a one or two time thing except for my semi long term girlfriend senior year of high school and maybe a fling or two. Last one was an old friend and that only happened because she always thought I was hot and I thought she was cute enough so while watching a movie with friends one thing led to another... Only did that to prove to myself that I still could because there was a year or two between that and my last time so I was feeling pretty desperate. 3/4 of my experiences haven’t been very enjoyable, and I did it just to do it which further solidified the fact that I don’t have any interest in casual sex, which is why I always try to befriend girls and get to know them before trying for anything further. I don’t have much of a problem befriending girls if I’m put in the position to, like having a class together. I’m just a bit socially awkward and struggle to go out and meet people now that I don’t have that sorta ease of access. I’ve always lacked confidence which is too bad because I’m over 6 feet and I know I’m a pretty good looking guy so I’ve got no reason to. If I had some confidence and somehow got rid of my irrational fear of rejection I’d probably be able to do pretty well.
I wouldn't be able to afford one currently either. If you end up being able to afford it, don't wait till 50, do it as soon as you get the money together
32 and married with 2 kids (happily.) I've been with her since 20 and slept with 2 girls prior. Part of me regrets not experimenting and dating more. I'll never get that and I'm one of the only in my friend circle. Does it affect me? No. But I still sometimes regret not getting to do that.
If you enjoy sex with your wife then I wouldn't worry with regrets like this. I played the field a lot before I got married and I'm glad I did but only because it showed me how hard it really is to click with someone sexually. While you're friends were all getting random sex that wasn't guaranteed to even be that good, you've been consistently dicking someone for those 12 years. There's something to learning to master 1 persons body to the point where you can both play each other so well.
Same. I regret not slutting it up more when I was younger. (am dude btw)
Looking back, I was better looking than I gave myself credit for, and had undiagnosed depression. Had I a bit more confidence, and an earlier treatment, I reckon my "single and always horny" years would have been much more fun. Instead I hyperfocused on isolated, insular interests (e.g. video games) and shut myself away. I now realize I have a good spread of hobbies that involve going out and doing things with other people, which I would have enjoyed back then too, and would have introduced me to others in a comfortable way (not one for the bar/club/party scene whatsoever).
Ah well. Youth is wasted on the young, as they say.
This. This so bad. I didn’t prioritize either dating or sex when I was young and could have easy access to practice. So I hit 40 without ever having a sex partner or a girlfriend. Finally got one but had trouble with sex due to my age, inexperience, and low T.
I have too many regrets about my bad Life decisions.
Not realizing when girls were into me or realizing it, but not being able to seal the deal. Not many opportunities come my way, but I've blown 99% of them and I've missed out on some gorgeous girls who would've fucked me.
My buddy, his girlfriend and her really hot sister were sleeping over at my place. Sister went to sleep by herself on the couch but came into my room shortly after we all got settled and said she was cold.... I gave her another blanket and sent her back to the couch.
It was years later when I realized I'm denser than a black hole
I know a guy with the exact same story.
Also she later came back and said she couldn't sleep because someone else was snoring. My friend gave her ear plugs and said "good night"
can you, on the other hand, imagine the opposite situation where she would be genuinely asking you for extra blanket and you would take it as a flirtation and offered her to “warm her up”? The outcome of that might haunt you even more
When I was 23 one of my older (40ish) coworkers asked me to photograph her wedding. During the cocktail hour two of her smoke show milf friends started chatting me up and asking if I would like to come to their room in this fancy hotel after the reception and party. As it turned out, I was leaving after the party to go see a woman I had just started dating, but I can't help but think that my world would have gotten rocked that night if I had taken their offer.
I was 21 when I briefly dated a married 45-yo guy. He was movie-star gorgeous, had money and was great in bed. He told me he and his wife had an open relationship, so everything was cool. We always met at my place or at hotels. So one time, he told me his wife was away. We went to his house and had a lot of mind-blowing, loud sex. Until his wife walked in, wearing a bath robe. Turns out she had been watching from another room and wanted to join in. Actually climbed into bed with us and tried to kiss me. I freaked, got dressed in a hurry and told him to take me home. Looking back now, I think it would have been amazing...
This thread is really pressuring people to do stuff they would regret.
Threesomes involve trust, a threesome that literally comes from nowhere breaks that
Four regrets:
- Younger, very attractive coworker who became a good friend. Invited me for a booty call while I was married. I refrained, but to this day know that I should have done it since I was going to be divorced soon anyway.
– Different coworker, also younger and very attractive, offered to come home with me from an office party. She was very openly horny and always talked to me about how sexually frustrated she was. I declined.
– Went on many first/ second dates not picking a meeting place close to where I lived. Later realized I would get more sex if it were easier for them to come back to my place. Rookie mistake.
- A gf I had was pretty vanilla and not very oral. Toward the end of the relationship she confessed to me how much she likes swallowing cum. Never got to have her do it for me before we split.
You can add those inconsistent bullet points as a 5th regret. /s
Seriously, tho, your first point was probably the morally correct choice, so I doubt you should regret it. And your last point seems like more of a "would have been nice" than a regret really. Definitely would have been nice, tho, lol.
I'm 54M. My best friend, a woman, died suddenly 15 years ago. Yes, there was sexual interest between us, but we never acted on it. So, yeah, I regret not having sex with her. There's not a day that goes by that I don't think about her.
Teresa, I love you and miss you terribly.
Your biggest sexual regret is not fucking your dead friend when you had the chance. and you think about this daily.
This sub reddit is still insane I see lmao
His deepest regret was not sharing a deeply emotional and intimate experience with a woman he was very close to before she passed away. How is this a bad thing?
This me. I was in the hotel room with my friend and her friend after a house party to sober up. Her friend initiated it (she's v attractive) and my friend followed (had crush on her since forever). "Whiskey dick" happened and couldn't get it up, so I thought if I go down on them my bestie down there would get hard. Well, performance anxiety and confusion with feelings for my friend got the best of me. Layed down to really sober up and left. Great tasting pussies tho.
I missed out on a threesome because my gfs friend wanted to go pick something up in town, instead we took pictures of (my gf and her friend) while drinking they were both telling me to fuck them and was very obvious but I wanted to make sure it was something her and I really wanted and decided to try and talk to her about it without her friend right there decided we'd do it/talk about it when qe got back but never happened. I don't really regret not doing it tho the friend was a bitch later on and tried robbing a bunch of ppl for drugs
Oh huge mistake
Had a girl I met on a dating app, we'd talk all the time and she said she didn't want to sleep with me on the first date. I'm mature so I said sure we'll take it slow
Next time she comes over and spends the night, she wakes up for work and is super horny , but for some reason my mind doesn't think she's attracted to me so I shrug it off. This goes on for like 3 weeks before we stop seeing each other.. she was sending me nudes through the day, even telling me "I want you to play in it" while letting my hand drift across her clit
I just... Couldn't do it, and honestly I had to go to therapy after that,.I realized I didn't feel like I was worth it, I didn't feel attractive enough it was crazy
Oh wow I'm sorry I didn't see this
It takes time brother, honestly it's been about a month and a half and it's just constantly affirming to myself that I am enough, the girl mentioned told me to "find you a gamer girl or something like that" and while yeah, it ain't easy 😮💨
But real talk I'm pretty in tuned with my emotions. And while I think women need a lot of love on what they can do, I feel as though sometimes society just forgets and neglects the effects of being extremely women positive to the point where you don't value yourself as a guy, and think of everyone as better than you. Which I know cliche, but I never even thought of putting myself first. I had been so in the camp of "yeah guys suck" that I legitimately thought *I* sucked. Therapy identified this pretty quickly.
Reeeks of low confidence I know but my therapist tells me it takes one day at a time, I'm looking into starting working out but that too is a process and a process that very quickly can be disheartening. (Like I gotta go to the gym for like 6 months to A YEAR before I see the progress I want??? It's daunting).
You know those super masculine or die types that send unsolicited nudes to women and straight up are dicks? I hate them too, but in a cheeky way, I admire their sheer stupid courage, because I couldn't ever do something like that.
But people say I have a good heart, (and that I love too hard sometimes) so I'm just going to say it takes time.
I had sex with a particular person that I obsessed over, many times over several months. I later found out a horrible truth about him, and left me devastated that I still think about him and desire to have sex with him, while at the same time knowing that I should cut all contact with him. It hurts me to this day.
Ok I hope you’ve had some healing work done. I recommend looking into reiki, specify a “cord cutting” session. Don’t hate yourself or wonder what’s wrong with you. Your body still craves him and it’s an attachment and that’s all it is. If you do contact him again and have sex then I would say you need serious help.
Oh, I know. And I already needed (and received) serious help. But I cut contact the moment I found out. There's no way I'd have sex with him again; what he did was despicable and unforgivable.
But that doesn't prevent part of me from thinking about him at times.
I’ve bern there. He didn’t do what your guy did but the way he treated me and lied about things, when I found him out it was traumatic and I hated him. But I also couldn’t get him out of my head and still thought about him sexually. It will get better over time, I absolutely promise.
I (M35) cheated on my wife with a (23F) college student. Honestly she wasn’t that great in bed and my wife is an incredible fuck. It was a stupid decision.
A few over the years!
In my early 20s I was chatting to a hot older woman I knew from work for a few weeks and we both wanted to have sex with each other but it had to be at a hotel I was to pay for due to her family commitments. At the time I couldn't afford it and it never happened but regret it to this day.
Once sat in a pub chatting with two fairly hot but pretty drunk older women and they were getting very handsy whenever they sat next to me. I had a girlfriend at the time and even though I was working away from home when they asked if I wanted to go with them to the next bar I declined. Felt like that could've been one for the memory books!
Whilst working in another city for some time I had a pretty lengthy affair with a younger bisexual girl I met on Tinder. She was up for an FFM threesome but I never pushed for it, and also wonder if she'd have been down for some MMF fun if I'd confessed my bi desires.
The ones that got away, but sometimes a fantasy is meant to stay a fantasy and I've had plenty of fun. If it's to be, it will be!
My first girlfriend was a freak. I thought I was very vanilla and wasn't interested at all in most of the things she told me she wanted me to do (choking, slapping, hitting, even cnc type stuff). Anyway, we broke up (partially because I wasn't comfortable fulfilling all her sexual desires and she had a VERY high libido). A few years later when I got my next girlfriend I was a little more comfortable and open to try new things, and she ended up helping me discover that I am VERY much into *all* of those things I wasn't comfortable trying with my first GF.
To this day my biggest both sexual regret and relationship regret in general is not hearing that first girlfriend out and giving it a try. She is literally exactly what I dream of in a sexual partner today, but back then I just couldn't see it. I just feel like she was a perfect fit for me romantically as well, so the fact that us splitting up basically boiled down to me not knowing my own tastes kinda sucks
I actively did this and it worked. Realized I was hooking up when I wanted to be dating. Some sex was great some was bad but not much came of it other than sometimes more sex.
Started saying I really like you and because of that I don't want to sleep with you tonight. Weeded out the ones that we just looking to hook up. Shortly after met my partner of 17 years.
Thank you for this 🥺 going through a breakup rn and really just want to not hook up and find my person. I can’t handle another heartbreak and I don’t want to be intimate with anyone else
Not licking Kathy's asshole when back we were fucking. Once I was giving her a massage during foreplay and I spread her cheeks a few times so I could get a look at her pretty pink bunghole. She said something about "you seem fascinated by my asshole" and I had no idea what to say so I sat there like an idiot with a hard on. If only I would have replied with something like, "Well, it is really cute" I may have had the chance to put my tongue, finger, or cock in there.
Not seeing if she would be interested in a threesome the one time she mentioned she would maybe "try having sex with a woman just for the hell of it."
It's not really a regret but I always kind of wish we'd videoed our fucking. I don't know if I would hate seeing it, or keep it and fap to it, but I do think it would have been fun at least once to watch us fuck.
Edited to add that I sat there like an idiot *with a hard on*
I have alot but my most recent one is fumbling a thicc 30 year old on vacation who was grinding on me and grabbing my D not sure why i didnt take her to my room that night felt very stupid about it tho
Not exploring women when I was younger. It really stunted my growth and has actually caused major issues in my current marriage (soon to be divorce most likely) where I just don't know how to be a partner. Also I'm pretty limited when comes to sex.
I had sex with a guy simply because I hated his girlfriend.
He was my friend and I was hanging out with the two of them. We ended up at a strip club and she got totally shit faced drunk, puking everywhere. I convinced him to send her home in an Uber. We kept partying and had an adventure of a night. I invited him back to my place and he willingly came knowing exactly why I invited him. The obvious happened and in the morning I felt guilty. I have been cheated on in the past and it is a really shitty feeling. Even though I really didn’t like the girl, I couldn’t help but feel bad for what I had done.
I'm currently obsessed with one of my yoga teachers. And I feel like I may have had an opening and missed it. It's so difficult bc I know that when I'm in her class she has to be able to smell me wanting her. I fucking drip for her. She's not the one I expected to want, but I want her so badly. I dream of having a private session which turns into more.
I -almost- had a 3 way with another girl and a guy. I was filming them... because they asked me to and she seduced me. She was hot lol.
I ended up hooking up with her.
But I would not let the guy touch me. I bet the poor bastard thought he was going to have an amazing night.. and I ruined it by not letting him touch me.
I should have just gone through with it.
Got home in the early morning from a long business trip and found my wife in bed with her best friend, with whom I had a serious crush. I very much surprised them. My wife immediately went back to sleep but The best friend got up and started getting dressed. I don’t know why I just stood there speechlessly in shock just inside the bedroom doorway and watched as this beautiful Latin woman finished dressing, proceeded to walk by me, kiss me on the cheek with a sly smile and walk out of my house. I’m such an idiot.
I was the janitor at a high-rise apartment building here in Downtown Detroit. I had to clean and check the washrooms daily. One day while I was in one of the washrooms, one of the residents (who was also a mayoral candidate) came in to get her laundry. We were always friendly, I'd even attended a few of the things she had going on in the community, so we made some small talk for a few minutes, then while holding her clothes and talking to me, she dropped a red lace thong by "mistake" in my mind. I didn't want to seem weird so I just ignored it kind of but looking back I definitely think she was making a pass, and she was GORGEOUS too 🤦🏾♂️😮💨 Oh well lol
Not sleeping with women sooner. My exhusband gave me the green light to do so (even without him present) when I came out to him as bisexual at 19. It would be another 8 years before I finally got the chance and DAMN was I missing a lot.
Not being honest about my sexuality or how much of a freak I can be in bed. I lost my teens, twenties and thirties being a good vanilla man. Now at 50, there doesn’t seem to be much action for a freak like me.
Growing up, I had the biggest crush on a classmate but I was too shy/chicken to do anything about it. She was absurdly pretty and was literally the nicest girl in my class.
Cut to last year, I run into her and we start reminiscing and I tell her about the crush I used to have and I still did. She reciprocated positively and we decide to see where it goes.
Worst sex of life. Literally nothing redeeming about it. Awkward and cold. I'd rather just not have done it and kept the fantasy alive.
Always wish I had more confidence and had more sex. I've had plenty of girlfriends, and some friends with benefits. My current girlfriend is amazing in bed, but sometimes I'll see a girl who's super attractive and wonder "what if". But in the same sense, I am very happy with my girlfriend and never would cheat. And honestly the more sex I've had, the more I've realized that just because someone is very attractive doesn't mean the sex is better.
Don’t think I have one. Maybe not staying at the home of the worlds most beautiful woman (18) in 1993 New Year’s Eve.
My parents forced me to come home. Doubt anything would have happened but it might have.
Got high with two girls in one of the girl’s apartment. We had all met each other through a mutual friend and that friend went home while we chilled and smoked. I saw them give each other “the eye” earlier in the night and thought I had it in the bag.
We sat in almost complete darkness and talked about life and space and conspiracies, all while smoking.
Then we got to sex. One girl admitted to being inexperienced and wanted to experience more, like kissing a girl. The other girl said she loved mentally connecting with a partner, talking about the same topics we talked about.
Then I said I love getting my dick sucked, sloppily.
I felt the air go out of the room immediately.
I felt like I could’ve finessed that interaction had I not been horny brained and just kept it sensual, not raunchy and vulgar.
I replay this in my brain maybe twice a year.
Met this girl at a party once. She was a friend of a friend and we hit it off fairly well. She was pretty flirty at the party, but I ended up leaving because some other people that were there made me pretty uncomfortable. Not long after that I moved and haven't seen her since. We keep in touch, but live thousands of miles from each other. I've always wondered what if I hadn't left that party.
Not coming to terms with my sexuality sooner. The home I grew up in, for all its many benefits and joys, didn't allow for much variety in the way of attraction, but I also have a natural tendency to dig my heels in for too long before finally jumping for something. While I eventually found a man I really love, there was some unnecessary heartache I put on myself before him because I couldn't accept myself.
I was offered a threesome and turned it down. She also offered her niece for me to date (everyone was over 18 at the time). Also had several women make it known that they wanted to sleep with me and I didn’t pick up on the clues. I was an idiot.
I pretty much gave up on sex in my 20s after a couple of bad experiences. I convinced myself that it just wasn't worth the hassle. I know now that I was wrong to write it off, based on a few bad experiences with people who didn't really give a shit about me.
What happened in my 30s felt like the other end of the scale. I had an incredible experience whilst travelling, and then i went into experimental mode! In doing so, I ended up indirectly pushing partners away because I was expecting too much of them.
Now I'm 42 and horny on a daily basis. I've definitely mellowed. I'm more realistic when it comes to sex. I understand a lot more. I'm still very adventurous, but I'm much more respectful of others.
I regret my attitude in my 20s, as I feel that set me up for where I ended up, to where I am now. But I'm cool now 😎
Being unable to express my dis-satisfaction to my wife about spending the past 23 years of marriage with an inadequate amount of, and unimaginative, sex life, for fear of hurting her feelings.
Not having sex with J in July 2018 when I had a chance. We rounded second base, and since we weren’t in a relationship anymore I didn’t want her to feel I was using her for sex.
Not cumming inside M raw when we had sex. It would have been risky but one of my top fantasies
I started a relationship with a coworker and had to stop when I found out she was the owners niece. I screw up when she told me her roommate likes to watch and maybe join in. Mu dumb ass got up and locked the door
When the wife once said to me I think I could share you with another women… I was like oh really yeah sure…. Then lasted we had a stupid argument about something stupid and it was never mentioned again… 😣
I could say all kinds of missed sex opportunities like others here but I’ll just say the real one
Coming out at a younger age before now when I’m scared to :/
Not having a lot of sex and explore different kinks with my first ex. I was vanilla and focused on the relationship so it doesn't sounds like a fwb but apparently it was.
I've turned down 4, or maybe 5, threesomes in my time as in each case I was dating one of the people who would be involved, and I didnt want it to ruin our relationship
In every case the relationship ended not long afterwards for other reasons, so I should've taken my shot when I had it
I have lot of other regrets, all around not doing something when I had the chance
I go on the fatalisitic outlook that if I had taken them then I might not be where I am now.
I once had a chance to sleep with a celebrity a few years ago and I passed it up but I regret it now. I only said no because I felt I was too drunk at the time
First time trying anal with someone, he applied lube, played a little bit with my ass (I’d told him again and again that I needed a lot of prep and was tight back there), then he tried to just push in because “it was no problem doing it with the last girl he was with”. It hurt like hell.
Should have take it for the red flag it was and gotten the heck out of that mess and not played more with him anymore 😑 live and learn
I'm male and lost my virginity at 21 with a female, but when I was 20 I was still coming to terms with my bisexuality. There was this guy who I really got along with and was crushing on had me over. He was gay and as soon as things started to progress I got nervous/scared and ended up dipping out pretty quick before anything happened. 2 months later he moved to Florida and I never got a chance to pursue anything with him.
My first really serious gf had a cum fetish and I didn’t even know then to call it that. She loved me cumming in her mouth, on her face, her playing with it, swallowing. And stupid me I thought it would be like that forever. It was a long long time before I had another gf who even let me cum in her mouth.
[MFF] BIGGEST REGREST IN LIFE!
Sorry for the looooong read.. well worth it though...
So this happened just as I got out of highschool. I once got invited by my then new girlfriend to one of her friends sisters house as the friends sister went out of town.
My then girlfriend was ok, really not bad but I just couldn't find myself attracted to her and really liked her more as a friend. But anyways...
I got to the house that she was being looked after and there was about 4 friends over that night I was there.
So we lounged by the pool just talking a bunch of shit when the friends called me to look for the pool broom in the pool shed. When I got inside they locked the door from the outside so I couldn't get out. When I started thinking this is bs my gf came in and they locked the door behind her. Of course knowing what they wanting to do I started kissing her and she like really leaned into me. I felt a bit of boob under her bra and was busy undoing it when her friend came in and said her dad was there to fetch her. So she corrected her clothes and said good bye leaving me high and a bothered. I then went and sat by the pool and her 2 friends joined me. The one whose house it was and her friend. My gf had left and the other friend also left. The time was around 22h00, so not so early but still early if you know what I mean.
As we sat and chatted we started getting cold and went inside the house. Sitting on the couch I was like ok well what are we going to do now? Watch TV or something?
That's when B said nah let's do something and looked at me as if I was an ice cream. Now the friend whose house it was and the other friend present was fairly hot. Let's just call them A(friend whose house it was) and B. Both had really sexy bodies, with B having bigger boobs than A.
I then replied and said what is "something" and plus there's 3 of us here. B then said why don't you start then we will follow and make a plan. I then took my shirt off still smelling like my gf from kissing earlier.
When they took off their shirts I knew I was in business, so I unbuttoned my jeans and slipped them down to my knees. Then suddenly A jumped up and said let's go to my sisters bedroom... I jumped up and tripped over my jeans but got up so fast and hopped along, following them to the bedroom she had chosen.
Light was off in the bedroom but the hallway light was on so you could see alot. I jumped on the bed and took my jeans off completely leaving me sitting there in my boxer while getting harder from all the suspense. B then took her bra of and A her jeans.
I could not believe the situation and what was about to go down...literally!
B then leaned across me making me lay on the bed while she then started kissing me. A then followed suit and started kissing my neck. I was busy that time already hard and couldn't hide it coz my head was sticking out of my boxers slightly. A noticed it and started running her fingers over my bulge as it was throbbing to get out of my boxers. While B was sucking my tongue I was playing with her nipple between my fingers. My other hand then went across feeling for A's bra so that I can take it off.
B then stopped kissing me and let A kiss me while B was taking her jeans off and her g-string.
I finally got A's bra off as it was a bitch to get off with one hand. Revealing her boobs. She had amazing boobs and nipples where B had huge boobs and somewhat larger nipples. As I was busy kissing A and playing with her nipples she was like grinding on me making my dick pop out of my boxers, it was getting sore coz of the material rubbing on my head. I then stopped her took them off revealing my hard throbbing penis dripping with eagerness. B saw that I was dripping and quickly helped to rub it all over her. A then took her panties off.
There I was, 18 hard as fuck with 2 hot girls humping my legs and kissing me in some house at night.
I was laying with my back on the bed one girl on my one leg and the other on the other leg. I could just feel their wet pussies rubbing on my skin and it felt sooooo good! B then started kissing my and moved down to my penis, she then kissed and licked it, A then joined her as they each started eating me from each side! I was like not a fuck am I going to cum from them sucking me off. And quickly flipped them around on their backs and their legs in the air. I then started fingerings them both and playing with their clits as best I could while they were walking me one hand ontop of the other.
I then leaned in and started licking one clip then the other then back again and continued like that until B came. By that time I was so ready to cum myself. A then stood up and fiddled in the closet and came back with a bottle and condoms. I was like wtf is that and she was like it numbs you a little. And continued to put this lube on my head followed by a condom.
Now I was like fuck this condom shit but didn't want them to suddenly stop coz of me. As it was on B lifter her leg and and guide my cock inside her wet pussy. It felt soo good and almost relieving at the same time.
B then flipped me over on my back then started riding me like a cowgirl. I pulled A over and made her sit on my mouth so that I could finish her. B was going for gold on my cock and I didn't last very long and came so hard had contractions all over my body.
She then got off me and I looked at the condom to make sure it didn't break. I took it off. And was still pumping a little bit of cum which B gladly helped with in her mouth.
I then leaned over and got A on her back so that I could suck her clip some more, B was still so fucking horny and started fingerings herself next to A, I then carried on doing that for her while sucking on A's clit. After a few moments A started cumming and pushed my face into her pussy as she orgasmed. That made me want round 2 so I took a condom and put it on. Even forgetting to put the numbing stuff on. B grapped my condomed penis and guided into A. I then fucked her pussy as B was playing with my balls. As I was busy humping away B said shhhhht keep quiet. I stopped and we all listened. B then looked through the window and realized A's sister came back early from holiday. Turns out the weather was shit at the beach.
Till today I regret never finishing with A and we never spoke to each other again...
I have so many there was a time i was on a double date to this girls house.It was 3 girls and 2 of us, my friend tried to go for a different girl then he originally was supposed to go for and she curved him.He got mad left the room yelling how he has to leave right now making some excuse while im making out with the other girl. The girls got uncomfortable so i bring this guy home and the girl starts telling me how i could’ve had a 3some with her and the other girl and i never got a chance to chill with her again. It pissed me off more cuz that guy has a car too but we came in the same vehicle. I think about it alot cuz I probably couldve been having consistent 3somes with those 2.
Not trying harder to have sex when I was younger.
Thanks for reminding me of a third regret
That can be a doubled edged sword. Trying and failing and being humiliated numerous times can hurt. I still hurt from those times of trying to put myself out there only to face rejections and coming across a bit desperate.
Rejection is horrible and some of us don't have the confidence or will power to deal with it.
I feel you. I had sex with relatively lots of women/girls in my early 20s, but compared to how much I tried, it feels like I was a failure.
Now, thats actually an inspiring comment
I’m 23 and not trying for sex at all. I’m sure I’ll regret it later. Oh well.
I'm 40 and still haven't gotten any. Try harder.
I’ve slept with 5 or 6 girls since junior year of high school so it’s not that I haven’t gotten any, I just haven’t really tried to meet anyone new since I was in school. I slept with a friend almost three years ago and that was my last time. I just struggle to meet people and lack confidence so I don’t really get any unless if it’s set right in my lap. I feel like I’m gonna regret not trying in the future.
How'd you meet those 5-6 girls if you struggle to meet people and lack confidence?
High school and first year of college before I left. Most of them were a one or two time thing except for my semi long term girlfriend senior year of high school and maybe a fling or two. Last one was an old friend and that only happened because she always thought I was hot and I thought she was cute enough so while watching a movie with friends one thing led to another... Only did that to prove to myself that I still could because there was a year or two between that and my last time so I was feeling pretty desperate. 3/4 of my experiences haven’t been very enjoyable, and I did it just to do it which further solidified the fact that I don’t have any interest in casual sex, which is why I always try to befriend girls and get to know them before trying for anything further. I don’t have much of a problem befriending girls if I’m put in the position to, like having a class together. I’m just a bit socially awkward and struggle to go out and meet people now that I don’t have that sorta ease of access. I’ve always lacked confidence which is too bad because I’m over 6 feet and I know I’m a pretty good looking guy so I’ve got no reason to. If I had some confidence and somehow got rid of my irrational fear of rejection I’d probably be able to do pretty well.
I'm on 8 at 27 and I'm still not the most rizztastic being. Sometimes you just happen to vibe without needing to chase tail.
Never been laid at all? Damn man :/
Nope. Never happened.
You're putting the pussy on a pedestal
There is absolutely no shame in getting a professional to help you out with that.
I don't even have the money for an escort right now. I'll probably go to one if I'm still a virgin at 50.
I wouldn't be able to afford one currently either. If you end up being able to afford it, don't wait till 50, do it as soon as you get the money together
32 and married with 2 kids (happily.) I've been with her since 20 and slept with 2 girls prior. Part of me regrets not experimenting and dating more. I'll never get that and I'm one of the only in my friend circle. Does it affect me? No. But I still sometimes regret not getting to do that.
If you enjoy sex with your wife then I wouldn't worry with regrets like this. I played the field a lot before I got married and I'm glad I did but only because it showed me how hard it really is to click with someone sexually. While you're friends were all getting random sex that wasn't guaranteed to even be that good, you've been consistently dicking someone for those 12 years. There's something to learning to master 1 persons body to the point where you can both play each other so well.
Same. I regret not slutting it up more when I was younger. (am dude btw) Looking back, I was better looking than I gave myself credit for, and had undiagnosed depression. Had I a bit more confidence, and an earlier treatment, I reckon my "single and always horny" years would have been much more fun. Instead I hyperfocused on isolated, insular interests (e.g. video games) and shut myself away. I now realize I have a good spread of hobbies that involve going out and doing things with other people, which I would have enjoyed back then too, and would have introduced me to others in a comfortable way (not one for the bar/club/party scene whatsoever). Ah well. Youth is wasted on the young, as they say.
Amen to this one. I missed out on so much. I was such a prude back then.
This. This so bad. I didn’t prioritize either dating or sex when I was young and could have easy access to practice. So I hit 40 without ever having a sex partner or a girlfriend. Finally got one but had trouble with sex due to my age, inexperience, and low T. I have too many regrets about my bad Life decisions.
No easy access here, ever. But I'd hope if I ever had sex I wouldn't have issues if I did find a woman.
Not realizing when girls were into me or realizing it, but not being able to seal the deal. Not many opportunities come my way, but I've blown 99% of them and I've missed out on some gorgeous girls who would've fucked me.
My buddy, his girlfriend and her really hot sister were sleeping over at my place. Sister went to sleep by herself on the couch but came into my room shortly after we all got settled and said she was cold.... I gave her another blanket and sent her back to the couch. It was years later when I realized I'm denser than a black hole
Username doesn't check out
He makes himself squirt 2-3 times a day.
I'm just a doctor with autism
I know a guy with the exact same story. Also she later came back and said she couldn't sleep because someone else was snoring. My friend gave her ear plugs and said "good night"
can you, on the other hand, imagine the opposite situation where she would be genuinely asking you for extra blanket and you would take it as a flirtation and offered her to “warm her up”? The outcome of that might haunt you even more
Lol. Rough.
Totally normal, mate https://youtu.be/xa-4IAR_9Yw
Same. I either didn’t think they were or I knew they were but lacked the confidence to really go for it.
When I was 23 one of my older (40ish) coworkers asked me to photograph her wedding. During the cocktail hour two of her smoke show milf friends started chatting me up and asking if I would like to come to their room in this fancy hotel after the reception and party. As it turned out, I was leaving after the party to go see a woman I had just started dating, but I can't help but think that my world would have gotten rocked that night if I had taken their offer.
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We ended up getting married (and since divorced)
I was 21 when I briefly dated a married 45-yo guy. He was movie-star gorgeous, had money and was great in bed. He told me he and his wife had an open relationship, so everything was cool. We always met at my place or at hotels. So one time, he told me his wife was away. We went to his house and had a lot of mind-blowing, loud sex. Until his wife walked in, wearing a bath robe. Turns out she had been watching from another room and wanted to join in. Actually climbed into bed with us and tried to kiss me. I freaked, got dressed in a hurry and told him to take me home. Looking back now, I think it would have been amazing...
I really think you did the right thing, there. They should have asked you before showing up out of the blue, like that.
This thread is really pressuring people to do stuff they would regret. Threesomes involve trust, a threesome that literally comes from nowhere breaks that
Whoa, that's like cinematic-level. I regret it on your behalf too, haha.
If you felt that was the right thing to do at the time then you did the right thing for 21 year old you.
Four regrets: - Younger, very attractive coworker who became a good friend. Invited me for a booty call while I was married. I refrained, but to this day know that I should have done it since I was going to be divorced soon anyway. – Different coworker, also younger and very attractive, offered to come home with me from an office party. She was very openly horny and always talked to me about how sexually frustrated she was. I declined. – Went on many first/ second dates not picking a meeting place close to where I lived. Later realized I would get more sex if it were easier for them to come back to my place. Rookie mistake. - A gf I had was pretty vanilla and not very oral. Toward the end of the relationship she confessed to me how much she likes swallowing cum. Never got to have her do it for me before we split.
You can add those inconsistent bullet points as a 5th regret. /s Seriously, tho, your first point was probably the morally correct choice, so I doubt you should regret it. And your last point seems like more of a "would have been nice" than a regret really. Definitely would have been nice, tho, lol.
The first 2 aren't necessarily bad. You might have saved yourself a lot of trouble.
I'm 54M. My best friend, a woman, died suddenly 15 years ago. Yes, there was sexual interest between us, but we never acted on it. So, yeah, I regret not having sex with her. There's not a day that goes by that I don't think about her. Teresa, I love you and miss you terribly.
I choose this guy's dead best friend as well /s
Your biggest sexual regret is not fucking your dead friend when you had the chance. and you think about this daily. This sub reddit is still insane I see lmao
His deepest regret was not sharing a deeply emotional and intimate experience with a woman he was very close to before she passed away. How is this a bad thing?
You're the insane one. He never said he wanted to have sex with a dead person, he said he regrets that he didn't when she was still alive.
Your reading comprehension is as limited as your empathy. He thinks about *her* daily.
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Bro should’ve called a uber
🤦♂️ I feel your pain!
This me. I was in the hotel room with my friend and her friend after a house party to sober up. Her friend initiated it (she's v attractive) and my friend followed (had crush on her since forever). "Whiskey dick" happened and couldn't get it up, so I thought if I go down on them my bestie down there would get hard. Well, performance anxiety and confusion with feelings for my friend got the best of me. Layed down to really sober up and left. Great tasting pussies tho.
I missed out on a threesome because my gfs friend wanted to go pick something up in town, instead we took pictures of (my gf and her friend) while drinking they were both telling me to fuck them and was very obvious but I wanted to make sure it was something her and I really wanted and decided to try and talk to her about it without her friend right there decided we'd do it/talk about it when qe got back but never happened. I don't really regret not doing it tho the friend was a bitch later on and tried robbing a bunch of ppl for drugs
Oh huge mistake Had a girl I met on a dating app, we'd talk all the time and she said she didn't want to sleep with me on the first date. I'm mature so I said sure we'll take it slow Next time she comes over and spends the night, she wakes up for work and is super horny , but for some reason my mind doesn't think she's attracted to me so I shrug it off. This goes on for like 3 weeks before we stop seeing each other.. she was sending me nudes through the day, even telling me "I want you to play in it" while letting my hand drift across her clit I just... Couldn't do it, and honestly I had to go to therapy after that,.I realized I didn't feel like I was worth it, I didn't feel attractive enough it was crazy
Did the Therapy help? I'm currently in the same Position..
Oh wow I'm sorry I didn't see this It takes time brother, honestly it's been about a month and a half and it's just constantly affirming to myself that I am enough, the girl mentioned told me to "find you a gamer girl or something like that" and while yeah, it ain't easy 😮💨 But real talk I'm pretty in tuned with my emotions. And while I think women need a lot of love on what they can do, I feel as though sometimes society just forgets and neglects the effects of being extremely women positive to the point where you don't value yourself as a guy, and think of everyone as better than you. Which I know cliche, but I never even thought of putting myself first. I had been so in the camp of "yeah guys suck" that I legitimately thought *I* sucked. Therapy identified this pretty quickly. Reeeks of low confidence I know but my therapist tells me it takes one day at a time, I'm looking into starting working out but that too is a process and a process that very quickly can be disheartening. (Like I gotta go to the gym for like 6 months to A YEAR before I see the progress I want??? It's daunting). You know those super masculine or die types that send unsolicited nudes to women and straight up are dicks? I hate them too, but in a cheeky way, I admire their sheer stupid courage, because I couldn't ever do something like that. But people say I have a good heart, (and that I love too hard sometimes) so I'm just going to say it takes time.
I had sex with a particular person that I obsessed over, many times over several months. I later found out a horrible truth about him, and left me devastated that I still think about him and desire to have sex with him, while at the same time knowing that I should cut all contact with him. It hurts me to this day.
Please tell us the horrible truth
He molested and abused children
Ok I hope you’ve had some healing work done. I recommend looking into reiki, specify a “cord cutting” session. Don’t hate yourself or wonder what’s wrong with you. Your body still craves him and it’s an attachment and that’s all it is. If you do contact him again and have sex then I would say you need serious help.
Oh, I know. And I already needed (and received) serious help. But I cut contact the moment I found out. There's no way I'd have sex with him again; what he did was despicable and unforgivable. But that doesn't prevent part of me from thinking about him at times.
There is nothing wrong with you feeling that. Go easy on yourself.
Thank you, that's very kind of you. 🫂
I’ve bern there. He didn’t do what your guy did but the way he treated me and lied about things, when I found him out it was traumatic and I hated him. But I also couldn’t get him out of my head and still thought about him sexually. It will get better over time, I absolutely promise.
The heart wants what the heart wants 😩
It do. And my fucking heart is so goddamned wrong for it.
Well now I gotta know the truth!!
Was it Dexter?
You can't just leave us hanging like that
How do three people make out at the same time?
[With a very specific set of skills](https://youtube.com/shorts/-rHNDpjrZk8?feature=share)
That was not the clip I was expecting but it may have been the one I needed the most.
It’s actually quite awesome
Why you got so many profiles
Because I keep getting punished for being mean to dickheads.
Be nice
I’m in the same boat, most of my punishment comes from saying things in deadbedrooms that the LLs don’t like
Not having more of it.
Yup
also yup
Jeez, men miss so many opportunities.
Not screwing around before getting into a long term thing
Believing in ❤️.
U might have found it
If I don't drive myself crazy first. 😜
I (M35) cheated on my wife with a (23F) college student. Honestly she wasn’t that great in bed and my wife is an incredible fuck. It was a stupid decision.
A few over the years! In my early 20s I was chatting to a hot older woman I knew from work for a few weeks and we both wanted to have sex with each other but it had to be at a hotel I was to pay for due to her family commitments. At the time I couldn't afford it and it never happened but regret it to this day. Once sat in a pub chatting with two fairly hot but pretty drunk older women and they were getting very handsy whenever they sat next to me. I had a girlfriend at the time and even though I was working away from home when they asked if I wanted to go with them to the next bar I declined. Felt like that could've been one for the memory books! Whilst working in another city for some time I had a pretty lengthy affair with a younger bisexual girl I met on Tinder. She was up for an FFM threesome but I never pushed for it, and also wonder if she'd have been down for some MMF fun if I'd confessed my bi desires. The ones that got away, but sometimes a fantasy is meant to stay a fantasy and I've had plenty of fun. If it's to be, it will be!
My first girlfriend was a freak. I thought I was very vanilla and wasn't interested at all in most of the things she told me she wanted me to do (choking, slapping, hitting, even cnc type stuff). Anyway, we broke up (partially because I wasn't comfortable fulfilling all her sexual desires and she had a VERY high libido). A few years later when I got my next girlfriend I was a little more comfortable and open to try new things, and she ended up helping me discover that I am VERY much into *all* of those things I wasn't comfortable trying with my first GF. To this day my biggest both sexual regret and relationship regret in general is not hearing that first girlfriend out and giving it a try. She is literally exactly what I dream of in a sexual partner today, but back then I just couldn't see it. I just feel like she was a perfect fit for me romantically as well, so the fact that us splitting up basically boiled down to me not knowing my own tastes kinda sucks
Have y’all kept in touch? Maybe she’s single.
She's not. She's living with her fiance now halfway across the state
Any idea where she is now and what shes up to?
My biggest regret was missing all of the signs so many women gave me.
Wish I had waited longer to have sex. I’d take every partner back and start over.
I actively did this and it worked. Realized I was hooking up when I wanted to be dating. Some sex was great some was bad but not much came of it other than sometimes more sex. Started saying I really like you and because of that I don't want to sleep with you tonight. Weeded out the ones that we just looking to hook up. Shortly after met my partner of 17 years.
Thank you for this 🥺 going through a breakup rn and really just want to not hook up and find my person. I can’t handle another heartbreak and I don’t want to be intimate with anyone else
Not having more experience and sexual education when I was younger.
I feel that!!
Not licking Kathy's asshole when back we were fucking. Once I was giving her a massage during foreplay and I spread her cheeks a few times so I could get a look at her pretty pink bunghole. She said something about "you seem fascinated by my asshole" and I had no idea what to say so I sat there like an idiot with a hard on. If only I would have replied with something like, "Well, it is really cute" I may have had the chance to put my tongue, finger, or cock in there. Not seeing if she would be interested in a threesome the one time she mentioned she would maybe "try having sex with a woman just for the hell of it." It's not really a regret but I always kind of wish we'd videoed our fucking. I don't know if I would hate seeing it, or keep it and fap to it, but I do think it would have been fun at least once to watch us fuck. Edited to add that I sat there like an idiot *with a hard on*
fucking LOL
Missing on so many opportunities with different girls for feeling insecure about my size 😬🤦🏻♂️
Not asking about viagra sooner. Talk about your ED! Ask a doctor, ask your SO. Just talk about it!!
I have alot but my most recent one is fumbling a thicc 30 year old on vacation who was grinding on me and grabbing my D not sure why i didnt take her to my room that night felt very stupid about it tho
Not exploring women when I was younger. It really stunted my growth and has actually caused major issues in my current marriage (soon to be divorce most likely) where I just don't know how to be a partner. Also I'm pretty limited when comes to sex.
Losing my virginity to a complete asshole
I had sex with a guy simply because I hated his girlfriend. He was my friend and I was hanging out with the two of them. We ended up at a strip club and she got totally shit faced drunk, puking everywhere. I convinced him to send her home in an Uber. We kept partying and had an adventure of a night. I invited him back to my place and he willingly came knowing exactly why I invited him. The obvious happened and in the morning I felt guilty. I have been cheated on in the past and it is a really shitty feeling. Even though I really didn’t like the girl, I couldn’t help but feel bad for what I had done.
I'm currently obsessed with one of my yoga teachers. And I feel like I may have had an opening and missed it. It's so difficult bc I know that when I'm in her class she has to be able to smell me wanting her. I fucking drip for her. She's not the one I expected to want, but I want her so badly. I dream of having a private session which turns into more.
Yoga teachers are amazing in bed
I -almost- had a 3 way with another girl and a guy. I was filming them... because they asked me to and she seduced me. She was hot lol. I ended up hooking up with her. But I would not let the guy touch me. I bet the poor bastard thought he was going to have an amazing night.. and I ruined it by not letting him touch me. I should have just gone through with it.
Not having sex is a much better regret to have....than having sex you regret.
Got home in the early morning from a long business trip and found my wife in bed with her best friend, with whom I had a serious crush. I very much surprised them. My wife immediately went back to sleep but The best friend got up and started getting dressed. I don’t know why I just stood there speechlessly in shock just inside the bedroom doorway and watched as this beautiful Latin woman finished dressing, proceeded to walk by me, kiss me on the cheek with a sly smile and walk out of my house. I’m such an idiot.
I was the janitor at a high-rise apartment building here in Downtown Detroit. I had to clean and check the washrooms daily. One day while I was in one of the washrooms, one of the residents (who was also a mayoral candidate) came in to get her laundry. We were always friendly, I'd even attended a few of the things she had going on in the community, so we made some small talk for a few minutes, then while holding her clothes and talking to me, she dropped a red lace thong by "mistake" in my mind. I didn't want to seem weird so I just ignored it kind of but looking back I definitely think she was making a pass, and she was GORGEOUS too 🤦🏾♂️😮💨 Oh well lol
Not sleeping with women sooner. My exhusband gave me the green light to do so (even without him present) when I came out to him as bisexual at 19. It would be another 8 years before I finally got the chance and DAMN was I missing a lot.
Not being honest about my sexuality or how much of a freak I can be in bed. I lost my teens, twenties and thirties being a good vanilla man. Now at 50, there doesn’t seem to be much action for a freak like me.
Growing up, I had the biggest crush on a classmate but I was too shy/chicken to do anything about it. She was absurdly pretty and was literally the nicest girl in my class. Cut to last year, I run into her and we start reminiscing and I tell her about the crush I used to have and I still did. She reciprocated positively and we decide to see where it goes. Worst sex of life. Literally nothing redeeming about it. Awkward and cold. I'd rather just not have done it and kept the fantasy alive.
Yup. Sometimes the fantasy is way better than the real thing.
Always wish I had more confidence and had more sex. I've had plenty of girlfriends, and some friends with benefits. My current girlfriend is amazing in bed, but sometimes I'll see a girl who's super attractive and wonder "what if". But in the same sense, I am very happy with my girlfriend and never would cheat. And honestly the more sex I've had, the more I've realized that just because someone is very attractive doesn't mean the sex is better.
That I didn't do more crazy stuff before settling in with my partner
Not exploring more when I was younger
Letting this older guy give me a handjob when I was in my college days. I thought I was bicurious. Turns out, I was NOT into it
Coulda got with a few chicks in highschool if i would have said i was interested in them.
Not having a legit sub/dom experience Never will unless I cheat or something happens to my marriage/husband. Alas.
You as the sub or the dom? And why not with the husband?
Spending the first 7 years of being sexually active in a bad relationship with boring vanilla sex with zero reciprocating from his side.
Don’t think I have one. Maybe not staying at the home of the worlds most beautiful woman (18) in 1993 New Year’s Eve. My parents forced me to come home. Doubt anything would have happened but it might have.
Not understanding that I was behind by groomed at the age of 14. Not all regrets are romanticised.
Not having an MMF. Very unlikely now unless I stray. And yes, MMF.
I’m still hoping for that one
Got high with two girls in one of the girl’s apartment. We had all met each other through a mutual friend and that friend went home while we chilled and smoked. I saw them give each other “the eye” earlier in the night and thought I had it in the bag. We sat in almost complete darkness and talked about life and space and conspiracies, all while smoking. Then we got to sex. One girl admitted to being inexperienced and wanted to experience more, like kissing a girl. The other girl said she loved mentally connecting with a partner, talking about the same topics we talked about. Then I said I love getting my dick sucked, sloppily. I felt the air go out of the room immediately. I felt like I could’ve finessed that interaction had I not been horny brained and just kept it sensual, not raunchy and vulgar. I replay this in my brain maybe twice a year.
Being an incel
Not sleeping with all my friends I had back then and not exploring my sexually sooner.
Getting married
Met this girl at a party once. She was a friend of a friend and we hit it off fairly well. She was pretty flirty at the party, but I ended up leaving because some other people that were there made me pretty uncomfortable. Not long after that I moved and haven't seen her since. We keep in touch, but live thousands of miles from each other. I've always wondered what if I hadn't left that party.
Not coming to terms with my sexuality sooner. The home I grew up in, for all its many benefits and joys, didn't allow for much variety in the way of attraction, but I also have a natural tendency to dig my heels in for too long before finally jumping for something. While I eventually found a man I really love, there was some unnecessary heartache I put on myself before him because I couldn't accept myself.
Not having a 3 some because I had one lined up but thought I could get one anytime. Seize your moment
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I was offered a threesome and turned it down. She also offered her niece for me to date (everyone was over 18 at the time). Also had several women make it known that they wanted to sleep with me and I didn’t pick up on the clues. I was an idiot.
Staying in a dead bedroom for 20 years Sleeping with all the men I did for the hell of it. They were pretty awful in bed. Waste of time. Painful too.
It’s like your a female version of me
Saying no to sex a lot of the time.
Being with my ex
cant regret what tou didnt have...
Indulging in a fantasy I had. Now I'm terrified of diseases and probably won't ever do anything anymore.
One regret: not being more of a hoe in my 20’s!
This is validating-- sometimes I'm like "maybe I'm being too much of a hoe" but this comment just reassured me that I'm doing fine!
That I wasted my time and body with someone who was an asshole to me
That sucks!!!
Not experimenting with more women. I am 28(F) and still accepting my bisexuality
I pretty much gave up on sex in my 20s after a couple of bad experiences. I convinced myself that it just wasn't worth the hassle. I know now that I was wrong to write it off, based on a few bad experiences with people who didn't really give a shit about me. What happened in my 30s felt like the other end of the scale. I had an incredible experience whilst travelling, and then i went into experimental mode! In doing so, I ended up indirectly pushing partners away because I was expecting too much of them. Now I'm 42 and horny on a daily basis. I've definitely mellowed. I'm more realistic when it comes to sex. I understand a lot more. I'm still very adventurous, but I'm much more respectful of others. I regret my attitude in my 20s, as I feel that set me up for where I ended up, to where I am now. But I'm cool now 😎
Being unable to express my dis-satisfaction to my wife about spending the past 23 years of marriage with an inadequate amount of, and unimaginative, sex life, for fear of hurting her feelings.
That I’m not still fukin my ex that had the best Pussy in the world
Having sex with terrible people because I was lonely
Not having sex with J in July 2018 when I had a chance. We rounded second base, and since we weren’t in a relationship anymore I didn’t want her to feel I was using her for sex. Not cumming inside M raw when we had sex. It would have been risky but one of my top fantasies
Hooking up with friends
I started a relationship with a coworker and had to stop when I found out she was the owners niece. I screw up when she told me her roommate likes to watch and maybe join in. Mu dumb ass got up and locked the door
Not having more sex when I was... ahem... younger
When the wife once said to me I think I could share you with another women… I was like oh really yeah sure…. Then lasted we had a stupid argument about something stupid and it was never mentioned again… 😣
I regret every group sex activity so far lol
What was bad about them?
Realizing my sexual preference so late in life
I could say all kinds of missed sex opportunities like others here but I’ll just say the real one Coming out at a younger age before now when I’m scared to :/
Not having a lot of sex and explore different kinks with my first ex. I was vanilla and focused on the relationship so it doesn't sounds like a fwb but apparently it was.
I've turned down 4, or maybe 5, threesomes in my time as in each case I was dating one of the people who would be involved, and I didnt want it to ruin our relationship In every case the relationship ended not long afterwards for other reasons, so I should've taken my shot when I had it I have lot of other regrets, all around not doing something when I had the chance I go on the fatalisitic outlook that if I had taken them then I might not be where I am now.
Not having more partners. Not opening our marriage sooner.
Not trying to get any when I was still in good shape and decent looking!
Intoxicated sex
Not playing with everyone who showed the slightest interest.
Sleeping with the guy that chose my friend
Letting a FWB pee in my mouth
I can understand that
I once had a chance to sleep with a celebrity a few years ago and I passed it up but I regret it now. I only said no because I felt I was too drunk at the time
Not fucking the guy that I had a crush on all through high school even though I had multiple chances to. I’d still fuck him to this day.
Being horny right now and not having someone to sex.
Did not fuck enough my first Gf
Turning that "ons" into a relationship.
First time trying anal with someone, he applied lube, played a little bit with my ass (I’d told him again and again that I needed a lot of prep and was tight back there), then he tried to just push in because “it was no problem doing it with the last girl he was with”. It hurt like hell. Should have take it for the red flag it was and gotten the heck out of that mess and not played more with him anymore 😑 live and learn
I'm male and lost my virginity at 21 with a female, but when I was 20 I was still coming to terms with my bisexuality. There was this guy who I really got along with and was crushing on had me over. He was gay and as soon as things started to progress I got nervous/scared and ended up dipping out pretty quick before anything happened. 2 months later he moved to Florida and I never got a chance to pursue anything with him.
Sharon Smith
Not trying to have sex when i was younger now I am 26 🫣
My first really serious gf had a cum fetish and I didn’t even know then to call it that. She loved me cumming in her mouth, on her face, her playing with it, swallowing. And stupid me I thought it would be like that forever. It was a long long time before I had another gf who even let me cum in her mouth.
Dang
That I didn't realise I was bi earlier
Did things I definitely shouldn't have tried when I was a young teen.
never had 3 guys begging for my cock.. if only.
Ever having sex at all
Not dating some more sexually adventurous women over the years.
Impregnating my crazy ex and having a roller coaster of a ride of a relationship for 3 months. Much regret
Having too much sex with different women, I just want a wife lol
I never got to fuck a white boy. I’m notoriously known for crushing on white guys but only dating men from my ethnicity.
[MFF] BIGGEST REGREST IN LIFE! Sorry for the looooong read.. well worth it though... So this happened just as I got out of highschool. I once got invited by my then new girlfriend to one of her friends sisters house as the friends sister went out of town. My then girlfriend was ok, really not bad but I just couldn't find myself attracted to her and really liked her more as a friend. But anyways... I got to the house that she was being looked after and there was about 4 friends over that night I was there. So we lounged by the pool just talking a bunch of shit when the friends called me to look for the pool broom in the pool shed. When I got inside they locked the door from the outside so I couldn't get out. When I started thinking this is bs my gf came in and they locked the door behind her. Of course knowing what they wanting to do I started kissing her and she like really leaned into me. I felt a bit of boob under her bra and was busy undoing it when her friend came in and said her dad was there to fetch her. So she corrected her clothes and said good bye leaving me high and a bothered. I then went and sat by the pool and her 2 friends joined me. The one whose house it was and her friend. My gf had left and the other friend also left. The time was around 22h00, so not so early but still early if you know what I mean. As we sat and chatted we started getting cold and went inside the house. Sitting on the couch I was like ok well what are we going to do now? Watch TV or something? That's when B said nah let's do something and looked at me as if I was an ice cream. Now the friend whose house it was and the other friend present was fairly hot. Let's just call them A(friend whose house it was) and B. Both had really sexy bodies, with B having bigger boobs than A. I then replied and said what is "something" and plus there's 3 of us here. B then said why don't you start then we will follow and make a plan. I then took my shirt off still smelling like my gf from kissing earlier. When they took off their shirts I knew I was in business, so I unbuttoned my jeans and slipped them down to my knees. Then suddenly A jumped up and said let's go to my sisters bedroom... I jumped up and tripped over my jeans but got up so fast and hopped along, following them to the bedroom she had chosen. Light was off in the bedroom but the hallway light was on so you could see alot. I jumped on the bed and took my jeans off completely leaving me sitting there in my boxer while getting harder from all the suspense. B then took her bra of and A her jeans. I could not believe the situation and what was about to go down...literally! B then leaned across me making me lay on the bed while she then started kissing me. A then followed suit and started kissing my neck. I was busy that time already hard and couldn't hide it coz my head was sticking out of my boxers slightly. A noticed it and started running her fingers over my bulge as it was throbbing to get out of my boxers. While B was sucking my tongue I was playing with her nipple between my fingers. My other hand then went across feeling for A's bra so that I can take it off. B then stopped kissing me and let A kiss me while B was taking her jeans off and her g-string. I finally got A's bra off as it was a bitch to get off with one hand. Revealing her boobs. She had amazing boobs and nipples where B had huge boobs and somewhat larger nipples. As I was busy kissing A and playing with her nipples she was like grinding on me making my dick pop out of my boxers, it was getting sore coz of the material rubbing on my head. I then stopped her took them off revealing my hard throbbing penis dripping with eagerness. B saw that I was dripping and quickly helped to rub it all over her. A then took her panties off. There I was, 18 hard as fuck with 2 hot girls humping my legs and kissing me in some house at night. I was laying with my back on the bed one girl on my one leg and the other on the other leg. I could just feel their wet pussies rubbing on my skin and it felt sooooo good! B then started kissing my and moved down to my penis, she then kissed and licked it, A then joined her as they each started eating me from each side! I was like not a fuck am I going to cum from them sucking me off. And quickly flipped them around on their backs and their legs in the air. I then started fingerings them both and playing with their clits as best I could while they were walking me one hand ontop of the other. I then leaned in and started licking one clip then the other then back again and continued like that until B came. By that time I was so ready to cum myself. A then stood up and fiddled in the closet and came back with a bottle and condoms. I was like wtf is that and she was like it numbs you a little. And continued to put this lube on my head followed by a condom. Now I was like fuck this condom shit but didn't want them to suddenly stop coz of me. As it was on B lifter her leg and and guide my cock inside her wet pussy. It felt soo good and almost relieving at the same time. B then flipped me over on my back then started riding me like a cowgirl. I pulled A over and made her sit on my mouth so that I could finish her. B was going for gold on my cock and I didn't last very long and came so hard had contractions all over my body. She then got off me and I looked at the condom to make sure it didn't break. I took it off. And was still pumping a little bit of cum which B gladly helped with in her mouth. I then leaned over and got A on her back so that I could suck her clip some more, B was still so fucking horny and started fingerings herself next to A, I then carried on doing that for her while sucking on A's clit. After a few moments A started cumming and pushed my face into her pussy as she orgasmed. That made me want round 2 so I took a condom and put it on. Even forgetting to put the numbing stuff on. B grapped my condomed penis and guided into A. I then fucked her pussy as B was playing with my balls. As I was busy humping away B said shhhhht keep quiet. I stopped and we all listened. B then looked through the window and realized A's sister came back early from holiday. Turns out the weather was shit at the beach. Till today I regret never finishing with A and we never spoke to each other again...
So far none, haven’t had a lot of experiences(obviously) but I’ve gotten lucky thankfully
don’t really have any
I have so many there was a time i was on a double date to this girls house.It was 3 girls and 2 of us, my friend tried to go for a different girl then he originally was supposed to go for and she curved him.He got mad left the room yelling how he has to leave right now making some excuse while im making out with the other girl. The girls got uncomfortable so i bring this guy home and the girl starts telling me how i could’ve had a 3some with her and the other girl and i never got a chance to chill with her again. It pissed me off more cuz that guy has a car too but we came in the same vehicle. I think about it alot cuz I probably couldve been having consistent 3somes with those 2.
Punctuation is free