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This is a question The worst sex I ever had

OK, enough of the fluffy.

What's the worst sex you've ever had?

(, Fri 15 Jun 2007, 10:41)
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This question is now closed.

I may regret this...
...but I'll share a tip or two myself on playing in the back door.

First of all: lube. Lots of lube. Insert some into the orifice with a fingertip before you do anything else, and make sure that what's going in there has a good layer on it as well. And before you insert the lube- trim your fingernails!

Second tip: relax. Both of you. If you're receiving, relax your butt like you're going to go take a shit. If you're giving, go very slowly- work it in there gradually, and if you feel resistance and your partner is making strange noises, back it out a bit. Use your hand to wriggle it around, as though giving a massage with it- which in truth you are, to get the muscles to relax. Eventually you'll find yourself sliding in- and at that point go slowly, rather than banging away at it like a rabbit. If you just go ahead and ram it in there, it hurts A LOT. As in, your entire universe shrinks to nothing but this screaming pain that makes you writhe and want to crawl away and hide.

Third: if you've never tried it, don't dismiss it out of hand. If it's done slowly and gently, it can be one of the most intense feelings you've ever had. And there I'm addressing both genders- guys, if you're asking her to trust you to do it, you should be willing to give it a go yourselves. However, it's fair to ask that the toy she uses be no larger than your own cock.

To keep on topic: I had a woman do it to me a couple of times, and not only did she have long nails (ouch), but she didn't exactly work it into me slowly (YEEE-OWWW!!!). Not to mention that it was substantially larger than my own equipment...

I let her try it a couple of times before I refused to try again. However, I have also had some incredibly good experiences with it... so keep an open mind.
(, Mon 18 Jun 2007, 16:33, Reply)
a toffee on the sofa
need i say more?
(, Mon 18 Jun 2007, 16:03, Reply)
ToMeToyou
I sincerely hope you are joking with your dildo story, because if not, it sounds like you committed serious sexual assault on that girl.

And if that's the case, you are mistaking "desire" in her eyes for fear.

Which really is most worrying
(, Mon 18 Jun 2007, 15:57, Reply)
I tried to pull...
...Prince Edward, but he said no. I guess that makes him the Wessex I never had.
(, Mon 18 Jun 2007, 15:40, Reply)
Harsh, but true...
I generally am a firm believer of "it's what you do with it that counts"... However, after getting out of a 2 year relationship and basically just snapping up any available offer of sex, I found myself seeing a guy (10 years my senior, and me being 18 at the time) who had the tiniest cock imaginable. Now, I remained optimistic, but seriously! It took me about 5 minutes to realise he was actually inside me... and it took him about 45 minutes to cum. Which basically left me lying there, covered in his sweat, making the occasional noise and wishing I could be anywhere else but there.

You had thought I'd have called it quits after that, but it carried on for another two months... the same routine everytime.

But even that terrible sex will never EVER outdo one of my exes, who had very questionable personal hygiene and giving him a blowjob was often peppered with a cheesy treat. I have to say, a big deal is made of intimate lady smells, but NOTHING is as bad as cockcheese. NOTHING.
(, Mon 18 Jun 2007, 15:13, Reply)
Ohhh, I have one!
It was when I was with my ex hubby, we'd been together years and years so it was very seldom 'The Urge' ever took us.

So one day our daughter was out with Granny and we were home alone...we start getting a little frisky...DURING THE DAYTIME!!! Old habits die hard so we head upstairs whilst kissing and trying to undress each other.

He took my top off, no probs...I tried his but the head hole on that particualr t shirt was quite small and a bit of a struggle for him so he had to yank it off on his own in the end...not in the least bit offputting, had a giggle, on we go.

A few more stairs up and I'm tugging at his jeans, I'm trying to undo them but I just can't...on closer imspection I discover a safty pin that's holding his zip up as it's broken, that's fine I think...goes to unclip it, cue pin in finger, ouch! Slightly more offputting but we carry on. Keeping with the trousers theme I pull them down only to realise he still has his shoes on and they won't go over his shoes. So he has to sit down and unlace his shoes and then take them off.

Anyway, by now we're upstairs and he's at my trousers...he gets them off then just idly flings them out of the room...to the landing, which is being decorated and there's paint and dust and all sorts everywhere, so off I scoot to retrieve them...they were my best kecks...

So there's us, just in our undies standing by our bed...which has our daughters toys all over it, *sigh*, so we start clearing all of them off and then, we get ready to carry on.

He comes over to me, slide his hands around my back and starts to undo my bra........and still he tries...and yet still he tries...in the end he settled for sort of sliding it down my body as opposed to undoing it...

I slip my finger into the top of his boxers to take them off of him and as I do...Riiiiiiiiiiip, they tear on my longish nails, he starts getting a paddy on about how he really likes these ones and they fit him really well and couldn't have I been a bit more careful...

After that he pushed me down on the bed and started kissing me...mmmmmm, lovely I think but my glasses are in the way...so I take them off and hand them to him to put down on the bedside cabinet as I can't reach it, he does so...lens down...I'm sure they're lens down...they're going to get scratched and I've just paid £70 quid for them...fuck it...I ask him to check, yes they were lens down and yes, with a big grumble he'll right them for me, so that's it...knickers come off with no trouble (hmmmmm) and we get down to it...

After all that bloody palava to get there it was shit, largly as I trod on his testicles as we changed position and really quite hurt him...sorry Luke.

We're not together now.

Something about length...this post...not Luke :)
(, Mon 18 Jun 2007, 15:12, Reply)
How Insensitive
My lass was having a shit in my mouth the other night when she suddenly farted, really put me off that did
(, Mon 18 Jun 2007, 15:12, Reply)
Used this for an embarrassing injury qotw, but fits here too
Ended up drinking at mine after a works do & getting better acquainted with nice new bloke @ work (diff. dept. - thankfully!)

Things move to the bedroom, hands move lower, and JESUS CHRIST WTF WAS THAT?!?!?!? OWOWOWOWOWOWOW! His very long fingernails felt as though they had gouged a big slice out of my most tender outer parts. Unfortunately, as I hadn't shouted out the above and just moaned in pain, the moan was taken the wrong way, the blood was mistaken for lubrication, and thus entered the thinnest dick I have ever had the misfortune to be in contact with.

Woke up to missing man & big blood stain on the duvet, extreme stinging on peeing (although for a change this wasn't due to cystitis), and a scab for about a week.

Wouldn't have minded if it had been worth it, but worst shag ever :o(
(, Mon 18 Jun 2007, 14:50, Reply)
Torn banjo string
I was seeing a girl at uni who was a wonderful shag - she could go at it for hours, and was up for trying just about anything. She really was wonderful, which is why I feel so guilty about my behaviour.

One night after much booze in the pub, we got back to mine and fell into bed in the usual drunken frenzy that alcohol brings on. We were doing doggy, and on one particularly aggressive stroke I felt a searing pain. I stopped momentarily, and then thought fuck it, and kept going.

Post climax I pulled out and to my horror saw that I'd torn my banjo string (or the Frenulum of prepuce of penis if you've studied anatomy)! not wanting to admit what had happened (why?!), I lay face down and went to sleep.

I woke up the next morning to an apology from my partner, who couldn't believe she'd been on her period. She took the sheets home to clean them, and as really nice to me for weeks...and continued to be nice to me when I confessed what had actually happened.

She was lovely, but the pain made it my worst sex ever.
(, Mon 18 Jun 2007, 14:49, Reply)
around the UK
Gosport: on the blob & then she did sloppies with my mate
portsmouth: A fat, wanted tying up then anal, 10months later-meet baby mikey
Crewe, skinny bird with a lousy mattress that went 'TWANG! as a spring ripped into my knee, laugh? i almost shat. no, that was her.
Hull: can you do me anal? i'm on and me boyfriend wouldn't like it if he knew you'd done me.
Cardiff; 2a.m, can't go to hers, so, public bog, interupted by noise thru the cubicle walls of pissed girls throwing up/shitting/making mobile calls.
scarred for life, but still trying!

"I'm not a gynaecologist-but I'll give it a look"
(, Mon 18 Jun 2007, 14:47, Reply)
I'd thought I'd add to the blob tales...
I was going out with a lass for a while who seemed to take particular delight in shagging whilst on the blob.

She'd make sure she was on top when I finished off, then move up and squat over my belly button so the cummy blood would dribble in.

Someone made this about it.
(, Mon 18 Jun 2007, 14:29, Reply)
Inappropriate lubricants
May have posted this before, I can't remember.

Anyway, it concerns an acquaintance of mine, Bob. He was in his student flat one afternoon, wanking to some porn video he'd borrowed, when he decided he could use some lubrication to enhance the experience.

Due to the lack of suitable proprietary products in the flat, he had to look for an alternative.

Mistake number one - he used Fairy Liquid.

Apparently it worked OK for a few seconds, then started to burn like hell, so he ended up running his cock under the cold tap.

Mistake number two - he told us about it.

He is still referred to in conversation as "Fairy Liquid Bob", 15+ years on.

Hands that do dishes may be soft as your face, but not half as sensitive as your bell end.
(, Mon 18 Jun 2007, 14:17, Reply)
As they say in IT.....
...documentation is like sex.

When it's good - it's very good, when it's bad, it's better than nothing.
(, Mon 18 Jun 2007, 14:06, Reply)
Sex by Accident...
This is not one of my own stories, but 1 of a friend in Magaluf. I won't tell the story, but instead quote the man himself from the day afterward....

"Well i was grinding with this girl, and she pulled by cock out. She was tossing me off, and I was thinking "this is alright!". But then I noticed it felt a bit different, and after about 5 seconds, I realised I was inside her, which confused me a bit. So I pulled out"


No apologies for length, but I'm a bit sorry about the girth. And the smell.
(, Mon 18 Jun 2007, 13:37, Reply)
Anal pointers...
[Rant_Mode]

I just want to say... That there's a bunch of assholes out there who have no idea what they're doing when it comes to anal.

I've met lots of lasses who have decided that they HATE anal because it HURTS.... And the same ones discover that once they're comfy, relaxed and feeling adventurous, that Actualy, anal sex feels awesome.

GUYS... If you're trying to get into someone's ass and they tense up.. STOP. They're not having a good time, they're not ready for it, and you're clearly doing something WRONG... and to make it WORSE... once they've dumped your inexperienced and insensitive ass, They'll tell their next guy that they don't like anal... because YOU hurt them.

And it has very little do do with size either... many can even take more in their ass than their mimsy.

[/Rant_Mode]

And Girls... never let a guy play with your all unless you've dropped the kids off at he pool... It's nearly as rood as farting when someone's going down on you...

Hopefully this post will lead to many more people *enjoying* Anal.. instead of being horrified for one reason or another.



Now.. to make up for ranting, I'm going to go find an answer that makes me laugh instead of making me angry at inexperienced and careless boys....
(, Mon 18 Jun 2007, 13:27, Reply)
Crazy Russian Girl
Well I had started dating this Russian girl who I had met in a night club a few weeks earlier. She seemed really nice, but very reluctant to get down to the dirty stuff. Only seemed to like fucking when she was drunk (maybe you need to be with me, who knows?).

Anyway, I get invited to a party in Luton (shit hole I know), and I am the only english person there.

BBQ ensues as does the plentiful flow of nasty tasting Russian Vodka. I decide to stay sober as I wasnt to pleased in being surrounded by so many crazy drunk Russians.

Anyway we are in the garden having a kiss and a cuddle with about 10 other people enjoying the BBQ. The girl I am seeing then decides she wants a good seeing to, right there right then!

I said no at least 10 times. This just seemed to spur the crazy cow on. I was swiftly told to "Shut the fuck up!" and my head was slammed to the ground and my member set free into the evening air. As you can imagine I was a little disturbed but also couldnt really do much as she had started sucking the fella. Anyway long story short, crazy Russian girl practically rapes me in front of the entire party.

But to the put the icing on the cake her fucking pervert brother had watched the whole thing and even brought me a beer over after I was done and asked "So do you like my sister?"

Russians, they are not big and they are certainly not clever!

Length? Who needs length when you can keep it going with her brother watching?
(, Mon 18 Jun 2007, 13:26, Reply)
I had a few months
in the 1980's where I was a toy-boy. She was 33, divorced & rich - I was 23, a student & skint. It was brilliant. She bought me clothes, records, drinks, drugs, dinner in restaurants, etc. All I had to do was shag her. And I did. Lots. (NB: The financial incentive was just a boon - she was gorgeous & I fancied her no end.)

My finest moment was her Chiropractor banning me for 2 months because I'd dislocated her pelvis during a fairly typically vigorous session. I was good in them days...

Then on my 24th Birthday she gave me a blowjob to remember - fantastic, if a bit violent. She bit a great lump out of my foreskin. It bled. It hurt. Then two days later it came up in a nasty rash. I slunked off to the clap clinic where I was diagnosed as having Herpes. She had a cold sore when she was gobbling me & it had infected the wound.

I'll never forget you, Jumpin' Jenny! Nor can I. You gave me the ultimate gift that just keeps on giving... for my Birthday...

Chizz!
(, Mon 18 Jun 2007, 13:13, Reply)
Broken Heart-Broken Fingers
I was seeing a girl who was (shoot me) still living with a boyfriend. At the time I was still at my folks so bedroom frolics were by nature impromtu moments.
I had met this girl at a nightclub and we had gotten a wee bit amorous while I was walking her home. Luckily we lived in Hull (lots of little alleyways to duck into!) and on the way home she dragged me into a dark and secluded place for a wee bit of stinky finger fun.
She was a fairly big lass (Hi Gemma if you are looking in) and was wearing the tightest of tight jeans. I undid the top button of these and slid me hand due south and inside her pants. I located the man in the boat and give him a quick touch-up before moving further down to wetter climes. So there I am, in February, the snow settling on my shaved head, with my fingers deep inside a fat lass in Hull. "Does it get any better than this?" I thought. It Didn't
My thumb relocated the man in the boat, and she seemed to enjoy so i rubbed more vigorously. My partner in friggage then whispered romantically "Fuck me, I'm cumming" and her legs gave way.
I mean GAVE WAY.
She landed on her knees and the following happened to me:-
2 x broken fingers,
1 x dislocated wrist,
1 x broken radius,
1x broken ulna.
Luckily we were just around the corner from Hull Royal Infirmary, and holding my arm, I staggered there with this girl still rosy cheeked with the FFG (Freshly Fucked Glow).
The Nurse took one look at my hand and said "erm, Mr Airliebird....... would you like to wash your hand before we go any further?"

Now that beats any banjo string snapperage stories.... I didn't even get him out!!!
(, Mon 18 Jun 2007, 11:38, Reply)
I wasn't going to bother, but...
After a heavy night in the pub I'd gone back to someone's house for more drinks. It's all a bit hazy but I ended up locked in with a lass I didn't even fancy (think that witch from chorlton and the wheelies). I must've thought "well, why not" so we get down to it in the living room in someone else's house.

What I do remember is me trying to work her up a bit with my fingers and her saying "just fucking stick it in".

The next thing I can remember is being stood in the bathroom with blood everywhere and in a very sorry mood. She'd manage to snap by banjo string.

Vague silver lining is that she said "it's your own fault for being too big". It's grown back a little but it's nowt like what it was.

edit: The next day I had to apologise to the house owner for the blood on the living room carpet. Fortunately she took it in good humour.
(, Mon 18 Jun 2007, 11:02, Reply)
copied and elaborated from my "losing my virginity" QOTW
I had a bottle of jack daniels first (I'm still amazed to this day that the event was even possible after that much booze. Ah, youth!) and it was a bit of a 'mare really, in retrospect. I wandered into a room at the 3-am stage of a party to find a large female partygoer who seduced me with the cunning line of "I'm bored, want to fuck me?".

The second-worst thing about it was her unconvincing and constant stream of "oh god, yeah, oh your cock's great, oh yeah" etc etc, which started a good 20 seconds before I touched her and managed to put me off enough that I considered faking my own orgasm. I needn't have worried, it was over very quickly. I think I may be the only (male)person genuinely glad to have come really fast their first time.

The worst part was explaining the following morning why there was a condom wrapper and a handprint in menstrual blood on the host's parents' white leather sofa.

Grim.
(, Mon 18 Jun 2007, 10:59, Reply)
Never answer your mobile when someone's sucking your cock
they will hit you - and you will have deserved it
(, Mon 18 Jun 2007, 10:48, Reply)
if you say boo first, does it count?
I tapped off with a really tasty petite blonde who wasted no time in getting busy on mr happy. After a great bit of foreplay, including one of the most memorable slow blowjobs I've ever had, we actually got to the full penetrative stuff. A couple of minutes in and shes panting fit to burst, I feel her muscles tighten and her whole body tenses. Suddenly shes screaming "Rape" at the top of her voice and punching me in the face. Apparently she always did it when she came, used to fantasise about forced sex and suchlike, and would I make her come again please. errr, no. one black eye and my housemates bursting through the door was enough thanks. I did let her finish me off with her mouth though, although on reflection she could have got her teeth stuck in if she had wanted.
(, Mon 18 Jun 2007, 10:45, Reply)
sickening rememberance
just remembered this and it's put me off breakfast.

One of my exes (the mad one) thought it would be fun to play with cream and then for me to go down on her.
What happens to cream when you warm it up your fanny?
Yep, her fanny was full of cream that smelt like it had been left in the sun for a week.

Nice. cheers for that one, I think I prefer the fish.
(, Mon 18 Jun 2007, 10:36, Reply)
Punishment
Ok, so not *technically* sex, but sex related :P

From time to time I wind my other half up - only playfully you understand ;) However, sometimes it annoys him a tiny bit and the punishment he devised was to threaten to bum me dry. Now, most of the times I've been a pest and wound him up he's just played about and *nearly* bummed me until I stop antagonising him - however, a couple of months ago when we were messing around with this 'punishment' again, his member went inside causing ALMIGHTY PAIN. My arse has never felt so sore! Fortunately he withdrew pretty sharpish and apologies ensued :)

Sex is actually pretty damn good normally, but we've stop the insane 'punishment' messing about thing - not good for my health!
(, Mon 18 Jun 2007, 10:14, Reply)
Stag weekend
A friend of mine was gettin married. Being a bit of a male whore, he wanted to celebrate the last night of freedom by getting laid. He wasn't bothered about quality or anything, just to get something.

Now, off into Liverpool we go. By 1:30am, the 16 that started the mission are down to 4. Me, the best man, some bloke called Phill and the groom. We hit this pub, and in to not well lit downstairs, the 3 others start chatting up anything that could be described as female.

Best man pulls, and buggers off. Phill pulls, buggers off. All of a sudden, Groom is pulling me over to these 2 girls. Both what I'd call 5 pinters. His eyes are on the rotund blonde, leaving me with the "friend". Groom and woman go off dancing, me and other girl have a drink.

3am, me and Kate say goodbye, nice talking to you. Groom and Sarah are nowhere to be seen. Go back to hotel room alone, drink the mini bar and pass out.

8am, wake up with Groom pacing in the room, shaking. Apparently, Sarah is slightly more kinky than was needed. Groom now has scratch marks down his back, 2 fag burns on his chest, teeth marks all over and more worryingly, a complete inability to sit down.

Yes, the kink had moved to her on him action, and had ripped him not a new one, but certainly enlarged the original.

Wedding day; 3 days later. Groom explained the stuff on his body as injures from paintballing. I still to this day don't know how he explained his newly enlarged schincter though...
(, Mon 18 Jun 2007, 9:41, Reply)
Stinky old women!
For all the women out there that say they like anal sex. You do realise you'll be shitting your pants everyime you cough in later life. I hope you dont end up in the care home I'll be in.
(, Mon 18 Jun 2007, 9:31, Reply)
true story
guy I used to know: I like Christina Ricci. She's got the body of a woman but the face of a child.
(, Mon 18 Jun 2007, 9:07, Reply)
Not me, but MrsMudskipper ...
.. still detests her ex with a passion after many years. She was quite happy to tell me about the only time she ever attempted to swallow (having not being given any advance warning - class bloke). The taste was so yuck she immediately threw up all over his todger and pubes and he couldn't get the stink out for hours.
(, Mon 18 Jun 2007, 8:44, Reply)
Posted this before, but it's appropriate here
A mate of mine had a girlfriend for a year before getting...ahem...'intimate'. He was waiting for the right time. The right time came on an excursion to Scarborough. Being in the hotel room next to them, I heard the gory details, included a large 'aaaaiiiiiieeee!!! It hurts'

Apparently, the guy covered his member with soap (for lubrication), and caused the girl great pain with it.

She thought it was best to see a doctor so, waking me up in the process, we went to the hospital, where she discharged after a few hours (ba dum tish!).

Unfortunately, the mate of mine, had forgot to wash off the soap after the incident, and by now, it formed an ever-tightening seal around his member. Causing him not only great pain, but worse, walking around with an erection wherever he went.

After a few days he told me that he had visited the GUM clinic, and said that he should soak his soldier in warm water for a few hours. Even then, it would take upto 3 days for his little guy to regain natural dimensions.

Never one to take doctors advice, he invented a quicker way.

He mastrubated with a piece of sandpaper.
(, Mon 18 Jun 2007, 7:58, Reply)
Smiling Still!
After many months of trying to woo Emma, for that is her name, it came to pass that we were sufficiantly drunk enough to sleep with each other.

Now, I did not know that she was totally out of it as I was at the time, but anyway, back in her bedroom she had a bedside cabinet. Now, this said cabinet had a collection of dildos and vibrators that would put Anne Summers to shame. I think she was a product tester really.

This came as a bit of a shock as she whispered in my ear that she would like to shove one of the things up my arse whilst sucking me off. I am not a prude but the postate exam at the doctors gives me enough tears in my eyes, let alone a ten inch dildo!

So anyway, whilst I was getting my back wheels, she fell asleep, comatosed. So I thought I would have some fun. Two up the front and two in the rear is what I managed. I left pretty quickly and laughed all the way home.

The thing is, even now when I see her, she has this knowing look in her eye that she wants to do it again!

It was the shittest sex I have ever had but the most fun!

not true by the way!!

Length: 2x 10"x 3" and 2x 6"x2" with knobbles!
(, Mon 18 Jun 2007, 6:46, Reply)

This question is now closed.

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