How I lost my virginity and took someone else’s
Much like last week’s entry, this one definitely contains very adult themes — no pictures or animations this time though, so it is work-safe! The title is a little misleading, but you’ll have to read the entire story if you want to find out why. If I disappear from the Internet for a few days after publishing this, it’s because I’ve gone to hide in a corner, whereupon I will be blushing like a schoolgirl that’s just accidentally touched a boy’s willy. If you want more Too Much Information (TMI) stories head over to Lilu’s blog — but my story’s probably far more embarrassing than any of theirs.
The hotel room itself was nice enough, functional. A king-size bed: a little firm, but good back-support would be ideal for the kind of weekend we had planned.
It was all going so well until she pulled out the tube of lube.
‘It’s time, Seb.’
Time for what? My mind was racing, desperately trying to work out what I’d agreed to. Was this another case of me forgetting the little details? Women are so good at remembering. Had I agreed to do something and then conveniently filed it into the ‘Nag Me So That I Remember’ compartment of my mind?
She shifted her weight. She must’ve noticed my hesitation. I’d been very, very keen so far to try anything and everything — so had she! — but now I was sitting on the bed, staring at the tube she held in her hand. There was an impish grin on her face. An impatient-looking grin.
‘Ohhh…!’ I still hadn’t a clue but, by now, I’d learnt to just go with it, be decisive — there’s a big difference between rushing out at the last moment to buy your girlfriend a birthday present and actually forgetting her birthday.
‘Right… hand it over then!’
[I'm struggling to write the story at this point, but I'll continue on... -S]
I squirted a little lube onto my hand. Cold, slimy. What was I meant to do? Just rub it on? Sure, I can do that… On it went. Slippery. A little chilly too — menthol? Wow, my nervousness slipping away, this was going to be wild!
She sat back onto me — the Asian Cowgirl (don’t click!), apparently – and… sure enough, the lube helped; a bit too much, if you know what I mean, boys. Before I know it, she’s bouncing around like a maniac, my biceps pumping like pistons. Faster, faster, DEEPER – penetration has never been this easy! In the heat of the moment I decide to go for one of my favourite moves, the back-breaking whip-it-all-the-way-out-and-then-thrust-back-in-even-deeper. I arch my back and push her upwards, escaping for just a moment. We take a collective breath and she grins at me over her shoulder. This is the run-up to the finishing line we’ve got to get it right. I pull down on her hips and thrust upwards.
BANG! Back in I go. But wait a second… this feels different. Really different. Tighter.
‘FUCK, Sebastian!’
I withdraw quicker than the head of a terrified turtle.
‘Shit, wrong hole! Er… not shit, I mean… er… DAMN!’
…
That was the end of that. Ironically, the lube was actually purchased with that purpose in mind! I think she’d anticipated a bit more warning and preparation. The lube went back into the bedside table drawer, never to be seen again…
But not the end of the story! Now the bad bit…
[Deep breaths, Sebastian... deep breaths...-S]
We’re in the shower now. It’s been two days since the incident and I’d all but forgotten about it. Heat of the moment. Controlling your penis isn’t easy at the best of times, especially not the tip of it, 8 inches away from the nearest cluster of muscles. Water under the bridge. What happens in the bedroom stays in the bedroom. Obviously though she hadn’t forgotten…
I finish rubbing the soap into her skin and rinse her off with the shower head, with a little teasing of course. I turn around.
‘My turn. Do me!’ So she rubs shower gel into my back, my shoulders, my torso. It’s slippery and soft and warm and wet. Her hands work their way down over my stomach to my hips and then she teases me with the soap, her hands, the shower’s jets of water. I’m getting quite into it when all of a sudden, out of fucking nowhere:
POP! Finger up ass. All the way up. My last virginity, taken ruthlessly and without consent. At least she’d lubed her finger first.
‘How’d you like that, Seb?’
Related posts:
- My mother and I, a tragic tale of thrush and condoms
- The meteor shower romance
- Shared accomodation is great until your housemate’s mother watches you screw your girlfriend




Hahahaha I think I love her…that’s ace!
I’ve only had one erm ‘without permission’ entry to THAT particular ride and I wasn’t impressed at ALL. It wasn’t just the fact that it was my first time with that particular guy (I mean, who does that the first time you sleep with someone?!) but you always ask before you go there, always…otherwise it’s just not cool.
May 21st, 2009 at 7:40 amHahahahahaaa! Oh, snap!
May 21st, 2009 at 8:04 amOw, my butt was tight the whole time I was reading this.
Hahahaha, great story and I must say that she is hilarious. I did the same thing to my ex.
May 21st, 2009 at 10:16 amWhat the fuck? If that had been me I would have crippled you for that. I’m sort of surprised you weren’t beaten to a pulp, actually. Debating whether or not I believe this story.
Also, she should have gone further at the end. A dildo, maybe, to get the desired effect.
May 21st, 2009 at 11:08 amholy mother of smothering! wahahahaha. her last line was precious! the head of terrified turtle indeed! wahahahaahahahahahhaahaha.
May 21st, 2009 at 11:35 amOh God. lol exactly what I need first thing in the morning.
She handled that well, I’d say. I’d have stories to reiterate your point… but, like I said, too early in the morning for me to be discussing anal.
May 21st, 2009 at 12:17 pmYou know, I’d totally forgotten that this was probably an inappropriate topic for early in the morning… I’d apologise profusely, but if you know anything about me… I’d be lying
Kali, as I hinted, I was meant to go there, just… not quite so brutally.
I blame the lube 100%. There was simply no way it’d even begin to work without lube.
Pink… really? Sounds like you had a porn-watcher on your hands, because don’t-ya-know, EVERY girl digs anal…
May 21st, 2009 at 12:41 pmI like her. Good show!
May 21st, 2009 at 1:24 pmBAhahaha. She is obviously awesome.
May 21st, 2009 at 1:25 pmAAAAAAAAAAAAAHAHAHAHAHAHAHA
Yes!
That is awesome! I prob would’ve done the same thing.
May 21st, 2009 at 1:43 pmI’m not sure if I’m liking this whole ‘YOU GO GIRL!!!’ thing…
Where are the sympathetic male responses?
May 21st, 2009 at 1:45 pmYep, just shoved it in, no warning or anything. Needless to say, it was the last time I saw him….
May 21st, 2009 at 2:07 pmseb, i’m giving you an award. lol. for being so dramatic LOL.
May 21st, 2009 at 2:29 pmYou mean for taking it like a man, right?
Or, um… like a hero.
May 21st, 2009 at 2:30 pmhahaha
May 21st, 2009 at 2:32 pmi like ass play but full-speed-ahead-without-warning is a bit much. ouch!?
good thing you were all lubed.
payback, karma…. it’s always waiting for you!
May 21st, 2009 at 2:42 pmOMG so dirty, lol !
May 21st, 2009 at 2:56 pmI guess it was just a fair way to pay you back for that surprise you gave her ! lol
you’re a better man than me. the butt is off-limits. why? you’d probably think the same thing if you pulled out once and you were covered with what she had for dinner. yep, sesame seeds and all. no, thank you.
May 21st, 2009 at 3:29 pmA MAN! Hooray!
I guess that’s almost sympathy… or at least… adulation…
I believe, F.B, that there are certain preparatory tasks that one should take.
To all the girls saying I deserved due repayment — it WAS a mistake!
May 21st, 2009 at 3:42 pmThis girl is my hero. LOVE HER!!!
May 21st, 2009 at 3:58 pmLMAO.
May 21st, 2009 at 5:17 pmOUCH!!!
Lube can be a slippery mess.
payback is a bitch!
May 21st, 2009 at 5:19 pmI feel your pain. the wife has been warned that I would break that finger off! No Entry: Exit Only! Did you feel dirty afterwards? Sesame seeds? For real? I think I’m gonna puke. Why are people fascinated with assholes? We crap out of those people!
May 21st, 2009 at 5:31 pmI think I could deal with sesame seeds. Beetroot… not so much.
Is the whole finger-breaking thing in the pre-nuptial agreement, or did you just stare into each others eyes one day at the supermarket, next to the tubes of lube, and agree that no more should ever be said on the matter?
May 21st, 2009 at 5:35 pmOK, I’m trying to get the whole beetroot image out of my head. Very Bad Cat is my significant other, nuff said!
May 21st, 2009 at 5:46 pmSorry, I was just going with the flow there, so to speak. Maybe went a little overboard.
Very Bad Cat winked in a way that suggested she might have had to endure a few trips to the hospital to get her fingers splinted…
May 21st, 2009 at 5:53 pmI think I’m scarred for life.
May 21st, 2009 at 5:59 pmHahahahahaha girl was merely returning the favour and hoping you would like it lol
I literally laughed out loud on a crowded bus wit many a snr citizens its moments like these I am glad to be black therefore when I blush no1 can see the red hot heat on my too cute cheeks:)
May 21st, 2009 at 6:41 pmoh my science. that’s hilarious. I love that girl.
May 21st, 2009 at 7:03 pmYet another mental scar courtesy of Seb. The writing was really good – a little too good – no animation required.
May 21st, 2009 at 7:55 pmwas that meant to be laughed at? ooops if not sorry. i really needed that post today of all days in more ways than one. thanks….
May 21st, 2009 at 8:06 pmAhahahaha! All’s fair in love and ass play…
May 21st, 2009 at 9:02 pmOh I’m glad, Rambles
I actually just fixed my blog so that it should load properly on mobile handsets! I had another friend that was trying to read it, and it wasn’t working… so now you should be able to laugh even more easily on the bus!
PDO, I’m not sure if I’m seeking sympathy, or just putting it out there for the world in general. I think it’s nice to know that there are girls out there that are willing to take vengeance into their own hands…
Was there a story to share there, LiLu, or were you simply referring to your infatuation with scatological stories?
May 21st, 2009 at 9:07 pmI TOTALLY did that to my ex…except it was with a….eh…. toy….
Just wanted him to see how it felt. apparently, not good.
May 21st, 2009 at 9:49 pmI’m shocked that no one noticed how I left out my actual REACTION to the incident…
*grin*
May 21st, 2009 at 9:53 pmI’m mouth is seriously gaping open. Oh my God. Hahahaha.
May 21st, 2009 at 11:22 pmJealous, in agreement with her actions, or just plain shocked?
May 21st, 2009 at 11:27 pm“for being so dramatic” I said.
“for taking it like a man, right?” asked Seb.
“like a manly hero, Seb” I replied.
May 22nd, 2009 at 1:05 amShocked? Not I, of course. I think it’s a very typical bedroom/bathroom sex scene. I’m not a fan of sex in the shower, though. You lose all the good juices.
She is obviously not entirely evil or your experience could’ve a lot worse. Hmmm?
May 22nd, 2009 at 1:10 amYeah, I’ve only actually had sex in the shower once, and I have to admit it wasn’t all that great — for the reason you state. And because the height difference between me and the girl is exacerbated by standing up, which can be a problem if they’re short (which they tend to be…)
It could’ve been a lot worse. It was actually quite nice…
May 22nd, 2009 at 1:15 amGood girls return the favour!
May 22nd, 2009 at 4:06 amyou’re lucky she only used a finger….
when i was just starting college, a wiser older girl give a little speech to us naive young ones about how one day, a boy would try to put it up our butts. her suggestion: say you’d be happy to try, as long as he would be willing to try first. and then go to a sex shop and buy a dildo the same size as his eager beaver. apparently not many guys continue on to the next step.
May 22nd, 2009 at 3:46 pmI’m not incredibly experienced in the matter, but as I understand it… men should actually enjoy it — unlike women, who simply have to take it because porn went and popularised it. I think it can be ‘OK’ for women, as an intense experience, but for men it’s actually in itself enjoyable?
But yes, there’s some psychology involved — you probably know about how impotent men gain a whole slew of other issues and complexes. ‘Being the bottom’ is a submissive thing, and most men are not so great at that — even if it would feel great…!
May 22nd, 2009 at 4:13 pmWOW. I’m taking a break at the moment while visiting the boyfriend and stumbled upon this gem.
Gives me some great ideas
May 22nd, 2009 at 5:15 pmyou made me laugh in a silent night !
May 26th, 2009 at 4:05 amNot because of that accident. The way you express it,
“I withdraw quicker than the head of a terrified turtle.”
Oh…the surprise slip. It’s happened to me way more than I’d like to admit. OUCH.
May 26th, 2009 at 5:00 pmSame guy each time, Maxie? In which case, you should take the hint…
Or multiple guys, and just never learnt your lesson?
May 26th, 2009 at 5:05 pmI had to leave the room half way through this to put a bandage over my ass.
I know someone who woke her very uptight (interpret that in every way possible) boyfriend like that out of anger.
OUCH.
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