Wes Mantooth

We've all been there haven't we? What should be a fun romp in the sack turns into a comedy of errors, miscommunication, blunders and bloopers so awkward that you still cringe when you think about it years later. Maybe when trying to undo her bra you hook your finger into the blinds above the bed and pull the whole thing down on top of you? Accidentally released the parking brake in the throws of passion sending the car rolling down a hill while nude and screaming? Ever reach into your wallet and pull out condoms that are way too small (or big) and you've got nothing else? Remember that time the girl you were crushing on really hard came over to hang out and you awkwardly tried to start something only to find out how so very wrong you were about everything?

I'm sure we can all look back on those bad sexual episode and laugh about them now so lets hear about it. Dig up something from the past or what the hell post something that happened last night if you want to. If anything it might make for a pretty funny thread.

EDIT: Alright I apparently can't sleep so why don't I start us off. Out of all the examples I posted above the first actually happened to me when I was in high school. I'd been trying to get the attention of a girl from my school and low and behold she actually invited me over on a weekend when her parents had left town. Of course that was probably the only thing that went right the rest of the night.

I show up at her place in my new truck with the contents of a few mini bars that somehow found their way from a local hotel to the back of my closet (don't ask, the liquor fairy works in mysterious ways). She seemed a little taken aback by all the alcohol but after I talked my way inside she went nuts with it...in a few hours she was so drunk she couldn't get off the floor and I had gone from lampshade on the head drunk to head in the toilet drunk. Yet somehow we groped and kissed or way into her parents bed room. It was going pretty good until until I tried to be smooth and unhook her bra, only somehow in my drunken state I hooked my finger around the sting on the venetian blinds, I fiddled with it for a bit, finally got fed up and just gave the whole thing a a good yank (I have no idea what I was trying to achieve with that). The string snapped, half the blinds somehow fell out, the curtains came with them and she completely looses it.

The night probably could have been salvaged, sure she was upset that her Moms new blinds (apparently they were brand new as were the curtains) had been broken but shit happens right? Well I insisted that I could fix it, too drunk to stand I climb up on the bed and figured I could just tie the string back together or maybe make it look good enough that she'll stop worrying about it and we could get back to business. In the process I loose my balance, spill a bottle of tequila on the mattress and knock over the bed stand shattering a lamp all while comically nude. She threw me out.

I was too drunk to even hope to drive home so whats a guy to do? I wasn't going to leave the truck I'd just spent the better part of 2 years saving up to buy in her driveway while I walked home so I crawled into the cab and fell asleep...it turned out that was probably a mistake. I'm awoken the next morning to her throwing tiny, empty bottles of booze at my truck and screaming something about her parents coming home any minute. We tended to avoid one another in the halls after that.

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Cimarron29414

Can't top that!

The only one I have is tame by comparison. Dated a girl in high school whose parents raised her Southern Baptist - hard core. I put in the time and slowly broke down the defenses - it was worth it, as she had the best body of any woman I have ever been with. Being perfectly normal, idiotic teenagers, we decide the best place to try our first time is upstairs at her house in the F.R.O.G. - which connects directly to the kitchen, where her mom spends most of her time (great cook!)

We are on the couch, her straddling me, my pants around my ankles, her panties on the floor, her skirt hiked up to her waist. We're working on the insertion part - which is not going well as it's her first time - when her mom calls for her up the stairs. It was one of those dead silences, which last too long. Are steps being climbed? Too scared to move. Deer meets headlights.......Like porno ninjas, we struggle to get our clothes on in 2.5 seconds and she goes and tends to her mom, flush with embarrassment. I stayed up there and reacquainted myself with acknowledging God's mercy.

I think back on it and know good and well her mom could have just as easily climbed the 12 stairs to the room to check on us without us knowing. We were REALLY concentrating. It would have been very...very...bad - perhaps even shotgun bad. Every time I think of this event, I shake and cringe at what could have been.

For the record, we dated for 4 years after that - and that part of the relationship was truly great. I still see her around town. She's still got that body.

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Gives a man a halo, does mead.

"Here lies The_Jazz: Killed by an ambitious, sparkly, pink butterfly."

Wes Mantooth

That's amazing Cim, I think a lot of us can relate to that one My god does first time, awkward teenage sex ever go right? Its also quite funny how brave we tend to be when sex enters the picture. We'll brave a 6'5", 300 pound angry father with a needlessly large gun collection watching football in the other room if it means 30 seconds of sweet, sweet sexual bliss.

Thanks for the response I enjoyed it.

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seamaiden

This didn't happen to me...it's a story from the emergency department where I work. A 64 year old women came in with a glass chandelier bulb inserted into her rectum, that she couldn't get out. Her husband had put it there, but then "somehow" it got stuck too far in. An x-ray showed it was about four inches deep so the Dr. tried to reach it with sponge forceps, but it was too slippery. He gave her the choice of surgery to remove it or let him try to reach it by hand. She agreed to let him try and luckily he was able to get it out after a few uncomfortable moments.
This is obviously a case of people too embarrassed to go to a sex shop to purchase a proper plug...I'm sure she was mortified to have to go to emerg. Her husband didn't go with her. Also, she could have been seriously wounded if the bulb had broken inside her.

Pearl Trade

Did you ever get to do the dirty without interuption?

And, Seamaiden, have you heard of the Russian who sat on a jar and it exploded in his ass? Your story reminded me of that...

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Our revenge will be the laughter of our children.
Give me convenience or give me death!

Shadowex3

Lets see... both of us were 18/19 years old, huge nerds, virgins, and while I'm a jew she's an athiest catholic schoolgirl. I'm already for some reason "allergic" to this girl. As in red watery eyes, runny nose, cramps allergic just from being NEAR her but being my first real girlfriend I have no clue what is going on and just figure i'm allergic to some product she or her parents use (or her cat).

Now, I'm good at massages and she's apparently at least as horny as I am and being a nerd not afraid to admit it in her own way, which leads to her getting a handjob and some head for an hour before getting off. We try to go further but I can't get it in. We figure it's a virgin thing and decide to try again some other time since her very catholic parents are

Eventually it's time for the second try. I've got the condoms, the spermicidal foam, and after an hour or so of H&H and one horrifyingly painful incident where she tried to take an inside-out condom off by pulling the end (SNAP) we get the idea that maybe the foam'll help keep the condoms from drying out and keep things lubricated (should've been a hint). It's one of those aerosol/plunger deals and I try to load it up with the plunger pulled all the way out... now I don't know if any of you have ever used one of these before but that plunger's airtight and the can is really well pressurized. In retrospect I was pretty lucky I only got foam in my eye and not the plunger, which actually put a small pockmark in the ceiling where it hit and got that damn foam everywhere. Yeah that kinda killed it.

Third and final go we're both back at it, I've got the condom on, foam's deployed properly and I've read up on anatomy and some cheap anatomic tricks to help out with this. We get going, I get the right hole, go in slow and finally we're bumping uglies (literally).

Now at this point I should take a moment to refer back to where I mentioned I'm apparently allergic to her, which meant I wasn't exactly feeling in perfect health. She's also a pretty tiny girl, maybe 5'4-ish, and built on a very slight frame. I on the other hand need to wear magnums for the width if not the length since regular trojans are so small that I basically go numb from the lack of circulation.

So I'm there feeling like I've got a head cold and some indigestion, numb, feeling like I'm getting kicked in the nuts, and then I get stuck. I can't get out. I've got no lube, and certainly no desire to call the EMTs, so I need to get her to relax before I need an amputation. I start joking around, "falcon punch", distracting her basically any way I can.

It works, thank god, and from here on everything is normal except that I'm left doing my best discovery-channel impression with this girl for three hours and even when I resort to trying to jerk off at the end I'm still numb and feeling like I got three swift kicks to the boys. Eventually other E/N style drama leads to a breakup followed by serious douchery on both sides, 2 years of silence, and us eventually talking to each other again after growing the hell up.

I'm just glad that we broke up before she got the nerve to try giving me a BJ. With this kind of comedy of errors I don't want to THINK about how that could've ended.

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Wes Mantooth

Okay I get being curious and maybe to shy to go buy a sex toy but nobody should be THAT curious! I'd love to have heard the conversation leading up to inserting a chandelier bulb...somebody had to be selling that one hard. I'm going to go with the husband, if I'd done that to my non existent wife I'd probably being laying low too.

Anyway...'nother one!

When I was in college I worked at a summer camp to earn extra money. It was a great job too, I worked as part of a 2 man maintenance crew with one of my best friends, it paid pretty good, the work was easy, we had lots of time to sit around getting high or drunk between jobs...and the camp was full of horny girls with nothing better to do at night then to knock a few back and practice being wild sex crazy college girls before the fall semester started. Summer heaven. (okay maybe not but it felt like it at times)

About a month or so into the summer we got a third crew member, a young kid named Sam. We liked him right off the bat, he clicked with us and seemed to be enjoying our summer of slacking off. He was a little sheltered, it was his first time away from home (I think he'd just turned 18) and obviously didn't possess any kind of girl gettin' mojo...he was just so god damned awkward. We'd invite him out with us after work to hang out with the girls but he always managed to fuck it up one way or another, strike out and go back to his cabin alone...I can't begin to explain how hard that would be to do in that environment. Eventually he asks if we can help him out and give him a few pointers so he could actually get laid just once before going back home. We obliged and to be honest he couldn't have made a worse mistake.

Hitting up camp 'tang for sex at that point was second nature to us, I don't think we even put any thought into it anymore so teaching somebody how to go about doing it was a lot more difficult then we imagined, if that makes any sense. Worse still by the middle of summer we were the very picture of burn outs and probably not the best people to take advice from. "Dude was she drunk? Just take into the canoe shed it should work itself out". Nothing was working and by the final week of summer he still hadn't gotten laid, it was getting awkward and quite honestly statistically he should have at least gotten a blow job or something by then. So desperate times called for desperate measures.

Having worked there for a few summers we knew a lot of town folk as well, including a girl named Jackie. She was, for lack of a better word "experienced" with the fellows but she was good looking and willing to help the poor kid out (we actually told her it was his birthday). So we stuck her in the cabin we used down by the lake, picked him up from dinner, liquored him up a bit, gave him a pep talk and shoved him through the door. Certainly nature would take its course right?

With all the time we'd invested in this we decided to hang around outside and see how the whole thing went down. We passed a bowl back and forth and listened for any sign of life inside the cabin, but there was nothing just complete and absolute silence. Suddenly there was a bit of commotion and Sam came hauling ass out of the cabin door (sans pants) and nearly sprinted down the trail, the poor kind looked like he'd seen a ghost. We head on inside and Jackie is laying there, half nude and smoking a cigarette. We asked her what happened and she explained that he no idea what he was doing, he had her tit in a vice like squeeze and was just standing there motionless. She took control and decided for some reason that she'd teach him how to properly fist a girl (really? kids first time and you think THATS a good idea?). Taking his hand she tried to guide him position and just as his fingers got into are about to touch the promised land, he blows his load, yanks his hand away and tears out of the cabin. I guess he wasn't quite ready for that just yet. Worse still she hung around the rest of the night trying to hit us up for sex and drinking all of our beer, what a disaster.

We apologized to him the next day and he was pretty cool about it but the great sex quest of '03 had run its course.

EDIT: Snuck in on me there Shadow, great story! Again I think we can ALL relate to awkward first time sex, seriously it would just be so much easier with a manual.

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Xerxys

^^ OMG!! I can't stop laughing! AWESOME!

Craven Morehead

fisting on first date - hilarious

Shadowex3

Thanks mantooth, every time I think I win the award for most horribly awkward first-time-intimacy stupidity the universe provides examples of just how much worse it could've been.

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Wes Mantooth

Yeah you could have had me and my buddy as sexual role models trying to guide you through it, that thought, now, even scares me...I still feel a little bad about it though and wonder if he gets panic attacks every time he makes a fist.

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Starkizzer

Guess I'll share, though I'm sure smrt will be slightly mortified.

We had been fooling around for a few months, not full blown sex but just about everything else. We would drive his van out in to a field at night and pull all the back seats out and fool around for hours. This was pretty much a nightly routine. Our disastrously funny events all involved us trying to incorporate food into our evenings.

So for whatever reason, we thought it would be fun/sexy to get a can of whipped cream on one occasion and Popsicles on another. Both went horribly wrong!

First the whipped cream: We bought a can of Reddi-whip and headed out to the desert to have our fun, I think we might even have bought some chocolate syrup. So there we are stark naked in the middle of the desert and he goes to squirt some of the whipped cream on my nipple. I am horribly ticklish and tend to thrash and flail when I am being tickled. Well the feeling of the Reddi-whip being expelled onto my nipple set off exactly this reaction. I flailed, hit he can, and the next thing I heard was im2smrt4u saying "owww". The can had gone flying at his face and left a star shaped cut about a cm from his eye. It was difficult to explain to our parents how he ended up with a cut in that shape near his eye.

The other incident involving the Popsicles went even worse. For whatever reason, smrt had the idea that it would be fun and an interesting experience for me if we played with Popsicles. This idea most likely came from a porn he watched and thought it would be great fun to try on me. I should have said no, but being a horny 18yr old, I was up for anything. So once again, we are in the van stark naked in the middle of the desert and in goes the Popsicle. Let me tell you this is the worst idea ever! Instant cold that made my whole body get goose bumps. As I recall this experiment was done in the middle of the summer which meant that even at night it was still about 90F. I swear I felt cold all night and the next morning it still felt like the popsicle was inserted into my vag. It was awful but all we could do was laugh at what a horrible idea it was.

We have never again tried to bring food into our sexcapades. Smrt really wants to eat sushi off me but I won't let him. All I can imagine is wasabi getting its way into my naught parts or some other awful event occurring.

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Frivolity, at the edge of a Moral Swamp, hears Hymn-Singing in the Distance and dons the Galoshes of Remorse. ~Edward Gorey

levite

OK, so this was with my First (a VERY long time ago). We had made out a couple of times, and finally decided we were going to be "secret boyfriend and girlfriend" (translation: fuckbuddies, but she didn't want her cheerleader friends knowing that she was shagging a geek, and I didn't want my emo-punk proto-goth friends knowing that I was doing a "popular" girl). Both of us were virgins, though we'd both "done stuff" before.

My dad was out of town, so I had the place for a couple of nights. She came over. I was big with the romance: wine, candles, roses, and I borrowed my dad's silk sheets.

Fortunately, I was spared the condom necessity by the fact that she was on birth control pills (and this was before everyone knew about AIDS and the need to always wear a condom no matter what). However....

Having never actually had sexual intercourse, I had no clue just how wet a girl might get, or whether it would be enough, or anything like that. And after all, she was a virgin. So I presumed that we would definitely need lube.
Which I duly procured: a large squeeze bottle of it. And when the moment came, I got it out, and squirted a generous squeeze right up inside this girl. Apparently this was stimulating for her, because as I brought the bottle away from her goodies, she moaned and gave my dick a firm stroke, which felt great-- but caused me to involuntarily squeeze the bottle again. Hard. Her junk. My junk. Her stomach. My thighs. The bed. It was like the Exxon Valdez crashed into our genitals. But we were young and horny, and felt like we couldn't be bothered to wait. So we tried to get down to it.

Anyone ever tried oiled-up wrestling? Hard to hold on, right? So maybe you get the picture when I say it took us a good ten minutes just to hold still enough for me to get it in. Another five to ten minutes of a couple of thrusts followed by me slipping out, or me slipping off of her, or-- I kid you not-- her squirting off my dick and sliding backwards on those damn silk sheets.

But also, ever put too much lube inside a woman? It's squelchy, am I right? So we're fifteen, twenty minutes into this debacle, when...I'm sorry, I don't know any other way to put this: pussy farts. Big time. Wet with lube. She was mortified. I couldn't stop laughing. She couldn't stop 'em. Didn't help that we kept slipping and falling and sliding around, all oiled up, on this silk.

Thus ended the "first time." It took a lot of sweet talking to convince her into a second time.

Which, thank God, was much better. It was also free of lube, and none proved to ever be needed. But I had ruined my dad's silk sheets, and had to tell him that I tried to launder them, but they caught on fire in the dryer. Whether he ever believed me, I still don't know.

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Dull sublunary lovers love,
Whose soul is sense, cannot admit
Absence, because it doth remove
That thing which elemented it.

(From "A Valediction: Forbidding Mourning" by John Donne)

Wes Mantooth

Oh my GOD! Levite thats such a spectacular failure! I love it

This one happened to me in the winter of ought 8, looking back on it it might have been one of the worst sting of bad decisions I'd ever made. I'd played a show with a band in downtown Nashville and was invited out to sort of an after party, it sounded like fun and my sort of gf at the time, Megan wanted to go so we went over. It was a little apartment on the north side, one bedroom, a small living area, kitchen and bathroom certainly not the best place to be crammed with 20 plus people looking for a good time.

For some odd reason neither Megan or I had really had much to drink that night so boredom set in pretty quickly when people started filtering out, by 1 or 2 in the morning the place was pretty much dead, a few people passed out on the couch (including this hot little blond number who had slept through having her shirt and bra pulled off...just slept there as her tits slowly moved up and down with the motion of her breath...damn I wished I'd had a camera), a couple was making some sweet love in the bedroom and the remaining stragglers had taken over the kitchen to play drinking games...it was getting pretty lame. Earlier in the night I'd made some bet with her over god knows what but the winner got oral sex at the time of his or her choosing...it was just one of those funny things we did for some stupid reason...anyway I was bored and it was time to pay up.

The apartment wasn't too accommodating, the staircase even worse and the small balcony far to public but for some reason I had it my mind that I was getting head at this party (maybe I'd been thinking about the blond on the sofa). So we turned to the bathroom. Now I have to shift gears here for a second and give a bit of back story. In this particular crowd of friends we know a fella named Rich. Rich is a great guy but just can't seem to hold his alcohol and when shit starts flowing heavy he usually winds up puking his guts out in the bathroom...this night wasn't any different.

Megan and I opened the door and sure enough there's Rich passed out and curled around the toilet, I poked him with a plunger and got no response but what the hell he was a good guy and I couldn't imagine he'd deny me a little after party head in the bathroom because he'd passed out by the toilet. So we thought fuck it, I drop my pants and lower my hairy ass down on the toilet seat her top comes off and she gets down to business. MY GOD was she amazing at giving head, this was head for the ages...wars have been started over blow jobs like this one...sonnets, symphonies, great literary works have been written over lesser ones. This is ball gargling, devouring a popsicle and swallowing the stick head.

So I'm moments away from blowing my wad and suddenly Rich begins to stir, he mumbles a little bit, coughs and suddenly yells out "WHAT THE FUCK!!!" Oblivious or I guess not caring we just keep going until he flips out shoves me off the toilet seat at full force and sends me and Megan tumbling into the shower door. Now you have to picture that one because I don't possess the writing skills to do it justice. She's throat deep in Mantooth cock and the shove sends me crotch first into her face like a giant hairy, flesh colored freight train. I know I was probably in the wrong here but having my oral sexfest interrupted at three in the morning by a lightweight toilet jockey set me to a rage.

Still pantless and my gf on the floor checking to see if she still has any teeth left he gives me a shove, I shove him back and we wind up rolling around on the kitchen floor swatting each other with half assed punches. Its about this time that fellow who owns the apartment comes around the corner to see whats going on and I can only imagine what was running through his mind as we wrestled on the floor with my ass displayed for the whole kitchen to see. Everyone pulls us apart, which was easy as we were already starting to laugh about it and a handshake later we'd made peace...Megan not so much as she stormed out of the apartment and pretty much out of my life.

Easy come easy go I guess but old Rich never ceases to share this story with ANYBODY who might be willing to listen to it including earlier this evening to a girl I was currently chatting up. Thanks buddy you owe me one brunette and barrel of of Lynchburg's finest.

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dlish

mine is not quite as funny. Quite the opposite really.

anyways, back in sydney she-lish and i were on the workbench in the bedroom getting things on. It was about midnight and it was in summer, so we usually leave the windows open and the blinds closed. our windows had security bars because our area wasnt exactly a bastion of safety.

The bedroom apartment faced a common area balcony that no one ever used because it was blocked off by railings, so it was pretty private and no one went there.

So she and I are going at it, and i get a weird feeling that we're being watched. It was a windy night, but the blinds are closed and there is backlight which casts shows on the blinds from trees swaying in the wind. So as much as i was in the mood i was distracted from this feeling of us being watched. I had no idea why i felt this way, but i did. The leaves twirled and tumbled in the night with each gust of wind, and i kept an ear and eye out on the blinds, while still doing my deed noises and all.

Then, i hear a rustling sound. its weird. its not your normal leaves rustling, but im thinking, its just my imagination. Then i see a shadow move in the shows cast by the trees. it couldnt be.. its just me seeing things. we continue, and we change positions so that i can keep watch on the window...i'm about a metre away from the window, and i sense a presense outside..in a quick motion i go to the window and brush the blinds to the side and see an african guy literally with his head on the security bars only centimetres from the glass.

as soon as he saw me, he split out over the garbage enclosure and onto the street. in my anger i screamed at him but i couldnt jump through the window to chase him because 1) i was naked with a hard-on ,

2) because there were security bars on the windows.

she-lish is upset and screaming by now and im enraged with the violation. Our suburb wasnt a very good one,. the crime rate was and still is quite high. so i wasnt sure if this was an intruder or a peeping tom. i quickly put my pants on and ran to the kitchen and grabbed a knife for safety. [ yes i know it may have been an overkill, but in the spur of the moment i was in a fit of rage, coupled with the fact that our area is crime-prone made me rationalise that i needed a knife for protection]

so i ran outside looking for this guy. deep down i was hoping id find him because i wanted to tear this guy apart, but on the other hand i didnt want to find him because it was either going to end up badly for me or for him. i searched the area, the bushes, the garbage enclosure and saw nothing. i asked a neighbour i saw outside and he didnt notice anything, so i headed inside.

all the while, she-lish had called the police, and so a few minutes later the police arrived knocking at my door looking for the intruder. while police scoured the surrounding area, i tried to explain to the female police offer what exactly happened. the two cops wrote their report with a feint smile on their faces...

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An injustice anywhere, is an injustice everywhere

I always sign my facebook comments with ()()===========(}. Does that make me gay?
- Filthy

Wes Mantooth

Yikes, that's creepy dlish. Thank god for the bars huh? So what do you think? Guy looking for a free show or somebody trying to break in at a VERY bad time?

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dlish

no idea Wes.

Till this day, i still dont know. He couldnt get in obviously, so im inclined to think that think he was a peeping tom. probably from the neighbours who lived next door, but i cant prove it.

i must have been too loud the night before and attracted the sharks

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An injustice anywhere, is an injustice everywhere

I always sign my facebook comments with ()()===========(}. Does that make me gay?
- Filthy

Wes Mantooth

HA!

"Well they seem to be having sex every night around 8...I could take in the show and still have time to steal the tv! SCORE!"

Good stuff, thanks for sharing it.

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