I dated a girl once who was younger than me (16 to my 17) and I told her that it was her turn to by condoms. She was really nervous about it, to the point that she bought them over the hill from coast, wearing sunglasses and a hat. Apparently she just walked in and grabbed the first box she saw, which was "extended pleasure." by Trojan. Well, we finally get some time alone to use them, and I had never seen "extended pleasure" condoms before, so I put one on. I didn't know that there was a numbing agent inside. Well, my whole dick started tingling, and then went dead. Not limp, I just might as well have had a strap-on on and been fucking her with that because I had nothing. So I decided to just go with it, as she was enjoying it, but I might as well have not even been there, as I was getting no feeling. We keep going at it, and after 25 minutes without feeling anything, I act like I here the gate to the driveway opening up so we go through the usual "oh shit, about to be caught by parents scramble", and I took the damn thing off, and threw out the box. Even if I was a guy who came after a minute I wouldn't use those damn things.
I received a chicks-dig-scars gash above my eye from a fucking Ginsu-sharp IKEA headboard. It was all good, though. It bought me three minutes.
I had a crush on this guy for ages and we had finally started to hook up/date. We had kept things pretty G rated for the first couple weeks but being the slut I am, it was getting boring and quickly. We went home after having a romantic dinner date and I started to instigate (pretty forcefully) us hooking up. We were both almost naked and I could sense he was super nervous but figured it was just jitters since this would have been our first time doing it*. It finally got to condom time and I was getting super excited at the thought of finally getting some dick but looked over just in time to watch him.... cum inside the condom while putting it on. I have never wanted to punch someone so badly for not being able to fuck me and I am pretty sure he understood that which made things even more awkward. Thankfully, he was able to rebound pretty quick and I did end up getting laid that night, but the vision of his pink face, flushed with orgasm and embarrassment, wasn't easily erased from my brain and we broke up soon after. We are still really good friends and when I was visiting last summer he got drunk enough to explain that I was "too much for him" and though he wanted to be with me at the time I was intimidating in bed and he needed someone who was more submissive. * with each other, not overall
Until recently, I've never had an issue with bad kissers. In my experience, women have been good kissers and on a whole it's been an enjoyable time; that is until recently. Now, I've got to preface this by saying the mere thought of kissing this woman again makes my dick want to crawl into my stomach and kick me in the lung. I've got fairly large lips, which from what I've been told, are quite the asset to good kissing. Problem is, if she's got little thin bird lips, it's not quite as enjoyable for me. The Bad Kisser (BK), had those thin bird lips and definitely didn't know how to use them. As terrible as it seems, she would just lay there and take it; wouldn't do anything, just do this strange, soft pucker up and kiss. It was like I was pressing my lips against two warm sandwich bags, except instead of plastic, the bags are made out of skin. Now, I can get over that part; not horrendous; the killer was when BK used tongue. She would just stick her tongue out into my mouth, no warning, just bam - all soaking wet tongue. I wouldn't have been surprised if she stuck her thumbs in her ears, and did that stupid "Na na na na naaa" dance and hand waving combo that little kids do. Oh and she didn't give blow jobs but was quite happy to let me eat her out - good thing I was drunk.
Worst definitely goes to the boy who felt that his awkward vagina probing was appropriate reciprocation to me giving him head. I can't even properly describe what he was doing because it was just so so so strange, but nothing about it felt any sort of awesome. And the best experience goes to the boy who ate me out on a picnic table. Now that was all sorts of awesome.
It was a rugby tour, called Maggot Fest, in a place called Missoula, Montana, many many moons ago. Male and female rugby teams from all over the world were there for a week of drunken debauchery and rugby. It was a few days into the tournament, late at night, she was the 8th "man" on her team, and we rutted like drunken farm animals on a small grassy knoll only a few yards away from my team's RV, much to the enjoyment of my teammates who were drinking around the campfire. Her nickname was "The Coke Machine" because, well, she looked like a coke machine. She was much taller than I was, and some of the more memorable quotes from the evening were "get your ass down, I can't reach...". Our theme was the Flying Nunns, so I was dressed in a nun's habit at the time... just to round out the lovely visual image. I was unanimously awarded the "Pig Of The Port" award for the tour, and bestowed a POTP Lifetime Achievement Award shortly after by the club.
One of my worst was with a woman who I dated for 7 or 8 months several years ago. I stayed at her place one night and we fucked the next morning. For some reason, though, I just couldn't finish. I was able (hard) and I was willing. I just couldn't get the job done. Perhaps I slept like shit and I was just tired. I don't fucking know. How did she handle it? By berating and insulting me, of course! "If this is happening now, what'll happen when you're 40?" Now... This was an ISOLATED incident. We'd fucked many times before and after. Her and I were always good together in the sack. Hell... She came. I'd been with her enough that I knew her signs and she'd even tell me when she did. So... Not only was I slightly embarrassed, but I had to deal with her fucking browbeating me over what was essentially a nonissue. We only dated for a few weeks after that. I had no desire to stay with her and I ended the relationship.
This is both timely and unfortunate. A couple of weeks ago, I had a girl over for what we had agreed was a booty call. We've been friends for a long time and for whatever reason, we decided we should fuck one afternoon because we had nothing to do and we were both horny. Never had sex before this. So she gets to my apartment and she's still dressed from work, she's some kind of receptionist or something. So I think, cool. She looks good. This could be fun. Until she reaches my door and I let her in. No deodorant at all. And it was the most awful thing, because she was really clean. Her hair was soft and fluffy, she had clearly washed it that morning. Her clothes were neat and fresh. Her skin was clear. There was nothing dirty about this girl, and yet... she stunk. Awfully. I couldn't wrap my head around it. I didn't listen to a thing she said, just nodded and "yupped". She sat me down on my couch, started giving me a blowjob. It was probably good... but I couldn't enjoy it. Every time she lifted her elbows to do something with her hands, I got a blast of stench. This was not the B.O. of a healthy girl. This was pestilential. Horrific. I couldn't take it. I then did something no man should ever have to do- I faked an orgasm. And my dick was in her mouth at the time, which made her ask the obvious question: Okay, so where...? I made up something about jerking off before she came over, and awkwardly sat around, making it obvious that no further sexual acts were going to happen. My dick, my best friend in the world, performed beautifully by immediately losing all hardness. It wasn't difficult- I think my eyes were tearing. Between my act of "oh gosh this never happens" and my dick's wonderful flaccidity, I managed to convince her that I was out for the count. She left and I febreezed the living room. Never again.
Worst is when I hooked up with my roommate's girl's friend. We didn't have sex just fooled around. We were drunk off our asses and I accidentally bit her lip in my exuberance. It wasn't to bad at the time and we kept going after it stopped. She gave me a blowjob and I didn't give her the curtsy tap. I exploded in her mouth and she backed off and had one of those, "you son of a bitch" look in her eyes an instant before she started coughing it all back onto my chest. She wasn't sorry but she still cleaned it up. We fooled around a bit after that and fell asleep. Sometime during the night her lip opened up and she bled a ton on her pillow and the sheets. She woke up first and dipped out way too embarrassed to face me in the morning. My roommate lives and dies by these situations and told everyone I had eaten her out on her period and left hickies on her ass. The girl had told his girlfriend the real story to begin with. Just some random totally untrue gossip he does for fun. I had to call him on it in front of a group of our friends before he came clean. He's a little shit. Best, another blowjob only story. Came from this ghetto ass girl I had been talking to from my work. One night after work I drove to some random neighborhood to park, so so classy. It was like that skit from Biggies Small's album. She was hesitant and kept claiming she never did it and didn't know if she was any good at it. We made out for a few minutes and I rubbed her crotch for about ten seconds before she said, "Fuck it I'll do." My oh my could she suck a dick. Had the head twist and opposing hand motion down and everything. Sucked me off in thirty seconds flat. Being some sort of fucking moron I never hooked up with her again. We still talked but I got a new job a few weeks later and stopped calling her. Part of it was me being young and stupid and the other part was me not wanting to get serious with her which is what she really wanted. I found her on myspace last year and came close to hooking up with her again. But she was married, claiming she was in the middle of a divorce. Her baby daddy found the myspace messages and she hasn't talked to me since. Probably a really good thing I didn't hook up with her again. Ghetto girls with tongue rings can suck a mean dick.
Two come to mind. First was the night I lost my v-card. Now we were both virgins and a bit retarded, and we didn't have experience to realize that: 1. I have a somewhat larger-than-normal dick and 2. She might have had the smallest vagina in the world. So, we're going at it and I finally shove it in (with no lube or anything) and am greeted with the best feeling in the world. She, on the other hand, couldn't handle it and after about 20 seconds of thrustin' she told me to get out. I do, we lay there a second, she sits up and says, "You broke my hymen you asshole." Probably the best thing anyone has ever said to me. We're still best friends and that story gets brought up a lot. Now, that story was only a bad experience because I never got to finish inside of her (she blew me after because she felt bad), but this next one was the absolute worst. The girl was a sort of random, I kind of knew her from a few parties but I'd never brought her back to my house. We start hooking up and she goes for my dick, which at the time I was definitely okay with. This sensation of excitement was immediately replaced by a new sensation, one of WHAT THE FUCK IS GOING ON WITH MY DICK WHY DOES IT HURT I don't know if it was because of the size of my dick, the size of her mouth, how bad she was at blowjobs, or a combination of all three, but that was the motherfucking most toothiest blowjob I've ever gotten. She didn't even get her mouth over the tip, she was basically just gnawing at the head the whole time. After about 10 seconds of that I was like "no fucking way," made her stop and told her goodnight, after which I promptly passed out.
Worst: (Shitfaced) Girlfriend hurling on me mid-blowjob. Best: Same girlfriend (sober) giving me head to make up for it. I saw God. And he was jealous.
I think my worst experience happened in high school, when my best friend who happens to be a girl and I decided we were bored one afternoon and decided to fuck. It was just...awkward. It was like I was kissing my sister, sooo weird. That story comes up from time to time and we always get a good laugh out of it. My best was with my last girlfriend. I was living in an old house downtown at the time and the A/C didn't really work very well. We had come home from a long night of drinking, hit it and promptly passed the fuck out. Well sometime in the night I guess I was ready to roll again, because when I came to, we were in mid-thrust. I call it sleep fucking...don't know what the rest of you call it. Well after a good hour or so of that, the room was so hot we were both absolutely COVERED in sweat. Sweat was pouring off of my head and face so much, it looked like I was raining on her. When I finally finished, I was absolutely spent. Rolled off of her onto my side of the now swimming pool of a bed and we kinda laughed about how hot that shit just was. Hell, she's married now and we STILL talk about how hot that shit was.
Worst: I really don't remember the reasoning for her doing, and before any cheese dick jokes I'm cut, clean and never had any complaints. Definitely before any fat jokes, this chick was a 7 on the body scale, huge tits, blue eyes, blond hair... but a 1 in the brains department. My senior year I had the obligatory freshman girl friend for awhile, who decided she needed a piece of candy in her mouth while sucking my dick. Not just a little piece either, like a Altoid or Jolly Rancher, this girl wanted a Reeses peanut butter cups. She'd eat a couple of them while going at it. Her family was poor, so I think that might of been her way of being the cheapest date of all time. Best: Probably one of the reasons I divorced her too, but my ex wife. I got the single greatest blow job ever from that woman, and have no idea where she learned that shit after four years. It wasn't one of those where it was 30 seconds and you couldn't hold it back any longer either, she was teasing me like a mother fucker. Either she was a cheating whore like I figured, or it was her new gay guy friend giving her pointers. I wasn't taking any chances.
This used to be a common problem for me, and is sometimes still is if I have to use a condom. From 2005-'07 were my best years in the hooking up department; every few months there would be a different woman. However, those were also the years of my heaviest drug use: I was usually so high on Darvon that you could have slammed my cock in a car door and I wouldn't have felt it. If it wasn't Darvon, I always had Valium and Xanax on me. Some of my friends called me Mr. Medecine Cabinet back then. I'd say out easily half of the women I have been with, I couldn't cum. Some of them were too fucked up themselves to notice, others were weirded out for some reason. Maybe they thought I secretly didn't like them or something, or maybe they thought there was something wrong with me. I don't know what the big deal is, I was able to get them off (unless they were faking). If I ever failed to get my ex-wife off for any reason, she would throw a big tantrum: yelling at/berating me, banging on the walls, the whole nine yards. Usually I would bring her off a few times every time we would have sex, and I guess she got spoiled.
FOCUS: Worst sexual experience? Do I really have to rehash it? My only sexual experience. Cliffnotes: She sat wrong and nearly broke my dick, and still expected me to perform. I'm sorry, but I do not have a huge penis - far from it, actually. Bruised dick, pissed razor blades for +- 1 week, etc. Pretty unpleasant. As far as I'm concerned, sex is still completely overrated. Still never gotten head. And I'm now 28 and now longer looking for it and couldn't give a fuck if I get laid again, ever. ANTI-FOCUS: I'll take computer games and music (and alcohol, if that's included) over sex. That's just how it is.
Worst: His dick never got completely hard. We both suspected that he had erectile dysfunction, but he was too embarassed to speak to a physician about it. In order for us to have sex, we would have to do missionary and I would have to keep two fingers on the underside of the base of his penis in order to keep it inside me. So...my hand was always between his ball sack and my vag during sex. Talk about awkward. Cut to senior prom: We've folded down the back seat of his Ford Explorer, and he starts heaving his body back and forth on top of me. My back is chafing against the rough fabric, he's throwing his body at me and making these loud "HUH! HUH! HUH!" noises because he's breathing so hard. His facial sweat is dripping onto my meticulously applied makeup, and I'm so drunk that the thrusting is making me nauseous. I'm concentrating on swallowing my vomit back down and then I realize that both of my hands are visible--uh oh. I sloppily reach between my legs mid-thrust to put my hand in the required position....and then I find out that he isn't even hard. His penis is completely flaccid, and he's just slamming his limp dick into my crotch area in crude mimicry of sex. I start to inch upwards away from his thrusting, sitting up on my elbows in the process...and then he cums all over himself! To add insult to injury, he puts his sweaty face into my satin bodice and passes out! I was fucking pissed. Seriously, why the fuck did I even need to be present for that!? I am a little ashamed to admit that I took a flip flop and slapped his face with it until he woke up and drove me home, but whatever. He SUCKS. Best: He was super talented in the sack...in fact, I don't think I've ever fucked anyone since who could do what he did with his dick. He gave me my first orgasm, my first multiple orgasm, and taught me almost everything I know about how to get myself off. Hands down, the best sex I've ever had was the first time I had a multiple orgasm. He started off slowly, and then we fell into a great rhythm. You know, the kind where you don't really have any conscious thought...you're just moving together and everything just feels so good that your brain stops. There's a slight sense of hurry, because your body feels that something awesome is building up and up and it's just around the corner. It's almost animalistic, and it's so goddamned hot. Anyhow, that mindless amazingness lasted for forever--until I started to cum. It was a great orgasm, one that started deep in my pussy and rolled upward and engulfed my whole body in waves. But then it just didn't stop...I kept cumming. I was grasping his ass and thighs and pulling him harder and harder into me, and I think I was screaming in the beginning but I'm not sure. It finally subsided into little quivers, but since I was still cumming I told him to keep going. We kept going gently for a while, because I was still having these baby orgasms every few seconds or so. And then I came again, followed by little aftershock-y orgasms. And again. And again. And again. My leg was twitching uncontrollably, my chest was brick red, and my thighs hurt from being spread open for hours on end. He told me he'd go as long as I wanted to, but he was tired and wanted to smoke a bowl...so we quit. A very anti-climactic end, but I don't know that we would have stopped unless my vagina broke or something--it was that good.