I've had sex with four different girls, two were girlfriends and two were little fling-type things. The shitty sex has always been with the fling girls.
GIRL ONE:
Did not expect to have sex with her, ever. She's staying the night at my parent's house with me, we're in my old bedroom. (I'm 27 now, this happened... maybe 3-4 years ago? I was in-between apartments and staying with them. Anyway.) So we're in bed talking or whatever and we start making out. Then things get heavier and there's some heavy petting going on. Suddenly she's on top of me telling me she wants me inside her.
Now, this causes me pause. I'm in my parent's house, and my bedroom is located in-between my mom's bedroom and my dad's bedroom. (Long story involving several back surgeries for my dad so they can't sleep together anymore ;_; ) Second problem: My bed frame had wheels on it and my bedroom had a hardwood floor. So I'm thinking, "If we have sex, the bed is going to roll around and it's going to make noise and someone is going to wake up and hear us." But I'm horny and she's horny so I ignore this and slide on the condom. Third problem: She tells me, "You need to ask me permission before you come." Uh, what? Immediate turn-off. Maybe now I'd be into that kind of thing, but back then, no. It's too late though and we're having sex.
Incredibly lackluster sex.
She's on top. Boring. I'm on top. Too noisy. We're on our sides. Too uncomfortable. We throw a blanket onto the floor and move down there to avoid the bed. The sex is just plain bad. She's trying to make it "hot" for me so she's over-acting and it's coming off as unnatural and fake and taking me out of it. I start to panic, how the hell am I going to get out of this sex without hurting her feelings?
I decide to fake an orgasm.
I mean it shouldn't be that hard, right? My 2nd girlfriend loved the feeling of me coming inside her because she could feel my dick tense up and get super hard when I came, so if I just pretend to come and flex my dick, no problem right?
But I have to ask for it.
We're in doggy-style position and I say, "I.. I think.. I'm getting close.. can I come?" (humiliating) She tells me yes I can, I do a couple harder thrusts, go rigid, and flex my dick as hard as I can. Pull out, yank the condom off and chuck it in the trash as fast as possible, and she completely falls for it. We clean up and get back into bed and she asks me to fucking rate her. She wants to know how she stacks up to the two other girls (at the time) I'd been with. I told her it's impossible to rate her because everyone is different and has different styles but sex with her was enjoyable and she did a good job? This satisfies her and we go to sleep.
BONUS: A day later she wanted to have sex again but I made up a story about not being over my ex yet, so she tried to give me a handjob instead. It was so bad I kept losing my wood. I told her I shot a blank to get her to stop. Once again she bought it. I am an amazing actor.
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GIRL TWO:
This is the more ridiculous of the two stories because of how badly I fucked this one up for myself. This was slightly more recent, maybe a little over two years ago.
I was kind-of dating a coworker, this super hot latina girl. We'd made out a few times, I'd fingered her a few times, it was all awesome. One night we're out at a bar, she gets buzzed and asks me to take her back to my place. (Alarms go off, I HATE dealing with drunk girls and I have strict rules about this because of events like this one). So we go back to my place and start watching Back to the Future. We start making out. She gets SUPER horny, is asking me to bite her neck, her nipples, she's tearing off her clothes, taking off my shirt, unbuckling my belt. She's naked on my couch and asks me if I want to fuck her. My brain shouts "NO! NO you don't she's buzzed and you're sober you do not want to fuck her right now!" But you can't tell a hot, naked, horny girl no when she has your dick in her hands and asks if you want to fuck her right? Ugh. "Yes?" I respond, and she looks at me like, "Well what are you waiting for then?" I go, "I'll grab the condom?" and she tells me to hurry. I run into the bathroom, grab a condom, look at myself in the mirror like "This is a bad idea" and run back to the couch. I try to hop out of my shorts and I twist my ankle. I clumsily fall onto the couch and get the condom on, she pulls me into her. I thrust a few times before I realize, my couch is HORRIBLE for sex! It is way too soft, it's not long enough, we are sinking into the cushions, I can't get any kind of leverage to properly thrust. I pause and ask if we can move to my bed. We do so and I realize my goddamn windows are open, meaning everyone else in the apartment complex will be able to hear us, but I have no time to close them. We get back into it. I'm inside her again, start to thrust, and she hits her head on the goddamn wall. I offer her a pillow, panicing, because that's the shared wall with my neighbor. At this point, I am properly stressed out. My foot hurts. The windows are open. She's hitting her head on the wall. She's not really making out with me or doing anything to keep me into it, expecting just the sex to be enough.
So my boner dies.
I pause. I try to make it go back up, but it's asleep for the night. I look at her and say, "Uh... I... my... I lost my.. I mean, I didn't come too quick, I just, it.. went away..?" and she looks at me like, "Are you fucking serious?" She gets up and goes into the bathroom to clean up. I flip out, I've had issues coming before with girlfriends but, they were girlfriends, they're understanding about it. I'd never lost my goddamn boner before, and with someone I was barely casually dating. She comes out of the bathroom, gets dressed, I try to apologize, and she leaves.
Fucking terrible.
We still talked and hung out after that, I was super insecure about it but when it finally came up (lolz) a week or so later she said it wasn't a big deal. I even still fingered her a couple times after but we never got to the sex level again. She moved away and when she visits she'll get drunk with friends and chew on my ear and tell me how horny she is for me but her friends always "protect" her from me and I've never gotten a chance to make it up to her.