Bitter and on the rebound, but lucked onto a winner [M29, F31]

It started as bitterness on my part. I had had yet another relationship crash and burn and was feeling like taking my frustration out on the entire female gender. Not physically, but mentally. Emotionally. And even though I wanted to do this, I knew how wrong it was to let my anger at previous girls taint future relationships, so I figured posting some rant-type diatribes on Craigslist would be a fun (and safe…and not particularly malevolent) way of going about it.

So I wrote a series of posts, sort of "Open Letters To The Women of Southern California", and put them on CL in the M4W section. Summed up every shitty relationship I've had since I was 14. Got a LOT of hate mail. A little more "God loves you" mail. A few "right on, brah!" type messages from dudes. And a VERY few e-mails from women telling me that as much as they hated me for being such an asshole, they did admired my writing.

I struck up a number of e-mail dialogues with the women of this last category, and after a period of online stalking via MySpace, Friendster, and Facebook (this was several years ago…), discovered that all but one of them were fat ugly single mom divorcee English teachers. But there was that one…Charlotte.

Charlotte's pic on MySpace was a headshot of Tina Fey. This did not impress me as she was clearly ugly enough to post a famous person's pic instead of her own. Still, though, our e-mail conversations did pique my interest. I was less bitter after three weeks of online flirting and dangerously horny, so I decided to break down and meet her for a drink. Note that this was the first time I'd ever met anyone online in person.

So I go to our planned meet-up spot (my favorite local dive bar) and wait at the end of the bar for her for about 45 minutes…when in walks a dead ringer for Tina Fey, if Tina Fey had biggish tits and no facial scar. No shit. She really did look EXACTLY like Tina Fey, only hotter…did I mention the tits and the lack of facial scarring?

So anyway, we sit at the end of the bar and she babbles nervously until she gets a few drinks in her, at which point she calms down and we seem to really hit it off. I'm playing the good listener but she actually is pretty engaging, very smart, and an incredible smart-ass. Out of the blue she pulls me into her and slams a big, sloppy, tonguey kiss on me. It was nice. No fireworks or anything, but nice. It'd been years since I'd made out in a bar, much less on a Tuesday night in a mostly empty one. We kind of laughed about it then kept talking.

So, the bar being close to my place, and me not knowing if she was actually going to show (and as such planning on getting drunk in the event that she stood me up), I had walked to the bar. She lived far away and had driven. She offered to drive me home…then offered to come up. Who was I to turn her down?

So we get upstairs, I pour some wine, and we sit on the couch…at which point the kissy-face immediately resumes. Followed quickly by her getting on her knees in front of me on the couch and pulling out my cock. She gasped at the size of it (I'm not setting any records or anything — I just think think all women are trained to do that at charm school) and proceeded to give me a sort of Busch-league blowjob. Not bad (she was great about avoiding the teeth), but not great either. I began puling her shirt (a black turtleneck sweater) over hear head to reveal that she was wearing a tank top underneath. So then I tugged away at that. By this point my pants were completely off and she was going to town on my cock. Apparently it was just the pants that were causing the trouble before because once she had free range of me, she revealed her true level of cock-sucking skill. A stellar effort all around. Jacking me off with her hand, voraciously bobbing up and down with her head, gently fondling my balls with her other hand, making eye contact from time to time, looking at me with those dark brown eyes and those black framed glasses. It was excellent.

So as she's slurping away I know that even though it feels great there's no way I'm going to come from just a blowie, so I set about trying to get her undressed. By this point the first two layers of clothing are off her top and she's wearing jeans and a boring bra (she told me later she had no intention of coming home with me that night, so she didn't wear anything too fancy.) I unhook her bra and her tits spill out…and literally, each one is damn near the size of my head. I've never seen tits so big. I don't know what sort of sorcery that bra/tank-top/sweater combination was working because I had no idea what she was packing until they were out. She's kind of thick but not fat — just a healthy girl with HUMONGOUS tits. Impressive. So I'm fondling them, pulling on her nipples and getting some moans in response, and she spits on my cock and starts titty-fucking me. Again, this feels great but there's no way I'm going to get off like this — the positioning was weird and I was still a little in shock at how quickly things were moving along. I didn't really want to fuck her (first date, online crazy, rebound bitterness, etc.) but the couch was awkward so I suggested we go to the bedroom, figuring we'd just go down on each other in a more comfortable setting. She looks up at me from my cock, her tongue doing little circles just south of my head, and nods slowly.

We go into the bedroom, me stripping the rest of the way though she left her panties and stockings on — knee high black ones. She proceeds to put me on my back and blow my mind with her blowjob skills. Just as I'm starting to think I can come from this, she reaches into my bedside stand like she owns the place, finds a rubber, and slides it onto my painfully hard dick with her mouth, then climbs up on top of me while pulling her panties to the right and guides me into her. She rides me like that for a while and I just lay back and enjoy the view of those huge tits swaying above me.

Hating condoms and a little drunk, I'm nowhere near coming. She gets off of me and positions herself on her hands and knees, ass in the air. "Do you want me like this? I'll come really quick if you fuck me from behind."

Not needing a second invitation, I knelt behind her, lowered her panties to her knees, and guided myself into her. She was tight in this position and true to her word, after a number of thrusts she started moaning and shaking, telling me she was going to come. She shuddered to a climax and I pulled out, telling her I came too (though I hadn't). We cuddled for a bit afterward and she left within an hour or so.

So things go swimmingly for a few weeks. Still using condoms, still not coming with regular sex, but she was fun and the sex was otherwise good so I was happy. The blowjobs went from great to fucking phenomenal, with one memorable afternoon spent with her using her hands only on my balls and her tongue only on the small patch of skin just below the head of my cock, gradually working me from completely flaccid to rock hard to violent explosion over the course of 25 minutes — I came so hard that I hit the bedroom wall above my head, the pillows, and my own face and chest…all of which she licked off of me.

One night we went out for a nice dinner and as we came home it started to rain. We drank wine and made dessert at my place and just sat on the couch looking out the window in complete darkness, the only light in the room coming from a candle and the distant streetlights. It was an actual thunder-and-lightening storm, very rare for the area. Before long we were naked on the couch.

She was straddling me, rubbing my bare cock against her pussy lips, her well-trimmed small mound tickling my head. The condoms were…somewhere. "Can you pull out before you come?" she said, holding my shaft and rubbing the head of my cock against her clit. "I think so," I say, wanting nothing more than for her to take me inside her without a condom on. "Good," she says. "I just had my period so we should be safe. I want you to fuck me without a condom, and when you're about to come I want you to pull out and shoot it in my mouth."

With that she raised up slightly, still holding onto my shaft, and guided me into her cunt. The feeling of her warm, wet pussy around my cock without anything between us was amazing. She slowly ground into me like this for a while as I reached up and kneaded her huge tits with my left hand, thumbing her clit with my right.

This went on for a while, but my couch was soft and not terribly bouncy so we couldn't get much going in the way of a rhythm or penetration — the cushions were acting like shock absorbers. So she stood up and bent over the chest of drawers which was right in front of the bay window. Her arms outstretched, holding onto the chest for support, and her ass in the air, she looked back at me. "Fuck me, John. Hold my hips and fuck me hard. I want to come like this and then milk all of your come out of you."

She was tall and as such the perfect height to fuck from behind while standing, I discovered. I stood behind her, my rock-hard cock in my hand, and guided myself into her slit. The smell of our sex filled the room and make me fuck her hard, like an animal. "Faster…faster…"she whispered as I slammed into her again and again from behind. The windows were open, allowing us to hear and smell the rain through the screens. Lightening punctuated my thrusts, and the low rumble of thunder mixed with her moans as her cunt pulsed around my cock when she came.

Weak in the knees, she could stand no longer … but she wasn't done. "I can come again. And I still want to taste you as you explode in my mouth," she said, turning toward me and pushing me down onto my back. Again she took my shaft in her hand and guided it into her cunt. Soaking wet now, I bottomed out immediately and she gasped.

"Holy fuck! You're going to make me come again really soon. Can you come with me like this?" she said as she ground into me faster and faster. Feeling my own orgasm building, I grunted an affirmative reply. She was bouncing on my cock, the lightening giving her a strobe effect as her huge tits flopped up and down and she rubbed her clit with her own hand. Again I felt her shudder and moan as the thunder rolled overhead.

On the verge of coming myself, I let her ride her orgasm out, then thrust her whole body up with my hips so I could get enough room underneath us to pull my cock out. I was on my knees in front of her, my cock standing straight up and so hard it hurt. She knelt in front of me and immediately took my entire length in her mouth. I reached down and squeezed her tits with my hands as she gently stroked my balls and bobbed rapidly on my cock.

"Fuck my mouth," she said, looking up at me as she fondled my balls, then licked her pinky and snaked it into my asshole. "Fuck my mouth hard until you come. I want to milk every ounce of come out of you and swallow it down."

I let go of her monster tits and grabbed her behind the head. I began to thrust faster and faster as she rubbed my balls and fucked my ass with her finger. The feeling was intense — something I'd never had done to me before. The pressure on my prostate was mind-blowing. Her tits were bouncing back and forth and I could hear my cock sliding in and out of her mouth. Before I even knew what was happening, I could feel rope after rope of hot spunk coursing through my shaft, meeting her warm tongue as she lapped it up, my asshole spasming around her finger as she sucked down every drop I spewed into her mouth. I blacked out from the sensation for a second and fell backward. She crawled up to me, my come dribbling down her chin, and gulped down the load I had shot in her mouth, smiling from ear to ear.

Source: reddit.com/r/gonewildstories/comments/375axa/bitter_and_on_the_rebound_but_lucked_onto_a