I’ll try to just get to the nitty gritty. I’m a successful, hot, alpha (in my opinion) male in Northern California (near San Francisco Bay Area / Oakland) who is very picky. I posted on a dating site (won’t specify because it doesn’t fuckin matter) what I’m looking for. I wrote a lengthy essay about myself and included that I did not want a chic who is apart of the itty bitty titty committee. I explained that men of higher status like myself who are successful, hot and have a big cock DESERVE women with bigger tits (I like at least a C cup but no bigger than Double Ds). It’s typically the beta males who don’t mind a chic wit smaller tits because that’s really all he can get. I’ve had so many women that had beautiful big breasts there’s no reason I would downgrade. I then made a comparison with women and bigger dicks. If women had the CHOICE, every single one of them would choose a guy with a bigger cock.
But this one redheaded bitch about 5’2 and 103 lbs wit A cup tits messaged me. She was somewhat successful herself (in Finance), age 28, we’ll call her Elizabeth. She started by telling me that I was somewhat of a jerk and an asshole for saying that right out in the open and I probably wouldn’t attract ANY woman with my cocky attitude. She also said that dick size doesn’t matter to her, though she admitted she never had bigger than average, but it didn’t bother her one way or another, because skill is all that’s required to satisfy a female. I wrote her back and told her that I’ve been with so many chics with C cups or bigger that it would blow her fuckin mind and when I do fuck chics with small tits than that (which is very rare, she has to be pretty hot in the face and body), I’m usually an asshole prick in the sack with them.
She responded saying I was such a dick and good luck in my search. I responded back saying she had walls up because she secretly wanted a higher status guy like me, which is why she reached out to me FIRST. Then I told her that I can PROVE to your lil ginger ass that DICK SIZE matters too! Then you’ll understand the reverse role here. When a guy experiences bigger tits, it’s the same as when a chic experiences a bigger cock. She won’t wanna downgrade just like he won’t wanna downgrade. I forewarned her though that because she has smaller tits (as well as her initial bitchy attitude), I’d most likely be more of a rough prick in the sack wit her. haha
I didn’t hear back from her until the next day. She started out by putting “LMAO” oh really? You’re really confident and cocky aren’t you? She then says well let’s make a deal then, because I don’t even believe you’re as big down there as you say. I’ve never had a guy I couldn’t wrap my hand around his cock and touch pointer finger to thumb, and none of them were very long either, so if I can wrap my hand around your cock and touch index finger to thumb, then you’re not as big as you claim and I’ll also measure to make sure you’re really 8.5 inches long. If you lose you have to take me on your next vacation trip (I mentioned in my profile that I travel everywhere because I’m successful). But if I win, then she’ll let me fuck her and prove her wrong about the size issue.
Even though her small tits initially turned me off, this was getting exciting and since I knew I was gonna be a rough asshole in the sack wit her anyway, I upped the ante and said if I win, then I wanna do a roleplay scenario with her. I’ll get to what that was later. I send it back to her and she agrees and then asks to meet me at a coffee place first to make sure I am who I say I am. So we meet and she did her makeup to the nines and wore a sexy black outfit that showed off how skinny she was. She had a good lookin face, at least a 7.5 out of 10 I’d say. Of course, her tits were super small but they looked a bit bigger than her pics (she was definitely wearing a tight pushup bra to trick me haha). Being the bold prick that I am, I immediately say “DID YOU STUFF YOUR BRA WITH TISSUES OR ARE YOU WEARING A PADDED BRA OR PUSHUP BRA? THEY LOOK BIGGER!”
She looked shocked at first and says UGH… I SHOULD’VE KNOWN YOU’D RECOGNIZE THAT! She sort of smiles and then looked down as if I humiliated her. I then said fuck the coffee, let’s go back to the hotel so I can prove I win this deal! She said she wanted to get to know me a bit first, but I straightout said “EH… REMEMBER YOU AREN’T EVEN REALLY MY TYPE WITH SMALL TITS, WHAT’S THE POINT?” On the way to the hotel, she told me that I was the first guy with enough balls to flat out tell her that her small tits were an issue. Every other guy assured her that small tits were fine, but she always had an insecurity around them, no matter how many guys commented that it was fine. She always felt inferior to women with bigger tits. She then throws a shocker in there, that the DEGRADATION kinda turned her on and that she knew deep down most guys would choose a big breasted woman over her if given the chance, so she appreciated my honest even if it was brutal.
I also mentioned that if (when) I win that deal, we’d do a rough fuck roleplay. I had tried this a few other cosplay / roleplays in the past with a few other chics (only tried this particular one with one other female). She would be a Russian spy, (the other one I did this with had a long black trench-coat with no bra and only panties, with red heels on), but her tight black outfit was good enough for the roleplay that night. I was a US Politician on an important phone call. She is hiding in my closet listening in. She accidentally makes a noise and comes running out in heels. I catch her and then basically fuck her any way I want. It was basically a rape roleplay.
She agreed and said she was confident she would win because she has pretty long fingers for her size (I compared them to mine and while they were decent for her height and weight, I knew she was gonna lose even before we got there haha). I made her think she had a chance at winning though. So we get there and I tug real hard on the middle part between her tits of her dress. Her tits deflate because she was wearing a padded type pushup bra. She looked embarrassed and I said I had a hunch you’d try that shit. So she asks how this works. I said I needed to be fully erect, and then she was allowed to have a firm grip on the cock (but no super squeezing). So I go in the bathroom and get it erect. I come back out and she’s laying on the bed. I lay next to her and I whip it out. She goes DAMN YOU WEREN’T LYING! YOU ARE DEFINITELY THE LONGEST DUDE I’VE SEEN!
So I say okay let’s do this shit. If you can wrap your hand around it (which I knew she couldn’t) then you win. She tries to firmly wrap it around and she couldn’t even barely touch middle finger to thumb let alone pointer finger to thumb. She said “DAMN YOU SHOULD BE IN PORN!” I said I told you I was a cocky prick for a REASON! She basically told me it was gonna fuckin hurt and to go easy because she’s super tight. She admitted that one of her girlfriends bought her a dildo around my size (8 inches and it wasn’t even as thick as my cock) and said she tried it once and it barely went in halfway without it hurting. I said I would (with crossed fingers in front of her face). She said I was an ass. She said if we’re gonna do this she would have to smoke a cigarette first (she was an occasional smoker). I said how about you smoke a cigarette while you’re the Russian spy in the closet while I’m on the phone. She agreed.
So we do the roleplay and she comes running out. I grab her and throw her on the bed, strip her naked, spank her ass and start degrading her on how small her tits were. Her pussy was drenched. I then put her in doggystyle position with upper torso laying on bed and feet / legs standing on the ground. She literally was the tightest chic I’d ever fucked so I could barely get in at first. She definitely had a shallow vagina and I was hitting her cervix because I could barely go in a bit past halfway before it bottomed out. She said it fuckin hurt like crazy over and over but thankfully I had it written in a previous conversation on the dating site that if she squirmed and said it hurt, I would fuck her harder (AND I DID). I put my hand over her mouth and kept fucking hard whenever she said FUCK or that it HURT.
Then I fucked her in the ass. She was moaning like crazy. I flipped her over and went inside her while fucking her in the ass with my fingers at the same time. She kept moaning and squealing that I was so fucking huge and thick. I kept degrading her over her small tits and telling her how worthless she was to a high status guy like me. At that point, she started shaking, her legs were going nuts and she said she was having an intense orgasm, over and over and OVER. Every time I would go as deep as I could, she would wince in pain and say FUCK… SHIT… and would put her hand up against my stomach to sort of push me back but I’d start fucking harder at that point. I was about to cum so I pulled out and stuck it in her mouth. I told her to swallow it like the good little worthless whore that she was. She did. We fucked a few more times that night for good measure. She said she never (not by herself or with any other guy) had as many orgasms as that, and never had intense ones like that either.
She said the degradation made her orgasm the most. She admitted that I turned her on like crazy and I was right about the size too. Even though it hurt really bad, she said it made the sex more intense. Every time we fucked my cock was so big for her that it hurt for her. She never got used to it. A few months later, she told me that she had sex with another guy who was average and even though it was big for her, it wasn’t as satisfying as mine. I’ve turned many women into SIZE QUEENS just like her as well. This is just one of the more extreme of my stories. Amber was my little fuck toy up until Summer 2017 before she moved to Portland. She still texts me telling me that she still hasn’t found a guy like me up there yet and can’t wait to travel back to the SF Bay Area so we can have fun again. I remind her that she NEVER WILL!
Source: reddit.com/r/Erotica/comments/85ad49/true_erotica_story_it_started_when_i_expressed
I think this is hot
You seem like an asshole tbh