My Wife Emilia The Ugly Duckling

I have gone to school with my wife Emilia since we where in grade school. She was never ugly but she was a red headed freckle girl with long hair. Pippy long stockings type. Was never mean to hear but wasn’t really super nice. As we grew up and got into girls around the 7th and 8th grade we dated or where a couple. She had a great sense of humor and she started to get cuter. Not going to lie she had a nice look to her. Still other girls were more developed. High school came and we hardly saw each other. Graduated and never looked back went off to school out of state. Absolutely hated it and came back a year later. Finished up at state which was very close to home and got an apartment and a big boy job. Out with friends and one evening I’m walking back from a bar we had been at and I see this red headed freckle girl with her hair in a pony tail glasses sitting at this diner by herself. She was very pretty very pretty. She was in sweats and a sweatshirt. Sitting having coffee reading a book. Then I realized it was Emilia my old class’s mate. I let my friend go on with out me and I went and said hello. She recognized me we spoke for a while. All the while my where blowing up my phone we sat and talked. She was still the same Funny shy girl. Had gone to state graduated still lived at home. Had friends but they where no where at rowdy as mine. I was absolutely blown away by her. She could have been a square or gained 200 lbs she was absolutely beautiful and we just connected. I spent the evening with her walking her back to her parents house and we kissed that was it. First on we text called each other as we where best friends. I told her that I’ve ate don’t be more then friends and pretty much spilled my guts to her after a few times of going out. She felt the same way and we became a couple. Oh and she has a killer body. Nice big rack a slim waist and an ass. Pale skin and some freckles but gorgeous. Never rushed her into anything we spoke about sex and she asked if I really liked her. I said yes she asked if we where exclusive I was honest and said I hoped so. She just let it go and a few weeks later she spent the night. She was a virgin most she had ever done was a handy and let a guy feel her up. She said she was close with a guy once but caught him cheating and dumped him. So she was always nervous and she was a bit shy. From the first time she spent the night I absolutely knew I never wanted her to leave. More and more she spent more time with me. Her parents where not completely happy she was moving in. It was almost a year and a half of not making it officially. She mentioned that her dad was not super happy. Kind of strong beliefs kind of guy. I totally understood so I went and bought a ring that I could afford at the time. Went out to dinner and while at the same cafe it all started I popped the question and she screamed yes. The best decision I ever made plus she still hot as fuck and after 2 boys she still a little adventurous in the bedroom. Always keep an eye on the ugly duckling is my point

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Anonymous

by Anonymous on Sep 23, 2025 at 8:37 AM

I have noticed in my lifetime, plain Jane’s and ugly ducklings, are usually the best fucks out there.

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Anonymous

by Anonymous on Sep 30, 2025 at 1:59 AM

Discovered early on, that the best way to get my perverse needs taken ae of, was a lady who would not normally be very attractive to an averagely good-looking male, older, plump, heavy glasses, untidy hair, let's say, and unsure of herself...plied this one with alcohol, got naked, pulled my rubber bondage-bag over my head, and shrugged it off my shoulders so it fell to the floor, enveloping me completely, then said "tie it at my neck and waist, then you can do ANYTHING you want to me, or with me..."

Her uncertain laugh quickly changed to an evil alcohol-boosted chuckle, and she said "Like ...this?" as she wound conveniently available thin rope as suggested, pulled it tight with surprisingly vicious effort, then demanded snidely "Anything? Like, leaving you like that, and going to a movie? Just joking,,,actually I'm not going anywhere this weekend, and neither are you! So you better get serious about keeping me amused, don't you think?"

She unzipped the nylon zipper at my crotch, pulled my already aroused package outside, and began to smack my balls harder than I was okay with, and wanked me clumsily but enthusiastically, until I began to writhe and squirm, eventually spraying her with generous white slime at which she exclaimed "Yecch! Oh man you're in trouble now! That is SO disrespectful, so I think I should stop you doing it again, despite finding this a very attractive handful...we've got all weekend, maybe more, for me to explore limits and limitations! I know you don't find me attractive, but this way you can just fantasize about some cute chick or another, and I'll do lots of this, and maybe even lay you down, get on top, and help you to be inside me, like couples do, I understand...anyway you're not in a position to argue, and I DO like that!"

We got married a month or so later, and have been together now for years, always to her consistant spedification, and duration, as she welcomes me on my return home from work with the greeting "Why don't you slip into something less comfortable...?" Which I always agree to do, often without any dinner, other than the occasional energy bar, which will pass through the small nylon zipper across my mouth, after her comment "Stand still while I "finish you off" so to speak!" Creating an involuntary shiver in me, especially on a Friday!

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