I’m a settled down, married man now but back in my late teens and early 20’s I had a knack for finding the girls that wanted to let their inner slut out. I was always the geeky guy; into anime and comics more than sports so I think that’s what made me so approachable once I messed around with the right girl or two.
I was always more of a giver than a receiver and so I would practice my oral skills on the odd Jesus freak in the class that was saving herself for marriage but the Bible said nothing about your mouth! (Or ass for that matter…)
Then there were the girls that were so sure they’d die old maids for one reason or another. I made it my sworn duty to pump up their confidence by.. well.. pumping their cunts.
Maybe they weren’t as conventionally attractive as others or chubby, or had a different body shape than an hour glass. (Pear shaped chicks with huge asses happen to be my thing!)
Which brings me to this one girl…
We met online, like ya do; and it seemed like any other other blind date. I had come out of a bad break up and she was trying to start her whole life over.
Let’s call her Maggie.
Maggie was bigger than most girls I dated and/or fucked in the past. Her bob haircut made her face look all the more round and her glasses were not a great fit. She had obviously taken very strategic selfies for her profile but it’s my duty to please that booty!
She was short; almost dwarf short. I’m no Andre the giant (in more ways than one) but it was kind of funny how I could rest my chin on he top of her head while standing.
Her breasts were 40 DDD; the first time I learned cup sizes could be tripled. Her big tits rested on her round belly and behind her was a great big ass that could barely be contained by her yellow floral dress.
We were trying to take it slow but for some reason the mood, and alcohol, was just right. We were getting along great; talking about college majors and the like.
My slut sense was tingling and I was betting that sense she was out of the dating scene a while and going back to school, she probably hadn’t gotten laid in a good long while.
I leaned over to kiss her.
It completely took her off guard and I could feel her tremble a little.
When I pulled away she smiled and said
“kiss me again. “
Cut to back at my tiny studio apartment.
We were making out heavily. Our tongues were were in each other’s mouths and seemingly just as horny as we were. I was massaging one of her tits with one hand and stroking her thigh with the other. I had already unhooked her bra and we were reaching for each other’s clothes when Maggie paused and said
“we should stop…”
“That’s perfection fine. I don’t want you to feel uncomfortable “
“It’s not that… you’re making me feel great; it’s just that…”
I could see her self confidence was not only lacking but it was severely damaged.
She looked down and then back into my eyes again.
“I don’t want you to think I’m an easy whore..”
I don’t know what possessed me but
“If you want to be treated like a lady then that’s what I’ll do. If you want me to treat you like a cheap whore then that’s what I’ll do. I won’t look at you any different. “
As soon as those words left my mouth I knew I had fucked up. I just knew that was gonna be the end of it. BUT Maggie smiled her sheepish smile and then pulled her dress up and over her head. She wasn’t wearing any panties and was clean shaven. She took her limp bra off her breasts and let it fall to the side of the bed with her yellow dress.
“Treat me like a lady tomorrow. I’m your dirty slut.”
Now folks, I’ve dated a couple of chicks that claimed they liked to be dominated. They had nothing on Maggie. This plump, fat little woman that looked like she’d be a librarian or school counselor.
I cupped her cheek with my hand and she whimpered. So I wrapped my hand around her throat and she moaned like I had put my dick in her.
At that moment it was like something primal went off in my brain. I licked her cheek. She moaned and shuddered. Removing my hand, I stripped my shirt off and grasped her throat again.
“What are you?” I asked sternly.
“Your slut.” She whimpered.
“That’s right Baby Girl. “ the name just came out. She liked it very much.
I pinched a nipple with my free hand, causing a sharp moan to escape her lips. I twisted it and she threw her head back.
“You love that don’t you Baby Girl?”
Maggie nodded fiercely. “Yes sir!”
I twisted and pulled on her nipple hard, making her convulse and gasp.
Without thinking, I started to choke her. Her hands flailed around a bit but not once did they reach for mine. She spread her thick thighs and started rubbing her clit and fingering herself with her middle and ring finger.
“What do you think you’re doing you fat slut?!”
I let go of her throat and nipple and she pulled her hands from her soaking wet pussy.
Gasping for air and coughing. “Sorry sir!”
“Let me show you how it’s done. “
I had no idea what I was doing but I was going to go for it. I had seen my fair share of “extreme” porn but still had no real clue or technique for this. I pushed two fingers into Maggie, absolutely no surprise, she was gushing and they slid in easy. So I added my ring finger and my pinky.
She opened her mouth suddenly but no sound came out.
I tucked my thumb in and formed a cone shape with my hand and unceremoniously pushed hard inside her.
Maggie groaned loudly and her body went limp. She had came. Her eyes rolled back and her mouth fell open.
“More Baby Girl?”
With my hand inside of her I attempted to flex my fingers and play with her cervix and g-spot; using my other hand to press down on her groin to cause her filled pussy to feel even more cramped.
This was the first time I had ever fisted someone and Maggie was the only person I’ve ever done it to.
I slowly pushed my hand in and out of her. Her cunt squished as I worked my fist.
“What kind of slut let’s this happen to her on a first date?!”
“Me sir! I’m sorry sir!”
“You’d let just anyone ruin your cunt wouldn’t you?”
“No sir! Just you sir!”
“Bullshit”
She whimpered while I fisted her harder. “I’m such a slut! I’ve needed this so long!”
I slapped her with my other hand. “I bet you want even more. “ I was honestly out of ideas and it seemed like the next logical step. Perfectly logical.
“Yes! Please ruin my cunt!”
And with that; I pulled my hand out just a bit, letting the thumb pop out. Maggie moaned as I lined up my hands in a praying pose and pushed both in. I was thinking it would be much harder.
Nope.
This may had been my first rodeo but this heifer was well ridden.
Both hands slid in with relative ease. I would glide them past each other; each time Maggie would shudder and seemingly orgasm again and again.
I couldn’t believe what I was doing. I couldn’t even believe my pants were still on!
I pulled both hands out of her and shoved a couple fingers in her mouth. She licked and sucked on my fingers like a new born calf.
With my other hand, I got my belt loose and the button undone before awkwardly pulling off my jeans and boxers and let them lay on the bed.
“Yes sir! Fuck me please!”
I squeezed her big tits. “Oh I’m going to fuck your ruined cunt but I’m going to fuck you like the dirty bitch you are!”
I would like the record to show I have never spoken to a woman like that before.
…
Ok only once before and it was also before fucking her.
I grabbed her fat thighs and flipped her over. She raised her huge ass up in the air in anticipation.
She waited.
I still hadn’t slid myself inside her. She was about to look over her shoulder when I took my belt and wrapped it around her neck like a leash. I pulled tight and caused her to arch her back. Only then, did I thrust inside of her.
While my balls slapped against her clit, I squeezed and slapped her ass and occasionally drag my nails down her back. Maggie’s big udder like tits swayed in rhythm with my hips while her fat ass jiggled.
I was completely soaked by her pussy. It didn’t matter what I called her or said; she loved it.
Knowing that my neighbors were probably awake I went for broke. I took my belt off her neck, doubled it up and swung down at her big ass. She cried out over and over again but followed up with “thank you sir!”
I could feel myself coming to an end and so could she. She bucked her ass back into me.
“Baby Girl, you want this cum?”
“Yes please!!”
My little head was all for it but not wanting to find out how Maggie would be as a mother, I followed up with “you don’t deserve it you fat slut!”
“No sir! I’m sorry!”
I pulled out and flipped her onto her back. She was a plump rag doll at this point. Just a fuck toy to use. I pulled her half way off the bed. Her head hung back and her mouth was agape. I squeezed on her big tits and fucked her mouth with all the energy I had left. After the first couple pumps I was filling her throat with cum. (Or people if you live in Alabama)
Believe it or not we continued to date like normal people who happen to have a sex life filled with insults and abuse. We went our separate ways only for her to marry my cousin. When we reconnected, we-uh.. reconnected a few more times.
Source: reddit.com/r/gonewildstories/comments/bubjsa/remembering_my_past_fling_and_first_time