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Preface: Upon seeing the success of my last story (which I will follow up on), I thought I would share a sexy story about someone else besides Ashley in Candace's family.
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Before I ever dated or knew Candace, I knew Leona.
A few years ago, I left a yearlong relationship and wanted to fuck around a little. I downloaded Tinder just for fun.
Some background: I'm 31 now, but I was about 25 at the time that this happened.
I matched with a couple cute chicks and talked for a bit, nothing clicked. Then suddenly I matched with Leona, 38.
Latina with dark hair held up in a bun. Very full figure BBW. Huge ass and breasts, by the looks of it.
Over the course of the evening, I found out a lot about her. She was a single mom with two kids in middle school. She also loved Star Wars and baseball.
Leona was looking for a no-drama hookup. She felt a relationship was too complicated at her current moment, but it had been years since she had been fucked. Even longer since she had been fucked good. Her words, not mine.
We decided on meeting Friday morning for coffee.
"Tim?" A voluptuous woman with long black hair approached the table. She wore a white low cut top and dark leggings that accentuated her massive thighs. "It's nice to finally meet you."
I rose from the table and we hugged. "It's nice to meet you too, Leona. You're so pretty!"
Leona smiled and covered her face with her hand. "You're making me blush."
Leona looked better than in the pictures. Her breasts filled out her shirt very well, and I could see a black bra through the semi-transparent white fabric. Leona's thighs jiggled as she walked.
The plan was to meet up, talk for a bit, and then go back to her place and fuck. We were both clean and weren't worried about the risk of pregnancy, so we agreed to do it raw.
I ordered a coffee and Leona got a chai latte.
"So, you said you work around here... Do you like working downtown?" Leona sipped her chai. Milk foam glazed her plump upper lip, and she licked it away.
"It's the best. Everything's within walking distance. I'm surprised I didn't know about this place. Good suggestion."
Leona smiled and took another sip. "This spot's my favorite."
I could tell by her eyes that she was excited. She looked ready to get fucked on the table in the coffee shop.
We finished our drinks and walked to our cars. "Just follow me, I live around the corner."
I obliged, and a few minutes later found myself pulling up to an off white townhouse complex. We parked and I followed Leona inside, my eyes stuck to her juicy, shaped cheeks.
Her house was dark on the inside, the curtains drawn. She led me to her bedroom.
Leona planted her ass on the mattress and looked up at me. The bed sank a little under the weight of her fat butt.
"So this is my house," she said playfully. "Welcome. Sorry if my room's a bit messy, I never really have guests in here."
To me, it looked basically clean. Some clothes on the floor. The bed wasn't made. Shit, it still looked better than my room. "Not at all," I said. "It's completely fine."
Leona gave a sultry smile and motioned towards the space next to her on the bed. "Come, sit down."
I sat down and put my arm around her back, feeling the heat from her curvy body radiating out. She seemed a little nervous, but she smiled through it all. "Soooo... do you do this a lot?" She asked. "Hook up with strangers from the internet?"
I could tell Leona was just trying to break the tension, because we already talked about our past experiences over text.
Still, I blushed. "No, actually. But when I saw you I couldn't resist."
I put my hand on her leg, feeling the sleek fabric of her yoga pants.
She laughed a little. "Okay, but I have to know... will I be the first MILF you've ever been with?"
I shifted closer to Leona, moving my hand higher up her thick thigh. "Absolutely," I said.
We leaned into each other until suddenly we began to kiss. Her big lips pressed against mine. Our tongues locked as we made out.
I began to feel her up. My hands moved from her upper thigh across her stomach up to her chest. I grabbed a handful of her giant tit through a sports bra.
I slipped my hand underneath and held her hot breast. The skin was soft, her nipple firm. Leona moaned into my mouth. Her tongue still tasted faintly like chai.
She moved on top of me, her dark hair falling over my face, and sat in my lap. I rubbed my hands across her body, squeezing her hips, her ass. God, what an ass! Her butt was probably twice as big as my own. I slipped my hand into her pants, tracing my fingers down her crack.
"That's my butthole!" Leona's eyes rolled back as I settled my hand over her warmth. I poked her anus softly with my fingers and felt a moist wetness coming from her hole. I reached down even farther and grabbed hold of her pussy.
We kissed some more, one hand on her breast and the other clutching her pussy. Leona's hand slowly moved to my groin. She traced the outline of my bulge with her fingers. My dick was already stiff, but now I was rock hard. Leona unbuttoned my pants slowly. "Can I taste you?"
No hesitation. I let go of her ass and she climbed off of me. Leona dropped to the carpet and gazed into my eyes. I flopped my dick out of my boxers and onto her chubby brown face. She smiled hungrily.
Leona kissed my balls gently. She licked my shaft from the base of my balls until my dick pointed directly at her. Then she took me into her throat. She pressed my cock to the back of her mouth. "Mmm," she moaned, looking at me. "I hope I'm not too rusty."
"You're amazing, please don't stop," I groaned as she pleasured me.
Leona spat down the length of my dick and jacked me. "Gimme that fat fucking dick."
Her head bobbed up and down as she blew me. One hand was wrapped around the base of my shaft while the other massaged my balls in a circular motion. "Your balls are so juicy... Don't come yet, though." She throated me to the base of my cock one last time and then stood up. "I want you to jizz inside me."
Leona pulled her leggings off, revealing a thin red g-string that barely covered a plump, shaven pussy. She climbed on top of me, kissing me again. Her mouth was covered in spit from sucking my dick.
I pulled her underwear to the side and inserted myself raw. She sunk her fat ass down on my shaft. Leona's pussy gripped like there was no tomorrow. We sunk into each other. She moaned deeply. "Oh fuck, that feels so good." Leona dropped her body onto mine and I felt the weight of her butt for the first time. Damn, was she thick. As Leona began to ride cowgirl, my hands wrapped around her butt cheeks. I spread them slightly as I gripped her fat ass. "Breed me daddy!" She yelled as my dick went in and out. I thrust into her excitedly. When a big girl like Leona rides you, you just let her do her thing. She kept riding. It was my experience that BBWs have very tight pussies, and Leona was no exception. Her hole gripped and stroked my cock as she bounced on me.
"Will you hit it from behind?" She asked.
I wasted no time in getting behind her. I had already fantasized about how it would feel to fuck Leona from behind. She sat with her face in the bed and her ass sticking up. Leona spread her cheeks. Just like that, Leona was throwing it back, her cheeks slapping against my balls.
Damn, this woman was horny. It was clear Leona was going to milk our time together for all it was worth. I stared into her asshole as she continually threw her hips back. My cock hardened, and I felt like I was about to come. "I think I'm gonna jizz " Leona started humping me more rapidly. "Come in my womb. I want you to come inside me." I pressed my dick deeper into her warm wet hole. Her chunky ass cheeks clapped as I plowed.
My penis twitched, and a rush of hot seed shot from my cock into Leona's hole. She moaned and sat as deeply as she could. "Oh god, your come feels so hot..." After a few moments of ecstasy and heavy breathing, I opened my eyes. Leona still sat on my dick, looking down at me through cock drunk eyes. As she lifted her ass from my crotch, come poured from her fat, wet hole. "You got me good."
We continued to hook up on weekday mornings for a while. Leona would send me pussy pics whenever she was horny. "It needs your come," she texted. I would pump a couple of loads into her, cuddle for a few hours, and then go home. Rinse and repeat. We also had something we called "face painting." That was when we would meet up somewhere random and I would ejaculate on her face. She said it made her feel young and dirty to leave a public restroom covered in semen. "I need to feel you on my face today," she would text me.
Months later, I met Candace, and we clicked so well that I felt it necessary to stop fucking Leona.
Before I made it official with Candace, I told Leona that I was going to start dating someone more seriously, and that we would have to stop our meetups.
Leona looked disappointed but understanding. "I totally understand. One last time before you're gone for good?" I excitedly agreed, and Leona and I made deep, intimate love for hours. I felt every curve and ridge of her pussy. I spread her cheeks and felt her anus pressed to my groin as I bottomed out in her. She humped and humped.
"I'm gonna miss that cock," Leona moaned. "She's a lucky girl. But I'm going to give you something to remember me by."
My orgasm grew as I plowed the fat MILF from behind, filling her with my penis. Leona's fat sweaty cheeks clapped against me. "Come on my ass this time baby." I kept pounding her big ass. "I'm your fucking whore. Come fuck this pussy if you ever get bored."
I started to jizz. I pulled out quickly as I exploded on her butt. My come shot on to her ass and asshole. I jerked as more come squirted from my dick onto Leona's round cheeks and open ass. "Take a picture so you don't forget what you're missing."
A few months after we began dating, Candace's family had a Super Bowl party, and I was invited. She had a big family and I hadn't met everyone, so it would be a good opportunity to put faces to names.
I carried a couple cases of beer in from the car as Candace's mom Ashley greeted us at the door. She looked cheerful. "You guys should eat. The niners are ahead."
We entered the house to a small crowd. I recognized a few of the folks: Candace's uncle, Tony. Her grandma. A few cousins I met before. And... Leona? What was Leona doing here?
My heart raced as I locked eyes with my former cum slut. Should you be here? Should I be here? Am I in trouble for something?
"Tim, this is my cousin Leona. Leona, Tim." She wore a black hoodie and green leggings. Her sweatshirt looked stretched over her massive tits.
"Hi Tim!" Leona said warmly. "It's nice to meet you. Leona's told me so much about you."
"Good things, I hope. It's nice to meet you, too." I felt nervous. Did Candace know about my past with her cousin?
Leona smiled. "All good, of course. You two should sit down over here when you get food."
I sat at the table between Leona and Candace. Surreal. Not too long ago, I would nut all over Leona's face, smearing her makeup with semen. Now, I was doing the same thing to her younger cousin Candace.
At some point in the afternoon, Leona caught me alone outside. I sipped from a beer. "Hey, how are you?" She asked.
I laughed and looked side to side. "I could be worse. This IS kinda awkward, though... if I knew Candace was your cousin, I wouldn't have..."
Leona interrupted. "It's not awkward. You got a type, I get it. You like Latinas. Clearly, we have a type too, and it's you. I won't make it weird if you don't." She gave a comfortable smile. "But I still miss our face painting sessions. And it is pretty funny to think that when you ended things, it was because you wanted to date Candace. Because Candace and I have talked about you so much and I never put two and two together. She really is a lucky girl. I know how good your dick game is." Leona glanced around. "I hope she gives it to you good."
So Leona and I agreed to ignore our past together for the sake of not fucking everything up, but every so often, I jacked off to the photo of Leona's spread booty marked with my load
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