Don't Kiss & Tell - Proposition 01

All characters are over 18

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My name Damon, I'm a 25 year old CEO of my own tech startup. I like to consider myself a high value man, I look good, have excellent shape, maintain my masculine frame and I'm overachieving in the finance department.

Though, I'm currently living with my girlfriend, Toya (age 24), in her childhood home with her 18 year old younger sister, Kayla, and her 45 year old mom, Monica. It's not that we couldn't afford to get a home of our own. Initially, we moved with them post-grad, but Monica asked if we could delay our plans to get our own spot so that we could enjoy some privacy. Monica thought it'll be nice to finally have a man in the house again for safety reasons.

According to Toya, Monica hasn't really dated anyone seriously since Toya's father died a few years ago, but Toya did mention that Monica has had a very active sex life since. Toya even admitted that she masturbated once to the sound of her mother moaning and getting dicked down by a bouncer she met while out with her friends. I would later find out how true that statement is. One night we were woken by the sound of Monica screaming for him to fuck her harder. It turned us on so much that we ended up fucking that night as well. It even seemed like Toya was competing with her mom with how audible she was being.

Monica looks incredible, definitely has a pornstar body. It was as if she came from the ebony porn golden era which featured Pinky XXX, Ayana Angel, Jada Fire and Cherokee D'Ass. She stood 5'4", with 36D-29-50 measurements, beautiful brown eyes, long black hair, and nice, even, blemish free, milk chocolate skin. She's definitely a Mother-I'd-Like-to-Fuck and if I was single I probably would have shot my shot. I'd even admit that on a few occasions I fantasized about fucking her, while I made love to Toya, even one time slipping up and moaning Monica's name. Toya ignored it but I know she heard it.

Monica's not innocent either, she often flirts with me and says if I wasn't her future son-in-law and what she would do to me. Sometimes she even bends over so I can get a better look at her ass when she catches me staring at it. I think she just loves to see that I can get that kind of reaction out of me and doesn't plan on actually doing anything.

This is not to say that Toya couldn't hold her own against any woman. I think my attraction to her mom stems from the fact that Toya looks like a younger version of her, except Toya's is slimmer from playing college basketball, which is actually how I met her.

-Flashback to 4 years ago-

I was 21 years old Junior Software Engineering major, writing for the University of Georgia newspapers sport column and I was covering one of the women's basketball games and I was assigned to interview her. Personally I've never been a big fan of women's basketball but as I watched the game, I noticed how good she looked in her uniform. Even in those baggy shorts it was obvious she had a body to kill for. With every dribble just watching how her ass jiggled as she ran up and down the court, every jumpshot her titties jiggle. Maybe I'm exaggerating a bit but she really made me appreciate her league a bit more. Once I was able to snap out of my lust, I remember why I was there. I started to pay attention to her play and damn she was killing it. Droppin' dimes left and right, not to mention making the occasional 3. It was amazing how God somehow brought my love of basketball and big booties together into one woman. It felt quite odd getting wood from watching a basketball game but I'm sure I wasn't the only one.

Her team the Bulldogs go on to win the game by a narrow margin, with her scoring the tie-breaking buzzer beater. I made some notes about other things I observed from the game. Then I went to meet her to see if I could get her to interview with me. The floor was crowded with other admiring fans still celebrating the win. People were shoving and bumping into me as I navigated through the crowd.I looked through the crowd and noticed her jersey number (#3) and proceeded her way. As I got close, I saw her backing away from some of the other students and was getting closer to me. I tried to back up to give her space but we were trapped on all sides.

Soon she backed into me and her ass landed square in my crotch. She tried to move away but the movement caused her ass to press against me. My dick responded as expected as I felt her ass sandwich it between her cheeks. In any other situation, I could probably enjoy the feeling but the fact that she must've thought I was a big perv was running through my mind at that moment. She continued her movement trying to separate, not realizing the effect it would have on my current situation. I looked down and saw her shorts had rid up to the point where my dick was logged between her cheeks and below I saw the bottom of her beautiful ass. Once the crowd started clearing, we were able to separate and compose ourselves. I tried to ignore the obvious and pitch my bid to interview her.

Embarrassed, I said "Hey, I'm really sorry about that... I know your probably want to get as far away from me as possible after what just happened but my name is Damon with the the university newspaper and I was wondering if I could maybe interview you for the sports section?"

"Oh, it's okay, I wish they stop them from running on the court after a win because I would really love a shower right now and this is a bit much. But sure you could interview me."

"Thank you so much."

"We can do it in the locker room, but you might wanna do something about hiding this.." She grabs and briefly strokes my erection. "Very forward of her," I thought.

I look around to make sure no one is looking, tgen I adjust myself so it's less noticeable. She grabs my hand as we force our way through the crowd into the locker room.

"As you know you shouldn't be in here, but it's cool since you're with me. Just don't make it a habit of coming into the girl's locker room." she teased.

Writing in my notepad I say," Athletic, Cute and Funny"

"Aww you think I'm cute? Well you better after having that monster in your pants between my cheeks for all that time." she turns around and points at her ass.

My dick twitches. "Wow...okay. I don't know what to say. Nobody's ever called it a monster before."

"Well whip it out and I'll know if it qualifies."

"Maybe later, but first my interview"

"All work no play? You're no fun." she teasily pouts. "But I guess it's always been the case with you."

"Huh? What do you mean?" I asked, looking confused.

"Nigga, I can't believe you don't remember me." She states.

"Remember you from where?"

"Freshman year, English 1101, we literally sat next to each other in the back of the class."

I sat there trying to put two and two together... "Oh yeah, that was like 2 years ago. How the fuck could I forget you?"

"How the fuck could you? Probably because you were too busy following around your bitch of a gf that you didn't notice anyone else. Y'all not still together are y'all?" She quickly backtracks.

"Haha, No we broke up sophomore year after I caught fucking my roommate on my bed none the less"

"Great... Not great that she cheated but great that your no longer wh her."

"Yeah I was definitely blind to who she really was."

"Now I bet you got all the ho's now, keeping that big ass dick wet." She walks up to me and gently strokes my hardening penis.

"Me? Look at you, I think I was watching that ass move more than the actual game and that's literally my job."

"You like this ass?" She bends over and slowly pulls down her basketball shorts to reveal her beautiful bare ass. "You wanna come feel how soft it is?"

"So I'm guessing that somebody had an ulterior motive to get me to interview you here, in a surprisingly empty locker room." I grab a handful of her ass.

"Yeah the other girl usually go out to celebrate after a win and just shower at home." She responds.

"Hmm. So this was your plan all along?"

"Well when I first backed up into you and felt that poking in my back, I wanted to punch whoever it belonged to. But when I looked over my shoulder and saw it was you, my pussy got wet and I just knew I needed to get you to help me "celebrate" in my preferred way. I just got lucky that you happen to want to interview me"

As she pushes her ass against my crotch I tell her "It's really sexy to see how you go for what you want."

"If you think that's sexy..." she walks over to lock the locker room door. "Wait til you get a taste of this wet ass pussy. I get sooo wet after a game and besides it feels like I've been waiting 2 years for that dick."

"Damn, I wish I knew you were feelin me earlier? You should've told me."

"Boy stop. You didn't even remember me. That girl had you sprung. How do you forget all this ass?"

I look her over again. "Okay I see your point, but what about my interview?"

She begans to laugh,"I happen to want the one nigga that doesn't think with his dick. I'll tell you what, make me cum and you can have anything you want from me." She finishes taking off her clothes and walks to the showers.

I took the hint and followed her ass to the shower area (first double checking to be sure we were alone). She gave me the best pussy of my undergraduate experience, there was no way I was gonna let this be a one and done. Just watching soap cascade off her chocolate ass made me hard as cement. I walked behind her, forced her against the wall and slid my dick between the lips of her pussy.

"Damn no foreplay... ah shit baby... this dick... feels amazing. Fuck me harder." she moaned in her ear.

"Uh huh" was all she said as threw her ass back, taking all of my dick into her soaking wet pussy.

Not to be outdone, I grabbed her waist and began giving it to her.

"Damn you don't know how bad I needed this. Definitely worth the wait." She put both hands on the wall as I went to work on her pussy.

She came first, so I wanted to maybe get some head before I came, but Toya had other plans. When she felt me starting to pull out she pushed back and spun us around so now I was against the shower wall and she rode my dick until I came deep in her pussy, and she came again.

That's our first time together and how our relationship began. That weekend we had so much sex that I didn't even get to actually writing my article. After that weekend everytime I come to the game and we would end the night at either her dorm or mine. It slowly turned from just fucking and staying the night to sometimes just hanging out, order takeout and binge watching shows together on netflix. Oddly enough after a couple months of fucking and hanging out we finally had our first official date. Weeks later we became officially a couple and the rest is history.

-Flashback ends-

Laying in bed with the love of my life I wonder how I got this lucky as she cuddled against my chest. I kiss her lips as I shimmy away from her embrace. I go downstairs to cook breakfast, bring some breakfast up to our room and sit it on our nightstand. Still sound asleep I crawl under the covers, part her legs, give her pussy a kiss, then begin slowly licking her pussy. Soon, I get encouragement from her in the form of her moaning and grabbing the back of my head. I put two fingers in her pussy as I moved up to suck on her clit. She removed the covers from my head, smiled and motioned for me to give her a good morning kiss. I kiss her and inform her of the breakfast I made her. She eats her breakfast as I resume eating mine.

Listening to her sounds of pleasure, from my cunnilingus skill and culinary skills, made my morning wood rise again. I travel up her body until my hard dick meets the gates of her vagina. Slowly began rubbing my dick against her wetness. She begins moaning louder and sits her plate down back on the nightstand. She then gives me a knowing look as my cue to fully impale her. Toya began gyrating uncontrollably as I saw the door fly open. "Thanks for cooking breakfast...oops..." Monica interrupts, but Toya's so into the sex that she doesn't notice. Like a deer caught in headlights me and Monica stare at each other for a minute, but the little nymph underneath me wouldn't allow me to freeze entirely.

As I continue to pump into her daughter while staring at Monica, I notice something in her expression, pure lust. I smiled and licked my lips as Monica began rubbing her pussy underneath her nightie. The more I sound I make come from Toya the more visibly turned on Monica get, even to a point of removing her boobs from the confines of her bra and rubbing her pussy juices soaked fingers all over her nipples. So I decided to put on a show. I pull out of Toya making sure Monica gets a good look at my cock, then I go down on Toya finishing my meal earlier. Slowly stimulating her g-spot and bringing her to a squirting orgasm. Backing up a bit to be sure Monica can see my get showered in her daughter cum. I go up and kiss her daughter and I notice Monica shake with an orgasm of her own.

"Damn, I taste good AF this morning." said as she went for another kiss and licked the remaining cum from my face.

"Lol you are so nasty, I fucking love it too." I said kissing her more.

"Omg baby you cooked for me too?" she sqeals, "What did I do to deserve such special treatment?"

"Baby you deserve this and more... I just wanted to show you that I appreciate you." I told her.

"Aww Baby I wuv you too, but you forgot to put my cream in my coffee, I guess I'll just have to drink it from the source." She grabs my wet dick and slides it in her mouth. Watching her mom Monica as Toya expertly sucks my dick and nutsack. Watching intently as Monica removes her hand from her pussy and shows me her creamy finger before taking them in her mouth and licking them clean, causing me to begin filling Toyas mouth up with my load. She expertly swallows most of my load but some escapes her mouth unto her cheek, chin, and blouse. I looked up and Monica was gone.

Kissing her again then pushing up off the bed. "I gotta head to the office, but when I get home tonight, you're gonna get this "monster"." I tease her.

"Wooow... when are you gonna let go that I said that... anyway be safe getting to work and have a production day Damy-bae. I'll walk you out"

"Ok baby." Walking with her to the front door we ran into her mom.

"Heading to work a little aren't you?" she asked with a smile.

"Yeah, I took a little long in the shower this morning." I lied.

"Oh must have felt orgasmic... Oh baby you got cream on your cheek." she says to Toya as she scoops it up and looks me in the eyes as she spreads it over her tongue and swallows. "My baby is such a messy eater. Gotta make sure to catch it all in your mouth and swallow."

"Not subtle at all." I think as Toya looks at me confused.

"Well, have a great day at work." Monica says as she kisses me square on my lips, letting her tongue slip in massaging mine. Then even more surprisingly she kisses her daughter the same way as her daughter kisses her back. Monica continues kissing her looking me in my eyes, then at my growing bulge, then smiles and walks away.

"Daaamn, that was so fucking hot, I'm hard as fuck right now." I admit

"Me too, I wonder if she knew it was your cum when she licked it off."

"I don't know, but she clearly needs some dick." I state.

Looking at me curiously and cupping my budge " You better not be thinking about donating the dick to the cause, besides she gets enough anyway. But I don't know what's gotten into her, kissing you like that, then kissing me..."

"Didn't look like you mind, you were kissing her back."

"Okay! I'd admit at first it was kinda weird but after a while... I dont know... she's a great kisser." she admits.

" Fuck that was hot."

"Let me stop you there Mr.Mommy-Daughter fantasy." she teased

"You need to clear your browser history more often because you clearly are into it as well." She withdraws and blushes.

"Nothing to be embarrassed about. If I had to pick a mom and daughter for it to actually make sense. Like who would really question you two being attracted to eachother. Anyone with eyes would be attracted to you two."

"So you don't think it's weird?" she asked.

"Of course not, if my mom was as hot as yours I would've been waist deep in her pussy a long time ago." I confess.

"You're such a freak."

"You love it though. For real though, even if I thought it was weird I'd still be open to it, I love you."

"I love you too, baby." she says I kiss her again as I head out of the door.

Arriving at my office, I greet my 27 year old secretary, Kimmie, and other employees, before heading into my office. I'm the owner of a startup sports news app company called CourtSide, similar to the Bleacherreport but we mainly focus on nba basketball and the e-league.

Normally I could come in anytime I want but I have to meet with investors today.

As I wait on my investors I get a video message from Toya of her playing with her pussy while smelling one of my shirts. She follows that up with a text saying she misses me. Watching the video I got aroused and decided to take care of my problem, not to raise any suspension. I choose not to shut the blinders in my office. Now really getting into the video I briefly close my eyes, enjoying how Toya's video is making me feel.

I was awaken out of my fantasy, by the sound of my secretary Kimmie barging into my office to inform me the investors are running late. Not oblivious to what I was just doing she decides not to let this opportunity pass her.

So a little about Kimmie, she's actually one of Toya childhood friends. She is about 5'1", blasian with big titts and a nice ass. The dilemma with her is that she fell on hard times and lost custody of her kids. Toya pleaded with me on her behalf to hire her at least until she's able to get her kids back. But my issue with the whole arrangement is that she has practically been trying to fuck me since she's got the job here and I don't know how to tell Toya but also her kids situation. I'm not trying to paint her as a bad person but I just thought that I'd be off limits, like on some girl code shit. I'm no psychologist but I figured it's because I helped out or saved her from her situation and she feels like she needs to even the scales a bit by "rewarding" me and the only thing of value she has to give( in her mind) her body.

So, Kimmie locks my office door and closes the blinds slightly and walks over to my desk and licks her lips at the sight of my dick.

"Kim, what are you doing here? Why did you lock the door?" I asked somewhat rhetorically but also hoping she would come to her senses.

"Well, I've wanted that dick since Tee told me how good you be fucking her and I saw it after looking through her pics one day, but DAYYAAMN it looks so good in person." she moans.

"We both know there's like a million reasons that can't happen, one being the fact that I'm basically engaged to your best friend." I plead.

"Three reasons we should... number one we're both horny as fuck and two if you don't I'll #MeToo the fuck outta you. Lastly, you have wanted me since the first time Toya introduced us. She asked me to have a threesome with yall, remember? I bet it was all your idea too."

My jaw dropped as I can't believe that she would not only put me but Toya through something like that all for some dick she can't have. While it is true, I did ask Toya to invite her for a threesome, but I stopped it because I didn't want to complicate their friendship.

She walks around the desk and gets on her knees, gripping my dick and says, "Don't worry I'll take it easy on you, I just wanna suck this big motherfucker right now." She says as she engulf my entire dick, fuck her throat with it.

Still in disbelief but slowly noticing the skill in which she's blowing me, for a moment I forget that she's blackmailing me. She's gonna make me cum quickly with the pressure she's applying to my dick. She slowly removes her head allowing me some temporary relief as she goes down to suck on my balls. She slowly strokes me while sucking my balls staring me in the eyes the whole time. Finally decided to give in to this succubus and the pleasure she's giving me, I reach down to plant a kiss on her lips as I place her mouth back on my dick. She smiles shortly before continuing to snatch my soul. Feeling my orgasm coming she deep throat me and holds it there at the base before retreating to the head as I filled her mouth with my cum. She shows me my load before dipping her fingers in it then start rubbing her clit with it and swallows the rest. She gets up and places the head of dick at the lips of her pussy and start impaling herself and begans riding me, but she abruptly stop and began to cry.