Twenty Year HS Reunion with Mom & Daughter

All characters in sexual situations are 18 years of age and older.

Twenty years had passed since I graduated from High School. Back then, I was a skinny, zit covered teen, who could only fantasize about being with girls. Things luckily changed once in college. My skin cleared up, my 6'6" body went from 178 to 220 pounds, and I got into a steady relationship.

I think my hormones told me I had some catching up to do, so I tried, sometimes subconsciously, to hook up with different women, even when I was in a relationship with someone. I got caught a few times and for some reason, that only made me smarter and bolder.

It would be a lie if I said that wanting to get married and start a family was not a desire of mine. However, it was buried deep inside of me and knowing which women were up for casual sex made it hard to wanting to settle. Things become too easy with a certain app coming out and it became harder by the month to stay satisfied with me sex life.

I did not even care that some of the girls either wanted gifts or straight up cash, before they spread their legs for me. My career and lack of family responsibilities allowed me to spend money on women.

"Dude, you like being a thirty-eight-year-old player?" my buddy Scott asked me over a beer. Contrast to me, Scott already had three kids and seemed happily married. I did not even give him a hard time and tried not to share too much about my sex life.

"Maybe I will find the love of my life at the upcoming High School reunion," I said. Scott and I did not go to school together, so he had to tried to imagine how some of the girls looked that I was describing to him.

"I had a crush on two girls in particular, and they could not be more different from one another. Samantha was a gorgeous blonde, kind, smart, and based on her Facebook profile is happily married. She actually ended up marrying her High School sweetheart. Then there was Tabatha, a hot ebony babe, who was the known slut in school. Rumors had it that she not only slept with half the sports teams, but the only reason why she got average grades was because she gave the male teachers blowjobs after school," I explained.

"Do you know what she is up to?" Scott asked.

"Nah. I don't think she has a social media account," I answered.

"Why did you have a crush on someone like that?" he asked.

"Man. She was all legs, had tits that were too big relative to her slender body and there was something about her promiscuity that was a turn-on," I explained.

"Watch, she is gonna show up to the reunion married and completely innocent," he predicted.

A few weeks later, I walked into the even space that was already packed. Out of the two hundred students that graduated with me, almost half signed up to come. I was easy to be recognized due to my height and I made my rounds, catching up with people who I had not seen in twenty years.

When I ran into Samantha, I could feel myself getting nervous.

"Hey Dan, you look great!" she said and hugged me tightly. I could tell that she got a head-start on the drinks.

"You still look as beautiful as you did twenty years ago," I said.

"Oh, thank you," she replied.

"Did you bring your husband?" I asked.

"Thad? No, he is traveling for work again," she replied. We ended up talking for a few minutes before we got interrupted by a few other girls, some of which I had completely forgotten about. Once the ratio was five-to-one, I felt like I had to remove my male behind from the group.

"Let's catch up later Dan," Samantha said while brushing my upper arm.

I caught up with a few more guys and just as we began talking about some of the sluttier girls from school, Tabatha walked in. All four of us turned to look into her direction and it was Mike who said what all of us were thinking: "Speaking of slut."

"Did you bang her?" James asked Mike.

"You know it," he replied and gave each other high-fives. Jay joined the high-fiving and before it was my turn to point out that I did not, I used my buddy John walking buy as an excuse to leave.

Even though I was having a great conversation with John, I kept looking over at Tabatha. She still looked gorgeous and wore a fairly short black dress and heels. She always used to dress to impress or attract and that night was no different. I watched her grab a drink and barely speak to anyone.

I lost sight of her for the next couple of hours but ended up running into her by the restrooms.

"Hey Tabatha. It's great to see you!" I said.

"Dan, right? I barely recognize you. You look amazing," she said. I could not help but notice that her cleavage looked more impressive up close. We walked out to the main area together and even though only a few people were dancing, Tabatha insisted on me dancing with her.

For the next thirty minutes, we either danced, grabbed a drink together or chatted.

"They are all looking at me like I am still the same slutty girl," she mentioned, seemingly getting a bit drunk. I don't know what came over me, but I replied with: "And are you?"

She smiled at me and said: "Don't you wish to find out."

Well, I ended up finding out. We left minutes later and since she took an Uber to get to the reunion, I offered her a ride home. It was only a five-minute ride, but she had already undone by pants and pulled out my cock.

"Holy crap, long and thick, just how l like it," she said and began bobbing her head up and down my shaft.

We stumbled into her modest home, making out the entire time. We did not even bother taking off her dress before we began fucking. She was bent over the couch, her thong pulled to the side, when I began taking her from behind.

I grabbed her shoulders and kept slamming against her body, causing her to cry out in pleasure.

"Shit Dan, that's it," she cried out. She used on hand to brace herself and the other played with her tits first before moving down to her clit. Seconds later, she came. I kept fucking her until I nearly came myself. I pulled back and stood there for a moment, allowing both of us to catch our breath.

"Do you want me to suck him?" she asked lustfully.

"Do it," I answered and without having to lay a hand on her, she got on her knees and began to deepthroat me right away. While she was not the first girl to swallow me balls-deep, I had never experienced one who did it so effortlessly.

"Fuck, you are gonna make me cum soon," I groaned. In response, she pulled back and licked my balls, leaving my throbbing cock alone.

"You want another round, don't you?" I guessed.

"Yep. Let's go into my bedroom," she said and was about to take off her shoes.

"Leave them on," I told her.

"Yes sir," she replied and planted her lips on mine. I got completely naked and watched her pull off her dress and bra. For a thirty-eight-year-old woman, she was in great shape. Even her 36D tits barely sagged. She opened her nightstand drawer and pulled out a vibrator that was as big as her forearm.

She laid on her back and wasted no time and placed the toy on her hairless clit.

"Come here and suck my tits," she demanded. I leaned over her and did as she asked. When she began to lick my ear, I felt goosebumps on that half of my body.

"I need your cock inside of me again," she suddenly moaned, and I straddled her. Literally the moment I penetrated her, she began to cum again. Her entire body was shuttering for the next twenty plus seconds. I watched my cock disappear inside her body, mesmerized by the contrast between our skin tones.

She threw the vibrator to the side and reached up to suck on my nipple.

"You know what? You are one good fuck Dan. If you can hold out a bit longer, you are gonna make me cum again," she said breathing hard.

"You are something else," I said and took a much needed break, staying deep inside of her without moving. I caressed her legs, reaching for her tight ass and began to ask myself why I did not try to have interracial sex more often.

"I am thirsty. Let me get my water bottle," she suddenly said.

"I can get it for you. I want to see you spread out like this when I come back," I said.

"Sounds like a plan. There are water bottles in the fridge. Maybe we should get another toy out," she said.

I stood up, feeling the cool breeze from the A/C vent on my sweaty body. As I walked out, I briefly imagined that this was happening in our senior year.

"Holy shit!" a loud whisper interrupted my daydream.

I looked towards the opposite hallway and saw a girl standing there, staring right at my naked body. It was pretty dark, but I could tell that she was young, dressed in some short jean shorts and a tube top. I covered my crotch, grabbed the bottle and hurried into the bedroom.

Tabatha was on all fours, and was rubbing an anal plug against her ass.

"Like the view?" she asked.

"Heck yeah," I answered and decided not to mention anything about my encounter. "Does this mean that I get to fuck that ass of yours?"

"Maybe tomorrow. I don't feel like cleaning myself for the next thirty minutes. I do love the feeling of something up my ass while I get fucked though," she replied. I handed her the water bottle and she chugged a bunch of it.

"Tell me, where does a woman like you let herself be cummed on?" I asked. getting into position behind her.

By the time I was ready to penetrate her, her ass swallowed the stainless-steel plug already.

"Ever cum on a black ass before?" she asked.

"Yes," I simply responded.

"Awwh, I thought I might be your first interracial experience," she responded disappointed. "Why don't you tell me where you'd like to cum."

"You do have the prettiest face and best tits, so...you know," I answered. I began to take her slowly and she already began to moan.

"I will let you cum on my pretty little face. You deserve it. Just don't get it in my hair," she said. "But before you do that, you need to make me cum one more time."

I increased my pace while grabbing her tight ass. I thought the plug-cock combination would be enough to make this vixen climax, but she grabbed the wand again and put her head down so she could use her hands to hold it against her clit.

With her ass sticking up in the air, I began to fuck her harder with each thrust. Tabatha was cursing into the bedsheets, seemingly getting close to another orgasm. I was afraid that she could not cum before I did, but she came just in time.

I think she was still cumming when I told her to turn around. I had to squeeze the base of my cock to prevent the first shot to escape too soon. I let the first stream shoot at her the moment she was on her back, covering her left tit. I leaned forward and unloaded the rest of my balls on her face. I did not want to mess up her braided hair, so I was glad that most of it landed right inside her opened mouth.

Just when I was about to sit back, she told me to bring my cock to her. She ended up deepthroating me one last time before I collapsed next to her. She quickly got up and took a quick shower. I suddenly realized that the door was cracked open even though I could have sworn I shut the bedroom door behind me. I began to wonder who that girl was and if she ended up watching us.

Tabatha was still butt naked when she walked out.

"I don't know about you, but I could use another drink," she said, and I got dressed. Tabatha put on her robe and got a head start.

As we sat on the couch, I saw a picture of Tabatha with the girl that I saw in the hallway.

"Who is that?" I asked.

"My daughter. She decided to spend the night at her friend's," she answered. I could not help but notice how beautiful she was.

"She is beautiful. Just like her mom," I said.

"Yeah, and I am afraid that she is as cock hungry as I am," she said. I did not know what to say. It was the oddest thing I ever heard a mother say about her daughter.

"Now that she is eighteen, I cannot tell her what to do," she explained.

One drink turned into four and both of us ended up drunk. Me spending the night was the natural conclusion and we passed out in bed together.

I woke up to an empty bed the next morning. Tabatha left a note for me.

"Had to go to work, sorry. Lock the door behind you. Make some coffee if you'd like. I had a GREAT time. Call me... - Tabatha."

She left out a folded towel, so I figured I was free to take a shower too. After drying off and getting dressed, I was ready to head out, but noticed that she had one of those fully automatic coffee espresso machines.

I grabbed a cup and pushed the button. The machine began to grind the beans and then filled my cup with fresh coffee. I blew on it, trying to speed up the cooling process so I could chug it and leave. Then I heard a door open and realized that Tabatha's daughter might still be home.

Seconds later, a gorgeous teen stood in front of me, wearing a white bra and underwear.

"Sorry, I will get out of your way," I said nervously.

"You can finish your coffee," she said and walked right by me. Her skin was considerably lighter than her mom's and even her curly hair was light brown. I stood there frozen, looking down her backside, her hair almost touching her thong covered ass.

I began to get an erection and quickly readjusted my pants.

"I am Destiny," she said and began to make her own cup of coffee.

"Dan, nice to meet you," I replied.

"So are you one of mom's high school friends?" she asked and turned towards me, holding her cup with both hands.

"Yes. Sorry for walking around naked last night," I said.

"Don't be. That was hot. I hope my man looks like you when he approaches forty," she said.

"Where does your mom work?" I asked, trying to change the subject.

"Wow, fuck her a few times and you don't even know anything about her," she said with an attitude.

"Guilty as charged," I said.

"She's a waitress. She tells her friends that she is the shift manager. All that means is that she gets paid an extra buck to put up with all of the nonsense from customers," she explained. "What do you do?"

"IT," I replied.

"Is that what pays for the Audi up front?" she asked.

"I guess it does," I responded, anxiously waiting for my coffee to cool enough.

"Listen," Destiny said and put her cup on the counter, followed by closing the already narrow gap between us, "I know my mom is fun to sleep with, but you have a horny teen right here in front of you. Let's have some fun before you go."

"Des, Destiny, I am intrigued, but I don't think we should," I answered, feeling my cock throbbing.

"The question is not if we should, but could. And as far as I can tell, we can," she said and ran her petite fingers over my crotch. "You know, I watched you fuck my mom last night and the boys I have been with don't stand a chance against you. I think you should show me how grown-ups do it."

I still stood there, frozen in place. She took my hand and placed in against her tight butt that was partially covered by her hair.

"Did my mom let you fuck her ass last night? I know she is into that stuff," she asked.

"Destiny, I don't know what to do here," I answered, feeling intimidated by this teenager.

"Just say yes and I will take care of the rest," she said. She got on her tiptoes and licked my neck. My hand was still on her ass, and I felt it flex. I could not help but to stroke it lightly.

"I take that as a yes," she whispered and I looked down at her. The next thing I remember was both hands wrapped around her ass and picking her up so we kiss each other. The tip of my cock pushed passed my belt and she happened to rub her crotch right against it.

"You are so fucking big," she moaned. "Follow me." I walked behind her like an obedient dog, watching her little ass sway. When I realized that we were going inside her mother's room, I stopped.

"What do you think you are doing?" I asked.

"This is where all of the fun stuff is," she said and opened the door.

"Are you sure she is not coming home early?" I asked concerned.

"She won't be home till dinner time. And aside, do you think it will make a difference if she catches you fucking me on her bed or mine?" she replied. She walked towards the closet and reached for items towards the back. Seconds later, she had three different sets of lingerie in her hand.

"How about I put one of these on for us?" she asked. First she held a black pleather looking corset with garters against her body. The other item was some sort of lace minidress and the last one was a schoolgirl micro skirt and some white top.

"Your mom wears a schoolgirl uniform?" I asked.

"I think she likes to tell herself that she is still an eighteen-year-old. By the way, is it true that she was gangbanged by a bunch football players?"

"Where did you hear that?" I asked.

"Someone messaged me on Facebook. I wouldn't be surprised," she said. "Fine, I will wear the schoolgirl outfit for you."

"But I didn't even answer," I said.

"You didn't have to."

"Any chance you can wear some stockings with that?" I asked.

"Let me guess, some heels too?"

"Well, of course," I replied.

"Well, lucky you, my mom and I almost wear the same shoe size, and she has heels that have slut written all over it. Here, take a pick," she said and pushed the closet door to the side to expose a rack of at least two-dozen pairs of high-heels.

I stood up to take a closer look. Before I got to the closet, Destiny stepped in front of me and grabbed my crotch.

"Listen, Dan. How about we make a deal? Pay me $300 and I will go to the bathroom to clean my ass for you so you can shove your big cock up my asshole," she suggested.

"Uhm, so that's what this is about, you want to get paid?" I asked.

"No, that's not it. Let's just say I know you probably would be willing to pay to have anal sex with a teen, and I want to get paid for the pain and suffering," she explained.

"You don't say," I simply replied.

"So we have a deal?" she pressed.

"Fine, deal," I said.

"Good, give me like ten, fifteen minutes. Pick out the shoes and if you want, you can open up that box over there and pick some other kinky stuff for us to play with," she said and walked away.

For a brief moment, I considered leaving her, thinking that my time with Tabatha was more than a one-night stand. That thought quickly faded as I was drawn to the heels that were displayed in front of me. Half of them were shoes most women would not try to walk in outside. One of them, I guessed, was at least seven inches tall.

I ended up choosing a black latex looking pair of 6-inch platform heels. They were red at the bottom and showed a lot of wear and tear. I was then drawn to a basket of thigh-high stockings. I grabbed a pack of black thigh-highs and proceeded to the box Destiny referred to.

If the kinkiness of Tabatha could be described by a collection of items, that was it. There was a pair of handcuffs, different ball-gags, a rope, clamps, neck collars, leashes, and a variety of dildos. I did not even know where to begin. I ended up choosing a couple of dildos, one barely as thick as a carrot and the other a bit larger than my cock. I also grabbed a leather collar. My cock was throbbing by the time I laid everything out on the bed.

I heard the toilet flush and seconds later the shower turn-on. Once she finally came out, she was smiling seductively. She put on some lotion that made her skin glow. I watched the teen getting dressed, not saying anything about the extra items that I selected for her.

"Shouldn't you get undressed?" she asked, just as she was finishing the outfit by putting on the heels.

"I will have you do that for me," I said and stood up.

She wasted no time and peeled off my shirt, unbuckled my belt and unzipped my pants. Now wearing the high-heels, she was within a few inches of my height. She squatted down once it was time to pull down my underwear.