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.
