Chapter 1

I couldn’t believe what I was doing. The fact that I agreed to this was way out of character for me, and now that I was mid-stroke in someone that wasn’t my girlfriend ... holy shit!

Okay, let me back up a bit.

My name’s Thomas Williams, but everyone just calls me Tom. I am an average guy in almost every way you can measure – medium-length brown hair, just under six feet tall, athletic build, but not cut by any means. I don’t have one of those ten-inch cocks people like to write about as if they’re normal. Mine’s average, and I like it that way because I am not limited on where I can put it, if you know what I mean.

I’m just decently in shape, you know, average. I’m not a virgin or some late bloomer that’s helpless when it comes to sex. I know my way around a woman and even had a nice little reputation by the time I graduated from high school, and I maintained it in college that I was one of the “good guys” for girls to experiment with.

There are a lot of reputations you don’t want when it comes to girls while you’re in high school. This one, however, was the one everyone would have wanted. Trust me. I basically had license for girls to let their inner freak out with me, and let me tell you, there were some shocking things some of those girls were curious about, but that’s a different story for another time.

Anyways…

I graduated from college last year and was just getting settled into the daily grind of post-college life. Not to mention all the responsibilities that come with officially being an adult. I had a girlfriend, Mandy. The two of us have been dating for a little over a year now. She was still in college and was set to graduate with a degree in psychology this year.

Mandy also happened to be one of my little sister’s best friends. Dating Mandy wasn’t planned on my part. I hadn’t secretly lusted after her since puberty or any such nonsense. No, it was nothing like that. To be honest, I hardly even knew she existed, not really. Sure, I knew who she was, but that was only in passing. I would have been hard-pressed to pick her out of a police lineup if I’d needed to.

Still, here I was, fresh out of college and dating my little sister’s best friend, and let me tell you, that took some getting used to.

Here’s the thing ... my sister, Stephanie, and I weren’t all that close when we were little. It’s not like we fought all the time or anything like that. We just ran in different circles and had different interests. We didn’t have any mutual acquaintances to bring us together at parties or anything. To put it bluntly, I didn’t want her around me and my friends, and she didn’t either. Aside from the rare late-night phone call where she needed a ride home from a house party, our lives were completely separate.

Things took a hard left turn during my summer break before my senior year in college. I was back at home, trying to save what little money I could, when Mandy had approached my little sister, asking if I was single.

I was shocked when Stephanie came to me to tell me about her friend. I probably should have reacted better at the time, but hindsight being twenty-twenty, that’s easy to say now.

“Hey, um, Tom?” I heard a knock on my bedroom door. I was already open, so I spun in my desk chair to find my little sister poking her head in my room, grinning like a lunatic. “You got a second?”

“What are you doing? Wait!” I heard another panicked feminine voice hissing from out in the hallway, out of sight. I saw a pair of hands grab onto my sister’s shoulders, trying to yank her away from my door, but Stephanie held onto the door frame, giggling as she held off her attacker. “Stop! Please, you can’t, not right now—”

“What, you wanted to know.” Stephanie’s cheeks reddened as she smiled at me, and quickly turned, batting away the strange hands desperately pulling at her tank top. “Trust me. It’s going to be fine.”

“Oh, God!” the strange voice whined, and then there was a strangled yelp as my sister freed herself from her attacker, and she turned to face me again.

It was crystal clear that whoever was in the hallway did not want my sister talking to me. That much was painfully obvious, but my sister thrived in those types of awkward moments. She loved to put people on their heels and call them on their bluffs or embarrass them in general.

Stephanie was a lot of things, most of which were directly related to annoying. Though I had to give her credit for one thing, she was fearless and always had been. She wasn’t exactly a rebel, but she wasn’t afraid to paint outside the lines either.

I sighed and rolled my eyes at my sister’s antics.

“What do you want?” I deadpanned, not having a clue what was coming next.

“Oh, it’s not what I want, not exactly,” Stephanie grinned evilly. “It’s what my friend wants.”

“Steph, oh shit!” I saw a head peek around my door frame. Whoever it was, she was so quick I almost didn’t see her before she retreated back into the safety and seclusion of the hallway.

“Yeah fine, whatever,” I groaned, sitting back in my desk chair with my arms folded across my chest. “What does your friend want then?”

“You.” Stephanie grinned.

My eyes widened in shock before reality set in, and my defenses were brought to bear. My brow furrowed, and I glared at my sister.

“Me?” I asked, giving her a questioning look as if I didn’t believe her. My sister had never been the most reliable when it came to answering questions or just giving you all of the information you needed.

“Yup, you,” she nodded, her eyes dancing with unbridled mirth as she wiggled her eyebrows up and down suggestively. “She wants to know if you’re single.”

“I don’t have time for your bullshit games, Steph.” I groaned and spun my chair around and putting my back to the doorway, thinking they would just go away.

I was wrong.

As it turns out, my sister wasn’t full of shit, much to her amusement. Her friend really was interested in me, and the next thing I knew, Mandy and I were regularly going out on dates. Even more shocking, we hit it off almost immediately. We were virtually inseparable from that point on.

There was one major unforeseen consequence to having a relationship with Mandy that I never really stopped to think about before I was already in neck deep. That problem was my little sister. Now that I was romantically attached to one of her best friends, Stephanie knew more about me than I had ever intended. In hindsight, I should have assumed that with me dating her best friend, that would be the case, and frankly, I should have expected it, but I didn’t.

I know I underestimated the level of detail girls shared when it came to talking about their relationships. Nothing, and I mean nothing, was left off the table, especially when it came to sex. It was bad enough to hear Mandy talking on the phone to Stephanie about such things. It was something completely different when they were together, in person, talking about it like I wasn’t there. That was something I just couldn’t wrap my head around. Even stranger was the fact that Stephanie wanted to know all the gritty details. To make things even more awkward, she was ... proud of me, and my sexual prowess.

I wasn’t naive enough to think some of those bedroom secrets would be shared. It was the level of detail that truly shocked me. It wasn’t a one-way street either. Mandy learned all kinds of things about my sister and who she was dating or had flings with.

Thankfully, Stephanie didn’t seem to date guys longer than one or twice. That meant that I was never thrust into the delicate situation of having to meet one of those ... guys. From the way Mandy and my sister talked, it was for the best.

Still, I learned early on that it was best to make myself scarce when Mandy and Stephanie talked. Honestly, as long as I didn’t hear them talking about me and some of those ‘sexy details,’ it really didn’t bother me all that much. I would still cringe if I thought about it for too long, but for the most part, I loved being around Mandy, and if my little sister knowing certain, extremely intimate things about me was the price I had to pay to be with her, then fine by me. She was worth it.

Alright, back to my beautiful girlfriend Mandy, and how I ended up in the surreal situation where I was fucking a girl I’d never met before, right in front of her.

Mandy was a small thing. Loosely curled blonde hair, big blue-green eyes, full lips, and a little button nose. She had been huge in gymnastics ever since she was a little girl, but had given up the dream of going to the Olympics due to an injury while she was in high school. The nice thing that came from that was her body started to really fill out once she slowed down on all the intense training. Since then, her tits had blossomed into perfect handfuls, and the firm, fullness of her ass was mesmerizing. She was a shade over five feet tall, what she playfully liked to call, “fun-sized.”