My rich girlfriend invited me to her family’s Halloween party. Little did I know it was actually an orgy!
So, you’ll be coming to the party this year?” Samantha, my girlfriend’s little sister asked eagerly, jumping into the couch next to me. It wasn’t hard to see she seemed to be crushing on me, but I had no idea what Jessica had told her about me and us. For me it was nerve wracking. She was old enough to be a knockout, but young enough to get me into trouble. And even if I wasn’t dating her sister, knowing her father was a big shot lawyer ensured that there was no way I was going to get in trouble being stupid with her tail-bait body. Every time I was over at her place I made very sure to be completely proper around her at all times.
“That’s the plan,” I answered, looking over to Jessica who was cooking with her mother in the kitchen. She smiled back at me, then turned away to her chore, so I resolved to entertain Sam until dinner was served.
“I’m so excited! Since my birthday is in two days Daddy is finally letting me go this year!” she practically screamed with joy. I knew there was going to be drinking and costumes, but even at eighteen she wasn’t legal to drink yet. But if it’s her father’s party I’m sure she couldn’t get into too much trouble. I had long since gotten over being excited for Halloween parties myself. Most nowadays were just big singles hookups with lots of alcohol, and since I’d somehow scored the hottest and smartest girl I’d ever met, there was no point to them anymore. In fact I was only even going because it was Jessica that had asked me to come as her date.
“Got a costume picked out already?” I asked, taking a sip from my soda can.
“Jess didn’t tell you much about the party did she?” Sam asked, already knowing the answer, with a strange crooked smile on her face.
“Umm, only that she already has a costume picked out for me,” I responded confused.
“Okay then,” she looked up at the ceiling for a moment, in thought I guess, then said, “Then I think you are going to be in for a great time,” then made finger guns at me, pretending to shoot me. I had no idea what she was talking about, but she just winked at me as if she’d just given me some kind of obvious clue, but either I missed it, or just didn’t get the reference. With way dinner was called and we both joined the rest of her family for a nice chicken dinner that was almost as big as my family’s Thanksgiving. Granted it was for five, and they were much wealthier than my family was, and being an only child there were two less people at our meals, but it was still pretty shocking how much food was filling the large table.
I’d never been over for dinner before, and while I think it was big as a welcome to me, I think they also were used to bigger meals in general. We ate and talked about college, and I think I made a good impression talking about my goals to someday be a great lawyer like her father was, even if I was working and taking out huge loans to get the same schooling their daughter was attending, no doubt easily being paid for on their family money. But I knew she wasn’t just a spoiled rich girl, but could someday be a great lawyer herself if she wanted to, though sometimes she pulled back in class instead of hammering her arguments. That was actually how I asked her out last year, taking up her point and then sealing it with a great case-study I’d just read about. She thanked me after class and I don’t know where the boldness came from, but I told her she could make it up to me over dinner, and she said yes.
We were friends and study partners for a few months, then one long night of preparing, her long brown hair looking frazzled at two in the morning in the very empty library, and I couldn’t help myself but lean in and kiss her. Our lips touched, and as soon as I realized that I’d actually done what my tired brain wanted to do, instead of just imagining it, I was worried I’d crossed the line, but suddenly she was kissing me back so I just went all in. We made out for a dozen minutes, then she politely broke away, saying it was time to get to bed. I agreed, and we picked up, then held hands walking back to the dorms, and as I stopped, hoping to kiss her goodnight before turning back to my own dorm, she asked, “Backing out already?”
I never expected that, and almost embarrassingly I followed her to her room. I’d been an excited virgin unsure of what would happen next, and I think she knew it, so she pulled a condom from her drawer and said, “When I get back I only want you wearing this.” Then she went into her bathroom and I rushed to do as she instructed. I was so hard, I easily rolled it on after I was naked five seconds after she closed the bathroom door, and she came back out, looking like a beautiful naked angel.
She kissed and teased me in my lap sitting on her bed, took my virginity slowly riding me, then after a bit laid down and spread her legs, saying, “I want you to fuck me good and hard. I jumped in and pumped the shit out of her divine pussy for the next hour, using every trick in the book to not cool too soon. I was pretty sure she wasn’t a virgin like me, but I made sure I did everything in my power to pound her so good she’d be walking funny for a week before I filled that latex nightcap.
We both passed out, and I was kind of proud to do the walk of shame back home in yesterday’s clothes back to my own dorm. After that we dated and did a hell of a lot of fucking, and twice as much after I got her to move in with me to an apartment last month. I’m sure her parents and sister must have known we were intimate, but they kept the questions about our budding relationship positive and friendly. I’d worried about how this might seem, but it all went swimmingly.
I shook her dad’s hand firmly, laughed politely at his bland dad joke, and her mother kissed my cheek goodnight, saying she couldn’t wait to see me again at the party next week. Then I drove us home and was surprised how handsy Jessica was on the drive home. I almost considered pulling over somewhere, but this was a wealthy neighborhood and I didn’t want to get caught fucking her in my car in someone’s security camera. Then we were on the interstate for a bit, and back to our small two room apartment, only making it past the front door before she was on her knees ‘thanking’ me for behaving so well with her family. I would have done that without a congratulatory blowjob, but I also wasn’t going to refuse one either. In fact, that whole next week she was extra horny.
When we first started dating we had sex sometimes two or even three times a day, that only lasted a month before our hormones finally calmed down. After that it was every couple of days, occasionally three or four if you were busy. But this week she was just unquenchable. I woke up to her riding my morning wood, being tempted into indulging an afternoon delight lunch quickie, and enduring her gently stroking me in my pants during class one afternoon so that she could dick me off in just five minutes before her next class. I had no idea what had gotten over her that whole week, but other than a bit of chafing, I wasn’t going to stop her for all the tea in China.
Halloween morning she woke me up rubbing me gently, but said, “Got a big day ahead of us, better get a good breakfast,” then left me to shower and shave alone. She was already dressed when I got out, so I did the same, and we went about our day much more normally. Honestly, I was kind of thankful for the break as it was becoming a bit much for me to keep up with. As every guy will tell you, sex every day is a great fantasy, but having to perform that often takes a toll on you after a while. And Lord knows, the last thing I wanted was for sex with the woman I wanted to marry someday to become a chore.