My name is Maddison.

I like to think I’m cute and sexy, if not a little thin. I’m at least not unhealthily skinny or fat, so that’s a plus.

My life has quickly spiraled out of my control recently, and I feel it’s time to tell my tale. I don’t know how it happened…well, I mean I know how it happened, but I don’t know how I let it happen like it did.

You see, I’m what people call a cuckquean. I’m sure you’re going to Love my story, so let’s dive into it!

I graduated college just a few years ago and have a decent job at an advertising firm here in the city. Three of my friends (Kayla, Britney, and Megan) from college also got different jobs in the same city, so we felt that was a sign and moved in to a big condo together. Let’s be honest, we all come from families with money, so we just had to pick who was going to buy the condo and the rest of us would pitch in each month for the mortgage. Kayla was the lucky one to buy the place (with her daddy’s help of course), so she got the master bedroom with attached bathroom. The rest of us each got a bedroom and one bathroom to share. It at least had two sinks and a big Shower stall. We agreed we could share Kayla’s tub if we wanted to take a nice bath or anything, so that was a bonus.

The place was nice in the main areas too. A big living room we furnished with a huge wrap around couch and tv, a big kitchen and walk-in pantry, a dining area (I’d say room but it was an open concept main living space so it wasn’t a separate room). The bedrooms even had l small balconies overlooking the street below. Overall, it was going to be a great place to live.

I was the last to move in. This also meant I had the smallest room, but I was ok with that. I was mostly going to be in the main living area anyway except to sleep and stuff.

So, it was a Friday night when I finally pulled in with a small moving truck to move my furniture into my room. Luckily, my boyfriend, Christopher, was there to help with the heavy lifting. Not gonna lie, he looked gorgeous carrying my furniture in. He isn’t like an Adonis all the time or anything, but he works out enough to have decent muscles. I always thought we were cute together, my clearly feminine if slightly petite build with his masculine slightly muscular build. I loved it.

Now, I know he would’ve done it out of pure kindness and Love for me, but I made it worth his while. Well, to be honest, it was also a bit selfish. You see, the best part about him physically is definitely his dick. I have only been with 3 guys in my life, but Christopher’s was far and beyond the best tool I’d been with. It was long and thick, it felt like it reached every inch of my insides. So, when I let him rest on my bed while I took control on top, it was partially to thank him for all his help, and also partially for me because I was just getting Horny.

I know you’re probably hoping for a ton of details about the Sex, but we are barely getting started with my story, so you’ll have to be patient at least a little longer for those.

After two nice orgasms for me and Christopher Cumming on my stomach, we decided it was time to clean up. I jumped up to take a quick Shower while Christopher waited in my room for me to finish. The Shower was definitely big enough for both of us to use at once, but we decided it was best to save that for another time. I finished my Shower in about 15 minutes, which was a pretty good time if you asked me. I toweled off, wrapped the big towel around my body, and l left to go back to my room.

As soon as I opened the bathroom door, I saw Kayla closing my bedroom door looking embarrassed. She made eye contact with me and spoke up.

“I’m so sorry. I was looking for you, but apparently you weren’t in your room.”

“Oh, yeah. Sorry. Hope Christopher didn’t scare you.”

“Oh no, it’s ok. He was definitely unexpected…” Kayla seemed to zone out for just a second. Then she continued. “I just wanted to see if you wanted to watch a movie with us tonight. We can all get comfy in the living room and enjoy our first night living together.”

“Ok, sounds great!”

“You can invite Christopher to stick around too, could be fun to have him around.”

“Ok, I’ll see what he wants to do. I’ll get dressed and see you in a few minutes.”

Kayla headed back to the main living area while I walked to my room. I opened the door and found Christopher on the bed naked still. Wait, did Kayla just see him naked too?

“Uh, did Kayla just come in here?”

“Oh, no. She just opened the door looking for you. I told her you were in the bathroom.”

“And you were naked the whole time?”

“What? No, babe. I pulled this sheet to cover myself. Nothing happened.”

“Ok, fine. I trust you.”

“Good!” Christopher jumped up, dropping the sheet and pulling me close against his body. His dick was already getting hard again. He took the opportunity to strip the towel off my body and ran his hands all over me.

It was then that I realized I was turned on again, and Christopher noticed quickly.

“Maddison! Are you wet again? Did you get wet thinking something happened between me and Kayla?”

“Uh, no. I don’t know.”

“Awe, that’s cute. Well, I gotta take a Shower.”

“Cover up before you go out there!”

“Of course babe!” He took my discarded towel and wrapped it around his waist.

“Also, the girls want to have a movie night and you’re invited to hang out if you want.”

“A night of being close to you? Hmmm I think I can make that work.”

“Fun! Ok, go Shower! I’ll see you in a bit.” I threw on a simple cozy shirt and shorts, ready to relax for the evening.

I had another surprise when I opened my door again. This time it was Megan closing the bathroom door just down the hall.

“Uh, Meg, what are you doing?”

“I’m sorry Maddison! I didn’t realize Christopher was there! I thought it was you or Britney and I just wanted to put my curling iron under the sink. Nothing happened! He was already in the Shower and I just threw it under the sink and left immediately once I realized it was Christopher.”

“Oh, uh, ok.” I literally had no idea how to react to that. It seemed like two of my three roommates may have seen my boyfriend naked and I’d only been living here for like 3 hours! I trust Christopher not to do anything with them, but the real issue was: why is my Pussy getting wet right now?!

I walked out and found all three in the kitchen talking. I only heard the last couple words before they all turned and greeted me as I came around the corner.

“…in there right now?”

“Yeah, but I think she is over there too. Hey Maddison!”

“Maddison! Congrats on finally moving in!”

I seemed to catch them off guard about something, but whatever.

“Haha thanks! I’m so excited to live with you girls! This is going to be awesome!”

“Of course it is! And this is a great excuse to have our first ‘slumber party’!”

“Yeah! movie night tonight!”

“Speaking of, I need to change in to comfy clothes. I’ll be right back!” Britney hurried out of the kitchen and out of sight towards our rooms. Not sure if I’ve mentioned it yet. But the kitchen was kind of the hub for the condo. The living room, dining room, and kitchen were first when you walked in mostly in an open concept setup. Aside from the big table with an overhanging table cloth and the kitchen island, you could see just about everything in all three “rooms” at the same time. Off of the kitchen there were two hallways, one led to the laundry room and master bedroom while the other led to the other three rooms and our shared bathroom.

A couple minutes later, Britney came back in her pajamas. She immediately looked at the other two girls and her eyes got big. Then they all started laughing. I’m not sure what the joke was, but they at least were enjoying it.

“Right?!”

“Yeah, definitely.”

“Ugh, so lucky.”

I clearly didn’t understand, so I took the opportunity to go check on Christopher. He was in my room again getting dressed.

“Ok, I don’t have a ton of clothes with me as I was just expecting to spend the night with you in here. But I have some shorts I can wear at least. My shirt from earlier is dirty, but I can wear the one I brought for tomorrow. It’s just a tshirt, but we are supposed to be comfy, right?”

“Yup, that works. I’m sorry about Megan walking in on you in the Shower earlier. She apologized too.”

“Oh, no worries! They didn’t bother me. They left fast.”

“They?”

“Oh. Megan came in earlier, and Britney accidentally walked in while I was drying off. They were both super nice about it though and we just laughed it off.”

All three of them had seen him naked already?!

“Wait, so all three have seen you naked?”

“Well, I guess. But babe, they were each accidents. You live with them now, accidents are bound to happen eventually. I promise, nothing happened.”

“Ok, ok. I’ll drop it then.”

“Good!”

Though, good wasn’t quite the word. I couldn’t figure out why, but my Pussy definitely started getting wet again when he told me about each of them seeing him naked. I’m going to assume it’s just residual hormones from our evening Sex.

Once we were both ready, we headed back to the kitchen together. The girls welcomed us again as soon as we walked in, but I’m pretty sure they each glanced down to our interlocked hands. I may have even imagined it, but I think Kayla tried locking eyes with Christopher. At least she didn’t look at me at all, she kept her eyes on him.

“Glad you two could join us! Enough time in your room already.” Kayla smiled at Britney and Megan as she said this and they giggled back at her.

“Oh no! Don’t tell me you could hear us earlier?!”

“Haha of course we could! It’s not that big of a place and the rooms aren’t sound proof or anything.” Britney was loving this.

“Oh my God! I’m so embarrassed!”

“Awe, don’t be! It sounded like you had a great time.” Megan smiled at me as she spoke.

“Well, we’ll be quieter next time. I’m sorry we made so much noise.” Christopher was such a nice guy and it was great to see him already getting along with my friends. He wrapped an arm around me, squeezing me tightly. I was so embarrassed and it just made me blush more.

“Like Megan said, no worries at all! We assume you’re going to be here often, so get comfortable. We won’t judge!”

“Ok. That’s enough about our Sex life for now. What did yiu have planned for tonight.” I just needed to change the subject as fast as I could. Kayla seemed to understand and helped me move the conversation on.

“Well, we have pizza coming in a little while for dinner. We have plenty of wine. We were thinking a movie and maybe some fun with a game. Tonight is your first night here Maddison. Which should we do first?”

“How about we start with a game or something? Then we can watch the movie until we are ready to fall asleep.”

“Sounds like a great plan Maddison! Ok, what do you think: Board game? Card game? Something different?” Kayla seemed to be taking charge. Maybe she felt having the master bedroom made her the leader?

“Ooo, what about a fun sleepover game! Cause this is basically the first night of our long sleepover.” Megan stuck her tongue out at us as she finished, clearly joking around.

“Great idea! Ooo! What about truth or dare?!” Britney had this extremely excited look, like a kid who just walked into the living room on Christmas morning. It seemed Britney either didn’t get the joke or just really wanted to play truth or dare.

“Ha! That’ll be fun and a great way to all get comfortable living together! Love it!”

We all moved to the living room with glasses of wine and some snacks. The game started off rather tame. A few truths to get everyone comfortable. Kayla had slept with 5 different guys. Megan had only ever slept with one guy and only once with him. Britney and Kayla were bisexual but had never had girlfriends. Christopher had slept with 2 other girls. Megan was afraid of deep water. Christopher had a celebrity crush on Natalie Portman (don’t we all?). I told everyone I had never had thoughts about other girls before, I was super afraid of heights, and my favorite Sex position was doggy (I know, I’m not super adventurous).

Britney was the first to say dare. Kayla set an interesting direction for the rest of the game with the dare.

“I dare you to send a sexy DM to a celebrity on Instagram”

“What?! That’s embarrassing!”

“It’s the dare, let’s see who!”

She ended up sending Harry Styles a sexy message, but we don’t really expect him to respond. Though, the dare dam had been broken so now there was the subtle pressure to keep doing dares. Kayla was next. She was dared to give a banana a Blowjob, which she performed enthusiastically. I’m not 100% sure, but I thought I saw her intentionally make eye contact with Christopher a couple times, but I may have just been making it up in my mind.

Just then, the doorbell rang.

“That must be the pizza!” Britney got up to get money.

“Wait! It’s Maddison’s turn! Truth or dare??” She turned to look at me with the same excited expression as she had when she brought up the game. I had a sneaking suspicion this was the whole reason she wanted to play. I knew I would probably regret it, but I also knew what I had to pick.

“Oh, uh, dare.”

“I dare you to take your pants off and get the pizza in just your shirt and underwear!”

“What?!?? I have a boyfriend!”

“I’m not telling you to date the pizza boy, just let him see you in your underwear! It’s not cheating or anything.”

“Christopher, are you ok with this?” I wasn’t going to risk my relationship just for a dare.

“Sure babe! It’s just in fun. You aren’t betraying me or anything. We are ok. Take them off!”

Well, no getting out of it now. I quickly pulled my pants off, laughing as Kayla ran off with them, claiming to do so to ensure I didn’t put them back on. Britney gave me the money and then they all sat to watch me answer the door.

I opened the door, and a younger guy was standing there with our pizza. He couldn’t have been more than 20 years old. He looked like an underclassman in college or something. His eyes got big when I opened the door.

“Uh, hel…hello. I have your pizza.”

“Yup, thanks!”

“Do you need me to come in and put it on the table?”

“Oh, no, I’ll be ok. Here let me take the pizza and I’ll give you the money.” I handed the guy his money (thanks Britney) and gave him a playful smile as I closed the door.

“That was so embarrassing! He saw me almost naked! I just had panties on!”

“Haha he loved every minute of it! And don’t pretend you didn’t Love it too.” There was no way I was going to admit how thrilling it was to them. Nope, that would probably be dangerous, just based on the excited look they each had plastered over their faces.

“Yeah, your nipples are hard and it isn’t from the cold!”

“Haha! What about you Chris, did you like it?” Christopher has always preferred people call him Christopher, so I knew he was going to correct Kayla when she called him Chris.

“Well, Maddison is beautiful, and I Love seeing her sexy body. So, yeah, it’s started turning me on!”

He didn’t correct her. Weird. He always corrects people for that mistake.

“Ok, bring the pizza over her Maddison. Megan, Truth or Dare?” Megan picked truth and admitted playing in public was one of her favorite kinks.

“And Chris, it’s your turn! Truth or Dare?”

He picked dare, turning and smiling at me while he waited for them to decide his dare. I expected the girls to go with something ridiculous, just based on me basically flashing the delivery guy. But they surprised me by all turning to look at me, as if waiting for me to come up with the dare. I was not ready for that and couldn’t think of a single dare.

“Oh, uh, I don’t know. Do you have any ideas?”

They all looked at each other for a few seconds, then started throwing around ideas.

“What about him being our servant for the rest of the night?”

“Ooo, we could dare him to flash us!”

“What?!?! No! Absolutely not!” I couldn’t believe Britney had suggested that.

“Ok, ok. My bad. You’re right, that was too far.”

“I think it could be fun to see how good of a kisser he is!” Kayla had a glint in her eye with that one.”

“Guys, he’s my boyfriend.”

“Then he can kiss you! Christopher, I dare you to show us how much you can turn Maddison on just by making out with her!”

My mouth dropped as Britney said it. I turned to look at Christopher, who looked excited as he turned to face me next to him on the couch. I didn’t even have time to verbalize my protest before he wrapped his arms around me and had his lips on mine. He pushed me back into the couch cushions as he also pulled my body against his.

Apparently I was more turned on than I realized as I melted into his kiss almost immediately. I opened my mouth invitingly as we continued to make out in front of my roommates. It only took about 2 minutes until I was desperate to take Christopher back to my bedroom. I’m not sure if it was because we had an audience or because I’d had a couple glasses of wine, but that was the hottest kiss we’d ever had. The girls cheered and whistled as we finished. I just sat there stunned for a bit.

“Fuck, I need a boyfriend.” Kayla spoke up as she stared at the two of us.

“Ha, yeah, he’s pretty good, that’s for sure.” I honestly didn’t know how else to respond to that.

I’m not 100% sure why we moved towards the sexy side of truth or dare so quickly. Maybe it’s just inherent to the game. Regardless, here we were.

We played another round of dares after that. Britney was now sitting in just her bra. Megan chose truth, but we forced her to change to a dare. Because she tried to back out, she had to flash her boobs from her balcony. We didn’t see her nipples or anything because we were behind her, but it was still fun to tease her as she completed the dare.

When it came or my turn, Kayla came up with my dare: “I dare you to pretend to be a dog for the rest of the game and movie! Like bark like a dog, play fetch like a dog…”

“Haha easy, I can do that! Bark bark!” They all laughed at my barks.

“Hahaha! Well, no dogs on the furniture! Get down girl!” Megan was laughing as she said it, but I played along and hopped off the couch. I think she was getting back at me for the teasing just a bit ago.

“Here, fetch!” Britney tossed a pizza crust a few feet away and we all had a laugh as I chased after it and brought it back with my mouth. Britney pet me on the head and said, “You’re a good girl Maddison! Wait, that’s a weird name for a dog. I think I’ll call you Maddy while you’re a dog.”

Everyone loved it and started calling me Maddy. I didn’t mind, so let them have fun with it. We joked around for a few more minutes with everyone getting a chance to make me fetch, or roll over, or bark. Eventually we decided to move on to the next person.

Kayla got up from her seat on the ottoman and said, “here Maddy, no dogs on the couch, but you can sit or lay down on the ottoman.”

That left just Christopher and Kayla. For this round.

“Ooo, I have an idea! It’s a dare for both of you!” Britney said, looking at Christopher and Kayla.

“What is it?” Kayla didn’t show any hesitation for a two-person dare.

“I dare the two of you to pretend to be boyfriend and girlfriend while we watch the movie!”

“What? Like just sit next to each other? That seems to easy.”

“No! You have to snuggle close, be all lovey-dovey, you know, the standard pda that people expect from couples.”

“Haha I don’t want to make Maddy uncomfortable though! He’s her boyfriend. But if she’s ok with it, I’ll pretend to be his better half for a while.”

They all turned to look at me. To be honest, I didn’t Love it. But I’d had a couple glasses of wine and I don’t know why, but my Pussy was tingling and distracting me. I made eye contact with Christopher to make sure he was ok. He nodded towards me. The peer pressure, wine, and arousal tipped the scales.