The Extraction
Copyright© 2025 by Canairs90s
Chapter 9: Charitable Endeavors
Coming of Age Sex Story: Chapter 9: Charitable Endeavors - With one week until they graduate from college, two long time friends need to finally confront their feelings for one another and figure out what comes next.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual True Story Slow
I woke up Saturday morning to the sound of the over-the-garage apartment door opening and someone bounding up the staircase. I quickly made sure I had not shifted too much in the night and there was still room for Madison to slide in next to me. When Katie appeared in the doorway I was surprised, and glad I had put on some clothes when Madison got up to go back inside her parents’ house the previous evening.
“Hey Drew! Sorry if I woke you up!” exclaimed Katie. “I felt really bad about having to leave last night so I woke up early this morning and brought everyone coffee! I didn’t know what you liked so I just got a vanilla latte since it’s my favorite! Wait, where’s Maddie?”
“Uh, thanks, she’s inside I assume,” I said groggily. I was still half asleep.
“Oh, okay. Their stupid parents’ rules, I bet. I thought you and Maddie might be immune since you’ve graduated. Oh, right, just friends, maybe you have to upgrade to boyfriend and girlfriend before she’s allowed to stay! Anyways, be right back, have to go put Maddie’s inside,” Katie babbled and put a coffee on the side table before running off down the stairs.
When she returned a few minutes later my brain had begun to function so I could process Katie’s appearance. She was wearing a pink yoga pants-sports bra outfit and sneakers, but she was wearing all the same jewelry she had been the previous evening, which seemed odd to me.
“It was so great to meet you yesterday! Maddie’s been like a different person since she visited you, so I was super excited to see her to lighten up a little bit,” Katie said happily. I had no idea how anyone could have this amount of energy at such an early hour.
“Yeah, uh, it was nice to meet you too,” I said, still a bit bleary. “You definitely bring a different energy to that group.”
“Thanks! I try, they are sort of ... stodgy, I guess? I don’t want to be mean, but they just don’t seem to like having fun that much. I was sort of hoping if you are around more we could sort of be allies since we’re kind of the outsiders,” Katie said.
“Yeah, I think that sounds good. I don’t want to judge, but while they were nice it did seem sort of stilted. Madison’s not like that when she’s not around them. Trust me, she’s fun.” I was thinking of some of our more adventurous college nights out.
“Oh that’s good to know, I’ll have to see if she wants to go out with me and my sorority sisters sometime! We love to go out,” Katie said.
“You live around here?” I asked.
“Sort of, my mom lives in Plano, but it’s boring in suburbia and the guy she’s dating is fucking weird. So I went in with some of my sorority sisters and we rented an apartment in Uptown for the summer. It’s kind of crowded with four of us, but it’s so convenient to all the best bars and clubs.”
“Cool, you’ll have to give me some tips on good places to take Madison if I visit again. Ha, let’s be honest, when I visit again,” I said.
“Good, I was hoping to get to see more of you!” Katie said. It seemed like an odd comment to me, but I was trying to be polite.
“So what are you doing for the summer?” I asked.
“I got a job working as an administrative assistant over at Parkland, that’s the big hospital you probably saw from 35 on your way in. I figured if I was going to stick with nursing, I should get used to the environment, plus I get to meet lots of interesting people,” Katie explained.
“I’m sort of surprised by that, wouldn’t think a hospital is a good place to meet people,” I said. My personal policy up to that point in life had been to avoid hospitals at all costs.
“It is if you don’t mind putting yourself out there a little bit. Plus I like meeting older people,” Katie paused, as if realizing she’d said too much. “I mean older people have a lot of wisdom I can learn from. I know people think I’m just a dumb blonde because I’m high energy and well, these.” She pointed to her disproportionately large boobs. “But I know I have a lot to learn in life and I think it would be dumb not to listen to those who have more experience. That’s why I asked about picking your brain about majors last night.”
“Interesting philosophy, probably a smart one,” I mused. “Speaking of last night, how did your little engagement go?”
“Oh it was great! I got to do two of my favorite things.” Katie paused and bit her lip as if she wanted to say more but knew she shouldn’t.
“Well good. Conor was a little pissy, but we watched a movie with him and cheered him up, so I think he’s all good,” I told her.
“Oh good, I always feel bad when I have something come up, but you know how it is with busy college life,” Katie said. She was apparently having a much busier college experience than I had.
“All good, I’m sure you can make it up to him,” I said.
“Oh I promise you I will,” Katie said far more suggestively than I thought was appropriate. “Uh, do you mind if I take a quick shower. I got up so early I didn’t have time to before getting coffee and I have my pole dancing class in like 30 minutes.”
“Uh sure, I guess, you know where the shower is?” I asked. Unlike a typical apartment it was not off the bedroom, but down the hall.
“Yeah! So this is a little secret, but Conor actually gave me a key to this place. I stay here sometimes when my roommate has a guy over then I sneak out in the morning. As long as his parents aren’t in the kitchen it’s easy to sneak past the house and I just park my car around the corner. Sometimes Conor also sneaks back here after they’re asleep and, well, you know. Sorry, that’s way too TMI!” Katie clapped a hand over her mouth.
My brain skipped right past Katie’s overshare to hone in on Conor sneaking out. “Hmmm, I wonder if Madison knew about her little brother sneaking out to meet up with you if she would have been so insistent about following the rules around not sleeping here last night,” I said.
Katie shrugged. “Now you’re seeing why I didn’t realize your ‘just friend’ Maddie had a fun side to her. Anyways, it was good to chat a little one on one, but I gotta grab that shower, see you at brunch!”
“See ya, thanks for the coffee,” I replied.
I grabbed my phone to text Madison I was awake and that Katie was there and taking a shower, then began to mull over our discussion. It had been a strange conversation any way you looked at it, but I also saw opportunity. If Conor was sneaking around with Katie, there was no reason for Madison not to stay the night tonight.
Madison arrived about five minutes after I texted her. In contrast to Katie’s arrival, she carefully opened the door to the apartment and padded up the stairs, so I only realized she was there when she entered the bedroom, coffee of her own in hand. I had been sitting up in bed checking baseball box scores on my phone.
“Morning,” I said casually, but couldn’t keep the smile off my face.
“Hey,” Madison said in a soft voice. She appeared to be having the same issue refraining from smiling. She handed me her coffee to hold while she got in bed next to me, then I passed it back to her and she thanked me. I liked that her first instinct was to climb into bed with me. It was exactly what I had been hoping she would do.
“You still don’t drink coffee, right?” Madison asked.
“Ha, nope, I guess nice of Katie to try though,” I answered.
“I told you she’s sweet. This is one of her go-to moves when she has to stand up Conor,” Madison said. “I’m always so impressed she can wake up so early and be so energetic.”
“I don’t know, Mads. We had a little chat this morning. I think there may be more to sweet little Katie than you think. Waking up too early to take a shower then asking to shower here makes no sense,” I said.
“Eh, there could be a bit more to it than that,” Madison said, then lowered her voice. “Maybe she had to take a huge dump. If I were her I would certainly have asked if I could take a shower to cover for that.”
“Hmmm, I suppose that’s fair,” I chuckled.
We heard the shower down the hall stop. Madison and I looked at each other. The question was unspoken - were we okay with Katie finding us in bed together? Madison shrugged, I nodded. It was hardly a secret we were romantically interested in each other even if we were just friends.
“Nothing weird about having coffee in bed with your best buddy, right?” Madison asked.
“Pass me my coffee? I don’t want to look rude,” I told Madison. She grabbed the cup and handed it to me. That’s how we let Katie find us, perched together in bed, fully clothed, and sedately sipping our coffee.
“Maddie! Good morning! You two are just so cute!” Katie exclaimed when she discovered Madison had joined me in bed. She had re-dressed in her pink workout outfit and her hair was dry, so perhaps Madison’s theory was correct.
“Thanks so much for the coffee,” Madison said in a tone I found annoyingly energetic. “Do you want to text Conor to get out here and we can chill for a bit?”
“Oh that would be so much fun! But like I told Drew I have a pole-dancing class to get to this morning, so I have to run. But I’ll definitely see you at brunch!” Katie exclaimed with characteristic enthusiasm. We listened to her bouncing down the stairs and throwing the door shut behind her.
“You joining Team Morning Person?” I asked, jokingly.
“Ugh, no. Although my internship is kind of forcing me to be more of one. That much energy this early though? Pass. Honestly? I feel like I have to at least try to match her energy a little because otherwise I’m the frumpy older sister,” Madison said.
“I don’t think ‘frumpy’ is applicable to you, Mads. Especially not after last night,” I said, then ran a hand up her thigh to emphasize what I meant.
Madison laughed. “Yeah, I am liking this new version of me much better. You and I have had plenty of talks over the years worrying about whether or not we were having enough fun. It’s the same kind of thing, I guess in some ways maybe I was the one giving myself the frumpy label, but since we’ve gotten together I feel like I’ve shed that. It’s nice.”
“Huh, I’ve definitely never thought of you that way, but I guess I can sort of see, between how serious you are, how studious you were, and not having much experience dating, why you gave yourself that label,” I said.
“Exactly! I feel like unless people get to know me, they think I’m this frumpy, stuck up Dallas girl.”
“I can see it, but it’s also an idiotic oversimplification of your personality. Honestly it makes me a little mad to think about because you’re so much more than that. I like how blunt and straightforward the real you is. The performative stuff is so lame,” I said.
“Oh yeah, and it’s worse down here, too. Girls are supposed to just have ‘energy’ and be ‘sooo excited’ all the time. I find it so exhausting. Performative is a good word. But I also feel like if I don’t match, and just be my cynical self, I get judged.”
“For the record, I very much enjoy your cynical side. I think it mirrors my own,” I pointed out.
“I think this is why we get along well,” Madison said. She had hooked her arm around mine during the discussion and now lay her head on my shoulder. I sensed that she had tired herself out peeling back another layer of the onion of her inner thoughts.
“Exhaust yourself with all those feelings?” I kidded Madison.
“Nah, I actually feel more comfortable discussing those around you these days. It’s just I’m not a morning person, vicious accusations to the contrary aside,” she said with a little chuckle.
“Team night owl for life!” I joked.
“So I know you never thought of me as frumpy, and really part of what made me start to even think about getting out of that mindset was all the fun we had in Spain. But there was one thing in that realm that kind of bothered me about our Nantucket trip,” Madison said. She had sat back up and turned to look at me.
“As I recall our little Nantucket rendezvous was a masterclass in not being frumpy,” I noted.
“Good point,” Madison replied. “But one thing I learned about myself is that I really liked giving you pleasure. You were so thoughtful and dedicated to pleasuring me. It turned me on and, unlike lame Dallas girl energy, that energy I wanted to match. But I didn’t feel like I did a very good job blowing you and that bugged me. You know I want to be the best at everything. So I’ve been practicing on a dildo for the last few weeks and was thinking, maybe I could try the real thing?” Madison asked, mischievous sparks in her eyes.
“I dunno, you studying and practicing sex is kind of nerdy.” I couldn’t help but tease Madison, although I couldn’t keep a straight face. Neither could she.
“Fuck, I’ll embrace nerd, just not frumpy nerd,” Madison joked back.
“This I can live with,” I said, smiling. “Joking aside, honestly that’s incredibly hot, Mads. Both that you were doing that, and doing it with me in mind.”
“I’m glad you think so,” Madison said, then dropped her voice to a whisper. “Just between you and me, sometimes when I was practicing, I got a little turned on thinking about you and our sex and the dildo ended up inside me in a different hole than my mouth.”
Picturing Madison getting so turned on she couldn’t resist masturbating was more than I could resist, I rolled on to my side and kissed her. She eagerly met my passion.
We came up for air and Madison put our coffees on the bedside table since it was on her side of the bed.
“I’ll let you get some practice time in on the real thing under one condition,” I said. “I also get to practice on the real thing.”
“I’m not sure you need a ton of practice based on last time, but I certainly won’t say ‘no’!” Madison replied. She pulled off the shorts and underwear she had been wearing as pajamas so she was naked from the waist down. I crawled between her legs, which she spread.
I experimentally ran a finger up Madison’s slit. There was a little moisture, but not a ton, which made sense, our conversation had only turned sexual a few minutes ago. I set about getting her turned on. I kissed and nibbled my way up one inner thigh and used my opposite hand to lightly tease her opening. After a few minutes I could feel her juices starting to flow and I replaced my hand with my mouth.
I had learned during our previous visit how delicious Madison’s natural taste was so I didn’t go wild the way I had the first time I went down on her. I kissed and licked around her outer labia before I began working my tongue into Madison’s opening and licking her inner labia. I was getting the groans I was learning meant Madison was working her way towards orgasm as the result of my efforts.
I continued to lap away, not in any rush. Madison tasted great and it excited me how much pleasure me eating her out gave her. I snaked my arms under her thighs, they were just long enough I could reach up under her shirt and play with her boobs. I heard a gasp when I made contact with her nipples and her own hands went over the top of mine. Madison began essentially rubbing her own boobs using my hands. I realized she was showing me how she liked to be played with up there. ‘Clever Madison,’ I thought to myself.
I was trying to see if my tongue could reach Madison’s g-spot, I didn’t think it was long enough, but for Madison it was having the pleasant side effect of my nose nuzzling her clit. Between that and the nipple tweaking the gasps and breathing had escalated. I sensed she was close and switched to licking her clit with broad strokes of my tongue. I felt her body tremble as she climaxed. Madison’s orgasm wasn’t cataclysmic like some of the previous ones I had seen her have. I sensed it was more of the ‘gentle wave’ variety that washed over her as she reached that state of pleasure.
I lifted my head so we could make eye contact. She had a blissful, happy smile on her face.
“I don’t think I’m ever going to get tired of that, it feels so good,” Madison said.
“Good thing I like doing it,” I replied. “It turns me on to make you feel that good.”
“I know and I feel like now I understand that better. I’m excited for my turn.”
“I’m more than ready after that, where do you want me?” I asked.
Madison laughed. “You know, that’s something I totally didn’t think of when I was practicing, I usually did it just sitting up in bed.”
“I guess I could try to get on my knees,” I offered.
“Nah, the angle is probably weird, do you want to just lay down?” Madison suggested.
I pulled off my clothing then took my original place in bed, but on my back. Madison seemed to get the hint and finally removed her own shirt before kneeling next to me.
I was fairly hard already and Madison started by ensuring I was at full mast. I immediately sensed greater confidence from her as she took my shaft in one hand and lightly stroked it while the other cupped my balls. She stopped for a minute and pulled a hair tie off her wrist to put her hair in a ponytail with a saucy look in my direction. She retook her place over me and began to lick my cock. She was still a bit tentative, not fully sure what she was doing, but it was obvious she had been doing research on how to slowly build things up. I was trying to make the appropriate noises of pleasure to encourage her.
After a few minutes she took the head in her mouth and swirled her tongue around it. It felt amazing, unlike anything she had done previously. I couldn’t help but gasp with pleasure. I was no longer just making noises to encourage her. She could get about half of my shaft into her mouth. She seemed to have a pretty good idea of the limits of her gag reflex, likely a result of her prior practice, and used her hand to stroke the base of my shaft where she could not get to with her mouth. She began to bob up and down, again using her tongue as she worked. Her technique was still imperfect, but it was good enough considering how turned on I already was.
“Mads, I’m getting to the limit here, I’m going to cum,” I warned her.
“That’s so fucking amazing,” Madison said happily, briefly rising off my cock although her hand continued to stroke. “Do you mind cumming on me again? That really turned me on last time.”
“Uh sure, how do you want me to?” I asked.
“Kneel over me,” Madison suggested and got on her back next to me. I got up on my knees and straddled her stomach. Excitedly she reached up and grabbed my erection with one hand and my balls with the other, giving me the last bit of physical stimulation needed.
“God I want to just be covered in your cum. Like your filthy slut. I want it so bad,” Madison breathed. There was the last bit of mental stimulation I needed. Over the cliff I went and my cock exploded. Most of my load hit Madison’s boobs. One rope shot as high as her collarbone, at the end a bit dropped to her stomach.
“I can’t believe how much that turns me on, phew!” Madison exclaimed. A bit of my jizz had gotten on her hand and wrist. She regarded them critically then gave a small shrug and began playing with what was on her boobs, apparently fascinated by the substance.
“That is unbelievably hot,” I said. Deciding I wanted to reward Madison I scooted back and got back between her legs. She protested but I grabbed her thighs and held her in place.
“If you’re serious about being my slut play with my cum while I lick you to another orgasm,” I ordered her. Without waiting for a replay I attacked her clit with my mouth. It did not take much, probably not even a minute before I felt Madison shake as she came again. She gave a small yelp as well.
I crawled back up the bed and plopped down next to Madison. She was panting heavily, eyes half closed. Her chest was a sticky mess.
“Kind of no fair you got to get me off twice, I can’t really complain though. That was amazing,” Madison said once she had started to regain her faculties.
“I was feeling charitable, it seemed like a fitting reward for all your practice,” I said.
“Two more firsts for me,” Madison said grinning. “First time getting a guy off primarily with my mouth.”
“And first time getting your clit licked while you play with a guy’s cum?” I guessed.
“Yep! Alright probably should get cleaned up, don’t want to be late for brunch,” Madison said.
We hopped in the shower, although Madison only stayed for a couple minutes to wash my ejaculate off. She pointed out that if she showered in the apartment instead of the main house, it would be weird and notable to her family. I admitted she was right although it did make my brain start thinking about what Katie had revealed about her sneaking around and Conor’s little trysts. I was up in the air on whether I should keep that a secret or try to leverage the information to convince Madison it would be fine for her to stay the night.
After my shower I dressed in khaki shorts and a polo - black, of course, per Madison’s preferences - and made the short walk from the apartment to the back door of the main house.
“Good morning, mimosa?” Madison’s mom called from the kitchen when she saw me.
“Uh sure, thanks,” I said, not wanting to be rude and noting she already had a flute. I had never been offered a drink during the morning. In college my friends and I mostly stuck to ‘normal’ drinking hours - Friday and Saturday nights, maybe an occasional thirsty Thursday or a beer during the week. It was one more subtle thing that reinforced this was a very different lifestyle from what I was accustomed to.
Madison’s dad and a freshly-showered Madison joined us over the next few minutes and accepted mimosas of their own. Her dad helped in the kitchen while Madison joined me on a bar stool at the kitchen island to chat.
“This is their routine, they do this almost every Sunday. It’s a throwback to their restaurant days to be cooking together,” Madison explained.
“Saturday this week,” I pointed out.
“Yeah, I pulled some strings,” Madison joked. It would only be later that I learned how big a deal this had been to Madison, altering the tradition of the sacred Highland Park tradition post-church Sunday brunch was a huge ask.
“It’s impressive how they work as a team almost wordlessly,” I noted.
“Couple goals,” Madison said, with a shy smile. I returned the smile. If Madison was thinking of her and I as a couple, much less one that could hold a candle to her idealized parents, that was a good thing.
Over the next hour Madison’s maternal grandparents arrived and I was introduced to them, followed by Katie’s return, which was apparently Conor’s cue to emerge from his room.
The food was fantastic - everything tasted like it was made from scratch and based on what I had observed in the kitchen that was likely the case. Eggs Benedict with possibly the best Hollandaise sauce I’d ever tasted, thick slices of crispy bacon, homemade hashbrowns with jalapenos mixed in for a little kick, fresh fruit, and the inevitable fresh round of Mimosas.
Conversation over brunch was much different than last night at dinner. Madison’s grandfather largely guided it instead of her mom, who obviously deferred to him. Katie was more subdued now and looked a little unhappy. I was the target of a few questions regarding my parents and education but the conversation quickly moved on to business and gossiping about members of their elite social circle. Madison and Conor were limited participants. It was not a children should be seen and not heard type of thing, just an expectation of deference. I did catch a ‘told you so’ look from Katie. I didn’t blame her, it was a pretty boring discussion.
After everyone had eaten, the ‘kids’ - Madison, Conor, Katie and I - cleared plates and cleaned up the kitchen while Madison’s parents and grandparents made coffee and settled back in to chat. Madison explained it was normal for them to sit and chat for a few more hours but we weren’t expected to join them. Katie begged off to go take a nap before the charity thing she and Conor were supposed to go to with his parents that night. Conor decided to hit the gym. I could almost sense the frustration radiating off the poor guy.
Madison knew I was a bit of a history nerd, so one of the activities she had suggested while I was in Dallas was that we check out the Sixth Floor Museum. We agreed that it seemed like a good time to do that and get out of the house for a bit.
I had low expectations for the museum - how much is there to really say about an assassination that lasted just a few seconds? I was pleasantly surprised, however, by the depth of the displays. There was a lot of great information about the political climate of the ‘60s that created the backdrop, the errors the Secret Service made, how the shooter was radicalized, and how he was ultimately killed in police custody.
“Gosh Mads, this is surprisingly interesting. I’m actually learning a lot,” I whispered after perhaps half an hour.
“I know, same. The last time I was here was a middle school field trip, they’ve made big improvements,” Madison said. We kept making our way through the exhibits and I felt a gentle companionship between us as we walked through the quiet museum. We did not feel like we had to read every word together, but we stayed in each other’s general vicinity as we read. I liked that it felt like we were learning the backstories together.
We met up at the last set of exhibits, which was about the various conspiracy theories surrounding the JFK assassination. I was surprised at how seriously they were taken and found it fascinating.
“Some of these do kind of make you wonder, don’t they?” I said.
“A little, I guess, but I don’t think any are really all that plausible,” Madison said.
Our next order of business was to meet up with Madison’s best friend from high school, Mary, who she wanted to introduce me to. I was looking forward to meeting someone who wasn’t a family member from Madison’s childhood and learning more about her background. If she was anything like me, her high school friends would have a significantly different perception of her than her college friends. We met at a cafe in Uptown, which was my first look at the neighborhood Katie had mentioned that morning. I could see why it appealed to her. It was already busy mid-afternoon on a Saturday, I could envision all the bars and restaurants would be overflowing later that night.
Mary greeted us and we ordered lemonade, which seemed appropriate for the hot day. The cafe was pleasantly quiet despite the hustle and bustle outside. The first thing I noticed about Mary was actually how normal she looked. She was a bit tall and gangly, but other than that she had typical shoulder length brown hair, wore no makeup, and had on baggy clothes. As I observed the two friends start to catch up I realized something pretty quickly that surprised me - Madison was really the one driving the conversation. Madison had never been a shrinking violet, but she also was never the most comfortable socially. That’s why she deferred to friends like Ashley and Alexa in college when it came to planning fun, and perhaps even Adrian and I in Spain. With Mary she was different though, more animated, more excited to hear about what Mary was up to. It reminded me a lot of how her mom had been at dinner the previous evening.
I learned that Mary had stayed local for college, attending UT-Dallas. She was working as a paralegal at a firm in Richardson, not downtown. She thought law school might be good, but didn’t think she could get into SMU and didn’t want to commute to Fort Worth. For now she was living with her parents. She seemed very unsure of herself and even a little embarrassed. I supposed compared to Madison’s attending SMU for grad school and internship with a prestigious accounting firm I could understand why.
“So how did you two meet?” I asked.
“Study hall,” they said in unison and chuckled.
“In middle school, most of the kids just messed around in study hall but we were actually trying to study, so the teacher monitoring the study hall let us use this little side room. We got to talking, realized we were both sort of homebodies and became friends,” Madison explained
“Eventually I got to know her family and vice versa, so then we could hang out at each other’s houses but still be homebodies,” Mary said, laughing lightly. I could tell from her expression she had treasured those times.
“Sounds like Madison,” I said wryly. Mary laughed.