The Extraction
Copyright© 2025 by Canairs90s
Chapter 7: We’ll Always Have Nantucket
Coming of Age Sex Story: Chapter 7: We’ll Always Have Nantucket - 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
The ferry ride to Nantucket took about an hour and Madison once again went to the ship’s rail to watch proceedings once the ferry decelerated as we entered the harbor. This time I joined her. I loved the view from the ferry of the town of Nantucket, which was built into a hillside overlooking the harbor.
“It’s always a good feeling pulling into the harbor, because vacation is just beginning,” I commented. I had explained my long history with the island to Madison over the past few weeks including some of the hijinks I had gotten up to as a teenager.
“I can already see why you like it here. This is sort of how I always pictured a quiet New England fishing town,” Madison said. I did not bother to correct Madison that almost no commercial fishing operated from Nantucket anymore and what she was seeing was primarily in support of tourist activity.
It was too early to check in, and we were starving, so we got lunch at a place near the wharf I knew had good fish sandwiches and fries. Out of the wind it was back to being a beautiful late spring New England day, so we got a bottle of wine with lunch and an outdoor table to people watch all the activity on the wharf as well as allowing us to keep an eye on our bikes. People watching was an old favorite activity of ours from Spain and we were having an amazing time checking out some of the eccentric types Nantucket attracts.
After that it was late enough in the day we could go check into the bed and breakfast. We made the ascent up Main Street, past the small primary commercial district, to where our B&B was located with a nice view of the harbor. The owner was a friendly middle-aged woman who briefed us on amenities, where to store our bikes, and kindly offered to help if we needed any tips on where to find dinner and entertainment. We thanked her, stowed away our bikes and made the short walk to our room.
Our room’s exterior door was up a narrow staircase. I let Madison go first. The black capris she was wearing made her ass look fantastic and I grabbed a handful playfully as we climbed. Madison giggled and gave me a look that suggested to me she was more than interested in picking up where we had left off the prior night.
The room wasn’t particularly large, but did have a king bed and a nice view of the town. I was much more interested in the bed and closed the shade before turning to Madison. Before I could even say anything she was in my arms and our lips were locked once again.
Whereas yesterday we had felt out of control, today I was determined to both maintain control and properly savor my time with Madison. We had this room to ourselves for three days and there was no reason to rush. Madison seemed to match that energy and we took plenty of time to explore each other’s bodies with our hands as clothes slowly came off.
“Sexy,” I said once Madison was down to her bra and panties - a white set with delicate turquoise trim.
“Thanks, I bought these for this trip. I didn’t want to be presumptuous, but a girl should be prepared, right?”
I laughed. “Well, you have excellent taste.”
The kissing and slow exploration continued until we were both naked. I retrieved the condoms we had bought earlier from my backpack and put one on then joined Madison on the bed. I lightly stroked her slit with my hand and found it already well lubricated with her natural arousal. I put a finger inside her and gently explored, trying to turn her on as well as get a sense for what she liked.
I did not learn much because Madison liked all of it. She whimpered and bucked her hips with pleasure. I added a second finger and kept at it for a few more minutes.
“That feels amazing, but I want the real thing now,” Madison requested. I was more than happy to oblige and re-positioned myself before slowly inserting my dick into her. Moving deliberately to let her feel and fully embrace the intrusion.
I had not had tons of sexual partners but I had had enough to know that the first time was often disappointing. There are so many subtleties about human sexuality that it takes time to learn the small things needed to pleasure a partner. Madison and I did not need acclimatization time however. We had good chemistry outside the bedroom and it turned out we did in it too. Like we were meant for each other.
As I began to thrust Madison moved her hips subtly to meet me. She was tight and the visual of her hot naked body writhing in response to my efforts turned me on. I suddenly worried that I had talked too big of a game the prior evening night - I was on the verge of climaxing in just minutes. I was not going to let Madison’s first real time with me not bring her at least one orgasm though. I refocused my efforts on using the angle of my dick to try to hit her g-spot and dropped one hand to her clit. It was tough to hold myself up on one arm, rub her clit, and thrust. Concentrating on those tasks distracted me from my arousal a bit and I was able to hold out.
It helped that Madison started to cum within 30 seconds of me touching her clit. I stopped thrusting and let her ride out the orgasm.
“That was fucking incredible,” she breathed, looking at me in awe. “Did you, you know, go?”
“No, I always let the lady go first,” I told her, explaining my personal philosophy and omitting some of the selfishness that had crept in during the late stages with Haley.
“I don’t understand how you can control yourself,” Madison said, confused. “But I’m certainly not complaining.”
I resumed my thrusting, getting Madison off had left me even more turned on than I already was. With my focus now on myself I got off quickly, although it was not lost on me that Madison was moaning with pleasure as I filled the condom.
I kissed her quickly and slowly withdrew, then dropped the condom in the waste bin in the bathroom, and rinsed myself off. I disliked the smell that condoms left on me.
Madison had barely moved from where I had left her, her legs were splayed and she stared at the ceiling almost glassy eyed.
“You okay?” I asked.
“Oh, more than ok. I just feel like I had a revelation. I know how to get myself off, but I have never had an orgasm from sex. To be honest, I have been confused since my first time why people get so excited and go to all these lengths to get laid. I feel like now I understand,” Madison said.
“I guess this is what the phrase ‘rocking your world’ means,” I said, climbing back on the bed and kissing Madison’s cheek. I rested a hand affectionately on her thigh. I loved the physical connection with her.
Madison laughed. “Yeah, I guess you could say that. I think I’m re-evaluating my entire belief system now. I have a whole new thing to pursue.”
“Good thing we have two and a half more days to ourselves,” I pointed out.
“I suddenly have so many things to try that I’ve heard about,” Madison said.
“God, this is going to be fun, isn’t it?” I said. I recognized Madison’s tone. It was the same one she used when a new topic really interested her and she wanted to learn as much as she could about it. I could feel the gears beginning to turn in her head as she shifted from post-coital daze to the analytical side of her that had just discovered something new to master.
“If you’ll teach me, I plan to be a very willing and attentive student,” she said. She had rolled onto her side and was grinning at me. If I knew one thing about Madison it was that she never did anything in half measures. Things were about to get really interesting.
A significant part of me just wanted to cuddle in bed with Madison all afternoon until we were ready for round two, but I was wary of letting the weekend become just about sex. The intimacy was awesome, and I was excited for what was to come, but I also liked Madison as a person and wanted to do more normal couple things with her lest she think I was just interested in the physical aspect of the relationship. So rather than laze about we got dressed again and walked around the town.
We walked arm in arm, even when navigating the narrow aisles of the shops. I got the sense that Madison needed the physical connection now that we had crossed that last physical barrier. As if letting go meant I would run off and find someone else. I would not have under any circumstances, but I liked the way she was hanging on my arm. I also have to admit having such a cutie obviously attached to me was not hurting my ego at all.
The small side streets of the town were a mixture of locally owned places selling knick-knacks, although upscale boutiques were starting to infiltrate the town’s commercial district. We walked and browsed in the shops. I bought Madison a few silly trinkets she liked. From my perspective it was a huge point in her favor that she gravitated towards the places selling kitsch instead of upscale clothing.
I regaled her with stories from my teens of my friends and I buying gag gifts for each other at various shops and slipping them into each other’s backpacks. The time I bought my buddy Kevin a pink My Little Pony bracelet and his older sister found it - he never lived that down. We had lost touch a little, but I wondered if the nickname ‘Brony’ still haunted him. Madison thought it was all hilarious.
“I made a reservation for a seafood place down by the wharf for 7:30. I don’t think we need to be dressed up, but I should probably at least put on a polo shirt,” I said to Madison after a few hours of traipsing around. “We should probably head back to the B&B in the next hour or so to change. It’s like a ten minute walk down to the wharf.”
Madison bit her lip as if unsure of herself, but then spoke up. “Uh, would it be ok if we maybe head back now and had more sex before we have to get ready for dinner?” she asked.
I almost laughed at Madison’s question. It was so blunt, but so her. Never anything in half measures with this girl, I reminded myself. I was a lucky man.
“I believe I have already volunteered myself as your instructor. It’s also a personal policy of mine to never tell a hot chick ‘no’ when she wants to get dirty,” I said.
Madison lightly punched my bicep in reaction to my crude language, but I could tell she liked being described as a ‘hot chick’. We practically dragged each other back to the B&B.
Once we were inside the clothes flew off. The slow, deliberate pace of our encounter earlier that afternoon was gone. We both wanted each other, badly. Before I knew it we were both naked and my cock was sheathed in a fresh condom.
“Um, would it be if I tried being on top this time?” Madison asked tentatively.
“Not only would it be ok, but as your guide, I insist upon it,” I replied, alluding to our earlier discussion. I got on the bed on my back. I was fully erect at the sight of Madison’s nude body, not to mention this new, sexually inquisitive, version of her. She knelt above me and played with my hard cock for a few moments, taking some time to get a feel for it. I liked it, it felt like we were truly getting to know each other sexually. It was unforced, comfortable intimacy.
Eventually she positioned herself above me and slowly moved her hips down, allowing me to penetrate her. She recoiled after a few inches were inside her, almost as if electrocuted and shot back up her knees.
“You ok?” I asked, concerned.
“Oh, uh, yeah. Honestly it just feels so freaking intense. It’s almost too much to handle,” Madison, a little breathlessly.
“Ok, well take it slow. Find out what pleasures you. I promise my hard on is not going away any time soon,” I told her. My goal was to reinforce how devastatingly attractive I found her as well as to make her feel no pressure.
She tentatively moved back down and slowly and steadily fed by hard dick into herself until she was fully impaled on my member.
“Oh fuck me,” Madison moaned as she slowly began to move her hips up and down.
“Literally am,” I pointed out. Madison cackled at that and I joined her. It seemed to break the tension and destroy her hesitancy. She dropped her torso down so that we could kiss and I wrapped my arms around her.
“This is fucking fantastic,” I told her. Our faces were inches apart.
“I love being in control, I can use your dick however I want, it’s like, so freeing,” Madison said. She had sat back up and resumed moving up and down my shaft vigorously.
“I’m shocked you like being in control,” I scoffed sarcastically. Madison laughed but quickly resumed her efforts. I carefully observed as she made subtle adjustments to hit just the right spots for her to get off.
I was a huge fan of cowgirl, generally speaking. There are few things hotter than watching a woman ride your dick and getting to play with her body while she does. That said, it had rarely resulted in orgasms for me. I tended to need to be more in control to get myself off. With that in mind, I was surprised to realize after perhaps ten minutes of Madison pleasuring herself on my cock I was actually somewhat close to my climax.
“I hope you are having your fun because you have me close,” I said breathily.
“Oh fuck yeah, this is totally doing it for me,” Madison said. “Fucking cum whenever you want, I’m so close.”
I appreciated her sentiment, but there was no way I was cumming before she did. I reached up and tweaked her nipples. She moaned and threw her head back. One of my hands went to her hip to steady her, the other sought out her clit. I lightly, but insistently rubbed her clit and Madison climaxed with an explosive wail.
She regarded me with a cynical expression. “I was supposed to get you off first,” she said with an exaggerated pout.
“Ladies always get to go first, it’s just basic manners,” I told her with a grin.
“Fuck, that’s hot. But seriously, fucking cum in me,” Madison said.
I was more than happy to oblige. My hands grabbed her hips and and I maneuvered her to where I needed her to be to get off. Before I knew it I was filling another condom with my jizz.
“That was fucking amazing,” Madison said once we had both come down from the high of our climaxes. She had dismounted, and I had discarded the condom, before we cuddled together. “Drawing your orgasm out of you, I felt so fucking powerful. It was so awesome.”
I laughed. “You’re a sexy girl, you have the power,” I said to her. She beamed and snuggled up to me. She liked that feeling.
I replaced the hoodie I had worn most of the day with a blue polo and Madison left her sorority shirt where it had been discarded on the floor and replaced it with a flowy purple blouse. She also switched from the flip flops she’d been wearing to wedge sandals with a two inch heel. The outfit changes transformed her look from college girl to classy young woman.
“You look fantastic, but you do remember Main Street is cobbled right?” I asked. A sprained ankle seemed like a good way to spoil our fun.
“The sidewalks are normal though, plus I have a dashing young gentleman accompanying me that I’m sure will be happy to assist me,” she said, smiling.
“Ok, good answer,” I allowed, returning the smile. We descended the narrow staircase to the street and walked arm in arm back down Main Street to the harbor. The sun was just setting, reflecting off the waves. It was a picture perfect evening.
The restaurant was more upscale than I realized. I was glad we had put on slightly nicer clothes. We felt a little out of place as the youngest couple there by many years, but having a woman as beautiful as Madison obviously attached to me boosted my confidence.
“I feel like I’m cosplaying being an adult,” I said to Madison once we had been seated.
“I know! I feel like I don’t belong in here. I think I should have worn a dress,” Madison said.
“You look fine, I promise,” I reassured her. My eyes lingered for a moment on the way her blouse framed her chest, and she blushed under the attention. She fiddled with one of the buttons like she wasn’t sure if she’d left too many undone, then smiled a nervous, almost apologetic smile. I sensed she was a little uncertain and wanted to learn more about this new more vulnerable side she had begun to share.
Our server interrupted before I could probe further to get our order. We picked cocktails and selected oysters for an appetizer. I was not necessarily a huge fan of oysters, but it seemed like the right choice for our fancy date and I was not above testing the theory as to whether or not they were an aphrodisiac. I was already cringing at the damage this meal was going to do to my wallet, but it was worth it to treat Madison.
The strong winds we had experienced on the ferry had calmed to a light breeze that streamed through the open windows and brought the pleasant smell of the ocean drifting through the restaurant to compete with the smells of cooking seafood emanating from the kitchen. Our drinks arrived and we clinked glasses before taking sips.
“I don’t see why you hate Massachusetts so much,” Madison said. “It seems pretty awesome to me.”
I laughed. “We got lucky with the weather. This is one of maybe two or three weeks before it will be hot and muggy for six weeks. Then we get the foliage in the fall which is ok, but whatever it’s just colorful trees. Then the gray for six months of winter. Minimal sunlight, cold. And once it snows that stuff is most likely sticking around until mid-March. Newly fallen snow is pretty. Snow that has been plowed to the roadside and sitting for weeks? Not so much.” I had made my disdain for Massachusetts well known to Madison when we first became friends. Part of it was genuine, I think part of it was also trying to appeal to her ‘Texas girl’ image. A yankee from the northeast was just too big of a contrast. I also did not consider myself a yankee. I had spent most of my childhood in the Midwest and identified more with that part of the country anyway.
“Blah blah, come visit Dallas in the summer. I don’t want to hear about your muggy heat,” Madison said, smiling. This was a conversation we had had probably had a dozen times over the years. One of us complained about the more unpleasant season where they were from and the other countered. If Adrian was around he told us both to shut up and come to the swamp known as Miami in mid-summer. However this time there was a new wrinkle.
“I actually would quite like to visit Dallas this summer, shall we examine calendars?” I asked. My question seemed to hit Madison like a lightning bolt.
“Oh shit. Uh, yes, we should. I mean I meant that jokingly, but yeah. I really want you to come meet the rest of my family,” Madison said. I recognized the importance of this, one of the things I had learned early on was how close she was with her family.
“That sounds good. I’ll check the schedule later and we can figure something out. We’ve had so many damn home games the last few weeks I’m sure there are some road trips coming up where I can get a weekend and a few days off. Now, what are we ordering?” I asked.
One of the little games Madison and I had had throughout our friendship was ordering food for each other. It had started in Spain, when I had been trying to convince her how good paella was. My host mother had been an amazing cook and made it frequently. Madison had been less lucky and her host family tended to just eat basic meals or takeout. One night at a restaurant I had ordered it and insisted she try. She, of course, loved it and we ended up swapping entrees. It became our thing. Usually we ended up sharing but had always kept up the game of ordering for the other. That night we settled on lobster and haddock. Wine was always my assignment when with Madison, since I had a bit more experience from my extended time in Europe. I picked a Sancerre I thought would pair well with the seafood.
The food was fantastic and I was very pleased with the wine pairing.
“You always nail the wine selection,” Madison said, polishing off the last of the bottle. “I am stuffed though.”
I tried to resist making the joke, I really did. “Are you, in fact, stuffed?” I asked, failing.
Madison laughed and turned her head skyward theatrically, as if asking the heavens why she had made this mistake. “You and Griff are never going to progress your humor past that of middle school boys are you?” she asked.
“It does seem improbable,” I replied, grinning.
I paid the tab, which was every bit as painful as I had expected and we strode out into the night. We agreed to walk around a bit to help our food digest before heading back to the B&B. The air had a bit of a chill to it, so rather than have Madison hold onto my arm, I put it across her shoulders to share body heat a little bit. She put a hand around my waist and put two fingers through a belt loop to hold herself in place.
We passed a cocktail bar that looked surprisingly trendy and felt a little bit out of place on quaint Nantucket. I suggested a nightcap before we headed back and Madison readily agreed. I ordered an Old Fashioned at the bar and Madison got a Cosmo. We found a two person high top that afforded a modicum of privacy in the corner of the bar and Madison initiated another cheers.
“That’s a fancy drink order for you,” I commented.
“This is kind of a fancy date night, wouldn’t you say?” Madison asked.
“I wanted to really treat you,” I replied.
“I feel very, very treated. Thank you. I’m not sure this level of fancy is really me, but it’s nice to be treated like someone who deserves the best,” Madison said.
“I like that about you,” I said. “You’re not pretentious at all, but you appreciate nice things. We could have gotten takeaway pizza from the little shop by the dock and you would have been fine. Or you can be comfortable in an upscale seafood place. You have versatility.”
“Huh,” Madison mused, thinking that over. “I actually kind of like that. You’re right. If we had gotten slices and watched the sun go down from the ferry dock I would have been perfectly happy, but I also totally appreciate that you made the effort to take me somewhere nice. I’ve never really thought of myself as versatile, but I kind of like it.”
“Well it’s been a day of revelations for you,” I said, alluding to our sexual discoveries.
“That it has. In a weird way it’s like you’re unlocking this whole new side to me. I think I like it.” Madison smiled and took a sip of her drink.
“I can’t wait to see what else I can unlock.” I put the hand not holding my drink on the table, palm up. Madison used her free hand to grasp it.
She made eye contact and thought for a moment before speaking, but when she did her voice had a confidence that surprised me. “I want to learn more from you about sex.”
I chuckled. “Madison, you make it sound like a damn research topic.”
“Damnit Drew, you know how I am, when I find something new and exciting I have to know everything about it,” Madison exclaimed. She had let go of my hand to gesticulate as she spoke. That was a telltale sign she was getting fired up.
“Well, assuming I remain your partner in this research, I guess I can get behind that,” I said. I couldn’t help but grin. Madison was basically inviting me on a sexual adventure. It was my dream come true.
She buried her head in her hand, embarrassed. This went against so much of her upbringing, but Madison had always had that maverick side to her that was not totally aligned with the good girl image she presented until you got to know her better. Her middle and ring fingers spread after a few seconds revealing her soft brown eyes. She nodded vigorously. She felt awkward about it, but she wanted this. I eagerly accepted her invitation.
“Ok, first we need to discuss terminology. What we did this afternoon, slow, gentle, face to face - that’s making love. What we did before dinner, more enthusiasm, more focused on pleasure, that’s screwing. What we’re going to do tonight, with how excited we are, that’s fucking,” I told her.
She nodded gravely. “Does it bother you that I seem to curse a lot when we, uh, screw?” Madison asked tentatively.
“Not at all, you know me well enough to know I don’t mind swearing in general, but when we’re fucking I would say it’s almost a requirement,” I said.
“Noted, bad words are ok,” Madison said.
“Fuck that,” I said, deliberately using foul language. “Those aren’t bad words. That’s called dirty talk. It’s when you describe the crazy stuff you’re feeling in the moment. The more you set aside normal convention and let it flow, the hotter it is.”
Madison nodded and took another big swig of her drink. She was processing. “I really liked that you let me have control and experiment before dinner, but would it be ok if when we get back I sort of let you take the lead?” Madison asked tentatively. “Ashley told me how she really likes to get thrown around sometimes and I’m a little curious.”
“Sure. But I’m not going to throw you around or do some BDSM shit. For one I don’t especially care for that, and for another you’re still learning the basics. I am more than happy to take the lead though. I promise you will still walk away happy. Actually fuck that, you won’t walk away, you’ll melt into the bed and wonder where you are.”
Madison shivered. I could tell she was getting excited. She was also a bit tipsy. “I’m, uh, a little turned on right now,” she whispered. “I’m not used to getting turned on in public.”
“How does it make you feel?” I asked. “If I’m being honest I am quite a bit too. You’re not alone.”
“I mean it makes me feel naughty. Like in a good way. Maybe even a little slutty, but back at you with the honesty, I kind of like it.”
“You know, that’s never an adjective I have remotely associated with you Madison, but I think I kind of like it for tonight. Shall we close out?” I asked. Madison nodded eagerly. Excitement was overriding her inhibitions.
Our walk from the bar back to the B&B was quick and purposeful. We were both excited by what was to come and eager to get back to the room.
Madison practically attacked me as soon as we closed the door to our room. We made out sloppily and aggressively for several minutes. It was reminiscent of our very first kiss in my college apartment. We pulled apart when we both became short of breath. I remembered my mandate to take the lead.
“How about you strip for me?” I suggested.
“Ok?” Madison said, slightly confused. Taking our clothes off was quickly becoming routine to her.
“No, I mean strip slowly, while I watch you,” I instructed. I took a seat on the edge of the bed.
Madison seemed to understand my instructions, but bit her lip, slightly hesitant about proceeding. Then she took a breath and her hands moved to the buttons of her blouse. She slowly unbuttoned it. She held the two sides together for a moment before dropping them to the side and revealing her tits encased in that same sexy white bra with the turquoise trim. She let her top drop to the floor. She gave me an unsure look, trying to confirm if she had followed the instructions correctly.
“Good,” I said. “Very sexy. Keep going.”
She brightened slightly and unbuttoned her capris. She seemed to have a bit of a lightbulb moment and turned away from me. She slowly lowered the pants, revealing her shapely ass in the same sexy panties as before. She bent over to pull the capris off, showing off her backside. Unfortunately she could not get her pants off over her wedge heels. Cursing she unbuckled the shoes and kicked them off, followed by the capris.
“Damnit, moment killed,” Madison said in frustration.
I laughed. “It’s not killed at all, you’re amazing and that was sexy. Come here.” I wanted to reassure her so I took my shirt off and Madison sat on my lap facing me. We made out again and I ran my hands over her body, naked except for the bra and panties. I loved the tactile sensations.
“Ok next lesson for you. Sometimes weird or funny stuff happens during sex. Like not being able to get your pants off over your shoes and looking like a doofus. You can either get yourself in a tizzy about it not going perfectly or you can laugh, remember that what you are doing is sharing an intimate moment with someone you trust, and get on with the fun.”
Madison laughed. “Thanks for not making me feel like an idiot. I thought this was fucking though, not sex?” Her grin was pure mischief. I gave her butt a playful swat in response.
“She does listen after all,” I joked. I put my hands on her sides and gently forced her into a standing position. “I want you to pace the room now. I love watching a hot girl in sexy lingerie.”
Madison complied, allowing me to admire every aspect of the body in the lingerie set she had bought just for this trip. She really had chosen well. She seemed to walk with an extra sway to her hips and did an exaggerated twirl at each end of the room. I took the opportunity to remove the rest of my clothes.
“You like?” she asked after a few laps. Her tone was still somewhat shy, but I could tell she was starting to get more confident.
I didn’t answer her. I just pointed to my dick, which was pointing straight out and could cut diamond it was so hard. She smiled.