Pining for Madison: Part 3

Pining for Madison: Part 3 Becky Is Not A Chaperone. By Secretauthor2021, in 5 parts. Listen to the ► Podcast at Explicit Novels. I continued for another hour and a half before finally calling it a day. The garden was looking great, and Mrs. Taylor was extremely grateful. I even got a "looks good" response from Mr. Taylor: definite progress. "Would it be okay if I used your shower to clean up?" I asked Mrs. Taylor. "Of course, dear. There should be fresh towels already out." "Lovely, thanks, Mrs. Taylor." I was just about to go up the stairs when Madison and Becky were coming down in the opposite direction. "Becky is just going home to get ready for tonight." "Oh, okay. See you again, Becky," I said, then turning to Madison, "I'm just going to have a quick shower, and I'll be right with you." "Okay, I'll be up in a sec." I left them at the foot of the stairs as I went to take a shower. After around ten minutes, I left the bathroom and went to Madison's bedroom to get changed. Madison was sitting on her bed, flicking through her phone, when I walked in. "Hey babe," I said before closing the door behind me. "Oh hey, do you have a minute?" "For you, always." I sat down on the side of the bed, my towel tucked around my waist. "Is everything okay?" I then asked. "Yeah, all is good. I just wanted to ask you something. Well, it's more of a favor, really." "Okay! This is sounding ominous." "Well, remember I said Becky was feeling a bit down." "Yes." "Well, I didn't fully explain her situation. If I tell you, you have to promise not to breathe a word to anyone." "Okay, I promise." She took a deep breath. "God, I can't believe I'm going to tell you this." "Tell me what?" I urged. "Well, she hates the fact she's still a virgin. Like, really hates it, and she doesn't want to, in her words, be the only one in the entire year that hasn't been laid yet." "Okay," I said, wondering where she was going with this. "In her head, it's like being the last one to be picked in Phys Ed. The one no one really wants on their team. It's really affecting her self-esteem." That, I could relate to. It was never a nice feeling to be picked last. In fact, at that point, you're not even picked; you're what they're left with. "Okay... so if she's that desperate, I'm sure someone will oblige." "That's the problem. She can't find anyone she likes, and on top of that, she doesn't want to come across as desperate in case someone takes advantage or accuses her of being a slut for throwing herself at guys." "Huh, quite the dilemma Becky has. But why are you telling me all this?" "You know how you said I was a good friend." "Yes," I replied. "Well, we were talking, and I might have mentioned how we started off, and how great the sex is." "Okay," I said still waiting for Madison, to get to the point. "Oh, fuck it, I'll just come out and say it. Will you take Becky's virginity?" "Um, what now?" I said completely dumbfounded by what she just said. "Will you have sex with Becky? This one time, as a favor for me." "Me? Do you realize, what you're asking?" "I do, and I thought about it, and I know this is a big ask, it's just, this sort of makes sense, plus we can be discreet about it." "A big ask! You're asking me to sleep with another woman, how can you be so cool about this?" "She's my best friend, you're my boyfriend, I trust you both explicitly. Besides, someone who is as good as you at sex - it would be mean to keep you all to myself," she said trying to appeal to my ego. "And what would you be doing, while all this was going on?" "I don't know, what would you like me to be doing?" I took a moment to think about it. "Can you get involved?" "What, like a threesome?" she replied. "Yeah, a threesome makes much more sense to me. A one-on-one with Becky would just feel like cheating on you, and I'm not comfortable with that." Madison started to come around to my suggestion. "Okay, I can do that, but the main focus has to be on Becky, though." "I'd rather focus on you." "I know, babe, but she really needs this." "And this isn't some elaborate joke or test designed to trap boyfriends?" "Nope." "Still, I don't know about this," I replied, still feeling skeptical about the whole thing. Madison then sloped off the bed and onto the floor, kneeling in front of me, looking up at me. "How about..." she began to say, then moving her hand beneath my towel, up my leg and running her fingers along the head of my cock. "I convince you." I looked down at her eager face, as my cock twitched from her touch. "Okay, okay, but it's still a big ask." I replied. "Hmm, okay, how about this? You do this for me, and I'll let you try that thing we talked about the other day." "Wait, seriously?" I said, my face lighting up. "Uh huh." Madison and I had talked on and off about trying anal for a while, but I couldn't quite get her to try it. Her ass was simply too amazing to ignore, and something I had fantasized about for a while now. "Fine, I'll do it, but I'm doing this for you okay, not Becky." "Thanks Ad, you're the best boyfriend ever. I better call Becky and let her know the good news. Madison tried to get to her feet, when I coughed to get her attention. She turned to look at me and I motioned with my eyes downwards. "Oh right, sorry. I'm sure Becky can wait a few more minutes." Madison untucked the towel from my waist and opened it. I had already started to get hard, just thinking about what Madison had offered me. She grabbed my cock and started to slowly jerk it, my cock continuing to harden in her soft hand. Teasingly, she licked the underside of my now swollen cock, then began planting kisses along the side until she reached the tip. It was then she took me in her mouth. God this felt so good, the feel of her lips, the warm, wet embrace of her mouth, the way she moved her tongue and swirled it around my head. Madison's head bobbed up and down in a steady rhythm now. As my mind drifted away in a sea of bliss, it suddenly dawned on me, that I'd actually be having a threesome with my girlfriend and her best friend. Isn't this what every boy dreams of? I had only ever had sex with one person and now Madison was offering Becky up on a plate. Fuck me this was crazy, but then again it was crazy when Madison and I hooked up the first time and look at us now. As I felt my orgasm rapidly approaching, I tapped the top of Madison's head as a courtesy to warn her what was coming. She continued to go at, until I couldn't hold back any longer. "Oh! Oh! Fuck, fuck, fuck," I cried out as quietly as I could as not to alert her parents. Madison continued to work my cock as I came, her lips securely locked around my cock, until I finished completely. Madison took a moment to swallow, before speaking. "Okay, so are we good now?" She said with a cute little smile, then proceeding to dab the corners of her mouth with my towel, almost as if she had just finished a delicious meal at a fancy restaurant. At this point, I would happily have given her all my vital organs had she asked for them. "Yes, we're good." I said exhaling deeply. "Cool." I had to give it to Madison, she certainly was prepared to go the extra mile for her friends. I helped her get to her feet, by offering her my hand. "Damn!" "What is it?" I replied. "I'm kind of in the mood now." "Well, you're going to have to give me at least ten minutes." She then sighed as she thought of another blocker. "We can't," she said somewhat disappointed. "My parents are downstairs. Rain check?" "Definitely. Here, why don't you call Becky." I said, handing over her phone. Madison took the phone from my hand, then swooped in for a quick kiss. "Thanks babe." Unlocking her phone, she went to her contacts and tapped on Becky's name. She waited a moment, then Becky answered. Once again I was left to hear only one half of the conversation. "Hey Girl, I just spoke to Adam, and we are a go." I could hear Becky's excited scream through the phone. "Uh huh, yeah, I know." "He does have one condition though. How do you feel about it being a threesome?" "Of course with me, silly. I'm not just rounding up people for you to have sex with. I'm not some sort of madam, although I do like the sound of that." "Yeah! Madam Madison," she said laughing down the phone, "it has a certain ring to it." "Uh huh, I know. It'll be like that time in summer camp remember, except a lot naughtier." I could hear them both laughing now. I however, had to make a mental note to come back to that one. "Anyway, I'll leave you to prepare, and I'll see you tonight. Later Becks." Madison hung up and then looked at me. "Guess we're having a threesome then." "Well, there's a sentence I'd never thought I'd hear." I replied, still somewhat in disbelief. "So, what's the plan exactly?" I added. "Becky's coming round at 8pm for the quote, unquote sleep over." "And what about me, there's no way your dad is going to let me stay after dark." "Well, what he doesn't know won't harm him, will it. It's date night tonight, so he's taking mom out, so they'll be gone for a while." "And then?" "Then the fun starts." She said with a mischievous smile. Madison appeared to be well up for this. I carried on getting dressed, thinking about the threesome. How does it work exactly? Who does what? I can only cum once at the end of the day. Although, I guess I'd have to save that for Becky in this instance. I had to get going and I could see on Madison's face, that she was deep in planning mode, so now was a good time to leave her to it. "I'll be off then," I announced. "Okay babe, I'll see you...." she kissed me on the lips, "and you, later," she continued, grabbing my crotch. "I'm probably going to go to Becky's now and give her a hand." I turned my wrist to look at my watch. "You've got like eight hours, babe." "I know, but it's a gonna be a big night for her, and us girls need time to prepare." "Well, I'll leave you to it. Just message me when it's safe to come over." I left Madison to it and went downstairs, making sure to say goodbye to Mr. and Mrs. Taylor. On the walk home, I wondered if there was anything I could do to prepare for tonight, wondering if I should look at some 'tutorials' on the internet perhaps. I also started to think about Becky, and how I was going to see her naked for the first time, and she was going to see me. I'd never really thought about her in any kind of sexual way before. I only had eyes for Madison. I mean, sure, she was a pretty girl, but she didn't have the same oomph as Madison. It was literally the thought of Madison that got me up in the morning, if you catch my drift. As I got home, I was feeling a bit hungry, so headed into the kitchen. My mom was at the sink doing the dishes. "Hey mom," I said sitting myself down on the stool by the breakfast bar. "Oh hey Adam, are you hungry? I can make you a sandwich." "Yes, please." My mom finished the last of the dishes and dried her hands on the towel. "So, how's your day been, so far?" she asked, grabbing the sandwich meats from the fridge and then bread from the bread bin. "It's been okay." "Are you sure? you seem a bit distant." "Something on your mind, son? Do you want to talk about it?" "God no," I blurted out rather abruptly. My mom was taken aback by my bluntness, so I quickly apologized. "Sorry mom, I didn't mean to say it like that. I'm fine really." My mom finished making the sandwich and handed me the plate. "Is it about, you know S E X?" She said spelling it out. "Because if it is, I can get your father." She took a deep breath, ready to shout out my dad's name, when I quickly cut her off. "Mom! it's not about that. Shush! No need to call dad." "Well, if you're sure. You know you can always talk to us about anything." While I appreciated her offer, there was no way I was talking this one out with her or my dad. "Honestly, I'm fine mom. No need to worry. I'm going to take my sandwich up to my room." "Okay dear, don't forget to bring the plate down afterwards. I'll see you later." As I carried my sandwich upstairs, I couldn't help but think how remarkably accurate my mom's instincts were. I guess mother's really do know best. I sat on my bed and took a big bite out of my sandwich. As I chewed, I tried to visualize what it would be like in my head. I thought about Madison and her rocking body, kneeling on the bed. Then I added Becky next to her, not sure what she looked like naked, so I had to improvise. Then the idea of the pillow fight popped into my head, the two girls bouncing up and down on the bed in slow motion, hitting each other with pillows, with an explosion of feathers everywhere, and jiggling, so much jiggling. I found myself smiling at the thought of it, this was shaping up to be quite a good fantasy I thought to myself. Before I knew it, the sandwich was finished, and I had just eased back on to my pillow. I'll just sit back and picture it some more, I thought. In mere moments, I had fallen asleep. The yard work must have really taken it out of me, as when I woke up it was 7pm. Feeling a bit groggy, I decided to have a shower to wake me up. With the shower done, I found myself waiting for the call. I suddenly started to get very anxious about it. Talking about it was one thing, but actually going through with it was another. I needed a distraction to stop me from overthinking it, so I decided to play one of the games on my Xbox. Just as I was getting into it, my phone chimed. It was a message from Madison. I paused the game and looked at my phone. From: Mads "They've just left, you can come over now xx" This was it, time to shine, I thought. I turned the console off, put my trainers on and headed out the door, yelling "I'm going out, be back later," as I left. As I made my way to Madison's I could feel my nerves kicking in. I hadn't felt like this, since the early days with Madison. Now, it wasn't one girl I had to worry about pleasing but two. As Madison said to Becky on the phone, this was so wild. I mean a threesome, me? I never thought stuff like this would happen to a guy like me. Madison's front door was now mere feet away. I slowly approached, mentally psyching myself up and then knocked on her door. Within seconds, Madison had answered, she was wearing her fluffy pink dressing gown. "Hey babe," she greeted, giving me a quick kiss on the lips. "Hey." "Becky's upstairs; do you want a drink before we go up?" "Sure, thanks." I followed Madison into the kitchen. "So, this is it? Our first threesome," I said, as she grabbed a glass from the cupboard. "I know, crazy right. But don't forget the focus of tonight is Becky, you and I will have plenty of opportunities for a one on one, so don't worry about me so much, okay?" She filled the glass with water and handed it to me. "You're the boss." I gulped the water down quickly, something that Madison picked up on. "You're not nervous, are you?" "A little," I replied, and put the empty glass on the counter. "Don't worry about it, I'll make sure you're properly taken care of," she said smiling. She gently pushed me against the kitchen unit and leaned into me, wrapping her arms around my waist; we kissed. "Now, come on stud, Becky must be wondering where we are." Madison grabbed my hand and lead me back through the house and up the stairs to her room. As we entered, Becky, also in a dressing gown, was sitting on the bed. She got up as soon as she saw us. "Hey Becky," "Hey Adam, I... I just wanted to say thank you for agreeing to do this. I know you and Mads love each other very much and this was a big ask on my part, but thank you, you don't know how much I need this." "Thank Madison, really, she's the one who did a very good job convincing me." Madison playfully nudged me as she walked to the other side of the bed. There was a brief silence as we all looked at each other, wondering how we were going to start this, when Becky remembered something and broke the silence. "Oh, before I forget. I wasn't quite sure what would happen tonight, or what you two were into, so I did a bit of research on the internet and brought a few things with me. I hope you don't mind." She walked to the corner of the room and picked up a nondescript carrier bag. Then walking back, she proceeded to empty the contents of the bag on to the bed. "Holy crap Beck's," Madison blurted out. On the bed in front of us, was a blindfold, a pair of hand cuffs, a couple of bottles of sensual massage oils, a medium sized purple vibrator and a box of condoms. "I didn't know... um, how big you were Adam, so I hope these are okay?" Becky said pointing to the condoms. "They should be fine." I replied, looking at the box. "After you left Mads, I went into that new lingerie shop in the mall. They had a whole section of this stuff at the back, so I grabbed all this lot." Madison and I looked at each other, then both looked back at Becky. "Wow Becky, you really went all out." Madison, picked up the massage oil, flicked open the cap and sniffed. Her face showing, she approved of the scent. "Well, they say you never forget your first time, so I wanted to make sure mine was unforgettable." There was no chance of forgetting this, that's for sure, I thought to myself. We all stood there, just looking at the pile of sex aids on the bed, waiting for someone to make the first move. "Okay then, shall we do this?" Madison suggested, with a hint of excitement in her voice. I think Becky and I were looking for someone to take the lead and it looks like Madison just volunteered. "Well, I think to start with, one of us is wearing way too many clothes." Madison announced as both her and Becky looked in my direction. "What about you two? With your dressing gowns on," I said defensively, even though I knew I would need to get naked. The two girls turned to face each other and smiled, they both unfastened their belts, and dropped their gowns to the floor, in what looked like a perfectly synced move. My eyes didn't know where to look first. On either side of the bed was a naked girl, standing there loo