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...