Chapter 21: Chaperone Duties

Shelly sat beside her sister in the passenger seat of the car and she was mad. This should have been her night. A night she should have looked forward to but Stacy was making it seem like hell. Her sister had been teasing her all day, and now, on the short jog to Tommy’s house, it had only gotten worse. Saying things like ‘Oh, I can’t wait until I get Tommy’s tongue on my pussy. Oooh, he was so good at it last time, feeling that tongue licking me all up and down. It’s going to feel so good!’

The worst thing about all this was that Stacy talked like Tommy was her boyfriend and not her own. She almost regretted the deal she made with this devil of a sister, but whenever she thought about reneging, her thoughts went back to that one night she had had with Tommy and how wonderful it had been. For weeks now all she could think about was how much she wanted to experience another one of those nights. She only wished her sister didn’t have to remind her what it was going to cost her. If she’d just shut up about it! Shelly thought for the hundredth time, but what could she do? In all her fourteen years she had never found a way to shut up her sister. So, she just sat there and fumed. I’ll just have to grin and bear it for a little while longer. She thought to herself. After all, what else can I do?

When the two girls knocked on Tommy and Emily’s front door, they were greeted by the younger of the teenagers. Stacy, upon seeing the young adolescent male on the other side, immediately accosted him with that shit faced grin of hers and proclaimed loudly, “Hey, Tommy, you ready for your big night?”

Tommy, whose eyes had been solely on Shelly, couldn’t help but notice his girlfriend cringe at her sister’s words. He also noticed how she jerked her head toward her sister only to stare daggers at her.

“Ehh, I guess so.” Tommy replied cautiously, as he looked back and forth between the two.

“Great!” Stacy exclaimed. “Where’s Emily?”

“She’s back in the family room.” Tommy replied as he tried to figure out all the internal dynamics going on between the two sisters.

Having received her answer, Stacy immediately pushed Tommy aside and took off down the hall and toward the family room. Tommy, having recovered from the slight shove, stepped back up to Shelly, placed his arm on her shoulder, leaned in, and gave his girlfriend a quick kiss on the lips. “Are you all right?”

“Yeah.” Shelly lied and forced a strained smile. “How about you? ... Are you okay?”

“Yeah, I’m okay.” Tommy replied, still worried about his girlfriend.

That’s when they heard a shout coming from the direction of the family room. “Hey you two, get your butts over here.”

Shelly grimaced and jerked her head angrily at her sister’s voice. She then sighed, grasped Tommy’s hand and said. “Come on Tommy. Let’s go get this over with.”

They walked into the family room still holding hands. Tommy had hers to give Shelly some reassurance, while Shelly had his because she was not yet willing to let Tommy go.

When they reached the family room, Shelly’s eyes flicked back and forth between the two older girls, who were both standing beside the couch, but her eyes always seemed to settle back over to her sister.

It’s sort of weird. Shelly thought to herself. Somehow, I trust Emily more than I do my own sister. Maybe it’s due to Emily’s congenial personality, versus Stacy’s loudmouth, pretentious one. Or it might be for the way Emily had literally and voluntarily bequeathed Tommy over to me and, after that, never touched him again.

Shelly knew that her last statement was not based on just faith alone. You see, after Shelly and Tommy had started dating, over time, Shelly had asked Tommy (interrogated more like) for the exact rundown on what exactly went on between stepsister and stepbrother. Exactly when it started; how it started; and the exact details of what happened between the two. And as she pried those details out, she’d also slipped in some subtle inquiries and asked if anything was still going on between the two. That’s how she knew Emily’s and Tommy’s sexual escapades had stopped the very day Shelly and Tommy had gone on their first date.

This hadn’t surprised her any, that was just the way Emily was. Not that Stacy had a reputation for going after other girls’ boyfriends. But that didn’t seem to stop her from messing around with mine! Shelly seethed as she continued to eyeball her older sister.

Shelly couldn’t help but notice the leer Stacy was giving Tommy and, for the umteenth time, Shelly thought about backing out of the deal, but then she realized what she’d be giving up. It was just too high a price to pay. So instead, she said nothing and just tried to convince herself that it would be just this one time. After this that would be it and soon both of the girls would be off to college there they would be sure to find their own boyfriends. Tommy would be completely hers again and only hers. She reassured herself.

Stacy, who had turned her full attention to Tommy, with an unabashed glee and a big smile, announced, “Okay Tommy, let’s go do this.”

Tommy’s only response to Stacy’s invitation was to look directly over to his girlfriend and once he got Shelly’s attention, he looked down to his hand that was being clinched within hers.

Shelly sighed and, what felt like the hardest thing she ever did, unclasped her hand and said, “Go ahead, Tommy.”

Once both hands were free, Tommy lifted them both to his shirt collar and promptly pulled it up over his head. He then folded it and placed it on the couch’s armrest. Next, he unbuckled his belt and the waistband of his pants and pushed both it and his underwear down to his feet.

The male’s actions caused all three of the girls to focus their attention on the young male, but it wasn’t until Tommy was standing on one leg struggling to strip the jean’s right leg off, that the youngest one yelled out, “Tommy, what are you doing?”

Shelly’s inquiry caused Tommy to stumble back down. The right pants leg was only half off his leg, the rest, underwear included, was still residing on top of his ankles. The ‘almost’ naked boy looked over to Shelly and answered, “Umm, I’m taking my clothes off.” He then half jerked his arm up in the direction of his sister before adding, “Emily always had me strip before I ... well you know.”

He had only half jerked his arm toward Emily because, while doing so, Tommy realized his big mistake. He was no longer taking his marching orders from his sister anymore, but it was now Shelly. She was in control, so he quickly amended his statement. “I can keep them on if that’s what you’d want.”

Emily, who had been enjoying the well trained actions of her submissive brother, graciously confirmed her brother’s story. “Yeah, he’s right, Shelly. Before I had my slave please me, or for that matter, either you or Stacy, I always had him strip naked.”

She then smiled at the younger girl and then nodded her head at her brother. “I found it humbled him.”

Emily then unabashedly scanned her young brother’s body both up and down, and added with a smile, “And don’t you think that body is sort of hot to look at?”

Emily then turned her head back to Shelly before ending the explanation with, “But you do what you like. He’s your slave now.”

Shelly’s attention had been on Emily while the older girl gave out her explanation, but once Emily got the part about Tommy’s ‘hotness’, she couldn’t help but look back over to Tommy and check out her almost naked boyfriend.

Shelly realized Emily was right, Tommy was hot to look at, all the way from his handsome face, to his pecs, which were just now showing signs of filling out and becoming a man, and all that stuff down below that.

As she looked down at that part of his body, she couldn’t help but notice that cock of his. It was just hanging there, framed, as it were, by his two testicles, but as she studied it, Shelly noticed its shaft was slowly expanding, getting larger, and longer. The corners of Shelly’s lips curled up as she thought. Emily’s right, but I knew that already!

She then imagined her naked boyfriend going down on the two older girls and felt a little twinge in her nether regions. She was a little surprised at her body’s swift reaction. She was also willing to explore it further. So, in as much of an unassuming voice as she could muster she said, “Oh ... in that case, Tommy, you can go ahead and take your clothes off.”

So that’s what the boy did, as all three females watched.

Stacy, who had also been admiring the young, naked, male specimen, waited patiently until Tommy had placed that last of his (neatly folded) clothing onto the couch’s arm, but once that was done, she quickly made her claim. “Ok, I get to go first!”

She then stepped up to Tommy, grabbed his wrist, and said, “Come on Tommy, let’s go do this in Emily’s room.” She then turned herself toward the hallway and started leading Tommy out of the room.

When Shelly saw Stacy lead Tommy away, she panicked. Her brain quickly became flooded with a multitude of jealous thoughts. Things like: What is my sister going to do with him? ... What if she plans to do more than just have Tommy go down on her? ... What if she makes love to him? ... And what if Tommy finds she’s a much better lover than me? ... What if Tommy ends up liking her body better? ... Likes her big breasts better? And so on and so on. So, before she was even aware of it and before Stacy and Tommy had stepped out of the room, her voice shouted out with a resounding, “STOP!”

And that’s what Tommy did, which in turn caused Stacy’s body to jerk back and come to an abrupt halt as well since her hand was still attached to his.

Both Tommy and Stacy now turned back to look at Shelly. The expression on Tommy’s face was of a confused but faithful boyfriend, while Stacy’s face showed her annoyance. She was getting pissed off that her little sister was interrupting all her fun.

Shelly, still fearful that Stacy would cajole Tommy to leave the room, gave her boyfriend a clear directive. “Tommy, don’t go anywhere with her!”

The puzzled Tommy acknowledged her with an affirmative head nod and a confused, long drawn out, “Okaaay?”

While doing so, he was thinking, What’s going on? ... Is the deal off now?

He continued to study his girlfriend for some additional clues.

Good, Tommy wasn’t going anywhere. Shelly exhaled in relief. But what do I do now?

Shelly wasn’t exactly sure, but she did know one thing, there wasn’t any way in hell that she was going to allow Stacy to take Tommy away into a private room. If I’m going to be forced to go through with this then I want to be there ... I want to make absolutely sure that Stacy doesn’t cheat!

And she also thought with a bit of a guilty conscience. And I want to keep my eye on Tommy too.

Shelly then came to the following conclusion. If I’m going to be forced to do this then I want to be there where I can watch them.

That resolved, Shelly shifted her focus back over to her sister. But what if Stacy won’t agree?

As she looked at her sister’s pissed off face. She could tell her sister was rather annoyed with her. Stacy’s hand still had not let go of Tommy’s wrist and she was still half pulling him toward the hallway but, fortunately, Tommy wasn’t going anywhere and Shelly knew that he wouldn’t go anywhere, not without her permission.

That’s when a small grin appeared on Shelly’s lips for she just realized that she had the upper hand. And that smile grew brighter as she realized something else. Just by happenstance, she may have just found a loophole out of this whole deal. A way she could still have Tommy and get her out of the agreement without actually reneging. So she stared down at her pissed off sister and calmly laid out her one condition. “If you want Tommy to get you off then you have to do it down here.”

“What! --- You’re not going to give me my privacy?”

“No!” Shelly quickly countered, while shaking her head, and then, with more than a smug smile, she added, “Why should I? You didn’t give me any!”

“Hey, need I remind you that the reason Emily and I were in that room was because you were too scared to be there alone with him.”

“And you wanted to see your little sister get off! --- And don’t deny it, Stacy!” Was Shelly’s rejoinder. “So I don’t care!”

Shelly’s smile was now unmistakable as she finally laid down all her cards. “You could either do my way, or you could just skip your turn.”

“No fucken way, you twerp!” Stacy shouted back. Stacy then dropped Tommy’s hand, stomped back to the couch, and angrily flipped off her left sandal.

“FINE!” That sandal was quickly followed by the right one. “We’ll do it your way!”

Next, her hands reached and unclasped the button of her jean shorts and then she pulled down the zipper. “I don’t care, pervert.”

She bent slightly over and pushed her cutoff jean shorts off her nicely rounded ass. Down it went. Immediately after that, down went her panties.

“I hope you get your fucken jollies off.” Stacy plopped her naked ass down onto the sofa and angrily went about stripping first the shorts and then the panties off her legs.

That was when Emily finally forced herself into the conversation. “Hey, wait a second! If we’re going to do it here, then let me get something to lay down on the couch.”

After that, Emily promptly left the room.

Stacy, who now had both her shorts and panties off and in her hands, stood back up and laid both articles of clothing on the couch’s back. She then turned herself back around and waited for her best friend to return. That’s when she noticed something. Something that amused her.