Chapter 1: Late Again. The Beginning

June turned the handle to the door hoping upon hope that her parents were sleeping. As she quietly cracked open the door, she saw only darkness and realized her prayers were answered. Her parents were in bed, asleep. She tiptoed up the stairs to the bedroom she shared with her older sister, Autumn. She reached her bedroom and quietly went over to her bed, undressed and was ready to get in when she heard her sister’s voice.

“You’re late again, you know. It has been only a few days ago when mom and dad told you that if you were late one more time, they would forbid you from seeing Roger again.”

“Yes, I know but the movie was over later than we thought and getting out of the drive-in took forever. Please don’t tell mom and dad” She answered.

Autumn’s reply was sharp and to the point. “Oh, I am most definitely going to tell them. For God’s sake, June, you only just turned 17 and he’s 23 and even served time in the Army. You know they’re concerned about you being the naïve high schooler dating someone who undoubtedly enjoyed many so-called ‘dating’ experiences”

June went over to Autumn’s bedside and pleaded, “Please don’t tell them. I’ll do all your chores for a month if you don’t tell them. Please don’t.”

“Do all my chores for a month? I’ll make you a deal. Do all my chores for a month AND do whatever I tell you to do no matter what. Agree to that and not be late again during that month and I won’t tell them. If you’re late again during that month though, I’ll add 2 weeks to the deal for every time you’re late. I’ll tell you this. I won’t be easy on you.”

June thought for a moment then answered, “Okay. I can do anything you dish out for a month.”

Autumn sat up, pointed to a spot on the floor next to her bed and said “We’ll see about that. To prove it, you can start now. Get out of your underwear and come over here. I want to examine you to see if you’ve been having any sex with him.”

“I haven’t. I swear. Yes, we’ve done some petting but nothing else.” June whispered.

Well, then. You don’t have anything to worry about, do you? Now do what I told you to do and do it NOW!”

June begrudgingly stood up and removed her bra and bikini panties, throwing them on her bed. She knew her sister was serious, and being a 2^nd year nursing student, knew what she was doing. Surely she would see that I was telling the truth she thought. She walked over to Autumn’s bedside and stood defiantly with her arms crossed across her. “Okay, let’s get it over with. I’m tired and want to get to bed”

Autumn smiled at her and stood up saying, “Oh I’m afraid it’s going to be a lot longer than you think. The inspection is only part of what I have in store for you tonight. Tonight, you’re going to prove you will live up to our agreement. Now get on the bed on your knees and head down flat on the bed facing the wall with your legs spread wide.”

June’s eyes filled with tears as she looked at her sister. “Why are you doing this? Are you a sick-o?” She spit out.

Autumn smiled at June and answered, “You don’t get it do you? What you need to do is learn about self-discipline. You do whatever you want to do without any thought about the consequences and when you are reminded about the consequences, you only say, ‘I’m sorry.’ and expect to be exempted from having to face the consequences. Well that’s not going to happen this time. You have a choice. You can either do whatever I want you to do or face the possibility of losing Roger. This month we’ll find out if you really like Roger enough to face the consequences of your action. If you agree to my proposal, maybe you’ll finally realize the importance of thinking about the consequences before you decide to act. So, do you get on the bed like I told you or not?”

“Okay,” June replied meekly as she climbed on the bed and placed herself in the position Autumn ordered, “I’ll do whatever you want me to do but let’s get this over with.”

“I warn you, June. This is only the beginning. The things I’ll ask you to do will be very difficult and humiliating for you. It’s the only way you’ll learn.”

June pushed her face into the mattress as Autumn put both hands between her legs and ordered her to spread them wider. When June did, Autumn slapped her ass and told her to spread them as wide as she could. After stretching them apart as far as she could, June started crying. She shuddered when she felt her sister’s hand brush against her inner thigh and then again when she felt both hands spread her labia. Suddenly, the darkness was broken by a beam of light as Autumn turned a flashlight’s beam towards June’s vagina.

“What are you looking for?” June whispered, “You know my hymen was torn years ago when I was only 12.?

“Yes, I knew that.” Autumn spit out. “When you were taking those riding lessons. I’m just checking for any signs of semen. I don’t see any and your vagina seems pretty tight, so I guess you didn’t have any sex tonight, thank God”.

“I told you so.” June replied sarcastically.

“Well, one more place to look.” Autumn replied and proceeded to apply a dab of Vaseline to her finger and then to June’s rectum.

“Oh, God no!” June said. “Please not there. I swear I wouldn’t even think of having him do anything there.”

Slowly, Autumn worked her finger into June’s anus and moved it around in circles. “You’re right. Your ass is very tight.” She exclaimed as she withdrew her finger. Then noticed June’s vagina was suddenly moist and her labia had taken was a shade darker pink.

“Well it looks like you enjoy having something shoved up your ass. I see your pussy is soaking wet. Stay there just as you are. I’ll be back in a moment.” Autumn stood up and walked out of the room. She was gone for several minutes before returning with her “prize”. She held up a carrot, which had the tip cut off and rounded, to June’s eyes before easing it into June’s behind.

“Ow, Ow, Ow,” June whimpered, “Take it out. It hurts”.

Autumn giggled before answering. “No. That will stay in all night. If I check on you during the night, and I may do just that, it had better be right where it is now. The reason it’s there is to make your anus stretch out a bit and become a little more flexible. You see, June, Roger is a young man in his sexual prime who has, I’m sure, has had sex with several woman. It won’t be long before you’re faced with succumbing to his ‘needs’ or risk losing him to another woman who will. If you do decide to allow him to have sex with you, you should not allow any normal vaginal intercourse to take place for fear you would become pregnant. Ideally, you could get on the pill but that would be allowed only with parental consent since you’re still technically a minor or you can insist that he wear a rubber which he will not be enthused about or may not even have one available. Now you can masturbate him but that won’t satisfy him for long. You can offer either oral or anal sex which probably satisfy him longer – maybe until you turn 18 and can obtain the pill without mom or dad’s consent and they would not even have to know. Sooo, my dear, getting your anus a little more flexible, should you decide to have anal sex, will go a long way in making the first time a lot less painful. You may not think so now, but when it does happen, you’ll be glad I thought of it.”