Carree Loves Billy: Holiday Weekend
Chapter 1: A little background...

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Teenagers, Romantic, True Story, First, Oral Sex, Anal Sex, Sex Toys,

Desc: Sex Story: Chapter 1: A little background... - Bill meets me on a ski trip with my girlfriend who agrees to give us a day alone to experiment and get to know each other on a more intimate basis. I give Bill a special surprise that he never expected to prove my love for him. The story entails our first time sleeping and waking together. We experience tenderness and passion as young lovers as we experiment with our bodies and sexual freedom.

For the third straight year, Megan and I took off on a ski trip the day after Thanksgiving. We had went to Okemo Ski Area in Vermont and stayed at The Tyrol all 3 years. They had a motel and a group of chalets. Our first year, we went with Meg's parents and stayed in our own chalet. Last year we got a room in the motel together to cut expenses, as we went alone. This year we had saved money to get our own chalet again.

It was, as usual, perfect timing for both of us to get away together. This being our senior year, we didn't know how many more "best friend" trips there would be.

Bill went to Vermont to visit his grandparents and relatives with his family, as was usual. While family is important, this was a Holiday week, and for as long as Bill and I had been together, he was gone this whole week. Wanting him around for Thanksgiving was just me being selfish, I know. Traditionally he packed up with his parents after school on Wednesday and came home on Sunday afternoon.

This year, Megs' boyfriend, Jimmy, was still in rehab after a horrible accident he suffered last Christmas vacation. It looked like he might be walking on his own by Christmas this year. It was a close call for Jimmy. If he could walk enough without depending on crutches, walkers or wheelchairs, he would finally finish his senior year with our class. (Megan had tried to sneak away with Jimmy last year on this same trip, but couldn't work it out to get past her parents.)

Bill called me Tuesday night about 10 o'clock from his writing room over the garage at his place. He was telling me how nice and cozy it was with the fire in the Franklin, and the only thing missing was me.

"So you called me just to tell me you were missing me, you're so sweet," I said. "But you also are going to end up frustrating me", I scolded him. "I know it's been a while since we really got it on together".

Bill and I didn't have regular intercourse so I could remain a virgin, which I really didn't care that much about from a physical standpoint. But, by remaining so, I would never have to lie to my parents about if I was sleeping with him, and foremost, I couldn't get pregnant. I just can't tell you how much I worried about that happening. Bill and I had major plans for our lives and we had seen what "doing it" could do to ruin that, if we slipped up.

In its place, we satisfied our urges with mutual masturbation, either watching each other, or doing each other, and oral sex. We had decided to save oral sex for times when we could get together, get naked, and be uninhibited. In plain words, no backseats of cars or "hiding behind the barn". But, our oral sex sessions were pretty intense and were probably as satisfying as any other liaison could be. Our first such oral extravaganza took place just one year before, in the very room Bill was speaking from. We had been there a few times since.

"We seem to have time for everything else", Bill said, "but finding time for us has been impossible. I know it's not my fault or yours, but lying here looking at the fire and thinking of you, well..."

"Bill you don't have the monster in your hand, do you, you bad little boy?" I asked.

"No, I don't, really. But, it may end up that way. Listen to why I called and tell me what you think.

While at my Grandmothers for Thanksgiving, we are going to take her car home.

She can't drive anymore and she is going to give it to me. She can't grasp that I have my own car, but my Dad says to take it and make her happy. She has been talking about giving it to me for 5 years. It's 8 years old and runs pretty good. Dad says to take it, fix it up and we can sell it, or sell mine, whichever is the best option after we work on hers.

Anyway, I was going to take her car skiing on Saturday, as I usually do. My parents say that as long as I am going to drive that far to ski, why don't I just drive the car the rest of the way home afterwards, and they will meet me at home on Sunday.

This way they can antique on the way home without me whining about it. Plus it gives them more room, without me there, if they buy more of that old junk.

Anyways, I usually go to Bromley, but I COULD go to Okemo.

Ummmmmmmmmmm... what do you think of that? And if you like that idea, how pissed off would Megan get if you deserted her for a couple, 5 or 6 hours in your room, or we could get our own?"

"Oh Bill, you are devious", I said. "This would be Saturday, huh?

That is usually Meg's marathon day. She likes to get at least 10 runs in on our full day. I don't think it would be a problem if I weren't there the whole day, but I would ask her first. See, normally, I won't ski THAT much. I get wind burnt to easy, and I'm just not good enough a skier to keep up with her."

"I don't want to horn in if this is a real 'girls' thing, it just seems like a good opportunity for us to be alone and, a...

special.", Bill said.

"It is a great time for us to be together, but she would hardly notice I was gone, I don't think. Let me get back to you." I said and I hung up to call Meg.

Meg didn't have a problem with Bill and I using the chalet for a love nest. She said she was a little jealous because she and Jimmy had such a hard time being alone since the accident.

Besides being in hospital, in the rehab center, and home with his family taking care of him, there was almost zero alone time. They committed themselves to their relationship just before the accident and she found out right away how tough some commitments were.

I called Bill back and told him that we could work everything out. I gave him our Chalet number and told him that Megan should be on her way to the slopes by 10 o'clock that day.

Although I would see him in the morning to ride me to school, I really wanted to stay on the phone with Bill all night that Tuesday. I knew he would be gone from right after school and I wouldn't see him till Saturday. We rarely ever went that long without seeing or touching each other. As we talked I was getting a little aroused and I let my mind wander about our Saturday 'date'. It was then that I wondered if we should try to open a new horizon in our sexual lives, anal intercourse. I just wanted to feel him inside me.

Two different times in our love making Bill had expressed an interest in my butthole, that is, tonguing it. Once, the first time he brought up to his writing room over the garage (I had showered within a couple hours before), and another time when we showered together the first time. I always worried about being clean for him there when he would go down on me and I thought he might want to go lower. I remember one night when he wanted me to turn over and show him my ass and I refused. He took it as a rejection, but I had recently voided myself and was quite uncomfortable about that. What do you say at a hot moment like that? There are no gentle words to keep the moment alive.

We talked about the possibility of anal intercourse a couple times and let the subject die each time. While it seemed like an improbability, I remembered the video Kim showed us where the girl on the screen absolutely loved the act. Plus, from reading at the library from The Joy of Sex, Kinsey and other books, it was something many couples considered.

My entire interest in it stemmed from one thing. I wanted to feel Bill inside of me. To feel him within me and to hold him heart to heart was my wish. However, I was not willing to go through a lot of pain to accomplish this. Love should not hurt. A woman says the greatest pain you have is bearing children, and I want to keep it that way. If it's painful it is not making love. I remember Kim told us that her sister preferred anal over regular intercourse, although it was not something she and her husband did on a regular basis. To her it was "as intimate as a couple can get". I suppose she was right.

I wasn't totally sure if I wanted to go through with this. For that reason, I never made mention of it to Bill, so as not to disappoint him if I chickened out. Clearly, from our conversations, he was not interested in having me go through the pain of it to please him. But, I know the girl in the video wasn't experiencing pain, and I know from a tongue in my butt, there are good feelings to have back there. I went to sleep Tuesday night weighing my options.

When Bill picked me up for school in the morning he was clearly excited about our upcoming chalet date. He said he was going to make sure we had the best time ever and couldn't wait to shower and hold me naked under the hot water. Needless to say, I went to first period with a case of the warmies down below. My second period that day was a study hall and it was there I decided I would try to be prepared for butt sex when Bill came that day. If I changed my mind he would be none the wiser. I knew the preparation would be uncomfortable and a little embarrassing to do together. To properly prepare, consensus was that an enema was necessary. An enema is, to me at least, a private thing. When Kim's sister was detailing her tale about anal love to Kim, she talked about the doing the enema together, but I couldn't do that. (My God, she told Kim she gave him oral sex while she was expelling the enema.) Some things should be left to privacy.

However, whatever two people do together, that they both agree upon, is OK, I guess.

From reading different things on the subject, many couples that do it on a regular basis have said that the enema is not necessary as long as the female has had her BM that day. To me, the enema takes away any chance of an unexpected surprise afterwards. THAT would certainly ruin any special moment. If I had to go through a little discomfort for that assurance, so be it. It's funny, about human nature. The mention of anal sex usually conjures up perversion, homosexuality, etc. But when you think of it with someone you love and trust it is really a sensuous thought.

I did fear the pain and possible rejection of the idea by Bill or myself. But to think of that "private place" as something sexual is easy if you have the right attitude towards your partner, and making both he and you happy.

I saw Bill right after school and he said he had to go right home so they could leave, and if I wanted a ride, or to use his car while he was gone I had to go right away with him. Since I had errands to run I told him I would take his car. Since I got my license, Bills parents didn't mind if I used his car for short trips in town, shopping, errands, etc. Usually, if he was working I could either ride in with him or my Dad would drop me off and I could pick it up. It was just one more thing that we began to share as two people planning to be together.

Bill drove to his house and we had a long goodbye parked in front of the garage. As I held him and kissed him I wondered what the prospects for a wild lovemaking session held for us. I am sure he was looking forward to being alone with me, but I think I was going to surprise him with what I had in mind.

As we stood by the car Bill took his keys off the ring and he whispered to me "Make sure you save your shower for me on Saturday. I'll make sure you're squeaky clean", and with that he gave my breast a caress and my butt a squeeze.

"BILL!", I said "What if your Mom is watching?"

"I just don't care anymore. I love you and I don't care who knows. If she saw us, she is peeking at something that isn't her business. Besides, she's busy inside packing", Bill said.

The words were no more out of his mouth when his Mom came round the corner from the front of the house where she was packing their car.

"Can you two stop smooching long enough so we can leave?", she laughed. "Hi Carree, you look pretty today. Are you letting your hair grow out? I like the big wave thing you are doing."

"Thanks Mrs. Wilson. Bill likes it longer, with the big curls.

But come summer I think I'll cut it. I hope we didn't hold you up. We were just saying goodbye." I said as I took the keys from Bill and began to get in the car.

"Oh, you'll see him soon enough. Have a nice Thanksgiving Carree, and express the same to your family", Mrs Wilson said.

I stopped short of sitting in the car to go give Bill's Mom a hug and kiss. The first time I did that.

"You folks have a nice Thanksgiving too. I know it's special to go and visit your families. That's what the Holidays are all about", I said turning back to Bill's car. "Bill, if your car isn't back when you get home, call me and I'll bring it right back. But, I think I'll have my Dad follow me out tomorrow before dinner. I Love You Bill Wilson", I said as I started the car and began to back up.

"I Love You too, Carree Kasc" he said with a wink as he watched me roll passed he and his Mom.

When I got home to change I heard a passing car beep and it was Bill and his Mom riding by on their way to town to pick up Bills Dad from work and go to Vermont. My Holiday weekend had begun.

The first thing I had to do was a little shopping for my "date"

with Bill. I needed some things at the pharmacy. From reading about the act itself, anal intercourse could be easiest facilitated with something to dilate myself. I believe this was from a book, that I was surprised to find in the University's library called, Alchemy of Ecstasy. I read so many I forget which was which. (Amazing how many sex guides etc., can be found in a psychology section of a library) I wanted something called a butt-plug or anal dildo or vibrator.

I was a little paranoid going into the pharmacy to get the things I needed. I was sure if I bought Fleet enemas and KY jelly at the same store the clerk would look at me and say "Oh?, a little anal sex this weekend?" So I did go to 2 separate pharmacies to get each. Then I drove to a third to buy condoms. One of the books I read said that if the male wore a condom, initial penetration might be easier because of the smoother surface. I took the package of small round discs to the counter, put them down and fumbled in my purse waiting for the clerk to give me the total.

It may have been the longest 3 seconds of my life, but soon I was in the car on my way home. There was one more place I wanted to stop, but I was sure I would not have the nerve to go in. There was an adult bookstore just off the main drag on the other side of town. It wasn't in a bad section, just definitely off my home turf. I parked right in front and watched, with the doors locked, as people went in and out. In 15 minutes I saw 6 people go in and the same 6 come out. I didn't see anyone else on the street for a block or two, so I got up my nerve. I got out of the car and went inside.

One entire wall was pornographic movies with explicit pictures on their covers and the back wall had a curtain hanging over a door way with a sign that read "Peep Shows - tokens required". I looked right and saw a huge glass counter and a large displays of sex toys on hooks behind it. I was relieved to see a woman, a little tough looking, but a woman, behind the counter.

"Hi, I guess I look a little out of place here but, I need some help. I'm going to a bachelorette party and want to get a gag gift", I said nervous and sweating.

"Sure honey, we get those requests all the time. What'll it be, do you have anything specific in mind?", she asked.

I'm not sure, something tasteless I guess," I said as my eyes perused the wall of toys (many of which I did not WANT to know WHAT they were used for)

How do you ask for a butt plug, I thought to myself as my eyes searched for the item that it might be.

"For those type of parties rubber cocks and butt plugs are common, maybe a riding crop?", the woman asked.

"Um... I'll take those,... a, what you said", I answered hurriedly. I couldn't wait to get out of here.

"All three?, she asked.

"No,... umm just the first one, no... two. Yes, those 2 things", I said as I pulled out my wallet from my purse.

"OK, sweetie, that will be $18 dollars. Do you want some cock and balls wrapping paper for them too?", she asked.

"No, just put them in a bag for me" I said as I counted out my money to her.

We exchanged money, got the bag and I went out the door in a hurry. I kept my head low and pulled sunglasses from my purse to disguise myself a little. No one was on the street and I made a clean get away.

18 dollars!!, I thought to myself. They must be making a fortune in that joint. Then I thought that if I had the courage to say,

"No, just the butt plug", I could have saved myself $10 dollars.

But, considering that I never, ever, thought I would be able to get the courage to buy a butt plug, it was worth it. I might even have a little fun with the rubber cock. No, I couldn't do that, could I? That would be cheating on Bill, right?

I got home and began to run upstairs as my Mom met me at the door.

"Hello dear, she said. What did you buy?"

"Oh, you know, Mom. Just personal items for the ski trip, my period is due is a couple days. Plus I have to shave my legs (and my pussy, I thought to myself)", I answered as I bounded passed her.

"Whats your hurry", my Mom said.

"I gotta pee Mom," I said as I went into the upstairs john.

Just as I went into the bathroom with my bags and all in my faux pee rush I realized that I hadn't even looked at what the clerk had given me. I sat on the lid of the toilet and looked at the bag that I had stuffed into the pharmacy bag. "Oh God", I thought to myself, "What if she gave me joke sized toys for my 'gag' gifts?". I reached into the bag afraid of what I would pull out.

I wrapped my hand around what was a soft, long, full shafted penis. I pulled it from the bag. It was snow white and felt like hard jell-o. It was stiff, but pliable, and just a little bigger than Bill. "What in Gods name am I doing with this?" I asked myself. I actually thought of flushing it down the toilet, except if it plugged things up and a plumber came, I would be hard pressed to explain. Maybe Bill and I could graduate to a new level of perversity with this, I thought. Maybe not. My mind raced as I took it and wrapped it in one of the pharmacy bags and thought of a place to keep it safe from discovery.

I reached into the bag again and through the plastic wrapper I could tell the butt plug was made of the same gel like stuff, but was much smaller. What a relief!! I pulled it from the bag and saw a clear azure blue item about 7 total inches long. It was thin as a pencil eraser on one end and expanded to at least the girth of Bill's penis and then bulbed abruptly down to about the size of a broom handle with a large round disc on the end. It was obviously made to slip in easily to get past the hard muscle and then fill the anus, closing down on the skinniest part of the shaft. The disc prevented it from sliding all the way in. It was scarey to say the least. My God, what had I got myself into? I couldn't do this, and I couldn't let Bill use this on me, it was way too embarrassing, plus I bet it hurt like hell.

"Carree, are you OK in there", my Mom shouted from downstairs, startling he hell out of me.

"Yes, I just got caught up in a piece I was reading", I yelled back.

I quickly rolled the plug in the bag, grabbed the other bag with the white rubber dick and put them in the bathroom closet on the top shelf under my extra sheets. I came out of the bathroom and my Mom was walking by with a pile of my clothes she was going to put away.

"It's not good to sit on the toilet a long with your privates all distended like that. You could get hemorrhoids, and you won't have a problem getting those after childbirth. No sense in rushing them", she said matter of factly.

"You sure have a way to keep the joys of life from creeping over me, Mom", I said laughing.

"Well, you're not a child anymore, and you should begin taking care of your adult body so it stays healthy so you can enjoy life and its pleasures", she said.

"Like sex?", I said to get a reaction from her.

"Yes, like sex, smarty pants. Childbirth, and raising kids too.

You need to be in good shape for all of that. It's not so sexy to go to bed with your lover if you have hemorrhoids or other problems down there. Plus you have to watch your weight. If you have kids you're bound to gain weight. Your husband may not like a fatter you. Nature builds our bodies to expand after having kids. We have wide hips to carry children on them", she said.

"Mom, Bill will love me no matter what happens to me or what shape I end up. He LOVES me. ME the spirit, not the body", I said.

"I hope you're right about him. I'm sure he likes the body your spirit runs around in", she added.

"Mom, he made googie eyes for me when I was a flat chested 7th grader too. He loves ME. My body is just a bonus for him", I said to get some response from her.

"Remember, he doesn't need to buy the cow, if he's getting the milk for free", she said.

"Do you suppose his mother is telling him that I won't buy the pig if I get he sausage for free, Mom? Come on. No need to talk to me in that tone. I am a grown up woman, and I think I make pretty good decisions, and I think that WE, Bill and I, make pretty good decisions. They don't accept dummies at the colleges we're going to...", I said.

"Don't be thinking about getting the sausage young lady, you have an education to get. That's not quite the way a young lady talks.

Do you think you'll spend every waking minute mooning over him in college, I doubt it", my Mom snapped back.

"You're the one who thinks I meant penis when I said sausage, Mom. It wasn't that kind of analogy, but I like it... Our college lives will be less than 50 miles away from each other Mom. If we both have cars, that's a half hour each way for us to meet as we wish. It takes 10 minutes to get to our house now.

Twenty five minutes each way won't make a whole lot of difference I think we'll be seeing a little of each other at school", I said to make the point that they won't know one way or another.

"Carree, my point is; you have a college education to worry about, and you shouldn't be tied down to a commitment with a boy.

Running every day to meet each other to do whatever you do will only serve to take time away from your studies", my Mom said.

"Mom, he's no boy, he's a man. He is also the man I plan to live the rest my life with. So, if I see him everyday, or every month in college, that won't change. Mother (I started to tear up with emotion), I love Bill. We are not 2 kids who found a new toy, full of infatuation. In 5 years I hope we can be married and both have careers. Bill is going to intern with Time magazine while at school. They are helping him pay for his college. How many high school students do you think get that opportunity? He must have impressed a few more people than just me,... huh? In twelve years we plan to have children. That's how much we have planned.

Along with you and Dad, he is what I love about my life. I have 3 people who love me unconditionally. Please don't speak of him like he is something I am going to outgrow. (I was crying pretty good now) We plan to support each other in our studies, and won't do anything to scuttle our plans for our lives and our futures.

Please give us some credit, Mom. When you give me that 'young lady' crap you do it to show me you are the boss, not my Mom. I want you to be my Mom, OK? Treat me like a grown up daughter, because I am", I tearfully finished.

Mom came over and hugged me, saying "Carree, I am sorry if I made you feel that way, I really don't mean to. I have a hard time thinking of you as anything as my little girl. We never thought we would have to give you up to a man so soon, that's all. We want you to make the right choice. I know your relationship is more than puppy love. I just don't want to see you hurt".

"Mom, I trust Bill as much as I trust you to never hurt me", I said. "I expect you and Dad to trust me to make the right decisions. Believe me, Bill is the right decision".

"OK Carree, I'll trust your judgment. And, if it means anything; your Dad and I really like Bill a lot. Speaking of your Dad, I better go start dinner. He wants to go and look at new cars tonight. We have appointments with 2 dealers. Imagine, the night before Thanksgiving, he wants to buy a car. The financing deals end on Saturday and he has to work this weekend. I'll call you for dinner", she said as she kissed my cheek and went downstairs.

I was now even more determined to try and make my Saturday morning with Bill a very special time. With my Mom safely downstairs, I went to the bathroom to retrieve my sex toys. I put the plug in my pillowcase so I could see how to use it later. The rubber penis might never get used, but I did want to leave that option open. I put it behind the false bottom in my travel trunk in my closet. We were supposed to go on a cruise one year when I was small and my Grandma bought it for my birthday. I kept my old dolls and doll clothes in it now. I don't think anyone knew it has a false bottom hiding place in it.

Dad got home and we had dinner almost as soon as he walked in the door.

"Sure, we have to hurry so these low life car salesmen can get home to their families the night before Thanksgiving. How about me? I have a family too", was the essence of my Dads mutterings all through dinner.

"Poor Daddy", I said. "Tomorrow, Mom and I will make a special Thanksgiving for you. Just think you will have your Mom and Dad here, plus your brother. It will be special".

"Thanks pumpkin. I know you and Mommy will make it special", he said as he chugged down his water and told my Mom to leave the dishes for me to do so they could leave.

"Go ahead, I'll get everything. I can clean up", I said. "Try to get a red convertible if you can. Wouldn't I look great driving to college in that?"

"Yes, you would look great, Carree. It's not going to happen, but you would look great" My dad said grinning like he played a joke on me.

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Story tagged with:
Ma/Fa / Teenagers / Romantic / True Story / First / Oral Sex / Anal Sex / Sex Toys /