Caution: This Sex Story contains strong sexual content, including Ma/Fa, Teenagers, Romantic, True Story, First, Oral Sex, Anal Sex, Masturbation, .
Desc: Sex Story: Chapter 1 - Carree Kasc met Billy Wilson in grade school. Together they grew as chums, then pals and friends. This story is about how they went from innocent teens and grew to be responsible, sexual, loving adults. The reluctant Billy is brought out of his sexual shell by Carree, whose repressed hormones finally explode as her body and mind mature in the world around her. Their fantasies come true as they experiment with their new found sexuality.
Billy was the only boy I ever thought about. From the time I was 14 he was my boyfriend. We went to St Pius X together from the eighth grade until we graduated from High School. From that time until he got his drivers license we were really "pretend" boy and girl friend because, beyond an occasional smooch here and there, after a movie or a chaperoned school dance, we were rarely alone together. His Mom and Dad, as well as mine, made sure of that.
What I knew of sex would rattle in a thimble and if Billy had an interest or knowledge of it, he never let on.
Once we turned 16, (our birthdays were on successive days) our parents lost a little of the control they had over us as Billy got his license. He was allowed to drive the family car, and eventually his own, to work, and, as long as I lived along the way, he was allowed to stop and see me. I finally talked my Mom into letting us go for little drives on hot summer nights to cool off.
"Tell Billy not to let his parents know I let you get away alone", she would say and smile.
They all had little to worry about because when we did park, we mostly talked. If Billy had any pent up sexual energy, he released it by talking. By that summers end we had gotten into each other's head fully and totally about every aspects of life and what we expected of it, except for sex. I began to think I was obsessed with Billy's seemed ignorance of the subject.
Towards the end of that summer our goodnight kisses began to have a tenor that bordered on necking. I was hoping he and I were both waking up to new horizons.
It wasn't that I wanted to HAVE sex, at least intercourse, but I was curious about it. I was not a big masturbator, but I knew what felt good when I showered and washed. My first real session occurred after a Show and Tell at a slumber party at my girlfriend Kim's house. There were 4 of us sleeping over and we spun a bottle and HAD to tell the truth about the subject on the card we picked, after the bottle landed on us. Megan got
"describe the last sex you had, when you weren't alone". She flushed a beet red, so we all knew she had something to say.
She had dated Jim Beachamp, a senior, since he asked her to the Winter Snowball in December. After 8 months of a sophomore dating a senior, something had to be going on. Megan made us all swear never to whisper a word, and she went into detail of a session at Jim's parent's camp.
A trip to a Mets game in New York actually was a trip to the camp in the Catskills. She described every touch and feel and told us what a wonder a penis was to hold in your hand. I don't know if her story was all true, but she made me wet. It was the first time I ever really got juicy and wanted to touch myself to some finish.
When we finally retired that night I volunteered to put my sleeping bag on the parlor sofa instead of in the bedroom. (a lack of space) I was alone and laid on my stomach with both hands between my legs. I had what I thought then was a pretty good orgasm, as I bit down on the sleeping bag to muffle my noises.
Another night a few weeks later I repeated the same scenario as I replayed Megan's words in my head. I was beginning to wonder if and when Billy would make a move on me.
Was I pretty enough? Did Billy find me attractive? Were we too much pals to become anything more? I had lots of self-doubts about my looks and my body. That summer, before my junior year I went bathing suit shopping and tried on some bikinis. My Mom scared the crap out of me by just walking in my dressing stall, checking on me.
She saw me in the bikini and said, " With your body, you won't wear that! Your father would throw a sheet over you and douse you in Holy Water."
I didn't think I looked THAT good, but Mom said that attracting a crowd would not be a problem. Although I was never obsessed with my body, I figured my measurements to be 34c-22-34. That sounded pretty good to me, but when I looked in the mirror, I was not impressed.
If Billy was impressed, he never showed it. He never ever tried to even give me a squeeze or a feel. But, he sure liked kissing me. He would kiss me often in public, and when we said goodnight, it was always a long tongue kiss, but never anything more.
I decided I had to be the aggressor. So, one night, as we said goodnight at the end of my drive (we never kissed in front of the house), I put my hands around his head and fell back onto the seat making him press his body to me. I liked it. HE liked it.
His tongue way down my throat, he ground his chest into mine. I thought he was going to try and feel me, or do SOMETHING, but after about 3 or 4 minutes, he sat up and said we better get going before someone got suspicious.
On subsequent nights we replayed the same scenario, but he was the one who pushed me back onto the seat these times. Finally in our third night of this I feigned a leg cramp and got him to let me shift my legs, and he, in turn, his.
We returned to kissing and tongue battles, but now I felt his erection against me. Little by little, without him really trying or thinking it, he began to grind me.
I thought, "Oh boy, here we go, he'll try something and I can set some ground rules". But, he just necked and ground and pawed at my back and shoulders.
How could he not feel my breasts as I pushed my hard nipples and chest against him?
But, after a while he would call time and finish the trip up the drive to drop me off. Three nights in a row of this was having its affect on me. In 17 years of Catholic upbringing I had masturbated twice, now I had done the deed these 3 nights in a row, and it was getting better every time.
If I was getting hot pants and the need for release, what was Billy doing?
I could only figure that he respected me too much or was afraid of my reaction to try anything else. I was vexed at this notion because he was the only boy I was ever interested in and anyone at school knew it was Billy and Carree: couple.
If he touched me inappropriately I was not about to tell him to let me out of the car and never speak to me again.
We just knew each other too well for that. But, it was becoming apparent that if anything else was going to happen, I was to be the initiator.
Sunday morning the public library was closed, but the University's was open. I asked my Dad for a ride to their library saying I had a school project due at the end of the spring recess. Right after church I changed and Dad brought me there saying he would give me a few hours before family Sunday dinner.
Once at the library my mission was to find books on sexuality with hopes of answering the questions I did not want to ask anyone else.
When I went to the look-up to find books on the subject, there were two books that answered all my questions, "The Joy of Sex", and "Sexual Revolution; a woman's perspective". They were not exactly textbooks, but they answered what I wondered, frankly and to the point. From my reading I discovered that,
Interest in sex is normal.
Masturbation was normal, and healthy.
Good sex can be had without intercourse.
No sex is "dirty" if both agree to it.
Billy's aversion to even breaching the subject was a fear factor he got from his parents.
Billy probably talked openly and spoke of his wishes or conquests with his friends.
Billy definitely masturbated each night when he got home from our sessions.
The fact he would not make the first move was another parental stigma.
When I had "wet pants", he was probably "leaking" too.
By the time I was ready to leave I was definitely awakened on many subjects of sex, and wondered why I hadn't spoken more frankly about them with my girlfriends.
The night Megan had to describe her sex session with Jim to us at our slumber party, I bet she and my other 2 friends whispered details after I left the room that night to take the parlor sofa.
My "virgin Mary" reputation may have made them uncomfortable talking in front of me. (I was the only one who worried about Sunday church that night). I heard them giggling, but with both hands on my vagina and groaning into my sleeping bag, I really didn't care or wonder what the subject was then.
In my mind, I released Billy from blame for the fact I was going home horny, wet, and frustrated from our recent dates. It was apparent I was going to have to take the bull by the horns on the sexual front of our relationship. Whoops, didn't mean that pun, but...
Going back to school on Monday, I looked at every girl and wondered what sex experience they had.
Some, I said, "No Way", and others "probably every night". (why do some girls make themselves look so cheap?) But one thing I did see. I was better endowed and developed than most of the girls in school. Lots had larger breasts, but not the good shape mine had.
Some had shapelier butts, but were flat chested. Of course, by the end of the day I wondered if I was a lesbian. God, I am sooo paranoid.
But, I was convinced that, unless Billy was gay, (No - not more paranoia!), he had to want me, and thought about it often. I was just going to have to make the first move and speak frankly to make sure the door was open wide to honest talk that would not be embarrassing.
Billy brought me home from school as usual on Monday, but had to get right home to change for work. We spoke little on the way making small talk about lunch and homework. I leaned over to kiss him goodbye, a nice deep kiss, not one we usually shared at this hurried moment, and I followed it with 3 more pecks on his cheek and forehead.
I smiled and scooted over, opened the door, got half way out and turned back and caught him square in the eyes with a question.
"You DO know how much I care for you, right?", I said.
Stunned at first, he answered, " Yes, I guess so... well of course I do!"
"You think I'm pretty, right?", I countered.
"Are you kidding me? You're the most beautiful girl in the school, and everyone knows it. I'm proud to walk down the street with you."
I was stunned; Billy actually said something flattering with sort of sexual overtones (for him). Trying to be cool, I closed the door and looked through the window.
"That's sweet of you to say, what took you so long say it? Girls like hearing things like that, ya know", I said teasingly.
With that, I turned and walked up the walk and was surprised he didn't speed off as normal.
When I turned at the door before I walked into the house I looked back to find him watching me walk away and into the door. I mouthed a kiss as I went in the house. I watched his car roll down our long drive to the county road, before he finally sped away.
I wonder what he was thinking as he coasted down the drive?
I didn't see Billy besides at school the rest of the week. We both had track practice the rest of the week and that took up our after school time.
The girls' team was bussed over to the University track to run, while the boys used the school facilities. I was a second on 3 of the event teams; I was only there for the exercise, although I did actually compete once on a relay.
Billy was more serious about it, but was not a star by any stretch. He wanted to play football, but having to work weekends to save for college made it impossible.
By Friday I was ready for a night out with Billy. There was a dance at school and firehouse block party in town. I told my parents we would go to the dance and meet them at the block party. That way after we showed, we could sneak off together.
My mind raced as to what Billy and I might do for intimacy alone.
I was pretty sure I had him interested, or at least aware that I was interested.
My world crashed when Billy called and said that his uncle, the one he worked for, invited him to hunting camp for the weekend.
Deer season had just opened and the testosterone must have been running with his family's men. They were all hunters and Billy wanted into that rite.
Megan called me about 20 minutes later and said her Jimmy was going with them and wanted to know if I wanted to slumber with some of our friends after the dance. It was going to be 4 girls, all dateless, because their boyfriends were out hunting Bambi. We each felt jilted and we knew the boy's ears would be ringing.
The dance was fun, but there were way more girls than guys and we danced with each other. A couple of the more cloddy guys came over to ask for a slow dance. Each of our group of four decided to accept at least one invitation and hope the word got to our boyfriends. I danced with Mark Smith, a short, shy, kind of cute guy. We made small talk as we danced where he was quite outgoing.
I told him he was a nice dancer and thanked him for asking. He was nice, but he wasn't Billy.
Megan's Dad picked us up after the dance and brought us all to her house. It was a big house where Megan had almost the whole second floor to herself. She had a huge bedroom and the other room was converted into a TV and study room for her, plus her own bathroom. We each took a turn getting changed into our sleepwear and settling in the TV room.
Meg's Mom came up and said good night and reminded us to stay in the TV room side of the house so we didn't disturb she and Meg's dad, who slept underneath. With that, we closed the door to the TV room and took up spots on the floor, sofa and lounger.
We were all quiet for about 10 seconds until Kim said "OK, Lets talk about sex!!", and we all laughed.
Megan looked at me and said, " I know you have a church thing, but get into the girl talk, it will be fun."
"Meg", I said, " I don't know where this religious thing about me got started and why you guys have to whisper dirty jokes and stories around me, but I am really not the virgin Mary."
"Don't get so upset, it's just a reputation you had in junior high when you wanted to be a nun", Megan defended.
"A nun?", I said. "Where did you ever hear that?"
"Well" Kim added, "that was the rumor for as long as I knew you."
"Not true, not true, not true", I chanted. "I go to church on Sunday with my parents, because they make me. That is as close as I am to a nun. You've seen me in the locker room, do I look like a nun?"
Megan, Kim, and Jennifer all looked at me, then at each other, and then Kim spoke up.
"Well duh, you have the most incredible body, you go out with Billy and he tells his friends you are frigid. He says you're saving it for God!"
I was stunned. "Well that little DICK, that son of a bitch", I said, surprising my self at my language. "I've all but had to tear my clothes off to get him to touch me. He's never even tried to feel me up."
"He tells another different story" said Jennifer, " He told Rob (Jenny's new boyfriend) that he got you to jerk him off and you put your finger in his cum and tasted it."
I was mortified and embarrassed. I got up to go home. "Meg, tell your Dad I need a ride home, NOW."
Megan came and put an arm around me to console me.
"Look", she said. "All guys are assholes when it comes to this shit. They make up stories to tell their friends of their conquests. It's a guy thing. They all do it. Somehow they don't think it ever gets around. It goes with the territory. He told one person you were saving it for God, and another you were a cum-eater.
He gets his stories mixed up.
When Jimmy took me up to his Dads cabin in the Catskills, he told his friends that we spent 2 days there, making love, and we did every thing. The truth: We were there for about 2 hours, with about 15 minutes of the inny-outty, just like I told you guys.
Don't let this ruin your night, our night. We will have fun, just us girls. We're gonna talk about sex and find out what's going on in each other's heads. I even have a pornie movie we can watch later. These nights are special. I have 2 sisters and they both told me to do this as often as we could. Sex and boys and life are all so confusing. Here we have each other to cry, laugh and wonder with."
Wiping tears, I said, "Wow, you're the sister I never had."
Jenny and Kim came over and we had a group hug.
"We're all sisters", Kim said. "Now lets get to the dirty talk."
That broke the ice and we all laughed. I felt a lot better knowing I was invited to this intimate party because they all liked and cared for me and each other.
"Yeah", I said. "Fuck the boys.wow, I do believe that's the first time I ever said that word out loud."
We all laughed again.
Megan stood up and said, "Lets raid the kitchen and get back up here and make the guys ears really ring. Maybe we can even make up a few stories about them."
"Yeah", Jenny added, "GAY stories!!!"
We all laughed like hell as we went down the stairs to the kitchen.
Armed with soda, chips, pretzels, and some frozen things that tasted like pizza after you nuked them, we all went back up stairs and took our spots in front of the TV. Conan had just started and we all munched for a few minutes, apparently hungry with a need for a sugar/salt/carbo high.
My mind drifted a bit and then said aloud, "I can't believe Billy said I did that."
Kim looked at me saying "What the jerking off, or the tasting."
"The TASTING", I emphasized. "The masturbating thing is OK, I guess."
After a second or 2 of silence Megan spoke.
"We'll all do it, not just the jerking off thing, the tasting thing, at least that what my sisters tell me. They say all women suck it; it's inevitable and natural and just a part of sex."
"My sister says the same thing", Kim added. "I was watching a movie with her and when Demi Moore went down on Michael Douglas I said Eeewww! She told me she would love to suck him, and so would I, someday."
I threw a pillow at her and told he she was a whore, and she said that oral sex was natural and fun and happened more often that regular sex.
She also said that a guy licking you down there was the best orgasm you could have."
"Two votes for the same from my sisters too", Megan added. "they both said that I might think of it as disgusting, eventually giving and receiving it would be the most regular sex you can have, especially when a bed and a room aren't handy. My sister Judy says it's the best foreplay because it makes the guy harder and really lubes you up, but I can't picture myself..."
There was a stone silence in the room as we all took in the sudden sex talk; just Conan and Marissa Tomei were heard in the background, but no one was paying attention.
"I walked in on my Mom doing my Dad", Megan shocked us by daying after a 10 second lull.
"Right in the living room one night when I got home from a dance early. I was quiet coming in so I wouldn't wake anyone and I saw them in the light of the TV. I stepped back to the door and opened and shut it again letting it slam a little. I heard them shuffle and my mom said something a bout my being home early, and that she was looking for a contact lens on the floor. But, I saw her with her shirt pulled up and my dad's thing in her mouth.
That was the reason I asked Judy about it."
I think we all tried to picture Meg's Mom and Dad in our minds
"doing it" for a second when Jenny, who had been quiet for the whole exchange finally blurted out;
"I've done it,... really. Don't think of me as a slut. It really was quite natural and fun. Remember last summer when Rick (her old boyfriend - 3 years older) went to Denver U. orientation in Colorado, and I went to my sisters in New York?
It was a scam.
We really shacked up for a week in the City.
My sister covered for me with my parents. Students who lived over 1000 miles were not required to go to the orientation, but Rick used it as an excuse for us to go away alone. With him going into college and my just starting my junior year we figured it might be the only time we might have to be alone. Plus, with him so far away, I knew we wouldn't be together anymore.
God, we did it 3 times a day... umm, not the blowjob thing, the screwing thing."
Three sets of eyes trained in on Jenny.
"Wow, true confessions!!!!" Kim said, "Tell us more."
Jenny sort of smiled and then got a little teary.
"It seemed so right at the time", she said. "Giving it up to him.
He taught me so much about sex. But, now I realize he used me.
I only heard from him once after he left. The first time he came home this past Christmas, he didn't even call me. I finally called him and he said he heard I was dating someone else, and that he was so much older and his life changed.
Being older didn't matter when he had me alone in a waterbed suite in New York. I felt so grown up at the time, but it was a lot of fun, then."
Jenny started crying and we all hugged her and tried to comfort her.
"Don't feel sorry for me. I thought I was King Shit, putting things over on my parents and my friends. I even let the bastard take pictures of me nude, and with his... his dick in my mouth. I was so fuckin' dumb", she spat.
Finally I was going to be the voice of reason and get the party going again.
"Jenny, you can't change what happened", I said. "Take it as a lesson learned and use it to grow with. You have so much going for you right now, you have great marks in school and can go wherever you want to college, you have a nice boyfriend, and you have lots of friends. Everyone does things they regret in life, and at the time you were sure it was the right thing to do. Who could have talked you out of it."
"You're right," she said. "I thought I was quite the grown up, and you know what, I had fun, even though it hurts now."
Megan scooted over on the floor and put her arms around Jenny and said, "So, tell us, what's it like?" Should we be afraid? Does the purple monster bite?"
We all chuckled, but really wanted an answer to her supposed joking questions.
"It's what your sisters said", she agreed as she looked at Megan and Kim.
"It seems a little funny at first, but it feels so natural when you do it, you feel powerful and subservient at the same time.
But any doubts about it are dashed once he puts his tongue in your... vagina, oh... PUSSY!! Why get medical? THAT is awesome."
Kim looked at Jenny as if she were going to say something and she stopped herself, then started, then stopped. "Never mind", she said.
"Go ahead", Jen said. "Ask me, I know what you want to know."
Kim half smiled, "OK, did he shoot it in your mouth? Oh God Jen, I'm sorry, it's none of my business."
Jennifer smiled, now somehow OK with her new stature as
"Yes, he did and he told me to just swallow without tasting, but you couldn't help but taste it. I was salty and a little sweet like, but had the consistency of egg white or unset Jell-O. It seems gross now, but at the time, and I suppose it makes a difference if you really care for the guy, it seems like a reward and you have something from him in your belly. If you aren't using it as foreplay for sex, and IT is going to be the sex, it seems like the thing to do at the time. Plus the swallowing motion of your mouth makes them go nuts afterwards. You know the supersensitive feeling, like when we, you know... diddle around down there."
Wow, a few minutes ago we were deciding if 90 seconds was too long for a pizza roll in the microwave, and now we were getting a review on the taste of sperm... well,... cum. It was quiet for a second. I suppose it was the assumed revelation that we all, "diddle around down there". That opened a whole new door if we wanted to talk about that, I guess.
But, I had one more question." Am I the only virgin here?"
"Well", Kim said, "since we know Megan and Jenny have both "done it", I guess you are asking me. I am still a virgin. I really fear getting pregnant. But, I have been so close, where I really wanted it and only common sense stopped me from doing it. As long as we are telling true confessions, Brad and I jerk each other off. He wants me to put it in my mouth, but I won't. My sisters both tell me not to do it until he's (Kim motions quote marks with her extended fingers) eaten my pie. God, they talk gross."
Megan reeled around on the floor and stared at me'
"So, kiddo, my friend Carree, the supposed and now denied Virgin Mary, but still an admitted virgin, who never wanted to be a nun, what have you and Billy done at the end of that long drive to your little house on the hill? Jimmy B and me have seen you guys parked there at least twice in the past weeks on his way to bring me home.
I know all and see all."
"Well", I began a little sheepishly, "I wish I had something juicy to tell you guys but I don't. Billy just lays on me and necks.
He's a great kisser, but I don't know what to do to get him to take a little initiative. I take and make all the first moves. I want to reach down and grab that hard thing he's pressing up against me, but shouldn't he make the first move? He's leaving me frustrated, and I figure he must, you know... do it - when he gets home. I don't want to have intercourse yet either, only for the fear of getting pregnant too. But, isn't it normal to get the warm and wetties and then want to do something about it?
Jenny looked at me and smiled "Wow, a guy who doesn't know what to do, where did you find him? It's just I don't know if its a good thing or bad. Have you tried just saying 'hold me squeeze me' to lead him on a little?"
"I know it's stupid" I said, "But, I don't want him to think I'm experienced or anything, you know - cheating on him."
"JeeeSUS, don't worry about that, guys even like a girl whose whorey in private... a... so I've heard" Megan said.
"My sister coaches me all the time, saying to be a little aggressive to let him know whose the sex boss. Like George on Seinfeld; 'you gotta have hand' in the relationship."
"Well,", I said " you guys gotta remember that I don't have sisters or an experienced partner. So I don't have a sounding board or a teacher. And this is the first time we ALL really opened up about sex. I mean, is it about sex or is it about love and caring for your partner, or are they both the same."