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The Education of Heather - Part II Couple , Oral , Anal

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The Education of Heather - Part II

Hello again . Those of you who read part one need no intro but bear with me as I describe myself to the newcomers . I am Heather , 28 y.o. slim of build , 5'3" , 105 lbs and a not so dumb blonde . What I did not mention before is that I have a very healthy sexual appetite (although some may have guessed that) and I am bi . The reason for my appetite is my introduction to sex as a young girl . The "special education" I received is for most , one to be envious of .

Now to continue...

I was now 15 y.o. and thinking I knew pretty much all there was to know about sex . Boy , was I wrong . My sis who was now in college had shown me the joy of girl to girl sex and how to bring toys into our lovemaking and of course the big "O" as in orgasm . She had introduced me to our neighbor Mrs. Jackson where I babysat for a few years and she continued where Carrie my sis had left off although it necessitated a little push from me . This came after the incidents I am about to relate . I had also experienced sex with a few boys but there was always something lacking you know , like my orgasms ! My sis had talked to our mom and I was put on the pill for this reason although my folks preferred not to talk about it . Anyway , what I wish to relate now is how I used my little brother Billy to round out my "education" .

It all began one afternoon when I was watching him as my folks both worked and what had been Carries job was now mine . We had a hard rule not to invade each others privacy (at my insistence of course!) so walking into each others rooms uninvited or without knocking was not to happen . That day I was feeling bitchy and he once again had been in my room as my lingerie drawer was messed up so I burst into his room to give him hell . Lo and behold , there he sat with a look of horror on his face and wearing nothing but a pair of my panties and pulled down so his cock was protruding ! In his right hand he had another pair of my panties which he was stroking it with !

"Billy , what the heck are you doing ? I demanded .

"Golly sis , you aren't suppose to walk in like that !" he answered .

The interesting thing was how it all struck me . Seeing his cock , although small in broad daylight caused a stir in me which I didn't understand .

"Those are my panties Billy and mom is going to kill you " I said .

"Oh gosh Heather , don't tell mom , please." he replied .

He was frozen in position and all I could do was stare as the stirring in me became stronger . His cock seemed so beautiful . An evil thought was forming in my mind not just for the moment but for future considerations as I knew at that moment he was mine ! I guess you could say I was on a power trip . He finally became aware of his position and started to cover up .

I took a breath and said , "Billy continue what you were doing" .

"What?" he replied .

"You heard me" I said again in a mildly threatening tone, "continue what you were doing " .

"Aw gee sis don't make me do this " "Do it" I snapped "like I wasn't here" .

He rather reluctantly wrapped his panty covered hand around his cock again stroking it nervously causing it to regain it's firmness lost due to his scare . It didn't take him long to get into it almost forgetting I was there . It was getting redder as he slid his hand up and down the shaft . Then he rubbed the silkiness of the panties across the head of it , then back to stroking it . So that's how boys do it I thought . I saw his body start to shake as he laid back on his bed as a string of cum shot out from his cock all the way to his chest . This of course explained why I feel guys shooting into me I thought .

"Now clean up . We have to talk" I said . I watched him as he used my panties to wipe his cum off himself and removed the pair he was wearing and said "Mom is going to think I made that mess Billy" I scolded . "Okay , I'll get some tissue " he replied .

I watched as he walked to the bathroom with his cock still pretty erect and cleaned up . Afterwards I had him sit on the bed still naked and I asked if he could do it again right away . He replied "no, I don't think so ".

"Want to bet?" I stated reaching over and wrapping his cock in my hand . He just stared at me with a look of disbelief and then said "aw gee Heather" . It wasn't long before I felt it start to swell again in my hand .

"Show me how" I insisted .

"Are you sure you want to do this sis ?" he asked .

"Yes , now show me" I again insisted . By now he was rock hard again .

"And by the way , no one is to hear about this!" . I insisted .

"Of course not sis " he replied .

"Okay , lets do it" I said .

So he said "First wrap your hand around it and just slide it up and down . Yes , like that . Now rub the end lightly as you slide up and back . Yes , that's it sis". That was the last instruction I needed as nature took it's course . I squeezed a little harder and stroked a little faster as I felt his precum oozing out lubricating his cock . It wasn't long before he started squirming and trembling and once again cum shot out of him but a lot less this time .

"That was fantastic sis " he complimented me .

"Was I good ? " I queried .

"Oh my yes , you can do it for me anytime you want " .

"You damned right I will and whenever I want and I intend to . Just remember who's running the show here !" I informed him .

"Okay boss" he said with a smile .

Well it wasn't long before I decided to have another go at him . I now was able to walk in on him whenever I wanted to and did . Two days later I looked at him and asked , "with or without panties" .

"With" he said and with that he proceeded to get a pair from the laundry and put them on as I watched . His cock was all ready getting hard so he tucked it into my panties and said "Okay" . I rubbed it through the panties for a while then slid them down exposing all . I grasped it and stroked it and squeezed it and watched to see what got him going the most . It wasn't long before shot all over my hand and blouse . "Yuck " I said and without thinking I jumped up and removed it He just stared at my breasts in my bra . I noticed his stare and asked if it excited him seeing me with just a bra on .

"Oh my gosh yes " he said . I figured what the heck . I reached behind my back and unsnapped it and as it fell away his jaw dropped .

"Ever seen breasts before" I laughed .

"Just in pictures but they were nothing like this" he said .

"You can touch them Billy" I offered . He jumped off the bed with his cock still hanging out of the panties and placed his hands on them .

"Rub them gently" I insisted and as he did I looked down and saw his cock growing again . I felt my nipples get hard and that feeling start in my pussy . I was unsure just where to go from here as after all he was my brother . What I was sure of was I needed to do something as I was getting hot over all this fooling around .

"Lick my nipples Billy " I demanded and he went right for them .

"Suck each one into your mouth now" which he did quite eagerly .

"Wow , this is super " he said , "I love this " .

Now his oral play really had me going . I removed my skirt and sat on the bed in just my panties .

"Okay , now I am going to show you how girls do it " I told him as I slid one hand into my panties onto my pussy . I was not at all surprised to find wetness there . I slipped one finger over my clit into my tunnel .

"But sis , I can't see anything" he stated .

"Oh , all right" I answered and removed my panties .

"Have you seen a cunt before?" I asked feeling like a teacher and I guess I was .

"No again , except in pictures" he replied "but they didn't look as good as yours . He was once again rock hard with his cock sticking out of the panties .

"Want to do this?" I asked as I slid my finger in and out of my pussy .

"Gosh yes Heather , can I ? "

"Okay , but just be gentle and do as I tell you" I insisted . With that he placed a hand over my cunt and slipped two fingers into my wetness .

"Not bad for a beginner " I laughed . He wasn't laughing though as his eyes were popping out of his head again .

"Slide them in and out until I tell you to stop , yes like that . It feels really good Billy .

"Me to sis , I love it" . This went on for quite some time as I to was really loving it but finally it was time to move on .

"Okay , now slide your fingers up between my lips and rub that little bean you see there . Yes right there , that's my clit . Now rub lightly and move your fingers around in a circle" , yes just like that" . I was plenty wet by now and he certainly was an apt pupil I thought .

"Okay , that is real good so now take turns sliding your finger in and out of my cunt and rubbing your fingers on my clit" . That was the last instruction he needed so I layed back and let him do me . I could see his cock sticking straight up and urged him to move closer so I could reach it which he was happy to do . I wrapped my hand around it and stroked it gently while he fingered me . This was so nice I thought . Not too surprisingly he cum again before me onto my stomach but I warned him not to stop as I was getting close . He hardly missed a beat . When I finally did cum I cum hard and shook all over grabbing his hand and pulling it into my pussy .

"Wow , girls get that feeling to?" He asked .

"We sure do" I answered . "Do you think all this is just for you"?

"No , I just didn't know but I am really glad ".

The next encounter was the following week as I had gotten busy studying and babysitting . I could tell by his daily looks toward me that he was anxious . I just smiled and shook my head no .

It was a Wednesday and I was feeling horny so when I walked into his room and yelled strip he did so in record time . I laughed again as he was once again wearing my panties .

"Do you wear them all the time " I asked .

"No, I put them on when I get home from school ".

"Every day" ? I asked incredulously .

"Most days " he replied a little embarrassed .

I stripped down to my panties and bra so he would be more comfortable and told him to sit in the chair by his desk . My intention was two fold . First I wanted to see close up and personal what one of these things looked like and this was a perfect opportunity . Secondly , I had been thinking of doing this for quite a while but was always afraid to try it with a date for fear of getting a bad reputation as some of my girlfriends had . Here was another perfect opportunity . I knelt between his legs and removed my bra and put one hand on each of his thighs spreading them .

"No one but no one hears about this , OK ?"

"Gosh yes but what are you going to do ?" . " he asked .

"Just sit back and enjoy it" .

I held his cock in one hand moving it around to better check it out. It was only about four inches long but shaped like all the rest . I ran one finger of my other hand around the head of it which caused him to groan , interesting I thought . I circled the rim with a finger causing him to groan more . I concluded correctly that there was more response touching the head and it's rim than the shaft . I bent it down toward my mouth a little , moved my head forward and wrapped my lips around it .

"Oh my gosh sis , are you really going to do this ?"

"Uh huh" I replied as best I could as his cock was in my mouth .

"Aw Geez " was all he could say .

I slid my lips forward engulfing all four inches in my mouth , slid back a couple of inches and ran my tongue around the head . After doing a bunch of times he was going crazy which made me proud . I surprised myself as I was thoroughly enjoying this , never guessing I would like the taste of cock . I sucked a little harder and moved my mouth up and down a little faster . He was moving all over the chair by now .

It wasn't long before "Sis , sis , I'm going to shoot " he cried .

I hadn't thought of that aspect of it , that is , him cumming in my mouth but what the hell I thought , I might as well experience it all . His cum splashed against the back of my throat with quite a bit of force causing me to involuntarily swallow . I kept up my sucking , draining his balls and swallowing until he went a little soft and pushed me away saying the feeling was too great . I didn't really care for the taste of his cum but thought that swallowing was the neatest way of disposal . I was to discover later that guys prefer that . What a little whore I am becoming I thought with a chuckle .

"Sis , that was a hundred times better than with your hand !" he said .

"I know " I said "and now you're going to do the same for me !" .

"You mean ...."

"Yes that's exactly what I mean " I said "now get out of the chair and let me sit ." We reversed positions and I said "first remove my panties" which he did . Before tossing them aside he sniffed them . Wow , he really is into panties I thought . I moved forward so my pussy was at the edge of the chair . I reached down with both hands and with my fingers spread it wide open for him . He just stared at it until I said "get to it" .

"I don't know what to do Heather " he stated .

"Do the same thing with your tongue you do with your fingers for a start " I replied . He brought his face forward stuck out his tongue and inserted it between my folds . Mmmm , nice I thought . He slid it in and out for a while then moved up to my clit lapping at it . Mmmm , real nice I thought . I let this go on for quite some time not hearing any complaints from him . I lay there thinking how great this was but finally I felt it start inside me and couldn't put that off .

"Okay Billy , purse your lips around my clit , suck it in and run your tongue back and forth over it " I requested . This was just how Carrie , my sis had taught me and he caught on quick . Once again I thought , he is an apt pupil as he was driving me insane with his oral maneuvering . Yup , here I go I thought and sure enough I started to cum all in his face as I was pulling him into my cunt . And he was right , it was a hundred times better than with a hand which I was all ready aware of . I don't think he will ever replace Carrie but he was for now the only game in town and would do fine .

"That was nice Billy ". I complimented him .

"Hey , I loved it to Heather " .

"Really" I asked .

"Oh my yes!" He insisted .

"You're quite the little cunteater" I said .

"And you quite the cocksucker" he replied a little sheepishly .

"We'll do this whenever I want , okay" ?

"Oh my yes sis , I love it to " he exclaimed .

And indeed that was the case . Whenever I felt horny I would signal him with a smile and he knew it was going to happen that afternoon . It even got so he would give me a questioning glance and I would smile in response . I figured fair was fair as he liked it to , although I never failed to enjoy his oral play . We tried different things like sixty nine and I showed him how to use my dildo in my pussy . And what a confidence builder it was for him . Although he never once talked about it to his friends they all knew something was up just in the way he interacted with them .

Many weeks went by of mutual sexual satisfaction . It was great for both of us but I started thinking I needed something more and I am sure you can guess what that was . Billy to was feeling it as lately I had noticed when I was sucking on him he would pump his cock in and out of my mouth . At one point when we were in a sixty nine and he was on top I removed my lips from him and suggested he fuck my mouth .

"I'd love to sis " and the way he said it I knew he had been thinking about the issue as I had been . I wrapped my lips back around his cock and held my head still and sucked on him tightly . He slid his cock in and out hitting the back of my throat . He slowly fucked my mouth for a while but when he started pumping a little too hard and I had to say , "Easy Billy . It's not my pussy " .

"No , but I sure wish it was " he replied . There ! It was now out in the open .

He continued sliding his cock in and out of my mouth but it wasn't long before I felt him speed up and then his cum splashed against the back of my throat and as usual I swallowed it all . Meanwhile , my pussy had lost his attention so I had him get off me , turn around and lick my cunt until I got off .

Afterwards , he lay next to me and stroked my breasts . I looked directly at him and said "We can't Billy !" .

"Why not? " he asked . "You said you were on the pill and I want to fuck you so badly" .

"I want to also but you are my brother and we have to draw the line somewhere " .

"I dream of cumming in you every night" he said .

"Sorry Billy , it just wouldn't be right" .

The oral play continued for a few more weeks but it was getting harder and harder to put it off . It was one of those things where by putting it off , the desire continued to grow and grow in both of us .

Then it happened . One afternoon he was licking my cunt and I was at the the point of orgasm when he slid up and licked my breasts . I felt his cock at my portal and I cried , "No Billy , No! " . But there was little conviction in my voice so he continued by pushing forward . I did resist some but not enough and his cock entered my cunt all the way .

"We can't Billy , we can't " I screamed but his cock in me was so very exciting that I ended up wrapping my legs around him pulling him deeper . We fucked and fucked and it was like nothing I had ever experienced with any of the other boys . This is what fucking is suppose to be like I thought in my bliss . My orgasm caught me off guard as I was sure he would cum first .

Realization then took hold and I pushed him up off me out of my cunt just in time for him to cum all over my belly .

"Aw gee sis , that's not fair!" he exclaimed afterwards .

"I'm sorry Billy , I had a weak moment . You can't cum in me !" . I told him . "We can't get me pregnant no matter what. I am not one to blame it on someone else and mom and dad would kill both of us ! The pill doesn't always work you know " .

Well , those weak moments started happening frequently as I absolutely loved him fucking me . We fucked every way we could think of and I never failed to have an orgasm . I made him promise not to cum in me if he wanted to continue this and he swore he wouldn't . What he didn't realize was that I was as hooked as he was on all this . Eventually , he got hold of some comdoms and I let him finish in me . I didn't like the feel of them at first and he complained that most of the feeling he experienced didn't happen wearing them . Although I have to say when he was wearing one I sometimes cum twice as he was able to hold off . I layed out the ground rules for him to decide . If he wanted to cum in me , he must wear a condom , otherwise pull out first ! Little did we realize we were playing with fire as neither of were aware that there is sperm in precum ! . Very , very , fortunately , thanks to the pill, I never got pregnant .

What a wonderful sex life we were living . My girlfriends all asked why I didn't date and I jokingly replied that masturbation was enough for me . If they only knew !

Everything was so perfect with me as I could have sex anytime I wanted and I could dictate just how I wanted it . Whether I wanted to go oral or get fucked was entirely up to me . But I could sense in Billy a disappointment , something lacking especially when we fucked . I knew it was not being able to cum in me without a condom but he knew the ground rules and wasn't about to give it all up . I guess it was me that finally decided to do something about it as I really cared for him and wanted him to be fully satisfied as I was in all fairness .

I had heard of people that enjoyed anal sex but I was really put off by it as I heard there was pain . Well Billys cock wasn't very big and I thought that this would be a great way for him to cum in me without the worry of getting me pregnant . Of course I was also curious what it would be like being the little whore I had become I thought laughingly .

Billy's favorite way to fuck was doggy style so I formulated a plan . It happened one afternoon while he was fucking me in his favorite way without a condom . I had lubed up my ass with baby oil liberally and on one of his backstrokes I asked him to hold off which he did . I reached behind me and grasped his cock , lifted it to line up with my other hole and said "Push it in Billy " .

"You're kidding Heather , you really want it in there?" he asked .

"No kidding Billy , put it in my ass but be gentle ". I insisted . He moved forward and I felt the contact where I wanted it so I pushed back slightly . He grasped my hips I felt the head start to enter me and that certainly felt good but when he hit my sphincter it would go no further .

"Push Billy " I said which he did but my muscles involuntarily tightened up and he could go no further .

"Keep pushing" I insisted but every time he did the same thing happened .

"It's not working sis " he answered .

"Okay , one more time and I'll try something" and this time when he pushed I pushed with my stomach muscles like I was trying to squeeze out a big one and in it went along with the pain I was expecting . Ouch .

"Oh golly Heather , my cock is in your ass " he exclaimed .

"Hold it right there for a minute until I can get use to it as it does hurt some" I said . It was the weirdest feeling being filled this way and as the pain subsided , not altogether without some pleasure . After a while "Okay , slide it in all the way but go slowly ". When I felt his balls hit the backs of my thighs he stopped again for a moment . This isn't too bad I thought .

"Now fuck me but be very gentle and do not take it all the way out as I don't wish to go through that again ". I rested my head on my arms on the bed and felt him slide his cock out almost all the way out then back in again . As he moved faster in and out of me I started to rock back and forth keeping time with his strokes .

"Oh my gosh Heather , you are so tight back here I am not going to last long . Can I cum in your ass? " he asked .

"Of course silly , that's what this is all about" I replied although I was beginning to actually feel enjoyment which really surprised me . I reached back with one hand and inserted two fingers into my cunt rubbing my clit while he fucked me and was a little surprised at the wetness I found there . Not so bad I thought . When he started to cum in my ass he slammed forward crying "I'm shooting , I'm shooting Heather " this really set me off and much to my amazement my orgasm started catching me off guard once again . He unloaded his balls into my ass as waves of pleasure passed through me . When he went soft he slid it out saying what fun that was and hoping we can do it that way again soon . I replied , "yes , that was great" .

After wards , I lay there thinking I'm becoming quite the little fuck machine aren't I . For a few days after I felt like I needed to hit the toilet constantly but other than that and the initial discomfort , I found I thoroughly enjoyed anal sex !

Well , needless to say that became Billy's favorite way to engage as I allowed him to cum in me . We both used a lot of baby oil applying it to both his cock and my ass and his entry did become less uncomfortable . We also tried it with me on my back and my legs up at my request but found we both preferred it from the rear especially him .

It was still my call as to how we were going to perform when we did have sex but I did allow him his due .

This "arrangement" went on for a few years although I did add considerably more spice to my life by way of my involvement with our neighbor Mrs. Jackson who I babysat for . But once again , that's another story ...

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