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The Final Dare

Taboo
2004-11-08

I am almost six feet tall and I just turned 16 and starting high school.   I lay awake early in the night having just returned from my work at the local grocery store.   I am home alone since my parents went on vacation and I had to stay because of my work responsibilities.   Usually when I'm home alone or spend the night at my friend Jeff's he and I experiment with each other in a game of sexual truth or dare.
I hadn't called him yet tonight because I wasn't sure if I was in the mood.   I went down to make myself some dinner and as I walked passed the dining room I saw some of my mother's laundry in a basket.   I took it to her room as usual and set it in front of her dresser.
I got this urge to look through her underwear because my mom had a decent body with nice curves.   I rummaged through the drawer making sure she couldn't tell I was in her dresser.   While looking through her clothes I was slowly building up my mood and I noticed she had left her closet light on.
I went in to turn it off, but knowing I intended to scan her clothing items there too.   I noticed a smaller dresser in her closet and opened the top drawer and found a several thongs but most noticeably a black satin one.   Quickly I ran to my room and stripped myself of my clothes and ran back to my mom's closet.   I reached into her drawer and pulled out her black thong.
As I slowly slid it up my legs I could feel the softness of the fabric against my skin giving me goosebumps.   The thong slid into my butt giving me an odd but pleasurable feeling.

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    I looked in her other drawers and pulled out black stockings and they fit nicely since my mom was only a couple inches shorter than me and about the same build.
I rolled the panty hose up my leg making sure not to ruin them and I grabbed a garter belt out of another drawer.   The kind that have suspenders for the hose.   I then walked over to my mom's mirror and looked my bulge coming from my mother's small thong panties.   I grabbed a pair of mother's high heels and a black nighty she had hanging in her closet and ran into my room, completely forgetting about dinner.  
He said he didn't know what I was talking about but said he was in the mood so he threw on his coat, since it was in early December and came over to my house a couple blocks down the street.   He walked in the front door and there was a pair of my silk boxers and my silk robe on the staircase with a note that said, "Get changed and meet me in my room. "
Jeff arrived in my room and saw another note that simply said "Get comfortable".   He sat back on the bed with his robe still tied.   I walked out of my closet with the high heels, stockings, thong, garter belt and the teddy on to see his eyes widen with surprise.   He asked me with a chuckle, "Why are you wearing girls' clothes?"  I said, "If you don't like it we don't have to do this" (since I was really in the mood to go all the way) and as I walked back towards my closet he reached his hand for mine.
He said he was sorry and that I looked beautiful.   I said I just wanted to make him happy and he leaned back once again.   I leaned in and kissed him just like we had done on our last night full of dares and I whispered in his ear, I dare you to take off your robe.   He shuddered with desire as he slowly undid the knot.

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Once the robe was off I moved my hands from his stomach slowly up to his chest and lightly pushed him back so he was laying on the bed and began to lightly kiss his neck and suck on his nipples.   He leaned up and whispered you don't need to dare me, I've been waiting for this ever since our first dare.
With that comment I made my way southwards as his hands lifted the teddy over my head making my underwear completely visible to him.   He said, "You really thought this one out didn't you?", as he sat up.   I slowly slid my boxers off of him revealing his 6 inch teenage penis stiff and pointing right at me.  
I reached my hand out and grasped his shaft and slowly slid my hands up and down sometimes caressing his balls and nervously leaned into kiss my first penis ever.   He let out a soft moan when my lips touched his head.   I then moved his cock into my mouth more ane more until his whole cock was in my mouth.
      It was just long enough to toy with my gag reflex but not make me gag.
    I began to bob my head back and forth and he moaned a little more each time.   Then he placed his hand on the back of my head and began forcing himself deeper.   I can't say it didn't hurt but I can't say I didn't like it.
    After a couple of minute I took my head off his head and stood up as he undid the suspenders and slid my thong off and reclipped the supsenders to the hose.   I began to take off my high heels and he grabbed my hands and softly said "No, leave them on".
    I stood there in front of him and he began to suck me off, just as I did him, until I was hard then he pulled me out.

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        He asked me if I was done or if we could finish this.   I nodded that I wasn't done.   He whispered for me to grab my ankles.   He grabbed my nearby bottle of lotion that I use when I masterbate and he squirted a little over my asshole.   I grimaced when I thought the pain I was about to be in but smiled in my awaiting pleasure.
    He rubbed the lotion on himself and all around my hole.   He asked me again for reassurance and I nodded my head.   He stuck a finger in and slowly moved it about and then two fingers to widen my tight hole he was about to ram his cock into.   He fingered my asshole for a couple of minutes until he was ready and had me lean up to suck his cock to make it hard.
    Jeff's tone suddenly changed when he commanded me to grab my ankles and asked me "Are you my bitch?"  I sheepishly whispered "yes jeff".   He then spanked me once to get my hole open and grabbed both sides of him waist.   His throbbing cock flopped around until it was at it's entry hole.   He pushed his cock but it wouldn't go in.   He said relax and I tried but he still couldn't get in so he shoved through and I let out a scream but he didn't hear.   He fucked me for hours that night we did the ultimate dare.

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