I really hope you enjoy this story. It is one of many that I have experienced over the past few years or so. I enjoy sharing them so please give me feedback at looseboy_girl@yahoo.com.au if you want to hear more of my adventures.
My maths teacher in senior year was a middle aged man called Mr Lees. He was probably in his late 50's and was quite tall at around 6 foot and while he was slightly overweight you wouldn't call him fat. He had strawberry blonde hair and a strikingly large nose. Mr Lees was a dirty old pervert. It became quite evident early on in the year when he'd always single out the girls with short school skirts to climb up and open or close the windows. I loved it, especially early on when the girls were being caught unaware and a couple of them gave a good little upskirt while wearing some skimpy panties. One girl Shannon even had a thong on one day when he made her get up. From my angel you could just catch the bottom of her ass cheeks. Unfortunately the girls caught on pretty quickly and started wearing bike pants under their skirts. it was a sad day for all.....none the less he was still and old perv.
Jazz was having one of her "parties" on the weekend. I was getting invited pretty much every time she held one lately. I must have been providing some good entertainment. I packed all of Jackie's clothes and accessories in my bag and made my way into town. Jazz greeted me at the door and after exchanging the usual pleasantries and such I began my transformation. I always wore some of my older clothes for these parties as they usually ended up being quite messy by the end. Tonight was simple. I went goth in all black, black thong, bra, skirt and singlet to match my black long hair. I had dark purple lipstick on and dark black mascara on my eyelashes and some shaded eye shadow. I thought I gothed up quite well.
I came out and met Jazz and she took me into the party. Jazz started introducing me to the guys. There was about 4 men in one corner, Gary, Ben and Doug and Neil (from Loose Ends 10). I said my hellos and Jazz led me over to the other side of the room. Two men were over there having a chat Jazz introduced me to the man facing me. His name was Jacob. Jacob was quite tall, about 6 foot 5 or so I would guess. He was fair in complexion and had very blonde hair and bright blue eyes. There had to be some Scandinavian in there somehow. He looked about 45 to 50 years old.
"Hello Jacki, welcome to the party" he said as he grabbed and kissed my hand. Awwww how gentlemanly I thought. OK you can fuck me tonight.
I hadn't even looked at the man standing next to him yet as his back was still towards me and then he spun around. OH MY FUCKING GOD!!!! I thought to myself. It was Mr Lees my maths teacher.
"Jacki, this is Kevin" Jazz said introducing us.
Wow, this could be interesting, I thought to myself. I knew he was a perv but I thought only for girls. Wow. "Hi Kevin" I said with a smile
Jazz left me with the two men and went back over to the other group. Jacob poured me a Vodka, he really was a nice man, Mr Lees showed his sleazy side instantly. He slid up right next to me giving me this creepy little grin.
"So Jacki, you must surely be a naughty girl to come to a party like this. I bet your parents don't know you are here."
He seemed quite drunk already so I didn't feel the need to disguise myself that much so I answered " Oh daddy would give me a real hard spanking if he knew how naughty I was"
"Just how naughty can you get?" Mr Lees asked as his excitement grew
"I can be bad. Real bad. If you're lucky you may see just how bad" I said with a wink.
Jacob rejoined us and we chatted and had a few more drinks. We moved to a lounge and sat. I was feeling a little drunk by now, Mr Lees was considerably drunk and Jacob just kept being the perfect gentleman. He'd get rewarded.
On the other side of the room Neil was on his knees working on Gary's cock. From my angle he looked quite well endowed. Probably about 8 inches or so. Jazz was sitting on a lounge next to Doug leaning over servicing Dougs rod. They looked like they were set. We all watched for a few minutes. Mr Lees had his hand rubbing up and down my thigh. It was gradually working it's way up under my skirt and flicking my panties. Jacob was behaving himself. He would alternate between watching Mr Lees hand and watching the couples on the other side of the room. I felt he needed some encouraging, I reached over and placed my hand on his leg and started rubbing him up and down. I started unzipping his trousers and slowly slid my hand in. He was hard already. I could feel his shaft through his underpants and it felt quite large. I slid his underpants down below his balls and pulled out his rod. it was nice. Very nice. I stroked all 9 or so inches up and down. Mr Lees
kept rubbing me up from the other side watching intently as I leant over and licked the head of Jacobs cock. I licked all around his head and part way down the shaft. I moved back up to the head and opened my lips and took it in my mouth. He had a nice aroma about him lowered my mouth deeper and deeper over his joyous pole. Mr Lees was clearly getting very horny by now. he had slid his and around and over my ass. He pulled my thong to the side and started working his finger around my eager hole. Within a few seconds he buried one of his fingers deep into my ass. I pulled my head away from Jacobs cock and turned and gave him a gasping smile to show my appreciation. I then went back to work on Jacob. I kept sucking Jacob hard for several more minutes and I could sense that Mr Lees was getting keener for some more action. He had pushed up real close behind me now and I could feel his cock pressing onto my ass cheek. Ok, I thought, it's time to give the sleazy prick some action. I manoeuvred myself around and got myself onto my knees. I remained leaning over Jacob blowing him steadily and I spat on my hand and reached back and grabbed Mr Lees cock coating it with my saliva. Without seeing it I could tell that it was quite generous in size, possibly 8 to 9 inches. I guided it towards my waiting hole. Placing it at the opening he paused briefly and then slowly pushed it in. Apart from the saliva on his cock I had no lube on my ass at all so it was a slow push in. It felt great though as I could feel Mr Lees fill me up from behind. I turned to him and smiled again in ecstasy before returning to Jacob.
Mr Lees started increasing the tempo as my rectum adjusted, faster he started driving into me and I started to feel the air being pushed out of me as I had to remove Jacob from my mouth to catch a deep breath. He spanked me on the ass and started with the dirty talk
" So is this how naughty you can be you little slut?"
With that I pulled away from Jacob and spun myself around quickly taking Mr Lees member into my mouth enthusiastically lapping up all my juices from his cock.
I looked up at him and went "No that's how naughty I can be"
"Mmmmmmmm, I like you" Mr Lees said pleasingly.
I moved myself over to Jacob and straddled his lap, grabbing his pole I lowered myself onto him. He wasn't quite as thick as Mr Lees but it still felt good as I felt him fill my ass up. I rode him slowly up and down. He was a nice gentle man so I thought I wouldn't go too rough on him too soon. He seemed to enjoy it as I rode him like a good cowgirl. I leant forward and gave him a little kiss on the lips. He returned the gesture by leaning back towards me and kissing me back. We started making out while I could feel him increase his thrust from below. His tongue started exploring my mouth as I met his tongue with mine. I started moaning as his thrusts became harder and harder. Mr Lees looked like he was missing out again so I motioned for him to stand over next to me on the couch. I pulled away from Jacobs mouth and grabbed hold of Mr Lees cock. It was a nice cock upon inspection about 8 and a half inch but it was pretty thick. I took it in my mouth giving it a firm grip with my lips. Sucking hard I pulled his shaft back and forward with my lips. He placed his hand on my head as though he was some sort of porno star and put on a bit of a pose while I continued to service his rod. We kept going for a few more minutes and my thighs were starting to burn from riding Jacobs cock. I climbed off Jacob and laid on my back across the lounge. I told Mr Lees to move up between my legs and he promptly did so and within moments pushed himself back inside of me. I called Jacob over to straddle my chest facing towards Mr Lees. When he was there I grabbed him under his thighs and raised him up a bit pulling him back towards my face. I started working on his balls with my tongue giving them a good licking and taking them one by one into my mouth. I'd bend his cock down as far as it could go and lick as much of it as I could. I worked on his balls fro a while longer while Mr Lees kept fucking me hard. I moved my head back a bit to expose Jacobs ass to me. Reaching out with my tongue I gave his hole a lick. It was fine, there was no foul smells and he was shaven down quite well so I proceeded to give his ass a fair rimming licking all around it and pushing my tongue as far in as I could get it though his tight lips. He seemed to enjoy this. I kept rimming him and I could feel his body jerking above me. Mr Lees had grabbed Jacobs cock and was jerking him off. Within a few minutes Jacobs body became rigid as he moaning with pleasure. I could feel splashes of warm cum hitting my tummy. I pushed him off my face and grabbed as much on my fingers as I could and tried to lap up as much as possible. Mr Lees was blatantly excited by this and his thrusting increased considerably. In what seemed like no time at all he pulled out and exclaimed that he was going to cum. He straddled my chest and started shooting loads onto my face. I opened my mouth and started taking in all I could. It tasted nice as he filled my mouth with his load and I swallowed it down with glee.
It all seemed to be over so quick. On the other side of the room Jazz had Doug bent over the couch ramming him from behind with her massive cock and Neil was also copping it from Gary. I moved over there and didn't get too involved. I just waited really for Jazz to explode what is always a enormous load. She didn't take much longer and she pulled out of Doug and pointed in my direction. AS per usual I gagged at the force and volume of her load as it filled my mouth and throat. I swallowed as much as humanly possible before falling back to breathe. I watched as Neil jerked himself to climax and shortly after Gary filled Neil's ass with his load. Not sure what happened with Doug as I didn't see him cum.
Ahhh another fun party at Jazz house. I had a shower and got changed and made my way home not long after.
It was Monday afternoon. Lunch was finishing and I had double Maths coming up. I got into the room early and placed a not that I had typed onto Mr Lees desk slightly hiding it under a book.. He was not in the room yet.
It Read " I hope you had fun on Saturday night!" I left no sign off.
The class entered shortly after me as did Mr Lees. He didn't notice the note for some time then while he had ordered us to do an exercise from the text book I saw him take a peek. He looked up in a panic, looking all around the room. I avoided eye contact as his face turned red. A few minutes later I looked up and he was staring straight at me. So he had figured it out I presumed.
Class finished "Jack, can you stay back a moment"
Everyone left apart from me. I walked up to his desk.
"Jack or should I say Jacki, who would you prefer to be known as?" He asked
"The better question is, who would you prefer to know me as?" I fired back like a smart ass.
"We cannot talk about this now. You have afternoon detention. I'll see you here after school" He said almost angrily.
I was sort of pissed off. I hated detentions but at the same time I was excited. Who knows what this dirty old bugger had in mind for me.
School, finished and I went to Mr Lees classroom for Detention. I was clearly the only one on detention this afternoon.
"So Jack, how did you know that I would be at that party on Saturday night?" Mr Lees asked
"I didn't know Sir. Jazz just invited me as usual"
"I have never seen you... I mean Jacki there before"
"Well I have only been going for a few months as I haven't known Jazz for long" I answered.
"Ok, then. So what do we do with this situation. It' a very sensitive matter you know. I could get in big trouble for this." He said almost worryingly
"You won't get in trouble sir. I had a great time." I lowered my voice and added " You can fuck me again if you want" an gave him a cheeky grin.
" Yes I can see that an arrangement can be made here then Jack. Thursday afternoon you have detention. We will stay here for about half an hour and then you will come to my house to complete your detention there. Depending on your behaviour I will decide on how many more detentions you have."
"Ok sir"
"You may go now Jack. Please make sure that Jacki comes to the detention as well"
I nodded and left the room. I wondered whether this was too dangerous territory to be getting involved with. He is my teacher after all. Then I woke up to myself and decided fuck it. He wants to fuck me and I want to be fucked. Everyone wins!
Thursday morning rolled around. I packed a smaller bag inside my school bag. In this bag was the making of Jacki. It had all the usual supply's, clothes, wig makeup. I would have to keep it well guarded at school on this day.
3:15pm came and the bell went to finish the school day. I headed for Mr Lees classroom. I went in and he was in there alone.
"Hello Jack, are you ready for a detention with a difference?"
"yes sir" I replied
" Good. Please take a seat up the back for a while. Take out your text boko and look as though you are doing work." He instructed
I followed his instructions and did as asked. I sat at a desk in the back corner and got out my text book. I didn't even really look at it I just waited for time to pass. I looked up the front. I could see that he had his hand under the desk. From his shoulder action it appeared that he was rubbing himself up.
He stood up and headed towards where I was sitting. He stood behind me and said " Ok Jack, I know how very hard it is but just hang in there a little longer and you will benefit from it." As he was saying it he leant forward a bit and I could feel his crotch touch my shoulder. I could also feel his throbbing hard on through his quite tight pants. As he walked away I could see the outline of his cock through his pants. It made me so horny.
" It's ok sir, the harder it is the more I strive to get a satisfying climax" I said as he looked at me and smiled.
The time went quite quick and before long I was instructed to pack up and get ready. We exited the classroom and I was told to wait around the corner from the school gates. I went to the location and he very soon arrived to pick me up in his quite new looking Volvo. The car was quite spacious, especially the backseat. It definitely looked big enough to have a good shag in. Maybe one day.
In about 15 minutes we arrived into the underground car park of his apartment block. We got out of the car and he led me towards the lift and we made out way up to his apartment. Just quietly, what a messed up crappy apartment he had. He had a nice car but his apartment was messy and full of shitty old furniture. It was a nice apartment block so I thought if he could afford to live there he could afford some decent furniture. Maybe the rent was too hire for him to buy some, I didn't know and by now didn't really care anymore. As long as the bed could hold two of us I would be happy.
We went into the living room " Jack I have something for Jacki to wear" he said as he handed me one of our schools girls uniforms. It was quite large and should fit. There was the blue skirt and white blouse. He also had some long white socks for me to put on. "The bathroom is the first door on the left down the hall he told me. Get changed and I'll meet you back in here"
"ok" I said making my way to the bathroom. I got myself changed into the schoolgirls outfit and did my makeup and hair. It was pretty exciting wearing the girls uniform from my own school. Especially with a teacher nearby. I had a matching read bra and panty set. It wasn't a thong just a sheer nylon brief that was quite high cut, unlike the hipster boy underwear that girls wear these days. I was ready and I thought I looked pretty hot.
I went into the lounge room. He wasn't in there. I sat and waited for a few minutes. I could here him shuffling about in another room. A couple of moments later:
"Jacki, can you come in here please"
I headed towards the door where he was in. I walked in and got a pleasant surprise. Mr Lees was also dressed in a school uniform. He had a long blonde wig on and was wearing a matching outfit to me.
" Hi Jacki, I'm Leigh. Do you want to have some fun" He said in a pretty poor girly voice. Sure it was poor but at least he tried.
" Hi Leigh, do I ever! What do you feel like doing?"
" Well Jacki, I thought we could have a little pillow fight on the bed and then well................... we could fuck each others brains out all over the house."
"That sure does sound like fun!" I said joining Leigh on the bed. Once on the bed I grabbed the first pillow and whacked her across the head with it. She picked one up and whacked me back. We playfully had a little pillow fight before she pushed me onto my back and laid on top of me. Pulling my legs apart Leigh positioned herself on top of me and moved her head above mine. She lowered herself down and planted a big kiss on my lips. It wasn't long before we were having a messy porno tongue wrestle. Leigh was all over me putter her tongue as far down my throat as possible while her hands explored my entire body. She started rubbing my crotch through my panties. My tiny cock grew very hard real quick. Leigh started sliding her body down my torso and her head was soon at my crotch. She was kissing and biting my cock through my panties, it was driving me wild. Soon enough Leigh pulled my panties down and took them completely off. She grabbed my cock and started jerking it. It felt great whenever someone grabbed my cock as I'm so used to be the receiver and not the giver, and very soon took it in her mouth where she proceeded to suck my with force. Fuck, I thought I would cum straight away but I held on. She kept sucking my tiny clitty and I moaned in delight. She soon stood up and moved up next to me. Lifting up her skirt she revealed a lovely red lacy thong. Oh do I appreciate a nice pair of panties . I found myself rubbing her bulge through the panties and soon enough her rod poked it's way out the side. I grabbed it quickly and took it straight in my mouth. I was so horny by now that I just sucked it intense vigour. I opened up as wide as I could and took as much down my throat as possible gagging a bit from the reflex but adjusting soon enough, I kept sucking and sucking but I wanted her in my ass and I wanted it now!
" Please fuck me Leigh, please fuck me now" I pleaded
Leigh flipped me over onto my stomach. She leaned down and pulled my ass cheeks apart and using her tongue she lubed my waiting fuckhole up real good. She pulled back up and I felt her cock press against my hole. She rammed it in with a mighty force pushing my chest hard into the bed, that thrust was followed by another and another. Many more furious thrusts followed and I was breathless as Leigh's big cock drilled into my pleasure pipe.
" Fuck I need to stop!" yelped Leigh quickly withdrawing from me" She was clearly about to cum but it was waaaaaaaay too soon for that.
" Jacky, how about you show me what you can do with your little cock" Leigh said as she got on all fours on the bed next to me. I hadn't fucked anyone for a fair while so this was fun. I got in behind Leigh and put my cock up to her waiting asshole. It didn't really take much of a push and I shoved it straight in. Leigh was pretty loose. I doubt she could hardly feel me but she made me feel good by moaning in pleasure and telling me to fucker her harder and deeper. I obliged to all her commands and was fucking her with as much force as I could. It wasn't long before I too felt like I was about to explode and I pulled from her.
" Do you like toys Jacki?" Leigh asked
" I like big toys" I replied
"Well I think you will like my toys" Leigh said as she walked over to her set of draws. From the top draw she pulled out two massive dildos. One was a 12 inch one similar to mine and the other was shaped as a fist. I'd seen one in a sex shop before called the Fist of Adonis. Both had suction caps on the end. She brought them to the bed. She handed me the Fist and she kept the 12 inch cock. We positioned on the bed for a 69. I was underneath her. She quickly had the head of her monster toy poking at my ass. I heard her spit on it and make it all wet. My ass was already wet enough. She pushed and I tensed a bit. I've taken my 12 inch dildo thousands of times but that first thrust still makes me tense. In a bit more it went and a bit more until it was a fair way in where she left it. My turn I thought. I lubed up the fist (to be fair it's no that much thicker than the dildo buried deep in my ass) and I placed it at Leigh's waiting hole. The difference between the two toys was the width of the tip. This one was much wider at the tip. I had to push quite firmly and it suddenly just sucked straight in. She moaned as I pushed it ever so slowly into her ass. Wow, this was cool watching from this close as I slid it further and further in until it was about 10 inches in. She started thrusting her toy into me again and soon we were both fucking each other faster and faster with these massive toys. I love the feeling of something big stretching my hole and rubbing on my prostate, it gives me a real tingle all the way into my cock.
We continued for several more minutes when Leigh said " Lets go into the living room"
Ok I thought. I pulled the toy from her ass and she from mine and we went into the living room. She turned on the television and hit play on the DVD player. There was a Porno playing. It was a hetro gang bang movie and this little white chick was being ploughed severely by about 10 guys. The room had a glass coffee table. Leigh stuck his toy onto the table. I followed suit and stuck my toy on the table. I still had the fist with me and Leigh quickly straddled over the cock and lowered onto it. I stood behind him and watched as he went down all the way on it taking all 12 inches inside his ass. It looked fantastic. I moved around in front and positioned myself over the fist. I put the tip at my hole. Firmly I had to push it in to get the large tip through the opening but it did easily enough. I lowered down as far as I could go. I was nearly at the bottom but not quite.
"Keep going baby, you're nearly all the way" Leigh encouraged. I pushed down further, it was like it was pushing into my bowels but I persevered. Eventually my body accepted it and it became comfortable. Damn it was massive inside me filling up every last millimetre of my ass. We both started riding the toys while watching the move. Two black guys had their huge cocks in the tiny white girls ass. It was impressive effort by the little girl and Leigh also seemed impressed as she started bounding up and down on the monster cock with great haste. She leant over and kissed me and grabbed my cock and started jerking it. I responded and grabbed hers and jerked it fast as well. We kept riding our toys while jerking each others cocks and soon enough I was ready to shoot. My tiny clit shot all over the glass table in front of me. Not long after she was ready to go and she started shooting all over the table as well. I quickly climbed off my toy and knelt next to the table. I started licking up the massive pile of cum that had splattered the table. Leigh was soon down on her knees with me licking it up. Both our mouths were covered in each others cum and we just lapped up whatever was in front of us. I grabber her head and pulled her towards me and started licking the cum from around her mouth. We licked the cum from each other face and tasted the cum in each others mouth. It was nasty and great!
We finally settled down and relaxed.
"Jacki, you told me that you were a very naughty girl. You were right. I hope I was naughty enough for you"
"Leigh you were equally as naughty as me. That was great" I replied with delight. I soon enough got up and cleaned up and went home from detention. Detention had just become fun.
I fucked both Mr Lees and Leigh for a few months after that but it all came to an abrupt halt. One day he never fronted to class. Apparently some of the girls had made a complaint against him for his perverse ways towards them and he got suspended to face an enquiry. He never taught at our school again and I never saw or fucked him again. It's a pity really.