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The VP (Story Code: MILF, male teen, first time)

phtlc · 1911

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Offline phtlc

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on: November 26, 2014, 12:12:24 AM
The VP

I had never been to Detroit before, and I had to admit it was an exciting experience, seeing a big city like this when I lived across the border in Ontario. I was in town for some second cousins wedding, as I had a few relatives in the US. I didn't really know them well, but my mom had been close to that part of the family, so we went. We were in a nice hotel with several conference centers that doubled as ballrooms. I really wasn't into being there, but as circumstances were, I at least got my own room, which gave me a tiny bit of privacy. Initially it was supposed to be a shared room with two beds that I was to share with another cousin who I sort of knew but he suddenly became quite sick so I had a hotel room all to myself, which made me feel very grown up. The hotel/spa had a 24 hour pool and gym, a great restaurant and several other amenities, including a separate bar.

The wedding had been as exciting as watching paint dry, however the reception was great. Buffet meal, and even an open bar, not that it did me much good. The bartenders carded me right away. My mom did agree to buy me one drink, but only one, so I enjoyed a beer. After that I managed to convince my uncle to buy me a couple of beers too, so it wasn't all bad. My cousin had several of her best friends there as bridesmaids and I have to say they weren't half bad. I felt like a big man, talking to one of them, holding a beer in my hand and even managed to dance with her a few times, but she quickly found other things to be doing, politely thanking me for the dance. I guess being in her late twenties or early thirties high school boys weren't really her thing. I did manage to convince her to get me another beer though, so I was feeling pretty good. She looked hesitant when I asked, not wanting to get in trouble, but I assured  her it was ok, so she agreed to go to the bar and get me one and only one. After that one of the bartenders spoke up and told the father of the bride that if he saw anyone else buying me drinks he would close the bar down, so that was me....cut off.

I later wandered out of the reception hall. My parents didn't mind me wandering around the hotel, as it was in a more suburban area which was pretty safe. Granted they did not want me going outside and wandering the streets, but so long as I stayed inside the spa/hotel complex I could go of on my own, go to the restaurant or the gym. To be honest, with a few beers in me I felt bold enough to go to the actual hotel bar and try to fool the bartender into serving me a drink. I tried chatting him up first, talking about work (as though I wasn't a high school student), acting manly and all that crap, and actually felt I was doing pretty good. After lying about how the local mechanic ripped me off on a fictitious break job, on a car I pretended to own I said "You know, I could use a beer before bed....how about a Budweiser", I said, confidently.

"Got ID"? he asked firmly. Damn!

"I forgot it at work, but if you can help me out I'd owe you one" I tried

He raised an eyebrow at me as if to say "yeah right" before saying "Sorry I can't serve you". Fuck!

Walking out, feeling nicely buzzed, I saw a lady staggering out of the other reception hall where another wedding was taking place. She was wearing a nice formal gown, and had a nice figure. She was staggering a bit, and her foot caught on a carpet that was sticking up causing her to fall down hard. Immediately I moved over to assist as she tried to stagger to her feet.

"Let me help" I said, being genuinely chivalrous, as I reached down to help the lady up I took her arm and helped raise her up onto two unsteady legs which was in itself tricky as I had a few in me. As she turned to speak, I froze in shock.......

"Mrs Treynor?", I said in astonishment. Mrs Treynor was the Vice Principle at my school. She also taught history, and had been my teacher for a few classes. She was pretty OK as far as teachers go. Not super friendly, but at least fair I guess. As VP she had gotten to know me quite well in my first year as I had spent copious amounts of time in her office for one disciplinary act after another. One time I had been skipping school, and she literally happened to be in the same shopping mall I was in when I was checking out the HMV store. I had been a bit obnoxious a few times when she cracked down. She didn't seem to hold grudges though, so when I finally cleaned up my act she seemed to be more pleasant to me. Many of the guys noticed she had a great body, which was amazing as she had to be in her early 40s, but she tended to dress rather conservatively.

She looked at me somewhat bewildered.
"It's me...Greg".

She smiled a drunken smile, and slowly repeated "Greeegg" as she held onto my arm for support. "I'm trying to get to my room...can you give me a hand" she slurred. Holy shit! Mrs Treynor was smashed!

"Sure" I said, taking her arm and letting her lean against me as we walked together  down the hall. It felt kind of exciting having her body leaning against me, not that I let it show. She was after all the VP and I didn't want to do anything awkward. I helped her into her room, and moved her past the door.

"Need a hand" she said, grabbing my arm as she  lifted one foot and took off one of her high heels. Repeating the process with her other foot, she stumbled for a second, but I caught her. She burst out laughing at her own clumsiness.

"OK, I can stand a bit better now" she slurred, standing there barefoot. Looking around, I saw she had a few bottles of liquor, and immediately thought to take advantage of the situation and get a drink out of her.

"Hey, mind if I have a drink?" I asked, as casually as possible, hoping I would get away with it.

"Just so long as you pour me one!" she said in a tipsy voice. Score!!!! I wouldn't say anything or get her in trouble, but this was just too great. She was in such a party mood she didn't even care that I wasn't legally old enough to drink. "Vodka and ....seven" she said. I poured her that, and opened her fridge, hoping to find beer and bingo...she had some American beer called Pabts I think. Popping the tab, I drank quickly, knowing that I probably didn't have much time and I wanted to grab at least one more.

She patted the bed beside her as an invite to sit down. Now part of me was excited at this, drinking with an older woman, while sitting on her bed with her, but I was careful to hide that. She brought one leg up on the bed, which gave me a fairly good view up her inner thigh. I tried to act casual, but that long expanse of inner thigh flesh kept teasing my peripheral vision. She looked at me, and raised her glass to her mouth and drained half of it with one gulp, before smiling and laughing. She really wasn't saying anything. I tried to keep up and chugged my beer quickly.
"Wow, so you look like you've had a fun night" I say tentatively.

"Hardly" she slurs. "My asshole ex was also invited to this...he brought his new girlfriend....she's 26" she said bitterly, before gulping back her drink and holding out her glass to me, implying she wanted another. This was fine with me, so long as she allowed me to drink.
Gulping back my beer as quickly as I could, I grabbed another one, and poured her another drink, sitting back beside her on the bed, feeling awkward about her confession.
"I'm sorry Mrs.....",
She cut me off. "I'm not...the slut just wants his money...she was fucking him when we were still married". I stared in wide eyes astonishment at the language coming out of my vice principals mouth.  I sat there with her, looking sympathetic, but at the same time enthralled that I was having a few drinks right in front of my VP.

"The last few months of our marriage, he barely even touched me. Either banging her or cruising internet porn", she said with drunken bitterness, as she gulped back her drink, gesturing for me to get her another.

Getting up, I grabbed a beer and was about to pour her another one, when I saw a bottle of Jack Daniels. Everyone raved about "Jack" but I never tried it. Raising it I looked at her. "Any shot glasses?".

"No....just bring the bottle here. I think that's what I need right now" she said. I brought the bottle over to her and she grabbed it between her thumb and forefinger and held it up to her mouth before taking a large swig, swallowing repeatedly as I amazed at her capacity to swill this stuff without puking. She swallowed hard and handed me the bottle. Not wanting to waste the opportunity, I held it up, then placed it to my lips and took a swig. It burned like hell, and I had to blink a few times as she snatched it out of my hand and took another large swallow. She was trying to get smashed. Passing it back to me right away, she watched as I carefully raised it to my lips, and moved to take a small sip of the burning liquid. As I tilted my head back, she reached out and grabbed the bottle tilting it straight up so as to pour a large quantity in my mouth.

"Take a man sized swig" she slurred, as I tried to gulp back the fluid pouring into my mouth for a second or two before gagging and having to pull my mouth away as I spilled a bit, and coughed from the burning sensation. She laughed at my inexperience and gestured to me to grab another beer, which I did just to wash the taste of jack out of my mouth. I also prepared her another drink.

"Thank you!" she said in a drunken voice "I needed that!" as she gulped it back.

"Fuck!" she slurred. I couldn't believe this was Mrs Treynor. "I mean she's a bloody trophy, way too young for him and ...OK she clearly has implants" she babbled on drunkenly.

"I mean that doesn't even look good does it? " she asked rhetorically. "For god sake, any bimbo can have implants. I take care of myself, these are natural" she slurred, gesturing to her own chest. I didn't know what to do or say. Here was my vice principle, referring to her own breasts.
"I mean for Christ's sake...does some sort of inflated body modification really look that good?' She asked as she drained her drink. I shook my head, agreeing with her, as she grabbed the JD again.

"I mean sure, I don't have her quadruple D's but these actually look real, like a real woman" she said, gesturing to her chest again, looking to me for approval. I was bouncing between turned on and weirded out. Sure she was hot for her age, but she was in her 40's and my VP!

"She's just a skinny boned whore who has fake tits! Once her metabolism slows down, she won't age as well as I have" she babbled while taking another slug of JD. I worried she might get sick.

"I did dance for years, and work out and actually have conditioned toned legs, not skinny legs like his 26 year old arm candy" she said bitterly, her eyes glazing and her words slurring.

"No way she will have legs like this at my age" she said, shifting her body and sliding her dress up slightly so  could see her thigh. "No cellulite! See that?" she slurred as she pointed to her leg and took another swig. "That's not just skinny, but toned! Go ahead, touch it, there's no soft flabbiness there..go on touch it!" she said, gesturing to her thigh. I had to admit it was a sexy thigh. Some mild thickness to it do to years of dancing and training, but very toned.

"Go on" she said, grabbing my hand and bringing it to her thigh.. I took a deep breath at the luxurious feel of Mrs Treynor's thigh. I had to admit it felt real good. She took incredible care of her body. She could have passed for 10 years younger easily. I tried to control my breathing as I slid my hand along her incredibly sexy thigh. Soft, yet firm, with no blemishes or flab. I felt a stirring in my groin as I did that.

"That's right" she said, looking at me as though she knew what I was thinking. "See his skinny teenybopper fake tit skank have that effect" she said as she took another slug of JD. As much as I enjoyed drinking with her, I was a bit concerned that she was drinking way too fast.

"Mrs Treynor, maybe.." she cut me off with a wave of her hand. "Call me Joanne" she said, smiling naughtily at me.

"Ok, uhm, Joanne, maybe you want to slow down?" I more asked than said.

"What, you can't keep up?" she smirked, handing me the bottle. I held it up and took another swig, but was starting to feel like I had had too much now. She was breathing heavily, obviously from intoxication and even sweating a bit.

"Don't worry. I can handle my booze as well as any 26 year old bimbo" she slurred bitterly.

" I didn't mean it that way Mrs....Joanne, I just.." my voice trailed off, as I noticed she looked terribly sad in her drunken state.

"I'm an attractive woman right?" she slurred drunkenly, looking to me for approval. This was awkward of course. Many of the guys spoke of what they would like to do alone with her, despite her age, but she was still my VP. Sure she was hot, in an older MILF kind of way but this was awkward.

"Yeah, of course" I said.

She reached out and gently took my hand in hers and held it to her chest rather suddenly, shocking me, smiling sweetly as she looked at me.

"You're so sweet!" she said in her drunken voice, peering into my eyes with a look that made me feel somewhat awkward. I was sure she meant to hold my hand to her heart, but all I could think was that my hand was partially touching her breast. I became acutely aware of the sexuality of the mature woman sitting on the bed with me. Her form fitting dress, her nice sizeable bosom and the toned, semi-muscular legs she had, crossed. Her perfume was also intoxicating, but sadly overpowered by the alcohol on her breath.

We maintained eye contact for several awkward moments, she holding my hand to her bosom. With her other hand, she reached out, and placed it around the back of my head and started to pull me towards her. I tentatively resisted, more out of shyness, as she pulled me in, and leaned her own face forward, her mouth opening slightly, but quickly relented. I was more excited than awkward.
When our lips touched, I felt the excitement course through me. Sure she was my vice principle, and in her 40's but smoking hot! Her breath did of course reek of booze, and she seemed a bit sweaty and out of breath, but it was an incredible kiss. Our lips lightly pressed together as we hungrily explored each others mouths, her tongue probing into my mouth.

I was shaking, but I was not nervous, just....ok nervous but in a good way. This was amazing. She was beautiful, and I was enamoured with her as we sat there kissing romantically. Her hands started to caress me, rubbing my back, pulling me in against her and I took this as my cue to do the same. Her body was firm, and well toned for her age, indicative of someone who took very good care of herself. She was a bit sweaty, but that was to be expected given the warmth of the room, and her intoxication. Her hands aggressively roamed me, hungrily exploring me as she panted in my face while kissing me sloppily, like a hot drunken sweaty mess in a sexy form fitting dress.

My erection was straining against my pants as her hands started to rub my legs, moving up my inner thighs, while I was still working towards her breasts. Just as my hands touched the front of her dress, feeling her fairly sized mounds though the material, half expecting her to slap me, I felt her hand slide over the bulge in my pants, grabbing it clumsily as I gasped. She was not wasting much time with preliminaries. I on the other hand was carefully feeling her soft breast through her dress. She quickly reached back with both hands, undoing the clasp on the back of her dress and sliding the zipper down , exposing her upper torso. In what seemed like a blink of an eye, she also undid her bra, removing it and exposing to sizable swollen breasts to me as I stared in shock at the sexy mammaries staring me in the face. As she was 40 they weren't quite as perky as those of a teenager, but they were still fucking hot! Before I could react, she grabbed my head and pulled my face into them clumsily as she gyrated her chest into my face. Thus far I had been inside the bra's of two girls in my school, but had never been able to take anyone's nipple in my mouth and subsequently was excited at this erotic opportunity. The fact that it was so naughty, doing this with my VP made it even more exciting. I sucked on her nipple, licking it my hands gripping her well formed waist as she immediately went back to groping my crotch. I could already feel quite a bit of wetness inside my underwear, indicative of my excitement.

Suddenly she pulled herself away from my face and pushed me back on the bed so I was laying down with my legs hanging over the end of the bed. Hiking her dress up, so I had a good view of her panties, she moved to straddle me as I got a great view of her vulva pressing though the material of her panties. When she lowered her crotch down onto the bulge in my pants, I opened my mouth in shock and excitement as she clumsily started go grind herself against me. I had grinded like this once with a girl from school, but we were both wearing jeans. I could feel Mrs Treynors soft and seemingly plump pussy lips pressing through her panties against the erection contained within my pants and it was amazing. She straddled me like this, grinding erotically for several minutes as she occasionally leaned down to kiss me passionately. I had been toying with her tits for awhile, but finally built up the nerve to grab her ass with both hands as she ground against me. This was the most incredible moment of my life. Up until now it had been a few titty feels on some girl from school, some kissing and usually in someone's basement, always listening to make sure the parents weren't coming. Now I was in Mrs Treynors room, her semi naked on top of me grinding away as I felt her ass, and she had a great ass; it was toned and firm yet full and rounded, with no unnecessary fat. I was in erotic heaven, feeling her gorgeous body up as she responded in kind, her hands exploring me eagerly.
After a few minutes of this, she broke the kiss and stood up, staggering as she did so, grabbing my pants and underwear in her hands, yanking them down off my legs. Then she slid her dress off, and looped her thumbs over the waistband of her panties and slid them down stumbling drunkenly as she did so, exposing her bush as she stood there in all her naked beauty, a sexy woman giving a young guy the thrill of a lifetime.

She moved back into the bed, swaying sexually yet at the same time slightly unbalanced due to the amount she had drank, as she crawled over me to resume kissing and fondling. I had watched some porn, but I had never imagined just how arousing it would be merely to have a woman's bare skin against mine, but just the lightest touch of her bare thighs against my legs, her abdomen pressed against me as her breasts pressed against my bare chest had me almost catatonic with excitement as I already started leaking some preliminary fluids while feeling her pubic hairs brushing against my sensitive organ as heat radiated from her mound which was pressing lightly against me.

We kissed like this for several more minutes, her aggressively mauling me with her hands as she unleashed her sexual hunger upon me. As excited as I was, she was getting quite passionate herself, moaning, breathing heavily as though this was something she had been deprived of for some time.

Her tongue probed aggressively into my mouth, almost gagging me as she explored my body, her weight pressing down on me. Her hands slid rapidly down my chest, towards my erection and grabbed my hardness aggressively, eager to explore my phallus.  I lay there delighting in the feel of her hands on me, touching my sensitive organ I had an overwhelming urge to investigate between her legs. My hands started sliding around her hip, towards the front of her pelvis, and glided towards her pubic area. Just as my fingers started to brush through her pubic hairs, she slapped me hard, stunning me. Looking at her in astonishment, she was biting her lip trying not to burst out laughing.

"Go ahead" she said, laughing.

I moved my hand again, and again she slapped me hard. Baffled I looked at her in amazement, and she burst out laughing; "Oh you poor dear...I'm just giving you a hard time" as she grabbed my hand and guided it to her pussy. I wasn't sure exactly what to expect, but I was not disappointed at all. It was very wet, soft and warm. None of my friends would believe me if I said I touched a woman's pussy for the first time this weekend. They would believe me even less if I told them it was Mrs. Treynor's. As my fingers probed her, sliding between her lips, probing inside her depths, I delighted in the intimacy of feeling the inside of a woman's body. I had a pretty good idea where her clitoris was and when I stroked the little bump, she squealed and bit my lip hard, drawing blood. I jerked my head away, yelping and she smirked erotically. She was really into this kinky rough stuff I guess. She kissed me aggressively and squeezed my cock, taking charge of this situation.

Rolling off of me, she lay on her back and pulled me on top of her. Reaching over to her left, she grabbed the bottle of JD and splashed a bit on her tits and said "Now be a dear and clean that up will you" as she grabbed my head and pulled my face towards her gorgeous round tits. Eagerly I went to work, licking and slurping, as she moaned and squealed, squirming underneath me.

"Looks like your still thirsty" she slurred, and took a quick swig before pouring some on her belly. I had a pretty good idea where this would eventually lead (or at least I hoped so) so I went along, using my tongue on her belly as she grabbed my head with her hands, bucking her body up and down beneath me. We played this game for awhile, dragging out the suspense as she splashed it even lower down on her belly, her thighs, her inner thighs, higher up her inner thighs until she finally guided me to her hot womanly flesh.

I often wondered how I would react when given the opportunity to go down on a woman. Guys talked about "eating" a girl, but part of me worried I would be grossed out, yet here I was just dying to get my mouth in there.

Stroking her gently with my tongue, I shivered when she squealed and grabbed my head tightly in her hands. I had never done this before, but she was already so turned on that even an amateur job would drive her over the edge. I stuck to my understanding of the matter, and focussed my efforts on her clitoris, be it licking or sucking. She spread her legs wide, drawing them back up to her chest as one went over my shoulder, and one around the back of my head, using it to pull me into her. There seemed to be nothing demure about my VP!

As I worked on her, she bucked herself up into my face, wrapping her legs around my head and shoulders, grabbing my ears with her hand as she cried out in ecstasy, grinding her crotch into my face as I eagerly went at my first experience with giving oral sex as I tasted my vice principals flesh in my mouth. After a few moments of this, she screamed, squeezing my head between her thighs as her body started to convulse, tensing up before she relaxed, sagging on the bed, breathing hard.

"Oh fuck I just want to keep that cute face of yours between my legs all night!" she moaned, before sitting up. Reaching she grabbed the bottle of jack and took another swig. I personally don't know how she handled all that. She was getting seriously fucked up, and when she handed me the bottle I wanted to decline, not wanting any more of that burning liquid in me but.......I grabbed it and took a big swig, wiping my mouth with my forearm in an attempt to look manly.

Grabbing my head she pulled her face close and said "I want you to fuck me right now!" as she lay back on the bed before me. I sat there not even believing she had just said that to me, but quickly shook my disbelief and went to my pants to retrieve a condom. It was a good thing I had remembered to bring them. I often wondered why I even bothered, it didn't seem like I would ever make use of them any time soon, but perhaps it had been hopeful thinking...that said, I had them tonight.

Crawling back to her, I looked at her body, laying there on her back as I thought Holy shit! This is it! I'm about to score for real! as I moved to kneel between her legs and started to open the package. As I did this, she reached out and took it from me saying "Let me help you with that" before tossing it aside and saying "Oops". She then grabbed my ear and pulled me towards her, on top of her and whispered in my ear "I didn't say to put that on, I said fuck me....now fuck me!" as she placed one hand on my ass and used the other to grab my cock, guiding it as her legs wrapped around me. I was a bit concerned about having unprotected sex, because it went against what we were taught in sex ed, but I figured Mrs Treynor was safe, and as for pregnancy I could pull out.
So aggressively was she pulling me to her that I really didn't have time to marvel at the fact that this was the moment in my life where I would lose my virginity. When I felt the soft wet petals of her flesh touch the head of my cock, now dripping with pre cum, I gasped and opened my mouth in shock at the sensation. As her hand manoeuvred my erection she guided my head past her meaty outer lips, which tenderly parted like soft petals around my twitching young hardness. My face must have looked ridiculous because I couldn't even close my mouth as my eyes opened wide while she guided the head past her labia to her entrance. Upon situating my erection at the entrance, she released her grip on it and brought her other hand to my butt. Using both hands she pulled me into her as she pushed her pelvis up, taking me inside her quite rapidly. I lost all control at the exquisite sensation of her soft flesh sliding over my sensitive organ, and actually made a high pitched gasping moan, as I felt myself sliding inside the warmth of a woman for the first time in my life. Quickly I penetrated all the way in, and felt the pleasure of a woman's inner flesh wrapped around my sex, gripping it, pleasuring it as I felt my scrotum resting against her ass. The reality of this physical sensation was overwhelming, and right away I felt an orgasm stirring before I even had the opportunity to start thrusting. My first reacting was to try to stay real still, and control it, but she started grinding herself up against me, squeezing me and whispering "Oh god I feel you inside me...fuck me" in my ear, so I lost all control and felt the orgasm start. I quickly tried to pull out, but she wrapped her legs around me, not letting me go as she ground up against me slurring "fuck me",  while I gasped "I'm going to....." before it tore through me and I started to ejaculate inside her, pumping my fluids into her vagina as she moaned and squealed, crying "fuck me" in her drunkenness. I shuddered and gasped as I felt my very first orgasm inside a woman, and was completely overwhelmed by the incredibly pleasurable feeling of it. this continued for what seemed like an eternity at the time, as she gyrated and talked dirty, while I released every last drop inside her. Please tell me she's on the pill I thought as I considered the implications of what had just happened. It became evident to me that she was not even aware that I had climaxed, in her drunkenness and excitement , as she kept grinding her pelvis up against me, pulling on my ass with her hands, as she nibbled on my ear.

If nothing else I had been spared the humiliation of her knowing I had came within seconds of penetration. I decided right there and then to just pretend it didn't happen, and started to have sex with her, with slow and even strokes, focussing and making sure I savoured the experience of feeling a woman's vagina repeatedly sliding over my sensitive flesh, marvelling at the fact that my cock was actually inside a woman's pussy! Holy shit! Holy....fucking...shit! This is for real! I'm really doing this!!!

I didn't know if this was lovemaking or fucking, but I knew it was incredible. She was beautiful, clearly experienced and was quite evidently turned on by what we were doing. She had her legs wrapped around me and was using them to pull me in as she rocked against me, as she ground her pelvis hard against me, gyrating her body, and moaning excitedly. She didn't really need to do all that as the physical sensation of fucking was plenty enough for me, but this was hot.

As I thrust into her, she nibbled on my ear, licking it and talking dirty into it. I was so fucking turned on by this, as it almost seemed like something out of a porn movie and it was my vice principle doing this!!!!
"Fuck me!...FUCK ME!" she commanded aggressively in a drunken slur, as her legs kept jerking, pulling me in. "Hard.....Hurt me....treat me rough!" she cried, as I complied, pounding hard and aggressive as she cried "Yesss!!!".

"Grab my ass!" she said, as she bucked against me, her inner muscles actively squeezing me. She certainly didn't need to tell me twice, so in an instant I had both hands on her ass as I thrust my hardness into her soft womanly core, with hard aggressive thrusts while she squealed in ecstasy. It had never occurred to me that my VP could be so kinky, but then why not? She's as human as the next person with all the same urges...I guess sometimes we don't think of adult authority figures as being that way.

"Faster..faster, I'm gonna come soon!" she gasped. I was already getting close to my second orgasm, so I eagerly went at her with everything I had, slamming my pelvis between her legs, while pulling her ass up towards me with my hands, spreading her cheeks with my hands as I drove myself urgently towards climax until I felt my orgasm start, as she started to cry out in mutual climax. As her orgasm ripped through her, she raked her nails across my back, gouging me to the point where I was sure she had drawn blood. I cried out in shock from the sudden pain, mixed with the sheer ecstasy of my orgasm happening inside the body of a squealing woman, as she bit down hard on my right shoulder, adding to the pain mixing with the pleasure as she convulsed beneath me, squealing while my semen pumped repeatedly into her depths. Please...please tell me she is on the pill!. After a few moments of pain and pleasure, we each finished our climax simultaneously, as I sagged on top of her.

Releasing her bite, she started kissing me hungrily, before biting me on the lip, causing me to pull away in surprise, bringing my hand to my mouth, and noticing she had drawn a tiny bit of blood. She quickly pushed me onto my back and climbed aboard me aggressively, straddling me.

"I'm going to fuck you like a bitch!" she slurred excitedly, as  she aligned herself and then slid herself down on my erection, already prepared to go again. As weird and creepy as it was hearing her talk this was, it was also extremely hot. Mrs. Treynor getting all dirty and kinky like a porn star!
She started to undulate on top of me while I lay there, enjoying the feel of her insides sliding over my erection as her sexy body moved like a dancer on top of me. This was way beyond anything I could have imagined in my wildest dreams as I saw the tender beautiful woman above me gyrating sensually, as she grabbed my hands and placed them on her breasts. as much as I was enjoying the physical sensation of her riding me as her insides gripped me, sliding over me, I was captivated by how beautiful she was. As much as we all saw her as pretty at school it was still hard to see her as a sexually active woman, mostly because her job required her to carry herself with a degree of formality.

She rode me for at least fifteen minutes, her buttocks pressing against my pelvis as she rode me, grinding erotically, whining and moaning as though lost in some lustful moment. Our movements were heated as she rode me aggressively, while I bucked my hips upward. driving myself into her depths. I couldn't resist letting my hands wander down to her pussy as I started to toy her clitoris while she rode me, causing her high pitched squeals to rise as she rode me faster until I felt another orgasm approaching.
" Oh god...I'm coming" she squealed as she ground herself down on me, squeezing my shaft with her inner muscles as I felt another orgasm rip through me, causing me to spew my seed upwards inside her belly as she reached down with her hands, pacing them on my chest with her finger tips just below the collarbone and ripped her nails downward towards my belly, leaving gouges and drawing blood as I cried out, trying to control my reaction lest I appear unmanly, but it fucking hurt, and she clearly was drawing blood, as she leaned back, throwing her head in the air, before her shudders passed and she relaxed.

Reaching over, she grabbed the bottle of JD and took a swig before holding it over me and saying "Open your mouth" before pouring it down. I must admit this was not as cool as I thought it would be, as first it stung my eyes, and secondly I really couldn't handle any more, but I wanted to appear macho so I opened my mouth and did my best as the JD/gasoline burned my eyes and throat.

Turning around, she squatted over me in the reverse cowgirl position with me still laying on my back.. I played with her butt cheeks as she did this, and at one point she even lay herself back slightly, allowing my hands to reach around her and explore her front, as we both worked feverishly for about a half an hour towards our mutual orgasm, which exploded through our souls simultaneously as I again sent my fluids into her body.

Getting off of me, she went for the JD bottle again, grabbing a swig. I couldn't bear to drink anymore, for fear I would be sick, so I just raised the bottle to my lips and raised it, pretending to swallow, hoping she wouldn't notice. Eagerly she crawled back on the bed again, and started kissing and fondling me, as we made out for a bit, me exploring her curves and crevices some more in my excitement. Before I know it, we were both kneeling, me behind her as her back pressed against my chest, while one hand fondled her breasts and one played with her clitoris. It wasn't long before she reached between her legs and grabbed my erection, pulling it into her from behind as I slid in with ease and began to make love to her from behind, both of us upright and kneeling. It was actually quite sensual, and it turned out to be my favourite position. It really felt oddly tender and hot at the same time as I kissed her neck from behind, while my hands roamed and I thrust gently into her, again and again. We did this for awhile, in mutual exploration of pleasure.

Before long, she leaned forward placing her hands on the bed, putting us in the doggy style position. Heck I was getting quite the education this night. Placing my hands on her hips, I proceeded to thrust into her from behind, enjoying the visual of her ass sticking out like this, and the feel of my pelvis rhythmically slapping against her ample butt cheeks as I drove myself inside my teachers intimate depths. She moaned and squirmed like a sex kitten as I did this turning me on like crazy as I marvelled over the fact that I was inside the body of Ms. Treynor! I was making love to my VP, with no protection! At one point she urged me to go faster, so I accommodated. When she demanded that I grab her buttocks and spread them hard as I fucked her, I did so eagerly. It was a hot and dirty sensation to be looking at her asshole, as I could clearly see my cock sliding in and out of the hole right underneath it.

"Slap me!" she gasped. I wasn't sure I heard her right.

"What?"

"Slap me...slap my ass!" she said urgently

"Seriously?" I inquired, not sure if I heard her right

"YES!...Fucking slap me!" she cried. Tentatively, I delivered a light slap to her butt as I fucked her from behind.

"Harder!" I slapped her harder

"Harder!!!!' she almost screamed. Winding up I smacked her butt nice and hard, a loud crack resounding through the room, as she screamed "Yes!". I kept this up for a while slapping and fucking, actually finding it to be quite a turn on, if not somewhat weird.

"Pull my hair". I knew what I heard her say, so instead of being silly I just complied, pulling her hair back.

"Harder! Pull my head right back!". Complying, I yanked her hair hard, pulling her head back as I pounded her.

"Good, now fuck me hard! Hurt me! Pound me like a dirty street whore and punish me with your cock!...Rape me!". Under any other circumstances that dialogue would have me busting up laughing at the cheesiness, but it was fucking exciting to hear it first hand from her and I hate to admit I threw myself right into it. She kept giving me instructions, telling me to talk dirty to her, to call her things like "whore" and "bitch" as I pounded her. On one hand, I felt a bit uncomfortable speaking to my Vice Principle like that, given her authority over me but then I suppose having doggy style sex with ones vice principle is also pretty unconventional, so I did as instructed. Oddly, I've never had any misogynistic tendencies, or felt any sense of dominance towards women, but there was something exciting at a visceral level to be pounding a woman from behind, pulling her hair, slapping her and talking to her like that.

I pounded Joanne's vagina from behind, excited as hell from the sheer dirtiness of what we were doing, feeling her insides milked me, as my pelvis slapped hard against her buttocks, battering them with a repetitive beating pattern, as she screamed and squealed in delight, me spanking her, calling her dirty names as I pulled her hair.

"I'm going to cum soon......bite my neck!". I was caught of guard by this, yet heard her clearly, and leaned forward, carefully placing my teeth on the back of her neck and squeezing feeling my own climax approaching.

"Hard! Bite me like I'm a bitch dog! Dominate me!" Who are you and what have you done with Mrs Treynor? I thought.  Complying, I bit down hard, causing her to cry out as I pounded her, feeling my orgasm about to start while I continued to pull on her hair. A few more rough thrusts and I felt it happen, while she started to squeal in the throes of orgasm. We both seized up, her crying out loudly as it seemed like we shared the same orgasm, the vibration rippling through is both as her insides contracted and I pumped my sperm into her depths, clamped on to her as I spent myself inside her body until it was all over, and I realized how exhausted I was. I was drenched in sweat, and breathing like I had just ran a marathon. I also noticed that my erection was finally starting to soften. Of course after five consecutive orgasms that should be expected. I needed to lay down and rest.

Joanne had other ideas. Pulling away, she turned and faced me, slapping me across the face. My head rung for a moment, and I looked at her in astonishment as she gave me a naughty grin that said I'm so nasty as she pulled me in, kissing me hard. Grabbing my balls, she slurred "I want fuck you till your crying!" in a heated lusty voice, breathing excitedly as she said it.

Again? Holy shit I was exhausted. How the hell does she manage to keep going like this at her age? I was ready to have a heart attack.

"Whoa...can we just take a breather for a moment?" I said, looking at her apologetically. She was also sweaty and breathing hard, just too excited to care I guess.

"Tired?" she inquired? "Here" she said, gesturing to me to sit on the edge of the bed. Sitting there, my feet on the floor, I watched as she moved in front of me

"I'll do all the work here" she said, moving to sit in my lap, facing me. Before she could, she noticed I had started to soften.

"Uh-oh...let's bring him back!" she said, shoving me hard so I ended up laying back. Laying on top of me, she quickly moved herself down, her breasts running over my penis, before she  positioned herself kneeling in front of me. Opening her mouth, she leaned forward towards my flesh as I lay there in amazement. Is she about to blow me?
"Mrs Treynor...." I started before I gasped from the most pleasurable sensation as she went to work with her mouth and tongue. I lay there, my whole body tensed, my mouth wide open as I actually whined in excitement; unable to even comprehend how someone could possibly inflict so much pleasure as she expertly did things with her mouth and hands that had me rock hard again in no time at all.

When she stopped, I actually felt incredible disappointment. She was not planning on finishing me in her mouth. Maybe some other time I thought as she stood, crawling over me while gesturing to me to sit up. I was seated on the edge of the bed, while she straddled me, facing me and wrapping her legs around me as we both embraced while upright. Quickly, she raised herself, and grasped me, lining me up with her portal before lowering herself to be impaled on my hardness.

It was an intimate feeling that transcended the mere physical sexuality of the moment as the two of us embraced, looking into each other's eyes, kissing as she brought herself up and down slowly, impaling herself on my flesh. We made love like this for what seemed like an eternity, the two of us wrapped in each other's embrace as my body remained embedded in hers, as we made love slowly. Of course as things picked up, she started to speed up her actions, as the intensity of our sexual bond heated up, and the friction of her insides against my organ reached new peaks while her soft sweaty skin pressed against mine. This was a real switch from the last round. This was lovemaking. This was tender and affectionate yet still sizzling hot. Her well toned thighs drove her body up, causing me to slide almost all the way out with only the head remaining before she would lower herself all the way down, impaling herself on me until her buttocks rested on my thighs. Then she would squeeze me with her internal muscles and gyrate in my lap as I felt my tip pressing deep inside her belly as she kissed me passionately, her nipples brushing against my chest each time she went up and down.

As we felt ourselves moving towards climax she spoke;
"Touch my ass!". I eagerly grabbed those soft tender butt cheeks of hers. "No...I mean my asshole", she gasped excitedly. What the fuck?
"You want me to touch you're..."

"Take your middle finger and just touch it to the rim....it's fine, trust me" she said urgently. I didn't want to kill the moment or disappoint her, so I complied, but found this a bit icky. Carefully I reached with the middle finger of my right hand and slid it down her inner butt cheek until it made contact with her anus, causing her to gasp erotically at the contact.

"OK, now just lightly rub it and tease it", she whined. I did this, and the reaction I got out of her was unreal. She was getting hugely into this as she rode me, whimpering and crying out in pleasure.

"OK....push the tip in lightly" she said "and then probe in and out with just the tip". Mrs Treynor, you do realize that you crap out of there right? I thought, but again did not want to disappoint as I was really enjoying the sex. Pushing my fingertip against her resisting ring, I felt it pop through the tight elastic openning, and she screamed, and for a second I thought I might have hurt her. I also worried someone might call security if they heard her.

"Are you OK?" I inquired, genuinely concerned

"Yessss...oh my god keep doing that...in and out!" she moaned. I did just that, and her sex kitten routine went into overdrive, as she squirmed and fucked me like she was starving for it. For a teen boy, who thus far had almost no luck with girls, this was an education. My only regret was that I would never be able to tell anyone for obvious reasons. I continued exploring the inner rim of her butt, getting mildly excited by this while still a bit weirded out as she continued to grind her body upon mine

"I'm going to orgasm soon!" she whined. I felt myself approaching climax too. "When I come, push your finger all the way in!" she urged. I was undecided as to whether I found that idea exciting or gross or both, but I said "OK", as we worked towards climax urgently needing that release.

"Now...now!" She cried. At this I plunged my finger into her forbidden depths at the same moment I felt my climax start with hers and she shrieked loudly as she impaled herself on my cock while her whole body shook almost violently. As this happened I felt the most intense orgasm I had ever known, as I literally felt it throughout my body, as I started pumping my fluids into her womb. She bit down on my other shoulder this time, quite hard, and I knew she would leave teeth marks that would last for a week or so. It hurt, but I resisted crying out. When her fingernails went to my back, I knew what was coming, but still winced when she tore them across my back viciously. It hurt quite a bit, but did not distract from the tremendous pleasure vibrating through my body from my groin. It seemed like this orgasm lasted forever, and when it finally passed, I gasped, as she continued to shudder, and squeal. Aftershocks? Multiple orgasms? I didn't know, but she moaned and shuddered for almost 20-30 seconds after I finished, before she also sagged against me, our two sweat drenched bodies heaving and gasping for air.

We collapsed on the bed, wrapped around each other, skin on skin, sweat covered and breathing hard and passed out soon thereafter. I recall vaguely at one point in the night waking and pulling the covers over us, as she snuggled up against me in her sleep, laying one leg across me.................................................................

"Greg!" an alarmed voice cried out, shaking me from my slumber.

"Greg! Wake up!" I recognized it as Joanne's voice, but she sounded hysterical, and upset. Opening my eyes, I saw Joanne looking at me in horror and shock.

"What are you doing here!" she demanded, clearly upset, as I felt my head pounding from my first hangover.

Confused by her reaction, I cleared my throat and tried to ask what was wrong. "Joanne.....?"

"Mrs Treynor!" she corrected me looking bewildered and furious. Sitting up, I allowed the blankets to slide down a bit, exposing my upper torso. Immediately her eyes zeroed in on the scratches and bite marks on my chest and shoulders. She gasped, and brought her hand up to her mouth, looking at me with eyes that looked both shocked, and ashamed...almost like she was about to cry.

"Oh my god...Greg......" she couldn't stop staring at the injuries she caused. She blinked her eyes a few times and looked like she was trying to hold back tears.

"OK get up and get dressed" she commanded, her voice faltering. When I turned away from her, to get out of bed, she saw my back, and literally cried out in alarm.
"Oh no......Greg...." she said in a very maternal sounding voice. I guess she knew right away that she had done that as obviously this was a kink of hers. "Greg...your back" she said in an apologetic voice.

"It's fine...really" I said, standing and turning to face her. Of course as soon as I did that, exposing my nakedness fully to her, at which point she brought her hands up in front of her eyes, and awkwardly said "Please..just put something on before you say anything" I quickly scrambled to put on my boxers, and then started pulling on the rest of my clothes.
"Greg" she started, sitting up and making sure to cover herself with the blankets. "What happened...did we....", she had a look that said she knew the answer, but was hoping against hope to hear that it wasn't true.

"You don't remember?" I asked confused

"NO!" she cried out in exasperation..."I would never...", as she sat up more, her hands went to her head. "Oh my god". She stood on wobbly legs, making sure to hold the covers around her. For a second she looked like she was going to cry.....then she rushed to the bathroom, closing the door behind her and a moment later I heard her being sick. She emerged a moment later, looking pale and sick, her makeup smeared and her hair a mess. She grabbed her robe, and disappeared into the bathroom again. Emerging a moment later, she looked mortified, and made her way over to the small couch.

"What happened?" she asked in a shaky voice that sounded like she was a hairs breath away from a nervous breakdown. I moved to sit beside her, but evidently sat a little too close for her comfort and she gestured to me to create a little space between us.

"Well, I saw you in the hall, we talked, and we came back here. We had a few drinks..." at the mention of her giving me alcohol she flinched, "...and then we talked for a bit. You were upset about your ex, you were being very friendly and I guess it just sort of happened."

"What happened" she emphasized each syllable. "Did I ....did I interfere with you?"

Interfere? What the hell does she mean by interfere? I looked at her quizzically

"Did I ...abuse you?" she inquired.

"Not really, I mean you did some scratching and biting, but it wasn't really abusive...actually a tiny bit exciting I guess..."

"Greg!" she snapped, cutting me off. "Did you and I have sexual intercourse?"

"Yes" I said, not seeing why she was so upset. When I said yes, she reacted as though someone had slapped her very hard.
"Oh my god! Oh my god!" she said, lowering her face into her hands as her voice had almost a sob to it.

I felt terrible. Reaching out I put a hand on her shoulder to comfort her. "Joanne...."

"Mrs Treynor" she corrected again, pushing my hand away.

"OK, Mrs Treynor, I'm really sorry. Sure you were drunk, but you recognized me, you knew my name...I didn't mean to do something you didn't want", I said apologetically. She looked at me with devastated eyes.

"Greg, don't apologise. You have nothing to apologise for here. You did absolutely nothing wrong" she said, looking at me intently. "I'm the one who is at fault here. What I did to you was horribly wrong!" she said in the saddest voice I had ever heard.

"No, Mrs Treynor, I'm fine with this. It was great I swear. I loved being with you, you were beautiful..."

"Greg, just please stop talking for a moment" she cut me off again, shaking her head, almost as though she wanted to deny this to herself. She ran back to the bathroom again to be sick a second time. She then rinsed her mouth, brushed her teeth and gargled mouthwash before making her way back to me. Looking over she saw the bottle of JD and realized how much of it she and I had drank, as she also noticed several empty beer cans, and that the vodka was out with a few seven up cans.

She sat down again, wrapping her arms around her chest.

"I'm going to have to write up a report in this, and step down as Vice Principle" she said, her voice sounding like she was going to cry.

"What?..No!" I responded, "Why? I mean it's not like you did anything really that wrong here"

"Greg. I am your vice principle! I have authority over you, I am responsible for your guidance and development. You are my student. I'm supposed to guide and protect you, not....." her voice trailed off as her eyes started to tear up. I tried to comfort her, placing a hand on her thigh.

"Look Mrs Treynor.." she again pushed my hands away, and I looked at her a bit hurt.

"Greg, it's nothing against you, but please don't touch me" she said her voice quivering.

"Mrs Treynor, it's not like you had a gun to my head. I wanted to...I'm not upset at all. It was really great".

"Greg, it doesn't matter if you were willing. I'm the one who is supposed to make the right choice, and do the right thing.

"Ok, can I say something without freaking you out...please...just listen?". She looked at me. "Ok, maybe you made a mistake, but last night was something special for me. You were my first..I had never done it before.." her hand went up to her mouth again at the mention of my having been a virgin. "I'm sorry that you regret it, but I don't want to be responsible for destroying your career..."

"Greg, I am responsible for this, not y......." she said, cutting me off. I cut her off just as quick;

"Look, Mrs Treynor....please, just reconsider. Everybody has to have a first time, and I don't want mine to end like this. I don't want to remember you being shamed, getting into trouble, and losing your career every time I think of my first time....this meant something to me...I don't want it ruined.......and I don't want to see you hurt over it....please". She looked at me sympathetically, but was still shaking her head, and opened her mouth. "Greg....I can't..." her voice trailed off again.

"Look, I really like you as a teacher.....you have made a difference for a lot of people. Don't throw that away. You love being around students......I don't want you gone" I said.

She paused, took a deep breath

"Greg, I always swore I would protect my students. I swore that if any faculty member put so much as a finger on a student I would destroy that person, and I have told other faculty members that. Now if I let this go, I'm a hypocrite. Everything about me would be a lie, and I can't live with that. I have to do the right thing here"

I shook my head desperately

"Look, Mrs Treynor, can you please just not rush into anything...please...for me. Just don't do anything yet....can you wait a few days.....can we just wait until you've had some time to calm down and we can talk. Please?" She looked at me, conflicted.

"And I swear on my life I will never tell anyone, not even my best freind..ever"

"But Greg, I would know", she said, but I sensed I was making some headway here.

"Please....I want to at least talk to you before you do anything. Just to talk about what happened...after that experience, I really would just like to be able to talk about it...talk about my feelings before you go and tell the whole world"

"Greg....I don't know" she whispered.

"Look, wait a week and let's talk. After that if you still feel the need to report it then I can't stop you. I just want to talk once. Please?"

Blinking rapidly, she swallowed audibly, and nodded, whispering "OK"

"Thank you" I said

I awkwardly made a move towards her, wanting to hug her. She looked resistant at first, but then figured at this point a hug could not really do any harm. She embraced me, in a sort of maternal way as I held her, listening to her sniffle as her hands gently rubbed my back. Breaking the hug, she placed a hand on my face and gave me a sweet yet sad look.

"Ok I should probably get going...." I said, looking at the clock, noticing the time and realizing my parents would be up soon if they weren't already up.

"Oh my god, your parents.......you didn't make it home last night...they must be hysterical" she said

"No, it's OK. I have my own room and they would assume I was there....but I really should get going"

At that point a loud knock came from the door. I don't know who jumped more at that sound, her or I but we both froze. I looked around and immediately decided the washroom was the best place to hide.

"I'll hide in there" I said as she nodded. Making my way in, I partially closed the door as another knock came from the door. Joanne opened it a crack, and answered.

"Shannon?" she said with a bit of surprise in her voice.

"Hey, you left early last night. We were worried about you" this Shannon lady said through the barely opened door.

"I'm fine" Joanne replied, "I just needed to lay down"

"Is everything OK?" Shannon asked, evidently finding Joanne's behaviour suspicious as she allowed the door to only open a few inches instead of inviting her in.

"Yes, I'm fine. Just had a few too many last night and now I'm feeling it." she replied.

"OK, well a few of us are meeting for breakfast in about twenty minutes if you wish to join us" Shannon finished.

"Uhm, maybe. Let me see how I feel and if I can get ready in time", she replied.

"OK, see you later then".

"Bye", Joanne said before closing the door.

Stepping out, I looked at her inquisitively.

"She's an old friend" Joanne said. "Ok, let's get you out of here" she said, as I went towards the door. She opened it and peaked out, making sure the coast was clear.

"OK, get back to your room" she said, ushering me out the door.

As I stepped out, I looked at her, and cleared my throat. "So, we're going to...."

"We'll talk. Now get going" she said.

Nodding I headed back to my room and not a minute too soon. I literally had barely got in there when my own door knocked. It was my mother, saying they were heading to breakfast soon, telling me to hurry up and get cleaned up. I felt very awkward, hoping she didn't suspect anything.

At the restaurant, I felt horribly hung over, but still ordered a light breakfast. The thought of greasy eggs and bacon would have made me spew everywhere after all the booze I drank last night. Holy fuck my head hurt!

Sure enough at one point my mother tapped me on the shoulder and said "Hey, isn't that Mrs. Treynor over there?". Confirming that, yet acting surprised to see she was here at the same restaurant, I managed to convince my mom not to go over to say hi.

Later that day, we drove home, and I spent the next several days wondering what it would be like to see Mrs. Treynor at school. What had happened between us had meant something to me and I really wanted to see her again. I planned all week for the meeting, and thought about the things I would say.

When we passed each other in the hallways, she looked extremely awkward. I made a point of not doing anything that would make her uncomfortable. I knew she stuck around late every Thursday so I would stay after school that day and talk to her. I just went over what I would say in my head as I tried to find the right words.

To be continued................

While you're waiting in vain for that apology, why don't you make yourself useful by getting on your knees and opening your mouth


Offline Meatbot

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Reply #1 on: November 26, 2014, 03:30:59 AM

Wow, I am so convinced that you are simply remembering this stuff and writing it down... very realistic, and sexy... makes me realize what a mundane life I led as a youngster...

Anyway, great story, look forward to more.

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Offline SouthernGent

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Reply #2 on: November 26, 2014, 01:57:11 PM
Loved it, can't wait for more.

The Gentleman Freak.


Offline redhatlover

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Reply #3 on: November 26, 2014, 06:35:09 PM

I am like Charlie the Tuna.  I don't want women with good taste, I want women who taste good.


Offline Scotty

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Reply #4 on: February 02, 2015, 05:09:05 PM
Thanks you grabbed my head and took me along for that wild ride ! I liked that story and I'm going to imagine that it really happened. I couldn't stop reading it.