This is a bit of a confession. Actually it’s a lot of a confession and could get me into serious trouble but I feel compelled to write this down.
My name is Sally and I’m an English teacher in a private school for boys in the Oxfordshire countryside. I’m 32 years old, curvy, 5’ 8" and have long straight strawberry blond hair. I have bright green eyes and lots of freckles all over my body. My boobs are 36C and my hips are quite wide. My friends say I’m good looking and I have no difficulty in picking men up. Boyfriends do not tend to last too long though as I get bored easily and like my independence.
The school I work in is a weird place. The headmaster runs it like a traditional public school with strict dress codes for pupils and staff but his teaching policy is very modern. Most of our pupils are boarders and staff members live on school premises in single bedroom apartments which double as an office. The school in return for supervising evening study sessions and weekend activities with pupils provides the apartments. Hard work and a lot of time but for the excellent pay and 14 weeks holiday a year it’s worth it to me. Also I get to teach attentive students who actually want to learn.
So the thing I want to confess happened in my third year at the school. His name was Roger and he was the second son of Lord Somebody or other. Roger is a pleasant boy if a little geeky. Our school doesn’t stress the need for physical exertion as much as some public schools so Roger was fairly normal. He was passionate for computers, spending hours in the computer room designing web pages and little Java applets. Part of my extracurricular work was to supervise and assist boys using the computers during the evening and weekends. I was hardly needed since most of the boys who used the computers out of hours knew far more than I would ever know already but I liked it because my office/apartment was directly opposite the computer room. The boys knew that they could knock on my door if they needed help and I wasn’t there and I could sit and read a book in comfort.
The computer room shut at 9:00pm so the boys had time to get back to the dorms on the other side of the campus by their 10pm curfew. If an older boy was working hard on a project I would ring his dorm master and get him a curfew extension until 11pm. Roger took advantage of this a couple of nights a week as he was working on his family tree for a history project. For a week he was the only boy in the computer room after 9pm, seated at the back and more or less hidden from the rest of the room. Pupils were free to use the internet for research and for personal email. We had a software filter set up to stop pupils from looking at inappropriate material so there should have been no danger. How wrong can you be?
On the Friday evening I had left Roger on his own and returned to my apartment to finish my book. I was dressed in my usual lounging outfit… soft jogging bottoms, thick socks and a baggy t-shirt. I had no underwear on. I finally put the book down at 10:40pm and walked across the corridor into the computer room. I could see Roger in the corner and heard heavy breathing. I could see his hand moving in his lap. My heart skipped a beat as I realised he was masturbating. I slowly walked over the floor in my thick socks, making no noise on the polished wooden floor. I was suddenly very excited, my nipples were hard and pressed against my shirt and I could feel my vagina moistening. Rogers eyes were fixed on the screen and he didn’t see me as I stood next to him looking at what he was looking at… a high resolution picture of a woman sat on a man’s penis. I gasped at the site of the guy’s long cock impaling the woman’s shaven vagina. Roger looked from the screen to me just as his body decided it was time to orgasm. He shook and looked at me helplessly as his cock shot sperm over his bare legs and on to his shirt.
‘Oh shit, Miss. Jesus, I’m sorry!’ Roger said pulling his trousers up and trying to stuff his still hard cock into his underpants.
‘Stand up. Get dressed.’ I shouted trying not to laugh at the poor lad. ‘I trusted you. How did you get porn on the computer?’
‘I hacked the filtering software and switched it off for this workstation.’ he admitted.
‘How did you do that?’ I asked a little more calmly. I was still really turned on.
‘I saw Mr Lincoln’s password and used that.’ he said.
‘Right, you are on weekend report. Go to your dorm and report to me tomorrow morning in my office.’ I said.
Roger practically ran out of the door. Weekend report was a way of punishing boys who had broken the rules. Basically it meant that they sat indoors for a couple of hours doing something pointless. I didn’t agree with it as a punishment but it was all I could think of at the time. My mind was not working correctly. I sat in front of the computer and looked at the open windows. Roger had got the images from a link site called thehun.net. I shut the computer down, locked up and returned to my room.
My mind wouldn’t leave the image alone. I tried to read a book but my mind returned to the image of the cock deep inside the girl. I hadn’t had sex for six months at that point and the last experience was nothing to write home about. I gave up with my book in the end and sat at my desk in front of my computer. I loaded thehun.net and started following the links on anything that looked interesting. 30 minutes later I was sitting at my desk naked looking at pictures of a pretty young blond girl having sex with two men. I gasped as I opened a picture of her been penetrated both vaginally and anally by the two guys. My fingers were already pressing gently against my clitoris but the site of a huge cock penetrating the girl’s tight arsehole made me push two fingers inside myself. I opened the next couple of pictures to reveal both men squirting cum over the girls face. This pushed me over the edge and I gripped one of my pink nipples as I orgasmed. I switched the computer off and had a shower before going to bed. I couldn’t sleep. I just kept thinking of the sight of Rogers’ cock and wondering what I was going to say to him in the morning and how I could punish him.
The next morning I spent 20 minutes deciding what to wear. My usual school teacher attire was a dull blouse with a skirt and jacket. School dress codes forbid me from wearing trousers when teaching and weekend report came under those rules. I settled on a beige wrap around skirt over flesh coloured stockings (I dislike wearing tights but the rules don’t allow bare legs) and a white blouse. My underwear is all pretty much the same… cotton thongs and plain bras. I also had a couple of silk bodies that I liked to wear in the winter and I pulled one of those on today. Looking back I guess I choose to wear that particular body because when it’s combined with the blouse I had on it makes my breasts sway rather nicely as I walk.
Roger was waiting outside my door at 9am. He was dressed in his uniform as the rules insisted and looked scared. I motioned him inside without saying anything and he walked through into the small office area of my apartment. He stood in front of my desk with his hands held nervously behind his back. Like a soldier standing easy I suppose. I sat down at my desk and opened my report book.
‘I have to make a note of why you are in weekend punishment. This book is then reviewed by the head of year and further action could be taken. What you were doing last night is grounds for suspension or expulsion. What do you have to say in your defence?’ I said sternly.
‘I have nothing to say.’ Roger said quietly. I got the impression he was bordering on tears.
‘Nothing? Not even an explanation as to why you chose to abuse the trust I’d shown in you?’ I said, still not knowing how far to take this.
‘I hacked the firewall out of curiosity. Then I found the web site and couldn’t help myself. You’re right, I have abused your trust and I am truly sorry for that. Is there anything I can do that will make you reconsider expulsion? My father will be livid!’ Roger blurted very close to tears now.
‘OK, calm down. I don’t think I’m going to report you. You’re a bright boy and you were doing no real harm. I wouldn’t want to destroy your life because you let your hormones get the better of you.’ I said soothingly. ‘However you must learn that ill thought out actions cause unpleasant consequences. If we were still allowed to use corporeal punishment I would suggest it. What do you think your father would do to you?’
‘Strap me. The school might not allow corporeal punishment but he still believes ‘spare the rod, spoil the child’ holds true. You could strap me if you like. Anything would be better than reporting me.’ Roger said sounding rather desperate.
‘I can’t do that Roger, it’s illegal and could cost me my job.’ I said in shock.
‘I wouldn’t tell and you wouldn’t have to tell my father.’ Roger said.
‘Roger, are you excited at the prospect of me spanking you?’ I asked, my heart pounding in my chest.
Roger hesitated for a moment looking into my eyes then slowly nodded.
‘I’m supposed to be punishing you for being a little pervert and you’re trying to make your punishment into a fetish. Are you trying to convince me to report you?’ I asked.
‘No. I’m not. I’m just sorry!’ Roger said in a panic.
I sat back in my chair and looked at Roger. He avoided my eyes and looked at the floor. He was a good-looking boy, short blond hair, a little shorter than me at 5’6" and slim. He was well tanned, probably from spending the summer somewhere expensive. He looked older than his 18 years although not by much. I shook my head to clear the sudden image I had of me kissing him. What the hell was I going to do? The rules of the school dictated that I should report Roger but I really didn’t want to. What I actually wanted was to take him to my bedroom and make him do to me what the pictures I’d been looking at showed.
‘Bend over the table Roger.’ I said suddenly making his head jerk upright.
‘Miss?’ he said.
‘What I’m about to do is against school rules. What you did was against school rules. I think that will make us even.’ I said hardly able to believe that I was even thinking about doing this.
Roger leant forward and grasped the table. I walked to the door and made sure it was locked. My apartment is in the oldest part of the school and the door is made of thick wood which makes it virtually sound proof. My office is well away from any windows and I’m on the third floor.
I stood behind and to one side, lifted my hand up and then brought it down on his left buttock three times making a satisfying smack sound each time. My nipples hardened against the silk of my body and I could feel my vagina moisten. My hand stung from the impact and it didn’t look as if Roger had even felt it.
‘Roger, drop your trousers. If I’m going to risk everything doing this I might as well do it right.’ I said making a decision that could ruin my life.
Roger quickly removed his shoes, socks and trousers and stood in front of me. A little too quickly and eagerly I thought in the back of my mind.
‘You might as well take the rest off.’ I said looking at his hairless legs and the bulge in his underpants.
Roger eagerly stripped naked and stood in front of me. His body was smooth, tanned and hairless apart from a tangle of blond pubic hai. His cock was rock hard and pointing vertically up his body. It was of average size and circumcised something I’d not really seen before. My mouth watered and my nipples were so hard they were hurting. I walked into my living room and beckoned him to follow. I sat on the edge of my leather sofa and opened my wraparound skirt to reveal my stocking tops. Roger looked as if his eyes were going to fall out.
‘Bend over my knee boy!’ I said strongly.
Roger almost leapt on to my knee, bending over so his bum was over my thighs. I could feel his hard cock pressing against my thigh and wiggled around a bit to get comfortable and for the pleasure of feeling his hard cock against my thigh. As soon as I was comfortable I began spanking his bum, alternating cheeks with occasional smacks of his thighs. I stopped after about 20 slaps and caught my breath. I was horny as hell now and my crotch was soaking. Roger was moaning and breathing heavily. For the last few smacks he had been wiggling against my thigh, rubbing his cock off against me. I caressed his reddening bum and reached between his legs to feel his balls. He opened his legs to allow me access and increased his wiggling.
‘Are you getting off on this Roger?’ I asked releasing his balls and slapping his bum again.
‘Yes miss.’ he groaned.
I spanked him a dozen more times, letting him wank himself on my leg, then put my hand back on his balls and began to squeeze them gently. I ran my thumb between his bum cheeks and over his anus. He groaned loudly at that and I felt a shiver run through his body then he jerked and I felt him cum on my thigh. I held his balls as he squirted twice more then pushed him off my knee and on to the floor. My stockings were covered in cum and it was in danger of dripping on to my expensive skirt. I quickly unfastened the skirt and stood up leaving it on the sofa. Roger was laid on the floor looking up at me as I looked around for a tissue. I looked down at him and decided it was his mess so he should clear it up.
‘On your knees boy, lick up your mess.’ I said standing over him.
Roger got on his knees and knelt in front of me. He tentatively put his hands on my hips then leant forward to lick his cum off my stockings. I put my hands in his hair and pulled him closer. His hands explored my hips then slipped around to my bum fondling my fleshy cheeks through the thin covering of silk. He quickly lapped up the mess he’d made then started to run his tongue further up my legs. I pulled his head away and looked down at him.
‘Lick my cunt. Do you know how?’ I asked.
‘I’ve never done it before but I’m willing to learn.’ Roger answered.
I unbuttoned my blouse and threw it on a chair then sat back on the sofa. I opened the poppers on the crotch of my body and opened my legs wide. Roger stared at my ginger haired pussy his breathing speeding up again.
‘Kneel in front of the sofa and put your head between my legs.’ I said.
Roger moved in front of me and I pulled my labia apart then fondled my clit causing it to stiffen.
‘Lick and suck my clit. You can lick all around my labia too, that feels good. Push your fingers in me if you like.’ I purred.
Roger started to lick me starting on my clit and moving around my pussy as he gained in confidence. I felt his long tongue probe me for a couple of minutes then he moved back to my clitoris. I held his head as he sucked my clit into his mouth and began to run his tongue over the tip. I wrapped one leg over his shoulder to hold him in place and told him to keep doing exactly what he was doing. I came in less than two minutes, mashing his face into my cunt and pulling his hair. Finally I let him go and pushed him away from me.
‘Not bad for a beginner.’ I said when I got my breath back.
‘I like my punishment so far Miss.’ Roger said cheekily ‘Much nicer than fucking boys.’
‘Bloody hell, you do that?’ I asked.
‘Most of the boys do it at some point. Or have it done to them. It’s just something we do for fun.’ Roger said ‘I’m sure the masters know about it, hell half of them were at public school so they should.’
‘God, so do you fuck or allow boys to fuck you?’ I asked.
‘Both. I am both a giver and a receiver.’ Roger said ‘But only with a select few if you see what I mean.’
‘Sounds like you have orgies over in the dorms!’ I laughed.
‘Not really. You usually stick with a best friend because everyone does it but no one wants to admit it. Too gay.’ Roger said ‘And we never kiss each other.’
‘Have you ever kissed a girl?’ I asked.
‘Yes, tons of them. But only on their mouth, not where I just kissed you!’ he replied smugly.
‘Cheeky little bastard.’ I said standing up ‘get in the bedroom.’
Roger walked into the bedroom with me and I stripped off my body leaving me wearing my stockings, heels and a smile. Rogers’ cock was hard and I was wet so I pushed him on to the bed on his back and put 2 and 2 together. I straddled him and sank his cock into my cunt then leant forward over him and pushed my big breasts into his face. Roger looked awe-struck as I began to ride his cock.
‘Does your roommates bum feel like this then Roger?’ I asked as I fucked him.
‘God no. And he’s never sat on me like this. And he doesn’t have tits!’ Roger gasped.
I leaned over and pushed my lips to his forcing my tongue into his mouth. I was totally into fucking this boy now and didn’t care about any consequences that might arise from it. Roger moved his hands over my body, feeling my nipples and bum as we kissed and fucked. Eventually I could feel my second orgasm building and sat up so I could get to my clit. Roger put his hands on my tits and played with my pale, pink nipples as I rode myself to orgasm on his cock.
When I’d cum I slipped off Roger and lay on my back on the bed. Roger climbed on top of me and spread my legs, quickly slipping his cock inside me. He braced himself with his arms then began to slide his cock in and out of my slippery pussy. I wrapped my legs around his waist and put my hands on his bum pulling him into me. Roger spread his legs and I felt my long fingers slip between his buttocks as we fucked. I probed for his anus, remembering what he’d said about getting fucked there and gently rubbed my fingertip across it. One of my ex-boyfriends used to love me doing this but would never let me penetrate him. I pushed harder and felt my finger slide into his bum. I pushed harder and got my finger deeper into him.
‘Ouch!’ he said.
‘Sorry!’ I replied backing off a little then gently finger fucking with the first inch or so of my finger.
‘Need something to lubricate it!’ Roger gasped.
‘I should know that!’ I replied ‘It hurt like hell the first time I had anal sex.’
‘Oh God!’ Roger said thrusting hard into me and filling my pussy with cum.
I held him until he finished shaking then we lay on the bed side by side both breathing raggedly.
‘That was great Miss.’ Roger said.
‘It’s Sally. Call me Sally. You can’t call me Miss when you’ve just fucked me.’ I said.
‘OK, Sally. That was great.’
I cuddled up to him and began to doze slightly. I was woken by the telephone half an hour later. It was my mother calling for her weekly chat. I sat on the edge of the bed and tried to concentrate on what she was saying but Roger was erect again and I was aching to fuck him. I made my excuses to my mother telling her I had a pupil who needed my attention then jumped back on the bed with Roger, grabbing a bottle of KY jelly I use when I masturbate, on the way. I pushed Roger back on the bed as he reached for me then straddled his chest. I moved back until I was squatting over his face then lay down on him and took his cock in my mouth. I began to suck and lick him, pushing his legs open so I could get to his balls with my fingers. Roger eagerly took my clit in his mouth and pushed first one, then two fingers into my pussy.
‘Use this on your fingers.’ I said throwing the bottle of KY behind me.
I felt Roger move around under me then the cold, wet feeling of the KY jelly being smeared on my pussy and over my bum.
‘Sorry, got too much out!’ Roger stammered.
‘So use it then.’ I purred ‘And throw the bottle back. I need it for you.’
Roger threw the bottle down the bed and I felt his fingers push against my pussy, two of them slipping into me. His other hand probed my anus, one finger sliding over the puckered hole then slowing pushing past the tight muscle to penetrate me. I felt him push his fingers together inside me and shuddered at the feeling. I squeezed some KY on to my hand and used it to lubricate his balls. Roger groaned as I squeezed his scrotum and sank his cock deep into my mouth. I pulled his legs back so I could see his anus then sank a lubricated finger into him. I began to finger fuck him, pushing the fingertip hard against his prostate. I felt his cock twitch in my mouth as I found the right spot. We fucked and sucked each other for a couple of minutes, both of us adding a second finger to each other’s anus. I was getting a warm feeling in my bum now and I knew that the only way to satisfy it was to get Roger to fuck my arse and spank me. I love this feeling as I so very rarely get in the mood for anal. I finally couldn’t stand it anymore and pulled myself off Roger and bent over the end of the bed.
‘Come and fuck me up the bum Roger.’ I said.
Roger moved behind me at an indecent pace and I felt his hard cock push against my anus then slip inside me. Roger went slowly at first; knowing from his own experience that he should takes his time. He was soon deep inside me and began fucking me with slow hard strokes.
‘Fuck me really hard and spank me Roger, make my bum red.’ I demanded.
Roger responded and started hammering his cock into my arsehole and slapping my soft bum with his hands. At first he was quite gently with his slaps but he began to make my bum sting, as I demanded more. I pushed my hand underneath me and fingered my hard clit making myself orgasm immediately. The best thing about anal sex for me is the build up. I have lots of small orgasms, which build to a huge one. This was happening now and I hoped that Roger wouldn’t cum before I did. The second orgasm hit me followed quickly by a third and a fourth. Roger leant over me and pushed his hands under my body to feel my tits. I could feel his hot breath on my neck as he fucked me hard. Orgasm five hit me and I knew the next one would be the big one.
‘Keep going lover. Keep fucking me hard. I’m nearly there.’ I gasped as my body began to shake.
Roger accidentally pulled his cock out of me on a backstroke and slammed it into my pussy, something I’ve never allowed before. This pushed me over the edge into a huge orgasm. Roger thrust a couple of times into my cunt then seemed to realise his mistake and pushed his hard cock back up my arse. I was in throes of orgasm by now and could hardly catch my breath. My legs collapsed from under me and Rogers’ cock fell out of my arse as I slid to the ground at the end of the bed.
‘Jesus, are you OK Miss? I mean Sally.’ Roger asked.
‘Oh Good God yes’ I managed to say ‘do whatever you want to finish yourself off.’
Roger nodded and helped me on to the bed on my back. He knelt over my chest and pushed my tits together around his cock and began to tit fuck me. I lay back and watched him wank himself off between my tits moaning as he played with my nipples. After a minute he leaned forward and shot cum in my face and hair rubbing the end of his cock over my lips. I opened my mouth and sucked it, not caring that it had been up my arse. Roger eventually lay next to me and licked my face clean then we slept for an hour or two. Eventually he had to leave or he would be missed in his dorm so I made him dress and sent him away.
Did I see him again? Yes I did. We had to be careful so Sunday was the only day we could really have sex together. We managed a couple of furtive fucks during the week but Sunday was our day of exploration of each other. I might write more about what we discovered later.
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