4 comments/ 35421 views/ 9 favorites Detention with Ms Marshall - Day 01 By: Esprade It was another regular day in early Spring, just a couple weeks after I had turned 18. English class with Ms Marshall. I don't remember what we actually done in class that day but I just wanted to go home and do something that wasn't schoolwork like everyone else. "Could you wait behind please. I need to see you about your homework." Damn, I just couldn't catch a break. Now I had to stay for five minutes to hear a lecture about putting in more effort. Bell rang. Everyone left. I put my jacket on, stood up and walked up to the front desk. Ms Marshall waited until the last person left and she closed the door after them. She then turned the lock, which made me panic a little that I was in real trouble. "I'm going to ask you a question. And I want a straight answer." Here we go. The usual teacher talk about how you're a an intelligent student that could achieve a lot but you just aren't putting in enough effort. "Have you ever masturbated about me?" Time froze. My heart started racing with panic. I was something of a late starter when it came to females and beyond a first kiss at a party a few months back I didn't know anything about talking to women. "What?" I stammered back. "Have you ever masturbated about me?" She asked again, hands on hips. Ms Marshall was my English teacher. She would have been in her late 30s, maybe pushing 40. Something of a trophy-wife look about her - too much heavy make-up, bright red lips, platinum hair in a bob, neither slim nor fat but with a large chest for a woman her size. She was wearing a white business suit jacket and a short skirt with high heels. "No, Miss." Now that was a lie. I went through a phase of jerking off about Ms Marshall a couple years earlier, mainly alternating between thinking about sucking her tits and her giving me a blowjob afterwards, but I had since moved on to younger models like 20-something French teacher Miss Whitton. "Well I'm going get you to. Right now. Sit up onto my table." To say that I was in a panic would be an understatement. I didn't know what to do or say so I simply complied. I sat on the end of the table and wondered what was happening. "Lie down, and relax for a moment." I awkwardly turned and lay down, staring at the ceiling. My heart was about to smash through my chest and I had that a terror feeling in my stomach. I turned and looked at Ms Marshall -- she was looking at me with a stern facial expression. This was actually happening. Was I being punished for something? "I bet you have masturbated about me. I can see it in your face. You are going to do it in front of me right now. Pull your pants down." I loosened the top button and shuffled them down my thighs a little. I looked at Ms Marshall's ample chest and wondered if I was going to get to touch a woman's breasts. This did little to help my panic. "Start. Keep your boxers on, do it through them. Tell me when you are about to finish." She was still just staring at me with her hands on her hips. I stared up at the ceiling and slowly brought my hand down to on top of my boxers. Nothing there. I was too nervous. I turned and looked to her again. "Look at my tits, and start." I couldn't believe my ears. There was something shocking about hearing a teacher talk like a girl in of a porn video. I gripped my cock and started pulling through my boxers. I stared at Ms Marshall's chest and after four or five strokes was getting hard. "Good boy. Now keep going." Now THAT was more of a turn on than any extreme thing I'd ever seen on the internet. This WAS really happening, and I was going to have an orgasm in front of a woman who wanted to see it. I sped up, as if it was somehow showing off. I imagined her ripping open her shirt and breastfeeding me, and quickly realised I was in trouble. I started flexing my feet to diffuse the building tension. "Make yourself cum." Now I could normally make a session in front of the computer last a good fifteen minutes of stop and start, but this was a whole new culture shock. I was on the brink after about twenty seconds and she knew it. I started to hold my breath and let out a squeaky sigh of pleasure. I was past the point of no return and was actually going to cum in my underwear in front of my English teacher. I suddenly panicked, what was I actually meant to do? Just squirt it all out? Should I look at her or back at the ceiling. I held a strong grip and stopped for a second as the sensation built. "Go on, do it, and keep pumping till you've squirted every last drop out." My whole body shook for a second, one more tug and I came. I let out a moan as I felt the hot cum run out onto my legs. My hand was quickly damp as the wet patch on my boxers grew. "Good boy. Get it all out." The orgasm was over and a new wave of panic set in. What now? Reality came back -- I was lying on my English teachers desk having just cum in my pants in front of her. She firmly placed her hand on top of mine and mashed the cum into my groin. It was warm and sticky and having a woman's hand that close to my cock was nearly enough to make me cum again. "Pull your pants back up. You can go now." I didn't know where to look. I quickly gathered my things. "Come back here tomorrow. I have chosen you as my subject for an experiment. You're going to experience a lot. Don't tell anyone about this." TO BE CONTINUED... Detention with Ms Marshall - Day 02 Day 2 I'd been checking my watch constantly all day. Desperate for the school day to end, but not for the same reasons as everyone else. I spent most of last night in a combination shock over what happened and excited fantasizing about what might happen next. I masturbated three times thinking about what Ms Marshall was planning to do to me. She would probably be naked when I entered, oiled up and commanding me to fuck her as hard and quick as I could. Maybe she would get me to cum on her face at the end like in practically every porn video I watch. 3:30, finally it was time. Nerves were creeping up on me again, but I felt I was ready for this huge step into manhood. I knocked on the door. "Come in." She was marking work at her desk in a blue business suit. No smile. Serious. "Take a seat." I sat down. She quietly put away the work and locked the door. She turned back to face me. "You're in trouble." This seemed deadly serious. My excitement turned to panic. Was she going to tell everyone -- my parents included -- what I did on her table yesterday? "You made a mess on my desk, now you're going to have to be punished for it." I still couldn't tell if this was part of a game or I really was in serious trouble. She pulled out her chair to the centre of the floor and sat on it. "You will be spanked for your misbehaviour." Yes! I smiled, nodded and stood up. "GET THAT SMILE OFF YOUR FACE. HERE, NOW." A teacher shouting at you, under any circumstances, will strike fear into you and this was no different. With my heart in my mouth, I approached her. "Drop your pants and boxers. Lay across my lap." Her stern commands immediately went straight to my cock. I was suddenly too embarrassed to lower my boxers and display my semi-erection. "Miss, I can't right now." She looked at me and could see the bulge. "I'm not going to ask you again. Take down your boxers. Now." I gingerly lowered them. She did not seem impressed by my now raging erection. I manoeuvred around into position and went to lower myself down. I had never been this physically close to a woman -- her breasts were right there only an inch from me under the suit. "Don't you dare look at my tits. This is a punishment. Down, now". I gulped with fear and nodded. I carefully started to lower myself down. I was worried as to where I was going to put my erection but then noticed it had disappeared again with nerves. I lay on her lap and stared at her left shoe. I had never really had a foot fetish but at that exact moment her black heeled shoe was the most erotic object in the universe. My cock quickly grew again, flat against my stomach and her skirt. "I can feel that. I did not give you permission for it. Place it between my thighs." I reached down with my hand and wedged it downwards against her left leg, pointing at the floor. She squeezed her legs together and clamped my throbbing cock in place. I put my hand back on the floor. "Now, I will spank you ten times. Say thank you after each one." CRACK! It was like an electric shock through my whole body. "Thank you, miss." I wanted to grip my hand on her shoe but feared getting into more trouble. CRACK! Again. The automatic thrust made me pump my cock between her thighs. Oh no. CRACK! I inadvertently thrust down again. OH NO. I was going to cum over her legs. "Miss, I might cum." I grimaced, awaiting the next smack as I continued to stare at her shiny shoe. SMACK! "Don't you dare. This is a punishment." CRACK, CRACK, CRACK. Three in a row, I started to feel the contractions, there was nothing I could do to stop it now. I considered standing up and running to the sink to finish out over there. "Miss, I'm going to come." She widened her legs again so that my cock was not touching them. "BAD BOY!" CRACK, CRACK, CRACK. I was trying to hold back with everything I had but I was a second from squirting. There was nothing I could do to prevent it now. "BAD BOY!" I reached back with my hand to cup the head of my cock but she grabbed my hand. I was helpless but to orgasm onto the floor there and then. I groaned and shuddered with the orgasm as she gripped my hand hard. "Look at the mess you're making." I looked back as I saw my writhing cock squirting three more hands-free strings onto the floor. The last one dangled off the end and didn't fall. She let go of my hand and I wiped it off. "Get up and put your clothes back on." She seemed furiously angry, I was shocked and embarrassed at what I had done. I carefully stood back up, terrified at getting an after squirt onto her skirt - thankfully I didn't - and pulled my boxers and trousers back up. I looked at her, she broke into a smile. "Good boy. I know now that you can follow my orders and also take a punishment. Come back tomorrow, we will do more." Was that my cue to leave? What about the mess. I didn't dare look down at it. "Miss, what about..." She raised her hand up to indicate I stop talking. "You do not ask me questions. You follow my orders. Take a good look at the mess you made, then clean it up." I looked down at the milky puddle an inch from her shoe. Without question, I would be masturbating about that later. I lifted two tissues from the box on her desk and mopped it up. "Put them in the bin, and go home." I didn't know why or how this was happening to me, but I didn't want it to stop any time soon. Tomorrow was going to be interesting. TO BE CONTINUED NEXT WEEK Detention with Ms Marshall - Day 03 Day 3 I'd been thinking about Ms Marshall all day. It was the only thing I could think about. What she might do to me, or get me to do to myself. I snuck to the toilets and jerked off an hour earlier to "buy myself some time" for later -- no more embarrassing incidents like yesterday. I was in her class earlier, but we didn't make eye contact. Still, all I could look at was the patch of floor where I shot my load. I approach the door. "Come in. Lock it behind you." A hint of a smile, she was definitely less intimidating than before. A black suit, jacket buttoned all the way up. She placed her hands to where her breasts were and nudged them upwards. "Have you ever touched these?" My heart skipped, this was it! I shook my head. "Well, you're going to be introduced to them right now. Unbutton my jacket." I couldn't believe this was actually going to happen. Five years of jerking off over porn, desperately fantasizing about what a woman's breasts would actually be like. I raised my shaking hand to her top button and undid it. I instantly realised there was no shirt underneath. I exposed a valley of cleavage framed by a red bra. Once the last button was undone she took the jacket off. "Squeeze them." I instantly complied. It felt great. The bra was silky and I ran my thumb over where the nipples were repeatedly until she took a step back. "Lie down on the table and get your cock out." She was smiling again, which eased my nerves. I sat up on the table, swung round and instantly grabbed my cock out. "Not yet. You've more tits first." I swallowed with excitement as Ms Marshall undone her bra. Her breasts were a good size, like ones in a porn video although they sagged down a little. She grabbed my hands and rubbed them over them. My cock was an iron rod. "Flick my nipples with your thumbs." I rubbed them crudely and they quickly became erect. I don't know if I was too rough with this, but she flinched away after twenty seconds or so. "Good boy, now would you like to suck on them?" Did I? At that moment it was the sole purpose of being alive. I nodded. "Say it." She turned stern again, and this only turned me on more. "Can I suck on your breasts, miss?" This power play made her smile. She pulled up a chair and sat down at the table. "Turn your head over here and suck on this one." She cupped her right breast in her hand. I turned and raised my own hand to it as well and sucked directly onto it. The first thing I noticed was the taste, or rather lack of. I don't know why but I had assumed there would be a taste but it was no different to licking any other piece of skin. "Enjoying yourself?" Thinking back to porn movies, I pulled my head back slightly and flicked the nipple with my tongue. She put her hand on the back of my head and pushed my back onto it. "Suckle on it like a baby. Back and forth." I panicked a little that I had done something wrong. I started rhythmically sucking quite hard, pulling her whole breast forward slightly as I rocked my head a little. Her nipple occasionally slipped down and I made a slurping noise. "Good boy, that's it. Now, I want you to masturbate while you suck my tit." This was going to be the greatest jerk off in the history of mankind. I eagerly started at a fast pace. "I want you to make a good mess. Don't worry about where to cum, just erupt it over your hand." Being spoken to was I done this was still too much to take. I sucked hard and started to approach the end zone. I let out a muffled gasp as she gripped the back of my head harder. "Come on, let it out. Shoot it everywhere." That clinched it. I started shaking as I felt it build. I couldn't see it, but I suddenly felt a warm jet land on my hand as I kept going. Then another, and another. A warm pool collected on my groin. "You're making a lovely mess." I slowed down and stopped, I let her breast go and gasped for air. "Let's clean this up." She grabbed a tissue, and wiped up the cum which I took a look at for the first time -- it was a MESS. She then took another and wiped the saliva around her nipple. "Trousers up, that's all for today. I want you to masturbate at least twice tonight about this experience. We need to work on your longevity." I nodded as I pulled my pants back up. I turned and left as she was putting her bra back on. I couldn't wait for tomorrow. Detention with Ms Marshall - Day 04 Day 4 I had taken Ms Marshall's advice and masturbated several times last night and this morning, not that I needed the encouragement after being breastfed by her. I was desperately excited for whatever lay in wait today. Was she going to give me a blowjob? Maybe I will get to cum all over her face like in a porn movie. Knock knock. "Come in." I hesitated for a second as I put my hand on the door. She sounded like she was in no mood for fun. Still, if she wanted to give another spanking with a sticky ending that would be fine with me. "Take a seat, I will be with you in a minute." I headed over to an empty desk. Ms Marshall was wearing a low-cut white top and a short pale-blue business skirt. She was also wearing shiny black heeled boots which went up to her knees, rather than her usual high heels. "Have you been masturbating like a good boy?" She asked as she locked the door. I've still not got over the idea of a teacher talking like this to me, and I felt myself starting to get hard. I nodded. "What were you masturbating about? These?" She lifted off her top as she walked over. I don't know if it was the type of bra, but her breasts looked even bigger today -- encased in two large blue holders. "Well?" I nodded and smiled. In actual fact, I had masturbated twice about sucking them, and twice about HER sucking ME. "I think you should do it again." She put her hands on her hips and looked at me, still with a stern expression. The sight of her looking slightly angry, but only in a bra and skirt, was practically too much to handle. I stood up to unloosen my pants and started to walk towards her to get ahold of her breasts with my free hand. "What do you think you're doing?" She snapped at me. I froze, pants around my ankles and a raging erection poking through my boxers. "I haven't finished giving my orders. I want you to get down at my feet and cum onto my boots." Okay, this was going to be different. I nervously lowered my boxers and kneeled down in front of her. I didn't dare look up her skirt, but I had to fight an instinctive urge to lick her thighs. "What are you waiting for. Get going." I looked down at her shiny black left boot and started jerking away. Little was happening. Perhaps I had overprepared for today, perhaps it was nerves. Either way, I was feeling the pressure. I looked up, she was looking right back at me, hands still on her hips. "Don't you dare flop on me. Pull harder. Grip my other boot with your left hand." I leaned over and hoped for the best. I grabbed ahold of her right boot around the ankle. The smooth, almost slippery, PVC material sent a tingle right down my cock and I started getting hard right away. I moved my hand around the boot, round to the heel and back, as I got a good rhythm going. "I thought that would work. Now, I want to see you shoot your load over them." Her command gave me a judder, and I realised that I would no longer need to worry about failing to perform. I sped up a little, and edged slightly closer to her. I looked up at her again. Still staring at me, but now with a slight wicked grin. I assume today was meant to be a punishment rather than pleasure, but I was feeling both. I juddered again and realised I was getting close to finishing. "Right, time to cum. Get it all out, and don't spill a drop." That done it. I started to feel an orgasm build, and I gripped hard on her boot as I suddenly realised I had no idea what to do next and I had no time to figure it out. Was I meant to cum over both her boots, or just one? Was I to deposit a careful pool on top of her foot or just blast streaks everywhere. I let out a little gasp of tension as I slowed down to buy some time. "Good boy, here it comes." One more wave and I would be done. I leaned in close enough that the end of my cock practically touching the tip of her left boot. I looked at the other boot rather than see what happened. I gave another tug and felt the cum rise up my cock. "Don't hold it back, let it out. NOW." The shock of her suddenly shouting at me again was all it took, I released my grip on my cock and felt a huge load rush out. I let out a little whimper as I felt the orgasm rush all the way down to my feet and back. I gave another tug and another load came out. I still didn't dare look. "You're making a real mess, look at what you've done." I finished cumming and relaxed slightly from the nicer tone of her voice. I hesitantly looked down to get a glimpse. I had shot three large loads that criss-crossed the top of her foot and ankle, and another one that had dribbled onto the toe. "I like a load of cum on my boots, you've been a good boy." I didn't know what to do or say, I was still on my hands and knees up close and personal with a load of my cum, which was starting to run off the boot and onto the floor. "If you were a bad boy I might have ordered you to lick it back off, but I think you've been good. Tomorrow you might get a reward. Get your pants back on." I stood back up and pulled my boxers and pants back up. She was still standing there, hands on hips, cum on boot. I took a quick look at it and then a glance at her breasts still encased in that blue bra. "You can leave now. I'll deal with the mess." I turned to leave. "One last thing. No masturbating tonight, I want you to have a big load waiting to get out tomorrow." There was absolutely no chance of me not doing my homework tonight. Detention with Ms Marshall - Day 05 Day 5 After what happened in Ms Marshall's detention yesterday, the only thing I could think of all day was what she would make me do next. It was the end of the week, Friday afternoon at last. While everyone else was going to race home when the bell rang, I only had one destination. Knock knock. "Come in." I entered the room. Ms Marshall was standing by table. It was cleared of all the books and papers. Sat at the end were two boxes -- one of tissues and one of disposable latex gloves from the science labs. She was wearing a navy blue business jacket that was already unbuttoned to show some cleavage. Yesterday's boots had been replaced by heeled shoes. "Pants down. Boxers down. Sit up on the table." My heart skipped a beat of panic. She seemed very serious and I had no idea what she had in store. "Quickly. I don't have all day." I complied, lowered my boxers to my ankles and shuffled towards her in a very undignified way. I was already hard from the excitement of the fact whatever she had in store, it would involve me cumming. I sat on the end of the table. She looked at me with disdain. "I gave you a task for yesterday. Did you manage it?" She had told me not to masturbate. I had failed. Nevertheless, I nodded and figured she would never know for sure. "I hope that's the truth. Now, move forward and lie down on the desk. Face upwards." I slid down the desk and lay on it, facing upwards as if awaiting a doctor's examination. The table surface was quite cold against my bare legs. I put my hands by my sides. "Have you ever had a woman touch your cock?" I couldn't quite believe me ears. I shook my head. My entire sexual history up until detention on Monday was a lifetime of jerking off. "Well, let's have a little feel around here." She slowly pulled out a glove from the box and pulled it over her hand tight with a snap. This was so slow and deliberate it had to be designed to turn me on. It worked. She then pulled out the second glove and repeated the ritual. My penis was like an iron rod watching this. My heart was about to burst through my chest. "Have you ever jerked off with a rubber glove?" She asked with a wicked grin. I had been stealing gloves from the science labs for this very purpose for years. Filling them with various substances from chocolate pudding to whipped cream to see what it would feel like. But I couldn't admit that to Ms Marshall. I shook my head. "Well, this is going to tingle a little." She grabbed my penis with her right hand. The shock of the sensation made me sit up and gasp. It was a much harder grip than I would use myself, probably similar to the grip of holding a tennis racket. She let go again. "Lie back down." I lay back again. My penis was throbbing with anticipation. "Tuck your hands under your ass. If they come back out, or you sit up, we stop and detention was over." I nodded and done as she said. There was no way I was going to blow this chance. "Now, we'll start again. This time with a little action." She gripped me again, and pulled me up and down three or four times at a slow pace. The grip was hard enough that her hand wasn't actually sliding up and down me, she was pulling my whole cock up and down with her hand. I gasped with the sensation -- no matter how elaborate a masturbation set-up you can have with props and everything, it doesn't compare to actually being stimulated by a woman like this. "How does that feel." I let out another gasp. Unless she changed things up this wasn't going to last long. Thankfully she stopped. "Now, do you like to play with your balls?" Before I could answer she grabbed them with the other hand and gently gripped and released a few times. It sent a tingle all around me. I knew if she started jerking me again while doing that things would be over in a flash. "Would you like a little of this?" I looked up and she pulled a little bottle of lube from her pocket. She squeezed a little onto her hand and looked at me with a grin. "This might be a little cold." She slapped it around my penis and twisted her hand up and down. The cold shock was replaced by the electricity of the lube stimulating the entire length of me. She was going up and down with a twist round the head, and it had me near the brink. I tilted my head to get a proper look at what she was doing, seeing the gloved hand slide around me was the greatest thing I had ever seen. She caught my watching and stopped again. "What did I say? Look at the ceiling until we are done. Last warning." I lay back down and stared straight up. But all I thought of was the image of her white gloved hands working me. "Because you were bad, I'm going to finish you off now. This is going to be fast and hard." I tensed up slightly from how angry she sounded and in preparation for what she was going to do. She gripped me hard and started roughly jerking me at top speed. "Cum for me. Cum for me right now." I could feel an orgasm on the way. She was pulling so hard and fast it didn't even really have time to build. I tensed up harder. "That's right. Cum." I started to feel the contractions of an orgasm but she was still pulling so fast that I started to erupt before the orgasm peaked. I felt a hot blast land on my and then more run down my penis. She didn't stop. "I'm going to give you a little extra for being bad." She slowed down and kept on pulling hard. I wasn't ejaculating any more but was still writhing from the orgasm. The head of my penis was starting to feel sensitive with each tug and I grimaced a little. "Just a little more, then you can go." She pulled another couple times and them my hand instinctively came up to reach at her to make her stop. She gripped the top of my penis hard and I shot up in a jolt with the pain. "That's for not doing what I said. Now clean yourself up and go." She was furious. I looked down for the first time and saw the mess. There was one blast on my stomach, the rest on her gloves. I grabbed a tissue as she peeled off the gloves and put them in the bin. I quickly pulled up my pants and stood up. "I was going to let you have a suck on my tits to keep you going over the weekend, but you're not getting your hands on them now." I had no response to that. I just stared at her chest. "You can leave now." I turned to leave. Had I blown everything? I wanted more. I opened the door when she called out for me to turn round. "Be back here on Monday. You have detention all next week." She had that wicked grin again. I nodded and closed the door behind me. In the corridor I gulped a nervous thought. What was going to happen next week?