Note: This story was dynamically reformatted for online reading convenience. >Sharon's Education by De Von Copyright(C) 2021 by De Von Chapter 1 My name is Sharon, but all my friends call me Cher. I was something of a party girl in high school, and had a reputation as a fun person to be around. I -(TM)m 5 -(TM)4 -, naturally light blond, in great shape with 32C breasts and a pretty face, so I -(TM)ve never had a problem getting dates. The problem was I would go out with guys, and even make out with them, but I didn -(TM)t let them in. At 19, the biggest thing I had ever had inside me was my own fingers. My brother is 3 years older than me, and a couple of years earlier when the high school guys began to pass me by for girls who would put out, I went to him for advice. -Look Cher, - Brian had told me, -You can -(TM)t get a guy all hot and bothered and then just leave him cold. We need some relief when we get all worked up. If you -(TM)re just calling it off at that point then that -(TM)s why the guys are avoiding you now. - -So what do I do? Use my hand on a guy? Do I just stroke up and down until he squirts? How long will it take? - All the questions came out in an embarrassed rush. -You can, and the guys will like that, but they -(TM)ll like you more if you use your mouth. - I just sat looking at him, waiting for more. Some sort of explanation. I was really pretty clueless at that point. Brian just looked at me. -Oh hell, - he sighed, -you don -(TM)t have a clue what I mean, do you? - I blushed fiercely as I shook my head slightly and tears vegan to well up in my eyes. Just then Mom shouted from the kitchen, -I -(TM)m going to Sam -(TM)s. I -(TM)ll be back in a couple of hours. Either of you need anything? - -No thanks! - Brian replied. -Dr Pepper! - I yelled down the hallway. -Oh sure. Never have too much of that! Unload the dishwasher before I get back. And feed the dog. - -Ok Mom! Will do! Be safe! - Brian and I just looked at each other as we heard the door close and then Mom -(TM)s car start up and drive away. -How do I do that? - I asked, after the sound faded. -Go in Mom and Dad -(TM)s room, look in the second drawer under the shirts and bring the toy back in here. - -Toy? - I said hesitantly. -You -(TM)ll know it when you see it. Go. - I walked down the hall into Mom and Dad -(TM)s room and over to the chest of drawers in front of the bed. I didn -(TM)t go in there often, and certainly didn -(TM)t go thru their stuff. I quietly opened the second drawer and gingerly lifted the T Shirts, as if I was afraid they would somehow magically know. I still didn -(TM)t really know what I was looking for, but my eyes fell on a very lifelike dildo as I moved the shirts out of the way. I swallowed hard and reached in with one hand to pick it up. It had an interesting feel in my hand, and I turned it over and examined it. -Today would be a bonus, unless you want mom to catch you with it, - Brian called from the other room, breaking my reverie. I put the shirts back and took the rather lifelike, to me anyway, rubber cock to Brian -(TM)s room. -There -(TM)s a pretty big gap from kissing and letting a guy feel my boobs to this, - I said, holding the dildo in front of me. -How do I bridge that gap? - -I can -(TM)t believe I -(TM)m doing this, - Brian muttered. -Give it here. Now sit down next to me, like I -(TM)m your guy and you -(TM)re sitting center in my truck. - I sat on the side of the bed next to him, feeling kind of weird. He put his arm around my shoulders and turned me slightly to him. -Ok, so we -(TM)re parked and making out. - He laughed at the look on my face then. -Pretend, silly girl! Pretend. You really are blond. - I giggled and relaxed some. It was his standard joke for whenever I showed my naivety. -So you already said you -(TM)ve let them feel your boobs. You ever feel them up in return? - -A couple of times, on the outside of their jeans. - -Ok. So you have a little experience. Give me that towel. - He pointed to his shower towel from the night before, hanging on the bed post. I took it and handed it to him. -So, these are my jeans, - Brian said. He put the dildo on top of his crotch and covered it with the towel. -Get the point? This is so you can pretend and practice. - I nodded. -Ok. - -So I -(TM)m your guy, and we -(TM)re making out. Turn this way. So I -(TM)m copping a feel on a boob. - He held his hand up in front of me. -So now you start to explore more downward. - He took my hand and put it on his stomach. I noticed he was holding the towel and dildo with his other hand. He pushed my hand downward slowly, over the towel, until I reached the bulge of the dildo underneath it and he let go of my hand. -Keep going. - Brian said simply. He turned my head so I was facing him, rather than looking down where my hand was. -Remember, we -(TM)re making out, so you can -(TM)t see. Move your hand by feel. And close your eyes, unless you -(TM)re that rare girl who kisses with her eyes open. - I shook my head and closed my eyes, then swallowed hard as I let my hand side down over the dildo. I was relieved when I felt Brian -(TM)s hand on mine, guiding my movements. -Move up and down slowly, like this, - he said, moving my hand up and down the towel covered dildo. -Your guy is going to be responding now, maybe moaning or moving his hips. Oh yeah, baby. That sort of thing. That -(TM)s how you know it -(TM)s time for the zipper. Course, this towel doesn -(TM)t have a button and zipper, so pretend. - He moved my hand up above the dildo. -Here -(TM)s the button. Undo it. - I worked my fingers like I was unbuttoning my own jeans. It seemed pretty natural. I reached down and held a piece of the towel, then slid my fingers down, like I was pulling down a zipper. -Now you -(TM)re getting it, - he said. -Now you -(TM)ll probably find his undies still covering it up. Start stroking him up and down again. - I moved my hand up and down the dildo, outside the towel again. -They -(TM)ll be elastic, so you -(TM)ll have to work your fingers under the band. - I noticed Brian was holding the edge of the towel. When did he move his hand off of my shoulder? I slid one hand under the edge of the towel and felt the head of the dildo. -Keep going, - Brian said. I didn -(TM)t realize I had stopped. I slid my hand down the length of it and back up again. -Ok, you can look now. I -(TM)m going to show you some things. - I nodded. Brian moved the towel away. He held the dildo by the base, in about the same spot as his cock. -So move up and down with your fingers wrapped lightly around it. Pause a little around the head, right below where it meets the shaft. - I did as he said, and he continued to guide me for a few minutes. -After a bit, you break the kiss, and kiss his neck and down his chest now. - He gently pushed my head down as he said this. I turned my head toward him and put my hand on his chest, moving it down in place of my lips. -He -(TM)ll know what you -(TM)re doing now, and he -(TM)s getting excited. You -(TM)ll probably be able to tell. He might flex his hips. - He did then, pushing the dildo up in my hand. -At some point he -(TM)ll encourage you. -. I felt his hand on the back of my head then, gently pushing me down until my lips bumped the tip of the dildo. -Open your lips and slide it in, but be careful of your teeth. It -(TM)s kind of tender. Wrap your tongue around it and suck gently as you move down. You can gently stroke his balls, or put a hand on the base of you want. Move your head up and down, your lips from the head down the shaft and back. - I put my hand over his then, holding the dildo in place as I practiced sucking up and down it. It was a smooth, natural motion for me, and I enjoyed it. I liked the feel of it in my mouth. I was really glad Brian was patient with me. He had always been my guide in life. -Slide down and take in all you can, but be careful not to gag. You don -(TM)t want to puke on him. - I could feel him grinning at me. I nodded my head and moved down again. I moved my head gently in circles, taking my first cock, even though it was a fake one, in deeply. Before I knew it, my lips touched my fingers at the base of the dildo. -Damn it, girl! - Brian said from above me. -You deep throat a guy like that and he -(TM)s gonna be in love! - I giggled then, backing up quickly. -It just seemed natural, - I smiled. -That -(TM)s good, - Brian said. -But was it an accident? Do it again. - I leaned down and took the dildo balls deep in one smooth motion, sucking it into my throat repeatedly. For some reason, it made me incredibly excited and I was breathing hard. I could feel my juices soaking my panties. -It won -(TM)t take much of that and your guy will be ready to squirt, - Brian said. -Any reservations with that? - -No. I guess not. I -(TM)ve never been that far before. - -Ok. You -(TM)ll feel him get really hard, and it will swell up and you -(TM)ll feel him flex before the first squirt. You can hold the head in your mouth and stroke the shaft with your hand as he comes. He -(TM)ll squirt several times, maybe 6 or 7 even, before he slows down. Ok, you -(TM)ll have to pause a minute. I know you -(TM)re my sister, but this has ME all worked up, and I -(TM)m uncomfortable. - With that he moved the dildo and towel to one side and I watched in semi slow motion as he slid one hand into his jeans and adjusted himself. I could see the bulge of his hard cock thru his jeans as he turned back to go on. -Sorry. I couldn -(TM)t take it anymore. Anyway, he -(TM)ll squirt several times, - Brian went on before I interrupted him. -In my mouth?!? What if I don -(TM)t like it? What -(TM)s it taste like? - -My girlfriends say it tastes salty, but that -(TM)s all I know. If you don -(TM)t like it, just open your mouth and let it slide out. Then next time you can pull back just as he starts and finish him with your hand. But if you like it, or are at least ok with it, then he will love it if you swallow it down. Some girls swallow each spurt as it comes out, and some catch it all and then swallow. How is up to you. - -So what -(TM)s it like when that happens? - I asked, in my innocent curiosity. -I dunno. Never sucked a dick before. I -(TM)m always the suckee. - He laughed as he finished. -Ha, ha. - I said. -How -(TM)s a girl supposed to figure that out? - -Guess you just have to experience it, - Brian said. -I -(TM)m sure any guy you -(TM)re with will be more than happy to come in your mouth so you can see what it -(TM)s like. - He laughed. -Yeah, but what if I -(TM)m embarrassed? I -(TM)ll look like an idiot! - I pouted. I looked down, embarrassed, and my eyes fell on the bulge of Brian -(TM)s hard cock under his jeans. Before I could really even think about it, I reached out and popped the button on his jeans and pushed the zipper down in one smooth motion. I slipped a hand into his briefs and wrapped my fingers around his shaft. It was much warmer than the dildo, and felt softer, even as it was rock hard in my hand. As I pushed his briefs down and lowered my head toward it, he stopped me. -Cher? What are you doing?!? - -I want to experience it without being embarrassed. I won -(TM)t tell anyone. Please? - I looked up at him, pleading with my eyes. I could hardly believe what was coming out of my mouth. -Besides, are you really going to tell me you would object to getting sucked off by a hot girl? - -You -(TM)re my sister! - Brian said. -I mean, yeah, you -(TM)re hot. But you -(TM)re my sister. - -Relax, - I said. -It -(TM)s not like you -(TM)re gonna fuck me, and like I said, I won -(TM)t tell anyone. - I gently pulled his hands away from my head then and leaned down, inhaling the scent of him as I got close to his cock. I hesitated then. Was I really about to suck my brother -(TM)s cock? It was now or never, I decided. I opened my mouth and sucked the head of his cock in. It tasted faintly salty, and the texture was similar to the dildo, but different at the same time. I heard Brian gasp as I slid my mouth farther down his hard shaft. I worked my head up and down for a bit, but the position I was in wasn -(TM)t really comfortable. I paused and moved from where we had been sitting on the edge of the bed to kneel in front of him. As I did he raised his hips and pushed his jeans down to his knees, completely freeing his cock and balls. I moved forward then, taking him in one hand and guiding the head back into my mouth. I slid smoothly down his shaft until my nose pressed against his skin. Brian moaned as I worked my throat around his cock. I softly caressed his balls with one hand as I sucked him. Brian -(TM)s hands were on my head now, guiding me up and down his shaft. -Damn, you -(TM)re good at this! - Brian said. -If I didn -(TM)t know you -(TM)d never done it before, I -(TM)d never believe it. I -(TM)d swear you were lying to me. You -(TM)re an absolute natural! - I smiled to myself as I kept on sucking his cock, taking him deep again and again. Brian moaned and gasped, -Oh Cher! I -(TM)m gonna come, Baby! Get ready. I -(TM)m gonna come! Here it comes Baby! Aaaah, AAAAAAHHHHH! - he groaned loudly as his cock swelled and a powerful blast of semen pulsed into my mouth, hitting the back of my throat. It surprised me and I almost choked, but swallowed quickly, just in time for the next blast to fill my mouth. It had a strong, salty taste. Different, but not unpleasant. I held still and stroked him with my hands as he squirted more come into my mouth. Jet after jet shot out of his cock as I stroked him. I was surprised at how much there was. I swallowed a couple of times as he slowed down and finished. I closed my lips around the head of his cock and gently sucked as I pulled back and sat looking up at him. -Wow! That was incredible! One of the best blowjobs I -(TM)ve ever had! - Brian said. -It Was incredible! - I smiled. -Much better than I ever would have thought! Thank you for letting me do it. For being my first. I won -(TM)t tell anyone! But I -(TM)ll never forget it! - I stood up then, leaned forward and kissed him, squarely on the lips, before hugging him tightly. -I love you! - I turned and left the room quickly, my mind still reeling at what had just happened -- Chapter 2: Learning to Cover Your Bets Sharon gets a lesson in what happens when she makes wagers she can -(TM)t cover. She finds a way, but it costs her something precious. After that first time with Brian, I sucked a lot of cocks. I really enjoyed the feeling of power I got sucking a guy off, and I loved feeling them flex and pulse as they came down my throat. My dating life quickly resumed. The guys didn -(TM)t even care that I wouldn -(TM)t let them fuck me, as long as I sucked them off. And none of them every complained about coming in my mouth. :) The summer I graduated, I had just turned 19 and was at a party Brian -(TM)s fraternity was hosting. There was a guy there named Brad. He was sort of standoffish, a little bit of the bad boy type. I found him exciting. -He likes you, - Brian said from beside me as I poured myself a drink. -But be careful with him. He -(TM)s strong willed. Don -(TM)t get yourself in a compromising position. - -Would he...? - -No. He won -(TM)t force you, if that -(TM)s what you -(TM)re asking. If you tell him to stop he will. But if you don -(TM)t he might not, so if you get to that point just be clear with what you will allow. - -Ok. I -(TM)m pretty good at handling that. - I replied. -But I do need your help with something. - -Name it, - Brian replied. -I made some stupid bets, and I owe some money to a couple people from school. Well, one guy in particular. And now he wants me to pay up this weekend. One way or the other. I don -(TM)t have the money, and I certainly don -(TM)t want to fuck him, but I -(TM)m running out of time. - -Shit, I spent everything I had on my car yesterday, - Brian said. -How much do you need? - -500, - I replied. -Damn! You need to stay small time, Cher. Brad -(TM)s the only one of us who would have that on short notice. Be sweet to him this evening, then ask him nicely and he -(TM)ll let you borrow it, I -(TM)m sure. - I smiled. -I -(TM)m pretty good at persuading guys to do what I want. - -Just remember, be careful. - -Always! - I laughed as I skipped away in search of Brad. After I found him, we danced and drank most of the evening. I was careful to regulate our drinks, so we were relaxed but not drunk. As a particularly slow song ended, I looked up at Brad and smiled shyly. -Let -(TM)s go somewhere quieter. - He nodded and we went to the back of the house, where there was a separate sitting room. It was empty, and Brad closed the door behind us. I melted into his arms and he kissed me softly. I lingered in the kiss awhile, enjoying the feel of his body next to mine. I broke the kiss and approached the subject of my debt, telling him the story briefly, including my offer of several blowjob -(TM)s, which was turned down, before asking if he would loan me the money. -I don -(TM)t want him to be my first fuck, so I have to find a way to pay him. Can you help me? - -Well, I don -(TM)t make loans, - Brad said. My face fell. -But since you -(TM)re a betting girl, I -(TM)ll make a wager with you. - My stomach fluttered. -What kind of wager? - I asked softly. -Well, I -(TM)m intrigued by your oral talents. And since I -(TM)m a guy, I love a good blowjob. - I was starting to like the direction this was going. -Ok. I -(TM)m game. What -(TM)s the bet? - -You agree to suck my cock, and if you can make me come in three minutes, I -(TM)ll loan you the money. - Three minutes! That was forever to me. If I just wanted a guy to squirt, I could be swallowing 30 seconds after my lips touched his dick. This was going to be easy! -And what if you can hold out for more than three minutes? - I said, though I really doubted that would happen. -We -(TM)ll deal with that if we get there, - Brad said. -So what do you say? You in? - I slid a hand between us and groped his cock. I could tell it was a nice size, even thru his pants. -Sure! I -(TM)m going to like having this in my mouth, - I smiled as I stroked him and felt him growing hard. -Just one condition, - he said. I cocked my head to one side and raised my eyebrows. -I get to see you naked. - Brad smiled. -No touching without permission. Just because I get naked doesn -(TM)t mean anything is going to happen. - I replied. -Deal. - Brad said. -Take it off slow for me. - I backed up a couple of steps and started a slow striptease. I took my time undressing, but soon stood naked before him. I reached and unbuttoned his pants then, freeing his cock from its restraint. It was a nice size, as I had surmised. Brad pulled his shirt off and dropped it on the floor as I leaned forward. He pulled his phone out of his pocket. -You ready? I -(TM)ll start the timer when you start. - I nodded. -I -(TM)m ready. - I leaned forward and he hit the start button as I sucked his cockhead into my mouth. I figured I would play with him a bit before I made him squirt. I licked softly around the head of his cock before sliding slowly down the shaft, stopping when I felt him touch the back of my throat. I didn -(TM)t want to give away all my talents up front. I stroked slowly at first, keeping an eye on the timer on his phone. A minute had passed already. Time to get down to business. I really wanted to take my time and pleasure him properly, but I figured I -(TM)d get another chance to do that. I sucked him in completely then, pushing his cock deeply into my throat and working him with my tongue while caressing his balls with the other hand. It wouldn -(TM)t be long now. It never was, when I started deep throating them in earnest. He wasn -(TM)t moving as fast as I wanted, and the second minute was ending. I let some spit drop onto my hand at the base of his cock, then slid the hand upward and caressed his ass. That almost never failed to make guys come in my mouth, but still he didn -(TM)t squirt. I slipped my finger into his ass then, waiting eagerly on the reward I knew that would bring. Instead of his warm juice in my mouth, I heard the beeping of the phone as my 3 minutes expired. How had he held out that long? No guy had ever been able to last 3 minutes when I really wanted him to come. I felt Brad -(TM)s hands under my arms, and released him as I stood up. He kissed me passionately. -Nice effort, - he smiled. -I thought you were going to get me with that ass play. - -Me, too, - I replied. -What now? - -~Well, I think sucking my dick got you more excited than it did me. If it didn -(TM)t, and you -(TM)re not soaking wet, I -(TM)ll GIVE you the money and we -(TM)ll get dressed and go back to the party. - -And if you -(TM)re right? - I asked softly. -A bet -(TM)s gotta have two sides. If I -(TM)m right, and you -(TM)re soaking wet, I get to fuck you. Right now. I -(TM)ll still give you the money, though. Deal? - I couldn -(TM)t really say no, since I owed him from the original wager. I already knew the answer, but I hoped he would give me a break. I swallowed hard and just nodded, unable to say it out loud. Brad stepped closer to me then and put one hand between my legs. -No fair! I -(TM)m 19. I -(TM)m always wet. - I said with a pouty look that I hoped would gain me sympathy. I shuddered and gasped as his hand touched my soft center and his fingers slipped between my slick outer lips and quickly became coated with my juices. -Mmmm. So it seems, - he said. He took a half step back, and I wondered what he would say next. He surprised me by grabbing a handful of my hair and pulling me backwards, not hard enough to hurt, but just enough to pull me off balance. I yelped as I went down, landing on my back on the futon I had been standing next to, my legs flying into the air. Brad caught my legs in his hands and stood between them, his hard cock sticking out in front of him. He lifted up on my legs and pulled me to the edge of the futon. Then he went down to one knee, which put his cock even with my wet, virgin pussy. This was not how I had envisioned losing my virginity, but I guessed there were worse ways, if he truly intended to go thru with it. And it seemed he did, as he took his cock in one hand and rubbed it up and down my slit, coating the head in my juices. I looked up at him, my breathing ragged. -For real? You -(TM)re really going to fuck me? - Brad smiled. -A bet -(TM)s a bet. Unless you don -(TM)t want me to. Are you going to tell me no? - I was still breathing hard. I couldn -(TM)t believe this was about to happen. I shook my head. I wasn -(TM)t going to tell him no. I had made the bet, and if he wanted to fuck me, I would let him. He pressed the head between my outer lips and nestled it at my opening. It looked so big there. I wondered if I could handle it. I wasn -(TM)t completely tight. I had broken my hymen with a finger several years before, and I routinely rubbed and fingered myself, but my fingers were nowhere near as large as Brad -(TM)s considerable cock. My legs were in the air, my ankles on his shoulders. -~He -(TM)s really going to do it. He -(TM)s really going to fuck me. -(TM) I thought. Brad grabbed my hips and pulled me toward him as he pushed forward then. -Guh! Aaaaaahhh! - I cried out softly as his cock sank into my body. He went completely into me in one smooth thrust. I had been right. His cock was by far the largest thing that had ever been inside me, and oh fuck! It hurt! Brad wasn -(TM)t moving. He was looking down at me as I bit my bottom lip and struggled to adjust to the feeling of insane fullness I felt at having a hard cock inside me for the first time. It was a bit of a struggle, but I kept my legs open, even though my first instinct was to close them against the invader that was filling me up. I was beginning to adjust to having him inside me, at least a little. -You good, baby girl? - I realized my eyes had been closed. I opened them and nodded up at him. -Yeah. I -(TM)m ok. - Brad drew back and thrust into me again, drawing another soft cry from my lips. I was moaning steadily now as he thrust in and out of me repeatedly. His cock was still uncomfortably large in me, but it didn -(TM)t hurt as bad now that he had established a nice, slow rhythm. I still felt insanely full, and was amazed that all of his cock fit inside me, but it did. He pulled out of me then, and I felt him slip his hands under my arms and pull me farther up on the futon. Brad climbed up on top of me then and I parted my legs to accept him again. He lined up and sank balls deep into me again, holding his weight off me, but still maintaining full contact between our bodies. He began flexing his hips and rocking his cock in and out of me. I was still very full, and it still hurt, but it was manageable now. I wrapped my arms around him and just held on. I laid my head back on the futon, my eyes closed as Brad slowly fucked me for the first time. I was gasping and moaning steadily as he stroked me. After a while, I became aware that Brad was saying something to me, but it didn -(TM)t register. I shifted my focus from the big shaft between my legs to Brad -(TM)s face as he looked down at me. -Huh? Wha? - -I was asking if you -(TM)re on the pill. - -No, why? - I asked in my dazed state. I hadn -(TM)t even considered the ramifications of him coming inside me. I hadn -(TM)t planned on getting fucked anytime soon, so I -(TM)d never worried about birth control. -Well, because I love fucking your tight pussy, and the only thing I -(TM)d love more would be filling it up with my hot come. But the last thing I need is to knock you up, so I guess we better figure out another way. - Realization dawned then, and brought a touch of panic with it. -NO! No! - I shook my head vigorously. -Don -(TM)t come inside me! Please! Please don -(TM)t come in me! Don -(TM)t make me pregnant. - -SHhhh -, Brad whispered. -I -(TM)ll take care of you. I won -(TM)t make you pregnant. -. He pulled back then, raising up and turning me onto my side before straddling my leg and entering me again. He spoke again as I felt his cock filling me up once more. -I DO want to come inside you, but I -(TM)m gonna go down your throat instead of up in you. - I nodded slightly as he began stroking his cock into me again, faster now. He was holding one leg straight up, and had grabbed my arms and was pulling me to him with each thrust. I was moaning again as he fucked me steadily, thrusting into me again and again. I began to wonder how much more of this I could take. I was completely his now, and he knew it. He could do whatever he wanted with my body, and I would let him. I could feel his thrusts growing ragged and hear his breathing changing now. I knew he was getting close, and it felt like he had decided to come in me, after all. I wondered what it would feel like; if I would be able to feel his come blasting into me the way my girlfriends claimed they could. I was waiting to feel him swell and pulse when suddenly he pulled his cock out of me. Dropping my leg, he pulled on my arms, drawing me close to his body. I felt him grab my hair and pull and I opened my mouth just in time as he thrust his cock into my throat and came, spurt after spurt of his hot semen filling my mouth. I closed my lips on his cock and managed to swallow most of his come as he held my head and finally finished. I sucked on him gently as he pulled back and let go of my hair. I rolled onto my back, breathing heavily, doing my best to recover from my first fucking. -So, was it what you thought your first time would be like? - -Not exactly, - I replied. -Actually, not at all. No. Nothing like I thought my first time would be. - -So how was it? - Brad said with a sly smile. -It was ok, - I said. -Not too bad. I -(TM)m sure next time will be better. - I gave him a slight smile. -Well, it was damn good for me! Thanks! Hope we can do it again soon. - I nodded. -Looking forward to it. -