Chapter 1: Mysterious Chat Friend
My name is Stephanie although everyone calls me Steph. I was only just 15 when this story started. I’m an orthodox Jew so I’ve been brought up in a very sheltered environment. We didn’t get told anything about sex, for example, but the internet is a friend and I’d managed to educate myself at least somewhat. My parents live out in the country and they decided that I should go to a better school, an all-girl’s orthodox school. The school doesn’t have any dormitories so they assign the girls from out of town to live with host families.
What I think of as the adventure started fairly soon after I arrived. The wife of my host family, Rachel, had been using the computer. I went to use it. Suddenly someone said “hi” on AIM. I didn’t reply at first since it was obviously one of Rachel’s friends and I wasn’t Rachel.
However, the person sent a second message.
“hi stephanie. i know that this is weird. rachel told me she had a new guest and she told me your name and your age. but that is all i know. i’ve chatted with several OJ teenagers. here’s the deal i make. i will answer any question you are brave enough to ask”
I wasn’t really sure if or how to respond. I had no idea who I would be chatting to. I was still wondering what to do when another message came in.
“i don’t even know if you are there but i’ll tell you a bit about myself anyway so you don’t feel threatened. my name is paul. you can check with rachel if you want to make sure i’m not a creep. i’m a long time chat friend of rachel’s although we’ve never met. i started as her escape valve from the OJ community so she could discover how the rest of the world worked. i live thousands of miles away so you don’t need to worry i might show up in person”
I wasn’t sure I wanted to chat but it seemed rude not to say something so I replied.
“hi. yes, i’m steph”
“rachel wanted me to chat to you since she found it useful to have at least one non-OJ friend. i discovered that there are lots of questions OJ girls want to ask but don’t dare ask anyone in the community”
“i don’t know if i want to chat but we can try”
“are you cute? my experience with OJ girls is that they don’t have a clue if they are attractive or not since they rarely meet boys”
I wasn’t really sure what he meant. “what do you mean by cute?”
“attractive. to boys. if we keep chatting and you get comfortable enough then one day you can send me a picture of yourself. i’ll give you a personal rating lol”
“ok. i’ll maybe send you a picture another time”
“i’m intrigued what you have learned about sex already.”
“i know plenty. but they do not teach it in school”
“you have the internet. and porn.”
“yes, i have the internet”
“have you ever watched porn”
“no, but i have seen some pictures”
“then you have a better idea than i did at your age as to how all the bits fit together”
“rachel is back and wants the computer”
So that was the first chat I had with Paul. I had no idea that it was the start of an adventure. Only the fact that he had asked me how much I knew about sex gave even a hint of what type of adventure it was going to turn out to be.
Rachel asked me if I’d chatted with Paul and when I said that I had, she gave me her password so I could chat to him whenever I wanted.
Paul started a course of education. He told me he wrote erotic stories and he sent me some. I couldn’t keep my hand out of my panties when I read them. Then he sent me some porn. A teenager auditioning for a porn movie where she had to strip and spread her legs and touch herself. A teenage girl sucking off an older man. I’d read about that sort of thing but seeing it happen…wow. Of course I immediately wanted to try it, not that there was any way for me to try. I had a mouth, but the other prerequisite was missing from my life. No boys.
Chapter 2: Flirting
The following Sunday I was at school in the computer room. I opened up AIM and logged in.
“hey”
“are you steph or rachel?” Paul replied.
“steph”
“we should have a way for me to tell since you are sharing an account. instead of saying hi just tell me the color of your panties”
“lol. ok. black today”
“are you alone?”
“no. there are other girls here. plus the teacher. there’s always a teacher.”
“is he hot?”
“lol. not bad”
“flirt with him”
“i haven’t a clue how. teach me”
“talk to him about movies. ask him what his favorite movie is. tell him you think some actor you like is hot”
“ok. back in a moment”
I logged out and went over to the teacher. I started asking some computer questions. Then I summoned up the courage to do it.
“Have you seen Jurassic World?” I’d seen it the previous weekend.
“No,” he said. “My wife and I might go on Sunday when the crowds have died down a bit. Is it good?”
“I enjoyed it,” I said. Then I took a deep breath. “I think Chris Pratt is hot.”
He laughed. “Does that mean you want him to kiss you?”
“That’s not allowed.”
“I know. But that wasn’t what I asked.”
“I’m not going to get into trouble if I say ‘yes’ am I?”
“No. You’re a teenager. Feelings like that are normal.”
“Then ‘yes’. I do want him to.”
He laughed again. “I’m afraid it’s not going to happen.”
I frowned. “I know. But it would be amazing. But so against the rules.”
I went back to my desk and logged back in.
“that was out there”
“did you do it?”
“yes. i asked him about jurassic world and told him I thought chris pratt was hot.”
“what did he say?”
“he asked if i wanted chris pratt to kiss me. i said i’m not going to get into trouble if i say yes. and he said no. so i said i wanted him to kiss me. then i came back here”
“brave girl. you lost your flirting virginity”
“the other girls left. there is just me and him. i want to go further”
“ask him which actresses he thinks are hot”
“ok. i’m going to leave but i’ll ask him on the way out”
I gathered up my stuff into my school-bag and walked towards him.
“So which actresses do you fancy?”
He laughed. “That’s a secret. But you look quite like Lindsay Lohan.”
“I don’t really know what she looks like.”
“You’re a smart girl. I’m sure you can find out. I need to lock up the computer room now.”
“OK. Goodnight.”
Chapter 3: Lindsay
I went back to my host family. Late that evening I logged in again.
“still black” I opened. I was still in the same panties as earlier, of course.
“how did your second flirtation go?”
“he said i look like lindsay lohan,” I said. “what does she look like?”
A moment later Paul had found a photograph. Not just any photograph. Lindsay with no bra on and her blouse open to her waist. Basically her breasts were on view, her nipples barely hidden.
“oh wow. do i look like that?”
“you see yourself in the shower. you’ve a better idea than i do. photo”
“lol. i’m not ready for that”
“are you alone?”
“yes. everyone has gone to bed”
“do you want to see some more porn?”
“ok”
“take your panties off”
“i can do that”
This time he sent me a link to some people having sex. Real sex. The girl was on her back with her legs spread. His cock was inside her. It’s not like I didn’t know how all the bits went together but seeing it like that was incredible. You could see everything. I never knew such stuff existed. Even my own forays onto the internet had only found pictures, they were tame compared with this. Of course I masturbated the whole time. It was fast, with the porn on the screen. It only took a few minutes before I came.
Somehow he seemed to sense it. “did you cum?” he asked.
“lol. yes.”
I was so aroused from the porn and the masturbating that I’d probably let the host father do me if he’d walked into the room. Then I had a thought.
“i want to go further,” I texted. “i’m going to show him that picture. ask him if he thinks i look like that”
“you go girl. but keep safe and don’t go too far too fast”
It was a couple of days later before my opportunity arose. I was in the computer room. He was there. The last other girl left. I was alone with him. I had the picture on my screen but covered with another window. He came over to chat to me, small talk really.
“So you think I look like Lindsay Lohan?” I said.
“Yes. But with black hair.”
“You think I look like this?” I uncovered the photo. I’d seen it dozens of times by then but it was still shocking bringing it up on the computer at school in front of my teacher.
He smiled. “She’s hot.” Wow, that means my teacher thinks I’m hot. I felt my nipples harden.
“You’d be OK if I dressed like that?”
“I don’t care how you dress.”
“Really. I wouldn’t get into trouble if I dressed like that. It’s against the rules.”
“It certainly is. But I promise I won’t get you into trouble.”
“Wow. Do you want me to? To…do Lindsay?”
“If you want to. I really don’t care how you dress.”
“Are you supervising the computer room next Sunday?”
“Yes,” he said.
Back home I logged in.
“pink today”
“nice”
I told Paul the whole story. Him as good as daring me to do it. Me as good as saying I would. Him telling me he wouldn’t out me.
“how do i do it?” I texted
“how do you mean?”
“well i can’t just show up at school as lindsay. lol”
“my suggestion. get dressed that day. no bra of course. the blouse already unbuttoned as far as you dare. then put a loose sweatshirt over the top. so it’s not obvious”
“my breasts are not small. but i guess it’s not that obvious”
“keep the sweatshirt on while there are other girls there. then take it off”
“gosh this is getting me all worked up. just thinking about it. what’s going to happen?”
“i don’t know. probably not much. you’ll be shaking with fear and arousal. he’ll be looking at you. maybe he’ll come closer for a better look”
“i’ve never done anything like this. i’ve always been good”
“you’re a teenager”
“as if that makes it easier haha”
“are you touching?”
I felt a little like I’d been caught because of course my hand was up my skirt and inside those pink panties. How could it not be?
Chapter 4: Being Lindsay
The couple of days until Sunday dragged but finally the day arrived. There were several other girls at the computer room when I logged on.
“red”
“red panties for lindsay”
“lol. yes”
“are you dressed like her”
“yes. like you said. no bra. blouse half undone. loose sweatshirt over the top”
“are you going to dare to do it? or will you chicken out”
“i’m not chicken”
“are there other girls there?”
“yes. but they’re leaving”
“you’re alone with him. are you scared?”
“terrified”
I summoned up the courage to do it. I pulled my sweatshirt off over my head.
“it’s off” I texted to Paul.
“is he looking?”
“yes. he is coming over. should i log out?”
“no”
The teacher walked over until he was standing in front of me, inspecting me.
“Undo more buttons,” he said.
My fingers seemed to be under automatic control. Suddenly, without planning it, all my buttons were undone and my blouse opened completely. My breasts were on view for the first time in my life.
“Who are you chatting to?” he said as he stared at my breasts. I could feel my nipples going hard. He moved behind me and started to read the chat conversation I was having with Paul.
“he wants to know who i’m chatting to,” I typed.
“can he read the screen?”
“yes”
“i’m a friend. in california. her personal trainer. i would be touching her breasts if i was there”
“he asked if i want him to touch my breasts” I typed.
“of course you do,” Paul texted
Suddenly he reached over and grabbed my breasts and started to rub them. It was the most thrilling feeling. For some reason it seemed important to keep chatting to Paul.
“he’s touching my breasts. he told me to say i’m enjoying it”
Almost immediately I had what I think was an orgasm. It wasn’t like when I masturbate at all. More intense. My hands were still on the keyboard so I typed complete nonsense, I was way beyond being able to think.
“Dcvvgc cfcdsdedccfrdcccc Llllllllllllllllllllllllllllllllllllllllllll”
Once I calmed down he was talking to me again. I passed the message on.
“he told me to ask you if i’m ready to suck his cock”
“do you want to?”
“he wants your phone number”
The teacher walked to the front of the room and got his phone. By then Paul’s phone number was on my screen. He dialed Paul’s number as I got down on my knees and he opened up his pants. I got to see a cock in the flesh, as it were, for the first time in my life. It was shockingly big and hard. Thank goodness Paul had shown me those porn videos of girls sucking cocks so I had some idea of what I was doing.
“My cock is in her mouth,” I heard him say as I started to move up and down on him.
“Yes, she has fabulous tits.” I had no idea what Paul was saying, I could only hear my teacher. He started moaning into the phone.
“Oh, she’s a natural. She’s good.”
“Yes, she’s my first student.”
“I know. And you are a dirty old man for being her trainer.”
Although I had never seen a guy cum for real before I could sense he wouldn’t last long. Without warning he suddenly blasted into my mouth. I tried to keep it in my mouth but it dripped out onto my breasts too.
“I just came in her mouth,” he said to Paul. “You need to teach her not to spill any.”
He disconnected the phone and reached over and closed the chat window. We were alone. Suddenly I realized how out of control things had got. I was just going to let him see a little of my breasts in the opening to my blouse, not touch them, not orgasm, not suck him. Especially not with him on the phone to Paul at the same time. It was wild.
“You won’t tell?” I said to the teacher.
He laughed. “I think I’d get into a lot more trouble than you.”
“I guess. But I’m still scared.”
“Don’t worry. Did you know there is an apartment in the main building? I’ve got a key. We’ll go there tomorrow.”
“Gosh. Really? I suppose.” I couldn’t think to be honest. Given how out of control that afternoon had been, who knew what would happen next. It seemed very anti-climactic as we both did up our clothes, left and locked up the computer room.
Later that evening I went on the computer to chat to Paul.
“still red”
“I bet they are wet”
“lol. soaked”
“was it good”
“yeah. i still can’t believe it”
“i want you to go on the pill. it might not happen but it might. be prepared”
“ok. there’s a clinic near the school”
“when are you going to see him again?”
“apparently there is an apartment in the school. he has a key”
“better wear your best panties”
“why? i don’t think he is going to see them”
“i’ll have a little bet with you. three things. one, he’ll see them. in fact he’ll take them off. two, he’ll lick you, your pussy. three, you’ll have a huge orgasm. biggest of your life”
“wow. you really think so? it doesn’t seem likely”
“let’s see who is right. are you shaved or hairy?”
I paused. It seemed almost too personal a question. But I decided to answer anyway.
“hairy”
“shave for him. he’ll love that you did it for him”
I wasn’t quite sure how to do it exactly, but I’d seen shaved women in a lot of the porn and it definitely looked sexy. Even though I’m a girl. Using a razor out of sight between my legs seemed, if not dangerous, at least risky. I didn’t want to cut any of the stuff down there. But I did it that night and it turned out to be pretty easy. It felt really sensitive. Well, OK, when I masturbated. Which, of course, I did.
Chapter 5: The Room
That afternoon I went to the apartment with him. It felt good to have some privacy. Not to mention a bed. He put his arms around me and kissed me. My very first kiss. My whole body responded. I felt my nipples go hard, felt my pussy twitch with arousal. I knew I would be wet. I was sort of humming, almost vibrating with pleasure. His hands were on my ass, on my breasts, just stroking me everywhere. I was still dressed but it didn’t seem to matter. It was as exciting as when he had grabbed my breasts in the computer room. Much more happened. I told Paul about it that evening.
“white lace”
“nice. did you put them on twice today?”
“what do you mean?”
“did they come off in the room? so afterwards was the second time today you put them on”
“haha. yes”
“tell me the whole story”
“we got to the apartment. he kissed me. it was amazing”
“your first kiss”
“yes. it was wonderful. hard to describe. like it made me melt with feelings. he took my top off and unclipped my bra”
“and he played with your breasts”
“yes. except he insists on calling them tits. fabulous tits”
“did he make you suck him again?”
“yes. but first he did something else”
“he took your panties off?”
“yes”
“so you were completely naked?”
“yes. i’ve never been naked before. i mean with someone. you know what i mean”
“and he licked you?”
“yes”
“and did you have a huge orgasm?”
“i’ve never had one like it. it was all over my body. not just between my legs. i was shaking. my brain shut down completely. i couldn’t think. i might have passed out”
“so i’m three for three on my bet”
“were you ok being naked in front of him?”
“i suppose. it felt really odd. especially when he spread my legs”
“nobody has seen you down there before”
“no. he was surprised i was shaved”
“did you tell him i told you to do it for him?”
“yes. i said you told me he’d like it. he said you were right.”
“what happened then?”
“i was lying on the bed after my orgasm. like i was almost passed out. then he was naked too. his cock looked bigger than last time. a bit scary to be honest. he made me suck him again. but this time instead of kneeling in front of him he was lying on the bed and i was bent over him”
“how did you do when he came?”
“i didn’t spill any, if that’s what you mean. he made me open my mouth to show it to him and then swallow it”
“were you ok with everything?”
“totally. more ok than last time. it didn’t feel so out of control. i mean i sort of knew what would happen this time. i’m not stupid”
“whereas last time was a surprise”
“totally. i expected to show him my shirt half open and no more. i don’t know how i ended up with it completely open. then sucking him. i was in a daze”
“you’ll remember it for the rest of your life”
“for sure. he told me i was really good at sucking cock”
“lol. just what a 15-year-old orthodox jewish girl should be hearing”
“it’s unbelievable. i don’t know how it happened. you started chatting to me and a couple of weeks later i’m naked with my teacher’s cock in my mouth”
“what was it like being licked?”
“nothing like touching myself. soft but intense. hard to describe”
“you enjoyed it?”
“oh yeah. it was a bit embarrassing at first but i got over it lol”
“someone inches away from a part of your body that even you cant see?”
“yeah. i guess. where i pee”
“did anything more happen?”
“not really. after that we lay on the bed for a bit just kissing. then we put our clothes back on and went home”
So that became our routine. Once or twice a week I would go to the apartment with my teacher and we would kiss and lick and suck. He never tried to go all the way, he could sense I wasn’t that ready. But I did take the first step towards being ready: I went to the clinic and went on birth control. I thought it might be embarrassing but they pretty much knew why I was there.
“are you on the pill now?” Paul asked.
“yes. but…”
“but what?”
“i’m don’t think i’m ready yet”
“how will you know?”
“i don’t know. how would i? i guess one day it might just happen”
“haha. like you just accidentally get a cock in your pussy”
“you know what i mean. i didn’t expect to get a cock in my mouth”
“have you ever stuck your finger in?”
“where?”
“your pussy of course”
“yes. it seems tight”
“do you use tampons or pads?”
“tampons. so yes, i know where it is lol”
“what’ll you do if i tell you that you’re ready”
“i don’t know. get fucked i expect. do you think i’m ready?”
“yes”
Chapter 6: It Happens
It started like any other Friday. I went to the computer room. Paul was online.
“dark blue. they say ‘friday is my second favorite F-word’”
“i wish i could see”
“i’d be happy to show you if i could”
“i’d want to take them off. and F”
“i know. i might even let you”
“is he there?”
“yes. but there are other girls”
“you will have to wait for cream for your coffee”
“haha yes. but i want something else”
“some juice for his breakfast”
“exactly. oh, the last 3 girls are all leaving”
“unbutton your blouse for him”
“i’m going to have to go. he’s waving the apartment key”
“ok. have fun”
“bye”
He locked up the computer room and then we walked across to the other side of the school where the apartment was. He went ahead. I followed a couple of minutes later making sure nobody was paying attention to me. He opened the door. His arms were around me, his mouth on mine, his tongue urgently seeking mine. I love being kissed.
His fingers fumbled with the buttons on my blouse. I could feel the sense of urgency as he gradually stripped me.
“Cute,” he said when he got to my panties.
“I bought them specially for you,” I said.
“And what is the first favorite?”
“I’m only guessing I’m going to like it.”
I knelt down and reached out and undid his pants. As I pulled everything down, he unbuttoned his shirt and took it off. I pulled his underwear down and his cock, rock-hard already, sprung free. I wrapped my mouth around it and used my tongue to caress his knob just the way I had learned he loved. With my hand I stroked his shaft too, as I started to move him in and out of my mouth. I could take him deeper by then. I sped up, knowing that he would not last long before my mouth was filled with the cream I craved. But to my surprise he pushed me away. It is obvious now where he intended to cum instead, but at the time I was too naïve to realize.
I moved onto the bed, lifted up my hips and slipped off my panties. I was naked. I wasn’t shy with him any more. I spread my legs, inviting him. He kissed little trails up the insides of my thighs, teasing me by not quite getting as far as my pussy. Finally the kisses started to land on my fleshy lips. I was glad Paul had made me shave, it made them so sensitive. I reached down with one hands and use my fingers to open myself up. Immediately, his tongue was inside me. I could hear myself moaning as if it were somebody else. The tip of his tongue found my clit. My body started to tremble as it always did when I got super-excited. He pushed a finger inside. I was so wet.
I moved the other hand to my breast and started to pinch my nipple. Hard. Really hard. I felt my orgasm swell up like an orchestra building up to the crescendo at the end of a symphony and then I was cumming. My body was shaking, I was moaning, my pussy was clenching around his finger. It seemed to go on forever. My hips couldn’t keep still. It was as intense an orgasm as the very first time he’d licked me. After the final ripples faded away, I lay limply on the bed, half-asleep, letting my body recover.
Suddenly I felt his finger at my pussy again. Then I realized it didn’t feel like his finger. I tried to open my eyes but my body wasn’t working. He pushed hard. It hurt but instead of pulling back my body had its own ideas and it sort of thrust my hips up against him despite the pain. Like wiggling a loose tooth, despite it hurting I couldn’t stop. My hips pushed up and he pushed forward. In retrospect it was like having a wedge driven into me with a hammer but I was so ravenous I couldn’t have stopped if I’d tried.
I’ve no idea if there is a gentle, slow way to do it. But for whatever reason we were neither gentle nor slow. He thrust his hips forward hard and it was as if my body was torn apart. I screamed with pain and his cock was suddenly buried in me and I was no longer a virgin. My eyes were still shut although I was crying and could feel tears. I felt his mouth kiss away my tears and then he was kissing my mouth. It was so romantic, like I was in love, his tongue in my mouth, his cock in my pussy. I wrapped my arms around him as he started to move inside me.
“OK?” he asked.
“It hurts like hell but don’t stop,” I managed to say with difficulty.
Gradually my body got used to the assault, the pain faded and the pleasure started to take over. It didn’t feel anything like I expected. I hadn’t really expected the pain, sex is supposed to be so wonderful, and then slowly but surely it was wonderful. I realized that my hips were under autopilot, thrusting up to meet him each time he pushed his hips forward and slid his cock inside my body.
“Squeeze me,” he said.
“How?” I wasn’t sure what he meant.
“Your vagina. Squeeze it.”
I’ve never really tried to do that before but I did what seemed like it would work.
“Oh yes,” he cried immediately.
He started to thrust more softly and I felt his cum inside me. Actually it felt as if my body had suddenly sprayed a lot of extra wetness inside me but I knew what it really was. He’d come in my mouth enough for me to know how it all worked.
He pulled out and moved up the bed. His cock was smeared with blood and what was presumably a mixture of my juices and his cum. He put his cock into my mouth and I started to lick him clean. It tasted totally different from when I just sucked him off.
I realized he was dialing the phone.
“She was a girl but I made her a woman,” he said.
“She’s fine. Do you want to talk to her?”
He pulled his cock out of my mouth and held the phone to my ear. I could hear Paul talking to me but my brain wasn’t functioning enough to do more than whimper. Plus it was odd. How many girls talk to someone else on the phone within a minute of her defloration?
“hey. still the second f-word ones”
“you ok?”
“fine. i went all the way. i effed”
“i talked to you”
“i know. i could hear you. i didn’t seem to be able to talk. i think i was in shock”
“were you ok with everything”
“yeah. you were right. i was ready”
“how was it?”
“i’m tight. it was hard to get in. fucking hurt too”
“haha. but he pushed hard”
“we both pushed hard. i don’t want you to think i was just passive”
“good. did you decide to do it or did it just happen”
“it just happened. he licked me. i’d cum. i was lying there with my legs wide, sort of recovering. i felt his cock there. for a split second i wanted to push him away”
“did you?”
“nah. my body had its own ideas and my hips sort of pushed forward without my making a decision”
“did he use a condom?”
“lol. i have no idea. my eyes were closed”
“good job i put you on the pill then”
“what about diseases?”
“i think you are safe. you’re clean, you were a virgin. he and his wife were virgins at marriage i’m sure. i bet you are his first indiscretion. he told me you were his first student”
“good. we did it again this morning”
“in the apartment”
“yes”
“was it better than the first time?”
“it only hurt a little. plus i knew what to expect so my brain was working and i was more aware of everything. it’s pretty cool”
“sex you mean?”
“yeah. i want it all the time now”
“haha. that beast once awakened does not easily go back to sleep”
“sounds like something from the bible”
“well i don’t think it counts as adultery since you’re not married. so you didn’t break any commandments”
“i can’t believe i did it. i’ve never done anything bad before. now look at me”
“don’t tell anyone. not even your closest friends”
“i’m not stupid you know. they wouldn’t believe me anyway”
“maybe. but let’s not find out”
“ok. i’ve got to go now. bye”
“bye”