History and Prologue:
My parents first sent me to boarding school in grade seven. I don’t know why it was at that age, or even why I went willingly.
In grade six, in public school, I didn’t know half of the swear words, what a cunt or a twat was or what a meat or how long your dick was meant to be. I didn’t even know what slut or whore meant. I mean I was ignorant on sex. I was also really really prude. I mean I defined the word prude. I had never kissed. I thought that kissing was gross. I thought that you had to be in love to do anything like that. I had never even thought of a blow job or eating somebody out or even what that could be. I wasn’t curious to know. And no it wasn’t because I wasn’t sexually attracted to girls yet or that I hadn’t gone through puberty. I was going through it. I had started to get those brown pubic hairs around my crotch. My balls had started to itch and it was weird. I liked girls in my class. They were starting to get little bumps of tits on their chests too. It was strange.
I hadn’t even thought about masturbating yet. I thought that that was really nasty too. I thought that only retarded kids would do something like that. I mean when I was younger I would sit in bed and move my penis around and stick my thumb inside it. It wasn’t until about grade that I actually realized that I of the few kids in my class that hadn’t been circumsized. I didn’t feel any different about it. But when I was playing with it when I was younger nothing even began to happen. It was as though it was just there to pee out of. Yeah, sometimes I got erections but that wasn’t very often and when I did, I just didn’t know what to do with it.
There was this girl in my class that I think had a crush on me. She for definitely sure was not prude. She was tall, pretty, relatively large, and she was definitely developing big tits. She went for another guy, and during the lunch recess, I snuck into the woods to spy on them . I didn’t really feel that what I was doing was wrong it was just a curiosity. It also turned out that half the other students in my class did the exact same thing and all that they did was kiss, and rove the hands over each others body. I didn’t know it then but what they were doing was actually making out.
So this is the state I was in when I went to this boarding school. Prude, Ignorant and Unprepared. This school was not big. Let me tell you. It had 39 students when I first arrived. 39. That is really small for any school. And half of them were below grade 6. I wasn’t really excepted that year. But one girl did like me. She was black(I soon found out that this was a big turn on for me) and she was big. Around 200 pounds, not very tall and she was in grade. One grade ahead of me.
Let me now tell you something of our sleeping arrangements. It wasn’t like a regular private school with dormitories. This school had houses. Each house had about 10 kids. Two people to a room, and five rooms. In each house there were two adults who lived in the apartment and they were meant to look after you. Put you to bed and basically don’t let you screw yourself over. So this girl was in my house. Lets just say that her name is Katie. I lucked out and didn’t have a room mate and half way through the year she lost hers too, due to problems with her own room mate. So we were both without room mates. Our house parents did room checks at around 10:00PM and sometime in the morning, who knew when.
I didn’t really like her. At first I did but not really. The thing was she liked other guys too. It was just that I was the easiest to go for because I was there. She wasn’t really liked by people in the school either.
A few months previously she had been skiing at a local mountain and had had an accident. A BAD accident. She fractured her skull and her right eye closed. She missed school for about a month. The night she got back to decided to take me and some other people to town. Some how we got landed with the back seat. Half way into town she scooted over a tiny bit and really cautiously began to touch and stroke my hand. Before this I had had no idea that she could even like me. I had had no idea that I could be attractive to anybody else. So after dinner, I responded to her stroking and sqeezing my hand, by doing the same thing to her hand. As we got back to our dorm, she leaned over and asked “Will you go out with me?†Such a big question. I said: I have to think about this. She asked when will you tell me? I said by the end of the night. So I mulled it over in my brain. And by the end of the night, I had said yes to myself. So At my bedtime I went across the hall to her room, walked in without nocking and said to her, Yes. I had to repeat it, because I hadn’t said it loud enough. She looked at me. And I could tell that it had made her really happy for me to have said that to her. The next day I told her to keep it secret because I didn’t want to have to deal with the teasing and all the other crap that goes on behind going out with somebody. So we did.
Then one night up at our house. We had a family come over. And we also invited another girl over. So we had me, Katie, two other girls, and my best friend Ted. Ted wasn’t prude. And one of the other girls wasn’t either. We will call her Jesse. Jesse and Ted weren’t going out but they were doing stuff on the side. They could have done anything at anytime. So there we were. Two couples and another watching. So we decided to do truth or dare. That eventually spilt over to 7th heaven. Which is seven minutes doing whatever you want to each other in a closet. So I was with Katie. Ted was with Jesse. This is where I got my first kiss. And it wasn’t any kiss. It was a french kiss. Tongue and all. Katie and I were both pretty nervous. We eventually leaned in and our lips met, and bang, we were kissing wildly. Slobbering all over each other and exploring each others mouths. It was great. When we went in for our seven minutes of fantasy. I didn’t know what to do. So we kissed some more, then she took my hand and put it to her breast. I didn’t know what to do. Inside I was like AHHHHHHHHHHH. I’m touching a girls forbidden parts. With her permission. What do I do? So, I rubbed them a bit. Then I went under her shirt, and felt them through the bra. Her shirt was all bunched up by then. Then I went under her bra. It was fantastic. It was the best feel up that I had ever had. Just as she was about to take off her shirt and bra for me to suck or those tits of hers, Ted and Jesse called to us in urgent voices. Hurry up the house parents are in the hall looking for you. So we had to stop and come out looking calm while inside both of us were aching to go back at it.
It was her idea from the start. Just that others had to help her to pull it off. Katie asked our house parents if those of us in our house who wanted to sleep downstairs could. So of course Ted, Jesse, Katie and I and a few others decided to spend the night sleeping downstairs. The others went right to sleep after talking a little bit. Then Katie and I got to it. We kissed. But inside I was aching to go back to her tits. I mean that is all I wanted. So I unbuttoned her shirt and there was her bra. Her tits held inside firmly. Since she was laying on her side with a blanket over her, only I could see her tits. One of them was slightly leaning off to one side and the other was resting right above it. I felt them. I put my hand over her nipple and felt it rise at my touch. I didn’t know what that meant. But by this stage my instincts had turned on. I knew that I had to get at her tits. I put my arm around her back and felt for the clasp. I didn’t want to seem like the dumb ass that I was. I couldn’t find it. Then I realized that it was a pull on bra without a clasp. She had to sit up, slightly wrecking the moment to pull up and off her bra. It was white. No lace no frills. But perfect for the time. I felt like I was in heaven or something close. She lay back down. Now those beautiful light brown tits with the darker nipples were facing me and open to my touch and my tongue. She was completely willing to let me try whatever I wanted.
First I went and rubbed my hands all over them. Some things she said OW to. Others she was like yeah. Do that more. I found out that if you mix a bit of sucking, nibbling, and flicking with your tongue over a nipple, you can give her pleasure. After a while I got tired of this. So I started to kiss her all over her body. You know like how they do it the movies. Starting at the neck or ears and working down. I didn’t know what to do. So I did a bit of all of it. Started at the ears and face planting kisses wherever I could. When I got to her stomach and pubic hair, I went back up to her lips and kissed her passionately. We kissed for a little longer. Since I had a really hard hard on by this stage. I slowly took her hand and put it under the blanket that we were sharing and she rubbed her hands all over my body. It was sensational. Then she when to my penis. I don’t think she had any better idea of what to do than I did. She played with my balls a bit and rubbed my dick. But I don’t think she was ready to do anything for me. So I was easy. I went to sleep. Before letting me though. She asked me: Do you want to do IT?. I was like maybe sure I don’t know. I didn’t really know what she was asking me. I thought she might be asking me to finger her or to eat her out. But I definitely wasn’t going to fuck her. Not then, not that night.
So I put my hand out and felt her warm tits one more time, before I went to sleep. I dreamt sweet dreams that night.
After that night. She always asked me to come to her room after everybody else had gone to bed. The first night I stayed up until around eleven. Then I crossed the hall and went into her room. I was sort of scared to wake her up. I mean I didn’t really know if she wanted me to. So I stood near her head for a little while. Then hesitantly I put my hand out, lifted the covers and tried to get into bed beside her. She woke up at this, but welcomed me. I was on top of her. I leaned down to kiss her. She accepted my tongue and kissed me back deeply. I took off my shirt and threw it on the floor. I unbuttoned her shirt and spread it asside. There they were again. But still in a bra. I couldn’t understand why any girl would sleep in a bra. I mean. I thought bras were like underwear. You took them off at night and put on P.J’s. Apparently I was wrong. So we took her bra off too. Her light brown tits were free to my roving hands. I loved them. I couldn’t get enough of them. I wanted to suck them and nibble them the whole night. So as I was sucking on these beauties. I slowly put my hand down her side, slipped under her pyjamas and into her pubic hair. Slowly she spread her legs, expecting something pleasant from me. I at that time had no idea what I was about to do, only that I should do something with her crotch. I wasn’t about to ask her either. So I randomly put a finger out and pressed in. All I got from this was an OW and a mumble that said something like I should punch you in the face for what you just did. So I retreated my hand quickly. I didn’t think that I would do that again. So one last quick kiss and I asked her to not wear a bra the next night.
Same drill again, only this time she woke up really quickly and asked me to get under the covers with me. Instead of her wearing a shirt and bra, all I found this time was a dressing gown. That meant a quick pull at a knot and she was naked beneath me. And I mean completely naked. She told me to go to her closet, reach up to the top shelf and get the small green bag that was sitting there. I did as she told and inside it was a couple of condoms and some lubricant. She told me to put the condom on. I did. It didn’t seem to fit right but I didn’t tell her that. She then told me to get back on top of her. The skin on our bodies met. We stuck together because we were both sweating mildly. I asked her if she was even close to her period. She said no. So I was somewhat safe. I had figured out that we were going to have sex. We lay on each other. Kissing and holding each other until slowly she guided me in. It took both of us a couple of tries to find the most pleasing spot. I slowly started. I glided in smoothly.
At first, all went well and smoothly. Then I started to hear a crinkling. I thought quickly and stopped. Pulled off the condom because it was too loose. And just started right up again. Quickly I got tired. I climaxed and came deep inside of her. I mean, that was the first time that I had came due to female aid. So it was really fast. I didn’t get her off that night or any of the other nights following. But I do know that we both had a lot of fun and that I certainly wish her many more fun evenings and remember that first night when we first fucked and the many nights after that.
After that first year, I was no longer prude and I nobody knew what we had actually done. The public thought that it had stopped at kissing and maybe feeling up or feeling down.
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Inexperienced but Fun
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