My First Time - Age 16


Hi everyone!My name is Megan. I am 26 years old and would like to write about my first sexual experience. If you decide to read this, you will have to pardon my grammar and punctuation. This is my first time writing a story and figured I would draw on experience to help.

It all started when I was 16. Looking back I perceive myself as a dorky kid. My father was a lieutenant on the police force and kept me under lock and key. My extracurricular activities included track and studying over a friend’s house. Parties and things of that nature were off limits to me. Having sleepover’s at Brandy’s house was as wild as it got. We could talk about the boys at school and the gossip that was going around.

I had an athletic build, with small breasts. My hair was long and brown and my best feature was my green eyes. I was self conscious about my small breasts. I even bought a B cup bra thinking they needed room to grow. Really though, thinking back, it was because it made my chest look bigger.

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  I spoke to a female doctor once (I could never have confided in a male doctor about my breasts) and she told me a lot of athletes have small breasts, something to do with lower body fat. I didn’t believe her because some of the cheerleaders had low body fat, except in the right places. Fuck, I am rambling!Sorry!

Anyway, my boring life was about to come to an end. Brandy’s parents were going away for the Memorial Day weekend to visit her grandparents and Brandy’s brother was home from college. He was to be in charge while they were away. I convinced my mom to let me spend the long weekend over Brandy’s house, but still needed my dad’s ok. I had something in my favor though, Darren (Brandy’s brother) was the star running back when he was in high school and my father loved football. When my father came home from work, I asked him if I could spend the weekend at Brandy’s. He smiled and said what are you not telling me?I hated when he did that cop thing to me. His tone changed and you always felt like you were being interrogated. Sighing, I told him the situation about Brandy’s parents and how Darren, who is very responsible, I added, would be in charge. No, he said. No, I said. That’s it, just No?He replied, yep, just no. I was fuming, but I knew better than to argue with him.

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  I ran up to my room.

Later that night after I refused to come to supper, I was brooding on my bed when my father came in. He sat on my bed and said, I hate to tell you no pumpkin, but it is my job to protect you. I am sure Darren is considered to be a very responsible boy, but boys at that age make choices that aren’t usually done with a lot of forethought. This was the opening I was hoping for. Waterworks time!I started to cry and grabbed him in a big hug. I told him while sobbing that he never lets me do anything. All the other kids are going to parties this weekend and Brandy and I are stuck home. School is almost out and I will have another long and boring summer. My friends will all be driving to the beach together, going to concerts and parties. You won’t even let me get my drivers permit, so I am stuck at home doing nothing, again. I bet you didn’t have to stay at home every day when you were my age. I could feel him giving in. His body went from being rigid to somewhat softer. I made my move.

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  Going from hugging to holding both his hands, I told him, Daddy, you could call Brandy’s parents. I let go of one of his hand to wipe my tears and quickly grabbed it back. You could speak to Darren; he really is much older inside than his age implies. He would set your mind at ease. Please Daddy, please Daddy, please Daddy.

Ok, pumpkin he replied, I will talk to them, but I am not promising anything. Will you call right now I asked?I know they are all home and you probably won’t get them all home again, not before Friday. He sighed and said he would. Bingo I thought. I should have gotten an Academy Award for that performance. I smiled to myself, thinking I was going to have a whole weekend of freedom.

I rushed down stairs to make sure my dad made the call. He looked at me and knew I was pressuring him. He picked up the phone and called Brandy’s house. He spoke briefly with Brandy’s parents and then Darren got on the phone.

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  I listened the best I could and realized he was talking about football. This was good I thought, he wasn’t grilling him on what was going on this weekend or was he laying down the law. I waited for my answer and waited and waited. Finally I sat down at the kitchen table to wait. After a year (really about a half hour), he hung up. He didn’t even look at me and walked into the living room. I felt like a puppy, trailing behind him. He walked into the den and sat at his desk, still the bastard wouldn’t look at me. I finally couldn’t take it anymore and said WELL?He laughed and told me as long as I check in regularly I could go. I jumped up and down and ran over and hugged him. He smiled and started telling me about Darren’s football career in college. I had to tune him out, I mean who cares?

Brandy and I conspired all week, we figured that when Darren’s girlfriend came over we could split and even if he did notice, he would have to make the choice of getting laid or coming to find us. No way would he call my father or her parents. Brandy said that there was a keg party at the gravel pit and figured we could go as long as we split if anyone started to get rowdy. I obviously couldn’t be there if the cops showed up.

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  All the cops new me and it would take half a heart beat before my father found out. He would send me to some nunnery in Montana or someplace like that.

Thursday night came and I was alone in my room. I just hung up from speaking with Brandy and she told me that Chris was going to be at the party. Chris was this really hot boy that sat next to me at lunch a few days prior. Brandy told me that he liked me and I should bring something hot to wear for the party. After our phone call I went to my closet. I knew what I would find, nothing. I couldn’t own anything hot. If my parents had only seen clear to give me an older sister, one that would be in college and would most definitely have something hot that I could borrow. Hell no, they gave me a nose picking little brother who wouldn’t stay out of my room. Rambling again!Sorry.

Anyway that night I figured I would at least shave my legs, I didn’t have a lot of hair so I really didn’t need to. Thinking I would wear the shortest skirt I owned and the prettiest panties, my legs should be smooth. During my bath I shaved my legs.

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  A crazy idea came into my head. I wonder what it would look like if I shaved down there (you know where down there is). Thinking about it made me flush, thinking about Chris seeing it made me hot. What the hell, it isn’t like anyone will see, I shaved smooth. It really felt good after it was bare; I was touching it, running my fingers lightly up my lips when I heard pounding on the door. MEGAN I heard, really fucking loud. It was my pain in the fucking ass little brother. Just so you know, he wasn’t the worst brother in the world, but right then I could have killed him. What do you want, I yelled?Mom wants me to take a bath and she won’t let me use her bath room, he said. Get out, he whined. I threw a towel on and pushed passed him. What a fucking mood killer I thought. Mood shot, I got dressed and went to bed.

Friday yes fucking Friday, I thought. Half day of school and take the bus to Brandy’s house.

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  Life is good!I was peppy; I guess you could call it when I came down to breakfast. No Captain Crunch for me, just coffee. I was feeling like an adult and hadn’t even gained my freedom yet. Dad grabbed me before I could shoot out to the bus stop and gave me the whole speech about how much trust they are giving me and how responsible I am to gain this trust. Bla, bla, bla I thought. I smiled and told him what a wonderfully good girl I would be. He gave me a sideways look and kissed me on the cheek. Bye daddy I said, see you Monday.
School was painful. You never do anything before a long weekend and all the teachers know that if they give you homework you won’t do it. So they don’t bother. The only good thing that happened at school, was, Chris asked me if I was going to the party tonight and I told him I would be there. I could have danced after that conversation; maybe I could do one of those silly cheers that the cheerleaders do. I was euphoric. Nothing could go wrong!!Well except for I didn’t have anything to wear and my tits were small, but other than that, yoo, hoo!

Brandy and I got off the bus at her house just as her parents were leaving.

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  Darren was standing out the yard with his shirt off. Apparently he had loaded the minivan, because he had this sheen of sweat that was reflecting off his skin when the sun hit it just right. I could feel my face getting red, it always did this at the most inopportune moments. I moved my eyes off his chest and noticed the bulge in his shorts. Fuck, fuck, fuck, I thought. Think of spiders or bats or something gross before your face burns off. God, I have to go talk to his parents, I can’t be all flush like this. I bent down to tie my shoe, thank god I had shoes with laces, otherwise I’d have looked quite the fool bending down like that. Compose yourself I thought. Spiders, bats, spiders, bats. Ok, Hi Mrs. Anderson I said as I stood up. I hope you and your husband have a great time visiting your parents. Shit, I am really a bumbling fool I thought, her mother is sick with cancer. This is fucking Darren’s fault.

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  Sorry, I meant I hope your time together is good, I said. I’m sure it will be, she said and thank you. What are you girls going to do this weekend she asked. Holy shit, we didn’t discuss what to say to her parents. Thank god for Brandy, she said girl stuff and maybe go down to get a ice cream cone. The local ice cream place just opened up (keeping the name secret, for privacy reasons) she said. I didn’t really pay attention to the rest of the conversation it took all my concentration to keep my eyes from reverting back to Darren. I wish he would put some fucking clothes on, I thought.

Finally the Anderson's left and Darren went in the house. Brandy asked me if everything was ok and I told her of course, what make you think everything wouldn’t be ok?She said you seemed flustered. I told her it was because I didn’t expect to lie to her parents. We went in her house and up to her bed room. I was complaining that I wanted something hot to wear, but my dictator of a father wouldn’t let me. She said we can look in her closet. Brandy, you’re filled out in places I am not, I said.

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  I won’t be able to fit in something you own. She said her mother has kept her clothes since she was a kid, she was sure she could find something to fit. Digging through her mountain of clothes we came across a skirt. I tried it on and it fit, but was really short. I was looking at myself in Brandy’s mother’s full length mirror when Darren came by and poked his head in. Holy shit, he said. Megan, I hope you don’t plan on wearing that outside. Brandy jumped in between us and said we were just playing dress up and unless he wants to put on a dress he can take his ass somewhere else. I noticed he was staring at my ass, but Brandy pushed him out and shut the door. I can’t wear this I said, it is just two short. Brandy said nonsense and asked if I had a pair of thigh highs. I told her no, I don’t have a pair of thigh highs and I want to look hot, not like a slut. She said it is hot, and don’t worry about feeling out of place; everyone will be dressed like that.

It took forever for Darren’s girlfriend to arrive. She was one of those girls that is easy to hate.


  For those guys who are reading this, you have to understand that girls never say we are envious or jealous of the way another woman looks, we just automatically hate them. Anyway she was beautiful; of course she was beautiful, Darren was beautiful. How could she be anything but beautiful?She was about 5’8” tall, long dark hair, perky tits and a tight ass. My eyes were better though. Anyway it was 9:30 when her highness finally arrived and of course we had to wait a few minutes for them to get settled in. So it was about 10:00 when we made our way down the street for the two mile trek to the pits.

We arrived and I immediately felt self conscious. Along with my very short skirt I had a laced up halter top on (which would have looked awesome on a girl who was better endowed). We had picked up a pair of white thigh highs earlier in the day and Brandy assured me they looked hot. A lot of people showed up for this party and they had started it at least an hour or two before we got there. Some people already had quite the buzz going. I wanted to find Chris and spend some time with him before it started to get rowdy. Brandy saw her boyfriend and told me she would see me later. I made my way over to the kegs and poured myself a beer. I figured if I waited here, Chris would have to show up at some point.

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  I was feeling pretty good, because I got some compliments from a couple of guys that I didn’t know. Randy came up to the keg (Chris’s best friend) and I asked him where Chris was. He said that he didn’t know, haven’t seen him all night. This was disturbing because they were always together. He was pretty drunk and after he refilled I followed his stumbling ass.

He led me right to Chris, and of course Chris was not alone. Did I mention that I hate cheerleaders?I didn’t need to get very close to see Mara hanging all over him. I moved away swiftly so Chris wouldn’t see me, because I knew I was going to cry. When I got to the outskirts of the pits, I turned and ran. I was back at Brandy’s house in an instant it seemed like and I knew I couldn’t just go in the front door. I snuck in the back door and went up to Brandy’s room to cry. Brandy came home about 2 hours later, she was pretty drunk. She asked me why I didn’t tell her I was leaving. I told her what happened and we were talking pretty loud. I said some things like, I was ugly and I looked like a boy.

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  Then we heard Darren yell up the stairs to ask if everything was alright. We told him fine and we got dressed for bed. Brandy was out in seconds. I on the other hand had to use the bathroom.

I snuck down stairs to use the bathroom but when I got there I could see the light on. I turned to leave when the door opened. Sarah, Darren’s girlfriend said don’t leave, its open. I turned but kept my eyes down. I tried to move around her but she stood in the door way. I finally had to look up at her and she bent over and whispered in my ear. She said you don’t look anything like a boy and you are beautiful. When she came away from my ear, she looked me in the eyes. I was so embarrassed that they had heard our conversation. I looked back at her and I could feel the tears coming again. She bent over and lightly kissed me on the mouth.

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All those feelings of self pity, jealousy and anger were gone. They were replaced by shock. She grabbed my hand and walked me into the bathroom. She brought me over to the mirror and we both looked at my face through it. I was wearing cheap make up and it was everywhere from crying. She grabbed a cloth and makeup remover and started to clean my face. She told me that I didn’t need any of this to begin with. When she was done she took me by the hand and walked me into the living room where Darren was. She told Darren that I was having a bad night and was going to spend some time with us. Darren said cool, he was rolling a joint and said this will help with a bad night. Sarah sat me down and I finally focused. Sarah was wearing Darren’s football jersey and a pair of panties. Darren was wearing boxers. I on the other hand was wearing jammies with unicorns on them.

Darren lit the joint and passed it around.

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  I had tried pot before, but remember my father is a cop and could tell if I came home high. So my experience was limited. When it came time for me to take a hit, I took it and sucked in on it, but didn’t really get a hit. I think I was holding it to tight or something. Sarah took it out of my hands and put the lit part into her mouth. She drew me closer to her mouth and blew. A white stream came out and I sucked in. I don’t know if it was the pot or the kiss by the bathroom door, but she was turning me on. After a couple of times with her blowing that smoke into my mouth she sat down on the floor with Darren and looked at me. She asked Darren if he thought I looked like a boy, for some strange reason Megan thinks she is ugly and looks like a boy. Darren laughed. He said to Sarah, have you seen her ass. How about those legs he said. I saw her in this little skirt tonight and her ass and legs blew me away. To think, little Megan is all grown up.

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Skirt, Sarah said?What skirt?Oh it was this really short thing, Darren said. I told her she shouldn’t go out with it on. Well we aren’t outside; surely she could wear it now Sarah said. Megan, why don’t you go put that on so I can see. I started stammering and said that I don’t think I should. I was cut off by Sarah. She said put everything on that you wore out tonight. Not like it is a secret anymore that you and Brandy went out. I want to see if you truly looked like a boy. She grabbed my hand and stood up bringing me up with her. She turned me and tapped me on the ass and told me to hurry up.

I was walking back up stairs fighting with myself. She was turning me on so much, but I could just put on an outfit so she could gawk at me. I guess you all figured out that I was more turned on than embarrassed or I wouldn’t be writing this story. Anyway I went into Brandy’s room and grabbed all my stuff.

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  I went back down stairs and headed for the bathroom when I heard Sarah say we are waiting for you. I went into the bathroom to get dressed and realized I was soaked. I had masturbated before and hadn’t been this wet. I couldn’t go back out there with these panties on. I couldn’t go back up stairs and start rifling through my stuff to find some more. It must have been the pot. There is no way if I was in my right mind that I would have decided to go out there with no panties on, at least that is what I was telling myself. I put the halter top on, the skirt and then the thigh highs. No panties.

When I came out to the living room, I was embarrassed. Sarah stood up and grabbed my hand. She put it above my head and told me to turn around. I spun quickly, thinking that Darren might not see that I don’t have panties on if I do it quickly. Logic wasn’t on my side. Darren was on the floor and I was standing up.

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  When I spun around quickly my skirt rose. I heard Darren say yea!She doesn’t have any panties on!Sarah, who was behind me stepped back and lifted my skirt, nope she said, she sure doesn’t. Sarah moved away from me and went to the entertainment system to put on some music. I didn’t know the artist, but it was soft with a beat. She came back and took my hands and started to dance. I figured I had better dance also, or I would look like a dork just standing there.

Sarah turned around and started swaying her hips and pushing her ass on me, I put hands on her hips to keep rhythm. Darren stood up and moved behind me and started dancing with us. His hands were moving up and down my thighs and ass. My head was swimming. I could feel dampness on my inner thighs. Sarah turned around and while holding my hips started to kiss me. Her lips and tongue were so soft and god I really liked kissing her. Darren was kissing my neck and grinding his hard cock against my ass. I felt like I was a volcano, it kept building and building.

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  My body was itching to be touched. If somebody didn’t do something soon, I was going to explode.

Sarah started to suck on my nipple; she flicked it with her tongue. Darren was biting on my neck and running his hand up the crack of my ass. Sarah pushed Darren away from me and lay me on the floor. She pulled off her panties and shirt and lay on top of me. She kissed me again then started to unlace my top all the way. When she was done she pulled it open, exposing my breasts. She moved down and started to kiss my inner thighs. Darren moved down to massage and suck on my nipples. He came up and started kissing me. That was it, I was on fire now. Every touch and nibble was sending me into oblivion. The only rational thought I had was please don’t stop!

Daren placed a knee on either side of my head and lowered his balls into my mouth. I was so happy to have something to do, something to focus on.

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  Sarah had moved to my pussy and If Darren’s balls weren’t in my mouth I would have screamed. I was making these panting almost crying sounds that I couldn’t believe were coming from me. Sarah was making something happen with her tongue (I hadn’t ever had an orgasm before this), I could feel myself convulsing, I was gushing so badly, for a minute I thought I was peeing.

Sarah was kissing my pussy now. My clit was so tender, that whenever she brushed it I jumped. I could focus a bit now and saw Darren’s hard cock. It was huge (it really wasn’t, but it was the only hard cock I had ever seen, so it looked huge then), for some reason I told him I was a virgin. He smiled, moved to my ear and said don’t worry my baby Megan, when I am done, you still will be. I remember being somewhat relieved, again I had no idea why. Sarah moved up and pulled me up to face her, she started kissing me again. She leaned back and brought me with her. I was now on top of her and I kissed her mouth, her chin, her neck and I moved to her breasts. They were beautiful, firm and her nipples were rock hard. I sucked them and flicked them with my tongue.

Darren had moved in behind me and started to kiss on my ass.

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  He kissed the bottom of my cheeks and I was surprised how good it felt. I moved down Sarah’s hard belly to her belly button and licked it a bit. I knew I needed to taste her. I couldn’t think of anything else, so I moved to her inner thighs. This brought my ass up and Darren to full advantage. He licked and kissed my asshole. Somewhere in the back of my mind I was surprised by this, but I needed, badly to taste Sarah. When I finally got to her pussy, I inhaled hard. She had this sweet musty smell that didn’t smell anything like my pussy. She smelled like moist heat with a mix of some perfume. My tongue moved to her wet slit and I felt my whole body jerk. I wanted so badly to please her. I started running my tongue up her lips, and oh my god,I thought her mouth was soft. This was like velvet. She was clean shaven and open.


  I ran my tongue back up her slit for more of her essence when Darren pierced my ass with his tongue. I was jolted but pleased.

I found Sarah’s clit and started to tease it. She was moaning now. Darren was pushing something against my asshole and it hurt, but it seemed like it wasn’t real. Then there was pressure, intense pressure. I concentrated on Sarah’s clit. Watching her body quiver when I brushed my tongue across it, was fueling my fire. I was feeling myself getting wetter. My thighs were sticky. I started to rhythmically rotate my pelvis and push against the pressure. My tongue was darting faster and faster over her clit. Sarah was moaning louder and louder.

Something, the pain, the pleasure, my emotions, everything was so confusing. Darren pushed his cock into my virgin ass.

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  I screamed. Did it hurt?Was it pleasure?Sarah was going to climax. My head was spinning. Darren was fucking my ass; he was fucking it fast and hard. Was I cumming?Sarah dug her nails into my shoulders. Did that hurt?I don’t know. Sarah is cumming. I moved lower and licked her wetness. Fuck, I thought. Darren was pounding me now. He gave one last thrust and grunted. He stayed there for a minute and pulled out. I rolled on my side, laying my head on Sarah’s inner thigh. I was so fucking spent.

I lay there for a few minutes breathing hard and I had this stupid thought.

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  They didn’t care that my breasts are small. I smiled to myself. Darren came down and kissed me on the cheek. Nice touch Megan, shaving your pussy like that. I sat up and so did Sarah. She asked me if I was still having a bad night. I hugged her and said no, thanks to you.

Sarah and I are still friends today. We sometimes talk about this time we had together, although if she knew I was sharing it with you she may not be happy. She is a mom now and a great one. Her wild days are behind her and she tells me she needs to keep it like that.

I hope you liked my story and maybe I will write another one if you would like. Hey I spent 4 years in college after all!