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The First Time Never Comes Twice

"Natalie had no intention of leaving high school as a virgin, but first came a few detours."

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This is my story as I remember it!  A few details have been left out, but this is basically what happened

Ever since I had my first period, I began thinking about sex in new and different ways. To make it simple, I was curious and wondered what it was like to have sex with a guy. By the time I was seventeen, I had blossomed physically and my new hormones took me in unexpected directions too. It's just that I didn't quite know how to deal with my newly formed assets. I was unsure of myself and a little naive. Naive, that is, until I came home from one of our football games. Apparently, I wasn't expected home because my mom and one of her boyfriends were downstairs in the family room.

It didn't take much imagination to know what was going on downstairs. I mean both of them were pretty vocal, so the sounds of sexual pleasure was unmistakable.

It really wasn't unusual for Mom to be entertaining a guy in our house. She was sexy, pretty and had a really ample set of boobs. I think I take after her in that regard. Anyway, Mom never tried to hide the fact that she liked sex. It wasn't that she talked a lot about it, but I had the impression she was screwing lots of guys. She never tried to keep that a secret.

My plan was to go downstairs and watch, staying out of sight of course, a voyeur. Okay, I'll admit it. I had seen couples fuck on porn websites, but I had never seen real people having sex. So, my curiosity got the best of me and wanted to be closer to the action. It didn't work out that way.

After taking off my coat, the sounds from downstairs had stopped and I heard Mom say, "Natalie, is that you?"

"Yes, Mom. I'm home a little early."

A few minutes later she came upstairs with a stranger close behind. I had never seen the guy before. It wasn't surprising for Mom to be entertaining someone new. She was quite liberal about her choices, and there were many.

As for me, I now had an elevated interest in sex and didn't intend to start college next year as a virgin. The problem was that I had no boyfriend and wasn't even dating.

I began to take stock of my better qualities. I had a couple of things going for me. An important one was that I had developed a respectable, if not a sizeable set of boobs, but was afraid to let them show. I just needed more confidence and wear clothes that showed a little more of me. Another positive was that I finally made the cheerleading squad giving me the chance to be with the popular kids.

There were some things I needed to work on, like my personality. I had been a little shy, kind of a shrinking violet type during my first years in high school. At sixteen, it was natural for a girl to lack self-confidence while acquiring a curvy physique. Now that I was older and physically mature, I needed to become more assertive and more available to guys. I was a fun girl on the inside, but it didn't show on the outside. Some things like my visibility I could control. My new hormones were going to be a little harder to keep in check.

After I said hello to my mom and the stranger, they disappeared in Mom's bedroom, and I ran upstairs to mine. I needed to get some satisfaction of my own after hearing what had been going on in the family room. I masturbated like crazy and must have gotten myself off a half dozen times. Oh, that's another thing. I like pleasuring myself. I've been doing it for about a year. My orgasms cum pretty fast, and are frequent once I get started. I absolutely love the feeling it gives me. The problem is I have to do it myself.

Let me explain that I'm an only child. I guess you could say I'm a love child because my mom had me in high school as a result of an unexpected pregnancy. It's pretty well accepted that most high school pregnancies are "unexpected," so when I turned sixteen, my mom started me on birth control pills. She wasn't against me having sex. She was only against being a grandmother at her age of thirty-four.

Teachers really don't like their cheerleaders to show off their tits, so the uniforms are conservative and didn't show my best assets. Because the uniforms weren't doing me any favors, I decided to push the envelope a little and wear a thong under the short cheerleader skirt. It could be a little chilly at football games, but it was worth a try. I decided to risk it at the next game.

There was no way to tell who noticed. At the post game party, a few guys came up to me and said, "Great cheerleading tonight, Natalie," and they laughed. They were idiots, and I didn't care that they were making fun of me. At least, that's what it seemed to be or maybe I had an attitude problem. However, there was just a chance the guys were taking notice, and that was my objective.

The next week I decided to dress more seductively at school. I wore a loose tank top so when I leaned down, my better features would fall into full view. The first day I wore it, I would see the other girls whispering about me. It wasn't the girls' attention I was after, so it didn't matter.

Later that same week I wore a shear bra, the kind where my nipples would show through a tight crop top. My mom noticed and said it was inappropriate for school. Then she smiled and said, "Go for it girl!" laughing her way back to her bedroom where another new boyfriend was waiting.

I wasn't sent home from school that day, but was given a strong warning from one of the female teachers. I was okay with it because during the weekend the text messages began. They weren't from my girlfriends.

Many were raunchy and one was obscene. Two boys sent voice messages. I only knew one of the boys. It was Greg, my lab partner, so I returned his message. I told him I'd meet him after school on Monday in the library. We talked for a few minutes, then he asked me out. I played a hard to get, and said I was busy that week. Of course it wasn't true, but I was looking for a better deal. Greg was nothing special, kind of a geek, so he became my backup.

The next day, a guy who towered over me said, "Hey sexy, didn't you get my message?"

I pretended not to be interested but asked, "Who are you?" Of course I knew who he was but not his name. He was the star player on our basketball team.

He said, "The name is James and hoops is my game!"

"Really, I said mocking him. "You mean running around in your underwear." I said sarcastically.

He said, "Yeah nympho, it's called basketball."

I guess I was the dimwit because I didn't catch the "nympho" reference. Anyway, he grabbed me forcefully and leaned me against the lockers. "My buddies are having a party and we're goin'. I'll pick you up at seven. Okay?"

It didn't think that 'no' would be the right answer. I was scared but excited so I said,"Okay," and gave him my address.

I wore a revealing half cup bra and my tank top showing plenty of cleavage. I was doing everything but begging the guy to fuck me.

The party didn't turn out like I wanted. I didn't know most of the girls, and the guys kept making rude remarks. I wasn't used to sexual innuendos. I felt isolated and lost. On the way home, he tried to rip off my bra and grab my tits. He was rough and really vulgar. He called me a cunt and other terrible names. James said I was a tease. I never wanted to see him again.

Later I learned, vulgar and sexual innuendos came with the territory. I eventually got used to it.

I wasn't going to give up on my new adventures, so I checked in with my backup, Greg. He was delighted to take me out after the next football game.

Greg wasn't at all what I had expected. We went for a pizza after the game then parked. I still wore my uniform with the thong, so that made it easy for him to do a little research. The research was between my thighs. Of course, before reaching my snatch, he was feeling me up. I guess I helped him a little by removing my bra. It felt good having his warm hands on my tits, and his fingers rubbing my pussy.

Well, I thought this was it. This was the night I was no longer going to be a virgin. It almost turned out that way.

Greg put my hand on his crotch. I unzipped his pants and pulled out a very firm thick cock. It wasn't long, but it wasn't dwarf length either. I just held it and gave him a hand job until he got really really hard.

To me, it was totally amazing at how super hard a guy can get. So while I massaged Greg's cock, he continued to massage my pussy. Like I said, I cum easily, so I was really wet the whole time. All at once Greg gave a grunt and his cock exploded. It was a spontaneous eruption for which I wasn't prepared. And he kept erupting. Cum shots went straight up into the air and kept exploding over and over again like fireworks on the Fourth of July. He was making a real mess of his clothes and the smell, well it was a smell I can't describe. It was pungent, kind of like bleach or maybe fish. All I know is it got all over my hand, so I wiped the gooey stuff on his car seat. I didn't want it on my clothes, that's for sure.

That was the end of Greg that night. He was drained and took me home soon after.

The weeks rolled by quickly my senior year. After the night with Greg, I started dating more regularly. Most dates involved parking and some kind of light sex, but not the real thing, not what I was after.

My girlfriend, Gail, had invited a few of her friends and some guys over for an after game party while her parents were out of town. Most of our teen parties were like that with no adults to "supervise" us. I knew everyone except for one guy by the name of Eldrick. He was new in the neighborhood, and Gail decided we should get to know him. He was a good lookin' guy and kind of a show off but then, I wasn't exactly the one to talk.

The party with Eldrick was different for a couple of reasons. First, he was the first black guy I kissed. I was accustomed to seeing my mom bring black guys home, so it was no big deal to be with a guy of color.

The other thing was that the party got out of hand pretty quickly. It wasn't exactly like the Tom Cruise film, "Risky Business," but there was plenty of drinking, mostly beer, and some sex that I only heard about later.

Anyway, I was downstairs in the rec room watching a football game with a few of the guys. They were kind of drunk and rowdy, but I didn't think twice about the fact I was the only girl. I had just finished my second beer, so I was a little relaxed laughing at some of the dumb things the guys were doing. That's when I met Eldrick.

Eldrick pulled me out of the chair and put his arms around me pretending to dance. "Come on girl, dance for us," he said. Well, maybe I was a little more "relaxed" than I thought because that's what I did. I started dancing and decided to put on a show for the guys who had instantly turned away from the TV. Hey, what girl wouldn't want to be the center of attention of three or four football players? They were the popular kids, and I wanted to be part of that group.

The thing is, I was wearing a light tank top that floated just above my navel and a revealing bra. The boys obviously noticed my nipples protruding through the tank top. Each of my movements made my boobs jiggle making the boys whistle and shout their encouragement. If it was heard upstairs, everyone had to assume it was guys watching the game.

Someone put on a Michael Jackson CD, so I continued to dance and show-off. They yelled, "Take it off, bitch. Let's see what ya got."

I didn't take anything off, only pulled up my tank top for a quick peak, then laughed as if I was having fun. I was really laughing in embarrassment. It was obvious the boys were getting a little more aggressive than I liked, so I grabbed another beer and tried to hide on the sofa.

Eldrick sat next to me and said, "You are terrific and really sexy."

That made me happy. Being called sexy was exactly what I wanted to hear. Then he moved closer, and I got kind of nervous. "What's your name?" he asked.

I told him my name. He moved closer so I was wedged between the arm rest and his body. I should have run upstairs at that point, but I didn't. He put his arm around my shoulders and moved in for a kiss. He kissed me and I kissed him back. We didn't stop.

Eldrick's hands where soon under my top feeling me up. My tits just popped out when he yanked down my bra. Feeling his large hands playing with my nipples put me into orbit. I didn't even notice that the guys in the room were watching us. Maybe I really didn't care.

His next move was to pull down his zipper. It was stuck. God only knows why I helped him get it undone. He was in such a rush he had trouble getting his cock out. I helped him with that too by unbuckling his pants. Finally his large black erection appeared and begged to be touched. I thought that if I touched him down there, that would be the end of it. It wasn't. Eldrick pulled my head down between his legs. He wanted a blowjob.

I had seen lots of blowjobs on the Internet websites, so I had a pretty good idea what to do. I did as Lauren Bacall said in the movies, "You just put your lips together and blow."

It isn't like sucking on a cold sweet lollypop. It's more like a banana only warmer and firmer. Eldrick showed me the motion he wanted by moving my head in rhythm with his hips. I heard it said, "It ain't the meat, it's the motion." He finished by depositing a nice load down my throat.

The taste wasn't as bad as the smell. It's salty and creamy, but I was okay with it. I thought it went well for my first time. Later, blowjobs on dates became the rule rather than the exception. I have to say that after awhile, I got really good at it.

So that should have been the end of my generosity that night in the rec room. Eldrick had gotten off with my help but not the other three lads. After I finished with Eldrick, I looked up and saw three hard one eyed dicks staring at me. The other three had their pants down rubbing their cocks waiting for my mouth. They weren't about to take no for an answer. The look in each of their eyes said they meant business; the look was of hunger, desire, and lust.

One of them said, "We need you to help us build team morale here."

Another said, "Hey, bitch, you need to take one for the team." He obviously meant three, not one.

The first guy came quickly. In fact, so quickly that I hadn't had a chance to have him pull out before he blasted cum down my throat. The second guy's appendage was bent, like that of a pronounced curve of a saber sword. He lasted longer. The good thing was although he wanted deep throat, he wasn't so big that it was a problem. Now I had swallowed three loads and prepared for a fourth. That's not what the last guy had in mind. He was so hard his cock stood upward at a forty-five degree angle and twitched like a dog's tail. After fucking my mouth for what seemed like hours, he grabbed his cock, creaming my face, repeatedly firing his cock juice straight between my eyes. Jesus, how that stung!

Thankfully, there was a bathroom near the rec room where I could clean up. I washed my face, put myself together, said goodbye to Gail, and walked home.

Who knows why I did it? Maybe I was a little too impulsive, or it was vanity to prove to myself that I could satisfy guys. Maybe it was my need to be popular. No matter, it was in the past.

Halloween presented a new opportunity. Our school was sponsoring a Halloween costume dance. I had the perfect costume for the occasion. I dressed as a French maid. My god, it made me look so sexy. My date was with Eldrick.

The French maid outfit was pure exhibitionism. Anyway, we had been at the dance for a half hour when we were asked to leave for wearing an inappropriate costume.

Here's the thing, we had been warned about clown costumes that year and told they were inappropriate and discouraged. "Discouraged" meant, they were not allowed. Last year sombreros and ponchos were banned because they would be considered "discriminatory behavior." The year before, pirate costumes were "discouraged" because they denigrated the handicapped. No one said that French maid costumes were not allowed. So where did I break the rules?

After being thrown out of the dance, Eldrick and I made out on his parents' living room couch. He had his hands all over me and his lips on my tits. The costume made it easy to get what he wanted. I had gotten accustomed to a boy sucking my tits and playing with my pussy. It was all exciting, but it didn't go beyond that. Some of the guys were too shy or not confident enough to take it to the next level. There were others that I didn't want to be my first and those who would be so horny they would cum before diving into my slippery slit.

Eldrick would have been fine and the location was perfect. Taking my virginity on a living room sofa would be so much better than like a whore in the back seat of a car. Only, Eldrick was more interested in getting another blowjob. He told me how the tip of his penis was the most sensitive part and how to lick it in circles while stroking his balls. He seemed to love my hands lightly touching his large firm sack of nuts.

It was that night that I learned what it was like to deep throat a really big cock. I had taken guys all the way down before, but they weren't big like Eldrick. At first, it was just letting him push to the back part of my throat, but he still had a couple of inches left. Of course, I gagged when he pushed past my tonsils. I recovered for an instant then he penetrated me further. I gagged and coughed again. Tears rolled down my cheeks but that wasn't going to stop him. On the third try, he took the back of my head and impaled my throat all the way. I was paralyzed and couldn't breathe. Finally, after several more tries, I learned to calm my gag reflex.  Eldrick continued to fuck my throat over and over again going deep every time, but without me gagging or tears.

He finished with a surge of creamy fluid that overflowed from my lips. The only thing was that some of it got on my French maid costume and that was going to hard to explain at home. Well, maybe not. My mom was an understanding type when it came to sex.

Eldrick told me I was the best, and he had never known a girl able to take him all the way down. I guess that might be considered a compliment. For me, it became a point of pride.

Following our first basketball game, I was busted for wearing the thong under my cheerleading skirt. I was thrown off the squad which was embarrassing but to be honest, it wasn't something I missed. I needed to concentrate on my studies if I planned to attend college next year. My interest in boys became more intense and time consuming too. I was now dating a couple of nights a week.

Thanksgiving was a non-event. Most of my friends were either with family or were out of town. That was not the case with my mom. She was hosting friends, men friends of course. One guy was particularly memorable. His name was Anthony. He spoke English with a wonderful Italian accent. Anthony was from Italy and had been in the United States for a little over a year. He thought nothing about walking around the house wearing only bikini briefs. He said things are different in Italy and that was obvious. The prominent bulge between his legs was a walking advertisement for his virility. My mom had a sixth sense about a man's vitals.

I think Anthony wanted to fuck me. When Mom wasn't in the room, he would get real close, give me a hug, then say nice things about my body. One time he came up to me from behind and wrapped his hands around my breasts. He got a handful and said, "Bella, bella." Anthony would have been perfect for my first time, but we had no chance. Mom was off work for the holidays, and he was only at our house for two nights.

The other guy mom had that week was a jerk. I stayed as far away from him as possible. Luckily, the only time I saw them was at dinner time.

After Thanksgiving, I fantasized about having someone in my bed like my mom. To keep me from going crazy, I used the handle of my hairbrush for some pleasurable relief. I could only imagine that it wasn't a brush, but a hard cock pumping my pussy.

Leading up to the winter break was a busy time. Mom had me decorating the house for Christmas on the first few days of winter break. She said she had to work overtime during the holidays. It also gave me a lot time to myself.

For entertainment, I would masturbate watching porn videos on the Internet or look at the DVD Mom had hidden in the family room. One of the "models" in the video looked a lot like my mom at a younger age. I always wondered if she did porn back then. Maybe she's still doing it, and kept it a secret. After all, Mom certainly liked her men.

One guy from my class, I think his name was Josh, came over to our house on an afternoon during winter break. Mom was at work, of course. We were doing the Netflix and chill thing. We watched a video together assisted by some heavy petting that developed into something more. He had a stub of a cock, so he wasn't going to be my first. Sure, Josh got hard and gave me a good shot of cum to swallow, but we weren't going to go all the way. By that time, making a boy cum had become an obsession.. There was something very compelling, if not rewarding, in knowing that I had the control to gratify a boy in that way.

Despite Josh's inadequate anatomy, he was able to satisfy me in a way that was completely new. I was nearly naked except for my panties when almost without warning, Josh pulled them down and spread my legs. He had his tongue on my clit and two fingers in my pussy in an instant. He ate me out for a good half hour. The boy really knew a girl's anatomy and how to satisfy her. I probably came three or four times with his head between my thighs. He said I was the tastiest girl he had ever had.

From then on, if I was going to give head to a guy, he was going to do the same for me. "Tit for tat," you might say but in a good way.

So I was having light sex with lots of different guys, but never scored. Either it wasn't the right guy or the right place. Perhaps I was too choosy, but I wanted it to be memorable. There's only one first time. You know how they say, "The first time never comes twice." That explains why I was technically still a virgin.

The new Natalie was now one of the most popular girls, at least with the boys. Rumors started to circulate around school that I was a slut. Some of my girlfriends no longer talked to me. I really wondered if they were jealous, or because I gave their boyfriends blowjobs at Gail's party. The thing was, while my friends were fucking those guys, I still hadn't screwed anyone. It just seemed so ironic and hypocritical.

That all changed after New Years. January began with a huge winter storm. They called it a hundred year blizzard. It arrived on a Thursday night. Friday, schools were closed and many businesses didn't open until noon, if at all. My mom was out of town with some guy for a four day weekend. I was all alone and stuck inside.

Alone, that is, until the doorbell rang. I wasn't exactly dressed for company. I was still in my after shower robe with my hair all wet and tangled. I looked like a girl in a slasher movie.

At the door was Joe Flynn, Gail Flynn's father. Gail was my next door neighbor, and my best friend since the third grade. They had moved from London to the United States a decade ago.

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She was the girl giving the after game party when I indulged in some over-time activities with the football players.

Mr. Flynn had used his snow blower to clear our front walk so I could get outside. That was great, but there was no place for me to go! Mr. Flynn was checking up on me to make sure I was okay. Anyway, that's what he said.

He was covered with snow and looked frozen like Frosty the Snowman. He was shivering.

"Hello, Natalie. I hope you don't mind me turning up at your door like this, but I'm a bit wet and chilled. How are you doing? Are you okay? Do need anything?"

I said everything was fine and thanked him for doing the walk.

"Do you mind if I step in for a moment. I need to warm up for just a minute?"

So I invited him in. I took his coat and hung it on the coat rack while he pulled off his boots. I offered him coffee or hot chocolate. He said, "Actually, I could use a shot of brandy, if you have it. Brandy just warms me from the inside out," and he gave me a comforting smile.

I looked in my mom's liquor cabinet and found a bottle of Five Star brandy and a shot glass. He gulped it down like a thirsty man in a desert, then he asked for another. I just handed him the bottle. We sat on the couch for awhile talking about the weather.

Here is were it gets either interesting or embarrassing, maybe both. From downstairs came voices. Oh my god. I left my mom's video playing when I went upstairs to open the door.

"Is someone downstairs?" he asked.

I started to say, "It's only a    " He didn't wait for me to finish when we heard a woman's loud moan followed by a piercing cry from downstairs. Quickly he raced past me, and down the stairs to the family room. I stayed upstairs waiting for the inevitable. It was not going to be a pretty scene when I got down there.

"Come down here, Natalie. I want to talk to you," he hollered.

I was in no hurry to join him. I took my time. My face was flushed with embarrassment when I reached the last step. Mr. Flynn was sitting on the sofa where my mom had been fucked so many times and the video was still on. It was an orgy playing out on the TV, a gang bang scene in HD color. It was my mom's video that I had been watching to wait out the storm.

"Natalie, do you watch these often?" he asked in a stern parental voice.

"Once in awhile," I lied. "All the girls do."

"Does Gail watch them too?"

"I don't know, Mr. Flynn. She hasn't been here to watch TV."

"You know, Natalie, this is really a shock. Would you be an angel and bring me another brandy?"

"Yes sir," I said politely. I was in no position to argue.

I ran upstairs returning in slow motion with the bottle and a more dignified glass. When I reached the bottom of the stairs, Mr. Flynn had his shirt off hanging it by our glowing fireplace. He was naked from the waist up. I couldn't help noticing his bulging muscles. He was a man in his middle forties, fit, and ruggedly handsome. To my surprise, he was still watching the video.

"Have you ever had brandy, Natalie?"

"No," was all I could say, then I asked, "Why did you take off your shirt, Mr. Flynn?"

"It's soaked all the way through. I'm letting it dry off by the fire. Do you mind?

"Not really," I said, but it sure was a surprise and to be honest, a turn on.

"Here, give this a try," and he handed me his glass.

I took a sip. It tasted awful! It was like taking medicine. Mr. Flynn could see my displeasure when I wrinkled my nose.

"Yeah, I know. The first sip isn't so good. It's an acquired taste, but it keeps getting better each time you try it. Sit here. I want to talk to you about watching porn."

I did as he said. Then in a voice filled with guilt, I said, "Look Mr. Flynn, I don't watch porn, but my mom left it in the player and I was curious."

"Don't worry, Natalie. Your secret is good with me as long as you can keep my secret."

"What's that, Mr. Flynn?"

"The truth is that I've never seen a porn video before, so I'm curious just like you. Sure, I've browsed the Internet but never seen it on TV. My wife would divorce me if she knew I was watching this, especially with a pretty girl like you. She's kind of a prude. Why don't we just enjoy watching it together, and keep this between the two of us."

I took a couple more sips of his brandy and said, "Okay. I guess it's fine with me if it's okay with you."

"All right, we have a deal," he said with a sly grin. "You haven't left me much in that glass. Go ahead and finish it and I'll pour myself another one if you don't mind."

I did as he said sipping it slowly. "How's it taste now?" he asked.

I said, "It's okay. A little better, but not great." The truth was that it still was like medicine. On the other hand, the brandy had a calming effect. I felt so much more comfortable, less nervous. I was beginning to relax. Also, there was a naughty side of me coming out with Mr. Flynn next to me watching a full breasted woman in the video being double teamed.

"Maybe I shouldn't say this, Natalie, but does that lady in the video remind you of your mom. I mean, your mom is really beautiful and sexy like this girl."

I was noncommittal as we watched the trio of actors moving about the bed displaying a variety lewd acts. I couldn't stop watching.

"Would you like to give brandy another try?" Mr. Flynn asked.

"Okay, why not," I giggled. At this point, the taste didn't matter.

He smiled and said, "Come here and sit on my lap for a minute."

It was cozy snuggling up on his lap. I imagined he was the daddy I never had. I was really really happy and in a serene melancholy mood. I think Mr. Flynn was feeling the same way when he put his hand behind my head and gave me a kiss that I'll never forget. Believe me, it was not a father-daughter peck on the cheek kind of kiss. It was deep and passionate like nothing the high school boys had done. My heart nearly jumped out of my robe that kept slipping open from time to time. I returned his passion with my tongue deep into his hot mouth. I could feel my breasts swell and at the same time noticed an unmistakable bulge in Mr. Flynn's lap. This always happened to guys when we make out, but this was different. Mr. Flynn took my hand and placed it firmly on the mountain rising between his legs.

"Have you ever felt a boy like this, Natalie?"

My heart was pounding, and I didn't know what to say. Finally I murmured, "Uh huh."

"Natalie, I'm thinking that your breasts are as lovely as the lady's in our video here. Would it be too much to ask for you to show them to me?"

Maybe it was the exhibitionist in me or because my head was swimming with lust, but I so much wanted to show them to him. I didn't say yes and I didn't say no. He took it as a yes and put his arms around me. Mr. Flynn was delicate with his touch as he drew back my robe. There I was naked from the waist up with my best friend's dad. It didn't seem real. It was more like in a surreal dream.

All he said was, "Oh my god, you're fabulous."

He just stared at my boobs for what seemed like forever. I had never been so embarrassed before. Then he said, "You, my love, have been generously endowed. Natalie, you are smoking hot. Your body is absolutely sensational. To be honest, I can't take my eyes off of you." At that he held one of my boobs in his hand and began sucking on my nipple. He followed that with the same attention to my other tit. It was hard to catch my breath feeling the tingling sensation all the way down to my engorged clit. I nearly had an orgasm just from his touch.

From then on, everything happened so quickly and with little forethought. With a free hand, I fumbled with his zipper. Finally he had to help, then pushed his pants down to his knees. Mr. Flynn wrapped my fingers around his already hard cock that stood straight up like a flag pole. He didn't have to show me what to do next. I couldn't resist stroking it. Massaging a guy's dick is something I'd done many times.The best part is looking at the boys' faces as they fall into a hypnotic trance. Mr. Flynn was no different.

This was a man's cock, not a boy's. It was so thick, almost muscular by how hard it felt, and more than a handful. Almost immediately he was oozing precum. Without his encouragement, I had my lips around his firm long love stick and gently cradled his taut balls with my hand. Maybe that wasn't the right thing to do, but at that moment I just couldn't help myself. Anyway, that's how it happened without thinking twice.

I began to suck at the knob of his prick like Eldrick taught me, then slowly engulfed him further. He held my head moving it in a steady motion while I mouth fucked his throbbing shaft. When I picked up the pace, I expected him to release a load of cum down my throat like all the boys did. Mr. Flynn was no boy. He knew how to hold back his ejaculation for a better deal. That better deal was waiting between my legs. By this time, I prided myself at giving great deep throat. Although he was thick and lengthy, I was able to go all the way down to the root of his cock.

"Ahhhh, good god, you do that so well, Natalie. You have the face of an angel and the mouth of a whore."

I wasn't sure if that was a compliment or an insult but either way, his hands wandered down between my thighs. Tucking his hand between my legs, I moved them apart making my wet steaming cunt more available. His finger, then two fingers entered my smoldering twat. As he finger fucked me, at the same time his thumb found my plump clit pushing me over the edge.

"Love, you are dripping wet. Let's not play games here my sweet little tart," he growled. "I've been wanting to shag you ever since you acquired a woman's body. It's time to show you how a real man satisfies a girl."

I was just short of my eighteenth birthday, and he was referring to me as a woman. That for sure was a complement. I felt so grown up. I was totally taken by his easy charm, his British accent and his body. I didn't resist when he pulled my robe completely off. I didn't care. I was so horny. Mr. Flynn dropped his pants to the floor and the two of us were completely naked. A vision of my mom and her boyfriend fucking here in the family room sofa flashed in my head at that moment. This was it. It was the moment that I had waited so long to happen, Now it was finally going to be my turn.

In the background, the sounds of men and the woman in the video achieving their climax enhanced our lust. The video was about over but my moment of passion had just begun. My fantasies of having intercourse for the first time had been an illusion playing in my head. It was only like Hollywood, unrealistic. It was nothing like the real thing. A girl can never have it in her imagination the way it actually happens, and for sure, it was going to happen this time.

Mr. Flynn stretched me on the sofa spreading my legs far apart. His mouth, lips and tongue tasted my pussy sucking on my swollen clit. He found no resistance with two fingers sliding into my gaping sex hole. I was dizzy with desire. He continued to give me oral pleasures, enhanced pleasures that I had never experienced like that before.

Mr. Flynn whispered in my ear, "Natalie, I need you. I want you so bad. I want to make love to you in ways you will never forget."

"Oh yes, Mr. Flynn. Please, I want it so much. I've waited so long. I want you inside me. I want to know what it feels like with you inside me."

He didn't have to be asked twice. The tip of his penis found the lips of my virgin opening, sliding his knob up and down my slit making me delirious with desire. Then all at once he shoved himself all the way in. I let out a little yelp, more from surprise than in pain. He had entered and filled that neglected dark cavern just waiting for this moment.

I hadn't expected the sensations. At first it reminded me of squeezing into a new pair of shoes, a little uncomfortable, slightly tight, but accommodating. And like wearing new shoes for awhile, it soon became a good fit, a satisfying fit. But unlike the shoes, I felt a rush of excitement and extreme pleasure with each of his thrusts. There was something else that had me giddy with lust and that was feeling his balls slapping against my ass. It's something you just don't get with a hairbrush.

He soon became more animated plowing into me with what only can be called raw power. All at once he was high energy; his breathing became heavy, and he was making guttural sounds like those in the video. I could feel myself working up to an orgasm and soon a massive climax that I had never experienced by pleasuring myself. He turned me over on the sofa with my ass in the air when he slipped into me from the rear. This seemed to energize Mr. Flynn again as he pounded into my pussy with stroke after stroke of determined energy. I screamed out, "Please don't stop Mr Flynn! Fuck me, fuck me hard." The urgency in my voice made him crazy. Mr. Flynn drove himself all the way in, balls deep, and I felt his contractions and spasms pumping wad after wad of cum deep in my womb." It was at that moment I had my strongest orgasm and yelled, "I'm cumming. I'm cumming." They were sensations I could never have imagined before.

He was finished. I was exhausted and totally fulfilled. It was over. I no longer was a virgin. It was time to celebrate.

We said nothing to each other while he poured himself another glass of brandy. For a long while, I didn't know what to say, and I was afraid to look him in the eye. Should I feel ashamed? Should I feel guilty fucking a married man, my girlfirend's dad? I wondered while I drank the brandy.

He kissed me again, a good hard passionate kiss, and said, "There isn't another girl in the world that can compare with you."

I barely heard what he said. I hadn't come down from the high of multiple orgasms. It was if I was in a daze, lost in the nirvana of pleasure.

"I think," he continued, "that it would be best to keep this between us. You know, it's better that you don't mention what we did to any of your girlfriends, especially Gail."

Of course, what he meant was to keep the fact he fucked me a secret. "Okay, Mr. Flynn," I murmured. "God, how I wanted you the moment I saw you with your shirt off. You made me the happiest girl on the planet. I only wish we could do this again.  "

"I'm glad you feel that way, love. We'll meet again if you like, but I have one question. I don't wear condoms. As you know, I didn't just now. You probably felt me cumming inside you. I think it's more pleasurable for both of us that way, don't you?" He sounded nervous.

"Of course, Mr. Flynn," I said, but I really didn't know anything else. "Don't worry, Mr. Flynn, I won't get pregnant. My mom put me on birth control in my freshman year in case something like this would happen. It never did until today. I'm so glad it was you that took my virginity."

"I'm so glad to know I was your first, Natalie."

At that, I gave him a huge hug and a deep passionate kiss. I begged him to do me again, one more time before he left. The thing was, the girls at school said they didn't like their first time. I loved it. I just think they did it with the wrong guy.

He fucked me twice more. The last time he was seated on the sofa with me on top. Mr. Flynn said that watching my boobs bounce was so spectacular that he was able to cum for a third time. I liked it too because I was in control. From then on, I wanted to be on top.

My god, these were my first times, so I hadn't anticipated how to deal with his cum leaking from my cunny hole and drooling down my thighs. That was a little embarrassing but Mr. Flynn didn't seem to notice. If he did, he didn't say anything or didn't care.

He finally said, "I've never cum three times like this. You totally drained me my dear girl with that lovely tight muff of yours." Then he added sounding a bit guilty, "You should know that I normally don't come on to a woman like I did today. The thing is, I haven't had sex with a woman for over a year. My wife doesn't like having sex. I needed you, Natalie. You are a wonderful girl. You gave me so much pleasure. I hope you feel the same. You are a princess who made me feel like a king today."

Of course, that made me feel like we had done the right thing. The actual physical part of it was as gratifying as my fantasy. I just wanted it to happen all over again.

He left for home just before dark. What he left behind were memories, three loads of his cum inside me. and a few stains on the couch.

In the morning, my pussy was so sore that I couldn't even think of having sex for a few days. When that passed, I invited Eldrick to drop by the house after school on a cold Friday afternoon. Mom was working late again, and she wouldn't be home until ten that evening.

I greeted Eldrick wearing Mom's teddy with her garter belt and mesh stockings. I wore no panties. He stared at me for a split second then threw off his coat. I led him to my bedroom with him pulling off his clothes on the way. He didn't have to be told what was going to happen next.

He was already hard when I sat him on the bed. My face engulfed his cock, and I could already taste his precum. This time I wasn't going to take his load in my mouth like before. He was getting dangerously close to blowing his wad when I pushed him back onto the bed and sat on his dick. My cunt was already convulsing with orgasms when I stuffed his cum-stick all the way in. I rode him cowgirl with my breasts bouncing rhythmically with each pounce, until I could feel his cock begin to throb and pulse. He let out a vulgar grunt and yelled, "Fuck, fuck, fuck," releasing streams of hot creamy sauce into my wet fuck hole. We collapsed together on the bed and just laid there for a long long time.

His first words were, "You are a great fuck."

I said, "I want you to do me again."

He said, "I need some time."

We spent the next hour exploring each other's body. I played with his balls and teased his cock until it was finally clear that he was ready to fuck me again. I was on my knees and he plunged in from behind. I had my share of orgasms while he banged into me hard and fast. This time we had a longer fuck session before he began shooting liquid bullets of semen into my hot twat. When we finished, both of us slept until it got dark. I ordered pizza, and we sat at the kitchen table nude, laughing the whole time.

When the pizza was gone, he said, "Let's try anal."

"Huh?" I replied. "You want to fuck me in the ass?"

"Sure, why not? Check your mom's dresser and see if she's got some lube. We need to get greased to do it."

"How would you know about my mom's dresser?"

"From my dad. He's been here a couple of times with your mom. They do anal all of the time. Didn't you know?

"I didn't know he was your dad."

"Okay but he said you were pretty, and we should hook-up. You didn't think it was an accident that we met at Gail's party, did you? I asked Gail to fix us up."

I had no idea Gail was in on it.

I already knew that Mom had a stash of sex toys so a tube of lube had to be hidden somewhere. When I got back to my bedroom, Eldrick was already stroking his cock. It stood at attention when I handed him the lube. He squirted a glob of it on his dick. Next he turned me on my knees and liberally lubed my anus. I really didn't know what was going to happen next.

He used his fingers fucking my ass before mounting me like a male dog fucking his bitch. Eldrick took his time slowly penetrating my bum. As he squeezed himself in, the feeling was weird and it hurt at first. The further he pushed in, the more relaxed my butt hole became. Deeper and deeper he went until he was all in, but he wasn't thrusting. I started rocking giving him the idea I was ready for a good pounding. He quickly responded.

It surprised me how the inside of my ass gave me a tingling sensation. This was fun, almost as much fun as in my next door hole. Anyway, it took awhile until he creamed me deep into my intestines. It had such a grunty feel, as if I had to take a shit. In fact, when he was finished, I headed for the bathroom.

He left for home before my mom arrived an hour later.

As for Mr. Flynn, we meet on occasion during the rest of the winter and early spring to renew our relationship. Sex got better each time. He never seemed to tire of my girly giggles. He claimed my youthful screams at the peak of my orgasms made him cum even longer and harder. Sometimes we met in our family room with my mom away like the first time or at his place when no one was home. Mostly we found other opportunities like in his van and even once on a warm night on a park bench.

Our outdoor sex was great especially the time we were in a forested area in the middle of an April day. It seemed so dangerous and exciting to be in a public place where hikers and bikers came near us as we exchanged our carnal desires.

Several times Mr. Flynn took me to a seedy motel at the edge of town where he taught me so many things about having sex that I'll never forget. I was his girl slut, and we both loved it.

Mr. Flynn delighted in pouring his seed into my young pussy as much as I adored his creamy fluids flooding inside me. I liked it best when he fucked me hard and fast never stopping until I had repeat orgasms. Of course I was usually on top when he finished with blast after blast of cum deep into me. Like he had said the first time, "It's more pleasurable for both of us that way."

He would often come back for seconds and an occasional third. He enjoyed doing me doggie style. That's when he liked to tease me. He knew from my moans when he had brought me close and on the edge of an orgasm. He would then slow the pace and stop until I begged and begged for more. All at once he would shove in his pulsing cock banging away until I screamed from a powerful orgasm. It must have been the begging that turned him on.

If he wasn't copulating inside me, he pressed his cock between my voluminous breasts, tit fucking me until a geyser of his love cream sprayed my neck and chin. The feeling of his hot cum erupting all over me was likes a hot shower on a cold day.

One time when he was down on me with his head buried between my legs, I got so horny that I came all over his face. He smiled then delivered a never ending torrent of semen that covered me with an unforgettable facial. He scooped it up with his fingers and had me lick it off. I gave him a wink and licked the last creamy drops from my lips as if to say, "Yummy." I was just pretending to be like the woman in my mom's video, but that's another story. Mr. Flynn smiled, then gave me a deep romantic kiss. It was our last.

At the motel in late May is when we got busted. His daughter, Gail, was near the motel, and spotted the family van parked outside of one of the rooms. She was curious of course. After awhile, Mr. Flynn and I left our room. She saw us together. That ended my romance with her dad.

But the question remained, what was Gail doing at the motel late at night? It turned out that she was there fucking our American History teacher. Who would have guessed? As for a double standard, she hasn't spoken to me since.

It was sad not to see Mr. Flynn again, but then, I still had Eldrick to keep me happy and several others before graduation.

Published 
Written by xhardx13
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