Category: first times

A Surprise At The Party

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I was at a party. A typical college party. Beer flowed from kegs and cigarette smoke filled the house. Men all moved about desperately trying to be cool and attractive for the ladies. The ladies moved about in various outfits. One wearing a teeshirt and jeans, one in a tight black dress, another in a halter top and shorts, and with each different outfit there was a different figure.

The girl in a teeshirt was not fat, but full figured with long dark brown hair and large breasts firmly standing underneath her shirt. The girl in the dress was almost her opposite, tiny features, tiny figure, tiny breasts, tiny blue eyes with soft blond hair. The girl in the halter top had a slim figure that curved around her body and lead to firm C-cup breasts, almost popping out of her top. If you could look up, you were drawn to her eyes which called for sex. Whatever the dress and figure, they were all beautiful and sexy.

I laughed. The room longed for sex, but not many of us would have the opportunity. I looked at the empty cup in my hand and turned back to the keg.
Bump. Slosh

“Oh shit, I’m sorry.” I hadn’t realized that there was a girl right next to me and had bumped into her, spilling her beer on the floor. “Shit, ummm, let me get that.”

She didn’t say a word, just looked at me. So I looked at her.

She was beautiful. A small body. Long, light brunette, slightly curly hair. A soft face. Deep green eyes. Long lashes. A figure that curved up and down her side, around her tight ass, and along her long legs. She had breasts that were the perfect size for her body, probably a C-cup, firmly pressed together and proudly standing on her chest. She wore a white tank top that showed a little cleavage, a long, brightly colored hippie skirt, and sandals. She was a dream woman.

She didn’t say a word, but her eyes washed over me, assessing me.

I didn’t know what to do, so I spoke, “I’m really sorry. Do you want a towel? Should I get a towel? I should get a towel.”

She took my hand. Her eyes gave me one last sparkle, then she turned, leading me through the crowd.

I didn’t know what to do, say, think, so I followed.

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Virgin Schoolgirl Needs Better Grades

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“Mr. McCoy, I just have to start getting higher grades in your class if I’m going to get admitted to any of the best colleges. I’m acing every class but yours and I’d do anything to get straight A’s from you too.

“Anything? Do you really mean that?” His smile widened as he asked her that and lecherous thoughts swirled through his mind.

“Yes, I do. Anything. Anything at all. I would even be willing to have sex with you but I’m a virgin and I have to stay that way until I’m married. My parents are very strict and so are the mother and father of my fiancé. Even so, I would be willing to have sex with you but it would have to be some any way I can do it and still keep my virginity?”

“I’m quite sure we can work something out, Ruth. Suppose you come to my office after school ends today and we’ll see if we can think of something.”

Dennis McCoy already knew what he was going to be thinking of and he hoped Ruth would be as willing as she said she would be. She was about the hottest girl in the high school where he taught Geometry, with long red hair, green eyes and a few scattered freckles that enhanced her perfect ivory complexion. Her breasts were big and shapely too but neither they nor her face was Ruth’s main attraction. As he watched her walk out the door of his office in her long knit dress, he knew what was. He was a man who loved female asses and the body he was eying had a bottom that was as close to perfect as any he had ever seen, big and curvy with a truly delightful sway. He would talk with her after classes ended for the day but he already knew what he wanted to do to her later when her dress would be bunched up above her waist and she would be leaning over his desk.

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18th Birthday Picture

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For Maggie Crane’s 18th Birthday, her bestfriend Lisa surprised her with a free birthday photo shoot by a famous cameraman, John Lucy.

Lisa is envy of her bestfriend Maggie. She thought Maggie was beautiful, though Maggie didn’t think so herself. She didn’t like how pale white her skin was. She didn’t like the fact that she was really tall. Like around 5’8 or 5’9. She thought her feet were kind of big because she wears a size 10 in shoes. Her dirty blond hair is just plain looking and she always had it either tied in a ponytail or straight down. Her ass was pretty much the only thing that looked right on her body. The biggest problem Maggie had was her enormous breasts.

She outgrew all the other girls in high school by the time she was 15. She was already wearing a double d bra. As she grew, her bra size increased and now that she was 18, her tits are now a whopping 34FF.

Her ample breasts started low on her chest and sloped out to huge mountainous soccer balls. The bottoms of her mighty mounds rested just above her belly button with natural sag. If she had the money to get her breasts deduced, she sure would have done it.

Lisa knows that her bestfriend Maggie is kind of shy about getting her pictures taken. That’s why she wanted to surprise her. Over the years in recent pictures, every camera had zoomed in or focuses on Maggie’s upperbody. No one besides her family has ever taken just a regular face shot without including her huge tits in the frame.

Since Maggie had no idea where Lisa was taking her in the middle of the afternoon, she didn’t get all dressed up for the surprise photo shoot. Instead, Maggie wore her favorite double X-Large light blue tee shirt, with a picture of a dolphin stretched out and distorted across her large chest. A pair of dark blue jeans and her favorite tennis shoes. Maggie was never into dressing up for any occasion and wanted to feel as comfortable as possible.

“Can I take this stupid blindfold off please?” asked Maggie as Lisa drove the both of them to the photo shop.

“Not yet?” said Lisa as she pulled up into the parking lot.

Lisa got out of the car and opened the door for her friend. She guided Maggie into the photo shop. Once inside, Lisa guided Maggie to a long, black leather sofa and Maggie fell backwards on it. Her enormous breasts bobbed underneath her shirt and Lisa couldn’t take her eyes off them.

“Gosh! Maggie’s breasts are HUGE!” Lisa said to herself. “Ok Maggie! You can remove the blindfold now,” said Lisa.

Maggie took off the blindfold and saw she was in a photo studio.

“LISA! How could you set me up to take pictures for my birthday?” questioned Maggie.

“It’s my present to you Maggie… So please just get a couple pictures taken for your birthday. Then I promise we will go somewhere fun,” Lisa pleaded.

“I guess someone doesn’t like having her picture taken,” said a man’s voice.

“Oh my god Maggie! It’s John Lucy. The famous cameraman for the stars,” gasped Lisa.

“Oh yeah! He does take the prettiest pictures of the celebrities. Even the ones that are not so pretty,” Maggie said.

“How do you do girls,” John Lucy greeted them.

John walked out from the shadows to reveal his tall, dark, and handsome self.

Lisa and Maggie were both drooling over the hot blond 25-year-old cameraman.

“Please! Tell me why don’t you like getting your pictures taken birthday girl Maggie?” John asked.

“Well….because…I never turn out right in pictures,” Maggie said slyly.

“Well Maggie. That’s all going to change tonight. I think you have a very beautiful face for photographing,” John said.

“Thanks!” Maggie said blushing.

“You’re gorgeous too Lisa,” John flirted.

“Thank you John! You’re very gorgeous yourself,” Lisa commented.

“Why don’t you take a seat next to your friend Maggie? I would like to see how you guys work together,” John said smiling.

Both Lisa and Maggie were memorized by John’s good looks and muscular body, which showed in his tight shirt and black jeans. They were so memorized by him that they would end up doing anything the man wanted. And John knew that.

Lisa took a seat next to Maggie. Lisa’s body was nowhere near voluptuous as Maggie’s. She was thinner the Maggie and shorter. She had dark black curl hair and was prettier then Maggie but Lisa didn’t want to gloat it to her bestfriend.

John started taking pictures of the duo. He had move close together. So close that, Maggie’s massive double F cups crushed against Lisa’s C cups. John started to get very hard and it showed as a large bulged formed in his jeans.

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A Very Horny Birthday

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I’m a single father raising two teenage kids: Sara, who is 19, and Mike, 18. My wife Julie decided after three years of marriage that she wasn’t the family type and left us. It’s been just the three of us since.

For Mike’s 18th birthday I decided to rent a skin flick, buy a six pack of beer, and just have a “guy’s night” with him. Mike has always been a little introverted, always studying to get good grades, and shy toward the girls. I figured our celebration might loosen him up a bit and let him have some fun.

We were about ten minutes into the flick and had just finished our first brew when Sara walked into the room. Immediately I became uncomfortable because I didn’t know what she would think about what we were watching. She was the type who would consider a porno movie chauvinistic or immature. To my surprise, she just asked if she could watch too. I said sure and she plopped down on the couch next to Mike.

During the slow parts of the movie I glanced over at the two of them to see their reactions. Mike was riveted to the TV; I was sure he was a virgin and that this was the first time he had witnessed sexual acts. He studied every scene intently. Sara seemed nonchalant. Unlike Mike, I knew Sara had been sexually active because she had asked me to buy birth control pills for her since she was sixteen.

As the movie neared the end, Sara began to shift her legs around during each of the hot scenes. She had shared a beer with us and I figured the movie was starting to get her aroused. Mike’s face was still glued to the TV. It had an effect on him too: the lump on the inside of his left leg was growing quite long. Sara became increasingly fidgety and finally placed her hand on Mike’s leg. This startled him out of his gaze for a moment, as if he realized for the first time that his sister was sitting next to him. He immediately turned his attention back to the TV, not wanting to miss a moment of the action.

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Cock Tease

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There she was, running the track again in those short very tight fitting pants and sports bra. She was the biggest flirt around always teasing guys with her skimpy clothes. I was there playing footy (I’m an Aussie). We were doing tackling practice and I was staring at her running past us. Little did I know it was my turn to get tackled. I may be 6 foot 4 but when your standing flatfooted with one hand down your pants being tackled really hurts. I pulled the grass from my hair and got up staring at her again, she was giggling as she ran on past.

After training she came up to me to say hello. ‘Hi Smitty,’ How was training. She asked doing her beautiful blonde hair into a pig tail. “Hey Nikki, yeah not too bad.” I started to shake, she was soo hot.

Nikki was my next door neighbour, we used to hang out as kids but when we mad high school she got sexy and lost interest in me. “Will you walk home with me Smitty?”

“Of course.”

We got walking and I could tell a few of my footy mates were excited for me. When we got to her house she asked if I wanted to come in for a while. I asked if here parents were home and she said the wont get back till late. I complied and walked behind her, her shorts had rode up and I got a great view of that sex ass of hers. I guess this would be a great time to describe her. At just barely 18, she was a very sexy blonde not too good with heights or bra size but I guess she is about 5 foot 4 and a very descent cup size. She has a beautiful firm ass with sexy legs.
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Her New Bra

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Kimberly O’ Brien was stretching before gym class started. All the guys in the class couldn’t help but watch as Kimberly stretched. Even the girls eyed Kimberly’s stretching. This was an everyday event for the guys and girls to watch Kimberly stretch. The 18-year-old had a massive bust.

Kimberly would notice her fellow gym students looking and glancing at her chest. Kimberly knew her huge 38EE cups were a spectacular sight. She had the biggest boobs in the entire school distract. Even some of the female staff was jealous of Kimberly’s bust size.

Today would be a day that Kimberly and her gym class would never forget. As Kimberly continued stretching, she bended her back and thrust her chest out forwards. The weight of her huge tits really took its toll as her bra straps completely snapped. The massive support cups fell under her tits and they now hung down her chest with the nipples resting near her navel.

The guys in the class immediately felt their cocks harden as Kimberly’s oversized melons jiggled and wobbled freely under her plain tee shirt. Her big nipples poked through the material of the shirt and Kimberly’s face became red. Kimberly immediately cradled her boobs and run out of the gym. She felt embarrassed and knew this was one of the wrong times in her life.

Kimberly’s mother Lucy came to the school to pick Kimberly up. Kimberly explained everything to her mother. Lucy decided that it was time for Kimberly to get a new bra because she might have outgrown her current bust size.

They arrived at Victoria Secrets. Lucy stayed in the car and handed her daughter her credit card so she could buy as many bras as she liked it.

Kimberly entered the store wearing her favorite hooded shirt. She didn’t want her breasts to bounce obscenely in the mall.

“Can I help you miss?” asked a man in a squeaky girl voice.

Kimberly knew he was gay and could trust him.

“Yes. I’m Kimberly O’ Brien and I’m looking to get my bust re-measured and to buy some new bras,” Kimberly said.

The man felt a small prickly in his crotch.
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Nineteenth Birthday Present

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It was the night before my nineteenth birthday, and, hell, had I waited long enough.

And I’m babysitting. Kids snoring in bed; me, alone watching a film downstairs when the door opens and the guy, hmmm, we’ll call him, hell, we’ll call him ‘you’ and his missus walk in. Home early. Her not well… Overindulged (hic), maybe… She goes straight upstairs, barely acknowledging me, and I hear her crash down onto the bed in the room above me. Small houses these. No secrets here,

The guy, you, you say I can stay and finish the film, pours a drink… Asks if I fancy a cider… Yeah, yeah, at almost 19 I’ve been drinking for four years or more already… And you hand me a can, cracking it open as you do so… Sit down next to me. Close enough. Far enough away.

I can smell you. Sweet, rum maybe, but my nose ain’t as refined as it’s going to be, smoky. And, not meaning to, I chew my bottom lip and pour a swig of cider down. You, I can feel you next to me, dark, moody, and I think you might be looking at me, but when I peer discreetly out of the corner of my eye, nope, your eyes are staring at the TV screen, not noticing me, now talking. Indifferent. And I push my arse back into the cushion behind me and relax.

It’s a bog-standard rom-com, a 90s film I just caught on the TV. I’ve got work tomorrow and I should be going but the cider slips down nicely, and you, though not watching get us both another drink, picking up a DVD on the way. Waving it at me, you ask if it’s okay to change, and I say cool as I take the can. Now I’m watching you, openly, just curious. You, still no interest in me, in talking, you sit down, a little closer. Warm.

I pluck up my courage and ask what we’re watching. You shrug. You don’t really know. A buddy leant you it, and then you just wink, all casual, told you to watch it with a girlfriend sometime. And I’m a girl, hell, a woman, aren’t I, and we both smile, laugh, and I take a sip.

Now you aren’t, this I know, the kind of guy to lure your babysitter into watching hardcore porn, because, baby that would be bad, you a married man and all. But something just a bit softer, a storyline slightly above, Chloeville and her amazing turkey baster. Something with a bit of story, tension… And we sit and there’s a tension all right. Tangible. Fucking tangible.
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Cheerleaders Diary

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Dear Diary,

Sorry that I haven’t written lately, but it has been a most amazing time at college. After eighteen years of being told by my parents, teachers and sometimes it seemed everyone else in my world, especially older brothers, what to do and when; these first few weeks have been amazing.

Of course, before they all drove me to college, my parents and every last one of my seven older brothers and their families threw me a fabulous eighteenth birthday party. I got all kinds of things for my dorm room and new clothes. I used the party to tell my high school boyfriend Steve that it was O-V-E-R. Since we were going to different colleges, we both knew it would never work…his fault for not making better grades so he could get into a good school like I did. I think he was cheating on me anyway; not that we ever went all the way.

That reminds me, the most exciting news of the past couple weeks…I lost my virginity. Well, had it taken is more accurate. Like in high school I tried out for the cheerleading squad. But things are different here at college. Instead of just entertaining the crowds and motivating the team at games, you have to entertain and motivate the players…off the field.

I was surprised and frightened at first when I found out. In fact, I almost decided not to try out at all, but I have ALWAYS been a cheerleader. My Mama was a cheerleader. Even Nana was a cheerleader, way back. Of course, they were only high school cheerleaders. I want to be the first girl in the family to make the college squad. I could not let a little thing like my virginity stand in the way of that.

I didn’t really know what it would be like. I heard the other girls, whose turn came before mine, talk about it though. It was simple really. You went to the dorm where most of the players lived and you signed in as someone’s study buddy. They came down and escorted you back to their room where you had sex with him…and any of his friends around. But you had to be done and out of there by ten o’clock curfew.

I was really nervous when it was my turn. At lunch, Sally May, the head cheerleader, gave me a slip of paper that contained the name and room number of the player that I was to…entertain and motivate. Wouldn’t you know it; it was Tyreese Moore, the star running back and possible Heisman Trophy candidate. I got even more scared then. I had hoped for someone more…well, like me; maybe the hot, blonde quarterback, who was known for his high grades as much as his throwing arm. If he did not make the NFL, he would certainly be a Rhodes Scholar.

Tyreese was the exact opposite of all that. He was a kid from the inner city, who could have never made it to college without football. He was also black. Having never actually been with a guy before, the thought of having a black guy as my first was terrifying. Was it really true? The size thing.
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Slumber Party Fun

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Mom and Dad had gone to the Caribbean for the weekend. They were going to be gone for ten days. I was at home with my two sisters, Jill, 19 and Janet, 18. Jill was studying with her friend Sylvia. They had a chemistry midterm Monday and were doing some last minute cramming. Janet was expecting some friends for a sleepover to celebrate her friend Monica’s nineteenth birthday. I was relaxing, listening to the alternative radio station and surfing around online.

The phone rang, and I picked it up. It was Janet’s friend Judy. Judy is a slim redhead with pale skin and a very few freckles.

“Hi, Steve,” Judy giggled. “How are you doing?”

“Fine, how is your car?”

Judy hesitated, “I wish I could say that I was done, but I had to get a new part, and it has not come in yet.”

“I’ll get Janet.”

I went downstairs to get my sister and went past Sylvia who was bringing up two glasses of coke. Sylvia has wavy black hair.

At the bottom of the steps, I looked up to see up Sylvia’s skirt. I got a quick peek of her round ass, which was visible, since she was wearing a thong.

I licked my lips to imagine how soft and smooth her ass would be to the touch.

Janet’s door was closed and the music was loud.

I knocked on the door, “Jan!”

“Come in.”

I walked in and saw that Janet was not alone. Sitting on the bed, legs crossed, wearing white socks and a blue summer dress was Janet’s blonde friend, Beth.

“Hello, Steve,” Beth smiled swinging her pony tail as she turned to look at me.

Beth was 18 and had been friends with Jan since junior high. I smiled back.

“Hey, Beth,” I smiled back.

Beth was no longer the skinny, flat chested girl I remember when she played soccer with Jan. Her breasts were nice and full, probably a C-cup. Her ass was nice and round without being too fat. In High School, I always had a crush on Beth, probably because I saw her so often.

“Judy is on the phone.”

“Thanks bro,” my sister was the youngest of her friends, having turned 18 last month and she still had braces. Like me, her hair was a sandy brown. But she had gray eyes where mine are green.

I walked out of my younger sister’s room when the door bell rang.

It was Monica, the birthday girl.

Monica was a short, brunette, like my sister, but her hair was a reddish brown, which she kept in a short, almost boyish bob. She was a tomboy, who liked to play touch football with the boys, and ate steaks instead of salads.

“Bye, Mom,” Monica waved to the SUV with one tire on our drive-way.

Monica grabbed me in a hug. She was wearing denim overalls over a pink t-shirt. Her tits were full like Beth’s and I felt them pressing against me in the hug. I thought how nice it would be to press my face into her soft tits. I wonder if she knew how much she was turning me on.

“Hi Steve,” Monica was always affectionate and was known to kiss me on the cheek if I did her a favor.

“Hey, Monica” I punched her on the shoulder.

“I want to talk with you about something.”

“What is it?” I asked.

“Not now, I’ll tell you later,” she walked past me to Janet’s room.

I went upstairs. At the top of the steps, I noticed that Sylvia had left my sister Jill’s door open. I walked over and peeked in. I could not believe what I saw.

My sister was standing in front of Sylvia and has one hand on her skirt covered ass. I could still picture the round globes of her ass that I had peeked at.

The two girls were French kissing. I knew my sister Jill had a boyfriend, Mike, so I figured she must like girls and boys. My sister turned Sylvia around and I could see that Sylvia was massaging my sister’s ass with both hands.
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Cheerleader Gets Fucked

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The superintendent promoted me from teacher to principal the same day Janet turned 18. I’d been watching that little girl shake her ass down the hallways of Jefferson High for more than three years. Every Friday during football season, she came to school dressed in her green and white cheerleader uniform. The mascot, an eagle, stretched across her luscious tits. All I could think about was making her spread like one. Now that I’d been given the powers of a principal and she was legal, I became determined to make my fantasy come true.

I told the secretary to summon Janet just before lunch on my first Friday as principal. Janet was a dutiful student; it took her no more than a few minutes. Her black hair was up in a ponytail, tied with a green ribbon to match her cheerleader uniform. School records said she was 18, but she could’ve easily passed for three years younger.

“Hi,” she said.

“Close the door Janet,” I said.

She gently shut the door.

“And lock it,” I said.

“Is there something wrong?” she asked.

“Just do as you’re told,” I said.

After the lock clicked, I motioned for Janet to take a seat in the chair on the other side of my desk. The skirt left plenty of bare thigh exposed. I imagined running my tongue up against that soft skin and making her sweet, virginal pussy wet for the first time. My dick turned hard as a librarian’s glare.

“Janet,” I said. “Do you plan to go to college?”

“Well, yes,” she said. “I’ve already applied to Brown, Yale and Stanford.”

I swiveled my chair so I could close the blinds on the window behind me.

“Do you know what a letter from your principal can mean to those colleges?” I asked as the room darkened.

“Not exactly,” she said.

“Let me explain it,” I said, turning around to shoot her a stone-faced glare. “If your principal writes a good letter, it can greatly enhance your chances of getting accepted to the school.”

I stood up and looked down at Janet. The lights were off. Slits of sunlight cut across her face. I sensed fear and vulnerability in her big, brown eyes, and then I knew I could have my way with her. I walked around the desk, knelt next to her and put my hand on her thigh.

“But if your principal writes a bad letter, it reflects poorly on you,” I said. “And do you know what that means?”

“It means I won’t get in,” she said.

“That’s right,” I said. “I knew you were a smart girl.”

I slid my hand under her skirt and rubbed her pussy over her panties. She already had a wet spot.

“Has a boy fucked you yet, Janet?” I asked.
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