Annie's First Time Adventure

Story Info
A girl's story of losing her virginity.
2.6k words
4.04
47.6k
6
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Annie hated her Intro to Sociology class, the only thing that kept her attendance up was Miles. Sitting right in from of her, for 80 minutes every Tuesday and Thursday, she could look at him. She was mesmerized by his short light blond hair, and every once in a while, when he looked over at his friend, she caught his bright hazel eyes. She wanted him, but Annie knew he would never want her. 'Who wants a virgin?' she thought to herself, but she couldn't help by fantasize about him.

She didn't have another class for the rest of the day after Sociology, so she would race back to her dorm and thanked that her roommate was a science freak and spent every minute she could in the lab. Annie laid down on her bed, and unzipped her shorts. Pulling them off of her, she began to rub her pussy through her silk panties. She was wet from the moment Miles sat down in front of her at ten o'clock this morning. As she envisioned Miles taking off her panties, and licking her pussy, she found herself rubbing harder, and eventually, took of her panties and was touching herself madly. Annie fantasized about sucking Miles, what she had hoped, enormous cock and choking on it, she thought about him sliding his cock in and out of her pussy and pounding it. Annie rubbed and rubbed herself until she began to shake. She always tried to muffle her moans, because she knew the walls were not sound proof, and someone could always be listening at the door. As Annie envisioned Miles cumming in her pussy, Annie came.

Annie steadied her breathing and covered herself up. She was sick of being a virgin. She wanted to know what it was truly like to have an orgasm. At 21, she knew it was time, in fact, she thought she would have lost it by now. She was too uptight though, and she knew it. "Loosen the fuck up, Annie," she told herself as she lay on her bed. She got out of bed and dressed herself, then went to go look in the mirror in her room. She wasn't hot, but she was cute. Long blond hair that was halfway down her back, green eyes that she supposed were nothing too special. She wasn't too tall, about 5'5" but she took care of herself; she exercised regularly, and was tan, thanks to the Arizona sun. She was average, but had the potential to be so much more. She never wore tight fitting clothes, although she bought them in hopes she could be daring enough, and never really wore shorts or skirts that were shorter than her knees.

She played it safe. "Fuck!" Annie yelled at herself in the mirror, as there was a knock on the door. Annie answered it, and her friend, Rachel, was standing in the doorway. Now Rachel was hot, as Annie did a quick once over. Rachel was wearing shorts that were almost at her crotch, and had her ass almost hanging out, and a strapless top, her 32B boobs seemed to be perfectly perky to Annie, and Rachel was good at makeup: not too much to make her look desperate or anything, but enough to compliment her blue eyes, slender cheeks, and she was able to do her long brown hair in a way that complimented her heart shaped face. Rachel was a little taller that Annie, and her legs showed off her height beautifully. Annie was jealous, but she never showed it.

"What's your problem?" Rachel asked, "I heard you yell 'fuck' a moment ago."

"Nothing, just stressed with these papers and midterms, that time of the year."

"Chill out, we got English figured out, and psych. If anything, you should be freaking out over that fucking Sociology class. Dr. Pine is such an ass," Rachel said. "Maybe we should put together a study group, and get that hot guy that you stare at all class in it." Rachel said as she giggled.

"Rach, no.. He doesn't even know I exist anyways. Speaking of Sociology, why weren't you there?" Annie asked.

"I was out late with Rick, so I slept through my alarm. I probably didn't miss much anyways, and what I did I know you took notes, so you can explain it to me.. That's if you were paying attention enough to the class and not Mr. Hottie Miles." Rachel said as she looked over Annie, "You know, you probably would get laid if you stopped looking like you were so uptight, no if you stopped being uptight! I know that body of yours, you're hot Annie! Show it, be confident!"

Annie sighed, "You know me, I've never been confident. At least not as confident as you."

Rachel sighed, and then clicked on her phone, "I'm going to text Kyle, he knows Miles, and we are going to arrange a study group for this midterm, and then we are all going to go out to the bar, get wasted, and you and Miles are going to have a great time, if you know what I mean," she said as she laughed. "And I'm going to pick out your outfit and do your make up, and you are NOT going to protest. If you don't want to be a virgin forever, you'll do as I say." Annie gave in, she knew if she had any chance of getting anywhere with anyone, let alone Miles, her hope rested with her best friend, Rachel.

__

Thursday came, and as she sat down in the lecture hall, she felt slightly uncomfortable in what she was wearing, but slightly empowered too. Rachel had picked out a slim fitting tshirt that showed off Annie's physique and also her 36B breasts, and a flirty skirt that was mid thigh length, as well as cute flip flops that complimented the look. Annie's make up was subtle, but framed her face, and made her blue eyes shimmer ever so slightly, and her hair was curled at the bottom, and teased at the crown to give it volume. Annie had to admit that she looked good, and as she walked to class, the looks made her feel good. Annie sat down in her usual seat, and pulled out her books and looked up as Miles walked into the classroom. She expected him to stop at the row before hers and take his usual seat too, but she was surprised when he stopped and walked down her row, and took his seat next to her. She watched as he pulled his books out as well, and then he turned to her.

"You know Rachel, right?" he asked.

"Yea, she's a good friend of mine" Annie replied.

"She texted Kyle and asked if we wanted to join you guys for a study group today, and then tonight go to the bar," Miles said, as Annie watched Rachel and Kyle walk into the room together. Rachel looked at the conversation that was going on, and with her eyes, said 'I told you so," as Rachel took her seat next to Annie, and Kyle next to Miles. "Are we still on for tonight?" Miles asked.

Annie paused, and Rachel nudged her. "Yes!" Annie said, a little too loudly and over excited. She could feel her face turn red. 'FUCK! I just blew everything!' Annie thought to herself. Miles smiled, "Awesome," he said. Rachel and Annie looked at each other and smiled, "Awesome," Annie said. The next 80 minutes was torture as she tried to concentrate on the lecture and not on Miles. Every so often she would sneak glances at him and smile to herself. 'I'm going to get laid tonight!' she thought to herself, and could hardly contain herself by the end of class. They all got up, and walked out of the class together when it was over. "So where did you guys want to go?" Miles asked.

"I'm fucking hungry, lets eat first," Kyle said, "You guys hungry, I'm fucking hungry."

"I could eat," said Rachel, as she bit her lip.

"Yea, lets go eat, I'm hungry too," Annie replied, "we will study better after we eat anyways."

They all ate, well, Miles and Annie ate. Rachel and Kyle took off somewhere, saying they needed to go to the bathroom. Annie knew what they were doing, and she wished that she was brave enough to do that with Miles. Instead, she sat awkwardly through lunch with Miles, making small talk. She did however, catch Miles staring at her a few times, which made her pussy wet. Rachel and Kyle returned shortly after, and as much as they tried to study, they knew it wasn't going to happen. Instead, they talked about the professors they hated, their up and coming summer plans, and the venue at which they will go that evening.

"Well that was a good study session. I guess we will call a quits, and see you ladies tonight," Miles said as they all got up from their table.

"Absolutely," Rachel said; "see you tonight," Annie said. She felt confident enough to smile seductively at Miles, and hoped that that what it looked like. It seemed to work, because Miles stared at her with a ravaging look in his eyes as she walked away. "The outfit I have for you tonight is going to make Miles drop his pants at first sight of you," Rachel said once they got back to her room.

"Are you sure about this?" Annie asked, "I mean I know I want to fuck Miles, but just a meaningless fuck?"

"Those are the best kind! Look, you're going to be fine. You're on the pill, so you're protected. And you're young! Have fun, loosen up Annie, for me! For yourself! You've always done what's right, do something that feels wrong for once! Let go!" Rachel pleaded.

"Okay, I'll let go." Annie said.

"Woohoo! Tonight is going to be awesome!" Rachel said, as she pulled out an outfit that Annie never thought she would ever wear.

-

As Annie and Rachel walked into the club, she could feel that all eyes were on her. She felt so good, and the three shots of tequila she had had just before helped. She smiled as she knew every eye attached to a dick was fucking her in their mind. Rachel had picked out a tight fitting dress that had cut out sections along the ribs, and a cut out section that dropped low, showing off her incredible cleavage thanks to Victoria Secret. She wore heels that complimented her sleek legs, but didn't make her too tall either. Her make up was so seductive, that when Rachel was done with it, she looked like she was going to make out with her. Annie looked hot, and she embraced it.

"Every guy is looking at you, Annie," Rachel yelled over the loud music.

"Who cares, I only want one! Where are the guys?" Annie asked.

"At the bar, Kyle texted me a minute ago. They are waiting for us," Rachel said. They pushed their way through the crowd, not that it was too bad, most of the guys made way for Annie and Rachel, probably to check them out. Annie had to admit that her ass did look ravishing in this dress. "I see them!" said Rachel. The guys waved, and the girls walked over to them.

"HOLY SHIT!" said Kyle, "You looking fucking hot! If you don't fuck Annie tonight, Miles, I will!"

Annie blushed.

"You do look amazing, Annie. Drink?" said Miles.

"No, let's dance!" Said Annie as she pulled him onto the dance floor. It didn't take long for her fantasy to become a reality.

"Wanna get out of here?" yelled Miles, "I'm not too drunk to drive, we could go back to my place?"

Annie nodded, as she let Miles guide her out of the bar. She caught Rachel as she was leaving and smiled. Rachel gave her the thumbs up, and Annie left the bar. Once they were out of the bar, at Miles' car, he wrapped his hands around her and pulled her in close. Annie was drunk enough to have no second thoughts, but sober enough to have composure. He kissed her hard, as he pushed her up against his car. Annie found her hands running down Miles' body, and began to rub his cock outside his pants. Miles' breathing quickened as he kissed her neck. 'It going to happen!" Annie thought to herself, 'not here though.'

"Not here," she whispered in Miles' ear. He pulled his head back and smiled. He opened her door as Annie slid into his car. Miles came around, got in, started the car and took off. Annie felt daring. She reached over and continued to rub his cock through his pants. His head went back slightly, and she could tell he was enjoying it. They finally reached his apartment, they got out of the car, and Miles led her to his door. Once unlocked, the door was barely closed before they were on each others lips. Miles' shirt came off, as Annie kicked off her shoes. Miles unzipped Annie's dress, as she undid his belt and pants. Her dress, his shirt and his pants seemed to come off all at once, and then Miles pushed her onto his bed.

Miles unhooked her bra and began to kiss and lick her breasts. Annie was in heaven. Slowly, she felt his tongue find its way to her thong. He pulled it off and opened her legs to find a clean, shaven pussy. Annie's head went back as her back arched when Miles began to eat her pussy. He drank her juices, and Annie found herself screaming and moaning; it was not possible for her to be silent. Miles got up, and took off his boxers. Annie stared at his cock, and it was just as she had imagined it to be: glorious. She smiled at him, and the look in her eyes told him everything: 'fuck me!' He entered her, and Annie felt a slight pain. She could feel herself being stretched open by him, as he pumped in and out of her. She screamed, moaned, and squirmed under him as the pleasure took her over.

"Fuck me! Fuck me hard! Make me cum!" she screamed.

Miles fucked her, and it felt so much better than she had ever fantasized about. She was building an orgasm.

"I'm cumming!" she yelled in ecstasy. She was lost in her mind as the pleasure took over her, and she could feel herself shaking, and moaning, as her legs wrapped tightly around his body. "YES!" she screamed as she came all over his cock.

It was too much for Miles, and he came inside of her as her pussy juices flowed all over his cock. "Holy fuck, that was amazing," he said as he lay there, panting, still inside of her.

Annie, taking deep breaths, felt numb. "It was incredible." she whispered.

Miles rolled over, and propped himself on his elbow. "Were you a virgin?" Miles asked.

Annie didn't feel ashamed, or shy, or anything; she felt alive, for the first time in her life. "Yes," she said, "I was."

"Jesus, how the fuck did you stay a virgin for so long? You're so fucking hot Annie. I've always wanted to fuck you," Miles said.

Annie looked at him and said, "you can fuck me anytime you want."

And for the rest of the night, every fantasy of Annie's came true. She never knew that it was possible to have so many orgasms.

Annie knew, she would never be the same.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
plumberdonplumberdonalmost 4 years ago
Her first time is more than enough

What a great story you have us.Thanks again

You should always remember that special someone who shared that time with you😇 I remember my first w a girl.😁I was only about six or seven the first time I ate pussy😄. I was scared to death. Had no idea what this hairless thing was in front o f me. She was older about 10 or 11 but she new what she was doing even at that sge. Well needless to say you start learning from older people😁 I was taught very well and still love to eat puss y at my age 90 years young.😁

AnonymousAnonymousalmost 10 years ago
My fucking god

Damn

AnonymousAnonymousalmost 10 years ago
I like the idea...

...although I'd like to see some more work on the details.

For example, having a hot friend do her hair and makeup are very plausible. Obviously she had plenty to work with. It would be nice to see a little more seduction, where she talks to Miles more (let's say for 1-2 weeks) and progresses in getting bolder with him, gaining confidence. Definitely spend more time on the sex--how he enters her, what she feels, how he feels, what he says--because in some ways it felt like a quickie and not much to enjoy.

AnonymousAnonymousalmost 10 years ago
My wife's experiences were 180 degrees different!

My wife and her boyfriend were young and in high school when he took her cherry. They'd been together for a year or so with her giving him handjobs. Finally one day at his house and no one was there, he was able to get her hot enough to bed her. She told me it was awful.

She said she was dripping juice everywhere, lubrication wasn't the problem. It was that when he was on her missionary style, his dick would bend and not go in because it was so tight. Apparently, they tried to get it in for quite a while when she came up with the idea of her on top.

I've read since, that is the worst way. She said it hurt so bad she almost threw up. Thankfully she said he lasted for about 5 or 6 pumps in and out and it was over. She was in tears and he took her home because she wouldn't quit crying. About what, she's never told me. But she said she hurt badly for a few days and felt raw for a week.

The next weekend she was ready to go again. She told me that while it wasn't quite as bad as the first time, it was close. She was still very tight and very raw inside. He was quick on the trigger (both their second times) and it wasn't until about the 4th or 5th time it started feeling the way it should.

When I asked her if she orgasmed the first time, she looked at me like I'd grown a third head and said HELL NO. It wasn't until about a half dozen times or so before she thought she started cumming when she was fucked.

I will take the time to say one single thing about that. But first you need to know, I was a virgin when we got married and she was... lets just say, well broken in... After we consummated our marriage, which I will take the time to say was beyond anything I could have imagined, she was in tears. As a very young man (I was 19, she was 18) I was sure something was terribly wrong. It was but not what I feared, that she hated having sex with me, I knew she was well experienced.

No, she was in tears because she didn't wait until she was married to lose her virginity. To this day (she's almost 60 now) she wishes she would have had the self control to share the most precious gift a young woman has to give to her mate for life, her maidenhead and the tears and consoling and sharing that goes along with sharing everything her body had to offer.

Share this Story

Similar Stories

Blackmailing Betty I entrap and fuck our voluptuous cleaner.in NonConsent/Reluctance
Extra Credit To graduate, a student must learn a lesson about life.in Erotic Couplings
Fun on the Class Trip Dumb slut gets taught a new type of lesson on the class trip.in NonConsent/Reluctance
Trinity A young homeless virgin is taken in by an older man.in First Time
Bagging Groceries Young man takes a lover.in Erotic Couplings
More Stories