Leanne Becomes a Woman

All characters in this story are 18 or older.

Leanne was an eighteen-year-old girl who just graduated from high school and was going away to college in the fall. She was raised in a very religious home, went to church every Sunday with her family, and was a member of her church youth group. Her strict father kept a watchful eye on her and didn't allow her to date boys until her senior year after she turned eighteen and only after her mother interceded. Word quickly spread around the school on how strict and scary Leanne's father was so most boys were too frightened to ask her out on a date. Her lack of experience with dating led her to be quite naive when it came to the opposite sex.

Leanne was determined to remain a virgin until her wedding night and she would rebuff her date's efforts to try and get her to have sex with them. Gradually, her hormones got the best of her and she began to let her dates touch her boobs through her clothes or maybe fondle her ass but not for very long.

She was an attractive young lady, not as pretty as some of her classmates but she wasn't ugly either. Leanne had light brown hair, and hazel eyes, and was on the tall side at 5'8". She kept her 34B breasts mostly covered with loose tops and never wore dresses that showed off much of her long legs. She had a nice full ass that she couldn't hide in her jeans.

Word spread around school that Leanne wouldn't do that much on a date so not many boys even tried to date her. Some would ask her out hoping to be the one to crack through her shyness and conservative demeanor but they were quickly disappointed.

Through all her trials and tribulations, Leanne leaned on the advice of her friend Chloe who was far more popular and sexually experienced than she. Chloe was always trying to get her to loosen up and have some fun but it went against Leanne's upbringing so it was difficult for her. It was at Chloe's urging that Leanne first began to go further with boys.

Chloe would tell her, "You know, there are other things that you can do with boys where you can still remain a virgin. If you keep up the way you are going, no one is going to go near you."

"What do you mean, Chloe?"

"You know, use your hands or your mouth."

"Oh, I couldn't do that. I wouldn't know where to start. Do you really put your mouth on, you know, it?"

"Oh my god Leanne, it's called a dick and yeah, I've given plenty of blow jobs. It's not so bad. Once you get used to it, it's kind of fun."

"What about with your hands?"

Chloe used a pencil to show her friend and said, "Here, pretend this is a dick. You just move your hand up and down on it like this. You keep doing that until, you know, he cums. I mean, that's the least boys expect nowadays."

"Really?"

"Uh yeah. Wow, you really are naive."

Leanne shook her head as tears welled up in her eyes and replied, "I don't know about all this. It still seems like a sin to me."

"Ah, don't be silly. Trust me, even your parents were doing stuff before they were married. You have a date with Brad coming up, don't you?"

"Yeah, tomorrow night."

"Well, here's your chance to start with a hand job."

"I don't know, Chloe."

"Come on, it's fun. He'll love it."

"I'll think about it."

Leanne thought about what Chloe had told her and couldn't get it out of her mind. She was nervous and scared about her date with Brad. They had graduated together and she liked him a lot. They went out once before and after a movie, they went up to a lover's lane down by the river and made out. This date was similar to the last one and Brad quickly picked up where they left off on their last date and had his hand on Leanne's breasts. This time she let him slip his hand up her blouse to touch her boobs over her bra.

She got nervous when he took her hand and placed it between his legs. She got even more nervous when she felt the lump and heard his soft moans when she touched it through his clothing. Leanne heard Chloe's voice in her mind telling her to keep going. Brad was encouraged when Leanne didn't pull her hand away.

She rubbed the lump lightly for a short time when Brad told her, "Take it out."

When Leanne fumbled with his belt, Brad helped his own cause and unzipped his pants, and pulled out his hard dick. She was scared but curious at the same time. She had never seen a dick before. Brad took her hand and placed it back on his dick. It took all of her might to keep her hand from shaking as she wrapped her fingers around his hard member.

"Go on Leanne, stroke it for me."

As they started to kiss again, Leanne slowly stroked her date. Brad got more aggressive and tried to slip his hand up her dress. She let him get up to her thighs before she brushed his hand away. He tried a couple of more times but she wouldn't let him touch her between her legs. Frustrated but on a mission to see how far he could get, Brad returned his hand up Leanne's top and began feeling her tits again. This time she allowed him to get his hand inside her bra. She felt a dampness between her legs as Brad played with her nipples. While they were making out, Brad instructed Leanne on how he wanted her to stroke him.

"Hold it tighter. Faster."

He was starting to breathe faster and they stopped making out. Leanne curiously looked at the hard cock in her hand but she couldn't see too well in the darkness of his car. She saw the tip of his dick glistening in the moonlight. She was too inexperienced to know it was precum leaking from the tip.

Leanne was caught off guard when Brad said, "Suck it for me, baby. Come on, put your mouth on it."

She was too scared to go that far and when she didn't start to blow him, Brad took Leanne's hand to guide her masturbation efforts the exact way he wanted. She figured he was about to cum and wanted to pull her hand away but his hand was tightly clenched over hers.

Brad started to thrust his hips upward and took his hand away from Leanne's as he started to cum. She was fascinated at her first sight of a man's orgasm which startled her with his cum shooting out of the top. Her hand was soon covered with his jizz. That was something that didn't occur to her when she started jerking him off. She was surprised at the amount of cum he had and was glad she didn't put her mouth on it. She was intrigued and a touch disgusted by having all of that cum all over her fingers and hand. As Brad was searching under his seat for a rag, Leanne was looking at the cum on her hands.

When she got home, she immediately sent a text message to Chloe, "I did it. I masturbated, Brad."

"No shit. How was it?"

"It was OK, I guess."

"I'm proud of you. We'll talk tomorrow."

The next day, the girls got together to talk more. Chloe gave her friend a big hug and told her she was proud of her for taking a big step in her stagnant sex life.

"So what happened between you two last night?"

Leanne gave Chloe all the dirty details and told her friend, "He wanted me to put my mouth on it but I couldn't do it."

"Sucking a dick isn't so bad. You should try it."

"I thought about it but I was too scared. What do you do when a guy cums?"

"Well, a guy loves it when a girl swallows. Some girls even let a guy cum on their face."

"Get outta here. You swallow it? No way I'm letting him cum on my face."

"Yeah, it's not so bad once you get used to it."

"I'm not sure if I could even put his thing in my mouth. I know I couldn't let him cum in there."

"Just try sucking it first. Take it one step at a time."

"I don't know."

"Try it. Trust me, it's not so bad. I kinda like it now."

Brad was making progress with Leanne and was quick to ask her out again. From the rumors going around from his friends, he knew he had gotten further than anyone else. It was a challenge for him to see if he could be the first to get her to go all the way. They had a date scheduled for a couple of days after their last one and Leanne and Chloe were once again talking about what might happen.

Chloe told her friend, "You should try blowing him. There has to be a first time and there is no better time than tomorrow night."

"I don't know if I can go that far so soon."

"So soon? You're already eighteen and going off to college in a couple of months. You're already far behind the rest of us. Damn girl, it's not that hard. It's like a hand job but with your mouth."

"We'll see what happens."

After going to dinner the next night, Brad and Leanne found themselves back at the lover's lane as expected. Leanne was sort of looking forward to it in one way and scared in another. She liked kissing Brad and got a warm feeling between her legs when he touched her boobs and legs. She still wasn't sure she could put her mouth on his dick but she figured she would at least end up jerking him off again.

There was no doubt Brad was expecting more because once they were in the back seat of his car, he almost immediately slipped his hand inside her bra moments after they started making out. This time, Brad had her shirt pulled up and pulled Leanne's bra down to expose her breasts. No one had ever seen them before but she felt helpless to stop his advances. Any thought of resisting Brad was distinguished when she felt his lips on her nipple as he started to suck on them.

Brad pulled his shorts to his knees and placed Leanne's hand around. It. She instinctively began to stroke him. Brad had one hand on her leg and was gradually going higher until he reached her upper thigh. Leanne didn't stop him this time as she felt his finger press against her panties. His finger felt so good rubbing against her pussy. She stopped him from putting a finger under her panties though.

When Leanne opened her legs a little more, Brad asked her, "Hey baby, how about giving me a blow job? Come on, try it."

"I'm not sure, Brad. I don't think I'm ready for that."

"Come on, baby. Give it a try. If you don't like it you can stop. Okay?"

Leanne didn't refuse so Brad kept on pleading with her to try blowing him and exerting gentle pressure on the back of her head. She started leaning over and found herself staring at his hard dick which was now inches from her mouth.

"If I don't like it, I can stop, right?"

"Sure baby. Go ahead, put your mouth on it," Brad said while putting more pressure on the back of her head.

Leanne stared at the dick in her face while knowing Chloe would be encouraging her to suck it. She opened her mouth, lowered her head, and closed her eyes. Her tongue was the first to touch the tip of Brad's dick as it slid between her lips and into her mouth. The dirty deed had been done. She took her first dick in her mouth. She couldn't get much of it past the head into her mouth and started to bob her head while Brad began to groan. She wasn't sure if she liked having a dick in her mouth but Brad's reaction encouraged her to continue.

"Oh yeah baby, that feels great. Keep going."

Her hand was holding onto Brad's shaft when her teeth scraped the head of his dick causing her date to say, "Ouch. Be careful. That hurt."

Leanne mumbled, "I'm sorry," and continued blowing Brad.

However, her teeth scraped him again, and Brad told her, "Ow. Why don't you just jerk me off? I'm about to cum anyway."

Leanne was devastated at her lack of success and lifted her head in disappointment. She continued to stroke Brad until he began to moan and squirm. She felt his hard cock pulsate and watched as his cum shot out of the tip once again covering her hand. She wasn't as disgusted at his cum this time but still wondered how anyone could swallow all that jizz.

Afterward, Leanne had Brad take her home as she fought back her tears. She immediately sent Chloe a text message and told her of the date from hell. Chloe tried to reassure her not to give up and to keep trying. She consoled her friend by telling her that everyone scrapes a dick with their teeth from time to time. All she had to do was cover her teeth with her lips. Leanne felt better but not great.

Leanne was hopeful for a better outcome next time but wasn't confident. On her next date with Brad, there were similar results. She let Brad finger her but wouldn't have sex with him so he asked for a blow job again. There was no hesitation on Leanne's part. She wanted to keep trying to get better at sucking dick.

The next time started better and Leanne was blowing Brad for a couple of minutes before she scraped him again. When she continued, she decided to fondle his balls and squeezed him a little too hard which made him wince with pain. She gagged a few times and almost got sick. When she scraped Brad's shaft with her teeth again, he stopped her and told her to finish him off with a hand job.

While Brad was looking for a rag to wipe up his cum, Leanne licked some off her finger to see what it tasted like. It tasted a little tangy and a touch bitter. She didn't like the taste but it wasn't as bad as she thought it would be either. She still wasn't sure she could take a mouthful off it though. She had Brad take her home where she took comfort in text messages with Chloe to tell her what happened.

Leanne told Chloe, "I think I'm going to give up trying to give blow jobs. I'm obviously not good at it. Maybe it's a message from above that I shouldn't be so anxious to sin. Maybe I'll stay a virgin or become a nun."

"LOL. Don't be so dramatic. My parents are going away for the weekend starting tomorrow. Why don't you spend the night? We'll have a girl's night and we'll figure this out together."

"Thanks, Chloe, you're the best. I don't know what I'd do without you."

The next night Leanne went over to Chloe's house early and they ordered a pizza. Chloe went to the fridge to get a couple of her dad's beers and handed one to her friend.

Leanne said, "That's okay. I don't drink much and besides, I don't like the taste of beer."

"Take it, Leanne. It will get you used to the taste of cum. Cum is an acquired taste just like beer."

The girls had a good laugh at that and Leanne took a sip of the beer. They changed into their sleepwear and waited for their pizza. Chloe wore a tank top with no bra and satin sleep shorts. Leanne wore a simple oversized V-neck t-shirt with only her pink bikini panties underneath. It didn't bother her that her nipples were visible through the white cotton material or that the shirt barely covered her ass seeing that she'd be alone with her best friend.

The girls were sitting on the sofa watching a movie waiting for the pizza to be delivered when they heard a car door. They thought it was their pizza but Chloe's older brother, Neil, walked through the door. Neil was twenty and home from college for the summer. He was tall with dark hair and dark eyes. He played basketball and baseball in high school and had an athletic body. Leanne always had a huge crush on him but he never noticed her.

The first thing Chloe said to Neil was, "What are you doing home so early? I thought you had a date."

"She turned out to be boring so I ended it early."

"You mean you weren't going to get lucky," Chloe replied as the girls giggled.

"Yeah, pretty much," he said with a laugh in response.

"We are waiting for a pizza to be delivered. You can have some if you want but this is a girl's night so you have to make yourself scarce."

"Don't worry, I don't want to watch some chick flick anyway but I'll have some of the pizza."

Now that Chloe staked out her territory, Neil greeted Leanne and said to her, "How are you doing Leanne? I haven't seen you in a while. My you've become quite the good-looking lady."

"Thanks, Neil, I'm doing fine."

Leanne felt self-conscious as she noticed Neil's eyes scanning her body. His eyes went from her face down to her chest and down to her bare legs and thighs. He sat in the lounger across from the sofa after grabbing himself a beer.

"How old are you now, Leanne?"

"I'm eighteen."

When he grinned, Chloe told him, "Keep away from her. She's my best friend."

"I just asked a simple question."

"I know how your mind works."

"The last time I saw her, she was a young girl. She's a pretty young lady now."

Leanne blushed but was flattered that an older man was paying attention to and complimenting her. She also felt like she should cover up her body but didn't want Neil to think she was rude.

When the pizza came, the delivery man was eyeing up Chloe and stared at her chest and ass while she got the money to pay him. Neil then followed the girls into the kitchen to get a slice for himself. Leanne didn't realize that her panties were showing through her t-shirt and Neil was staring at her ass and legs. He stared even more when she got three more beers from the bottom shelf of the fridge. When she bent over, it caused her shirt to lift, exposing her panty-covered butt cheeks.

Chloe caught Neil staring at Leanne's exposed panties and ass. She gave him a dirty look that sent him a message not to look at her like that. He raised his hands and gave her a look like what was he supposed to do? Leanne's nipples got more pronounced from the cold refrigerator air. She blushed when she saw Neil looking at them. It also gave her a warm feeling between her legs.

In return, Leanne was looking at the physique of her longtime crush. Neil was cute and was wearing a tight t-shirt that hugged his taut, muscled body and exposed his strong arms. He was wearing shorts that revealed his toned legs and tight ass. The beer was making Leanne's thoughts drift to wondering what he looked like naked. She wondered if he was thinking the same about her.

They went into the living room to talk, eat their pizza, and drink their beer. When Leanne would reach for her beer on the coffee table, she would inadvertently part her legs which exposed her panties to Neil. As she leaned over, her hanging breasts were visible to Neil's wandering eye.

After chatting with the girls and sharing a couple of slices of pizza with them, Neil excused himself and went up to his room to leave the girls alone. Leanne was a touch disappointed to see him leave but she also had a lot to talk about with Chloe.

Leanne never drank much and the two beers went right to her head. She told Chloe every detail of her failed blow jobs. It pained her to relive her traumatic experiences but she was relying on her best friend for some advice. She was truly frightened to even try blowing Brad again. Leanne wasn't sure he would even want to go out with her again. He was already telling her he was too busy to go out again that weekend.

Chloe felt horrible for her distraught friend and said to her, "Let's grab another beer and go upstairs."

"I'm not sure if I can drink anymore."

"We'll take one for you just in case, okay?"

"Alright, but what's upstairs?"

"Trust me."

Leanne laughed and replied, "I did trust you. That's why I'm having these problems."

They went upstairs to Chloe's room and she pulled out her laptop. Leanne saw her typing away and then showed her the screen. Leanne was shocked at what she saw. It was a porn video of a woman giving a man a blow job. She wanted to turn away because she was taught that watching porn was a sin but she couldn't take her eyes off of the woman on the screen using her tongue and lips to work over the cock in her mouth. She was stunned when she took the entire length of the big dick into her throat.

Chloe looked at her and said, "Now that's how it's done."

"Oh, I could never do that."

"Sure you can. You just need experience, that's all."

"How am I supposed to get that when I'm no good at it?"

"I'll think of something."

They watched a couple of more videos and not only was Leanne intrigued by their expert technique but she was also getting turned on by watching a woman please a man in that manner. She saw how much pleasure the man was having and she wanted to do the same for Brad. Leanne still wanted to remain a virgin no matter how warm and wet her pussy was getting.