Taking Ashley's Virginity

Author's Note: Although I have practiced writing stories many times in the past, this will be my first time posting one publicly. Please leave any comments or tips to give me a better understanding and improve my work.

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Part One

A Big Surprise

James only lived a mile away from his girlfriend, Ashley, so during one of his regular jogs he decided to pay her a visit. As he walked down her street to her house he texted her asking to come outside. There was a bench on the side of her house out of sight from anyone. She was excited to see him. James smiled as he watched her walk toward him. She was a beautiful girl and they'd been in love with each other since the end of middle school. Her shoulder length chocolate brown hair curled around her face accentuating her natural beauty. Her skin was flawless and her green eyes stood out. James could feel his heart beating rapidly in his chest. He had already calmed down from his run, but after looking Ashley up and down as she walked toward him he couldn't help but get excited again.

Ashley was wearing a modest outfit that wasn't even slightly revealing, but nothing could hide her naturally curvy features. She was wearing jean shorts and a black shirt exposing no cleavage at all. Her chest always caught James' attention and surely lots of stares from other boys too. Her breasts were enormous. They were like nothing he'd ever experienced or daydreamed about. She had the biggest chest of any girl at school and it drove James crazy with lust.

When Ashley sat beside James, neither of them could help but feel nervous. They'd only ever gotten to second base through her shirt. Ashley had always been a shy and introverted girl. James thought it was cute about her and didn't mind taking charge when it was needed.

James reached out and held her hand. Ashley blushed and held it back. Her touch was soft and warm. He couldn't help but think of her hand somewhere else. He tried shaking those thoughts from his mind. That wasn't why he was here.

"I really love you Ashley" James admitted.

"I-I love you a lot too" Ashley blushed. James stared at her lips.

"Would it be okay if I kissed you" James normally asked before starting anything to avoid startling or making Ashley uncomfortable. She only nodded in response.

She was too shy and nervous to say anything. He leaned in and kissed her. She was a great kisser. Her lips were soft and every kiss tasted like cherries even though she didn't wear anything on them. This was a moment he'd been fantasizing about for a long time. His heart was pounding in his chest and he felt the blood rushing to his crotch uncontrollably. Ashley glanced down and giggled nervously at the sight of James' erection.

"I'm sorry I didn't mean too" James apologized.

"It's okay I don't mind" Ashley's cheeks were bright red.

Everything was going so well and James was getting so horny being next to his dream girl. His mind was blank. He couldn't focus on anything but Ashley's body.

"Can I see your boobs?" James blurted out. Ashley's only response was a nervous giggle. "Please" James begged. Ashley rolled her eyes and grabbed the bottom of her shirt.

"Are you ready?" Ashley asked as James nodded eagerly.

Ashley lifted her shirt up exposing a beige bra straining to contain her breasts. It was clearly ripping in the middle. Ashley reached behind and unclasped the bra then pulled the shoulder straps down while keeping her shirt on. She grabbed the center of the bra and gave it a tug down exposing her big boobs to James. She lowered her shirt a second later too embarrassed to keep it up much longer.

James was teased by barely seeing her breasts and only became hornier. Ashley's breasts were flawless. They seemed even larger after being freed from their bra. They were full and almost perfectly round. Her cute little nipples were incredibly sexy and already hard from making out. James wanted them in his mouth. It was the first time James had seen bare breasts before and it excited him even more that his first boobs were so huge. James gasped at the first sight of Ashley's boobs. His penis twitched and his whole body shook with lust for her. He wanted more of Ashley's perfect body.

"No don't put them away. Please Ashley can I see them again?" James begged.

She shook her head no and bent over as James reached for the bottom of her shirt keeping him from lifting it. She was bright red and very embarrassed. Although nobody could see what they were doing from the street if any of her neighbors looked out their windows from the second floor they'd see the naughty things they were doing.

James bit Ashley's neck which he knew would set her off. She let out a moan in response. He continued doing it. Ashley eventually leaned back and eased up. She wrapped her arms around James and pulled him to her. He moved from biting her neck to kissing up it working his way to her mouth. They kissed passionately. Ashley loosened up and became less tense. She was pressing James tight against her chest, but he still went for it. He began slowly lifting her shirt up and when he got to where the bottom curve of her breasts pressed against him he pulled away from her grasp barely and inch and slid the shirt up over the rest of her breasts. He broke the kiss and saw a look of near ecstasy across Ashley's face. Then he looked down. His eyes widened and his cock twitched again. Now fully erect it stood prominently in his tight running shorts.

"Omg they're just so huge" James blurted out. Ashley smiled slightly and giggled. "How big are they?"

"My bra size is a 38G. I had to get them measured recently" Ashley explained.

James knew they were big obviously but a G cup? That was unheard of especially for a senior in high school. Most of the girls in their school were barely a C cup. James placed his hands flat on top of her breasts. He admired how much her breasts expanded out from his palms almost two inches each way. He wanted to be gentle with her. He rubbed her breasts with his hands around then gave them a playful squeeze. She let out a faint moan.

"Am I doing good? Can I continue?" James asked.

He didn't want to seem too forward or risk taking advantage of her. He was already worried he'd overstepped. Ashley nodded giving him the permission he desired. James continued to play with Ashley's massive breasts.

As they made out some more, he squeezed them gently sometimes bouncing and jiggling them in his hands. He was mesmerized by them. They felt incredible. He broke the kiss once more and moved his head down first flicking his tongue around Ashley's nipple then circling it. She moaned loudly and pressed the back of his head into her breasts. He began sucking one of her nipples while squeezing the other breast and occasionally teasing that nipple with his fingers. Ashley continued moaning and pressing James harder into her breasts almost suffocating him.

Ashley began gyrating her hips against the bench. James figured she must be getting pretty horny from all this playing around he was doing. He was too. His cock shook and bobbed. James pulled it out of his shorts which surprised and delighted Ashley. She continued giggling nervously. Her face was still blushing bright red. James grabbed her hand and placed it on his cock. She held it in her grip. Then realizing this was her first time as well as his he guided her hand up and down. He himself let out a soft moan which made Ashley very happy. He continued making out with her. Then James reached down and pulled her shorts open aggressively. He shoved his hand into her underwear and felt her wet pussy. Ashley jumped in surprised, but as James continued rubbing it and fingering her she moaned loudly into his mouth.

"Ashley I need to cum really bad. Can you please get on your knees for me? James asked.

Ashley wasn't sure and hesitated thinking she knew all too well what he wanted. She pulled her shirt back down as she kneeled in front of James.

"Oh no honey I need that up. I want you to titfuck me" James stated.

"Um...I don't know how to do that" Ashley sighed thinking it'd be something simpler like a blowjob.

James new this probably made her uncomfortable, but he loved her and couldn't imagine doing this with a more perfect girl than Ashley.

"I'm sorry sweetie. I'll help you get started then you can go from there" James apologized.

Ashley positioned herself between James' legs. James lifted Ashley's breasts up into his lap. They felt heavy in his hands. James wrapped them around his cock and squeezed them together moving them up and down. It felt great, but it also felt strange to be doing this to himself using her. He then guided Ashley's hands in place of his. Ashley squeezed her breasts tight around James' cock. His modest 7" cock was completely engulfed by Ashley's massive breasts as she repositioned herself. They felt softer than anything James could imagine. The space between Ashley's breasts was impossibly warm likely from being squeezed together all day by her tight bra.

Even though this was her first titfucking she performed excellently. She moved up and down along James' shaft occasionally repositioning to place him deeper between her cleavage when he slipped out. She would jiggle her breasts in little waves shaking them against James' shaft or alternate moving them up and down separately. James was getting closer to the edge of his orgasm. He didn't want this feeling to end. Ashley looked beautiful. Her dark brown hair shook and her cheeks were slightly red and blushing from the embarrassment of doing this semi-publicly. She began gasping and panting too as she became turned on by the small moans James let out to indicate she was doing a good job.

James was getting close to cumming. He moved his hips in rhythm with her strokes. James bent down and tried making out with her briefly. He began to feel the rush of ecstasy build up inside him. He moaned into Ashley's mouth before breaking the kiss then arched his back and erupted between Ashley's breasts. It was the most powerful orgasm he'd ever had and he kept shooting spurt after spurt of his cum between and on top of Ashley's breasts. James fell backwards. He still felt aftershocks from his orgasm. Ashley was still kneeled in front of him with her breasts now covered in James' cum.

"What am I supposed to do with all this?" Ashley asked confused.

She took one finger and tried rubbing it into her skin. Then she lifted her breast to her mouth and began licking the cum off as much as she could. James' eyes were glued to the show in front of him. He was already getting aroused again from watching her lick his cum off her amazing tits. Ashley noticed James still had a full erection and uncharacteristically removed her pants halfway and pulled her panties to the side as she squatted above him on the bench.

"I don't know if I can cum again" James admitted. He felt bad about it. This was what he wanted most of all, but didn't think she was ready to have sex already.

"That's okay. It's my turn to cum now" Ashley panted. She was lost in her need of release. Her lust increased her confidence and pushed her to act impulsively unlike her normal shy demeanor. This was a fantasy come true. His dark haired girlfriend with her breasts out about to wrap her tight virgin pussy around his cock. Ashley was struggling to get his cock in her. "I need this. I need to feel it."

James held his cock steady as Ashley pressed her opening on his thick head. He placed his hands on her hips and thrust up to help her. He was a little too forceful and thrust almost half his length inside her. Ashley let out a whimper of pain. James began moving slower and gradually added more length inside her until she was able to fully accommodate him.

Ashley wrapped her arms around James and pulled him close to her. Her huge breasts were pressed tight against James' chest and she began grinding her hips matching James' thrusts. Ashley's whimpers of pain quickly turned to loud moans of pleasure. Her virgin pussy was crushingly tight around James' cock. The feeling was incredible and they were both on the verge of cumming together.

Before that could happen their fun was interrupted when James heard a door creek from the front of the house and footsteps on the walkway.

"Ashley somebody's coming" James whispered.

"I know I'm almost there just a little longer" Ashley moaned.

It was clear she hadn't noticed yet. James reluctantly pulled out, but Ashley wouldn't let him go. She slid him back inside her tight hole. James slammed his cock deep up into Ashley. A few thrusts later Ashley came. She came so hard she almost screamed. Instead she bit James' shoulder trying to contain herself.

James wanted to cum too, but reluctantly pushed Ashley off of him. If they went any longer they'd definitely be discovered. Both of them fixed their clothes and kissed goodbye. James managed to sneak around the other side of the house as Ashley's mother rounded the corner. Ashley's appearance raised her mother's suspicion. Ashley was clearly out of breath, her hair was frazzled, and there was still a wet spot on her shirt from where James came on her chest. Luckily her mother didn't ask any questions and just demanded she come back inside.