Julie and Ashley Ch. 03

Story Info
Ashley prepares to lose her anal virginity, a plan develops.
8.3k words
4.46
21.7k
13

Part 3 of the 3 part series

Updated 06/08/2023
Created 02/09/2018
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All characters are over the age of 18, any likenesses or similarities to real people is completely coincidental. Hope you enjoy and any constructive criticism is appreciated.

*****

Hi everyone, Ashley here. The morning after watching Julie get DP'd by my boyfriend Rob and his friend Chad, I woke to the feeling of Rob's morning erection pressed against my ass. He had me wrapped in his arms and the memories of last night filled my mind.

After I dragged Rob to my room, he threw me on the bed. He quickly flipped me onto my belly and grabbed my hips, pulling me to my knees. He devoured my pussy and ass until I orgasmed on his tongue and fingers. He smacked my ass hard and knelt behind me.

I begged him to fuck my pussy, just before he positioned the head of his fat dick and shoved it all the way in with one thrust. I could only groan as he filled me. Rob grabbed my hair to use as a handle, thrusting hard and fast. He lightly pressed his thumb against my asshole and rubbed it with a circular motion. I shuddered at the thought of him fucking my ass.

Rob continued to fuck me hard and fast, as he forced me onto his cock by my hair. Telling me how good my pussy felt and that he wasn't going to stop until I begged him to cum. He asked me where I wanted it. I was so hot and wet my juices were coating my thighs.

"Cover my face and tits! In my mouth or my pussy! I don't care just keep pounding my cunt!" I screamed.

He quickly pulled out and told me to turn around. As I spun around to face him, his slick cock brushed my cheek. I opened my mouth and took half of it. Rob grabbed my hair with both hands a pushed the rest of his hot throbbing cock into my mouth. When the head hit my throat, I gagged slightly. Rob told me that I was a great little cock-sucker.

He pulled me off his cock and pushed me onto my back. Climbing between my spread thighs, Rob hooked my knees with his arms and pushed my knees towards my shoulders. He lined himself up and shoved his hot thick cock deep inside me again. I cried out, as an orgasm wracked me to my core.

Rob pounded me into submission. I gripped his shoulders as another orgasm approached. "Oh God Rob, you are going to make me cum again!"

He leaned down and bit my left nipple and pinched and pulled the right one. My pussy convulsed around his cock as I came again. Rob pulled out and straddled my chest. Stroking his thick cock, he aimed it at my face. "Here its comes Ashley!" He groaned.

I took his balls in my hand and massaged them gently. His hand flew back and forth as his orgasm approached. He grunted once more as I saw, then felt his hot thick cum fire at my face. The first shot landed on my nose and forehead. His second and third plastered my left eye shut. He leaned forward as a final glob landed on my lips.

Rob rubbed the head of his cock across my lips and exhaled deeply. I reached up and scraped his seed out of my eye socket and opened my mouth to lick the cum from my fingers. I repeated the process until I cleaned up as much as I could.

We told each other how good the sex was, as I pulled the sheet over our bodies. Rob snuggled up behind me. He thanked me for letting him fuck Julie. I told him how hot it was watching him and Chad fuck her and I soon fell into deep, restful sleep.

There was no doubt that Julie thoroughly enjoyed the guys fucking her ass and pussy. And now I needed to fulfill my promise to Julie. Up until a few weeks ago, there was no way I would have done anal. I thought it was gross and that it would be painful.

But watching Julie's orgasms from it; not only last night, but two weeks ago when I caught her masturbating, had changed my mind. I shifted slightly and Rob's dick slipped into the valley of my cheeks. He shifted his hips, causing his hot shaft to rub against my anus.

My body shivered with apprehension, but my pussy began to heat up and moisten. I wiggled my ass a little as Rob pulled me tight against his body. He slowly slid his cock back and forth between my cheeks.

"Mmmm, baby your ass feels so good against my cock." he whispered in my ear.

I pulled myself away and pushed him onto his back. Straddling him, I pressed my dampening pussy against his thick cock. "Do you wana fuck my ass stud? Would you like to see me suck Chad's dick while you pound my pussy from behind?"

"Hell yes, I wana fuck your ass so bad, and I know you would love to be spit-roasted!"

My pussy was getting wetter as I slid back and forth on his dick. I raised up slightly and let the head slowly enter my hot slit. Rob grabbed my hips and pressed up, slowly filling me.

I raised up when I felt his balls press against me. Rob reached up, grabbed my tits and began kneading them. I slowly rode his cock, thinking about giving him my anal virginity. Reaching back with my right hand, I grazed my anus with my middle finger. My body shuddered as I pressed lightly against it.

I still had reservations about anal, but I knew Julie would guide me through to process. I put my hands on Rob's shoulders and rode him faster and harder. When he gripped my nipples and tweaked them, my pussy gushed.

"That's it Ashley ride my cock. Your pussy feels great wrapped around me. I'm gonna fill that pussy with my cum."

As I dropped down on his hot shaft, I ground my clit against his pubic bone. I was quickly approaching orgasm. Thoughts of him and Chad filling me with cum, only pushed me closer. I crushed my tits against his hairy chest and forced my tongue into his mouth.

As our tongues dueled, Rob reached back and pressed a finger to my asshole. I shivered at the sensation. Every time I raised up, it would force his finger against my remaining virginity. I moaned into his mouth as my body hovered on the precipice of orgasm.

Rob grabbed my ass with both hands and forced his hips up as mine came down. I pushed myself up. Reaching down with my right hand, I rubbed my clit. Pressing hard, I groaned.

"Fuck me Rob, I am so close! Fill my pussy with your hot seed!"

His cock throbbed and he moaned that he was cumming. The feeling of his sperm coating the walls of my pussy sent me over the edge. I clamped down on him and cried out that I was cumming also. As my orgasm subsided, I leaned down and Rob took me in his arms. We laid together for few minutes as we rested.

I wanted to just la there all day, but I had a 1 PM class. I gave Rob a quick kiss, thanked him for a great night and a wonderful morning. As I climbed out of bed, he gave my right ass cheek a playful smack.

That night Julie and I sat down to dinner and talked about last night. She told me how it had been the best sex she had ever had and how Chad fucked her again to a tremendous orgasm. I told her how Rob gave me exactly what I needed as well.

"OK Julie, you piqued my curiosity about anal and double penetration. I need your help. Tell me what I need to do. I want Rob to be the one I give my anal virginity to."

She smiled brightly. "That's great Ashley, try not to worry too much. We will go slow and by Saturday, you should be more than ready."

We finished dinner and Ashley told me to go take a long hot bath while she finished cleaning up. And that she would meet me in my room when I was finished. I went upstairs and ran a bath, making the water as hot as I could stand it.

I pulled up some soothing music on my phone and slipped into the tub. I just laid there relaxing for about ten minutes. Then I picked up my shower sponge and lathered it up. Starting with my shoulder and working lower, I lightly worked down my arms. Then across my collar bone and down to my breasts.

My nipples stiffened quickly under my ministrations. As my hand went lower, I felt my pussy tingle with excitement. By the time I finished with my legs, my entire body vibrated with excitement.

The time had come. I rose to my knees and add more body wash to the sponge. I leaned over and began rubbing my ass in large circles. I slowly slid it in between my ass. When it grazed over my asshole a deviant thrill ran though me. I continued to work it over my tight asshole.

I had to know what it felt like. I set the sponge aside and leaned on the edge of the tub. I squirted a large dollop of body wash on the middle finger of my right hand. Reaching back, I pressed it against my anus. The cool gel felt nice as I pressed in. When my ass finally opened a little, I felt a slight pinch.

It wasn't too bad, so I pressed further. When I got it in to the first knuckle, I stopped. My virgin hole ached. I pulled back slightly and pressed back in. I slowly relaxed as I gently fingered my butt. I couldn't convince myself to go any deeper. I knew Julie was waiting for me, so I eased my finger out. I got out and toweled off and quickly dried my hair.

I walked out of the bathroom and was shocked to find Julie waiting for me, wearing a white baby doll nightie, white silk panties. and a plethora of sex toys splayed out on the bed. She smirked when she saw the shocked expression on my face. She had laid out an old beach towel on the foot of my bed and another on the floor.

There was a huge bottle of lube, with a pump top and 4 butt plugs. The smallest was barely wider than my index finger, but not quite as long. The biggest one looked huge, I didn't know how that thing would fit in my virgin butt.

She had a device that looked similar to something I had seen at the local pharmacy. They called it a "Neck Massager", but this one was pale pink and looked smaller. It also had an electrical cord that looked to be about 3 feet long. Next to that laid a translucent purple jelly dildo that looked to be about the size of Rob's dick. Her rabbit vibe laid next to that.

The last toy was something I had never seen before. It was well over a foot long and looked to be made of same material as her dildo. It was similar in color as well. There were a series of balls connected together that gradually increased in size. At the end with the largest ball there was a loop. I could only assume it was used for removal.

"Holy shit Julie! How long have you been into anal? There is now way you are putting all that stuff up my ass tonight!" I exclaimed.

"Ha ha ha, I knew I would freak you out. Sweetie, I love you. But I wanted you to get an idea of what's available. We a going to start slow, but before you let Rob fuck your ass you and I are going to use all of these. And you will be buying your own butt plug."

I was partially relived listening to her. Although the thought of buying my own butt plug frightened me more than putting things in my butt or giving Rob my final virginity. What if someone saw me going in or out of one of those stores? Even worse, what if someone someone I knew was in the store and saw me buying a butt plug.

As I walked over to Julie, I dropped my towel. Leaning down, I took her face in my hands. Pressing my lips to hers she put her hands on my hips and kissed me back. It was soft and sweet. My pussy tingled and moistened with excitement, as Julie slipped her tongue into my mouth, searching for mine.

We broke our kiss as she stood up. She turned us around and pushed me back until I felt the bed on the back of my thighs. "Hop up on the bed baby. Let me show you how good anal truly is." She whispered in my ear.

I nodded and positioned myself butt in the middle of the towel. As I laid back she stepped between my splayed thighs and laid light kisses all over my belly. When her tongue dipped into my navel, my pussy grew wetter. She kissed and licked her way down to my baby smooth vagina.

Julie nudged my thighs farther apart. I heat of her breath on my mound made my desire soar. She finally licked the length of my weeping slit. I moaned when she place her thumbs on either side of my pussy and peeled me open to reveal my clit.

Her talented tongue danced over my clit, down my pussy to my ass. Her touch was so delicate in comparison to Rob's. Neither was better than the other, just different. Julie focused her attention on my sphincter, getting it wet as she massaged it with her tongue. I reached down with my right hand to massage my clit.

Slowly Julie moved back up to my now dripping pussy. I was getting closer to an orgasm. She dipped her tongue inside me, then slid towards my clit. I pulled my hand away and let her pleasure me. Her tongue danced across my nub.

"Julie please! I am so close baby, please make me cum!"

She sucked my clit into her mouth and lashed her tongue over it. That was all it took, I grabbed the back of her head and pushed her hard against my pussy as my orgasm washed over me. My moaning increased as she continued to pleasure me.

When she pressed a finger against my asshole, I was so relaxed that the tip of her finger easily slipped in to the first knuckle. Her tongue moved down and slipped between my soaked folds. Julie was pushing me towards another climax within seconds and she knew it. She sucked my clit back into her mouth and hummed.

"Oh Fuck, you are making me cum again!" I cried and grabbed a pillow. Screaming profanities into it as I came again.

With that, she pulled away. I was beside myself as I lay on there recovering from a glorious orgasm. When I moved the pillow away from my face, I saw Julie standing there with that big bottle of lube and the smallest stainless steel butt plug. I was as ready as I could possibly be.

"On your knees Ash. It's time to pop that cherry ass of yours." She smiled.

I got to my knees quickly and positioned myself as close to the edge as possible. Grabbing the pillow once more, I pulled it under my chest and gave Julie full access. I started getting nervous when I heard her step up behind me and place her had on my left cheek.

"Just relax bae, I am going to lube you up. You have a beautiful ass, your balloon knot. it's so pink and perfect. I can't wait to see Rob slowly slide his fat cock in this hole." Julie was building my confidence. She knew what I didn't and I trusted her completely.

As Julie squirted some lube on her fingers, she warned me that it would feel cool. None the less, I jerked suddenly when I felt it hit me directly on my asshole. Three spurts hit me and quickly ran down to my pussy. When she dropped the bottle to the floor, I knew her fingers would be inside me soon.

She gently rubbed the lube around my sphincter. Then dipping lower, scooping up what had slid down to my pussy. My arousal began growing once more. When she pressed her finger against my hole, I subconsciously tightened up. She uttered words of encouragement as she pressed forward. Telling me to relax and let her in.

As I willed myself to open, her finger slipped in quickly. My pussy spasmed as she sank into the first knuckle. She slowly withdrew and pressed forward again. The sound of the massager broke the silence, as it vibrated to life. A deep moan burst from me as she pressed it against my pussy.

Reflexively, I pressed against the massager. The wide pink vibrating head felt amazing. Julie continued to finger my butt as my arousal grew. I couldn't help but relax and when I did, she sank her entire finger inside me.

"Good girl Ashley. You took my entire finger"

"Fuck, I had no choice, that thing feels amazing. Please make me cum again Julie."

My orgasm kept building as she finger fucked my ass. Her vibrator was relentless. I moaned and begged for another orgasm. When she removed he fingers, I knew what was about to happen. I was so close to cumming, I pressed my face into the pillow and waited for her to violate my ass again.

"Ready for step two? This is the second smallest plug." She told me, I could only nod into the pillow. I was ready for more. NO, I needed more.

Julie pressed the stainless butt plug to my anus gently. I once more willed myself to relax. With steady pressure I felt myself open, but it hurt as she pushed. I couldn't breath. The more she pushed, the more it hurt. I was close to asking her to stop.

"Push out and let it in Ashley, it will only hurt for a second. I promise sweetie."

Her words of encouragement helped. Combining that with the vibrator was enough. I did as she asked. I felt her stretching me wider as I pushed out. And just that quick, she seated the butt plug fully in my ass.

"Bitch!" I screamed into the pillow.

Julie massaged my left cheek as she slid the massager up to my clit. My ass ached, it was stretched and full. As I grew accustomed to these new sensations, my orgasm began to build once more. My pussy juice began to seep out, coating my thighs. She leaned down and I felt her tongue on my ass, as she ran it around the edge of the plug. I couldn't help but clamp down on the plug.

"Cum for me baby. Just let go." Julie told me as she jiggled the plug.

Fuck, it was really starting to feel good. I was once more teetering on the precipice of an orgasm. She started to pull on the plug. I felt my ass expand and a groaned louder into the pillow. Just when I thought it would slip out, she let it back in. Julie did this over and over.

On the fifth or eight time of her fucking my ass; I can't remember a gut wrenching orgasm wracked my body. I clenched every muscle in my body and I ached everywhere. It was gloriously awesome. I felt a gush of wetness expel from me in the process.

It took me a few minutes to recover from that mind numbing orgasm. And when I was able to extract my face from the pillow, I turned onto my side. There was Julie, with the biggest shit eating grin on her face. She didn't waist much time though, as she leaned over and gave me a slow sensual kiss.

"To hell with those guys Julie! That was the best orgasm of my life."

"For as much as I like playing with girls and you especially, I still need a hot throbbing cock. As far as I am concerned, there is no substitute." She giggled. I had to agree with her. I would never give up riding a hot throbbing dick or a guy pounding my pussy from behind.

"Go get that plug out of your ass. Clean it real good. I am going to leave the lube. You need to put that back in before class tomorrow and keep it in at least till you get out of class"

Julie giggled at the shocked look on my face, She actually wanted me to put it back in and wear it to class. I was flabbergasted at the idea of having it up my ass, out in public. How would it feel to walk with it in? What if someone figured it out.

"But Julie..." She cut me off.

"Yes Butt! This is all about your ass. You are on the accelerated anal training program. It took me months to get to this point. And you are insinuating at giving your ass to Rob in just a few days? And if I have my way Chad will be involved as well"

For a crazy as Julie was about certain things, I fully trusted her. When it came to anal, I needed to do as she told me. She gave me a playful slap to my ass, then turned and began gathering the rest of her toys. When I rolled to the other side of the bed, I felt the plug shift and press in new ways. An "Oh Shit" escaped my lips. Julie just chuckled as she unplugged her incredible vibrator.

The next morning, I woke earlier than usual. My mind preoccupied with my "anal training", as Julie put it. I went downstairs, started a pot of coffee and dropped a bagel in the toaster. As I stood there, staring out the window, I couldn't help thinking about Rob fucking my ass. Visions of Chad's head between my thighs, as he licked me to orgasm, had me preoccupied. Julie snapped me out of my revere when she smacked my left ass cheek.

"Damn it Julie." I exclaimed.

She hugged me and kissed my cheek. My bagel popped and the coffee was almost ready. I pulled a plate and a mug from the cabinets. Meanwhile Julie grabbed the cream cheese from the fridge. We continued the practiced dance of our morning routine.

I had just finished rinsing my dishes. As I passed her, Julie grabbed my arm and stopped me. "Don't forget what I told you." She said.