My High School Sweetheart’s Little Sister -pt. 9 (Cindy’s Deflowering) by JadeGrey

Stacy’s ass spread apart like that looked pretty fucking hot; it was darker, less innocent, than Cindy’s tiny pink hole, but the center was pink, and wet. I really wanted to stick my cock in there… I don’t know if she would go for that, but I still was not quite ready to stick my tongue into it.

……maybe a finger… let’s see how her little ass feels

First, some lube… I grabbed the bottle and poured some down the crack of her butt, and rubbed it into her ass. Her little pucker would wink and relax every time I pushed my finger at the opening. I slid one finger inside her… up to the second knuckle. No complaints…she was still spreading her ass with both hands, so I added a second finger and it slid in pretty easily. I have to admit, her asshole felt pretty fucking amazing. Tight, slippery, and hot, gripping my fingers… I could imagine what that would feel like sliding down on my dick.

Cindy was now sitting up and watching intently. I looked down at the toys on the floor, pulled my fingers out of Stacy’s ass and grabbed the pink vibrator.  I turned on the vibrator and gently pushed the tip slightly into her ass… still no complaints… I pushed my fingers back into her pussy and her g-spot was swollen up like mad. I stroked her with my fingers pretty aggressively and started pushing the vibrator further into her ass until the larger part was fully inside her. She was moaning lightly and rocking her hips against me as I finger-fucked her pussy and fucked her asshole with the vibrator. Cindy leaned forward to look closer and put her hands on Stacy’s hips. Her eyes were wide and locked on the pink sex toy sticking out of Stacy’s butt. I grabbed Cindy’s right hand and moved it to the vibrator… she looked at me, then back to the vibrator, then started slowly moving it in and out of her friend’s ass.

Stacy was gyrating around and moaning loudly now, obviously enjoying the new feelings she was experiencing, but I didn’t think she realized it was Cindy who was shoving the vibrator into her ass.

“Cindy, push that thing harder in her ass… like it was a cock fucking her,” I said to clarify things. Stacy’s eyes popped open and she looked up to the side to see her friend’s arm pumping.

She gasped… then it only took a little furious finger play on her swollen g-spot and a few more strokes in her ass before a spray of fluid shot out of her pussy and she shrieked as she came. She bucked and humped my fingers and the vibrator in her ass for several waves, then her arms fell to her sides. I could feel the inside of her pussy change from the thicker lube to a post-climax wetness, and I gently pulled my fingers out of her. Cindy let go of the vibrator and looked at me with wide eyes. “Slowly pull that out of her ass,” I spread her wide with both hands and Cindy grabbed the vibrator again, “Slowly… I want to see her gape.” Cindy slowly pulled the vibrator out of her friend’s ass, and her asshole gaped wide for a bit before it winked closed, then opened again. She was clean… and wet… my cock was right there… rock hard and dripping pre-cum down to the floor.

…..her ass is ready for anal. I wanted to feel that tight asshole around my cock. I never really enjoyed any good ass-fucking… only a few bad attempts. I inched forward lusting to push my cock into her gaping little butthole

I held her ass open, my cock inches from her opening. Cindy stared into her friend’s asshole for a moment, then looked up at me with a blank expression. I realized I couldn’t fuck Stacy like this… not now. Cindy asked me to take her virginity tonight. I may get another chance to play with Stacy, but tonight I needed to be a bit more respectful. I needed to take care of Cindy. I inched backwards from Stacy and smiled at Cindy.

Still breathing heavily, Stacy stretched her legs out and laid down on her tummy flat on the floor. I don’t think she realized how close she came to getting fucked in her ass right then. “Oh my God… that was crazy. I can’t believe…”, and started laughing. “Jesus, Cin… I can’t believe you did that!”

Cindy laughed a little, “You didn’t seem to mind it”, and lightly spanked her friend.

“I think it might be time to take care of your needs, miss Cindy-Lou.” I got up and walked out to the pool, grabbed my clothes and brought them back inside.

“Are you leaving?” Cindy said, with a shocked look on her face. “No! Certainly not!”, I laughed and felt around in my jean pockets until I found the pack of condoms. “I just wanted to grab these.”

Cindy waved it off, “You don’t need those. I just finished my period yesterday. We should be safe for a week or so.”

“And we still have the turkey baster!” Stacy popped in, laughing at the reference. I thought of lecturing her on birth control, but quickly dropped the idea.

I didn’t like the idea of going without a condom, but the thought of working my bare cock into Cindy’s little body outweighed the concern. I walked over and picked up Cindy and set her down on the edge of the couch. She immediately spread her legs open and reached down to her little pink slit. She slid a finger inside, and brought it back out and spread her lips. She was being so bold… so much naughtier than just a short while ago. I felt a bit of guilt, but her tiny naked body, thin legs spread wide, exposed and aroused, quickly wiped away any feelings but lust from my mind. Stacy sat up, leaned over and grabbed Cindy’s left knee and pulled it closer, further spreading Cindy’s pussy open.

I walked over and knelt down between Cindy’s legs. My cock was still dripping pre-cum; a long string of it hung from the end. Stacy reached over and grabbed my dick, “I can clean this off for you,” and pulled it towards her open mouth. She reached around my ass with her other hand and pulled me closer, and started sucking greedily on me, pushing her head forward until she choked. She pulled back for a moment, then pulled me towards her and gagged again when my cock hit the back of her throat.

….. dammit, now I wanted to deep-throat AND ass-fuck Stacy.

I pulled my cock away from Stacy’s mouth and smiled at her when she looked up at me, ‘this is Cindy’s time’.

Edging forward on my knees I laid my cock down on top of Cindy’s little slit. She was still quite wet from Stacy’s oral work on her, and her own arousal. Rubbing my cock up and down her thin labia a few times, I put the head at her tiny opening. I leaned forward and kissed Cindy deeply, and pulled back and stared into her eyes. I pushed the head a little inside her and watched her. She was locked on my eyes and was smiling slightly, the edges of her mouth quivering.

I looked down at my cock pushing into her tiny little body… it was obscene, and was my every fantasy for a couple of years now. I didn’t want to hurt her, but my whole body desperately wanted to fuck her.

I pulled out and slid two fingers inside her. She was definitely dilated more than I have ever felt her, but I still couldn’t imagine I could fit my cock in her. I guided my cock into her opening again, and started rocking into her. She continued to stare into my eyes, and she would wince a bit each time my cock came to a halt.

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