My High School Sweetheart’s Little Sister -pt. 9 (Cindy’s Deflowering) by JadeGrey
This is the ninth chapter of this story from my late teens, where my girlfriend’s little sister made it through puberty only to lose her innocence due to my uncontrollable lust for her. In this chapter, I finally get my cock inside of Cindy, with the help of her friend Stacy. , Note: This is a continuation of a 9-part story. It would be better to start at part-8 to understand the situation leading up to this chapter, or better yet start at part-1 to get to know the characters and slow build-up to this rather hard-core climax. Click on ‘JadeGrey‘ in the above title for links to all stories.
——————— Part 9: Cindy’s Deflowering ———————
I carried Cindy over and set her down on the couch, lifted her legs, and pulled her butt to the edge of the cushion. I felt a tugging on the back of my underwear, and turned around to see Stacy pulling them off of me. She worked them down over my ass and when she finally pulled them down over my erection, my cock sprang up throwing a line of precum onto the cushion just below Cindy’s ass.
I think there is going to be a lot more mess on this couch before the night is over…
I pulled Cindy’s legs up onto my shoulders, lifted her ass off the couch, and slid a towel under her. Kneeling down in front of her, I folded her legs towards her chest and started licking her little pussy. “Hold your legs like that,” and she pulled them up tighter to her chest. I licked her little opening again, and pushed a finger inside. God, she was still so fucking tight… her little pussy was going to have to stretch a lot more if I was ever going to get my dick in her. I added a second finger and worked them deeper into her. Looking up from her tiny mound I could see Cindy was enjoying this, but she grimaced now and then when I pushed my fingers in further. “Am I hurting you?”, Cindy just shook her head.
I didn’t really realize how exposed I was to Stacy, who was behind me. I flinched when I felt her hand reach underneath, between my legs, and grab my dick. She worked it for a bit, played with my balls, then I felt her squeeze some lube over my ass with her other hand. She pulled her hand from my cock and started rubbing the lube all over my ass… I was trying to concentrate on going down on Cindy, but was shocked when she ran her fingers right over my asshole and down to my balls, then back up. Then she stopped and started rubbing her thumb right on my asshole. This was not expected… no girl had ever played with my ass, and I wasn’t too sure about this new direction. I was beginning to love ass-play, but on the receiving end? She rubbed it all around, then started pushing her thumb (I think it was her thumb) into my ass.
I reached back and pulled her hand away, “Don’t… I don’t like that,” (hypocritical bastard that I was).
Stacy huffed loudly, “Really? You can dish it out, but you can’t take it?”, and slapped my ass before she came around to my side. “Fine… what can I do to help?”
I took both of my hands and spread Cindy’s pussy open. “Do you think she is ready?” Stacy leaned in and stared at her friend’s little pink opening.
Cindy lifted her head and looked at us between her legs, “I’m sorry I’m so small. I look like a little girl… I wish I was more mature. I swear I’m going to be a virgin forever.”
Stacy kept staring at her friend’s tiny pussy, “I love the way you look… you are sexy as hell… I could just…”
Suddenly she just pushed me aside and threw her head down between Cindy’s legs and started licking her. I wasn’t expecting this, and by the shocked look on Cindy’s face, neither was she. Cindy quickly closed her eyes though, and laid her head back, obviously enjoying what Stacy was doing.
Now I was outside of the game, although the view was erotic as hell. I moved back and watched Stacy going down on Cindy and tried to burn the memory into my mind. Stacy pushed two fingers inside her, and was aggressively slurping on her pussy. I moved behind Stacy and grabbed her ass, spreading her cheeks apart. She reacted by moving her knees apart, and arching her ass so I had better access. Her pussy popped open when I spread her cheeks, and her lube was flowing out of her opening… no shock there. I pushed two fingers into her and I swear she was nowhere near as tight as the last time I felt her. I looked over to the bar where she set down the toys she pulled from her mom’s side table and could see a pink vibrator and some other items.
…has she been masturbating with those toys?
I pulled my fingers out, stood up, and walked over to the bar. The vibrator was a little smaller than my dick, and tapered at the end. There was a larger black dildo shaped like a cock and balls, some beads on a string, and a little silver bullet-shaped thing with a cord and control. I had never seen these last two things before, but if Stacy grabbed them I imagined she knew how they were used. I grabbed all of them, and the lube, and looked back at the girls. Cindy was still holding her legs up to her chest, her tiny feet in the air, but now her arms were reaching around and her hands were on Stacy’s head. She was gently rocking her hips against her friend’s mouth.
I walked over and knelt behind Stacy, setting the toys on the floor to my left. I grabbed her ass again and spread her open. My cock was inches away from her spread pussy… or her ass for that matter. I pushed two fingers inside her, and as always, she was wet as hell. I started stroking her g-spot and it began to swell up almost immediately. I grabbed a towel and laid it down under her, knowing what was going to happen before too long.
Stacy was sucking on Cindy’s pussy like mad. Cindy was now panting, mouth open, and aggressively humping Stacy’s face, “God… Oh My God, Stace… that feels so good… Fuck… FUCK!” I pushed my fingers harder into Stacy, pushing her mouth harder against Cindy.
Cindy’s body started bucking and her legs shook in the air as she came, her hands pulling Stacy’s face hard against her pussy. I could hear slurping and sucking sounds as Stacy struggled to breathe.
Cindy’s convulsions finally slowed and she relaxed her grip on Stacy’s head. She was still breathing heavily as she opened her eyes; her mouth still open, but slowly changing to a large smile as she gazed at her friend between her legs. “Oh My God, Stace… that was… (panting)… that was amazing… I’m sorry if I…”
Stacy pulled her head back and interrupted, “You were wonderful. You ARE wonderful… and sexy as hell.” She kissed her on her little button, which made Cindy jump.
Stacy then looked back at me and pushed backwards against my probing fingers. She reached up and grabbed a pillow off the couch, and put it under her, “I would say it’s my turn”, and laid her head down on it, her ass still up in the air. She reached back with both hands and spread her cheeks apart. This shocked me at first, but I realized she probably didn’t like that I was so eager to eat Cindy’s ass, but hadn’t shown any interest in hers. I looked at Cindy and smirked at her. She just smiled, still in a state of euphoria.
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.