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

…..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.

“God, that is fucking hot!”, Stacy blurted out. She was leaning in so close that her hair was partially blocking my view. I grabbed her hand and stuck her fingers in my mouth to get them wet, then pushed her hand down onto the top of Cindy’s little pussy. She immediately started rubbing her friend. Cindy continued to stare into my eyes, but her mouth dropped open and she started panting lightly.

I rocked my cock in and out of her, trying to push it in further each time. She was so fucking tight… I looked down and was surprised how far my cock was inside her now. I started pushing harder until it felt like I was hitting bottom… I was hitting what must have been her hymen. Cindy was visibly wincing each time I hit it, “Are you okay? Am I hurting you?”

“It hurts a little, but don’t stop… it feels good at the same time. It’s feeling better the more you do it.”

Stacy pulled her hand back to get a better look. Cindy grabbed her hand and pushed it back to her pussy, “Don’t you stop either… that feels really good”, and closed her eyes. I reached forward and started squeezing her breasts… pulling on her puffy little nipples until they were hard. I kept pumping into her, pulling out further until the head almost popped out, then pushing harder inside her tiny pussy.

I pumped my cock hard into her and she let out a shriek… I could feel my cock break through and slide deeper inside her. I stopped for a moment, concerned for her pain, but she opened her eyes and stared at me, almost angrily, “Don’t Stop! Keep going!”

I pumped harder and my cock drove deeper into her… I was in shock… I really didn’t think this could happen.. she was so fucking tight it almost hurt… but it felt so fucking good. I pumped harder and faster into her… I could feel my cock sliding deeper into her with each thrust. Looking down my cock wasn’t all the way in, but it felt like I was. God.. her pussy was unbelievable.

Cindy grabbed Stacy’s hand and pushed it harder against her pussy, “Like that… rub me harder… Oh fuck… Jeff.. fuck me…”

Cindy’s legs started shaking, “FUCK ME! GOD…. I’M CUMMING…”

I pumped hard into her, driving deeper and faster until I was ramming my cock nearly balls-deep into her tiny body. My God.. it looked so obscene… my thick cock pumping into her. She was so young.. so fragile… and yet she was fucking my cock like an animal. Her legs were shaking like she was having a seizure as she rode through her climax.

I slowed my thrusting as her body relaxed… she fell limp under me… I loosened my grip on her legs, which, in my passion I had pushed up to her shoulders.

I looked over at Stacy, who was still hanging over her friend. Her eyes were still fixed on Cindy’s little body impaled on my cock, her right hand on Cindy’s pussy, and her left was rubbing her own. I slowly pulled my cock out and could see some blood around the base. “Are you okay? Did I hurt you?”

Cindy was still panting, “I am more than okay… that was fantastic.” She paused a bit to catch her breath. “It did hurt a little at first, but kept feeling better and better until… well… then it felt REALLY GOOD”, she laughed.

Her expression changed to concern, “But you didn’t come yet, did you?”

“Not yet, but the night is still young,” I replied, and looked at Stacy. She glanced at me, then thrust her head down and shoved her mouth onto my cock.

I was shocked… the blood on my cock didn’t even phase her, or she was so drunk she didn’t realize.

“Slow down… I think there is another climax or two in each of you,” and pulled back from her mouth.

Stacy looked up at me like a spoiled child being denied ice cream. Cindy looked at her and laughed, “I think we can take care of you,” and Stacy’s pout quickly turned into a smile.

————————— Fun Sandwich on the Floor —————————

I stood up and grabbed a towel and spread it out on the carpet. I picked up Stacy and laid her down on the towel on her back. She was a bit heavier than Cindy, but I would guess still under 100-pounds wet.

“Cindy, can you give me a hand?” I asked, like I needed her to help me move a couch. Cindy walked over and knelt beside her friend. “I want to see what these toys do.” I grabbed the little silver ‘bullet’ thing and turned the dial on the control. It started buzzing, and the further you rotated the dial increased the vibrations. I handed the control to Cindy, and held the silver button against Stacy’s pussy. She immediately reacted with a squeal, then started gyrating against it, “WOW! That feels nice…,” like she had never felt it before. I kinda doubted that.

“Spread her open for me,” Cindy looked at me like she was surprised at the request, but quickly dropped the control and reached down and spread open Stacy’s pussy. I grabbed the black dildo and pressed it against her opening. Stacy’s eyes sprung open and looked down in feigned surprise, “Oh my gosh!” Now I knew she had been masturbating with these toys. I started pushing the dildo into her, and the head quickly popped in with only a little resistance. She closed her eyes and laid her head back, clearly enjoying the feelings.

I grabbed Cindy’s left hand and handed her the silver ‘bullet’. She immediately pressed it against Stacy’s clitoris. I grabbed her other hand, “Hold this for a moment,” and placed it on the black dildo. Again, she looked shocked, but started slowly pumping it into her friend’s pussy. Stacy opened her eyes and looked at what was going on, and her mouth formed a large open smile, “Gosh, Cin..”

…..her fake shock was amusing, and turned me on even more

I stood up and grabbed Cindy’s hips and lifted her up off the floor. She awkwardly tried to hold onto the bullet and the dildo, but had to drop the bullet to regain her balance. I rotated her around and set her knees on either side of Stacy’s head, so they were in a 69 position, her just-fucked little pussy right above Stacy’s face. Stacy immediately reached her arms around Cindy’s legs and grabbed her waist, and ran her hands up her ribs and started fondling her pointy titties.

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