My high School Sweetheart's Young Sister - S01 E20

My high School Sweetheart's Young Sister - S01 E20
Read Story: SEASON 1 EPISODE 20
-------Cindy's attempt------
"Be gentle...", Cindy said, looking a little scared.
I reached over and slid two fingers into Stacy's pussy, and came back with a nice amount of her lube, and rubbed it all over the condom. Stacy laughed, then licked her fingers and rubbed her wet fingers all over Cindy's little slit. Cindy gasped at her touch, but didn't stop her.
I laid my cock on top of Cindy's opening and started gently sliding it up and down the length of her pussy, which was actually only about 2-1/2" from top to bottom. Cindy closed her eyes and lald her head back.
Looking down at her tiny body. that little pink slit, spread open for my cock... unbelievable... my 8" cock looked absolutely obscene in proportion to this petite little girl.
Stacy decided she was too far from the action and crawled up on the pool table on the right of Cindy, and reached out with both hands on either side of Cindy's pussy and spread it wide for my cock. Cindy opened her eyes and stared at me, wide-eyed, then looked over at Stacy's ass, which was right beside her.
I placed the head of my cock at Cindy's little opening and started pushing gently, rocking back and forth. Stacy's eyes were locked on my cock pushing against her friend's little pussy... she reached her hand down to her own, and pulled it back cupping a small puddle of lube in her fingers, "Here, use this", and grabbed my cock with her other hand, pulling it away from Cindy. Stacy held her hand over Cindy's little hole and let the lube drip down directly in her opening, and rubbed it in place all over Cindy's pussy, then slid her middle finger inside her. "Oh My God, Cin! You're so fucking tight!"
Cindy gasped, and by the look on her face she had never seen this side of her friend. I had to admit I was shocked at how bold this young girl was.
Stacy moved her hands back to the sides of Cindy's pussy and spread it wide again for me. I slapped my cock down on Cindy's slit, which made her jump, then started pushing the head into her little hole. I was having little success... the head was barely inside her and I could see Cindy was in a bit of pain.
"Push harder!", Stacy directed, impatiently.
"Ouch! Be gentle... that kind of hurts"
I looked down and the head of my cock was only in about half way. We all knew this wasn't going to happen, but Cindy wanted to keep trying. I started rocking a little more and pushed harder against her.
'OUCH! Jeff. I'm sorry... but that really hurts."
I pulled my cock out and the head had lost all color and was squished down to about half its normal size. This wasn't going to happen very quickly.
Stacy sat up, "I told you that big dick was never going to fit in you." She then laid down on the table beside Cindy, scooted up to the edge, and raised her legs. Using both of her hands, she reached down and spread herself open for me to see. Stacy's little pussy looked so much larger and mature than Cindy's, especially with her swollen labia. She was sopping wet, primed and ready for my cock.
"Okay! My turn... let's see if you can fit that big thing in here!", and with that, she slid two fingers inside her pussy, and started masturbating.
I looked over at Cindy and was surprised when she just shrugged.
She was clearly frustrated, but had a look of lust on her face and was staring intently at her friend masturbating. I asked her, "Are you really okay with this?"
She nodded her head, "As long as I can watch", and laughed.
She sat up, and knelt beside Stacy, like Stacy had done with her. I moved over and stood between Stacy's open legs and slapped my cock on her meaty little pussy.
"Spread her open for me"
Cindy hesitated for a moment, then leaned forward and placed her tiny hands on each side of Stacy's pussy and pulled the lips open. "Jeeze, Stace... your lips are so much bigger than mine. I look like I haven't even reached puberty compared to you."
"I dunno, Cin.. your pussy looked pretty darrın hot to me" Stacy
replied, and reached over and slapped Cindy on the ass.
This was getting too much for me. My cock was rock hard... I needed to fuck her now. I put the head against her small opening and started rocking. The head slipped in almost immediately, but the thicker shaft stopped short. Stacy took a deep breath, "Oh, Fuck!... you are so big... but it feels good... just go slow..."
I pulled back, then pushed forward with a little more pressure, and my cock came again to an abrupt halt at the thicker shaft. I grabbed Cindy's right hand from the side of Stacy's pussy and placed it directly on the center, and moved it around.
Stacy moaned, "That feels good... keep doing that..." I wasn't sure if she was talking to Cindy or to me, but kept rocking my cock against her pussy, increasing the pressure each time I pushed in. I noticed Stacy's hand was still on Cindy's ass where she had slapped her. Cindy didn't seem to mind, or at least didn't move it and continued to rub Stacy's pussy.
God, she was so fucking tight... I grabbed Stacy's hips and pulled her against me, pushing my cock harder at her tight opening. "Does that hurt?"
"Maybe a little, but it feels good... don't stop.
...I thought to myself, maybe it doesn't hurt now, but I bet you are gonna be pretty damn sore tomorrow
I reached out and pulled Cindy towards me. She scooted forward on her knees and kissed me, sticking her tongue deep in my mouth. I reached between her legs and rubbed her pussy... she was very wet... I noticed she was rubbing Stacy more aggressively. and Stacy's hand was still on her ass. I kept pushing harder into Stacy, and finally felt my cock slip a little further into her pussy. Stacy gasped loudly, "OH.. FUCK... that feels so fucking big... God..." I held my cock there for a moment.
I reached out and grabbed Cindy by her legs and lifted her petite body up, and sat her back down straddling Stacy, placing her knees on either side of Stacy's ribs. Cindy was shocked at the move and sat up straight for a moment, but I reached out to her and pulled her in for another kiss. I knew this would arch her body so her pussy and ass would be open and exposed inches above Stacy's face.
I moved my hands back to Stacy's hips and pulled her harder
against my cock and started pumping further into her. I was glad
that we were all rather drunk... these girls were allowing things
they would have never done sober. Stacy now had both hands on
Cindy's ass, and Cindy's knees were spreading apart, lowering her body close to Stacy's face.
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