Hillary: The Summer of '92 Ch. 09

"Oh...Jesus! This...this feels so...Oh, God!...it feels so wild!" she whimpered as my finger moved in and out of her. "I...never...knew it...would be...so...so good!"

While my index finger continued to move in and out, I again took the tube of lubricant out of the hot water and opened it. I squeezed more of the warm, slippery fluid onto the finger invading her tight butt, and on the finger next to it. Then I pulled my finger out of her.

"Oh, God! No...don't stop that, it feels too good!" Hillary whimpered.

I pushed two lube-slippery fingers back into her anus.

"Ohhhhhh!" she groaned. "God! Oh, God!" She may have been moaning, but I knew what I was hearing weren't sounds of pain.

I resumed finger-fucking her bottom, moving my hand around a little, trying to open her more, to lubricate her, and to make room for the eventual entry of my erection which by now felt hard enough to cut whatever substance they use to cut diamonds. I wanted to be in her bottom so bad, but I had a feeling once I was finally there, I wasn't going to be able to last long.

After it her bottom seemed to have loosened up, I asked her, "Are you ready?"

"Are...are you going to...put...you know...your...um...in...me?" she stammered.

"If you're ready, I'm going to try," I replied.

"Do it!"

I slid front a little, until my bouncing erection slapped her bottom, then I squeezed some lubricant on it and made sure it was well-covered. Once that was done I pulled my fingers out of her, grasped my rigid shaft in my hand, and placed the tip against her anus, which was still spread open a bit from having my fingers in it. Very slowly I shoved my hips forward...and the slick tip of my erection slid off her anus and up through the valley between her buttocks.

"In me! Please!" she moaned. "Please put it in me there!"

"I will," I told her. "It's just that I'm not so good at this."

I repositioned the tip of my swollen member at her anus and held it in place with my hand this time when I began shoving gently forward with my hips. This time it didn't slide off. Instead, I could feel myself pressing into the tightest, warmest opening I'd ever been in. A rush of delight swept through me. I actually was taking Hillary's anal virginity.

"Oh, God! You feel gigantic!" my teenage lover groaned as I slid ever-so-slowly into a place that no man had ever before entered.

"Am I hurting you?" I asked. Part of me was scared I'd somehow do permanent damage to her. Another part of me wanted this so bad that not even a fire hose spouting icy water could have stopped me.

"God, no!" Hillary replied. "It's awesome! I...I never felt anything like it! It's so awesome!" She shoved her hips back a little, taking another inch or so of me into her.

Eventually I managed to get all of my erection into her. It felt as if I'd slid into an opening three sizes too small for me. It also felt incredibly good. I had to call on ever last bit of self-control I had to keep from spouting into her right then and there. I could feel her moving, then her hips began twisting and she began making even more fervent sounds. Hillary had started caressing her own clit.

"Do it!" she murmured. "Take me! Fuck me!"

I grabbed a buttock in each hand and slowly pulled my erection almost out of her, then I slid it back in slowly, but not as slowly as the first time I'd entered her.

"Yeah! That's it!" Hillary groaned. "Do that! Do it more!"

I kept sliding in and out of her, feeling the waves of incredible pleasure washing over me, fighting coming with everything I had, but I was rapidly losing the battle.

"This feels too good, baby, I'm going to come," I warned her.

"Do it! I want to feel it!" she responded. I could feel the movement of her hand on her clit grow faster. "I'm gonna come, too!"

I think I got two or three more strokes into her, then bright lights of joy began flashing behind my closed eyes and my body went into spasms of joy while ecstasy roared through me like a hurricane. I could feel my fluids being pumped up from my insides, through my pulsing erection, and spraying into her. I was making wild, animalistic sounds and my fingers were digging into her taut butt as I lunged against her.

"Oh...I...I can feel you! It's so hot! Oh, God! Oh, yeah! I'm cumming, too!" Hillary cried. Her back arched, she lifted her head off the bed and twisted it from side to side, making her hair whip back and forth. "Ahhhhhhhh!! Ohhhhhhhhhh!! Oh, damn! Ohhhhhhh! Ohhhhhh, yeahhhhhhh!"

As my orgasm calmed, I leaned forward, supporting myself on wobbling outstretched arms. Hillary's movements and the sounds she was making calmed, too, and she eventually relaxed onto the bed with my softening penis still ensconced in her snug opening. I didn't want to crush her, so I pulled myself out of her and rolled onto my side on the bed next to her, laying on my side facing her.

Hillary immediately rolled onto her side and pressed against me, kissing me on the face and lips. "God...Oh, God...that was so awesome!" she babbled. "Thank you for doing that for me!"

"I think I'm the one who should be thanking you," I told her when she allowed me enough time to speak.

"I have a surprise for you," she said after kissing and thanking me some more.

"Another one?" I asked. "Besides supper and that dress you were wearing?"

She nodded. "Yeah, besides them."

"What is it?" I asked. "If it's as good as the last ones were..."

"It's better," she said, interrupting me. "I can stay all night. I told my folks I was sleeping over at Melissa's."

I kissed her. "You're right," I told her. "That's the best surprise of the night."

We did finally have to get up to go to the bathroom, but after we did that, we snuggled into each other's arms and fell asleep. I was glad she didn't have to go home.