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Best Night of My Life Part 4

Three cheerleaders prove that sometimes a nice guy can finish first.
Authors Note: Although based on certain true events, this story is a work of fiction. It is intended for entertainment purposes only. It builds slowly and contains a lot of details. Yes, there is sex in this story. No, it doesn't happen right away. If you are looking for a story with raunchy sex at the get-go that never lets up, you probably won't enjoy this. Most of the scenes are a build-up of erotically charged circumstances.

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continued from Part 3

Ashley climbed onto the bed behind Sara and unhooked her lacy pink bra and tossed it aside, leaving Sara’s magnificent breasts on display. Sara allowed herself to be pulled up onto the bed and layed down on her back, allowing total access for both girls. They wasted no time, Ashley engaging her in a full mouth kiss and then starting a serious make out session while Lauren was basically straddling Sara while kissing and sucking on her breasts and nipples.

This left Lauren’s heart shaped ass pointed straight at me, barely concealed by the little thong panties she was wearing, so I took the opportunity to admire and handle the merchandise some more. I had to just shake my head again at how damn sexy and perfect Lauren’s tight ass was, my hands roaming all over and massaging every inch of it.

Ashley broke the kiss with Sara and nodded to Lauren. Lauren disentangled herself from Sara and allowed Ashley to take her place, straddling Sara. Ashley leaned down to kiss Sara softly on each breast, and we all knew this was her first time doing anything like this with another girl. Sara smiled and rewarded Ashley with a little moan of pleasure.

While that was going on, I pulled Lauren over to me. We were face to face, both kneeling on the bed and Lauren arched one delicate eyebrow while staring at me with her gorgeous, baby blue eyes. I knew she was wondering if I could work a bra, not many guys could. I leaned in closer to her, reciting a silent prayer to the lingerie gods, reaching my hand around to her back and went for it. Her bra practically unhooked itself (YES!!) and within seconds it fell off, revealing Lauren’s curvaceous set in all their glory. Lauren’s smirk turned into a huge grin of surprise and admiration as she picked up the bra off the bed and tossed it aside.

I leaned in very close to whisper into her ear only, “Lauren, you now know how much I have always admired your tight, heart shaped little ass. And I know every guy at school does to. But I just have to tell you, from every guy who has ever paid too much attention to your ass to admire your beautiful breasts, we are all very sorry. You are magnificent.”

Lauren had closed her eyes and we started to kiss, both on our knees on the bed, softly at first and then more passionately. We laid down, me on top of her, still kissing and making out as my hands started to roam over her supple breasts, caressing them. I moved a little further down, kissing and sucking on each breast in turn.

Looking over, Ashley and Sara were right next to us, in the same position, Ashley still playing with Sara’s twins. Ashley looked over at us, her and I locked eyes for a moment. I grinned and winked at her.

Moving perfectly in sync with each other, Ashley and I each moved down a little further on our respective girls, slipped our hands into the sides of their panties, and with one smooth motion slid them completely off.

Lauren and Sara were looking at each other too, both fully nude now, they reached out and held hands in anticipation of what was about to happen, this experience they were about to share. They parted their legs and I saw little smiles on their faces.

Ashley leaned over to me and whispered “I don’t even know what to do next!”

I wasn’t an expert on this subject either, but my older brother had given me once piece of advice that I hoped to God was true. “Spell the alphabet with your tongue,” I whispered back to her. She nodded her agreement to my suggestion.

I turned my attention back to Lauren. I leaned in between her legs, noticing now that she was completely smooth. I guess the girls did more prep work than I realized and wondered if Ashley had shaved also. I put my head down to her pussy lips, parting them with my tongue, trying to be as gentle as possible. Lauren was starting to breathe heavier and I could feel little goose pimples start to rise on her skin. I stuck my tongue in as far as I could and started to go to town.

I never really thought about it until now, but I have a talented tongue. I could stick my tongue out far enough to touch my nose, I could roll my R’s, I could eat a cherry and tie the stem into a knot without taking it out of my mouth, and I could contort my tongue into a cloverleaf shape. I read in one of those strange facts books that less than 5% of the population can do all of those things.

I was thankful now for all the weird, strange things I could do with my tongue. I was determined to make sure than my first time giving oral pleasure to a girl was just as good as the oral pleasure she had given me earlier.

I started off with the alphabet, like I had told Ashley to do, and Lauren was making her little mewling sounds of arousal again almost instantly. I heard Sara’s moans as well so I knew that Ashley was having similar success. After finishing the alphabet both forwards and backyards, Lauren was starting to cry out and she was getting close. Not sure what to do my next, I started to twirl my tongue like I did when rolling my R’s, and Lauren started to go wild. She was bucking and arching her back, grabbing hard onto the bed with one hand and Sara’s hand with the other. I thrust my tongue as deep into her as I could, twisting it into a cloverleaf shape at the same time and that sent Lauren over the edge.

“YES! YES! OHHHHHHH!!!!” she was screaming at the top of her lungs, vibrating all over and her juices spraying out as I lapped up as much as I could.

Ashley seemed to be having similar success with Sara, who as I looked up was also close to climax. Ashley seemed to be licking in concentric circles and soon Sara was howling with orgasmic intensity and now it was her turn to hold onto Lauren for support.

Both girls needed a minute to recover after that.

“That was amazing!” said Lauren. “Jeff, the things you were doing to me with your tongue, I had no idea…”

“Don’t forget our girl here,” Sara chimed in. “She knew exactly where to go without me needing to guide her at all.”

Ashley smiled at the compliment. “I just went on instinct, what I would like to have done to me.”

“Is that a hint?” asked Sara. “I would be happy to return the favor.”

“Well, maybe a bit later,” said Ashley. “I am feeling a bit left out though. You two have already gotten off 4 times tonight, and me only twice.”

“She speaks the truth,” said Lauren. She got up from the bed and pulled me up with her, Sara did the same with Ashley. “And you two are the only ones still with any clothes on. I think it is time to resolve both those issues.”

Lauren walked around to one side of me, Sara to one side of Ashley. Lauren hooked her petite hands into my silk boxers while Sara placed her fingers under the straps of Ashley’s teddy. Simultaneously, they slid down our respective coverings, revealing our full nudity.

I could see instantly that Ashley had shaved herself completely smooth also. Ashley and Sara were both checking me out from their position.

“Jeff!” Sara practically shouted. “You trimmed!”

“Really?” asked Lauren, on her knees right next to me, slipping my boxers off and tossing them aside. She walked on her knees to my front side. She took hold of my cock and lifted it up, inspecting. The other girls came over and dropped to their knees as well, and they all started to handle the merchandise, nodding their approval.

“It looks so much nicer now,” said Ashley. “I mean, not that it looked bad before. It’s just, neater, I guess.” The other girls agreed with her, and with all the stroking and attention I was quickly back at full mast.

I wasn’t sure what the next step was, but the girls seemed to know right away. They picked Ashley up off her knees and led her to the bed, lying her down on her back. Then they came back for me and led me to the bed as well, and I quickly realized that I was about to enter a girl sexually for the first time.

Sara laid down next to Ashley and reached over to cradle her in her arms, giving her little kisses and whispering sweet words to her. Lauren produced a delicate glass bottle of some type of nice smelling oil. She poured a little out onto her fingers and rubbed it into Ashley’s waiting pussy, and then announced that it was time.

I lowered myself down onto the bed, missionary style over Ashley, looking into her hazel eyes which were showing a mix of both trepidation and anticipation at this moment we were about to share together. I positioned the tip of my cock at the entrance to her pussy and slowly began to ease my way in.

The effect was immediate. Ashley began to cry out in sexual pleasure the second I entered her. She closed her eyes to savor the moment, as I pushed in another couple inches, slowly, trying to make this last. She continued to make sounds of satisfaction and with one final motion I thrust myself all the way in. Her eyes flew open as she gasped out “Oh My God!! Ohhhhhh!!” and she was clearly already very close to climax.

My cock had been transported to another world, a world of softness and warmth. It was pure ecstasy and I couldn’t believe the sensation. This may have been my first time but I knew enough at least to not just lay there motionless. I began to move my hips back and forth, working my cock almost all the way out of her incredibly tight pussy and then all the way back in with one continuous thrust, and then repeating the process over and over, increasing my pace faster and faster.

Ashley quickly exploded and continued screaming with primal, sexual pleasure. She had given herself over completely to her primitive sexual needs. She was beginning to shake and convulse as her bodies desires started to completely overwhelm her conscious self. I continued to thrust in and out, as fast and as deep as I could, using every inch of my cock. Another orgasm shook her body as she continued to howl in ecstasy, and then another just a moment later.

I was unbelievably hard at that point, my cock felt as though it had swelled larger than it ever had before. I could have continued to do this all night but somewhere in the deep recesses of my brain I recalled that I still had two other girls to see to and I needed to pace myself. Reluctantly, I slowed my thrusts down and then with all final swerve of my hips I pulled out completely.

I stood up and looked down at Ashley, laying there on the bed, completely nude and covered in sweat and her own juices, breathing heavily and her eyes closed in complete contentment. She was a goddess and I almost felt a compulsion to kneel down and worship her.

Sara, still cradling Ashley in her arms, leaned over to kiss her on the lips and she whispered something into her ear but I couldn’t hear what she said. All I know is that Ashley smiled and nodded her head in the affirmative before finally sitting up and trying to compose herself.

Ashley stood up and came over to me, she kissed me passionately and then turned me around and pushed me down onto the bed on my back. Sara, still on the bed, held out her hand to Lauren, who handed her the glass bottle. Sara poured out a little into her hand and then reached over to me and began to give me a quick handjob, spreading the lubricant all over my cock. As soon as that was done, she rolled over on top of me, straddling me and then with one smooth motion she rose up and positioned the entrance of her pussy just above my waiting, full mast erection.

Gently, she lowered herself down onto me, and then leaned down to kiss me as she began to rise herself up and down in a slow but steady rhythm. I don’t recall what song was playing on the stereo, but her hip thrusts were in a perfect staccato timing with the music, as though our love making was a sensuous dance between the two of us. I quickly picked up on her pattern and adjusted my own thrusts to match hers. As the song began to increase the pace of its music, we increased our pace accordingly, and as the music reached its crescendo so to did Sara.

Previously, Sara had been the loudest of the girls but this time was different, as she reached her climax in complete silence, her entire body shuddering but no sounds came from her lips. It was all in her look however, her face so close to mine, the light of the candles reflected in her brilliant brown eyes.

With a playful groan of reluctance, Sara rolled off of me, laying next to me on the bed. Ashley crawled onto the bed, sliding her nude body up into Sara’s arms and cuddled with her.

Lauren was the last girl left. Somehow it seemed fitting that she was the last. I was closer to her than the other girls, had known her longer. If it was not obvious so far, I can confess that she was my favorite. It forced to pick just one girl, I would have chosen her in a heartbeat.

I continued to lay on my back, right next to the other two girls as Lauren glided effortlessly into my arms. We began to kiss, and she seemed to melt into me with a sort of feminine willingness, a need to be so close to someone that you no longer knew where you ended and they began. This kiss was different from anything previous in the night. It was more sensual, more arousing, more emotional. Lauren and I were connecting in a way that I hadn’t been able to with the other girls, and I gave myself over to it completely.

Somewhere in the passion of our kissing, Lauren’s sweaty and nude body right on top of mine, I slid into her with one smooth motion, an almost unconscious act on my part yet it seemed the most natural reaction in the world. Lauren received me with a private smile of pleasure, and in her eyes I could see that this was different for her too. She broke the kiss, rising up from me like an Angel rising up into heaven. She leaned back, her flexible cheerleaders body arching further and further back until she was grabbing her own ankles. She began to work herself up and down, affording me a perfect view as she slid herself over every inch of my cock. I timed my thrusts in opposition to her own, and then back into rhythm and then opposite again, alternating back and forth.

The candlelight was reflecting off her nude form, a perfect vision of beauty and sexual desire. It was a moment of pure sensual bliss, and we were both very close to climax. It happened all at once, both of us together, exploding with a force that shook the bed and Lauren threw herself forward onto me as it did, her mouth finding my own with a kiss that was so soft compared to the power of our combined finish.

Our story ended there. We all fell asleep, the candles burning themselves out, absolutely spent from our night together, our nude bodies all nestled together until the next day when we finally awoke, well past noon.

I stayed through the weekend, as intended. Ashley and Sara chose to leave back to their own homes to give me and Lauren a night alone. It was a night well spent, just the two of us, and even after Joe and his parents returned Lauren and I continued to see each other. The other girls and I never spoke of the night again, it was a special moment in time that needed no discussion, but it remains to this day the greatest night of my life.

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