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Parting Lilly's Petals - Part 1 of 3

A teenage girl experiences an unforgettable first time…

“How are you doing?”

“Mmmm… I’m good.”

I watched through the sounds of her innocent but piercing moans, as my girlfriend tasted and teased my step daughter’s sweet, young pussy.

“Do you like how Cassandra's mouth tugs on your pussy lips?”

“Oh yes… I do.”

I could tell by how she slowly flapped her spread legs and gently gyrated forward her hips that she was telling the truth. Observing the motion of my girlfriend’s auburn mane between Lilly’s parted legs was a sight to behold. But Cassandra's blanket of hair shielded my eyes from observing how she was pleasuring my Lilly.

“Oh, fuck... oops, sorry.”

Cassandra had clearly done something with her tongue to cause Lilly to arch her back and release her profanity, but both of us just ignored it. That type of language was expected in this type of situation. I knew Cassandra was going to do everything she could do for us to hear more of the same.

My girlfriend took great pleasure to be the first to touch and taste a fresh one. She felt she had a responsibility to those girls to ensure they had a wonderful, first experience. The first time Cassandra saw Lilly, she insisted that Lilly’s cherry would be hers. She was immediately smitten by the petite, rhythmic gymnast virgin that lived part-time under my roof. However, Lilly, now sixteen, would be gone in less than two years when she left to attend college on her scholarship. Cassandra was determined. After some devious and manipulative female bonding, Lilly easily succumbed to Cassandra’s comforts and calculated advances.

“How does it feel, Sweetie?”

“Her mouth is so warm and wet, and her tongue is very hot.”

Lilly then moistened her lips with her own hot tongue as her heavy breathing encrusted them dry. I watched her slippery and flushed red tongue run over her top, and then bottom lip, before she bit down, squeezing her braced white teeth against her puffy lower lip. Lilly continued with her high-pitched little girlie moans that easily aroused me.

“Oh shit… Mmmm."

Lilly continued her pleasured sounds of profanity as Cassandra devoured her tasty morsel of flesh.

From Lilly’s fair skin and fine, blonde hair, Cassandra knew this tiny, doe-eyed teen had a bright pink pussy and matching bumhole. Cassandra, and men and women both, dreamed about and drooled for what Lilly had between her legs.

Cassandra had once sneaked a peek of Lilly’s small, burgeoning breasts, which also confirmed her pink suspicions. She pretended to accidentally walk in on Lilly’s as she was changing. Cassandra timed her violation to see as much of Lilly’s naked body as she could. She saw all she needed, to confirm what she already knew.

Cassandra tossed her long locks to the side to give me a view.

“Oh… my… shit!”

Lilly whispered to me as Cassandra flicked her little clitoris with her experienced tongue and rolled Lilly’s tender, untouched nipples between her painted finger nails. Lilly rocked her head side to side as Cassandra’s tongue now sadistically teased where no one has teased before.

“Just relax and enjoy, honey. Cassandra knows what she’s doing. Are you comfortable?”

Lilly nodded as she turned her head towards my voice and I could see my reflection in her excited, baby blue eyes. They no longer reflected anxiety and reluctance, but beamed with delusional arousal.

Early, we had bound Lilly’s hands behind her back for the fun of it, as Cassandra expressed to her. However, Cassandra wanted that psychological advantage stating Lilly has no place to go. We led Lilly to my closet and she picked a neck tie that she had given me for Father’s Day. Cassandra also suggested to Lilly that she would better enjoy her first time this way, making it more memorable. Of course, under Cassandra’s spell, Lilly listened and complied.

What Lilly and I didn’t know, was that my naughty girlfriend had something else in mind.

“Ben, her mound is so smooth. We did such a good job with your razor. You should touch her pussy.”

Lilly’s mouth dropped open when Cassandra suggested I approach my step daughter. Cassandra convinced Lilly that she should be her first, and that my presence was only to observe and assist, if needed. Oddly, she agreed and it seemed to give Lilly some comfort knowing I was near. I don’t know how she convinced her, but Cassandra knew her way around the psyche of a teen aged girl. She also knew her way around an eager, young pussy. She somehow knew Lilly wanted me next to her on the bed.

“Ben,” Cassandra mouthed as she pointed between Lilly’s spread legs. “Come here and taste her pussy. It’s so sweet, so pure.”

This was not part of our initial discussion, but I admit, I was curious. As I motioned to approach, Cassandra placed her mouth on Lilly’s mound and by Lilly’s erupting moans, I could tell she was, at the very least, intrigued by the concept of my touch. Well, that's what I had hoped.

“Ooh… Cassa… ,” was all Lilly could say before her heavy panting took over her words.

Cassandra had parted Lilly’s pink folds with her tongue, marking the first time a person had oral penetrated her virgin opening. With that sudden, intimate violation, I felt like a third wheel, so I leaned back, caressing one of Lilly’s small feet.

“You are doing a wonderful job, Cassie. I’ll just watch.”

Lilly’s chest sighed with relief as Cassandra removed her probing tongue from Lilly’s depths. Cassandra just grinned as I saw her tongue now dance around Lilly’s labia and clitoris. She loved to play mind games, especially with this young one. She was going to build her up high until she exploded.

However, this distraction gave us the opportunity to observe Lilly’s reaction. Cassandra had warned me Lilly might want my touch. If she did, she would beg for my cock too. This was the sign. Cassandra quickly removed one hand from Lilly’s breast, and replaced it with mine.

“Oh!” Lilly yelped as my nipple roll must have been rougher than Cassandra’s.

“How does that feel, Lilly?”

“Yes. It’s good too. Just… a little softer, please.”

Lilly smiled through her again, parched lips. Her words purred as she watched me watch her tongue circle her pouty mouth. Cassandra then pulled my other hand off of her leg, and placed it on Lilly’s the other side of her naked chest. I played with both tiny nipples. I then felt Cassandra’s hand on the back of my head as she pushed me towards Lilly’s face. I held my head above hers as Lilly closed her watery eyes. She gently parted her soft lips waiting to receive mine. As our lips touched and my tongue found hers, we both heard Cassandra’s voice.

“This will be a little uncomfortable at first, but I guarantee it will start to feel much better.”

Cassandra gently inserted her finger, searching for and then relieving Lilly’s hymen with cautious circular motions. I kept my mouth on Lilly’s and I could feel her humming vibrations reverberating through her lips. Lilly exhibited little pain but lots of pleasure. From Cassandra’s stories of prior conquests, I knew this was her move. But this time, she was preparing her prey for something else.

“This will be a little uncomfortable too, but I promise you will grow to love it.”

Cassandra inserted a second finger and began slowly sliding them in and out of Lilly’s freshly opened pussy. As she did this, she also spread her fingers apart, carefully stretching this now claimed virgin territory.

“Oh shit, that feels so good… so good.”

Lilly hissed as I began pulling her cherry pit nipples with my lips.

“I think she likes this, Ben, wouldn’t you agree?”

I concurred with a hum of my own from my mouthful of flattened breast. Cassandra continued to gently massage Lilly’s insides and Lilly continued to blow dry my hair with her intermittent breaths. As I sucked and bit her raw nipples, I could hear her smacking her lips and I could feel her tummy rise and fall with each smooth, penetrating finger thrust.

“Lilly, do you want to feel his cock?”


We didn’t… I mean… what are you doing?

“Yes… I do,” she softly repeated.

“Then you must tell him. Tell him what you want him to do.”

We both stood up and looked down at this nubile body lying on my bed. Her hands bound under her ass and her legs spread wide, with enormous amounts of wetness shimmering from her small openings and inner thighs.

“Please, put it in me!”

Cassandra reached over and rubbed my hard cock through my jeans.

“Baby, you have to tell him you want his cock.”

“Please… put your cock in me… “

“You heard the girl. Let me help you with your pants.”

I watched Lilly’s eyes as she followed my lowering zipper. She smiled when Cassandra unbuttoned my pants and pulled both my boxers and jeans to my ankles. Cassandra then stroked my quickly engorged cock and looked at Lilly’s awaiting slit.

“Tell him again what you want, Lilly darling.”

“Ben, please! Please put your cock in me!”

We both were nervous but Lilly seemed more comfortable with this than I was. However, it was clearly something we both wanted. Cassandra and I walked toward the bed and we both climbed on, me between Lilly’s parted legs and Cassie beside me, still holding but now guiding my cock.

“How badly do you want it, baby girl?”

Cassandra hissed her question at Lilly.

“A lot, Cassandra. I want it a lot.”

Cassandra guided my hard cock and rubbed it up and down Lilly’s glistening, pink pussy lips. That first touch of my teenage taboo sent shivers down my spine. But Cassandra waited for more words. We watched Lilly as she thought of what next to say. She then adopted a demanding tone and pleaded for it just like Cassandra said she would.

“Put your fucking cock in me, Ben!”

Cassandra smiled at me as she squeezed my throbbing erection.

“That’s a good girl. What do you want Ben to do when he puts his hard cock in you?”

“I want him to fuck me.”

“Tell him.”

“I want you to fuck me, Ben! Now! Please fuck me, now!

Cassandra smiled and nodded her approval. I really thought it was going to be her, but all along Cassandra knew it was going to be me. She had been preparing Lilly for this very moment. When Lilly told her during one of their bonding moments that she wanted me, my girlfriend knew what she had to do. Now I know why she wanted me in the room.

“It’s going to be a little uncomfortable at first, but like I said before, it will start to feel much better, especially once he’s all the way inside you.”

Lilly’s prior expression of anxiety-riddled anticipation was now completely wanton lust.

“I can take it!” she growled. “Put your goddamed cock in me! Will you fuck me already?”

I leaned forward and pressed the tip of my cock again against my step daughter’s tender, pink lips. I then pushed and the tip of my cock began stretching her opening. Lilly’s face grimaced, and then her little girlie voice filled the room with screams from her first penetration pain, then quickly changed to an enveloping moan of pleasure. This transition was a lot quicker than I expected.

“Lilly, lean forward. I want you to watch Ben’s cock disappear inside your body.”

Cassandra ripped off her clothes and crawled behind Lilly. She then lifted and held up Lilly’s head to ensure she could see every inch my cock slowly slide between her unsullied pink petals and then inside her tight, little body. I then pushed.

“Oh… my… FUCKING… GOD!”

Lilly screamed as her tight pussy slowly swallowed my cock. I inched it back and forth until finally, her smooth, pussy lips kissed the dark, curly pubic hair at the base. I placed my thumb against her tiny clitty, and rubbed, as I watched my girlfriend straddle Lilly’s face.

“Do you want your mother to still pick you up or would you like to spend the night with Cassie and me?”

Lilly tried but could not answer. Cassandra had lowered her own sopping, hot cunt onto Lilly’s eager mouth. It was only moments later that our darling Lilly experienced her very first of many orgasms that evening.

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