Second Time With Skippy

Second Time With Skippy

Status: Finished

Genre: Erotica


Status: Finished

Genre: Erotica



Shy Lark goes on her first date with Skippy, a guy from the neighborhood where she grew up. At their second encounter, she looks forward to experiencing more intimate pleasures already introduced to her by him.



Shy Lark goes on her first date with Skippy, a guy from the neighborhood where she grew up. At their second encounter, she looks forward to experiencing more intimate pleasures already introduced to her by him.


Submitted: August 29, 2016

A A A | A A A


Submitted: August 29, 2016



Second Time With Skippy


I felt like I dreamed when Skippy arrived at my house to pick me up for our first date.  This tall, really good-looking young guy in jeans and T-shirt that amplified the hard body beneath stood in front of me.  The neighborhood kid, now a man, touched me with those calloused hands.  On the previous day at Jon’s high school graduation party, the same hands took me on my first sexual trip.  I was enthusiastic to experience that again.  Burned inside at the thought of it and those worker hands of his.

Skippy endured the interrogation by Daddy and my brother Desmond like a pro.  He promised my return unharmed before curfew.  Now this hunk held my hand and led me to his beater pick-up truck.  The door creaked when he opened it for me.  For sure, the truck had seen better days.  A number of dents lined the body of the older Ford, but the engine ran smooth.  The interior was clean if not just a bit worn. 

Skippy drove us to Union Station on the edge of downtown.  An Amtrak train hub, it was linked to the subway, the Greyhound bus station, and fell on a public bus route.  Around it were well-placed specialty shops, unique restaurants, and an AMC movie theater.  A busy place for people watching, my friends and I frequented it every weekend. 

Us girls, Sabrina, Kim and I, liked to hang out at the decently priced food court (with a McDonald’s) and movies on the lower level.  The shops were a little pricy, but we liked window-shopping.  In particular, the bookstore on the upper level always received a visit from me to see what was new.  My friends let me indulge there before insisting a stopover at the hip clothing store to drool over some trendsetting ensemble.

When Skippy parked and opened the truck door for me, he lent a hand to me like a gentleman.  “Have I told you how pretty you look, girl?” he whispered in my ear when he stepped close.

Feeling bashful, I shook my head but glanced up into his eyes that sparkled with warmth.  “No, but thank you.”  I wore my favorite pink and white floral mock-wrap dress and some comfortable flats.  I had no idea where we would be going and what we’d be doing so I wanted to be comfortable but still cute.  I left my dark hair down and lightly curled at the ends.  I wasn’t much into make-up so I just used a little mascara and lip-gloss to keep it as natural as I liked.

Hand-in-hand, we strolled into Union Station.  Many people rushed about, but we took our time, smiling at each other like we had all the time in the world.  I leaned into him on the escalator and kissed him on the cheek.  His smile brightened at me. 

“What’s that for?” Skippy asked while touching his cheek I kissed.

“Thanks,” I replied with a sigh feeling so happy.

“Why?  I haven’t done anything yet?” he inquired as he stepped off the escalator and moved over to the side out of the way of walking traffic.

“Sure you did.  I just thought, you know, you’d been drinking yesterday, and ummm, you might not come for me today.”  I looked down at our hands linked together and still couldn’t believe it.  My heart pounded so fast.  I felt a little nervous, but when I looked up at his face again, I felt more at ease and warm butterflies at my tummy.

Skippy blinked at me in surprise.  “I wasn’t drunk.  I knew exactly what I wanted.  You.”

I shrugged.  “Well, I’ve been stood up before and—“

He cut me off as he leaned down and kissed me on the lips.  His fingertips gently tilted my head up to him and then I felt his thumb lightly along my jaw.  The kiss was chaste.  Only lips, not anything near what I knew it could be behind closed doors, but I liked it all the same.  It communicated what he already said.  He wanted me. 

I moaned without a thought when I grabbed a hold of the side of his face and kissed him back.  Someone bumped into us with their large suitcase though.  “Oh!  I’m so sorry,” the heavy-set old lady apologized as she tried to maneuver the luggage on the tiny wheels away from us.

Skippy grabbed me before I fell and deposited me to safety away from the old woman and her wobbly luggage.  His biceps bunched at the effort exerted and felt hard under my grasping hands.  I lost my breath.  We both watched the old lady and chuckled. 

“Thanks again.  I’m glad you have fast hands because that could’ve been ugly,” I said gratefully with my hand in his again.

“We better get out of traffic,” Skippy advised as he led the way again toward the lower level.  He entered the line for the movie theater and paid for two tickets to see some action picture.  To tell you the truth, I couldn’t remember what it was about now.  I suppose I was too distracted by my hunky date who not only held my hand, but progressed to touching my arm, my leg with his calloused fingertips.  A number of times he leaned close.  Perhaps he meant to whisper something about the movie to me.  It all served only to drive my lust for him into overdrive. 

I loved the feel of his hands.  The casualness of his use of them to brush my hair behind my ear or along my cheek drove me crazy!  All that he did in the movie theater provided far better entertainment value than whatever happened on the big screen.  Believe me.

By the time the love scene started, I already was on fire.  Not because of anything that the characters in the movie were doing.  Those calloused fingers belonging to Skippy roamed again.  Daring they became in how they rubbed circles clear up to my inner thigh.  I know I stared at the screen, but I couldn’t see straight.  My breathing flowed out of me in little pants.  My heart fluttered faster than a hummingbird’s wings. 

If his fingers ventured north and slightly west, Skippy would have discovered that my panties were soaked because of him.  In that moment, my mind turned back the clock 24 hours before where he fingered me to my first ever orgasm.  Just the memory of that incredible moment seemed to send me on that journey again.  I couldn’t believe it, but it was true.  In the middle of a crowded dark theater, Skippy touched me and set me ablaze.  His other hand?  Oh, it was busy feeding that sexy mouth of his popcorn.

I found eating and drinking impossible with how turned on I was.  When the movie ended and we left the theater, I was glad for a break to cool down from simmering for the last 90 minutes.  All Skippy had to say for himself was, “Did you enjoy the movie, Lark?  I sure did.”  Then he licked the fingertips he touched me with.

I stared at him unsure whether to be angry or happy he was so good at distracting me.  I sure wasn’t nervous anymore.  He teased me well throughout the movie, but did not make me come.  I almost hoped he would.

“I’m hungry,” I said, realizing, of course, the double meaning that could have, but it was accurate on both fronts.

Skippy merely grinned at me with the flash of teeth.  “Me, too.  Tell me what you want,” he said mysteriously.



I walked away from him.  “Follow me,” I said and led him up the escalators back the way we came.  Instead of heading toward the garage, where I was sure he wanted to go, I headed toward the bakery and sandwich shop Au Bon Pain.  It was my favorite.  I loved the soup and salads prepared fresh daily.  Out of the corner of my eye as I looked up at the menu, I saw Skippy nearly pout.  I smiled in amusement to be able to tease him back!

“Something light?  What do you think?” I suggested as I glanced at him.

He shrugged.  “Sure.”

We ordered and ate our food of soup for me in a yummy bread bowl and a whole turkey sandwich for him.  Our conversation was light as we watched people pass.  Once done, we returned to his truck.  I thought for sure that we would be heading back to my house.  Skippy assured my dad and Des that he’d return me home before curfew.  That’s not what happened, though.

We showed up at the park not far from my house, which had stables.  It was afterhours and the park was closed.  Skippy entered the access road anyway.  He parked his pickup far enough away from the main road not to be noticed by traffic.  The truck’s lights went off, the engine shut off yet love songs from a CD he burned still played. 

I did start to get nervous and fidgeted with my ears.  Skippy turned to me and said, “I want you to close your eyes.”

“Okay.”  I did as he wanted but felt even more nervous.

Skippy climbed out of the truck.  I heard some noises coming from behind me, yet I could not figure out what he was doing.  Some moments later, my door opened.  He said, “Take my hand.”

I reached for him, and he took my hand in his.  “Skippy, what’s going on?”

“Keep your eyes closed and following me.”

I did as he asked and then he stopped.  “Okay.  Open your eyes.”

I saw that he rolled back the tarp covering the truck bed, and there looked to be a mat with blankets in the bed of the truck.  I then watched him hop up on the tailgate.  He kneeled down to me with his hands out. 

“What is this?” I swallowed nervously as my heart beat so fast. 

“Lay with me under the stars?” he asked sweetly.

I gasped because I had never heard of anything so romantic.  While even more nervous, I knew what I wanted.  I wanted it all night and knew he could show me that pleasure again.  Any opportunity to be closer to this guy who made my heart rush, and palms sweaty, was favored.  I wanted Skippy.

“Okay,” I said while lifting my arms to him.  He reached for me and as he stood he lifted me up to the bed with him. 

We lay down shoulder to shoulder.  Two T-shirts rolled up under our heads like pillows.  I stared up at the sky amazed how clearly the stars could be seen that night from this new vantage point. 

“Beautiful,” I whispered with a smile.

“It’s my favorite spot right here.  I would come here when my mom’s boyfriend would get drunk and try to kick my ass.  It soothed me, you know, to look up at them and think of my real dad watching over me from up there and now my mom is up there with him.”

“Oh…Skippy.  I’m so sorry to hear about that,” I said in sympathy as I turned to him and touched his chest.  He wrapped his arm around my shoulder as he looked up at me.  His other hand reached to cup my hair behind my ear.

“It’s okay.  The old man at the shop where I work kinda took me in after that.  He gave me the place behind his house to rent after she passed.  I really couldn’t have gotten through her illness and stuff without him.”

I nodded as I remembered that Skippy’s mom passed away a few years ago.  That’s about around the time, I stopped seeing him around the neighborhood except at the auto repair shop.  “My dad says he’s a sweet old man, which is why he always brought his car there.”

“Yeah.  He really is.  And fair.  All the customers love him, miss him.  I talk to him every day almost.”

I leaned my arm across his chest and leaned my chin down on that.  “He sounds like a good friend.”

“The best I’ve ever had, believe me.” 

I rolled to my back and looked up at the stars for a minute or two.  The only thing I felt was the vibration of the truck’s speakers that still played music around my body and Skippy’s fingers wedged between my own.  My nerves were calm.  I was relaxed until Skippy turned on his side looking at me.  The light was dim but the night bright.  I couldn’t see his face in the dark as I turned toward him.  I did feel his rough fingers on my cheek lightly tracing it.  It sent shivers of delight through my body or more particularly my foo foo.

“So what does the future bring for you, Lark?  College I bet by the way your dad talks, huh?”

I swallowed.  It seemed so far away.  In the fall, I would start at college so far removed from where I grew up.  It was clear in another state I never visited before, but the school offered the most money to go there.  I accepted the best deal.  That move would take place in late summer though.  Graduation was a few days away and then I had two solid months at home to enjoy family and friends.

“Yeah,” I said quietly.

“Aren’t you excited?” he asked, and I could almost hear the frown in his voice.

I nodded.  “Sure.”

“Doesn’t sound like it.”

I pushed out a sigh.  “I’ve never been away from family and friends.”

He nodded.  “I have no doubt you’ll do fine.”

“Why do you think so?”

“You’re the kind of girl that when she puts her mind to it, she can do anything.”

I frowned as I blinked at him.  “How do you know that about me?”

Skippy chuckled lightly.  “I told you, your dad talks about you a lot.”

My eyebrows lifted because evidently he had been listening.  He knew more about me than I thought.  I felt flattered that he did.  “Evidently.  I’m shocked that he’s not bored you to death.”

He chuckled more.  “I can’t believe that any guy would be stupid enough to stand you up.”

I shook my head.  “Believe it.”

He caressed my lips with his thumb.  “You’re a wonder, girl.”

“I am?”

“So sweet.”  Skippy kissed me softly.  “I’ve always liked you.  I just thought I was so far below your standards.  That you deserved better than a grease monkey.”

My eyes widened at his admission.  “Are you kidding me?  I’ve always had the biggest crush on you.  Sweaty palms and everything whenever you talked to me.”  I slapped my hand over my mouth so embarrassed to share that fact with him.

He only laughed harder.  “Oh, yeah?  I had no idea.  I wish you told me.”


“Why do you think, girl?  So we could be doing what we’re doing right now.”  He ran his hands over my head gently and kissed my nose.  I giggled at him.

Now I thought about the meaning behind his words.  Gosh!  All the time I wasted pining after Skippy, and I could have been in his arms?  He pulled me close, and I came to him happily.  I wanted him.  I always did.  Always would.  I didn’t think about the future that would pull us apart, or our wasted past.  Right now was what we had.  Skippy and I felt like the only two people on the planet in that moment.

“I want you, Lark,” he said huskily as he held me close to his firm chest.  He felt like a warm poker against my hands.  I felt so flushed and hot as it was.

“Want you, too, Skippy,” I replied in a whisper.  My heart fluttered like it was a little bird in my throat.  I trembled when his palm cupped my face.

“Don’t be afraid, sweetheart.  I swore, I’d take care of you, didn’t I?”

“But that was yesterday.”

Skippy shook his head.  “Always.  Do you believe me?”

I nodded without hesitation.  How could I forget how wonderful he made it for me yesterday?  I didn’t doubt him, but I still needed to question.  My nature, I guess.  “I do, but do you have a condom?”

“Always for that too, sweetheart.  Relax, okay?”  He kissed each eyebrow and then between them.  “I’ll make this good for you, too.”

“Wait, but what about you?  Will it, umm, be good for you, too?” I asked with a frown.

“Oh, yeah.  Why do you ask?”

I felt my cheeks burn.  “Because, umm, I don’t know.  It just seemed to be all about me last time.”

“Because it was.  I wanted to please you, and it was your first time, too.  I wanted to make it the best I could.”

“Oh, Skippy.”  I almost wept at the sweetness of his tone.  “It was.  I…I…” I was so at a loss for words at the thoughtfulness of this guy.

Skippy kissed me softly on the lips, and I kissed him back with all I felt for him.  What had been light and sweet turned passionate.  My fluttering heart thudded and vibrated through me like the bass of the newest love song drifting out to us over the truck speakers.  Skippy maneuvered me on top of him to my surprise, but the kiss never stopped.  His hands found the hem of my dress, and he crept it up my thighs that straddled him.  He sat up running his fingers along my thighs and my hands eagerly ran up beneath his shirt.  He broke the kiss and removed it.

I gasped when his lips touched mine again, and we switched places.  In the process, my dress came off and I was exposed to the elements in my white bra and matching panties.  Skippy laid me on my back as I stared up at him.  My hands reached for him, and he kissed my fingertips.  He unzipped his jeans, but that was all.  His hands busily slid the cups of my bra up to free my breasts for his avid mouth.  The hot wetness of his tongue circled my areola and nipple.  I grabbed his head to me as we moaned. 

It felt so good what Skippy did to me.  How he sucked me into his world.  I never knew I could feel so much pleasure.  He treated my other breast to much the same treatment that sent me higher to the heavens.

His kiss resumed, but this time down the center of me.  Down the soft lips traveled until his rough thumbs snagged the side of my panties and tugged them down at my gasp.  Skippy buried his face in my hairy mound where I gasped again.  I hadn’t expected that or the snaking heat of his tongue searching me the way the memory of his fingers had.  He groaned when he struck the tender bit of flesh that throbbed with my pulse.  My booty lifted off the bed, and he cupped it in his strong hands.  Groaning, he drew me deeper against his face. 

His tongue parted my lips and took the cream I produced as I trembled with my soft whimpers.  When his mouth clamped on me for the sucking and swirls of his tongue, I lost it.  I cried out in the beautiful but intense sensation Skippy summoned between my legs.  I gripped his hair and the blanket beneath me.  Skippy hadn’t stopped licking and groaning.  Rather, he added a finger to his play and sent me over for another body shaking orgasm. 

He let me rest for only a moment before he started all over again.  Skippy licked me and sucked on that bud of pleasure I discovered at his fingers yesterday and his hot mouth today.  More fingers entered me sounding off with their own sucking sounds in and out of me faster than before.  He pounded me with them as he licked and sucked me to another orgasm, but this one lasted longer.  I couldn’t catch my breath and I begged him to please stop.  I couldn’t take anymore.  It was too intense.  Skippy seemed to have mercy on me and kissed my inner thigh softly.

As I came down from the heavens where he sent me, I heard something tear and noted that he was naked over me now.  He helped me untangle myself from my bra and panties.  Then Skippy was over me, skin touching skin, kissing my mouth hungrily.  There was no softness to him now as he dominated my mouth.  He stole my breath.  His face buried at my neck, and I felt him coating a hard thickness against the lips of my foo foo.  Skippy then pressed that same hardness just at my entrance.  Slowly he lodged it within me.  My mouth opened at how I stretched to fit him.

“Lark,” he moaned hoarsely and shoved inside me.

Oh, God!  It felt brutal to be so full so quickly!  I couldn’t say anything as I didn’t breathe.  His full weight pressed down on me.  His face buried at the crook of my neck, panted hot breaths from him.  His hips withdrew slowly and I could breathe again only for him to shove forward again.  I grunted and clutched on to him.  He reached between us and rubbed my clit shooting me high again with his stunning fullness inside.

“Skippy!” I cried when he withdrew just to shove inside me again.  He was the deepest he could go as he waited for an eternity.  I trembled again, cumming, and chasing after my breath.  His hands slipped along my curved sides and under my booty.  My legs spread wide for him and shook.  I couldn’t feel them, but I felt him touching me from within with heat. 

When Skippy moved, he did so easily along the slickness I produced for him.  He added me in meeting his thrusts with his hands under my booty.  I held on clutching at his muscular back, bunching with the effort he propelled us. 

I stared up at the stars twinkling down upon us, burning with tiny fires as I did with each of his consuming thrusts.  They came faster as did my grunts.  It was all I could manage now.  Skippy moaned with me with each climb, so deep inside.  His sweat covered me as I’m sure mine did him.  His breath at my neck was harsh like mine and still he filled me.  The harder he came, the wetter I grew.  His pelvic bone shifted sharp and fast against my clit.  His hardness conquered every cranny I willingly offered.  I was his in my release. 

When he shouted, my name while thrusting for his final descent inside me, I knew Skippy was mine.  I smiled knowing that I was not the only one so consumed or in that moment so satisfied.  We held each other just like that, under the stars in the bed of his truck.  Our bodies exhausted and soaring but so wonderfully entwined.  Skippy covered us with a blanket, refusing to let me go.  I certainly didn’t mind.  I loved the feel of his strong body against me.

The sounds of the night reached up to us, calming us with the sound of crickets singing their own love songs.  Skippy and I drifted along in the flow of that and the love songs still in play through the old truck’s speakers.  Linked by touch, we both stared up at the stars, locked away in our own thoughts.

Looking back, I still wondered if at that moment I knew my infatuation graduated to love for the neighborhood kid.  My time with Skippy burned so brief but so bright.  Other ambitions fueled my drive to succeed beyond my circumstance and would separate me from him.  Nonetheless, from that point until I left for college, we made the most of our time, living in the moment, not caring a bit for what tomorrow would bring.  

Skippy… He was the first boy to steal my heart.  This man also showed me a love that was tender and so beautiful.  For that taste of heaven during a perfect summer, I remained forever grateful.

© Copyright 2020 Amy F. Turner. All rights reserved.

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