Best Of Both Worlds - Cover

Best Of Both Worlds

Copyright© 2002 by Iolanthe Dance

Chapter 2: Backseat Thrills

Erotica Sex Story: Chapter 2: Backseat Thrills - A couple's romantic and sexual history (and their particular kind of sex play) is told in a series of vingettes beginning with a shameless seduction.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Teenagers   Consensual   Romantic   Heterosexual   Humor   MaleDom   FemaleDom   First   Oral Sex   Anal Sex   Petting  

Basic strategy: learn where the enemy is weak. I've learned and I was attacking accordingly. Kate loved having the back of her neck kissed while I played with her breasts and I'd be giving her nape and ears a solid ten minutes. I wasn't yet in the ideal position though. She loved being fondled and kissed from behind while she sat between my legs facing forward.

My arm had been around Kate during the drive. Snugged up to me already, she'd started putting small kisses on my neck even as we pulled up the little maintenance road where I took her to park.

I turned off the engine but left the accessories power on so that we could keep the music playing. I turned my face to hers. Our lips met softly at first, then with more pressure. I felt her take my lower lip between hers and I slid my tongue out of my mouth and into hers. Our heads did the counter-tilt and our mouths mashed hard against one another. I sucked her tongue and she returned the favor so hard I thought mine was going to get pulled down her throat. Our teeth bumped and felt her tongue exploring all around inside my mouth. Her hand went around my neck, tickling the short hair at the nape.

Kate always liked having her head stroked and I always liked slowly running my fingers run through her thick hair. I was doing just that as I kissed her. I opened my fingers feeling the hair run between them and she gave a little yelp.

"You ok?"

"Yes!" she breathed.

"Did I pull your hair?

"Yes"

"Sorry"

"Do it!" she said. For a moment I wondered, did this mean she was asking me to fuck her now? To take her virginity? I thought of little else back then. I was dying that we should have our "first time" together and I wanted it to be very very soon. I froze.

"Do it again. Put your fingers in my hair." she said. I told myself that I was an idiot and gingerly did so.

"Harder" she said "just a little harder."

I tangled my fingers in her sweet clean hair and ran them across her scalp down to her neck.

"Kiss me!" She said at the same time as she pulled my other hand to her right breast. She held it against her breast though, I couldn't explore or pinch or fondle... just press against it.

My cock was so hard! It throbbed and radiated heat. I had reached a state I mentally call Erection King Mode. I feel like I had the world's greatest erection, as hard as steel, and when I am in that mode, my erection is clearly my King. In Erection King Mode not only is there no judgement, there isn't even enough blood reaching the brain for language. It felt great! It also felt really really cramped. One of my moans must have sounded more like a whimper.

"What's wrong?" she asked.

"Need to adjust"

"Ohhh, poor baby! You could just take them off!"

"I will if you will!" I knew I sounded too eager. She laughed.

"I didn't say that!"

I sipped my hand into my waistband and in a moments time I had my hard cock safely stowed pointing upwards. Since we'd untangled anyway, I took the moment to

put the top down. It was a clear warm night so we could look at the stars. This was also our cue to change positions. I had one leg across the seat and my back to the door. She lay back against me and we talked as we looked at the stars.

"I had to read my poem today in English."

"You read it out loud?" I was surprised.

"I had to," she said, "I didn't know we would have to, but we did."

"So... did anyone know what it was about?"

"I don't know? I don't think they should be able too, but I think maybe a couple of the guys got kind of sprung. I think, they think I was all innocent. Like I wouldn't know."

Kate's poem was eight sensual lines describing licking a melting Popsicle on a hot day. She'd written it in class the week before. She told me she'd had this erotic dream about us and that was the inspiration. What those kids were thinking of, was in fact what the poem was about.

The mere mention of that poem got my motor running again. Her contented smile as my lips started to gently kissed her neck made me suspect she'd intentionally gotten me restarted.

My hands grazed lightly over her delicious shirtfull. Slowly but surely my hands held and squeezed those amazing firm fruit harder and my tongue came out and started flicking and sucking on her earlobe. She ground her bottom against my crotch and tilted her head back gasping as I bit down on her neck. This arching elevated the bottom hem of her Abercrombie & Fitch midi top and my hands didn't hesitate to slide over her belly and up her rib cage until they slid over the cups of her bra and touched to the bare flesh above. I could feel her hard nipples through the fabric. My mouth was applying to her collarbone what was surely the greatest hickey seen in this generation. She turned her head and put her hot mouth against my ear. Her staggered breathing excited me no end, and when her tongue started laving the ridges inside my ear, I nearly came in my pants.

My fingers had started out dipping awkwardly into the cups of her bra. At first, I could just rub across each nipple with the side of my finger. Soon though I had somehow gotten the cups pulled down under each tit and my hands had complete access. Her breasts felt hot against my hands and I loved their heft and firmness. I alternated between focusing on the nipples and enjoying the entire breast. It was nirvana and if I could choose a moment of my life to spend eternity in this would have done nicely.

I have probably sung the praises of Kate's incredible ass so much you might have thought that was her best feature. It's a great ass and I could go on about it all day, but most people first notice Kate's breasts. Even today they're excellent and when she was in high school, OhMyGod! They were like two missiles sticking out of her chest at a completely improbable angle. For breasts that size it would have been fair to expect a pretty large areola something like a Eisenhower dollar piece. I've always loved smallish nipples and Kate's were adorable, despite all the wonderful conical breast flesh they were capping. At this young age, they were somewhere between a quarter and a half-dollar.

I was starting to really pinch both nipples and biting down on her neck when her head tilted way back again and her mouth against my ear.

"Harry," she said, 'let's get in the backseat.

She sat up and started to crawl over between the seats. I watched her plaid-skirted rump go past my face and leaned over to give it a little bite.

"Hey!" she said.

"What?" I said, all innocence.

"Are you coming?"

"Almost!" I laughed getting out and walking around to the back door. Big American convertible or not, I felt awfully big to be climbing over the seat.

Stepping in I saw the end of the bra trick. She'd undone her bra and slipped out of the straps all without taking her top off. She pulled the bra out through her sleeve. Though I'd seen this a few times before, I still stared like a monkey watching TV. It was all I could do to not clap my hands and beat my chest.

I climbed right on top of Kate, running my mouth up her body on the way towards her mouth. As I skimmed her legs she shut them tight, but I felt them relax as I reached a nipple and started nipping at it through her shirt. I slid one of my legs between hers as I bit gently. She ground her crotch against my thigh and her skirt slid up a little. I started kissing and licking her neck and the top of her chest over her collar. Her fingers played n my hair and her nails scraped my scalp.

I raised up and my mouth found hers open. I socked my tongue in and ran it across her teeth. I took a wrist in each hand and held them up over her head against the car door. She teethed on my lower lip hard. The pain, while not great, was like a jolt to my system shooting electricity straight down to my already aching cock.

Up until now, I'd been taking sexual ground in measured almost tentative ways. I was seriously about to lose my ability to keep control. I wanted to just take her. I'd put both her wrists into one of my hands and the other hand dropped to her hip and gave her skirt a yank upwards. It only moved a fraction, but from her thigh I could now push the front up further, and when that was stuck, my hand just went right under it. Her legs closed tight but I pushed hard and wedged my hand just too the edge of her panties.

It took a lot of strength to press the edge of my hand against her humid sex and for all that I just got the slightest contact but it was so worth it. The heat emanating from her pussy and the wetness of her panties thrilled me. I thought a moment or two of this would be it, as much as I could get, and I made the most of it trying to rub her from top to bottom. I tried to learn the landscape by feel through her panties, to identify her lips, her clit, her hole. All this while I could only get the slightest contact, her legs were still squeezed tight.

"Harry... you have to stop... you have to," she moaned "You're making me crazy!"

Do you think I stopped? I was stupid with lust but I wasn't crazy. I pressed on. I put my lips on a nipple and sucked it roughly into my mouth. Her legs stayed clutched tight but they started bucking together like a mermaid flapping her tail. Inside my mouth I flicked her nipple with my tongue batting it to and from while I sucked. We were both breathing hard. She grabbed each of my ears and arched her chest up at me. Then something unexpected happened. Kate spread her legs.


"So when's the wedding?" asked Stevie. I watched his eyes through his sunglasses track Kate's butt as she walked by.

"September 21st." I said. I'd been answering this question a lot today. It was my annual Summer Barbecue and Pool Party. Actually, I have two, one in mid June and one in late August. Stevie asked the second question I'd been getting from all my friends, acquaintances and party-crashers today.

"That's not so far away. You have all the plans made?"

I made a face as if to say 'God, no' and Stevie laughed.

Steve ("but you can call me Stevie, Man") seemed when I first met him, like kind a dirtbag. He's very funny, though and when you get to know him you see he can be awfully kind and charming. I don't know him very well but Kelly, my personal assistant, has been with him over a year. He looks a little like Kid Rock, which I think is totally gross but I guess it works for Kelly (and apparently it didn't totally turn Kate off either. She talked to him for an hour the first time she met him, and she was the one who convinced me to actually get to know him a little.)

Stevie was telling me about his band (Big surprise that Stevie's in a band right?) and I was keeping my end of the conversation up on autopilot while I watched Kelly heading for the pool. My sunglasses were darker than Stevie's and I hoped he wouldn't spot me gandering at his woman as I'd caught him looking at mine. Unlike Kate, Kelly wasn't in a bikini. I couldn't really make out her tiny rump, (which was one of the great disappointments of my day) because the suit had a little skirt around the bottom half. The front of her swimsuit had a big cursive L'il Princess written across it. Another purchase from the young teens department, I thought to myself.

Kelly was a pedophile's dream, a twenty-five year old woman who looked fourteen. She was petite and probably weighed all of eighty pounds. She was also a fireball and I wouldn't want her mad at me. Kelly's hair color varies but lately she's been wearing a gingery red-brown that hung a few inches below her shoulder. She told me that she has two tattoos, but I have thus far only seen one. I'd thought maybe I'd spot the second tat today (I knew she'd wear a swimsuit.) Damn!

As an assistant, Kelly was exemplary and I considered her a good friend too. I know friendships that spring from that sort of unbalanced work relationships often don't hold up in the real world but I honestly think Kelly and I know we can count on each other, if we really need help.

My eyes flicked to Stevie and I saw that far from watching my eyes, he was staring too.

"I am the luckiest mofo I know!" he said with a shit-eating grin.

I smiled back not sure exactly how to respond.

"Though, you might be a close second" he said graciously.

"I think I've got you beat," I said "but it might be too close to call." Stevie laughed.


How ironic... Kate finally gives me access to her pussy and my brain locks completely. In retrospect maybe it was good that I didn't just shove my hand straight at her and that I had this moment of getting my bearings first. Probably it was only seconds but it seemed like longer. I felt her hand taking mine, and pressing it against her pussy and I was back in business. I rubbed the whole of it and slid my hand through the leg-band to start touching it directly. It was wetter than I expected. She was soaked and squishy and that made me feel great. It also turned me on.

"Oh, Harr..." She moaned.

"Kate," I said "you know I love you"

"Oh, Harry, you make me feel so good!"

I was fingering her then with my middle finger while my thumb rubbed around where I figured her clit was. Her legs spread wider and her hips moved languidly up and down. We were both breathing fast.

Her hand was exploring the front of my pants and finding my hard-on rubbed it through my jeans.

"Oooooooh! Ooooo!" her moans were becoming grunts. She stopped stroking my hard cock and just grabbed each of my shoulders.

"Don't stop!" She said. I didn't. I added a finger and pressed my thumb straight down on her clit with each stroke of my fingers into her sopping wet pussy.

"Ohh Ohhh, Oh, God Oooohh... Oh-Ahhhhhhhhhhhhhhhhhhh!"

You can usually tell when Kate hits an orgasm. I love that about her.


The party ran into the evening. I'd finally fulfilled enough of the hosting duties (and people had had enough to drink) that the party just sort of managed itself and I could just enjoy relax and enjoy it myself. Eventually people abandoned the swimming pool for dancing and for the hot tub.

I was having a ball dancing. Kate and I did a mean cha-cha to Santana's "Smooth" then Kate went to dance with Stevie and Colleen, Kate's sister jumped up in front of me and asked for a dance. Past Colleen, I saw Kelly with a sour expression, she'd been heading my way. I mouthed "next one" to her, and I think she got it.

Colleen doesn't really partner dance but she can certainly shake it at you and near you. She'd been swimming earlier but at some point had borrowed a sarong from Kate. I tried not to stare, well I should say I tried not to be noticed staring at Colleen's bra-less breasts (larger and rounder than Kate's) bouncing under the thin fabric. Colleen kept her private life to herself. Kate and I both thought that Colleen was probably lesbian or maybe bisexual. I leaned towards the latter. Kate had "loaned" me to Colleen a couple times for functions where Colleen really wanted an escort. I don't know if Colleen was just experimenting with someone safe or what, but she seemed to be enjoying generating a little chemistry with me. Nothing came of it, of course. I am monogamous with Kate, the girl with whom I lost my virginity. The song ended and I thanked Colleen and headed right towards Kelly. I saw Kate had been heading my way and I gave her a little shrug. She winked and turned back to Stevie. Then a slow song came on.


Kate had taken a few minutes to recover from her orgasm and despite my urgent need of one myself we cuddled and chatted.

"You did a really wonderful job re-creating this," she said "have you hired a cop to interrupt us?"

"Nope. That was for me the part of our night I wanted to change"

"I'm not sure I ever told you this," she said "but you know, I kind of liked that."

"You did?"

"He was really cute, and you know I've always liked men in uniform."

"Should I buy a policeman costume?"

"No!" she laughed "... well, maybe."

This was the same spot Kate and I used to park in when we were in high school. It was where we took each other's virginities. I'd even gotten a hold of similar model convertible.

All the slow advances on her body were much as I've told you but the truth is it took longer. I compressed about two weeks of parking into one night. It's not that Kate wasn't lusty back then. She's told me since how often she came to raping me long before I was actually getting under her clothes and how much she was masturbating to thoughts of having me touch her, lick her and come inside her. She was a good girl struggling with bad girl instincts and she held back as long as she could.

She'd intended to wait for my birthday, but about three weeks early she gave in.

I'd worked hard for it trying to get her really hot so she wouldn't resist. I thought I'd made a mistake when she came. I thought that like a guy she would be done then. In fact after lying against me a couple minutes she started showering my face and neck with kisses. Kissing me lightly and quickly and burrowing her face into me. She sat up on top of me. Her hair was all disheveled and her face still had a blush and sheen. The night was clear and there were stars behind her.

"You are so beautiful." I said.

"Help me with your belt." She said.


John Hiatt's "Have a Little Faith in Me" was the song I danced with Kelly. She'd pressed herself up against me and I tried just a little simple shuffling blues-step back and forth. Kelly barely came up to my chest, so I bent my legs way down. One leg went between hers and she sort of slipped up my leg so she was tight against me. I kept my legs bent, at great personal discomfort and her head could rest on my chest almost on my shoulder. Her arms were around my back and I marveled at her trim tiny body.

"This is nice" she said.

"MmmHmmm" I'd tried to make a positive sound but I was starting to feel the strain on my legs.

"Not comfortable for you, huh?"

"Shhh, Kelly, I am having a wonderful time"

The light was fading. I could see Stevie's arms around Kate. I was pleased to see neither of his hands on her ass.

"Me too" said Kelly, and her arms tightened around my neck. She pulled herself up my body and wrapped her legs around me.

"Hold me," she said in my ear "hold me up."

My hands worked down to her legs and boosted her up and my legs gratefully straightened. I danced with her like I might with a child. Well except with Kelly there was a little grinding.

"Better?" she asked.

"Definitely" I said "but uh, will Stevie object?" By now I'd found that to hold her up, the best position put my hands on her but. One cheek in each hand, to be specific. I asked myself, for how long have I wanted to fondle this butt and how that I had a perfect excuse couldn't wait to stop?

"Probably less than Kate will" Kelly giggled "You're not the first person I've danced with this way. You have to learn tricks like this when you're my size"

"I like your size"

"All men like my size" she said "except for my non-existent tits"

"I think they're perfect" I said "I've always thought so." It's further than I normally would have gone, but the alcohol and proximity were affecting me. I had developed a nice little treat for Kate later.

"You're a tease and a liar!" she said. There was a long pause and we just danced, then she added,

"And you're marrying a woman with a perfect womanly shape."

I had no response, so we danced out the rest of the song. Then I lowered her down to the ground, and let her slide off of me. Her bottom slid right past my hand and she giggled at me and gave me a kiss on the cheek.

The sun was nearly down and I didn't see Kate around. I was lighting the tiki torches when I saw her heading my way with a funny look on her face.

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