Best Of Both Worlds
Copyright© 2002 by Iolanthe Dance
Chapter 3: Plans and Improvisations
Erotica Sex Story: Chapter 3: Plans and Improvisations - 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
"Did you know that Kelly and Stevie are swingers?"
"You're kidding me!" I said. We were lying in bed together, after a pool party. Kate's head was on my shoulder.
"Nope."
"So Kelly never told you?"
"I had no idea. She works for me, that sort of stuff doesn't come up"
"It's come up now. Apparently so has something else."
"Well you've been playing with it, what did you think was going to happen?"
"You're saying it has nothing to do with you thinking about doing Kelly?"
This was hotly whispered into my ear. Her lips trailed down my neck lightly kissing me. I was a walking colony of goose-bumps with one magnificent sky-scraper.
The fact is, Kelly is pretty easy to think about. She's short and looks young and always brings out the Humbert in me. I've never been with her though. I am in love with the woman beside me, my fiance Kate.
Kate was wearing the top from my pajamas. I found one of her large breasts with my hand and started squeezing it through the thin cotton. I ran my palm lightly over the nipple several times before I caught it between my thumb and first finger. She bit me where my neck meets my shoulder.
"I'm saying I want you, Kate!"
She threw a leg over me and climbed up to straddle me. I could feel a slight dampness on my chest where her pussy lay. Lifting the bottom of the pj top she pulled it off. Her body undulated slightly from her bottom in a slow wave rolling up her to her gorgeous chest. Holding one sleeve in each hand Kate spun a twist into the pajama top, like you might with a towel you were about to flick at somebody. I knew what she wanted and put my hands together beside the headboard. She tied them there and smiled.
"You want me? Which me?"
Airport bars rate really high on my list of weird. They attempt to create a cozy atmosphere mere steps away from the brightly lit and bustling terminal. They are as convincing as a 1950's roadside dinosaur park. I didn't care much about this though. I was delighted to be sitting in this one. It was a Friday afternoon and this is where Kate asked me to be.
Airports are actually a good place to watch people. You can see it all; young couples saying goodbye, grandparents being picked up by the whole clan, women with young children meeting their husbands and medical couriers carrying troubling white coolers with a big red cross on each side. Mostly though, I watched the stewardesses.
Ahhh... the 'stews'. Naturally they avoided the bar with its faux 'Cheers' decor. They had their own watering holes, not far but not advertised to the general public. But in the airport lounge you could watch them stroll by, pulling their wheeled luggage behind them. Their outfits aren't what they once were but there's still something about those polyester blazers and skirts and the scarf tied around the neck above the undone blouse collar.
If that vision of stewardesses seems old fashioned it probably is. I was born too late, I think, to enjoy that world as an adult. I can remember though a flight to visit my grandparents when I was twelve years old. It was my first time flying alone and I was put in the hands of a stewardess named Virginia. Virginia smelled of perfume and cigarettes and her hair was coifed higher and larger than the women I was used to seeing. Her skin was darker than most of the women I knew and she had a southern accent. Her uniform was cut high on her legs and tight around her rump, but the most noticeable thing, for me, was her chest. She had a really large pair of breasts and they stuck out like torpedoes. I could make out her bra under her white blouse and because the shirt was tight, little gaps between her buttons gaped open. When she sat next to me I could sneak peeks from the side and see a little of her bra and a little of the slope of her breast. She would sit with me when she didn't have other duties. I loved the attention. For me, Virginia's presence was a turn-on. I am sure she had no idea what reaction she would evoke in a boy my age. Otherwise why would she put her hand on my thigh several times, so close to my adolescent hard-on? I masturbated to thoughts of Virginia for years afterwards. I imagined her undoing my pants and pulling them down and straddling my lap positioning her pussy right over my cock. I wanted her to sink down onto my cock, and then, facing me, my penis inside her I saw her undoing the buttons of her blouse and opening her bra for me to suck on her breasts. Of course all that happened is we chatted a little. I felt pretty grown up about it, and about flying myself. When the plane landed she walked off with me and stayed with me until I saw my grandparents.
I've never forgotten Virginia.
Decades later when I told Kate the story I described Virginia as a 'Big Blowsy Blonde'. Consequently, I wasn't completely surprised when the big blonde stewardess showed up.
"'Scuse me, Sugah, is this seat taken?"
"It sure isn't... " I made a point of looking at the name-tag on her breast "Virginia."
"So which me do you want tonight?"
"What are my choices?"
"Well... " she had an evil grin "there's Bitch-Me!" She punctuated this idea with a hard slap across my face. It was all I could do to not jerk my arms out of the makeshift tie.
"Or" she went on sweetly "there's Uber-bitch Me, but she doesn't put out at all. Those are your choices, for now, Harry."
"I'll take the Bitch-You, please."
"You sure?"
"That whole putting out part kind of settled it for me."
"Good. Now eat me. You can talk again after I've come."
Kate had been sitting on my chest. She rose off me and then slung one leg over my head and facing my toes lowered her crotch to my face.
Kate was very excited and she anointed my whole face with wet strokes of her pungent muff. I put out my tongue and she started riding my mouth, swabbing herself back and forth across me. I sucked her tangy juices in and tried to get my tongue up her. She seemed to prefer grinding hard onto me though so I made my tongue stand up as much as my cock and let her lathe it.
This wasn't me giving Kate head. I wasn't tonguing, sucking nipping and kissing her to bring her off. This was Kate using my mouth as a scratching post. She rocked up and down across me. Her juices wet my face and I could even feel one droplet slowly agonizingly tracing a cool trail down my check towards my earlobe.
Kate's pace increased and she bent over so she was on all fours above me. She grabbed my dick roughly and held on to it tightly. Her whole body undulated in a wave which crested as she slid her pussy across my tongue and lips. Then she crashed down onto my mouth grinding herself in a circular motion onto me.
My cock, in Kate's hot hand, had been hard, but she hadn't really been paying much attention to it. Suddenly her face came down onto it and she roughly took it into her mouth. I admit, I was worried for a minute. Kate was at a high level of passion and I could feel teeth. Somehow though she gave me just enough pain and my erection was suddenly much harder.
Kate's lips covered the head of my cock. She worked it with her tongue circling it inside her mouth and she sucked it hard, really hard. Again, just as it seemed like it was going to really hurt she eased back just enough and she thrust her face down to my crotch, swallowing my cock whole.
I wanted to pull my arms free of the knot and throw Kate down and rape her but I wasn't going to spoil her fun. Our sixty-nine continued with her using my face for her pleasure. it was probably good that she didn't need a lot of finesse from me. By this point, my cock had gotten painfully hard and her head bobbing down onto it was making it very difficult to think straight.
Suddenly in mid-stroke she stopped. She froze over me for a moment and then pressed her pussy against my face with more weight behind it. She ground it hard on me and started thrashing. My cock still in her mouth was getting seriously gnawed on and he suction was so strong it was slightly painful. My balls had that fiery itch building and as her orgasm subsided mine began.
It hurt but felt so good to and was such a relief. I knew I'd feel sore in the morning but tied down feeling my cock deep in her mouth as she sucked out my semen into her mouth and swallowed it, I didn't care at all.
Kate's quakes subsided and she collapsed on top of me. Her head lying on my thigh. We stayed there for a bit listening to each other's breathing settle. She covered my now very sensitive cock with light gentle kisses. and licked the tip whenever a drop more come appeared.
"You want up" she said eventually. I did, my arms were tired of being tied over my head. She climbed off me and I could move again. I wanted to see if there were any actual scars on my cock. She saw me examining it.
"Harry?"
"Yeah?"
"I love you." She said it with the innocent voice of someone worried she'd done wrong.
"I love you too, Kate"
We settled in to a nice cuddle with her head in the crook of my shoulder. I was exhausted after the party and the lovemaking and was pretty much asleep when she spoke again.
"Harry?"
"Hmm?"
"Are you awake?"
"Hmmm?"
"Guess not. Sorry to disturb you?"
"What?" I was finding my way back to consciousness.
"Never mind, Sweetie, you go back to sleep."
"I'm up now," I said, "what is it?"
"I'm sorry. I should have kept quiet. It's nothing we can't talk about in the morning."
"OK," I said kissing her forehead "whatever your little heart desires."
I laid my head down and let my breathing slow. Sleep would come easily tonight.
"It's just that..."
I started laughing. I couldn't help it, this was so unlike her.
"I'm sorry, I'm sorry!" she said. Kate caught the giggles too.
"So what is it?"
"I told you, Har, it can wait!"
I gathered my breath and gave a great bellow.
"Out with it!"
"... but, we should just go to-"
"Out with it!"
"It could have waited Harry. I'm sorry. Here it is; regardless of how we respond to their proposal for a uhh... let's call it a double-date, Kelly and Stevie
want to throw us bachelor and bachelorette parties."
"They do?" We had decided not to have the traditional pre-marital shindigs. Not any involving other people anyway.
"So think about it. We can talk tomorrow about this and the other thing."
My mind raced through possibilities. Would Stevie throw my party and Kelly do Kate's, or would it be the other way around. I was thinking of Kelly popping out of my cake. I liked the idea. Then I pictured Stevie showing Kate a good time and liked that thought somewhat less.
"OK, something to talk about" I said, "I think, given their other proposal I need more information as to what they have in mind. Did Kelly or Steve talk to you about it?"
Kate didn't respond. She was sound asleep.
Flight attendant Virginia was apparently quite the round-heels. After just a couple drinks she invited me to her hotel.
"I shouldn't I know, Sugar, what with you being so young and me old enough to be your... big sister. You're such a handsome boy, though and I am sure I could teach you some things you'd appreciate. I have to tell you," this she said right into my ear. "On the flight, I was seriously wishing I could throw a blanket over both our laps and snuggle up with you." She emphasized her point with her fingernails clutching my thigh.
"Really?" I said, trying to make my voice crack like that usher character on the Simpsons "Then what?"
"Sug-ah! With a blanket, why, we could be touching each other and no one would know. You could touch my legs, would you like that?" She hiked one side of her skirt up to her mid-thigh. She took my hand and put it on her stocking covered leg.
"I really would!"
"And I could touch yours." she said. Her nails dragged up my thigh and right over my crotch. She felt my cock, already hardening jerk under the gabardine.
"Oooh!" she said, all innocent "What do we have here?"
And so we adjourned to a nearby hotel.
"It's good I already got the room, Sugah," she said "I don't think the place would approve of me bringing in someone as young as you."
The room was small and cheap but I was pretending to be, well younger than you should really think about and so I acted pretty excited to be there. Virginia set her drag-a-suitcase on the bed and unzipped it. She started pulling out scanties dropping them into a pile on the bed. Eventually the case was empty, it had carried nothing but lingerie.
"Sugah, why don't you pick something out you'd like to see me in."
I started towards the bed nervously. As I passed her she stopped me with a hand on each shoulder.
"You evah been alone with a woman before, Sugah?"
"Uh, not really" I said.
"Well, no worries. Virginny is gonna take good care of you." She put one hand on the back of my neck and leaned in slowly. Her glossy lips met mine and slowly opened them up. She ran her tongue over my lips and across my lower teeth. I extended my tongue to touch hers. She tasted of alcohol with a hint of cigarette. She gave my lower lip a suck then backed away.
"Not bad for your first time, Sugah. Now you go pick something out you'd like to see me in, then I've got another surprise for you"
There were panties of varying styles (though I didn't see any thongs, which is Kate's usual preference), bras, camisoles, stockings, a garter belt and a merry widow. I suddenly realized it was all pretty retro stuff. I picked out a cream colored lacey number that looked liked it couldn't possibly fit Kate. I thought the odds were good I'd get some thong effect with it. It had a snap at the crotch and holes in the cups that nipples would poke through. It had a Fredrick's of Hollywood label. It's good to know that Fredrick's is still out there. God bless America.
"Don't be a shy pup, now what've you got?"
I handed it over.
"That's not what I meant Sug" she said grabbing the front of my pants and pulling as if to give herself a peek inside.
"Too dark to tell" she said jamming her hand into my pants and fondling my joint through my underwear "good thing I speak Braille." Then she gave this low in her throat giggle.
Virginia's lips brushed past my cheek and her teeth gently fastened onto my earlobe. She smelled of perfume and cigarettes.
Incidentally Kate doesn't smoke. I guess she figures Virginia did. It's that sort of DeNiro-like dedication to her roles that makes Kate so good at this.
"My goodness you're a big fellow!" She said.
"Really?"
"Oh, Sugar, yes. I am going to enjoy this more than I thought."
"Thanks!"
"While I'm changing you can get your surprise out of my purse." She kissed my nose and headed for the bathroom. I watched the action of her butt as she walked away then opened the purse.
Interesting! I thought to myself as I pulled out the Polaroid camera and extra pack of film.
She returned and she looked succulent! She'd tarted up her Virginia makeup a bit and her hair was still pretty big but it was Kate's body. I was overwhelmed by all of it. I could see her caramel nipples through the lace the curve of her neck, those legs, those feet! Oh my God, those hips.
It was a moment of epiphany. I'd always thought I didn't have a "type". There was no specific physical trait I wanted in a woman. From the beginning Kate and I have played games, being different kinds of lovers for each other to offer variety and excitement. I've always cherished that aspect of our relationship. I realized now though, that it wasn't as if the games were a big part of our staying together. True, we both enjoyed the role-play, but at this moment, I knew for certain we could leave the games behind completely and I would still want to be with Kate forever. I'd been wrong; I had a type and I was looking at it. It wasn't about variety after all; it was about Kate.
"Y'all right, Sugar?"
"Listen, Kate"
"Kate?" she acted outraged "It's Virginia, Honey!"
I took a breath.
"Listen," I said, "I have to run out and get something. Can you turn yourself back into Kate while I'm gone? I'll try to be just a half hour."
"Harry, What's wrong?" It was Kate's voice.
"Absolutely nothing, I promise. I've just had a bright idea. Sit tight and trust me, ok?"
"I love you Harry. If there's anythin-"
I interrupted her with a kiss on the mouth.
"I promise, nothing's wrong. I'll be back as soon as I can."
I dashed out.
This wasn't the sport of hotel with a concierge but I needed help and I headed for the front desk first. When I saw who was on duty my heat sank. The girl looked like she was twelve. I had sort of been hoping for someone like Hector Elizondo in Pretty Woman.
"Excuse me, is there anyone in charge here I could speak to?"
"What can I help you with?"
"Well, a couple things;" I pushed on "I would like a bottle of champagne - the best you have, sent up to my room but please leave it in the hall, I will grab it when I'm ready. And uh... is there anyplace near here one could buy a ring?"
She looked at me for a moment and I could see the gears working as she figured it out. She turned to the door behind her and shouted
"Papa!"
Papa was a big man in every dimension. He listened and informed me that there were no jewelers nearby.
"How about pawnshops?" I said, "I just want something for now for proposing. We will go buy her a nice one later"
He considered and made a face that implied he wasn't hopeful but he grabbed a phonebook.
"Why don't you just use that?" piped in his daughter. She was pointing at my pinky ring. I felt like such an idiot. I had a ring all along. It might fit and even had a diamond in it. I wear the ring everyday and have since winning it in a poker game in college. It's the only jewelry I wear and I'd completely forgotten about it.
"I guess I'm set."
"We'll bring the champagne up and leave it outside your door" said Papa.
"On the house." Said daughter.
Walking back to the elevators I heard Papa start to admonish her.
"Celia!"
"Be quiet Papa, I am in charge of the desk until two, right?"
In the elevator another problem arose. I couldn't get the damn ring off. When I got to the room Kate had added a long silk robe over her outfit. Her face had less makeup and her hair was... well frankly, her hair was a mess. It was obvious she'd used too much product to make her hair stay up as Virgina. Now she'd let it down and brushed it out and it was kind of a bizarro big hair version of Kate's coif. I love her so much, I thought, my heart aching happily.
"Please sit down" I said rushing into the bathroom, "I'll be right there!"
I tried soap and water without success. I found a mini-bottle of shampoo though and that did the trick. The ring slid off and I washed it thoroughly and tried to wash the scent of Prell off my hands too.
I knelt down and realized I hadn't thought what I would say. I thought when I had gotten onto one knee she would know what was happening but I could see she was still concerned something was wrong.
"I know you're probably confused, Kate. It's all going to make sense in a moment. First though I need to tell you a couple of things. You will probably already know most of them."
"First off, I guess you know; you were my first love and my first sex partner. I never told you though that you're the only woman I've ever had. In college, when we were apart, I barely dated and I never really pursued any other women. I worked hard and I moped and I thought of you. You're the only woman I've ever slept with."
"I don't know" I continued, "if you've ever been with another man. I don't need to know. I am sure you've been faithful during the times we've been officially together because I know you. You have integrity. If there was anyone else in-between, I don't need or want to know. I want to make sure though that there is never anyone else"
I could see she really wanted to interject something here so I hurried on.
"What I am about to propose" as I said the word I think she picked up on what was happening "though, isn't just about that. I love you, Kate. You're the only woman for me. If you say yes to the next question I promise to never cheat on you and always try to make you happy. I think we could have a wonderful life together." I looked up at her, tears were rolling down her face. I was feeling a bit moist myself.
"Kate, will you marry me?"
Have I told you yet about the time I showed up at Kate's door as one of those door-to-door Jesus salesman? She invited me in and I shilled for my church while she teased me with peeks at her body. She seduced and corrupted and we wound up with rug-burns and rug stains. Then there was the motorcycle bar adventure, we planned that one together. Oh and in senior year Kate worked on roller-skates at a fast food joint that was trying to resurrect the whole Happy Days thing. That was fun. All right back to our story.