Jack n’ Jill

By Shoeslayer

This story is a ‘spin’ on one I read quite a while ago, not being able to find it but remembering the plot, I decided to ‘Do it my way’. Sorry Frank.

*****

Well, it is a Saturday afternoon and I am brushing up on a few songs for later this evening as I play keyboard at a bikers joint. It is a pretty good job and since I also ride I can appreciate seeing new bikes roll in at times, also I get half off on the menu including drinks.

So, the evening is going well, everyone is having a fine time, bikers are talking about that new shorty carb for their sporty 1200 or some biker got a nice set of Vance & Hines headers for their Low Rider and doing a great job tearing into that tall stack of onion rings.

I had my eye on this redhead across the bar and she looked cute. She is wearing a pair of shorts and a blouse with a low cut neck that gave a guy a good look at some serious cleavage. What I like is the pair of square gold glasses she is wearing. She looks a bit like the redhead who just dumped me for enjoying a rum & coke at times.

Well, she walks over to me and asks,”Can you play a song, “Wanna see you kiss him Goodbye, by the group ‘Steam’ back in sixty nine.”

She is very cute and what large breasts. My cock was just dying to get up between those tits..

“I can’t play a song by request until I know your name.”

“My name’s Jill.” she said with a pretty smile on a face with some cute freckles.

“You gotta be kiddin me, Are you serious?” I asked her.

“Yes I am, why would you ask that?”

“Only because my name is “JACK! I said laughing, and Jill began laughing as well.

“So Jill how would you like to come back to my place after, have a drink and we could play a different tune.”

“Oh that sounds good, sure, you have any Rum & Coke?”

“Yeah that’s one of my favorites, not that I drink much. I’m more of a beer an wine kinda guy.”

The night was over and I couldn’t wait to get Jill back to my place she followed me over to my place in her purple Volks Wagon Bug.

“OOOH Jack, this place is nice.”

“Thanks, have a spot onna sofa and I’ll get ya a rum’n coke.”

I put some music on the stereo and had the lights low, then brought in a couple of drinks.

So we talked abit about our life, what Jill’s been doing, what I am up to, just regular light talk. I kept looking at her and she asks me,

“Why do you keep looking at me like that?”

“Ya won’t believe it.” Jill.”

“I think I will, Jack, this have anything to do with my glasses?”

“Yeah actually it does, they make you look so serious and that turns me on., How did you know your glasses were turning me on?”

“Mom told me that some guys really get turned on by a young woman in the right pair of glasses. How would you like me to touch you down there with them? would you like to cum them so I can lick your guy sauce off them?”

“Oh Jill.” my mind is somewhat blown when I begin to think what Jill’s offerings can do for me.

“I know you like my boobs, you want to cum them? You can stick it right up my cleavage? as I hold my tits together.”

Well, Jill seems to like sex as much as I do and within a minute her blouse was off, revealing a nice mauve colored bra in satin with lace.

“Ah Jill, that bra’s just begging for a good time, whaddaya say I screw your boobs with your bra on, that way she’ll get some of my man sauce all over her.”

“Guess what Jack, I have another pair o’ glasses in my purse, I can wear a pair and touch you with a pair. That’s it, I want to touch you to get you hard as you lick an’ kiss my tits, then you can stick it up my bra.”

“Jill, sit onna sofa and I’ll get on my knees and play with your knockers.”

“Sure.” she said with a voice of a young woman who knew she’d be satisfied.

So Jill is dragging her sexy gold square glasses all over me as she looks at me and sometimes licks me, getting me nice and hard. . .

“So Jack, you gonna cum all over Jill and mess her bra up really good? mess up some of my lace an get your cum ta make stains in my bra?”

“So that’s what Jill wants. . . huh?”

“Oh yes Jack, I know you like seeing the light in my glasses, specially when you’re gonna blow your load up into my bra, This bra has been lookin’ good for too long now an it’s time it saw some life.”

Well I sure want her back and I’ll do whatever it takes to make her happy.I wrapped my arms around her with my cock up between the ‘Big rock candy mountains’ her sexy bra keeping my cock where it belongs and I begin to thrust myself into her boobs and they are the nicest pair of tits I have seen in a while. She is looking at me with a pretty smile as she drags her other pair of glasses over my balls and then, my sexual juices hitting a mad boil and the position of my cock, I blew a load straight up and covered her face and glasses.

Jill laid on the sofa and I got on top of her, my hands were wrapped round her and my glistening cock rolling around on her belly while I played with her tits and man alive these are great, forty two D’s whatever there’s enough boob here

“So Jack, how was it?” she asked with a wide grin.

“You’re askin me? your bra’s a mess the lace don’t look too good, cum all over your face an glasses and you ask how was it? It was damn good Jill!”

We laid there for a while holding touching and talking.

“So Jack, are you gonna want some good head after, wanna see the light in my glasses as my head goes up an down on your fat red cock? Would you like me to bring Mom’s black half-glasses the next time um here?”

“Well Jill, as much as I’d like to see another pair, I don’t wanna see her miss out on the Dagwood & Blondie comics.”

“Oh don’t worry Jack, she has a new pair, I could bring them and you could pretend Mom is sucking you off. Would ya like that, getting sucked off by an older lady, could you like that?”

“Sounds good and I love the idea of an older woman getting me off. I had a woman do that with her patent black hi-heels. Somwehow they turned me on and she asked why I kept looking at her shoes. I told her they looked so hot, sexy, and serious.”

“I could do that if you wanted me to Jack. Heck Mom might like it too.”

I couldn’t believe my ears.”What, your Mom could like doing this stuff?”

“Yeah, Dad split for the secretary at work and is no longer around. Mom always had a thing for the ‘Older woman younger guy thing’ and since I have no brothers or sisters, we do a lot of things together. I know she’d like to come for a visit and see what pops up.”

It was a great night, Jill had her hand around my fat and purple cock, jerking me off as she stroked my nuts with her other pair of glasses.

She knew what she was doing and when I came, well her glasses were covered with my man sauce and she cheerfully licked’em clean.

I was just about out the door when Mom caught me snagging her new gold half-round glasses with the beaded chain. I never lied to Mom and I wasn’t gonna start now.

“Jill, what are you doin’ grabbing my glasses?”

I already have her black half-rounds in my purse but figured, the more the merrier.

“These your old glasses, Mom?”

“No, they’re my new ones, are you having a hard time reading?”

“No Mom, I’m going to give Jack a hard time with them, he has a fetish and being almost hung like a horse, the way he came mine last week was so great, Oh Mom, I touched him all over with them as I wore a pair, he stuck it up my bra and made a beautiful mess. That bra has finally seen some life.”

“If I didn’t have to help in the quilting party, I’d go with you.”

“He’d like that Mom.”

“Jill, I have another pair around here, take the ones you have, my new ones. I want him to cum them but don’t clean them, bring them back so I can see what he did to them, tell him, ‘Mom wants you to cum these for her. and I am sure you will help him do that for me. . . right?”

“Oh Mom, he’ll love that.”

“What else does he like, Jill?

“Patent black hi-heels, Mom.”

“I’ll have to meet him for sure, have him over for a home cooked meal.

“Ah Jill, so glad you’re back.” Jack said as he had his hands on my ass and pulling me onto him and I loved getting grinded.

“I have a surprise for you Jack.”

“Your Mom’s glasses with beaded chains?”

“Yeah and the best part is is, I have to help you cum them for her BUT not to clean them, she wants to see what you can do to them and she’ll want you over for supper fairly soon.”

I got my clothes off and laid on the sofa as Jill was taking off her blouse. My eyes feasted on her mammoth sized tits and I knew I’d get to fuck those boobs. She took a bottle of creme from her purse and poured it into her cleavage and then began to rub her Mom’s black half-round glasses all over me down there.

“Oh Jill, this is s nice.” I said with every bit of sincerity.

“Watch this Jack.”

Jill began to jerk me off, the chains of her Moms glasses around me and her looking at me as well as her two tits Jill then got on top and had my cock stuffed into her bra and between her boobs and we both started to fuck her gorgeous tits. Somehow she knew I was about to cum and she got up and began to jerk me off again and held her Mom’s glassses to catch my guy sauce. Oh yes the feeling was more then great as Jill kept jerking me off to cover her mom’s glasses with my jism. She rolled the messy sticky glasses up in her bra and put them in her pocketbook.

“Jack, how about taking me for a ride on your bike?”

“Fine, that Low Rider will give you as good a ride as I’ll give you later on.”

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