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I shouldn't


Warning. Contains strong sexual content. Our stories are written for
fun and are free. Permission is not granted to post anywhere for

Captain Steve and Linda

Thanks to Marie Durois for adding all those pesky little commas.

I Shouldn’t...
“I shouldn’t be doing this.”

“Want me to leave?”

“In a bit. But what the heck, finish your wine.”

“Good, I’m enjoying it and the conversation.”

“Did you get your car all the way in our garage with the door shut?
Neighbors you know.”

“Yeah, car hidden. Guess I’d like another glass of wine too, if you
have it.”

“Coming up. I shouldn’t say this, but relax. Sit on the couch for a
few minutes.”



“I’m not sure what to do next.”

“Me neither. I, er, well, we shouldn’t be doing this at all.”

“I said I would leave soon.”

“No harm far. I shouldn’t be saying this, but stay just a
tiny bit longer. I’m enjoying the evening---so, what would you have
done next, if you were going to stay? ”

“Well, as I remember from my days in college, as the great seducer of
women, I would need to turn the lights down low, put on some soft music
and ask you to join me on the couch?”

“ Pretty complicated stuff. Ok, I shouldn’t say this but we’ll just
act like we are going to...uh... I’m turning the lights down. Is jazz

“I love it.”

“Ok, I’m sitting on the couch next to you.”

“You smell so good.”

“Wow Dave. You get points for that. You must have been good in

“So I’m doing ok?”

“Better than I expected. Oops, guess that didn’t come out just right?”

“I know, Jim and I heard you and Lindsey talking about us.”

“Those two. What do you suppose they’re up to?”

“I’m sure they’re not having half as much fun.”

“Agreed. Are you having fun?”

“Yes. But I’m not sure what to do again. Somehow I just can’t grab you
and start a mad passionate kiss.”

“Remember we aren’t going any further.”

“Yeah, I know.”

“I shouldn’t be saying this, but if we were, what would you really do

“Well, if we weren’t just talking, I... let’s see...I notice you aren’t
wearing a bra, so I guess I would put out my hand and touch your

“Just like that. Not even try to kiss me first?”

“Kissing is for...I’m not sure. Allison we’re not falling in love.
We’re having an affair. Is that the right word? Actually we’re not,
but if we were, it’s not cheating since Jim and Lindsey are doing the
same thing and know what we are doing, or thinking of doing. So would
it be an affair or a sexual encounter, or what? Anyway that’s why I
probably wouldn’t start with a kiss. Does this make sense?


“I didn’t think so.”

“Anyway, now that we’ve agreed that we’ve gone as far as we’re going
to, tell me again, without any preliminaries, you would just reach over
and touch my breasts? Not asking permission or anything?”

“Like I said, I’m out of practice. Not too cool, I guess.”

“Not too cool.”

“Well, I never was too good at it. Well, my wine is about gone.”



“Would you like some more wine?”




“I shouldn’t be saying this, but would you like to touch my, uh...them?

“More than anything.”

“I’m really surprised. I thought you would ask me to dance or
something and sort of to try to grope me. Then we’d get into some big
clinch, just like you said. I just couldn’t see doing that either. I
don’t love you. Strange, all week I was thinking it would be nice,
actually, more than nice, okay, even a real turn on it with you, but somehow kissing wasn’t something I
wanted. So I was kind of nervous about that. I never expected you to
say you would just touch me. It’s so clinical. Makes sex seem more
impersonal. The passion can be there, but not the emotional
attachment. All sort of reduced to the lowest common denominator. Or
as you guys call it sport f’ing. ”



“What are you talking about?”

“I don’t know. We’re both talking too much. Putting off decisions I

“I promise I won’t kiss you.”

“Ah, a real gentleman.”


“So what?”

“So, do you want me to touch you?”

“Oh me. I shouldn’t be saying this, but do it slowly. There’s just
enough light. I want to watch your hands. I’m just testing my theory
of clinical sex with the emotion removed.”

“I understand.”

“No you don’t. You just want to touch my boobs. I don’t understand
what I just said myself.”

“Ok, watch my hand.”

“Slowly, slowly you’re almost to them...Ohh, that feels good.”

“Damn, your nipples are hard.”



“No, stop.”

“Damn that was fun. Your breasts are firm and nice or actually
beautiful and soft and...hell, here I am as excited as a teenager
copping a feel from his first girl.”

“So, I guess we’re done. Well, clinically speaking, I don’t feel so
bad. No harm done. We haven’t exactly ‘done it’ or anything that we

“I’m going to unbutton your dress. I see the buttons go all the way

“ My, my, getting bold aren’t we?”

“Purely scientific Allison. Just another experiment. Let’s see how
you feel as I undo each one.”

I shouldn’t be saying this, but yes, undo the first four. Do it
slowly. I want to watch. But just the first four, you understand.”


“I’m still calm.”


“Feeling detached.”


“Tingling a little. I see your hands are very steady.

”Four. I can see half of each breast.”

“I shouldn’t be saying this, but, open it...slowly. Perhaps we could
continue the experiment just a little and...

“There they are. Damn they’re beautiful. Such pretty little rosy

“They sag.”

“No...perfect...I’m going to put a little wine on each one and lick it

“Oh no, no, no...yes, please. Slowly now. I’m watching your hands
again. You’re touching my nipple. Your tongue. It’s going to my ohh. OH MY GOD, OHHH. NOT ALREADY.

“Damn. You went?”

“A little. I can’t believe it.”

“Hmmm, didn’t know I was that good?”

“Shut up. I shouldn’t be saying this, but I have another nipple that
needs attention. Yes, there. Like that. More. Oh.”

“Dave, I shouldn’t say this, but I see you’re excited.”

“Yes. It’s your fault of course.”

“Yes, I’m guilty. I excited you on purpose.”


“Well what?”

“Are you going to leave me like this? Remember, it’s your fault I’m

“I can’t...”

“Yes you can. Just move your hand and we can watch it like we watched
mine. Clinically speaking of course.”

“Just another little experiment?”

“That’s it.”

“Well I shouldn’t, but lay back on the couch. Ok, see my hand it’s
moving towards your uh... what shall I call it?”


“Yes, thanks. See, I’m touching your knee and slowly moving my hand up
your thigh, right at your zipper. There, one finger is on your zipper.
I’m tracing the outline of your...uh...”


“Oh yes. Oh my, it’s more excited. I shouldn’t be doing this.”

“Do you want to stop?”

“Just a little more. And maybe, I shouldn’t be saying this, but think
I’ll unzip you. Just an experiment, of course. Want to see the
clinical reaction.”

“Just like that Allison? You’re not going to kiss me first?”

“Quite. Oh, the zipper is stuck. Shift your hips a little--there. Oh
my. Clinically speaking...oh my. Silly white cotton shorts. And I see
the excitement has increased?”

“Well yeah. Good looking women unzips my pants.”

“So, it doesn’t bother you that she’s married to your good friend?”

“No, matter of fact it makes it more fun...exciting...erotic, whatever,
thinking that your Jim is probably screwing my Lindsey as we speak.”

“Do you think so?”

“If I know Lindsey, and I do, it doesn’t take much to get her going.”

“And what about me?”

“Allison, this is one of the most erotic evenings I’ve ever spent.”

“Oohhhh, more points. I shouldn’t be saying this, but look, my finger
is caught in the little flap in your cute, white-cotton shorts.”

“How about that.”

“These flaps are so funny—Maybe, I’ll just slip my finger inside.”


“You like that?”

“Yes, you could slip it in further.”

“No way.”


“But, I shouldn’t be saying this—if you were to shift your hips again,
I could...”

“Like this?”

“Yes, oh your belt is kind of tight. Help me get it. There, I can do
it now. A little higher. Hmm, guess I’ll have to actually pull your
pants down--kind of hard to do the underwear alone. My Dave, that’s
very impressive. Seems like it’s gotten bigger.”


“Don’t mention it. I know I shouldn’t do this, but since you were so
nice and made me feel so good when you, ah, sort of, ah licked my boob,
maybe I could sort of put my fingers around it like this and, oh yes,
you seem to... I’ll just move my hand and...

“Oh shit , that’s nice.”

“Dave, I shouldn’t say this but, if you wanted to sort of, kind of,

“Unbutton the bottom of your dress?

“Well yes.”

“ Ok, one, two three...

“That’s nice. Is that your hand I see under my skirt?”


“I should stop you. I see it moving up and, oh it does feel good, it’s



“Shift your hips. I’m going to pull your panties off.”

“I shouldn’t do that—here, like this?”

“Now, put your feet on the floor and pull up, yes I have them.”

“ Dave, I shouldn’t have done...Oh God your hand is on my....stop, no,
yes, stop, no, no, nooooooooo...”


“Are you okay?”

“Oh, yes, very. That never happened to me twice in a row like that.”

“Stand up. Now turn your back to me. Now sit down.”

“You mean...”

“I shouldn’t, oh damn. Oh Dave. Just a little, I can’t.

“Yes you can. Just for a moment.”

“What are you doing?”

“I’m pulling up your dress in the back. I’m folding it up so it won’t
get wrinkled.”

“Such a thoughtful man. But I’ll be naked when I sit on your lap. I
shouldn’t...but maybe just a little...’

“Carefully, slowly, I’ll put myself between your legs so that we don’t

“Dave this is hard on my legs. I’m going to have to sit all the...oops
feels like you sort of accidentally went into me a little...”

“Do you want to get up?”

“Yes, I have to. But my thighs are a little cramped. I can’t. Stop.
No. Oh, yes. I shouldn’t...more, harder. Oh my god you slipped all
the way in, we’re...”

“Yes we are.”

“Dave, we shouldn’t be doing this.”

“Yes we should.”

“No, I shouldn’t let you do this. Just sit. Don’t move. We can’t.
Damn you’re moving. Stop. No. Don’t do more. Put your hands on my
boobs. No don’t. Oh my god now we’re...oh yes. I
shouldn’ like that...can’t

“Ok Allison?”

“More than okay—you’re still hard? Then since we’ve already...move,
more, there, the feeling is so, don’t stop, yes. I didn’t think it
would feel this good. There, now more, more, moreeeeeee...”

“Dave, you still awake?”


“That was nice.”


“Bet Jim and Lindsey didn’t have that much fun.”

“I wouldn’t think so.”



“I know it’s only been about ten minutes, but can you get it up again?”


“I know I shouldn’t do this but, maybe if I kissed it and...”



“Wonderful idea. Just thinking of your kissing is working already.
And I know I shouldn’t say this, but I think it’s a little late for you
to keep saying---I shouldn’t.


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