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Having both been pleasured in the past couple hours we now snuggled together in bed. Spooning with me behind and my spent cock tucked between Cindy's legs, my arm wrapped around her casually holding her left breast feeling her nipple between my fingers.
Thinking. "She stuck her finger in my ass" "Where did that come from?"
Cindy's thoughts were elsewhere. She asked, "So how was it to have my sister looking at your cock?"
"Hmm, oh. Kind of unusual. I don't know. It was kind of cool to show it to someone else."
"You want to fuck her?"
"Oh hey, I never said that. Your sister is nice looking and all, but not really my type. Why, are you worried?"
We were snuggling in bed. This is and was our 'no bullshit zone'. Truth telling and honesty. When you're naked and wrapped around the person you love most there are no lies. But this was uncharted territory.
"Just wondering. Would you fuck her?"
Careful here Tim. Tell the truth but protect yourself. "If it was ok with you and she was sitting on my lap nude, I guess I would"
"So you'd check with me?" "Dearest Cindy, do you mind if I fuck your sister Sandy?"
"Something like that." "Now how about your brother? You want to see him too?"
"Well, except that he's my little brother, I'm kind of jealous that Sandy saw his big dick." "Even if an accident."
"You had to throw in the 'big' part?" "You know, he's probably a show-er. Looks big but gets harder not longer."
"Now who's jealous? Sandy did say it was soft and still bigger than yours."
"Thanks for the reminder."
"Oh stop, yours fills me just fine. You get right near the bottom and stretch me on the way. It's perfect for me."
"So you don't want to feel your brother's full length?"
"I don't think so."
"Hmm." I decided not to push it, giving Cindy some leeway. And the talk had caused little Timmy to grow some and poke out between Cindy's legs. It also made me think, "She put her finger in my ass."
"So that was something new before. You never poked my ass before."
"You didn't like it? Seemed like you liked it. I thought your cum would shoot through my head."
"Oh it was amazing. Unexpected. Which is probably why I came like that. I was surprised, you're usually not the inventive type."
"The morning was so unusual, it just occurred to me to try it."
I filed that one away for future reference, then eased back just a little and repositioned myself so I could slide my cock into her nice wet pussy. She felt so warm, I continued snuggling that way. For a little while.
A couple of days later on my way home from work (yes we did have lives outside of Naked Day) I stopped off and picked up some lube. I had plans. She put her finger in my ass! We'd never done anal. I hadn't really thought of it. Not everyone was doing it in those days, I don't think. But the die was cast, now my perverted mind had thoughts.
Later that night we were in bed. I asked, "Do you trust me?"
"Yes, completely."
"Then lie on your stomach and put your hands up over your head." Cindy complied and I gently tied her to the headboard.
"Hey now, what's up my sex machine?"
"Flattery will get you nowhere, or everywhere. Relax and enjoy a massage. And whatever comes next. If you want me to stop at any time, the word is banana."
"A stop word? Maybe I should be nervous."
I poured a little oil on Cindy's back and proceeded to massage her from shoulders on down. I wanted her as relaxed as possible. Working hard on her lower back and ass I then continued down her left leg and up her right. As she sighed with pleasure I slipped two fingers into her wet pussy. This girl is always ready. I lifted her by the hips and slid a pillow under her to give me a better angle. She moaned softly when I licked the length of her slit and poked my tongue between her lips. I gently squeezed her tight little ass cheeks and pulled them apart. Cindy let out an
"OH!"
When I did something I'd never done before. I licked her puckered anus. Then poked just the tip of my tongue into it.
"Oh, what are you doing back there."
"Are you ok?"
"Um, yes, so far. It's just, different."
With that as encouragement I plunged two fingers into her sopping wet pussy and used the lubrication to help push my middle finger into her ass just a little. I heard some noises, moans, sucking in of air, but no magic word. Going carefully I eased my finger in until I reached her sphincter. She grimaced as I pushed further. "Hold on, slow."
"Want me to stop?"
"No, it's ok. I want to try this."
With a little more force I got past that barrier and felt her squeezing my finger. How was I going to fit my cock in there? Did she know I planned to fit my cock in there? One finger, in and out, getting her used to the feeling. Then a second finger.
"Oh fuck, you going to stick your whole hand in there?"
"No not my hand" I think she then got the idea. This wasn't me just one upping her finger in the butt. No, this was something more.
"Are you ready"
"Oh god"
"OK lift your butt up like we're going doggie style. That's it. Now more lube"
I squeezed a good bit on her now not so puckered anus and used my fingers to work it in. Then removing my fingers I added more lube and generously coated my raging hardon. It took all my control to continue taking it easy and slow. I placed my cock head against her anus and pushed, oh so easy. Constant pressure, but gently.
"Oh, oh fuck, oh my god. Fuck, I can feel it stretching my ass. Will it fit?"
"Oh it'll fit. Going slowly here. It feels like the head is in. It's SO fucking tight. Your ass looks amazing."
"OK, ok, keep going. AH FUUUCK, it's in. You're fucking stretching me. Oh keep going."
And I did. Until my pubes were tickling her ass and my lube coated cock was buried in her colon. It felt fantastic. Everyone should do this. But then I had the easy part. So I pulled back halfway. Then pushed forward more forcefully.
"Oh for fuck sake, just fuck my ass already. Stop with the gentle shit. Fuck me. FUCK me"
Well damn, ok. I grabbed Cindy by the hips to get some good balance and started pumping in and out trying to match her movements which were more irregular. She gasped, she groaned, she moaned, she cursed up a storm (I kind of liked the dirty talk). Then I felt my balls tighten, my cock get a little harder and I let go, filling her with several jets of cum. Finally, I leaned down, kissed the side of her sweating face and my softening cock fell out of her ass.
"I'm not cleaning that off", she said. I understood. She also had an odd little smile on her face.
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