From Junior Cuck to Sissy Pt. 07

Disclaimer: All characters in this story are 18+. They are all ending high school and starting college.

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After an exhausted nap, we both got out of bed, and I fixed us something to eat. She was starving, and she explained that beyond the douche, the best way to keep our asses clean was to avoid eating much before one of these "special dates".

It made sense, realizing how many times I have had Daniel's yummy cock in my mouth right out of her ass, and it was always miraculously neat, tasting wonderful, mostly of sex, saliva and precum, with no traces of shit, as I had been afraid.

"Wow. It is really hard for... girls... Isn't it?" I wondered.

"Not for many. If you just rinse your pussy you are mostly done. But for anal sluts like you and me..." she told me, winking. "Yes, it requires careful planning, which is not always easy. You need to start practicing right away to be prepared, honey!".

"But... Daniel said he won't fuck me! And I'm not sure, really..." I resisted.

"Oh, please, Sam! Stop denying it! You begged him for it! And I saw your disappointment when he said no. I know you are dying to get your pretty asshole filled! Indeed, I will help you cleanse it AND stretch it, because you might have a chance pretty soon!" she said enthusiastically.

"What?!" I asked, confused and slightly worried.

"Well. Daniel told me he has a friend who might be more interested in lovely boys like you... So we'll try to set up a double date asap!" he confessed with a feline smile.

"Oh, my! Lana, I'm not sure! I'm still uncomfortable around Daniel, and you want to bring a stranger?" I stuttered, feeling chills in my spine.

"Umcomfortable... until you see his cock, bitch!" she snickered. "Come on, Sam, you have to admit you are as slutty as I am. And I say it with pride! You know too well many of those stupid and boring girls that can't fully enjoy sex because they are so fucking uptight and repressed. I know it might be a bit more difficult for you, as you still tried to consider yourself a "macho man" a few days ago, but now that you realize what gets you off, you have to embrace it! Stop now and you will always regret it!" she bluntly said.

It was a lot to take in, but I have to give her some credit, because she sounded right, and in no time we were in the bathroom again and she helped me douche myself. It felt weird to fill my rectum with warm water, but as we did I couldn't help getting horny, although my dick remained soft and curled. I noticed it and, for a moment, worried about not being able to get hard again, but Lana's instructions quickly distracted me from that.

It took more rounds of water in my ass for her to be satisfied, and she told me that to make sure, the moment of truth was to stick my middle finger as far as I could up my bum, move it around, take it out, and if it looked clean, lick it all around. It sounded gross, but she told me it was a great way to not lie to myself and get sloppy. "If you don't dare suck your finger, just imagine sucking a cock after it pumped inside you hard and deep". I blushed, obviously ashamed and aroused by the image in my mind, and she laughed pointing her finger to me, "You, little slut!".

Next I had to lube my ass, and then she brought me back to the bed, made me kneel on all fours, and produced a pretty big dildo from her backpack!

I tried to complain, but she kissed my lips deeply, and immediately pushed the fat dildo between our mouths, and after we licked it together, she made me suck it. "Think of it as Daniel's cock, honey. I know it is not as big, but it would be enough for your virgin ass, so make sure to paint it all nicely with your spit". She knew how to warm me up, and soon she felt I was ready and I felt her fingers start to push in my tight ass.

The lube helped her to quickly get a fingertip inside, and by smoothly moving it in circles, she managed to relax some ring muscle inside me, deep up my bum. The massage continued while I sucked on the dildo, and more fingers started to get into me, until she was pumping a four-finger cone in and out, making me moan.

Lo and behold, the dildo was out of my mouth, and when she asked me if I was ready, I breathed out a "Yes, please..." and she quickly replaced her hand with the silicone pole, which felt different from the moment its tip pushed in. Her fingers felt strange at first, and even while they started stretching my hole, the sensation of fingers was somehow pleasant but very weird. The dildo, instead, felt "right" from the start. It pushed gently, and it was pretty hard but spongy at the same time, and as she pushed it in, I could feel I was opening to something proper and longed-for. I could feel my tight anal muscles stretching to acommodate the wide shaft as it invaded my rectum, and while it was kinda distressing, it was incredibly sexy at the same time. I abandoned myself to the sensation and I imagined it was a man who was grabbing my hips and stuffing his cock inside me.

The whole thing seemed to have entered me, my little balls felt stiff and tense, and I felt my dick smaller than ever, like it was curling inside my groin. The hidden tip felt warmer and wetter as the cock started pumping in and out.

My arms yielded at that point and I fell face down over the bed, my ass hooked by that pistoning dildo making me groan and drool. Lana knelt behind me, grabbed my waist with both hands, and pumped the dildo with her pelvis. I had the sensation of being overpowered by a man.

She kept fucking my ass while asking me if I liked it, and if I still had any hesitation about getting fucked, she made me confess I really needed a man to fuck me hard.

My shriveled dick started leaking long strings of precum that stuck to my legs and to the bed sheets, slender and transparent threads, oozing non-stop, very different from what Real Men's cum.

And she went on and on for a long time until we were both exhausted, then she took one of my hands, putting it on the tapered end of the dildo to keep it in, flopped onto the bed to my side, placing herself against some pillows, opening her legs and asking me to lick her and make her cum.

With the dildo in my ass, I placed my face onto her drenched pussy and started eating her while still pumping my hungry asshole.

She grabbed my hair and pushed me up and down to guide my service until she had a noisy orgasm, and then we finally stopped and let ourselves doze off.