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Aliah's first anal training. A proper young girl's guide to anal pleasure

She couldn't quite believe it, but yes, it was happening. 20 year old Aliah- one of my neighbor's daughter- finally came to me for her first anal experience. She grew up in a very traditional and religious family. This time I asked one of my female friends, Jen, to join me as my assistant. As Aliah entered the room, without saying a word to interrupt, she took the demeaning position by bending over and laying across my lap as she felt her panties sliding off. Her thighs were strong and she could have easily clenched her butt tightly in an impenetrable manner. Instead, she relaxed and let me spread her young cheeks. For almost 15 minutes, me and Jen rubbed her bottom, crack, thighs, lower back, and her hair to make her more relaxed.

It felt strange. As an anal virgin, Aliah now had two trainers, staring directly and touching her anus. When Jen spread the cheeks further apart, we had a clear view of her bottom crack. The thin, feminine fingers on Jen spread her alluring butt cheeks even further, and Aliah could feel air flowing on her tight, untouched and virgin hole. This was a different sort of shame. All her life, only one female doctor had seen this very private area. Now here it was, for her neighbor and the assistant to admire, or whatever they were doing to her behind.

                                          

Her body suddenly jerked when she felt the lube being poured on her anal region, as two fingers held her bottom cheeks open. It felt cold and it tickled her anus. What came next seemed even more intrusive. Aliah felt a bare index finger touch the outer ring of her anus. I didn't even bother to use a glove. The hand rested on Aliah’s plump butt and the finger gently massaged the anal ring in firm circles. "I can't believe this is happening to my asshole," Aliah sighed. The more she relaxed her cheeks, the more she enjoyed my finger circling her winking hole. It felt so tender and vulnerable. There was nothing to compare this too.

Suddenly, the lubed finger plunged into her asshole and Aliah's eyes widened. Although it was my pinky, it made an impact in her virgin hole. My finger probed inside her rectum in a circular motion, coating her tight passage. When the finger quickly pulled out, she was left with a false sense of relief.


OK Aliah, stand up and lay on the couch with your bottom up in the air, legs spread wide and face down. She then felt the smallest butt plug pressing against her anus. My assistant used both of her hands to hold Aliah's bottom cheeks open, to help me slowly push the plug in. Aliah resisted every urge in her body and fought to remain calm. She could only imagine what her rear end looked like, with her anus being stretched in the most unnatural way possible. As the plug kept on being pushed, and Aliah's asshole opened, the plug was able to enter. Penetrating the anal ring was the most difficult part and she felt her lubed rectal passage being overwhelmed as the plug made its way in. I gave her butt a soft rub, then a spank, which only made her ass clench around the plug.

"Is it done?" Aliah asked, slightly aroused. It put a smile on my face, "would you buy a car without a test drive?" "What does that mean?" she asked, turning her head to us.

"Stand up. Lose the skirt. Then walk back and forth. Like I said, we'll need a test drive of your anus." When she stood, she felt an incredible uncomfortable but arousing feeling as her butt clamped around the plug. Her anus had never felt like this since... ever. She removed her black and white plaid skirt and stood naked in front of both of us. She walked back and forth across the room like a fashion model, trying to be as bold as possible with her own nudity. She refused to look us in the eyes; that would only make her more nervous and self-conscious that she was the only one naked.

"Excellent," I said with a pleased look. Now, bend over the dining table. Each of Aliah's butt cheeks were squeezed tightly and held apart. She pressed her face onto the table and waited for her first anal fuck session. She heard me unzipping my pants and positioning myself behind her. The tip of my hard cock touched her sensitive anus and she felt Jen doing all the work to ensure that the cock would have a smooth entry passing her anal ring and into her rectum after removing the plug.

"You're very tight," I said after a light thrust of my cock head...It was the first time we heard Aliah's moaning from real pleasure...


*Different name has been used to protect Aliah's privacy

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Update:                                                                                                                                                         

Aliah sent me "thank you text" 3 days after our play,         a part of her text was:

..My face and chest tingled with excitement over everything that happened, and that was still happening. I was worried about the embarrassment of someone seeing me in a shirt and panties, and I ended up letting you guys see my breasts and pussy and naked body! I'd only had one boyfriend in the past and we mostly did things in the dark because I was so shy. Nothing like the audience I got the other day, or the view you and Jen enjoyed. It was humiliating and also incredibly arousing how far things had gotten, especially seeing the effect I had on your big cock. Thank you for training my asshole and I want more.

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