The following day they all decided to go back to the Bavarian town's bakery for breakfast. The route there and back would pass Tad and Jan's cabin so they could pick up what they needed. In addition to the training kit and butt plugs they found some desensitizing lube they had bought for Leah's introduction to back door entries.
Back at Becky's it was decided that there's no time like the present so they all stripped and headed to the bedroom. The original idea was that Tad would train Becky, but as he was being trained as well it was decided that Jan would take his place. Becky and Tad laid face down on the bed with a pillow under their hips, raising their asses a bit.
Leah took the regular lube and slathered it on Tad's asshole and the medium vibrator, while Jan used the desensitizing version on Becky and her small vibe. "Okay guys, remember to relax. Take deep breaths, calm yourself, and focus on the enjoyment this will bring you, once you get used to it," Jan instructed.
Nodding at Leah, Jan placed the tip of the vibe on Becky's asshole while Leah did the same to Tad. They both slowly pressed in, guiding the vibes as they breeched the two sphincter muscles. Tad recognized the vibe was larger than the fingers he was used to, but found it very easy to adjust.
"Stop, please," Becky told Jan. "Just hold it there and let me get used to it for a second. It doesn't hurt, but as Leah said it's a new, weird feeling."
"Is the desensitizer helping?" Jan asked her.
"I think so. Can you rub my ass around the vibe with your fingers?"
"Sure," Jan said as she did as Becky had asked.
"Yes, it feels a bit numb. Not completely like the novocaine the dentist uses, but just a bit less sensitive," Becky told her. "You can push it in further now."
Meanwhile Leah had pushed the vibe as far into Tad's ass as possible, given that she needed to leave a bit outside so she could hold it. "How is it, Tad?" she asked him.
"It's fine. It feels good, but not great. I'd never cum from this, but maybe larger things will do more to get me going."
"Let's try this,' Leah proposed, turning the vibrator on at a medium-low setting.
"Whoa! Now that's interesting," Tad exclaimed. "Stroke it in and out but leave it on, please."
Leah did and also reached her other hand under Tad, encircling his cock, which was rock hard. "Want a hand job, hon?" she asked him.
"No thank you. I want to concentrate on my ass. Once I get used to this we can try all sorts of things, since there's only one of me and three of you."
Becky had taken all of the small vibe in her ass and allowed Jan to stroke it in and out. It wasn't long before she was encouraging Jan to speed it up, and then again. Jan's hand was actually getting tired, trying to hold the small vibe by its end and rapidly fuck Becky's ass.
When she feared she'd tire so much as to have to stop she turned the vibrator on medium and slowed down the stroking. "Wow, that's different!" Becky said. "I like it!"
Leah began varying the vibration speed up and down and when Jan heard the changing buzzing sounds she followed suit. Finally Becky asked Jan to turn it off and remove it, and Leah decided to end Tad's session as well. As the vibe left his ass Tad was slightly surprised to realize he missed it. He made a mental note to ask the women about it.
Leah got up and retrieved two warm, wet washcloths. Returning to the bed she tossed one to her mother and used the other to clean the lube from Tad's ass. Jan first lightly wiped Becky's wet pussy and then mimicked Leah's actions. Once cleaned up, both 'students' rolled over and propped themselves up on the headboard.
"So, what do you think?" Leah asked them.
"You and Jan were absolutely right. I'm assuming you treated us the same way Tad did you. Starting small is the right approach. We'll have to wait to see if I feel the same after moving up to the next size. I'd like to try this again later today with the small vibe but using regular lube," Becky shared.
"It was interesting, but not terribly different from the fingers until you turned on the vibrations. It's a bit larger than the fingers but almost not enough to notice, to be honest. I think I'm ready to move up in size," Tad told them. "But I do have one comment and question. When Leah pulled it out completely at the end I felt disappointment. Is that the same for you and do you also feel that way when a cock leaves your pussy?"
"Yes and no," Jan said. "If I've had a great orgasm from either, I usually don't feel disappointed. But if I didn't cum, or if you're just pulling out of my pussy to change positions, yes, my first thought is 'oh darn'"
"I agree with Jan," Leah said.
"I do too, with regard to the pussy part. We'll see, perhaps, about the ass part," Becky said.
"I think I'll take a pass when Becks has her second session later today. Tomorrow I want the large vibe and, if she's ready then the medium one will be available for Becks," Tad explained.
The next morning Becky announced that she thought she was ready for the medium. Her second session yesterday went perfectly, even without the desensitizing lube. She recognized that she had instinctively learned to relax, even being able to open her sphincter to an extent. Jan had expected Tad to take over since he wasn't having a second session but he explained that he thought it best to stay consistent. Since Jan had done session one, she should continue all the way with Becky.
Tad took the large vibrator without major problems. He did finally understand the 'full' feeling everyone talked about. Beyond that, neither the girth nor length of the vibrator was an issue, although he recognized that it was still noticeably smaller and thinner than his cock, and its clones. He had minor trepidation about being able to accommodate that.
Beyond the training sessions, all four were also still having sex in various combinations. Instead of the usual twice a day encounters they were only having one as the ass training sessions took up time and energy as well.
On Day 3 Becky asked for the large vibrator and found that, with patience and a caring guiding hand from Jan, she could handle it as well. When Jan had fully inserted it into her and then turned on the vibrations, starting at low and slowly increasing it to maximum, Becky actually felt as if she could climax from just that. Looking to the future she decided that, if she was capable of an anal orgasm, she wanted the first to be at Tad's hands, or rather cock. She asked Jan to end the session and she, of course, did.
All three women wanted to watch as Tad took a 'cock' for the first time, so he observed Becky's ass fuck with the large vibrator. When she ended, he took her in his arms, saying "I'm so very proud of you, my love" before kissing her long and deep. When they separated first Jan then Leah reiterated those sentiments.
It was now time for Tad. Jan suggested that they move to the living room. "When I first took Tad's cock in my ass, he had me kneel before an armchair like that and rest my head and arms on it. He kneeled behind me and took me that way. Since then we've done it in many places and positions but I honestly believe that's is the best place to lose one's anal virginity."
Tad kneeled at the chair and Leah handed the dildo to her mother. "You're his full time partner, Jan. You should be the one to pop his cherry."
Jan laughed and said, "Thank you, my dear. Someone raised you right!"
Putting plenty of lube on Tad's hole and the dildo, Jan positioned herself just to the left of his butt. "Are you ready, sweetheart?" she asked.
"Yes, go ahead," he replied.
Jan placed the head of the dildo on Tad's asshole and firmly but slowly pressed it forward. Despite Tad consciously relaxing his muscle, she met resistance. She pressed harder, prepared to stop instantly if Tad objected, but he remained quiet, even pushing back to impale himself.
All of a sudden the head popped past the muscle. Jan had wrapped one hand around the shaft of the toy, most of the way to the head end. When she broke through that hand met Tad's ass and stopped any further insertion.
"Okay, hold still and let me get used to this for a moment," Tad requested. Breathing deeply he made an effort to relax every muscle in his body. He'd realized that his shoulders, fists, and even abs had contracted involuntarily.
"I'm ready for more, but please go slowly," Tad asked Jan.
Jan pressed in slowly. Both of them expected Tad to ask her to stop when about half way in, as Jan, Leah and the other virgins Tad had taken had done. Tad had no way of knowing how far in Jan was, unlike when he was the fucker instead of the fuckee. He could feel her ass on his cock and knew how much had gone in. Never having taken anything this size, he had no frame of reference.
"Are you okay, hon?" Jan asked him.
"Yes, you can keep going."
"I would, but you've taken all of it already," Jan told him, a hint of pride coming through her voice.
Becky and Leah broke into a round of applause while shouting "Great!" and "Fantastic!"
"Cool," Tad said. Go ahead and pump me. Just make sure you don't let the head pop out - I want more experience before having to do the breeching again."
"Do you want us to play with your cock," Leah asked.
"No, thank you. I want to concentrate just on this. I'm not looking to cum. Y'all can make that happen later on," Tad told them.
Jan pumped the dildo in and out of Tad's ass for more than five minutes when he said, "Okay, I think that's enough for the first time."
