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Author Topic: A New Family Dynamic  (Read 76484 times)

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CuddleBunns

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Re: A New Family Dynamic
« Reply #70 on: June 25, 2020, 09:29:11 PM »
sissyboy1212,

Thank you, but by all means, please do! I'm absolutely loving your story so far. I'd hate to keep it from the rest of the world. Thanks for the hugs and I really appreciate your feedback. Best wishes!


sissyboy1212

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Re: A New Family Dynamic
« Reply #71 on: June 25, 2020, 09:44:17 PM »
Hee Hee!  Ok, but a big kiss and kudos to you!


Sissy Little Girl

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Re: A New Family Dynamic
« Reply #72 on: June 25, 2020, 10:29:19 PM »
CuddleBunns, Poor Lilly, she is in such a conundrum.  She's breast fed, told not to talk, must keep her pacifier in her mouth at all time and is now going to have a babysitter.  What she didn't know was the fact that her babysitters were going to be two of the girls from his former school. 

The girls will enforce everything they have been told, especially not letting Lilly use big girl words.  The spanking that ensued should have made the point very clear to Lilly.  :'( :'(

Another GREAT chapter and I can't wait for the next chapter.
 :P :P :P :P :P :P :P :P :P :P

dolly bo peep

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Re: A New Family Dynamic
« Reply #73 on: June 26, 2020, 08:03:16 AM »
CuddleBunns,

I agree 100% with Sissy Little Girl and love your last chapter.

It certainly looks like Sissy Baby Lilly is getting everything he wished for in his journal and then some!

I think that former high school friends Alexis and Samantha are the perfect choices for babysitters and look forward to future babysitting scenarios with them.

CuddleBunns

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Re: A New Family Dynamic
« Reply #74 on: June 26, 2020, 05:03:52 PM »
Thank you, Sissy Little Girl and dolly bo peep. I'm very excited to have more of Alexis and Samantha involved in the future. Let me know what you all think about the dynamic of their relationship with Lilly, because after I'm done with this story I've been planning on writing another (albiet probably shorter) story with a similar sort of dynamic in it.

Part 23

 Alexis jumped in surprise when her phone suddenly went off. She looked down at her screen and saw it was an alarm she had set hours before. "Aw man. Sam, it's already time to start getting the baby ready for bed", she said sadly. Samantha looked at Lilly for a moment, then over at Alexis, then back at Lilly again. "Hmmm...", Sam began to ponder aloud, "I guess thats true. Its been so long since we've all been together though. I really want to spend some more time together, the three of us. Maybe...". Sam paused and looked Lilly directly in the eyes before continuing, "...and this is a big maybe....if our baby is co-operative we could all watch a movie or something after we give Lilly a bath and get her all dressed in her pajamas? Her mommy and sister won't be home until 11, and its only 6:30 now. That would give us plenty of time to eventually put her down to bed before they return. It would have to stay our little secret though."

 Alexis clapped her hands together and smiled. "That sounds perfect! What do you say girly girl? Do you want to spend some more time with your lovely babysitters?", she asked Lilly in a cute and playful tone. Lilly was unsure how to respond. He was not allowed to talk, and nodding felt so impersonal. Still, it was the only real way he'd be able to answer. After a few moments of silence he reluctantly nodded, and was rewarded with an exited squeal and another big hug from Alexis. This caused his tiny member to get exited and strain against his cage. Alexis had always been a hugger, but now that he was not considered a sexual threat whatsoever, both girls seemed to be much more touchy-feely with him then he ever remembered them being in high school. He felt Alexis' breasts push up against him as she wrapped her body around his and squeezed.

 "I'll start her bath while you get her night time clothes ready. Find something really pretty for her", Alexis said to Samantha. Her friend nodded and got up to head into the nursery. As Samantha left, Alexis suddenly picked Lilly up and giggled at the ease with which she was able to do it. "Wow baby, you weigh practically nothing", she teased while Lilly sat comfortably perched in her arms. She began to carry Lilly up to the bathroom, where she turned on the hot water in the bathtub and began to fill it up. Lilly had been bathed by his mommy at least weekly in the past couple of months, but it was usually a very efficient and mechanical affair. However, the idea of being washed all over by his high school crush was very overwhelming to Lilly, who knew there was absolutely no way he would feel comfortable in his chastity cage for any of this ordeal. His pen-is was already straining when he heard the words he had been fearing for the past couple of minutes: "Alright Lilly, time to take your clothes off!"

 Alexis reached down and unbuttoned his pink onesie, taking the opportunity to remove his wet diaper before instructing him to hold his arms up so she could remove the onesie entirely. Soon Lilly was standing (albeit with unsteady legs) completely naked save for his pathetic pink chastity device, which Alexis could not help but snicker at when she saw it in its full glory for the first time. "Now that, I definitely approve of", said Alexis with absolute certainty. "Before you get in the tub, I want you to see something real quick"

 Lilly watched as Alexis pulled out her phone and started to look through it. She eventually found what she was looking for and gave him a mischevious smile, flipping the phone around so that he could see it. Sitting there right in the middle of her brightly illuminated screen was a picture of an absolutely hung, thick pen-is that easilly dwarfed Lilly's in size, even without his chastity cage. Alexis giggled to herself. "That's my boyfriend's", she explained, "Isn't it nice sissy? He's big and thick, like a real man. I wonder how it compares?"

 Alexis held the phone screen side by side with Lilly's caged pen-is and shook her head at the comparison. It was absolutely no contest. Alexis could feel the abject shame exhuding from Lilly's beet red face, and she was starting to feel absolutely intoxicated by it. In truth, even though she had always thought of Lilly as a friend, she had always enjoyed teasing him, even back in high school. Although she never had any real sexual feelings for the boy, a part of her always enjoyed the idea of him being a pet of sorts, or a completely subservient toy she could bend to her every whim. Now she was here with the perfect opportunity to do just that, plus the added bonus of there being absolutely no way he could get the wrong idea. A lightbulb went off in her head as she stared at his tiny sissy clit side by side with a real man's coc-k.

 "Wow that thing is absolutely tiny", she said to Lilly, who could only stare at the floor ashamed of himself. "It's honestly more of a clitty than a real dic-k. I'm sorry baby, but do you see what your competition is? You should be glad you don't have to try any more. The life of a baby is honestly what you've always needed. I wish you told me this is what you really wanted in high school so I wouldn't have had to keep worrying about you trying to date me all the time. Instead I could have just dressed you up in pretty clothes and we could have spent all of our time cuddling together. You could have been like my little doll!". The harsh words left a sting on Lilly's ears, causing his eyes to start watering at the verbal humiliation he was receiving. Alexis started to feel a bit bad about this, so she reeled back a little. "Oh baby, dont cry. It's just the facts of life. I like you much better like this. And to show it, I'm going to let you do something you've always wanted to do."

 Lilly's ears piped up curiously at what Alexis said. It could be any number of things, god knows he had wanted to do a lot over the years. Alexis smiled when she noticed his tears temporarily stop and met his eyes when he finally looked up at her. "See? No need to cry baby. This will be fun!", she exclaimed. She next began to remove her top, much to Lilly's surprise, and threw it at him in a playful manner. Her body looked absolutely stunning as she walked in front of Lilly and put her hands on his shoulders, crouching down slightly so she was at eye level. Not that it mattered, Lilly was too busy staring at her wonderful shapely breasts to notive, which were pressed together by a sexy black push up bra. She leaned in closer and began to speak softly into his ear.

 "If you do exactly what I say right now, I'll let you do the one thing I know you've most wanted to do since tenth grade". Lilly felt a tinge go down his neck when she began to speak into his ear. His tiny pen-is seemed to be straining against his cage constantly by now, like a moth trying to fly in through a closed window. Her touch felt like a surge of electricity to him, edging him on as she continued talking. "I know how badly you want to kiss me. I know you've been dying to since we met. Well guess what? I'm going to let you do it. Is that what you want puddle pants? A kiss from your sexy babysitter?"

 Lilly's eyes were beginning to tear up again as he nodded. The strain against his cage was becoming too much to bare, driving him absolutely insane. Alexis laughed at the sad sight in front of her. "You can answer me when I ask you questions baby. I won't tell your mommy", she said.

 "Yes! God yes!", Lilly cried out in a constrained voice. His pain was making it hard to concentrate.

 "That's what I thought", Alexis responded. Her grin was growing wider by the second. She was loving this more than she thought she would. "Now remember, you have to do exactly what I tell you if you want to kiss me. Right?"

 "Yes! Yes! I'll do anything!", Lilly spat out impatiently. It was becoming too much to bare. Lilly wished she would get to the point already before he broke down from all of the anticipation. Alexis grabbed her phone and held it up to Lilly's face. He now found himself staring directly at the huge, bulbous coc-k she had shown him before. Alexis' voice grew much more stern as she began to bark orders at him. "Kiss my boyfriends dic-k, you pansy", she commanded, "and kiss it like you mean it".

 Lilly closed his eyes and shuddered as he prepared for what he was about to do. He leaned in reluctantly and kissed the screen on Alexis' phone. As he pulled away from the meaty digital coc-k in front of him, Alexis shook her head in dissapointment. "You call that a kiss? I said kiss it like you mean it, not like it's your great aunt on thanksgiving. Kiss it again, and give it a little more love this time. Show me that you crave his coc-k. Make me think you're really savoring it". Lilly sighed and leaned in once again, puckering up in an exaggerated manner as he passionately grinded his lips against her phone, making loud moaning sounds as if he was enjoying every second of it. He felt absolutely disgusted with himself, but he figured the reward would be well worth it.

 Alexis tried her best to contain her laughter as Lilly pulled away from her phone again. With a highly amused voice, she praised him for obeying her. "Good girl. See Lilly? It wasn't so bad was it?", she said with a pat on the head. Lilly tried his best to forget what happened and began to grow anxious about getting his reward. "C..can we kiss now?", he asked Alexis in an unsure voice that could only be described as pathetic. Alexis responded by giving a chuckle and waving her finger at him. "Ah ah ah", she teased in the voice one might use for a dog, "you still have to do one thing for me".

 Lilly bunched his fist in disappointment. Despite being disgusted by what he had just done, his pen-is had not stopped in its quest to try getting hard, and although he wanted the pain to end, the same sensation that drove his pen-is to insanity was driving him to keep pursuing the one thing he had wanted for the last four years. Lilly shook as he demanded to know what more he could possibly have to do.

 Alexis swiped the screen on her phone and brought up a picture of her boyfriends face. He was the exact kind of hunk she had always ignored Lilly for back in high school. His chin was perfectly chiseled, his skin was well tanned and smooth, and his eyes were confident and domineering. He was everything that Lilly wasn't. Alexis giggled and held the phone out again. "Isn't he cute? His name is Mark. I want you to look him in the eye, and I want you to say thank you daddy", she commanded him with a cruel smile.

 Lilly was very close to the verge of crying now. He tried to compose himself, thinking about the kiss from Alexis he wanted so much. His voice stammered as he looked directly at the mirror opposite of what he was on Alexis' phone and forced himself to get it over with. "Thank you d...daddy", he finally managed to say after quite some hesitation. Alexis pulled the phone away with a look of accomplishment, clearly very proud at what she had done.

 "You absolute pansy...that was great! You're a natural!", Alexis praised Lilly with a hug to his naked body. By now Lilly could take no more. He needed his kiss and he needed it now. Alexis seemed amused by his obvious discomfort. She leaned down directly at Lilly's eye level, finally ready to give him his reward. "Alright baby, you earned your reward. Come give your cute old babysitter a kiss".

 Lilly leaned in to kiss Alexis only to be held back before their lips could meet. Alexis giggled at the confused boy. "Oh no no no, I think there's been a big misunderstanding here. I said you could give me a kiss. I never said you could kiss me on the lips, you silly baby. I have a boyfriend you know."

 Lilly stood there in shock. What was this nonsense! Had she really just tricked him into humiliating himself for nothing? Alexis put her arm around Lilly and turned her face, exposing her bare cheek to the upset and degraded sissy in front of her. "Come on baby, you earned it. Give me a wet one right on the cheek. It's the only time it's probably ever going to happen, so make it count", she said to him.

 Lilly started to break down sobbing as he leaned in and planted a tiny peck on the cheek of the woman he once wanted more than anything in the world. It was a perfect book end to any thoughts he may have had about the nature of their relationship, Alexis thought, because from now on he would know exactly where he stood in her eyes. She felt a bit bad for him, of course, she did like him as a person after all. Still, she couldn't deny that she really enjoyed the power she felt as she sadistically told him what to do, and looked forward to the future of their relationship as babysitter and baby. "Alright doll", she said as she suddenly picked him up and brought him over to the tub, "time for baby to take his bath".



sissyboy1212

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Re: A New Family Dynamic
« Reply #75 on: June 26, 2020, 05:49:33 PM »
Love it love it.  The excruciating denial and humiliation for little Lilly is wonderful.  Poor little Lily is getting all she wanted and more.

Lovely story ??

sweet baby katie

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Re: A New Family Dynamic
« Reply #76 on: June 27, 2020, 12:04:18 PM »
This is a wonderful story.  You capture the sweet ambivalence of slowly accepting the feminization and infantilism that is the deepest heart felt desire of all sissy ABs.  Sigh...

 

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