Betty Pearl's Sissy Stories 20.1
Menu => Active Sissy Stories => Topic started by: antonia on May 24, 2026, 03:46:54 AM
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It has been a while but another attempt to entertain you.
Chapter One
Olivia was a successful business graduate who had made rapid progress in her father’s financial business and drove an expensive sports car that she had plenty of room to park in the five bedroom house that she had just purchased in Salisbury. Her piercing blue eyes, long flowing brown hair and perfect figure made her a much desired date with the opposite sex. This was a lady who was not for controlling but had her own rules and was not loose with her favours. Despite the gossip among the studs in the office, nobody had made it into her knickers or even come close to scoring that base.
Andy was her current suitor and had the normal passions and ambitions as every other hot blooded male. He had been going out with Olivia for three months and to date had made first base which was walking hand in hand as they promenaded. She was tall at over six feet tall, whereas he was diminutive in stature and barely cleared five feet. From a distance you might be forgiven for thinking that you were looking at a mother out with her child. His arm slightly raised in order to engage with her hand.
They really did get on extremely well, chatting and laughing, sharing a love for good food, fine wine and the ambience of a lovely restaurant. On a number of occasions, Andy had moved in for a kiss only for Olivia to pull back or turn away. “Do you really need to snog in the street?” She asked him “it’s a bit juvenile don’t you think?”
Andy just shrugged and put his arm around her, which was basically hugging her round the waste like a child, his head almost on her breast. She turned suddenly as they were crossing the road and he almost ended up with her tit in his mouth as he looked in the opposite direction for traffic. She chuckled and pulled him in tight, “naughty baby” she exclaimed. Andy responded with a mighty erection that almost stopped him from walking and a blush that was incandescent.
They arrived back at his car and he held open the door for her. He struggled to get in with his rising passion. He drove her home and walked her to the door, but he made no attempt to kiss her passionately and satisfied himself with a peck on the cheek. In his mind he had decided that this relationship was going nowhere.
“Would you like to stay the night?” She asked him “it’s very late and it’s Saturday tomorrow”. Andy was too surprised to answer immediately. Spend the night? He never saw that coming.
“I would love to stay” he said in a rather goofy voice that did nothing to support his maturity. They crossed the threshold, Olivia holding his hand to guide him into her lovely home. She took him into the lounge and sat him down on the sofa while she gathered a bottle of Montepulciano and two glasses. She poured them both a generous measure, giving one to Andy. “Cheers” he toasted her.
Olivia went to her bureau and removed a small box “here, try this it will help you relax” she said with a knowing wink. Andy accepted the proffered pill and washed it down with a large slug of his wine. In no time at all he felt himself swirling in a hazy dream state; he felt a warmth and need to be compliant. He hung on her every word, each word resonated like a crystal note that burned into his head. He floated upstairs being led like a toddler to his crib.
Words flowed over him as his clothes were taken off piece by piece. “You will lie with me. You will not make a mess in my bed. You will not put your seed in me. You will not do a wee wee in my bed. No poo poo in my bed. You are going to be protected from your eliminations”. She smiled at him as he had a huge smile on his face and gave her a look that was pure adoration. Olivia was giving him gentle instructions as she folded and pinned and crinkled with him. He felt secure and protected, a feeling he had not experienced since his earliest day. He felt himself being laid down in her bed. Olivia joined him wearing a simple but accessible night dress. He took her breast with her guidance and with gentleness he began to suc-kle. Olivia tingled In excitement and after a happy time moved Andy’s head lower down where he continued his administrations with oral stimulation. She came with a huge crescendo of orgasms that bounced from one to another until she was satiated.
Andy was away with the fairies, in a place where reality was mixed with his wildest thoughts. He snuggled up to Olivia who hugged him and gently patted his bottom as his mother had decades before. He moved to kiss her on the lips and received not her tongue but a rubber nipple that filled his mouth. It wasn’t her breast but the large shield rubbed comfortably across his face. Instincts previously dormant came rushing back to his new reality and the large dummy started to bob back and forth as he suc-ked it with relish. His last thought was something soft being placed around his neck as he drooled and dribbled. Then blackness.
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Mmmmmm!!! What a lucky boy Andy is. Taken in by Olivia and, it seems, turned into Her sissy Baby slave already. Look forward to next episodes. :)