Mom's Boyfriend CHAPTER 4

Chapter 4

June 18, 2026 View all chapters

Gradually the others slipped away until all that were left were Ryan and his Mom, Claire and another woman, a hot Latino called Megan. The three women were definitely the wrong side of tipsy and whilst Brandi was pushing up against her son, so he was squashed against the rest and she had two thirds of the sofa, the other two were getting close and giggly… very close and very giggly. Ryan watched as they moved nearer and nearer each other, their hands slipping over each other and their thighs rubbing together. His Mom was leaning her head on his shoulder also watching, though she seemed to have seen it all before, "Go on," she said with a girlish laugh, "Dare you to make out with tongue."

"What do you think?" Megan said to her friend, running her tongue over her bright red lips.

"A dare's a dare," replied Claire.

Ryan watched, literally open mouthed, as the two women came together and began to kiss passionately — as his Mom had dared their tongues darting forward and into each other's. He'd certainly heard cheerleaders could be wild — though given the cheerleaders at his school were all desperate to get good grades and go to a high class college, he felt it might be an urban myth. But certainly these two were and from the way his Mom was urging them on, she certainly had a side which he had never seen.

"Mmnn, how was that?" giggled Megan, it was unclear whether she was talking to Claire or Brandy, as both seemed entranced.

"Let's try again," giggled Claire, "And this time you can grip my boobies."

"W…" said Ryan trying to formulate a word.

"You go girls," his Mom laughed, squeezing his leg as she pressed against and over him, "You've not lost your touch."

The two women separated again, looking at each other with obvious desire before Megan stood up, "I'm calling it a night Brandi, see you tomorrow Ryan, Claire you coming with me?"

The other woman stood up, turning to smile at Ryan and his Mom, "See you tomorrow lovebirds, don't stay up to late." She took Megan's proffered hand and followed her out the bar.

Brandi drained her drink as well and Ryan quickly saw his opportunity, "We should go to our room as well."

"Spoilsport," his Mom giggled, "but yeah that enough drinkies for tonight, we need to keep something for tomorrow."

She stood up and as soon as he followed her, slid her arm through his and laid her head upon his shoulders in a less than familial way. They walked across the lobby and whilst she may have drunk too much she was still steady on her feet and as she spoke her words were clear and unslurred, "Enjoy tonight? What did you think of my friends?"

"Yeah," he led her into the elevator, "They were fun." He punched in their floor, though as it was only a couple up they could have easily taken the stairs. "Very open."

His Mom giggled, "I know what you mean, you naughty boy, the lesbian floor show."

"Um, yeah, that kinda threw me," he admitted, blushing slightly — talking about watching hot women making-out was not something you normally discussed with your mother, especially when they were her friends.

His Mom didn't seem to mind, however, "Cheerleaders are very friendly with each other" she said smiling. The door pinged open and she stepped out. "We all used to be very friendly when we were at school."

"Um, are you saying…?" he wasn't sure whether she even knew what she was she saying or whether she was just drunkenly burbling — not that she seemed out of control drunk, just merrily tipsy.

She giggled some more and broke away from him to look conspiratorially down the corridor as if she was checking whether they were alone, "Are you asking if I've been pussy to pussy with another woman?" she giggled. He blushed and so she answered for him, "You are, you dirty boy," she smiled as she spoke, before slipping her arm back through his. "It's not the thing a Mom should tell her son," she added with obviously mock sincerity, before breaking apart in peals of laughter.

"Okay," Ryan said.

"However as you're my lover this weekend," she continued, "and it's the type of thing women can tell their younger boyfriends…"

"You don't have too…" he began.

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