The Bridge Club - Illustrated
Copyright© 2026 by rlfj
Chapter 11: Alison Doyle
Erotica Sex Story: Chapter 11: Alison Doyle - Cullum Doyle’s mom is a member of a bridge club and one of the members has had a couple of drinks too many. Cullie is asked to help get her home. Complications ensue. This new version is re-edited and expanded, with two new chapters and over 80 illustrations. Enjoy!
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa School Group Sex Harem Anal Sex Oral Sex Illustrated
“I can’t believe we are doing this,” said Alison.
“We aren’t. You are,” replied June.
Alison rolled her eyes for the hundredth time. This was absolute insanity. She was meeting her son at the Marriott on Wolf Road. She was meeting him for a date. A sex date! This was beyond insanity!
It had all started a week ago, Friday night, at her house. Her three best friends had convinced her that she wanted what they were all getting, amazing sex with her son, Cullie. Then they had dragged her into her bedroom to decide what the best outfit was for her to wear. It needed to be sexy but not slutty, something that said she was available but not too available. It almost broke down at that point. When they went through her closet, she had begun crying. Every dress there was one she had worn for Joe, her late husband and Cullie’s father. “I can’t wear these! Cullie has seen them! I wore these for Joe!”
“Then they need to go,” replied June ruthlessly. “If you aren’t going to wear them, then they can go to Goodwill or the Salvation Army.”
“Maybe you can sell them online. There are websites you can do that,” added Janet.
Amanda said, “We need to go shopping. We can do that Monday over at Colonie Center. We’ll meet you there after work.”
“Oh, no. She’ll just chicken out that way. We’ll take her shopping. If we don’t find anything there, Tuesday we’ll take her to Crossgates,” argued Janet. June nodded in agreement.
Alison thanked God they had found something at Colonie Center, since her friends promised they would drag her to Crossgates Tuesday and then start going to boutiques on Wednesday. They settled on a black cocktail dress in a soft and satiny fabric, mid-thigh length, with a Vee neckline front and back. It was long enough that she could wear stockings, at least if she was careful, and went well with a pair of three-inch ankle-strapped black stilettos.
Now it was Friday night. Her sister had insisted on driving her to the hotel, for ‘moral support’ she said. They got there at six-thirty and Amanda had walked her to the Lobby Bar, where they took seats at the bar. Then, after ordering a drink, which Alison desperately needed, Amanda said, “Okay, have fun. We’ll talk on Sunday. I’ll get your bag up to your room.”
Amanda Dropping Alison At The Hotel Bar
“What! I thought you were having a drink with me?”
“Are you kidding me? The only reason I drove you here was so you couldn’t chicken out! I know two’s company and three’s a party, but you haven’t worked your way up to that yet.”
“AMANDA!”
“Bye! Don’t do anything I wouldn’t. Well, that might be fun, too. Bye!” Then she turned on her heel and left the way she came.
Amanda went back to the parking lot and looked around. She waited until she saw her nephew climbing out of his car and she waved to him. They met beside her car and she said, “Are you ready for this? I mean, really ready?”
He gave a wry smile. “I guess. It’s a little late to back out.”
“No, not really. If there’s a problem, call one of us. We’re all going to be waiting to hear how it goes.”
“Oh? Do you want us to set our phones to broadcast it to the cloud, so that the three of you can watch along?” he asked sarcastically.
“Would you?”
“NO!”
Amanda laughed. “Okay, that might be a bit much. We’ll do the live broadcast another time. Where’s your bag?”
“I’m leaving it in the trunk for now. Taking it into the bar and dropping it on her table would be a bit much, don’t you think.”
“Wait a sec.” She went to her car and grabbed Alison’s bag. She carried it back to Cullie and tossed it in his trunk after he popped it open.
She smiled. “Take care, Cullie. Let us know how it goes. We are all rooting for you, both of you.” She leaned into him and gave him a soft and gentle kiss. “Now, give her the night of her life!”
Cullie And Amanda In The Parking Lot
“I’ll give it the old college try,” he laughed. He reached into his car and pulled out his sport coat. The weather was a bit iffy, but he didn’t want to put on his trench coat. The beige sport coat went well with khakis, brown socks, and brown deck shoes. He hustled across the parking lot and went inside. The bar was just off the lobby.
Alison couldn’t quite believe what she was getting involved in. She was sitting at the bar in the Lobby Bar of the Marriott on Wolf Road, where her sister, who she swore was about to become an ex-sister, had just dropped her off. She was dressed in a skimpy ‘Little Black Dress’ and waiting for a potential lover to come and pick her up. That the lover was her son, a nineteen-year-old that her three best friends all considered the greatest lover they had ever had, was just beyond insane.
The bartender came over to her and smiled. “Miss?”
It took Alison a second to register he was there. “What?”
“Can I get you something?”
“Yes, please!” He kept waiting, eyeing her curiously. Then she said, “Oh, sorry, can I get a whiskey sour? Thank you.”
“Sure thing. Just give me a second.” The bartender moved down the bar a few feet and pulled the sour mix bottle from a small refrigerator under the bar. Thirty seconds later he had it in front of her. “Here you go.”
“Thank you!” Alison took the drink and finished it off in three quick swallows. It was good, but she needed more, a lot more. Intravenous Everclear came to mind. She pushed the empty glass back towards the bartender.
“Another?”
“Please.”
The bartender took the glass and put it with the other dirty glassware. He wondered if the beautiful woman was going to be a problem. He liked beautiful women, but not when they were drunk.
The problem ended after a fashion when a young and well-dressed man entered the bar. He walked up to the woman, who gave him a startled look, like she hadn’t been expecting him, but the young man smiled. He was on her right side and leaned down and said, “Alison, you look gorgeous. Thank you for coming.” His left hand was on her back, and his right was on her stocking-clad right leg. Then he leaned in and kissed her. The woman looked shocked but then responded hungrily. The bartender hoped the guy, whoever he was, would calm her down.
Alison couldn’t believe it! Her son was standing next to her, one hand on her back, half on the sheer fabric of the dress and half on her bare skin above the Vee. His right hand was on her legs and had slipped between them to caress the bare skin on her thighs above the lace tops of her stockings. Then there was the kiss, soft and gentle but when the tip of his tongue slipped out to touch her lips, something broke inside her. Gasping softly into his mouth, her tongue dueled with his as she reached up and pulled his face to hers.
Cullie Greeting Alison At The Bar
After a moment, Cullie pulled away and smiled. “That was very nice,” he whispered.
“Oh, Cullie ... oh my God!”
“I only have one question. Are you Alison or...” ‘Mom’ was left unstated.
She smiled at him and said, “I’m Alison.”
“Then, Alison, I suggest we try to space out the drinking. I know you’re nervous, but that’s not something I want to see you do. I’d rather take you home than watch you try to drink the bar dry.”
She pulled his face down again and gave him another kiss. “No, I don’t want that either.” She turned towards the bartender, now at the other end of the bar. He had moved away but was keeping an eye on the couple. He noticed her wave and returned. She had passed her untouched whiskey sour to her friend, and she asked, “One more please, and then I think we’ll be having dinner.”
“Of course.” The young guy looked old enough to drink, and even if he wasn’t, technically he hadn’t served him.
Cullie waited to sip his drink until the bartender returned with what was now Alison’s second. Then he sipped his drink and said, “Very nice. Now, we can finish our drinks and then get a table.”
“I’d like that,” admitted Alison.
With that, he set his drink on the bar and stepped closer. He put his hand back on her legs and slid it under her dress again. “You are just so beautiful. Is this a new dress?”
Alison shivered at the touch but then got her breathing under control. “You need to stop that, Cullie, or everybody is going to hear me screaming any second now.”
“Not in pain, though, correct?” he teased. He touched her thighs and then pulled his hand back, picking up his drink smoothly.
“Oh my ... no not in pain.” Alison composed herself and straightened her hem. “The girls didn’t tell me you were so naughty.” Then she took a deep breath and said, “No, we went out this week and bought a new dress. I ... I couldn’t wear a dress...” She lowered her voice to a whisper and continued, “ ... a dress your father bought me.”
“Maybe not,” said Cullie, nodding in understanding. “Well, if you’re Alison, should I call him Joe?”
Alison shrugged, which did wonderful things for the considerable cleavage she was showing. “Maybe, at least tonight, here. That might be weird at home.”
Cullie smiled at the sight of Alison’s C-cup breasts jiggling under her dress. Leaving aside any Oedipal or incestuous thoughts, Alison Doyle was a very beautiful woman. She could have any man she wanted, and now it looked like she wanted him.
They finished their drinks at the bar, and then Cullie led his mother towards the dining room. A hostess seated them at a booth near a window. It was a U-shaped booth, and after Alison sat on one side, Cullie sat on the other. Then he surprised her by moving sideways, so he was at the back, facing out of the booth. He grinned and tapped the seat between them and Alison slid around the booth until she was behind him. In so doing, the hem of her dress got slightly bunched up and she blushed as she untangled it and straightened it out. She saw Cullie grinning and looked down to see the hem was up above her stockings.
“I am loving the view,” he laughed.
“I bet you are! You are an awful person! The girls never told me that!”
Cullie grinned even more. “From what I have seen, the worse I am, the better they like it.”
Alison rolled her eyes but smiled at him. “I can believe that.”
“If we order another drink, will that be it for you?”
A Special Dinner
“Yes. It’s just ... I’m kind of nervous, Cullie. I haven’t been on a first date in over twenty years. Leaving aside the whole thing about you and me and the others, I’ve got the same nerves as I did back when I first met ... Joe.”
“Well, that worked out, didn’t it. And June, Janet, and Amanda got over their nerves, too.”
“I know. It’s just ... I don’t know. Yes, we all decided I was ready to start dating again, and last week proved that I was ready for what came next, but still. It’s like nowadays everybody is using apps and services and staring at their screens and phones. Maybe I’m just too old for that stuff.”
Cullie shrugged. “I think that’s a good thing.”
“Why? A good-looking boy... man ... like you can find a cute young woman anywhere,” said Alison. “Be honest, you can find a party on campus and find a young hottie in no time at all! Why haven’t you?”
“Let’s consider this from my point. First, I don’t live on campus. That means I might not be getting invited to all that many parties. Second, let’s assume I do get to a party. Do I end up getting drunk and stoned and finding a girl who’s also drunk and stoned? That just doesn’t sound all that appealing to me. From what I’ve seen of my classmates they spend an incredible amount of time, money, and energy chasing each other around, and for what? Sure, they might be younger than you guys, but not any better looking, and I can guarantee they aren’t as ... knowledgeable.”
“Knowledgeable. Is that another way of saying ... what?”
Cullie shrugged. “Knowledge is good. All sorts of knowledge.” He smiled and waggled his eyebrows; Alison blushed. “Anyway, again, from my viewpoint, I have three ladies who are beautiful, in their sexual prime, and very knowledgeable. Do I stay with them or do I spend all my time after class trying to find one-night stands. It’s an easy decision for me.”
Alison was becoming excited by the possibility of being added to Cullie’s harem of knowledgeable older women. She was sure that Cullie could see her nipples hardening under the thin fabric of her dress, and she knew he was occasionally looking at her legs under the table. Just then, however, their waitress came over and asked if they wanted something to drink. They both ordered another whiskey sour, but Alison also asked for glasses of ice water. The waitress handed them their menus, mentioned the nightly specials, and left them alone.
Alison glanced at the menu but then asked, “Do you really want dinner? Or did you want to go upstairs.”
“Alison, I can go either way. I’m actually kind of hungry, but I don’t know as I want a seven-course banquet either.”
“Maybe a salad and an appetizer? Some of the appetizers look like they can be shared,” she asked.
Cullie glanced at his menu and nodded. “I think that would be perfect. Something simple down here, and dessert upstairs?”
Alison blushed and nodded. “Good.”
Then she was surprised when Cullie put his hand in his lap and then moved it to her lap. “Spread your legs,” he told her. Alison looked wildly around the dining room, but there were tablecloths that would hide anything and nobody was paying them any attention. She gasped as her son’s fingers slipped between her thighs and began caressing the skin above her stockings. Then they moved higher, to slip between her pussylips and touch her clit. It was like the room exploded around her and she had to grip the table tightly to keep from screaming out her orgasm.
“Oh, Cullie!” she whispered. “That was amazing!”
Under The Table
“That was just the start. Yes, I might be enjoying a light dinner now, but dessert is going to be so tasty later!” Then he diddled her clit a second time, only stopping when a busboy filled their water glasses. Then the waitress came back with their drinks and took their orders, simple house salads with dressing on the side and a sampler platter of appetizers.
When their salads came out, Alison sighed. “Now eat your salad and give me a chance to catch my breath! You need to behave yourself.”
Cullie chuckled. “I’ve been told that. It never took, but I’ve been told that.”
“You just behave and keep your hands where I can see them.”
He shrugged. “I thought they were.”
“Behave!”
Cullie simply smiled and put a hand in his mother’s lap; Alison squealed quietly and reached down to stop him. He laughed and went back to eating his salad.
Their sampler platter came with two small plates and consisted of onion rings, petite crab cakes, stuffed clams, and taco chips with artichoke cheese dip. Alison took a look and smiled. “At least everything is in multiples of two.”
“Oh?”
“I’ve had a few samplers where you get an odd number of wings or whatever and you end up with family fights over who gets the extra.”
Cullie smiled. “So, who gets the extra tonight?”
“Maybe the person willing to perform the most exotic sexual performance?”
Finally, their small dinner finished, Cullie looked at his mother and asked, “Are we going upstairs? Or not?”