All sexual participants are older than 18. Much older.
It was two weeks after his first experience that he decided to go back to The Den. He didn't really have any expectations. He hoped to find another pickup as good as his first. That was probably unlikely.
It was around seven when he got there. He sat at the bar and ordered a Bourbon. As his eyes adjusted to the light, he was sure he saw some of the same women he had seen before. He sipped at his drink and looked around the bar. He had to admit that most of the women and a lot of the men were above fifty. This was certainly a place that catered to the older crowd. Even the music was sixty's and seventy's.
As he watched what went on around him he realized that the older men approached the women, but most of the younger men were approached by the women. He really didn't see any likely candidates. He ordered another drink. His second was gone and he was about ready to leave when a woman came in that attracted his attention. She sat at a table on the other side of the room and ordered a drink. She seemed to take in her surroundings.
She had big, perfect hair, and her makeup was just right. It showed her features to the best effect. She was overweight but she dressed to highlight her best assets. It showed off her full breasts and cleavage without seeming too obvious. It came down almost to her knees and her stockinged calves were shown to good effect Her heels helped as well.
At some point their eyes made contact and after that they kept coming back to each other. Their gaze lasting longer each time. She finally smiled at him and he returned the smile and lifted his drink to her. Several older men came over to her table and she even danced with two of them. He watched her carefully.
The big woman was surprisingly light on her feet and a good dancer. She seemed to enjoy it. Enough that she did two dances with each man. When a third asked, she smiled and indicated that she needed to use the powder room. She picked up her purse and went past him on her way there. She smiled at him as she passed and he returned the smile.
When she came out, she stopped by his table and asked "So are you Robert?"
"To some. And you are?"
"I'm Tiffany. You come highly recommended." She smiled at him.
"I'm flattered."
"You should be. Violet seldom talks about her encounters, let alone recommend someone." She looked him over critically. "You dance?"
"Seldom. If I drink enough to dance, it affects me later for other things." He smiled at her and she returned a knowing smile.
"You interested in other things?"
"Yes. Yes I am. You?"
"Your place?"
"Fine with me."
"I'll ride with you. I came in a cab. Shall we?"
He finished his drink, left a tip, stood, and held out his arm for her. She put her hand through his elbow and he led her to his car. After they were on their way it took some time before he asked "So you know Violet?"
"For years. Magnificent lady." She expected more questions but he stayed silent. She knew it wouldn't be a long drive. Before the end of the trip she put her hand on his shoulder. "You really impressed her you know."
He turned to look at her for a moment. "Really?"
"Oh yes. Really!" They remained silent for the rest of the trip.
When they arrived, he went to her side, opened her door, and helped her out. He led her to his apartment door, unlocked it, and motioned her inside. He was kind of uncertain as to what to expect. Was he supposed to woo her? Was she going to be as direct as Violet?
Tiffany looked around. It was a nice place. Clean, sparsely furnished, a typical bachelor apartment. She put her purse on the table, turned to him, and held her arms out.
Bob moved to her and embraced the big woman. They moved into a kiss. It became an exploring passionate kiss quickly. He moved his hands to cup her firm ass and lift it as his tongue explored her mouth.
When they separated, Tiffany looked at him and moaned. "Damn boy." She took his hand in hers. "Take me to bed!"
He led her into his bedroom and turned on the bedside lamp.
"Turn on the lights Robert. I want to see what I'm getting. I like to watch."
He turned on the overhead light and stared at the big woman. "Me too. There's going to be so much to see." He began to undress. She watched attentively as he exposed his body. The last article was his underpants allowing his hard cock to spring out and up.
"You do have a Goldielocks cock. Damn boy, that looks so good. Hell, you look so good." Now she stepped out of her heels and turned her back to him. "Unzip me please." When he did, she turned back towards him and allowed him to watch her undress. When she removed her bra he was surprised at how little her breasts sagged for their size. She had big hard nipples on puffy, bumpy, dark areolas. She pushed down her panties and stepped out of them. Her bush sparkled with her wetness. She still had a garter/girdle affair and her hose on.
"Leave them on. I love garters and stockings." His eyes devoured her whole body. "You might want to remove the jewelry. Don't want it to get tangled or lost."
"Good idea. Besides, I don't want to appear over dressed." She smiled at Bob. "Please eat me first? It's been some time and Violet raved about you." She moved to the bed and sat with her legs spread wide. "Besides, I don't expect you to after you've filled me with your hot cum. And I do expect you to fill me so full of your hot cum." She smiled and held her pussy spread with a hand on each side.
Bob knelt and moved his face between her legs. He moved forward to put his tongue to her wet lips. He put his hands on the exposed skin above her stockings and began to work at her with his fingers. Feeling her wonderful warm thighs. He pushed his tongue between her lips into her wet, hot furnace that was her cunt. He loved the moisture. The heat and the smell. His lips and tongue worked up and down her crease getting her wet and ready to proceed. The whole time continuing to gently work at her thighs. He now found her clit.
Tiffany moaned and her hands went to his head. Grabbing him by the hair as her body tensed. "Oh yes! Eat me! Like that. Lick my clit! Like that. I love this." She pulled his mouth tight to her.
He moved his tongue to her clit and licked at it. It was very hard and bigger than he expected. It pushed out like a tiny cock. He moved his lips to it and sucked at it. He felt her tense and gasp at his attention to it. He lashed at it with his tongue as he squeezed at her thighs with his fingers. He worked his mouth and tongue all over her pussy and thighs. He admired what he saw, tasted, and felt. She was big but smooth all over. She didn't show cellulite like many heavy women. In fact, she didn't show her age much at all. She was very pleasing to him.
"Oh God." She pulled at his hair and squeezed at his head as she pushed it into her pussy. Her legs went tense and pushed down against the floor. "Don't stop!"
He kept up his actions on her with his mouth and tongue but now moved one hand to join them. He moved two fingers into her and began to work them in and out. He moved them to the rough patch at the top of her now very wet pussy. He felt her go tense when he rubbed at this. Squeezing harder at his head. It encouraged him to move his fingers faster and harder.
"That feels so good Robert. Please don't stop. You're gonna make me cum." Her pussy flowed her juices freely. It squeezed at his fingers as he worked at her. He kept his fingers busy as his lips continued to suck on her huge clit. They were both loving this journey towards her climax and didn't want it to end. But, as all good things must. "I'm coming. Right there Robert. Just like that!" He felt her body tense up. Her stomach muscles clenched tight. She gripped his head. Pulling at his hair. He couldn't see her but her mouth was open as if to scream. Eyes clenched shut. She began thrashing now. Twitching in convulsions.
Bob held his fingers inside at her g spot and her clit squeezed between his lips. He held there as the pleasure washed over her. It seemed to go on forever. She gave several strong jerks with her stomach muscles and hips, then relaxed onto the bed. Seemingly spent. Short of breath. Her hands released his head and went to her sides. His face was soaked with her abundant, tangy, wetness. He slowly withdrew from her and moved to stare at her limp figure. She was soaked.