Jake had worked the rest of his shift in a daze. As he pulled into his driveway, he still couldn't believe what had happened with Mrs. Taylor. The thought of a 35 year old woman sucking his dick was unbelievable. He knew he would never be able to tell any of his friends about this because they would think he was lying. He thought about her suggestion for home deliveries from the grocery store. Did she want more? How far would she go with him? Would she go so far as to fuck him?
Thursday rolled around and Jake drove in to work with his mind made up to talk to Mr. Bailey, the owner and manager. Ed Bailey had been in the grocery business for over 30 years and had seen it all from the super stores to the smallest Mom & Pop stores. When he was a teenager, he had worked as a stock boy and the store he worked at made home deliveries, mainly for the elderly. He had mulled the idea over for the last few weeks but never made his mind up to try it. When Jake knocked on Mr. Bailey's door and opened it, he politely waited until Mr. Bailey hung up the phone before speaking. He told Mr. Bailey that he had been thinking about a suggestion one of their customers made to him about home deliveries. Mr. Bailey's mouth dropped open. He told Jake that he had done deliveries when he was a teen and working in a grocery store and that he had been thinking about trying it here for a few weeks. He said that they would try it. He and Jake sat down and hashed out the details, including hiring another stock boy to stay in the store and having Jake work on Tuesday nights also as long as he kept his grades up.
As Jake worked his shift that Thursday night, the possibilities running through his mind seemed endless. He knew that the majority of the customers using the delivery service would be elderly. However, there was always the chance that he would come across those like Mrs. Taylor. At the thought of Judy Taylor and her luscious lips, his cock jumped in his pants. He knew he had to get that thought out of his head before he had a full-blown erection and someone saw it.
Saturday arrived and Jake drove in to work. He had spent the previous night dateless once again. Still, the night wasn't a total loss. He read several more of his favorite older lady/younger man stories on Literotica and had a jerked off 3 times to the combination of what he was reading and what had happened to him the previous Monday. When he pulled into the parking lot at the store, he saw the sign in the front window. It said that a grocery delivery service was now available on Monday, Tuesday, and Thursday nights and on Saturday afternoons. There was a $20 minimum order with a delivery fee of $5. Jake walked in the store and punched the time clock. Mr. Bailey was waiting for him. He said that there had been several calls already for deliveries and that it was looking like a great idea. He handed the lists to Jake and told him to get after it.
Jake zoomed around the store, filling the orders. He bagged them separately and wrote the customer's name on the paper bags that belonged to them. He was so busy filling the orders that he didn't notice the last name on the list until he was done with all the others. It was for Judy Taylor and listed her address for the delivery and specified a delivery time after 7:00 pm. He had gotten an instant hard-on when he read her name and had to make his way out of the store somewhat sneakily, hiding his 'problem' behind the shopping cart. After loading them in the back of his truck, he took off.
His first delivery was to sweet Mrs. Fisher. She was an elderly lady that was the spitting image of how one would think of everyone's grandmother. He drove up in her driveway, got out and walked to her door and knocked. She came to the door and asked if she could help him. He told her that he was here with her groceries. Her smile could have brightened the darkest night. She told him how hard it was for her to get out and about and run her errands. This new grocery delivery service was a God-send. After he brought her groceries in, she paid him and gave him a nice tip. He thanked her sincerely and left. As he drove to the next drop-off, he was thinking how much more money was possible from this. He made 3 more deliveries and had to go back to the store to pick up the last order.
As he rounded up all the items on Mrs. Taylor's list, he wondered if she regretted what she had done. Maybe she was taking pity on him. Surely with her looks she could have any man she wanted. Why did she do that to him? With these thoughts running through his head, he almost missed Mr. Bailey calling his name. He told Jake to just go on home after this delivery and keep the money with him until Monday since the store was closing at 8:00 pm. As Jake drove to Judy Taylor's house, he called home on his cell and told his mom he would be working a little late tonight due to a big shipment of groceries coming in. She told him to be careful coming home later and told him goodnight. He felt guilty about lying to his mother but the possibility of what might happen made him feel it was worth it.
Jake pulled in the driveway and turned off the lights on his car. He didn't notice many lights on in the house. There seemed to be a fire in the fireplace from the flickering on the front drapes. He knocked on the door and patiently waited. She yelled "Be right there." After a few moments, the door opened and Jake couldn't believe his eyes. She was standing there in the sheerest lingerie he had ever seen. It was white and floated around her body like a covering of thin smoke. There was nothing hidden from his sight. From her dusky colored areola to the darker, protruding nipples, down to the strings of the white thong she wore, everything about her electrified him. He could feel the front of his pants getting tight as his cock swelled to its full size. She told him to come in and follow her. She led him to the kitchen and told him to put the groceries on the table. She took him by the hand and led him back into the den and over to the over-stuffed couch in front of the fireplace.