Chapter 2: Milf Jill Beds Another Young Man

Jill Ayers is sitting at her kitchen table on an early morning summer Tuesday, a stormy, rainy day, sipping coffee. She’s wearing a simple short white cotton baby doll pajama top with matching panties. As usual, she has no bra on, a side benefit of being small breasted. She is a 5’ 6”, 115 pound delight, with long brown hair and an athletic body. At 38 years old, she could easily pass for 33. Jill is separated from her husband. Her two 13 year old twin daughters are staying with Jill’s best friend, “Aunty” Janice. Her 15 year old son, Jason, is on a camping trip with his father. Jill has the house to herself this week.

Jill is startled when the doorbell rings. She wasn’t expecting anyone. Getting up from the table, she slips on a white robe which is opaque, but barely so. When she opens the door she sees Andy, one of Jason’s older friends who has often been in her house. He is 18 years old, 5’ 6”, 140 pounds. Andy has medium length brown hair with a cowlick that Jill had always thought was cute. He had been on the high school wrestling team and often came over to give Jason pointers. Andy was quiet, well-mannered and Jill had always liked him. She often tried to draw him out when he was over and she knew he enjoyed the attention.

Opening the door, Jill said, “Better get in out of the rain, Andy. What can I do for you?” She definitely noticed how his wet cut-offs and t-shirt clung to his well-defined body.

Stepping inside, Andy said, “Thank you, Mrs. Ayers. Is Jason up or is that lazy sleepyhead still in bed?” His mischievous grin just added to his cute factor in Jill’s eyes.

Jill replied, “Oh, I’m so sorry, Andy. Jason is on a camping trip with his dad and won’t be back until Sunday night. He must have forgotten to tell you. The girls are gone too. Since it’s just the two of us here, you can call me Jill. Just like pals, Andy and Jill.”

Andy slapped himself on the side of the head. “Actually, I think he did tell me and I forgot. Dummkopf, me. I came out in the rain for nothing.”

Jill laughed, with Andy, not at him, and said, “We all make mistakes. Let’s make the best of it. As long as you’re here, why don’t I make breakfast for the two of us – eggs, bacon and toast? I miss doing that for Jason. It’ll be fun.”

Andy brightened up and replied, “That’d be great, Mrs ... um, Jill. I only had a breakfast bar this morning.”

Jill smiled and said, “Excellent. Now let’s get you out of those wet clothes. Follow me.” Then she walked to her first floor bedroom with Andy in tow. Andy was happy to admire her trim legs and shapely rear. When they got to the room, Jill went into her closet and came out a few minutes later with some sweat shorts and a t-shirt, which she threw on her bed. “Here are some old things of mine which I think will fit you, Andy. Take off your shirt, shorts, socks and underwear. I think you know where the dryer is, set it for 30 minutes. While you do that, I’ll cook up breakfast. Join me when you’ve changed.” Jill left and closed the door.

Andy was amazed to be standing naked in the bedroom of a MILF, Jill’s bedroom no less. As he put on the borrowed clothes he couldn’t stop thinking about her changing clothes in this room, being nude in this room. He didn’t mind wearing a girl’s clothes for the present emergency, but Andy quickly noticed that the shorts could not hide his boner. He started to think about the ugliest, grossest guy he had seen in the school showers, which made his groin appearance manageable. He then put his things in the dryer and rejoined Jill in the kitchen.

Jill smiled to herself when Andy walked to the kitchen table because of the bulge in the sweat shorts that was betraying him. Just last week she had seduced another of Jason’s older friends, Brett, and the memory of that still excited her. Why not Andy too, she thought. “Eat hearty, Andy, and we’ll think about how to salvage this day for you.” Andy nodded and dug into the food with gusto. When he was finished, he took his plate to the sink and rinsed it. His erection had quieted down for the moment, but Jill appreciated the outline of his flaccid penis as he returned to his seat.

Jill said, “Andy, from time to time today, you’ve looked like something was bothering you. Is anything making you sad or troubled?”

Andy answered, “Gee, Mrs. Ayers, I wasn’t going to say anything, but you make it really easy to talk. Last night this girl, Debbie Burkhardt, called me and told me I’d never have a girlfriend because I kiss sucky. We sort of made out a little on Sunday. Guess I’m a late bloomer, I don’t have much experience with girls. That bugged me and I didn’t sleep well last night. Maybe that’s why I forgot about Jace’s camping trip.”

Jill’s motherly instincts kicked in on behalf of her son’s friend and she straightened up in her chair. She said, “Well, you know what I say? I say fuck Debbie Burkhardt. She’s too snooty for her own good anyway. I know she’s pretty but she’s probably just mad because you haven’t asked her to be your girlfriend. You’ll do better than her when the time comes. That’s what I say.”

Andy grinned and said, “Jill, you’re awesome. You always know how to make me feel better. Jason is so lucky to have you as his mom.”

“I’ll always have your back, Andy.” Standing up, Jill said, “Now let’s have a hug.” As Andy stood up also, she put one arm around his shoulder and her other hand on the back of his head, pulling him against her upper chest. That left her waist available for Andy to grasp. She kissed him on the top of his head. She didn’t pull his body closer the way she would have liked, knowing that he would be hard now and not wanting to scare him with physical contact that intimate this soon. It sounded to her like he was a virgin still. All the better. She knew that she needed patience to bring him along slowly on this hoped for journey. She had no doubt that he was feeling turned on. She herself was feeling warm between her legs. If Andy had grabbed her ass, Jill knew that she would have lost it and dragged him to her room and ravished him without mercy. But she also knew that such an expectation was unrealistic.

Jill broke the embrace and gently pushed Andy back to his chair as she sat back down, a little bit flushed. “You’re a good hugger, Andy, I liked that. I hope we have more hugs in the future if it’s alright with you.” Andy smiled widely and nodded in agreement. He felt relieved that the tabletop hid his large erection. Did Jill know what her touch did to him, he wondered. Jill continued, “OK, I’ve come up with a plan. How about a lunch date? Bet I’m the first girl to ask you for a date, ha! There’s a place I took Jason to not long ago. It’s a couple of towns over and it has a new arcade with some hot video games and old-fashioned pinball machines. They also have great pizza by the slice. Would you be up for keeping an old woman company on a dreary rainy day? My treat.”

Andy couldn’t believe his ears or his good luck. He knew she was joking about it being a real date, but he’d get to play games, eat pizza and spend time with a MILF. It was already a super good day just for being around her while she was semi-undressed. His buddies would be green with envy, they all thought Jill was really hot and were filled with lust for her. Every one of them had wanked off to the thought of her. Andy wasted no time in his reply, “Geez, Jill, I’ve never been asked out before by any girl. I’d love to go, it sounds like so much fun. And especially with you, you’re the prettiest girl I know, except for Mom! I only wish Jason were here to join us.” Andy, of course, was lying about the Jason part and the mom comparison but he wanted to be polite and also not fall all over himself in saying yes.

Jill smiled and said, “OK, boyfriend, call your mom and hand me the phone so I can tell her what’s going on.” Jill spoke with her friend Cheryl and filled her in, telling her that Andy’s company would help her not miss Jason so much and sort of make up for all the times Cheryl had fed Jason dinner at her house. Andy’s mom appreciated knowing who her boy was with and where he was going. Cheryl then spoke to her son again and told him to behave. Ruffling the boy’s head, Jill then said, “We’re good to go, Andy. You’re mine for the day unless you drive me crazy. Go change back into your dry clothes. Then I’ll get dressed while you finish your orange juice.” She watched Andy leave the kitchen with a little swagger in his walk and reflected upon how cute his muscular behind looked in her sweat shorts. She also idly wondered how many ways the young boy might drive her crazy today. Jill did miss her kids, but she was very satisfied that none of them would be home today.

After Andy returned Jill went to her room and put on a hot pink low cut A-line cotton sleeveless mini sundress. She also put on a light pink bra and matching nylon bikini panties. She looked sexy without being flashy. She left the dress unzipped. Returning to the kitchen she said, “Will you help me with this zipper, Andy? I can do it but it’s so much easier if someone else does it.” Turning her back to him, she knew that seeing the waistband of her panties and bra straps up close would arouse any teen boy. A very much aroused Andy put a hand on her hip and zipped the dress, taking his time doing so. He couldn’t help but wonder if she’d ask him to unzip it when they got home. The two then hopped into her sports car and left for the arcade. Because her car was a manual transmission, her already short dress tended to hike up when she shifted. She knew that Andy was watching her legs and trying not to be too obvious. She said, “I’m glad the rain is starting to fizzle out. Maybe we can put the top down when we return.” They talked about junior college and wrestling during the 20-minute drive to the arcade, Andy constantly checking out her legs “on the sly” and Jill smiling about his attempted subtlety.

When the pair got to the arcade, they walked briskly through the light drizzle to get inside. Jill’s dress was wet enough to be more clingy than usual. Good thing she had worn a bra, since she didn’t want to be flamboyant with Andy in public. First thing they did was get pizza. Jill leaned over the table several times, knowing that her “date” would get a look at the swell of her breasts under her thin pink bra. She almost felt guilty teasing him like that. But she planned to make it up to him after they got home so she didn’t feel too bad. The sense of anticipation was delicious for her. She was already a little moist between her legs. Then they went off to the video games. Jill didn’t play but stood behind Andy, sometimes placing her hands on his hips, sometimes letting a thumb sneak under the waist of his cut-off shorts. Sometimes pushing her small tits against his back. When he won, she kissed his neck to celebrate. If they hadn’t been in public, she would have wanted to reach in front of him and feel the erection she was sure he had. Then they moved on to play some two-person classic pinballs.

Finally, the two called it a day and headed home. Andy said, “Thanks a lot, Jill. That was great, I loved it. You’re a really fun date!”

“You’re welcome, Andy. You’re a lot of fun too. I’m glad that you like spending time with your buddy’s mom, a lot of guys wouldn’t. It was sort of like a date, wasn’t it? A guy and a girl get together, do fun things together, talk and eat. Trust me, I’ve had worse dates with men who should have been better. And guess what, the day’s not over yet. I have you for the day, unless you want to go home sooner.” Andy vigorously shook his head no and laughed. Jill laughed too.

When they got back to the house, Jill sent Andy to the living room while she got some soft drinks. Then she sat right next to him on the sofa, her tanned legs crossed seductively. They talked a while about their excursion to the arcade. Jill flashed a devilish smile and said, “I have another idea, Andy, now that we’re by ourselves again.”

Andy smiled back and said, “What’s up? You’ve had nothing but good ideas today.”

Jill replied, “Why don’t we practice your kissing skills? I want to prove that bitch Debbie wrong. Kissing is like anything else, you only get good at it by doing it. Besides, people who enjoy a fun date usually kiss afterwards. I won’t tell anyone you practiced with me. It’ll be our secret. What say you?”

Andy was visibly excited by this idea. Jill was making today a really fine day. He had often dreamed of kissing an older woman. He said, “I could sure use the practice. Is it OK for me to pretend you’re my girlfriend?”

Jill answered, “That’s exactly how I want you to kiss me. And I’m going to pretend you’re my steady boyfriend. Put your arm around me and make your move. But when our lips touch, let me take the lead. I’ll show you how girls want to be kissed. And how they kiss if they’re into you.”

Andy needed no further prompting. He put his arm around Jill and she put her hand on his thigh. He put his other hand on her waist and moved his mouth to hers. Jill started with quick butterfly kisses on his mouth, then switched to lingering closed mouth kissing. This continued for about five minutes. Then she opened her mouth. Andy followed her move and Jill let her tongue dart into his mouth. She did this several times before she let her tongue linger and engage with Andy’s tongue. The sensation was electric for them both. She was feeling warmer between her legs and he was rock hard. Jill pulled back and said, “OK, baby, you take the lead now. Make me hot.” He responded and took his time exploring her mouth with his own, letting his tongue slide deep inside but without gagging her. Then he boldly cupped her boob, before backing off. He said, “Oh, sorry, Jill, I got carried away. My bad.”