Jack settled in for a round of masturbation in the bathroom. He had all his equipment: his laptop, tuned to his favorite porn, his Aunt Peggy’s bra and nightie, a pack of her Winston Red 100s, a couple of belts to tie up his man boobs so they stuck out more while he teased the nipples with his fingers or the cigarettes. Quite some fetish he’s developed. He was glad to be out of the college dorms, and happy to not have to live with his parents. Aunt Peggy was nice enough to let him live in her basement apartment. He had pretty much everything he needed, including privacy. All he needed was a girlfriend. 

He donned all his gear, and looked in the mirror. Everything was in place, so he pulled a couple of cigarettes out of the pack, put his hands under the nightie and bra, and began to stroke his nipples with them. Oh, it felt so good. He was getting worked up, put two more cigarettes in his mouth. He started the video he had found, of a gorgeous woman encouraging him to smoke. He didn’t smoke, but he loved the smell, and the taste of tobacco, and watching women smoke. He secretly watched Aunt Peggy. Suddenly, he heard a  noise behind him.

“Jack? I’ve got a problem with the car, and...Oh my god!”

Jack hurried to spit out the cigarettes and put his penis away.

“Jack! What the hell are you doing? What is all this? Is that my nightie? Jack!”

“Oh, god. I’m sorry, Aunt Peggy. Can I have a minute? I’ll be out in a minute.”

“You have a lot of explaining to do!”

He took everything off, piled his stuff in the bathroom closet, put on pants and a shirt that he had left in the bathroom, and came out. He was bright red, partly from embarrassment, partly from arousal. He couldn’t look at her. He handed her the nightie and the bra.

“Jack.” She was not yelling anymore, but still very angry. “Please tell me exactly what you were doing. I mean, I know what you were doing, but tell me why.”

“I’m sorry, Aunt Peggy. I was... well, I was masturbating.”

“Yes, I saw. That’s not what I was asking about. I want to know why you were wearing my stuff. And what’s with the cigarettes? You don’t smoke.”

“I...like cigarettes. The taste and the feel, while I’m...you know.”

“Okay. And my clothes?”

“I like to dress in women’s clothes. At least the lingerie. I don’t know why.”

“That’s also obvious. My question is why my lingerie?”

“They were available.”

“Not a good excuse, Jack. You know I have rules around here. I’m not concerned about your...interests. I’m unhappy that you didn’t ask permission. I expect you to ask to borrow stuff. I’d loan you anything, Jack. I love you and care about you. But I don’t like you sneaking around and taking stuff.” 

“I’m sorry. I won’t do it again.”

“Well, now I know why some of my clothes seem a little larger lately. You stretched them out. And are those my cigarettes?” Jack nodded. “I wondered. I thought I was smoking more and not remembering. See, Jack, you’ve got me thinking things about myself, just because you didn’t tell me.”

“What can I do to make it up to you? I’ll do whatever you say.”

“You need a lesson. Maybe several. First, I want you to get dressed and take care of my car problem. I’ll think about the rest.”

Jack sheepishly got up off the bed, and went upstairs to the garage. He tried to start the car. Nothing. It was trying to turn over but wouldn’t. He figured it was the battery. He rode his bicycle to the auto parts store, bought a new battery, and brought it home. After installing it, the car started right up. 

“Okay. The car is fine now.”

“Thank you Jack. Have a seat.” Jack sat at the dining room table.

“I’ve been thinking about things. And I’m wondering, do you think about me when you masturbate?”

Holy shit. Time to come clean. “Um, well, sometimes. Part of it is the lingerie. It has your smell on it, and so it’s hard not to think of you when I’m wearing it.”

“Oh. That makes sense. Are you attracted to older women?”

“Yeah. Always have been, since I was in junior high. That’s who I think about.”

“I see. Jack, I’m not criticizing your sexual desires. And I don’t mind if you think about me. But I value honesty over everything. Especially after your uncle…”

“I get it. I’ll tell you anything you want to know. You know I love you, Aunt Peggy.”

Peggy got a curious look in her eye. “When you say you love me, what do you mean by that?”

Jack thought for a moment. “Well, I mean like an aunt. You’ve always been my favorite aunt.”

Peggy smiled. “You like me more than Aunt Molly or Aunt Sarah?”

“Yeah. You’re cool and fun to be around. I mean, I love them both, but Aunt Molly is boring, and Aunt Sarah had a stick up her butt.” Peggy laughed.

“I shouldn’t laugh, but I think you’re right. And I’m glad I’m your favorite aunt. You’re my favorite nephew.” She reached over to hug him.

“But I get the feeling that there’s more.”

“Yeah. I think you’re so beautiful. It’s hard not to think about you, that way.”

“Oh. I’ll take that as a compliment. It’s nice to be thought of in ‘that way’ sometimes. It doesn’t happen often enough these days.”

“Why haven’t you started dating? I would think that guys would be lined up at the door to take you out. You’re really cool.”

“Thanks, sweetie. I just haven’t made myself available, I suppose. Maybe I’m not ready yet. I’m just not sure. Anyway, I have a chore for you to do.”

“What’s that? I’ll do anything.”

“I’m having my friends over this afternoon for coffee. Sue, Amy, and Carlene. I’d like you to be the entertainment.”

“What do you mean? You want me to tell jokes?”

“No. I want you to masturbate in front of them.”

“What? I can’t do that! My god, I’ve never done that in front of anyone! I’d be so embarrassed.”

“That’s partly the point of it. You need a good lesson to remember to ask me before borrowing. And, I think that you might get something out of it too.”

“What, you mean mortification?”

“No. You said you like older women. All three of my friends are single. Well, divorced. I called them, and they would love to watch you jerk off. They think it’s cute and kinky. And if you impress any of them, you might find yourself a girlfriend who suits you.”

Jack thought about this insane state of affairs. Maybe Aunt Peggy was right. There could be an upside. But could he bring himself to masturbate in public?

Jack’s debut occurred at 3 o’clock. The ladies had just finished their coffee and sweets that Peggy had supplied, and were ready for this bizarre show. Peggy stuck her head into the kitchen. 

“Are you ready? You look fantastic!” 

“I feel like an idiot.” Jack was dressed exactly as he was in the morning, and had a pack of cigarettes in his hand. The nightie only extended to just below his waist, and so his penis was easily visible. His legs were shaking. He took a deep breath, then made his entrance. 

The ladies were arrayed in a circle in the living room. Sue was on the far side. She had blonde hair and big boobs. Amy was to the left. She was a tall, slender redhead. Charlene had long, dark hair, and a beautiful smile. He had met them all before, and thought all of them were pretty. Oh, god, they were all smoking Aunt Peggy’s Winstons. The room was filled with smoke. Peggy took her place. 

“Woooo! Let’s see some action! Shake it Jack! Wow, nice outfit! Sexy!”

Jack slowly moved around the circle, taking in each one’s gaze. He was bright red, but getting aroused by their stares, the calls, and the smoke. He began to stroke his nipples. 

“Oh, yes Jack! Those nipples need a workout! How about those cigarettes? More!”

Jack slowly turned in a circle so that everyone could see. He pulled out four cigarettes. His hands shook a little. Then he stuck them all in his mouth, tobacco-end first.

“Suck those cigarettes Jack! Oh, that looks so good! Hey, Jack, give me a couple!”

He walked over and handed Sue two cigarettes. She put down the one she was smoking, and put them in her mouth, just like Jack had. He moaned. They all giggled. Jack was getting hard. He looked over at Peggy. She smiled at him approvingly. Her eyes were half closed, as if she were getting aroused too. This turned Jack’s penis into a rock.

“Jack, that cock looks delicious! Oh, my god it does! Jack, you’re making me wet!”

The ladies seemed to be having fun, and oddly, Jack was starting to as well. He loosened up, and approached Amy. She reached forward and plucked the cigarettes from his mouth with her teeth. Loose tobacco went all over the floor. Jack looked at Peggy. She shrugged and smiled. Jack figured he’d be doing some vacuuming later. He slid over to Charlene, and she took out a dollar, stuffed it into his bra, and hollered, “Yee ha!” He laughed, and moved over to Aunt Peggy. She was grinning at him. 

“Nice job, Jack. You’ve got some good moves.” He wasn’t aware that he had any. She leaned forward and kissed him on the cheek. The other ladies hooted, and yelled for kisses. He went to each one, and offered his cheek. Each one planted a kiss firmly on his lips instead. Charlene shoved her tongue into his mouth. He wasn’t going to last much longer. He went back to Sue. She grabbed him by the penis and stroked a few times. He tried to control himself, and pulled away. She laughed. Then he moved to Amy. She grasped his penis harder, and licked the tip. 

“Mmmm. Tasty.” Jack was breathing hard, and leaking semen.

Charlene spun him in her direction. She got down on her knees and took his penis into her mouth. Jack started to come. She deep throated him, and sucked up all his semen as he spurted.

“Thanks, Charlene. I didn’t want that on the carpet!” Aunt Peggy, ever practical. Laughed.

Charlene swallowed and smiled. “My pleasure.”

Jack bowed to each lady, and made his exit to applause. He went into the kitchen and toweled himself off. A few minutes later, he was joined by Aunt Peggy.

“Jack, that was great! I wasn’t sure you could pull it off.”

“Aunt Peggy, that’s a terrible pun.” She grinned.

“I think you have a few admirers. You might want to go back into the living room once you get dressed.”

Jack went downstairs, and put on some deodorant and some clothes. He headed back to the living room. Sue and Charlene were sitting on the couch with a space between them. They invited him to join them.

“Hey, when do I get to sit next to the stud?” Amy asked.

“You’ll get your turn.” Sue and Charlene began to snuggle next to him. 

By the time they left, Jack had dates lined up for Thursday, Saturday, and Tuesday. He’d never had that many dates in one week’s time in his life. At least he had a couple of days to rest. He put chairs back where they belonged, and vacuumed the living room.

“Thanks for helping me clean up, Jack. I’ve got the kitchen under control. You’ve been a good sport about being punished.”

“It turned out to be more enjoyable than I ever imagined.”

“They all like you a lot. You probably figured that out from the cock grabbing. I think they’ll like you in lots of different ways. You’re a great guy, Jack. By the way, you can keep the bra and the nightie. You’ve kind of stretched them out.”

“Thanks. I appreciate that. Well, at least I didn’t get spanked.”

“Do you like spanking?”

“I don’t know. I never spanked anyone or got spanked.”

Aunt Peggy lit a cigarette.

“Jack, I’ve been a bad girl. I think I need to be punished. Would you spank me?”

It promised to be a long evening.