Jack was glad he had an extra day to recover from his date with Sue. She tired him out. He thought about her on Friday morning as he washed his face and brushed his teeth. Then he considered Amy. So different in so many ways, but Amy was more of a mystery. Tall, slender, with long red hair, her striking appearance seemed at odds with a reserved personality. He wondered what his date might be like. He decided to call her.

“Hi, Amy. It’s Jack.”

“Hello, Jack. It’s good to hear your voice. I’ve been anticipating our date tomorrow night.”

“Me too. I was wondering if I should bring anything?”

“No, nothing at all. Just bring your sweet smile.”

“Why thank you, Amy. You’ve already brightened my day.”

He went upstairs to see about breakfast. He wasn’t sure if Aunt Peggy was around, so he got himself a bowl of cereal and sat in the kitchen, looking out at the back yard. It was time to do some lawn mowing. After he finished eating, he got himself some coffee, then checked to see if his aunt was still in the house. Her car was in the garage. He went to her bedroom door, and began to knock, but stopped. He heard sounds inside. Crying. He knocked.

“Aunt Peggy? Are you all right?” The crying stopped. After a minute, the door opened. Peggy was still in her nightgown, her eyes red.

“Hi Jack. Come on in. I was just feeling sorry for myself. Pay no attention to an old lady who feels like nobody loves her.”

“I love you, Aunt Peggy. You know I do.”

“You’re a relative. That’s different.”

“Maybe not so different. I love you in more than one way.”

Peggy looked at him. He stood there, tall and strong, and so sweet. She smiled.

“Yes, I know. I love you too. It’s all silliness. I’ll be fine.”

“You told me we were going to be honest with each other. Tell me.”

“Okay. I just woke up missing Hal. He left six months ago. Even though he’s a rat, I still miss him.”

“I guess I understand. You haven’t replaced him in your life. You need someone.”

“Yeah. But I’ll be okay.”

“I know you will. Would you like me to hold you for a while?” She nodded.

They went over to her bed, and curled up together. They spooned, with his arms wrapped around her. Jack felt needed. Aunt Peggy seemed to be comforted by him.

After ten minutes of so, Peggy said, “Jack, would you kiss me?”

He moved around so they lay face to face. “Of course. I could kiss you all day.”

That made her smile. “You just might have to.” And she brought her lips to his.

He stroked her hair and her face gently, trying to make her feel better. She stroked him back, then began touching him elsewhere. She explored his chest, then slipped her hand down his pants, searching for his cock. He stroked her breasts. She sighed.

“Jack, could we take off our clothes? I need to feel your body next to me.”

He pulled his clothing off, and helped her off with her nightgown. Cuddling close, he kissed her deeply. “What do you need? I’ll give you anything.”

“I think it’s time you fucked me, honey. I need you inside me.” Her whisper made his cock instantly stiff. Jack got a condom, and Peggy took it, rolling it onto his erection. He reached down to stroke her pussy and discovered that she was sopping wet.

“How about if you get on top?”

Jack lay on his back, and Peggy climbed onto him, positioning his cock, then easing herself down on him. She gasped, settled a moment, then began moving up and down. Jack tried to match her movements. She was so warm inside. He ached for release into her.

He began to talk to her softy, whispering encouragement, and moaning to show his appreciation. Well, he could hardly help the moaning part.

She moved faster and faster, then suddenly stopped and held her position, tightening her muscles. She gushed, the warm liquid spilling from her. Jack felt it all over his groin. He began to have an orgasm, and arched his back, pumping semen. More than anything else he loved to please his partner, and when she came, he came.

“Oh, god Jack! That was incredible!” She stayed where she was, holding on to him. “I need more. Can you do it?”

“I’m good. I can stay hard all day for you.”

Peggy began moving again, hard and fast, holding his cock as hard as she could. She came again in a minute, bucking on top of him like a cowgirl at the rodeo. He loved it. Finally, she rolled off of him, and lay on the bed. She was dripping sweat.

“I really needed that.” She reached over and got a cigarette, lighting it.

“Are you sure you’re done?”

“What do you mean?” She looked at him. He moved closer.

“I think you need more,” he whispered into her ear, breathing in her smoke. “I think you need me to lick your dripping pussy until you come again.”

“Oh, god yes, Jack, please lick me.”

He got down between her legs, and inhaled the rich scent of their sex. Then he sampled its flavor, licking all around her labia. She twitched with pleasure, and he began massaging her.

“How would you like me to do this?”

“I like everything. Surprise me.” She gave a throaty laugh.

He pulled at her labia with his fingers, moving and stretching them gently. He ran his tongue up and down, licking her clitoris, then finally plunged his tongue into her.

“Oh, oh, oh, please, keep going, oh, oh.” 

With his face buried in her, he took a finger and explored her anus. As he touched it, it puckered. His finger wet, he slowly inserted it.

“Oh my god! Yes, yes!” And then she came again, wetness flooding from her all over his face. He lapped her up as she trembled in ecstasy. Finally, her spasms slowed, and she collapsed in a puddle on the bed.

“How did you hold onto your cigarette all that time?”

“Purely by accident. Oh, Jack, how did you learn how to do that?”

“I’m not sure I learned it. I just moved with you and did what seemed like you wanted. I guess pretty well.”

“I guess so. You should advertise.”

Jack crawled back up to face her. He kissed her long and deeply. 

“When we’re in bed together, is it okay if I don’t call you Aunt?”

She started laughing, and couldn’t stop.

He arrived at Amy’s house at the appointed hour. He wondered what she had in store for him. And why were there so many cars parked on the street? Oh, well, somebody must be having a party.

“Hi Amy. Wow, you look fantastic!” She was dressed in a tight, black top, with matching pants. It contrasted beautifully with her striking red locks.

“Thank you, Jack. I appreciate you’re saying so. Please come in.”

He walked in the door, gave her a hug, and proceeded into the living room. He’d been there once before, but it seemed different this time. A circle of chairs.

“I have something interesting planned for you. I think you’ll like it.”

She led him to the middle of the room and began unbuttoning his shirt and pulling off the rest of his clothing. He didn’t object.

“After watching your performance at your aunt’s house, I wondered if you might be into bondage and public humiliation?”

“Wow. I don’t know. I’ve never tried it.”

“Well, today’s your lucky day. I happen to enjoy being dominant, and if you put yourself in my hands for the evening, you may discover things about yourself you never knew.”

Jack was happy to go along. “I place myself in your tender care.”

“I have an outfit for you to wear. Please put it on, and then I’m going to put some restraints on you. After that, you will follow my instructions.” Jack nodded, and now mostly naked, took his pile of clothes and went into the bedroom, looking over the outfit. It was somewhat similar to his makeshift bra and nightie, but more professionally done. It was tight, with holes for his nipples to peek through. It lifted and separated, so his man boobs stuck out farther than he’d ever seen. There were silk panties, also tight, but with a hole for his cock to stick out. Once he had it in place, he came back out to the living room. Instead of just Amy, there were five other women as well, all sitting in the chairs. Very nice looking women, who smiled as he entered. They were all smoking Winstons, his favorite.

“Come here, Jack. I am going to tie your hands to your sides, so you can’t move or touch anyone. I’ll try not to cut off your circulation. If you find anything too painful, I want you to say the safe word, ‘Winston’. " Jack nodded. “You won’t be gagged for this, because we want to hear you, and use your mouth for various tasks. And from this point on, you will address me as Mistress.”

“Yes, Mistress.” The group applauded at his compliance.

“See, they like you already. You’re a good boy. During this time, you will be polite, and say please and thank you to each woman you encounter.” She tied his hands in the proper place, and slowly led him around the room to each woman. Each one did something to him, slapping his ass, pinching his nipples. One kissed him. Nothing hurt much. They were gentle. 

“Now, I want you to go to each woman, beginning here--we’re not using names--and get down on your knees in front of each one. Tell her one thing you like to have done to you. Be explicit and detailed. I’m sure you can find five things.

Jack thought for a moment, and said, “Yes, Mistress,” then kneeled before the first woman.

“I love to have my nipples stroked and played with, especially with unlit cigarettes.”

The woman reached to him and stroked his nipples, then pulled two cigarettes from her pack and rubbed them on him. He moaned. The others murmured and nodded approvingly. The woman smiled at him. “I’ll tell you what I want you to do to me after you’re done going around.” Jack thanked her, and crawled to his right, to the next woman. He was starting to get hard.

“I love to have someone stroke my cock. Long, slow strokes that don’t make me come, but keep me excited.”  She nodded, reached down, and pulled gently on his cock, one, two, three strokes.

“That’s enough for now. More later, perhaps.” Jack thanked her and went to the third woman. 

“I love putting unlit cigarettes in my mouth. I love the taste of the tobacco when I masturbate.”

The woman grinned. “I will feed you cigarettes soon, but right now, you need to be able to talk.”

Jack thanked her and crawled to the next woman. He was beginning to drip semen from his cock. He looked toward Amy, and said, “Mistress, I’m worried that I might make a mess on your carpet.”

Amy looked. “That’s very thoughtful of you, Jack, but don’t worry. Semen comes out of this carpet very easily. You may drip as needed.” A couple of the women chuckled.

“Thank you, Mistress.”

Jack was really enjoying this. More than he expected. He faced the fourth woman. 

“I love to eat pussy. I love the smell of my partner and want to breathe it in, and taste her. It gets me really excited.” The woman smiled. 

“Oh, you’ll get the chance to do that tonight.” Then she let out a hearty laugh. He thanked her and moved along to the last woman. She was older than the rest, perhaps fifty.

“I don’t think I knew this before, but I really like being on public display like this. I’m very aroused from everyone looking at me, and with anticipating what might come next.” 

She smiled at him. “It’s good to learn new things about yourself, Jack. Is there something you’d like to have done?” 

“Yes, please. I’d like you to suck on my cock, just for a moment.”

“Since you asked so politely.” She helped him stand, and sat back on the chair. Then she pulled him forward and placed him in her mouth, slowly bringing in the shaft. Her tongue swirled around the head of his cock, making him gasp. She pulled him out. 

“Not quite yet, my boy. You have some way to go before you get to come. By the way, you’re pretty tasty.” He thanked her and came back to Amy.

“Very good. You’ve caught on quickly. Now, tell me what you want from me. What you need from me.”

Jack looked at her, then sank to his knees. “Please, Mistress. I need your love and affection. I want to make love to you and give you all the pleasure you want.”

Amy looked down at him. “That’s a lovely thing to say, my dear. We might have a date another night where we can explore these desires. In the meantime, we have things for you to do here.”

She pulled him to his feet. “I’m going to have you lie down on this bean bag chair so that you are available for these ladies to do what they wish to you.”

“Yes, Mistress. Thank you.”

She nodded in response. Two of the women helped to get him into position. He was face up, and about eighteen inches off the floor. It was reasonably comfortable. Then, the first woman came over to him and kneeled next to him. She whispered into his ear, "I’m going to straddle your face so that you can lick me. While you’re doing that, I will play with your nipples."

He nodded, and said, “Oh, yes, please.”

She positioned herself over his face and lowered herself. Her knees touched the floor, and her pussy was right at his mouth. He took a deep breath and savored her aroma. Then he began to lick her. He was a bit frustrated in not being able to use his fingers but began a nice rhythm with his tongue that she responded to. As he did so, she began softly pinching and rubbing his nipples. He got rock hard.

The second woman came over and began to stroke his cock in the long, slow strokes he said he liked. His legs trembled with pleasure. She stopped short of making him come and patted his belly. “Don’t worry, I’ll be back.” 

The third woman approached and took over the task of playing with his nipples. The first woman got up and was replaced by another woman. He was starting to get confused about who was doing what, but remembered to say “Thank you,” as she left, before his voice was muffled by another pussy.

He could tell when fingers were replaced by cigarettes on his nipples. They felt different, silkier, smoother somehow. He closed his eyes as he enjoyed the multiple sensations of the new woman’s pussy. His nipples exploded with pleasure, and his cock was being stroked by...somebody. He couldn’t see, but the mystery was exciting. Soon, he was being mobbed by women taking turns straddling him, and women rubbing him in lots of places, with their hands, with cigarettes. Then someone started using her mouth on his nipple, and another on the other nipple. They sucked and bit gently. Finally, a woman began sucking on his cock, gently at first, then with increasing vigor. He only lasted a minute, and came in huge amounts into someone’s mouth. He let out a gasp and a roar that went into a woman’s vagina. She laughed at the sensation. Slowly, everyone stopped what they were doing, and left him lying there, spent for the moment. His tongue was tired, but managed to say, “Thank you,” although it sounded funny. The women laughed.

“Is everyone done with him?” Amy asked the group.

“Not completely. Do you have enough strength for one more pussy?”

“I’ll do my best.” She came over and straddled his face, opening her legs as wide as she could.

He licked and probed with his tongue. Her sweetness was a wonderful tonic, and gave him the strength to continue until she began to shudder with pleasure. He could feel her orgasm, as wrapped as he was in her thighs. She finally stopped and got off him.

“Thank you,” he managed.

She kissed him on the lips. “Thank you. You’ve been a good sport.”

They helped him get up to his feet, and Amy allowed him to sit in a chair, which she had draped with a towel. The women were putting panties back on, and lighting cigarettes. 

“May I ask a question, Mistress?”

“Of course, my dear.”

“Which one of the ladies swallowed my semen? I would like to especially thank her.” The older woman raised her hand, and the others applauded. 

“May I approach you?”

“Please do.”

Jack got up and walked over to her. She stood up, cigarette in hand.

“Thank you so much. That felt like heaven.” He kissed her on the cheek.

“Young man, if you’d like, we could get together next week for a date.”

“Thank you. That would make me very happy.” More applause.

“Well, I see you won over at least one of my guests. Any others?”

Two more of the women raised their hands. 

Amy announced, “Anyone who wants to spend more time with Jack can leave their number with me, and we’ll get something scheduled. Is that alright with you Jack?”

“Yes, Mistress. Thank you for all you’ve done. May I kiss you?”

“Of course, Jack. You’ve been a good boy. I’m going to put myself in the schedule for a regular date. I’ll buy you dinner.”

“Thank you, Mistress.”

“Are we done yet?” Amy asked the group.

One of the women spoke up. “Jack hasn’t had his daily dose of cigarettes yet.”

“Oh, how could we have forgotten? I have an idea. Jack, you’re going to stand here, and this woman will make sure you don’t fall over. Ladies, we’re going to feed Jack cigarettes until he has an orgasm. This time we’ll all get to watch him come. Won’t that be fun Jack?”

“Yes, please, Mistress!”

Three of the women got cigarettes out, while one held...