Punished by Mother, Sister and Wife Ch. 04

"I'm thinking he should have some little girl style panties," Mom added, "you know the kind...... with little animals or hearts on them, maybe with some frilly lace or ruffles. Use your judgment and get whatever you can find."

"See if you can get some help from one of the sales girls." Mom continued. "Just tell her they're for a larger child and she should be able to take you right to them."

"Or," Cassie said, giggling, "I could just tell her they're for my big, strong, sissy brother who's dying to be dressed up like a ten year old girl."

"Cassie, be nice." Mom scolded. "I think he's being punished enough as it is without you making it worse for him."

Then, after taking a bite, Mom put down her fork and said, "See if you can get a training bra, too. I'm sure they'll have larger chest sizes because it's an outlet. You'll probably have to find something stretchy, though....... probably a 38 inch bust size, and the cup size won't matter for a training bra."

Cassie was trying her best to contain her amusement, and Mom turned to me and explained. "I'm going to take you to the grocery store to help me with the heavy stuff and the bags, Sweetheart. But, just because I'm allowing you to be dressed for that short amount of time, it doesn't mean your punishment stops. I think wearing the little girl underwear under your clothes is a reasonable substitute for being naked. Don't you?"

My mother probably knew my heart was jumping for joy at what she was proposing. I sat there and tried to pretend like I didn't like the idea, but inside, my brain was exploding with happiness. Maybe she'd read in one of my stories about my desire to be dressed up like a little girl, I don't really know for sure, but, my cock was lurching at the thought of having the two of them put me in a training bra and cute, little girl panties.

We were half way done with breakfast when Mom asked to see my little sister's fingernails. As Cassie held her hands up, Mom reached out to feel each fingernail and looked at each one closely. "You can't have any jagged nails on your fingers when you milk your brother." Mom said. "You'll need to go trim a few of those so they're shorter and smoother."

Cassie looked at me, then looked at Mom and replied, "Well, we're only talking about putting one finger in him, aren't we?"

"Well, one might think so, Dear." Mom answered. "But we might need to use two in his bottom to get him relaxed and prepared, and your other hand has to work that sensitive area under the head of his penis called the frenulum."

"The what?" Cassie, asked.

"The frenulum." Mom said, taking a sip of her coffee. "It's a very sensitive spot filled with nerve endings on the underside of the penis. While you're massaging his prostate gland with one hand, you'll use your other hand to gently rub the frenulum. If we do it right, he shouldn't get enough stimulation to reach a pleasurable climax. And since he's wearing a condom, the only way to tell when the milking actually happens is by feeling his semen flowing through his penis. If you press your fingertips on his frenulum, you'll probably be able to feel his semen leaking out."

"No shit?" Cassie replied. "The frenulum, huh?"

"Cassie! Please watch your language." Mom said. "I'm not one of potty mouth college friends."

I sat there in silence as I listened to my mother explain all about the milking. She had been a nurse for a long time, but, I had no idea she knew so much about how to milk a man's penis. I was certainly learning as much about her and she was about me.

When Cassie's plate was almost empty, Mom told her to hurry up and finish and then run upstairs to trim her nails. "I want to try to get this milking out of the way soon so you can go get your brother's underwear."

"Oh yeah. The little girl underwear." Cassie replied, smiling and teasing me. "How could I forget that....... a cute little training bra and ruffly panties. That's gonna look so cute."

When Cassie stood up from the table, there was a definite crease and wet spot on the crotch of her panties. She saw me looking and she paused for a minute as she smiled down at me. She took her time picking up her plate and coffee cup, and I continued looking at her panties as she stood there. After a few seconds, Mom told her to quit showing off and get going. Giggling as she left, Cassie took her dishes to the sink and then trotted up the stairs to trim her nails.

"You can't keep from looking at her in those panties, can you?" Mom asked, looking at me. "We intentionally dressed like this so we could keep you aroused and erect, so..... look all you want, Sweetheart."

I looked down at my crotch and told her it was working. Mom chuckled a bit and asked me to stand up, and when I did, she reached out and bent my straining hard-on down and looked at it closely.

"I knew you'd probably be leaking by now." Mom said, smiling up at me. "See?"

Of course, I wouldn't have felt it happening, but she was obviously right. There was already fluid pooling in the tip of the condom, and as she toyed with it with her fingertips of one hand, her other hand went between my legs and she cradled my balls gently in the palm of her hand.

"They're heavy." She whispered. "The milking is probably going to be unbearably agonizing for you, Sweetheart. It's not going to feel like a normal ejaculation. You probably won't even feel it happening."

"I figured that part out already." I replied.

"Just remember what I said." Mom reminded me. "If you're good and play along with us, there will be a treat in store for you after it's over. Your sister thinks I'm punishing you for writing those stories about us, peeking at us and taking our panties. We'll just let her go on thinking that and I'll make it up to you later, I promise."

I smiled when she said those words. I wasn't sure what the 'treat' was going to be, but, it sounded like something I was going to enjoy, and after spending a day naked with the two of them, I was probably going to need it in the worst way.

Mom was still sitting, but, she swung her legs around to face me, wrapping her hand around my cock and dropping her other hand down inside her panties. "You have such a lovely penis, Sweetheart." Mom whispered, as she pulled me closer. "It's been so long since I held one in my hand.... since before the divorce."

Mother's head tilted down and the next thing I knew, she was sucking on my condom covered cock right in the middle of the kitchen. She was actually sucking me – holding me tight and taking me into her mouth and sucking around the head of my cock. I was shocked, to say the least. I suppose I understood why she came into my room this morning and asked me to jack off for her, and she clearly explained why she let me see her pussy, but I wasn't sure why she was sucking me, and you know – it didn't matter. What she was doing felt wonderful and it was the third time already today I wondered what sex with my mother would be like.

My sister was just a tease, I knew that. She always had been popular and had boys chasing after her. Cassie was good eye candy, she had a good body to jerk off to, and her panties were usually wet and slimy with her girl juice. But, Mom was different – she was sensual and sexy without having to try. She was sophisticated and she had some refinement and an aura around her that was genuinely attractive. On top of that, she was a former high school beauty queen, and college swim star. And in the last few hours, I'd thought about my mother more than I'd thought about my wife. For that matter, I'd thought about sex with my mother more in the last two hours than I thought about sex with my wife in the last two weeks.

Her mouth was still lightly sucking, kissing and licking its way up and down the length of my cock as I looked down at what she was doing. When she peered up and saw me watching her, she pulled off my cock and flicked her hair behind her shoulders and smiled.

"You're not going to have some kind of emotional problem, or be scarred for life if I have a little fun with you later, are you?" Mom asked me. "If so, tell me now."

"Absolutely not." I whispered. "You should read my story, 'My Lovely Mother' and you'll know the answer to that question."

"I'm intrigued," Mom answered, as she tugged on my package for a few seconds. "I'll have to do that tonight."

We heard the sound of Cassie's footsteps on the stairs. Mother immediately pulled away from me, and I turned and walked to the sink to hide my wet, slobbery cock. When Cassie bounded in, she walked right up to Mom and held her hands out, asking if her fingernails were okay now. When mother said they were fine, Cassie giggled and began chanting in a childlike voice.

"Time for the milking! Tommy's getting milked now! Fingers up the butt time!" Cassie sung her little rhyme three or four times in a row before Mom stood up.

"Cassie!" Mom exclaimed. I turned from the sink and watched as Mom took a step toward Cassie and shook her finger at my little sister.

"Cassie, enough is enough!" Mom said sternly. "Your brother is being punished and what he's going through is not expressly for your personal amusement and entertainment."

"I don't mind you taking some enjoyment from his predicament because I think you deserve some payback for all the things he's done," mother added, "but, if you don't cool it with your snippy comments and start showing some maturity and at least a hint of compassion for your brother's situation, I can think of some equally embarrassing and humiliating punishments to put you through in front of your brother."

"Like what?" I interrupted, with a grin on my face.

"Like maybe a full female exam." Mother replied, looking right at my little sister. "Breast, pelvic and rectal. Don't forget I worked in a gynecologist's office for years."

Cassie's eyes popped open and she looked at Mom. "You wouldn't! Not in front of him!" Cassie exclaimed.

"If you keep this up, I guarantee I would." Mother replied. "So you better show some empathy for your brother's circumstances or you'll find yourself naked with your legs wide open....... and it'll be his fingers in your butt – and maybe other places, too!"

Mother sure got Cassie's attention and it was obvious my little sister got the message. I sort of felt sorry for Cassie because I knew she was just having a little fun. And, I wasn't mad or upset with her at all. Mom calmly and politely asked for Cassie to apologize to me and as I stood there waiting to see what was going to happen, Cassie walked up to me gave me a quick hug, pressing her small, bra clad chest into mine.

"I'm sorry." Cassie said with a sincere look on her face. "I know this isn't any fun for you."

"Thank you." Mom said to Cassie. "Now please, act your age from now on."

Just as she was finished speaking, the kitchen phone rang and Mom reached over to the wall to pick up the wireless handset.

"Oh! Beth...... uh, hold on a second....." Mom said into the phone as she looked in my direction. Then pointing her finger right at me, she covered the microphone on the phone with her hand and whispered "Watch him" to Cassie, and then turned and took the phone upstairs. I assume she wanted to talk to Beth alone, and that made me incredibly nervous.

"Well, let's hope Beth hasn't forgiven you so soon and wants you to come home." Cassie said as she walked up next to me and wrapped both her hands around my straining cock. "That would ruin all our plans, wouldn't it? You don't know how much I've been looking forward to learning how to milk you, Big Brother."

"Don't get me wrong." My little sister said immediately as she started to giggle. "For your sake, I hope she does forgive you. But not for a couple of days."

I gave Cassie an exasperated look and rolled my eyes. In return, she let go of my cock and then re-grasped the middle of my shaft and began tugging on me furiously.

"I read two more of your stories last night after our little play time, and I've got to say," she said, looking up into my eyes, "you've given me some great ideas of things we can do together. And, uh..... things I can do to you. So, from my point of view, I hope Beth is still mad at you, 'cause if she is, we'll at least have all day today and tonight together."

I looked down at my little sister and she had a grin on her face that stretched from side to side. All of a sudden, she stopped stroking me and stepped right up in front of me and started rubbing my hardened cock back and forth across her belly. "I like seeing you naked, Tom." She said softly. "In fact, I'd like it to continue if that's possible."

"I can't wait to see you dressed up in the bra and panties I'm going to buy for you at the store today." She whispered. "You looked so cute last night in my nightie and my panties, just wait until Mom and I dress you up later. I'll be sure to get something ultra feminine and girlish. You'll like that won't you?"

She waited for my answer, rubbing my cock across her stomach and bending it down so the tip of my cock grazed across the material of her panties. "That is what you want me to buy, right?" Cassie asked. "You don't want to miss a chance like this do you? A chance to dress up the way you've always dreamed about? A training bra just your size and some cute, pink panties with little butterflies on them?"

"What was it you said in that one story?" Cassie said, holding her finger to her chin as if she was trying to remember what I'd written.

"Oh, I remember." She said, giggling out loud. "You wanted your own training bra. Not a bra for a grown up woman that had boobs. You wanted a real training bra, with thin, soft cups..... no padding..... and one that would fit you perfectly. Something embarrassing and humiliating. Wasn't that it? "

"Pink, if I remember correctly, and matching cotton panties, too. Isn't that right?" My little sister asked as she began to stroke my cock up and down again.

"You might only get this chance once, Tom." She said with a somber tone. "If that's what you really want, you better tell me now so I'll know what to look for."

I felt the heat of my embarrassment spread from my neck to my face. "Come on." Cassie urged. "Just say it. I know that's what you want. Just tell me."

Cassie kept stroking my cock, and I was amazed at how well she could give a hand job. But hoping to change the subject, I warned her she ought to back off or I might cum.

"Then you better answer my question pretty quick, then huh?" She answered. "You know Mom won't be happy if you cum."

"Okay," I replied, "yes..... a real training bra that will fit me. One that's my size if you can find one. And, matching panties, too."

Cassie let go of my cock and giggled up at me. "Okay." My little sister answered. "I'll try to find exactly what you want, and, Tom......." she added, "it would be a huge shame if you had to leave and go back home before you had a chance for us to dress you in them."

To be continued.