Personal Assistant Pt. 04

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"Well, I shared almost everything with her. It was sort of my duty as the older sister."

"Everything except...?"

"Boys." Marjorie blushed.

"And are you going to correct that oversight now?"

"Yes. Yes, I think it's time I told her about boys and how much fun they can be."

"Then what do you want Michele to do, Marjorie?"

"She should..."

"Don't tell me, Marjorie. Tell her."

"Michele, go over and take Jason's shirt off. Good. See how big and strong his arms are?"

Tom did so, then decided that if he was going to play the 'naive younger sister,' he would play it to the hilt. "He's kind of hairy, isn't he?"

"Yes he is, but not much. Only a little. Most boys are like that. But that's part of the fun. See how nice it is to rub your face on his chest?"

"Yeah... kind of tickles!"

"OK, now help him take off his shoes and socks... That's good. Now have him stand... and undo his belt. Good. Now unbutton his pants and pull down his zipper. That's right... now pull his pants down and help him step out of them."

"He's sort of bulgy in front."

"Let's find out why, shall we? Pull his... his shorts down to the floor."

"Wow," said 'Michele'. "What's that?"

Marjorie blushed a little at the question. "That's his... thing."

"Come now, Marjorie," said Jason. "she can't just call it a 'thing' all the time. Tell her what it is. You can say the words. It's only the three of us here."

"Well... the real name for it is a penis." Marjorie's blush deepened. "But some people... especially if they're being rude... call it a 'cock.' Sometimes a 'dick' or a 'peter' as if it was a little boy all by itself."

"That doesn't look very little. I guess it isn't a dick or a peter. It must me a cock, right sis?"

"I think you're right, Michele."

"So do all boys have cocks?"

"Yes, that's what makes them boys."

"And not girls like us, right?"

"And that is the most fun part of a boy to play with," Marjorie grinned.

"And how do you play with a cock?"

"Well, bring Jason over here, and I'll try to show you."

Tom/Michele led Jason to the bed and waited with big eyes for Marjorie to continue.

"First, you take it in your hand..."

"Like this? Ooh, it's warm!"

"Yes... and then you rub your hands all over it, gently."

"Like thi... OH! It moved! It's getting bigger and warmer! Did I hurt you, Jason?"

Jason winked at the nice bit of role-playing and said, "No, Michele. You didn't hurt me. That's just my cock's way of showing that you made it feel good."

"You're right, Margie... this is fun to play with!"

"I'll show you an even more fun way to play with it. Bring it here and put it in my... my..."

"Go ahead, Marjorie... she has to know the words. Remember, it's just us three."

"Well...you remember Mama used to call it my 'vijayjay" but that's just silly. The real name is a vagina, but when boy's think they're being sexy, they call it a 'pussy.' And if they're being mean, they call it a 'cunt.'"

"Why do people have all these names for things, Margie?"

Jason answered. "Because they think the things are nasty and you shouldn't talk about them. But sometimes it's important to talk about them, so you can tell someone what make them feel good."

"That's right, dear. And now you need to take Jason's peni... his cock and put it into my.. my pussy."

Tom started to do just that, but when the tip was right at the opening to her moist tunnel, he decided to tease them a little. "Will that big thing fit in there? It looks like it would hurt!"

Marjorie was starting to pant in anticipation, but said, "When I'm all wet and ready for him, my insides -- my pussy -- stretches and it feels so good! Now, be a good sister and help him slide in!"

Tom guided the tip of Jason's now-rigid member (which was showing some lubrication of its own) to Marge's entrance, and watched it bury itself deep in the sheath that awaited it.

The two lovers performed their dance of love for a few minutes, then Tom spoke up again. "Does that feel good, Margie? Are you having fun?"

"Ohh-h-h-h... yeessssss," Marjorie moaned.

"And do all boys have cocks that big?"

"No... **pant**... no, they don't. Jason is larger than most I've seen."

"Then bigger is better, right?"

"No...nnngh... no, I don't think so. I'm sure... ssss!,, I'm sure I could be... uhhhh... satisfied with a smaller cock. It isn't the size... oh god... the size that makes it better. It's how the boy uses it...OOOH!... uses it and does the other things that make this the most fun of anything you can do. MMMMMMmmm. And Jason is... ahh... is the... AHHHH.... the.. BEST!!!! OH GOD!! OH GOD!!! OH, JASO-O-O-ONNN!!!!"

The couple finally fell into a sweet exhaustion, exchanging kisses and endearments as the slowly got their breaths back. At last, Jason pulled back from Marjorie's limp body, and as he did, Tom moved in the lap the fluid that were seeping out of Marge's opening.

"MMMM... hah...hah... Michele? Wha...what.... what are you doing? Oh my god that feels good. But... eww, isn't that a bit... gross?"

"It looked creamy, so I thought I'd try some. It is a little strong, but it's kind of,,, I don't know... tasty? A little like oysters in some exotic sauce, and a little like thick whipping cream, and a little like... I don't know. You want to try some?"

With that, Tom sucked a big dollop of the combined juices into his mouth and brought it to Marge's lips where he passed it over during a kiss. They passed it back and forth with their tongues for awhile, then Marjorie said, "I never thought anything could be so naughty, so obscene, and so... so... delicious!"

"So," said Jason, "did the experiment work? Do you feel any guilt about what just happened?"

"No, none. At times, I forgot Tommy was even there. Sorry, dear. But you just looked so cute...especially when you were licking out my... pussy. (I still can't say that word easily, but I'm getting better at it.)"

"In that case... let me make a few phone calls while you and Thomas get... reacquainted, if you will. I'll be back shortly."

Marge pulled Tom's head down and kissed him deeply, tasting again the gift he had given her. "Tommy, thank you, thank you, THANK you for your help. I don't think I've ever gotten so much pleasure from sex. Don't misunderstand, I loved making love to you, always did. And it's a wonder Susan is an only child. But these past few days.... it's like heaven has opened its doors. And I owe it all to the wonderful sacrifice you've made for me. I just wish I could make you feel pleasure, the fulfillment, the absolute peak experience you've made possible. I only feel bad that you're being left out a bit."

"Marge, I know I've told you that I love you and that I love seeing you have that sort of climax. If I can't be on that ride with you, the next best thing -- by far -- is being able to see you enjoy it."

They were still kissing and fondling each other when Jason returned to the room. "Are you rested enough to be up for a short trip?"

"Why? What did you have in mind?"

"Well, since Michele played such a big part in the proceedings today, don't you think you ought to take her on a shopping trip? After all, she needs more clothes than just a nightgown."

"What?!?"

"I've called the airport and they're warming up the corporate jet right now. Denver is only an hour away, and there's a shop there called Transformations. Nobody in Denver is likely to know you, and the shop specializes in providing clothing for girls like Michele. I've called ahead, you're to ask for Tiffany, and she'll show you all the things Michele will need for an extended period. Michele can live here in my house, while Thomas goes home with you and to work with me. But when you come to visit, she can come out and play."

"You mean...?"

"I'll provide you with a $2,000 shopping budget, and the two of you can go wild. You can even get a swimsuit while you're at it, if you like. Does that sound like a deal?"

"Oh, Tommy, this could be so much FUN! Please say yes, please?"

"Anything you like, dear. You should know that by now."

One the return trip from Denver, Marge enthused about all the purchases they had made that day. "Michele got a nice blue skirt with a white blouse to go with it, some short heels, some flats, a very becoming sundress, a one-piece bathing suit, and a second wig. Oh, and Tiffany -- a very pretty transgender woman, by the way -- showed us some breast forms in a C-cup and bras to wear them with. She also showed us something called a gaffe... to help keep everything 'down there' stay in place while she's visiting us. She even taught Michele the basics of using makeup. Tommy, when we get back I want Michele to show Jason what she's learned. Jason, she just looks so...so CUTE, you just won't believe it!"

"So you two girls had a good time?"

"Yes, we did. Oh, and I got a cute bikini for myself as you suggested. Thank you for making it possible. And Tommy, thank you for helping. I never really had a younger sister, and you made her come to life. I realize I'm asking a lot of you, making you pretend to be a woman for me, but I really love you for it. I hope I never let you forget what it means to me."

"Your happiness and thanks are all I need, Marge."

"I'd like to spend one more night at Jason's, but when we get home I plan to make you the BEST dinner... and show my appreciation in other ways, too."

That evening, they went swimming for a half-hour or so, with Michele wearing her one-piece and Marjorie showing off her new bikini (taking off the top for the last 15 minutes). They they had a light dinner and a night filled more with cuddling than sex. Marjorie continued to explain to Michele some of the other fun things a girl could do with a man, but didn't bother to demonstrate much of anything.

Sunday morning, there was a lot of kissing, foreplay and -- eventually -- sex, highlighted for Marjorie when, during a break in the action between her and Jason, Michele decided to take an active part and knelt to lick her 'sister' a second time. Marjorie was having little orgasmic thrills when Jason asked, "May I try something? If you find it distasteful, I'll stop, but..."

"What...? Oh, yes, Michele... keep doing that, it feels wonderful! Whatever you want, Jason, I trust you, and I'm sure Michele does, too"

The 'sole male' approached Michele from behind and poured liberal amounts of lubricant over her upraised bottom, rubbing it in and spreading it between the legs of the 'younger woman.' This set up a chain reaction, with Jason rubbing, Michele twitching and moaning, and Marjorie moaning louder and grabbing Michele's head. Then, without further warning, Jason moved in closer and pushed into Michele from behind. Michele's groan of combined shock, slight pain and excitement drew Marjorie's attention, and she cried out "Oh, my god! Oh, Michele!! That just looks so... so... I don't know what else to call it but HOT! Seeing my man make love to you as you're making love to me... it's... it's... making me.... ARGHHH!!!"

Marge's spasms of sexual delight triggered Tom's own release, while Jason reached his climax at nearly the same time. It was a very happy but sexually exhausted trio that decided to end the extended visit that afternoon. "Michele" moved into her new home in Jason's closet, Tom and Marjorie rather reluctantly got into their car to drive home, and Mr. Taylor waved to them with a wistful smile on his face.

That night, Marge kept her promise and made one of Tom's favorite meals, followed by one of the most romantic/erotic nights of their married life. However, something had subtly changed in their relationship. There was nothing for Tom to really complain about. They still were good friends, sharing a bed every night (and less regularly their bodies); Tom still was a loving husband and provider: Marge was still a loving and supportive wife; but something seemed... different, somehow. Tom still went to work every day, and stayed most nights after hours, but there, too, something was not what it was. Jason asked for fewer 'services' and offered fewer spankings. Rom was still as devoted as ever, but....

Most weekends (but not every weekend) the Wilsons would visit the Taylor estate and bring out Michele to play. Michele for her part helped Marjorie to perform her first blowjob ever... and shared the resultant stream of semen. Tom couldn't pin down where or how things had changed until one weekend when Jason had to make a trip to the West Coast and invited the Wilsons to join him. It was when they drove from San Francisco to Los Angeles and stopped at the Harris Ranch Resort and Restaurant that things finally came to a head. Jason noted something a little different on the menu and ordered it as an appetizer, offer some to the other two.

Marjorie tried some, and when she then looked at them menu to see what it actually was exclaimed, "These 'mountain oysters' are... bull testicles? Really!? But they taste so good!! Why can't we get them back home?"

"Well," said Jason, "they are sort of a specialty item."

Marjorie got an evil grin on her face when she turned to Jason and said, "Maybe we could get Tom to make a donation for dinner sometime.,, they would be sort of small, though."

The two of them laughed, until Marge saw the stricken look on Tom's face. "Oh, Tommy...! That was needlessly cruel, I'm so sorry! I didn't mean to hurt you feelings like that. It was meant as a joke, but I admit it was in very poor taste. Please forgive me."

Tom said nothing, but couldn't help wondering what she would think if she knew that the pain he was experiencing was not from her casual insult, but from his realization that if she had asked... if either of the people sitting across from him had asked him seriously for that sort of sacrifice, he would have given it. With some tears and pleading, perhaps, but he would have made the cut himself to make either of them happy.

The end, when it came, left nothing for Tom to complain of. The divorce was very amicable, with Marjorie taking less than half the marriage assets and moving almost immediately onto the Taylor estate. Jason was true to his word and never told anyone of Tom's indiscretions, either financial or sexual. In fact, when Jason and Marjorie married the next year, Tom was asked to be Jason's best man, but Tom respectfully declined, thinking the irony of the title too much to bear.

With his reputation intact, Tom sold the house and, with the good references he had from Taylor/Durand found an excellent position at a company in Austin, TX. Even after repaying the 'loan' to Jason, he was able to find a very nice house in the Austin suburbs, and lived well there.

Still... Tom brooded over the realizations he had back at his old job. He had always thought of himself as a man of integrity... as a man of leadership potential...as a man of

adequate -- if not exactly exceptional -- prowess as a lover... as... a man. Now he had learned just how far from that he actually was.

Wiping away a self-indulgent tear, Tom returned his attention to the personal ad he was writing: "Lowly sissy seeks a dominant owner of any gender to show him the guidance and discipline he desperately needs. Please contact..."

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4 Comments
WailAndGnashWailAndGnash3 months ago

Haha, mattenw. I'm inclined to agree!

mattenwmattenw6 months ago

Idiotic. After John's blackmail, he has so much ammunition against him that he doesn't have to worry about reporting him. John is going to prison, that's for sure! And the divorce from his wife is also certain. So what's the point of this shit?

HeadMstrHeadMstr9 months agoAuthor

I think Tom's saga is complete. You might like "Taking and Liberating of Penelope" however. It's more of a "bodice-ripper" than hard-core porn, but still has those perverse notions we all love

mrdangerzonemrdangerzone9 months ago

Great story! You paced it really well. I loved how you wrote Tom's humiliation. I would love to see another chapter if you think the story has more potential. Would love to see Tom get humiliated in new and different ways by a new owner. Loved the financial aspect.

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