Personal Assistant Pt. 04

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Tom hits bottom... or does he?
6.3k words
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Part 4 of the 4 part series

Updated 07/22/2023
Created 07/21/2023
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Tom hadn't been in Mr. Taylor's office on Monday for no more than a moment when the phone rang. Jason picked it up.

"Hello?... Why Marjorie! Thomas and I were just talking about you... Yes, he's here. Just a moment. Go ahead."

Marge's voice came over the speaker. "Mr. Taylor... Jason... I've been doing a lot of thinking about what you said at dinner here the other day, and I think I have finally made up my mind. You have to understand: other than a couple boys back in college, I've never had sex with anyone other than Tom. Since we've been married, I have never once had any thought of cheating on him. My marriage, my husband, my home have always had first priority in my life."

"I understand, Marjorie," Jason said with obvious disappointment in his voice.

"No, Jason, I don't think you do. Tommy, are you listening?"

"Yes, dear. I'm here."

"Tommy, I love you dearly. You've been very good to me, and I have never had any reason to complain, in or out of the bedroom. Jason, you a very charming and attractive man. In fact, as my father used to say you...well, you've charmed the pants off me. Jason, if you meant what you said, and Tommy, if you agree... I'd like to spend tonight with both of you. Is that asking too much of either of you?"

Jason didn't hesitate. "As I said earlier, I will be satisfied with any conditions you set."

Tom spent only a second before answering. "Marge, if it would make you happy, I will do anything. I agree, readily."

"Then I can expect both of you here for dinner at 6:30?"

Jason laughed and said, "If I can concentrate on business and avoid wrecking my car on the way over, I will be there wearing a huge grin."

"Thank you, Jason. And Tommy, thank you so very much!"

Ir's uncertain which of the three people had the hardest time staying focused that day. As the time finally arrived for dinner, Tom and Mr. Taylor pulled into the driveway at the Wilson home within 5 minutes of each other. Tom went immediately to his wife and gave her a lingering kiss, then broke off to answer the doorbell.

"Tom, now that our guest is here, go wash up for dinner."

Jason grinned, "To quote Eliza Doolittle, 'Oi washed me face and 'ands before Oi come, Oi did.'"

Marjorie laughed and said, "Then go have a seat at the table. I made pot roast, I hope you like it."

"If it's anywhere near as good as your meatloaf, I'm certain I will."

Dinner was slightly awkward, with little of the free-flowing conversation which had marked the previous two meals together, but at least the pot roast was gone and Mrs. Wilson said, "I'll just clear the table, you two boys go sit on the couch and I'll join you in a moment."

When she came to the living room later, she saw both men seated on the couch looking at her with nervous grins. She sat between them, putting her arms around both their shoulders and pulling them in closer to her. She pulled her husband's head in for a long, loving kiss, her breath slightly ragged as she opened her mouth for a deep lingering exploration of his tongue. Finally she whispered, "Tommy, will you... show Jason it's alright?"

Tom took the hint and slowly unbuttoned his wife's blouse, somewhat surprised to note that she was not wearing a bra. How could he have missed that, when her hard nipples were pressing so firmly against the fabric? He caressed her breast, then reached over and brought Taylor's hand to place it on her left breast while he himself concentrated on her right breast. Marjorie looked down, enjoying the sight of her pale pink nipples being teased by the two men, the right going into Tom's mouth while the left was being lightly -- and achingly -- caressed and circled by Jason's fingers. She pulled Jason's head in for a kiss, her breath coming to her even more quickly and raggedly..

Jason kissed Marjorie softly, touching her lips, cheek and eyelid with his lips, while gently caressing her B-cup breast with his left hand. As he pressed his lips more firmly against hers, his hand lowered to pass briefly over her firm belly, only to return to the puffy left nipple.

"I'm so glad you resisted the temptation to have your breasts augmented.," he murmured. "They are perfect just as they are."

Marjorie's only answer was a soft moan, and when Tom's hand lowered to her thigh, she stood and led both men towards the bedroom. Luckily, it was a king-size bed and could easily accommodate the three of them. She quickly slipped out of the rest of her clothing, then turned and helped Jason to undress, slapping away his hands and kissing her way down his smooth, hard torso. While her tongue explored his navel, she undid his belt and unbuttoned his trousers. She pulled back slightly to pull down his pants, but gasped when she caught sight of his erection as his briefs lowered towards the floor.

Jason lifted her up on tiptoe to kiss her, then bent and picked her up to carry her to the bed. Tom was already there, and Jason gently lay her down so he and Tom could pick up where they had left off. They pair of them proceeded to cover her body with touches, kisses and the occasional soft nibble, eliciting moans of pleasure. Marjorie ceased to have any conscious thought as she gave herself over to the extremely pleasant sensations the men were giving her. In fact, when her legs opened involuntarily, she didn't even notice that it was Tom's hand that guided Jason's steel-hard penis into her dripping cleft.

Jason's love-making was slow, relentless and intense, as he drove into her again and again. He would speed up on occasion, but always returned to the steady rhythm that brought her to two small orgasms, before finally reaching a rising crest that seemed to take forever to peak. Had the neighbors been any closer, they would surely had heard her cries as she finally reached her climax, calling out "Ohhhhh... JASON!!" in an unknowing echo of her husband's cry two nights before. Her spasms continued on and on, finally letting her catch her breath as Jason lay atop her in his own post-coital release.

When Jason finally withdrew, Marjorie turned to her husband and said, "Tom, come here. Take me." As Tom moved between her legs and began thrusting his own smaller dick into her dripping pussy, she murmured in his ear, "Tommy,,. thank you so much for this wonderful gift. He is everything I never knew I wanted. Thank you, thank you, thank you. I could never have done it without knowing you wouldn't think less of me. I love you for sharing me with him."

"I could never think less of you, my love. Your happiness is the most important thing in my life. It was wonderful seeing the way you reacted to him. I only wish I had ever been able to give you orgasms like that. It made me so excited that... I think.. I...I... I'm cummng, love!"

15 minutes later, in the afterglow of their mutual exhaustion, Jason started to get out of bed.

Marjorie asked, "Aren't you going to stay the night, Jason?"

"I would love nothing better, but if I did your neighbors might notice, and I won't damage your reputation for anything. I would dearly love to do this again... often. But from now on, perhaps it would be better for the two of you to come visit me instead. My house is much more isolated, and no-one is likely to notice who comes to visit. Good-night, Marjorie...Thomas. Please know that you have given me the most wonderful night of my life."

Tuesday started off normally. Tom entered his boss's office, was greeted with a slight smile and sent on his way. After office hours, though, when Tom had changed clothes and knelt at Mr. Taylor's chair, He was rebuffed slightly.

"Not tonight, Thomas. After the exquisite time I had at your house last night, I just can't work up the enthusiasm. I don't think I've ever been so... fulfilled."

"Yes, sir. From her remarks last night and this morning, I'd say Marge feels the same way. That reminds me, sir: she told me to ask you for your address and a time when we should come to see you."

Mr. Taylor gave an address on the outskirts of the city, in one of the 'high-rent' neighborhoods, and said he would expect to see the Wilsons there at 7PM on Friday.

"Thank you, sir. I'm sure she'll be looking forward to it all week. Are you sure I can't do anything for you tonight, sir?"

"No, Thomas, nothing."

"But sir... I still need to be... punished for my misbehavior. If you won't order me to see to your sexual needs, then would you... would you..."

"Would I what, Thomas? Speak up."

Tom took a shuddering breath and answered in a voice so small it was almost a whisper. "Would you... spank me, sir?"

"Spank you? Are you sure? You know, I won't be gentle."

"Nor should you be, sir. My actions might have hurt the company, and you, very greatly. Please, sir... will you spank me?"

"Very well. Come lie across my lap, with your head pointed to my left. Now give me your right arm... no, behind your back, so you can't squirm off my lap. Here, hold the hem of your gown so it's out of my way.

SWAT! SMACK!

"Is this what you wanted, you bad little girl?"

SMACK! SMACK! SWAT! SMACK! The next four blows came in quick succession.

"Hmm, these panties seem to be in the way. Let's pull those down and continue."

SMACK, SMACK, SMACK, SWAT, SMACK, SWAT, SWAT, SMACK, SMACK!!!!

"Ow!"

"Did you say something, sissy?"

"No, sir."

SMACK! SMACK! SMACK!

By now, Tom's butt was turning a deep shade of red, and Taylor paused to feel the heat he had produced and fondle the smooth contours of the exposed mounds.

"Now what was it I heard once? That the most sensitive part of the buttocks was just above the crease between them and the legs... is that true? Let's see."

SMACK!! The force of the blow moved Tom's body slightly to Jason's left.

"Ow!"

SMACK!!

"Ow!"

SMACK!!! SMACK!!! SMACK!!!!

"Ow, ow, OW-W-W!!"

"What's the matter, sissy? Are you going to cry?"

"No, sir"

"I think you are. In fact, I'm going to continue this spanking until you DO cry. So come on, girl... cry for me"

SMACK!! SLAP!! SMACK!! The punishment went on and on for what felt like hours (though was likely only a few minutes), and Tom yelled and involuntarily kicked his legs, but Taylor held him securely and continued the brutal assault on the defenseless backside. SLAP!! SMACK!! SMACK!!

Finally, something clicked inside Tom's head. He found himself letting go of his pride, and let the pain, the humiliation, and the deep feelings (which he refused to name, even to himself) open up the floodgates and he cried. Not tears alone, but deep, wracking sobs, pouring out without restraint. Tom cried as he had not cried since his father died in his junior year of high school... cried like the little child he had been when his dog died... cried like... like... like he would never stop.

Mr. Taylor rubbed Tom's back, soothing his hiccups and comforting him. "There, there, Thomas. Let it all out... Yes. Yes. It's over now. You've done well... let it all go."

At long last, Tom's tears stopped and he managed to get his breathing under control.

"You had better go wash and splash some cold water on your face. It would never do to let Marjorie see you with red eyes. She would wonder what had happened. Now, is that the sort of spanking you expected?"

Tom said, "Yes, sir. Thank you, sir... Sir, before I go... may I kiss your hand?"

Jason's eyes widened slightly. "What? Well, if you wish."

Tom turned slightly to his boss's right, then reached out respectfully... almost worshipfully... to the hand that had delivered his punishment. He covered the back of the hand with a whole series of kisses, then gently turned it over. He proceeded to kiss each of Jason's fingers, lingering on each one for a moment, then kissed and licked the still blazing hot palm. Finally, he held the hand to his face and let the tears -- tears of gratitude, this time -- flow again briefly.

"Thank you, sir. Thank you. I'll go now."

Wednesday and Thursday were a return to... well, not really "normal," but to the established routine. On Wednesday, the day ended with Tom kneeling by Taylor's chair and being fed his hard shaft. On Thursday, Tom had a brief spanking which prepared him nicely for the anal workout he received.

On Friday, Tom worked (legitimately) a bit late, then was sent home to get ready and to pick up his wife. When they arrived at Mr. Taylor's gate and were buzzed in, they were both impressed by the split-level house with the manicured front lawn. A 10' high wall did nothing to block the view from the street, but effectively screened the back yard and pool from view. When Jason greeted them at the door, Marge was taken at the tasteful decor, and said as much.

"I'm so glad you like it, Marjorie. Please, put your coats in the hall and join me in the dining room."

"Speaking of dining," asked Tom, "what is that fabulous smell?"

"I had the chef at Leonardo's prepare duck a l'orange and sent over here. It was just a matter of setting the table making a good presentation. I hope you enjoy it."

Dinner, which included a very nice Chardonnay, was deemed a success, and the three of them chatted over coffee for a few minutes before Jason led the way to the bedroom. Marjorie asked to use the bathroom (exclaiming over the appointments), and while she was there the two men undressed and Jason handed Tom a Robe while taking one for himself. When she returned, Jason had Tom turn down the bed while he himself helped Marjorie to slowly disrobe. When he started to kiss her, he noticed a slight hesitation on her part, and asked her about it.

"Jason... I'm very fond of you, and I love the way you're treating me. But... I've been married for 20 years, and it still feels like I'm cheating on Tom. I know he knows, and I know it's ridiculous, but I can't shake the feeling that I'm letting him down."

"Thomas, did you hear that? What are your feelings on the subject? Should I stop playing with your wife? I don't want to disrespect you in front of her."

"Oh, no sir. She seems to enjoy being with you and I wouldn't deny her the pleasure."

"Marjorie? Does that satisfy you?"

"Well... I know Tom loves me and wants the best for me... but... how can I know he really approves?"

"Thomas? What do you say to that?"

Tom thought for a moment then brought his wife to the huge bed, laid her down and proceeded to crawl between her legs and applied his mouth to her groin. He spent several minutes licking her and making her moan, then reached out to his boss and positioned him on his knees if front of her. Then, risking everything, he took Jason's member, stroked it to hardness, then licked it to provide lubrication, finally inserting it into his wife's waiting vulva.

"Does that prove it to you, dear? I want you to be happy and enjoy your time together."

Marge reached up and pulled Tom's head down to her, kissing him and whispering, "Thank you, Tommy. I love you."

What followed was an hour filled with activity that was much more... athletic than the previous session. Jason took Marjorie in several different positions, first in classic "missionary" style, then letting her ride on top, then taking her from behind. Tom meanwhile was involved, kissing his wife when possible, tweaking her nipples gently in the way he knew she liked, licking both boss and wife as their genitals joined and providing what encouragement and comforts he could.

As the trio lay panting after the explosive climax to their efforts, Tom leaned in towards his wife and asked, "Did you enjoy that? It certainly looked as though you were having fun. No guilt about having sex with him? You'd do it again?"

"I'd love to, next time we're invited."

Mr. Taylor spoke up. "Tomorrow is Saturday. There's nothing at the office that can't wait until Monday. The two of you are welcome to stay the weekend, if you'd like."

"Jason, dear... I'd love to. I'd like to try out that swimming pool in the back yard, but I didn't bring a swimsuit."

"No need for that. We have plenty of privacy, no-one can see us. We can skinny-dip, if you don't mind risking a little sunburn."

"Ooh, you tempt me. It sounds so... naughty. You do inspire me to do things I never would have dreamed I would. Still..."

"Or I can go buy you a suit, if you like."

"it isn't that, really. It's just... well, when I was younger, we had a name for women who needed two men to satisfy them. And now I'm feeling... well... am I a.. slut?"

"I take offense at anyone -- even you -- using such a term for the woman I adore! But... let me think... it's just the idea of being with two men at once that makes you feel this way?"

"I... I guess so."

"Then lets get to sleep, and in the morning I think I may have a solution."

Jason dimmed the lights, and they fell asleep. Jason and Marjorie spent most of the night cuddled together, though Marge did reach out to fondle Tom's genitals a few times during the night.

When the Wilsons awoke the next day, Jason was already dressed and ready to leave. "Help yourselves to whatever you can find for breakfast. Eggs are in the refrigerator, along with milk, cheese, and ham. Bread is in the breadbox, and ingredients for coffee and tea are in the cupboard. If you think of anything you need for tomorrow, make a list and we'll see about restocking the larder. I'll be back in about an hour. Meanwhile, treat this house as your own." With that he left to get into his car and drive off.

Marge made omelets, and by the time she and Tom had finished eating, Jason had returned with a plastic bag in hand.

"Are you two feeling refreshed? Then let's return to the bedroom and I'll show you the solution I mentioned last night."

He had them sit on the bed and proceeded with what might have been a parody of an excellent corporate presentation. "Marjorie, I did listen to what you said last night, and as I understand it, you're feeling more than a little immoral, mainly because you're sharing your body with two men at once. Is that essentially correct?"

"I wouldn't put it quite that way, but.. essentially... yes. That's correct."

"What if the situation were different? What if you were being given the choice to share a lover with another woman? Would that make you feel less like a 'shameless hussy'?"

"That's not the case, though."

"But hypothetically, would it make a difference?"

Well... I hadn't thought about it but... yes, I think it would."

"Good. Now bear with me a moment, I'll explain shortly -- do you have a large family?"

"Family? No, I was an only child. I have relatives living in Florida and Montana, but I've never met them. Why?"

"Did you ever fantasize about having a sister or female cousin you could play with?"

"When I was very little, I used to have an imaginary sister."

"And what was her name?"

"Michele. But what does that...?"

Jason opened the bag he had been carrying and revealed Tom's costume from the office. "What if Thomas would agree to play the part of Michele? Would that change your feelings?"

Tom blushed furiously, feeling his boss had come very close to betraying a secret he had sworn to keep.

"Tommy? Would you actually do that... for me?"

Tom looked at her, then looked at the floor. "If it would make you happy and help you feel good about yourself... then yes, dear. I love you."

"Thomas, why don't you go in the bathroom and change? We'll be here when you get back."

Tom did as asked, then came back to stand in front Marge and Taylor.

"Marjorie, won't you introduce us?"

"This is my... sister. Michele."

"Delighted to meet you, Michele."

"Sir."

"Go on, Marjorie..."

"Michele, this is Mr. Taylor.... I mean, Jason. My... my lover."

"Michele, Marjorie has told me almost nothing about you. Are you her older sister, or her younger sister?"

"Younger," Marge answered. "By about 2 years."

"And did you share everything with each other when you were younger?"

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