the apprentice – part 5

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6 (tom, Ms. Gray, Marianne, Wendy)

Ms. Gray had been friendly to me for the couple of weeks since I was at her mountain house, but she hadn’t suggested anything else happen between us. One evening when several of us were working late, though, she called me into her office, a big smile on her face.

“Tom, I’m sorry to have been ignoring you, but I’ve been very busy. And so has Marianne. But we both want you to join us again.”

“I’d be happy to, Olivia,” I said. “You say when.”

“I think this Saturday, if you can tear yourself away from your other weekend activities.” I know I was blushing, since Jack had said that none of these people had any secrets from each other. “At my cabin again,” she said, and her smile was really big now.

“That would be wonderful,” I said.

“And . . . you might invite someone to join us.”

“Who?” I asked. I was genuinely mystified.

“Wendy, the intern. I’ve noticed that you and she are big on touching and making eyes around here, and I’m presuming you’ve been unfaithful to me.”

I toed the rug. “Gee, Olivia, I didn’t think that you and I–” She laughed loudly. “I’m just kidding you, Tom. I expect you to find pleasure with others, just the way I do. And I’m actually glad to hear that you don’t limit yourself to one gender. It will make your life much more interesting.”

Now I wanted to crawl under the rug. I knew that she probably knew, but now she was making it terribly clear. “And–and you don’t think that’s wrong?” I asked.

“Heavens, no, Tom. I do women, so how could I think that it’s wrong for you to do men? That would make me a . . . hypocrite.” She was laughing openly now. “Don’t be offended. I’ve been with that bunch when they do each other, and I rather enjoy seeing a man getting it in the ass.”

“I guess I’m out of my depth again,” I said, feeling stupid.

“You’re just young. And so is Wendy. And you’re both delectable. I’ve told Marianne about her, and we both want you to bring her with you. Do you think she’ll come?”

“I’ll ask her,” I said. “What–what do you plan for her?”

She laughed again. “You’ll have to wait to find out. But knowing you, you’ll like it. A lot.” And she made a motion with her hands to let me know that I was excused. “Ten o’clock at the cabin, Tom. And bring refreshments. Named Wendy.” I hurried down the hall hearing her laugh all the way to my cubby-hole office.


Wendy quickly agreed to go with me on Saturday, even after I made it clear to her that it was probably going to be company fun and games. In fact, that made her excited, since she had told me that, except for Mr. Leslie and me, she felt left out of such things and didn’t want to be.

I picked her up on Saturday morning, and we made the two-hour drive into the mountains. It was a gorgeous day, although Wendy only saw a little of it; she spent most of the drive down on her knees on the passenger side, first playing with my cock and then sucking on it. I told her to take it easy, since that item would be needed later in the day, but she just laughed and continued to stroke me and suck me.

Through great effort, I managed to hold back, and she finally sat up and enjoyed the scenery for the rest of the drive. We parked, went up on the porch, and found a note saying ‘enter.’ We went in, an found Ms. Gray sitting in the living room looking very delectable in a shorty robe. Wendy suddenly became rather shy, and Ms. Gray indicated that she should come and sit down. I looked around the room and asked “Where’s Marianne?”

Ms. Gray said, “She’s in the back. You’ll see her in a few minutes. Wendy, I’m glad you could join us. I hope you know what sort of things the people in this company do, although I’ve never seen you at any of our . . . functions.”

“I’ve never been invited, Ms. Gray,” Wendy said.

“Well, that’s obviously been an oversight. You’re a very attractive young lady. I know that Tom has found that out to his enjoyment. And Mr. Leslie.”

Wendy looked mildly unhappy. Ms. Gray quickly said “Oh, don’t think for a minute that Tom or Mr. Leslie has said anything. I am very interested in what goes on in the office–and out of it– and I’ve just been observing. I can tell that you and Tom like each other, and your body language has told me that you and he have been something more than friends.”

Now Wendy looked less unhappy, and brightened up. “I’ll never tell,” she said, and smiled.

“That’s good to know. It would be good to know you feel the same way about today.”

“Whatever happens, I don’t intend to talk about it. Except with you and Tom, perhaps.”

“Good. You are in for a pleasurable day, as long as you have an open mind.”

“It’s pretty open. What am I expected to do?”

“Just participate. With Tom. And with my friend Marianne. And with me.” She looked as though she would eat the girl up. Wendy sat for a moment and looked at her. “If I understand what you’re getting at, you should know that I’ve never done anything . . . with women.”

“That’s understood. Are you against trying something new?”

“Like what?” Wendy asked.

“Doing something with a woman. Or rather, with women. Getting pleasure from other women . . . and giving it.”

I was getting very aroused listening to this verbal foreplay going on, and hoped that Wendy wasn’t going to be upset. “I’ve suspected that people were doing things with all kinds of people,” she said. “And, as I said, I’ve felt left out. I think I’m open to new things, as long as you under- stand that I don’t really know the limits of what you’re talking about.”

“That’s fair. I’ll show you something of what I’m talking about,” she said, and stood up. She undid the sash on her robe, and shrugged it off her shoulders. She wasn’t wearing anything under it, and Wendy’s eyes got bigger as she stared at the lovely nude body of one of her bosses. “Will you take your clothes off, Wendy?” asked Ms. Gray.

Wendy nodded, and stood up. She began to undress, and I saw Ms. Gray’s eyes glittering as the luscious body of the girl became exposed. “You get undressed too, please,” she said, looking at me. We have no intention of being naked while you’re fully-dressed.” I got up and obeyed, quickly taking off everything I was wearing. Wendy now stood by the couch, looking very


“You have a beautiful body, dear,” Ms. Gray said.

“Th–thank you, Ms. Gray.” Wendy replied.

“And that’s enough of ‘Ms.Gray,’ said Ms. Gray. “My name is Olivia. Come here, dear, I want to hug you.” The girl walked reluctantly into Olivia’s open arms, and was enveloped by them. Olivia pressed her belly against Wendy’s, and her hands dropped to grasp the girl’s ass-cheeks and pull her even closer. Then she kissed the girl, long and passionately.

I could see Wendy practically melt, and it was obvious that she was returning the kiss. I stood there feeling like an idiot, my hand stroking my erection slowly. Olivia looked over at me and said, sternly, “Now you stop that! It’s the only one we have, and we can’t afford to see it wasted.” She smiled, and Wendy laughed. Olivia looked at her. “Will you let me make love to you?” she asked.

Wendy nodded, and Olivia pushed her gently onto the couch. She lifted her legs onto the cushions, and got on between Wendy’s legs. “Let me look at you,” she said simply, and Wendy complied by opening her legs completely and raising them. Olivia looked down at the girl’s eager pussy, and said “I’d like to put my mouth on you.” Wendy nodded again.

“Tom, why don’t you come over here and give Wendy something to hold onto.” I moved to the couch, and Olivia caught Wendy’s hand and guided
it to my cock. “Stroke it, dear. But not too much.” Wendy began to give me a long, slow handjob, and Olivia at that moment lowered her face into the girl’s groin and be
gan licking her pussy.

Wendy went mad. She started moaning, and bucking, and pulling Olivia’s face into her snatch. “Oh,” she said, “that is wonderful. I had no idea how much I would like it. Your tongue is so good. Eat me, oh please eat me.” And her body rocked under Olivia’s tonguing, as her hand jerked me off even harder.

I was only a moment from cumming, but Olivia had other plans. She suddenly stopped and sat up, which caused Wendy to moan “no, no, don’t stop.” Olivia reached over and disengaged Wendy’s hand from my swollen member, and said “Time for us all to go into the bedroom.”

I had really forgotten all about Marianne, which is unusual considering how lovely she is and the things we did together the last time I was here. But I’d gotten so wrapped up in watching Olivia seduce Wendy that I had forgotten that Marianne was even there. We walked down the hall to the bedroom, and there sitting in a chair was Marianne. She was nude, or apparently so; there was a blanket over her hips and legs, so I couldn’t see whether she had anything on her lower half.

“Marianne, this is Wendy,” Olivia said. “Wendy, my best friend Marianne.” Wendy smiled at the other woman, and looked around the dimly-lit room. “Glad to meet you. This is really nice.”
She looked at the big bed, and Olivia watched her.

“Why don’t you get on the bed, Wendy?” she said. And perhaps Marianne would join you. Tom, please sit where Marianne was sitting, and wait for just a few minutes. You don’t mind watching, do you?”

I grinned. “You know I don’t.” I was curious as hell to see what was going to happen, since it was obvious that the two older women had something very definite planned. It was only a moment before I saw what it was; Marianne stood up, the blanket fell away from her hips to the floor, and she was standing there wearing a dildo belt. The fake cock was at least seven inches long, and made of hard black plastic; it had a large knob at the end, and looked pretty menacing.

Wendy’s eyes got big. “What is that thing?” she said, aghast.

“That’s an object you’re going to become very familiar with today,” Olivia said. “Would you lie on your stomach please?”

Wendy was positively pale. “What are you going to do with it?”

“I’m going to put it in you,” said Marianne. “Please lie on your belly.” Olivia grasped Wendy’s arm and assisted her in turning over. She sat on the side of the bed and began stroking the girl’s shoulders and neck. “It will be all right,” she whispered. “Marianne is very good with that. I know from experience.” She took Wendy’s hand and pressed it between her thighs, and Marianne got on the bed between the girl’s legs.

Wendy was whimpering, and Olivia slid up the bed and straddled the girl’s head. “Look at mine, will you? I looked at yours.” And Wendy peered at the widening pussy of our boss there in the dim bedroom, as Marianne put the dildo against the girl’s wet pussy and shoved about four inches of it in. “Ahhhh,” Wendy moaned, and then got very quiet as she apparently realized that the big thing felt all right. “Ahhhh,” she said again, sounding pleased, and then “Mmmm,” as Marianne began stroking into her.

“Put your mouth on me, Wendy,” Olivia commanded, and the girl closed her eyes and gingerly put her tongue against the humid slit which was in front of her. After a moment, she began licking it in earnest, and her hands started playing over Olivia’s body. “Oh, that is so nice,” Olivia said, “eat me, eat me eat me, oh yes.” Wendy was really into it now, slurping away in the dripping pussy, cupping Olivia’s ass with her hands.

Just then, Marianne pulled out of Wendy’s snatch, and moved up to place the large knob against the girl’s anus. Wendy tried to move away, but Olivia held onto her shoulders, pinning her to the bed, and Marianne held her hips firmly in place. She began to work the long tool into Wendy’s
ass, rocking back and forth to give her leverage and causing the thing to go deeper into the girl’s anus with each motion. Suddenly Wendy stopped struggling, and Olivia began whispering to her. I don’t know what she said, but Wendy suddenly got up on her knees and began rocking back against the large weapon violating her backside. She was actually fucking the thing, and just then Olivia came with a little mewing sound as she flooded the girl’s mouth with her fluid.

Olivia quickly got up, and patted Wendy on the shoulder. “Tom,” she said, “why don’t you take my place here,” and I quickly got up on the bed and put my legs on either side of Wendy’s head. “Suck him off, dear,” Olivia said to her, and then moved down the bed to come in behind Marianne and plunge her face into the other woman’s ass.

Wendy raised her head and looked at me glassy-eyed. “Oh, Tom, give it to me,” she said, and I pushed my bursting erection into her mouth as far as it would go. After what I had been watching, it only took me a minute to have a wonderful climax in Wendy’s mouth. A moment later, Wendy screamed with pleasure as she came. Marianne slowly subsided in her motions, and pulled the long tool out of Wendy’s ass. Olivia quit what she was doing, and Marianne unstrapped the device and threw it aside. She lay on her back, and looked at me. “Tom, I’m the only one who hasn’t been satisfied here.”

I moved down the bed and put my mouth on her pussy. I licked and sucked her sizeable clit, and then pushed my tongue deep into the slit. She bucked and moaned, and came in a moment; I think she had been close the whole time she was fucking Wendy.

We all lay on the bed, touching each other gently here and there, saying nice things to each other. I looked at the dildo lying there, and said to Olivia, “why don’t you put that on?”

“And do what with it?” she asked.

“Use it. On me,” I said. “I want you to. And you can do it afterward,” I said to Wendy. “And you too, Marianne, if you want. Violate me. Fuck me there.” Olivia had the thing almost on already, and I got on my knees so that she could get in behind me and put the thing into my ass. She spit on the head of it and placed it at my anus, pressing first gently and then more roughly to get the thing inside me. It wasn’t warm the way the three cocks had been last week, but it was hard and she was good at using it. She fucked me for five minutes, and then stopped and took it off. She showed Wendy how to put it on, and she pushed it inside me and fucked me again. Marianne declined, but made me promise that she could do it some other time.

Later that day, I watched all three of the women eat each other in a daisy chain, while I jerked off sitting by the bed. After I came, Olivia motioned me to the bed and, as I stood there, all three of them took turns licking the semen off my shaft and the head of my cock. It was a wonderful day. When Wendy and I drove home that night, I went into her apartment with her we fucked to another orgasm. She was one of us now.

7 (tom, Ms. Thornton)

Today I was called up to Mr. Walker the big boss’ office, on the top floor. I’ve only been there once, the day I was hired, and had only seen him striding down the corridors once or twice since. I had no idea why I’d been summoned; I was only told to report to his secretary, Miss Thornton. Or Thorny as everybody called her, and not kindly. She was reported to be something of a dragon, and I hadn’t heard anyone say she had taken part in any of the extracurricular activities.

I went into the outer office in the executive suite and found it empty. I crossed it, and knocked on the big door, heard her say ‘enter,’ and walked in to the boss’ inner sanctum. She was standing by the desk, and greeted me with a smile. “So you’re Tom,” she said. She didn’t seem to be too bad a person; I looked her over carefully, and realized that there must be a dynamite body under the expensive tailored suit. Her hair was done up
on top of her head, she was wearing glasses, and she looked every inch the cliche of an executi
ve secretary. She exuded a natural air of sexuality, and I quickly decided that she didn’t participate because she was the boss’ private preserve.

When I’m the boss, I’ll have to get someone who looks as good as her, I thought. It amused me to think that it wouldn’t be her since, by the time I became the boss, she’d be in the old-folks home. “Why don’t you sit here for a moment,” indicating a chair on my side of the big desk, “and I’ll be right back.” I sat, and she went out through the door at the back of the office.

I looked around at all the stuff the boss had, and then noticed a photo album in front of me. It looked like it was there for general perusal, so I picked it up and opened it. I nearly fainted. There was Miss Thornton, her face clearly visible, sucking a whole page of cocks. I couldn’t see who any of them belonged to. I turned the page, and the first picture showed her on her back, nude, with a woman’s head between her legs. The leg nearest the camera was raised to hide the identity of the woman. The next one showed her face-down on a woman, her body disappearing on the left of the picture along with the woman’s head. The third picture on the page showed her standing, looking at the camera, wearing a harlequin mask, spike heels, and good lingerie including stockings and a garter-belt. I felt my cock getting larger.

I was about to turn the page when the door at the back of the office opened and Miss Thornton emerged, wearing exactly what she had on in the picture I was just looking at. “Did you enjoy my album, Tom?” she asked.

“Yes ma’am,” I answered. “I’m–I’m sorry if I wasn’t supposed to look.” This was silly to say, considering that she was standing there with very little on.

“Oh, you were supposed to look at it. That’s why it was right in front of you. Very few people can resist opening a photo album.” She waited a moment. “But you did enjoy looking at it?”

“Very much. I’m really a voyeur.”

“I heard that about you. From the reports that I get.” I was desperately trying to figure out what she wanted, why I was here, where the boss was, and how to hide the erection which was blessedly shielded by the desk at the moment.

“Reports?,” I asked stupidly.

“Company reports. Mr.Walker and I get regular reports from . . . friendly employees on who is doing what. It’s our form of voyeurism.”

“Where is Mr. Walker? I was told to come see him,” I said.

“No, that was just me. I sent for you. I wanted to meet you and to see if you were interested in the same things I am. From what I hear, you are.” She smiled at me broadly. I couldn’t see her eyes well because of the mask.

“I probably am,” I said. “I’m certainly interested in you, dressed that way.”

“Good. It’s just my little conceit. Why don’t you come with me over there, to the couch, and get out of those clothes.”

“But Mr.Walker? Won’t he be coming in?” I asked.

“No, he was called out of town this morning. I’m all alone here. But not now that you’re here.”

“All right.” I began undressing, and she stood by the couch watching. I looked at her near- perfect figure in the black panties and bra and the lovely stockings, and I began to swell with pride at the idea that she wanted me. It was the last thing on me capable of swelling, as anyone could see when I finally stripped off my shorts and stood there naked with my huge erection out in front of me.

“Come over here,” she said. “I’ll get out of these things in a minute, but I think every young man has fantasies of being serviced by a woman dressed like this. Do you?”

“Oh, yes ma’am. I do. I really do,” I babbled as I reached the couch. She sat on it and spread her legs so that I could step between them. Then she reached out to put one hand on my cock and pulled it toward her face. The fingers went under it to brace it in an upright position, although it hardly needed any help. Her other hand went between my legs to stroke my balls as her mouth closed on my yearning cock. I pushed into her face, and then drew back so that she wouldn’t be offended by my aggressiveness; she clutched my balls and pulled me back closer to her face. Soon my entire cock was in her mouth at the end of each stroke, and in only a minute I came in a gush which I thought would gag her.

It didn’t, though. She looked up at me and smiled, made a big deal out of gulping my semen down her throat, and then began licking the knob to get every drop off it and in her mouth. “I’m so sorry,” I said. “I didn’t mean for that to happen. I just got so excited.”

“It’s all right. I meant for you to cum. I don’t know if you know about such things, but some women get off on doing that. And I mean get off. I had a climax at the same moment you did.”
She smiled. “And now I’ve got to get out of these panties. Would you help me?”

She lay on the couch and arched her hips. I unhooked the straps on the belt from the tops of her silk stockings, and pulled the skimpy panties down and along her beautiful legs until I slipped them off over her feet. I gazed longingly at her luscious pussy, and she chuckled. “You really like to look, don’t you? What else do you like to do?”

“Almost anything. But you’ve already made it.”

“Only once,” she pouted, “I could certainly do it again with a nice tongue in me.” I moved between her legs and sank my face into her sopping slit. My tongue drove an inch into her, and she moaned with pleasure. My hands went under her ass, and I played with her anus using my thumbs. “Ohhhh, that feels good. Put your finger in my vagina,” she said. I pushed my middle finger deep into her snatch, moving my tongue up to circle her large clit and lick it. I worked her up to a climax very quickly, and she came with screams and whimpers such as I have never heard before. I found myself hoping this wasn’t my one time with her, since it was fun to give this much pleasure to another person.

I lay between her legs for a long time, licking up as much of her fluid as I could. My thumbs continued to knead her ass, and she sighed with satisfaction when I finished. “Tom, that was really good. I want you to come to my apartment soon; I’m surely not done with you yet.”

“I’d be honored,” I said. “Maybe I could get into your album.” We both laughed.

I got dressed and went back down in the elevator a few minutes later. At lunch, somebody commented on having had a call from the boss that morning, and having to go up there with some papers to give him. “What time was that?” I asked. He didn’t seem to think the question odd; “about nine,” he said.

That was twenty minutes before I got the call to go up there. So he wasn’t out of town. Where had he been? I’m really odd; rather than being upset by my thoughts, I was intrigued by them. I started imagining peep-holes and other exotic things, and so help me the idea excited me. I wondered if I would ever find out.

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