the apprentice

Part two-chapters 2-3

2
(tom and wendy)

Monday morning was very interesting. Ms. Gray was somewhat distant and proper with me, and I understood that we couldn’t give anyone any idea about what had gone on during the weekend.
I only saw her a couple of times during the day, and I quickly took her hint and acted cool and professional myself. After all, if I had come on like some kid, fawning and playing up to her, it might have made her decide that she had made a mistake. And that would mean no more chances at that delicious pussy.

The day passed uneventfully, and on Tuesday I was assigned to clean up the supply room with one of the interns, Wendy. We quickly divided the work, and set to it, and cleaned out a lot of overage forms and other useless stuff by noon. We went to lunch together, and then went back to the supply room to start in again. Wendy is a lovely girl of about 19, and has dynamite legs; I found myself daydreaming a little about seeing them splayed open on a bed, with her pussy inviting me to come in.

We were moving some boxes when our hands touched, and I must admit that it was a very electric experience. I looked at her face, and I could see that she had noticed it too. “Tom,” she said, “do you ever date anyone at work?”

“Well, I haven’t,” I lied. But it wasn’t technically a lie, since I hadn’t gone to the mountains on Saturday thinking of it as a date. A date is a movie, or dinner, or something. Not rolling around a mountain house fucking two beautiful women. That has to be called something else.

“But have you ever considered it?” she persisted.

“Sure. If someone’s attractive, and likes me, you bet.”

“Could we go out sometime?”

“Yes, I’d like that. How about dinner on Friday?” Notice I was keeping my weekend open, just in case. But a regular date with a girl my own age would be fun.

“That would be nice. I think we’ll hit it off–but I’d like to make sure.”

“Make sure? How?” I was perplexed.

“See if there’s any chemistry between us. We’re in here alone; will you kiss me?” She moved very close to me.

“Glad to,” I said, and took her in my arms. She melted into me, and we kissed very passionately. She held the kiss a long time, and my cock rose quickly.

“That was nice,” she said, disengaging. “And now, I’d like to see what that bulge is in your pants.” She smiled broadly.

“Wendy! You’re shocking me, and I didn’t think that was possible.”

“Tom, I’ve been here four months, and nothing has happened. And yet, I see and hear things that make me think there’s a lot of fun going on around here. Since I haven’t been invited to participate, I decided to generate something on my own. You didn’t know it, but I volunteered for this grungy cleanup assignment when I heard that you’d be in here.”

“So I interest you?” I asked, grinning.

“You couldn’t tell that from the way I kissed you? If you won’t open your pants, at least kiss my breasts.” And she stripped off her blouse and unhooked her bra. I moved over to her, and said “You interest me too.” I lowered my head to take one of her nipples in my mouth. “Ohhh,” she said softly. “That feels so good.” My hand cupped her other breast, and she stroked my hair as I sucked on her large nipple.

With her other hand, she began caressing the front of my pants, and now my erection was really bursting. “I’d still like to see that,” she whispered. “I haven’t seen very many. My education has been very limited.”

I took my mouth off her breast. “Ah, you haven’t. Well then, I should tell you that mine is the largest one in the Western hemisphere, and much sought after.” We both laughed.

“I’m sure it’s big enough for my purposes. Will you let me see it?”

I stepped back and unzipped my pants, feeling like a pervert in a park exposing himself. But she said she wanted it, and I wasn’t going to refuse such a welcome request. I pulled my cock out, and said “There. A poor thing, but mine own.”

“Ohhh,” she moaned, “It’s beautiful.” And she moved forward to grasp it in one hand, circling it firmly but lovingly, and then knelt to look at it intently. “Yes, this will definitely add to my education,” she said, and took the head of it in her mouth. She did it expertly, and I was surprised because of her youth; she sucked on it for two minutes, and then removed her mouth and began kissing it up and down its length.

Then she stood up, and began putting her bra back on. “That’s enough danger for me,” she said. “We’re lucky no one came in.”

“Around here, we wouldn’t have too much to worry about,” I said, “except maybe someone wanting to join us. Or so I’ve heard,” I added quickly.

“Have you done anything with anyone?” she asked.

“No,” I lied. “But I hear the same things you do. Wouldn’t it be funny if none of it was true and you and I just started a new tradition?” Again we both laughed.

By now she had put on her blouse and buttoned it, and I zipped up my pants. “That was really special, Wendy,” I said.

“I’m sorry I couldn’t finish it. I just got worried about someone walking in. To get some staples or something.” She giggled.

“Well,” I leered, “maybe another time.”

“Maybe Friday,” she said, and smiled. Then we went back to our work and finished cleaning up the supply room. It was fifteen minutes before my erection subsided completely.

3
(Tom, Mr. Barrett, Mrs. Barrett, and Ginny)

I watched the other people at work to see if anyone was giving me any knowing looks, since I was afraid that Ms. Gray might have told someone. Or maybe I was afraid that she hadn’t. But I knew that she had been pleased by what I’d done to her and to her friend, and I know that she wouldn’t bad-mouth me to anyone at work. No one seemed to be giving me long looks, so I have to assume that she hasn’t said anything. Probably wants to keep me for herself, I thought smugly.

On Friday, Mr. Barrett called me into his office, and complimented me highly on the work I had been doing. “I haven’t had a lot of opportunity to observe you, but people whose opinion I trust tell me that you have a real future here.” I know I was blushing, since how often does anyone get compliments like that? “Thank you, sir,” I said.

“Tom, I’d like you to come over to my house tomorrow, if you wouldn’t mind a little weekend work.” He looked at me intently; I supposed this was a test to see how much of a company man I was. I wasn’t about to disappoint him. “I’d be glad to sir. Is there anything I need to bring from the office?”

“No, everything you’ll need is right there at the house. Ten o’clock all right?” I told him that it was, and he wrote down the address. His house is in the best part of town, and once again I started dreaming of my future in eight or ten years. I was looking forward to seeing how an executive lived.

On Saturday morning, I was right on time. The house looked enormous as I walked up the steps. I had presumed that I didn’t have to wear a tie, but I had a neat sport shirt and slacks on. Mr. Barrett greeted me at the door, and said “Come on through, Tom. We’re out back at the pool.” I followed him through the sliding-glass door and out to the biggest pool I’d ever seen. It had a jacuzzi off in one corner, and the landscaping was perfect and expensive.

And speaking of perfect and expensive, one of the most beautiful women I’ve ever seen was lying on a chaise longue next to the pool. She had a violet two-piece bathing suit on, a towel around her head, and cool sunglasses. “Tom,” said Mr. Barrett, “This is my wife Sandra.” She held out her hand for me to shake. “It’s a pleasure to meet you, Mrs. Barrett,” I said.

“Please,” she said, “it’s Sandra. And at home my husband is Jack.” She smiled, and patted the longue next to her. “Sit down. What would you like to drink?”

“A rootbeer,” I said, and Jack trotted off for the house to get me one. “I’m having bloody marys,” she said, “but you’re young and probably don’t need the stimulation this early in the day.”

“No. I’m pretty stimulated most of the time, but I do drink in the evening.”

“Well then, you have something to look forward to this evening. Would you like to swim?”

“I’m sorry,” I said. “I didn’t even know you have a pool, and I didn’t bring a suit. Jack said I was here to work.”

“He did?” she asked, just as Jack came back with my soft drink. “Jack, did you tell this fine young man that he was coming here today to work?”

Jack smiled. “I didn’t specify. I did say ‘a little weekend work,’ as I recall.” She pouted. “Shame on you. I didn’t know you thought of it that way.”

“Sorry, my dear. Tom, we invited you here for a social afternoon, swimming and good times.”

“I’m sorry, too, sir. I didn’t know, and didn’t bring a suit.”

“Well, you’d never be able to use one of mine,” he said, looking jolly. “I guess you’ll just have to go in au naturel–that’s French for naked,” and he laughed.

Sandra was smiling broadly, and I was starting to realize that the things that went on in the company apparently extended to this posh place. But what did they have in mind? I looked at Sandra for several seconds, taking in the lovely body inside the bathing suit, but I also looked at Jack and decided that, if this included an old man, I was out.

“I’d be embarrassed to go in nude,” I said. I know I was blushing. “But you wouldn’t be the only one, dear boy,” Jack said. “My wife swims nude all the time, don’t you Sandra?”

“Yes, I do. When there’s someone interesting to swim with. Why don’t you strip?” Gad, was she blunt!

“Ohmygosh,” I stammered. “I can’t get undressed in front of a woman I just met.”

“Why not? I can get undressed in front of a man I just met,” and she stood up and removed her top and then snaked the bottom of her suit down her thighs. I was staring at eye-level at one of the most beautiful bushes I ever hope to see, and I gulped. “Come on, Tom. Now you, or I’ll be embarrassed.” I stood in a kind of trance and kicked off my shoes, removed my shirt and pants, and sat down to take off my socks. Then I just sat there.

“Come, come, my boy,” Jack said. “You can’t stop now.” I stood up and hooked my thumbs in my shorts, dropping them to my ankles. I was so nervous about what was happening that I didn’t have an erection, but that didn’t stop Sandra from looking longingly at my dangling cock. “Let’s get in the water,” she said.

I slipped in at the shallow end, and she stood on the edge and held out a hand for me to guide her down. When she was in the water, she moved against me, and clutched my hips. “Oh, sir, don’t let me drown,” she teased.

Her hand came around the front of my body and grasped my growing cock. She stroked it lovingly, and after a moment pronounced it “Satisfactory, Jack. It grows to a nice size. You have picked well.” He was positively beaming!

Now her other hand went between my legs to cradle my balls in the palm of her hand, as she continued to stroke me. “Lovely,” she said. “Lovely. But I need to feel your hands on me, too.”
She let go of my cock and grasped one of my hands, moving it to her breast. “Are they nice?” she asked in a little-girl voice.

“V–very nice,” I said, as her hand returned under the water and caught hold of my bursting erection.

“You don’t think I’m just an old lady?” she asked coyly.

“No . . . Sandra, I don’t.”

“How old do you think I am?” she asked coyly.

“I don’t know. Forty?”

“You sweet boy. I’m nearly fifty. Old enough to be your mother. Does that bother you?”

“It would only bother me if you were my mother,” I said, and she laughed. So did Jack. “This boy has wit,” she said. “I’m going to enjoy knowing you.” She reached around behind me and put her hand between the cheeks of my ass, inserting a finger partway into my anus. “Do that for me, will you?” she asked dreamily.

I did as she asked, putting both my hands on her ass and working my fingertips into the crack between them. She bent forward and pushed herself back against my hands, moaning softly as she put her head on my shoulder. She continued to fuck her hand into my ass, and I felt the beginning of an orgasm. “You have to stop,” I said firmly, and she did.

She hoisted herself out of the water, and sat on the edge of the pool. Then she spread her legs wide open and looked at me. “See anything you like?” she asked. I moved through the water and came up on the side of the pool with my head between her legs. “It looks good enough to eat,” I said, and plunged my face into her pussy still dripping wet from being in the water. She leaned back on her hands and threw her head back; Jack meanwhile had stripped completely and walked over to turn her head to the side and plunge his cock into her mouth. She sucked on it voraciously, while I licked and slurped between her legs. We kept at it for a couple of minutes, and then I knew she was climaxing by the amount of fluid running out of her pussy, over my lips and chin, and into the pool. Jack came a moment later, and she smiled up at him with his cum trickling out of the side of her mouth.

“Ohhhh,” she said. “That was special. You do that very well, Tom. I think
it’s time for lunch.”

I got out of the pool, and we moved toward the house, all of us still totally naked. Just then a young woman we
aring a maid’s uniform came through the sliding-glass door with a tray of food and brought it to the table just outside. I moved to cover my naked front, but Sandra laughed and said “Tom, this is Ginny. She sometimes participates in our games, and you don’t have anything she hasn’t seen before.” Ginny put down the tray and smiled at me.

The three of us sat down, and took sandwiches from the tray. There was a big pitcher of lemonade, and I poured myself a glass. I was trying my best to act as though it was an everyday occurrence for me to be cavorting around a ritzy house wearing only my skin. “So what do you think, Ginny. Is he acceptable?” Sandra asked the girl. She was a handsome blonde with a good figure, which looked even better in the standard sexy maid’s costume.

“Oh, yes ma’am. Very acceptable,” Ginny said.

“Well then, let’s see what you can do for him,” Sandra said. The girl came around the table and knelt by my chair; she reached out and began stroking my cock with both hands. I quickly became erect. “Mmnnn,” I murmured. “That really feels good.”

“Turn your chair so Ginny can get at you better,” Jack said. He looked like he was about to cry, with the lust making his eyes sparkle. I turned the chair, and the girl slipped between my
legs and brought her face over the head of my erect cock. “I’d like to suck it,” she said.

“Oh, yes, please do,” I croaked, and her head descended to take the entire length of my cock deep into her mouth and throat. She began to move her head up and down, sucking me very expertly, and I began fucking up into her mouth in perfect rhythm.

Jack got up from his chair and came around behind the girl. He got down on his hands and knees, and lifted the little skirt over her ass; then he pushed his face between her cheeks and began licking. She whimpered and twisted a little, but she didn’t miss a stroke sucking my swollen cock. One of her hands had left it, and was jammed in between her legs; she was working herself over pretty good, while Jack kept licking away in her ass. I looked over at Sandra, and she was fingering herself absently while she watched with glazed eyes at what was going on on this side of the table.

I came in the girl’s mouth, and she raised her head to smile at me, the ropy strands of my semen running from the head of my cock to the inside of her mouth. Her eyes closed as she gave herself an orgasm which made her body shudder, and Jack quit eating her rear end and got up. “Well,” he said. “This is going to be a great day.”

***

Ginny and Sandra went swimming an hour later, and Jack and I sat at the table and looked at the two women floating in the pool. I was smugly happy, realizing that I was now an insider; Jack is a big executive, and I knew that being invited to his house was a sign that I had arrived. I wondered what else was in store for me.

“Are you enjoying yourself?” Jack asked.

“Oh, yes. It’s a pleasure to be here. Ginny is a doll, and your wife is a lovely woman.”

“Well, they like you too. You weren’t here five minutes and Sandra was making woo-woo sounds about you.”

“I didn’t hear that.”

“You have to know her. She was making little mewing sounds under her breath, and I could see her eyes eating you up. I knew that she’d want to include you.”

“Why did you include me, Jack? I’m really unknown in the company, and you had no way of knowing what I was like.”

“Oh, I get reports. I have a–friend in the steno pool, and she says the girls have been talking about you since you started work. And there’s a certain woman executive who gave you a very high mark for something you did last weekend.”

“Oh? Who is that?” I was stalling for time.

“Olivia, of course. Tom, you have to understand that there have been many alliances over the years, and none of us has very many secrets from the others.”

“Ah. Well, I’m just glad to be included. All my boyish fantasies are coming true.” I smiled to let him know I was kidding.

“We all like you, Tom. You have a great future here. I wonder what your limits are.” He looked at me intently.

“I’m not sure I have any. I’ve done just about everything you can do with a woman in the last couple of years.”

“Only women?” he asked. Migod, his eyes were wet.

“Well, yeah. I don’t go both ways, if that’s what you mean.”

“That’s what I mean. It’s all right, a person either does it or he doesn’t.”

“Does–what?” I asked, and was amazed at how interested I was in the conversation.

“Sucks cock, Tom. And has his cock sucked by another man. And sodomizes and is sodomized. It’s just another aspect to a sexual life to many people.”

“I’ve never really thought about it. Too many women left to do,” I joked, trying to keep it light.

“I understand. But you should know that, now that you’re in with all of us, various men might make a pass at you. You’ll have to handle it as it happens.”

I sat staring at him. “Does that include you, Jack?” Now his eyes were really wet.

“Yes, it does,” he said softly. “I have done that sort of thing, with several men. I like sucking

cock as much as I enjoy eating pussy.”

I was surprised to notice that my cock was swelling as we talked. I moved my leg to cover the growing erection, even though the table shielded my legs and hips from view. “I guess I’ve never thought about it,” I said lamely.

“Until now? Are you thinking about it now?” He was smiling knowingly.

“It’s an interesting subject,” I said.

“And if I were to come around the table and look at your cock, what state would it be in?” he asked.

“California?” I said, and we both laughed. “It would be quite large. I like sex talk as much as anyone else does.”

“And if I were to put my mouth on it, what would you say?”

“No, I couldn’t do that. Sandra and Ginny would see, and that would be too weird.”

“Is that your only reason? Because we can go inside. I’d very much like to suck that lovely cock, Tom.” He stood up, and he had a full erection. “See what you do to me? You don’t have to do anything for me, just let me take care of you.”

“All–all right,” I decided. In for a penny, in for a pound, I guess.

“Let’s go inside.” As I stood, I saw his eyes feasting on my fully-erect cock.

We walked into the house, and he ushered me down the hall to his den. Next to the desk was a big leather couch, and he indicated I should sit down. I did, and he walked over to me and reached down to circle my cock with his hand. “It is so beautiful,” he said, and began stroking me. I sat dazed, unsure why I was doing this. Was it something I’d always wanted, but hadn’t admitted to myself? Or was I just going along because Jack is a biggie in the company and I don’t want to offend him? My thoughts were interrupted by his dropping to his knees and taking my erection into his mouth. With one hand, he held it firm, and with the other he caressed my
balls. His head went up and down on my knob in long arcs that forced most of me into his mouth on every downstroke.

I was amazed to discover how much I was enjoying it. A blowjob is a blowjob, I decided, without regard to whose mouth is doing it. I wondered if I could ever do what Jack was doing, take a man’s weapon between my lips and suck it. I don’t believe that I can, but it did feel good to have it done . . . .

I shot into Jack’s mouth, a complete orgasm which drained my cock and made my balls shrivel. He continued to suck long after I had stopped cumming, and I knew that he was swallowing every drop of my semen. I was amazed to realize that I had had an orgasm twice in two hours, and into two different mouths. It was exciting.

I looked toward the door, and turned red when I saw S
andra and Ginny standing there with their arms around each other. “That was lovely, dear,” Sandra said to Jack, who had gotten up and sat on the couch next to me. “That’s the first time Gi
nny has seen that, isn’t it my darling?” The girl nodded. “I think she’s excited, Tom. Why don’t you do something for her?”

“What would you like me to do, Ginny?” I asked.

“Go down on me,” she said, and walked over to climb up on the couch and spread her legs. I stared at her beautiful pussy, and reached out to stroke it with my fingers. Then I lowered my head and began grazing over her lower body, kissing her belly and her thighs before fixing my mouth high on her hairy mound. My tongue flicked out and touched the nub of her clit, and she moaned softly. I ate her as well as I’ve ever done anyone, and I suppose it was to prove to these two lovely women that I was really a male and not a sissy who would allow another man to suck him off. I doubted that it meant much to them, but it seemed to mean something to me.

I paused several times and withdrew my tongue from Ginny’s slit, which caused her to twitch with frustration and finally to grasp my head and hold it in place in her pussy. Her legs braced my head also, and I was sweetly trapped eating a beautiful woman. It turned out there was method to her madness, since, locked in place as I was, I couldn’t move freely when Sandra knelt on the couch behind me and pushed her face into my ass. Her tongue found my anus, and she began licking me while her hand reached under me and stroked my balls. I got half an erection, despite having just come ten minutes before; I had never had that done for me, and it felt wonderful to feel her tongue probing in such a private place.

Ginny pumped into my face and mouth until she climaxed, and she continued to hold me in place until I had licked her pussy clean. Then Sandra sat up, and so did I; Jack was sitting at the far end of the couch, beaming his approval for the show we had just put on. “Sandra,” he said, “I think we should adopt Tom, don’t you?” She wiped her mouth, and nodded. Ginny chuckled from her spot on the other end of the couch, her head thrown back in ecstasy and her eyes closed.

Jack stood up and said “well, I’m going for my nap. Have fun.” And he left.

Later, Sandra and Ginny took me to the girl’s bedroom, and I got to see them eat each other. It was like having my own porno movie, but live. And with me in it as an observer. I’ve long enjoyed seeing movies of women going down on each other, but I’ve never seen a film of men doing it. Now I realized that I was curious about observing such a thing. And not in a movie.