14 years ago I posted a couple of stories from my first sexual experience, which…
the apprentice – part 6
8 (tom, Mrs. Barrett, Ginny, Mr. Leslie)
Mr. Barrett, I knew, was on a long business trip, so I was surprised and excited when his wife Sandra called and asked me to come to the house. I asked her if I needed to bring any papers or other materials from the office, and she just laughed and said “this isn’t business.” I was really aroused as I drove toward their big home, taking off early from work as she had suggested. When I got there, she greeted me at the door. “Hello, Tom,” she said, “we’ve missed you. Ginny and I.” I had parked behind a car in the driveway, but I didn’t give it a thought. When I got into the living room, however, there sat Mr. Leslie. “Sir,” I said. “I didn’t know you’d be here.”
“Did you think you’d have these lovely ladies to yourself? Tom, isn’t it? I think you and I already share one friend, so what’s a couple more?” He leered at me. He was sitting in a big wing chair looking back at me, and when I walked around the front of it I saw that he was totally nude and Ginny was sucking his cock. “She’s really good at this, don’t you think?” he asked me.
Trying to be a gentleman, I said “Sir, I don’t have any way of knowing,” and he snorted with laughter. “Doesn’t he know that everyone talks in this company?” he asked Sandra, and she smiled. “Perhaps he doesn’t want to believe it,” she said. She was standing next to me, and her hand was caressing my ass through my pants. I had a huge erection, and her other hand came around to caress the front of my pants. “That’s why I like you, Tom. You’re always ready, unlike some of these old guys–present company excepted,” she added quickly before Mr. Leslie could say anything.
“You notice I’m not having any trouble,” he said, defensively. “But you’d better stop, Ginny. I might have trouble getting it up again very soon.” Ginny stopped sucking on his knob, and got up. She walked over to me and unbuckled my belt, undid my pants, and let them drop to the floor. Then she knelt down and took my cock in her mouth, sucking on it for a minute or two.
“Let’s go into the bedroom,” Sandra said in a thick voice.
In the bedroom, she and Ginny quickly stripped, and I finished taking off my clothes. Sandra got on the bed and invited me forward with her hands, opening her thighs invitingly. I crawled on to the bed and got between her legs to begin eating her. Suddenly Mr. Leslie was hunched over me, and he said in a low voice in my ear “I wasn’t included last time you were here, because I’m sort of on the outs with Jack and his crowd. But I’ve thought about it a lot, and Sandra set this up today so that I could do what they did.”
To my amazement, his words excited me, and I reached back to grasp his cock and guide it between my cheeks. “Ah, an eager victim,” he said. “There’s nothing better.” He began to press his cock into my ass, and it didn’t feel too bad; it wasn’t as big as two of the ones I’d taken on that other day. Ginny crawled around and lifted my right leg, crawling under me and taking my cock in her mouth. After that, every time Mr. Leslie pounded into my ass, I was driven forward to ram my cock deeper into Ginny’s throat.
Just then, Sandra came with a loud moan, and crawled away. I looked back to see her settling between Ginny’s thighs and dipping her face into the blonde girl’s luscious pussy. She clutched the girl’s cheeks in her hands, lifting her partway off the bed and burying her tongue deep inside.
Ginny groaned with pleasure as I came in her mouth, and she continued to suck me until my
cock had become small and shriveled. She urged me forward, and her lips closed on my balls which she licked lovingly for another couple of minutes.
With a grunt, Mr. Leslie climaxed in my ass, and I felt the hot fluid running up inside me. I now knew that that was a feeling I wanted to have over and over again, and I guess that defines what I’ve become. I’m now a boy-toy for a bunch of older men and women, who do to me whatever they feel like doing. On the other hand, I get to do to them whatever I feel like doing, so I guess we’re more or less equals. Except they all make a lot more money than I do.
Ginny came a moment later on Sandra’s tongue, and we all lay on the bed recovering. We got up and moved around the house, but no one put any clothes on; I think we were all thinking about what and who we would do next, when our stamina returned.
As it turned out, it was me who came back fastest, because I was the youngest. Ginny was sitting on the couch after we had some dinner, playing absentmindedly with Mr. Leslie’s flaccid cock. “Not much hope there, Ginny. I guess you’ll have to make do with my tongue,” he said.
“That would be all right,” she smiled. I was sitting next to them, and just the conversation caused my tool to reinvigorate most of the way. “Ah, to be young. Look at that, it’s getting really big,” said Mr. Leslie. “Ginny, could you wait a few minutes for me to take care of something else?”
Her eyes sparkled as she caught his meaning. “As long as I can watch,” she said.
“Tom, I want to suck you off. May I?” I sat half-dazed, but I nodded, and his hand immediately circled my nearly-erect cock. He began pumping it, and it quickly swelled to fill his hand. “It’s really beautiful. I want it in my mouth,” he said softly, and leaned down to take my cock deep into his throat. He was really good at it, and I knew that it had grown to be as big as it had ever been. His hand played with my balls, brushing them lightly with his fingertips and sending a thrill through me.
Ginny climbed across him and stood up next to me on the couch. She leaned down and took my head in her hands to begin kissing me, and my hand found its way between her spreading thighs to toy with her clit and finally to thrust one finger deep inside her. Mr. Leslie continued to suck me off, putting a delicious pressure on the shaft of my cock with his lips. His tongue played over the head of my tool, and I could feel the climax coming. Sandra stood nearby, her hand sawing away in her groin, fingerfucking herself. She actually climaxed before I did, but I was only a few seconds behind her as I squirted semen into the mouth and throat of yet another man. I was really becoming sophisticated.
After Mr. Leslie finished with me, he waved me off the couch and told Ginny to lie down. Then, with his mouth and tongue still slimed with my fluid, he went down on her and tongued her to a screaming orgasm in just a couple of minutes.
On my way home that night, I ticked off the executives in the company trying to think of any that I hadn’t had sex with. None came to mind, except Mr. Walker of course. What a great company.
9 (tom, Mr. Barrett, Heather)
At work, I learned that Jack’s ‘friend’ in the steno pool was, of course, the prettiest woman there. One lunch hour, I decided to eat a sandwich at my desk to get caught up, and I watched as she went to the elevator and pushed the ‘up’ button. She got in, the door closed, and I knew she was on her way up to the executive floor. Probably for a little dick-tation, I thought, amused by my own joke. Since I had figured out who she was, I had paid attention to her and noticed her upthrust breasts and the nicest pair of hips I’d ever seen. If Jack was balling her, he was a lucky man.
Three minutes later the phone rang. “Oh, Tom, good. You’re there. This is Jack. Can you come up to my office? There’s something I need you to do.” A minute later, I was in the elevator, headed up. I went into his outer office, and there was no one there. I tapped on the door and heard him say ‘come in.’
There spreadeagled on his belly on the couch was Jack, and standing over him was the girl from the steno pool. She was totally nude, and I marveled again at her lovely hips and thighs. They were even better when th
ey weren’t covered with clothes. She had a large dildo, and she was cramming it into hi
s ass, causing him to grunt with pain and pleasure with each thrust. When she saw me, she stopped. Jack looked up and said “Tom, this is Heather. She’s the friend I told you about. She comes up and does this from time to time. And then after she’s fucked me with that thing for a few minutes, I fuck her there.
“But Heather is a needful girl, and wants to be fucked the usual way. How droll. The problem is that I always cum in her rear end, and can’t do her any good the other way. That’s where you come in. Heather, would you like Tom to fuck you?” She nodded, and smiled at me broadly.
“Get undressed, Tom, and lie down here.” I started to strip off my clothes, and Heather took the big tool out of Jack’s ass. He stood up and patted the couch to indicate to me where to sit. I sat, and then stretched out.
“Heather, please mount him,” Jack said. She crawled on top of me, and her hand found my swollen member and guided it to her pussy. I could feel how wet it was, and knew that what she had been doing to Jack had turned her on. I put the head against the lips of her slit, and she slid forward to be impaled on my eager weapon. Jack stood there a moment, looking at us with approval.
“Beautiful. Two beautiful young people doing that thing. It’s a wonderful sight. As is your lovely ass, my dear,” he said, and climbed up over her. He must have pushed it right in, because she stiffened for a moment, and when she did her pussy contracted and gave me a really nice squeeze. “Mmnnnn,” I said, “that feels good.”
“Do I please you?” she whispered. I nodded. “I’ve been thinking about this since the day you started. When Jack suggested this today, I was thrilled.”
“Knock off the chit-chat please. I need to concentrate on what I’m doing,” and he began pushing into her in earnest, each thrust driving her sheath down over my cock. She kissed me on the lips, and I kissed her back; I knew that I was going to have an orgasm in just a minute, and I pumped into her with new fervor, hoping to give her the same pleasure I was about to get.
I did, causing her to cum with sobs and moans at just the moment I shot upward and bathed her womb in my juices. Jack was really fucking into her rear, and he lifted the top part of her body off my prostrate form and clutched at her breasts as he made his last few strokes. “Unh-unh- unh,” he moaned, and a triumphant look filled the girl’s eyes as her boss emptied his balls into her ass. Ah, she has the power in this pair, I thought. Heather had obviously realized that her body was a tool to get her to wherever it was she wanted to go. And I know she’ll go far.
When Jack rolled off her, she came up the couch and planted her pussy on my face. “Lick me a little, will you please?” she asked sweetly, and I put my tongue on the lips of her slit and kissed and licked her for two minutes. She jumped up and leaned over the couch to kiss my cock lying there lifeless. “Sometime when that’s come back to life, we should get together,” she said, laughing. Jack was watching admiringly.
“Tom, is there anybody in this company you haven’t had sex with?”
“Uh–Mr. Walker?” We all laughed uproariously, and I went back down to the floor I worked on. Heather came down two minutes later, and smiled as she walked down the hall to the steno room.