This is a print version of story Learning about jacking off Part Eighteen by handsomepeter47 from

Learning about jacking off Part Eighteen

I woke up in the morning with a mouth on my cock. I opened my eyes and there was Gloria slurping on me. She was naked and intent on my cock. I moved my hand to her bare ass next to me and shoved two fingers into her cunt. Her head jumped up with that and she laughed. "Careful with that stud. It's lucky I didn't bite you."

She asked if she could have a free fuck and I shrugged my shoulders in a way that meant 'sure'. She wanted to talk to me face to face so she straddled my cock and slid herself down onto it. She asked me about my gig with 'Ruby'. I told her it was fine. The client had enjoyed it and so had I.

Gloria was moving slowly up and down on my shaft, wiggling her hips a bit as she did so. Her nipples were very very hard. "Peter, I have been thinking about our relationship and the one you have with Mrs. Wilson. I have been talking to friends who have talked to friends about you. Your story, so to speak, and your skills, which are excellent! I know that for the summer you work for her during the days while your parents are at work. I am wondering if there might be a way you could be available for me on select evenings, say one or two nights a week up to maybe as much as eight or ten times a month. I know you have to deal with your parents. By the way, where did they think you were last night?"

I told her about my Mark sl**p-over thing. I did tell her I might be able to work out up to five nights a month, but my parents would become suspicious if I did anything more. She asked about weekends and I said there was a chance there, but it couldn't be all the time since my parents were home. We finally decided that I would call Gloria on a Thursday when I got home from school. She would tell me if there were clients coming up in the next week or weekend. She HAD to have a reliable way for me to service the women or the business would go bust. For the eight weeks of summer that were left it would be easier to contact her.

She was working this all out as we fucked. It was a working fuck, like a working lunch. Finally she said, "I know! Let's have it be a rare thing. I will have anonymous testimonials from women who have been fucked by you to share with the prospective clients. Of course you will have women clients that have already been with you. I will have some pictures of you for the new ones, maybe you should wear a mask for that. The Robin mask would be perfect. So, since it would be a rare thing, and the demand would, so to speak, be built up, I would offer you to women who are willing to pay a certain premium amount, let's say $700 for a night. That would be $500 for you and the rest for me. It would be a little cheaper if they had friends who came along with them. We would make more money and they would pay a little less.

I thought about it and said that sounded just fine. She laughed and clapped her hands together. She leaned forward, clamped her mouth on mine as she rode my cock like a jockey heading for the finish line. She was doing all the moving and she did have quick hips. I shot my semen up into her as her tongue and mine were working together simulating that cock/cunt action.

When we were done, we took a shower. She handed me my money for last nights assignation. I tucked the money into my pocket and she said she would take me home. I had her drop me at the same place she had dropped me before.

She waited for me to turn down the alley before she drove her car away.

I walked the block and a half to home, went in the back gate and on into the house. Once in my room I found another note pinned to my pillow. It read, "Peter, I really enjoyed myself last night. If your father asks you why you are spending so much time with Mark, he did ask ME that question, just tell him you and he are working together on jobs, mowing lawns, raking yards, watching homes while people are gone on vacation. Tell him you are making money to pay for your school clothes next year. All that will make him feel better about it. You might show him some money you have made...I think about $80 would be enough for him to know that you are working. The panties I wore last night are under your pillow. You probably don't even need that anymore, but I had to give you something personal."

I put everything in my special box and wandered over to the window. Mrs. Wilson was nowhere to be seen. I stood there for a while, then looked over at Ellen's window. She was there waving at me. I waved back. I saw her disappear from the window and minutes later she was knocking at my door.

I opened the door and she had a look on her face. Closing the door behind her I asked if something was wrong. She didn't talk for a while then asked, "Daddy says that you have been having sex with other women Peter. He says you are getting paid to fuck them. Is that right?" I was kind of glad the cat was out of the bag, because I really liked Ellen and didn't like lying to her, even if it was lies of omission. We sat on the couch and talked it through. I told her the other women weren't my idea. They were her mother's idea and that I thought it was great because I was making some money and having fun doing it. I told her I hadn't talked about that because it wasn't my business to say so. Now that Dan had done it, I didn't mind talking about it at all.

She asked how much money I made doing that. I told her. Her mouth dropped and she just stared at me. After a while she asked how many women I had fucked already. I said ten since that was the quick answer I had given Gloria. I didn't talk about Gloria though since she was an interloper. We sat in silence for a while then Ellen asked if we could fuck. I brightened at that and asked where she wanted to do that.

She thought about it for a while then said, "I want to fuck other guys Peter. I mean you are fucking other...women." It took me a little while to explain that I liked Ellen, and the women I fucked for money weren't exactly like just a job, but I didn't think I knew anyone who would pay to fuck her. I said I wouldn't know how to set that up at all. Apparently Ellen wasn't thinking about money. She was thinking about what it would be like to fuck another guy or guys. She said she had been thinking about Mark and Buddy. "Those poor boys don't know how to be around girls...isn't that what you said? Don't you think they would like to be around a girl like me who likes to fuck and is willing to help?" I thought about that a minute and knew she would be the right person to help them get over their nervousness with females. I suggested I could call one of them and ask him to come over to the house.

"I think that's a great idea Peter. Whoever you call, make sure that he knows you want him to come over for something special that he can never tell anyone else about. I don't want this all over school. I said I didn't want that either and I thought I would be able to get a promise like that from each one of them. She asked if I could call one of them now. She followed me downstairs to the hall phone. I called Mark. The phone rang a long time then finally he picked it up. "Hello, Arnold residence." His parents certainly had him well trained. I laughed and said, "Hey asshole it's Peter. What are you doing right now?" He gave me some shit back and said he was doing nothing special. I asked if he could come over to my house because I had something that was really special to talk about with him. He asked what it was, but I wouldn't tell him. I told him to come to the back door and I would be at the kitchen table. He said he would be there in fifteen minutes, then asked again what it was about. I just said, "I know you'll like fact you will LOVE it. Just get over here."

After we hung up Ellen and I talked about the best way to do this. We decided that she would stay in my room and would be naked on my bed. That was her suggestion. I would talk to Mark at the table in the kitchen about this girl I know and that she was interested in him. I would ask him if he would like to see her. I told her it wouldn't take much to get Mark charged up about this. Ellen asked again if I knew if he had ever jacked off. I was pretty sure he hadn't, but who knew. She took off her clothes. She put the shoes and socks on the floor, her panties, shorts and tee shirt on my desk. She gave me a kiss and said, "I am really excited Peter." I felt her cunt and said, "Yeah, you really are excited." That was when I heard the knock at the back door. I kissed her, then bolted out of the room, shut the door and ran downstairs.

Mark was my age. He was as tall as I was, but while I had light brown hair and blue eyes, he had dark wavy hair and brown eyes. He had a prominent nose he called his 'wop nose'. His f****y was Italian.

I opened the door and I could see that he had broken all kinds of records getting to my house by how hard he was breathing. He asked right away, "So what is it I am going to LOVE?" I got out some lemonade, poured myself a glass and asked if he wanted some. He nodded so I poured two glasses. We sat at the table.

I took a sip and then asked, "So how is your love life Mark?" He was silent for a while then said, "My love life? Don't tell me you've gone queer on me now." I laughed and said "No" and then asked if he had kissed a girl yet. I told him quickly that I had kissed a girl and done more than that. His eyebrows shot up and he asked, "What do you mean by 'done more than that.'"

I got serious then and told him that he had to promise to keep what I was about to tell him a secret between him, me...and the girl." Mark sat there quietly so I went on. "There is a girl in my room right now. I have fucked her more than a few times. She is a wonderful person and you are never to call her any bad names. You are never to tell anyone else from the neighborhood, or at school what we do with her. She goes to our school."

Mark's face was red. "'ve...fucked her? More than one time?" I nodded my head. "And she...this girl...she would let me fuck her too?" I nodded my head. "Is she pretty?" I nodded my head and then said, "You don't fuck a face Mark, you fuck a pussy." He asked if she was older than we were. I told him she was two years younger and that he probably would recognize her from school. I made him promise then to never tell anyone and to always be nice to her. I said, "She is not a slut, but she loves to fuck. I told her I thought you had not ever fucked a girl and she thought it would be nice if she let you fuck her."

Mark promised and asked in a cracked voice, "She's in your room?" I nodded my head and then said, "She is totally naked and lying on my bed." Mark's face was beet red now and he said, "Well what are we waiting for?" The next second he was saying, "I don't really know what to do." I asked him if he had ever jacked off. Mark didn't know what that meant. I told him then, "If you just do what comes naturally you will find that everything will be just perfect. Ellen is on the pill, so you don't have to worry about her getting pregnant." He nodded his head quickly. "And she is upstairs in your room? and she's naked? And she wants me to fuck her?" I smiled at all three questions and ended with a firm "Yes."

We stood up and Mark's cock was very hard. As we walked up the stairs I said that I sometimes would fuck her two or three times before we were through. He mouthed the word 'WOW'. Then he thanked me for doing this.

When we got to the room, I whispered that he should knock on the door and say it's Mark. I told him to ask if it was all right to come into the room.

He knocked lightly on the door. In a musical voice Ellen said, "Yes, who is it?" Mark croaked out, "It's Mark." He asked me in a whisper if I was going to be there while this all happened and I nodded my head.

"Please come in Mark. I am on the bed and I don't have any clothes on." The door creaked as Mark slowly opened it. I think he might have thought it was a joke on him until he saw the naked girl on my bed. She was sitting up, one foot on the bed and the other foot on the floor. The sun was shining in the room and she was beautiful. She stood up then and held her hand out to Mark as he walked closer to her. Mark tried to look at her face, but they focused on her naked slit between her legs. She shook his hand then said, "I hear you have never kissed a girl before." Mark nodded his head. She moved her naked body to him, put her arms around his neck and fortunately he moved his head down to kiss her lips. The first kiss was quick. Then they pulled away from each other and Mark licked his lips. The second kiss was obviously Mark's introduction to French culture. That kiss was epic. Ellen pressed her groin against Mark's obvious erection. Finally the two of them sat on the bed.

"Don't you think Mark it would be good if you took off your clothes?" He stood up immediately and pulled off his shirt and then unbuttoned his Levis and tried to take them off. Before he got his shoes stuck in his jeans Ellen said, "taking your shoes off first would be a good idea Mark." He thanked her, sat on the bed and removed them and then his pants. His underwear was still on. He stood up then and took them off.

I sat at my desk chair and watched the whole thing proceed.

Mark stood there in front of her, his cock hard as rock. Being Italian, he had lots of black hair around his prick. Ellen sat on the bed and said, "You have a very nice cock Mark. Would it be all right if I touched it?" He just shook his head yes and moved closer to her. Ellen's slim wrist and hand moved slowly to the throbbing member. I could almost feel her silky fingers as they slid along his shaft. Mark jerked involuntarily at the first touch, then pushed his cock forward for whatever Ellen wanted to do. She gently stroked his cock and said, "I would love to feel this cock inside of my pussy Mark. Would you like to fuck me right now?" Mark said, "Right NOW." She took my pillow and placed it where she could lay her butt on it. She lay back on the bed, her ass on the pillow and her legs spread. "You've never fucked a girl have you Mark?" He shook his head no. "You might want to go slow until you know how to move in me so you don't pop out...though that's okay too. I am ready for you Mark."

Marked went to the foot of the bed. His body was shaking, but he moved steadily forward until his cock was just inches above her slit. Ellen smiled at him and spread her lips apart. Mark's eyes burned into the open red cunt she offered him. He put his hands on either side of her hips and moved his cock so it could meet the opening she was offering. Ellen used her right hand to hold her lips apart and her left hand to guide Mark's thick cockhead into her cunt. "I am very wet Mark. Your cock will be able to slide all the way into my cunt. You can move as you wish. I have heard that boys come soon the first time they fuck. Don't worry about that because you will be ready for more. I will be ready for more too."

I watched the purple plum at the tip of his cock push into Ellen. He seemed amazed at how slippery she was and mouthed the word "Wow". She put here hands on his chest as Mark slid his cock all the way into a cunt for the first time. When he was all the way inside her he stopped. She lifted her head to his and kissed him tenderly. She whispered then, "It would be good Mark if you moved your cock in and out of me. I love the feel of your cock inside of me, but I want you to MOVE."

Mark went to town then. Soon the sounds of his cock slapping into her bare cunt was filling the room. That lasted about thirty seconds and Mark had his first orgasm. He didn't really know what was happening except that it felt really really great. He was buried in her cunt saying, "Oh Fuck! Oh Wow O Fuck." Ellen giggled and kissed him and asked, "So, now that you're not a virgin anymore Mark. How did you like it?"

Mark kissed her hard then and when he pulled away said, "Thank you so much Ellen for letting me do this." She put her hands on his bare ass and said, "I'm ready for more fucking. How about you lover boy?" He nodded his head and kissed her again. He started moving inside her again and Ellen said, "This way to fuck is nice for the first time because we can see each other's face. There is another way Peter and I fuck that I like even better. Want to try that one?"

Mark nodded his head and pulled his cock out. His shaft was coated with semen. Soon after it was out of her red slit, semen started flowing from her. I piped up then and said, "That was your semen Mark...all that white stuff. Your sperm is swimming around in there. If Ellen wasn't on the pill she would probably be pregnant right now." Mark leaned back and watched the semen flow.

Ellen got up on her hands and knees and said, "This is how dogs do it Mark. Fuck me from behind. I would like it if you touched my ass. If you want to reach around and touch my nipples that would be nice. I'm sorry I don't have much for tits right yet. Someday I think I will be almost as big as my mother."

After she was in position Ellen put her face on the pillow, reached around and spread her lips. "Fuck me Mark, Fuck me hard and Fast. FUCK ME!!"

Mark had the head in and slammed into the girl. His big balls were pounding against her hard clit. Ellen was groaning and pushing back as he pushed into her. By this time I had my cock out and was jacking off slowly as I watched them fuck. The second time lasted about twice as long as the first time. The third and fourth times seemed to have a mathematical progression to their duration depending on the order in which they came.

When it was all over Ellen asked Mark if he would like to watch Peter fuck her. He grinned and said, It's only fair."

I stood up and stripped. Ellen got up so I could lie on the bed. Without looking at Mark, she said, "This was the way Peter and I fucked the first time. if you know about the cherry or if you don't, there was a membrane inside of my pussy that had to tear when his cock pushed against it that first time when I was still a virgin. I fucked him like this so I could control my movements. Now my cunt doesn't hurt at all and I love this way to fuck too.

Mark's jizz cushioned my shaft as she moved down on me. When she pulled up, his white semen coated my cock. Ellen fucked me in a languid motion, moving her hips from side to side sometimes. I looked over at Mark and he was hard again. Ellen saw where I was looking and said, "Mark, come here please and I will suck your cock while I fuck Peter's cock." He tried to get his cock at the right level for her. She stopped us though and said, "Peter, if you fuck me doggy, Mark could sit on the pillow and I could easily suck his cock."

He did that and I had my first threesome that day in my room. Mark came over for the next three days and we fucked there. After that day, when Mark had left, Ellen asked about Buddy. I had to think about that a bit. The decision was made that I would call him for Monday.

More later.

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