Growing Up A Master - Cover

Growing Up A Master

Copyright© 2006 by MWTB

Chapter 35: A Visit to Boston

BDSM Sex Story: Chapter 35: A Visit to Boston - A coming of age story about a boy, from childhood until college, discovering his inner Master. Golden Clitoride Winner, 2006, Best BDSM Story

Caution: This BDSM Sex Story contains strong sexual content, including mt/ft   mt/Fa   ft/ft   Fa/ft   Teenagers   Consensual   Slavery   Incest   Mother   Son   BDSM   DomSub   MaleDom   Spanking   Light Bond   Humiliation   Harem   First   Oral Sex   Anal Sex   Masturbation   Sex Toys   Water Sports  

I couldn't believe that I was doing this, but it was time for me to start picking colleges. I had pretty good grades, despite all the time and energy that my extracurricular activities took, and I knew I had a pretty good chance of getting into the university of my choice. I was looking at three or four of them, but the one that I really wanted to go to was in Boston, on the east coast. It was far from home, and I wasn't quite sure how I would make the transition, but I guess that was what college was about.

I wanted to go visit the colleges that I was planning to apply to, to see what they were like up close and personal. I planned a trip to the four colleges that I wanted to look at, starting with my Boston pick. My father couldn't come with me, because he had to work, but my mother was going with me. In addition to that, it turned out that all the Harrisons would be joining me as well.

"Kari and Helen are going to go on your trip, too," Cheri had told me one night during dinner at her house.

"Why?" I asked.

"Well, Kari has applied to the same schools that you have, and Helen has applied to two of them, so it makes sense to all do the trip together," Cheri said.

I turned to Kari and asked, "You applied to the same schools? Which one do you want?"

"The one that you go to, of course!" she replied, looking at me like I had two heads.

"But..." I sputtered.

"Did you really think that you were going to be rid of me when you went off to school? I stayed here for you, and I'll have my associate's degree when I transfer, but I've worked hard to get excellent grades so that I would be sure I'd get into whatever school that you get into."

I sat back and thought for a minute. I knew that she had stayed in town for me, but I never correlated it to what would happen when I went away.

"You really are dense sometimes," Helen told me. "I could have told you last year that this was going to happen."

"But what if they don't have the major that you want?" I asked Kari.

"I'm not that set on one thing yet," she said. "I'm sure I'll find something. Don't worry about me getting in your way," Kari assured me. "I'll be available when you want me, but I won't get in your way when you don't."

I sat back and just shook my head.

"I've already spoken to Mary about this," Cheri said. "We've got the hotel rooms and airplanes booked."

I gave up to the greater forces of women, and accepted the inevitable. I didn't necessarily do it gracefully, however. For weeks I had conversation after conversation, however the end result was the same as when Kari decided not to go away to college. Finally, my father reminded me of the futility of my efforts, and I ceased trying, accepting that this would not be the worst turn of events.


I'd flown before, and I never particularly liked it when I was stuck in the middle seat. The flight to Boston, I was in the middle seat, yet I didn't mind it at all. I guess that having Cheri on my left and Kari on my right helped with that.

The little minxes had dressed to tease. Both were wearing short, loose skirts and button down shirts, but Cheri was wearing a man's shirt, while Kari was wearing a woman's, which, given that they kept quite a few buttons undone, meant that either way I looked I was able to affirmatively ascertain that neither was wearing a bra.

Both of them claimed to be nervous at takeoff, and each held one of my hands tightly to their bodies. I would have been more inclined to sympathize with their fears if they hadn't been grinding my hands to their crotches. It was a night flight, and after a quick meal, the lights were dimmed and people went to sleep. I, however, was not given the chance to sleep.

Shortly after covering themselves with blankets, my two sexy ladies grabbed my hands again, this time proving by touch that they were wearing no underwear whatsoever. I obliged their unspoken request, and soon I had two fingers of each hand well moistened. The two of them had their heads on my shoulders, quietly panting. Or so I thought.

My mother, who was in the row behind us with Helen, stood up and leaned over my seat. "Son," she said quietly, "unless you want everyone in the plane to know what you are doing, you might want to consider gagging your little sluts."

I turned to her, looking in her eyes, my hands not stopping their activities, and said, "I'd love to, but I don't really have anything to do it with."

"Use their panties," she suggested.

"I'd love to, but they seem to have left them at home. Perhaps I can use yours?"

She smiled evilly, and said, "Give me a minute."

She sat back down and I heard whispering from the row behind. I couldn't really pay too much attention, because two hands, one from either side, worked together to undo my pants, and both of them were slowly pumping my cock.

A short time later, my mother was back. "I can see that your hands our busy, so I'll just help out a little. These are for Kari," she whispered, and she turned Kari's head away from the aisle so our across the way neighbors couldn't see what she was doing before she pushed a tiny pair of panties, crotch first, into Kari's mouth.

She then moved to Cheri's sideand pushed another pair into her mouth. She whispered to Cheri, "Your daughter says that since it is your actions that got her that wet, she hopes you like her taste." Cheri's eyes opened wide, and it was a good thing that she was gagged as she groaned in orgasm. My mother reached forward and into Kari's shirt and squeezed her nipple hard, which caused Kari to follow her mother into orgasm.

"Thanks for the help, Mom," I said.

"No problem," she replied, kissing my cheek before settling back into her chair.

A few minutes later, my girls had recovered, and their hands began moving on my cock again. "While that feels amazing, I think you'd better stop. As messy as you are," I told them, pulling my hands out and licking my fingers off, "I make more of a mess."

They groaned disappointedly in stereo, but they did as I instructed. A little bit later, I got up and went to the bathroom. After relieving myself and washing my hands, I started to return to my seat, however as soon as I opened the restroom door Cheri pushed me back into the bathroom. I had picked the one bathroom on the plane with some space, in the center of the plane, so there was room for both of us. About three seconds after she locked the door, both pieces of clothing were off of her and she was down on her knees in front of me, retrieving my cock.

She slurped it up, and as talented as her tongue was, I was hard again in just a few minutes. She stood up and leaned over the small counter. She looked back at me and told me, "Kari and I flipped for it, and she lost, so I get to induct you into the mile high club."

I always believe in extracurricular activities, so I was willing to join this club. I took the half step forward and slid all the way into her. She groaned, then reached down and pulled something out of the pocket of her discarded skirt. She shoved it into her mouth, and I saw that it was the pair of panties.

I pulled her head back with her hair so that I could look at her in the mirror. "You really are a nasty slut, aren't you?" I reached forward and used the dispenser to get soap all over my thumb, which I promptly and roughly shoved up Cheri's ass.

"There's a boy young enough to be your son, younger than your oldest daughter, in fact fucking your oldest daughter, who is plugging both your sloppy cunt and your dirty ass, while you've got your youngest daughter's pussy in your mouth. How nasty is that?"

Her eyes got wider, then squeezed closed as she screamed into panties and came. While she might have gotten her rocks off, I wasn't quite ready, so I pounded her for another few minutes, reaching forward to maul her breasts and pinch her nipples. She had two more orgasms before I came in her.

I stood there panting for a minute, then pulled out. Cheri slumped to the floor. I moved my cock to her face, rubbing it clean all over her face. I tucked it back in and washed my hands, while Cheri lay on the floor, panties still in her mouth.

I crouched down over her and told her, "You are not to clean up at all. You may put your skirt and shirt back on, but you are not to button or tie your shirt in any way. It should cover you, but be open."

I stood up and unlocked the door. "Oh, and you might want to lock this after I leave."

I opened the door, and a flight attendant was standing there smirking. The smirk dropped off her face as I started to move away and she saw Cheri on the floor, naked, cum dripping out of her red pussy, panties gagging her mouth. She rushed into the bathroom and asked, "Ma'am, are you OK?"

Cheri pulled the panties out of her mouth, her face reddening, and said, "Yes, I'm fine. Really."

The flight attendant looked back at me, but I just shrugged and walked away. I moved in carefully, trying not to wake Kari. When I was seated, however, Kari turned and snuggled into my neck, dropping her hand onto my crotch. I was going to move her hand, but I liked how it felt. A few minutes later, a disheveled Cheri climbed past me and collapsed into the seat next to me.

"You really are a bastard," she said, though her voice was tired, not angry.

"What happened?" I asked.

"After you left, the flight attendant came in, closed the door behind her and helped me sit on the toilet seat. She kept asking if I was OK. I had to explain that it was consensual, and that I was not attacked. She asked about the panties, and I explained that I had to gag myself or I would have screamed. She offered to help me get cleaned up, and I had to tell her that I couldn't. She tried to help me get into the panties, and I had to explain that they were not mine. It was humiliating!"

"Are you ready to cum again?" I asked.

"Maybe," she acknowledged.

Just then, the flight attendant came up with a glass of ice water in her hand. She looked curiously at me and at Kari, particularly Kari's hand. "I thought you might need some water," she said, handing the glass to Cheri.

"Thank you very much," Cheri said.

"Is he your son?" the flight attendant asked.

"No, his mother is in the next row," Cheri told her.

She glanced back to where Mom was sleeping and then pointed to Kari and asked, "And her?"

"She's my daughter," Cheri said.

"Both of you?" the flight attendant asked.

"One of us couldn't keep up with him," Cheri lied.

The flight attendant looked at me and I just shrugged.

"My name is Karrin. If you need anything else, just ring."

I watched Karrin's ass as she walked away. "Do you want her?" Cheri asked.

"What?" I replied, my attention shifting from Karrin's ass to Cheri.

"Do you want her?" Cheri asked again.

"What do you mean?" I asked.

"You could have her, you know," Cheri said.

I glanced over to the front galley, where Karrin kept glancing at us. "Very tempting," I said, "but it's me that can't keep up with you!"

"Whatever!" she said, then put her hand next to Kari's and snuggled into my neck. The only thing better would be if we were naked. Just before I drifted off, I noticed Karrin slowly walking past us, looking the two hands caressing my cock.


I heard some vague whispering in my sleep just before Kari shook me awake. "What?" I asked.

"It's my turn," she told me.

"Your turn for what?" I asked.

"My turn in the bathroom," she said. "You go first."

I stretched and glanced at Cheri, who had a broad smile on her face. "Give me three minutes," I told Kari. "I need to actually use the bathroom."

"Do you need help?" she asked.

"If you helped, I wouldn't be able to use the bathroom for its actual purpose," I reminded her.

"Oh well," she said with a grin.

I gave her a little kiss, then climbed over her, walking back to bathroom. I saw Karrin watching me, and I winked at her. I got to the restrooms and got into my favorite one; it would have been really difficult to accomplish in one of the smaller ones. I rid myself of the extra fluids and washed my hands, then opened the door. Kari was standing there, and she pushed me in. Before she closed the door, she turned and winked at Karrin.

Kari flowed into my arms and all thoughts of Karrin were gone. She kissed me hard for a few minutes, then pulled back and slipped out of her clothes. "My mother may have gotten you initiated into the Mile High Club first, but I'm going to be the first ass you take over a mile high."

She turned around and bent over the counter, pouring soap on her hands. She reached behind her and started lubricating her asshole, pushing one, then two fingers in. Then she poured more soap on her hand, and stroked my cock, which I had exposed when I dropped my pants.

She put both her hands behind her and spread her cheeks. "Do me!" she moaned.

I nestled the tip of my cock up against her little hole and pushed. She groaned, and I realized that she didn't have a gag. Oh, well. I stroked in out with little pushed, going a little farther each time. In no time I was buried completely in her, and I started lengthening the strokes. She reached under her and started fiddling with her clit.

"Fill my ass, fill my ass," she kept grunting. "Oh god, I'm going to cum!"

"Don't scream!" I warned her. She tried hard, but she wasn't completely quiet; I just hoped there was no one standing right outside the door. Her ass squeezing around my cock drained the cum from me. I held her hips as she came down from her orgasm. She folded her hands under her head on the counter and just laid there breathing heavily. I pulled out and Kari slipped to the floor. I got some towels and wiped my dick off, but Kari was not making any move to get up.

I started to pick up her clothes for her when she said, "Leave them. Go back to the seat. If that flight attendant is out there, leave the door open a crack, otherwise close it and I'll get myself together."

"You and your mother make a dangerous team!" I said, kissing her on her nose.

I stood up and opened the door, and sure enough, the hallway was empty except for Karrin. I nodded and said, "Karrin," acknowledging her presence before going back to my seat. I saw Karrin begin to move towards the bathroom.

"What did you do to my daughter?" Cheri asked.

"Just what she wanted," I told her.

I sat back and Cheri snuggled into me, her hand slipping onto my cock again. A few minutes later, Kari came and sat down, Karrin helping her into the seat.

"Any more trips to the bathroom?" she asked me.

I looked her up and down slowly and said, "You tell me."

She looked flustered for a moment, then said laughed. "You're a dangerous kid, aren't you?"

"I repeat, you tell me."

She just smiled and walked away. "What happened when he left?" Cheri asked.

"She came in almost immediately, saw me naked on the floor, and closed the door. She asked me if I was OK, and I told her yes, but I'd have a hard time sitting down for a while. She didn't look like she knew what I was talking about, but when I got up and turned around, she saw the cum dripping from my ass. She helped me into my skirt and then gave me my shirt, then walked me back."

Karrin came back with a glass of water for Kari. "Thanks," Kari said.

"No problem," she said.

When the plane landed, we walked out past Karrin. "Come back any time," Karrin said. I hoped that I would have a flight with her again.


When we checked in the hotel, I discovered that my mother had booked two adjoining rooms, one for Helen and my mother and one for me, Cheri and Karen. When I asked my mother about it she said, "They would just end up in your bed anyway, so I figured why not save the effort and money of booking a third room. Helen agreed."

I raised an eyebrow to Helen and she said, "Your mother's right. Those two sluts are going to be at you all night, so why fight it?"

"And you're just going to be one room over?" I asked.

"I've heard you all fucking before," Helen explained. "Hell, I've seen it! At least I'll be with one other person who's not after your cock!"

I looked at my mother, who had the grace to blush.

It was early in the morning, but I was beat. I hadn't gotten much sleep the night before, but we had anticipated being tired, so the first day was for rest and for seeing Boston. After unpacking, I stripped to my underwear and got into bed. Before I fell asleep, Cheri and Kari stripped, then pulled my undies off as they got into bed. My mother walked in through the connecting door when they had them around my knees.

"Oh, I see you're already busy. I was just going to tell you that Helen and I were going down to get some coffee and pastries, and I wanted to know if you wanted any."

Helen peeked in behind Mom and said, "Jeez, didn't you have enough on the plane?"

"These two nymphos probably haven't, but I have. I need to go to sleep!" I said. I looked at the two naked women in bed with me and said, "No playing with my cock!"

"Sheesh!" Helen exclaimed, leaving the room.

Cheri and Kari obeyed, and I quickly fell asleep.


I guess that my two nymphos couldn't help themselves, because I woke up with a nail gently dragging along the underside of my cock. "I told you not to touch it!" I grumbled sleepily.

"You told them, not me," I heard my mother say. My eyes popped open and I saw her sitting on the other side of Kari, her fingernail going up and down my clock. "Plus, your body probably didn't mean it, given that it was like this when I walked in." She gave my cock a quick squeeze. "Now get up and get your two slaves up too. We need to go see Boston!"

I did as she asked, but before we left I called Sandy, who attended the school we were visiting. She was excited to hear me, and she invited herself to dinner, even recommending the restaurant. We left and went around Boston, not visiting the tourist attractions, but getting a feel for the school and its surrounding community. We checked out a Realtor and figured out the best places to live and the available accommodations. It would be interesting to see how we would figure out living arrangements with Kari coming as well.

At the appointed time, we arrived at the restaurant. We hung out in the entryway until Sandy arrived. She walked through the door, saw us and squealed, running up to me and jumping into my arms, giving me a 120 volt kiss. She released me and said, "God, I've missed you." Then she noticed my mother standing next to me, smiling, and said, "Sorry Mrs. Alexander."

My mother just smiled more broadly and said, "Call me Mary, and don't worry about it. I'm in the room next to Jake's, and unless I'm mistaken, I'm going to be hearing a lot more than kissing coming from there tonight."

Sandy smiled mischievously and said, "I can find another place for us."

"Not a problem," my mother said, hugging Sandy hello.

Someone cleared her throat behind Sandy, and I looked up to see another pretty girl, roughly Sandy's age, standing there. "Oh, sorry, I got distracted," Sandy explained.

"I could see that," the girl said.

"Everyone, this is my roommate Natasha," Sandy said. "I hope that you don't mind that I invited her along. She's heard quite a bit about Jake, and wanted to meet him. Natasha, this is Karen. She's also a JG." She wrapped her arms around Kari and told her, "It's good to see you again."

"This is Helen, Kari's sister. Hi, Helen."

"This is Mrs. Harrison, Karen and Helen's mother." She waved.

"Cheryl," Cheri said.

"This is Mrs... I mean Mary, Jake's mom. And finally, this is the Jake."

"Hello Natasha," I said, holding out my hand. "Don't believe half of what Sandy told you about me. She's just an excitable girl."

"Half is still impressive," she said with a cute little smile. Natasha was about 5' 5" with hair to just above her shoulders, cut close to her head, streaked through with red and purple streaks. She had a bunch of earrings in each ear, and I thought I saw a tongue stud when she spoke, but I wasn't sure. When she took my hand, rather than shaking it, I lifted her hand and kissed it. She blushed slightly.

We were seated at our table and we ordered our food. "So, which of you are thinking of coming here?" Natasha asked us.

"All of us," Helen replied, "though I think it's higher on Jake's list than mine."

"And you Karen?" she asked.

Helen laughed and the mothers smiled. Natasha asked, "What's funny about that?"

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