A Mother’s Promise Ch. 16

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Author’s note: I have received literally hundreds of emails on this story, and I apologize it took so long to resume. To make up for it, this chapter is a bit longer and the next chapter (chapter 17) should be posted right away, perhaps within a week (or less) after this one.

This chapter begins a phase of chapters that clearly take Bobby down a road which he is destined to follow. We pick up the story immediately at the end of chapter 15 without any refresher. I apologize for that.

Lastly, please be aware this is a story about a young man’s sexual discovery and journey down many non-traditional paths, aided by his mother. If this is not your thing, Literotica has many wonderful authors and stories you can read.

Thanks again for your emails and comments. Enjoy.


I waited at the bottom of the stairs for mom to finish talking to my sister, Linda. I was excited to be going out with mom; I wasn’t exactly sure where she was taking me, but I had a pretty good idea.

When she came down the stairs, she walked over to me, ran her hands through my hair, put her hands on her hips, and smiled.

“Bobby, sweetheart, I have to say…. the way your sister did your hair, and the clothes she picked out…. I swear, you could just about pass for a girl…. or, a tomboy at least!” She said.

“The look is very subtle,” she observed, “just a slight touch of feminine, but, it’s not that noticeable, either.” Laughing, she added, “Maybe you should let her dress you more often. Now, wouldn’t that be interesting?”

“That’s an understatement.” I said. “The only thing is, uh…. this bra feels a little weird under my shirt. It’s a ‘nice’ weird, though, not a ‘bad’ weird. It feels a little tight, too.”

She pulled me into the kitchen and kissed my cheek. “Oh, sweetie, I wouldn’t worry about that too much,” she reassured me, “I think maybe you’re feeling a little awkward and self conscious right now, that’s all. Keep in mind, it’s not everyday you put on your sister’s bra and panties and go out in public. Anything new is bound to feel weird until you get used to it.”

“There’s just one thing I would change, though.” Mom replied, as she unbuttoned my shirt and held it open to look at the bra on my chest. “I think you need a little more up here to complete the look.” She said, patting my non-existent boobs in the training bra. Not a lot more, just something to make the shirt poof out a little more. Let’s see what we can do.”

She walked over to the counter and pulled a handful of tissues from the tissue box. Walking back to me, she crumpled up the tissues and carefully pulled the bra cups away from my chest and placed a few tissues into each cup of the bra. Then, plucking the cups this way and that to make it look right, she stood back and admired her work. “That should do it. It’s not too much, but it’s enough to make the shirt hang better. It gives you a little bit of a bust, sweetie.”

Buttoning up my shirt, she left an additional button open at the top. “Sometimes,” she said, “leaving one more button undone can make all the difference in the way you look and feel.” Standing back and looking at me, she said, “Ah, that’s much better.”

I looked down and there were now two small bumps under my shirt. She walked behind me and pulled the material of the shirt taunt from the back. “See how much better that is?” She asked. “It’s perfect now. It will give you the feeling of having breasts. Are you comfortable with that?”

Needless to say, I was. The style of the shirt was such that it could be worn by a male or a female. If anyone paid any attention to me, they would see my slight chest and my hair and probably think I was a girl. Okay, maybe a homely girl, but, none the less, they would think I was a girl.

I have to admit I felt a twinge of excitement and a little bit nasty knowing I was going out in public like this — imitating a girl. I mean its one thing to put on bra and panties in the privacy of your own home, or even let your mother or sister dress you up in bra and panties, but once you venture outside your front door dressed like that, it’s a completely different ball game.

“I’m proud of you for having the courage to go out, baby. It’s kind of a big step.” She said, complimenting me. “But, no one is going to recognize you where we’re going, and to tell you the truth, I think you look just fine.”

Mom glanced toward the stairs to make sure we were alone and then reached to feel between my legs. “Are you hard?” She asked.

As her hand squeezed my inflated cock, I could only smile. I always had a hard on when I was around her. And, she knew that perfectly well.

Squeezing it, she said “I would be worried if you weren’t, sweetie. But, I guess I shouldn’t be surprised. Your Uncle Mike had perpetual erections that lasted days, I think. Or, at least it seemed like days. It was so much fun teasing him and driving him wild. Oh, Never mind,” she continued, “Let’s get going. I can’t wait to get güvenilir canlı bahis siteleri you there!”

“Mom, before we go, can I ask you something?” I said.

“Sure, baby.” She answered.

“Well,” I said, “you know you woke me up this morning before I had a chance to, uh, you know, make myself cum. And you didn’t let me cum with Linda after breakfast, and you told me not to cum while you were gone to your appointment. So, do you think, I could uh….”

She held up her hand and interrupted me. “Bobby, I know where this is going and the answer is ‘no’.” She replied as she put her arm around me and walked me to the front door. “It’s not going to kill you to hold off for a while. Plus,” she giggled, “I kinda like it knowing you’re horny and carrying a full load.”

As I got into the car with my mother, I found myself grinning as I pulled the seat belt over my body and pushed the end into the buckle. Peering over at me, she asked, “What’s the smile for, sweetheart?”

“Uh, nothing,” I answered, “I’m just happy to be getting out of the house, I guess. Out with you, I mean.”

“Oh, that’s sweet of you to say, Bobby.” She said as she backed the car out of the driveway. “Maybe we should do this more often. You know, just mother and daughter.” She peeked at me out of the corner of her eye with a sly smile. I don’t know if it was a slip of the tongue or some foretelling of things to come.

But, I hadn’t told her the real reason for my big smile.

The real reason I was smiling was because I was recalling the promise she made when I was in her bedroom after breakfast this morning.

When she made me that promise, I had just finished licking her juicy pussy through her panties and my face was completely covered with her wetness. Specifically, she promised me if I kept my hands off my sister while she ran an errand this morning, she would give me a nice surprise “later”.

Then, right before she left to run her errand, she mentioned something about taking me shopping. So, based on all of that, and her comments over the last few days that I should have my own panties, I think the facts were falling into place perfectly, and it was clear to me: she was taking me shopping to buy panties!

As additional proof, she told my sister to make sure I had a good shower, shaved the teenage stubble off my face and she told Linda to dress me in some nice clothes. Then, to top it all off, she told Linda to dress me in a bra and some “pretty” panties. That was the clincher! I knew I was right. And apart from a few nervous butterflies in my stomach, I was excited as hell.

Figuring I would play dumb for a while, I asked, “By the way, where are we going?” I tried my best to keep a straight face. I even bit my tongue to keep from smiling.

“Well, that’s a surprise, but you’ll see soon enough. Why? Where do you think we’re going?” She asked, glancing over at me while she drove.

I couldn’t contain my excitement any longer and my face broke out in an uncontrollable grin. “Oh, I don’t know,” I replied sarcastically, “but you DID promise to take me shopping, remember?”

“Ah, now I see what you’re getting at. So, you think we’re going shopping, eh?” She playfully answered. “You’re right! I did promise to take you shopping because we need to get you your own bras and panties, sweetheart. You can’t continue to wear mine and your sister’s lingerie everyday.”

It was like every word she said turned a key on my jaw and my grin got bigger and bigger. The first time the topic of “shopping” ever came up was the day I helped her do the laundry. That was the day everything came out in the open about my panty desires and panty fetish. Since then, there were several conversations where she said I needed my own lingerie.

“Well, Bobby,” she added, “I guess we’ll just have to see where we end up. Maybe it’s shopping and maybe it’s not. Will you be heartbroken if it’s not?”

“Nah.” I answered. “Not really. I just figured that’s why you told Linda to put me in bra and panties after my shower. I mean, you know…. uh, in case I had to try on something at one of the lingerie stores.”

She smiled and reached over to pat my hand. “I think you’ll enjoy what I have planned, sweetheart. But, tell me…. speaking of your sister…. did you and your sister ‘do’ anything while I was gone?”

I thought for a moment about how I should answer. Should I tell her nothing happened? Or, should I tell her half of what happened… or everything that happened? Weighing everything, I decided on the cautious approach and said “I promise I didn’t touch her…. and I didn’t cum, Mom.”

“But,” she asked, “I know you guys did more than just try on clothes the whole time, right?”

“Well, come on, mom! She didn’t make it very easy for me.” I answered. “She took her panties off and started teasing me and…… asking a lot of questions and saying a lot of things to get me hot. Then, the next thing I know we’re both naked, and, uh, uh….”

“Go güvenilir illegal bahis siteleri on.” She said.

“Damn, Mom,” I replied, “do you know she’s completely bare down there? I mean like….. totally hairless? You can see everything! She let me look right between her legs!”

“Well, I expected her to try to entice you, Bobby.” She reminded me. “That’s why we had that little talk in my bedroom, remember?”

“Yeah, I know, but, you don’t understand. I mean she’s permanently bald there now.” I said.

“I know,” mom replied, “your dad told me all about it last night. Did she tell you why her pubic hair was removed?”

“All she told me was that dad paid for it.” I answered.

“Well, trust me, there’s a lot more to the story than she’s letting on, dear. And, don’t change the subject on me. So, did she touch you?” Mother asked.

“Yes,” I said, “and she threatened to make me cum if I didn’t tell her more of the things you and I have done. Then, when I was in the shower, she got her fingers all soapy and, uh….”

“Okay, I get the picture.” Mom replied, interrupting me. “It should be obvious to you that your sister is more sexually advanced than you are, sweetie. She’s undoubtedly learned how to tease and control boys your age. You’ll have to get accustomed to that with her and learn to recognize when she’s manipulating you. According to your dad, she can be quite persuasive and convincing.”

“Yeah, well ‘devious’ if you ask me,” I replied, “but I didn’t touch her and I didn’t cum — although I wanted to. And before you left you promised you would have a surprise for me if I could restrain myself, which I did.”

“Oh, I have every intention of keeping my end of the deal, sweetheart. You can count on that.” She said, laughing. “And I think it’s safe to say you’re going to be, uh…. how should I say it…. properly rewarded.”

“Listen, Bobby,” she said after a few moments, “can we have a serious discussion for a few minutes?” She looked at me to make sure she had my attention. “Your dad and I had a long talk last night concerning you and your sister. He’s going to come home this afternoon while you and I are out. He’s going to talk to her, so, that leaves me to talk to you.”

I began to panic, not knowing where this was heading, especially after my sister confessed that she’d sucked dad’s cock. “Are we in trouble?” I asked. “Is he mad?”

“No, no,” she answered, “nothing like that.” She reached over again and clasped my hand in hers. “It’s just that we both realize the two of you aren’t children anymore.”

As we came to a stop light, she took a breath and turned to me. “Bobby,” she continued, “by the time I was your age, your Uncle Mike and I had done just about everything two people could do together. Sexually, I mean. And I think your father and I realize that the more we try to keep you two apart, it’s only going to force you to go looking for sexual pleasure somewhere else. And quite honestly, we would much rather you and your sister find what you need at home until that special personal comes along for you.”

“I think what I’m trying to say,” she continued, “is that I’m releasing you from your promise not to mess around with your sister, provided whatever might happen between the two of you is consensual. Of course, that means never doing anything in front of non-family members and never talking about it outside the family. As long as you keep it in the house, you two can have your fun. And we decided that could include intercourse, sweetheart.”

Did I hear that correctly? I thought about it for a minute. I immediately had thoughts of Linda and I having non-stop sex and finally losing my virginity inside a real pussy. Correction: my sister’s pussy. Double correction: my sister’s bald pussy.

Although I was surprised and extremely happy about what she just said, her explanation didn’t say anything about either her or dad. The more I thought about it, my initial happiness started to turn into confusion. Did this mean things had to end between my mother and me? Given the choice, I would gladly give up my sister if I could have my mother under the same circumstances.

“Where do you and dad fit into all of this?” I asked.

“Well,” she sighed, “your father and I are going to discuss that very topic with the two of you tonight after dinner. He and I have already talked it through and we’ve got it all figured out, but, that will be a discussion for this evening. Okay?”

I started to analyze what she just told me, but she broke the silence of my thoughts. “Oh, crap!” She exclaimed. “I didn’t realize we were almost there. Look, Bobby, there’s one more thing we need to talk about. Do you remember all the times over the last few days where I asked you to trust me?”

“Of course.” I replied.

“And in any of those times, did I ever let you down?” She asked.

“No, mom, not once.” I answered.

“Okay then, I’m asking you to trust me again. When we get to where we’re going, güvenilir bahis şirketleri I want you to go along with whatever I ask you to do. Don’t bother thinking about it; I’ve planned everything down to the smallest detail. You have my word that if you play along, you’re going to really enjoy yourself. Fair enough?” She asked.

“Fine with me.” I replied.

As soon as I had answered, we pulled into a strip mall. I was trying to figure out exactly where we were, but, I didn’t recognize any of the landmarks.

If we were going shopping, wouldn’t we be at the mall? So much for that brilliant idea, I guess.

But, what was in this strip mall besides shopping? It all seemed puzzling, but, she didn’t let me churn on it long, because in a matter of seconds she had me out of the car and before I knew it, we were walking down the walkway in front of many different stores.

As we walked, she took up the time by chatting away, saying, “Baby, this is going to be so breathtaking for you…. I can just feel it.”

I don’t know who was more excited, her or me. Maybe I was just nervous. I wasn’t even paying attention to the names of the stores as we walked, so when she finally pulled me to a stop, I looked on the door and suddenly, a lot of things started to make sense. The name on the door said: “Brenda’s”.

Now, my Aunt Brenda owns a chain of hair salons in one of the suburbs close to us. This was her newest one, but, it wasn’t just a hair place. I overheard mom and dad talking about it while it was being built and after it opened. Mom came here occasionally and sometimes my sister came here, too. But this wasn’t your everyday hair salon. When we walked in, there was a lobby — kind of like a doctor’s office waiting room. It was a fancy looking place and when we opened the door, none of the women seated in the lobby paid any attention to us, or to me, as we walked in.

There was a large desk where a nicely dressed woman with glasses sat with a computer. My mom pulled me over to the desk and we stood there until the woman looked up and greeted us. “Hi,” my mom began, “is Brenda here?” She asked.

“Hold on and let me check. Can I ask your names?” The woman answered.

“Just tell her it’s her sister-in-law and her niece.” Mom replied.

The woman gave me a nice smile, picked up the phone and punched a few numbers. In just a matter of seconds, she told us my aunt would be right out. I replayed my mom’s words back in my head…. the ones where she said I was Aunt Brenda’s niece…. and then slowly looked around to see if anyone was looking at me. I was astonished to see no one was staring and the woman at the desk had gone back to her work without even a second look at me.

In less than a minute, I saw Aunt Brenda coming through one of the doors and as soon as she was upon us, she hugged mom and then turned to me. I felt embarrassed for a minute, but when she hugged me and kissed me on the cheek, the embarrassment melted away. “Oh, you look so cute!” She whispered, almost silently, as she hugged me.

“Come on,” Aunt Brenda said, “I’ve got everything ready.”

I walked behind them, looking around as we made our way through a hallway to a door with a nameplate that said ‘PROCEDURE ROOM’. “What kind of ‘procedures’ go on in here?” I wondered. Aunt Brenda smiled and opened the door to show us in.

I think the only way to describe this room is that it looked like a fancy hotel suite. It was big, I mean really big. It had a desk with a computer and a phone, a TV, comfortable looking chairs, a recliner, and yes… a bed. Looking over to my right, there was at least one or two more rooms back that way. There was also another piece of furniture in the room…. it looked remarkably like a hospital bed. There were rails on the side and it had wheels. “This is getting seriously weird.” I thought to myself.

“Bobby, it’s been too long since I’ve seen you,” my aunt said, “here… let me look at you.” Aunt Brenda held my hands in hers and stepped back to look at me. After giving me the once over, she hugged me to her and I felt her breasts crush into mine.

Releasing me from her hug, she turned to my mom and asked, “Sherri, did you tell him?”

“No,” my mom answered, “I thought it might be best if I told him here. You know, like a surprise.”

“Oh, I see. Do you want me to step out while you two chat, then?” My aunt asked.

“Not at all, Brenda. In fact, I think you should stay.” My mom answered as she lay her purse down on one of the chairs.

Mom sat on the bed and then reached toward me. Beckoning me over to her, she grasped one of my hands and pulled me in front of her. Then, looking at my aunt, she patted the bed next to her and asked Aunt Brenda to come and sit with her.

When my aunt was seated next to my mother, mom looked up at me. “Bobby,” she began, “when I went out this morning, this is where I came. Your aunt and I sat in this very room and I told her everything you and I have been through since the day I found all those panties in your room.”

I think my mom was fully prepared to see the look of distress on my face. Actually, I think she expected it. So when I started to pull away from her and my facial expressions signaled my unhappiness, she held my hand tight and said, “Bobby, please hear me out.”

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