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.
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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 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.
