As Billy approached his aunt's house, he couldn't help but remember the last time he came for a visit and how embarrassed he was at first to learn that his mother had seen him masturbating, then passed along that information to his aunt. At first, it was an uncomfortable conversation to say the least, but somehow his aunt Debra found a way to put him at ease. Not only did she make him more comfortable talking about sexuality and masturbation, she even managed to get Billy to undress in front of her, leaving him naked and displaying his erection to her. At 18 years old, Billy had acquired a great bit of experience playing with himself, but nothing could compare to the feeling and sensation of his aunt's hands on his penis, stroking him, coaxing him to cum with her calming, mature, and sultry voice. That was truly an ejaculation to remember.
Billy found he needed to adjust himself in his pants, his penis beginning to swell at the thought of his last visit. After a deep breath, he rang the doorbell, wondering what this visit might bring.
"Oh hello Billy!" Debra exclaimed as she opened the door. "So nice to see you again. Here, come in, come in"
"Hi auntie." Billy replied. "It's good to see you, too."
"Well, I hope everything went well with your mother after you left the last time you were here."
"Yeah," Billy said, "it was a little weird at first, but I told her you talked to me about it."
"Oh good. You know, your mom isn't mad at you. She just wanted to make sure you knew that masturbation was ok and that you shouldn't be ashamed." Debra explained. "She just didn't know how to bring it up with you directly."
"Um, yeah but," he hesitated, "did you say anything about what happened here? You know, about me... um..."
"Ejaculating?" she interjected. Billy's face turned deep red again. "Of course not Billy. I told you that would be our naughty little secret. Remember?"
"Yeah. Thanks auntie." Billy was relieved.
"Well, you're welcome. I think you needed that. I know how young men get and what they need." Debra told him as she winked. "Now, let me tell you why I asked you to come over today. The last time you were here, I noticed that your underwear seemed a bit old and worn out, so while I was out shopping earlier I decided to buy some new ones for you."
"Wow, um... thanks auntie, but I still have plenty at home." Billy responded.
"Oh nonsense," she countered, "you can never have too many. Besides, don't you like the feel of fresh new underwear? I know I do."
"Um, yeah. I guess" he accepted, not sure where this discussion was heading.
"Well then, why don't you come see what I bought for you. Follow me" Debra suggested as she grabbed Billy's hand, leading him down the hall towards her bedroom.
Billy's mind raced not sure what to expect next, but if was anything like the last visit, he was in for a treat. As he entered the bedroom, he glanced around noticing some of his aunt's décor and the objects nearby. On her nightstand, he could see a small stack of magazines. "Oh my god" he thought to himself, "they're Playgirl mags!" He knew his aunt was progressive about sex but now Billy found himself imagining her spread on her bed, touching herself as she explored the pages of naked men.
Debra guided him over to her bed. "I already laid out the styles on the bed for you to see. I wasn't too sure what sizes to get so I think the best thing to do is to try them on. The full length mirror should help you see which ones look the best. How does that sound?"
Billy struggled to compose himself, thinking that he would get another opportunity to undress in front of his aunt. Again, he felt his penis twitch, sensing the beginnings of another erection. "Uh, ok auntie."
"So I bought you three different styles. It seems that you usually wear boxers, right?" she asked.
"Yeah" he replied.
"Well, I did buy you some boxers, but I also bought you some boxer briefs and some bikini briefs, you know, for some variety. Ok, let's try these new boxers first. Go ahead and get undressed, ok Billy?" she asked.
Billy, almost without hesitation, began to undress. He recalled how his aunt made him feel more comfortable with his body and how encouraging she was. After kicking off his shoes and taking off his socks, he pulled off his t-shirt and began unbuttoning his jeans. As he slid down his pants, he noticed his aunt watching him, casually scanning his body from head to toe. After a short pause, he finally pulled down his underwear and threw it in the pile with the rest of his clothes. Instinctively covering his genitals, he turned toward his aunt.
"Oh Billy, don't be shy. You know you don't have to cover up with me, remember?" she reminded him. "Now come on, hands at your sides and let me look at you again. Remember, I want you to feel comfortable with your body. You don't have anything to be ashamed of."
Billy was again amazed at how quickly his aunt could put his at ease. Her calm, soothing, almost motherly voice melted away any anxiety. At last, he let his hands fall to the side, leaving himself completely exposed.
"There you go. Doesn't that feel better?" she asked as her eyes drifted once again to his genitals. "Did I mention what a wonderful penis you have?"
Billy's face turned red, hearing is aunt compliment his penis. "Thanks auntie."
Well now, let's get started. Here," Debra held up the first pair of underwear, "why don't we try these boxers first?"
