Billy and His Aunt

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?"

"Ok" Billy replied.

As Debra held the underwear near the floor, Billy stepped in, one foot at a time. "Let's pull these up. There. Nice new undies. How do they feel honey? Do they fit alright?"

"Um," Billy paused, "they feel alright" not knowing what to say. They felt the same as his old shorts.

"Go ahead and walk around the room for me Billy" she suggested.

As Billy walked around his aunt's bedroom, he couldn't help feeling he was part of some strange, but erotic fashion show. He could sense that maybe Aunt Debra was enjoying the show, almost too much.

"I know they probably don't give you much support," she observed, " In fact, you're probably swingin' free down there aren't you?" she chuckled as Billy sheepishly grinned. "Come here. Let me feel the waistband" she said as the placed her fingers inside the waistband and traced around its edge. "Well? What do you think? Do you like these?"

"Um, yeah auntie. They feel nice"

"Ok, let's get those off so we can try on another pair. Here, let's try the boxer briefs next. I know, I know, you're probably not used to wearing these, but the woman working in the men's section of the store said they're popular with young men. Ok, go ahead and step into these and I'll pull them up."

As his aunt pulled up the boxer briefs, Billy immediately noticed how different they felt from his regular boxers. The fabric fit snugly against his body and seemed to caress every part of him.

"How's that, honey? Feel nice?" she asked. "They should give you much better support, especially if you're out playing sports. Now go ahead and walk around again for me sweetie. I want to see how they look on you."

Billy once again walked around the bedroom, enjoying the feel of support from this style of underwear.

"Well," his aunt paused as a wicked grin emerged, "I must say that I like these much better. They definitely make your butt look nice."

Billy blushed again, hearing his aunt compliment him in that way.

"Oh stop it now, no blushing. It's ok for an aunt to compliment her nephew. And yes, you do have a very nice butt. Now come back over here so I can feel the waistband. I want to make sure this is the right size" she said as she placed her fingers once again inside the waistband of the underwear. "How does that feel? It's not too tight is it?"

"No auntie, it feels fine" he replied as his aunt continued to feel around his waist.

"And how about the front? Everything ok there? Just let me check something sweetie. I'm just going to run my hand right down here and take a feel" as Debra slid her hand over the front of Billy's underwear and cupped his package. "Hmm, yes, it does seem like the pouch is holding you in nicely. What do you think honey? Do you like these?"

"Uh, yeah auntie. These feel really nice" he managed to say as he struggled to suppress a growing erection while his aunt continued to fondle his genitals.

"Yes, I think I'll have to go back to the store and get you a few more pairs just like this" she said as she continued massaging the front of Billy's underwear. "Uh oh, it feels like the front is getting a little bit tight. Oh my," she exclaimed, "is that your penis? Are you getting hard honey?

"Oh, um... I'm sorry auntie," Billy confessed and blushing once again, "I couldn't help it."

"It's ok Billy. Just don't get too excited. We still have one more style to try and we might not be able to fit everything inside if you have a full erection. Now take those off and get ready for the last pair."

Debra picked up the last pair of underwear, the bikini briefs. She smiled as she recalled her conversation with the salesperson earlier as Debra explained to her what kind of underwear she was looking for. Debra wanted something that would really show off a man's package. Of course, it was her nephew's package that she really had in mind. The woman working in the men's section instantly knew which style Debra should purchase, having bought the same style for her boyfriend.

Billy nearly gasped at the size of the tiny garment. It would not leave much to the imagination. Still though, Billy was enjoying the whole experience too much to stop and was still struggling to maintain a semi-flaccid state. Soon though, he would lose the battle.

"Ok Billy, here's the last pair. I know, I know, these bikini briefs do look a bit small, but the woman at the store recommended these too. She said they made her boyfriend look extra sexy. C'mon, what do you say? Will you try these on for me honey?"

How could Billy refuse his aunt's request? "Ok auntie, I'll try them."

"Good, now go ahead and put your legs through and help pull them up for you." Debra paused a bit not knowing if the fabric would contain Billy's genitals in their excited state. "Just relax honey, I'm just going to try and arrange you so that everything fits right" she explained as she positioned his penis with one hand and pulled the garment over with the other hand.

Billy was already losing control of his erection as aunt continued to arrange and position his penis and testicles.

"There! I think we got everything in" she exclaimed. "Now turn around for me." Billy turned in a complete circle as his aunt watched, surveying her nephew's nearly naked body.

"Hmm, the front is looking pretty tight though. Let me feel what's going on down there" she said as her hand cupped Billy's package. "Well, well, I think I feel what the problem is" Debra said in her playful, yet sultry voice. "It feels like my nephew is getting big and hard for me, aren't you?" she asked as she continued massaging the front of the Billy's briefs.

"Sorry about that auntie," Billy blushed, "but I can't help it when you keep doing that."

"Do what?" Debra replied, feigning ignorance. "You mean this?" Debra gripped Billy's penis through the fabric, casually repositioning it until it pointed upwards, the head now poking above the waistband.

"Yeah, that." Billy moaned as his aunt continued to fondle his erection.

There was no stopping Debra now. She knew what she was doing and she knew what she wanted to do next. "Well, I guess I did kind of cause this, didn't I?" Debra confessed in her wickedly sexy and sultry voice. "I can't leave you here like this, all hot and bothered, with your penis so big and hard, can I? In that case, I'm going to go ahead and help you with your, um 'problem'. How does that sound sweetie?"

"That sounds really good, auntie" Billy answered, barely able to contain his excitement about what he imagined was coming next.

"Ok honey, first, let's take these sexy briefs off" Debra directed as she pulled down the underwear, finally freeing Billy's erect penis. Debra grabbed his hand again and led him back toward the bed. "Ok, now I want you to go ahead and sit down on the edge of the bed. Now lie back and let me sit right next to you."

Billy lied down on his aunt's bed, his penis erect, pointing toward his belly button, and throbbing to the pulse of his heartbeat. Debra sat down next to him and placed on of her hands on Billy's thigh, slowly stroking upward towards his testicles.

"We're going to take care of your nice hard penis and you're going to ejaculate again for me and relieve your tension. How does that sound honey? Can you give your auntie a nice big load of cum?" Debra asked as her hand cupped Billy's testicles.

"Oohhh..." was all Billy could manage as he felt his aunt's warm, experienced hand massaging his genitals.

"Ok Billy, I'm going to take your hand and I'm going to put it on your penis" Debra explained as she took his hand and placed it on his erection. "Go ahead, just wrap your fingers around it like you're going to masturbate. Now I'm going to put my hand over yours and we're going to stroke it together."

Billy gripped his cock tightly as his aunt fingers closed around his. Debra then began guiding Billy's hand up, then down, slowly stroking Billy's thick, stiff manhood.

"Mmm, how's that?" Debra purred. "Do you like that honey? Does that feel good?"

There was no need for Billy to answer. He was lost in the moment, surrendering completely to the pleasure.

"Oooh, look at all that precum," Debra noticed as she took one of her fingers and traced a circle around the head of Billy's penis, spreading the slippery fluid all over. "Hmm, I want to try something," Debra said as she raised her finger to her lips. "Mmm, you DO taste good!

Billy couldn't believe his aunt did that. This night just kept getting better and better.

"Oh Billy, let's switch" Debra said as she pulled Billy's hand away from his penis. "Now it's my turn to wrap my hand around you and I want you to put your hand over mine. I want you to show me hard to squeeze and how fast you want me to stroke. Can you do that for me sweetie?"

Billy knew he wouldn't last long. He could sense his impending orgasm. Billy's penis twitched and throbbed as Debra gripped his erection. He then placed his hand around hers and began to slowly guide her hand up and down his slippery shaft.

"Oh Billy, your penis feels so nice in my hand. So thick. So hard" Debra whispered in his ear. "Oh yes baby, let's stoke your big, thick penis together. Keep going honey, keep going. That's right, up and down, up and down."

Billy squeezed his hands hand tighter around Debra's hand and his penis and quickened the pace of their stroking, faster and faster.

"Oh yes, that's it. I want you to give me a nice big load of cum" Debra said, gripping her nephew's penis tighter, feeling it throb in her hand. "I want to see you shoot. I want to see you spurt your semen up in the air. C'mon baby, show me. Shoot it Billy. Shoot it!"

Billy grunted and felt the explosion, shooting his cum high into the air with the first three spurts.

"Oh yes Billy! Yes! Keep going baby" Debra encouraged as she continued to stroke. "Give it all to me. Give it all to your auntie."

As Billy's orgasm subsided, Debra slowed her stroking, but kept a firm grip on his penis. "Good job honey. That was wonderful. Here, let me just stroke you a few more times and give you a nice squeeze," Debra said as she milked the last few drops of Billy's cum.

"Wow, look at the mess we made!" Debra chuckled. "You sure do produce a lot of semen. As Debra finally released Billy's penis, she noticed some of his semen had flowed onto her hand. She then brought her hand towards her mouth and began to lick his cum off the back of her hand.

"Mmm, your cum tastes as sweet as your precum" Debra commented. "Maybe next time, we'll have to find a different place for you to shoot your load, if you know what I mean" Debra winked.

Billy couldn't believe his ears. Was she really suggesting what Billy was thinking? Billy collapsed back onto the bed, exhausted from the night's erotic adventure.

"Don't go anywhere sweetie. I'm going to get a washcloth and get you all cleaned up." When Debra returned from the bathroom she began to slowly wipe the semen from Billy's chest and genitals. As she finished cleaning him up, she leaned over and kissed his forehead. "Thanks for letting me shop for you sweetie. And thanks for putting on that little fashion show for me. I want you to promise that the next time you're here, you'll show off your new undies to me. Will you do that for me Billy?"

"Oh yeah auntie" Billy responded. "I will. I can't wait" Billy really couldn't wait for whatever his aunt had planned for him next.