Sexting with My Aunt Judy

Sexting with My Aunt Judy

When I was 10, both my parents were killed in an auto accident. The only relative that would take me in was my Aunt Judy, the youngest sister of my mother. She was barely twenty at the time but willing to take on the monumental task of raising her nephew. Somehow, she was able to attend and graduate college, which led her to a lucrative position with an ad agency. Incredibly, she accomplished all that while at the same time giving me the guidance and attention that any mother would give to a child. Patient and kind, she showered me with the gift of her love, and never once did she ignore me in preference to her own ambitions. In short, she was the perfect mother.

Judy always was available for me, including me on every vacation that she took, every weekend away. She was an avid hiker, an activity that we enjoyed together. As I grew older and began to play golf, she took lessons and would frequently join me on the course. There was no activity that we did not enjoy together.

Although she was shy and reserved with others, she was always open with me. I distinctly remember the times that we just sat and talked, and in many ways, we were best friends. Rarely was any topic off limits, but as expected from an aunt/nephew relationship, we only peripherally touched on any sexual subjects. Our openness with one another did not allow us to broach that subject, even as I grew older and began to attend college.

Judy dated infrequently, preferring to be a home body. This fact was surprising since Judy was pretty by any standard. She was a compact 5'2" tall, with shoulder-length, light blonde hair and bright blue eyes to match. She was slender, with a fair complexion and a gorgeous smile. Her body was athletic, almost boyish, but her perfect bubble butt ass was something that I quickly noticed as I matured. Aunt or not, I always watched her as she walked past me. More than once, I wondered exactly what she looked like nude.

Coming home one afternoon, I noticed that her friend, Carol, was visiting by her car which was parked in our driveway. Her best friend from high school, Carol a constant in our lives. She was a frequent visitor as she and Judy were seemingly joined at the hip. Although Judy seldom dated anyone, Carol was just the opposite. Carol went through men as rapidly as others would go through paper towels. One love interest would be replaced in quick order in Carol's life. Her conversations with Judy and me regaled us with funny and crazy stories of her love life. On any given week, Carol would recite who she was dating, what night club was she haunting, and any other detail that she could remember. She was an open book and did not mind spilling any of the specifics to us.

Walking in the kitchen from the garage, I could hear Carol and Judy in the living room talking. I caught the tail end of the conversation with Carol saying, "just have him send a dick pic." Judy responded, "You know I can't do that. At least, not yet." As I entered the room, they quickly hushed their conversation and looked in my direction.

Carol inquired, "what's up, Golden Boy?", a nickname that Carol had given me several years ago referring to my hereditary blonde hair. I gave the customary "nothing" as my perfunctory answer as I sat down in a wingback chair opposite the couch.

"What are you two discussing?" I asked, slightly raising an eyebrow with a suspicious smile and tilt of my head.

Carol and Judy glanced at another, and in unison answered awkwardly, "nothing."

Pressing the point, I pushed further. "Well, define 'nothing'."

"OK Mark, you got us," Carol interjected. "Your aunt was just telling me about her boyfriend Daniel. Quite the mystery man, you might say. Have you met him?" I admitted that I had not. As I did, I noticed that Aunt Judy's face flushed slightly. The news of a man in her life was quite unexpected as she had not mentioned anyone in her life, nor did I remember her going on any dates in the past six months.

"No," I mused. "But I caught a glimpse of him when he picked her up the other night." I noticed a slight smile emerge from Judy's face. "What's the matter, Carol? You think you have the boyfriend market cornered?" I teased.

"No," Carol continued. "It's just that I hadn't heard about this 'Daniel' before today. Your aunt has kept him a closely guarded secret."

"Of course," I countered. "She's afraid that you're going to want him as well." Carol and Judy laughed. We continued the conversation for a bit before Carol had to leave. After her departure, Judy plopped down on the couch and sighed.

"Thanks for backing me up there, nephew. I just got tired of Carol's bragging about all the different guys she had dated. Then, she started trying to convince me to go out with one of her old boyfriends, and I just blurted out a story that I was dating someone named Daniel. I got in over my head before I knew it. The worst part is that I made up the fact that he is married. It was the only way I could explain why she hasn't seen us together. Now, I don't know what I am going to do. I've made up an imaginary, married boyfriend, and I just can't bear the thought of fessing up to Carol. She will never let me live this down."

"You came in at the right time," Judy resumed. "She was insisting that I get him to text me. She didn't believe me and wanted proof. I just can't admit to Carol that I made up this story."

We sat and talked for an hour. She told me that she had just not wanted to date any of Carol's friends. They were boring people who were all into themselves and were only interested in getting her in bed. Plus, she was a little embarrassed that she could not match any of Carol's dating stories, thus falling into a trap of her own making. I readily agreed that admitting that she had made it all up might be a mistake and perhaps Carol would just forget about it.

"OH, NO!" Judy exclaimed. "She's not going to let this one go. She is going to keep prying until she gets more information about 'Daniel'. I have no idea what I am going to do." She shook her head.

Shrugging my shoulders, I offered, "if she wants proof, let's give her some proof.

Judy looked at me with skeptical eyes. "Mark, what do you mean?" she asked.

"Just change my contact info on your phone where it will show Daniel as the name of the contact. I'll send some text messages to you, and you can pretend it is from Daniel. I send the usual 'I had a great time last night' and 'I can't wait to see you again', and you can respond. Show her your phone the next time you're together. Give it some time and dump me, I mean him. Easy peasy, Japanesy."

Judy readily agreed, and we began our clandestine strategy to create a series of text messages between the two of us. Back and forth, Judy and I would text each other during the day and late at night to match when they were to meet. At first, we would be in the same room conspiring on the content of the messages. After a few days, we just texted what we thought a blossoming romance might entail in text messages. In any event, we hoped that showing Carol the messages would end any suspicion. Of course, that was not going to be the case.

Two weeks after initiating the texting plan, Judy came home with a frown on her face. I knew instantly that the texting plan was not working in some respect. I asked what was wrong.

Frowning, she explained. "Carol is not buying the text messages. She wants me to produce a picture of him. Where am I going to get that? I can't come up with a random picture. Carol is too smart for that. We must create something that convinces her before we drop this scheme. I've come too far to give up now."

I thought for a moment and then offered the following. "He's a married man and married people wouldn't want to have his face on his girlfriend's phone, right?" Judy nodded. "So, we can't send his face, right?" Judy nodded again. "What if I sent something a little more 'intimate'?" Judy looked at me with a disapproving expression.

"What do you mean, 'intimate'?" She asked. "Are you talking about what I think you're talking about?" Judy continued to stare at me.

"Well," I offered, "that would prove that Daniel is real. The next time you are with Carol text me, and I will respond with a pic that is supposed to be only for you. You show it to Carol and that should satisfy her."

"I don't know, Bryan", she continued. "Texts are one thing, but you are offering to send me a picture of your... dick. You are my nephew. I don't think that's appropriate. Plus, what if Carol finds out. I would never live that down." She shook her head as she ended her sentence.

"Don't worry. I'll make sure that I only capture enough of me that would keep her from knowing that it is me. You can delete it later."

Judy thought about it for several minutes as we continued to debate the question. Finally, she relented. "Okay, but make sure that you are careful. I cannot even imagine how humiliated I would be if Carol figures this out."

So, we concocted a plan where I was conveniently out one afternoon when Carol came to visit. I went to a secluded parking garage and parked on a deserted floor. I waited for a while before I got the text.

"Hey babe, send me another pic like the other night. Deleted by accident."

Sitting in my car, I pulled my cock out of my pants, and began to stroke it. After a couple of minutes, I was hard and ready for the photo op. Placing the camera about just inches away, I snapped several pics from which I chose the appropriate one. Just before I sent it, I had a thought and added "How about something from you?" I had always wondered what Judy looked like. I was stretching the boundary, but I thought it was worth a try.

After sending it, I began to have second thoughts. I thought I had crossed the line, but it was too late. After several minutes, I began to worry about the consequences of my request. Just then, my phone vibrated, announcing the arrival of a response to my earlier text. I opened the message.

What I saw stunned me. There was a perfect picture of the most beautiful breasts that I had seen. It showed my aunt lifting her blouse and bra to show me her tits. Although the pic only showed my aunt's breasts and not her face, I quickly recognized the blouse that she had worn when I left the house.

I had to respond. "WOW!!!! Love those. Can't wait to see more." I pressed SEND. I tucked my cock back into my pants and started up my car. But before I could back out of the parking space, I heard my phone signal the arrival of another text message. What I saw next was amazing.

There on my phone was a vivid picture of my aunt's torso, her jeans and panties pulled down and her pussy there for me to clearly see. Her blonde pussy hair demonstrated that the "carpet matched the drapes." Neatly trimmed, her bush was not thick but thinly covered her vulva. Her pussy lips were distinctly visible. From the perspective, I could tell that Carol had snapped the picture. It came with the caption "something special. Girlfriend helped."

Without another thought, I quickly put the car in park, pulled my cock back out, and quickly masturbated to an orgasm. As I came, I was deep into an imagined liaison with my aunt, with me on top and her breasts pressed against my chest. My hand as a substitute, I envisioned my cock deep into my aunt. As she orgasmed in my mind, I came over and over. After calming down (and checking to assure that no one had witnessed the last few minutes), I grabbed a napkin from the glove compartment, cleaned up, and tucked my cock away for a second time. Leaving of the parking garage, I just drove around as I waited for the signal from Aunt Judy that was safe to come home.

As I walked into the kitchen, Judy was there grabbing a coke from the refrigerator. I felt a little nervous for the dick pic, but I had comfort in knowing that Judy had sent a couple of pics to me as well. Judy looked up and gave me an embarrassed look. Standing there for few seconds, we looked at each other without speaking. As if on cue, we both began to laugh.

"I guess that worked?" I laughingly said in a sarcastic tone that suggested more of certainty than of doubt.

I guess you can say so. To be bluntly honest, she seemed quite impressed with Daniel's size. And well, so was I." Judy giggled as she ended. "But you have something to answer for. What made you think that you could demand a pic from me?" She placed her hands on her hips in mocking protest. "Carol was not going to let me off the hook on that one. She practically pulled my blouse up before I could. Your second request asking for more just made her insist that I send a pussy pic. I hope your satisfied."

Hoping not to betray my sexual reaction to her pics, I said, "absolutely. And I must say, I was impressed with what I saw." I glanced from her breasts down to her crotch with a smirking look.

Crossing her arms across her breasts, she said, "well, you can just delete those right now! That was a one-time event. You do not get to keep those."

"Sure," I quickly responded. "And you have deleted my pic, right?" I tilted my head and narrowed my gaze at her.

I could see I caught her off guard. Stammering, she said, "uh, well, of course. I don't want to look at your dick on my phone." As I stared into her eyes, I could tell she was not telling the truth. Despite her representation to the contrary, she had not deleted the pic, and I certainly was not going to give up my newly granted treasure. We ended the conversation after a few minutes and went to our separate bedrooms.

A week later, Aunt Judy came home from work. Once again, Carol had raised the ante.

"At lunch Carol started in on me again about you... I mean Daniel. She insinuated that you had supplied the pic. She studied the pic closely and accused us of setting all this all up. I tried to argue that I would never ask my nephew to send a dick pic, but she is not buying what I'm trying to sell."

Thinking about what she said, it suddenly hit me. "What do you mean 'she studied the pic'? Carol has it?" I stared at Judy.

She hesitated while she tried to think about how she was going to respond. "Uh... well, she asked for it and I didn't know how to turn her down. I'm so sorry."

I shook my head slightly. "I don't care. I find it funny, even sexy that Carol is looking at my pic. I wonder if she is using it to..."

Judy cut me off. "Don't even think that Mr. Pervert. Besides, now she wants more proof." What proof I inquired. She hesitated and with a blush on her face said, "she wants a pic of us." I looked at her inquisitively and raised my hands palms up to ask silently what she meant. What kind I asked.

Again, she hesitated. "A pic of Daniel and me... together." Her voice trailed off as she nervously twisted her hair.

"Let me get this straight," I said. "She wants a pic of us?" With a look of resignation, she simply nodded. "Like how?" I asked.

With her face flushed red, "well, you know," Judy began, "a pic of us 'together.' It does not have to be actual sex. It just should be something to show us together in the same frame. I know I am asking a bunch, but I was thinking if I was just holding you, your dick." Once again, her voice trailed off to a whisper. Nervously, she looked down to the floor and then sheepishly up to my eyes.

If Judy only knew how much further I was willing to go, I was not sure how she would have reacted. But I kept my thoughts closely hidden.

"We are just going to keep this to ourselves, right?" I began. She nodded. I looked down in mock contemplation for a moment. Then, looking back to her, I continued. "Okay, when do you want to take the pic?"

Hearing those words, Judy immediately relaxed. "Nephew, you have no idea how much this means to me. Thank you, thank you, thank you."

Hoping that she was not going to change her mind, I suggested that we go ahead and get the pic. She had other ideas.

"Let's wait until 10 p.m. I told her that I was going out with Daniel tonight and we were going to a hotel. I want to keep everything in line timewise." I agreed. So, we waited until 10 p.m.

At that time, I knocked on Judy's bedroom door and she said come in. As I entered, I was greeted with the sight of my aunt dressed in a white baby doll nightie. Sitting on the bed, she looked nervously at me, her arms folded across her breasts as if to hide them. My cock was instantly stirring.

"Wow, you look amazing," I blurted out. Instantly, I worried that she would back down, but my worry was unfounded. Instead, she rose from the bed, walked to me, and kissed me gently on the cheek.

Looking into my eyes. "Thanks. I needed that. I'm a little self-conscious about my body to begin with, not to mention that I am going to be holding your dick in my hand soon." She looked away in embarrassment. "We better get this done before I lose my nerve."

Trying to break the ice, I made the following suggestion. "I've been thinking. To take a pic of you holding me, wouldn't it be better if I was nude? I don't want her to recognize my clothes, and she certainly hasn't seen me naked. What do you think?"

Judy thought for a moment and said, "you're probably right. I know it is asking for a lot, but you probably need to take off your clothes." I simply nodded and began to disrobe.

As I began with taking off my shirt, Judy sat back down on the bed and continued to watch me. At first, we both looked directly into each other's eyes, but that quickly changed to her watching as removed each article of clothing. In the meantime, I could not help but gaze at the perfect melons held in place by the skimpy nightie she wore. As I unbuckled my pants and stooped to pull them down, I looked directly between her legs to catch a glimpse of the pussy that I had seen in the pic. I could just make out the fact that she did not have any panties on.

Stepping out of my pants, I tossed them to one side and stood back up. I could feel my hard cock straining to be released from my underwear, the tip protruding slightly from the top. All the while, Judy's eyes were locked on my groin, waiting to see in person what she had seen before. Allowing both of us to enjoy the moment, I took a few seconds and then pushed my underwear down as I stooped. Again, I tossed them to one side with my foot.

Without another word, Judy stood, took the two steps necessary to stand in front of me, and kissed me again on the cheek. She then handed her phone to me and dropped to her knees.

At first, she just sat on her knees, looking directly at my elevated and now fully erect cock. I noticed that the head was bobbing slightly up and down with every heartbeat. I wanted frantically for her to touch me, to hold my hard cock in her hand, but I knew I had to allow her a few seconds. After what seemed an eternity, she looked up.

"Well," she started, "I guess we need to take those pics. Why don't you take a bunch so that we can choose the right ones?" And with that, she gently reached grabbed my dick with her right hand. "What do you think?" she said, asking my opinion as to how she held it.

"That's great right there. Let me take a few shots." Taking several pics from different angles and distances, I made the next suggestion. "Rather than just holding it, maybe it would be better if you stroked it while I took the pics." I held my breath for her response, but she simply began to lightly stroke my cock. Doing my best to take more pics, I somehow kept it together as she slowly increased her movements in tempo. After about 20 more pics, I could feel myself getting close.

"Judy, I hate to say this, but I might, you know, cum." She looked up briefly but never stopped.

"If you do, get the pics. Surely, that will convince her," Judy suggested. That was all that I needed.

So, with my aunt stroking my cock like an absolute expert, and with me looking at her perfect tits, I somehow kept taking shot after shot. Finally, I could not prolong it any longer, and I began to cum. Stream after stream of my hot cum fired from cock at Judy's face. Miraculously, I kept clicking pic after pic. Finally, after my balls had completed emptied, I let the phone drop to my side just as Judy stopped stroking.