Date With My Aunt
Date with My Aunt
My aunt Sharon has always been a secret crush of mine. She’s my mom’s younger sister by a couple years currently aged 45. She’s blond with a hint of grey, bright blue eyes a pleasant demeanor and just as sweet as can be. Her body, after a daughter, is surprisingly tight, solid B cup. Her husband founded a manufacturing company, and in a short while exploded into wealthy relative to the rest of my extended family’s standards.
I’m Ryan and I come from a fairly comfortable middle-class family. Our families grew up just a couple towns over from one another, and we would see each other often. Being from money, all their children were beautiful. I remember one time coming around the corner in my house at an informal gathering of our two families, and seeing my Cousin Rachelle’s black g-string sticking out the top of her sweatpants. I still reminisce to that view and regret never getting the opportunity to panty raid, as anytime we were at their house, nay mansion, there were always a lot of people, so it was never secure to mosey in and snoop around.
Since junior high, I have always had a fetish for panties, especially thong panties. I love seeing them peak up the back, and when I can see them through or just the line of the girl’s thong through their leggings, I can’t help but rub myself a little. My heart flutters, and I feel like I’m in on their little secret.
One day, after mulling it over in my head, I decided to raid my sister Brenda’s panty drawer. Only thongs! I had hit the jackpot and thus started my wearing habits. First it would be one a week, wear it, jerk off into them, feel shame, and put them back in the middle of a full laundry hamper in hopes she would be none the wiser. It progressed into every other day until almost nightly. Thankfully, Brenda had so many thongs that there was no shortage. I eventually learned that my other sister, Kendall, and even my mom wore thongs. So I was able to diversify, but I had to be careful which one I put them back into.
One time, I accidentally put my sister Brenda’s thong back into Kendall’s laundry, but Kendall doesn’t own as many as Brenda, and when Kendall asked what her panties were doing in her laundry, she just shrugged. I was watching TV stiff in fear that I was caught, when Kendall turned away, I saw Brenda look at me from my periphery, and kind of smirk. I laid low for a week. Fortunately, I had a stash to tide me over, but eventually I was back at it.
I became more confident. No longer was I just stealing thongs to jerk off into, but I began wearing them around the house and under my clothes when I went about my day in the world at large. I got such a thrill in the beginning, having my little secret that nobody else knew about, and it got me so turned on, I could hardly contain myself in the soft little panties. But when the honeymoon phase ended, the thrill had passed and I no longer got the kick I once had. It almost felt strange to not wear thongs, and would become embarrassed for wearing boxers.
I explored wearing my sisters’ clothes, and I found myself getting aroused, wondering if they had ever sucked cock while wearing this dress, or ever got cum on that shirt. I began to fantasize that I was one of my sisters being a slut for their boyfriends.
Brenda almost caught me one time. I was wearing one of her dresses dancing with myself in her room, when I heard the front door open. I rushed to get everything in order and dashed across the hall to my room just as the top of her head was visible at the top of the stairs. I quickly flung her dress over my head and into my closet and held myself with my back to the door. I heard her say, “Strange. I don’t remember leaving my closet door open.” She closed her closet door then left her room. I heard her stop just outside my door and then suddenly turned to go downstairs. My heart was racing as I heard her leave out the front door, get in her car and drive off. I learned to be more careful.
This went on for a number of years. Sometimes, I would get lucky and spy on my sisters in all stages of dress. My favorite times were when the girls would go out on dates and bring them home late at night. I would stay up waiting for them; mom and dad long asleep. I remember hearing Kendall bring her boyfriend in, and they went to the living room just under my parents’ bedroom. I crept downstairs, sure not to step on any of the squeaky boards, and poked my head around the corner. I was expecting them to be making out but I got a better view. Kendall was on her knees in front of her boyfriend, his pants around his ankles, her straight auburn hair bobbing up and down.
“You like that dick in your mouth, baby?” he’d say. She’d mutter an, “mmhmm” with her mouth full of his cock. “You wanna swallow Daddy’s cum?” “Yes, Daddy. Cum in my mouth I want it all!” as she’d go back to her head bobbing. I had my dick in my hand as fast as I could get it. hard as a rock, I stroked myself.
“Ok, here it comes!” with a small grunt, her head stopped moving as she took his load in her mouth. Kendall looked up at him, smiled, and I could hear a loud swallow. I couldn’t help myself, and I came all over the floor. I held my mouth shut with my other hand stifling any noise I may have made. When I came down from my orgasm, I realized I had to scarper and made haste back up stairs as careful as I could. On the top stair, I made an error, and I hit a squeaky board. I heard scrambling downstairs, and then her boyfriend left shortly after I closed my door to my room.
My golden memory though was Brenda. I remember, just like Kendall, she brought her boyfriend over, but this time, mom and dad were gone for the weekend. I was playing videogames, and Kendall was having a girls’ night out, and Brenda was out with her boyfriend. I was just settling into a jerk off session, when I heard the door open and heard Brenda and her boyfriend rush upstairs and get giggling, and the bed started squeaking. I didn’t hear her door shut.
I turned off my light and quietly opened my door, and saw a blade of light coming from her bedroom. I crawled over to her door, and peered around it. The sight was glorious. Kendall is kind of on the chubby side, but she has an ass and tits to make up for anything less than perfect, but Brenda… Brenda was thin and pale with solid B cup tits and a cute little butt. She’s definitely not without an ass, there’s plenty of jiggle in her step. She’s perfect. When I saw her, she had her back to me, on her knees, naked but a black g-string. Her wavy dark brown, almost black, hair tied up in a ponytail whipping back and forth as she gave her boyfriend a very practiced blowjob.
I rub myself through my pants, not able to thank my lucky stars enough and enjoyed the slurping bobbing show. She then stood up and I backed away from the door a little as she crawled on top of her boyfriend. She moved her thong aside and guided his, what I now see, massive dick into her pussy. I’m astounded as I watch it disappear and all I see is his balls up against her ass, and she begins to gyrate on him. Back and forth she rides him, and they’re just having at it. I see her tense up and gasp as she cums on his cock. She giggles, leans in and kisses him.
“Get on all fours.” He tells her, and she nods her agreement. She turns around and is looking back at him and at the bed as he begins to get up to mount her. She looks to her door, and I swear we make eye contact, but she says nothing, only smiles.
“On second thought, how about you stick it in my ass tonight?” Brenda suggests.
“You sure?” a wild Cheshire cat grin crosses his face.
“mmhmm” she confirms.
She looks straight ahead, out the door at me, shocked. I watch her face turn from a smirk, to discomfort, to melted within a span of three seconds as he pushes his cock through her sphincters and into her forbidden zone. Her grunts were loud and feral as he slammed his giant cock into her asshole.
“Where’s my dick?”
“In my ass!”
“mmm yeah, spank me again! Fuck my tight little asshole!”
“aah fuck! I’m going to cum!”
Just as he’s about to unleash, she pulls away from him and gets on her knees in front of him, her mouth open. With a loud groan, he unloads a copious amount of cum all of her face. Much of it goes in her mouth, but mostly on her forehead, cheeks, and eyes. When he’s done cumming, she takes him back in her mouth and sucks any remaining bit out. She grabs her phone and takes a cum selfie.
“I’m going to go clean up.” She says. I take that as my cue to make myself scarce. She goes into kiss him, but he quickly avoids her advances. She laughs and makes her way to the door to wash up. They ended up watching a movie, and Brenda left her phone upstairs to charge. I had figured out her passkey sometime ago to steal other nudes she had sent, but never one like this. When I got it, I found it, and emailed it to myself from her phone so I can delete it from the sent mail and not have to erase our current thread. That was the best.
But tragedy hit our family a year later, as my mom was diagnosed with cancer, and within a year she had passed. My family became kind of unglued, and distant. Many things just weren’t as fun as they used to be. I found myself in a depression that lasted for about a year.
A new normal was found, and we were kind of back in our normal routine, and one day out of the blue on a Wednesday, by aunt sends me a text. This isn’t completely unheard of, but definitely not a regular occurrence.
“Hey, how are you holding up?”
“I’m alright, how about you?”
“I’m doing ok. Hubby’s been at work a lot, so I got the house to myself.”
“Sounds lonely. What do you do with yourself?”
“Oh you know… work out, garden, shop ;)”
“I was think, why don’t you and I go on a date?”
“A date?” What does she mean, a date? I like a date date?
“Yeah, just the two of us, and catch up, it’ll be fun!”
“Great! Are you free this weekend?”
“Cool I’ll come by around 6 and pick you up”
And with that we signed off. I was a little nervous, and excited. It was something to look forward to. I haven’t seen my aunt since the funeral, and it’ll be good to talk to someone.
Saturday came quickly. Kendall and Brenda were both out, and dad got to drinking himself into a stupor. I got into a nice pair of dark blue jeans, and a long sleeve shirt with the sleeves rolled up. Underneath I wore a bright neon pink VS v-string that I stole from Brenda. It was exciting to be going on a date with my aunt whom I’ve had a crush on for years now. My aunt came in her black Mercedes to pick me up. My phone buzzed.
“I’m here ;)”
I didn’t even bother saying where I was going. I just left and met my aunt. It was still light out when we got to the restaurant. My aunt was wearing a tight dark blue midi bodycon dress. The sun was to our backs as we walked to the restaurant and I saw the faint outline of her thong. I didn’t even know she wore thongs then again I sort of assumed every girl did. I pulled out my iPhone and discreetly snapped a few pictures. She stopped just shy of the door before going into the shadow of the awning, bent over to adjust the strap on her heel, and plain as I was on a date with my aunt, I could see she was wearing a pink and green striped thong. My cock in my own pair became incredibly uncomfortable. I took a few more shots and prayed those came out alright, I’d have to check later. My aunt stood upright, turned and smiled at me and said, “You ready?” with a large pleasant grin on her face. She offered her arm, I took it and we entered the intimate restaurant.
My aunt Sharon had made reservations so we got in right away.
“How have you been doing?”
“I’m alright,” I responded shortly. She gave me a stare that knew more was going on.
“No, dear, I meant since your mom passed. How have you been holding up? I know for me it’s been difficult. I want to talk about it with John, but he’s always at work, so I’ve next to nobody to talk to.”
“Well, now that you mention it. I have been feeling kind of distant from everyone. I don’t really feel like talking about it, but I probably should. The hole left is tangible.”
“Mmhmm, I know just what you mean. Your mom and I used to chat on the phone almost every day, and now I don’t know what to do with myself. I’ve even reverted to my vibrator.”
My eyes went as wide as saucers, did my aunt just admit to masturbating? I went stone quiet, and blushed a little. She noticed.
“Oh come now, you didn’t think I didn’t need some of my own gratification. You’re 19, I’m sure you masturbate.”
I looked around to see if anyone was listening in on our conversation. It was kind of early in the night still, so there was plenty of space between us and the nearest party.
Sheepishly I responded, “well, yeah.”
“There it is. Your mother and I used to chat about these things. Tell me, what do you think about when you masturbate? Or do you have a girlfriend who helps you out?” She sipped her drink and had a suggestive grin on her face.
“No, I’m single. I don’t know. Loads of stuff I guess.”
“What? No girlfriend? Why not?”
“I don’t know. Girls around my age are coy and timid. They just aren’t really my type?”
“What is your type?” That same grin crossed her face.
“I guess, a strong girl who has no issue either taking what she wants or making it hers. You know?”
“I do, I think.”
The food came and it was delicious. The menu didn’t have any prices on it, so I have no way to calculate how much everything cost. I imagine expensive. We had dessert, and were just wrapping up. As we left the restaurant, my aunt in tow, the sun had gone down some, but there was still plenty of light and warmth. Thinking we were just going to go home, I was ready to check my phone for the pictures, and jerk off. I noticed my shoe was untied and bent over to tie it.
“Hello…? What’s this?” I heard my aunt suddenly say then give a long whistle. There was an elderly couple who looked at her as they passed by, and I had no clue what she was referring to.
“What’s what?” I asked
She stepped up behind me and snapped my g-string. I went pale, and my hands and face suddenly went cold. I was mortified. I looked up and she towered over me. That same grin painted across her face. I now became in her pocket. How deep it goes, I’m not sure.
“Get in.” Sharon ordered.
Sheepishly I got up and got in her car. She stepped around the front, eyeing me the whole way as she sat gracefully into her respective seat.
“How long have you been wearing panties, mister?”
“Um…” was all I could get out. Sharon didn’t start the car, just looked at me. Her face was hard to read, but there were machinations happening, “a few years now.” I lied.
“Where did you get them from? Kendall? Brenda?”
I could only nod.
“Are those Kendall’s or Brenda’s? Do they know?”
“Not that I know of… please don’t tell anyone!” I pled with my aunt.
“Shh… there’s nothing to worry about.” She purred, and tapped my nose with her finger playfully. “This is our little secret. There are conditions, of course.”
“Which is…?” I was afraid to ask.
“You’ll do exactly as I say.” She said frankly and with the depth of an abyss.
“I could only nod.”
“Good boy, we’ll finish what I had planned for the evening, and then I’ll put your loyalties to the test.”
My heart was racing as she shot off a text and started the car. We headed to the movie theater and she chose the movie. We sat in the very back row of a theater filled with next to nobody. I felt my aunt tap my arm and point as we saw a boy and a girl on their date as the girls head disappeared into her date’s lap. His head rolled back. After about five minutes, we saw her head com back up, and she took a sip of their soda. Sharon gave me a cheeky little grin, and looked at her phone. The display was all the way down and I couldn’t see what she was typing or who she was texting. She put her phone away and we finished the rest of the movie. My aunt’s hand found its way to my thigh, and gave it a loving caress. I was getting hard. The movie ended and we got back in her car.
“What did you think of the movie?” My aunt asked.
“It was alright.”
“I noticed you were getting a little shifty in your seat. Does you cock get uncomfortable in your thong?”
“Yeah a little.”
She simply smiled as she put the car in gear and started driving. We were heading to a completely different area than hers or my home.
“Where are we going?”
“You’ll see, my little toy, I’m putting your fidelity to me to the test. Will you do whatever I ask?”
I had completely forgotten about that, but I couldn’t risk my reputation being blown so I simply submitted.
“Answer me honestly, do you only wear panties, or do you like to wear women’s clothes too?
“I sometimes do,” not being completely frank, “not very often though.”
“Is that right? Does it make you feel sexy? Or how does it make you feel?”
“Yeah I guess.”
We continued driving until we pulled up to a house I’d never seen before. It was dark, and she ordered me to come. I got out and slowly walked with her up to the door. A man opened the door.
“Good evening, Mistress.”
“Good evening, slave. I have a new arrival. Get us some drinks will you?”
‘Mistress’? What is all this about? Isn’t she happily married? Who is this guy?
“Come.” My aunt ordered as we stepped inside, and walked up the stairs. The house was cream and white decorated and there was a slight sandalwood smell in the air.
We made our way into a large well furnished bedroom. “Strip!” Came my aunt’s command, and I did what I was told. I started to reach for my panties, “ah ah ah, not those sweetie.” Seeing I was only standing in Brenda’s thong she circled me like a shark.
“Hmm, yes, I see.” She disappeared into the closet and pulled out a tight light blue bodycon dress, and a pair of matching wedges. She also had a wig of shoulder length dark brown wavy hair.
“Put these on.” She demanded then disappeared back into the closet.
Just as I was straightening up the wig, she came out a knock out. She had on a black and red burlesque outfit with a red bustle, black shiny heels, black stockings, red corset with black trimming and matching red panties. In her black gloved hands she held a black leather riding crop, with a red heart as the business end. And atop her perfectly held blond beautiful hair, a tiny black and red top hat, cocked to the side.
My dick was instantly diamonds and I was ready to serve. I was very aware of the tight dress rubbing against my body, and the keyholes on my exposed ribs. It no longer mattered what she had on me. Here was a woman who oozed power, and demanded respect and obedience.
“Good boy, I see you’ve done as I’ve told. Now sit at the vanity.” I gingerly walked over to the vanity in the wedges and sat down. Having been in dresses, and other women’s clothing, I tried to mimic the part, being prim and proper, even though I looked like a whore. Just as I sat down, her slave came in with a cocktail for her and a shot glass filled with some liquid. Sharon took the martini glass, took a sip and set it on the vanity. She told me to take the shot and down it.
“I’m only 19, drinking age is 21.”
“Did I stutter, sissy? Drink it! You’ll be glad you did.” She spat at me. I recoiled at her sudden fury. She watched me and took a sip of her own drink as I took the tiny glass and upturned it into my mouth. It was fiery and strong. I usually only do mixed drinks or with a chaser, so it was pretty rough going down, but it stayed. She set down her own drink, “Good boy,” she cooed into my ear. In the mirror I saw the bustle was slightly see-through and I could see she was wearing a g-string. My cock stayed swollen
My aunt pulled out a huge array of makeup. She spent know time considering, as she grabbed mascara, lipstick, foundation, eyeliner, and eye shadow. She deftly went to work. I could see what she was doing as she was blocking the mirror, but I could see her slave simply sitting on the bed, naked, not moving. He almost looked afraid to. About fifteen minutes later, she stepped aside and I saw for the first time what she had done, and the transformation was out of this world. Had I otherwise not known I was a guy, I would’ve been fooled. My aunt grabbed her phone and started taking pictures.
“Look pretty, sissy.” The shot was taking its toll, and I could feel a pulsing through my body whenever she called me that. I clambered out of the chair and began a pinup photo shoot for her.
“Ok, Sissy. Have you only dressed up like a girl, or have you ever done real women activities?”
“What do you mean?”
Exasperated, “I mean have you ever sucked cock, or been fucked in the ass like a real woman?!” There’s that fire again. I quickly shaped up.
“N-No, I haven’t.”
“Good… I love a good cock virgin. Crawl slowly over to my slave and stay on your knees in front of him.”
I was about to resist, but then I found my body involuntarily slowly making its way to where he was on the bed.
“Good, Sissy,” my aunt purred.
I crawled slowly before him, and awaited her command.
“Do I really need to spell it out for you? Suck!”
I didn’t know how to feel about it. I had so many conflicting notions and tradition, that I sat there on my knees looking stupid.
“Suck or I let the whole world know what you are.”
I meekly nodded, and gingerly took a hold of his dick, and inched my face closer to his dick. I looked a lot bigger than I imagined, as I was about to put it in my mouth. It was also a lot softer. I opened my mouth and put it in and began to suck. The spongy texture felt weird, but as the blood swelled to his member, it became larger, and I could see why my aunt might fancy this guy. He was huge when erect. No longer spongy, but still somehow velvety, I began to bob my head up and down the length of his cock. My aunt sidled up to me, her face inches from mine and simply smiled her wicked grin.
She stood up and laughed and held the phone up taking a video recording of me pleasuring this man.
“This is your first time sucking cock,” my aunt announced. “How does it taste, slut? Do you like it?”
“Mmhmm,” was all I could muster as I was sucking her cock.
She whacked me on my ass with her riding crop.
“Excuse me, sissy. What was that?” Fire once again in her voice.
“Yes, Mistress?” I hazarded.
“Much better.” She cooed. She looked up at her slave, “Are you going to cum soon?”
I could already taste his precum filling my mouth. I only knew it was that as I knew it wasn’t my own saliva drooling out my mouth.
“Yes, Mistress.” He responded.
“Good, keep sucking. Since you’ve never sucked dick before, I imagine you’ve never swallowed cum, either, except maybe your own. I bet you would, sissy! Get your legs up above your head and jerk off all over your face while you wear your sister’s panties.” She laughed throatily. She rested her hand on the back of my head and gently stroked my wig, “now be a good slut, and before you swallow, show Auntie Sharon the load.”
“Yes, Mistress.” I obliged while still jerking him off and moving my shoulders to the motion.
I could feel him swelling in my mouth, and his breathing became ragged. Here it comes. With a great grunt, he unleashed a torrent of cum in my mouth. The salty goo, was more than I could handle, and I began to cough a little.
My aunt was on me instantly, “Don’t you fucking dare lose that load, he has been saving it for three weeks and I was going to use it for something else, but then this happened, so don’t spoil my sacrifice, you cock sucking slut!” She screamed at me with such force, that I immediately stopped coughing.
It rested in the back of my throat, and I was looking down embarrassed and highly aroused. Sharon put one finger under my chin and with a gentle loving smile she said, “Show me that cum, you dirty fucking slut.”
I was put at ease by her tone, and opened my mouth. Cum was dribbling down my cheek a little, but most of it was in my mouth. My aunt took a few pictures then switched to video.
I obeyed and swallowed what felt like the bitterest pill. It must’ve shown on my face because she laughed a big belly laugh.
“Don’t be such a pussy. You’re my cock sucking cum guzzler now, so you’d better get used to the taste.” She said with the voice you use when talking to babies or puppies and smiled warmly.
“Thank you slave, you are dismissed.”
“Yes, Mistress.” And he got up and left.
“Get showered, and put your regular clothes on. Our first date is almost over.”
I showered and got dressed and we left. She drove me home and we didn’t exchange a word. When we were in front of my house, she looked over at me and warmly reminded me, “Remember, this is our little secret.” She leaned over and gave me a kiss on the cheek and I got out of the car. She drove off, and I walked to my front door bewildered and a little confused. I got inside and everything looked different somehow. Everything was exactly as it was earlier, but I had changed. I was viewing the world from inside my aunt’s… nay, my Mistress’s purse.
Thank you everyone for reading. I really enjoyed writing it, and am happy to continue this story line. If you have any suggestions on which direction you’d like to see it go, or anything like that, please leave a comment. I’d love to hear any feedback.