Just Another Visit to her Mother's

The lock on the door screeched as it turned. Too late. No time to run or hide, a moment later and the door swung open as Stacy barged in.

"You know she needs- Oh my god!" she was planning on saying something but stopped and exclaimed when she saw me standing in the middle of the living room.

Nevermind what I was doing. She thankfully didn't see that. She did see me frozen still, standing in plain view, clad in nothing but a bra, panties, and thigh high stockings. Her bra, panties, and thigh high stockings to be precise. She knew they were hers too. They were good garments, black lace outlining a deep red satin.

Stacy slowly marched into the room and threw her keys on the coffee table. I didn't say anything, I had planned to avoid this situation, she wasn't supposed to be back already and I never planned what to say if she caught me.

"So," she drew the word out, "just, why?"

"I don't know. They're just sexy. I love the way they feel." I said pedantically. I tried appealing to her esteem, "They remind me of you."

Stacy was trying to hide her smile, "Oh do they? So that makes it okay? You're going to stretch them out and stain them. Seriously! A thong too! For fucks sake, I'm not wearing that again after it's been up your ass!"

"I'll wash them!" I promised. "I washed myself too, before I..." I wanted to avoid actually going on record saying I put her underwear on so I just trailed off.

"Don't care. Goddammit. You have your own!" Stacy fussed.

It was true. I had my own underwear. Womens underwear. Panties. Thongs. Bras. They weren't the same. I never actually went to a store where I could try out different pairs, I just ordered what was available online that looked like they might fit.

Stacy's underwear were always so much better than mine. Soft silks and cottons, laces and nylons. Everything was so comfortable and firmly held in place, it felt like I was wearing nothing at all. Her underwear had the most vibrant colours and patterns, they were adorned with adorable little doodads like dolphins and unicorns, rainbows and cupcakes. And don't get me started on the sexy negligee, that bolstered and highlighted the curves and shapes of the body. I couldn't bring myself to shop in the same stores she did. I asked her to buy some for me but she said she didn't want to keep track of my dimensions and the hassle of being in charge of my garments.

So on occasion, when she was out for the day, I would slip on her clothing. I had my own leggings, skirts, and overalls, blouses, t-shirts and tank tops. I didn't have any dresses, or all the other cool assortments women have. Everything she had was better than mine and we were about the same size, so they fit well.

Stacy was supposed to be visiting her mother today, an exercise that would have taken hours, but she wasn't gone more than twenty minutes before returning home. She must have forgotten something. I had only put on her undergarments so far and I was already turned on, so I was posing in front of the entrance mirror when she started unlocking the front door.

"Those are yours now, and you are paying me wholesale." she decided, as she sat down on the couch. I nodded, that not only seemed fair, now they were officially mine!

She was still scratching her chin, deep in thought, I knew that wasn't going to be the only repercussion. I didn't think I'd get off that easy, especially that she knew she was doing me a favour selling her underwear to me.

"I mean obviously we are starting with a spanking." she said ostentatiously.

"Obviously."

I waited. Spankings were thrilling. She hadn't firmly landed on a real punishment yet.

"Oh!" she started laughing to herself. I loved the way she covered her mouth with her hand when she giggled. She started laughing hard. "What if- What if you visited mom?!"

Oh god, not a day with her mother. My shoulders slumped.

"No, but get this! You wanted to wear my clothes today, wish granted!" she was still laughing and kept going, "I'll pick out some stuff that will still pass as, well, you. But it's still going to have to suck! Oh! We can put some makeup on too! Just a little!"

I nodded. Honestly, I just wanted to get to the spanking as soon as she mentioned it. She could have told me to eat rusty nails.

Stacy promptly gave me a nice, hard spanking on the couch before we did anything else first. I was already in a thong so that was bare bottomed enough. She put out her hand, which I placed mine in, and she pulled me over her lap and went to town on my bum. We really did need to get going though, unfortunately it was short. I wasn't as fond of short spankings: without the dirty talk and further development into other kinks and fetishes, it almost felt more like a juvenile punishment. She still finished me proper, she was good that way. She gave me a good jerking for the last minute of spankings and when I was about to cum she rolled me onto the floor and put myself in her mouth and sucked hard. She kept sucking me long after I came, cleaned me up real good, afterall, I was about to put her clothes on.

The rest of the day was going to be rough, but she always made everything worth it.

After she finished in the washroom and spent a few minutes in the bedroom, she came back into the living room. I was still lying on my back on the floor where I came, eyes closed and nearly asleep. She kicked me in the shoulder and I opened my eyes. Her hands were full with enough clothing to outfit a shelter.

We started with a pair of ripped jeans. These were good, I'd tried them before, but they hung low and my thong stuck out at the waist.

"Oh, not bad!" she squealed. Of course she liked them. "I like how the thong sticks out."

"Your mother. YOUR mother."

"Fine, fine, we'll try to find something else, but let's keep that in a backup pile."

Next we tried on a pair of her formal pants, they were a dark grey and almost would have worked, but they were terribly tight. I recalled how firm and juicy her ass looked in these and even though I had recently cum, I was back at half mast. The zipper wouldn't move and the hems were already half up my calves.

"Okay, okay, stop before you rip something. Bad idea." she confessed.

Next we tried on some black yoga pants. These were skin tight every inch around and went right up my bum. There was no way I was leaving the home with these on.

"Too casual." she shook her head.

Finally we put on some white jeans. I didn't know how I felt about them, they were tight. Really tight. But at least they were jeans and were somewhat straight legged from the knee down. I could pass as a boy wearing tight white jeans in these, her mother would hate me just that much more, but at least strangers mostly wouldn't take a second look. It was good.

"I like it because the red and black from that thong really shows through!"

Okay, that wasn't so good.

Whatever, if someone saw it and didn't like it, fuck them.

Stacy must have pulled out a good ten shirts for me to try on, but the clock was ticking and she looked determined, digging through the pile. She knew exactly what she wanted to pair with the white jeans. She pulled out a small, white, v-neck t-shirt that barely fit me, my tummy and back were exposed under it, but she handed me a zip-up hoodie, horizontally striped in thick black and white stripes, to wear over it. The hoodie was also tight and just barely came down to meet my pants. All hope of concealing my visible thong was gone. I put on a pair of my white ankle socks and my black and white running shoes, and away we went.

I was glad we skipped the makeup. We were late enough as is, and I really looked like a boy in girls clothing, I might have been willing to go farther, but not if we were going to be spending time with her dusty old crank. Sorry, I meant her loving mother.

At least I thought we were skipping the makeup, until we pulled up the car in her mother's driveway and Stacy turned to me, "Oh for fucks sake! The whole reason I had to go back in the first place was to get my- and you didn't put on any makeup!"

Stacy reached over me and pulled on the passenger door handle, opening the door in a rush.

"Okay, well you go and say 'hi' to mom, I've got to go back home quickly. I'll bring my makeup kit too."

I knew better than to argue, she was frustrated. I took off my seatbelt and reluctantly stepped out of the car. I made my way to the house entrance as Stacy pulled the car out of the driveway and peeled off.

"Hi, Agnes!" was all I decided to say when Stacy's mother answered the door. She took one look at me, and the bland half-smile she was forcing faded away.

"Ms. Oliver." she grunted as she turned around and walked back inside, leaving the door open. I let myself in.

"So, Stacy forgot... something." I hadn't realized until now I had no idea what she had left at home, she was always running around in a flurry.

"Oh, stop with the bullshit." I had never heard Stacy's mom swear before, I was caught completely off guard and stared at her wide-eyed. "What are you wearing?"

Well, I knew she'd get right to this.

"Oh, you don't like it?" I always antagonized her. I think that's part of why Stacy liked me.

"In my days only two people dressed like that, faggots and clowns, and my home isn't a circus."

"Clowns wear makeup." I corrected her.

"So do faggots!" she yelled at me. "Where's your makeup, faggot?"

I was done with this bitch. I never had much patience for her to begin with.

"I forgot to put it on! Don't worry, Stacy's bringing her kit!" I yelled back at her.

"Is that what you make my little girl do? Waste her time with your sick perversions?"

I didn't want to respond to that, I didn't want to bring Stacy into this, so I just turned my head and remained silent. To my shock, Agnes grabbed me by the ear and twisted it.

"You want to wear makeup, you learn how to do it yourself." she let go of my ear and disappeared down the hallway. "Come on, faggot!"

I hesitated. What was going to happen now? Was I going to find out where Stacy got her crazy side from? Her mother was old, decrepit and utterly insufferable, still, I was at half mast. Maybe it was just the tight pants rubbing against me.

"Now!!" she shrieked down the hallway. I followed her down the hallway.

I could hear her in her bedroom, but I knew this old crank so I stood in the doorway before entering and waited for her to invite me in. She nodded at me and motioned for me to sit on the bed. I silently obeyed.

Agnes was pulling out her makeup set and pulling items from it. She turned around and had a brush in one hand and blush powder in the other. Without a word, she started applying it around my face. I closed my eyes and tried to breathe softly and stay still. I should have been thinking about what I would say to Stacy when she saw her mother had put makeup on me, but I was too concerned with my penis.

I sat there for a while with my eyes closed, moving only when Stacy's mother asked me to look in a certain direction or to pout my lips.

"Open your eyes, it's time to apply the mascara." she said as I opened my eyes. There wasn't a nearby mirror and I really wanted to see what I looked like, so I turned my head to look in the ensuite bathroom mirror, but Agnes cuffed me over the top of the head. "You can look after, you silly perv. I don't have all day."

I looked straight and kept my head still while the mascara was applied to my eyelashes. I kept my mouth shut, even though I wanted to mention I wasn't learning anything, she was just putting makeup on me.

"Okay, I you're finished." Agnes said as she said as she started putting her makeup kit away. She barked at me, "Get off my bed!"

I stood up, but was quickly met with a hand twisting my ear.

"On your knees when you are in my bedroom."

I dropped to my knees and Agnes let go of my ear. I knelt in silence as she put away her makeup kit and grabbed her handheld mirror.

"Look. Quickly!" she said as she briefly held it in front of my face.

I didn't get to stare and marvel at myself, from what I did see, I don't think I would have wanted to. I looked like a painted whore. The lipstick was a bright and deep red, applied generously. My eyes were rounded with dark purple and white and my cheeks were a rosy pink. Way too much of everything, but I politely thanked her with a pleasant "Thank you."

My ear was twisted yet again.

"Who?" was all she said, as she continued twisting my ear.

"Thank you, Agnes!" I squealed. Now my other ear was being squeezed at the same time as the first. Agnes didn't say anything. I knew what she wanted to hear.

"Thank you, Ms. Oliver!" I howled.

My ears were released and I instantly held them with both of my hands. Ms. Oliver left the bedroom and quickly yelled back, "Follow!"

I wasn't sure if she wanted me to stay on my hands and knees, I hadn't forgotten she demanded I stay on my knees in her bedroom, but I wasn't sure if all the rules had changed and she was just looking for another opportunity to twist my ear. I didn't like the ear twisting, but I was fully erect in my thong and tight white jeans. I didn't want her to twist my ear again, and I didn't want her to stop, so I stayed on my hands and knees and crawled out back into her living room.

I had never once heard Ms. Oliver laugh before, but she snickered when I made my entrance, crawling on my hands and knees, wearing tight white jeans and drawn up like a prostitute.

I had never thought of Ms. Oliver in any sexual way before, but now the floodgates were open. I wanted her to do all the kinky things Stacy did. If I was a dog I would have been wagging my tail. Instead, some pre-cum came out of my penis and left a spot on my white jeans. Ms. Oliver noticed.

"You filthy rat!" she cried out. "You are just always horny, like a little dog aren't you?!"

I guess I wasn't the only one thinking I looked like a dog on all fours right now. Ms. Oliver stomped over to me and I thought she was going to twist my ear, but instead she pinched something else. She firmly squeezed the head of my erect cock between her thumb and forefinger. Despite how old she was, she was still able to clench down on me hard. It hurt, but I was able to handle it, Stacy had done much worse.

Ms. Oliver wasn't impressed by my pain tolerance and moved her entire hand to cup my testicles, she squeezed hard. I was familiar with this pain too, but it was hard to resist. I fell onto my side and groaned loudly. Smiling, or at least what counted as a smile for Ms. Oliver, she let go of me and stood back up, looking down on me.

"That sap needs to be extracted from you. Constantly. I don't like you dirty little boys always masturbating or having sex, you lack focus! You need to have the serum continually pushed out." she explained.

I had no idea what she was talking about, but I liked the sound of this.

She disappeared back into her bedroom. I stayed put on my hands and knees and waited. Stacy should have been back by now, I was going to be caught by her the second time today and the consequences were going to be much worse. This was her mother! But I couldn't stop, not now. This was her mother! Things were just about to get interesting.

Ms. Oliver reentered the living room, but stayed out of my sight. She was behind me, and I felt her unbuttoning and unzipping my pants. With a few quick jerks, she had my pants and thong down.

I felt something very cold touch my anus and pushed right inside me. I knew exactly what it was. Come on, Ms. Oliver, you really think that is anything I can't handle? I almost chuckled and she almost gasped. Instead she quickly pulled out the anal plug and, growling, I could hear her stomp back off to her bedroom.

For a moment, I started worrying. Does she really have a collection of anal plugs?

Apparently, because she came back and started pushing something much larger inside my ass. This one was met with resistant and I started groaning as I relaxed myself.

"I should have known to go right for the biggest one with you!" she scorned as she struggled pushing in what I can only imagine was an enormous anal plug.

I know my limits, Stacy and I worked within them and slowly expanded upon them. I wasn't prepared for this. I was about to try and explain all of this to Ms. Oliver, when with one final hard push and a large grunt, the bottom of the plug squeezed it's way in. I gasped and my mouth wouldn't close, drool slid out down my chin.

"Shit!" was all I could exclaim when I caught my breath.

A hard spank quickly followed on my bum, Ms. Oliver shouting, "Language!"

Usually I would be incredibly turned on right now, but I realized my penis was limp. I needed a moment. Man up, bitch! I tried telling myself.

Another hard spank quickly followed. She reaffirmed, "I said, language!"

I hadn't sworn again, but I knew this old crank. "I'm sorry!"

Another hard spank came down hard, followed by another three in quick succession.

"I'm sorry, Ms. Oliver!" I screamed. I was back at full erection.

"Good!" was all she shouted as she pulled my thong and pants back on. "Stand up!"

I slowly made my way back onto my feet and stood up. The anal plug adjusted itself and a tear squeezed out of my eye as it did so.

That's when the doorbell rang.

The door wasn't locked, and it swung open as Stacy rushed in. I wiped the tear from my eye, not realizing until after how much I smeared my makeup.

"I'm sorry I'm so- Oh for fucks sake! Really?!" she blurted out as I had a feeling of deja vu. "With my mother?"

"Stacy," her mother began, "I'm tired of you wasting your time with little rats like this! If he wants to wear makeup, he needs to do it himself!"

Again, I abstained from mentioning I hadn't been taught anything, but Stacy just glared at me and asked again, "With my mother?"

I didn't know what to say, part of me was waiting for her to join in on the fun, but she was genuinely upset. I couldn't think of anything to say that might fix this, as I was contemplating, Ms. Oliver continued talking.

"I told you he is a dirty rat! He will do anything with anyone as long as he gets his little penis excited!"

Stacy stared at me a moment longer, frowning. She looked sad. I thought she was going to say something, but she abruptly turned, opened the door and left, slamming the door behind her. I stood there, not sure if I should chase after her, or stay here and see what happens with Ms. Oliver. Sometimes inaction is action, and a moment later I could see her blazing off down the street in the car. I turned to Ms. Oliver, my erection was coming back.

"Oh no!" she grabbed me by the ears with both hands again, "I'm not keeping your filthy hide here!"

Ms. Oliver had a strong hold of me by the ears and pulled me to the door, somehow this decrepit old lady was still able to overpower me. She let go of one of my ears to open the door, and with a quick thrust pushed me outside. The door slammed closed and I heard the lock turning.

That's fine. Fuck her too.

I started walking down the sidewalk back home. Stacy might have been there, I really hoped she was. I pulled out my phone and unlocked it, as I heard a cyclist approaching from behind. I knew these jeans were so tight that the anul plug was probably visible sticking out of my ass, I hoped he wouldn't notice, but I heard him break into laughter when he got near.

"Nice heart!" he yelled as he passed by.

I had no idea what he was talking about, was he implying my butt was shaped like a heart? I was flattered for a moment, but I turned and looked behind me to try and get a view of my back. I saw what he was laughing at, it was clearly visible. Centred on my ass, outlined through my tight white jeans was the large heart pomel of the anal plug sticking out from my ass.

Whatever. Fuck him. And fuck the other group of boys on the street corner that I passed and sent in an uproar.