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James Finds Trouble

Maybe having your roommate know your secret isn't a good thing.
This late on a Monday night, the subway car rumbled along nearly empty. Trying to avoid the looks of the couple at the front of the car, I found a seat near the back. I slowly sat down, and even then it was too quick. Holy crap, it hurt. It had been real--not a dream. Despite telling myself that, everything still had a surreal feel to it. The lights in the subway car. The couple holding hands but not talking or looking at each other. Even my breath going in and out of my chest. Nothing felt real. I looked at my reflection in the window. Everything looked the same. Nothing was.

I was on my way home from my first session with a Dom.

Hunched forward, I used the front of my hoodie to cover my crotch, needing to come badly. My cock stood rock hard in my jeans, and had been hard for a long time. The train hit a bump, and I felt the tenderness of my ass again, gasping over it. Standing would be better, except for my cock standing straight out, the bulge obvious for everyone to see. And it would be odd to stand on an empty train.

Like most people searching for this kind of thing, I found my Dom online. After months of searching and surfing, I spent another month worrying and talking myself into it and then out of it. Last week, I’d finally made an appointment with Andrea. I’m still surprised I actually showed up. It helped that she seemed so nice and kind online and on the phone (the phone conversation was a requirement of hers). At one point, I actually worried if she’d be able to give me what I needed. I wasn’t worried about that anymore.

Andrea was probably ten or twelve years older than me (I’m 21), a beautiful, tall brunette--she had to be five-ten or five-eleven--with long, dark hair, amazing legs, and beautiful, blue eyes. After a long interview, where she had been kind, understanding and professional, she left me in the room, telling me she’d be back soon. After ten very long minutes, she came back. For a moment, I wondered if it was the same woman. Kind and understanding were gone, her entire demeanor nothing but ice. She made me strip and face the wall while she took my clothes into another room. Then she put me on my knees and bound my wrists tight behind my back. After an extended session of licking and sucking her toes, she’d spanked me--with a hairbrush over her knee, a paddle over a chair, and finally her riding crop.

Of course, she hadn’t let me come. She completely ignored my cock.

Finally my stop arrived, and I walked through the rain as quickly as I could to my apartment. With every step, I could feel my boxers move against my sore ass. It was worse as I ran up the stairs to my apartment. The small front room was empty, but I could hear my roommate talking on the phone through her bedroom door. My cock dying for a release, I slipped into the bathroom, shut the door and pulled my jeans down to my ankles. I told myself to be patient and take my time, but there was too much excitement built up. I started pumping my cock as fast as I could, three hours of pent up energy ready to explode.

I liked to jack off into the sink, both to contain the mess, and to let my balls rub on the edge of the sink--the cool sensation intensified my orgasms.

My orgasm seemed to get close, then it would dance away; I couldn’t get over the edge. My cock wasn’t used to waiting three hours to come, and I don’t think it could believe it was finally time. Then I remembered her toes in my mouth, the feeling of being over her lap and my cock against her thighs, the sting of the crop, and the thrill her cool, calm voice sent through my body. Imagining that it was her hand pumping away on my cock, her cool voice ordering me to come, and the thought of one hand spanking my sore ass as the other pumped my cock, I felt my balls tighten and I closed my eyes as the first beautiful, incredibly intense spurt hit the far side of the sink.

The door opened.

I opened my eyes to see Mandy staring at me, her phone still in her hand, her mouth open in surprise. Another spurt hit the sink. In a panic, I turned away, then remembered my ass was red and covered in welts.

“Sorry,” she said, then closed the door. I heard her say on the phone, “What? Oh, nothing, never mind. Just my roommate--I’ll tell you later.”

I laid on the bathroom floor, wanting to die from embarrassment, come still pulsing out of my cock.

***

I avoided her for two days. Really avoided her. I stayed at a friend’s house one night, sleeping on his couch, then came home very late the next night. The following morning, I left while it was still dark.

Thinking of my Dom, I jacked off every chance I got. I knew I’d be going back. Had to, really.

After class, I clocked in at the library. Putting away books, I turned back to the book cart and my heart jumped up into my throat. Mandy walked down the aisle, a strange and worried look on her face. I literally turned to run away, but there was no where to go--the aisle was a dead end.

“James,” she said, “Eventually you have to talk to me.”

My face no doubt blushing bright red, I said, “Ok.” I figured she’d want me to move out, like in the next hour. I just hoped she didn’t tell the world about what happened. Looking down at my sneakers, I said, “I’ve got a break in few minutes. Meet me in the coffee shop?”

She nodded, but I could tell she didn’t think I’d show up.

***

We didn’t know each other very well. I’d ended up her roommate after a girlfriend of hers had flunked out and gone home. Mandy’s lab partner was a co-worker of mine and knew I’d been looking for a new place. I liked Mandy from the first moment I saw her smile and heard her sweet voice. A junior, she was a psychology and history major--a double major fully allowing her to be a waitress, she joked when I first met her. I remember blushing after she said that, and saying something painfully stupid.

Though I’m on the baseball team and fairly athletic, I’ve always been painfully shy. Mandy’s no supermodel, but she was cute as hell. Only five-four or five-five, she was a touch chubby, but she had the cutest face and cutest smile. It seemed like the more I saw her and the more I looked at her, the more attractive she got. And her big, dark brown eyes showed the sweetness of her heart. She liked to wear this pair of white shorts around our apartment that hugged her ass like I don’t know what. I jacked off thinking of those tight, tiny white shorts I don’t know how many times. And she had the very nice habit of simply ignoring my shyness.

I found her in a quiet corner of the coffee shop and gently sat down. She looked down towards the chair, then back up to me.

Quietly, she said, “So, we need to talk about what happened.”

I couldn’t look anywhere near her. “I’m so sorry,” was all I could say.

She said, “I’m sorry, too.” That surprised me. I risked a look at those wonderful eyes. “I should have knocked. I didn’t know you were in there.”

“I should have locked it. I was in a rush...”

She laughed. “Obviously. What happened to your ass?”

My heart froze. I stared at her, my face turning bright red. I’d hoped she hadn’t noticed. Then she looked down, at the chair I was sitting in. “It still hurts?”

I could only nod.

“Did you ask someone to do that to you?” I could hear the judgement in her voice. That I was a freak.

I put my forehead down on the table and nodded. “I hired a dominatrix,” I whispered.

“Oh my God.” Then she laughed a little. “I’ve heard of things like that, but...”

“It was my first time,” I said. Like that made it okay.

She laughed again. God, I loved her laugh. “Are you going to go again?”

Head still down, my face hidden, I nodded again. “I’ve got another appointment, in two weeks.”

***

Two weeks later, I was riding the subway again. Cock even harder, if that’s possible. And my ass was in much worse shape.

I ran up the stairs, to our apartment on the fourth floor, and through the door. Mandy was sitting on the couch, her bare feet up on the coffee table. She was wearing the white shorts, and a tight, white t-shirt. It was obvious she wasn’t wearing a bra, her maybe C-cup, maybe bigger breasts threatening to tear through her shirt. I stopped, mouth open, taking her in. A cute, little smile played across her lips.

She asked, “Did you get what you needed?”

I nodded.

“Are you going to go into the bathroom and play with yourself?”

I nodded again.

“I’m going to watch this time.”

I almost came in my boxers.

She stood up and motioned for me to go into the bathroom.

Once there, I was suddenly very nervous and uncertain.

Standing not a foot away, she said, “It’s ok. Take down your pants.”

I unbuttoned them, then let them slip down. My cock was rock hard in my boxers. “It’s as big as I remember,” she said. “I thought I was imagining it, since I only saw it for a second.” I was pretty certain it wasn’t that big, but I appreciated her saying it.

Her fingers reached out and tugged on my boxers. “You are going to take them off, aren’t you?”

I closed my eyes, not believing what was happening, and pulled them down to my knees. My cock sprang free, bobbing up and down. She chuckled.

Her fingertips reached out and touched my ass. I sucked in a breath. “Wow, it’s redder than last time. What did she do? Tell me.”

I could tell she’d gotten into it, over the last two weeks. She never said a word, but she sent me texts like Only four days to go. Are you nervous? She counted down every day for me. Teased me with texts like, Tomorrow you won’t be able to sit down. Even wished me Good Luck as I rode the subway there. She was so sweet.

I started to stroke my cock.

“Not yet,” she said. “Tell me first. Tell me.”

My mouth dry, I stuttered and stumbled. “Well...when I got there, she was with someone else, so another woman led me back to a room. A different room than last time, which made me even more nervous. It was nearly empty, just a chair in the middle of it, and a tiled floor. Everything was white. This new woman, she had me undress.”

“Were you hard?”

“Very, and I tried to hide it, but she didn’t seem to care. Then she took my clothes and my shoes, even my phone, and left. Not knowing what to do, I sat on the chair.

“About fifteen minutes later, she came in.”

“Your Dom?” She sort of giggled as she said it.

“Yes. And she was none too happy. She asked me why my nose wasn’t in the corner. She also asked me if I properly thanked the first woman. I moved to put my nose in the corner, and she told me it was too late for that, and ordered me down on my knees. Then she pointed down at the toes of her shoes.”

“Did you kiss them? Just like that?”

My face turned red, but it felt good to tell someone about it. For all of this not to be a secret after so long. I nodded. “I did. I had lots of practice the first time. She moved over to the chair and sat in it, then slid one foot out of her shoe and had me suck on her toes. Well, first she had me beg for it, then she let me kiss and suck them. I could tell she was still annoyed with me.

“She asked me again about thanking the first woman properly. I asked her what that meant, and she got even more annoyed. She made me take the hairbrush in my mouth and crawl back down the hallway and ask the woman--she was at the reception desk--if I could properly thank her.”

“Oh my God. Did you?”

I nodded. “I crawled back to her and dropped the hairbrush at her feet. I asked her if I could kiss her toes and thank her for earlier. I was hidden by the desk, but still, on the other side is the waiting room, I knew there were two guys out there that could hear me. She turned her chair towards me--she’s a tall red-head with pale skin and I think she’s a dom in training--and slipped her foot out of her shoe and extended it to me. She let me lick her toes--all of them--a long time. Then she asked me what the hairbrush was for. I told her it was to teach me a lesson about thanking her properly. She made me ask for a spanking.”

I glanced in the mirror, at Mandy’s eyes. She was staring at my cock, then looked up and smiled at me.

“Were you still hard?”

“Yeah. Chinese math hard. So she put me over her lap and spanked me. Not as hard as my Dom, but still pretty hard.”

“Did you like it?”

Like isn’t really the right word for it, but I didn’t think it was the right time to say that. “I did. She was wearing this short skirt, and I could feel a bit of her skin just below her skirt. My cock rubbed some back and forth as she spanked me. She stopped right before I could come.”

“Oh, your Dom would have killed you had you come on her.” Mandy said it with a squeak.

“After thanking her for the spanking, I crawled back to my Dom. She had me stand up and bend over in front of her while she sat in the chair. I had to grab my ankles. She told me to close my eyes, then her fingers ran all over my ass.”

“Did you like that?” Mandy’s hand reached out and her fingertips ran across my very sore ass. It was so tender I could feel her fingernails, even though she was extra gentle. I couldn’t breath for a moment. My hand found my cock and I started pumping it. She brushed my hand away, and one finger brushed against the head of my cock. It was almost enough. She said, “Not yet, baby, tell me the rest. Did you like her hands on your ass?”

I nodded. “She used a finger to tease my asshole, then ran it down, over the base of my cock, and over my balls. Before, she’s always ignored my cock. She tapped the head a few times, then said, ‘It would disappoint me if you came without my permission.‘ She told me to stay exactly as I was, and she left the room.

“She left me there a while, and when she came back, she sat back in the chair. She said, ‘I’m not happy with your bottom. I doubt it’s red enough for you to have learned your lesson.‘ Her voice was very cold, but she played with my ass as she said it. I heard a snap, then something cool on my ass. She started pushing her finger in, her other hand teasing my balls as she did it. Then I felt something else start to push in. I opened my eyes, and she had this bright blue butt-plug against my ass. I told her it was too big. She said, ‘My dear, I’m afraid this is the smallest thing I’m ever going to put in your ass.’ She smacked me hard, several times on each cheek, then told me to keep my eyes closed. Then I felt it back against my asshole.”

“How big was it?” Mandy’s hand was still on my butt, her fingertips near my crack.

“I don’t know. Smaller than my cock, not very long, but wide at the bottom.”

“Did that turn you on?”

I found her eyes again, in the mirror. I nodded. “It did, but it also scared me. She asked if I was going to please her, and she made me answer her. Made me tell her that I was. Then she pushed it inside me. It felt so huge. She left me like that, and I heard her get up and move around. She moved the chair away, then I felt something wide against my ass. Wide and with holes in it. A paddle. She told me she was now going to finish the punishment that Amanda should have given me. Then she went to the door and called Amanda in to watch.”

“I bet you liked that.” Her fingers slid a little further down my ass. Would two women violate my ass today?

“She made me ask for twenty, and made me count them.”

“Is that what made these round spots on your ass? The paddle?”

“Yes, it hurt.”

“Did it make you cry?”

“Some. By the end, tears were running down my face.”

“Did you learn your lesson?”

I laughed. “Probably not. Then she said we could now finally get on with what she had planned for me.”

Mandy said, “Oh boy.”

“That’s what I thought, too. She had me stand up straight, then she put cuffs on my wrists. Like real, police cuffs. They were tight. Then she put another set around my ankles.”

“Was Amanda still watching?”

“Yes. She asked little questions now and then. Mostly embarrassing ones about how hard I was.

“My Dom made me lie on the floor, on my stomach, and hooked the ankle cuffs to the wrist cuffs. It’s called hog-tying someone. She told me she needed to go spank another client. She said, ‘I need you to keep quiet while I’m gone.‘ She reached under her skirt and pulled off her panties. She made me open wide, and she put her panties in my mouth.”

I looked at Mandy in the mirror. Her eyes were full of merry disbelief, her free hand covering her mouth. “Were they wet? Could you smell her?”

“It was all I could smell. She was very wet. She ordered Amanda to put tape over my mouth.

“I heard her walk across the hallway. I was facing the wrong wall, so I couldn’t see anything, but I could hear that she left the door open, and that she was in the room right across the hallway. She made a woman beg and beg, then she spanked her long and hard. The woman was crying and begging and promising she’d be good-- she was really loud--then my Dom asked her if she could take more, for a taste of her pussy.” Looking at Mandy again, I wondered if she’d like to go with me sometime. If she’d liked to be spanked, too. Her legs were held tight together, but I could tell she was super turned on, her nipples threatening to pop out of her shirt.

“My Dom started spanking the woman across the hall, and the new dom must have gotten bored. She kneeled down next to me and started playing with my sore butt. She pulled out the plug and pushed it back in. It felt weird, being tied like that and her able to do anything she wanted to me. She spanked me a few times, then ran her hand below my ass. She played with my balls and teased the base of my cock. I was super hard and not far from coming--”

“So you liked being tied like that? It turned you on?”

I wasn’t sure I liked Mandy making me admit all of this. Or her knowing all of this about me. Still, I nodded. “She started whispering to me that she was going to make me come. Leave me there like that, a mess under me, for my Dom to find. Told me that my Dom would use the cane on me, for that. Or send me home and not let me come back for a month or more. I was so close, I could feel my balls tightening up and getting ready to come. I was humping the tile floor, but I couldn’t do that very well, tied up like I was. Then she stopped, saying ‘This is the interesting part.’ She rolled me on my side, and I thought she was going to jack me off with her hand, but she only smiled at me and told me to be still. I watched her walk out the door and across the hall.

“My Dom made the other woman beg for a spanking. A licking. On her pussy. And the woman did. She begged for it, then I heard something leather cracking into her. The woman cried out after each one, promising to be good. After maybe a dozen of them, my Dom asked her if she could take ten more, for a taste of her pussy. Crying hard, the woman begged for more. And she got them.”

“Oh my God.”

I couldn’t really tell what look was on Mandy’s face. Some mix of pain and pleasure. “I’m pretty sure my Dom sat on her face. She ordered the woman to lick her ass. Eventually my Dom came. I liked hearing her come. Wished I could make her come.

“A minute later, I heard her stilettos walking back towards me. She helped me slide my hands down lower, then pulled me up onto my knees, her panties still in my mouth and my hands still tied to my ankle cuffs. It wasn’t very comfortable.

“She sat on the chair, slipped one foot out of her shoe, then ran her foot across my face. She asked me if I liked the taste of her panties in my mouth, and if I’d like to taste her pussy. I nodded hard, really wanting that. She called me a silly boy, saying I’d have to be good five straight sessions, and please her, to taste her pussy. But she did say that if I was very good the rest of this session, and took the hard, hard spanking she was about to give me, that she might be persuaded to let me suck on one of her nipples. I nodded that I wanted that, that I wanted to please her. That made her smile. It was a wicked smile. She pushed my head down against the cold, tile floor, which put my ass up high in the air.

“First she used her hand, which only hurt a little, even though she was wearing long, leather gloves. Then she used a small paddle--it was wicked and curved, and the wood was at least a half inch thick. That brought back the tears. Next was her riding crop--her favorite--and that went on and on and on. Eventually she reached between my legs. ‘Maybe we’ve reached my silly boy’s limit. He’s not hard anymore.‘ She played with my ass, and pulled the plug out and pushed it back in a few times. That’s all it took, and I was hard again. She chuckled at that.

“She told me to stay just like I was. She undid all the cuffs and pulled the tape off. She had me kneel again, then asked if I’d still like to taste one of her nipples. I told her that I did. I begged her. She told me that I’d have to take one more spanking, with the hairbrush. My ass was so tender, I wasn’t sure I could, but I wanted to please her. She told me to crawl across to the room across the hall and bring her back the hairbrush.

“I was wondering how I’d find the hairbrush, but the woman she’d punished was still there. She was tied on her back, on a low bench that slanted down, with her head down towards the floor. Her legs were tied wide apart, and there was a hairbrush in her pussy.

“Her ass was beet red, with stripes all over it. And her thighs, too. I could even see where her pussy had been spanked.” I looked up at Mandy. She didn’t even meet my eyes--hers were closed, as if she was imagining the moment. “I knew I couldn’t use my hands, and that Andrea was watching, so I took the brush out with my mouth. The woman moaned as I pulled it out.

“I crawled back to Andrea. She was smiling, which made me very happy. She took the hairbrush out of my mouth, then held it out, handle first. She made me clean it off with my mouth." 

“Could you taste the other woman?”

“I could. Andrea patted her lap, and then I climbed over it. I had to beg for a spanking. She asked me if it should be an easy spanking or a hard one, for her nipple. I told her hard. She said, ‘Good boy,‘ and then she spanked me hard. Until I was crying again. But I didn’t go soft, with my cock against her leather skirt.

“Finally she was done. She had me kneel again, and thank her extensively for my spankings, by kissing and licking her toes. She put a blindfold on me--I hadn’t yet earned the right to see her breasts. Then, finally, she pushed her nipple into my mouth. She teased my cock a little with her toes as she let me suck on it, telling me how easily she could make me come.

“I only got one minute of her nipple--all I had earned. She put me back in the corner, and made me wait there until Amanda came back with my clothes. I thanked her properly, this time.”

Mandy said, “That is the wildest thing I’ve ever heard. If it wasn’t for your ass, I’m not sure I’d believe it.” Her hand reached out and settled on top of mine, against the sink. She lifted my hand and brought it to my cock. “Are you ready to come, James?”

“Yes, please.”

That made her smile. “Stroke it for me. Come.”

Who would argue with that? I wrapped my hand around my cock and started pumping. She moved closer to me, her body against my side, her fingers still on my sore ass. Her hand cupped one cheek, then squeezed it. I gasped. I could feel her shorts--her pussy--against my leg. God I wanted her to wrap her hand around my cock and pump it. If I asked, would she?

While I searched for the courage to ask her that, her other hand found the crack of my sore ass. Very slowly, a fingertip slid down. Would she do it? Would sweet Mandy play with my ass while I stroked my cock? The fingertip moved down so slowly, teasing, then back up. She did it again, getting closer and closer. Then the fingertip stopped, right above it. I started to feel disappointed when it touched my asshole. She looked at me in the mirror. With a smile, she pushed her finger in slowly. All the way in, until I could feel her hand against my ass.

She mouthed the word, ‘Come.’

Her finger slid in and out of my ass, still so teasingly slowly. I pumped my cock, fast, fast, faster. Thoughts spilled and ran through my head--my Dom’s toes, my cock against her skirt, the taste of her toes in my mouth, the scent of her panties, her finger in my ass, the hairbrush against my ass. I looked down, at Mandy’s pretty toes, her toenails painted a bright, cheery purple. Then at her nipple, so close. I wanted to lick it. Suck it. That was the thought that did it. Hours of being teased and spanked welled up inside me, spinning inside my balls, and finally broke free. I came. Came like it was the first time I’d ever come. A splatter hit the wall above the sink, then another hit beside it. Her finger kept pumping in and out. Another splatter hit the sink.

She whispered in my ear, “Keep coming, baby. Empty your balls for me.”

I would have done anything for her in that moment. I kept pumping, feeling spurt after spurt jump from my cock. Finally it was too much--too sensitive. I leaned forward, my hands on the sink, my body shaking.

She kissed my shoulder. “That was incredible,” she said. Her voice was low and husky.

I could only mumble my agreement.

“I’ve never watched someone come like that.” She slipped her finger gently out. Still, I gasped. Her body so close to mine, she washed off her finger in the sink. “Make sure you clean up your mess.”

I nodded. “I will.”

She kissed me again on the shoulder, then walked out of the bathroom. The sight of her ass in those white shorts was enough to stir my cock.

She walked into her bedroom and shut the door. I knew she was about to play with herself. Wondered if I’d be able to hear her come.

***

Thursday night walking home, I considered asking Mandy if she wanted to watch me again. Since Monday night, she hadn’t said a word about watching the first time. She had texted to ask me how my ass was. I wasn’t sure if I could even bring any of it up, but my cock was hard as hell and full of encouragement.

The first thing I noticed when I came through the door was the smell of perfume. Not too much of it, just a hint, but it smelled good. She didn’t normally wear perfume. Then I saw Mandy sitting on the couch. “Wow,” I said. She was wearing a tight, tight blue dress--she couldn’t have been wearing a bra, or panties for that matter--and tall, matching blue stilettos. I had never seen her dressed up like this before--she looked amazing.

She stood up and walked towards me. “You like?” she asked.

“Yes, very much. Are you going out?”

“No,” she said, a bit coyly.

Then I noticed a pair of yellow panties sitting on the coffee table. Next to her hairbrush. My cock wasn’t sure if it should get harder or run away.

“James, I’m afraid we need to talk about your behavior. I clearly told you to clean up after yourself Monday night, didn’t I?”

Not sure what was happening, I swallowed, hard. Mandy’s voice had taken on a cool, wicked tone that made my knees weak. What happened to sweet, sweet Mandy? “I...I’m...”

She walked towards me. “You do remember me telling you?”

“Yes. I...I...”

“And yet today, I found a spot on the floor. And on the mirror. You don’t expect me to clean up after your messes, do you?” She took her finger and tapped it against my jeans and my very hard cock.

“No. I’m sorry. I must...”

“I’m not interested in your excuses, James.” She picked up the hairbrush and smacked it against the palm of her hand. Holy fuck. I was so scared and excited, I couldn’t move or speak. “And worse, earlier I couldn’t find my yellow panties--my favorite pair. And where do I find them? In your room. That’s horrible behavior, don’t you think? Using my panties without my permission? Were you planning to come in them?”

Well, I may have borrowed a pair of her panties from time to time (and I always washed them afterwards, of course), but I hadn’t done that in a week or more. I’d never seen the yellow ones before.

“Well, James, what should we do about this?”

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com with this note attached, it has been posted without my permission.


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