<p>Click here to read the previous parts of the story.</p><p><img data-media-id="71330675" src="/31/02/3102563e4639f840c5fabc279401de07e886e55dd9f590589428183860ae44b4.jpg"></p><p>“Logan, could you come out here?” Margaret called from the living room.</p><p>Logan rushed out of his bedroom to answer his roommate’s call and found her standing next an older woman he’d never seen before.</p><p>“Logan, this is Caroline,” Margaret said. “She’s going to be your babysitter for the evening.”</p><p>“What?” Logan said as he looked at the older woman.</p><p>Caroline was unquestionably pretty but there was a hardness to her face and in her demeanor that made Logan a little fearful of what his evening would hold. She wore a pair of tight-fitting jeans and a buttoned-up cardigan sweater that clung to her sizable breasts but offered not even a hint of flesh.</p><p>“Did you think your punishment was over after your date with Larissa?” Margaret said. “Did you really think that would be all you’d have to suffer for being a pervert?”</p><p>Logan shook his head. He’d certainly hoped his punishment was over, but he wasn’t naïve enough to think that Margaret would let him off the hook after one night.</p><p>Logan looked at Caroline and wondered how much Margaret had told her. Did the older woman know he was wearing a pair of panties as he stood there in the living room? Did she know that Logan had been caught stealing his roommate’s panties and that he’d already subjected himself to various forms of punishment to satisfy Margaret’s need to make him suffer for his crime?</p><p>“You were a very naughty boy,” Caroline said in a throaty voice. “I agree with Margaret that you need to be punished and I’m quite pleased that she asked me to spend the evening as your babysitter. After all, a pervert like you can’t be trusted to keep out of his roommate’s panty drawer, can he?”</p><p>Logan shook his head. Margaret had clearly shared everything with the older woman.</p><p>“Caroline lives right down the hall, Logan, so if tonight goes well she’ll come over to babysit anytime I have a date,” Margaret said.</p><p>Logan wasn’t sure what to say. He wasn’t really interested in having a babysitter anytime he was going to be alone in the apartment, but he couldn’t really tell Margaret to fuck off. After all, she still held a certain amount of sway over him, given that she could very easily file a report that would label him the kind of pervert that ends up on lists on the internet.</p><p>“Are you going to be good for Caroline?” Margaret asked.</p><p>“Yes, I will,” Logan replied. He didn’t have a choice.</p><p>Margaret turned to the older woman and said, “You can do whatever you’d like with him. Remember, he doesn’t get to say no, and if he does you can feel free to make him suffer for having the temerity to disobey you.”</p><p>Logan saw a smile spread across Caroline’s face. It made him fearful of how she might make him suffer. He made a note to avoid Caroline’s wrath at all costs. She seemed far too excited at the idea of inflicting pain.</p><p>“I’ll be back later tonight,” Margaret said.</p><p>“Take your time,” Caroline replied. “I’m sure I can come up with all sorts of activities to keep Logan busy.”</p><p>“Have a good night, Logan,” Margaret said as she picked up her purse and headed out.</p><p>Logan watched his roommate leave and turned to Caroline, who had a wicked smile on her face.</p><p>“Strip,” she said.</p><p>“What?” Logan asked.</p><p>Caroline took a step closer and her face hardened. “Strip. I want to see your panties.”</p><p>Logan considered refusing, but only for a moment. There was something about Caroline that he found a little frightening and he suspected she would relish the opportunity to make him suffer in a truly painful manner if he disobeyed.</p><p>He stripped as Caroline stared with her hands on her hips. She didn’t move and her gaze never left his body. She smiled when Logan revealed the navy blue lace panties he’d put on that morning.</p><p>“I didn’t believe Margaret when she told me about you,” Caroline said as she stared at Logan’s panties. “Not at first, at least. I didn’t think it was possible a man would steal his roommate’s panties because he wanted to wear them. I didn’t think it was possible a man would enjoy wearing panties.”</p><p>Caroline’s gaze returned to Logan’s face and she smiled. “I guess I was wrong, though. Men like you do exist.”</p><p>She stepped closer and Logan felt his heart rate increase. Caroline was a wild card. She could subject him to all sorts of pain and humiliation or she could have him get dressed and they’d spend the night watching TV together. It seemed that anything was possible.</p><p>“You’re quite small,” Caroline said. “Your cock, I mean. It’s quite small. Embarrassingly so, really. Have you actually fucked someone with this thing?” she asked while reaching out to squeeze his soft dick through the lace of his panties.</p><p>“Yes,” Logan answered.</p><p>“You haven’t made anyone cum with your cock, have you?” she asked.</p><p>“I think I have,” he replied.</p><p>Caroline laughed and squeezed his cock again as Logan felt it come to life. “I seriously doubt it,” she said. “Women don’t care for dicks this small. My ex-husband was an asshole, but at least he had a big dick that I enjoyed. I can’t imagine what our marriage would have been like if he was saddled with this disappointing excuse for a dick.”</p><p>“What happened?” Logan asked as he tried to change the subject.</p><p>“With my marriage?” Caroline asked as she moved behind Logan.</p><p>“Yes,” he replied.</p><p>“I married a man,” she said.</p><p>Logan thought there would be more to her explanation, but Caroline left it at that.</p><p>“Sorry, but I don’t understand,” he said.</p><p>“You’re a man. How could you possibly understand?” Caroline asked. “Think of yourself, Logan. Imagine you were married to Margaret. Imagine she caught you stealing her panties. Imagine she caught her husband jerking off in them.”</p><p>“Did your husband steal your panties?” Logan asked.</p><p>Caroline swatted his ass hard enough for Logan to cry out in pain. “No,” she said. “My husband was a man, which means he was a disappointment. It means he couldn’t help but surrender to his cock. It means he let his need to spill his seed indiscriminately ruin our marriage.”</p><p>“He cheated on you?” Logan asked.</p><p>Caroline swatted his ass again. “He did,” she hissed.</p><p>Logan empathized with Caroline’s ex as pain emanated from his ass. She seemed like a harsh woman and he wondered if it would be possible to have a satisfying sex life with someone like that. He didn’t dare vocalize those thoughts, though.</p><p>“I’m sorry he cheated on you,” he said.</p><p>“Thank you, Logan,” Caroline replied as she rubbed his ass. “Do you have any satin panties?”</p><p>Logan smiled as he thought of the pink satin panties he’d recently purchased. “I do.”</p><p>“Go change into them for me,” Caroline ordered.</p><p>Logan headed for his bedroom, where he changed into the satin panties. He savored the way they felt in his hands and how pleasing it was to pull them. He loved how snug they fit and how they clung to his cock and balls, leaving a telltale bulge in the front.</p><p>“Those are lovely,” Caroline said as Logan returned to the living room. She’d poured herself a glass of wine and was seated on the couch with her legs up on the coffee table. “They make your little cock look absolutely adorable.”</p><p>Logan looked down at the bulge in his panties and found it impossible to deny that his cock looked rather small.</p><p>“Masturbate for me,” Caroline said. “In the panties. Rub your cock like it’s a clit.”</p><p>Logan stood in the middle of the living room and rubbed his cock through the panties as Caroline stared at him and sipped her wine. He felt like her toy and it was surprisingly thrilling.</p><p>“Do you understand that you have a useless little cock, Logan?” Caroline asked.</p><p>He nodded.</p><p>“Do you understand that even when your little cock is hard it’s useless? That a dick that small can’t possibly please a woman?”</p><p>He nodded again.</p><p>“Are you flexible, Logan?” Caroline asked as he continued to play with his cock.</p><p>“Kind of,” he replied.</p><p>“I want you to try and suck your cock,” Caroline said with a naughty smile. “Right now. On the floor. Get down and see if you can suck your worthless little dick.”</p><p>Logan dropped to the floor and pulled his panties aside, freeing his small but fully-erect cock.</p><p>“Flip your legs up,” Caroline said. “Put them behind your head and try and suck that sad little dicklet.”</p><p>Logan lifted his pelvis into the air and rolled his legs backwards. His feet reached the floor behind his head and his cock got surprisingly close to his mouth. He was several inches short, though, and no matter how far he bent or how much he craned his neck he couldn’t quite get there.</p><p>“That’s a shame, Logan,” Caroline said. “I really wanted to see you suck your dick. You should have wanted it, too, because I don’t see many blowjobs in your future. Nothing will dry up a woman’s pussy like going down on a guy with a tiny dick. It’s easy when a guy is small, but there’s something about it that’s just kind of sad. It’s like blowing someone that’s not a real man, you know?”</p><p>Logan’s legs were still bent behind his head as he looked over at Caroline and tried to nod. She hadn’t given him permission to unfold his body and he was committed to doing as his babysitter desired.</p><p>Caroline swirled the red wine in her glass and smiled. “I think you should be punished for your failure. I think you should piss in your mouth.”</p><p>“I’d rather not,” Logan said.</p><p>“That’s precisely why I want you to do it,” Caroline replied as she stood up. “Now piss in your mouth or I’m going to spank your ass until it’s bruised. Don’t worry if you miss some of it. It’s a hardwood floor and piss cleans up easily.”</p><p>Logan looked at his still-erect cock and tried to decide if he’d rather take the spanking or piss in his mouth. Ultimately, he decided that the humiliation and unpleasantness of pissing in his mouth was a better choice than the pain of a spanking.</p><p>Logan opened his mouth and did his best to aim his cock correctly in the hopes of actually filling his mouth instead of making a mess.</p><p>Caroline smiled and sipped her wine. “Do it, panty boy.”</p><p>Logan unleashed his bladder and the piss hit his chin and dripped down his neck before he redirected the stream. It hit his tongue and the back of his throat, making him cough some of it up before getting the direction just right. Soon enough Logan’s mouth was full of steaming hot, pungent urine.</p><p>“Swallow,” Caroline demanded as he cut off the flow. “Swallow your piss and finish your punishment.”</p><p>Logan closed his mouth, girded himself against the horrible taste, and swallowed. He coughed violently as his legs remained above his head, his body bent like a pretzel.</p><p>“That was lovely,” Caroline said with a smile. “Maybe I’ll let you drink my piss before the night is over. Would you like that, Logan?”</p><p>He shook his head. He had no interest in consuming more piss.</p><p>Caroline smiled and knelt next to Logan. “Would you like a reward?” she asked.</p><p>Logan nodded vigorously.</p><p>“Stay right there and play with that cute little dick of yours,” Caroline said.</p><p>She stepped over Logan and walked down the hallway. He played with his cock as she turned into Margaret’s bedroom. Just a few moments later Caroline reappeared with a small dildo in her hand.</p><p>“It looks so simple,” Caroline said as she put her glass on the coffee table. “But this little toy can provide such pleasure. I’m sure it’s given Margaret countless orgasms. Do you think it can give you an orgasm, Logan?”</p><p>“I don’t know,” he said.</p><p>Caroline dropped to her knees in front of Logan and ran her hands up his thighs as he continued to slowly stroke his cock.</p><p>“Would you like to find out?” she asked.</p><p>He nodded.</p><p>Caroline pulled Logan’s pink satin panties aside, spread his ass cheeks, and spit on his asshole. She lifted the long, thin vibrator into the air, twisted the base, and turned it on. The low, delightful sound of buzzing filled the air as Logan realized what she intended to do with the toy.</p><p>Before he could object Caroline penetrated him with it. He yelped as she filled his asshole, but it didn’t take long for the pleasure of the vibrations to spread through his loins.</p><p>“Oh, wow,” Logan said as he closed his eyes and stroked his cock a little faster.</p><p>“It feels good to get fucked, doesn’t it?” Caroline asked.</p><p>Logan nodded.</p><p>“Yeah? Do you like it, Logan? Do you like getting fucked?” she asked.</p><p>“Yes,” Logan said.</p><p>“Do you want it harder? Do you want me to fuck you harder, panty boy?” she asked.</p><p>He nodded.</p><p>“Say it, Logan.”</p><p>“I want you to fuck me harder,” Logan said.</p><p>Caroline pumped the vibrating toy in and out of his asshole as Logan jerked off with his legs pinned behind his head. It was a little hard to breathe in that position, but the pleasure in his loins was astounding. He had no idea that his night with a babysitter could be so thrilling.</p><p>“Are you going to cum, panty boy?” she asked.</p><p>Logan nodded. “Yes. It feels so good.”</p><p>“Have you ever taken a facial, Logan?” Caroline asked as she pumped his ass even faster and harder.</p><p>“No,” he said.</p><p>Caroline smiled as Logan realized that there was only one place for his cum to go. Of course it was going to land on his face.</p><p>“It feels fitting, doesn’t it?” Caroline asked as she reached up to play with his balls while fucking him with the toy. “This is how a little panty boy bitch like you should cum, isn’t it? You should blow your load all over your face, shouldn’t you?”</p><p>Logan stroked his cock faster. His orgasm was coming. There was no way to avoid it. He was going to cum on his face.</p><p>Caroline leaned a little closer and squeezed his balls hard enough for it to hurt. That didn’t stop Logan from cumming, though.</p><p>He grunted and his cock exploded. A huge dollop of cum landed on his forehead as pleasure coursed through him. A heavy dose of humiliation followed as more cum hit his face. Some landed in his mouth, some on his eye, and some on his cheeks as Caroline continued to pound his ass with the toy.</p><p>“You look better with cum all over your face,” she said as the toy moved in and out of him. “You really are meant to be a cum-soaked panty boy.”</p><p>Caroline squeezed his balls a little harder and Logan noted that she seemed to find genuine pleasure in his suffering.</p><p>“Was that a good orgasm?” she asked. “Did you enjoy cumming all over your face?”</p><p>Logan nodded.</p><p>“Good,” Caroline said as she stood up, placed the vibrator on a tissue, and unbuttoned her pants.</p><p>Logan watched as she lowered her pants and panties, exposing a rather lovely looking pussy.</p><p>“Put your legs down,” she demanded.</p><p>Logan lowered his legs until he was lying flat on his back. Caroline stepped over his head and lowered her pussy onto his face. Almost immediately she began to ride his mouth, smearing his cum over her pussy lips and his face and making a spectacular mess in the process.</p><p>“Just stick your tongue out and stay still,” she said.</p><p>Logan did as he was told and Caroline continued to move her pussy over his face in small circles. He felt his juices mixing with hers and coating him in a sticky combination of their bodily fluids.</p><p>“Mmmm, I’m going to have to babysit more often,” Caroline said as her thighs began to tremble on either side of Logan’s head.</p><p>He was being used. He’d been humiliated and made to cum and now he was being used as she made a mess of him while getting off. He felt gross, but there was something a little bit thrilling about it too.</p><p>“That’s it,” Caroline said. “That’s it, make your babysitter cum. Make me cum. Make me cum, panty boy!”</p><p>She climaxed a few moments later and a slippery liquid seeped out of her pussy, down Logan’s cheeks, and onto the floor beneath him, mixing with his piss and cum and creating a particularly nasty concoction.</p><p>The moment her orgasm passed Caroline stood up, put her panties and pants back on, and said, “Get on your hands and knees in front of the couch. I want to use you as an ottoman.”</p><p>Logan moved to his hands and knees and crawled until he rested in front of the couch. Caroline sat and rested her legs on his lower back, using him as furniture just as she’d promised.</p><p>“You’re wearing that mess on your face until Margaret gets home. I want her to see what a nasty little pig you are,” Caroline said with a laugh as she turned the TV on. “Until then you can be my furniture.”</p><p>Logan hoped Margaret’s date wouldn’t go too late.</p>