18 comments/ 393095 views/ 21 favorites Cumming on Mom By: tendernips I couldn't wait for my mother's car to pull out of the driveway. She was headed for a three-day conference about 200 miles from here. I had just returned home for the summer after my junior year in college and was eager to relive some of the favorite masturbating sessions of my youth. They usually involved some form of crossdressing. Twenty minutes after my mother had left, I began to explore her walk-in closet and her dresser drawers. As a 45-year old divorced professional woman, my mother's wardrobe and shoe selection were extensive. I soon found what I wanted. I took the silkiest pair of pantyhose I could find and put it on. My cock was beginning to get hard, but I was determined not to let this distract me just yet. Afterwards I looked at my mother's shoes and boots, and decided to try on a sexy pair of knee-high leather boots with three-inch stiletto heels. They were extremely tight but, after several tries, I was able to pull up the zippers on both boots. I took a look in the full-length mirror that stood in one corner of my mother's bedroom and decided that I needed to find a tight skirt. From previous masturbating adventures I knew that my mother had a sexy knee-length leather skirt that barely fit me. I eventually found it again. I stepped into the skirt and pulled it up to my waist. However, I must have gained a few pounds in college because it took me awhile to pull up the zipper. But the leather skirt was very tight and looked fabulous. Again, I looked at myself in the full-length mirror. By now my cock was crying out for some serious attention. I rubbed it slowly for about a minute, but I had other items belonging to my mother to retrieve. Among them was a pair of sandals with four-inch heels. My cock knew them all too well because I had fucked the toe holes – large enough to accommodate my cock - numerous times. I also put on a pair of my mother's leather gloves because my cock loves the feel of cold leather. I attached one of the sandals to the post of my mother's bed. The other I held in my right hand for future use. I pulled up the leather skirt, lowered the pantyhose, and inserted my cock into the toe hole of the sandal on the bedpost. The feeling was fabulous as my pre-cum lubricated the bottom of the sandal, allowing my cock to slide back and forth easily. I lubricated the heel of the other sandal with my saliva and inserted it carefully into my asshole. The feeling of having my anus penetrated almost made me cum, but I didn't want to just yet. I withdrew my cock from the sandal and decided to lie on the carpet in front of my mother's bed. I brought my knees and feet over my shoulders so that my cock was directly over my face. Having found the right position, I opened my mouth as a target for my cock. After a few more strokes, my cum shot out of my cock's head, hitting me in the face and landing on my tongue. I swallowed my own cum and straightened out on the carpet after my lengthy masturbating session. The boots and the leather skirt were beginning to hurt and I slowly took them off. Afterwards I headed for the shower to clean up my cock and my face. At the time, I thought I heard a car door slam, but I felt secure in the knowledge that my mother had left over an hour ago. A couple of days later, my mother returned from her conference and asked me to help her carry her work-related materials and several department store bags up to her bedroom. I did as I had been told. Once inside her bedroom, my mother told me that she had returned to the house three days earlier because she had forgotten her cell phone. I was beginning to fear the worst. My mother continued to tell me that she had walked upstairs, seen me fuck her sandal, and making myself cum in my mouth. While I was dying from embarrassment, my mother assured me that she did not object to anything she had seen. Masturbation, she said, is healthy. She then pulled a fantastic leather mini-skirt out of one of the bags and told me to put it on. She had seen me struggle with her skirt and decided that I needed my own. The skirt fit perfectly. She also produced a pair of red knee-high patent boots with 4-inch heels. The fit was still tight, but they were clearly several sizes bigger than my mother's boots. By now my cock was rock-hard. My mother told me that I could masturbate if I wanted to and should not feel ashamed. I pulled my cock out from under the leather mini-skirt and began to stroke it slowly and deliberately. After a few minutes I realized that I was close to cumming. Throwing all caution to the wind, I asked my mother if I could cum on her tits. With a smile and without hesitation she opened her white blouse and pulled two beautiful, medium-sized breasts from her bra. She held them up and pushed them in my direction. I came almost immediately, covering my mother's boobs with my hot cum. To clean up the mess I had made, I licked my cum off both tits. "That's horny," she said and made her breasts disappear into her bra. "Now let's have dinner." Cumming on My Sister's Face Holy fuck. I thought, as I swiped my thumb across my sisters iphone revealing yet another nude selfie. This one was from above as she held her blonde hair up and pouted in that stupid duck-face way that teenage girl do these days. Claire was three years younger than me. She was eighteen and she was the biggest pain in my ass you could imagine. She was the 'it' girl in her high-school and she walked around like the world owed her a fucking debt of gratitude with her short skirts and her blonde hair and her fake tan. Don't get me wrong, I understood why she acted like this, she was hot, sexy actually but god damn did she know it!? She treated me like shit, always whining at me when she decided that it was her turn to watch TV or screaming through the bathroom door when it was her turn to use the shower. But now I had this! She had left her phone in my room after explaining that her friends were coming over and I'd better not 'embarrass her' or even show my 'stupid face'. I plugged the phone into my laptop and copied all seven pictures onto my desktop. I then plugged my phone in and moved the pictures into its memory. This was going to be awesome. Mom and dad had left that day and were gone for the entire weekend. It was their anniversary and Claire had decided to have a few friends over to get drunk. Fine by me. I was going out for some drinks with Kevin anyway but first I knocked on Claire's door. "You left this in my room," I said and held out her phone. "Oh, shit. I was looking for that," she replied and grabbed for it. I pulled it away. "Fuck you, creep." She said and grabbed the phone out of my hand. I walked away. # It was around my fourth beer that I decided to send the first picture to my sister. "What you doing?" Kevin asked me. "Oh, nothing, just texting someone," I said. "A girl?" he asked. "Uh, yeah, actually, it is." She replied within a minute. YOU PRICK! DELTE THEM NOW! She sent. No way. I replied DELETE THEM OR I'LL FUCKING KILL YOU! She said I think I'll put them up on facebook. I said. There was a long wait in between this message and the next but finally.: What do I have to do to get you to delete them? I'll be back later with some suggestions I sent. Smiling I got back to my beer. "What are you grinning about?" Kevin asked. "Are you gonna get laid? Is she hot?" "She's pretty fucking hot, Kevin," I said And you know what? I might just get laid. I thought. # I got in at around 1AM. Claire was sitting on the couch. Her friends had gone home. "Give me your phone right now," she said standing up from the couch. She was wearing her blue pyjama shorts and a yellow vest, she looked incredible. "Claire, you think the only copy I have is on my phone? Don't be stupid." She ran a frustrated hand through her hair. "Mike, listen, I need you to delete those pictures. What do you want me to do?" "That's a very good question, Claire. How about you start by not being such a brat all the time?" "Fine, I'll work on my attitude, I know I can be kind of a bitch sometimes." She pouted. "Yeah, you can be a bitch sometimes and you're also kind of a slut judging by these pictures!" I said. "You're right, if you promise to delete the pictures I'll promise to be less of a slut." "Now, hang on a second. I only pointed out that you were a slut. I didn't say I wanted you to stop being one," I said and smiled. "I don't understand," She replied. "Well, perhaps in a situation like this, being a slut might actually work to your advantage." "What are you saying?" "I'm saying that being a slut might get these pictures deleted from my phone and from my computer." I said and undid my belt. "Mike, you're fucking crazy. There's no way that's happening!" She said and turned to walk towards the stairs. "I wonder how many people in my contacts would like these pictures? Oh, look, there's a 'select all' option but that would include Mom and Dad! I better not select that!" I mocked. She stopped at the foot of the stairs but didn't turn around. "What would I have to do?" She asked quietly. "Well, why don't you come over here and start by taking off my pants and I'll let you know when you've done enough." I said. She stood still for a few seconds longer before taking a deep breath. She turned around and walked towards me, her blonde hair bouncing in unison with her perfect, firm tits. She got down on her knees –which made my cock twitch in my pants- and grabbed at the button on my jeans. She expertly unzipped and then pulled them down until they were around my ankles, she hooked her fingers into the waistband of my boxers and then looked up at me. "Are you sure there's no other way?" She pleaded. "I'm sure," I smiled. "Fuck it," She said and pulled my boxers over my growing cock. It sprang out at her and she stared at it with her mouth open, obviously impressed by its size. "N...Now what?" She asked without breaking her gaze from my shaft. "Oh, I think you know what to do next," I said. She reached out both hands and grabbed it about half way up. She slowly stroked it up and down, deliberately and expertly, still staring intently at the purple head which seemed to inch closer and closer to her mouth with every stroke. "I can't believe I've got my brothers cock in my hands," she marvelled. "And I can't believe how fucking big it is!" For the first time since she'd released it from my boxers, she looked away from my rock-hard dick and into my eyes. "Wow." She stuck her tongue out and licked the tip, a string of clear pre-cum strung out and she used her teeth and lips to fold it into her mouth. "Mmmm," she moaned and then opened her mouth wide to engulf the tip. She gave it an exploratory suck, satisfied with the taste she took it deeper, about half way, her cheeks sucked in as she slid it back out until just the tip was between her lips. "That feels so fucking good," I moaned. She popped my penis out of her mouth and smiled. "You like it when your little sister sucks on your cock?" She asked. She was enjoying it! Holy shit, she was enjoying it. "I love it when my little sister sucks my cock. Keep going." She did, this time she took the whole thing, all seven inches until she gagged and then she began sucking and stroking at the same time. I reached down and grabbed the bottom of her yellow vest and pulled it over her head, she raised her arms up to help and then got right back to work on my big, hard, veiny dick as I grabbed handful of her firm tits. She spend up, I could feel her tongue wrapping around the head of my prick and then probing the slit, in and out of her expertly sucking mouth faster and faster. I wanted to fuck her, I really did but I quickly realised that wasn't going to happen, I was already close and what she said next pushed me even closer. "Do you want to cum all over your sister's face? Huh? Does my big brother want to cum all over my pretty face?" Fuck I knew she was a whore but this was insane. "Oh god yes. I want to cum on your face." She slid my dick out of her mouth and kept jerking it as she moaned and sucked my balls into her mouth, she sucked hard, almost enough to hurt but she counteracted it by jerking me even harder. "I'm going to cum!" I told her and grabbed my cock out of her hand so I could jerk it out onto her face. She lowered herself down so that her face was perfectly in line with the tip of my dick and she smiled, waiting for the load. It built up like nothing I've ever felt before, her beautiful tits, that flat stomach, the little bits of spit around her lips that had spilled out while she was sucking me and that god damned smile on her beautiful face. I fired the first load almost clear over her head. It caught the top of her forehead and some went in her hair. The next shot of thick, gooey cum hit her left cheek and her smile widened, the third hit her across the nose and she opened her eyes, just as the fourth spurt blasted out she engulfed my penis into her mouth once again, she sucked even harder than before, drawing the last few loads deep into her throat and sucking out all she could get. She swallowed and then slurped my cock back into her mouth moaning as she did. She dragged my penis into the inside of her cheek and let it slop out of her mouth. "Your cum tastes so good," she said still smiling. "You suck cock so good," I replied. "Thanks bro. So, you're going to delete those pictures?" "I was thinking that we've still got two nights until Mom and Dad are back. Maybe I need more time to decided when you've done enough." I replied. She kissed the tip of my dick one more time. "I'm sure I'll find a way to convince you," she said and stood up, grabbing her vest as she did, and walked up stairs.