15 comments/ 104439 views/ 53 favorites They're My Sister's! By: grgy56 I've always had a "thing" for Women's underwear; panties, bras, stocking, lingerie, the works. When I was growing up, I often donned my Mother's sexy stockings and panties when alone in the house. Not that I had any sexual feelings towards my Mother, I just loved having my body surrounded by silk and satin. The feeling was amazing. Later, my Mother kind of went slack and didn't bother buying new frilly things as the old ones wore out. Guess she couldn't be bothered anymore after Dad took off somewhere. Granny underwear did not do anything for me. My sister Cheryl is a gorgeous, 24 year old, "up and coming" secretary who worked at a law firm. She always dresses to the nines to go to the office; nothing overly sexy but professional with that hint of "je ne sais quoi." Always stockings and never pantyhose which are rinsed and hung to dry in our adjoining bathroom. Cheryl is about 5 years older than I but we are about the same height, 5' 7" with similar bodies build-wise 35-26-36 except she had busts. 35-C's to be precise. Not into sports or anything, I was pretty slender for a guy. The laundry was common loads and we often got our clothes mixed up. I would put on a pair of jeans not even realizing they were hers until much later. Sometimes I would find a pair of her panties mixed with my briefs. If I was really lucky, they would be a sexy thong or T-back. I would wear them around and jerk off in my bedroom before returning them to their rightful owner. This summer, I went into Cheryl's room a lot while she was at work. I could easily use the common passage through the bathroom to sneak into her room even if Mom was home and "borrow" her set of bra and panties to walk around in. It was a hot mid-July morning. I was bored stiff, literally. I had been surfing nylon stocking porn all morning and had a huge 5-inch stiff in my shorts but was tiring of the same slut poses so it was starting to soften. I needed something else to distract me from my boredom. I made sure Cheryl's and my bedroom doors were shut. I pulled off my t-shirt and pulled down my shorts before entering Cheryl's room. I went over to her dresser where I knew she kept her lingerie and opened the drawer. The sweet, perfume smell wafted upwards into my noses and made my head spin and my cock hard. I carefully moved items around looking for something special and there it was; a full black lace and satin strapped widow under padding support. The back was lace up but the front had hook and eye closures. The stitched-in boning narrowed at the waist and had three stocking straps hanging down on each side. It had to be pretty new since I hadn't seen it before. I brought it to my cheek and took in a deep sniff. I swear I could still smell Cheryl emanating from it. I wrapped it around my body and felt her body warmth, and then with nervous fingers, I managed to hook the front. It fit perfect! Our bodies were identical and I needed no adjustments (other than no breast). I looked and found matching French cut panties. I slipped my right then left foot through and shimmied them up my legs. The gusset cradled my cock clit like it was made for me. I rubbed my pee hole of my uncircumcised cock and felt the pre-cum start to leak. I didn't want to dirty my new panties like this but it was too late. It felt too good and big wet spot started to form. In her stocking drawer, I found a pair of black fishnets. I sat on the edge of her bed and rolled them up my hairless legs. Not that I shaved them, I just had little body hair to speak of other than my head and a sparse patch of pubic. I clipped the suspenders even though the stocking were really stay ups. I just love the feeling of garter straps on my legs especially as I walked. I looked in the mirror and admired my reflection. My body was perfect. Pointing my toes really showed the slim muscles of my legs, but the fishnets really didn't go with the outfit so I removed them. I rummaged through her draw again and found a pair of sheer black stockings. The toes and heels were reinforced with pink and had Cuban heels. The tops were pink lace with a pretty pink bow. I slipped them on and clipped them. Perfect. I went to her closet and found a short skirt to put on. Too short for her business attire but perfect for evenings out. "Shoes! I need shoes!" I said to myself. I bent over to look in her closet and found a number of 4 ½ " heeled strappies. I searched and found the ones; black with a small open toe. I reached down to pick them up when I heard a familiar voice. "Nice ass Cheryl." It was my best friend Chris. I froze. I didn't know what to do. What would I say? Should I stand up or stay bent over and try to ignore him. "Have you seen Sam? Your Mom said he was up here." Chris asked. I slowly straightened up and turned around with my shoes in hand. Chris looked from my toes upwards to my head and down again. His expression went from grinning excitement to jaw dropping amazement. "Sam? Is that you?" Chris was shocked. "What the fuck is ....?" "Err. Hi Chris." I was totally red faced. "Umm. How did you ....?" "Your Mom let me in and told me you were in your room. When I opened your door and couldn't find you I saw Cheryl, I mean you bent over in her closet." Chris said. "Why are you dressed like that?" "They're Cheryl's clothes." I answered. "I like wearing women's lingerie. It feels so nice against my skin." Chris is my best friend since grade school. Neither of us was athletic and was of similar built, maybe just a tad taller. Neither had a lot of life experience. As we grew up together, we would jerk off together to the free internet stocking porn. Sometimes we would jerk each other off, but I never let Chris know of my other fetish of wearing lingerie. "I think you look great!" Chris told me. "Even sexy." "Fuck off!" I retorted. "You think I'm a weirdo!" "No, really, I think you look hot. Put the shoes on!" He instructed me. With trepidation, I slipped on the black strappies. The heels made me taller than Chris. "Fuck Tim. From the neck down, you look like a real hot slut!" I didn't know if that was a compliment or not. I took it as a compliment. "You think so?" I asked as I went towards him with a practiced stride. I stared down into his brown eyes. Suddenly I felt his arms around my waist and him pull me towards his body. He grabbed hands full of my ass and started to grind himself into me. I could feel his stiffness grow against my leg. I'm not sure why I did it but it felt so right. I held his head with both hands and gave him a deep, hard, wet, French kiss. His tongue danced with mine as we exchanged saliva. I dropped to my knees. The tent in his shorts belayed any shock he may have initially had. I unbuttoned his shorts and let them fall to his ankles. We had long both agreed that when we were together to surf for porn, we would not wear underwear (stupid I know, but it got in the way when we whacked off together). His boner was proud. It was the same length as mine but a bit thicker (we measured them). I looked up at Chris. He smiled and nodded. I grabbed the base then opened my mouth and closed it around the head. It was really the first gay thing we've ever done. It was a bit salty at first, but the texture was amazing; soft yet firm. Slowly I started to move my head back and forth like I watched on the porn site. I was able to take in almost half before Chris grabbed the back of my head and starting thrusting his hips into my face. I had to relax my throat to avoid gagging on him and then I was able to take the rest with a little effort. "Fuck Sam!" Chris exclaimed. "You're an amazing cock sucker!" Not that either of us really knew from experience, just from watching the internet. He continued to pump his cock in and out of my mouth. His head fell backwards as he gave me a few hard and final thrusts with his hips. His white hot goo spurted out and filled my mouth. I had nowhere to spit it out in Cheryl's room so I just swallowed it. My tummy now filled with Chris' cum. He slowly pulled out his cock from my mouth, but I pulled him back and finished cleaning the remainder of his spunk off his shaft. "Wow!" Was all Chris could muster. "That was a huge load Chris." I told him as I stood up. "I don't ever remember you shooting that much even when we jerked each other off!" By then, my boner was tenting my skirt. Chris reached under my skirt and between my legs. I spread my feet a bit as his hot hand started to caress my balls and the underside of my shaft. Without a word, Chris dropped to his knees. His fingers grabbed the sides of my panties and pulled them down my thighs. The suspenders prevented him from pulling them down further. Chris opened his mouth. I plunged my cock into his waiting throat. There was no gagging reflex. "Chris, you took the whole thing without gagging!" I said. Chris stopped sucking for a second. "I've been practicing on a dildo to see how much I could take." "What?" I asked. "You what?" "I bought an 8-inch lifelike cock started throating it." He continued. "You're a little smaller by comparison so I can take you easily." With that said, he went back to sucking my cock. I could feel the head of my cock hit the back of his throat. He took it all. His tongue even lapped my balls as his nose mashed into my sparse pubic hair covering. I was just about to cum when Chris stopped. "Turn around." Chris told me. "Bend over face down on the bed." I did as he said as I felt Chris lift my skirt over my hips. His fingers spread my ass cheeks. Then I felt the wetness of his tongue prod my asshole. Chris could extend his tongue out almost 4 inches. He used all of it as it pushed into me. "Fuck Chris!" I gasped. "Don't stop!" as I felt his tongue wiggle inside. I wanted to whack off, but I couldn't reach it. I really needed to cum badly. Chris suddenly stopped. I turned around to complain but as he stood, I noted his cock was stiff again. His left hand held me tummy down on the bed. He used his feet to spread my legs wider. He took his monster in his right hand and moved it towards my virgin hole. I felt the fat head press against the rear opening. I turned and watched as a big gob of spit fell on to his knob. Chris slowly started to work it into my hole. Unbelievably he was able to enter my well lubricated entry with only a bit of effort. First the head spread the opening a bit more; he pulled back slightly and then pushed in a little firmer. I felt it pop in. A slight pull back then Chris pushed it in deep and all the way. "Fuck Chris!" I moaned. "That feels so fucking good!" Chris started pumping me slowly at first, but gradually picked up the rhythm before he started to really pound my ass. "Sam!" Chris shouted. "I'm going to cum again!" "Do it Chris!" I moaned back. "Give it to me!" "I'm going to cum in your ass." Chris grunted. "Right now!" With a final few hip thrusts, I felt his shaft pulsate as his balls emptied into my bowels as mine emptied onto the bedspread and carpet. Chris collapsed on top of me as we both panted for breath. His deflating cock slipped out of my backdoor as I could feel his second load of day dribble out and down my legs. "That was incredible!" I gasped. "Yes it was!" said a strange voice. They're My Sisters Too! To recap, I sneaked into my sister's bedroom through the adjoining bathroom and dressed in some of her clothes. My best friend Chris caught me. He was shocked at first but then quickly recovered especially after I sucked him off and he exploded in my mouth. After a short recovery, he ended up fucking me in end. Then with Chris' cum dripping out of my ass .... "That was incredible!" I gasped. "Yes it was!" said a strange voice. Well actually not strange but not Chris' voice. We both turned around to look. Standing there with hands on hips and legs slightly apart was my sister Cheryl. She was dressed in a fitted business blue pinned striped suit. The skirt was about 3 inches above her knees. The jacket covered a crisply pressed, white Italian cotton shirt unbuttoned three down. Chris looked at me then at Cheryl then at me again. Before I could say anything, Chris grabbed for his clothes and tried dashing out of the house. As he scrambled to his feet, Cheryl tripped him and dropped him face first. She placed her four and a half inch heeled stiletto in the middle of his back. "Stay there." Cheryl ordered Chris then just turned and stared at me. "I .... Ah .... I can explain." No I couldn't. There was almost nothing I could say that could explain what Cheryl just viewed. Cheryl went to closed her bedroom door, then stood over me and stared; legs slightly spread, arms across her full bosom. I tried to stand up but Cheryl placed her high heeled shoe on my sternum and pushed me to my ass. "Don't even try to go anywhere either!" She ordered me. "What the fuck are you doing in my room? In my clothes? On my bed?!" What could I say? My panties, um her panties were pulled down to my knees; her stockings were wet with Chris' and my cum; my dick was still as solid as when Chris was fucking me. "Cheryl!" I started. "I'm sorry." "What? Sorry you got caught you fucking little pervert!" She screamed. "Sorry my ass. Actually it's going to be your ass that's going to be sorry!" "No. I just always loved to wear women's lingerie. Mom stopped buying sexy things and I knew you had some beautiful stuff so ..." "YOU wore Mom's underwear?" Cheryl said aghast. "You're sicker than I thought!" Cheryl stared at me. "So what about Chris?" I tried to explain further. "Well after you left for work, I snuck into your room and found ..." "My favourite lingerie?" Cheryl finished my sentence. "I thought there was something weird happening to my stuff but couldn't figure it out. It was you, wasn't it?" "Yes it was me." I admitted sheepishly. "Anyway, I got dressed and Chris caught me when I wasn't expecting him. Things just happened. I sucked him off until he came in my mouth. Then he sucked me for a bit until he recovered enough to fuck my ass. That's when you walked in." "Well unfortunately for you, the building had a black out and the air con wasn't working so they closed the building and gave us the rest of the day off." Cheryl told me. "Fortunately for me; unfortunately for you." Suddenly an epiphany stuck Cheryl. She looked directly into my eyes and smiled. "Chris, get dressed and go. I'll deal with you some other time." Chris my ever faithful BFF (Bum Fucking Friend) gathered all his clothes and took off faster than Bolt on steroids. I'll deal with him some other time too. "Sam! Stand up!" She ordered. I obeyed. My shriveling penis was still dripping cum. "You know, you're kind of cute all dressed up." I could see her mind work. I didn't like what I was seeing. "Pull up your panties. I don't want to see your puny little excuse of a dick." I pulled them up and fixed my now shrunken penis beneath them. "You can keep them, too. I don't want them after you soiled them with your cum!" Cheryl said with disgust. I immediately started feeling a surge of blood rush towards my groin. Cheryl watched my growing erection with amazement. "Well from your excitement, it seems like you really like wearing girlie things don't you." There was no denying Cheryl's statement. The little boner I sported under my panties was extremely obvious. "Lay down on the bed.... Face down." I looked at her in puzzlement. "Do it now or I'll tell Mom!" I was warned. As I laid down on Cheryl's bed, I heard her move around to her bedside table, slide open the drawer and retrieve something. She then climbed on the bed and straddled me across my back. I felt her buckle a strap around my right wrist, then my left before pulling my arms behind me and locking them together. "What are you doing to me Cheryl?" I asked as she dismounted me. "Well something Greta and I play around with when we're alone." Cheryl responded. "Now to make sure you can't deny anything..." "Click! Click! Click!" "Huh?" I muttered as I turned my head towards the sound. Cheryl was taking pictures of me with her cell phone. Pictures of me dressed in my hot lingerie. "Now for some frontals!" Cheryl forced me on to my back. "Click! Click! Click!" "There! If I ever have any problems with you, I'll send these to all your friends!" Cheryl chuckled. "Click! Click! Click!" Close ups so there was no mistaking me for anyone else. She pulled one of the leg holes over my swollen dick. "Click! Click! Click!" "Just to show your friends you really enjoy dressing like a sissy girl!" Over the weeks, Cheryl enjoyed her power over me. She made me wear some sleazy French maid costume she had from Halloween. It included a short skirt, tight lace up corset with a push up bra, some with black fishnets and garters and a pair of black high heels. I cleaned her room and did all her chores including cleaning the bathroom. Actually I kind of enjoyed it. But the best was when Cheryl made me wash out all of her sexy underthings. I slowly and carefully rinsed everything afraid she would stop me if I did it wrong. Sometimes as a reward, Cheryl would buy or give me some lingerie of my own including a pair of pink lace panties, white stocking with satin garters and matching bra and one of her silk camisoles. Other times, Cheryl would lay on her bed and watch me jerk off while dressed as her maid. While she was at work, Chris would still come over almost daily. I'd show him some of the outfits Cheryl bought me. It was fun parading in front of Chris dressed in my girlie things. I would pretend to be a fashion model and let Chris feel me up. Cheryl started making me shave all over so my skin was soft and smooth to the touch. Chris would always get so hard and always ended up coming in my ass. One late afternoon, I was dressed in a kind of school girl outfit: white blouse with a red push up bra underneath, a short red tartan kilt and white thong panties. I pulled up a pair of white knee hi's and wore a pair of 5 inch strappy black heels. I kneeled in front of Chris and pulled down his jeans. His cock was already solid. I took it into my mouth and was just starting to take him down my throat when the adjoining bathroom door opened. "Is that all you two do all day?" It was Cheryl. She had caught us again but wasn't as pissed as last time. "Don't let me stop you. In fact, I insist you continue." Cheryl grabbed a chair and sat down as I started to pump Chris' cock in and out of my mouth. Chris for his part didn't skip a beat. His cock remained its optimal hardness as he grabbed the back of my head and started rocking his hips. I peeked over at Cheryl. She had pulled up her skirt over her thighs and was fingering herself through her black panties. Her other hand was under her shirt pulling and pinching her nipples. She signaled her approval to me by staring me right in the eyes and smiling. I dropped to my hands and knees with my ass towards Chris. Chris was a bit wary of continuing. "Chris! Please fuck me from behind!" I pleaded. Chris fell to his knees between my legs. He slowly pulled up the hem of my kilt and flipped it over my ass. He pulled the thong string from between my cheeks and placed the head of his cock on rear entrance. "Do it Chris!" Cheryl told him. "Fuck him like the girl he wants to be." Chris wasn't that big and since he had been fucking me so often now, my ass was use to him and I needed no lube. With some slight pressure, his bulb pushed into my hole. "Oh yeah!" Cheryl moaned. "That's fucking hot! Put it in all the way!" With one slow push, I felt Chris' cock penetrate me as deep as he could go. "Pump his ass!" Cheryl was ordering Chris like she was producing a porno. "Hard! Harder!" Chris was fucking me as hard as he could now. I could barely support myself on my hands. "Fuck Sam!" Chris grunted. "It's still so tight! I'm going to cum!" "Cum in his ass Chris!" Cheryl commanded. "Fill his ass with your cum!" "Arrgh!" Chris grunted as I felt him start to spasm. The first spew entered deep into my bowels. Chris always could shoot huge loads, this one was no exception. It felt as if a quart of his cum filled my ass. The action was enough for Cheryl too. "Fuck YES Chris! Cum in her ass!" Cheryl screamed. "I'm c... c... u... mmm... ing!" I watched Cheryl orgasm as a huge flow of her pussy juice soaked through the crotch of her panties. Chris fell backwards onto the floor. His boner still angry red and pulsing. My ass was still pointing upwards, Chris' cum pouring out and down my legs. After a few moments, Cheryl spoke. "Chris, get out of here before our mom comes home." Chris groggily gathered his shit and left. "Sam." I snapped to attention from Cheryl's voice. "Help me get undressed and wash out my panties. You and Chris made me soil them so you can clean them." I stripped Cheryl and covered her with her kimono robe. I collected her things and rinsed out her delicates. "Hi kids! I'm home!" They're My Sister's Wicked Ways! Thanks for all the great comments. I know this third chapter has been a really long time in cumming but I hope you enjoy this one as much as the others. ***** So the first time I was caught by my sister, I was dressed in some of her sexy lingerie. That was bad enough but she also caught my best, bum buddy (literally) Chris fucking me and cumming in my ass. Cheryl my older, professional, law office working sister, basically made me her sissy maid. Of course, she insisted that since I was her maid, she got me to wear a sexy maid's outfit as I performed the many tasks she assigned me to do. I actually enjoyed it since I got to put on my girlie things and I especially enjoyed washing out Cheryl's delicates. Again, Cheryl came home and again caught me dressed up; this time as a school girl and sucking on Chris' boner. I needed to feel Chris inside me and begged for him to pound my ass. Cheryl had pulled up her skirt and masturbated as she watched us fuck. We all orgasmed together. We had just finished. Cheryl had sent Chris home when we heard, "Hi kids! I'm home!" It was our mom arriving back from a long day as the Vice President's executive assistant at the architectural office. I had just finished rinsing out and hanging up Cheryl's underthings which were soaked with her juices after watching me and Chris but I was still dressed in my school blouse and skirt. In my room, I quickly tried to unbutton my blouse and unzip my skirt but my shaking hands fumbled so much it took longer than it should have. I stood there with them in my hands when I heard... "Hi Cheryl." I heard Mom say to my sister. "Oh, that's a nice gown you have on. Is it new? Feels like silk. "Oh hi Mom. Yeah kind of. I love the way silk feels." Cheryl answered. "I just got home and was changing." "Cheryl, it's a nice kimono, but you have a younger brother around. I think you should make sure to keep the front closed up when you're naked underneath. Or at least close your half of the bathroom door." "Oh Mom!" Cheryl whined. "Where is your brother anyways?" Mom asked. I didn't hear Cheryl reply, but Mom said, "Oh! That's why I mean you should cover up." I started to panic. I shoved my blouse and skirt under the bed pillow but I was still dressed in my red push-up bra and white thong panties. I grabbed my dressing gown and had just managed to wrap it tightly around me but fell onto my bed as Mom entered my room through the common bathroom. "Hi Sammy!" Mom said as she walked over to me as I sat there, bent over and gave me a motherly peck on the cheek. Then she paused for a second, looked at me and gave me kind of a sniff. "Are you feeling okay, honey? Why do you have your housecoat on?" By that time, Cheryl was standing by my side of the bathroom door trying not to laugh. Her kimono hung open showing me her naked body beneath. I started getting a hard-on. I tried to think quickly on my feet, "I, uh... was napping kind of in my underwear and ..." Then it donned on me. "My feet!" I still had my knee highs and heels on. Mom stood up and looked at me. "A nap in the middle of the afternoon? Are you sure you are okay?" She put her hand to my forehead. "Do you think you'll be able to eat some dinner?" I looked over at Cheryl. She was smiling at me. Her index finger was diddling her clit. I could see the wetness form on her pussy lips. "Uh.. yeah Mom. I good. Dinner sounds great." I managed. Cheryl quickly covered up and said "Oh is poor little Sammy not feeling well?" Mom turned to her. "Stop teasing your brother." Mom scolded. "Dinner will be ready in a half hour." After Mom left my room not noticing my feet, Cheryl giggled at me. "Wow that was close, eh?" "Yeah!" I answered in a whisper and I stood up. My gown fell open. "She almost caught me in this! And you standing there fingering yourself was no help either." My hard dick formed a small lump in my panties. "Well come here and lick me clean. It's still a little slimy from watching you and Chris." Cheryl spread her slit apart. Obediently, I knelt in front of her and lapped it clean. Lapping it dry was difficult since she's a bit of a gusher. My face was soaked and dripped on to my chest. "Dinner's just about ready. Come on down kids!" We heard Mom call out. "You don't have time to change." Cheryl said. "Just take off your shoes, but leave your knee highs on. Then come into my room." I did as she instructed. She threw me a couple of things at me. I held them up. The shorts she gave me were her tight white mini shorts that would barely cover my ass. The shirt was kind of a hockey jersey with her university logo on it. "Put them on." "Are you nuts?" I replied. "I can't wear this!" "Mom!" Cheryl called out. "Cheryl, no! What are you doing?" I was fretting. "If you don't put them on, I'm going to tell Mom what you've been doing when she and I aren't at home. Don't forget I have pictures and I know where you keep your girly things." "What is it, Cheryl?" We heard Mom shout back from downstairs. "Okay." I reluctantly agreed. I pulled the shorts up and over my hips. They fit me more like a pair of high cut panties rather than shorts. It felt like half my bum was expose and then I couldn't pull them high enough to cover the waist strings of my thong. I pulled over the shirt. Fortunately it was long and fell to my upper thighs. It looked more like a short dress than a shirt. At least it was blousy enough to hide the fact I wore a bra with stiff C cups underneath. "We're coming down now!" Cheryl called back to Mom. Cheryl had already changed into some baggy sweats pants and a tight white spaghetti strap tank top with a white demi cup bra. Her nipples were rock hard. Cheryl and I walked to the dining room. I was kind of hunched over so the cups of my bra weren't poking out the front. Mom looked at me kind of funny but didn't say anything. She had changed from her professional business suit to a more casual, light summer dress. She was putting the food down on the table. The sun shone through the back patio door. I could easily see the silhouette of her shapely legs through the thin material. "Sammy! How many times do I have to tell you not to slouch and stand up straight?" Mom said sternly. "And what's on your face?" "Yeah! Sloughing makes your bum stick out." Cheryl agreed as she slapped my ass. Her hand pressed against my back and along my bra straps. "Stick out that manly chest of yours!" "That's enough, Cheryl." Mom admonished. Mom didn't even notice what Cheryl was wearing. We managed to have dinner without further incidences or comments, although Cheryl was acting a little strange. Her left hand was always under the table and moving. "Okay kids. Please clean up the table." Mom told us. She left the table and went to the living room to watch some TV and read the newspaper. Cheryl and I cleaned off the table. Well mostly I cleared the table. Cheryl supervised. Every time I kind of bent over, her hand was under my shirt and grabbing my ass. "Nice fuckable ass!" She'd say. In the kitchen, I was up to my elbows in soap suds washing the dishes since our washer was on the blink. Cheryl was supposed to dry but instead stood behind me and pushed me forward slightly. She raised my shirt above my waist and pushed her body into mine. There was a familiar feeling pressing against my rear. "Cheryl..." I turned to her and whispered. "Shhh!" She hushed me. She pulled down her sweats and out popped a cock! Cheryl had been wearing the strap-on and stroking it all through dinner. It looked so realistic. About ten thick inches long with a big bulbous knob. Definitely much bigger than Chris'. My eyes widened. Cheryl took hold of my shorts and panties and yanked them down enough to expose my ass, but my hard little cock was still trapped inside my panties. I spread my legs as wide as I could but my thighs were restricted by my clothes. She grabbed the bottle of dish soap and squirted a generous amount at the top of my ass. I felt it ooze downwards to my aching hole. She kept pouring it on and used her cock to spread it into my crack and on to my ball sack. "My little Sammy girl has been a good little sissy and I think desires a reward. Don't you?" Cheryl asked still taunting me by running her knob up and down my crack. "Oh please Cheryl! I want it! I need it!" I begged. "Please stop teasing me." She used one hand to pull my cheek open and the other to guide her beautiful cock in between. Her tip was almost touching my hole. "Good girl, Sammy." Cheryl pushed a bit forward. My ass hole easily spread open for it, but Cheryl continued to tease me and pulled back. She pushed forward just a bit more before pulling back again. "Is my Sammy slut enjoying this?" Cheryl had pushed into me enough that the wide part of her knob had almost pushed through inside me. "Oh please! Oh please!" I cried as softly as I could. "Cheryl, please I need it all!" Without warning, Cheryl jammed the rest of it up my ass and started to fuck me with all her might. I could feel her harness bang against me each time. "Oh fuck! Oh yes! Cheryl fuck me! Fuck me harder!" I moaned. "Are you kids okay in there?" Mom called out from the living room. "Yeah Mom! Every.. thing.. is.. cool!" Cheryl called back nonchalantly as she continued pounding my ass. She reached under my jersey and grabbed my bra and tits. The roughness of the lace against my nipples was driving me over the edge. I started cumming hard in my panties. "Uuuh...! Uuuh...! UUUH! Uuu...hhhh!" I filled my thong with my white, messy cream. I was completely spent. I leaned on my elbows against the edge of the sink to support myself as Cheryl slowly continued to pump her length in and out of me. Her hand grabbed my now teeny, flaccid dick and smear my cum into me. "What's going on in there?" Mom called out again but her voice was really close. Cheryl pulled out and covered up. She let the back of my jersey fall down and just cover my naked ass. I remained leaning over the sink. Mom walked in the kitchen. "We're okay, Mom." Cheryl said, picking up a glass and pretending to dry it. "Hmm?" Mom looked at us suspiciously. "Look. I just got an email from Jennifer and I need to accompany her on a business trip to Chicago for a couple of days." Jennifer was Mom's boss at the firm. Mom started working there as a secretary, long after Dad left us and she recovered from her depression. She quickly worked her way up the ranks; quicker than most people would have expected. "Oh. Okay Mom." Cheryl answered. "Then, is it okay if I invite a couple of girls over for a girls night?" "Yes, but be considerate to your brother. He lives here too." Mom said agreeing to the request. "Don't worry, Mom. I'll take good care of Sammy!" Cheryl winked at me. Later, Mom called me into her bedroom as she was packing for her trip. "Just wait here. I need to get something from my bathroom." She was dressed in a full length, silk slip that came down to mid-thigh. It looked like she wasn't wearing a bra. Her breasts were still pretty firm for a woman in her forties. While she was in her ensuite, I was able to peek inside her luggage. She had packed a number of very sexy and intimate items. Some of her bras were very lacy with satin. There were both full and demi cup bras. And panties! Matching high, French cut. Lacy boy shorts. Full cheekies. And even a couple of crotchless ones. Six strap garters. And stocking, both very sheer and reinforced toes and heels. There were also a small selection of toys: a small vibrator and an eight inch cock dildo. Mom came back into the room, she paused. While I had changed my outer clothes, Cheryl made me keep on my panties and bra. Mom peered at me quizzically before speaking. "Now, I'll be gone for a couple of days. Don't let Cheryl boss you around too much. But she is older so please do as she says. I'll be back on Saturday." That would be no problem for me, especially when Cheryl allowed me to dress up around the house. "Okay, Mom." I answered. Mom came over and kissed me on the cheek. "You're a good kid, Sammy." She placed a hand on my shoulder and ran it down the middle of my back. I'm sure she could feel the hooks of my bra. She pulled me in and gave me a big hug. Our tits smashed together. "Good night, Sammy." As I turned to leave, Mom gave me a couple of friend pats on the bum. I got back to my room. Cheryl had already laid out some things for me to wear to bed. A cute, white trimmed, baby blue nightie and crotch-less, ass-less panties. The crotch part was tied closed with five, pretty white ribbons. "Get a good night's rest, Sammy. We have a girlie night to plan for." Cheryl kissed me on the cheek.