Check out the first two parts of this series, WHEN SIS CAUGHT ME and POPPING SIS'S CHERRY
As I related before, Mary and I started having sex when she was 14 and I was sixteen. The problem of privacy in a small house with a big family was solved when I discovered one of the neighbors had a heated garage and I knew where the key was kept. I finally got my chance to pop her cherry there late one night. We thought everything would be perfect now, but we were wrong.
Since we started having sex, I had turned seventeen and Mary was on the verge of turning 15. It was now winter, and very cold in Maine. It was a Saturday, and Mary whispered to me that she was getting really horny. I quickly came up with a plan. Grandma was in the living room when I told her I was going skating for the afternoon and turned to all three of my sisters to invite them along. As I expected, the two younger ones weren’t interested in going out in the cold, but Mary said she would like to tag along if it was alright. Since I invited all three, Grandma was not suspicious. I did mention that I had to stop by Mr. Jones’s house and she would have to wait outside as I promised not to let anyone else in the house. Our plan was in motion.
Just in case, Grandma or someone else was watching; I went in and feed the birds while Mary waited outside. Then we cut across the back field toward the skating pond. Once we passed out of sight of our house, we doubled back and approached the garage from the woods in back. There were enough trees and fence to prevent us from being seen as I retrieved the key and let us into the garage.
As soon as we were inside, Mary threw herself into my arms for a passionate kiss. We broke apart to quickly strip out of our clothes in the heated garage. Naked, we lay down on the couch pawing each other and sucking face. I tried to move down to eat Mary’s cunt out and get her wet, but she stopped me. She said, “I’m wet enough already. Just put it in.” My dick had already risen to full strength due to her warmth and caresses. As she rolled over onto her back, she parted her legs. Her pussy was red with desire and glistened with juice flowing out of her hole. She was in heat. I lined up my dick and shoved it to the hilt in one stroke. She gipped me with her tight walls and groaned as ripples in her cunt walls rode up and down my cock. I gave her what she wanted, hard and fast. She panted and yelled for me to fuck her harder, harder. I obliged. My balls were slapping her ass as the juices leaked out of her pussy and trailed down her ass crack. I twisted and pulled her pert tits and she squirmed in pleasure. We had never just flat out fucked so hard before. Rather than tenderness, we express our love with brutal animal passion. Of course, it was not long before I felt the cum rising from my balls. I tried to hold back to time my climax with hers, but it was a losing battle. I told her I couldn’t hold it, and she just said not to. She want my cum now. I jabbed deep and held as my cock jetted load after load of my juice into her.
After cumming, I rolled over on the couch. Mary turned her body around and took my slimy cock into her mouth and started to suck it clean. She moved her crotch close to my face and held her legs open to beckon me to eat her. I looked at her cunt covered in pussy juice and leaking my white cum. Without hesitation, I reached over and parted her lips to see her gaping hole. I leaned in to inhale the aroma of fresh fucked pussy, and was excited by it. A little timidly, I lapped the outer edges of her fold. Her moans encouraged me to lick a little harder. The initial hesitation about sucking out my own load was overcome by the pussy juice taste and smell, as well as the talented tongue action she was giving my dick. Soon I was slurping away without a care. I drilled my tongue into her hole almost scooping out our combined liquids. Truthfully, more got smeared on my face than I swallowed, but I did swallow a copious amount.
Since Mary was considerably smaller than me, I could lick the entire area from her clit to the area between her vagina and asshole. When I would get to the bottom, my nose would be buried in the cleft of her ass. I touched the puckered ring with the tip of my tongue and she jumped. I leaned further and started to lick a circle around the ring. She squirmed again. She pulled my cock out of her mouth to announce she was ready to come. I returned to fasten my lips on her swollen clit and batted it with my tongue. Dipping one finger into her pussy, I coated it in juices. Then I reached behind and shoved my slick finger in her ass. She stiffened and nearly crushed my head between her legs as her body convulsed. I continued to suck and tongue her clit as my finger drilled in and out of her ass. Tremors shook her body as she reached a nerve shattering climax.
Coming down from her high, she rolled over letting my dick plop out of her mouth. I turned to mount her again, but she stopped me. She told me she wanted to feel my dick in her ass this time. I looked around and saw a saw horse over by the tool bench. I grabbed the cover on the back of the couch and placed it over the saw horse. I pulled Mary up and pushed her to lean over the covered saw horse. With her ass so totally exposed, I crouched down and started to eagerly tongue her brown hole until she was yelling for me to fuck her ass. I stood up and shoved my dick to the hilt in her back hole. She grunted and gasped as she lost her breathe from the sudden assault. She put her hands back and pulled apart her ass cheeks so I could get as deep as possible. It was amazing to watch my dick slide in and out of her ass. Each time I pulled back, her ass ring would pull out as it tried to grip my dick only to be pushed back in on the inward stroke. I kept this up for about five minutes before my second load fired. I was more in control this time. I would pull back and then plunge in deep to spurt in her ass, and then pull back again for another plunge and spurt. I shoot three spurts into her before my cock started to deflate. As I pulled out the final time, a dribble of cream ran out to join the mixture from her pussy. Wobbling, she got up and put her arms around my neck. I lifted her to sit astride the saw horse, and bent down to suckle at her tender tits for a couple of minutes. We moved back to the couch and lay twined in each others arms fully satisfied for the moment.
It was fun to just lie together and fondle each other with no rush to get it over before we got caught. She would caress my dick and balls, and I would take a suck or two on her tits as we kissed and enjoyed a restful repose. We didn’t fuck anymore that afternoon, but it was one of my fondest memories. When we figured it was time, we got up and cleaned up before getting dressed. I looked outside to be sure the coast was clear before we hurried out and back into the woods behind the garage. We walked around a little to get our faces red and noses runny as if we had spent the whole afternoon outside before we headed home. When we got home, Mary said she needed to take a nap after all that “skating” and headed off to bed to revisit the memories of the afternoon. Being a male, of course, my first concern was getting something to eat since I had worked up an appetite “skating”. We foolishly thought we had gotten away with it all.
A week later, Mary had another babysitting job. My other two sisters were in a school concert that same night that Grandma wanted to attend. Being a Friday night, both my uncles had plans and Grandpa had to sleep as he had a 4AM shift. So Mary and I went to the dress rehearsal the night before, and I was going to stay home the night of the concert and walk her home after the babysitting job was over. The plan was for Grandma to take the two girls for ice cream after the concert and be home by ten o’clock. Mary was expecting to get out of the babysitting job by nine which would give us an hour of free time to stop by Mr. Jones’s garage. As luck would have it, Mary called at 7 just after Grandma had left. The woman she was babysitting for had gotten sick and came home early. She wanted to know if I could come get her now. I immediately imagined the fun we could have with this extra time. I hurried over and quickly escorted Mary back, but to our secret place instead of home.
Since we were no longer in a rush, we took our time. We undressed and lay down on the couch. Soon our naked bodies were melded into a loving 69. Mary’s talented tongue was working my cock and balls while I licked and sucked her pussy. I played teasingly with her clit to arouse her but not enough to get her off yet. We were so engrossed in enjoying the sensations of each other, we did not hear the door open. Until he spoke, we were unaware that Mr. Jones was there. He gruffly said, “What is going on here?” We sat up in a start. My face was glazed with her pussy juices, and Mary had spittle and pre-cum drooling down her chin. I reached for our clothes, but Mr. Jones was standing between us and them. Mary covered up her nakedness, and hung her head. Mr. Jones scooped up our clothes and said, “I think we should go into the house to discuss this.” I thought he was going to pass the clothes to us. The thought crossed my mind that once dressed, we could run away when we got outside. However, he turned and started out the door with our clothes. He said, “I left you your boots and coats. It’s cold out there.” He left and we stared at each other. We had no choice. We would have to follow him into his house to get our clothes back.
Mary and I looked outside to be sure it was dark enough nobody could see us and then sprinted across the yard to the kitchen door. Once inside, Mr. Jones instructed us to leave our boots by the door. He headed into the living room still carrying our clothes. We followed with our coats tightly wrapped around us. Mr. Jones waved us over to the couch. As we went to sit down, he reminded we did not need our coats inside. Mary looked at me and shook her head. I started to object when Mr. Jones said, “I don’t know whether to call your Grandmother about this, or let the Police handle your trespassing.” I knew we were at his mercy. I shrugged off my coat and sat down on the couch. Mary hesitated, but I nodded for her to comply. She doffed her coat and sat huddled up to me trying to cover up as much of her body as possible. Mr. Jones seemed to be ignoring our nakedness as he continued to ramble, “I knew someone was getting into the garage, but I wasn’t sure who or why. It was easy to see who when I checked the outside cameras. Oh, you didn’t know about the cameras did you? Well, once I saw who was getting into the garage, it was a simple matter of hiding a camera inside the garage and waiting.” As he talked, he was putting a tape in the machine. “Great system,” he continued, “can record up to sixty hours on a bank of recorders. Wish I had been here last Saturday to watch you two in action, but I did enjoy catching up with the tapes.” He started the player, and the TV came alive with images of last Saturday. Everything was there from my pounding Mary’s pussy to fucking her up the ass. “Brother and sister, tsk tsk. Wonder what people will say if this gets out? Wonder how your Grandmother will take the news that you have been fucking your Sister, and she sees how much Mary likes it up the ass? Oh, doesn’t that expression on your face tell it all, Mary?” He pointed to the TV where Mary’s face was twisted in agony and satisfaction as I fucked her ass.
I had no idea where this was going, and poor Mary was on the verge of crying. He paused before saying, “You know nobody has to find out about this, and you don’t have to stop having your fun.” Now, I was the one to be shocked. He turned to Mary, and tilted her face up by the chin. I started to stand up, but froze with one glance from him. “Mary, do you want to keep on fucking your brother? Get that hard cock shoved in every hole you have? And do you want to keep it a secret?” Mary nodded. He smiled and released her chin. She stared at him as he reached for his zipper and pulled down. When his hard cock flopped out, her eyes glazed over. It was as long as mine, but fatter with a deep purple head and bulging veins on the side. “You know,” he said, “three can keep a secret as well as two.” He moved forward until his dick was inches from her face. Mary reached out and wrapped her fingers around it. He smiled as she gave it a stroke and put his hand behind her head to coax her toward his cock. Mary willingly opened her lips and took him in her mouth. She greedily slurped as she worked her mouth on his shaft. He warned, “I’m so hot from watching the tapes of you two all week that I’m going to cum fast. Swallow it my dear.” Mary looked up and nodded before going back to work. She reached up with her hand and fondled his hanging balls. It was the first time I had ever watched someone else getting a blowjob. Unlike me, Mr. Jones stood still and let Mary do all the work. I remembered I was always trusting into her mouth. She seemed to like the difference. I could actually see his balls draw up as he groaned and jerked his load into her mouth. Driblets of cum oozed out of the corners of her mouth as she greedily swallowed. Mr. Jones finished and sat heavily on the couch between us. He reached over and scooped up the strands of cum on her chin on his finger and feed it back to her.
Looking at the two of us sitting there naked, he commented “Guess I’m a little overdressed for this party.” He stood up and stripped off his clothes before sitting back down between us. Mary hugged close to him, and I began to feel left out. Mr. Jones leaned over and whispered something in Mary’s ear. She slid off the coach and positioned herself between us but facing us. She wrapped her hands around each of our cocks and began to stroke us. Despite having Mr. Jones there, my cock responded by stiffening and growing. Mary leaned in and took a flick of her tongue on first his cock and then mine. Continuing to stroke us, she slid her lips down on my cock and gave it a few strokes and then switched to his for a few and then back to mine. Mr. Jones put his arm around my shoulder and pulled me close. He said, “God, you trained her well. Can’t wait to try some of her pussy. I bet she’s a great fuck, yeah?” I nodded. It was strange to be sitting here sharing my sister, but it was hot.
Mr. Jones looked at the clock and asked how long before we had to be home. I explained that my Grandmother would be home by ten. He stood up and took Mary’s hand to pull her up. “Well,” he said, “we better move this party on upstairs.” Wrapping one arm around Mary’s waist, he guided her up the stairs. I blindly followed. We entered his bedroom and he lay down on the bed. His erection was sticking straight up. He motioned Mary over and guided her onto his lap. He held his dick up as she lowered her pussy down. I was feeling left out again until he motioned me to join them on the bed. He asked Mary, “You like getting fucked up the ass, don’t you?” She nodded. He continued, “Ever have a dick up your ass and your pussy at the same time?” She shook her head no. He pulled her forward and motioned me to get behind her. Reaching over to the nightstand drawer, he pulled out and handed me a bottle of lube. Without further instruction, I coated my fingers and greased up her brown tunnel. Soon I moved in to line up, and shoved my dick up her ass. It was a weird sensation for me to slide into her familiar tunnel while feeling another dick just a membrane away. Once I was all the way in, Mr. Jones pushed his dick in further. I don’t know about Mary, but the feel of his dick sliding along the length of mine was mind blowing. He paused and I pulled back and shoved in again. Mary groaned. When I paused, Mr. Jones pulled out and in. Soon we had a steady pace going. Mary was babbling about how good it felt and swearing a blue streak about dicks and fucking and cumming. She hit hers first and hard, as her entire innards tensed and she screamed. At the height of it, she collapsed and seemed to faint. I was afraid we had hurt her, but Mr. Jones said it was normal. Now it was our turn to get ours. We started mutually fucking in and out of her sweet holes. Mary’s limp body flopped back and forth from the force of our thrusts. By the time we were ready to cum, Mary came out of her trance and was yelling for us to cum inside her. I felt Mr. Jones dick throb as I assumed he unloaded in her pussy. That was the signal for me to fire my load deep in her bowels. I can not describe the feeling as both our dicks throbbed deep inside her squeezed side by side by her pulsating tunnels.
We were all spent now. We lay there for a few minutes before Mr. Jones reminded us we had to get cleaned up and get home. He led us into a bathroom with a huge shower. I commented that it was the biggest shower I ever saw outside the school gym. Mr. Jones smiled and explained he and his wife use to entertain guests and needed the extra room in the shower for multiple people. I was amazed that an old man his age would be like that. He laughed and told me he was only 38, maybe old to me but not too old to enjoy life. Before turning on the water, he had Mary sit on the floor. He signaled me to come over and stand beside him. Grabbing his dick, he pointed it at Mary as he started to piss. At first, she reacted with horror, but as the warm liquid flowed over her body and down between her legs, she relaxed. I quickly joined in the fun. When we had both emptied our bladders, he lay down and motioned Mary to stand over him. She obliged with a stream of yellow liquid right into his face. He rose up enough to lick her pussy as her piss sprayed everywhere. When she was done, he turned on the water and we took time to lather up and wash each other. I kind of tensed up when he started to soap up my ass. However, Mary soaping up my balls drew my attention elsewhere. Even when one soapy finger slipped up my ass, I no longer protested but enjoyed.
We finished washing and dried off. Mr. Jones even took time to dry Mary’s hair for her before handing the dryer to me. They kissed like two high school kids as I dried my hair, tonguing each other. When we went downstairs to get dressed, he invited us to return again soon. He kissed Mary goodbye. When I went to shake his hand, he drew me in and planted his lips on mine. It surprised me when I willingly opened my lips and sucked on his tongue. I blushed a little when our lips parted and caught Mary smiling at us.
We hurried on home. Just before we got into the house, I paused. Mary looked at me and asked if anything was wrong. I admitted I had enjoyed tonight, but was worried if she liked Mr. Jones more than me. She laughed. She told me sex with him was fun, but sex with me was part of our love for each other. She said she would like to do it again with the two of us, but not to fear. She would enjoy sex with me without him, but would never enjoy sex with him without me. I smiled and said I was glad because I wanted to have another threeway, but didn’t want to lose her. She smiled and whispered, “Mr. Jones told me that I wasn’t the only way with a cute ass. Next time, he suggested I blow you while he fucks you up the ass.” I looked shocked at this revelation, but my tired dick still took a jump at the thought.
We had many more fun times with Mr. Jones, and yes he did pop MY anal cherry the next time. Look for the next story soon.