My Sister’s Boyfriend

My name is Darren and I am 17 years old. My older sister Katie started going out with a boy she met at college and they’d been together about four months. I hadn’t met the guy but she was always gushing about how gorgeous he was and how much she loved him. She teased me a little about not having a girlfriend yet but I laughed her off. I’ve always known I was gay but being shy, never really went out of my way to meet any other gay guys and was a virgin but spent every evening shut in my room with my thick cock in my hand imagining a hot, horny guy with his mouth around it, cumming all over my stomach and hand instead of into a wet, sexy mouth.

I was in the kitchen one day after a long day at college when my sister burst in through the door with a huge smile on her face. “You look like the cat that got the cream!” I said, smiling at her. “Well actually that’s exactly what I am” replied my sister with a wink. She walked across the kitchen and closed the door before taking a seat at the breakfast bar. “Come on Katie what’s happened?” I asked. She asked me to promise not to tell anyone and I agreed; she then confided in me that she had, that very afternoon, lost her virginity to Sam, her boyfriend of four months. They had skipped a lecture and gone off in his car to a place he knew, hidden away down a track and there she had let him take her. “You’re a naughty girl!” I teased playfully, tutting at her. “Darren don’t be so old-fashioned!” she laughed “we love each other and it was wonderful, it hurt a bit but after a while I started to like it”. I stood up from the counter and asked her if she wanted a drink to change the subject, I didn’t want to hear any details about my sister’s sex life and I was a little embarrassed but pleased she felt she could confide in me. Our parents weren’t home for another couple of hours so I told Katie I had an essay to write and she said she wanted to take a bath. She also told me that she was planning on asked Mum and Dad if Sam could come over for dinner one night soon so we could all meet him. I said that was a good idea and excused myself.

Up in my bedroom I couldn’t help thinking about my sister getting fucked by her 18 year old boyfriend and my cock was soon swelling whilst I was wondering how big his cock was, if it was uncut like mine and how thick it was. I soon had a full erection and allowed myself a few moments of pleasure teasing myself, stroking my cock, wetting my fingertip in my mouth and rubbing it lightly over the sensitive underside of my cock head before taking my cock in my hand and masturbating hard and fast until I ejaculated long creamy ropes of cum that landed on my chest and arm. After a quick clean up I settled down to my essay and was making good progress when I heard my mother’s car pull up. I pushed back my chair and made my way downstairs. When I got to the kitchen my sister was in the middle of asking Mum if Sam could come for dinner and Mum agreed that he could come over on Thursday after college.

Katie was excited all week about showing off her boyfriend to us and took extra care getting ready that Thursday morning. She wore a pretty pink sundress that showed her legs and a hint of cleavage where it hugged her small, pert breasts. She wore her dark blonde hair in a ponytail and wore a little make up, just some pink shiny lip gloss and some mascara to show off her wide green eyes and she went off to college smiling and excited.

I had a study day so I spent most of the morning surfing the net and looking at sexy pictures of hot guys, imagining what it would be like to suck and fondle their cocks and balls, I fantasised about touching their assholes and licking them. I was so hard I couldn’t resist pulling on and playing with my cock and cumming hard and fast. After satisfying myself I managed to get a little studying done until my dad arrived home and called me downstairs to help him mow the lawn. We had just about finished when a dark blue car pulled up with my sister in the passenger seat. The car stopped and she jumped out looking radiant and pretty. The driver door opened and out climbed Sam. He was tall with dark hair, blue eyes and full lips. He looked quite muscular and he had thick, strong thighs inside his jeans and a tight ass. My cock stirred just looking at him. Katie was babbling away and it took me a minute to realise that she was introducing me. Sam smiled and said hi and offered me his hand. I shook it slowly, enjoying his warm, firm touch. My dad was smiling and saying something about how nice it was to meet him but all I could think about what his body looked like under his clothes.

We walked into the house and my mum pulled into the driveway, she had left work early so she could be there to meet Sam. We all stood around in the kitchen talking while Mum started cooking dinner. My dad said he would leave us youngsters to it and disappeared into his study. Katie, Sam and I went and sat down in the living room and Mum brought in a tray of coke and cookies.

We chatted for a while about college and when Mum called us in for dinner we all had a good time, talking and laughing. Sam was really on the ball and funny and he had lots of funny stories, I enjoyed his company immensely and fancied the pants off him but I forced myself to act cool and be a bit aloof so nobody suspected. After dinner Katie and Sam went to her bedroom and I shut myself in mine to masturbate over the image of Sam in my head, I couldn’t stop thinking about him and I was so horny, I wanted to taste his cock, I wanted him to be my first lover but I knew it could never happen.

I didn’t see Sam again for a few weeks and during a conversation with Mum I discovered that her and Dad had given their permission for Sam to stay over with Katie at the weekends, as long as his parents were ok about it and according to Katie, they were. Mum explained she would rather let them sleep together safely under her roof than in Sam’s car somewhere! I was madly jealous but of course, couldn’t show it. My family has no idea I’m gay; I don’t think they’d mind too much but I was afraid of coming out yet but I knew I’d have to eventually!

Saturday rolled around and Katie was having Sam to stay for the first time and was really looking forward to it. I was just hoping to catch a glimpse of him coming out of the shower in a towel or his underwear!

Sam turned up at about 5pm and took Katie out to the pictures and then for pizza. They arrived home at about 10pm and Mum and Dad were already in bed. I was in my room reading and I heard them come upstairs. I haven’t mentioned it before but my room is next to Katie’s and a few years ago I asked Dad to hang a picture in my room. He got a bit carried away with his drill and the result was a little hole in the wall. It occurred to me that if I took the picture down then I would have the perfect peephole into my sister’s room and I was dying to see what her and Sam were getting up to. I felt a bit guilty but not enough to stop me so I stood up, removed the picture and put one eye to the hole.

Watching Katie and Sam I could see them both naked on the bed. They were lying next to each other and I could see Sam’s fingers buried in Katie’s pussy. She was neatly trimmed and her legs were parted. Her eyes were closed and her nipples were hard. Because of how they were laying I couldn’t see Sam’s cock so I kept my eyes on his ass and legs. His arms were muscular and his thighs were delicious, hard and thick. Suddenly Katie sat up and placed one hand on Sam’s chest, forcing him back onto the bed. I got my first glimpse of his cock and it was exactly how I imagined it would be. It was at least 7 inches long and very thick, Katie’s hand looked tiny around his huge shaft and my own cock started to harden and throb as I stared at his beautiful cock. I wanted to keep watching but I knew it was wrong to look at my sister so very reluctantly I stepped away from the wall and lay down on my own bed, stroking my penis and thinking about what I had just seen. I could hear them through the wall, Katie was obviously being fucked hard and fast as I could hear her moaning and gasping; then they were silent. I lay there wishing that it was me that Sam had shot his load over and after cumming I drifted off to sleep.

The next couple of weekends Sam stayed over but I resisted the urge to spy on him but I did meet him a couple of times coming out of the bathroom, once he was just in a towel and his hair and chest were wet and his muscles were shining but I just mumbled a quick “hi” and scurried back to my room trying to hide my erection. I tried to act normal at the breakfast table though and he was always friendly, my parents really liked him and Katie was completely smitten.

The following Saturday Sam stayed again and this time I couldn’t resist another peek once I knew they were in bed. I removed the picture and looked through the hole and I could see Sam kneeling behind my sister fucking her hard doggy style. His back was to me so I could see his arse clenching as he thrust in and out of my sister, his thigh muscles were tensed and his back was arched so his shoulder blades were prominent and he was covered in sweat. I could feel the pre-cum oozing from my swollen cock head as I gazed at the beautiful sight before me, I could hardly breathe. I had to wank so I grabbed the picture and went to hang it back up but one corner slipped out of my hand and before I could get hold of it the picture had crashed to the ground, banging against the wall and floor.

I ran across my room, turned off the light and jumped into bed, my heart pounding. I was waiting for my sister or Sam to come in and ask me what the hell was going on but there was only silence. I had lost my erection so I just turned over and tried to sleep, my mind buzzing over what I’d witnessed.

The next morning my dad had to take my grandmother out and my Mum and Katie wanted to go along; my Mum said to me “Why don’t you and Sam stay here? You can play on your X-Box”. I felt shy and embarrassed to be alone with Sam but I couldn’t come up with a good reason not to so all I said was “Ok”. After telling me they would be back around 4pm my family piled into Dad’s car and they left. I found Sam in the kitchen making himself some toast. I tried to make small talk but he just gave me a funny look. “How about a game on the X-Box?” I asked, trying to sound normal. Sam put down his butter knife and turned to face me. “See anything interesting last night Darren?” he asked, a small smile playing on his lips. I couldn’t think what to say and started to stutter out a reply but he put his hand up and said “I found your peephole. You’re a dirty pervert for spying on your sister, do you like watching your own sister getting fucked?” I couldn’t think of anything to say and I could feel my face turning red. I managed to force out ” I wasn’t watching my sister” before realising that I certainly couldn’t say who I’d really been watching. Sam walked towards me and put his face up to mine. I tried to step back but he grabbed my arm. “I know about you Darren” he whispered, “Did you think I hadn’t noticed the way you look at me?” Before I could deny it he leaned forward and kissed me. I pulled back in shock but he pulled me towards him and put his lips on mine. I closed my eyes and let him kiss me, starting in surprise when he tried to push his tongue into my mouth and after a few seconds, I relented and allowed our tongues to touch, my mind was racing and my cock started to harden, I tentatively reached behind Sam and put my hand on his ass and he took me by surprise by taking my hand off his ass and pressing it against the bulge in the front of he jeans. He broke the kiss and we stood there looking at each other, both of us out of breath.

He leaned forward again and murmured “How about we go upstairs and get more comfortable?” I protested weakly, telling him that I couldn’t hurt my sister and I’d never done anything like this before but my desire for him was so strong, I didn’t resist when he took my hand and led me to the stairs. We made our way to my bedroom and stood next to the bed. Sam pulled his t-shirt over his head and unbuckled his belt. He let his jeans slide down and kicked off his shoes before removing his jeans completely. He stood before me, naked except for a pair of boxer shorts that were straining against a large erection. I was so nervous and excited and I said to Sam “I’m shy, I don’t know if I can do this. I want to but I’m not sure I can.” He assured me that it was ok and said “I’ve wanted to be with you ever since I saw you, Katie never needs to know, I only go out with girls so my parents don’t find out I like boys.” I still felt bad for betraying my sister but I wanted to be with Sam so badly I couldn’t stop myself from undressing and sitting down on the edge of the bed. Sam took off his boxers and displayed his swollen cock. It was inches from my face and, swallowing slightly, my heart beating fast I reached out and wrapped my hand around it. Sam closed his eyes and stepped closer to me. I started to rub my hand up and down his cock, pulling back his foreskin and enjoying the sensation of another man’s cock in my hand. After a couple of minutes I noticed a bead of pre-cum appear from his cock head and feeling brave, I leaned forward and licked at it. Sam let out a soft moan and I felt encouraged to go further so I opened my mouth and took his length into it, sliding my lips down his shaft and using my tongue where I knew he was most sensitive. My own cock was bursting and I’ve never been so hard in my life.

Sam was thrusting his cock into my mouth and pulling at my hair, moaning and telling me how good it felt to have my mouth on his cock and I was stroking his balls and sucking and licking his cock, my own cock dripping pre-cum and throbbing. I put one hand on my swollen penis and stroked it gently. Sam slowly pulled his cock from my mouth and pushed me back onto the bed. “Your turn” he said, smiling at me. He knelt on the bed and lowered his head to my groin. He ran his hands down my thighs and kissed the insides softly, licking his way up to my heavy, swollen balls. He touched them carefully, rubbing his thumb over the smooth, sensitive part, sending shivers through me. I though I was going to explode. He drew his fingertips lightly over my shaft, teasing my cock then took it firmly in his hand. “Put your legs up” he ordered. I did as he asked and pulled my legs up, exposing my tight asshole to him. He stroked the cheeks of my ass and complimented them saying they were tight and firm then I nearly shot off the bed as he ran his tongue down the crack of my ass and he told me to relax. He had one hand massaging my cock and now I could feel his hard tongue poking at my virgin asshole. I let my muscles relax and he pushed his tongue straight in. I was in Heaven as he tongue fucked my hole and wanked my cock and I managed to croak out that I couldn’t last much longer. Sam stopped tonguing me long enough to tell me to go for it and then pushed a finger into my anus and took my cock back into his mouth. I could feel my orgasm starting in my balls and I was moaning and writhing on the bed, Sam knew I was close and sucked harder, using his tongue all over my cock and I flooded his mouth with my hot cum, jet after jet down his throat. He couldn’t manage it all and some was spilling down his chin.

I managed to struggle to a sitting position and we kissed. I licked the cum of his chin and tasted myself on his tongue. He lay down next to me on the bed and placed my hand on his cock. It had gone down a bit from non attention but it soon hardened fully and I knew I wanted it in my ass.

I sucked Sam again and he whispered that he wanted to fuck me. I asked him to be gentle and take it slow and he promised that he would. He spat on his fingers and slid a couple into my asshole, I tensed at first but started to relax as it started to feel good. He worked another finger into my hole and slid them in and out as he finger fucked my ass. He asked me to turn onto my stomach; I rolled over and felt his legs against mine as he lowered himself, positioning his cock against my hole. I felt the tip of his cock nudge against me and took a deep breath, trying to relax. There was some resistance at first but he used some more spit and worked my asshole with his fingers and all of a sudden his cock was inside me. It took my breath away and I lay still just trying to get used to the feeling. It was painful at first but he started fucking me with slow, shallow thrusts and I started to enjoy it. I played with my cock as he started to pound my hole harder and harder; he pushed my hand away from my cock and started wanking me roughly; I was crying out and begging him to fuck me harder and faster and he did as I asked, the whole length of his cock was inside me and I had never realised anything could have felt so good. I pushed away the image of Katie’s face that popped into my head and concentrated on what was happening to me. Sam quickened his pace and I felt my balls tightening up as my orgasm approached. “Fuck me, I’m fucking cumming” I cried out to Sam and my cum spurted out all over his hand and arm as he pulled hard on my engorged cock; seconds later Sam let out a shout as he emptied his sperm deep inside my bowels. I could feel it trickling down in between my ass cheeks.

We lay together on the bed for a while kissing and stroking each other’s limp cocks. “I’ve always wanted to do that Sam, I’m glad my first time was you; I wanted you since I first saw you” I admitted. Sam smiled and kissed me softly on the lips. “My turn” he said and got onto his hands and knees. The sight of his tight hole and firm cheeks had my cock stiffening again and a few strokes was all it took for me to be fully hard again; I’d never been so horny in my life. Sam knelt up and asked me to lie on my back and I did so willingly. Sam spat on his fingers again and opened up his asshole for me and then slowly lowered himself onto my erection. He’d obviously been fucked in the ass before because my cock slipped in easily. He took a moment to get comfortable then he started to rock back and forth with my cock deep inside him. He played with his cock and I couldn’t take my eyes off him, he was so beautiful. He reached behind him and fondled my balls and I couldn’t stop myself from thrusting up inside him as deep as I could. He started to rock faster and let go of my balls so he could wank his cock properly and slapping it against my belly. I couldn’t hold on much longer, his hole was so tight and every movement was bringing me closer to ejaculation; I put out a hand and he let me take hold of his cock. I started rubbing it up and down, using my spit to make the head wet and Sam shouted out that he was cumming. He shot out an amazing thick, long stream of cum that landed on my chest and face. I licked off what landed on my lips and then let myself go; filling his asshole with my cream while he sat on top of me, panting and covered in salty sweat.

We collapsed onto the bed in each other’s arms, our cocks touching, both limp and sated. I couldn’t believe what had happened. I didn’t know if it would ever happen again, or even if I really wanted it to; after all, he’s my sister’s boyfriend.