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Rimming and Fucking my Brother-in-law

by Orangebinder
21 Oct 2025


My twin sister and I were always really close. She was the most supportive of everyone when I came out. She knew long before I said anything. When she brought Tom home for the first time, I nearly creamed my jeans. He was fucking gorgeous, just an effortless natural physique, really handsome, and a head full of bright red (almost orange) hair. He was funny, engaging, and could strike up a conversation with anyone. I nearly fell in love with him on the spot but he was taken. Also, I had no reason to believe he would swing for my team. Shelley and Tom got married about a year later and I couldn’t have been happier for them. They seemed perfectly suited for each other. About a year later, I happened to be with Shelley and she seemed upset about something. We had always been completely honest with each other so I finally pried it out of her that Tom really like to be rimmed and pegged. He was 100% straight, not the least bit interested in cocks or men’s bodies but he had this itch in his butt that could only be satisfied with a good pegging. Shelley had done her best but she really didn’t enjoy it and found it borderline disgusting – not when other people did it, just when she did it. She told me that she really tried rimming but just couldn’t get past the idea of putting her tongue on the hole where shit comes out. What made is even worse is that she knew how much Tom got off on it. He absolutely loved being rimmed. I offered a few suggestions on how she might pleasure his hole without actually using her tongue. As I talked and explained, she asked if I did this a lot and I said, “of course. I love to rim.” She just nodded. “How about fucking? Do you do that as well.” “Of course I do. Why do you ask?” “Oh nothing,” she said. I didn’t think much about it until she called me about a week later and asked to have lunch with me because she wanted to discuss something. I was intrigued. When we met for lunch a couple of days later, I could hardly wait to hear what she wanted to talk to me about. She made sure we got a table off in a corner away from anyone else. She said that she had had a long talk with Tom and they came to an agreement. They wanted to know if I would join them in bed to rim and fuck Tom while he ate her pussy, or sucked on her tits, or she sucked him, or whatever they wanted to do with each other. I was more than a bit taken aback. I certainly didn’t expect this and didn’t know how to respond. (My cock jerked alive but I tried my best to stifle that.) Sure, in middle school we used each other to practice kissing and I had seen Shelley naked many times because we were twins, we shared a bathroom growing up, and I was gay. And she had seen me naked many times but that is different from joining her and her husband for an evening of sex. I asked for some time to think about it for a few days. (My dick was still hard as a rock in my shorts.) I called her about a week later and was still rather indecisive. She suggested that I come over for dinner on Friday night and after a couple drinks, we could see what felt natural. I dressed, re-dressed, and re-dressed three or four times. I couldn’t figure out what to wear. What does one wear to go have sex with your sister and brother-in-law? Do I go formal, khakis and collared shirt, shorts and a polo? The options were whirling through my mind. Also, which underwear? Do I go with something with lots of coverage like boxers, or a bit less like fitted boxers or boxer briefs. Or, do I go with sexy? How about a sexy black bikini or a jock strap or something else with a bare back? After an hour I was so confused that I wasn’t sure what I had on under my pants when I got to their house. I ended up with khakis and a polo with no socks in my loafers – easy on, easy off. I was nervous as hell and I was glad to see that both of them were equally nervous. I had never seen Tom so tongue tied. We started with a cocktail and rather than nursing the drink, I just about guzzled it. We had a light meal with lots of wine. I think I had two glasses. I was really relaxed. Before I knew it, we had finished dinner and now it was time for the main event. Shelley took Tom’s hand and my hand and led us to the bedroom. She sat on the bed and started to slowly undress. I had forgotten how perky her tits were and how smooth and tight her body was. Even if I wasn’t the least bit sexually attracted, I could certainly appreciate good form. I was pleased to see that she completely shaved her pubes, that was something new since the last time I had seen her in high school. She sat there on the bed for a moment letting us look at her body. It was as though Tom and I were paralyzed. We just stood there and stared at her. She got up and started undressing Tom. She unbuttoned his shirt and unzipped his pants. When he was in his underwear (tight boxer briefs), she turned her attention to me and helped me pull off my polo and unzip my pants. I was wearing a white jockstrap, the kind you wear in high school PE class. I don’t remember putting it on but both Shelley and Tom took note. She lightly kissed me on the lips, then did the same for Tom. She knelt down in front of Tom and nudged his shorts down as well. His half-bloated dick plopped out and she sucked it into her mouth. He was in heaven, or clearly on his way to heaven. I was incredibly turned on by Tom’s body – athletic but not overly muscled, tight everywhere it should be tight, and soft and fleshy where it should be soft and fleshy. His nipples were pert with just a whisp of hair leading down his chest in a line to his neat and tidy pubes. I couldn’t get a good view of his ass but from the side he was gorgeous. His butt was rounded, tight, and had the cutest and deepest dimple on the side when he flexed. At this point he was oblivious to my presence. Shelley led Tom to the bed with his dick in her mouth and he followed. As she laid back on the bed, he bent over her and moved to his pussy attacking it with his mouth. That was my cue to move behind him and get a really good look at his butt and his asshole. It was gorgeous. No time like the present so I knelt behind him, gently pulled his cheeks apart, and dived in with my tongue. I buried my face in his gorgeous but. He wiggled his butt a bit as he pushed back against me. We were already in a rhythm. The rest of the night could not have gone better. I fucked him in three or four positions, sometimes with me on top, sometimes with him on top. He had his attention focused on pleasuring Shelley as I fucked him. I dumped at least three loads of cum up his butt and he squirmed and squealed like a stuck pig as I fucked him. I think he pumped at least the same number of loads into Shelley’s pussy or mouth, or whatever. I discovered that both Shelley and Tom were screamers. I don’t think I’ve ever been with anyone who made more noise than them. When we were done, we laid there exhausted in a tangled heap of nakedness. We gasped for air, covered in sweat, and completely spent. If I hadn’t been there, I imagine they would have just drifted off to sleep. I eventually stirred and untangled myself from the two of them. I was suddenly self-conscious and got dressed as quickly as I could and was out of there before they really got up. Shelley gave me a call the next morning and she practically gushed. She said that not only did she have a good time but she had never seen Tom cum so hard and so often. She said that she and Tom, but especially Tom, wanted me back the next Friday night. Maybe I could plan on spending the night too. I immediately agreed to come (cum?) over. The next Friday night, I was less apprehensive but I wouldn’t say I was anxiety-free. When I got there, I saw that I shouldn’t have worried. Shelley was in a bathrobe and Tom was in a pair of baggy boxers with a mostly open fly. Shelley flashed her boobs at me as I entered the front door. They both gave me a big hug, and I swear Tom specifically pressed his crotch against me as we hugged. We shoveled the food in as quickly as we could. We were obviously all horny as hell and ready for a re-match. Tom made a point to bend over to pick up something from the kitchen floor and flash his butt in the process. He was wearing a white jockstrap like I had worn the previous week. I was ready to take him there and then on the kitchen floor. I wanted to eat and fuck his gorgeous butt all night long. Like last week, Shelley was the first one naked. When we had finished eating, she dropped her robe and said she was headed to the bedroom. Tom and I glanced at each other, smiled, and followed her. Tom also dropped his bathrobe and I was right behind his perfect ass. He bounded up the stairs to the bedroom with his butt cheeks flexing and relaxing with each stop. He made me hard as a rock before we even got to the bedroom. They both lept onto the bed as I threw off my clothes and joined them. As quickly as we jumped into it the first week, we were even quicker to get going the second week. Tom was on all fours on the bed with Shelley under him 69ing. He knees were spread apart on either side of her head giving me a great view of his asshole and access for my face and tongue. I dove in and ate like a man who was starving. He moaned and squirmed his butt as he ate Shelley’s pussy and she sucked his dick. We were each incredibly content. I fucked Tom like I had never fucked before and he took it like a man. He loved it. At one point I was laying on my back with him fucking himself on my dick when he impetuously bent forward and kissed me long and hard. Our tongues intertwined and we shared our spit. Shelley loved it. She surprised herself how turned on she got by watching Tom and me make out. She encouraged us to keep going as she fingered her twat watching us. She came hard as Tom and I kissed and he fucked himself on my dick. Before the night was over, I even took a swipe or two with my tongue at Shelley’s pussy. I didn’t gag but it reinforced what I already knew – I am not meant to eat pussy. We abandoned ourselves to sex and came and came until our balls were drained of all cum. When we were done, we lay gasping but this time I didn’t have to leave. We drifted off to sleep, had another round of sex sometime in the middle of the night, and then again most of Saturday morning. By the time we were done, my dick was sore and balls ached. It became a standing appointment every Friday night through Saturday morning. If there was a three-day weekend, we did the same Sunday night through Monday morning. I eventually brought all the toiletries I needed so I didn’t even have to bring a bag with me. I would just wear the same clothes home in the next morning – its not as though I had them on very long. About two months after this all started, Tom had to go on an extended business trip and would be gone two weeks. I didn’t need to fuck Shelley while he was gone so we talked on the phone a lot, even did some three-way phone sex but Shelley and I didn’t get together. I gave Tom one night at home on his return to get rested up and I was there the next night raring to go. Little did I know that while Tom was gone, they had made some changes. First, they replaced the queen-sized bed with a king. Queen was plenty big while we were having sex but three grown adults trying sleep on a queen-sized bed was an issue. Second, and even bigger, Shelley had done a quick bathroom remodel. They used to have a tub and stall shower but she had both ripped out and in their place a large glass shower with a long bench down one wall was in its place. It was more than ample for the three of us to play together or just have a leisurely after-sex shower. But, that is another story.

Orangebinder@yahoo.com

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