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Cuckold: First Strap-on Anal Sex & Bi 3someLet me start by saying I’m a white Jewish man in a cuckold marriage. I’m in my mid 40’s and I’ve been sexless for the last six years, while my wife has had many sexual partners and boyfriends over the last 16 years, most of them hung black men. Even though this is not how I expected my life to turn out, I’m content being a sexless cuckold and get turned on by the humiliation of my wife fucking other men, but it’s definitely something I’m not proud to admit to people I know! My first story titled “Teenage Cuckold – Catching My Cheating Girlfriend” was about my ex-girlfriend Christine when we were teenagers. This story is about my ex-girlfriend Claudia that I dated in my 20’s just after college.I met Claudia when I was 23 years old and she was 26. She was a very pretty Goth Girl with strawberry blonde hair (more blonde with red highlights/tone). The left side and back of her head was buzzed with her hair on top grown out just under shoulder length. She had tattoos on the back of her neck, back of her shoulder, arm, calf and ankle and her nipples were pierced. One of her jobs was a spin instructor, so she was thin with firm muscular legs and a killer ass! Her tits were a c cup that hung naturally and she often went braless! She was unlike any girl I dated before and I was extremely attracted to her looks and style. I had lost considerable confidence since dating Christine and I was going on two years of being sexless and not having a girlfriend. I first noticed Claudia at an alternative dance club. I use to go there every Friday with a buddy of mine because I loved the music, but maybe more so to see her, not that I ever approached her. One night another friend of mine, Derek, came out with us. He hated the music, but was more into going to hook up with a girl even though he had a girlfriend. When my other buddy pointed out Claudia to Derek and said I’ve been checking her out for months Derek said I should “get off the sideline” and talk to her. When I didn’t he said he show me what to do.Derek was bi-racial and very confident, a womanizer. He often bragged about the size of his cock and his conquests. What shocked me was by “showing me” he didn’t mean with another girl, he approached Claudia! The two of them soon spent a good portion of the night at the bar doing shots and talking. I felt sick to my stomach seeing him hooking up with her. My worst nightmare occurred when the two of them left the club together. I would hear from Derek that he went back to her apartment and spent the night “pounding her pussy as hard as he could and the slut took it like a champ”! The next Friday I saw Claudia at the club I was so pissed I got the courage to approach her. We actually hit it off, though I’m not Derek and didn’t leave with her or even get her number, though this was a major accomplishment for me! I spent the next couple of Fridays talking to her and getting to know her and I fell for her more each time. Meanwhile I heard from Derek he was fucking Claudia twice a week on the side without his girlfriend knowing. Eventually, I asked Claudia out on a date and to my surprise she said yes. Derek wasn’t taking her on dates or spending any money on her just fucking the shit out of her, so I made sure to spoil her with a great date. Things went great on the first date and we continued to go out and talked on the phone most nights, but she was still fucking Derek and she had no idea we knew each other, so I felt I needed to be honest with her because I had really fallen for her. When I told her the whole story she was pretty shocked and even embarrassed. She suspected Derek was dating a girl and even admitted he wasn’t her type but the sex was incredible and she hadn’t had a boyfriend in about a year before they hooked up. She felt used by both of us and I begged her to believe that I never intended to use her. She ended things with both of us and Derek was pretty pissed at me for ruining a good thing for him. He did things to her his girlfriend wouldn’t do like fucking her ass!A couple weeks later at the club I apologized to Claudia again and she said she missed me more than Derek and we started dating again. Things were going well, but I often thought about the things Derek told me he did with her! Sometimes I’d look at her and think stuff like “I can’t believe she use to take Derek’s cock up her ass but I haven’t had her ass yet”, but overall the sex was absolutely incredible! Claudia was much more dominant in bed than any other girl I had dated or had sex with. She often would be on top during sex and ride me with vengeance with her hand around my throat telling me not to cum! She also loved to spank my ass hard and got a kick out of seeing that make my soft cock grow and get hard! Now when I say the sex was incredible that was from my perspective and I know I wasn’t fully satisfying her, but she would often let me use a dildo to canlı bahis siteleri fuck her pussy after we were done having sex in order for her to cum so I thought things were good and she seemed to like me being submissive to her. About six months past. Then one night while in a 69 with me on top, after giving me a good rimjob, she reached into her nightstand and pulled out a thin but long sleek black vibrator and some lube. I felt the cold lube pushed into my asshole with her finger, I momentarily stopped eating her pussy, but continued upon her orders to get back to licking her. Next came the vibrator, it wasn’t thick but it was bigger than anything I’ve ever experienced and it hurt a little as my asshole was being stretched out by it! She began slowly sliding it in and out of my asshole and that’s when it hit me I was getting my ass fucked! It felt uncomfortable at best, but I was turned on by Claudia’s words of how hot this was making her! Then after a few minutes she switched on the vibrator and the sensation was overwhelming! She continued to fuck me with it and push it deep inside me. My moaning became much more intense so she upped the speed of the vibration and fucked me faster with it. There was still some pain, but the pleasure far outweighed the pain. As she rested it deep inside my ass the buzzing against my prostate began to give me an orgasm! My cock was rock hard without her touching it and all of a sudden I started to cum! When she felt my cum shooting onto her belly she exclaimed “Oh yes! Cum for me baby!” It was probably the most intense orgasms I ever had, but there was definitely some humiliation when it was over.What I didn’t know was Claudia began fucking Derek again after his relationship with his girlfriend ended. Slowly I realized we were hanging out less and she was busy more. The sex decreased too and she seemed content just doing stuff to me, like blowjobs, handjobs and even playing with my ass and fucking it. Derek started showing up to the club again even though he said he hated that music and when he was there I could see he was interested in Claudia. I was very insecure knowing he fucked her and better than I do, but he assured me not to worry. He joked, “You just need to invite me to your wedding so as she is wearing her gown and saying I do you will both see me sitting in the front row knowing I fucked her”. I’m not a dumb guy and began to be very suspicious of her cheating on me with him. I was also masturbating thinking of them two having sex. I wasn’t confrontational about my belief she was cheating on me, but I asked her a number of times if she was satisfied sexually with me. She then said two things to me (1) she told me she thought I might be gay and that I was at least bi because I enjoyed anal sex and (2) she wanted to have a two guy 3some. She suggested the guy be Derek because we knew him and she knew he was good. She also thought it would be really hot because he is my friend and he is dominant and I’m submissive. When I said I wasn’t that submissive she laughed and said “Oh my God you are such a sub…just own it I like that you are!” I didn’t give in right away, in fact Claudia got pretty frustrated with me and basically withheld sex from me for a couple of weeks until I caved into her wishes and agreed to the 3some. When I agreed she didn’t seem happy or satisfied and told me “I’ve been having second thoughts about us and you being able to make me happy.” She continued “I might want to see you suck his cock now” She chuckled and said “We can have our 3some and find out if you are gay at the same time!” I pleaded “I’m not gay” and she responded “then you won’t like it and will never have to do it again, but at least I will know I’m not wasting my time dating a gay guy”I told her I would set the 3some up with Derek, but I wouldn’t guarantee I would suck his cock and I doubted he’d let me. Little did I know they already discussed it and Derek was intent on humiliating me in front of Claudia! All of a sudden the 3some was the least of my issues! Then again secretly I wanted to watch him fuck my girlfriend and I thought back to catching Christine cheating on me and how often I’ve masturbated to that image even until today!The night of the 3some the three of us met at a bar near Claudia’s apartment. I drank the most of the three of us and Derek even brought me a few shots almost like her wanted me a little drunk. When we got to Claudia’s apartment and they wasted no time getting started. They began kissing and undressing each other, leaving me to undress myself. Once they were naked Claudia dropped to her knees and began sucking his cock. It was huge! As big as he bragged about. It was ten inches and thick with a round head! I instantly got turned on and began stroking my already growing cock. Derek saw me and quickly stated “you like watching her suck my big cock!” He then added “Wow is that as big as it gets?” tipobet güvenilir mi referencing my cock, which was literally half the size of his massive cock! I felt humiliated and inferior, but didn’t say a word and that set the tone for the night.After sucking his cock for 5 minutes she stood up and told us we should move to her bedroom as she lead Derek there by holding his hard cock. When we got there he pushed Claudia onto her bed and flipped her around so she was on all fours and I watched as his huge cock entered my girlfriend’s pussy! He grabbed her by her hips and fucked her deep and hard right from the get go. He told me “pay attention I’m gonna show you how Claudia likes to be fucked!” He proceeded to pound Claudia’s pussy for 15 minutes until her moans became cries of pleasure and she yelled she was cumming! I never made her cum so fast or so hard, even with a big dildo! Derek withdrew from her pussy still hard but he had not yet cum himself! He looked at me and with complete arrogance told me “That’s how you fuck her!”Claudia got off the bed slowly still recovering from her big orgasm. She went to her dresser and pulled out a strap-on and without saying a word put it on. I was like a deer in headlights as I looked at her wearing it, a black cock hanging between her legs, she looked so hot! She was stroking it applying lube to it as she walked over to me. She stood right in front of me and said “It’s your turn to get involved” as she placed my hand on her cock and had me stroke it. I was so nervous, but I was giving her a handjob as we kissed! She told me to get on the bed on all fours and I hesitated. She whispered in my ear “Don’t worry he knows I’ve played with your ass”. It was surprising to me she would have told him that, but in the moment I didn’t connect the facts that Derek wanted to see me get me ass fucked and this was part of his revenge on me for ending things with Claudia almost seven months ago.I did as was told and got on my hands and knees and Claudia gave my ass 7 or 8 hard slaps across my ass, which stiffened my already hard cock and made precum leak out. If she continued spanking me I think I would’ve cum right then. Instead she applied a generous amount of lube to my asshole and began pushing her cock into me. The pain was pretty intense as my asshole was stretched out more than it had ever been in the past! Her cock like dildo looked so hot, but the pronounced head was making my asshole burn as it pushed into me. My eyes watered up from the sensation and Claudia could tell I was in pain taking her big cock. She went slow and offered me encouragement. Then there was a sense of relief as the head fully sank into me and my asshole closed a little around her shaft. I heard Derek exclaim “Damn!” as Claudia pushed her cock deeper inside me. I felt embarrassment and a sense of regret that Derek was watching this be done to me! Claudia slowly built up her pace she was fucking me and I moaned uncontrollably. She regularly reapplied lube and I started to adjust to the girth of her cock as she kept fucking me. My cock had gone limp once she started fucking my ass, but now after 15 minutes she had a steady pace going and with the head of her cock now bouncing off my prostate the pleasure began to outweigh the pain. My cock began to get hard again and Derek noticed and laughed as he saw it grow! He told Claudia “You are making his cock get hard…he really does like taking it in his ass!”With that Claudia moved her hands from my hips to my shoulders and started fucking me even harder and faster! I didn’t know what was worse, the increased pain or the humiliation that I felt like I was about to cum and I desperately didn’t want to in front of Derek. I wanted her to stop, but I could only manage to get out one word, “PLEASE!” Claudia didn’t stop and continued to pound my ass. My moans became so intense she knew I was about to cum, so she quickly pulled her cock from my ass and rolled me over. Before I could even catch my breath she had her cock back in my asshole as I laid on my back and she stood at the edge of the bed with my legs d****d over her shoulders. I said, “No more” but she sternly replied “we are done when I say we are done!” I didn’t protest anymore and at that moment I surrendered myself to her for the rest of the night! At this pointed I wanted to cum so bad it felt good to give into her completely! Laying on my back I could also now see Derek standing next to Claudia watching me. He was still hard and stroking his huge cock as he was clearly enjoying seeing me fucked like a sissy! Then it hit me! I began to feel the most intense orgasm of my life! I dropped my head back onto the bed and closed my eyes! Claudia knew I was about to cum and grabbed my small but rock hard cock and held it firmly pointing it toward my face. So much cum began to fire out of my cock hitting me in the face and chest as I tipobet giriş moaned so loud! She started to jerk my cock to milk it for more cum as she fucked my ass as hard as she could!I then felt a hand on my head grabbing my hair and pulling my head up. I opened my eyes and Derek was on the bed next to me jerking off hard! Without warning cum shot from the head of his cock and splattered hard across my face making me flinch, but he held my head firmly in place and ordered me to open mouth! I did and he continued to cum filling my mouth as Claudia was still fucking my sore asshole! Derek grunted and moaned loud as he emptied his balls into my mouth! Claudia shouted “Oh my God!” as she watched Derek cum in my mouth and on my face. As Claudia then slide her big cock out of my asshole Derek slide his huge cock into my mouth! I was forced to swallow some of his cum while some spilled out over my chin! He fucked my mouth as he demand I keep it open wide.He then pulled me all the way up so I was sitting up on the edge of the bed and he stood above me feeding me his cock. He had both hands on my head and he stopped fucking my face and told me to suck his cock. I started moving my head back and forth on it as he removed his heads from my head. I was now freely giving my friend a blowjob which which was much more embarrassing than be forced! He moaned and said, “mmmmm you are good at this! Using your lips and tongue with no teeth! You sure you haven’t done this before?” Claudia laughed as I just continued to suck his cock. He added, “You are a natural!” The humiliation was crazy but it was actually turning me on! Derek told me, “Don’t forget my balls” so I obediently started licking them! As I licked all around and under his big balls I stroked his thick veiny shaft. I could notice the size difference of stroking his cock compared to my thinner shorter penis and I really enjoyed the feel of jerking off a bigger cock! When he told me to go back to his cock I ran my tongue up his long shaft until it reached the top of his cock head and I put it back in my mouth! At this moment I was doing what I never wanted to admit to myself I was interested in…I was sucking a cock and I liked it. The fact I was going to feel like a big loser later didn’t dawn on me. I kept sucking Derek’s cock until he was ready to cum again! He moans intensified and Claudia made comments how unbelievable hot it looked watching us two! Derek grunted as he started to cum and let Claudia know he was cumming in my mouth. I did my best to glurp down all of his thick gooey cum! When he finished he pulled his cock from my mouth and with my face still covered with both of our cum he said “Now we are even!” He didn’t elaborate but I knew what he meant at the moment and I felt used and realized Claudia was in on this. He then added “I kinda always thought you were a fag but damn!” I knew what I just did could never be undone. But the night wasn’t over and Derek fucked Claudia a couple more times that night and marveled at how amazing he was! I ate her swollen used pussy after both times! I got to fuck Claudia once when Derek gave me permission to join as he switched from fucking her pussy to fucking Claudia’s amazing ass. We were giving my slut girlfriend a DP and it felt pretty incredible for all three of us! After that we concluded a few hours of sex by taking showers, they took one long shower together and I took a shower alone. When I arrived back in the bedroom, Derek told me there wasn’t enough room for all three of us to sleep in her bed so I should sleep on the couch. Claudia looked at me and told me “Yeah I think that’s best” so I left Derek to sleep with my girlfriend! The next day Claudia broke up with me. She started by saying “I think you know what I’m about to do so it’s best I don’t say much except we need to break up.” I wasn’t surprised, but I did ask why and if there was anything I could do to stay together. She didn’t want to discuss anything and just asked me to leave. Derek was in the next room as Claudia broke up we me and as I passed him on my way out of her apartment I couldn’t even look at him because I felt ashamed after sucking his cock the night before, They started dating and I sort of stayed friends with Derek even though I avoided hanging out with my friends when I knew he would be there. The funny thing was I wasn’t mad at Derek, it was like he proved he was the alpha male and took my girlfriend and I kind of believed he deserved her. When I did see him it was more like I always felt embarrassed that he took my girlfriend from me, but also because I felt he knew I liked sucking his cock and wanted to do it again! As for Claudia, I always missed the sex with her, her amazing body and how she dominated me! I was hurt by what she did, but not for cheating on me but for allowing Derek to humiliate me and for making me feel conflicted about wondering if I was gay or straight. That lead me to secretly having a couple of gay experiences that I regretted afterwards, yet I still had a desire to be with Derek again! It was very confusing and at that point in my life I didn’t realize what I really was is a cuckold and I wouldn’t know that until I met my wife!

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