I guess you could say it all started when I met Jenifer a few years ago, I was 26. She was three years younger and we met through friends of friends. Jen is outgoing and extroverted, maybe a bit of show off and she excels in all social situations. All things I am not. Not to say I am shy or lack confidence, but I am definitely reserved. She is also a lot more experienced then me and has a higher body count, despite the age gap. While it took me until my 20s to start getting lucky, she had been at it since her late teens. She had even slept with a couple of mates before we made it serious. It didn’t bother me and if anything, I found it a bit of a turn on. I mean, here was this geeky boy who had a hot, sexy girl in love with him. Who cared if she was a flirt. Not that the flirting was an issue and she would never do anything else. Jen was completely infatuated with me and I never had to worry about her being unfaithful. Though ironically, this was the one relationship where she could have been. You see, for a long time now I have had a fantasy of sharing a girlfriend. When it started I just wanting to be cheated on, but it then graduated to the full cuckold fantasy as I understood it more. I never told anyone about it, let alone Jen. I am ashamed to say I was embarrassed and did not think she would ever understand or be in to it. Though that was soon to change. Back in 2019 we went to a Halloween house party at a friends, we only knew a couple of people there but they had put on an amazing night. Jen went as a cat. A sexy cat. She wore a tiny, high waisted, black leotard, that left three quarters of her bum exposed. Finished off with, fish net tights, cat ears, tail and stilettos. With her slim figure, long brown hair and rich brown eyes she looked amazing. Needless to say she was getting a lot of attention… and was enjoying it. Maybe too much. That night she drunk too quickly and from I was told, was more then a little tipsy. She left me chatting in the kitchen and was running around the party showing off her outfit, flirting with everyone. It wasn’t until her friend confronted her that she realised she was in the wrong. She came back to me in tears, feeling incredibly guilty. I took her home and comforted her as she apologised and told me she loved me. She kept asking if I was jealous and how she could make up for it. I repeatedly forgave her. Though to be honest I didn’t even mind. And it wasn’t long until we were having some of the best sex of our lives. The leotard was so small she didn’t even need to take it off. I still remember her saying “wow I should make you jealous more often if that’s how you react.” The subject lay dormant until January, when Jen was trying to get me to be ‘naughtier’ in the bedroom. She had been pushing me for some time. Jen loved anything dirty and really wanted to share I my fantasies like I shared in all hers. Eventually I broke and told her I liked it when she made me jealous at the party. Her face was a mixture of confusion and intrigue. She had many questions and I slowly but surely opened up about every aspect of my fantasy. Threesomes, watching her, her on her own with another guy, the whole filthy lot. I was expecting her to be shocked. Maybe even think I didn’t fancy her anymore. But she didn’t, she took it like any other fantasy, taking her time to find out more and understand it. After telling her everything she paused, before asking “is this something you like to think about, or something you actually want to happen?” I could’t reply and just mouthed breathless that I wanted it to actually happen. She didn’t look surprised but told me she needed time to think. A couple of days later she asked me for a talk. I can’t remember the conversation 100% but it started “So… you want me to have sex with other men?” “Yes.” “Full Sex?” “Yes.” “And you want to watch?” “Watch or join in, or without me. I don’t mind, its about you doing it with someone else.” “I’m not sure about a threesome, I’ve had one with two guys before and it was a lot of work, pleasuring two the same time.” “Oh, I didn’t know, but yeah its fine it’s down to you.” “And if I say yes, do I pick him?” “Yeah you can decide on everything if you want.” “But only me yes, I couldn’t handle it if you slept with another girls.” “Errr yes, never thought about it but yeah, this is about you and another guy.” It went on back and forth like that until finally, looking me deep in the eyes, she told me she would do it. But only for me, she wasn’t interested in sleeping around anymore. God, I felt excited but nervous at the same time. Over the next couple of weeks we not only talked about it, but started to work out the logistics. We were too scared to ask a friend to join us, so turned to apps to find someone new. We both downloaded one and set up a couple profile looking for a male third. It was more or less like tinder but for groups. But quickly we discovered it was full of catfish and weirdos, so we were very careful to be discreet. It wasn’t going well and I don’t think we ever expected to find someone, but then we matched with John. I am not into guys, but even I could tell he was hot from his profile pictures. Scrolling through them, I saw Jen pausing on one of him just wearing some white boxers, showing off his muscles. Normally she found toplesse or nude profile pictures a turn off, but his body was so perfect she was practically drooling. Fortunately he had the personality to match and the conversation flowed easily. Even I got on with him really well, we had so much in common. But Jen seemed to have an instant connection on a different level. Then slowly, as we got to know and trust him, we told him what we wanted and how. He seemed to understand and was happy to help us out. We had found our guy. Jen still wasn’t sure if she wanted a one on one or a threesome, but we all agreed to meet up for a drink to get to know each other a bit more before anything happened. This was in late February 2020. By the time we managed to fix a date things started to get bad and any chance of meeting up died with the new lockdown rules. He only lived a 10min drive from us, but we were keen to follow the rules so our plans got put on ice. Jen kept in close contact with John over WhatsApp during the lockdown. Their conversations started off fairly innocent but didn’t stay that way for long. Their flirting led to sexting which led to photos. I still remember Jen asking me which photo she should send him one night. I was expecting to pick the one made her eye looks nicer or something, but instead of I was confronted with three of her nudes, her small perky boobs and pink nipples on show but nothing more. I presume it was her way of asking permission, so I picked one and watched nervously as she sent it. I couldn’t believe it, another guy had topless pictures of my girlfriend on his phone. But it didn’t stop there, by the end of the week she had progressed to full nudes. They started subtle, but it wasn’t long until I was helping. I remember one night taking a picture of her. She was on her hands and knees, naked, back arched with everything on show. John had pictures of every inch of her body from every angle. And although it may not sound like it, this really wasn’t like her, I think the lockdown had made her a little crazy for attention. Not that the conversation was one sided, John was sending just as many nudes back. I had never seen so much of another mans cock before. Eventually the news came that people living alone could make bubbles with other households. Johns house mate had moved out, so technically we could join up with him. I am not sure which one out of Jen and me actually suggest it first, but it seemed so obvious. I appreciate it was a risk, but we spoke all the time and had built up a friendship. Besides he was lonely and we wanted to help out. Before we could ask John, Jen needed to decide if she wanted me there or not. She had already ruled out a threesome, too much work apparently, but she wasn’t sure if she wanted to be alone with him or have me watch. Of course I wanted the latter, but she was doing this for me so I had to let her make this decision. When she finally made up her mind, I remember her sitting me down and telling me that, if she was going to do this for me, she wanted it to be one on one. She explained that she wouldn’t be able to get into it with me watching, she would be too concerned about me getting hurt, especially if she was openly enjoying herself. I reluctantly agreed that she was right, it would probably be awkward anyway. It was decided then, another man was going to have my girlfriend and I wasn’t going to be involved. All that was left, was to ask John. They had started face timing each other by this point, so on the next call she asked him. I was in the other room when she came running in and threw her arms around me. He had agreed to bubble. She would go round his place for date that coming Saturday. Which only left a couple of days. She told me it was only dinner at his, to get to know each other but nothing else was going to happen. Of course I wanted her to sleep with him immediately, but we had got that far, waiting a little longer wouldn’t hurt. The following days were something else. I couldn’t stop thinking about it and it didn’t help that we were stuck at home. And we had also decided not to have sex until after their date. She said she wanted us to be wound up ready for when she got back from his. When the night finally came, Jen took her time getting ready. It was odd watching her get ready for a date with another man. I remember walking into the bathroom to ask her something and found her shaving between her legs. I watched as finished off, leaving the whole area completely smooth. Then sat with her while she picked the perfect underwear. She decided on a matching black lace set. The bra pushed her boobs together into a killer cleavage and was so see through, you could see her nipples. The matching tiny thong was just as transparent and she wore the string sides pulled up high on her hips. It was probably my favourite set and it was odd watching her put it on for another guy. Next she picked out a black strappy dress that hugged her petit figure. And finally finished it all off with sliver high heels and a thin black choker around her neck. She asked me what I thought. I was speechless. Her outfit was to die for, her long flowing dark brown hair was prefect and her make up was beyond sexy. Jen was drinking so I agreed to drive her. Now that was a surreal experience. We chatted like nothing was happening, but in fact I was driving her to go on a date with another man. Yes, she told me she wasn’t going to do anything, but still. I pulled up outside his, and she gave me an air kiss, not wanting to mess her deep red lipstick. She told me she loved me and would text me in a couple of hours to pick her up, but I insisted she text beforehand to let me know he’s not some psycho. She agreed and the last I saw of her, she was strutting down the path to his flat, rearranging her dress. I waited for about 15 minutes around the corner until she text simply “hes cool, having a nice time already.” Knowing she was safe I headed home. I wanted a beer, but ended up having a coffee to make sure I was ok to drive. After two hours there was no text, then after three just one saying she would be a bit longer. Then finally, just before 1am she texted asking to be picked up, but told me to just message when I get there and wait outside in the car. The drive there was a blur and before I knew it, I was waiting outside. But it took her well over 15 minutes to come downstairs. Eventually she emerged from the flats holding her shoes. She got straight into our car apologising for taking so long. She swerved my kiss and instead gave me one on the cheek, telling me to drive home. She was smiling and looked happy, yet somehow was not herself. Her cheeks were flushed and she looked out of breath, but it wasn’t that, something was different. On the drive home and I am paraphrasing a bit, I asked her “did you have a good time?” “Yeah it was really good, he’s a great cook” “So you got on well?” “Yeah he’s such a great guy, it was so natural, you would really like him.” “So you just had dinner?” “Yeah we had dinner and then talked and then…” “And then?” “And then we had sex.” She said it so normally, so matter of fact, that I was taken by surprise and missed a turning. I wanted more but Jen, while laughing her head off, told me to wait until we got home, she didn’t want me to crash. So for the next few minutes we kept silent, only occasionally peeking at each other and laughing. When we got home, I dragged her up to our room, desperate to find out more. She told me, she should really shower first and pulled her dress off to revile she was bottomless. She saw me looking and shrugged saying “I couldn’t find them.” It was a shame because I loved that thong. She slipped her bra off so she was naked and went to leave for a shower. I told her it was fine and to get into bed. She reluctantly joined me, but still wouldn’t kiss me directly on the mouth. I remember her explaining “you really don’t want to kiss me babe, I love you but let me clean my teeth or something first”. I didn’t really understand but let it go. The conversation that followed went more or less like this. I started by saying “So… you had dinner?” “Yeah we spoke for a while while he finished cooking and had some wine. It wasn’t awkward at all, I guess we spoke so much beforehand, it felt natural. The food was delicious, you would have loved it, roast pork belly.” “Then what?” “Then we had some more wine on the sofa and chatted for like an hour about everything.” “And then what?” “I mean, you know what, we fucked, what more is there to say?” I almost choked when she said that which made her laugh. She was starting to enjoy herself now. While I gathered my thoughts I looked down her naked used body. She caught me and lifted my chin so I was looking into her eyes again and said “Ok then, what else do you want to know”. “How did it start?” “Err… we were chatting and drinking then one thing led to another and we started kissing. Then, I guess we like, got carried away and suddenly I was naked.” “Did you, you know, do stuff before, Like with your mouth?” “What!? Well yes of course, I did him for a bit, then he licked me”. “Did he make you cum?” “No… not then.”’ “But he did?” “Well… yes.” “What happened next?” “He picked me up and carried me to his bedroom. Once he put me down he climbed on top and you know, it started, we had sex”. “Did you use a condom?” “No sorry, I don’t think he had any and I didn’t” “What was it like?” “Good, I mean what do you want me to say? He has a big dick and knows how to use it, we tried lots of different things, it felt really good” “Oh, so was it long?” “30 minutes, no probably more, I am really not sure.” It hurt to hear all that, but at the same time I was enjoyed it, a very odd feeling. She then went on to say “we started with missionary then swapped around a few times.” “What did you do?” “Mainly him on top or from behind, you know I like that more.” “And that made you cum!?” “Yeah he was behind me, but I was also… you know, I was touching myself.” “And then he came?” “Not we took a break, I was feeling too sensitive.” “What then.” “We started and stopped a few times. You know, we did doggy, then we had some wine, then I went down on him, then wine, then up against the wall etc. It was fun, he felt really good. But then I said I had to go.” “Ok, so then you text me?” “Yeah I text you, but we were still messing around a bit and then we started again.” “Wait what! So you were having sex again while I was outside?” “Yeah probably, I can’t really remember what we did, but he was going fast, it was hard to keep up, I think he was in a rush to cum”. “Did he?” “Yep.” “What so he came in your…” “My what?” “In your…” “Yes he came in my pussy. What’s the big deal I’m on the pill.” She then went on to describe saying goodbye to John in a rush and grabbing her stuff, not finding her thong and running out to me. After taking me through the night she went to the loo and grabbed her phone, which had been buzzing the whole time. When she came back he said “do what to see what we did” holding out her phone. Though she insisted I get naked first and smiled when she saw I was hard. She laid next to me, almost looking shy and gently stroked my cock while I unlocked her phone and saw the first photo. It was a selfi taken by John of them kissing. It was so odd to see her lips connecting with another guy, but it did not compare the next picture. For one, it was such high quality. It was taken from John prospective, he was sitting on the sofa, his hard cock devoured by Jen. He hair was pushed back away from her face, her eyes wide looking directly at the camera. Naked apart from the chocker. It was so detailed I could see her lips squeeze the shaft of his cock. I was staring at it for ages until Jen finally told me to move on, that I would love the next one even more. She wasn’t wrong. It was from Johns prospective again, but now they were in bed with Jen laying on her back. Her face was cut out but you could see the rest of her body. Her perky breasts, then down to her smooth flat stomach. Her legs spread so wide, her feet were out of shot. But what instantly drew my eyes was her pussy. It was full of Johns cock. He was about three quarters of the way inside her, parting her small pink lips. I could’t believe my eyes. I could see in graphic detail as another man was sliding into my girlfriend. Just when I thought I had seen it all, Jen got a text from John and she told me to open it. It was a video. I clicked to download and play it. It wasn’t long, less then two minutes. Jen was in the the doggy position while Johns cock slid rhythmically in and out of her. After a load of hard thrusts, he pulled it all the way out. The phone then moved closer to Jens ass and suddenly I was getting a close up of her used, open pussy. He didn’t pause for long before he shoved his cock all the way back in and went back to pounding her. I don’t think Jen noticed he was filmed at first and for the most part was just moaning, occasionally calling his name. She finally realised at end of the video and collapsed onto the bed, rolling onto her back. Her beautiful naked body fully on show. A massive grin on her face. When Jen saw me put the video back to the start, she laughed and moved to climb on top of me, cow girl. I was so engrossed I barely noticed until I felt her hand guid my cock into her hot, wet pussy. I put the phone down, but she put it back into my hand saying “I want you to watch John fuck me”. I did as I told and watched the video again as she rode me. I only got through it two times before I couldn’t hold back. I exploded insider her. The second guy to do that within the hour. She bent down to kiss me on the mouth for the first time that night. Then climbed off announcing she really needed a shower. We spoke about that night a lot over the next few days, mainly all positive. We both seemed comfortable with how things played out and had both obviously enjoyed it. I was happy to do it again, but before I could suggest it, she asked me if she could keep seeing him. I of course agreed and before long she was spending a couple of nights a week over at his, normally returning the next morning. She gradually stopped dressing up so much though. When she goes over to his now for a ‘dick appointment’ as she calls it. She will just shower, shave, throw on some gym cloths and drive round. She doesn’t tell me much about what happens, she finds it too awkward to talk about unless she’s really, really horny. But it seems as if they have tried everything in every imaginable way. They slowed down a bit as the year went on and now only meet up for sex a couple of times a month. Always just the two of them. Though I have met John a couple of times. Once we all went for a drink between lockdowns and Jen went back to his that night, a very odd experience. They are not dating but definitely have some sort of relationship. Friends with benefits I guess. But whatever they are, I am happy with their relationship because ours has never been stronger. I hope you liked hearing about us and I will update you if anything new happens!