I’ve always been obsessed with the cuckolding lifestyle but never really had the chance to try it. I am 5’11 skinny but athletic and my cock is nothing to brag about. I was good enough around women but never had the guts to express my cuckold obsession to them. At 23 I met this girl Maya, same age as me, very nice body and a beautiful face. She was the first girl I could say was way out of my league. She was sweet, caring and very romantic, but quite vanilla in bed. I fell in love with her pretty much instantly and I felt so fortunate to have her and from the day we got together I was sure I would never experience cuckolding as she would never do such things. She was very monogamous and traditional, which was great but still at times when I was horny I would love for her to be more slutty.
I tried hard to forget about my cuckolding obsession but every time I was alone I would consume a lot of cuckold related content.
Fast forward when we were 26 our relationship was still going great although the sex life calms down a lot after the first year. We lived together, hanged out with the same circle of friends and had a pretty quiet life. One night we went to our friend Tom birthday party and he presented us to Antony, a work colleague of him. Antony looked like a pretty cool guy, he played sports, mostly tennis, was into music and was also very passionate about tv shows and movies in general.
As both me and Maya were both big movie lovers he gave us some suggestions for a nice tv show he had just finished. We talked a lot with him that night and we became kind of friends. Antony was tall, pretty in shape and good looking. I noticed that he seemed to like Maya, I mean why wouldn’t he, she looked great. But in my dirty mind I was curious to know if she liked him too. Maya was almost never flirty with other people but that night she looked just a bit different. She was enjoying the conversation with Antony and I also made sure to leave them alone for some minutes.
Idk what I was thinking, I mean she wasn’t the kind of girl who would think about other men especially with me around, but I still enjoyed watching them together. Antony gave us his phone number and so we could hang out again sometime.
As we got back home I asked her what she thought about him and she told me he looked like a great dude and that he had really good taste in movies. Maya also added that she always loved the idea of playing tennis and that maybe we could try it sometime.
About a week later we were decided to start watching the tv show he suggested and as we were both in bed I got an idea. Maya was sitting on the edge of the bed wearing some classic black shorts while watching the show so I took a picture capturing the tv and her watching it carefully including her beautiful legs in the frame. I sent the picture to Antony telling him we decided to follow his advice and watch the show.
He replied that it was great and we would like it a lot and although it wasn’t nothing special I liked the idea of him looking at my girlfriend.
I told him we could hang out again sometime and he said he would like that.
We met him again at a bar together with Tom about one week later. I pushed Maya to wear something nice but without revealing any kind of intention. We had a beer and started talking about tennis. Antony seemed very passionate about it and Maya was following him. At one point Tom who was neither into sports or movies told us to change the conversation so I told him to join me at the bar to grab some more beers while Antony finishes telling the story to Maya. We stayed at the bar for a bit talking about our jobs while my girlfriend seemed very concentrated to every word Antony was saying.
As we got back she told me that Antony was willing to teach us tennis and that she would love so much to try it. I told her it was fine for me even tho I never liked tennis, I just wanted to see them together. Tom ofc opted out saying he was not interested as so the very next day Maya took me to a mall to buy some tennis clothes. We found a couple of nice outfits in a sports store and she asked if I liked them. The skirt was quite short so she wasn’t sure about it. I told her she could try it and we could ask Antony if it was an appropriate outfit.
Since she was very naive she did just that, she wore the first white outfit. She looked amazing in it. I took a couple pictures of her and told her to send them to Antony directly.
After sending him the pictures he replied that she looked great and that they were perfect. That day I saw her texting from time to time and when I asked her about it she told me it was with Antony. I didn’t ask more questions as I was enough for me that they were texting. We hedged to the Tennis court one Saturday morning and met Antony there. He started explaining us the rules and everything and I loved how he was giving Maya so much attention explaining to her how she should move and keep the tennis racket. The session went well although I felt exhausted afterwards. Maya had a lot of fun and we decided to do that every weekend.
A couple of weeks later we saw Antony play against another dude and win. Maya looked so happy for him and as he finished she have him a hug. It looked like she didn’t care that he was all sweaty. They would text more and more and they also touched each other more while on the court.
As they were finishing the match I told them I was going to hit the shower and change. I went to the locker room and after 10 minutes of a cold shower I came out thinking I was there alone. I removed my towel and then saw Antony enter the locker room. Of course he had a good front look at me and I felt so embarrassed as my cock when soft looks so small.
He didn’t say anything but I saw him clearly looking at it. I quickly grabbed my underwear and got dressed as he started asking me if I was liking tennis. I told him it was fine and that Maya is the one who was really getting obsessed with it. As I turned around after closing my locker I saw him in his underwear and as we kept talking he pulled them down. My god, his cock was so much bigger than mine. It had to be at least 7.5-8 inches and quite thick.
“Yeah Maya is getting really good at it, I must be a very good teacher then haha” se said before hitting the shower.
I said goodbye and left but the image of his cock never left my mind. The dude was so gifted, tall, muscular, handsome and had also a pretty big cock. The cuck inside me felt so insecure but at the same time happy that he was around my girlfriend.
At home that day I told Maya about it. I told her that he came to have a shower and that he was naked.
“So ? How was he?” She jokingly asked.
I told her he was pretty gifted and she asked me what I meant by that. I told her his cock was huge and that it was pretty uncomfortable although only for a few seconds. “Bigger than yours?” Maya asked trying to mock me a bit.
I told her it was noticeably bigger and although she didn’t say anything I felt like she liked that. Antony texted me a couple of days later telling me he was planning to watch a small tennis tournament in a couple of weeks and asked if we wanted to join him.
I told him I had to talk to Maya about it but that I was sure she would like the idea. The tournament was in another city, a couple of hours by car and Maya seemed to like the idea. I told him we were in but a day prior I told her that something had come up at work and that I most probably wouldn’t be able to come. She was very disappointed but I told her she could go with Antony as he was driving anyway and I didn’t wanted her to miss it for my fault. The tournament lasted 3 days so we had booked a hotel room for a couple of nights. I told her she had her room and that I would try hard to come at least one day.
Maya was ok with it and my plan of letting them alone for a while seemed to be working. Antony picked her up pretty early that day and I was so exited and hopeful something could happen. I was to afraid to bring up the cuckolding conversation with her, but maybe if she was the want who wanted to fuck him that would be a lot easier. I kept in touch with her all day that day and she told me how they went to the tournament, had lunch together and that afternoon she told me she was getting ready as she would have dinner with him and after they would probably go to a bar near the hotel.
I was so exited about all this. I told her to have fun and keep me updated on everything while also asking to see what she was wearing. She decided to wear some denim shorts and a black crop top. She looked so sexy in those. All night I fantasised about them fucking although I was sure nothing was going to happen. She texted me after dinner saying they went to the bar and were having some drinks. I told her to have fun and about one hour later I decided to text Antony asking how things were going.
He called me a minute later telling me everything was great and that they were having a lot of fun. He told me how Maya had already had two cocktails and that she looked a nit tipsy. I laughed and told him she couldn’t handle alcohol and then he asked me if I would join them the next day. I told him I would try my best but that at least I had left her in good hands. He told me not to worry about it and that he would make sure she had a great time.
The way he said it sounded a bit malicious but I loved that as I was hoping for something to happen.
I spend all night watching cuckold porn as I didn’t got any more news from her. The next day I called her. She told me she had a lot of fun but had too much to drink. They apparently got back at the hotel around 2 am and she went to sleep. She asked me if I decided to join them and I told her I still wasn’t sure as I got work to do. Maya told me not to worry about it and kept working as they could go ahead without me. It sounded a bit like didn’t noticed me not being there that much and that Antony was enough for her. That day they both posted a lot pr pictures on instagram from the tournament and also having lunch at a nice bar. She didn’t text me much but in the afternoon Antony called me.
He told me he was planning to have dinner at a nice restaurant with her as he knew she loved sushi and there was this nice place there where he was planning to take her. He then told me he was out trying to find a nice shirt for himself and since he was there he asked me if it was ok if he bought Maya a dress and apparently the restaurant had a dress code and he also wanted to give it to her as a present. It was so fucking strange man. I acted cool tho telling him he didn’t have to spend money and that I could buy it instead but he insisted.
He told me the place was expensive but that Maya deserved it as she was amazing. I agreed with him and told him to show me when he finds the right dress. He texted me some screenshots later that day from Maya. She had sent him pictures of herself in the dress and it was so fucking hot. That jerk chose a super tight and short black dress. I never saw Maya were such things but from the screenshots she looked happy to wear them from him.
As an idiot I told him she looked great and that she didn’t usually wore such exposing clothes and he replied telling me she looked very comfortable wearing them for him.
Then as a loser I said “You couldn’t wait to see her live you had to get pictures lol”
He said he did and then send me another couple of pictures in which she was wearing the dress in the mirror and showed how it looked from the back. The second picture she was sitting on the floor. I couldn’t believe she was sending him those. My sweet innocent girlfriend doing something like that. I know I always wanted that but never truly believed she would do it. I told him to have fun and take care of her and he told me he would. I waited for her to text me and tell me about his present but nothing.
I decided not to disturb them during dinner but I really didn’t knew what to do.
I texted Antony asking him if everything was going well and he texted me a selfie of them. Maya looked so beautiful. He told me they would leave soon and get back at the hotel as Maya’s feet were hurting due to her high heels. He texted me he was going to give her a massage so she could relax. At that point I was 100% sure that man was telling me was going to fuck my girlfriend.
I told him he was a gentleman. He asked me if I wanted him to keep me updated and I told him to please do so.
About one hour later he texted me a picture of her lying in bed with her dress still on. He told me they were back and that he had to take care of her now. I asked him if she was ok and he replied that she would feel great in a while. I couldn’t believe it. My girlfriend was wearing that slutty dress and was with him in his hotel room. Minutes really seemed like hours. I wanted to know what was going on. I texted Maya but got nothing back.
I waited about half an hour before texting Antony again but still nothing. He finally texted me around 3 am and told me they were busy. I asked him what he meant so he sent me a picture of my girlfriend fully naked sleeping next to him.
I asked him wtf was going on and he told me not to act crazy now as I knew exactly what was going on. I tried to act like I was clueless but he told me to jerk off and go to sleep now. The next morning Maya video called me from the hotel having breakfast. I asked her why she disappeared and she told me she just lost track of time. At that moment Antony appeared next to her putting his arm around her shoulder. He told me they had a lot of fun and that it was too bad I couldn’t come. It was such a pathetic acting. I asked her how last night went and she said she had a lot of fun and fell asleep early while I could see Antony and his malicious smile on his face. She told me they had to prepare their stuff and do the check out so she hung up the phone.
In half an hour or so I received a call from Antony. I asked him what he wanted but all I could hear was moaning. It was clearly Maya. I couldn’t believe it. He apparently left the phone on the bed to make me hear what he was doing. I decided not to hang up for a while and I listened to him asking her if she liked his cock. She was telling him how big it was and in between moans she was expressing how much she loved it and how it was the biggest she ever tried.
He then hung up after a minute or so and I felt so humiliated.
I immediately pulled down my pants and started jerking off and as I was doing soo I got some pictures of him fucking her doggy style on his bed. His huge cock was going in an out of my beautiful girlfriend’s pussy.
I came so hard my fucking body was shaking. That was the day they would get back home and I was so nervous about seeing hew after knowing what she had done. She came home that afternoon, she hugged me and kissed me as she always does telling me how much she missed me.
I was convinced I had to say something so that night I brought up the conversation with her.
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