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The second meet and becoming a Cuckold (not mine)

The second meet and becoming a Cuckold (not mine)

This is the continuation from my first post, which covered my first cuckolding experience and how Sarah and Simon had sex and I'd overheard it. Again, this is my historical cuckolding experience from 2017 - 2018, nothing current.

After having had my first cuckold experience (despite it being unplanned and unexpected), in the first few days after it, I definitely felt somewhat conflicted. I think this was due to the difference between the fantasy and reality, I wasn't angry with Sarah or Simon, I didn't regret overhearing them, but I just felt a little awkward about it. Plus, I was now posed with the dilemma of what to do next.

A part of me really wanted to talk to Sarah about it, because once I'd been able to really process it all, I really enjoyed it and hearing her get pleasured by someone else made me feel happy and I wanted her to be pleased. I didn't know how to approach it, I was worried that she'd think I was weird and on a couple of occasions, I basically bottled talking about it! Sarah and I had met up with Rachel and Simon shortly after to go for a meal one evening, I tried to make sure they were sat next to one another on the table we were on and they seemingly carried on as normal, but I wanted to see if there was any tension.

Probably 3 weeks or so after the evening I'd heard them having sex, whilst Sarah and I were at her place one Friday night, we'd had a few drinks and we were pretty tipsy whilst watching a film. The drunk feeling gave me a little courage and I told her I wanted to talk about something, but I didn't want her to worry and I tried to introduce it gently. I started to explain that I'd overheard her and Simon a few weeks back, whilst I'd left the living room and she burst into tears and kept saying sorry over and over again.

I tried to calm her down, I told her I wasn't angry with her and that I just wanted to talk about it, but she was a little hysterical. I told her to just relax, I just wanted to talk about it and I told her I had 0 intention of telling Rachel, just reinforcing to Sarah I was legitimately not angry. She asked what I wanted to talk about if I wasn't angry about it and I decided to come clean and just explained that for a fair while I'd had a thing for cuckolding, what that included and how hearing her and Simon made me feel that night.

Luckily, she didn't tell me I was weird, but she said she didn't know how she felt about it as she didn't know whether it was something she'd like, in terms of having sex with strangers. I explained that I wasn't going to pressure her, but I wanted her to know how I felt and I asked her how she felt about having had sex with Simon.

Sarah explained that she'd liked Simon for a while, since before meeting me and she felt like it was a one off that she cheated and she continued to apologise and asked me to not tell Rachel. Again, I just reinforced to her that I had no intent of that, I didn't want this to affect the relationship, but I wanted us both to simply be as honest as possible and that I enjoyed what she did.

Naturally, it was an emotive chat and in hindsight, having that chat whilst we were both so drunk wasn't smart, lesson learnt! We agreed to leave it there with that chat and we finished watching the film and went to bed. The next morning the realisation of the chat was hitting me whilst waking up and it was Sarah who brought it up the next day. She apologised again, she said she's glad I told her about how I felt and I again told her I was fine with her and Simon and what they did. She asked me if I'd want her to do it again, I told her if she felt comfortable with it, then yes I would like that, but I didn't want her to do something she didn't want to do.

Over the next couppe of weeks, the topic came up sporadically when I spent time with Sarah, we also spent a bit of time with Simon and Rachel as well going to some Christmas markets and a day of Christmas drinking one weekend. When Sarah and I were discussing what she and Simon had got up to, it would sometimes be just a one off comment, sometimes talk about whilst we were lay in bed and at times, when we were having fun ourselves.

Where it started to change and become more legitimate was whilst I was at Sarah's, we were watching Game of Thrones and a scene in which little finger uses peepholes to view his women pleasuring men came on the screen and Sarah flat out asked me if that's what I'd do if her and Simon were to have sex again. I laughed at first and said I'd definitely do that, but would probably want to be sat even closer to see and hear it all clearly. Sarah started laughing and called me a kinky fucker but she also said she liked the idea of it and she'd be willing to try it.

I was so damn excited but I wanted to know from her why she wanted to try it, I didn't want her to feel as though she was having to do this. We spoke very openly, she told me she really liked Simon and it was amazing sex, she told me she would try the cuckolding dynamic but only with Simon and we needed to keep it from Rachel. I agreed and we started to logistically plan how it could work and things, using mine and Simons friendship and the fact we watched football together at the weekends as a good cover for it.

As this discussion was going along, I felt confident enough to ask her what she and Simon did on the night they fucked. She told me that whilst they briefly chatted at the bar at the horror circus we went to that night, he started flirting with her and she wanted more, he suggested they get Rachel and I drunk downstairs and that Sarah and Simon both head to bed shortly after one another, as they knew drinking whiskey all night would eventually put Rachel and myself to sleep.

Sarah said that they also had a very brief conversation in the kitchen and they'd planned to do it in the spare room quickly once Simon went upstairs pretending to go to bed. Sarah explained that he came into the bedroom and she was already naked, she said they barely spoke but he pushed her back and opened her legs to eat her pussy and she started to moan really loudly, with Simon reminding her to be quiet. She said he kept licking her and fingering her whilst she lay on her back trying not to make too much noise but she ended up cumming quickly.

Sarah explained once she came, Simon moved his head up to kiss her and he slid his dick inside her bareback, she said there was no discussion about using condoms but she got caught in the moment. Sarah explained he originally fucked her slow and kissed her, but she asked him to fuck her harder a few times and he did as she asked. At this point, I explained I'd heard her saying that and I could really hear the bed creaking and hear the 2 of them moaning.

I asked Sarah where he came and she said she made him pull out and she sucked him off to swallow his cum, saying that a fair bit ended up on her chin but she cleaned it up before I came to bed. I told Sarah I'd heard Simon leave the room and go to the master bedroom and I was stood at the bottom of the stairs and that I'd wanted to come up immediately and eat her pussy for her. Having finally discussed with her what they had actually done and getting Sarah's confirmation that she wanted to do this more, we looked at the next hurdle: talking to Simon.

Simon and I usually watched football together on a weekend, neither Sarah or Rachel would join us as they hated it, so on one of the Saturdays before Christmas, we had planned to catch the 12:30 kick off. I suggested to Simon that he meet me at mine first and we'd walk to the pub to watch it. In reality, Sarah had stayed at mine and we decided to ask him about the possibility of becoming Sarah's fuck buddy together, so he could see it wasn't a joke or anything.

Once he arrived at mine, I told him to come to my room as Sarah was here so I wanted him to say hello before we went the pub. I lived in a house share and at this point I was a little paranoid they may hear this conversation lol!

I explained to Simon I knew about him and Sarah and his eyes widened and I think he was expecting me to explode at him, but I immediately told him I really enjoyed what they did and I'd heard most of it and Sarah and I wanted it to happen again, preferably regularly. Whilst it took a few weeks for Sarah to seemingly open up to the idea, Simon just laughed and said 'Where do I sign up?' ? The fact that he wasn't awkward about it and was keen made me feel so much more comfortable and I think Sarah was already set on them doing it again.

Simon asked me about how long I'd liked cuckolding and if Sarah was okay with doing this, to which she confirmed she was very much wanting to do it again. Simon was adamant that we kept it from Rachel, the 3 of us agreed on a shared responsibility and that we were in it together and had to be discreet. He asked about how we could plan it all and Sarah explained she had been looking into chat apps to use separate to WhatsApp, we all agreed to use Kik with notifications muted, but it would be a good way to keep everything anonymous and still communicate as a trio often.

Simon and I then went to the pub to watch the football and Sarah went home and after that game, Simon came to mine to play some fifa. We spoke really openly and he said he'd wanted Sarah for a while and he again wanted to know if I was okay with it all, to which I gave my side as someone who wanted the cuckold experience, that this was an ideal set up. We spoke about using our weekly football plans as a way of planning the meets, either at mine or Sarah's (predominantly at Sarah's as she lived in her own apartment, I was in a house share) and that would mean each meet would give us a solid 2 hours and he wouldn't be expected to be on his phone whilst at the pub with myself. As the Christmas period was busy for all 4 of us, Simon, Sarah and I agreed to the first proper meet to be 05/01/2018.

There was huge FA Cup game that evening between Liverpool and Everton so Simon and I had already planned to watch it together, Rachel wouldn't suspect anything else and it would mean we'd get a good 2.5 hours for the meet with catching the pre game stuff. I'd advised Simon to meet me at mine first, then we'd walk to Sarah's. In the build up to it, I know I felt nervous before leaving mine with Simon, but we just chatted as normal on the way to Sarah's, surprisingly talking about the football. I made a joke that we'd probably need to catch the highlights instead and it very much broke the awkwardness!

We arrived at Sarah's and she let us up to the apartment and she opened the door, dressed in red lingerie, she smiled and asked us in. I'd already bought wine for her and also a mixture of beers for Simon and I and she lead us to the living room. I got all 3 of us a drink and we all briefly chatted whilst they sat on the couch and me on the chair.

At this point, Simon asked how we'd feel about not using condoms, as he didn't like how they felt and he'd said Sarah also seemed to enjoy it bareback. Sarah looked at me and I told her she had my full support in what she felt comfortable with. It's worth noting, Sarah was on the injection, however, I always used condoms with every girl I've been with, including her. Sarah said she was fine with bareback, but she wanted Simon to pull out and not cum in her and he agreed to that. As a cuckold, it drove me crazy knowing she'd be taking him raw and I honestly couldn't wait.

Shortlynagter chatting a bit more, they started kissing and there was a lot of groping, Simon grabbing her tits and thighs and she then climbed on top of him to kiss him, whilst he slapped and grabbed her curvy arse. Sarah briefly turned round to look at me and mouthed 'are you okay with this babe?', I nodded and smiled at her, she then turned back around and kissed Simon. Sarah was soon completely naked, lay on her back whilst Simon fingered her and kissed her on the couch. I'd heard her moan when we had sex, but it really did sound different this time.

I suggested we go to the bedroom to get comfier and they both agreed, but before leaving the living room, Sarah stripped Simon and it was the first time I'd seen his dick. It was easy to see why Sarah enjoyed fucking him ? His dick was stupidly girthy and I knew that he'd stretch her and get deep in her pussy. Sarah lead the way to her bedroom and she quite literally jumped on the bed and landed on her back, legs open and giggling away. Simon followed and got straight into eating her pussy and I sat on the side of the bed watching them.

Watching her moan and caress his head whilst he pleasured her, along with her cute little feet and toes curling in pleasure and asking him to keep eating her out was driving me wild. I don't think I'd ever been more erect in my life. Simon then started to finger her pussy and he started to eat her arse with Sarah letting out a very different moan. This carried on for a short while before her Sarah came for Simon eating and fingering her pussy. She was screaming so loudly, her thighs tightening around Simons head and I could see her face flushed red whilst she came. I briefly wanted some slight involvement, so I leant over and kissed her passionately.

They traded places, with Simon lay down and Sarah starting to suck his thick dick and he started to moan himself. Sarah was teasing him with her tongue and made a point of telling me his dick was far bigger than mine and I honestly adored the humiliation. Watching her literally choke herself on his dick and gasp for air was unbelievable.

Simon was quite verbal and it seemed the more he asked of Sarah, the more she did, sucking his balls, trying to deep throat him and eventually, having her climb on top of him to ride his dick. I made sure I had a good view and watching her tight pussy stretch and slide down him and hearing her gasp and moan as she tried to take it all was enough to make me nearly cum. She started riding slow and she told me just how much he was stretching her and looking over at me. I blew a kiss to her, she smiled and started to really ride his dick deep, I could hear sound of his dick in her as she was dripping wet.

After a little while of riding him, Sarah ended up laying on her back and Simon slid inside her. At first, he was long stroking her and the noises she made when he slid in as deep as he could were unreal, I was convinced she wouldn't be walking the day after. Simon picked up the pace and started to fuck her much harder and deeper whilst they kissed. With the the angle of Sarah's legs as she was getting fucked her foot was really close to my head so I gently started kissing and massaging her foot and she reached out to hold my hand as Simon pummelled her really fucking hard.

It wasn't long after that Sarah came again, her thighs tightening around Simons waist and I could see on the bed how wet she was as it had run onto the quilt. Simon told her he was going to cum and she told him to cum in her mouth so she could taste it. He pulled out and put his dick in her mouth and he moaned as he shot ropes of cum into her mouth, thrusting his dick into her mouth. Once he'd stopped cumming, Sarah turned to me with a mouthful and motioned for me to come over to her and I positioned my head under hers whilst she gave me a very passionate kiss with all of Simons cum in her mouth. I'd asked Sarah to do this in advance, but I can't remember if we told Simon about it.

It was amazing to kiss her and taste another mans cum in her mouth and she then went onto suck simons dick a bit more, whilst I ate her pussy, her arse and kissed her feet. Simon made a joke about asking if we were catching any more football this weekend and once everyone had calmed down, we all had a little chat about the events and what we enjoyed.

To me, this really helped the experience, the check in with one another allowed us all to voice what we'd enjoyed, it helped reinforce that this wouldn't be a one off and all of us were very enthusiastic with what had happened. I went and got their drinks for them and I came back and Sarah asked if this is how I thought cuckolding would be, I told it exceeded everything I'd wanted.

They went for round 2 not long after, this time, with Sarah on all 4's facing me while Simon fucked her from behind. This was so amazing as I got closer to Sarah to hold her hands and kiss her, I told her how happy she made me and I asked if she was enjoying it, she told me how good he felt inside her and we spent a lot of time kissing. Simon briefly stopped and started eating both her pussy and arse whilst I kissed her and I was so so glad that she was getting the attention she deserved.

Simon slid back inside her but went balls deep and the noise that Sarah made sounded like she'd been fisted. He was stretching her and the look on her face was a mix of pleasure but also a shocked expression at what was happening to her. He continued to pound her from behind and she was throwing her curvy arse back onto him and Simon told us he was going to cum again. This time, he pulled out and came all over her chubby, gorgeous arse and I happily obliged in cleaning every drop for her, whilst Simon positioned himself in front of her so she could suck his dick again.

It was time for the epic evening to come to an end, Simon got dressed and we had a few beers and Sarah had some wine whilst we caught the very end of the football and we continued to chat about the night. I could see how comfortable they were and it made me feel at ease.

I must admit, at this point the fear of Rachel finding out was starting to creep in and I had the worry of a neighbour seeing and saying something, but I just refocused and allowed myself to take in the nights events. As Simon left, Sarah gave him a kiss and I said goodbye to him as well.

I stayed at Sarah's that night and we lay there kissing and chatting and I felt so happy, so sexually satisfied and I was really grateful that Sarah tried it. She told me about what she enjoyed the most about it and that if we could, she wanted to see Simon more often and I said I wanted the same. We then had sex ourselves and I came so damn quickly, I couldn't control myself, luckily though, Sarah had already had plenty of dick before me lol!

The next day, we had breakfast and chatted about the night before, Sarah was still very enthusiastic about it and legitimately enjoyed it, this meant everything to me. I didn't want her to do something she wasn't comfy with, so I felt so reassured when we spoke about it. We did a check in on kik with Simon, he too was very happy about it and we agreed to arrange another meet soon
Published by JimSparrow44
1 year ago
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Great read , looking forward to more of this series.
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