Masturbating with my buddy

Discussion in 'True Confessions' started by Roger Sullivan, Nov 21, 2025.

  1. Roger Sullivan

    Roger Sullivan Members

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    Hi, I posted this on another thread, but it seems apt here as it is a confession, this is an updated version.
    I'm 55. I have a friend in his 40s who has a very attractive wife. He knows I fancy her and he likes the idea of other guys lusting after her. When we were drinking at his house one evening, and his wife was out, he decided to show me some photos of his kit car. Ive seen it plenty of times and there was no need, but I went along with it as he is very proud of it. I soon realised his motive. He had the pics on his TV on a sim card. We went through the car pics and then surprise surprise there just happened to be some of his wife on the beach in her bikini. I didnt complain as she is very attractive. Then, they became topless. I asked him if he was OK with me seeing them and he said yes, as he knows I like her, and frankly, he enjoys it. I could see he was getting horny and aroused, and, so was I. He was asking me to comment about her body and at first I was a bit uncomfortable with it but I said a few remarks about her, the usual blokey stuff, which he clearly enjoyed. He asked if I would like to see more and I said yes, and the next set was of her naked in their hotel room, in various poses. I asked him if she would be OK with it and he assured me she would be. But I suppose he would say that wouldn't he? **(Update, she is aware and is pleased we are having fun with her.)** By this time he was very aroused which was obvious as he was wearing joggers. I was also in a similar state, but my jeans were hiding it. He then admitted that he was rock hard and the fact I could see his wife naked was driving him wild. I looked across and he was rubbing his dick through his joggers! He stopped straight away and apologised. He seemed to sober up at that point and apologised saying I must think he's a pervert, and switched off the TV. To be honest, I was quite enjoying it by that time and told him so. I also told him I was very turned on by the pictures and also the sight of him so hard and aroused. He didn't need telling twice. He put the pictures back on and asked me how hard I was. I showed him the bulge in my jeans He told me he loved the thought of me masturbating over her. I began to rub my cock through my jeans and he was groaning and doing the same. After a short time he had got his cock out and was stroking, and it wasn't long before we were both sitting there on his living room chairs, wanking over his wife. To cut a very long story a bit shorter, as you get the picture by now, we have repeated this many times since, but after a few times there is no awkward introduction, and we get naked completely. Then one time he said "Just imagine if Carol (name changed) came home and caught us at it! Looking at her pics and wanking each other!" "But we aren't wanking each other" I said. "But we could", he replied. I found the idea so horny I just sat back, put my arms behind my head and said, "Go on then, wank it! and so he did. I ejaculated so hard it went on my shoulder. It was so intense. So now here we are, regularly meeting up and wanking each other off over his wife. Is this a bad thing? **Update... she is very intrigued by our activities and wants to watch us play together. I'm not sure but I bet it will happen. He wants her to join in. I'm loving it but have a nagging doubt it will all end badly. Should I be worried? Should I stop? I would love to read your opinions.
     
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  2. Native Vee

    Native Vee Supporters HipForums Supporter

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    Thank you for being honest mate..

    Thats what its all about here on the confession base :)
     
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  3. Owen marra

    Owen marra Members

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    That's hot
     
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  4. SantaCruzRob

    SantaCruzRob Supporters HipForums Supporter

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    Why stop if everyone is having fun? :p
     
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  5. Sir Arthur

    Sir Arthur Senior Member

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    So fun. How tempted are you to put it in your mouth?
     
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  6. Roger Sullivan

    Roger Sullivan Members

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    I'm glad you think so. To be honest, sharing it gets me very aroused. I will happily tell you more if you like.
     
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  7. Roger Sullivan

    Roger Sullivan Members

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    I am sure that if she gets involved, she will want to see that.
     
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  8. Beatniks

    Beatniks Members

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    Had a similar experience. I was more like your friend during this particular experience. I’ll have to share someday.
     
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  9. Owen marra

    Owen marra Members

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    Please tell me more
     
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  10. Owen marra

    Owen marra Members

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    This one of my favorite things to do
     
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  11. Rosco Robert

    Rosco Robert Newbie

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    Extremely hot post. Think it is time to go oral.
     
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  12. Longzi

    Longzi Members

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    Me too
     
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  13. Hugh_36

    Hugh_36 Members

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    Get her to watch. I suspect he’d love to watch her sucking you off
     
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  14. dwva2017

    dwva2017 Members

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    Please do...would love to hear more & have a friend like that. But honestly...first chance to wank him, I'd have his cock in my mouth & be swallowing
     
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  15. SandBook

    SandBook Genderqueer. AMAB. Pic is Emma Roberts

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    I've been masturbating with a female friend lately. We've only done it three times in the past couple months. But we really enjoy it. Actually, the first time, only I masturbated and she watched me do it while naked. It was because we were showering together and she mentioned how much she admires how little I care about our friends seeing my penis given how small it is.

    I told her erect my penis is plenty big. The issue I've always had that I can't help and don't care about is cumming too fast. She asked how fast? I told her sometimes it's only a couple seconds and she wanted to see. Now, she really loves watching me masturbate and gets off seeing how quickly I ejaculate. And I have fun showing it off.
     
    6Sailor9 and Joe90 like this.
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