Act three
Mike
I had been dressing in Jane’s clothes for a few years now, and loved the thought of seeing her with other men. Luckily I had size 6 feet and could squeeze into her heels and I had collected a few things myself over the years and had them hidden in the loft. She loved to go out and party with her friends, and encouraged her and I loved to stay at home and dress and fantasies about her getting fucked by other men. I often dreamt of being with a man myself and loved the idea of being dominated, but always had to stay strong and in control for Jane. She loved sex, could not get enough of it, and always enjoyed joking about my small cock and teasing me … that’s why I got her the dildo as a surprise for her birthday, and she loves it when I use it on her and she teases me about my small cock, and getting a real man into fuck her whilst I watched. I had never had the courage to go through with it, and never sure how she really felt about me watching her. There was only that one time before when she went with that guy to his hotel room. At the time I was dressed at home, and chatting on line with a guy who wanted to fuck me. I had a private profile that Jane did not know about and I would flirt with guys on line. On this night, I had arrange for him to come over but he was running late and when Jane told me about her chance to go with this guy to the hotel room, I just said yes go for it, and took my opportunity to invite this guy round and had my first opportunity to suck a cock. I loved it, could not believe how excited I felt when he knocked on the door. He was very straight to the point and said he was on his way back from the pub and only had a few minutes. He pushed his way past me in the hall way and told me to get on my knees. He switched the light of, and pointed to his fly. I just unzipped him there and then, and pulled out his thick warm mass of cock. It seemed to unwind felt warm and sticky as it was a warm night. I hesitated, but he pushed towards me. Come on then slut, get on with it. I opened my mouth and his cock pushed into my mouth. Look at me whilst you suck he said, so I looked up and started to suck him of as quickly as I could, part of me now worried in case jane came home early. He came very quickly and I gaged when he went deep into my throat. I sucked him of, and started to feel that incredible feeling of humiliation and arousal as be face fucked me. Soon he pushed deep and released his jet of cum into my mouth. I gagged again, and the cum started to run down my chin as it was the first time I had swallowed cum.
On the day of Janes train adventure I was dressed again, and had arrange for the same guy to visit me, but as janes adventure continued I put him of so I could keep texting her . This time I felt more involved watching the messages and getting her texts and telling her how far to go. I felt in control, and this was so exciting.
I got the shock of my life when Kev introduced himself, how the fuck did he know where I worked. This was very unnerving. I could see immediately why Jane submitted to him. He was tall, mature, confident and turned out so be such a nice guy.
Act Four
The trap –
Kev talking with Mike
Then I smiled – “look Mike, don’t worry, I have come to apologise as I did not mean to scare Jane. I thought it was what she wanted, I could see from her fab account that she was into this so I just went for it – all at her pace – she could have backed out any time – so I just want to tell you personally – and maybe I could buy you a drink. I was going to ring Jane, but did not want to risk her going to the police.”
Having now paused I let him respond. “Err how did you know where I worked”. “Agh – I said, well, my turn to confess…. You see I am a private investigator and was once a detective with the police. I generally I get involved with fraud, insurance claims etc. - Here is my card” (it wasn’t real just one of many fakes), “so if you want to report me for harassment be my guest .. , Sometimes I just get carried away as well – I can’t help pushing boundaries , so some simple checks on line and I located your identity and then just using on line social media managed to find out where you worked. Look, relax, come on, let me take you for a pint, I have a proposition for you”.
Mike and I sat in the pub and chatted, he was now more relaxed and we got on well. I kept on with my firm but polite approach. “Obviously I said, if you and Jane are still together, then I can only conclude that your enjoy the cuck fantasies and like many other men get off on the thought of your lovely sexy wife getting fucked by other men. So why don’t we work together and spring a surprise on Jane. What do you think. I have a few friends who I can ask along, all safe and sane, and we can have a party”. Then I said, “Only if you’re sure Jane would be happy with me bringing a couple of friends round to fuck her whilst you watch,,, I could tie you up as well if you wanted me to”. I then went on to ask him …. “Is there any other fantasy you would like to explore?”… Mike paused, and then I just could not believe how quickly he opened up to me. He told me that he liked to cross dress often in Jane’s clothes when she was out, and in fact on the night of the train journey he was wearing her heels and stockings, and he has a wig as well, and has always wanted to be dressed whilst Jane was getting fucked. I moved closer as he was talking quietly, obviously conscious that we were in a public place, although we were sat at the back of an empty dimly lit pub, and I rested my hand on his leg, then as he talked I moved my hand towards his cock. “So what’s your girly name” I asked, he said “shelly”, I then asked – “do you have a profile”, and then he retracted slightly, “oh, well I used to but I deleted it”. He said how he loved reading the cuck stories and fantasies and often talked with Jane about them. So I asked him, “Have you ever been fucked by a man”. “No” he said, “I sometimes use Jane’s dildo and she has experimented a few times on me”. “Have you ever sucked a cock Shelly”, I asked him, using his girly name which I think worked, he blushed and was clearly starting to enjoy my line of questioning , “yes once” he said, “well you could suck mine if you wanted to”… he went quiet again, ”Mike, relax,,, Its ok let’s just see how you feel on the night, what about if I say to you… Mike do you want to be my tranny fuck whore” .. “would you like that… maybe be I could get you to dress up” … “No” he said, “Jane doesn’t know I dress”,,, “OK , what if I force you, part of the blackmail fantasy, imagine how it would feel ” I said … He smiled,,, “wow that would be perfect… God he said this could be an amazing night”. Then I paused,,, “ his cock was now straining against my hand,, “Mike, I have fucked men before,, I could fuck you if you wanted me to, when your dressed up in janes clothes, I bet you look great,, go on ask me”,,, and then I could feel mikes cock hard in his trousers,,,, I rubbed his cock gently with my hand and he said “will you fuck me, can I be your tranny whore sir”,,,, Mike was gone now, clearly very aroused. “So, Mike what’s it to be”…. Mike nodded. I continued to rub his cock, and I found his fly, zipped it down and slipped my hand inside his pants and started to wank him. His cock was small, and he opened his legs slightly to let me continue “Is that a yes then”, and Mike paused, “well,, mmm I am not sure to be honest, I really should tell her”, Then I squeezed his cock in my hand, taking control of the situation and said, “but that will spoil the surprise, you know how she enjoyed the train journey, being out of control”,, Then mike paused again, thinking hard, he said, “but I was texting her and knew what was going on and re assuring her “… then as he worked things through in his head he said, “but I will be there so I am sure it will be ok”, “Mike”, I said, “remember you get explore your fantasy too, I can force you to dress”,, ,, ,,, “ok . ohhh he said, you better stop I think I am going to cum, please stop…. your right he said , Yes, yes, it will be amazing, I have always wanted to see her get a good fucking by more than one man I am sure,, she will be ok I know how to handle Jane.” I cupped my hand over his small cock and balls, gave him a playful squeeze and then let go of him before he got to the point of no return, slowly zipped up his fly. Good girl, that’s settled. I put my hand out to shake his told him I will see him Tuesday at 7, and if he has any second thoughts just ring me and we can forget the whole thing. I then turned back to look at him,,, Mike, I said firmly, He looked up,,, “it’s your decision but don’t fucking dare piss me about”,,,
As expected, Mike was a weak and submissive cuck, and he was soon engaged with my plan.
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