Extreme Cuckolding Pt. 06

We spent some time working out how Richard could watch me having sex with Trent. In the end we just decided to go for a drink with Trent, and then back to our flat for something to eat, and see what happened.

I phoned Trent and all of a sudden he had a few suggestions. At first he said he wanted me to make it obvious to Richard that I was his girl for the night. I told Trent about us three going for a drink first, he said he would rather it was just me and him. I said that would probably be okay.

I had already asked Trent about when we went home, if he minded Richard wearing women's clothes. Trent said it was okay as long as Richard didn't look like a drag queen. I explained what Trent would see, I said there would be, no make up, and no wig and Richard would only talk if he was asked something. Trent said it sounded okay. I said he had to promise not to laugh at Richard. He said he wouldn't.

You know apart from wanting Trent between my legs again, I was really hoping Richard would like this experience too. In fact I was more worried about how things would go between Trent and Richard. I told Richard what Trent had said, and Richard told me he was okay with it all. He said a lot more but that was it in a nutshell.

Richard's surprise turned up a few days before Trent came round. I sat on the bed and told him to open the package. He just gulped and flung his arms round me. Two pairs of black shoes were in the box. One had a two inch heel the other a three inch. They were just plain black court shoes. The two inch heeled shoes didn't fit but the three inch fitted perfectly. I told him I'd send the lower ones back.

I instructed him how to walk and to take smaller steps, how to balance on them, and not get complacent, because as soon as he did he would end up on his ass. He did stumble a little a couple of times, but he was better than I thought he would be. He asked how I managed to keep upright on heels twice the height of his. I said I had been wearing them for years, and with high heels you have to find a comfortable pair. Even at that time I wasn't sure about him wearing women's shoes, but I also didn't want him going around in his slippers, or trainers.

So to the big night. I spent a little time looking at the clothes, and in my head I kept reminding myself what Trent had said, "no trying to look sexy and not like a drag queen," so keep that in your head while I describe what Richard wore.

I picked the white bra, white panties, and tan tights I had bought Richard, and the black skirt, and one of my old white blouses. There simple, and something which a woman would wear to work, agreed? I told Richard why I had picked this for him, and he said he understood, he even asked if he shouldn't wear a bra, I said I thought it was okay, because it wasn't a colour one, so it wasn't glaringly obvious. He smiled, he looked nervous but he smiled. I told him to take his shoes off, and put them on when he heard us in the car park.

Like I said in past parts, I get that some people have jumped right into dressing their husbands as sluts, but this had to be right for all three of us, and I didn't want to mess things up for all our sakes, especially Richard's.

I took a couple of photos of Richard on my phone. I told him not to smile, so in the first he was just stood up. In the second I got him to sit on the couch, cross his legs, and look at the telly, so he wasn't looking directly at my phone. I said I would show Trent how he looked, so it wouldn't be a shock when he walked through the door.

Richard is a good cook, and it is something we share between us, deciding on who will make dinner usually depends on who gets home from work first. It was Richard's idea not to eat with us, but he would happily make something and bring it in. I said to keep it simple we'd have a chicken salad, and we bought strawberry trifle.

I let him sit there and watch me get ready. I know this sounds a little strange, but I had in my head that I had to really outdo Richard in what we were wearing. It was more about Richard being pushed in the shadows. I knew Trent would look at him obviously, but I wanted to take away the limelight from what Richard was wearing for his own good. I put on red panties, tan coloured hold up stockings, which I had pulled up as far as I could. I didn't wear a bra. He sat there gawping as I put on my make up. I piled it on quite thick, and I could see he wanted to ask me why. Next came a heavy coat of bright red lipstick, and then I pinned my hair up.

I told Richard to pull out the box from under the bed. He took the lid off and moved the paper. He looked at me in shock. I put it all on. The skirt was sky blue, and came to just above mid thigh. The jacket was sky blue, and the hat was sky blue with a little pair of silver wings on the front. I even had sky blue high heels.

I waited for a question, but he seemed struck dumb. Finally stuttering words came out. So there I was Jenny the airhostess. I must admit I looked bloody good, and overdoing my make up I looked like the real thing. I guess the suit wasn't that obvious that it was from a fancy dress shop, not until you factored in the length of the skirt, and I wasn't wearing a blouse so there was a bit of cleavage peeping out, as well as my "slut wife" locket. Finally after what seemed like a long time he smiled, and asked me where the plane was parked. I said the skirt was too short for me to be the real thing. He nodded a little, but said everything else was right, although I should be wearing a blouse if I wanted men to think I really was a cabin girl.

I wore a coat to the pub, but I still got looks from guys who spotted the hat. I text Trent to say I was outside, and could he come and get me. I don't mind walking into pubs on my own, but I wanted to meet him outside first. I undid my coat as I saw the door swing open. He actually stopped and gawped at me. The first words from his mouth came out, "fucking hell."

I took my coat off outside the pub, and we walked in. I'm quite used to getting looked at, but everyone in the pub looked at me, some eyes lingered, some came back to me a few times. Trent asked me why I was wearing it. I said I wanted to wear something different. He laughed.

Even at 7 o'clock in the pub there were a few men who looked like they were drunk. One of them came up to us, and stood there swaying a little. He said he thought air hostesses were amazing, and they always looked like they had just stepped out of a salon. He asked me what airline I worked for. Trent told him I worked on a private jet for a rich Arab. The guy took it all in. He said I had sexy legs, and Trent said the Arab made me wear my skirts short. He said something about that not being right. Trent said she gets a little bonus for wearing it, and turning a blind eye to wandering hands. The drunk stumbled away then.

Then I heard, "Jenny, is that you?"

He looked at Trent, and then back at me. Then he looked me up and down.

I said, "Trent this is Adam who I work with, Adam, Trent."

Adam said, "I know who he is. Where is Richard and why are you dressed like that?"

Trent made what some people would call an asshole comment, he said, "We're off to a fancy dress party, Rich is still getting ready, are you going as Delboy, got your three wheeler outside?"

Adam had a sheepskin coat on. He just looked at Trent and then walked away. I looked back over at Adam later, and he was talking to two others. One guy I didn't know, but the other one Nick works at the same place as me. Nick was just staring at me, and I'm sure they were talking about me being with Trent. (Nick would fuck me in the future.)

The drunk who came up earlier came back with a couple of his friends. He asked if he could have a picture taken with me. Trent said he would take it. So I had these two drunks either side of me. I could feel the guy who did all the talking earlier; put his hand on my ass. Also I could see Adam, Nick and the other guy just watching it all. Trent said we should go, and gave the drunk back his phone.

I told Trent the guy had felt my ass. He said something about wondering why I wasn't smiling too much. He asked me if I was worried about Adam and the others. I was a little to be honest but I told Trent I wasn't. He echoed my thoughts, when he said, "They think we're having an affair or something."

We stopped outside the pub, and I showed Trent the two photos I had taken of Richard. He just scrolled back and forth between them. I said I could text Richard and tell him to change if he wanted me too. Trent said, he thought that would make it even more awkward, because it would mean he had told me Richard looked silly or something. I could see the logic in that and I was kicking myself that I hadn't thought of it. It just proves you can't think of everything. Then Trent asked what do we call Richard. I said Richard, wondering why he was even asking that. Trent said he looks more like a Rachel than a Richard. I said no you're not calling him that just call him Rich. By this time I was really wondering about calling a halt to it all. It just seemed there were more difficulties cropping up.

Trent said, "Stop looking so worried. We have to just act like everything is normal."

When we got to the flat I said I'd go in first and make sure Richard was okay. Trent said, no you won't, it'll be fine. I'm not going to laugh, and the sooner we get this done the better it will be. We walked in the flat, down the hall to the lounge, and then to the kitchen where Richard was fiddling around.

Trent said, "Hi Rich, how you doing?"

Richard was blushing, and I was just stood there hoping it things would be okay.

Richard was red, but he said, everything was fine, and dinner would be in 20 minutes.

Trent said, "Great we're starving. You look good mate."

Trent went in the lounge then. I said I'd sort us some drinks out. Richard actually pushed me away, and said he would do it, and bring them in. I really wanted to ask him if he really was okay, it must have showed on my face. He said he was fine, and to stop worrying, because I was making him more nervous. I guess I had been told, so I went and sat with Trent.

I asked if Trent if he was okay, and he said he was, and basically told me the same as Richard. He told me to stop worrying because it had gone well so far. But I wished he hadn't have said, so far, on the end of it.

I just sat there thinking I was missing something in all of this, or I was indeed worrying too much. Trent actually pulled me into a cuddle as we watched the telly. He had his arm round me, when Richard came in. Richard handed us the glasses of wine, he seemed okay even though he was shaking a bit. Trent said thanks and sipped the wine. Richard went back to the kitchen.

We sat at the table and Richard brought the food in. He asked if we needed anything, Trent said no, this looks great. Richard went back to the kitchen. I wanted to ask Trent if he was okay, yet again, but I decided to shut about it. I really think, I was expecting Trent to talk about Richard, but he just talked about the drunk in the pub. I think now looking back I was the one who took the longest to relax. It still amuses and befuddles me to this day.

We had the trifle, and another glass of wine, then coffee, all served by Richard. Trent told Richard he loved it all, and then he went to the toilet.

I went in the kitchen and Richard was washing up. I wanted to tell him to leave it, but I think he wanted to keep himself occupied. I said I was taking Trent to bed, if that was okay. Richard looked heavenwards, and said I shouldn't ask. I said okay. He said call me in if Trent doesn't mind, and I won't touch myself. He said remember what I like, and how to act. I said okay and I kissed his cheek.

How he wanted me and Trent to act was one of the things we had discussed, and I had passed it on to Trent, mainly about me talking to, or rather at Richard now and then. At some point while Trent and I were eating Richard had been in the bedroom, and lit a few candles. We had never discussed doing that, but I just went with it. I took off my clothes, and Trent and I got in bed. We kissed and touched each other. I had told Trent I needed to feel a little turned on before we asked Richard in.

I asked Trent to call Richard in, he said, "Rich you can come in if you like."

Richard came in and Trent told him quite gently to sit in the chair.

This is where things got a little awkward for me. I knew Richard would like me to have fun, but just how much. Trent started kissing me, and then he moved between my legs. I gasped a little as he put his cock in me. I could see Richard's face, as he sat in the chair. He looked sort of mesmerized by the whole thing. Trent was kissing me, and then he moved further in me which meant he couldn't reach my lips. I felt him pull the covers of us, and I heard Richard moan a little, because now he could see Trent's ass in motion.

Trent asked, "Are you enjoying it?"

I replied, "Yes."

He said, "I was asking Rich."

Richard just blurted out a soft, yes.

My hands were on Trent's hips, and because he had moved I couldn't see Richard's face. Trent started fucking me a little faster, but it was still about only half his normal pace. I got into it a little more, and started moaning like I did when Kelvin had fucked me in the flat below. I felt an orgasm growing and I tried to suppress it. I've said before I'm not a screamer, but I do pant and groan, but even that I was trying to keep under control.

Trent knew I was coming, he started saying in a soft tone, "Come for me Jenny, show him how you come for me."

I started being a little more vocal, I said I was coming and how good it felt. In my head I had my fingers crossed, hoping Richard was okay with it.

Trent kept going, and then went full speed ahead, for I guess about two minutes I got the hard fuck I usually get from Trent. He came and I think even he wasn't as verbal as he normally is.

Trent kissed me and said he would go and leave us to it. He said goodbye to Richard, he picked up his clothes and went out of the bedroom to dress.

Richard didn't move until we heard the front door shut. I asked him if he was okay, he didn't answer for a while, and then he came towards the bed. I could see a wet spot on the skirt. He said he wanted to go and change. I spent a couple of minutes there waiting. Those minutes were agonising. Okay I knew Richard had come, but I still wasn't sure if he liked it as much as he thought he would.

He came back in and got into bed. He kissed my cheek, and asked me why I wasn't like he imagined I would be. He asked if I was scared. So I told him I wasn't sure if he would really like it. He said he understood I was concerned but he really liked watching and I should know that. We talked a lot about it, and I told him I didn't want to hurt his feelings, or for him to suddenly get upset. He laughed, and told me, he thought it was sweet, but next time he wanted me to go full bore, and really enjoy myself.

It took me a day or two to get round the idea of doing it again and more importantly to just let go. I'm not going to go on about that anymore.

When I got in to work the Monday after Trent fucked me, both Nick and Adam asked about the fancy dress party. Adam said I looked really good. Nick I could tell was trying to catch me out. He asked why Trent wasn't in fancy dress. I said he had brought Richard home after their football game, and said he would drop us off, so we went and had a quick drink while Richard got ready. I don't really think I convinced them, but they couldn't really say a lot. It got round work that I had been to a fancy dress party, one of the girls came up and said she had been told I looked super hot, which made me chuckle, because of the way the two guys had talked to me. She asked to borrow my air hostess gear one day. She did borrow it a few months later, and when she brought it back, she looked a little annoyed. She said she got ready to go to a fancy dress party. Her husband took one look at her and said she wasn't going out of the house wearing that. She said she refused to go, and they spent the weekend not speaking.

The next part will be the fuck I had with Trent in front of Richard last December. You'll see how things had moved on.