Extreme Cuckolding Pt. 05

So on to my weekend away with my wonderful boyfriend Trent. I was 21 at the time, and looking forward to being his girl. I already had an outfit for a friend's wedding two weeks later, so I wore that. It was black, and like a skater dress, with a cream band on hem that was about 3 inches wide. A wide brim floppy hat came with it, in black with a cream band. It hung about 4 or 5 inches off my knees, so I could wear cream stockings with a seam attached to a black suspender belt, which was part of a set with a bra and panties. I had 5 inch black high heels with an open toe. I used black eye shadow and black mascara on my eyes, and red lipstick on my lips.

Richard wasn't allowed to see me until I was ready. He had seen the outfit I was wearing, but he hadn't seen me in it. I called to him, and he opened the bedroom door. I gave him a slow twirl and he really was speechless. Finally he said I looked, "beautiful."

One thing about the word, beautiful, it wasn't a word he used very often, pretty, sexy, or hot were his normal choices. I thanked him and part of me at that moment didn't want to go. There have been a few times like that since, and I'm sure if other wives are honest they have had similar thoughts. I hid it from Richard, and sometimes in the future there were things I have hidden, which will crop up.

I very nearly had tears later in Trent's car about it, and he stopped and I explained it. He said he would drop me back home if I wanted him to, which again, I thought was very nice of him. But I told him we should carry on and I'd be fine.

Anyway back to the bedroom. I got myself together, and took off my wedding ring. I gave it to Richard and told him to look after it. I kissed his cheek, and then left. I think that was quite odd too, because I sort of rushed out the door, before I changed my mind.

Sometimes weddings are a real pain. I didn't know anyone there, but I wouldn't have gone as Trent's girl if I did. It was one of Trent's old friends from university who was getting married. I smiled like you do, and in my head complained about the waiting. We had to wait for the photographer to take various photos in strict order, and he dithered with his light thingy a lot. We went to the reception which was in the hotel, and had to wait for the bride and groom to visit a sick relative somewhere to show off the dress. I was sure I didn't keep people waiting around at my wedding like that.

Even Trent said, "We'll still be here for their first anniversary."

We got seated with a group, which by the talk were more of Trent's mates from University, but it wasn't so bad. By midnight I had danced with all 3 of the men sat at our table. I got felt up by them too.

Trent whispered to me about going back to our room, and once we got in the lift, I realised two of the other guys were in with us. We all ended up in Trent's and my room. Trent asked me if I was up for a little fun. I just smiled at him, because it was obvious what was going to happen. We played strip poker, or as Trent said, "strip and poke her."

There was a slight variation on the rules, whoever won took a piece of MY clothing off. So there I was naked. I sat on the edge of the bed. The guy's stripped down to their boxers. I had to pull their boxers down and give their cocks a kiss and a suck for a whole minute. Trent was orchestrating everything. He sat on the bed with his back against the headboard. I started sucking Trent, while Steve pushed his cock in me from behind. His cock didn't feel much bigger than my husband's, although he lasted longer.

Greg was next, he was around the same size as Trent, and I stopped sucking Trent for a while, because the black cock in my pussy gave me a lovely orgasm. I went back to sucking Trent and took it all down my throat. I collapsed next to him, and fell asleep.

Trent told me the next morning, he had told the guys I was married when he text them earlier in the week, and he had said if they were lucky we could all have some fun. I said I knew something was going on, because at the evening party, I remembered Greg chatting up a girl, and she looked a little miffed when he walked away and danced with me. I had asked him as we danced if he fancied her, he said he did, but he was hoping there was something better on offer.

In the morning I saw an open pack of condoms on the floor, Trent had insisted on Steve and Greg wearing them. I remember getting up in the night and going for a pee, and seeing a condom sat there in the toilet.

I had a shower which woke me up, and then we had breakfast in bed. Trent had also booked the room for Sunday night, he had told me a few days before that he would, but it was up to me if I wanted to stay another night. He asked if I wanted to go sight seeing. I said I would. He said about me asking Richard first if he didn't mind me staying another night.

I just smiled at Trent and told him, "You don't ask a cuckold, you TELL a cuckold."

He just grinned and said he was going to shower and shave.

Remember this was early on in cuckolding Richard, and I wasn't really sure about just phoning him and telling him like I said I would. Richard knew I might be staying another night, he had already said I could, but I wanted Richard to be really sure while I was away from him. So I did what we planned and I text him, "Can I?" I had to wait less than a minute before he replied.

He had two replies which we agreed on. One was, "Phone me," the other was, "Some other time."

When the reply came it said, "Phone me."

So I phoned him, and he recorded everything, so below is actually what was said, 100%.

"Hello Rich, I've decided I'm staying here with Trent for another day. You don't have a problem with that do you?"

"No, of course not, are you having fun?"

"Yeah, of course I am. Trent has been wonderful, and I've got a few surprises to tell you later."

"Can't you tell me now?"

"No, I'm not wasting my time talking to you while I'm here with Trent, you'll have to wait. What are you wearing, as if I didn't know?"

"Your tights, and a skirt and one of my new bras."

I chuckled.

"Oh dear, well you see that's why I'm staying with Trent. In fact, you should wear your tights to your mum's for Sunday dinner under your jeans."

"Jen, I don't think."

"Stop right there. You can wear socks they won't see. If you love me you'll do it for me."

"I'll have to be careful."

"You're wanking aren't you?"

"Yes."

"Well you had better stop right now. Or I'll be phoning your mummy and telling her what you're doing behind my back and that I caught you dressed in my tights, and a skirt, and a little sissy pink bra. Oh and just so you know, I'd tell her to put it on speaker, so your stepsister and stepfather can hear it."

"Jenny tell me about, about him.........you know?"

"Hmmmmm, about your perverted stepfather who stares at my legs?"

"Yeah, does he?"

"You know he does, he tries to hide it, but he's a leg man like you."

I chuckled a little.

"I give him a little smile now and then, when I catch him looking. I cross my legs for him. You know I should ask him round one day to hold a ladder for me while I change a light bulb. I'll wear my shortest skirt. Tan tights and no panties so he can see my wet pussy."

"Christ......."

"Yeah you'd like that. I bet he's bigger than you. Do you think he would move in with us? I'd love that I'd move you into the spare room with all your women's clothes. Dave would sleep in with me. You'd bring us breakfast in bed wearing tights, and you'd go down on me, and eat his cum from my pussy."

"Hell..............Jen, I've..........thanks."

"Okay........hey, was it good?"

"Fuck yeah you know it was. I need to........you know?"

"Yeah Okay, and by the way I really think you should wear tights round your mum's. Right I need to get dressed. See you tomorrow, love you."

"Love you too."

We have recorded conversations like that a few times.

Again I think it is important to remind you, our cuckold talk was always more advanced and extreme. The little fantasies and the way I talked to him like the above, I had become more confident in saying, without having to ask if it was okay. The bit about him wearing tights to his mothers he had done before, but it was up to him. The bit about his stepfather leering at my legs is very true.

Trent and me went out and visited the castle. This is what Richard told me he liked hearing about also, how Trent and I would do things as a couple, and it wasn't just us fucking. Remember Trent and I were miles away from our home town, and totally relaxed about holding hands in public, and acting like a couple. I pushed an ice cream on his nose, and then wiped it off for him. I saw this old woman give us a smile as she passed. I just smiled back at her. I kissed Trent, and he put his arm round my shoulder and we walked on. I put my head on his shoulder, and my arm was round his waist.

I never had any illusions about Trent and me being anything more than a fuck, because while we liked playing these roles of being together, we both made it clear that was all it was. There would be times in the future when I would fall for a couple of guys, and I soon realised you don't chop vegetables and never cut a finger.

We went past a flower shop and he said, "No I'm not buying you a bloody rose."

We smiled about it, and just walked on. We had dinner in the hotel and then a few drinks in the bar, and then went up to our room. We had talked a lot about Richard and me, and then he said Tanya had told him the day she saw Richard wearing her tights, her dad was there too! Richard never told me that.

Trent asked me if Richard wanted to watch us have sex. I asked Trent if he would, and I'd speak to Richard. He gave it some thought, and said he would like to.

We talked quite a bit about that, and I got onto how Richard wanted me to bitch at him.

We started working through what might happen when we did it in front of Richard. While I've told you Trent is arrogant, and a bit of a bastard, he never once laughed or made fun of Richard while I was telling him everything. I'd go as far as to say Trent enjoyed talking it through, and was quite keen to make it as good as it could be for all three of us. I asked Trent if he minded if Richard wore tights, he said he wasn't sure, then I said he what if he wore a skirt. Trent smiled at me and said it sounded very kinky, but Trent said if Richard did wear a skirt, he wouldn't be able to see his tiny pecker. I asked him if he meant that about the skirt, and he said he thought he did.

Now remembering what he told me about fucking a few married women in the past. I asked him if he had ever done it in front of their husband's. He said he hadn't, but he did have thoughts about what it would be like. We agreed that he should think more about it, and I would, and if he was really keen to try it, then I'd tell Richard.

(I did text Trent a few links to stories that he should read to give him a clearer picture. It went from basic cuckolding, to being a Bull, I even sent one about the cuckold cleaning the bull's cock and sucking him off.)

We ended up fucking, and then going to sleep. I think the late night before had caught up with us.

When I got home Richard gave me a big hug. He said he had missed me and he had been shopping and done this and done that. He asked if I had a good time. I said yes and tonight in bed he would hear the whole thing.

He wore my suspender belt and cream stockings I had wore to the wedding. I told him basically everything, but in a different order. I said I hadn't enjoyed myself so much in my life. He hung on my every word, and didn't touch himself for fear of coming before I had finished. I really laid it on thick how wonderful Trent was, and how he should be more respectful to his boss's son, and my lover in the future. He asked if Trent was arrogant, I said of course he was he had me on his arm.

Even at this stage I hadn't mentioned the other two guys, as in us fucking. Richard said I should have let Trent buy me a rose. I said deep down I hoped he would, as it would mean a great deal to me. Richard was shaking a lot by this time. Richard said he would love to have walked behind us, and seen first hand how good we looked together, and seeing us stop and kiss.

Then I told him about the strip poker, and getting fucked by two of Trent's friends while I sucked Trent's wonderful cock.

Richard put his cock in me and came without hardily a jerk. It was the oddest thing, and while I didn't get anything out of it, I felt happy that Richard had found the events so exciting, he couldn't help himself.

He took my stockings off and we cuddled. We talked in a calmer non sexual way, about it after that.

He said he had worn tights to his mum's for Sunday dinner. I nearly asked about his stepfather being there when Tanya caught him wearing her tights, I didn't, because I didn't want to upset him as he seemed so happy and contented. It was something that he would tell me about later.

I mentioned the possibility about Trent fucking me in front of Richard, but Trent had to first make up his mind that he wanted to do it, and I was still considering it too. Richard said he was getting hard again. I said it was up to Trent, and to wait and see.

I know you might think just get on with it, because obviously Richard wants it to happen, but I didn't want to go blundering in and set it up only for it to fail. At this stage while I had cuckolded Richard, the talk like with the phone call from the hotel, was far more advanced than where we were physically. Also I had in my mind what Tanya had said about Trent playing the Dom side of things. While I thought Richard would like that I didn't want Trent going to fast or far too soon. In my head I thought Richard would be okay just watching, but the rest that Trent and I had discussed might be too much for Richard.

Trent phoned me a week or so later, he said he had read the stories I suggested, and he thought he would like to try it. I asked Richard and he said he would like it. I asked him if he wanted to wear a skirt and tights while he watched. He said he wasn't sure. A day later he said he would, as long as Trent kept it to himself.

I won't go into all the things we talked about, but I will say I spent time going back and forth between them saying what one had said and then the other's response. Okay they worked together, but I never expected them to talk about it. You know in all of this no one had asked me what I wanted, which looking back now I find funny, but at the time I was thinking, oh great this and that is happening, and all I have to do is lay down with my legs open!

So things were agreed, and I sent Richard to work with a framed photo to put on his desk. The photo was full length one of me outside a church. I was wearing my black and cream dress with the hat and with Trent's arm round my waist. Don't worry I cut the rest of him out. But they would both know who I was with that day. I had told Trent what to say when he saw it on Richard's desk.

Richard told me Trent picked it up, and said, "Your wife looks really happy in this photo, Rich. How about inviting me to dinner?"

Richard's reply was, "of course, my wife would like that?"

A quick bit on the day we went to dinner with Richard's parents. Oh by the way, I know I say parents and not mum and stepfather and so on. It becomes a little tedious to write.

Richard wore tan tights under his jeans that day. He said he felt nervous most of the time, but now and then he forgot about it. I had worn jeans that day, because several times I had caught Dave taking sneaky looks at my legs in the past. Part of me didn't mind, but I always had in the back of my mind that Anne, Richard's mum, might catch him one day, and I wondered if I would get the blame. She always seemed to be critical about my hemlines.

The day I mentioned in the phone call to Richard when I was away with Trent, about crossing my legs in front of Dave did happen, but I didn't smile at him. It was more about saying "sit and squirm and fuck you."

Richard liked wearing tights like that in front of them, but he was glad to get home. He knew why I had worn jeans, but as we fucked he said Dave was probably disappointed I wasn't wearing a short skirt. I whispered in his ear that I would next time. And that I would ask to speak to Richard's mother, and tell her I was sick of her perverted husband leering at my legs. I said I would tell Anne to make him apologise to me, and I would then say I would forgive him, if I could kick him in the balls. Richard said he would love to see that, and I added, that Richard should offer to kiss his balls better in front of his mum. I don't know why I added that it just came out of my mouth before I knew it. I expected Richard to tell me that was sick, but he just groaned and came in me.

So Richard watching me with Trent will be what part 6 is about.