Extreme Cuckolding Pt. 02

Story Info
The start of cuckolding Richard and him wearing my tights.
3.2k words
4.43
13.8k
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Part 2 of the 14 part series

Updated 06/16/2023
Created 03/28/2023
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JennySW26
JennySW26
104 Followers

Hi everyone.

So I told Richard our story was on the site. I told him to get changed while I read it. He put on his tights and a skirt, and his black bra and a white blouse. I checked he was wearing his locket that Trent had given him, (sorry you'll know more about that later on.)

Richard sat there reading it, while I sipped my wine. I asked Richard to be truthful about what I had written. He loved it, he said, "It is wonderfully humiliating knowing wives, Bulls, and cuckolds had read it, and it was very special to read the little things I didn't know about."

Richard gave me a lovely orgasm with his tongue afterwards, and as a special treat I said he could jerk himself off, while he kissed my bum, it didn't take him long to come in his tights.

So this is how cuckolding my husband all began, although he wasn't my husband at the time. In fact I had only spent a couple of hours with him. We met in a nightclub, I was pretty drunk and on the rebound. We didn't even fuck we just kissed and groped. I was 19 at the time and my long term boyfriend Matt, had been cheating on me. I went out with friends, and met Richard, and we kissed and I let him have a feel walking me home. He had his hand in my panties when Matt text me. Matt wanted to see me. So I gave Richard the elbow without telling him why. I spent the night with Matt fucking. It was wonderful, and to be honest I totally forgot about Richard.

Matt and I split up again. Even though I found out it was one of my friends he had been with, I would still have had him back. The six months I had been with Matt before that I could hear wedding bells, we were also on the verge of becoming engaged and talked about marriage, but sadly it wasn't to be.

A few weeks went by and I bumped into Richard again. We started going steady, but even at that time I was hoping Matt would call me, he didn't. In fact I found out from a friend Matt had moved in with his new girlfriend.

Richard and I had sex on our third date. It was okay, yes okay, I can't lie. After we had finished he asked me about previous boyfriends. I told him about the others, and Matt and me. I even said the first time I had met him I went off to see Matt. Richard told me he didn't care, because we weren't together. I even told him Matt and I had anal sex, and Richard asked if I liked it. I said I had gotten used to it over time, but Matt was quite big, and it hurt the first few times. Richard asked me as we were now going steady, did I want anal sex with him. I said no. I wasn't even thinking about how Richard felt about me saying no straightaway like that considering we were going out together, I'm afraid it just came out.

The conversation got weirder. Richard asked me if Matt was the only one who had fucked my ass. I said yes. He cuddled me and said so it was special to you and Matt. He asked if he could kiss my ass. I thought it was strange but I let him. I could feel his erection on my leg. I told him he wasn't going up there. He said he knew that he just wanted to kiss me there. I rolled over and he ate my pussy. I directed him a few times, but he was very good at it, despite telling me he had only done it a handful of times with an ex girlfriend.

A month or two later he was kissing my ass again, and I asked if he wanted to fuck me there. He said he wouldn't because it was special to Matt and me. I thought that quite odd, but it wasn't until a while later, when he confessed about wanting to be cuckolded, and then I realise the significance of it. Richard would later tell me, he loved that Matt had fucked my ass and he hadn't.

Richard loved me wearing skirts too. Then he asked me to wear stockings or tights.

By the end of our first year dating, I had told him about all my previous boyfriends, and he had told me about his two previous girlfriends.

Richard's stepsister asked me one day why I was wearing tights a lot more. I said Richard liked me wearing them. She asked me if he wore them, I said no, then she told me she had caught him wearing her tights once, and she said if we were serious about getting married, (which we were around that time, we had already moved into a flat a month previously,) I should ask Richard about it, before I married him. Okay I thought him wearing his stepsister's tights was weird, but I assumed it was a one off. Anyway I asked him if he wore tights, and he went red. He didn't have to say he did, because it was obvious. He said he thought he had hidden it from me, but obviously I knew he was wearing my tights and other items. That floored me because I hadn't noticed, but then I realised I had found my underwear drawer was sometimes not as I had left it, but even then I thought he might have put some of my underwear away from the airing cupboard to my drawer. It also explained why some of skirts and tops seemed to be hanging differently on hangers.

Over the next hour or two he told me about it. I listened as he told me, and when he realised I wasn't jumping up and down and calling him a pervert, he offered more and more about it, like telling me was getting it all off his chest. For a few days I considered everything he had told me.

The inevitable happened and one night after we had been to the pub, I asked him if he was still wearing my tights. He said no, but he looked to me like he was lying. He burst into tears and said he couldn't help it. I don't remember having seen a guy sob before, and it was quite awkward for me. I cuddled him and asked if he wanted to wear them in front of me. Eventually he said yes. He picked up the tights I had taken off. I asked him why he didn't get a clean pair, he said because I had worn them. I thought that strange but I let him pull them up. I could see how he put them on he had done it many times before. I just sat there in bed looking at him as he stood there.

At this point I didn't know what to do. I thought about telling him to take them off, but I felt I wanted to know more.

I asked, "so now what?"

He looked really sheepish and said he usually wanked. While I had guessed that I thought there might be something else he did. I said so show me. He went over to the bin and pulled out a pair of holed tights, and I watched him push the tights he was wearing down, and then feed his cock into the toe of the holed tights, and push the rest under his balls. He pulled the tights he was wearing back up, and then started touching himself.

My hand covered my mouth, because I didn't want him to see I was smirking. In the end I couldn't hold in a little snigger. I said I was sorry for laughing, but he told me he didn't mind. He said he wanted me to laugh at him, or make fun of him. I didn't understand that for a while. Not until he explained how it turned him on. Now despite not seeing this before, I wasn't naive. I knew about some fetishes. I asked him if it would really turn him on, me making fun of him. He said yes, so I tried a few things which didn't seem to work.

He asked me to imagine that he had done something bad, and I was punishing him in front of my friends, and they were all laughing at him. So I made a few comments about coming home and finding him jerking off wearing my tights, and this was his punishment, doing it in front of my laughing friends. He got really excited, and asked if Sue would be there. Sue was my best friend, I said yes she was there and laughing, and so was her husband Luke. I don't know why I added Luke, I just did. He knew I had fucked Luke before Sue started dating him. Then he stopped wanking. I asked him why and he said he did that a lot, not finishing himself. He asked if he could finger me. I asked him if he wanted to finish himself off, he said no so he started fingering me. I started touching his cock through the tights. He told me to imagine I had just had sex with Luke, and he was sat beside me in bed. I said okay, still wondering where this was going. Then he asked me to say something, I asked him to repeat it.

I said, "Go down on me and clean Luke's spunk from my pussy while we watch."

He told me to laugh at him while I was doing it. So I did, I told him Luke was laughing too. Richard just started shaking, and he came. He looked very red. He pulled the tights off his cock, and sort of balled them up so his spunk was hidden inside. It was like he had done that a lot of times before. I was still getting to grips with all of this in my head. He took the tights off and got into bed, and we talked.

I questioned about what he had said about Luke fucking me. Richard said it turned him on, not just Luke but other men. He said he imagined the same thing with Matt, where Matt had fucked my ass and he had to clean up afterwards. I asked him if he was gay, he said he wasn't. He just liked the thought of me fucking other men. We talked a lot about that and even before he told me, I was pretty sure he wanted me doing it for real.

What got me a little narked was he was suggesting men he wanted me to fuck with even before I had said I would. We slept and the next morning he wanted to talk some more. I was still processing everything from the night before. I asked him who he would want me to go with, just to get an idea of what sort of guy he saw me fucking. He said a few names and as I've said a few I couldn't believe. Then I said who I would fuck with in theory, because I wanted to stress this was just talk. When I said his boss's son he just looked at me like I had said the worst thing possible. He mentioned Fat Jake, and then I told him to shut up about it.

We talked about it again a few days later; by this time somehow it had grown in my mind that this was definitely going to happen, and as I said in the first part I wanted it too. The same names came out. But I added one more, Kelvin, the guy who lived in the flat below us. Kelvin worked behind a bar, he was 22 or 23, a bit older than us, and I had seen him with different girls. Kelvin had been in for coffee with me a couple of times, and yes I fancied him. We had kissed, but nothing more (Sorry cuckold but knowing what I know now, I'm sure you'll find it a turn on. X) Kelvin had dark hair and lovely brown eyes. His skin was tanned, and he wore some really smart clothes.

Richard and I went to the bar where Kelvin worked. We sat at the bar talking to Kelvin when he had the chance. It got near to closing time and Kelvin asked if we were going clubbing, Richard said he was tired, and Kelvin just looked at me and asked if I wanted to go. What happened next was something which Richard later told me was in his top ten of things to do with me seeing other men. According to Richard, I just slid my empty glass to Kelvin. He said it was the way I did it, and the way Kelvin and I just looked into each others eyes. He said he felt like we were both freezing him out, and I didn't even turn to Richard to ask.

I suppose I should say here that I was worried or nervous about fucking with Kelvin. But I wanted him, and after kissing him a couple of times in the past, I knew he wanted to go further, but I had stopped him. The bitch had risen up in me too. It was like I was sending Richard home, and my god the power of that was something else.

Kelvin and I didn't go clubbing, we just went back it his flat; it was one of those slow walks, with his arm round me. He knew sort of instantly what was going on. He said he knew Richard looked a little odd. I said he knows what we are going to do. He said he knew. I asked him if he was okay with it. Kelvin said he was more than happy.

It felt really odd going up the stairs and stopping outside Kelvin's door, and not going on up to my flat. I imagined Richard putting my tights on up above our heads.

I pulled up my skirt and sat on Kelvin's lap facing him. Kelvin opened my blouse; I shrugged it off and then my bra. He spent a lot of time sucking my nipples and kissing my tits. I had worn black stockings and a red suspender belt. My skirt was pushed right up, and Kelvin's hands stroked my thighs and stocking tops as he sucked my nipples. We went into his bedroom, which was directly under mine and Richard's. I knew from the past we could hear one of Kelvin's girlfriends getting fucked below us. We heard the gasping and her little cries.

We kissed and Kelvin started fucking me. I started moaning more than I usually do, which was for Richard's benefit. Kelvin was good and I came on his cock. It wasn't much bigger than my cuckold's even if it was as bigger, but it was nice, and it was a lovely slow fuck.

Kelvin talked about Richard over our heads. He said something about maybe they should have installed glass floors and ceilings. I giggled at that. He started fucking me again, and kept going for I think around 20 minutes. I loved looking up into his sexy brown eyes.

He watched my face as I came, and he said afterwards he loved the way my mouth hung open, and the look on my face. I was a bit louder than I usually am. He sped up after I had come, but it still took him I reckon another five minutes before he came.

He thanked me when we had finished. He said I could stay the night if I wanted to, but here's the thing, I wanted to get up to the flat and make sure Richard was okay. Kelvin said he would leave the door on the latch if I wanted to come back. I said I wouldn't.

I went up to Richard and walked in the bedroom. I asked if he was okay, he said yes. He said he had heard me sometimes. I felt under the sheets and he had my tights on. I asked him if he had cum, he said he had, but he had a fresh stocking on his cock. I dropped my panties on the bed next to him, and straddled his face.

I told him, "Kiss Kelvin's pussy, and stick your tongue where his cock has been."

Just so you know I did clean myself in Kelvin's toilet. Watching my cuckold's eyes and what I could see of his red face, I felt the power thing again. I can't explain it.

I asked, "Do you really like me humiliating like this?"

He whimpered that he did on a mouthful of pussy.

I said, "Kelvin has left his door on the latch, so I could go back to him if I wanted."

Richard asked me if I wanted to. When I left Kelvin's flat I had felt contented, and I was sure I wasn't going back to him. I weighed things up in my head. And then I told the cuckold what I was thinking.

I said, "To be honest I didn't want to until I felt your legs in my tights. Now darling I realise the only man in the block lives down below me."

I got off his face and put my panties over his mouth.

"Sweet dreams cuckold," I said.

I heard him gasp as l left him there.

I went back to Kelvin and we fucked. I actually looked up at the ceiling and said loudly. "I'm coming again Kel, I'm coming again!"

I had Kelvin about a dozen times after that in quick succession. But that first time always seemed to me to be the best. Kelvin would text me and I would go to him, even when Richard wasn't around. One time Richard was fucking me, and there had been no cuckold talk. I just looked up into his eyes and told Richard I had gone down to see Kelvin that afternoon. I said I had been really naughty, because I knew Richard's parents, mum and stepfather, were coming round at 3, to talk about the wedding. I said Kelvin was fucking me when we heard their feet on the stairs. I said I heard our doorbell, but I couldn't be bothered with them. Kelvin came in me, as they started going back down the stairs. I got dressed quickly, and rushed down the stairs, went out through the front doors of the flats, and walked round the side under the arch. Richard's parents where just pulling out of the car park, so I waved to them. They parked the car again, and we went up to the flat. I explained that I was delayed at work, and only just got home. I made them a cup of tea, and then went to the toilet and changed my sticky panties.

Richard came quite hard; he loved it and told me he wasn't sure if he should have enjoyed that so much. He did say a little while after he was glad I was thinking of myself, and that was how he wanted me to act. Like my first priority should always to have sex with other men!

Next time I'll tell you about Trent, Richard's boss's son. Trent had gone out with Tanya too. I sucked Trent off, and he came round for dinner while Richard was away on his stag do.

JennySW26
JennySW26
104 Followers
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5 Comments
Sissyjackie2008Sissyjackie20087 months ago

As a sissy cross-dressing cuckold, i am enjoying your stories immensely. I love how he like me goes deeper down the cuckold, emasculation, and humilation hole.

omnivorousomnivorous11 months ago

I like the story..and I think it was well written, as well. I think many cucks enjoy the humiliation and therefore it is perfectly fine if he likes to wear ladies things...simply adds to the joy of humiliation. i read where some, whom are not gay, yet enjoy the "clean-up" duties....and some enjoy the forced feminization coupled with actually servicing the gentlemen callers. I have dabbled with this behavior with my last girl friend....funny thing is, she has long left the scene...yet her EX, who she called to play with while I watched....he and I are still friends and have enjoyed some M2M nights...he wanted to try the "Bi" thing, but is very much an Alpha type...and has women to call who will join us, (He is much younger than I, but we get along well because I don't prance about acting girlie/gay---THAT is an option in the bedroom, but not my usual state, you see). Anyway, I like the story because I also enjoy the humiliation aspect, of surrendering control often...and I believe sex is always about "power"..."making love" is not...that is for reg. folk...lololol

RanDog025RanDog025about 1 year ago

This isn't a story but an admission to guilt.

AnonymousAnonymousabout 1 year ago

A submissive man, nothing wrong with that at all if it works for you guys.

BumperBobBumperBobabout 1 year ago

And that is where you lost me. Loved the humiliation, loved the cuckolding, but you lost me on the wearing of womens clothing. Others may enjoy it and I hope they do.... Thank you for writing your story.

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