Making of a Cuckold Sissy

NOTE: This is totally a fantasy tale, and not one I'd be interested in playing out. Hope you enjoy it!

"Oh god... yes... fuck me... fuck your little sissy slut..." I moaned into my wife's pussy as her (now our) lover fucked me, my short skirt thrown up over my back, my stocking clad legs spread apart.

But I'm getting ahead of myself. I'm sure you'd like to know how I got into this position

So who's who? Well, I was Alan, I'm now Alanna. I'm a late 40s office worker. And I'm a crossdressing sissy, with a maid fetish.

The owner of the pussy I'm eating is my wife, Sarah, who's in her early 40s and is an accomplished scientist. She's got a lovely figure, keeps herself in shape. We didn't have much of a sex life anymore as I'm not overly well endowed, but we had have some toys that she liked me to use on her and then I'd wank myself off.

The cock that's pounding me belongs to Tony, Sarah's co-worker and (it turns out) lover. Tony's a lot hunkier than I am, he's also early 40s, well hung, and another scientist with a lot of patents to his name.

About two years ago, Tony started working with Sarah in the lab. I met him a couple of times and he seemed a nice enough chap, although he was unhappy about having to commute in every day for over an hour. Sarah and I live 10 minutes from the lab and get on really well with the local estate agents. I pointed Tony to them and suggested they might be able to find him something more local. Little did I know that I was sowing the seeds of my cuckoldhood right there.

The agent came through, and found Tony a nice house, about 5 minutes drive from us. We helped him move in, and attended his housewarming party, which was a lot of fun. He throws a good party.

After he moved Sarah would sometimes invite him over to discuss some research paper or other, and they'd take over the dining room, spread out notepads, maybe even get out a whiteboard. It was all over my head and I just kept out of the way. After this happened a few times, Tony suggested that they meet at his place instead, as he could keep his spare room set up as a "co-working" space for them. I was OK with this, especially as it would give me time to enjoy my fetish. As I mentioned, I'm a crossdresser, with a fetish for doing housework while dressed as a maid and wearing a chastity cage, and then using a dildo stuck to the footboard of the guest bed to fuck myself with.

So we fell into a routine, alternate Saturdays Sarah would jump in the car in the morning and head over to Tony's place. She'd stay there over lunch and come back late afternoon. As I said, I was happy with this as it gave me my own time as Alanna. All Sarah knew was that the chores got done and I was always nicely relaxed when she got back.

So, on this particular Saturday, everything happened as normal. Sarah had breakfast, had a shower, got dressed, went out. I waited 30 minutes, just in case she had forgotten something (that had happened once before, but luckily she'd only needed to grab her briefcase from the hallway and I was upstairs). Then it was Alanna time...

I headed upstairs, had my own shower, shaved my bits, and applied some talc. Then into the guest room where I opened the box that I kept at the bottom of the wardrobe in there. This box had a false bottom, under which was Alanna. In my usual ritual, I took out my wig, shook it out, put it on its stand, then got out the box with the cock cage, tits, dildo, and lingerie, and put that on the bed. At the bottom was the key part of being Alanna, the maids outfit. I took it out and hung it up to air for a few minutes.

There was also a bottle of lube in there too, which I used to lube up my cock so I could get it in the cage. The click of the lock is almost like the starting switch for the transformation process, it's when I start to feel different, knowing that Alanna is on her way.

Next comes the stockings (black seamed of course), and the suspender belt. After that it's the bra, and my tits. Alanna is starting to emerge.

The knickers go on next (every gurl knows the knickers go on outside the stockings so they can be taken off easily), and my caged cock is covered up. I shake the dress out, and pull it over my head, smoothing it down over my tits and flouncing it out at the hem. One last thing... on goes my wig. And now Alanna is there, looking back at me in the mirror, ready to perform her duties and then get fucked by the dildo.

On this Saturday there wasn't much that needed doing, probably a couple of hours of chores, cleaning the kitchen, dusting, hoovering, all the sort of things that a maid should do. So I (or rather Alanna) got on and did them with her usual efficiency. She's so much better at cleaning than Alan is.

Two hours later the chores were done, and it was time for Alanna to get her reward. Back upstairs to the guest room, pick up the dildo, stick it to the footboard of the bed. There's a slight mark on there which I should probably clean off, but it does mean I can always put it in the same place.

I slipped my knickers off, applied some lube to the toy, got on my hands and knees, and sunk the full 10 inches up me in one smooth stroke. Alanna loves it a little forceful like that.

At this point I need to set the scene a little. Our guest bedroom is at the top of the stairs, the door is directly in front of the stairs, and the guest bed is at 90 degrees to the door. So if the door's open, as you come up the stairs, you can see the footboard. I hadn't bothered closing the door, I knew I had at least another three hours before Sarah was due home.

I was thrusting back and forth, loving the sensation of the 5 inch circumference stretching me, just relaxing into the rhythm, when I heard a gasp. Everything clenched up, I nearly squeezed myself off the dildo. I closed my eyes, hoping to hell I hadn't heard anything. But denial doesn't make things go away.

"So... this is... not what I expected." It was Sarah, I recognised her voice. "Stay there, don't move. I need to... I don't know... what... umm" she said.

I'll skip forward in time to explain what I found out later. She'd tried to call me to ask me to take some chicken out of the freezer for this evening's dinner, but my phone had died, and I hadn't noticed. I guess I didn't plug it in properly overnight. She got worried when I wasn't answering and came home. And bought Tony with her in case he was needed.

Now back to the moment.

I turned my head and opened my eyes, to see her stood there, leaning against Tony, a shocked look on her face. Tony was stood beside her, with his arm round her shoulder.

Looking at her face I could see emotions flitting across it in quick succession. Then they settled. Into a look that I recognised. She was horny!

"Stay there. Don't move." she repeated, as she stood up straight and turned to Tony. Some sort of look passed between them, and she nodded.

"I guess we all have secrets to share." she commented as she dropped to her knees in front of Tony. It was at this point that everything crystalised in my mind. They'd been having an affair. And I was about to see it in action. I didn't know how I felt, Alanna was no help, she'd retreated to leave Alan to deal with it.

Sarah unzipped his fly and pulled out his cock. This was the first time I'd seen it outside of swimming trunks. It was almost the same size as my toy! No wonder she'd been having sexy times with him!

She glanced over at me again, and told me "I mean it, don't move. I can see what's in your arse, and I expect you to keep it there".

This was a side of her I'd never seen before. Oh sure she could be assertive when work required, or when she was really certain of herself. I was in an emotional turmoil; I was also finding myself getting horny. I guess the sight of people doing sexy things is always sexy, even if it's your wife sucking off her lover (yes, there, I said it).

She slipped her lips over the tip, and opened her mouth wide, sliding down the length of it, until she stopped with about half of it in her mouth. Then she did something I've never seen before. She swallowed it! She actually made a swallowing motion with her throat and the rest of it disappeared until her lips were touching his pubes. I couldn't have looked away if I'd wanted to. He put his hands on her head, held it still, and started fucking her throat. Not the full length, just four or so inches, but I could see her throat pulsing as he penetrated her. I could also see her hand lifting her skirt, and going inside her knickers, as she reached for her pussy.

This went on for.. well.. I don't actually know.. I just know that I was getting more and more turned on, watching him use her mouth and throat as his sex toy, and her fingering her pussy.

Tony kept looking over at me, and suddenly he stops with his cock down her throat and says "the little sissy is enjoying watching! She's dribbling from that little cock. Here, look."

He pulled his cock out of her mouth, making her cough, and she turned to look at me. "Are you getting turned on? Would you like to see more? Or..." she got a thoughtful look "would you like to be sucking Tony's cock?"

I'd be lying if I said I hadn't been thinking about it. There was no way I could take it the way she had, but maybe he could teach me to be a cock swallower. I nodded bashfully.

"Use your words" she said "words have power."

"Yes. I want to suck Tony's cock" I muttered. "Louder" she responded.

"Yes. Yes. I want Tony to fuck my mouth. I want to taste you on him. I want..." I trailed off as I realised what I'd just said. I wanted to suck Tony's cock after he'd fucked Sally. That was something that had never crossed my mind until right that moment. Then I realised what had happened. Alanna had woken up. She was speaking now. She was the slut who wanted to be used, who wanted to... yes... she wanted Tony to fuck her. Not just her mouth, but her ass too.

She raised her eyebrows "yes? What else do you want?"

She put her hand on Tony's cock and started stroking it while she waited for me to speak again.

I had to give in to Alanna. Just let her speak. Let her tell her truth, but it was our truth. This was the moment when I realised that Alanna was more than just for fortnightly trotting out to do chores. She was a part of me. A part that I hadn't understood until that moment.

I spoke more confidently, channelling Alanna. "I want Tony to teach me to do what you did. I want to clean you up after Tony's fucked you. I want to clean Tony's cock. I want Tony to fuck me."

I could see Tony's cock twitching with each thing I said. He was clearly up for it. As was I. It all rested on Sarah. The moment came, time slowed down, the anticipation was electric.

She'd felt Tony's cock twitching. She knew he was into the idea. She knew it came down to her.

"Go and fuck her. Give her what you gave me." she said firmly. My cock twitched once more. I was going... no Alanna was going to get fucked. Alan could take a back seat until I sorted my own head out.

"Stand up slut," Tony said as he turned towards me. Sarah got up off her knees as I did the same, the dildo making a loud plop as it pulled out of me. I just stood there, my head bowed, waiting for instructions.

Sarah walked past me and lay down on the bed, her legs spread. "Get in there and clean her up. I've left you a little present," Tony said. I walked round to the bed and knelt down beside it. Sarah wiggled forward until I could press my face into her pussy. I know what her pussy tastes like normally, so I know the extra taste must be Tony's cum.

I feel Tony's hands on my hips as he kneels behind me and aligns his cock. I feel the top pressing against my ring for a second, then slam! My nose jams into Sarah's pussy so hard she squeaks, as Tony's cock fills me right up.

People say that a real cock is different to a toy of the same size. I hadn't believed it till that moment. But oh my god, it's so much better. It's warm, it twitches, the person fucking you can vary the depth, you're not in control, you're getting fucked, you're being used as his slut.

And that's where we came in... Tony is pounding my arse, and I'm licking his cum out of Sarah. But it's not going to end here. I know it's not. Alanna is in full control now, and that's how I want it.

Sarah's wiggling as I bring her closer and closer to orgasm. I can feel my sissygasm building. Tony must be getting closer. And somehow, I don't know how, it only ever happened that first time, we all came at pretty much the same time. Sarah was slightly first, moaning and crying out, as my tongue brought her off. That pushed Tony over the edge, and he thrust deep into me, his warm cum spurting into me. Which tripped me over the edge, and I had my first human induced sissygasm.

My knees were weak, and I'm so glad I was resting on the bed. Tony leant forward, putting his weight on my back, and whispered "you're my little cum dump sissy now, aren't you?"

I remembered to use my words. "Yes Tony, I'm Alanna, your cum dump sissy."

Sarah chuckled "you even came up with a name. Oh Alanna, I'm so delighted to meet you."

Tony pushed himself upright and pulled his cock out of me. I could feel his cum leaking down my leg I was so open from both the toy and then Tony. He wandered off towards the guest bathroom. It didn't occur to me at the time to wonder how he knew where it was. I found out later they'd fucked in every single room of the house one weekend while I was away.

I sat up, and rocked back onto my heels, knowing that I was going to have to clean the carpet of the cum that was dripping out of me. Sarah looked at me, smiled, and said "let's have a glass of wine to celebrate. Alanna," and she smiled the name, "go and get three glasses and a nice bottle, set it up in the living room."

"Yes miss," I replied, which brought a chuckle and a comment of "I like that. Good girl."

Getting to my feet I went downstairs, somewhat unsteadily, and did as instructed. Three glasses on the side table, with a bottle of Sarah's preferred white beside them. I then stood in an appropriate pose looking down, beside the table and waited for my mistress and her lover. While I waited, I was running through what had happened, and how I'd felt, and how I'd reacted. I realised that this was something that had been missing from my life, and my Alanna time was just a way to deal with that missing part. I had that missing part now. And I was looking forward to it.

"Alanna, pour the wine. But don't get used to having it normally. This is a special occasion," Sarah said as they walked into the room. I did as instructed and handed them a glass each.

"Tony, would you like to say anything?" she asked.

"Just to say, Happy Birthday Alanna. Sarah and I will decide what the rules are later, but I don't think you'll find your duties too onerous."

He held his glass out, and Sarah and I chinked ours against it. "Happy Birthday Alanna," said Sarah.

"Thank you, thank you both," I had a catch in my voice, almost as if I was about to cry. I took a sip of wine to had it, and Sarah and Tony chuckled and did the same.

I spent the rest of the day moving Alan's clothes out of my wardrobe while Sarah and Tony did some online shopping for me. They got me some nice sissy dresses, and some frilly knickers, and some heels, and a couple of butt plugs to wear during the day.

They also discussed what the rules were going to be. The end result of their discussions was that Alan was only allowed out to go to work, or if we had visitors who didn't know about Alanna. That shocked me, they were planning to let other people know? And yet it also thrilled me too.

I have to call Sarah "miss" and Tony "sir".

I have to wear a plug all the time I am awake and be caged 24/7 except for personal cleaning. I am available to Tony any time, and he is going to teach me how to swallow his cock.

Sarah can have sex with Tony any time they liked, and I have to watch unless my duties around the house have me busy. The first time I heard them fucking while I was cleaning the kitchen, I sissygasmed just from the sound of it. I then had to go and do another cleaning duty and lick Sarah's cunt clean of his cum.

We settled into a nice life, Alanna didn't have any worries, and Alan only had to come out for work. I was getting cock, and cum, and Sarah was getting what she needed too.

The only thing that worried me was the comment about "visitors who didn't know about Alanna". But nothing happened for ages, and I'd almost forgotten about that... until I was reminded about it. Which will be a later tale, I think.

Alana,

Sissy Slut for Sarah and Tony.