Jane’s Unusual Second Marriage
A Fictional Story by Quietoldie.
His mobile phone pinged, and he quickly got up to leave the house. She kissed him warmly on the lips. As they embraced, I unaccountably found my little penis growing. What was wrong with me, I thought.
“I noticed you looking at us,” Jane said. “You were staring, weren’t you?”
My face turned red. “I’m so sorry. You make such an attractive couple. I came here on my own. I have to confess, I love people-watching. I should have been more discreet about it, shouldn’t I? Did your husband have to go unexpectedly?”
She smiled. “We’re not married; I hardly know him. We are friends. I like him, but I’m only just getting over ending a previous relationship.
It was my turn to smile. “Has he only gone out for a few minutes?”
“No, it was his wife. She wanted him at home.”
“Are you okay if I sit with you on your settee?”
“Don’t be silly, it’s not my settee.” She patted the place recently vacated by her friend. I sat down almost as close as he was. Not content with that, she shuffled closer.
This emboldened me to say. “I notice you gave him a big kiss on the lips as he left.”
She reacted by doing the same to me. I couldn’t believe it, responding in kind. My cock stiffened.
“Thank you. That was an unexpected pleasure.” I said.
“What can I say? I’m a friendly person.”
I couldn’t take my eyes off her legs. Her short skirt had slipped up towards her waist.
She grinned. “You’re staring again.”
I blushed. “Sorry.”
“If we become good friends, you’ll find I will punish you for bad behavior.”
I’ve always fantasized about being disciplined by a strong woman. I turned my face away as a gesture of compliance.
“Feel free to put me across your knee if I’m being a naughty boy.” My voice had become more girlish than usual.
“Your words tell me you want to submit to punishment. Am I right?”
I didn’t know how to reply. There was a pregnant silence.
“Your silence speaks volumes. Are you a man or a mouse?”
“It depends on who I’m with. It seems like you’ve pressed my submissive button. I set off on the wrong foot with you, didn’t I?” I am truly sorry.”
“Stop apologizing. We are fine. It takes a strong man to admit he’s in the wrong. I like it in a man. My ex-hubby could learn a lot from you.”
“I’m just a bit curious, but of course, you don’t need to answer. Was he ever violent?”
“What makes you ask?”
“I’ve been working with domestic violence perpetrators in groups for the last few years.”
“Interesting. Is that in a prison?”
“No, in the community. But they’ve all been convicted of violence against their wives.”
“Does that mean you work as a probation officer?”
“Yes.”
She leans in and kisses me full on the mouth. I respond with enthusiasm, loving the way things are going. After a full year on my own, could I be starting a new relationship at last? But she’s way out of my league, isn’t she?
We go to the dining room for the evening meal and sit together. We are at a fairly small dinner party, so we turn to the other person on the other side of us out of politeness, exchange a few words, then continue our conversation.
“I’m blown away to be meeting an actual probation officer,” Jane says.
“Usually when I say what I do for a living, I get people changing the subject. It seems like the job is out of fashion these days.”
“The answer’s Yes.”
“What?”
“My husband; you wanted to know….” She saw the look of recognition on my face and stopped.
“Do you want to talk about it?” I asked. “I am interested but realize you might not want to rake it all up again.”
“I’m happy to talk to you, my darling. John was good in bed, but everything was always on his terms. He’s an old-fashioned husband and father. In his eyes, men are entitled to be in control. I wouldn’t accept that. And occasionally his attitudes got out of hand, and he’d hit me. He was always sorry afterward, telling me it would never happen again. At first I believed him, but repeated incidents forced me to leave him. Our split was acrimonious.
We tried to keep it away from Paul, our son; he’s twelve and idolizes his father. I wanted Paul to come with me when I left, but he refused. He’s old enough to decide for himself. I’d never involved the police after the violence, so I reasoned that provided I could maintain good contact with Paul, he would be okay with his dad. It’s not ideal, but he seems happy enough.”
“How often do you see him?”
“At least twice a week. He stops overnight most Saturdays and comes round after school midweek; sometimes I see him twice after school.”
“Are there any signs that Paul is picking up his father’s attitudes towards women?”
“I’m making sure he doesn’t. We laugh at his outdated views, which are inappropriate nowadays. He fully accepts the reason I left and supports me. He’s a good lad and might move in with me in the future. But I’d never put him under pressure to do so.”
After the meal, she invited me back to her flat. She told me she wanted to see me regularly.
“But we are not exclusive.” She said. ” So you can see other women, and I can see other men. Are you okay with that?”
I wasn’t all that happy but didn’t say so. I just went along with it. I wasn’t interested in other women. I’d have started seeing her with any conditions she might wish to impose. I’m going to tell her that. Am I crazy?
So on the way in the taxi, I whispered in her ear.
“I’ve fallen under your spell. I shouldn’t be telling you this, but I would agree to anything you want to do to me as long as we can be together.”
Her eyebrows shot up at this. “Really? You can’t be serious.”
“Yes.” My pecker rose in my pants. What was I letting myself in for?
“Good boy.” She kissed me again; this time with tongues.
Back at her house.
“You will obey me, won’t you?”
“Yes.”
“Yes, mistress,” Jane said sternly.
“Yes, mistress.”
“Okay. You asked for it. Strip off all your clothes.”
It didn’t take long. “I see your tiny cock is standing proud.”
My penis jerked and stood taller.
Does it excite you when I tease you about your little willy?”
“Yes, mistress.”
“I’ll have to think up a good nickname for you. How does Tiddler sound?”
“As you wish, mistress.”
“Now for your punishment. When you were doing all that staring, did you look up my skirt?”
“Yes, mistress. I’m sorry.”
“Okay, prove it. What color are my panties?”
“Red, mistress.”
“Okay. Get over my knees. Now.”
I didn’t know what to expect, but of course I complied.
She didn’t hold back. My bottom was red raw by the time she’d finished. Not far from the color of Jane’s panties.
I found the spanking quite erotic. She knew I would because of what I’d said earlier. She’d made me cry, but I wasn’t upset. She’d given me what I’d craved. I thanked her sincerely.
“Good little Tiddler,” Jane said.
—
“Now I want to get a bit kinky with you. Are you ready for another test?”
“Yes, mistress.”
“With my help, I want you to dress as a girl using my clothes. When I’m satisfied with what I see, we can get sexual together. Okay?”
“I’d like that, mistress.”
“Have you done this sort of thing before?”
I blushed again. “Yes, mistress.”
“Mmm. What is it about men with little dicks? Deep down you all want to become women, don’t you?”
I turned my face away, not answering.
“Answer me, is it Yes or No?”
“Sometimes I do. Not always. I’m trying to be honest, mistress.”
“Good girl. Now get your head in my panty drawer and find yourself a nice sexy pair.” My clothes are in the bedroom through this door. Here, have a look through this chest of drawers and these two wardrobes.”
“Mistress, please can you select my outfit? I promise I’ll wear whatever you think is best.”
Jane realized her suggestion was impractical. He’d be searching through her things for hours, and she wanted sex now. She was soaking after his spanking, but he had to be in girly clothes.
“Tiddles must be tired, poor thing. Have I worn you out? Come on, I’ll do it for you. But you’ll have to dress yourself and be quick about it. I’ll give you a hand with the stockings and suspender belt. I’ll bet you’ve never worn sussies before, have you?”
“No, mistress, but I do like to wear panties under my ordinary clothes.”
“Good girl. I thought so. In that case you’ll enjoy what we are going to do.”
“There we are,” Jane said. “What do you have to say? You’re all decked out like a proper sissy.”
“Thank you, mistress.”
“Now, you are going to lick my cunt until I have an orgasm. Have you experience of cunt munching?”
“Yes, mistress.”
So this was how it all started. I licked her to two noisy orgasms, by which time my tongue was sore, and my jaw was aching. She told me she didn’t want to fuck me.
“I’ve got a big cunt, Tiddler. I don’t want you inside me. Tell you what, have a wank in front of me. Think of me fucking the friend you saw me with. He’s one of my regulars.”
I did as she instructed. It didn’t take me long to spurt.
“When I’ve had a night with one of my fuck buddies, I’ll be sitting on your face. You’ll be slurping up all his spunk, won’t you, Tiddler?”
“Yes, mistress.”
—
The weeks that followed settled into a rhythm that felt almost ordinary, except that nothing about my life with Jane was ordinary at all.
She’d text me at work — short, commanding messages. Come over tonight. 8 pm sharp. Wear the things I gave you underneath your clothes. My cock would twitch in my trousers just reading the words, and I’d spend the rest of the afternoon half-hard, anticipating.
The “things she gave me” lived in a locked box she kept under her bed. A pale pink bra with a front clasp. Matching panties that were tight across my crotch and made my little erection obvious. Stockings — always stockings — in black or nude, with a suspender belt that bit slightly into my hips. She’d measured me herself the second time I came over, running the tape around my waist and chest with clinical precision, then ordered everything online. At the same time, I sat naked on her bedroom floor, watching her click through pages of lingerie.
“You’ve got narrow hips for a man,” she said, not looking at me. “That helps.”
I didn’t know whether to thank her or stay quiet. I stayed quiet.
—
The first time she had one of her fuck buddies over while I waited, she sent me home first.
“Go,” she said, standing in her bedroom doorway in a black slip that barely covered the tops of her thighs. Her hair was down, her lips freshly painted red. She looked devastating. “I’ll text you when it’s done.”
I sat in my flat for three hours, staring at my phone, my stomach in knots. I masturbated twice — both times finishing almost immediately, my little cock spurting into my hand within seconds. Each time, the shame hit me before the cum had even dried. I cleaned myself up and waited more.
At half past midnight, her message arrived: Come now. Bring wine.
I almost ran to my car.
—
When she opened the door, she was wearing a short silk robe, untied, hanging open. Her body underneath was flushed, her nipples still swollen, her hair tangled. The bedroom smelled of sex — sweat, skin, something musky and unmistakable.
“He’s gone,” she said, turning and walking toward the bedroom. “But he left something for you.”
I followed her, my mouth dry.
She lay back on the bed and opened her legs. The inside of her thighs was slick. Her pussy was red and puffy, the lips parted, and I could see it — a thick, white trail of cum leaking from her, pooling in the crease where her thigh met her groin. More of it had dried in the hair above her slit.
“Mark’s been saving up for a week,” she said, watching my face. “He’s twenty-six. Fucked me three times. Twice with a condom, once without.” She reached down and spread herself open with two fingers, and a thick string of his cum oozed out, sliding slowly toward her anus. “Get your mouth on me, Tiddler.”
I dropped to my knees beside the bed and pressed my face between her thighs.
The taste was sharp, salty, and slightly bitter. I licked in long, flat strokes, starting from where the cum had dripped down and working upward, gathering it on my tongue. She put her hand on the back of my head and pushed me harder against her.
“Deeper. Get your tongue inside.”
I pushed into her. The cum was warm and thick, coating my tongue, sliding down my throat. I swallowed and kept licking. Her pussy was looser than I imagined — stretched from a cock much bigger than mine. The thought made my own pathetic erection throb inside my panties.
“He made me come twice,” she said, her voice lazy and satisfied. “The first time he was fucking me from behind, pulling my hair. The second time I was on top, riding him.” She ground her cunt against my mouth. “You’ve never made me come with your cock, have you, Tiddler?”
I mumbled a negative into her flesh.
“No. Because it’s too small, that’s why you’re down there cleaning up instead of up here making a mess.” She laughed softly. “Keep going. You missed some.”
I licked until she was clean, until the only wetness was my own saliva. Then she pulled my head up and looked at me — my face slick, my lips swollen.
“Good boy,” she said, and kissed me, tasting Mark’s cum on my tongue.
—
After that, it became routine.
She had three regular fuck buddies that I knew of. Mark, the young one — twenty-six, athletic, apparently well-endowed. She described his cock to me in detail: thick, circumcised, about seven inches, with a prominent vein along the underside. She made me repeat the description back to her while I knelt at her feet.
Then there was David, a divorced man in his forties who worked in finance. He was rough, she said. Liked to spank her, liked to fuck her hard and call her names. I felt a strange, complicated jealousy when she told me this — not because another man was spanking her, but because she let him do it. She’d never let me spank her. She’d never let me do anything but serve.
The third was a woman named Claire. Jane didn’t tell me about Claire until the second time she’d been over.
“I had a friend round last night,” she said casually, sitting at her kitchen table in a t-shirt, drinking coffee. She looked freshly showered, her skin pink.
“Mark?”
“No. Claire.” She sipped her coffee. “She’s bi. We’ve been sleeping together for about a year.”
I stared at her.
“What? You didn’t think I only fucked men, did you?” She smiled. “Claire is gorgeous. Blonde. Small tits but incredible nipples. She goes down on me for hours.” She paused. “I didn’t make you come over to clean up last night because — well, women don’t leave the same mess, do they?”
I didn’t know what to say.
“But I did tell her about you,” Jane continued. “About my little sissy with his tiny cock and his pretty panties. She thought it was hilarious. She wants to meet you.”
My face burned. “Meet me?”
“She’s coming for dinner next Saturday. You’ll cook. You’ll wear your maid’s outfit.”
I didn’t know I had a maid’s outfit. She showed me later — a black dress with a white apron, short enough to show the tops of my stockings, with a little lace headpiece. She’d ordered it in my size without telling me.
—
Saturday came. I spent the afternoon preparing a roast, moving around Jane’s kitchen in the maid’s dress, stockings, and a pair of flat black shoes she’d bought me. My cock was tucked uncomfortably into my panties, half-hard all day from the combination of the clothing and the anticipation.
Jane got ready in the bedroom and emerged at seven in a deep green dress, low-cut, with her hair up and gold earrings. She looked at me over the kitchen counter and smiled.
“You look perfect,” she said. “If you’re a good boy tonight, I might let you watch.”
“Watch?”
“Claire and me. After dinner.” She adjusted my apron, smoothing it down. “You’ll sit in the corner and be quiet. If you’re very good, I’ll let you lick us both afterward.”
Claire arrived at half past seven. She was exactly as Jane described — blonde, slim, with small breasts visible through a sheer white blouse and no bra. She was taller than Jane, with long legs and a wide, easy smile. She looked at me in my maid’s outfit and laughed — a bright, genuine laugh that made my face go scarlet.
“Oh my God, Jane, you weren’t kidding,” Claire said, still laughing. She walked around me, looking me up and down. “He’s adorable. Does he really have a tiny one?”
“Tiddler,” Jane said. “Show her.”
I hesitated. Jane raised one eyebrow. I lifted the front of my apron and dress, exposing the pink panties underneath, my small erection pressing against the fabric.
Claire looked down and laughed again, harder. “Oh, that is tiny. That’s barely a clitoris.” She looked at Jane. “And he cleans up after your guys?”
“Every time. With his tongue.”
Claire shook her head, grinning. “That is the most pathetic, wonderful thing I’ve ever heard.” She reached out and patted my cheek. “You’re a good little sissy, aren’t you?”
I nearly came in my panties.
Dinner was surreal. I served them roast chicken, poured their wine, cleared their plates, all in the maid’s outfit while they sat and talked and ignored me for the most part. Occasionally Claire would look at me and smirk, or Jane would touch my arse as I walked past, sliding her hand up under the dress to stroke the bare skin above my stockings.
After dinner, they moved to the sofa. I was told to wash up. I could hear them from the kitchen — laughing, the clink of wine glasses, then quieter sounds. Murmuring. A soft moan.
I dried my hands and crept to the doorway.
Claire had her hand inside Jane’s dress, and Jane’s head was tipped back against the sofa. Claire’s mouth was on Jane’s neck. I watched as Claire pulled the dress down, exposing Jane’s tits — full, heavy, her nipples dark and hard — and bent to suck one into her mouth. Jane let out a low groan and looked up, catching me watching.
“I told you to sit in the corner,” she said. Not angry. Amused. “Come. Sit. Watch.”
I sat on the small chair in the corner of the living room, my hands on my knees, my little cock straining in my panties, and watched Claire undress Jane slowly, kissing every inch of skin she revealed. Jane unbuttoned Claire’s blouse and took her small, firm breasts in her hands, bending to suck Claire’s nipples, which were indeed extraordinary — long, pink, stiff.
They moved to the bedroom. I followed and sat in the corner chair as they lay on the bed together, their bodies entwined, kissing deeply. Claire slid down between Jane’s legs and licked her pussy with slow, deliberate strokes while Jane pulled Claire’s hips over her face, and they lay in a sixty-nine, mouths working, tongues sliding, bodies arching.
Jane came first, her back bowing off the bed, her thighs clamping around Claire’s head. Claire followed a minute later, grinding down against Jane’s mouth, her blonde hair spilling across Jane’s stomach.
They lay there afterward, breathing hard, touching each other gently. Then Jane looked over at me in the corner.
“Both of you,” she said. “Come here.”
I knelt beside the bed. Claire lay with her legs apart, her pussy pink and wet, her inner thighs glistening. Jane lay the same way, her cunt swollen and open.
“Start with Claire,” Jane said. “She’s our guest.”
I leaned in and tasted Claire — different from Jane, lighter, slightly sweet. I licked her clean while she ran her fingers through my hair, occasionally tugging.
“He’s not bad at that,” Claire said, looking down at me. “For such a little thing.”
Then Jane. I moved between her thighs and licked her to another small orgasm while Claire watched, stroking Jane’s hair.
Afterward, they sent me back to the corner, and I sat there, hard and aching in my panties, while they fell asleep in each other’s arms.
—
In the months that followed, my life with Jane deepened into something I no longer questioned. I kept my own flat but spent most nights at hers. I cooked, cleaned, ran errands, and served. She continued to see her fuck buddies, and I continued to clean up after them. She introduced me to new humiliations — making me wear a butt plug while I did housework, taking photos of me in lingerie to show Claire, making me masturbate in front of them while they pointed and laughed at my small cock.
I met her son Paul once, briefly. He came to the flat to pick up a book, and I was introduced as “a friend.” He was a quiet, serious boy with Jane’s dark eyes. He looked at me curiously but said nothing. After he left, Jane pulled me into the bedroom and spanked me hard, twelve strokes, for no reason I could determine.
“I needed that,” she said afterward, breathless, her eyes bright. “Now get your tongue on me.”
I never asked why. I’d learned not to ask.
—
One evening, about six months in, Jane came home from work and sat on the edge of the bed while I knelt to remove her shoes.
“I want to try something new,” she said.
“Anything.”
“I want to bring someone here. Not to fuck. To watch you.” She looked down at me. “A man. To watch you serve me. To see what a sissy you are.”
My stomach tightened. “Who?”
“David. The rough one. He’s curious. He’s never seen a man in panties before.” She paused. “He said he might want to use your mouth.”
I looked up at her. Her expression was calm, steady, certain.
“Would you like that, Tiddler? Sucking a real man’s cock? The cock that fucks me when you can’t?”
My small penis was rigid in my panties. I nodded.
She smiled and stroked my cheek. “Good boy. I’ll arrange it for next weekend.”
She stood, walked to her chest of drawers, and pulled out a new item — a black lace corset, small, clearly my size.
“Wear this,” she said. “And nothing else. I want him to see everything.”
I took the corset in my hands, feeling the lace between my fingers, and felt the familiar, warm, helpless rush of complete submission wash over me.
“Yes, Jane,” I said.
She kissed my forehead. “That’s my good little sissy.”
—
The Ending
—
The week before David’s visit was the longest of my life.
Jane prepared me with methodical precision. She laid out the black lace corset on the bed and made me try it on three separate evenings, adjusting the laces each time until it cinched my waist into something resembling an hourglass. She bought me matching knickers — black, high-cut, with a sheer panel at the front that left nothing to the imagination.
“His cock is bigger than Mark’s,” she said one evening, lacing me in from behind. “Thicker. He’s not as gentle.”
I stood in front of her full-length mirror, seeing myself — the corset hugging my torso, the stockings clipped to the suspenders, my small cock visible through the sheer fabric. I looked ridiculous. I looked exactly how I was supposed to look.
“Will he hurt me?” I asked.
Jane met my eyes in the mirror. “Probably. He likes to be rough with me, and he’ll enjoy being rough with you. But I’ll be there. I won’t let anything happen that I don’t want to happen.”
That was the thing — it was always about what she wanted. And I’d made peace with that months ago.
—
Saturday evening. Jane dressed me herself, pulling the corset tight, smoothing the stockings up my legs, positioning the knickers just so. She applied a light coat of mascara to my lashes and a brush of nude lipstick to my mouth.
“You look like a pretty little thing,” she said, stepping back. “He’s going to love you.”
She wore a dark red dress, simple, low at the back. No bra — her nipples pressed faintly against the fabric. Her hair was down. She smelled of jasmine and something darker underneath.
David arrived at eight. He was taller than I expected — over six feet, broad-shouldered, with greying hair cropped short and a square jaw. He wore jeans and a dark shirt, sleeves rolled to the elbow. He looked like a man who worked with his hands. He looked like a man who took what he wanted.
Jane kissed him at the door — a real kiss, deep, her hand on the back of his neck. He grabbed her arse with one large hand and squeezed. I stood in the hallway in my corset and stockings, watching.
“So this is the sissy,” David said, looking at me over Jane’s shoulder. His voice was deep, slightly rough. He released Jane and walked toward me, looking me up and down slowly. “Jane’s told me a lot about you.”
I dropped my gaze. “Sir.”
He laughed. “She said you’d be polite.” He reached out and gripped my chin, tilting my face up. His hand was rough, calloused. “Let’s have a look at this little cock she keeps going on about.”
He didn’t wait for permission. He pulled the front of my knickers down and looked at my erection — small, stiff, twitching under his gaze.
“Christ,” he said, and laughed again. “That is small. How do you even call that a cock?” He let go of my chin and flicked my penis with his finger. It bounced. “That’s a clit. Isn’t it, Jane?”
“Tell him, Tiddler,” Jane said from the doorway, leaning against the frame, arms folded.
“It’s a clit, sir,” I whispered.
“Good. At least you know what you are.” He tucked my knickers back up and turned back to Jane. “Pour me a drink. He can bring it to me.”
—
I served drinks while they sat together on the sofa. David’s arm was around Jane’s shoulders, his hand resting on her tit, kneading it absently through the dress. They talked like old friends — about work, about people they knew, about a holiday they’d once taken together. I knelt on the floor beside the coffee table and waited.
After his second drink, David looked down at me. “Get my cock out.”
My hands trembled as I reached for his belt. He lifted his hips slightly so I could pull his jeans down. Underneath, he wore dark boxer briefs, and the outline of his cock was obvious — thick, heavy, running diagonally across his thigh. I pulled the briefs down, and it sprang free.
It was the biggest I’d seen in person. Not excessively long — maybe seven and a half inches — but thick. Circumcised, with a broad head and a shaft that was darker than the rest of his skin. It lay against his thigh, soft but already heavy, and I could smell him — musky, warm, male.
“Suck it,” he said. “Get it hard for her.”
I leaned forward and took the head in my mouth. It was too thick to take more than the first few inches, and I worked my tongue around the ridge, tasting salt and skin. He put his hand on the back of my head and pushed me down, and I gagged, my eyes watering.
“Don’t be pathetic,” he said. “Jane takes all of it.”
I tried again, breathing through my nose, relaxing my throat. I got about two-thirds of the way down before I gagged again. He pushed harder, and I felt his cock slide into my throat, cutting off my air. I panicked, my hands gripping his thighs, but I didn’t pull away. I held it until he let me up, gasping, saliva running down my chin.
“Better,” he said. “Keep going.”
I sucked him for ten minutes, working my mouth up and down his shaft, licking the underside, tonguing the slit. He grew fully hard — rigid, the veins standing out, the head flushed dark. Jane watched, her hand between her own legs, rubbing herself through her dress.
“That’s enough,” David said, pulling my head off by the hair. “I want to fuck her now. You can watch.”
—
They undressed each other on the bed. I knelt in the corner chair, hands on my knees, my little cock straining against the sheer fabric of my knickers.
David’s body was solid — broad chest, thick arms, a flat but not defined stomach. His cock jutted out from a thatch of dark hair, thick and angry-looking. Jane stripped down to nothing and lay back, her legs open, her cunt already glistening.
“Come here, sissy,” David said, pointing to the floor beside the bed. “I want you close enough to see.”
I knelt beside the bed, my face level with Jane’s hips. David climbed between her legs and rubbed the head of his cock up and down her slit, coating it in her wetness.
“Tell him what you want, Jane,” David said.
“I want your big cock inside me,” she said, looking at me. “I want a real man to fuck me.”
He pushed in. Slowly, inch by inch, and I watched her cunt stretch around him, swallowing his thickness, her lips pulling and folding. Jane let out a long, low moan and grabbed the sheets.
“Oh, fuck, that’s good,” she breathed. “That’s so much better than anything Tiddler could give me.”
David fucked her with long, deliberate strokes, pulling almost all the way out before slamming back in. The bed shook. Jane’s tits bounced with each thrust. She wrapped her legs around his back and pulled him deeper, and I watched his cock disappear into her again and again, her cunt clinging to his shaft, slick and swollen.
“You like watching, sissy?” David grunted, not looking at me. “You like seeing a real cock fuck your woman?”
“Yes, sir,” I said, my voice cracking.
“Tell him why it’s better,” Jane said, her breath coming in gasps. “Tell him why his cock is better than yours.”
“Because it’s big, sir. Because it fills her. Because mine is too small to—”
David slammed into her hard, and she cried out, her back arching. “That’s right. Your little clit couldn’t do this.” He grabbed her throat — not hard, but firm — and fucked her faster. “Tell me what you are.”
“I’m a sissy, sir. I’m a cuckold. I’m—”
“Mine,” Jane said, pulling David’s face down to hers, kissing him deeply. “He’s mine.”
David came inside her with a guttural groan, his hips jerking, his cock buried to the root. I watched his balls tighten and pulse, and I knew he was flooding her cunt with his cum. Jane held him close, her legs locked around him, whispering in his ear.
When he pulled out, his cock was still half-hard, slick with their combined juices. Jane’s cunt was a mess — red, swollen, gaping slightly, and a thick stream of white cum was already leaking out, running down toward her arse.
“Clean me first,” David said, standing in front of me, his cock at my face. “Then her.”
I took him in my mouth without hesitation. The taste was overwhelming — his cum, her cunt, the salt and musk of their fucking. I licked and sucked every inch of his cock, cleaning the shaft, the head, the underside, swallowing it all. He watched me with a look of mild amusement, one hand resting on the top of my head.
“Not bad,” he said when I finished. “For a sissy.”
Then Jane. I climbed between her thighs and pressed my mouth to her cunt, and the cum poured out onto my tongue — thick, warm, bitter. I licked deep inside her, gathering it, swallowing, licking more. She ground against my face, her thighs tight around my ears.
“Get it all, Tiddler,” she said. “Every drop.”
I licked until she was clean, then licked her to a small, shuddering orgasm that made her grip my hair and pull my face hard against her.
—
After David left, Jane and I lay in bed together. She was on her side, facing me, her fingers tracing lazy patterns on my chest above the corset line.
“Did you like it?” she asked.
“Yes, mistress.”
“Did you like sucking his cock?”
I hesitated. “Yes.”
She smiled. “Good. Because he’ll be back. And next time, I want him to fuck you.”
My stomach flipped. “Fuck me?”
“In the arse, Tiddler. With that big cock you just had in your mouth.” She watched my face carefully. “You’ll take it for me, won’t you?”
I swallowed. “If you want me to, mistress.”
“I do.” She leaned in and kissed me softly. “You’re my good little sissy. And good little sissies take cock when their mistress tells them to.”
She rolled over and turned off the lamp. In the darkness, I lay still, my small cock aching in my knickers, my mind racing, my body trembling with something that was half fear and half desperate, shameful need.
—
It happened two weeks later.
Jane prepared me with a butt plug — the largest one she owned — and made me wear it for an hour before David arrived. When she finally pulled it out, my arse felt empty and open, and she slicked me with lubricant, working her fingers inside me, stretching me.
“Relax,” she said. “Breathe. If you tense up, it’ll hurt more.”
David came in without ceremony. He was harder this time, rougher — he grabbed Jane and kissed her, then looked at me kneeling on the bed in my corset and stockings, my arse in the air, ready.
“Ready for it, sissy?”
“Yes, sir.”
He climbed behind me. I felt the head of his cock press against my hole — blunt, thick, impossibly large. Jane knelt beside me, her hand on my back, stroking me.
“Push out,” she said. “Let him in.”
I bore down, and the head of David’s cock pushed past my sphincter. The pain was sharp, immediate, and I gasped, gripping the sheets. He didn’t stop. He pushed in steadily, inch by inch, and I felt myself splitting open around him, the fullness overwhelming, the pressure unbearable, and then — suddenly — shifting into something else. Something deep and dark and electric.
“There you go,” David said, his voice low. “Take it. Take my cock, you little sissy.”
He fucked me slowly at first, then faster, his hands gripping my hips. Jane watched, her hand between her legs, masturbating. The bed creaked. My arse burned, and then the burn became heat, and the heat became pleasure — a strange, full-body pleasure that radiated from somewhere deep inside me, making my little cock leak and twitch untouched.
Jane came watching me get fucked. She clamped her thighs around her hand and shuddered, her eyes fixed on David’s cock sliding in and out of my arse.
David pulled out and came on my lower back — hot, thick stripes across my skin. I felt it pooling in the dip of my spine, running down over my arse. Jane leaned in and licked it off me, her tongue tracing the trails of cum, and I shivered beneath her.
—
That was the shape of things after that.
David came over once a fortnight. Sometimes he fucked Jane and I cleaned up. Sometimes he fucked me. Sometimes he made me suck him until he was hard, then fucked Jane, then fucked me, then made me clean them both. Jane orchestrated everything, directed everything, and decided who did what, when, and how.
Claire continued to visit. Sometimes she and Jane would use me together — making me serve them drinks in the maid’s outfit, then having me kneel between them while they took turns sitting on my face. Claire developed a particular fondness for watching me suck David’s cock. She’d sit in the corner chair, legs spread, touching herself, while I knelt and worked my mouth on him.
“He’s actually quite good at that,” Claire said once, breathless, her fingers slick with her own wetness. “For someone with such a useless little thing between his legs.”
Mark came over less frequently, but when he did, Jane always made sure I was there to clean up afterward. His cum was the most copious — thick, abundant, and I’d spend twenty minutes between Jane’s thighs, licking every drop from her swollen cunt while she told me how good he’d felt, how deep he’d gone, how full he’d made her.
I never fucked Jane. Not once. My cock — my clit, as they all called it — stayed locked in panties, used only for Jane’s occasional amusement. She’d make me masturbate in front of her and her friends, timing me, laughing at how quickly I came, how little I produced. Sometimes she’d have me wank into a glass and drink it. Sometimes she’d make me edge for hours, then deny me, locking me in a chastity device she’d bought online — a small, pink plastic cage that fit my tiny cock perfectly.
“You don’t need this,” she said, tapping the cage through my knickers. “You have a mouth and an arse. That’s enough for a sissy.”
—
Paul moved in with Jane six months later. She gave him the second bedroom and introduced me as “a close family friend who stays over sometimes.” Paul was polite, quiet, and either didn’t notice or chose to ignore the details of my arrangement with his mother. He’d see me in the kitchen in the mornings, making Jane’s coffee, and give me a nod.
I wondered what he knew. I wondered if Jane had told him. I decided I didn’t want to know.
One evening, after Paul had gone to bed, Jane sat on the sofa and pulled me down beside her. She was wearing a soft grey jumper and leggings, her hair in a ponytail, no makeup. She looked younger. She looked like the woman I’d first met in the pub, a lifetime ago.
“I want to tell you something,” she said.
“Yes, mistress?”
She put her finger to my lips. “Not tonight. Tonight, just listen.”
She told me she’d been married for twenty-two years. She told me about the years of her husband’s indifference, his dismissiveness, the way he’d looked at her — through her — as if she were furniture. She told me about the affair she’d had that ended things, and how her husband had blamed her for everything, even his own neglect.
“I left because I was disappearing,” she said. “I was becoming nobody. And I decided I would be nobody again.”
She looked at me. “When I met you, I saw someone who wanted to disappear. Who wanted to become nobody. And I thought — I can give him that. I can make him small, safe, and looked after. And in exchange, he can make me feel powerful. Seen. Present.”
I stared at her. In all our months together, she’d never spoken like this.
“Do you understand, Tiddler? This isn’t just about the panties and the spanking and the cum. This is about you giving yourself to me completely, and me taking you completely, and both of us getting exactly what we need.”
I felt tears prick my eyes. “I understand.”
“Good.” She kissed me — softly, on the mouth, the way she never kissed me during our scenes. “Now go and put the kettle on. And wear the pink ones tonight. I want to play with you.”
I stood, and she slapped my arse as I walked past, and I went to the kitchen in my socks and trousers, already half-hard, already hers, already gone.
—
I’m writing this on a Tuesday morning. Jane is at work. Paul is at university. I’m sitting at her kitchen table in a pale blue nightie, drinking tea, looking out at the rain.
In the drawer beside me is a letter from my employer, offering me early retirement. I’m fifty-three. I’ve been thinking about it for weeks.
If I take it, I’ll have a small pension and a lot of free time. I could be here every day. I could cook, clean, serve, and wait for her to come home. I could be what she needs me to be, full-time, without the pretense of a job I don’t care about.
I haven’t told Jane yet. I want to see her face when I do.
I know what she’ll say. She’ll call me Tiddler. She’ll tell me to put my knickers on and kneel. She’ll tell me I’m a good boy and a pathetic sissy and that she owns me, and I’ll agree with every word.
And then, maybe, she’ll let me stay.
The End.

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