The Cuckold’s Babysitter

by Small Penis


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This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

These stories are the artistic expression of the authors who wrote them. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this post, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
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By yumacd (edited)

My wife, Tami, has been cucking me for a couple of years now. It started when I revealed my fantasy of watching her with another man one night after a party, me a little more drunk than usual. Appalled at first, she warmed to the idea after many nights of watching big-cock porn and some stories I’d sent her. There were months of cuckold roleplay in bed to also help her ease into the concept. Soon a big dildo enters the picture, one with more length and girth than my little cock. Although until I started using it on her, she always thought my cock was adequate.

* NOTE: An aside here for any Cuck wannabe’s: It’s pretty much all fun and games until that dildo enters the picture. The moment she experiences that first different orgasm with something bigger than you inside her is truly the start of the ‘cuckold-journey.

Before you know it you’re in a hotel bar with a strange guy you connected with on Craigslist, and after the first guy there are soon others. All with the commonality that their cocks are a lot bigger than yours. Once her big-cock taste is established, it’s a downhill roller coaster ride from there.

Luckily my wife and I have a very strong relationship. There were some unforeseen tensions along the way, but we have a stronger relationship now than when we were a ‘boring married couple’.

Boring no longer, though. Once the journey began, a number of accompanying fetishes arose to make it more interesting. Some she suggested after studying the subject online, and some actually recommended from other women she met on the web who are part of the Hotwife Community.

The reality of cuckolding is once she gets a better orgasm from a cock that isn’t yours, the aura of your manhood starts to diminish in her eyes. The first time just slightly, the second a little more, and if you continue beyond that, it soon fades until the aura completely disappears.

Before you know it, BAM, you’re a sissy husband with a useless clit for a cock who she treats like a walking-tongue in panties.

Control transference is what really happens once the process begins. It starts with all decisions being discussed and your input counting at the beginning, but over time it evolves to pretty much her calling all the shots. What started with me being an active part in every cuckolding event; has morphed into her meeting the guys alone and me sitting home with high level cuck-angst waiting for her return. Kinda hard to argue when you’re caged and wearing panties that she made you go buy yourself.

She cuck-dates (her name for it) usually once each week. Mostly just an overnight on Friday or Saturday, but there has been the rare weekend. She has a small pack of guys that she dates on random occasion. Like hungry wolves wanting to get at the bitch in heat; the texts start rolling in on Wednesday. She gets a real thrill out of ‘the chase’.

This was one of the ‘rules’ we made in the beginning. Having many men as opposed to ‘just one’ meant less chance for her to develop an intimacy that would jeopardize our relationship. So far so good. I’ll let you know if that changes.

Her newest thing is she feels I need a babysitter when she’s on her cuck-dates. And that brings us to the start of the story. Oh, and the other cast member, her Mom Janice, who is downstairs at the moment.

*****

Last month while on a date, my wife came home earlier than expected and caught me cruising some webcam sites. Lots of yelling and screaming (her at me) led to a heavy discipline session (many spankings with tears – mine). It wasn’t our best moment, but we got through it. The next day she spent all day on her tablet chatting with ‘her community’. Having a cuckold babysitter became the decided group solution.
“Sweetie, I know you aren’t happy with me having Mom watch you while I’m gone, but for this first few times I thought it best,” she said.

She’d explained this all before and she noticed the worried look on my face. “Whatever you say, Mistress,” I said.

“Don’t worry, sweetie, it’ll be okay,” she said, and chuckled. “Here, help me with my stockings.”
She sat on the bed. This is our pre-date routine. Me, freshly showered and shaved, cock caged and locked, in panties on my knees doing whatever task she requests to help her get ready for her date.

A year ago Tami’s Dad died, and her Mom has had a rough time adjusting. During the healing process my wife and Janice have grown much closer. Six months ago, Janice called while I was worshiping Tami’s toes on a lazy Sunday afternoon. My wife, who was deep into her second Bloody Mary, just happened to blurt out that I was licking her toes during the conversation. One Bloody Mary later and our whole cuckold journey had been explained to Janice.

Janice lives in our city and we’ve had her over lots since that phone call. To her credit, she has never made any comments about our ‘alternative lifestyle’. But I do catch them having secret chuckles, and sometimes I notice sly looks between them. I know there’s a private joke being made at my expense.

To make matters worse, Tami has made me wear my panties and cock cage on occasion when Janice has visited. She has whispered a few times that maybe she’d make me take my pants off and show Janice what I have underneath. Beet Red; would be my reaction explained.

“Sweetie, now we’ve gone over this right? Mom is going to babysit you and while she does, I expect you to do whatever she says. If not, then I’ll be very mad. Do you understand?”

“Yes, Mistress.”
I still can’t believe I’ve gotten into a situation where I’m being babysat, and by my wife’s Mom no less. The cuckold road has many unexpected twists and turns.

“Good, now I want you to put on the clothes I’ve laid out for you on the chair,” she said pointing at the chair in the corner.

I got up and went over to see what she’d chosen. Fuck, Fuck, Fuck, I thought! There was a pair of stretchy white yoga workout tights and a black Lycra workout bra. She saw my shock and with a little giggle said, “Go ahead, sweetie, put ’em on for Mistress. I want you to look cute for Mom tonight.”

This was a definite ‘over the line’ play. We have never involved people we know in any of our games. These clothes meant we were about to enter new territory and I didn’t know if I was up for it, but arguing about it wasn’t really an option.

I picked up the white tights and worked them up my legs. I could tell that they were going to be slightly see-through. They hugged my cage and you could see every plastic hinge and outline perfectly. My panties had little red hearts on them and I could see the hearts through the thin material. The bra was a little harder to negotiate. Tami was watching and smiling the whole time. I was afraid to look at myself in the mirror, but Tami had other ideas.

“Come here, sweetie, let’s see how you look,” she said, pulling me to the full-length mirror.

We looked a funny pair. Tami is 35, gorgeous with C’s on top, and killer tanned legs on the bottom. In her CFM’s she was as tall as my 5’9″ swimmer’s body. She totally rocked her LBD and her club makeup for the night screamed ‘Hotwife’ looking to get fucked. Then there was me. The sissy workout babe in cock cage and gym bra. She reached over and tweaked my nipples hard enough to make them poke out and show.

“Look at the time, I gotta get going. Let’s go meet your babysitter, cucky,” she said with a laugh.

*****

We headed downstairs, her heels clicked on the steps, me following in tights with no shoes. At the bottom of the steps I noticed Janice is sipping a drink. She looked at us as we reached the bottom and I could see her checking out my groin.

Janice is a firm 54 year-old mature woman with D’s that haven’t seen a bit of sag yet. She’s actually blossomed since Bob died. She joins Tami at the gym 3 times a week for various workout routines. Her thick blond hair is styled to make her look 10 years younger, it’s easy to see where Tami got her looks from. Tonight she was wearing a long skirt and loose blouse with the key to my cock cage hanging around her neck. This had been discussed, so it wasn’t a surprise to me.

“You look gorgeous tonight, honey, whoever you’ve chosen is going to be one lucky man,” she said, addressing Tami. Looking at me appraisingly, she said, “And you look so cute, James.”

“Mom, we talked about this, remember. I think calling him James is not going to work when you babysit. I’ve explained to you that when we are in cuckold-mode ‘sweetie’ is used. Under the circumstances, I think you can use ‘sweetie’ also.”

I gave my wife a sharp look. She gave me one back much harder with a glare that said, “Don’t even think of opening your mouth.”

“You two have a nice time now, I’ll see you guys Sunday sometime,” Tami said, as she gathered her purse and pulled out her mini-suitcase she’d hidden in the closet. I felt stunned, it’s Friday night, and she always lets me know if it’s going to be more than one night, but this time she didn’t tell me. “See you, sweetie,” she said, smiling, giving me a quick peck on the cheek.

Even though I was pissed, I knew under the circumstances, it would be better if I let it go without comment. “Goodbye, honey.” I answered without thinking.

She stopped at the door, turned and gave me one of those ‘you really fucked up this time’ looks. She stood there with her arms folded just staring at me. Janice looked on, confused.

“Try… Again… Sweetie,” she said in a very direct controlled voice.

“Uh… Good night, M-Mistress,” I said in a soft voice, but knowing Janice would hear.

“Mom, do you remember those sites I sent you about femdom discipline, and the ones about the best way to control your submissive.”

“Yes, I remember, dear,” Janice answered.

“To establish your role correctly, you need to be the one to take charge. As you can see our little sissy here is in need of a reminder of what’s what, after this little lapse in protocol. Do you want to watch me do what needs to be done, or do you want to do it?”

Janice looked at her daughter for a second and I could see she was making some kind of conscious decision. Finally, she said, “No, dear, you’re late. At some point it would come to me having to do this, I guess now is the perfect time.” Looking directly at me, Janice said, “Sweetie… Hmm, sweetie doesn’t feel right for me. Tami, you call him sweetie, but is it okay if I use a different name?”

“Sure, Mom, whatever you feel comfortable with.”

“Well, in that case, you just called him a ‘little sissy’, that’s kind of how I see him actually. I mean you’re dressed to kill and headed out to have sex with a real man, and he’s letting you without a whimper. I like ‘Little Sissy’, that’s how I see him now. So that’s what I’ll use from now on, if it’s okay with you, Tami,” Janice said.

Janice was sure pushing my cuck-buttons, I wonder if she knew she was. Looking directly at me, Janice said, “My little sissy, I want you to go down to ‘The Room’ and wait for me there.”

The Room was a secret space Tami had me design in the basement. I took an old storage area and walled off a small section. Then I disguised the doorway as a sliding bookshelf to keep the room hidden.

In the beginnings of our alternative lifestyle Tami wanted to experiment with everything and The Room became her petri dish. It’s where she disciplined me after catching me on the cam websites. Until now, we had never told anyone about it.

Like a deer in the headlights I stood there staring at Janice after her request. My wife had the biggest grin on her face. “Well, what are you waiting for, little sissy, get going. I’ll be down in a minute,” Janice barked.

“Yes, Mistress,” I said automatically, and started downstairs.

“Mistress. Wow… I really like that,” Janice said with a smile that matched her daughters.

Before I went down I saw Tami come over to her Mom and gave her a big hug saying, “Oh, Mom, I’m so proud of you, I know your time with my little cucky is going to really help you. I love you so much. Letting you have use of him is the best thing I could ever do. Whatever you do, don’t be timid.”

“Don’t worry, dear, I felt something a minute ago when he called me Mistress. You were right, this domination thing is very empowering for a woman. I can’t wait to explore it,” Janice said.

“Well, remember what I said, Mom. You can do anything you want, there are no limits.”

“Thank you, dear, you better run along you’re late. See you Sunday. Have fun. Love you.”

That was the last I heard as I hustled down to The Room.

*****

The Room is 10′ by 12′; it has a black marble floor with full mirrors on 3 walls and the ceiling and no windows. One wall has a couple of racks with various toys and there’s a big trunk with lubes and various S&M leather and lace outfits. There’s a sex-swing and a big padded table in the centre, and large standing candle holders, one in each corner.

My routine when sent down is to light all the candles and stand by the table and wait, eyes down. That’s how Janice found me 30 minutes later. I peaked and noticed she’d changed into Tami’s Japanese silk kimono that barely covered her crotch and butt, it was all she was wearing. Her smooth, firm legs were bare and I noticed she had Tami’s black stiletto 6″ heels on which made her slightly taller than me. I couldn’t see any bra straps underneath the robe or panty lines. I could feel the pressure in my cock cage thinking my Mother-in-Law was almost naked save the thin oriental covering.

She shut the sliding bookcase and without hesitation started right in, “James… Err, I mean… Little sissy, I want you to know I’ve never done this kind of thing. Bob was a real Man’s Man and he would have never put up with the games Tami plays with you. But I’m open-minded and I know Tami really feels that my participation as your babysitter is important. Tami also mentioned that I could do whatever I want with you. I’m not as experienced as Tami, so I don’t know if I’m supposed to ask if you agree. Am I supposed to ask?”

I wasn’t sure how to respond, but I knew however I did would probably be repeated to Tami later so I chose my words with care. “No Mistress you’re not required to ask my permission, if my Wife-Mistress says you can do whatever you want with me then my Babysitter-Mistress can feel totally free to use me as she wishes.”

“Really, I think I like that,” she said as she went to one corner and blew out a candle.

“Tami says I should spank and whip you, what do you think about that. Do you enjoy it when Tami does it?”

She went to another corner and blew out the 2nd candle. “Sometimes… No, that’s not right, I know I deserve whatever discipline she or you decide to mete out.”

She went to the 3rd corner and blew out that candle. If she blows out the last remaining candle the room will be totally pitch black, which she just did.

In the total darkness and soundproof room, I could hear her heels on the marble, she was right behind me. I could smell her perfume and then I suddenly felt her.

There was no visual in the blackness, she surprised me as she pressed herself up against my back. I could feel her silk covered D’s pressed against me, and then her pelvic bone as she pulled up tight against my ass. Her warm hands started rubbing up and down my bare sides. As they moved to my shaved stomach I could feel her breath on my neck.

“I’ve always thought you had a nice body, James,” she breathed in my ears, as her fingernails tickled my navel.

Her fingers started rolling down my tights. I could feel the silky robe on my ass. She started to grind on me. “You know it’s been two years since I’ve had any sex. Tami said I could use you any way I wanted.”
Her breath was laboured. Her fingers started fumbling around my cock cage, exploring something unfamiliar to her. Every time she flopped it one way or the other it elicited little groans from deep within me. She found my smooth shaved balls and spent a lot of time just playing with them.

“I find it fascinating that you allow my daughter to lock you like this. Don’t you like sex?” She asked, as she bit my earlobe gently. I felt a warm shiver pass from my neck to my cock.

The pressure was getting pretty intense. Sometimes Tami will tease me until the pressure-pain so bad from the blood engorging my trapped penis that I start to cry. Janice was pushing the right buttons and the pain was starting.

I wasn’t sure how to answer her question, “I love sex, but I’m locked. So only my Mistress can control my releases. The thing is, I have a… I have a small… I have…”

“I know, little sissy. Tami’s told me all about your tiny cocklette, and how it doesn’t please her anymore. I read that a Mistress will lock up her cuck’s inadequate appendage because it helps the cuck focus more on the Mistress’ pleasure than their own. Am I right, little sissy?”
Jamming her tongue inside my ear canal and grabbing onto both nipples forcefully as she said this last part. She was starting to twist and pull them exactly like I like, all the while telling me what a shame that my penis was too small to please a real woman. I could feel my pelvis involuntarily try to hump the airspace. I was really starting to lose it.

She reached down with one hand and glided her finger over the tip of my cage. She dug her fingernail into the gap and poked the head of my cock very hard. I jumped from the slight pain. “There, there, my little sissy, I haven’t felt one in a long time, sorry if I hurt you. Looks like someone is leaking a little boy-juice.”

Boy-juice is what Tami calls it too. She brought her wet finger to my mouth and slid it just past my lips. I sucked and licked her salty finger softly and then when she twisted my nipple harder I sucked it all the way in my mouth, hungry for it. She started pushing it in and out like she was fucking my mouth. “How does your boy-juice taste? My daughter tells me you’ve sucked cock before.”

Urgh… Oh my gawd… Does this woman know all my secrets, I thought wildly?

“Don’t be shy, little sissy, I’m just curious is all. Are you able to deep-throat them, do you swallow cum, do you lick their sweaty balls? My daughter tells me you swallow and do all that, and also clean them off after they’ve been inside her. That’s what good cuckolds do, she said. I have to tell you that when she first told me all this I was disgusted. Yet the more I’ve come to realise it’s all a part of the Dom/sub game that couples like you two play. I find myself getting excited by it. I’d love to watch you. Would you let me watch you suck a real man’s cock sometime?”

“Ugh…” I moaned, totally embarrassed yet totally excited thinking of it may be happening for real.

I could feel her removing the kimono; her shaved moist pussy was rubbing my ass. In the total darkness the sensation was incredible.

“Tami tells me you are especially talented with your tongue. I guess a man with a 4.5″ skinny penis who can’t get a woman off has to have one quality attribute in bed. Otherwise, they’d never be able to snare a woman like my daughter. Are you good with your tongue little one?” She asked, while twisting my nipples with more force than even Tami does.
“Yes, Yes…” I screamed, as much from the nipple torture as from the extreme sub-space she had transported me to.

“Why don’t we find out, shall we? Jump up on the table for me, on your back, of course.” I could hear the excitement in her voice.

It’s a large padded table. I had to build it wide enough so Tami could manoeuvre me any way she wanted and still make it comfortable for her.

I felt Janice pulling off my tights and I raised my arms when she wanted to remove my little bra. Not being able to see her and just listening and feeling added to the sensation. I imagine it was the same for her.

She climbed on my lower legs; I could feel her slowly dragging herself up my body. When she got to my cage, she started rubbing her pussy all around my plastic jail, the sensations to my cock were amazing and painful, but I knew not to utter a sound while she had her fun.

“Oh my God, that feels fantastic. You know, sissy, maybe there’s a use for your little penis no one has discovered yet,” she teased.

She reached down and grabbed onto my nipples for support to help move herself up further. Finally, she had managed to get my head between her thighs. Ever so slowly she lowered herself to my lips.

I’m not an expert, but I do know enough that when it comes to being in a situation where you might be licking pussy for a long time you don’t rush the process. I nuzzled my nose in first taking in her sweet womanly scent. I could tell she had made herself fresh for a ride she probably knew was going to happen. I spent a lot of time just flicking and lightly teasing. During this whole time she didn’t do anything to direct me, allowing me to my own ministrations. Every so often I’d hear a moan or a sigh.

I reached around her thighs with my hands and tried to pull her down more forcefully. She grabbed me by a hunk of hair and forced my head back.

“Slowly, little sissy, I haven’t felt this in a long time, we’re not going to rush this.”

I acknowledged her request by going back to my flicking and teasing. On an off chance this might work, I started to gently caress your clit on occasion. Tami mostly likes a hard tonguing when she cums, but on rare occasions she likes a gentle cum. Janice was starting to leak a little and I slurped loudly for effect.

“Oh yeah,” escaped from her lips.

A gentle one, for the first one, I thought.

It took but a couple of minutes of me just teasing her clit. When she came it made me feel proud that I’d done the job right for her. Like a slow moving ferry, her orgasm came to port with tender bumps here and there; with some added unexpected well-placed teeth-friction I was able to bring her to an intense orgasm like none I’ve ever had a woman experience before. I had to grab her thighs to hold on or she might have fallen off the table. The soundproof room amplified her screams that had been waiting for 2 years. On her orgasm’s downhill slide she grabbed my ears and pulled back my face so that gentleness was maintained.

I love a woman who likes to take control of her oral. My new Mistress was performing beyond measure. She was turning a reluctant son-in-law cuck into a full-blown submissive to a Mistress of worth.

“Oh Jesus, that was 2 years’ worth. God, you have an amazing tongue, little sissy. I can see why she keeps you around. Umm mmm, that was fun,” she moaned.

She couldn’t see but I was grinning and loving being her new sub and a part of this new journey for her.

“That was fun alright, but I need MORE, now hold still.” She slid off my face and shimmied down my body so she was facing towards my head and my cage was nuzzled up against her pussy. “I’ve read about this and want to try it, don’t move.”

She grabbed my cage and rubbed it up and down on her wet slit. Ever so gently she pushed my plastic covered cock inside her. I wear the CB-6000S which means it’s about 2.5 inches long. I could tell she had the full amount inside her.

“Of fuck that feels great to have something inside me besides my fingers. Fuck me, little sissy, come on, you still remember how to do it don’t you.” Then she grabbed onto my nipples and pulled them hard to encourage me.

Tami had never done this with me before. I was afraid that the cage’s sharper edges might bruise her clit, or worse, maybe, but Janice would have none of my tentativeness. She rammed her pussy right down hard, so hard it hurt, but I wasn’t about to complain.

“See I told you your little cock was good for something, I love it. Come on, fuck me, little sissy.”

So I did, just like I remembered. As hard as she dropped her pussy down on my cage, I hammered upwards. My cock was getting no pleasure, but I could tell my new Mistress was getting what she needed.

I could feel her thighs start to shake and her whole body starts to shudder. “Oh fuck, of fuck, I’m gonna cum, don’t stop, don’t stop… Oh Jamessss, oh JAMESSSS,” she groaned loudly.

I just did my best to hold onto her and keep the contact between us tight until her orgasm throes subsided. At the end she collapsed on me, burying her face in my neck. I couldn’t really tell, but it felt like she was crying a softly.

Finally, she quieted, collected herself and pushed herself up. Back in character, she said, “It’s a shame you have such a little dicklette, otherwise I would have let you cum inside me. I would imagine Tami is letting her lover do that as we speak.”

She exited our coupling and again moved her pussy to my face. In a very demanding voice I hadn’t heard before she said, “Clean me.”

She was soaked, so soaked her fluids were running down my cheeks despite my efforts to lick and slurp up all the liquid. Her third orgasm came suddenly and only lasted a few seconds. The force she drove her vulva on to me almost broke my nose. “Oh my fucking god…” Was her only comment before she moved off my face and stood beside the bed.

Moving close to my ear, she whispered, “I think I like being your babysitter. I think it’s time we do what we came down here to do in the first place.”

She was transforming, I could feel the slight change from novice to a real Dominant.

“Answer me this, little sissy, are you going to cry when I paddle you?”

Oh fuck, I thought.

The End.

 

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