My Mom met Dwayne a few months ago and has been dating him for over a month. She’s 43, and he is 33. She could easily pass as a woman in her early 30s. She’s medium height and curvy, with pale skin and perfect red hair. Dwayne is well over 6 feet tall, muscular, and black. You can tell he pumps iron and works out regularly.

I, on the other hand, I’m 24, not tall, just under 5 feet 9, as pale as my Mom, and skinny. Just like my Mom, I also look younger than I am, and many would believe I was in my late teens if I were to tell them. I started dating my girlfriend at a similar time to when my Mom met Dwayne. Becky is 19 and, like my Mom, she is also a redhead and pretty curvy; they could nearly pass for sisters. Although I have heard from a few sources that she is promiscuous, the most we have done is some heavy petting.

After another make out session and a little dry humping with Becky she left to go home, she didn’t look satisfied and neither was I. I often wondered if she hadn’t gone any further with me because she knew I wasn’t big. She’d felt it through my jeans and shorts many times. The last time I measured my erection, it was just under 4 inches. My last girlfriend said it was an OK size, but we all know how that goes.

Feeling horny after Becky left I went searching for a pair of panties to play with, I’d been doing this since as long as I can remember. To my knowledge, my Mom doesn’t know. At first I enjoyed the feeling of just wearing them and then masturbating but after watching some mother son porn I’d begun to not only sniff them but also lick her dirty underwear whenever I was horny.

Going through her underwear drawer was one of my favorite hobbies, and since she’d been regularly dating, her choice of underwear had become even sexier. My favorite was her thongs, and on this occasion, I picked out a little red one to wear. Checking through her dirty underwear, I found a pair that I assume were yesterday’s or maybe she’d taken them off before her date with Dwayne.

Having the house to myself, I took the dirty panties with me back to my room and lay on my bed in just her thong. I was sniffing the crotch of her panties and rubbing myself when I heard my Mom shout up the stairs.

“Dwayne, while you’re up there, could you bring a blanket down so we can cuddle on the couch?”

“Yeah, baby, I’ll bring one down.”

I had no idea how long they had been back; I’d been lost in my perverted thoughts. Quickly pulling on a pair of jeans over the thong, no time to put on my underwear. I shoved the dirty panties in my pocket, ready to put them into the laundry. To my shock, my bedroom door had been open, I couldn’t remember if I’d shut it, and for Dwayne to have gone to my Mom’s room, he would have had to have walked past. My heart began to thump loudly in my chest. All being well, he hadn’t looked in. If I hadn’t been enjoying her panties so much, I’d have heard them come back.

I threw on an old t-shirt and made my way to the laundry room, taking some of my dirty clothes for cover. Once in there, I placed the dirty pair where they had been and chucked my clothes on top of them. In a moment of bravery, I thought, what the hell, I’ll take the thong off in the laundry room and push that to the bottom, in the hope that my Mom didn’t realize she hadn’t worn it. Undressing as quick as possible, I took them off and had them in the hamper in no time. They were wet through with precum and a small climax. They should be dry before she washes them. I left the laundry.

“Hi Peter, has Becky already gone home? She’s fine, you pulled a looker.”

“Yeah, she left a while ago, she’s got work early tomorrow, yeah, I don’t know what she sees in me.”

“I know what they normally see in guys, if you know what I mean.”

He playfully tapped me on the shoulder with his fist, and in my embarrassment, I just nodded my head and blushed. With Dwayne in front of me, I felt like a caught little beta, and he was a huge alpha male. I couldn’t believe there was less than ten years between us. He had a small blanket in his hand and I could see the muscles in his arms bulging, his upper arm was as big or bigger than my thigh. He smiled as he went past and back down to my Mom.

“You must be packing to get a girl like Becky.”

“Sure.”

He went downstairs, and I returned to my bedroom, still red in the face. I waited in my room until I heard Dwayne’s car pull out of the driveway. Once he’d gone home, I went downstairs to say hi to my Mom. She was wrapped up in the blanket, watching reality TV. Her dress was thrown over the back of the chair. They’d more than likely been fooling around while I was in my room. I could see her bra in the gaps where she was fully wrapped.

“Hi, Mom, has Dwayne gone already?”

“You just missed him, Sweetie. He seems to like you a lot. I might be going away with him on holiday, he’s got a place by the shore.”

“That sounds fun.”

“It will be good to get away and let my hair down.”

We made small talk for half an hour before I excused myself to go to bed. I was tempted on my way back to the room to grab the underwear again and finish where I’d left off, but decided against it. Settling for a sock I wrapped it around my penis and fantasized over Becky, but in between thrusts I also imagined my Mom. Morphing between the two of them, before long, I had shot my load and then lay spent on my side.

The next morning, my Mom had gone to the gym, and I decided to sit in the hot tub. On swim shorts and a portable radio, I lay back in the tub and relaxed. My Mom, getting back from the gym, decided to put a bikini on and join me in there. To her, she was just enjoying the tub, but for me, it was like catnip seeing her in a tight bikini. I had to stay in there with her until the erection I had died down. The way her breasts glistened in the tub was nearly enough for me to come.

Talking to her and looking through her, not allowing my eyes to focus on her body my penis finally went down. Getting out the tub as the water dripped off my body I glanced down to see the material of my shorts glued to my body, if my Mom would have been looking she would have seen my tiny nub poking out slightly.

“Dwayne will be here tomorrow for dinner. You can invite Becky, too, if you like.”

“I might, Mom, I’ll let you know if she can make it.”

Placing my swim shorts in the laundry, I noticed not only her gym panties but the thong she’d obviously worn on her date with Dwayne. Not being able to resist, I took them both to her room and watched through the blinds to make sure she was still in the tub. I wore her gym underwear over my face, breathing in her musky scent while I used the thong to stroke myself. All the time I watched her from the window, I pictured her and Dwayne going at it, my private porno film playing in my mind.

I came straight into her thong, and by the time I’d made sure none had sprayed anywhere else, she was out of the tub and making her way into the house. Like Usain Bolt, I sped to the hamper and replaced her things. Seeing her sodden things, I decided to wring my shorts out over her stuff, with any luck, she wouldn’t tell the pool water from the clothes when she put them in the washer.

“Becky said she can come around for dinner tomorrow.”

“Perfect, Sweetie. I’ll be making homemade pizza and cheesecake.”

“My favorite. Thanks, Mom.”

She gave me a quick hug and kiss on the cheek; no matter how old I got, she continued to do this. I watched a movie before bed and slept before it finished. Waking up fully, I went to the bathroom. After doing my business, I washed my face and went down to grab some breakfast. Mom was already down there prepping the food for later.

Becky arrived around 3 p.m., and Dwayne shortly after that. Throughout the meal, they made small talk about life, the weather, and work. I watched as Dwayne eyed up Becky and my Mom. I could tell he liked them both a lot. Not only was he good-looking, but he was charming as well; he seemed to know all the right things to say.

“Thank you for the lovely food, Mrs. S. That was the best pizza I’ve ever had.”

“How many times must I tell you to call me Grace?”

“Sorry, Grace, I keep forgetting, but I’ll get used to it.”

After a few glasses of wine, Dwayne suggested going into the hot tub. He’d bought a spare change of clothes in his bag. He was obviously staying over. I hadn’t asked Becky yet if she wanted to stay over, but I hoped she would. Maybe after a few more glasses of wine, she’d loosen up a bit.

“Do you want to join us in the hot tub? It’s nice this time of day, cool breeze and hot water on your skin.”

“I didn’t bring any swimwear with me, Grace.”

“I’ve got a spare bikini. We’re roughly the same size. What do you say?”

“Sure, why not? I always wished I had a tub at home.”

We went upstairs to change into our stuff, and Dwayne stayed put. He already had his stuff with him. While finding a pair of shorts, I wondered which bikini my Mom would pick out for them both. I couldn’t wait to see the pair of them side by side. I went downstairs and jumped in the tub. Dwayne was already in there. His upper body was so defined, each muscle stood out. Before too long, they came out in matching skimpy bikinis, the only difference was the color, Mom in white and Becky in a hot pink.

I was in heaven, Becky sat to my side, and the four of us sat there. I didn’t know where to look. I kept noticing stolen glances between the three of them. It was obvious Becky was checking out his body, and Dwayne was checking out hers. I didn’t have any doubt in my mind that if he wanted, Dwayne could take my girl off me. My little pecker was straining in my shorts the whole time and when my Mom suggested I get them some more wine I panicked knowing I wouldn’t be able to hide my stiffness.

“Can I get the wine a minute, Mom? I think my leg has cramped up.”

“I’ll get it, Peter. I know all about legs cramping up in the hot tub.”

Dwayne smiled at me as he slowly got up to get the wine. I blushed, knowing he knew why I didn’t want to get up. As he rose further out of the pool I couldn’t help but notice his speedos bulging, his cock must be huge, I’d never seen anything that big in real life before, he’d put most porn stars to shame. I’m not sure if my Mom noticed me looking, but she definitely saw Becky ogling his package. She blushed, and my Mom looked at her with a smile and a slight blush of her own. Becky silently mouthed the word wow to my Mom. I felt totally emasculated by him.

We enjoyed a few more glasses of wine, then as it got a bit colder, we made our way back inside. Once we got out of the tub I could see the outline of my Mom and Becky’s nipples in the cold and the outlines of their pussies, Dwayne must have been looking too, because his package looked even bigger now, he wasn’t erect and he still stuck out further than if my erection was fully pushed out of my shorts.

“Ooh, it’s getting chilly out here now. I don’t want to shrivel up out here.”

“You won’t shrivel up too much, Dwayne.”

I couldn’t believe my girlfriend had said that to him. He chuckled, and my Mom and her giggled as they went back inside. After drying off, I went to my room with Becky, and they went to my Mom’s room. All of us were tipsy. I don’t know how many bottles of wine we had over the last few hours, but it was a lot. I stripped of and got into bed, my penis was achingly hard, she lay next to me in just her underwear, her head resting on my shoulder and we kissed.

While we were kissing, you could clearly hear my Mom’s bed creaking, moans of pleasure emanated from her room, listening intently, you could hear a hard and steady thudding as their bodies made contact over and over. Low guttural noises from him and more moans louder and louder moans from my Mom. The alcohol must have lowered her inhibitions. Becky held my 4-inch cock in her hand, moved it from side to side, a look of complete disappointment, she got up and made up an excuse then left and went home.

I was beyond angry at how I’d been cock blocked against my girlfriend by my mother’s boyfriend. They’d been carrying on like that for ages, and as I listened, I got more aroused and more curious. I snuck down the hallway to her room. The door was ajar, peeking through the small gap in the door, I watched as he pounded her from behind, flesh moving and rippling after every heavy thud.

I watched on through the gap and watched through the mirror, which was on the wall in front, it gave a clear view of her at an angle on all fours, I could see both of their facial expressions and saw the finale of her whimpering orgasmically putting her face into her pillow as she panted. He pulled out, and I saw just how big he was. It must have been as big and thick as a Pringles tube.

Admiring his specimen in all its glory, I think I must have made a noise, and was convinced that he saw me in the mirror. He turned around, and I scampered back to my room. Once my heart was at a normal rate, I listened to them as best I could.

“Just use my panties to mop it all up, you cum like a bull.”

“Baby, you make me cum that way.”

“Shush, be quiet, Peter and Becky might hear us, just wipe your cock clean and mop up this mess. Put them in the hamper, I’ll be washing them in the morning.”

I looked through the gap in my door to see Dwayne walking down the hallway completely naked. He hung low down his thigh, and although his thickness had decreased slightly, it was still as thick as my arm and easily 10 inches long. All he had was a pair of my Mom’s panties. I quietly closed my door before he walked passed.

I listened by my door until I heard him walk back passed my door and into my Mom’s room, the door clicked, and I could hear them talking quietly. Still tipsy and still horny I retrieved her panties from the laundry room, they were completely decimated with come, wet through and big thick globs of semen clung to them. Stealthily, I went back to my room. I never noticed my Mom’s door was ajar, and didn’t see Dwayne watching as I carried her panties to my room.

I lapped up all his come, knowing it had been in her and he’d been in her pounding away, I was hard as rock. After eating up all the visible come I wrapped her wet panties around my cock and achieved the best orgasm I’d ever had. I followed that by enjoying three more, and once I’d finished, I dropped them back into the hamper, with no need to hide any trace of my come that lay on them, I fantasized about my Mom licking what she thought was Dwayne’s come from her panties. By the time I fell to sleep, I was fully sober and completely limp.

Dwayne had gone by the time I went downstairs. My Mom was lying on the couch in just a robe, with a hot cup of coffee steaming beside her. She made no effort to turn around. I got myself some juice out of the fridge and then returned to the living room.

“Thanks for that dinner yesterday, Mom. Becky really enjoyed it.”

“That’s nice, Sweetie. My head is pounding from that wine, and my whole body is aching. I must have slept funny.”

Watching her as she said this, I had to hold back a smile and suppress my inner laughter. She’d probably struggle to walk for a week after seeing the size of Dwayne’s unit. I wouldn’t be at all surprised. I made her breakfast, then went upstairs to play on my old laptop.

I saw Becky a few times the following week, but each time she still didn’t seem too enthusiastic to do anything; she let me lick and kiss her nipples. At the same time, she fingered herself, and one night she sent me a video of her sitting in front of her camera, leg’s wide apart as she slowly fucked herself with a black dildo, it filled her nicely, enveloping the toy she pleasured herself. It was the most promiscuous she’d been.

“Hi, Sweetie. Dwayne is going to be staying over the next few weeks. His apartment is being decorated. I’m sure you don’t mind.”

“It’s fine, Mom. Have you decided when you’re going away yet?”

“No, we still haven’t made plans yet, but I’ll let you know when I book the time off.”

Dwayne had been at our house for two nights by now. It wasn’t bad having him around. We had similar tastes in music and films, and obviously similar tastes in women too. I was half asleep in bed when I heard a slight knock on my door, beckoning them in. The door opened up, and Dwayne was standing there fully naked. I thought he might have been sleepwalking, stranger things have happened, but he was fully awake. He flicked my light on, and my eyes squinted from the change in brightness.

I noticed two pairs of panties in his hand, one was completely covered in come, like the ones I’d taken, and one was in pristine condition. He handed the covered pair to me, and I took it without any hesitation. He pulled my duvet off to reveal how excited I was, smirking as he saw just how unfortunate I was compared to him.

“I noticed what you did last time I put these in the hamper, so I thought I’d deliver them straight to you. While I’m staying here, I want you to be wearing panties at all times, even if Becky is here.”

“What? Why?”

“I saw you wearing mommy’s panties, and I’ve seen you stealing her cum-filled ones. So, unless you want everyone to know, I suggest you start wearing them.”

“My Mom will find out, though. She’ll notice her panties going missing.”

“Don’t worry about that, I’ve bought her lots of new pairs, and seeing as she let me stay over, I’ve agreed to do all the laundry, but in all honesty, you’ll be the one doing that.”

“I promise I won’t do it again.”

“All sissy’s say that. You’re not the first guy I’ve had fun with. Put your new panties on and model them for me.”

I put them on, pulling them up my legs, the silky material tenting out with my swollen member. I could see Dwayne’s cock still glistening from my Mom’s pussy, come still dangling off of him. He looked to where my eyes were fixed, smiled, then used his finger to scoop the come off of him. Moving his finger towards my mouth, I instinctively opened up and allowed him to wipe it on my tongue.

“Just do as I say from now on, and your secret is safe from your Mom.”

“OK.”

Before he left the room, I began to lick my Mom’s panties, greedily I lapped up his come and her juices. He smiled called me a good sissy and left the room. I wore the clean pair the following day, and each night, Dwayne would give me a clean pair and a soiled pair. I enjoyed each visit. Throughout the day, whenever my Mom was in another room, if he said panty check, I had to show him. The first time he saw my soft pantied bulge, he couldn’t believe just how small I was.

“Your Mom is really enjoying how I pound her on a night, I watched cuck porn with her and I keep telling her how I’d love to cuck someone tiny.”

I didn’t object to anything he said but did think it would be impossible to cuck me from my Mom seeing as she wouldn’t fuck me anyway. I hadn’t seen Becky since I’d started wearing panties full time. I’d been putting off inviting her over. Dwayne commented on how he hadn’t seen her, so he told me I should ask her to come around. My Mom would be at work until late, and I assured Becky that Dwayne would probably stay in my Mom’s room. Letting her know the front door would be unlocked as requested by Dwayne, I sat and waited for her.

“I want you to wear these tonight. I got them for your Mom as a joke, but they will look cute on you, too. Hopefully, Becky doesn’t see them.”

He threw a pair of white silky panties at me, winked, and closed the door. On the front was a spade, and written in cute writing was the Queen of Spades. I replaced my underwear so as not to disappoint him. If he requested a panty check, I’d be punished in some way if I weren’t. I heard him go downstairs; he was probably waiting for her. No doubt he would charm her before she came up to my room.

He loaded up a cuckold video and unleashed his throbbing cock, stroking away slowly to assure he’d still be hard when she arrived. About ten minutes into the video, Becky walked through the front door. She saw him and his huge member, and her jaw dropped to the floor. It was bigger than the guy in the video he was watching.

“I’m sorry. I didn’t realize you were coming around. Don’t tell Grace I was watching this without her. She’ll be pissed.”

“Don’t worry. I won’t say a thing.”

He hid himself under a blanket, but there was no hiding the huge tent under there. She joined him on the couch and made small talk as she watched some of the video with him. He hadn’t even bothered to pause it. Reaching under the blanket, she wrapped both hands around it. One hand wouldn’t do the job, unlike her boyfriend. She rubbed up and down a few times, but he put his hand over hers to stop her.

“What’s wrong? Don’t you like it?”

“It feels great, but what about Peter? He’s a cool dude. Although me and his Mom fantasize about cucking someone, I’m not sure he’d like me to cuck him.”

“What if he enjoyed it too? I’d be so lucky to get with you.”

“If Peter truly wanted it, I’d be happy to satisfy you in front of him, think how dominant it would make us both feel.”

“Should I just ask him?”

“Try getting him used to the idea, watch a few videos with him, promise him something, if he’s small like the cuck in this video, get him to wear your panties.”

“He’s much smaller than that cuck, if I do all that, then we can have fun?”

“Work on him over a few days, if you persuade him enough, he’ll want to please you. Next time we have a free house, we can have some fun. Grace will be back soon, so not tonight.”

She removed her hands, bit her lip seductively, and agreed to start on Peter. She looked flushed as she entered my room and joined me on the bed. I put my arm around her and hugged her closely, kissing her. She straddled my chest and pinned me to the bed, sliding herself down until she straddled my crotch she began to dry hump, I was hard in no time.

“What’s gotten into you?”

“I’m just really horny babe.”

“Me too now.”

“I was watching porn before I came around here, it was so hot.”

She continued to hump away, kissing my neck and nibbling my ear. Breathing heavily into my ear, she gasped. She must have orgasmed before I had a chance to finish. Before her moan subsided, I came into my Queen of Spades panties. Noticing that I’d finished she rolled off and began to rub herself through her clothes, her moans were much louder now, if she hadn’t come while dry humping she definitely had now.

“It was so hot, we could watch some later together, it would be fun.”

“You want to watch porn together? Sure, I don’t need to be asked twice.”

Dwayne had turned the video off long before Grace got home, and after she’d caught up on how her day had been, they had some wine and food together. She enjoyed knowing the housework was getting done so she could relax more on her day off. They watched the video he was watching earlier, but in bed, she craved watching these with him.

“It’s a shame you don’t have a boyfriend, think how much fun we could have with a sissy around here.”

“Mmm yes, now fuck me hard.”

Me and Becky were now watching our third porno, each one had been cuck porn. She got off on it so hard. We were under the covers together, and I’d managed to remove my panties under the covers without her seeing. Both of us are completely naked. In our fourth movie, we went from pleasuring ourselves to pleasuring each other. My hand was completely wet with her juices. And just like in the video we’d just watched, I’d licked my hand clean. She was like a new person, wild like what I’d originally heard.

“That was amazing.”

“They’re my favorite videos, I’d love to fuck a little cuck boy after I’d been stretched out. It’s a shame we can’t do it.”

“It does look fun, but you’re right, we can’t do it.”

“What if we could? It would make our first time together so memorable, a once-in-a-lifetime experience. Would you want to?”

“If we could, I would for you, of course I’d do anything to make you happy.”

I really wanted to sleep with her so badly. We cuddled naked and while we kissed we heard pounding noises coming from my Mom’s room, Dwayne was fucking her loudly again. This time, though, Becky stayed until my Mom’s moans had stopped. We heard him walk passed the door and back again. Becky got dressed and kissed me passionately again.

“If only I could cuck you with Dwayne, I bet he could stretch me just right for you, and I’m sure he’d keep it a secret.”

“You want to fuck Dwayne?”

“If he’d let me, I would, think how much fun we’d have together after it, I’m wet just thinking about it.”

She left my room, promising to text me once she got home. A few minutes later, a knock at my door. Dwayne didn’t wait to be invited in; he just opened the door, demanding a panty check. I removed my sheets to show my naked flaccid cock, at first he laughed, but his face soon became harsher.

“Where’s your panties? I told you to wear them at all times.”

“I’m sorry, I got them wet while I was fooling around with Becky.”

“That’s not good enough.”

“I’m sorry.”

“Put them on and go downstairs and grab me a beer. On your way back, I’ve left you a treat in the hamper. Grab it and bring them both to me. I’ll wait outside your Mom’s room.”

I slid my wet panties back on in front of him, and a look of content spread over his face. Hoping that my Mom stayed in her room, I went down and grabbed a cold beer from the fridge, while down there I finished off the open bottle of wine on the counter. Walking up the hallway with a beer and dirty panties, he watched with a huge smile. I handed him his beer. He whispered into my ear.

“Kneel at my feet in front of your Mom’s room and lick those panties clean, I want you to thank me for coming in your mommy as you lick them.”

I got to my knees and began to lick them over, repeating quietly what he told me to say. I left no part uncovered. He drank his beer and watched as I followed his orders. He motioned for me to open my mouth, rolled the panties up, and stuffed them in my mouth.

“Suck.”

“Dwayne, what are you doing out there?”

“Coming, Grace. I was just talking to Peter about whether he wanted to come along on holiday with us. The more the merrier.”

“Ooh, Peter, what do you think, the beach is nice this time of year?”

He motioned for me to get up and nodded towards my Mom’s door. He opened it up and stepped in. I poked my head through the gap he had left open and nodded. She asked what I thought, with my mouth full of panties, I looked away, pretending to cough, and I answered her. With that arrangement, she would go ahead and book some time off work.

“Come in here, Peter, and give me a hug goodnight.”

“I need the toilet badly.”

“It will only take a minute.”

“I think he’s shy, babe. He’s only got his boxers on. It’s a bit embarrassing coming in just underwear to kiss your Mom.”

“It is a bit embarrassing, Mom.”

“Throw him something to wrap around him.”

He threw out a small towel, which barely covered me. I wrapped it around my waist and entered the room. Feeling vulnerable at how if I dropped the towel, I’d be standing here in only her panties, I slowly walked over and hugged her. She gave me a kiss goodnight. Before I could leave the room, she got out of bed, with only a skimpy night gown on, and she made her way to the door.

“I thought I told you to put my clothes in the laundry.”

“I only took your panties, and then I bumped into Peter.”

Dwayne was lying in bed at this point. She scooped up her clothes from the day and headed with me out the door. She was quicker than I was, so she saw her panties still lying on the floor, realizing Dwayne must have dropped them in embarrassment when he bumped into me. She tried to scoop the panties up with her foot, but failed miserably. She only managed to fling them a few feet down the hallway.

“Peter, Sweetie, can you pick those up and put them on the top?”

I lifted the soaked panties using just two fingers, trying to hold as little material as possible. I had to be careful not to show how used to handling her soiled underwear, so I grimaced to show displeasure. I put them on top of her things. And went to my room, before I could close the door, though my Mom popped her head in and asked for the towel. I got under my covers, removed the towel, and threw it on top of the rest of the clothes.

“Fancy being shy in front of your Mom, it’s not like I haven’t seen it all before.”

“Sorry, night, Mom.”

“Night, Sweetie.”

Grace put all the clothes into the laundry, smiling to herself at how shy her son had been. She didn’t admit it to Dwayne when she got back into bed, but seeing her son pick up the panties covered in come turned her on. She was surprised that there wasn’t that much on them; it felt like Dwayne had come more than that. She’d check the carpet in the morning to make sure that no one had seeped into it.

I slept in my Queen of Spades panties while I listened to my Mom getting pounded again; she was like a rabbit. I knew who I’d inherited my horniness from now. I rubbed myself to climax as I listened and fell to sleep. Dwayne entered early in the morning as my Mom slept. Checking, I had panties on, he was happy not to have to punish me today.

Becky and I watched cuck movies every time she came around now. The first few times, she was happy with how it had been, but then she left a bundle of her underwear for me to wear; she wouldn’t allow any fun until I wore a pair that she picked out. Every time I’d put a pair on, she would remark how much bigger Dwayne was.

“Last time I saw Dwayne, I asked him if he’d do what we said, with you watching as we did it.”

“What did he say? Are you sure this is what you want?”

“It’s definitely what I want, he said, as long as you wanted it and were prepared to show how much you wanted it.”

“If you want it, then I want it. I can’t wait to sleep with you.”

“It will be magical. I’ll ask him what he wants you to do, and you can do it for me. I’m so excited we’re just thinking about it.”

She texted Dwayne to ask him what he wanted. Telling me how much she loved me, we continued to watch more porn. Her phone beeped a few times. While reading the text messages, she looked ecstatic. She grabbed a few pairs of her panties and left the room. Not before she handed her phone over for me to read.

“I want you to leave two pairs of your panties in the laundry, I’ll fuck his Mom long and hard, and I want you both to listen in the hallway until I come out, I will use your panties to clean up all the come with and I will meet you outside of the room. If he will eat my come out of your panties he will earn the right to eat my come out of your pussy. I want you wearing only your underwear, and Peter to be naked, no exception. If you can do this, then I’ll rock your world.”

I read through the text, and she was back before I’d finished reading. She held my hand and looked at me with pleading eyes. At this point, I’d already done much worse, but the extra humiliation of doing this in front of my girlfriend made it so much worse. Still looking at me, she asked if I’d make her dream come true, and I accepted. She replied to him and he text to let them know when he was ready.

“I’m going to grab some of your underwear from the hamper. I would use the ones you’re wearing, but I want to enjoy undressing you a few times tonight.”

She waited on all fours on the bed, wearing a matching red silk set and black stockings. Dwayne didn’t bother to text; he just opened the door and said it was time. By the time we were waiting by my door, he had gone back up the hallway holding Becky’s panties. We followed him to their room, and he left the door ajar. It was obvious he wanted us to watch and listen.

Becky watched as Dwayne stripped off, talking about how he was going to fuck her hard so her little cucky wouldn’t be felt in her pussy ever again. They were deep into the cuck roleplay. Motioning me to watch, I saw from an angle my mother being stretched wide, panting hard, she screamed for more. Becky was fixated, her eyes glistened with joy, her hand was fully in her underwear, as she watched the thrusts speed up, she rubbed herself harder and faster.

My Mom and Becky climaxed multiple times, to my embarrassment, I had erupted onto myself, without a second thought, Becky wiped it off with her hand and fed it straight to me. Neither of us could understand how he had lasted this long, but when he did finally come, it was hard, all the muscles in his body fiercely clenched, and his legs bucked a few times with each shot. Her pussy was a gooey mess.

With the two pairs of panties he caught cum seeping out of her, it seemed like there was a whole pint but was probably a lot less. Once she stopped leaking, he dried her off with the pair that had the least cum on. She moved forward on the bed and collapsed in a heap. She didn’t even call to ask him to shut the door on his way out.

“Put these on, and get cleaning those, and I want you to join your boyfriend on his knees while you kiss a real man’s cock.”

Barely ten feet away from the open door, I put on the wet panties. Kneeling in front of him, I cupped the others in my hand; they were full and dripping out. Becky, kneeling beside me, looked at the sodden panties and nodded her head. As I lapped up all the coat, she kissed up and down the entire length of his shaft. I could make out every vein in his god like penis and could see a pulse too. Once Dwayne was satisfied with our performance, he left and went back into the room.

Becky practically floated back to my room, and I crept back too, each movement, I could feel the wetness of the underwear. She pressed play on the video she found, she played with herself as I kissed her feet, emulating what the cuck in the video was doing. Her phone beeped with confirmation. They had proved their worth.

“He said the next time your Mom is out on the evening he will fuck me like he just fucked her. You could look more excited.”

“I am excited, I can’t wait.”

“Hopefully you enjoy it as much as you enjoyed seeing him fuck your Mom.”

There was no point denying it; she’d seen how hard I was. Just the mention of their earlier adventure had my penis at full attention again. Sleeping over, they cuddled through the night. I had visions of how Becky’s pussy would look after it had been taken by his cock. I struggled to picture it for long, as she kept changing into my Mom. The days rolled by, and finally, on the following Friday, my Mom was going out with some work friends. Dwayne was back at his place now, but he still spent most nights at my house.

“I’m going out, Sweetie. Dwayne is downstairs watching TV. I think Becky just got here, too. See you later, enjoy your night.”

They were in the kitchen as I went down. I’d never seen Becky wearing such a hot little black dress. I found it funny that my Mom probably thought she’d been wearing it for me. He handed me the Queen of Spades underwear and told me to wait on my Mom’s bed for them. After what felt like hours, they came in. I was told to lie with my head at the bottom of the bed. Watching upside down as she took her dress off, she was wearing an identical red set that my Mom had worn.

“Dwayne bought them for me, aren’t they cute?

“You look so good.”

She got on all fours, copying as my Mom had done, the only difference being that I was lying under her, and her legs had my arms pinned down. I felt completely vulnerable and before long I had a monstrous view as Dwayne’s throbbing cock entered slowly into my girlfriend. For quite a while, I could see a lot of him; he was slowly opening her up, and as time passed, he got deeper and deeper. Juices dripped out of her and onto my face. With a face full of his balls, I tried to enjoy my view.

“Who’s big cock owns you and who’s cock are you going to cuck?”

“Yours Dwayne, your cock owns me. I’ll cuck Peter and his tiny dick.”

“Hit his tiny dick and balls, prove to me how much you need this cock.”

“Yes, Dwayne.”

I felt excruciating pain after she hit my pantied bulge over and over again. Each time he slammed her, she whacked my bulge. Carrying on like that until he came. Knees week she lay onto my body, my penis had gone completely limp from the beating. As he pulled out he ran his softening cock along my lips. I opened my mouth to catch the dripping come, first out of his tip and then out of her. I dutifully licked her until no trace of Dwayne remained except her gaping lips.

While Dwayne took a shower, Becky finally gained her composure, and she climbed off my body. She glowed about her, and I could see in her whole demeanor just how much she enjoyed it. She massaged my pantied bulge and before long she had my panties down and was hovering above my erect cock, she slowly sat down on it and moved up and down. No pleasure registered on her face, and after a little over ten thrusts, I came into her; if she hadn’t been as loose down there, I doubt I’d have lasted three.

“Thank you for cleaning my pussy up twice. You didn’t cum anywhere near as much though, so not much to clean. He was amazing. Sorry I hurt your little clitty dick and balls.”

“It’s OK. I know you were just in motion for what you were doing. Thank you for finally putting it out for me, too.”

“I hope he wants to do this next time your Mom goes out, I can still feel him inside me.”

I was hoping it was going to be a one-time thing, but by the looks of it, she was as hooked as my Mom. Becky had gotten dressed, and I was sitting, waiting for Dwayne, afraid to leave the bed in case he wanted anything else. He got out of the shower and left wearing a pair of shorts; he was heaving in them. Whereas my little nub barely poked out of my mother’s panties.

“Was it everything you both wanted?

“It was more than what I expected. It was the best moment of my entire life. My heart was still pounding until I let Peter have his little go.”

“Does that mean you want to do this again?”

“Yes, I would have it every night if I could.”

“If you do want it again, there will be rules, Becky. If you can accept them, I’ll rock your world again and again.”

“Anything.”

“If you’re serious, I’ll name my price. I never want you to have sex with Peter again, he can only touch your pussy if I say.”

“Wait, what?”

“Shut up, sissy. It’s your girl’s choice.”

“I agree to your rules, Dwayne. I need that again, I can live without Peter’s babydick.”

“Good girl, you made the right choice.”

I was stunned. I knew that we hadn’t been dating that long, but for her to completely give me up instantly, it broke my heart. Deep down, though, I honestly couldn’t blame her. I’d never be able to satisfy her as he had, and I’d rather still have her around than not see her at all. Any form of companionship was better than being on my own. I just hope she’ll still want fun, or maybe she just lied to him. She left to go home, and I was instructed to change all the bed sheets. Mom didn’t get home until late, and as expected, Dwayne took credit for changing the sheets and freshening up her room.

“Wake up, Sweetie. We’ll be going to Dwayne’s place by the shore for two weeks. You can bring Becky along. It’s not the biggest place, but I’m sure we won’t be under each other’s feet.

“I’ll let Becky know. When are you going?”

“Dwayne will drive down next Friday to air the place out, and I thought we could drive down Monday morning.”

“Sounds good.”

Over the next week Dwayne had started conditioning Grace to watch more and more porn together. Every time they watched porn involving a mother feminizing or cucking her son he would give her the good dick. They wouldn’t watch anything vanilla, and normal cuck movies he would only watch with her as a small part of their foreplay. And just as before, every time he cleaned her up, I would clean her panties. I only saw Becky once that week, but every day she wanted me to send a few pictures of myself wearing panties, getting myself to shave myself smooth to look extra girly. Apart from that, she didn’t seem interested at all. Dwayne had told me to make up a reason why she couldn’t go away with us, but he still wanted me to come. When I told Becky, she didn’t seem to care.

The Thursday night before Dwayne went down to the shore, I could hear them clearly; the door must have been open. Mom didn’t hold back at all. I heard them finish.

“For once, it would be nice if you just lay with me after sex, it spoils the mood with you leaving to dump my panties in the laundry.”

“I know, babe, if we had a real life cuck or a sissy we wouldn’t have that problem, he could take the panties with him or clean them in front of us.”

“That would be heaven, maybe we’ll eventually do it, if we find the right guy.”

“Life would definitely be much better.”

He walked down the hallway, opened my door, and threw the panties at me. I wasted no time at all. The following day, knowing I was safe from Dwayne, I wore my normal underwear. They felt so big after the skimpy ones I’d been wearing. It was nice just hanging out with my Mom. When she called Dwayne, I decided to give Becky a call to see how she was.

“You sure you’re OK? You have been quiet this week.”

“I’m good, I promise. But I do feel guilty.”

“I don’t mind that you did what you did. I still want to be with you.”

“I don’t feel guilty about that. I feel guilty because I didn’t tell you I’d be spending the weekend with Dwayne at the shore.”

“Are you there now?”

“Yes, I’ll drive back on Monday morning. We might even cross paths on the freeway.”

I spent the next two days moping around. I felt betrayed by Becky. She sent numerous pictures and a couple of videos; she was definitely enjoying herself. In the room I’d be staying in, she had left a makeup bag and a package of her panties. She had told me not to take my swim shorts with me, but I didn’t know why. From what I could tell from the pictures, videos, and a video call, it looked like a lovely place.

On Sunday evening, I went into our hot tub, relaxing until my Mom dropped in beside me. Her red bikini reminded me of that night we watched her getting fucked. I was rock hard in my shorts. We talked for a while until it was late, and with an early morning, we decided to call it a night. I was still aroused when she got up to leave the tub. On her way out, she slipped and brushed her hand against my crotch. She felt my stiffness for a brief second as she managed to get up and out. I still couldn’t help looking at how her bikini looked like a thong with how it was going up her ass.

“Don’t stay in there too long. Make sure you pack everything you need for the trip.”

“I’ll be out in five minutes. My case is packed. I’m already.”

I was woken up by my phone. Becky had text me before she drove back home, all it said was she’d left me a present. It was something to look forward to on my long drive down there. My Mom drove the first few hundred miles, and I drove the last two hundred. With my mind wandering about how this trip would be and classic rock on the radio, it didn’t seem to take that long until we arrived. The view of the sea from our vantage point was breathtaking. I didn’t realize just how much money Dwayne was worth, but judging by this place, he was a multi-millionaire.

“I missed you, babe. I’ve ordered some food. I’ll take those bags. Follow me, Peter, I’ll show you your room.”

On my pillow lay a single pair of cum-filled panties; she’d left a note explaining that I must record a video for her of me licking them clean. I put my clothes away, then made the video, even thanking her for allowing me to eat it all up. I jumped in the shower to freshen up after the long drive. Standing in front of the standing mirror, I admired how much I preferred my genitals shaved smooth. By the time I’d finished, the food had arrived. Fancy Mexican food, an assortment of different tacos, and red wine.

After food, Dwayne suggested sitting in the hot tub, making the excuse of having no swim shorts, I sat in the living room and watched TV. I could hear them splashing around like children. They came into the living room, and Dwayne grabbed a fluffy robe for my Mom to wear over her bikini. He changed in their bedroom. Before too long, I saw her rummaging around in her robe, moving from side to side, and out popped her bikini top onto the floor, nothing was on show to see. Then next she slid her bottoms off and kicked them next to her top. With the robe completely covering her, you would never know.

Watching a new action movie on TV, they half watched and carried on drinking. With the movie over, I decided to get an early night. My Mom opened her arms to embrace a goodnight hug good night.

“Can you take my damp bikini with you, Sweetie, and put it in the laundry? I forgot it was still there. I don’t want the floor to get ruined.”

“You don’t have to be embarrassed, Peter. I bet it’s not the first time you’ve picked up wet panties… I mean bikinis.”

Red as a fire hydrant, I picked them up and took them to the laundry. Grace didn’t realize that in a way it was mimicking what they’d watched in the porn, she’d watched so many it was as if it had a subliminal effect on her. Dwayne, on the other hand, took notice and smiled to himself. Pleased to know that she would be easy to convince.

They watched a sissy feminization movie and while they watched, both laying on their sides naked, he slowly entered her, not fully aroused he left half of his meat in her. The moment the Mom started dressing the son up, he began to thrust her gently. When the sissy son was begging his Mom for a strap-on Dwayne began to jack hammer her.

“This shit makes my dick so hard.”

“Don’t stop, keep going.”

I awoke to wet panties on my face. I checked the time, and it was just after 3 in the morning. I didn’t have to think, I cleaned them and put them into the laundry, her bikini greeted me as I left them both in the hamper. By the time I woke up in the morning, the house was empty. I was glad of the downtime. I got out my laptop, connected to the Wi-Fi network then enjoyed a few hours of gaming. I sent Becky a picture of the panties I’d worn under my normal clothes, then carried on gaming until my Mom came back.

“We’re going to take a dip in the hot tub, Sweetie. You should join us. Dwayne will let you wear one of his Speedos.”

“Speedos are uncomfortable to wear, especially around my Mom.”

“If you’re that embarrassed, I’ll close my eyes when you get in and out of the tub, don’t be a spoilsport.”

“I’ll show him where they are, Grace. You jump in the tub.”

We went to their room, and my Mom was already in her bikini and the tub. Dwayne, with no inhibitions, got undressed and stood there naked, looking through his drawers for a Speedo to wear. I could feel myself shrinking in his presence. He grabbed a navy-blue pair that showed off his bulge to the maximum. He handed me a skimpy red bikini bottom, which was obviously one of my Mom’s.

“Don’t give me that look, put your Mom’s bikini on and join us in the pool.”

“You want me to wear this in front of her?”

“She said she’ll close her eyes when you get in and out, so your little secret should be safe from her.”

He joined my Mom in the tub while I got changed into her bikini bottoms. They fit well, with barely a bulge at all, and the material was tight and showed my lack of manhood. Once I’d gathered up the courage, I walked to the tub. Shouting before I came out so she’d close her eyes. I saw Dwayne whisper something to her, and she playfully tapped his arm with her elbow, and giggled between them. Not once did she open her eyes, and I was submerged next to them.

Grace noticed as soon as she opened her eyes that Peter was wearing red under the water, and now she believed what he’d whispered to her. Her son had accidentally mistaken her bikini for Speedos. She wanted to see him in them, making small talk to waste the time until she’d ask him to get her something from inside.

“How are Dwayne’s Speedos, Sweetie? Are they too big for you?”

“They’re fine, Mom.”

“Not too tight either?”

“No, they’re OK.”

She couldn’t believe they were big enough for him; she struggled herself to get into them, his bulge must be sticking completely out from how tight they are. The more she thought about it, the more she needed to know.

“Sweetie, could you get my phone off the kitchen counter? I’ve been expecting a call. Don’t worry; I’ll close my eyes.”

She watched as he got out of the pool, but was gobsmacked by how small he was. He didn’t stick out like she thought, and he didn’t have much of a bulge at all. She told Dwayne he was right; as soon as she saw the red, she had no doubts.

“Did you notice how small his package is, babe?”

“Yeah I noticed when he got in the tub, he’s smaller than those sissies cuck movies we’ve watched.”

“I guess his future wife will cuck him.”

I grabbed my Mom’s phone off the side and made my way back to the tub. Once in the tub, my Mom dropped the bombshell that she’d seen I’d accidentally worn her bikini, she made a big joke out of it, and implied that she hoped they wouldn’t be too stretched out at the front. I was embarrassed until I got back inside. I didn’t stay around to hear any more jabs at how I’d worn her bottoms.

“It’s OK, Sweetie. I won’t tell anyone it’s not like you did it on purpose.”

I listened to what she had to say, then went to my room to escape the embarrassment. Loading a movie on my laptop, I put on my headset and turned the volume up. I didn’t want to hear them tonight. I knew Dwayne would bring in a pair of her panties at some point.

They watched a video together. She picked out which one; it was a feminization of a son, she was wet before Dwayne had a chance to push up against her. Once he was fully in, he worked up a rhythm, but then he stopped thrusting altogether.

“Grace, I think Peter is a sissy.”

“Do you really think so?”

“I wasn’t going to say anything until I saw some proof, but Becky confided in me by saying he gets off wearing her panties, she said he even stole yours too.”

“Do you believe her?”

“I thought I’d seen him snooping around the laundry hamper on a night, but apart from that, I’m not sure. Becky said he sends her pictures. If I had her number, I’d ask her to send them to find out.”

“I’ll add her on Facebook, and if she accepts, I’ll find out her number. I should really know it already to be fair.”

“She might not want to send you the pic because you’re his Mom, but seeing as I already know, I think she’ll send them to me. I’ll add her now, and hopefully tomorrow I can text her.”

With Dwayne’s plan put in motion Grace would find out her son was a sissy. The next day, as Grace searched his room, Dwayne and Peter had gone out to grab beer and groceries. She first looked through his suitcase, and found numerous pairs of panties, some looked like hers. Finding out his laptop, she loaded up his Internet history and she saw all the movies he’d watched, the majority were cuck, but there were more than ten which contained mother and son specifically.

Dwayne texted her to say he’d got Becky’s number through her Facebook and sent her all the pictures that Becky had sent him. There were at least a hundred pictures of him in various underwear. A few were of him naked and fully shaven; he looked tiny. The last thing Dwayne sent her was the videos of him eating came from panties; she couldn’t be certain, but they looked like her own panties. Heart beating hard, she went to her room and masturbated until she heard the car pull up.

“Hi, Sweetie. Can you put the groceries away while I speak to Dwayne?”

“Sure, Mom.”

They went into the bedroom and she explained what she had found in his room and on his laptop, along with all the pictures it was obvious how much of a sissy he was.

“What should I do?”

“Maybe you should help him become the perfect sissy, his girlfriend isn’t into it, but maybe with our help he could accept it.”

“Should we ask him over dinner?”

“He might try to deny it, but if you caught him in the act, he wouldn’t be able to.”

“You’re right, babe, let’s catch him in the act.”

Dwayne put his plan into motion; he’d already cucked Peter from his girlfriend, and now he was going to cuck him with his Mom. He placed the Queen of Spades panties on Peter’s bed, then went back to the living room. When Grace went to the toilet, he decided to have a chat with Peter.

“Tonight I want to fuck your Mom harder than I’ve done before, I’ve left some panties on your bed. I’ll leave the door open so you can watch, but if you do, you can only wear the panties.”

“OK, what time will you start?”

“You will hear us, and tonight I’m going to leave her panties in the laundry, and they better be licked clean when I check tomorrow morning.”

“How long do I have to keep this up?”

“Until I’m bored with you, maybe then I’ll allow Becky to fuck you.”

Dwayne and Grace were watching a sissy son film while in bed, he’d left the door open as he said he would and went through his plan with her.

“I think I’ve noticed him before peeping on us, I thought it was a trick of light but I’m sure it was him, and I think he must be stealing your wet panties out of the hamper after we fuck.”

“After seeing him eating cum off those panties it definitely seems that way.”

“I’ve set the hallway lamp to stay on all night, with the door open, we should be able to see his reflection in the window. After I put the panties in the hamper, you can watch from the doorway to see if he steals them.”

“What shall we do if we see him watching us?”

“We let the sissy watch.”

“And if we catch him stealing my panties as well, what then?”

“Then you’ve caught your little sissy, and from everything we know he will want it just as much as us.”

I lay in bed waiting to hear my Mom moaning, and once she did, I crept slowly up the hallway. It was hard to see much detail of them because their light were off, but the glow of the TV gave off enough light to see them. More than once, I thought they would turn around to face me, but they didn’t. My hand found its way to my bulge, rubbing myself to his rhythm. When he had finished, I hurried back to my room to wait for him to leave them in the hamper.

“Did you see him too?”

“Yes, I saw his reflection and I could clearly see him rubbing his little clitty, put those panties in the laundry and we’ll watch out for him.”

She watched from the doorway as Dwayne made his way back. Once inside, she shut it until there was hardly a gap, but enough to watch the hallway through. Within minutes, she watched as her son took her underwear and went back to his room.

“I saw him. He’s got my panties. What should I do?”

“Confront him. Then put the sissy in his place. Show him you’re in total control of him now.”

“Are you coming with me?”

“You should do this alone. You can always bring him in here to humiliate him further if you want.”

Unbeknownst to me, as I was lying in bed licking the dirty underwear, my Mom was standing outside the door, hand reaching out, and quickly she opened the door. At first, I thought it was Dwayne making sure I was doing as he said, but as the light switched on and she entered, I was mistaken. I was like a deer in headlights. I completely froze. Looking up at her with come around my mouth and her panties cupped in my hands, I was caught, and there was no going back. I dropped her underwear and just looked at her until she spoke.

“And just how long have you been stealing my things? I can’t believe my son is a sissy.”

“It isn’t what it looks like, Mom.”

“It’s exactly what it looks like, you’re eating my boyfriend’s cum straight out of those. Get out of bed and apologize at once.”

“Mom, I can’t. I’m not dressed.”

“I don’t care if you’re naked or not, get out of bed at once.”

I slid the covers off and stood up, wearing her Queen of Spades panties, and aroused, I put my hands in front of my crotch. The embarrassment was overwhelming. I felt my legs almost buckle underneath me. She hit both of my hands out of the way and pulled my panties down.

“Keep your hands at your side sissy. I know just how to treat people like you. You better start talking.”

“I’m so sorry, Mom. I’ve lost count of how long I have worn your panties. I won’t do it again, I promise.”

“It’s too late for that, Peter. I want you to finish eating all that cum and then I want you to thank Dwayne. If you’re lucky, I might let you eat some more cum.”

I stood there for a full minute with shame and embarrassment written on my face. A look of excitement showed between my legs. I began to lick them clean. She watched in complete fascination as I cleaned them all over. Once finished, she snatched them out of my hands and roughly forced them up my legs, the wetness made them plaster to my skin. She grabbed my crotch and squeezed.

“From now on, this belongs to me. If you want to fuck Becky or just jerk your tiny dick you will ask for my permission. Do you understand, sissy?”

“Yes, Mom, I understand.”

“I want you to go in and apologize to Dwayne. Then thank him for his cum. I’m going to enjoy having a little sissy.”

I slowly followed her to her room. Dwayne was lying in bed, smiling as the door opened and we walked in. Dwayne’s acting skills weren’t great, but he still looked surprised. I stood beside the bed and thanked him for all the food I’d eaten out of the panties. He just sat there smiling at my humiliation. Moving the sheets across he showed off his huge cock, it glistened.

“That is how big a real man is, Sweetie. Look how much bigger he is than you.”

“He’s so big, Mom. I wish I were that way, too.”

“You’ll never be man enough to fuck like Dwayne. But if my sissy wanted, maybe I’d let you taste my pussy. It’s so much tastier than mommy’s panties.”

I stood there, gobsmacked. I didn’t expect my Mom to be so open about all this. I still hadn’t fully taken in what she’d said in my room. Excited by the thought of her and Dwayne cucking me my clitty twitched, the already wet panties made it difficult to see my cum but you could clearly see movement. That was all the confirmation my Mom needed. She removed her clothes and had no embarrassment as she slowly opened her lips.

“Does my sissy want to taste mommy’s pussy? If you do, I want you to ask while I film you on Dwayne’s phone.”

I couldn’t believe I was actually going to taste her. I stared into the camera lens and ask my Mom to allow me to taste her pussy, she encouraged me to say more and in no time I was on my hands and knee’s begging her to taste her pussy. They both watched, knowing I would do anything they wanted. Dwayne started to grab his growing cock but Mom pushed his hand away. Grabbing him at the base of his shaft, she told me to lick him.

“If you want to taste mommy’s pussy then you can taste it off Dwayne. Then, if you’re a good little boy, next time I’ll let you taste it properly.”

Dwayne had the phone by now and was recording everything, Mom joined me on her knees and between the two of us we licked the entirety of his cock. Sticking her little finger into the opening of his urethra, she fed the last remaining remnants of his come to me. He stopped recording and messed with the phone, and I was allowed to stop licking. Mom led me back to my room, and as I got into bed, she leaned over and kissed my cheek.

“You’re going to be such a good sissy for mommy, tomorrow we’ll have more fun.”

As I lay in bed, I yearned to join them for more fun. My phone buzzed to alert me to a text message. I opened my phone to see that Becky had sent the video we had just recorded; obviously, Dwayne had sent it to her.

“I can’t believe how much of a sissy you truly are, begging to taste your Mom’s pussy. Dwayne has promised to let me get in on the fun, can’t wait to watch you and your Mom.”

“I can’t wait to have fun with you, too, babe.”

At the same time, Grace lay in bed with Dwayne, turned on, knowing her son’s girlfriend had watched the video. She, too, couldn’t wait to get Becky more involved. They decided they would buy more girly things for Peter. They watched a video of Mom and son chastity, she rubbed herself to a silent climax, stifling her breath.

The next morning, my Mom and Dwayne had already left the house by the time I got up. Walking into the kitchen, I saw a note telling me to pack up all my boy clothes and make sure I was only wearing something girly, the instructions allowed me to wear anything of my Mom’s. I’d also been instructed to remove all my body hair, too. She’d left razors and hair removal cream on the counter. I decided I’d start on smoothing myself up first, then find something to wear. After shaving myself and using the cream, I was completely hairless; all that remained was the hair on my head. I showered myself off and stayed under the stream of water until my body stopped tingling.

Dwayne and Grace were shopping for Peter’s new clothes, they found out numerous pairs of panties, from thongs to French knickers, all the colors that would make him feel more like a sissy. Finding him a few different starter bras and some silky night gowns, too. Grace picked out a few skirts, some were so short that she knew her son’s panties would show. Dresses as well as tight jean shorts, they filled a whole cart for him. Grace texted Becky while waiting in the queue to be served.

“Hi Becky, we’ve decided Peter will only wear girly clothes from now on. We’re out shopping for him. The reason I’m texting is that I wanted you to go to our house and get rid of all his clothes while we’re away. There’s a spare key under the flower pot by the bushes, and the alarm code is 7362. It would be a real help for us.”

With the message sent, Grace felt herself getting excited again. Peter wouldn’t realize just how terrible things were until he got back home. At first, he’d only think it was for fun, maybe a holiday game of dress up as mommy wants, but when he realized all his clothes were gone, he’d understand how his future would be.

I’d gotten out of the shower, feeling refreshed. I picked out a little red thong from my Mom’s case, I found a pair of Lycra shorts and a tank top, and put them on. I couldn’t believe how easily everything fit. The only clothes that didn’t fit her were shoes. I packed all my clothes up into my suitcase and shoes as well, a few days in my Mom’s clothes was going to be fun. No more having to sneak around. I put my case by the door, then I sat in the living room and waited for them to get back. Halfway through a YouTube video, I heard Dwayne’s car pull up. Hearing both doors close and the front door open.

“Peter, Sweetie. Come help me with our shopping.”

I saw bags and bags full of clothing. As I helped carry the bags to the house, I saw Dwayne putting my case into the trunk of his car. I had no choice at all now. I felt strange being outside in my Mom’s clothes. I could see cars driving past, but I knew that even if they looked my way, they wouldn’t be able to tell. Dwayne jumped into the driver’s seat and drove off. I wondered where he was going.

“Mom, where is Dwayne going? How come he took my clothes?”

“He’s gone to get rid of them, you’re only wearing girly stuff from now on.”

“Can I have my clothes back for the drive home?”

“No, Sweetie. You won’t ever get those back.”

My Mom looked down while we talked, and clear as day, my Lycra shorts had a little stiff bulge. Smiling away, she knew how much I liked my new predicament. I was happy knowing I’d soon have more fun with her. She showed off all the clothes she’d bought, and I throbbed the whole time. I tried on a few skirts and different panties. Mom loved how smooth my body looked. Grabbing my little bulge she kissed my cheek and let me know I was the best sissy son.

Dwayne came back with food. I wondered if he’d actually got rid of my things or if they still sat in the trunk. We ate our meal and then went into the hot tub, wearing one of my new red bikinis, top and bottom. My Mom decided to get in naked, and Dwayne followed suit. He sat on the edge of the tub, water up to his shins. His huge penis lay on his thigh, his balls hung down. We both couldn’t help but stare.

It felt like the whole time we were in the tub that I was aroused. They sat opposite me, and Mom kept putting one foot against my bulging bikini while I massaged the other one. Occasionally, I’d feel her toes rubbing my bulge up and down. I needed to jerk off so much. I tried to play it cool, but every time she asked if I was OK, I stuttered or blushed. I couldn’t help it.

That night I slept in my night gown and a new black thong, before that my Mom had gotten me to stand outside the door while they fucked. The way he pounded her, I could hear every thrust, even with the door closed. Once they had finished, I was called in and accepted a freshly covered thong, the come was soaked in, and I cleaned it straight away. I still wasn’t allowed to eat that treat straight from her box.

The days rolled on much the same, and on our last day, my Mom decided I needed a makeover. She painted my nails and toenails in a hot pink. With lipstick and foundation on, I wasn’t far from being a passable girl. She hinted at getting a wig in the future. I knew I was going to miss being here, but I’d be glad to get home, too.

“Sweetie. Do you want to see mommy get fucked tonight? You can stand by the bed, maybe I’ll let you finally eat me out.”

I couldn’t nod my head fast enough. I waited for them by the bed, wearing transparent white lace panties. When my Mom was kneeling in front of me, her face mere inches from my crotch. Dwayne got onto the bed behind her and mounted her. He started slow at first, but after a few thrusts, he quickened up his pace.

“Look at Mommy’s sissy clitty all hard. Does sissy want mommy?”

“Yes, Mommy.”

Holding tightly onto my crotch, she squeezed. Kneeling up, she moved forward and up slowly until her one arm was around my neck and the other was still tightly squeezing. Her body was pressed against mine. Kissing my neck and whispering into my ear. Dwayne kept his rhythm going, and every thrust shook my body. They both climaxed, and with a quick movement, he was out of her and had spun her around, the come was running out of her.

“Does sissy want his mommy’s cum? I’ll film you while you beg her.”

I begged them both repeatedly, pathetic but without a care about how I sounded. I repeated anything they told me to. Dwayne captured it all. As I begged, I could still see the remaining come slowly dribbling out. Her cupped hand had caught a lot of his seed, and she motioned that I should get closer, motioning forward until I was an inch away, she thrust her cum-covered hand into my face. Holding onto her arm, I licked it all off.

“I still don’t think you’re ready yet, Sweetie. Pass a pair of panties and I’ll clean the rest of this up. You’ll get it soon, sissy, but you need to really want it.”

“But I do want it, please, Mom, please. I need it.”

Dwayne caught every moment, and within a few minutes, Becky was enjoying every moment too, watching it on her phone. Becky rubbed herself before sliding a black dildo into her, imagining Dwayne pounding her. She rode it against her bed.

Travelling back home the following day, I felt awkward in my new girl clothes. They were nice to wear, but I got paranoid that every vehicle we passed saw exactly what I was wearing. It wasn’t until we stopped to get some food that I realized how vulnerable I seemed. Mom had picked out a pair of white Lycra shorts and a tight white tank top. To make things worse, I had a black thong and bra on underneath. They were clearly visible and I noticed at least a few people taking double double-take of my attire. I was a lot happier when I got back into the car to finish the last part of our journey.

Arriving home, I soon realized that things were going to be a lot different from now on; my whole wardrobe had been emptied. My male things had all gone; all that I now owned were the clothes Mom and Dwayne bought.

Grace took the last few items out of her suitcase. She placed a few different chastity cages and a strap-on on her bed, undecided which cage to have her son wear now. Peter’s life was going down a whole new path.

 

The End.

 

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