Closeted Family Secrets

So the day after I welcomed my daughter home in my bedroom and with my son Derek watching us, I decided to take a trip downtown. I waited until evening, when the person I was looking for might be out wandering 4th street, near the Walmart. It didn't take long to find a tall brunette wearing a short black skirt, high heels and black tights, and a v-neck blouse showing off a too-perfect set of size 'D' breasts.

I pulled the car to the curb, and when she leaned into my open passenger window, she gave me the once over, and stated, "Well, lady, I don't see many like you around here."

I handed her a twenty-dollar bill and asked, "Can we talk for a few minutes?"

She opened the door quickly and slipped inside, setting her hanging purse on the floor between her feet. "What's up darling?" she asked.

I said nothing and drove up to the parking lot and parked in the back, away from lights and cameras. I turned the cover page of my phone toward her and asked, "I'm looking for the cute girl who takes care of my husband sometimes. Does this guy look familiar?"

She looked panicked and spit out, "Oh, lady, I don't want to get into any of this, okay?" She seemed like she wanted to jump out, even before I stopped the car.

"No, no. Relax," I explained, "I'm here to arrange a date. My name is Vicki and that guy in the picture is my husband, Bill." She looked like she were not believing me, so I added, "I will bring him down here to do some shopping, and if he looks like he's worried, you don't have to get in the car with us. I just want to make sure I've got the right girl, and give him a night to remember." I handed her another twenty, and she took it unconsciously.

"So, what is the plan if Billy is up for it?" she asked me.

"Well, we will bring you back to our home for, um, a threesome, if that is good for you."

"Darling," she replied, "you're beautiful and all, but this date won't be cheap."

"I would hope not. I don't mind paying for an interesting play date. What are you asking, and what do I call you?"

She thought about my question for a moment, and offered, "I'm Danielle. And I will be losing a lot of cash if I spend time away from my corner."

"Then I think that $500 is a fair offer. What do you think.

Her crystal blue eyes lit up. "That's a good number. I need it up front, though." I responded by pulling out a fifty and suggested that ten percent now would suffice and that I'd give her the rest when Billy finalized the deal. Danielle took the money.

I took no time to tell her, "Well, Danielle, I think we have a deal. We will be back at 10 o'clock to pick up a few things from the store, and will see you then. Oh, by the way, I'm jealous of your D cups." She peered quickly at the flatness of my A cup breasts through my thin sweater, and then down at her own, and smiled broadly.

She said, "I had to turn a lot of tricks for these babies, but it was all worth it. My doctor did a great job on them." I asked her what favors my husband came to her for. She told me what I needed to know, so I could talk to Billy when I got home. I asked some other questions of her to prepare my plan for later tonight and felt I had enough information. Danielle lifted her bag from the floor, tucked the bills into it and popped open the door. "I'll meet you right here," she said, stepping away from the car. I smiled back, waved, and left for home.

When I got in, Derek and Ally were playing a board game in the kitchen, and Bill was in his favorite chair, watching TV. I said hi to the kids and whispered something into Bill's ear, which caused him to stand straight up and follow me up to our room. The kids stopped their game, and looked inquisitively at our interaction.

Once inside the bedroom, I had him sit down on the bed, but remained standing next to it. "Billy, the first thing I want to say is that I really appreciate how good you were with Derek and me the other night. You received your surprise well and you really know how to be my good cuckold."

Billy was quite fidgety, but thanked me for my comment. He sat on his hands, almost knowing that I probably had something else to tell him, and he was correct.

"Billy, I've come to find out that you don't always go to poker when you say you do. I don't know that it is every time, but someone I trust has told me that you don't always play cards when you say you do. Would you like to tell me about it?"

His face became pale. He stuttered, clearly not knowing what, or at least how much, he should tell me. His legs were shaking slightly, and I didn't want him to panic, so I added, "Now, before you say anything, I want you to know how much I really love you and all of the wonderful things you do to keep me happy. So, it's alright if we both have our own little kinks. Okay?"

His relief was palpable. He began, "Well, I've had my own thoughts, you know, since we started in this lifestyle. You know, since you've had me service your lovers. I kind of like playing with other men at times."

"Oh, well, that's fair. Any particular type of men?" I asked as if I didn't already know the answer.

Billy's discomfort returned. He was deliberate in his wording. "I like ladyboys. You know, who still have guy parts but also have boobs, and dress like women."

"Hmmm. I see," I replied, "And what exactly do you like doing with them?"

"Well, to be honest, I've only been with one person, a prostitute. He has taken drugs to grow breasts and one day plans to fully become a woman. But right now he has a functioning cock."

"Alright, that is fine. Is there any fucking going on, as in are you fucking him or is he...?"

He shook his head, stating, "No, its just oral sex. Like you have me do with your lovers. I suck him for a while, and he usually finishes me with his mouth. He says he doesn't cum easily with just oral."

"Oh, okay. Has he asked you if you want to fuck him?"

"Yeah, he has, but I'm just into the oral stuff."

I moved beside him, on the bed. "That's okay, Billy. You're welcome to find your own kinks. We have a good time in bed; just keep me in the loop. I want share in it with you and I don't want you to feel ashamed of what turns you on." I kissed him on the lips. It was a genuine, loving kiss, just for us. "I've got a surprise shopping trip for us tonight. Are you up for that?"

"Oh, sure. Where do you need to go?"

"Well, I want to stop and pick up something at the sex shop downtown, and while we're down there, maybe we can go to the Walmart on 4th street." As I said that, his eyes darted quickly to mine, looking for me to acknowledge that I might know something about that specific place. Having been playing these games with my husband for so long, my poker face relieved him of any concern.

"Oh, okay, that sounds good," he replied and kissed me lightly once more.

"Shall we go, then, honey?" I asked. Billy got up off the bed and I followed him down the stairs. As he reached for his keys by the front door, I called out to the kids. "Hey guys, Dad and I have some shopping to do. We will see you later." And off we went.

At the sex shop, we wandered about, him picking up the odd vibrator or cock ring, and I smelled some lotions and lubricants. Just as he asked, "What are you looking for?" the sales girl came up to us and asked if she could help us. She introduced herself as Emily and directed her questions to me.

I almost answered his question when she interrupted, so I turned her way and said, "Yes, please. I'm looking for something for a new kink; a strap on with maybe a thicker seven-inch cock for it. Do you have something like that?"

Emily nodded and said, "Sure, right over here," and motioned toward the next aisle. As she turned to lead us there, I noticed Billy's jaw had dropped.

He moved up to my ear and whispered, "For me, Vicki?"

"It's for me, silly. But if you want..." I continued behind her, letting that sink in for him.

Emily pulled a contraption from the shelf handed it to me, allowing her hand to linger over mine, as I looked it over. She advised it was a one-size-fits-all, but she looked directly at me and stated, "I can help show you how to put it on." I looked to Billy and saw his face turn crimson. "Um," I paused, "sure, I'd love that. But will it fit my cuckold, as well?"

She was unfazed, looking Billy up and down, and said, "Sure, he just has to adjust the different straps to fit over his gut. Just step in here," she offered, bending over to allow my foot to step into the leg loop.

I used her shoulder for support, and gazed down at her ample cleavage as she slid the straps up each thigh. She lingered, bent over, having to know she was showing me her goods. Emily fastened the upper clasps to fit it snugly over my hips, her fingers straightening the leather where it bunched up at the top of my thighs, front and back.

"How does that feel?" she asked, her fingers gliding along the roundness of my ass.

She had my attention now, and I said with a flirty smile, "I love how that feels, thank you." Emily licked her lips and looked me over.

The plastic base plate firmly pressed against my vulva held only a clip for attachments. Once I was strapped in, Emily pointed at a number of appliances that connect to the base plate, easily clicking in and out. She lifted the seven-inch silicone cock and clicked it in place, and I immediately felt strangely powerful. I looked down at the heavy phallus, and felt my juices begin to flow; her hand stroking the cock as though she were getting it off.

Billy stared at my wagging dick as I moved my hips side to side. I looked through the assortment and found a thinner four-inch cock, picked it up, and said to my husband, "Well, I don't need this one. I already have one of these at home, don't I?" She and I giggled a bit, and Billy did his best to smile.

Emily then suggested, "Well, the nice thing about that one is that you won't hurt anyone with it. It will get things opened up for something more fulfilling later." She reached to the base plate and unclicked the seven-inch cock from it and traded it with a four-inch cock. "I love that you can barely see a little dick like this, and you've got a great body. Imagine, with a beer gut, you wouldn't even be able to find your penis with something this small."

Emily looked at Billy as she slowly jacked my little penis with only her middle finger and thumb, making exaggerated, short strokes over it, while her other hand coveted my ass. I must say that I was becoming more turned on by this sweet blonde, as she openly belittled my husband for me.

She unclicked the small penis from my strap on and pulled down a similar dick to the first one I had on. She said, "This one is called 'Bad Boy" because it looks and feels like a real man's cock, plus it has this vibrating egg right here in the cock head."

She flicked a switch at the base, and the entire bulbous helmet began to vibrate loudly, almost as strongly as my magic wand. "This super stimulates the prostate as you pump back and forth across it. It guarantees an orgasm for him." Emily clicked it onto the base plate and, as it hummed, I felt my clit begin to tingle, and the sensations drifted down both of my legs.

She added, "You will likely get your own orgasm as well, because the vibrations increase as you try to push deeper and deeper. And, it will make you will feel really powerful." I enjoyed the sensation for a while and when Emily pulled the cock from me, her hand remained over the base plate, cupping my vulva through the plastic. "Oh, and if you're buying Bad Boy, you really need to get a butt plug to help get things opened up for it."

Emily reached for a spade--shaped plastic bulb that was really wide, that narrowed to a short shaft that was maybe one inch around. That short shaft was capped with a pink, heart-shaped jewel. "If he hasn't had anything of size inside him before, you start him with this and have him wear it around the house for the day while he vacuums and dusts. This girl never misses a chance to take a shot at Billy. "I bet you're really good at the domestic stuff aren't you?"

I agreed to the vibrating seven-incher with the strap on, and purchased the four-inch dicklet as well as the butt plug. I was pretty sure that Daniel wouldn't need the butt plug, but someone might want to try it out.

Emily got to the counter and reminded me about lube and batteries, which I hadn't thought of, so we bought some those as well. When she offered the payment terminal for me to tap my phone over, the bell chimed, indicating payment. Emily slipped the phone from my hand, smiling at me as she did so. She swiped until she found my contacts screen and then punched in her name and phone number.

When Emily handed back my phone, she said, "If you want some alone time, give me a call. I love cute Mommies." She handed the bag to Billy, and said, "Have fun, guys!" and walked us to the door. We got back to the car and put the parcel in the back seat.

While he drove to the Walmart, Billy said, "You really know how to push my buttons Vicki. And Emily really has the hots for you, I think."

I didn't bother responding, as both comments were inarguably true.

It was near 10:00 when we into the store. I took him back to the ladies' undergarments section and began looking at sexy undies. I asked Billy, which ones he liked, and his choice was no surprise, a sexy thong. He looked through the selection and asked, "You're a 34, aren't you?"

"Oh, Baby, I'm buying these for you. We need to find some 42s to fit you. Would you like that?"

Billy turned crimson and then looked around to see if anyone might have heard our conversation. "Hmmm. Yes."

"Would you like nylon, cotton, satin or lace?"

I looked down and he was pitching his tiny tent. He looked at both and answered, "Satin, please."

I couldn't help myself. I uttered, "I thought so," just loud enough to see him blush again.

I searched through the selection and found a robin's egg blue for him. "There you go, manly but cute. Am I right? Should we get some pink ones too? It's your choice."

Billy looked around, uncomfortably, "Can we just do the blue ones today, Vicki?"

"Sure, baby." I handed him the box and when we neared the cashier, I told him, "I'll see you in the car." When I got to the doors to go outside, I looked back to see the cashier trying to stifle a laugh as she cashed him out. Billy was red again, and peeked over at me enjoying his plight. I left and started the car. When he came out, he put the bag in the back seat with the toys and got into the passenger front side.

I drove the car around the lot and to the darkened corner, where I could see the silhouette of our ladyboy friend awaiting our arrival. So, as we neared her, I lowered the passenger window, and Billy looked to me with panic.

"Hey Billy," Danielle called out as I stopped in front of her. My husband almost died right there. Then she looked across to me and added, "Hi Vicki!" She leaned onto the window just as she does with her other customers. I swear that I could hear Billy's heart pounding. He looked to me for guidance.

"Oh, you were right, Billy. I can see what draws you here. She's really cute."

Danielle asked, "Are you looking for something extra tonight, Billy Boy?"

My poor husband was dumbstruck. I could see how he had no idea how I had set this all up. He stumbled his words as he turned to me, "Um, here? The three of us?"

"No, Baby, we can bring him home where it's comfortable."

His head flashed back and forth between us, and he said, "But the kids..."

"Oh, don't worry about them. We'll just sneak upstairs when we get in. It will be like old times!"

I looked to Danielle, and tilted my head, indicating to her to get in the back seat. When the door opened, Billy gave me a look that was a mixture of shear fear and excitement. I verified the latter by reaching into his crotch and felt his fully erect boy-cock.

Danielle closed the door and I reached into the back seat with an envelope in my hand. "$500, as we agreed." I said, and Danielle took a quick flick through the twenties, before zipping it into a pocket of her bag. I asked my husband, "Why don't you join Danielle and leave the driving to me? But I don't want you two spoiling things, so leave your clothes on. Would you like that Baby?"

Billy had the door opened before I had finished, and Danielle stepped out to let him into the middle seat. Danielle then sat into the rear corner of the back seat and parted her legs slightly, pointing them straight at me. The darkness of the car made seeing details beneath her hosiery impossible; I would have to wait until we got home to see her male prowess. This was going to be tough to view as I drove, so I directed my rearview mirror down and towards her just as Billy began to caress Danielle's yummy boobs over her v-neck blouse.

I kept turning back when I could, to see my husband's hand up her short skirt, no doubt fondling the young, hanging balls of our hooker friend. Danielle was rubbing over hubby's crotch as well, likely staining the poor boy's jockeys with pre-cum.

When we arrived, I told Billy to lead the way and to go straight upstairs, but as we entered, Ally happened to be at the sink in the kitchen, with a full view of the hallway entrance. Her eyes were bugged out and her jaw fully dropped as she recognized her father leading Danielle up the stairs. I was behind them and put my finger to my lips to shush her from saying anything.

As I neared the top of the stairs, I could hear Ally speaking in a hushed tone, which meant that Derek, too, was aware of our escapades. Stepping into our room, Billy was already seated in his chair at the corner of the bed, and Danielle stood beside the bed.

"Get out of my seat, Baby," I admonished. "I get to watch for a while." We traded places and then I began to direct things.

"Danielle, why don't you take my husband's clothes off for me" Without hesitation, Danielle flitted around my horny, rotund husband. She raised the t-shirt from him and ran her soft fingers through his chest hairs, leaning in and offering her lips to him. Billy seemed shy and nervous, and kissed back but just in pecks. Danielle's hand wandered to his pants, popping the snap and unzipping Billy.

When the pants hit the ground, I was shocked at how wet the front of his briefs were; you would have thought he had an accident. But as Danielle fell to her knees, Billy's chubby cock plopped out, and it was smeared in his pre-cum, dripping like a leaky faucet. I called him away from his suitor. "Here," i said, reaching into the bag from Walmart, "Put these on for Mommy." He stepped into them and I hiked them up like a mom would fit her five-year-old into his underwear, pulling them up snugly to his waist. The light blue satin immediately bled darker as the cum dribbled from his erect cock tip, the syrup oozing through the filmy fabric.

"Billy," I asked, half in jest, "are you going to make it? It looks like my little boy is a bit overexcited." My husband looked down at the already soiled panties and reassured me.

"I'm good. For now, anyway. I'll stop her if I need to." I reached up and caressed his cheek, and dismissed him to his lover. Danielle, still on her knees, pulled Billy to her and slid her manicured fingers around his ass, pulling him to her mouth. Her pink nails lightly scratched along the satin V-shaped material jutting down from the waistband, and slid further down to caress both of my husband's hairy cheeks. Billy's hands slipped into the locks of Danielle's brunette wig as she moved her mouth up and down the tented dick, licking at the salty wet spot on the front panel . At this point, the keyhole in our bedroom door allowed no light through it, telling me that Derek was watching us all play in front of him.

After some time of Danielle's teasing through the satiny garment, she tugged the waistband down, revealing his glorious four inches of manhood. Billy moaned softly as Danielle lightly sucked on his purplish cock head, making slurping sounds that I knew would drive Billy to a premature climax. I allowed only a few seconds of that before I called a halt to it. "Danielle, why don't you lay on our bed and let Billy show you how much he has missed you?"