With Chloe, my wife of fewer than two years, still away on one of her frequent business trips, I’d spent the morning bathing and shaving away any trace of body hair from myself. From there, I grabbed my laptop and watched dirty movies in the living room while sitting on the couch. I started out watching clips of girls flashing their bodies to strangers in public. But I was soon moved onto nastier topics. I even spent nearly an hour shopping for a chastity cage. I almost bought one too but was never able to bring myself to complete the sale. Chloe would have seen the charge on her credit card. She tolerated some of my kinkiness, but a chastity cage was something she couldn’t accept. Someday I’d buy one and keep myself chaste whenever she had to leave on a trip.

Going back to the movies, I wound up watching fem-boys in chastity cages milking themselves on dildos. I never once touched my skinny, little, smooth penis. It was aching for attention, but I kept myself from touching it. In the end, I made my way back to the chastity cage shopping. I even added it to my cart, but still didn’t finish the sale.

By then I was beyond any normal level of arousal. I left my computer on the couch and moved to my bedroom. From the box tucked away in the back corner of my closet, I pulled out a bottle of lubricant, my hot pink butt plug, and my long, flesh-colored dildo. These were the toys Chloe did not approve of. The only time I was able to play with them was while she was away. Thankfully, she’d been traveling so often for her work.

Butterflies arose in my stomach while I held the dildo and buttplug in my hands. I cherished my time alone with my toys. It started while still living at home with my mother. During that time, I used vegetables and anything else I could find with a phallus shape to penetrate my body.

After crawling onto my bed on my knees, I applied an ample amount of lubricant to the buttplug before lowering my shoulders to the bed and keeping my butt up high. I lubed myself thoroughly, between my cheeks and over my quivering little button. Very slowly, I began to work the buttplug inside of me. It had been more than two weeks since I’d had my special alone time and I’d been looking forward to it. I controlled my excitement and took my time with the initial penetration. Soft moans and whimpers left my mouth as I stretched around the wider parts of the unyielding plug.

When my tight ring of muscle stretched around the widest part of the plug, I kept my body from sucking it inside. I held the plug right where it was so my wrinkled hole was stretched over the widest, thickest part. It felt so good. My hips were wiggling around and my penis was leaking its excitement onto my bedcovers. I squirmed around on the bed dreaming of being just like the fem-boys in those videos. I whimpered softly when I thought about a video being made of me and people, strangers watching it and getting turned on.

After I’d nearly driven myself crazy with desire, I let the buttplug slip all the way into my body with its wide base nestled between my cheeks. Needing this afternoon to be as exciting as possible, I slid off my bed and tiptoed through my house toward the kitchen. With every step I took, I felt the plug moving inside of me. It was a delicious sensation!

I didn’t rush by any of the big windows, I took my time strolling by them naked and hyper-aroused. If our neighbors got a peek, it would only turn me on more. Unfortunately, or maybe, fortunately, I didn’t see anyone outside. In the kitchen, I got a small glass of water and stood by the sliding glass doors while I sipped on it. I was really hoping our neighbor, Mrs. Ross would be in her yard and see me. But no such luck. Ever since the day she’d stopped by to visit with Chloe and saw me standing, bottomless, in the corner with a red bottom, she had become very flirty. I’ll never forget how it felt to be standing in that corner while Chloe told her how I’d used her credit card to buy myself a buttplug.

Setting my glass down, I returned to the glass doors and slowly slid them open. Taking a deep breath and summoning all my courage, I stepped outside into the warm sunshine. I was completely naked with a buttplug buried in my bottom. I was extremely horny and my little penis was as stiff as a pencil. I stepped away from the door and made my way to the middle of our yard. Holding my arms up high, I spun around in circles and giggled before racing back inside. The fear of being outside and being seen was scary and a huge turn-on. But at that moment, it was scarier.

Once I’d made it back to my bedroom, I wiggled the plug out from inside of me. After cleaning it, I put it away in the box. It was time for the main event. I took my time lubing up the flesh-colored, realistically shaped dildo. My small hands sliding over the veiny rubber made me shiver with excitement.

After getting back on my knees with my shoulders against the bed, I lined the dildo up with my wrinkled button. I considered going back and buying the chastity cage I’d been dreaming about for so long. But when that slippery dildo bumped against my still gaping hole, I knew what I’d be doing for the rest of the day. Pushing gently, I opened up and the dildo slid inside of me. Still avoiding my desperate penis, wanting to cum like the fem-boys in the videos, if I let myself cum at all.

For the next several hours, I rolled around on my bed sliding that big, fat dildo in and out of my bottom. The orgasm within me grew every time that dildo slid over that special place deep inside of me. When I felt myself getting too excited, I slowed down or completely stopped until I settled down. That afternoon, I edged myself dozens upon dozens upon dozens of times. My little, bald penis was leaking like a faucet. My mind was fuzzy, I could hear myself panting and moaning. Naked, hairless, laying on my back with my knees bent, my penis aching for release and a dildo buried in my bottom, that was exactly how I looked when my mother-in-law barged into the room unannounced.

Her name was Betsy, but even before Chloe and I were married, she insisted I call her ‘Mumsie’. Mumsie was the sweetest lady. Whenever Chloe was out of town for business, which was quite often, Mumsie would stop in to check on me every other day. But she had been there the day before. She wasn’t supposed to stop by again as soon. And she usually knocked on the front door. She didn’t usually use her key.

Mumsie was wearing a white and red, floral print summer dress with large red buttons down the front. On her feet, she wore low, white heels. Mumsie was not a thin woman. She would best be described as full-figured. She had enormous breasts, each of them larger than my head. Her wide hips swayed with every step she took. And her big behind nearly filled the doorway she stood in. Her light brown hair was pulled back into a bun. She held her large-brimmed, white summer hat in one hand and was covering her mouth with the other in surprise. Her eyes were opened wide and I heard her audibly gasp.

Her voice matched her expression, surprised, “Sammy! Oh my! What are you doing?”

I squealed, let go of the dildo, squeezed my legs together, and covered my face with both hands. The combination of all I had done that day, seeing Mumsie in my doorway, and hearing her voice was too much for me to handle. With the dildo still buried inside of me, my skinny penis flexed hard and stood straight up. Right there with Mumsie watching, my little, bald penis erupted. My toes curled up tightly and my body began to tremble. I felt muscles all over my body quivering and flexing. My back arched deeply and then it happened, big spurts of my creamy love oozed from the squishy pink head of my penis. I lay there, not touching my penis at all. I kept my face covered to hide my shame but knew Mumsie had stepped closer to get a better angle. When I felt the bed shift, I knew she’d sat down beside me. I came with Mumsie sitting right there watching it all. It was the most powerful and intense sissygasm I’d ever had.

While I lay there, still hiding behind my hands, Mumsie laid her large, warm hand on my bare knee. “Sammy, Honey, you don’t need to be embarrassed.”

I whimpered from behind my hands, “Yes I do!”

She rubbed her hand up and down my thigh, “No, you don’t. Sammy, that may have been the cutest thing I’ve ever seen.”

I kept my hands over my face and looked away from where she sat, “No, you’re lying.”

“I’m not. I promise. I didn’t know a boy could cum without touching himself. And you shaved. My goodness, you look adorable!”

I slowly lowered my hands away from my face until I saw Mumsie’s smiling at me. “Do you really think so? When I’ve shaved before, Chloe says I look like a little boy.”

Mumsie smiled warmly, “You do look like a little boy. Especially with that little-bitty penis of yours. Chloe once mentioned it was small, but I thought she was fibbing.”

I scooted over and got a handtowel from the top drawer of my bedside table. I wiped up my mess and folded the towel over the gooeyness before setting it on the edge of the bed. Biting my lip, I looked into Mumsie’s eyes and whimpered, “Mumsie, Chloe hates it when I do this. She is going to punish me when she finds out I shaved again. She says it makes her think that I’m gay.”

She replied, “I won’t tell her, I promise. But are you? Are you gay?”

I spoke with a timid voice, “I don’t think so. But… I mean… I think about it. I think about lots of things. But I do think about being with a man.”

Mumsie’s hand slipped between my legs and she gently tapped on the base of the dildo still buried deep inside of me. “My sweet, little Sammy with a big, tall, grown man. Now I’ll be thinking about that too.” Every time she tapped that dildo, the sensation shot through my body and I twitched.

After not saying anything for a few moments, she looped her fingers around the dildo and pulled it out just a little bit before pushing it back inside. I whimpered softly and gripped the bedcovers with my fists.

Mumsie was staring at my little penis as it stiffened before her eyes. “Sweetie, tell me one more thing you think about.”

My hips began to grind when she slid the dildo back out and in. “I-I-I think about people, strangers seeing me outside, like this.”

Mumsie grinned, “Like how?”

I arched my back and squirmed while clutching the bedcovers with white knuckles, “Like naked… and horny… or maybe… maybe…”

She began sliding the dildo in and out of me at a steady pace. My skinny penis had never softened and remained completely stiff while the shame of having Mumsie see me began passing. I slowly let my knees spread further apart, allowing her an unobstructed view of my small, bald penis. I whimpered and moaned while she made love to me with the dildo.

Her voice was soft and understanding when she asked, “How do you want people to see you? Tell me, Honey, I promise it’ll stay between the two of us.”

I couldn’t look at her. I covered my face with my hands and looked away. “I have always thought about… I used to before Chloe… But I haven’t since… I mean…”

Mumsie slid the dildo almost all the way out before pushing it back in very slowly. My toes curled up again and my back arched deeply. It felt so good!

“What did you used to do before Chloe? Tell me, Honey. It’s okay. You’re safe.”

My voice cracked and I whimpered softly while spreading my legs as far apart as I could. “I-I-I used to wear… I’d dress up in my sister’s clothes.”

My bald, skinny penis was standing straight up again. Mumsie had found the magic spot inside of me. She was bumping the dildo against it and it was making me tingle all over.

Her eyes were moving from my stiff penis to face and back again. In that same kind tone, she asked, “When was the last time you played dress-up?”

I squeaked, “Before we were married.” I tried to calm down when I went on to explain, “When Chloe found my little suitcase of girl’s things, she got really upset and threw them all away.”

Mumsie looked sad, “You poor boy. You couldn’t even wear Chloe’s things, they would be far too big for you.”

Biting my lower lip, I nodded my head and whimpered, “I know!”

She spoke in a soft voice, “Sammy, I bet you’d look adorable in a little dress. I would love to take you out shopping. You could keep those things at my house. And whenever you wanted to play, you could come to visit me.”

I squirmed on the bed while she continued to slide the dildo in and out of my bottom at a slow, steady pace. I squeaked, “I’d love that, Mumsie!”

She grinned and uttered a single word, “Good.” She then pulled the dildo all the way out from inside of me. Mumsie then stood up from the bed, turned back to face me, and offered me her hand. “Let’s go shopping!”

I squirmed and writhed on the bed, “But Mumsie, I can’t go like this. I’m really…”

She smiled down at me, “You’re what? Horny? I know you are, baby boy. I want you to be just like this when you step out of a changing room and model a dress for me.”

Listening to Mumsie tell me I’d be modeling a dress for her in a store was like a fantasy come true. Not wanting to disobey her, I wiggled off the bed and rose to my feet. My little penis was pointing at the ceiling and my bottom was tingling from the attention it had received. Biting my lower lip, I looked up at Mumsie. Like Chloe, she stood a full head taller than my 5’2″ height. I was never sure how much Mumsie weighed, but she had to be 2 if not 3 times my 95-pound weight. While I stood there naked and extremely aroused before her, my eyes kept dipping to the ample cleavage left exposed by her summer dress.

Mumsie turned away from me and moved to my dresser. She began searching through my drawers looking for something for me to wear. She soon handed me a pair of gray cotton shorts and a white T-shirt. I didn’t have to ask about underwear, I knew she’d left that out on purpose.

She grinned, “Panties are going to be the first things we buy.”

Hearing my mother-in-law tell me she was going to buy me panties made me shiver and goosebumps rise all over my body. For a brief moment, I thought I was going to squirt right there. But the feeling calmed down and the danger of making another mess passed.

After I’d gotten dressed and stepped into my flip-flops, Mumsie frowned, “Hmm, something isn’t right.” She then took hold of the waist of my shorts and pulled them up, giving me a wedgie! She then rolled down the waist of the shorts far lower than my usual shorts sat which left a strip of my pale tummy exposed. Reaching back, I found the shorts were clinging to my cheeks and the center seam had disappeared between them. Moving my hands lower, I felt the bottom third of my cheeks were left out in the open and the impression of my little erection was right up front for everyone to see!

Mumsie took my hand and we left my bedroom and walked through the house locking it up. While passing through the living room, she noticed my laptop still sitting open. When she moved to close the lid, the screensaver ended and the chastity cages I’d been looking at caught her attention. She paused to see what I’d been looking at. After sitting down on the couch, she scrolled down the page to see the different styles and materials they were made from.

She eventually whispered, “Chastity cages?”

It sounds silly after all she’d seen me do, but I was terribly embarrassed when I squeaked, “Yes, Mumsie.”

She closed the laptop, set it on the table, and stood from the couch. While offering me her hand, she said, “Change of plans. We’ll get panties after we buy you a chastity cage.”

I shivered again and felt my skinny penis flex hard. When I looked down, I saw it had been leaking in my shorts and the wet spot looked lewd. The pink head of my rigid penis was resting right in the middle of that moist spot.

Mumsie didn’t give me time to dwell on that moist spot. She took my hand and after locking up my house, she led me directly to her car parked in our driveway. Mumsie kept looking at me and smiling while driving out of our neighborhood, but she seemed to be thinking and I didn’t want to interrupt her thoughts. I sat silently in the passenger’s seat while being driven to an unknown destination.

After we’d left my neighborhood, Mumsie finally spoke. “Chloe doesn’t tell me very much about your relationship. But she did once tell me that you liked some kinky things.” I squirmed in my seat and blushed. She went on to say, “What I can’t understand, is why she dislikes them and forbids you from playing. Sweetie, I find every kinky thing about you very exciting and I’d never discourage you from doing them.”

I giggled and teased, “I know! You’re taking me shopping for a dress!”

She smiled while turning into an adult bookstore. “I’m going to be buying you more than just a dress.”

After parking near the front door, she climbed out of the car and came around to my side. After opening my door, she offered me her hand. I didn’t take it right away. In a timid and frightened voice, I explained, “Mumsie, I don’t know about this. Maybe I don’t want a chastity cage. I’ve never been in a store like that and I don’t think I want to.”

She frowned while leaning down and taking my hand, “Nonsense. I think you do want your little penis locked up. And I know I’d love to do that for you. Come along. This is only our first stop of the day.”

After I’d slid out of the car, Mumsie led me to the front door. All the windows and doors were blacked out and it made the building look scary. Mumsie opened the door and had me enter first. I’d barely taken a step before a man’s voice called out rather firmly, “ID. I need to see your ID.”

Spinning back to Mumsie, I squeaked, “I don’t have my ID. I don’t have my phone or anything.”

Mumsie stepped toward the man behind the counter, “I’m sorry but my son-in-law doesn’t have his ID. But I can promise you the boy is of age. Just barely, but he is of age.”

The man didn’t look happy, but he said, “Son-in-law, huh? Okay, but be quick.”

Mumsie thanked the man and asked, “Could you point us in the direction of your chastity cages?”

The man leaned over the counter and took a long look at me. His gaze lingered on my still stiff penis and its small moist spot. He seemed to cheer up and pointed to racks along one wall, “Right by the handcuffs and gags.”

Mumsie thanked him, took my hand, and led me further into the store. After I’d stepped away from the counter, I happened to look back and caught the man staring at my butt and licking his lips. I turned back quickly and raced along to keep up with Mumsie’s long strides.

The aisle we walked down was filled with all sorts of kinky toys. There were edible panties, racy lingerie, blindfolds, dildos, and more. As we neared the area the man had sent us to, Mumsie paused and took a box from the rack. Glancing at the box she was holding, I saw it was a remote-controlled, vibrating buttplug.

Mumsie looked down at me, “We’re getting this too.”

I whimpered softly, “For me, right?”

She grinned, “Definitely for you. But I’ll hold the remote.” She then handed me the package to hold onto while she continued to shop.

I was shivering and squeezing my cheeks together as we finished making our way to the chastity belt selection. They had metal cages, plastic cages, big ones, small ones, there were just as many as I’d been fantasizing over online. When Mumsie asked which one I liked. I pointed to a clear plastic cage with an almost 3-inch length.

Mumsie frowned, “Baby boy, you could almost get erect in there.” She picked a package from the rack. It showed an opaque pink silicone cage with less than an inch-and-a-half in length. It was called, “The Sad Sissy Trainer”. She stood there in the aisle reading the package while I remained beside her throbbing in my shorts and holding the vibrating buttplug.