A few weeks went by, mostly uneventful, with the exception that I was "helping" Barry almost every day with bathing, during which we would have our own version of the "special time" he described having with his wife. I began learning what he liked, what he didn't, along with swallowing his cum rather than letting it go to waste all over the place. It was thick and sweet, which surprised me. I enjoyed it, and looked forward to it.
One evening as I was washing dishes, Barry approached me.
"Ashe, I'm sorry I haven't purchased you any more clothes recently. You've been wearing a lot of Sharon's clothes. It definitely makes me happy to see you enjoying her things, would you like me to buy you some more clothes?" He asked gently.
Over the weeks, I had dug through more of Sharon's closet during moments of boredom, picking out more pieces. I didn't really go outside the home, so I stopped caring about how "feminine" the piece was. I began wearing her sun dresses as they felt good to wear, airy and light. I stared at myself in the mirror with it on, feeling rather cute. These feelings confused me, but I was settling into my role as Barry's "House Boy" I guess you would call it.
I was wearing one of those sundresses now, with no underwear underneath. I turned to face Barry, realizing the sun shone through my dress. Barry's eyes glanced down at my small flaccid cock dangling between my legs, then back up at me. I chuckled.
"Sorry Barry, I should of worn underwear. I'd love some new clothes, thank you"
Barry chuckled back. "It's okay Ashe, underwear is optional. We can find something to take care of that." "That" being my penis. It *was* very tiny. If I ever stroked it, I used just two fingers. It was rather thin and only about 2.5 inches long, fully hard. Lately I had been opting instead to rub and finger my soft and smooth asshole, it felt better, it felt "right". After Barry and I's "special time", I'd get into bed and spend thirty to forty-five minutes rubbing and fingering until I felt an orgasm rising up, resulting in a small dribble from the head of my little soft cock. Barry seemingly heard my moans down the hall and mentioned it one day, resulting in him gifting me a pink vibrator to use instead. It was Sharon's favorite. I hadn't touched my cock since.
After our encounter in the kitchen, Barry left the house and returned a few hours later, holding multiple bags. I helped him carry them to the kitchen table.
"Oh wow Barry, I wasn't expecting this....thank you..." I said sincerely.
"I hope you like this stuff, Ashe. Take a look" as he motioned towards the bags.
I begun pulling out the articles of clothing, surprised by both the color and the pieces themselves. Pink and black thigh highs made of lace, more sundresses, pink and red and white thongs, small fishnet tops, a few blouses and skirts.
"Um, Barry, these are all women's clothing..." I said, slightly confused.
"I uh...well Ashe I kind of thought you were enjoying wearing Sharon's clothes, you seemed rather happy and comfortable in them. Even now, wearing her sundress." He motioned his head up and down at my thin, yellow dress complete with little flowers around it.
"Well uhm, Yes I mean, yes I have been enjoying it actually. I just uh...I'm...happily surprised" I said, not wanting to embarrass Barry. He had done me a huge favor. It would have been nice to at least have SOME boy clothes. But I can't complain, Barry hasn't talked of me getting a job, or any form of rent at all since I moved in.
"There's more" Barry said, his eyes lighting up.
I started digging through the next bag. It had two items. A black and white maids uniform, and a small black box.
"Oh wow Barry, this is....interesting..." I said, eyeing the maid uniform as I held it up. What could be in the black box? Jewelry?
"I think you'd look really good in it, Ashe. I know you do all of the chores around here, I figure it'd fit right in with your other clothes!" He said.
"Yes definitely!" Trying to stay positive. Although I *was* basically Barry's "Houseboy", this felt like an extra step further. A maids uniform? Once again, who am I to complain?
I picked up the black box. "What's this?" I asked.
"That's for your uh...ya know..." He glanced down at my little dangling cock, silhouetted through the sundress.
Confused, I opened the box and pulled out a very small, pink chastity cage, complete with a black strap to hold it tightly to my body.
"Oh my...." I almost gasped. "Barry..." I began.
"Well I uh" Barry interjected. "I know you've been using Sharon's vibrator a lot, to um...take care of yourself. I read online that this can help, it can make you feel better. It'll protect your....thing..." Barry's face reddened as he chuckled lightly.
"I uhm.......thank you" I say after a long pause.
"You can try it on now, if you want" Barry responds.
"Y-yes....Sure...." I say embarrassed. Carrying the pieces into the bathroom, I slip my balls through the ring, then my penis into the cage, it fit nicely, almost like it was custom made for my small cock. I clamped it on tightly, made sure the strap fit properly, then turned the key with a *click*. I exited the bathroom to Barry standing in the kitchen, waiting.
"Well, let's see it!" Barry exclaimed.
My face reddens. I slowly lift my sundress, exposing my tiny cage.
"It looks great!" he booms, chuckling. "It looks like it was made for you!"
"Y-yes...I guess so...heh" I say, looking down at my little pink cage.
Barry hands me the maid uniform. "What about this as well?"
"Oh....yes....thank you..." I take the maid uniform, opting to simply just change right then and there. I pull off the sundress, exposing my fully naked body to Barry. Pulling over the maids uniform, it fits snugly. The skirt is *very* short, not even enough to cover my cage, exposing it to the air, and to Barry. I can feel my ass hanging out of the back as well.
"Wow Ashe! That looks perfect!" He says excitedly. "I'll take the rest of your clothes to your room"
Barry walks upstairs with the bags and I'm left to think about the situation. A maids uniform? Thongs? Thigh highs? A chastity cage!? What was Barry's goal, to make me into a woman? Was this some sick way of making me into something resembling his dead wife? That must be it.
The thought of this simultaneously terrified me and excited me at the same time. I didn't want a job, I didn't want to go to school, I liked cooking and cleaning for Barry and him providing for me. I liked, well, servicing him. It made me feel good to see him feel good. At these thoughts, my little cock tried to stiffen, but the chastity cage stopped it. A surge of horny excitement shot through my body.
"Oh my..." I thought to myself, "Is this what the cage does?". Another surge shot through me, the cage stopping another erection. I suddenly wanted the vibrator, inside me, working it's magic. The image of Barry's fat, veiny cock invaded my mind. More images of it erupting cum, rope after rope, onto my face, in my mouth, deep inside me. "Deep inside me? Oh god..." I thought.
Barry's large footsteps interrupted my train of thought.
"You really do look great, Ashe." Barry says, eyeing me up and down. "Everything okay?" He fixes his eyes on my dangling chastity cage poking out under the maid skirt. My face reddens as I look down, a long drop of precum is dangling from the cage, down to the floor.
"Oh god I'm so sorry" I say, embarrassed. "I'll clean it up". I look down at the small puddle of precum on the floor. I walk to the sink and grab a wipe, getting down on the floor on my hands and knees, wiping up my small puddle. I can feel my fat, jiggling ass in the open air. Air on my asshole as well, it's easily in view of Barry. "Oh god, Barry can see my asshole.." I think as I wipe, the motion making my ass jiggle back and forth. My cage tightens again.
I finish my wiping and get back up, spinning around towards Barry. My eyes immediately dart towards the massive bulge in his pants. He was wearing sweatpants, and it was impossible to hide that he had an erection, I could even see his balls pushing through.
"I'm sorry Ashe, it's very pretty..." He says quietly, his face red.
"My uh...my..." I stammer out.
