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.
