Ilka's Place Pt. 02

Story Info
Brett indulges himself.
1.6k words
4.39
4.1k
3

Part 2 of the 9 part series

Updated 08/29/2023
Created 02/27/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
ValoryG
ValoryG
287 Followers

Well, Ilka finally did get around to my future. I figured she'd find a homeless shelter or some government program to get me off the streets.

But the night after her haircut, when she returned and changed into a tight skirt and thick sweater that was tight against her boobs, and after we ate one of her Hungarian meals, she had me clear the table and do the dishes. Then she bid me to sit down again. As usual, I expected the worst.

"Brett," you have been a good boy, I mean, good man here," she pronounced while sipping a beer. "I feel I trust you, you know."

I looked at the large rings on her hand.

"I have a thought, and maybe you like. I admit, I will admit, that I still miss my children. I only see new picture of them growing up once in great while. I think -- maybe this is, you think this is crazy -- but you could stay here like my son. You know, we could pretend. It would fill gap in my life."

"Oh, I see. I don't know; this is so out of the way; I mean, so unusual. Not weird though, because I understand where you're coming from."

"And," she continued, as she leaned forward across the table, thrusting her big tits toward me, "you could help me here. I have handyman for apartments, but old and should retire. I pay him well. I will pay him big bonus and say my sad goodbye! I would like you to take his place. Do not worry, Brett, it's only light work. If there's electric or plumbing, we call the experienced guys."

"Wow, that's very generous, Ilka. I could do that. So different from being a cook. But of course I could help out with the cooking here. Maybe introduce you to some new dishes you're not familiar with."

"Well, I'm not so sure about that, Brett. I am pretty set in my ways. But maybe.... While you do these things, you might have time to train for nurse, take some classes."

I felt buoyed up. I could certainly be Ilka's handyman for a roof over my head and some security. But there was one more arrangement to negotiate.

As Ilka and I prepared for bed that night, she appeared in a robe over her nightgown, and was practically in tears.

"I have just another request, Brett. I am little embarrassed by asking. Probably it is too much."

She looked at me, and I wasn't sure if the near-tears were genuine or not.

"I have a big bed," she said, "and sometimes bedroom seems so lonely at night. I ask you share bed with me? No sex, I don't need it. Just someone in bed with me. You don't have to. But be nice. My bed so much better than your little bed in spare room."

What the heck? This WAS getting weird. But her bed was very large and there was plenty of room for someone else without getting up close and smothered. I remembered her massaging me all over with her massager and feeling controlled. Some of that control continued to ooze over me as I reluctantly agreed to sleep near her.

This made Ilka very, very happy.

That night, after removing her earrings and turning off all the lights except for a weak nightlight, she eased into bed in only her flannel nightgown, which gave strong hints of her loose tits and big hips, while I ventured under the sheets in my boxer shorts and T-shirt. The bed creaked under her weight. She fell asleep before I did, but we both ended up sleeping solidly.

The next morning I got up first, and exited into my usual bedroom to dress.

After breakfast, she was off again to cut hair. Later in the morning, she called to say she'd made arrangements to release her handyman, and told him to meet me that afternoon to go over what my duties were. Once he filled me in, she would give him his final payment.

That left me alone in the morning. For some odd reason, sleeping in the same bed with a woman (any woman) had made me a little horny. It was a perverse horniness, to be sure, but when I had gotten out of bed earlier I'd developed a stiff one I had to conceal.

A half hour after she left, that horniness led me back into her room and to her corset drawer. There, I ran my fingers inside the lacy cups of her open-bottom black corselette. I carefully removed it from the bottom of the drawer and placed it against my now-nude body. Naturally, it was too large, but just the feel of the elastic and its sultry design were enough. My erection returned with urgency. I had to be so careful not to get any pre-cum on it!

If only it had fit me. I finally arrived at a solution of sorts. I stepped into the sexy garment and pulled it up, then folded it in back so the front was somewhat tight, then sat back in a tall chair, so the chair held the fold in place. I had already filled the cups with toilet paper, and I was in existential heaven. Now I had her boobs on me! I loved the feel of the straps over my shoulders and only wished that I could've attached the corselette's garters to some nylons.

I was still wearing my boxer shorts underneath to catch any moisture and they were doing the job. My cock, however, was begging for more attention. I ended up quickly massaging myself through the shorts and soon spurt, spurt, spurted into them. I was in heaven. God, there was a lot of cum. A couple drops even got on the corselette. I was mortified.

I carefully wiped the drops off with some extra TP, nicely folded the long garment, and carefully placed it back in its bottom-of-the-drawer spot. All this time, I was feeling quite guilty because... I had kinda stolen something, something very private and hidden.

I suddenly wished she'd pay me a salary so I could buy my own lingerie, and she would somehow be OK with me as, well, a crossdresser. Such a fantasy!

"Be very careful, Brett," I told myself, "don't ruin a good thing. She's most likely very sexually conservative and traditionally gender-specific, where women are women and men are men, with no inbetween..... "

But I WOULD need to buy some new clothing and would have to ask her for some sort of allowance to do that.

I learned what I could from the departing handyman (he was pleased with his bonus) and began my role in that department. I got to know all the people in the apartments. What I haven't said is that Ilka owned another nearby building with seven more apartments I was also responsible for.

Eventually I met all the occupants. There were immigrant families with lots of kids crammed into small spaces. There were couples without kids. There was one very gay couple, and a single guy who kept large aquariums with tropical fish. There was a single woman who had recently checked out from being a nun, a military family, and a single guy who I guessed could be a crossdresser. Then there was the nut who kept guns. Some were easy to please and some were too demanding.

It was the possible crossdresser, of course, who interested me. I entered his place one time to unclog his sink and noticed a pair of woman's shoes and a couple nylons drying over the shower bar. His name was Chris and he was shy and borderline nervous. But I talked him up and gained his confidence. He said he was the financial guy for a large food bank in town.

I looked at him closely to look for any evidence of makeup or wearing femme underwear, but no luck there. Maybe he had a female friend who visited from time to time. He was around 10 years older than me.

My relationship with Ilka progressed. She did give me an allowance (just like a son), which allowed me to buy the amount of clothing I needed (but no lingerie). However, instead of buying more old-style boxer shorts and loose T-shirts, I splurged and bought more expensive, tight-fitting briefs and skin-tight T-shirts. Ikla of course noticed, but didn't say anything. When I came to bed, I continued to wear loose shorts or a night shirt I'd purchased.

I became used to bedding with her. She snored a little, but I was usually too tired to let it break up my sleep. I could sometimes feel her body heat spreading across the bed. Sometimes I had fantasies of her reaching across and holding my cock or making me eat her out, but they remained passing eroticisms.

When I left the bed in the morning, she closed the bedroom door so she could dress. I could see hints of the corsets she usually wore under her dresses, or skirts and shirts. That was bit of a thrill too.

I continued to try on her corsets from time to time and of course nearly always ended up masturbating in them. I was so extra careful to hide my transgressions.

Our relationship seemed very hunky-dory for several months. I played along with her desire to have a son. Like sometimes she'd say, "Brett, dear, please get milk from the fridge," or "Are you happy, Brett? I want you always happy and to stay here."

But then. There was the Sunday when we were home all day except for her going to church. When she returned and I was watching some football on TV, she spoke just a little sharply: "Brett, have you been looking through my drawers? I think, I see some things have been moved."

(to be continued)

ValoryG
ValoryG
287 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
Gilmartin33Gilmartin33about 1 year ago

Enjoying the build up across these stories and looking forward to seeing what happens next, thanks

jennifurzoejennifurzoeabout 1 year ago

Just love where this story is going,Ilka noticing then questioning in what seems like a stern voice,can not wait for more so Please Please Please hurry up..💜

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Wanted: Maid (Male) Pt. 04 Young man falls deeper into a naughty couple's control.in Transgender & Crossdressers
Becoming Doll 001 Pt. 01 Young trans woman turns herself into a Rubberdoll.in Transgender & Crossdressers
Wanted: Maid (Male) Pt. 03 Mistress gets him into a maid uniform.in Transgender & Crossdressers
The Agency Mike finds a job, which may be much more than he expected.in Transgender & Crossdressers
Sissy Secrets Sissy learning what a sissy is.in Transgender & Crossdressers
More Stories