Ilka's Place Pt. 04

I felt small next to Ilka as she briskly made her way into the lingerie department. In her large leather purse with brass fittings was her list of my sizes and measurements.

I tried not to look closely at the racks of beguiling bras, girdles and panties as we passed by. Hey, I was just her son, unwillingly dragged along on a shopping trip!

But that pretense soon evaporated as she began to look at lingerie obviously not her size. She asked me which of several very feminine bras I preferred, which sort of slinky panties "suited" me, and which lace-embroidered nightgowns I desired. With each new choice, I felt my cock strain even further against my tight briefs.

Fortunately, no salesperson was around to help with the choices. After all, this was Kohl's, not Macy's.

Ilka arbitrarily chose a few things such as nylons. She didn't use much of my input in buying the outer clothing either, and they were rather plain, but still shapely enough.

Finally we arrived at the crème de la crème of our outing, the foundation display.

After buying a delightful panty girdle (with garters, she insisted) we came upon full-length corselettes. I couldn't resist touching the latter, just briefly.

"Aha, Brett, this is your fascinating, isn't it? You know I like them too. I always like, even when a teenager. But what looks nice to your eyes?"

There wasn't a big selection, because this was Kohl's, but I ended up helping her select a white, closed-bottom, 38B corselette shaper. It was some non-descript brand. We thought we had everything in her shopping bag, but just as we were about to leave, we happened upon a display of Rago corsets (that set my heart beating madly). Ilka quickly noticed my attraction to a lacy black, open-bottom corselette with garters. She must have been in a good mood, because she bought that one too.

Before we left, she bought one just like it for herself as well, saying, "Now we can be like mother-daughter, same girdles!"

I wondered where she was coming from with that comment, but didn't respond.

Heading back toward home, she offered to order some breast forms online. We then proceeded to stop at a seedy wig shop in a poor part of town. But there, too, I was entranced by all the choices of styles and hair colors. Here, there were more customers and sales people, so I tried not to be conspicuous in my comments to the boss.

We ended up choosing a so-called dirty-blond hairpiece that drifted into slight curls as it fell past one's shoulders. I had never worn a woman's wig, so I was intensely curious about how it would appear on me.

"Bill today come to over $400," Ilka announced. "I can afford, to make you happy."

On the way home, she added another reason for helping me. "In home town of Lebeny, I had very younger brother who liked dress as woman. My papa found out, and when wouldn't play soccer or other sport, or dress like man, made him leave house. We never saw him again, and that sad. Very sad. Want that not to happen to you, Brett."

"I understand, Ilka. Very sad."

Upon arriving back at the apartment, Ilka surprised me with a new chest of drawers all my own that had just been delivered and some space and hangers in her large closet. Then we proceeded to lay out all her purchases on our bed. "There," said the stout woman with pride, "is all you could like for now, yes?"

"Thank you so much. You are really too nice to me for indulging my thing for lingerie."

"What you mean, thing?"

"I mean, attraction, or love for, or hobby. No, not hobby -- but (I wanted to use the word fetish) diversion, would be a good word."

"OK, good. Now, put all these things away, but I want to see you in black corset, and nylons for garters, and wig, good? Want to see money's worth." She laughed heartily.

OMG, she wanted me to model this stuff? Really? Me with a hardon? But how could I resist my insistent, commanding mom?

I managed to snake my way into the Rago, carefully pull on the nylons and wig, and had Ilka show me how to close the garters against the soft and erotic nylon tops. I was breathing heavily as I displayed myself (with cups full of TP) to Ilka's gleaming eyes.

She silently applauded. "Brett, you look halfway like real woman. Do you like feel?"

"Very much," I replied honestly. "Like being in heaven." I eliminated saying what I wanted to: "erotic heaven."

Fortunately, my eager cock was contained by strategically wearing the panty girdle under the Rago.

That evening, after a celebratory dinner, after watching some TV together, and as we were performing out usual bathroom ablutions before bedtime, she told me to wear one of the nightgowns we'd bought. "And wig."

"Wear a wig all night?"

"Yes, you do for me, OK Brett?"

How could I refuse? Maybe after a while I could slip out of it and she'd never know.

So I slipped into panties, the best of the two nightgowns (pink and blue, of a satin-like material), and the blonde wig. Again, I was instantly turned on.

This time, in bed, she had me come to her side of the bed and get in with her. I was horror-stricken! Wearing a flannel-like gown, she proceeded to spoon me and nuzzle my hairpiece. Her large arm crossed my chest and a hand lay next to my nipple. I was quiet and still.

Ilka whispered, "Oh, Brett, I so happy you like to dress like woman. Maybe we pretend you a daughter, OK?"

I didn't answer.

"Now, maybe you be pretend daughter for Ilka? I like call you Bridget. You be my Bridget."

"OK, I guess."

My cock didn't know what to do. Partly, this prospect greatly excited me. On the other hand, this overbearing woman with her large tits pushing against me seemed oppressive and no fun at all. If only she was a vixen my age..... At least she wasn't raping me in some manner.

By the next morning, a Sunday, we'd separated in bed, and I'd removed the wig. I didn't want to get up before her; that would be disrespectful. So I lay there, rather horny because I hadn't beat off for a few days. My hand lay over my cock under the blankets, and I began to explore my dick. I was sure Ilka was still fully asleep, but I was wrong. She stirred and suddenly looked over at me.

"Brett, or maybe Bridget? -- you are sex? You young man and have the urge? I feel bed moving a little."

I was mortified, but my hand over my dick was still making a small rise in the blanket.

"Oh, I been married, Brett Bridget. I know what makes men tick and tock." She laughed a little. One of her big tits was almost hanging out of her gown. "You wait a minute."

Going off into the bathroom, she returned with a hand massager and a small towel.

"Not like barbershop massager," she pronounced. Truly, it was sleek and had a small ball on one end.

She pulled one blanket off (leaving a thin one over me), told me to spread the hand towel over my privates, turned her device on so it was humming nicely, and put its vibrating ball next to my cock. Needless to say, I was immensely embarrassed that she'd finally crossed the divide into the sexual arena. My god.

I had never used such a thing, though I knew women did. The subtle, insistent vibration began to reach my penis and balls. She moved it around a little, looking at me all the time. It wasn't long before a pleasant sensation began to arise in my genitals. Slowly at first, I felt a climax approaching. It was so extremely pleasant that I closed my eyes. She pressed a little harder, and suddenly I was over the edge and exploded into spurts and spasms. Oh, my god, it was good. After I minute, I opened my eyes.

"OK?" she asked. "Good for you?"

I nodded yes.

"We maybe pretend you Bridget and you have girl orgasm." She smiled and chuckled.

"I've never had an orgasm like that before," I admitted. "I think wearing girls' things made it better. Maybe better than ever before."

"I tell you something, Bridget," she said huskily, "I want you to wear girl's, women's, things all the time here. You can pretend daughter -- that OK? You like that? If you like, I help you sex. Better than alone."

"I don't know. I have never given that any thought. Both things, that is. Living like a woman, here? I don't know if that's right for me. I will give it some thought, for sure."

And I did give it some more thought. I was beginning to think Ilka had this sort of agenda for me all along. She had a keen perception about me from the get-go, and was slowly and diligently leading me down a path. She knew she could lead me in certain directions. So, what would happen to me if I became a Bridget?

There was not only this development but more, outside our cozy apartment. I got another call to repair a window at Chris' place. Oh, yeah, I did want to fix that window!

I went over that evening and was pleasantly introduced to Chris' Janice, in full female regalia. His personality had also switched accordingly. I was so taken with him. His apparel, appearance and makeup, movements, and even his voice all said "woman." He/she had sexy tits. I saw him as a woman.

"Well, you wanted to see me as Janice," she said. "What do you think? What kind of grade do I get?"

"A++," I replied. "I am so impressed. You are truly Janice."

Janice was more self-assured than Chris, as though now his/her round peg had found its round hole.

"Well," she said, I'm afraid that there's no window to fix."

"I'm so disappointed."

She poured wine into celebratory glasses, which we proceeded to click. She wanted to know what was happening with Ilka and myself.

"You would not believe this, Chris, I mean Janice -- forgive me! After the spanking, Ilka had a religious conversion that brought her around to thinking she should help me with my fetish needs instead of punishing me."

"Oh, wow."

"So, to make a long story short, she bought me all the lingerie I wanted."

"Double wow."

"Plus clothing, nightgowns, the whole nine yards. And then -- wait -- she started spooning me in bed, and used a vibrator to masturbate me and -- wait! -- now wants me to dress all the time at home and pretend I'm her daughter Bridget!"

"You're not making this up?" laughed Janice.

"Swear," I replied. "I have to make up my mind about this. A woman old enough to be my mother offering to help me masturbate me....."

"She paid for all the women's things?"

"Yes!"

Janice reached over and put her hand over mine. "Well, why not? Join my sorority! Take advantage. Who knows, you might enjoy being a Bridget. I can tell you, Brett, that my journey as a crossdresser began just the same way; being attracted to female lingerie. One thing led to another. Soon, I graduated to, well, wanting to look and feel like a complete woman. Except, of course, I haven't gone out in public dressed -- except for a couple crossdresser events. Maybe at some future time....."

I replied, "A sorority; I love that idea, Janice! What I fear is that now that Ilka has had a sex experience with me, she'll want more. Who knows?"

"But," said Janice, "remember that she said she wants a daughter. If she wants to go further, you could just play on that, and say, 'let's just leave it at the vibrator, mom.'"

"Anyway," I replied, "I have to make this decision. But if I go that way, maybe you could help me with my looks, cuz Ilka doesn't have much of a sense of makeup and all that."

"Glad to."

As we talked, we sipped more wine and I began to enjoy her company more, enjoying her faint hint of perfume. However, I told Janice I was spending too much time with her there and that Ilka would suspect something, saying, "To be continued."

"Are you sure?" she asked as she stepped over and surprised me with a full kiss. I mean, a full lips-to-lips, tongue-searching kiss while her hand stealthily moved up my thigh. This was a whole new Janice, for sure. I really felt a natural woman was seducing me. The lips felt like a woman's, and I welcomed her hand.

"I could make you feel better than Ilka did," she whispered in my ear.

As I sat there waiting, she undid my belt, unzipped me, and with my help pulled my trousers down.

"Ah, you like the tight briefs," she purred. "I'm not surprised."

Down also went the briefs -- that took a little effort. But as my cock came into view, it eagerly sprung up. My dick is longer than the average male's, and Janice obviously took delight in this.

"My, my, Bridget, you're already getting wet."

She smoothed drops of pre-cum around my member's head as I squirmed in anticipation.

"Getting to know you," she sang as she kneeled on the floor and proceeded to run my dick's head all around her lips. That made me involuntarily thrust it into her mouth, which she took easily. Now, she expertly ran her clasped hand up and down my shaft as she sucked away.

This was driving me crazy, and soon my dam was about to burst. After three maddening thrusts into her mouth I ejaculated mightily.

"Oh my god, oh my god, oh god," I exclaimed.

So different than a vibrator climax, a part of my brain told me.

She raised her head up, happy, with sperm surrounding her lips and dripping down a little. "There, Bridget. There is something to remember me with. I have fantasized doing this with you from day one. One of my fantasies coming true."

"Phewww. I've had women do me before but I'd swear it was nothing like this. It's like, because you've been a man, you know how to do it better."

"Maybe," she replied, wiping my cum away from both her lips and my crotch. "Getting to know you," she sang liltingly again.

I finally said goodbye, returning to Ilka's with my world thoroughly blown open. My god, would I ever feel like being a handyman again?

I wondered how Janice felt, going to work the next day as a man. I wondered if she wore lingerie under her male clothing.

(To be continued)