Ilka's Place Pt. 06

Life went on. There were always new twists and turns in my relationships with Ilka, Janice and Maryanne.

I began to enjoy being Bridget. My one complaint: My hair still wasn't long enough to avoid wearing the hairpiece. That would take three months more, or so.

When getting up in the morning, I so looked forward to putting on a delicate pair of panties and a fancy, filled-out bra, and then finding a dress that matched my mood. I enjoyed serving my momma, and playing the role of dutiful daughter. We were having a very good relationship.

Once or twice I fantasized taking hormones to give me real tits, more curves and a softer voice (Ilka had never mentioned doing so) but I read that that might make me impotent. I didn't want to diminish my wonderful climaxes and ejaculations. But who knew where my Bridget path would take me?

Once, Ilka and I talked casually about the possibility of my living and dressing as Bridget all the time, which is actually what I wanted. But we thought that some of her conservative or religious apartment dwellers might get upset when they saw my gender fluidity -- and would complain. I hoped this wouldn't be the case with Maryanne!

Now that Janice had me up to speed on dressing and makeup, I knew that Ilka would expect my visits to her to mostly end. So I let her assume that, but still managed to drop by Janice's apartment every few weeks. She'd greet me with a big kiss and rub her boobs and hips against me. We'd smoke a little weed, and she soon seemed the sexiest woman in the world, especially if I hadn't cum in a while.

During one late afternoon of making out on her bed, with me getting my panties all wet as we snaked together, she reached down, unbuckled me and held my hot prick. She began stroking it a little and I completely expected her to take me to the Big Bang. But then she stopped, asking softly, "Would you fuck me, Brett?"

I didn't know what to say. I had certainly seen porn of guys doing each other, and I'd seen porn of guys fucking sissies or trans women -- or even one crossdresser fucking another! But here was I, kinda pretending I was Bridget, and now Janice wanted me to Brett-fuck her.....

"Oh, I can see I'm embarrassing you," said Janice in her most womanly voice. "Don't feel you have to make me happy."

"Oh, I don't know what to say, dear," I said. "Hmmm. I'm assuming you've been fucked before?"

"Only once. Only once. It was a beefy guy I met at a gay bar when I wasn't crossdressed. I wasn't even that taken with him, but I was so curious about getting fucked. It was as though when we talked, my asshole was saying, 'I want to feel him in me!' Plus, I just wanted to see his dick."

We both laughed; laughed hard. That kinda broke the ice.

I said OK, and that I was somewhat curious myself. Janice thanked me profusely, and went to get a condom. I took off my trousers, which were already hanging loose on me.

"How should we do this?" asked Janice, now in just bra and panties. Fortunately, she was always cleanly shaven, with smooth skin. I knew she took low-dose hormones.

For such a confident woman, she now seemed a bit timid and unsure of herself.

"How did you and the guy do it?"

"He had me lie on my back on the edge of the bed and had me pull my legs back to my shoulders. He was a hairy beast, that guy. I told him it was my first time, but he still wasn't very gentle with me.

"After he lubed me up, I was laid wide open for him, and while holding my ankles, he pushed into me. I was, like, yeah, completely under his control and his dick owned me. I loved being occupied by it, which was larger than average, you know."

"I wish I'd been a fly on the wall to see this," I offered.

"He was the silent type. He began fucking. Began to speed up. I was imagining I was a woman, and that began to excite me. A couple times, he reached down to hold my wet cock in his beefy hand, and I absolutely loved that!"

"And then....?"

"It didn't take long. He gasped and shuddered and I felt him spurting inside. He had such a big load! When he pulled out, my hole was dripping cum. And that was that. He said goodbye, and I never saw him again.

"It took a while for my mind to get around that sex. I realized the only way I'd do it in the future would be with me as Janice, with more say."

"Well, Janice, I'd prefer to do it doggie style. That's what I'm familiar with, with women, you know. And in the future, you know, if we ever do this again, I'd love to do it woman to woman."

She seconded the idea.

With her white and pearly butt offered up, I first penetrated her gurl vagina with some lube and a slender finger, moving it around and in and out a little, and briefly held her gurl cock, eliciting some soulful moans.

"Janice, rover wants to come home," I joked.

"Mmmmm," was all she could manage.

With that, I held my very erect, condomed member and placed its tip on the very edge of her puckered anus. Maybe it was the weed we'd smoked earlier, but the idea of entering her seemed so sexy and pure.

I felt some resistance to my entry, so I purred to Janice, "OK, dear, completely relax and allow my beautiful dick to fulfill you." I loved the word "fulfill."

"Yes. I want you inside."

And there I was, slowly and magnificently entering while holding her hips. It was almost like fucking a real woman, like I'd done in this position before. But in my mind, for some reason, fucking a man-woman was even more exciting. It was exotic, and her boi cunt gave me so much cock stimulation.

I began to thrust, and soon sped up a little. Janice soon began to push her butt back against me in concert with my movements. This inflamed me so much I came.

Afterward, we lay side by side, and I stroked her to orgasm. We were both happy and very satisfied. It was such an intense experience I wouldn't want to do it too frequently.

Janice confessed the fuck made her feel even more like a woman, saying she wanted to live as a woman all the time.

"Maybe you could make that work," I offered.

About three weeks after that (I certainly didn't consider myself to be gay) I had another chance to spend time with Maryanne. Her reason for calling me this time: She couldn't open a window. Maybe there was a symbolic message there.

This was in the evening when I was dressed as Bridget at home, and after Ilka learned where I was going, she joked, "I think that lady likes to see you. She wants more than repair?"

I got around to telling her about Maryanne's experience in a cloister, and how I gave her a first romantic kiss. I waited for her reaction.

"Should have known this would happen. Grown-up daughter will be sex daughter! Maybe this woman has plans on you. Maybe she wants you for herself. Lonely woman; I know all about that."

"Oh, momma Ilka, I like being with you. We have good relationship. There, I'm even talking like you! This is my home. You've been so kind to me. And I like being Bridget, I truly do. You give me guidance, you know. I need that."

I continued, "This woman -- Maryanne -- doesn't know about Bridget. But she asked me out for a date, and I'd like to go. That be OK with you?"

"And then you get sex, and I lose you."

"Maybe sexual, but you won't lose me. She really wants to live by herself; that's her personality. She likes living by herself."

I was lying through my hat.

"But Ilka, you want me to be happy, yes? And having a relationship with someone my age is only natural for Bridget. It will make me a happy daughter!"

"Maybe she get mad when she find out about Bridget." Ilka brightened. "Maybe she not like lesbian."

What I didn't bring up was the possibility that Maryanne had been among some lesbians in her nunnery. I hadn't thought about that before.

So, without Ilka tacitly agreeing that I could see Maryanne, I knew her and my relationship could progress. Despite Ilka's worries and misgivings, she wouldn't put her foot down. That also meant that I had to continue to be a very loving and respectful daughter.

When I returned to my male clothing that night, with delicious panties underneath, I made my way over to Maryanne's. She greeted me with a brief hug and peck on my cheek. Her insect infestation was no longer a problem, and there was no stuck window, she admitted.

This time she was wearing a festive peasant skirt and peasant-embroidered blouse. Her hair was down again, and underneath I could just make out some wonderful filigree earrings. Best of all, her long leather boots peaked out from underneath her skirt.

"I'm so glad you could make it, Brett. I've been looking forward to this," she liltingly said as she handed me a glass of Riesling. "You're better dressed, I notice."

"Of course." (And if you could only see my panties underneath!) "I should tell you I just told Ilka I was interested in dating you. That was risky."

"She's like your mother, isn't she?"

"Like the mother of mothers, yeah. She was worried about losing me, but I reassured her and she didn't object."

"But you're not a momma's boy."

"No."

After picking an evening for a movie date, we sat down on her soft couch to watch some PBS historical drama she was following. Not exactly my cup of tea, but I soon pulled her to me and had my arm around her. She endearingly lay her head alongside mine.

It wasn't long before she playfully kissed my ear and neck. With that, I moved to face her and pulled her lips to mine. They met perfectly (she must've been practicing!). We deliciously smooched for a while, and then I kissed her neck.

"When I was in the convent, I often wondered what heaven was like," she said softly. "Now I know."

I laughed a little. "You're a beautiful person, Maryanne. Maybe we can make up for lost time."

With that, I reached under her blouse. She wasn't wearing a bra! Her titty fit my hand perfectly. She made a half-hearted attempt to push it away, saying, "Oh, aren't we moving too fast, Brett?" followed by, "Oh well, I love it."

After I played with her boobs for a time, while kissing, she suddenly took over, unbuttoning my shirt. Then she began kissing my nipples, which was a major arousal. All the time she kept looking into my eyes.

I was just about to move my hand up her skirt when she decided we'd gone far enough. It was tough for me to accept that, but I did the gentlemanly thing and sat back.

"Remember, Brett, this is all new and we don't want to be in a rush," she said. "Can you live with taking things slowly? It must be hard."

"Hard is a great pun, to be honest," I quipped, and we both laughed. "Sure, taking it slow can be fun, too. There's more time to enjoy the journey."

"Oh, good. By the way, I noticed something I want to ask about."

"Yeah?"

"I was looking into your eyes, and I'd swear there's just a trace of eyeliner and mascara. Not that I'm into those things; I don't use them. But are you a rock star or something on the side?"

I must've blushed. I was about to deny any knowledge of makeup, but I knew she wouldn't believe me. I frantically wondered how to handle her curiosity, and not disturb her. How could I explain my kinda weird relationship with Ilka without sounding like a momma's boy, which she obviously didn't like?

"I'm going to tell you a story, Maryanne, which you may find funny, incredible or sad -- I'm not sure which."

Suddenly we were way far away from our necking, and I was feeling extremely uneasy. I gamely set out to open Brett up and expose Bridget. And that's just what I did, detailing how Ilka rescued me from homelessness, and after discovering my love of lingerie, grooming me to be her son and then her daughter -- and, sleeping together!

During this lengthy reveal, Maryanne didn't interrupt once. She merely looked interested and bemused, not disgusted.

"So, Brett, or Bridget, you've embraced your female side, have you?"

"You're not upset or put off by this?"

"It's so unexpected and unusual, to say the least. But where do you see yourself now -- would you rather be Brett or Bridget? Or both, or what?"

I wasn't quite up to answering that question. "Maryanne, I feel like I've led you on a bit, presenting only my Brett side to you. That's the person you want to play with, right?"

"I like YOU, and whether you pursue the feminine or the masculine, or both, I know we can enjoy each other."

"Well, I have to confess that I'm coming around to wanting to be Bridget as much as possible. Not to have a sex change, my god, but to enjoy a woman's role and appearance. But I know as Bridget I may still look too masculine."

"Oh, I don't know. Let me decide that."

I then added the second part of the story -- about Janice helping me, leaving out the part about our having sex. She may have guessed that, but she didn't broach that issue.

"Thanks for telling me all of this, which I guess could be hard for a guy" she said with a smile.

Underneath, I still suspected she was just being nice, and this could be our last visit. She could decide to seek out "a real man" to enjoy.

"This is so fascinating," she said -- "because, once in a while, I've wondered what it's like being a man. And I've known women both in and out of the convent who were manish, or aggressive -- you know. It takes all kinds to make a world..... "

On that intriguing note, we made out some more, and I ended up kissing her nipples. I knew I had to leave things right there. Her hand had begun heading south, over my nipples and all, but it didn't pass the equator.

Yes, I was one lucky Bridget. How would we make the move to include my feminine side? Something told me there was much more to learn about Maryanne.

(To be continued.)