Accepting a New Role

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"I guess so," I replied a little sadly. He must have been able to tell I was feeling a little down, because he came over and hugged me and gave me a kiss. "It's OK, Kristen. This is a hard process, but you're going to be happier in the long run by admitting who you are."

He let go of me, patted me on the butt, and said, "I'd go use the bathroom, cutie. It looks like some of my seed is leaking out of you."

He was right, some mixture of cum and lube was running down my leg. I went and sat on the toilet and it looked like my cock had actually shrunk from the whole experience. I pushed out some of his semen and the lube, and some of my own cum came out when I peed. I was spent.

While I was in the bathroom, I heard him rustling around in my walk-in closet. When I came around the corner, he held up a pair of pink panties with a little bow on the front and then a frilly pink nightgown to my body. He'd gotten into the clothes Stephanie had left behind.

"Kristen, are you about the same size as your soon-to-be ex-wife?"

"Yes, we often joked about how we could be fraternal twins. Even our feet were the same size."

"Did it bother her that her man was the same size as her, and not bigger and stronger?"

"Yes, she joked around about it and teased me, but I think she thought of me as a little less of a man because I wasn't taller or bigger."

"Seems like she was right. Put these on for me, sweetheart."

I slipped the silky panties on and he lifted the nightgown over my head and shoulders. It felt kind of weird to just have my legs hanging out of the bottom of something that was basically a frilly pink dress, and I felt really vulnerable and "open."

"You look great. Should we cuddle up and go to sleep?"

"Sounds good, Jim." We got into bed and he spooned up behind me and held me in his strong arms. I felt very protected and safe, and dozed off.

In the middle of the night, I started feeling a big hand reaching up my nightgown and slipping a finger under the waistband of my panties. Jim carefully slipped them down my legs and I moved my legs to accommodate.

I heard a sound, which must have been him putting on some more lube, and suddenly I felt his hardness at my now exposed anus.

I lifted up my leg a little and he pressed in. It didn't hurt as much this time, and before I knew it he had rolled me onto my back. I hiked up my nightgown so it wasn't in the way and wrapped my legs around him, just like Stephanie used to do to me, when I was the man in the bed.

Jim leaned in and started kissing me while he started pumping. It felt more like he was making love to me like I was his woman this time, instead of just banging me from behind. My cock got a little harder, and his hairy belly would drag across it and lay some weight on it as he thrusted and got more on top of me. I started fucking him back in a way that accentuated the friction of my semi-hard penis on his belly.

He lasted longer this time (it being our third encounter in not many hours), but I didn't achieve a real orgasm (just some more "surrender leakage" of cum) before he let out a moan and pumped his semen into me with a final thrust. It was certainly a new experience to have sex and not have a regular orgasm, and I could understand how this frustrated Stephanie (and a lot of women) that were dependent on another person's cock for pleasure (now that I was experiencing their role). Still, there was something emotionally satisfying about it. He pulled out, and after I'd gone to the bathroom to freshen up, pulled my panties back up and got back into spooning position next to his hairy, naked body. He smelled sweaty and manly, and it felt good (and a little wrong at the same time).

The next morning I complied with his request to make him breakfast, and said he had a busy day and plans that night. Before he left, he said he liked his girls a little fitter, and picked out one of Stephanie's workout outfits for me (pink yoga pants, padded sports bra (Steph was conscious about her small cup size), a headband, even her workout shoes, and a purple tank top) and told me to do one of Steph's streaming step aerobics workouts and take a picture of myself when I was done and send it to him. He gave me a long kiss and said we should meet up again next week, and I said I'd be in touch.

I did as I was told after he left. I sometimes did step aerobics (and Stephanie made fun of me for it and called me a fem), but it definitely felt more feminine than ever with me dressed up as a girl (with a padded bra no less) as I bounced up and down in front of the wall mirrors in our home gym. When I was done, I took a picture of myself in the mirror, my ass on display in the tight yoga pants as I looked over my shoulder at the camera with a bit of a smile. Then I climbed out of her clothes and took a long shower.

My butt and jaw were sore, and while it was a very erotic 24 hours, I wasn't sure all this degradation and submission was what I wanted for the rest of my life. I realized I missed Stephanie, and that all my time fantasizing over gay sex was missing what was important and the emotional attraction I had to women, and all the societal benefit of being straight. I resolved to reach out to her on Sunday and see what I could do to patch things up one last time.

When I woke up Sunday morning, I was surprised to see an email from her. "Dear Chris (or should I say Kristen?): I came into town for a party at my friend Sarah's last night and met her brother Jim. We hit it off, and after a few too many drinks, and me telling him about my separation and how I was torn about whether to get back with you and learning towards doing so, we figured out that he went on a date with you on Friday night. He told me all about it - your latent homosexuality, your gay prison fantasies, the kissing, the blowjob, the sex, wearing my clothes, cooking him breakfast like his girlfriend. He showed me a picture you sent him of you all sweaty in my girliest workout clothes. I'm both shocked and not shocked. He told me how you confided in him that you had a hard time being in a marriage with a woman because you wished you were the woman, being taken care of by a real man.

I was blaming myself for what's happened lately, and I realized it's not either of our fault that you are gay, and we both just need to move on. It sounds like you are off to a great start with Jim, and that you'll be very happy being his "catcher" (he told me that's the term for someone like you). Jim is a very big, strong, handsome man, and I'm a little jealous! No offense, any you're a really nice guy, but he is the kind of "man's man" I want in my next marriage. We both wanted the same thing I guess. This is the closure that I needed, and I'm glad you found it too. I hope you're not upset, but I already told a lot of our friends who were at Sarah's party (and my family this morning) about how you've come out of the closet, and everyone is really happy that I found closure and that you've realized who you really are. I'll warn you, there were a few snickers and laughs from some people, but who cares what they think.

Maybe once I find a man to start dating again I can go on double dates with you and Jim! We are going to have to trade tips and tricks for pleasing our men (Jim said you were incredible, and that you could give me some great pointers for oral and anal (If you tried it, now I have to!)). I'll be by to pick up some things next weekend, and Jim said he'd be over too. Don't worry, I won't take all my clothes :). You'll have to put on a fashion show for Jim and me, and maybe you can even let me watch you two get intimate together. Talk soon, girlfriend :)

Steph."

My heart sank as I read this, and I realized that there was probably no way to unring the bell. Everyone would know about me and my night with Jim, and Steph, and all the other men and women in my circle of friends, would always look at me as gay from now on. None of those women would give me a chance at a normal, heterosexual relationship again, and even if I met women who didn't know about all this, would I harbor too much doubt about my sexuality to perform for them?

Part of me felt really betrayed by Jim, and part of me felt a little turned on that he just made the decision to out me on my behalf. Maybe it was for the best, and maybe part of me was relieved that I wouldn't be able to lie about this dimension of my identity anymore.

Maybe it was time to "accept my role" like Jim said and embrace life as his catcher, and just make the best of it. Maybe, like in my prison wife fantasy, I'd learn to enjoy it more over time and the sting of my lost pride and masculinity would recede, and I'd even fall in love with Jim. It was all I could hope for now.

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AnonymousAnonymous10 months ago

Lucky she got away from the sissy wimp before he shared his STD's with her.

AnonymousAnonymousabout 1 year ago

Nice story.

Good details on a sensitive topic

AnonymousAnonymousover 1 year ago

I really loved your story and your journey. For some of us this is a wonderful blueprint on how to fully embrace the need to be a total sissy for your man. I loved how you continually validated what was happening to you is how it happens to women and you absolutely wanted to be the women.

I'm very lucky, I have a man that lets me be as feminine and girly as I can and I love being a total Sissy for him. He is so masculine and strong and I'm petite and feminine. We are perfect together, but I make absolutely sure I do everything he wants without question because I don't want the ending you had. I guess if I had to I could live without his loving and his amazing cock, but I swear I don't want that.

cdCindy1cdCindy1over 1 year ago

I love this story more and more each time I read it. I know that one day I will have to come out to my wife and show her that not only am I gay but I'm also a sissy who wants to be a "wife" for a hot studly man. One excerpt from your story that rings true for me is:

"He was definitely acting like "the man" and pursuing me as if I was "the woman," which was something I'd never experienced before and found both exciting and a little strange. He was very masculine ... and he even picked up the check like a real gentleman."

This happened recently with one of my secret gay lovers. He took me out to dinner, pulled my chair out for me to sit down, ordered the wine for both of us, held my hands during dinner a couple of times (yes, the waitress noticed & smiled at us), and then he paid for dinner like a real gentleman. All evening he was truly the "man" and I was truly the "woman". I was the sissy who dressed up in my sexy lingerie for him when we got back to his place. We made out like 2 high school kids, I then sucked his cock and he fucked me missionary-style like a man fucks a woman -- he said that he was "making love to me". That made me feel so good, so warm inside, knowing that I've become a submissive sissy who is falling in love with a hot studly masculine gentleman. I am certainly on my way to becoming the "woman" I was always meant to be.

Wish me luck when I finally muster up the courage to tell my wife that her straight-looking husband is actually a submissive sissy faggot cocksucking bottom bitch who only wants to have sex with men. I suspect she won't be happy but at least I will be able to be with my lover full time. I will be able to be a wife to my male lover, who will then become my husband.

I can't wait.

cdCindy1cdCindy1over 1 year ago

I love this story more and more each time I read it. I know that one day I will have to come out to my wife and show her that not only am I gay but I'm also a sissy who wants to be a "wife" for a hot studly man. One excerpt from your story that rings true for me is:

"He was definitely acting like "the man" and pursuing me as if I was "the woman," which was something I'd never experienced before and found both exciting and a little strange. He was very masculine ... and he even picked up the check like a real gentleman."

This happened recently with one of my secret gay lovers. He took me out to dinner, pulled my chair out for me to sit down, ordered the wine for both of us, held my hands during dinner a couple of times (yes, the waitress noticed & smiled at us), and then he paid for dinner like a real gentleman. All evening he was truly the "man" and I was truly the "woman". I was the sissy who dressed up in my sexy lingerie for him when we got back to his place. We made out like 2 high school kids, I then sucked his cock and he fucked me missionary-style like a man fucks a woman -- he said that he was "making love to me". That made me feel so good, so warm inside, knowing that I've become a submissive sissy who is falling in love with a hot studly masculine gentleman. I am certainly on my way to becoming the "woman" I was always meant to be.

Wish me luck when I finally muster up the courage to tell my wife that her straight-looking husband is actually a submissive sissy faggot cocksucking bottom bitch who only wants to have sex with men. I suspect she won't be happy but at least I will be able to be with my lover full time. I will be able to be a wife to my male lover, who will then become my husband.

I can't wait.

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