So… that happened… Megan’s thread

Great talk with Heidi. She definitely saw how sissy hubby is during Girls Day. She sort of probed wondering if he was gay or transgender. Doesn’t want to become a woman for real but very bisexual. He confessed to her that he fantasizes about being “en femme” so completely that a man would pick him up and let him suck cock. Asked her if she would help him become passable. She agreed if I supported it. So she was clear that he wants to explore beyond a sort of fetishy girls day experience.

Now Heidi isn’t experienced in anything unusual (or so she tells me). Had some boyfriends but not right now. But her reaction to him was being a good friend and like he was one of the girls. Talking to me she was curious, lots of questions. So the fact that I wear a strapon, let him suck and then fuck him came up in answer to her questions. I told her if she ever wanted to see us in action we’d love to have an audience. Left her a bit speechless so the conversation headed to safer waters.

She did ask how I felt about his sissy stuff, the strapon sex and such. I told her that I love him and we both want the other to find their true selves and that sex is not the same thing as love. Indulging his requests and fantasies has made him so much happier/true to himself.

She asked me how he’s supporting me. I was kind of dreading this, worried that she would cool on our friendship when I told her the truth. But I did any way explaining how hubby and I shared bedroom fantasies about me being with other lovers. I explained that putting hubby in that position really turned him on. I veered into how close humiliation is to arousal (reading I’ve done). And mentioned that with hubby embracing femininity/sissy, there wasn’t much sex happen we ing between us. So I’ve had two lovers.

It was a lot for her to process. She didn’t look down on me but her questions sort of dried up.

Before we ended the evening, she asked if I was okay with her calling hubby which I am. Now we’ll see as she thinks it through.
Great and fascinating update. Thanks x
 
Great talk with Heidi. She definitely saw how sissy hubby is during Girls Day. She sort of probed wondering if he was gay or transgender. Doesn’t want to become a woman for real but very bisexual. He confessed to her that he fantasizes about being “en femme” so completely that a man would pick him up and let him suck cock. Asked her if she would help him become passable. She agreed if I supported it. So she was clear that he wants to explore beyond a sort of fetishy girls day experience.

Now Heidi isn’t experienced in anything unusual (or so she tells me). Had some boyfriends but not right now. But her reaction to him was being a good friend and like he was one of the girls. Talking to me she was curious, lots of questions. So the fact that I wear a strapon, let him suck and then fuck him came up in answer to her questions. I told her if she ever wanted to see us in action we’d love to have an audience. Left her a bit speechless so the conversation headed to safer waters.

She did ask how I felt about his sissy stuff, the strapon sex and such. I told her that I love him and we both want the other to find their true selves and that sex is not the same thing as love. Indulging his requests and fantasies has made him so much happier/true to himself.

She asked me how he’s supporting me. I was kind of dreading this, worried that she would cool on our friendship when I told her the truth. But I did any way explaining how hubby and I shared bedroom fantasies about me being with other lovers. I explained that putting hubby in that position really turned him on. I veered into how close humiliation is to arousal (reading I’ve done). And mentioned that with hubby embracing femininity/sissy, there wasn’t much sex happen we ing between us. So I’ve had two lovers.

It was a lot for her to process. She didn’t look down on me but her questions sort of dried up.

Before we ended the evening, she asked if I was okay with her calling hubby which I am. Now we’ll see as she thinks it through.
She’s processing. Clearly had/has interest. Now she’s trying to figure out, or admit to herself, what that interest is. Helping you, and being aroused by, participating in, the humiliation thing? You? Maybe the whole voyeur aspect of sexual activity she never contemplated? I’m enjoying being a voyeur to the whole situation. Thanks for sharing.
 
A friend asked me about how my husband and I got here. Thought I’d share my reply:

When we were dating he loved that I wore sexy lingerie, satin and such. I kept it on some of the time while we made love. So part of me wondered. About a year before we got engaged he asked if he could wear my panties. That became a non-bedroom discussion where he admitted that he’d always liked to wear women’s underwear, that it turned him on. I’m not a prude and we’d been pretty open about sharing our fantasies so after some adjustment, him in lingerie became part of our love-making. I started to buy him some I thought he’d be cute in. By the time we got married, he was wearing panties every day and somewhere along the way he threw out all his guy underwear. After we got married we kept sharing fantasies and exploring so the whole sissy/feminization thing emerged from him. After teasing him with it for a while I finally pegged him last summer. Sleeping with another man, humiliating my sissy husband emerged in our sex talk and eventually got so real and specific that I talked to him away from the bedroom if that is what he really wanted. I asked because the idea was becoming the centerpiece of my fantasies. And intercourse with my husband has become infrequent. He much prefers to take my “cock”. We were both very nervous but also turned on so we agreed that I should go ahead and if either of us felt bad we’d talk it over again. That’s how it all started.
 
A friend asked me about how my husband and I got here. Thought I’d share my reply:

When we were dating he loved that I wore sexy lingerie, satin and such. I kept it on some of the time while we made love. So part of me wondered. About a year before we got engaged he asked if he could wear my panties. That became a non-bedroom discussion where he admitted that he’d always liked to wear women’s underwear, that it turned him on. I’m not a prude and we’d been pretty open about sharing our fantasies so after some adjustment, him in lingerie became part of our love-making. I started to buy him some I thought he’d be cute in. By the time we got married, he was wearing panties every day and somewhere along the way he threw out all his guy underwear. After we got married we kept sharing fantasies and exploring so the whole sissy/feminization thing emerged from him. After teasing him with it for a while I finally pegged him last summer. Sleeping with another man, humiliating my sissy husband emerged in our sex talk and eventually got so real and specific that I talked to him away from the bedroom if that is what he really wanted. I asked because the idea was becoming the centerpiece of my fantasies. And intercourse with my husband has become infrequent. He much prefers to take my “cock”. We were both very nervous but also turned on so we agreed that I should go ahead and if either of us felt bad we’d talk it over again. That’s how it all started.
That's very open and revealing. You have a great relationship with him to talk so freely x
 
I would love to see a nice alpha fuck my sissy tonight. It isn’t happening as I’m already in bed and he’s primping in the bathroom. But I’m teasing him with it and I know I want to make it happen. I want to hear him beg for real cock not just my strapon. Yep pretty horny tonight lol.
 
uI would love to see a nice alpha fuck my sissy tonight. It isn’t happening as I’m already in bed and he’s primping in the bathroom. But I’m teasing him with it and I know I want to make it happen. I want to hear him beg for real cock not just my strapon. Yep pretty horny tonight lol.
Would love for you to describe how you'd like it to go down? Are you going to "prep" that cock? Are you going to rub yourself while hubby takes it? Will you guide it in while you're whispering in his ear? What will you whisper?
 
I would love to see a nice alpha fuck my sissy tonight. It isn’t happening as I’m already in bed and he’s primping in the bathroom. But I’m teasing him with it and I know I want to make it happen. I want to hear him beg for real cock not just my strapon. Yep pretty horny tonight lol.
Would your painter guy be open for that?
 
Would love for you to describe how you'd like it to go down? Are you going to "prep" that cock? Are you going to rub yourself while hubby takes it? Will you guide it in while you're whispering in his ear? What will you whisper?
He will have to be dolled up to the max, freshly shaved, wig makeup, perfume, finest lingerie and sluttiest dress and heels. I think I will be clothed and bring my lover home after dinner. One of us might have been drinking (his option).

Hubby will have to seduce my lover though the scenario will have been agreed upon ahead of time. I will instruct hubby from a chair in the room: “on your knees”, “undress him”, “suck that cock” but more importantly I’ll make him declare what he is, what he wants, and beg for it to prove he’s sincere. He’ll suck and he’ll get fucked.

At least that’s the plan. I may or may not masturbate. I don’t plan to prep anything. If hubby can’t get my lover hard or keep him hard that will be a lesson.
 
He will have to be dolled up to the max, freshly shaved, wig makeup, perfume, finest lingerie and sluttiest dress and heels. I think I will be clothed and bring my lover home after dinner. One of us might have been drinking (his option).

Hubby will have to seduce my lover though the scenario will have been agreed upon ahead of time. I will instruct hubby from a chair in the room: “on your knees”, “undress him”, “suck that cock” but more importantly I’ll make him declare what he is, what he wants, and beg for it to prove he’s sincere. He’ll suck and he’ll get fucked.

At least that’s the plan. I may or may not masturbate. I don’t plan to prep anything. If hubby can’t get my lover hard or keep him hard that will be a lesson.
Good plan. Will you fuck your date in front of him after? perhaps make him eat you while he's getting fucked in the ass - or has he already totally sworn off pussy? That must make your little kitty really lonely :-(
 
Progress with Heidi. We had lunch today at Molly Woo’s and she brought up hubby. She offered to do another Girls Day with him which I told him later and he was thrilled. But Heidi asked more about what else he does as a sissy. I ended up telling her about our sex life with each other, him always in sexy lingerie, perfume. I told her he eats me very well and then I bring out the strapon for him to suck and then Inleg him. I could tell she was fascinated and had probably been thinking of this since Girls Day (“episode 1”). I joked that we’d both be very happy if she wanted to watch. She didn’t decline that. Conversation continued and when we left I told her that I was serious that she could come watch us with no commitment to do anything. She said she’d think about it.
 
Good plan. Will you fuck your date in front of him after? perhaps make him eat you while he's getting fucked in the ass - or has he already totally sworn off pussy? That must make your little kitty really lonely :-(
He eats me regularly and has developed quite a talent (Glee!). I think hubby’s deflowering will be all him. I can get laid in front of him another time.
 
Progress with Heidi. We had lunch today at Molly Woo’s and she brought up hubby. She offered to do another Girls Day with him which I told him later and he was thrilled. But Heidi asked more about what else he does as a sissy. I ended up telling her about our sex life with each other, him always in sexy lingerie, perfume. I told her he eats me very well and then I bring out the strapon for him to suck and then Inleg him. I could tell she was fascinated and had probably been thinking of this since Girls Day (“episode 1”). I joked that we’d both be very happy if she wanted to watch. She didn’t decline that. Conversation continued and when we left I told her that I was serious that she could come watch us with no commitment to do anything. She said she’d think about it.
If she's this interested, I'd say it's going to happen, which will be another great event in your new lifestyle. Sounds exciting!
 
Progress with Heidi. We had lunch today at Molly Woo’s and she brought up hubby. She offered to do another Girls Day with him which I told him later and he was thrilled. But Heidi asked more about what else he does as a sissy. I ended up telling her about our sex life with each other, him always in sexy lingerie, perfume. I told her he eats me very well and then I bring out the strapon for him to suck and then Inleg him. I could tell she was fascinated and had probably been thinking of this since Girls Day (“episode 1”). I joked that we’d both be very happy if she wanted to watch. She didn’t decline that. Conversation continued and when we left I told her that I was serious that she could come watch us with no commitment to do anything. She said she’d think about it.
Progress! I bet she brings it up next time
 
He eats me regularly and has developed quite a talent (Glee!). I think hubby’s deflowering will be all him. I can get laid in front of him another time.
I love your commitment to the plan! That takes restraint, determination and focus-on-mission. I have the utmost confidence you will succeed. You may end up hornier than ever, but your willingness to risk that is quite admirable! Soldier on o fearless warrior in your quest for El Dorado! :)

PS - Has he ever watched you fuck a lover?
 
Bit of a setback. It’s over with the Painter. Nothing bad just circumstances in his life changed. So I’m back to trying to find a good lover. And it had been a couple weeks so I’m pretty horny for it. Tempted to do riskier stuff but don’t want to get unsafe.

I’m seeing Heidi tonight so maybe that will keep progressing…
 
Bit of a setback. It’s over with the Painter. Nothing bad just circumstances in his life changed. So I’m back to trying to find a good lover. And it had been a couple weeks so I’m pretty horny for it. Tempted to do riskier stuff but don’t want to get unsafe.

I’m seeing Heidi tonight so maybe that will keep progressing…

Stay safe, of course! :)

Looking forward to hearing how it goes with Heidi...
 
Bit of a setback. It’s over with the Painter. Nothing bad just circumstances in his life changed. So I’m back to trying to find a good lover. And it had been a couple weeks so I’m pretty horny for it. Tempted to do riskier stuff but don’t want to get unsafe.

I’m seeing Heidi tonight so maybe that will keep progressing…
Setback? or Opportunity :)
 
Heidi is in! We have a plan. She’s going to take him on another Girls Day and bring him back home. She’ll tell him he has to model what he got for both of us. I will already be wearing the strapon but hiding it in pants or skirt. I’ll declare that he’s so sexy he’s given me a hardon and I reveal the strapon cock. Heidi will tell hubby that sissy sluts have to take care of problems they create. Then we get into it a heidi watches, no further expectation from her but she’s free to talk or do anything. I’m very excited. Hubby is thrilled for another Girls Day but doesn’t know that she’ll see him suck and get fucked. Pretty sure it will spike his humiliation meter! Don’t have the date locked down yet but soon!!
 
For some reason I don't think you'll have any problems coming up with your next lover. You found the painter very well quickly after opening up your marriage and there's plenty of fish in the sea. You'll come out on top again!
 
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