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So… that happened… Megan’s thread

Yes! We made a date Thursday night. We met for drinks and ended up talking for about an hour. Nice guy, great painter but he’s also a grad student of history. The first time I’d had his cock in me after exchanging maybje 100 words. It was nicer to know him some and then head to the room. I loved his hand on my ass in the elevator exploring me. Fucked for a couple hours, I came at least four times and he came twice. Gotta love 24yo cock! I asked if he’d be willing to get tested so we didn’t have to use condoms and he said he would.
 
MeganFachs said:
Yes! We made a date Thursday night. We met for drinks and ended up talking for about an hour. Nice guy, great painter but he’s also a grad student of history. The first time I’d had his cock in me after exchanging maybje 100 words. It was nicer to know him some and then head to the room. I loved his hand on my ass in the elevator exploring me. Fucked for a couple hours, I came at least four times and he came twice. Gotta love 24yo cock! I asked if he’d be willing to get tested so we didn’t have to use condoms and he said he would.
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Did you take your well fucked pussy home for your husband to lick and and worship?
And yes, you need to have him fuck you bare so that you can bring a nice hot cream pie for hubby to clean.
 
No, hubby doesn’t get to fuck or touch me when I come home. I bring him home a “doggy bag” of all the filled condoms for him to swallow. Sometimes right from the condom, sometimes drizzled over my strapon. I am very nice that I keep them nice and warm between my breasts on the drive home.
 
So I got my third “date” with the Painter. Told him I wanted to go shopping with him. With his bulge he’d agree to anything. He also had his STI test results so we were going to play bareback.

I took him to Nordstrom’s dept store and the women’s section. I grabbed a bunch of dresses and lingerie pieces in my size with the help of Gwendolyn a salesgirl. Then I dragged him into the dressing room.

We kissed as I undressed and he took off his jeans and boxers. Once I was naked I slipped into a pretty pink satin teddy and knelt to suck him. As soon as he was rock hard I got up and turned around, bending over. I gasped as he slid easily into my pussy and gripped me by my hips. We fucked quietly like that for several minutes.

Then Gwendolyn came to check on me. “How is it going in there?” Painter almost froze but then kept thrusting. “Do you need another size?”

“No I don’t think I could handle any larger,” I said as calmly and normally as I could. Painter froze, biting his hand to keep from laughing.

“Okay, just call out if you need anything.”

“Thanks, Gwen.”

It didn’t take long for him to cum, deep and long inside me and I pulled him against me hard, relishing his bare cock erupting in me. He reached around and fingered me with his cock still hard in me and I came deliciously, stifling my own typical moans as best I could.

He bought me the teddy and a dress. 😁
 
MeganFachs said:
So I got my third “date” with the Painter. Told him I wanted to go shopping with him. With his bulge he’d agree to anything. He also had his STI test results so we were going to play bareback.

I took him to Nordstrom’s dept store and the women’s section. I grabbed a bunch of dresses and lingerie pieces in my size with the help of Gwendolyn a salesgirl. Then I dragged him into the dressing room.

We kissed as I undressed and he took off his jeans and boxers. Once I was naked I slipped into a pretty pink satin teddy and knelt to suck him. As soon as he was rock hard I got up and turned around, bending over. I gasped as he slid easily into my pussy and gripped me by my hips. We fucked quietly like that for several minutes.

Then Gwendolyn came to check on me. “How is it going in there?” Painter almost froze but then kept thrusting. “Do you need another size?”

“No I don’t think I could handle any larger,” I said as calmly and normally as I could. Painter froze, biting his hand to keep from laughing.

“Okay, just call out if you need anything.”

“Thanks, Gwen.”

It didn’t take long for him to cum, deep and long inside me and I pulled him against me hard, relishing his bare cock erupting in me. He reached around and fingered me with his cock still hard in me and I came deliciously, stifling my own typical moans as best I could.

He bought me the teddy and a dress. 😁
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atta girl!!!
 
Today was a big day. I talked to my girlfriend Heidi before Christmas. I’d already told her about him loving to wear panties and lingerie all the time and for sex. Heidi doesn’t gossip and is super not judgy so I’ve confided in her a lot. Not about me sleeping with other men, at least not yet.

So we talked about what a sissy he is and she agreed to my proposal to have her take him on a “Girls Day” including spa visit, shopping, light lunch and dinner. I paid for everything of course. Hubby was floored when I told him this was one of his Christmas presents.

They spent the day together and sent me photos at each stop. By the time hubby got home, my credit card was steaming and he also looked more like a woman than I’ve ever seen him. Makeup done by Heidi was better than when I’ve helped him and he even let a salon give him a women’s haircut. He says it is unisex but no one would look at it as anything but feminine. To say he was thrilled would be an understatement by far. I had him caged as usual which was good since he felt aroused countless times through the experience.

What he doesn’t know yet is that while he was gone, I spent time with the Painter. Three hours, no condoms now that he’s been tested and isn’t seeing anyone else. I love younger men and their fast refractoryrate!!!
 
MeganFachs said:
Today was a big day. I talked to my girlfriend Heidi before Christmas. I’d already told her about him loving to wear panties and lingerie all the time and for sex. Heidi doesn’t gossip and is super not judgy so I’ve confided in her a lot. Not about me sleeping with other men, at least not yet.

So we talked about what a sissy he is and she agreed to my proposal to have her take him on a “Girls Day” including spa visit, shopping, light lunch and dinner. I paid for everything of course. Hubby was floored when I told him this was one of his Christmas presents.

They spent the day together and sent me photos at each stop. By the time hubby got home, my credit card was steaming and he also looked more like a woman than I’ve ever seen him. Makeup done by Heidi was better than when I’ve helped him and he even let a salon give him a women’s haircut. He says it is unisex but no one would look at it as anything but feminine. To say he was thrilled would be an understatement by far. I had him caged as usual which was good since he felt aroused countless times through the experience.

What he doesn’t know yet is that while he was gone, I spent time with the Painter. Three hours, no condoms now that he’s been tested and isn’t seeing anyone else. I love younger men and their fast refractoryrate!!!
Click to expand...
You move fast. congrats. I was thinking part of the continuing humiliation could have been (could be) to have Heidi get him all worked up like she did, then bring him home where you have the Painter and another guy play with you and Heidi while he is forced to sit in his new panties and watch
 
Chazwill said:
You move fast. congrats. I was thinking part of the continuing humiliation could have been (could be) to have Heidi get him all worked up like she did, then bring him home where you have the Painter and another guy play with you and Heidi while he is forced to sit in his new panties and watch
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Heidi and I don’t have a sex relationship, sadly. Well at least so far. ;)
 
MeganFachs said:
Today was a big day. I talked to my girlfriend Heidi before Christmas. I’d already told her about him loving to wear panties and lingerie all the time and for sex. Heidi doesn’t gossip and is super not judgy so I’ve confided in her a lot. Not about me sleeping with other men, at least not yet.

So we talked about what a sissy he is and she agreed to my proposal to have her take him on a “Girls Day” including spa visit, shopping, light lunch and dinner. I paid for everything of course. Hubby was floored when I told him this was one of his Christmas presents.

They spent the day together and sent me photos at each stop. By the time hubby got home, my credit card was steaming and he also looked more like a woman than I’ve ever seen him. Makeup done by Heidi was better than when I’ve helped him and he even let a salon give him a women’s haircut. He says it is unisex but no one would look at it as anything but feminine. To say he was thrilled would be an understatement by far. I had him caged as usual which was good since he felt aroused countless times through the experience.

What he doesn’t know yet is that while he was gone, I spent time with the Painter. Three hours, no condoms now that he’s been tested and isn’t seeing anyone else. I love younger men and their fast refractoryrate!!!
Click to expand...
Love this thread. Looking forward very much to see where things go. Have fun 😘
 
Things have been quiet since my sissy’s girl day with Heidi. He’s talked about it a lot and would love to do it again. Spending time with another woman who he didn’t know all that well who knew about him being a sissy was humiliating for him and quite a rush.

I’m texting with the Painter every few days and definitely need his cock more. He sent me a dick pic new year’s eve which I’ve shown to hubby so my sissy can see how much he does not measure up.
 
We had sex tonight (meaning I pegged him after I masturbated) and I started talking about making some other things happen for real. I mentioned wanting to fuck a lover in my own bed and if he would want to be “made” to watch. I also suggested that maybe he wants someone to watch as I peg him. The second got his dick quivering in his cage as he admitted he wants to be fucked in front of Heidi. Very interesting thought and I’ll have to be careful about how I maybe approach making it happen.
 
MeganFachs said:
We had sex tonight (meaning I pegged him after I masturbated) and I started talking about making some other things happen for real. I mentioned wanting to fuck a lover in my own bed and if he would want to be “made” to watch. I also suggested that maybe he wants someone to watch as I peg him. The second got his dick quivering in his cage as he admitted he wants to be fucked in front of Heidi. Very interesting thought and I’ll have to be careful about how I maybe approach making it happen.
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...my cock, I mean the plot....thickens........
 
Made a drinks date with Heidi for tomorrow night. I want to get a real story about how Girls Day went, how Heidi feels, and tease her a little if she seems receptive. Hubby begged me to peg him a little while ago and I talked about how Heidi was coming to watch how much of a cock-craving sissy he is, to watch him suck my strapon and then “get railed”. When I teased that she might bring her own strapon he creamed his panties and moaned. Hope I can get it to happen.
 
MeganFachs said:
Made a drinks date with Heidi for tomorrow night. I want to get a real story about how Girls Day went, how Heidi feels, and tease her a little if she seems receptive. Hubby begged me to peg him a little while ago and I talked about how Heidi was coming to watch how much of a cock-craving sissy he is, to watch him suck my strapon and then “get railed”. When I teased that she might bring her own strapon he creamed his panties and moaned. Hope I can get it to happen.
Click to expand...
Sounds like you are well on your way. Heidi wouldn’t have indulged him or you if she wasn’t also in to it at some level.
 
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.
 
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