So… that happened… Megan’s thread

Hi girls and boys!

Mmmm I had a lovely date with Gary. Supposed to be drinks but became dinner too (which Hubby paid for it all). Gary and I got to know a lot about each other. He had moved to town last year for a job at the university. Was married earlier in his life but is divorced now, no kids. Our tastes in movies are different but he also plays Dungeons & Dragons from time to time.

He was very complimentary and made me feel beautiful. We definitely were flirting. I was open with him about my past and current situations sexually including sleeping with women and my husband’s development as a sissy and as a cuckold.

He took it in stride I would say. Told me he liked women’s panties too. I had him wait at the table, stopped by hubby’s table to tell him what I was doing, went to the ladies, removed my panties, returned to the table and gave them to him. He tried to hide from others seeing him but I watched him sniff my panties deeply and he was quite turned on.

Even though I was quite aroused with him, I held off doing anything further sexually with. Let him build up his interest. ;). Told him to call me so we’ll see how long it takes.

Hubby very much enjoyed watching us and being forced to pay for his wife to date another guy.
Sounds like it went very well.
 
And when's the last time your Sissy had some cock - just that one time with your vendor stud? He needs another does of cock and cum. Maybe if things go well with you and Gary, at the least your Sissy can lick your well fucked pussy clean of his cum when you get home, as you tell him all the nasty details.
Yes, sissy has been good, at least let her have some cum in your panties
 
Nothing as exciting at tight panties up against a cunt! Pink, of course!



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Saw Gary tonight at his place. We’d been on the phone the last few days a lot and texting. I couldn’t wait anymore. I had to have that cock.

I had sissy dress me to be fucked by another man and then I put sissy in her flamboyant pink satin sissy dress, extra crinolines to floof her skirt, high heels (both heels and dress locked on her). Instead of panties I diapered her. She did the rest and looked very femme and sexy especially in her blonde wig. Sissy drove me to Gary’s house and parked in the street. It was a quiet suburban street but a car or dog walker would go by every so often. Sissy had to stay in the car while I went inside to get fucked. I left her with bottles of water and she did have her diaper after all.

I went inside with Gary and had a quick drink. He had groove music on. Then he kissed me and I kissed him back like I’d never been kissed. We started peeling off our clothes down to my lingerie and his underwear. Went to his bedroom and called sissy. Told her I was going to suck Gary’s cock and then let him fuck me like an animal. Set up my phone with Facetime on and forgot about Sissy.

Gary wasn’t a porn star in the cock department but had a beautiful 6-7” cock which was rock hard when I pushed him back on the bed and climbed on to suck him. Gave him one of my finer blowjobs and he erupted in less than five minutes. He apologized and said I was so hot he couldn’t help himself (good answer!). The condom was very full of cum so I saved it carefully.

He took over, stripped off my panties and enjoyed sniffing them with my encouragement. That revived his cock fast. He licked me for a while but wasn’t that great at it. I begged for his cock so he got a fresh condom and set to fucking. We did several positions where I could enjoy his thick cock and energetic thrusting. Came a few times before he did. Kept the second condom too.

He wanted me to sleep over but I reminded him of hubby outside. Left Gary’s around ten. Sissy had wet herself.

Went home, let sissy out of her heels but not her dress. Gary hasn’t had his std test yet so I couldn’t let sissy drink it. I chose to change her diapers and pour the cum all over her cock and ass before putting the new one on. She’s in bed next to me squirming In her cummy diapers.

A very good night!
 
Saw Gary tonight at his place. We’d been on the phone the last few days a lot and texting. I couldn’t wait anymore. I had to have that cock.

I had sissy dress me to be fucked by another man and then I put sissy in her flamboyant pink satin sissy dress, extra crinolines to floof her skirt, high heels (both heels and dress locked on her). Instead of panties I diapered her. She did the rest and looked very femme and sexy especially in her blonde wig. Sissy drove me to Gary’s house and parked in the street. It was a quiet suburban street but a car or dog walker would go by every so often. Sissy had to stay in the car while I went inside to get fucked. I left her with bottles of water and she did have her diaper after all.

I went inside with Gary and had a quick drink. He had groove music on. Then he kissed me and I kissed him back like I’d never been kissed. We started peeling off our clothes down to my lingerie and his underwear. Went to his bedroom and called sissy. Told her I was going to suck Gary’s cock and then let him fuck me like an animal. Set up my phone with Facetime on and forgot about Sissy.

Gary wasn’t a porn star in the cock department but had a beautiful 6-7” cock which was rock hard when I pushed him back on the bed and climbed on to suck him. Gave him one of my finer blowjobs and he erupted in less than five minutes. He apologized and said I was so hot he couldn’t help himself (good answer!). The condom was very full of cum so I saved it carefully.

He took over, stripped off my panties and enjoyed sniffing them with my encouragement. That revived his cock fast. He licked me for a while but wasn’t that great at it. I begged for his cock so he got a fresh condom and set to fucking. We did several positions where I could enjoy his thick cock and energetic thrusting. Came a few times before he did. Kept the second condom too.

He wanted me to sleep over but I reminded him of hubby outside. Left Gary’s around ten. Sissy had wet herself.

Went home, let sissy out of her heels but not her dress. Gary hasn’t had his std test yet so I couldn’t let sissy drink it. I chose to change her diapers and pour the cum all over her cock and ass before putting the new one on. She’s in bed next to me squirming In her cummy diapers.

A very good night!
Sounds like everyone had a good time. I'm glad you've found a new stud since Vendor seems to have moved on..

Did Gary like having your Sissy listen to you two fuck, or was so so? Any chance you think of him trying out Sissy's mouth and ass? Did you slut cum from hearing you two fucking away?

Stiff and hard, and jacking my cock, reading all this, thanks for the update. Wish I had a pair of your panties to use like I'm sure Gary did.
 
Have your Sissy buy you panties, to give to your lovers to jack off with. She'll love the humiliation.

Promising about Gary and your Sissy. Lots of men are hot for kinky things, but are worried about how that will make them look, and feel about themselves. Maybe if you take things slow and a step at a time, he'll want to try some new things out, including your sissy's hot and needing to be fucked ass.

He just have Vendor's cock so far? And just that one time?
Bet she loved having your lover's cum all over her cock. You should have rewarded her for being such a good girl and jacked her off using the cum for lube.
 
Do you think your hubby wants to be feminised and submissive because he crossdresses? Sure there are plenty of guys like that, but there's also another side to crossdressing, which is the one that kind of turbocharges a man's libido (I'm the latter: wearing lingerie turns me like crazy and fucking in it is the best, for me)
Have to agree with this, and whilst I can’t claim to be a cross dresser, a girlfriend did ask me to arrive at her place wearing panties and hold ups. The effect on her was amazing, and some of the best sex ever for me. I think the moral of this is, if you can relax and enjoy another person’s kinks, without letting go of who you really are, then you’re going to have a lot of fun…
 
I did leave my panties with Gary. This will get expensive if we get regular!

Gary warmed up to sissy watching him fuck sissy’s wife. Said some bull like things. He’s got potential to go further with that.
Excellent date! Sissy will love Gary turning into a more serious bull. Maybe Gary will let sissy fluff him up for you?
 
I would LOVE to lick your ass, as long as you dont mind me cumming in my pink panties.......
 
Every once in a blue moon you see someone who takes your breath away.
I thought about this post the instant I saw her.

We were out getting takeout tonight, standing in line in this little tex-mex place. She was in front of us. Nothing in particular would scream "Wow", but the whole package just screamed "WOW!"

Brown hair, brown eyes, and tanned skin. A little taller, and just the right amount of soft, supple skin showing. (She kinda reminded me of your AV picture actually). She was wearing shorts, and a loose fitting tank top, just warm weather summer wear. She was placing her order, dancing and quietly singing to the music as she did. Just grooving in a completely care free way. She didn't care what anyone thought, and that made it all the hotter.

Of course she forgot her wallet and phone in her car, bounding out the door right past us to grab it. As fast as she was gone she was back again, payed, and apologized to us for the delay. (All I could do was smile and shrug...)

The place is tiny, so she was standing next to us waiting for her order, just grooving away to the music playing. I couldn't stare, and I couldn't not stare. Every single thing about this goddess was perfect, without being obviously so.

We grabbed one of three tables in the place to wait, and she danced over next to us as more people filled in. As she grabbed her order and stepped into her car, I stole a glance through the window. She looked back, saw me, smiled and was gone.

The whole time my wife was just grinning at me, knowing exactly what was on my mind. She didn't see it. She wasn't struck as I was. To her she was just one more person shuffling past.

The wife knows if this ever happens to her, and she wants to pursue it, all she has to do is call me and say "You know that thing we talked about? Yeah...".
This would have been my "Yeah..." I would have used a once in a lifetime hall pass on her. WOW! Just WOW!
 
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Busy weekend! Hubby had a birthday. We went and saw Deadpool & Wolverine (loved it).

Took him to the adult toy store. Told the girl that my sissy needed a bigger cock for my strapon harness and asked her to help us. Sissy was obviously very hard in his shorts which she saw. We had fun teasing him about each option. My favorite moment was when then salesgirl asked him if a particular one would look better in his mouth or pussy. (I love adult store employees… they see this every day and can have fun with it).

We bought a bigger one (african skin color, veiny, thick and 11” insertable) than Goliath. He can only fit the head in his mouth. We call it Terry because we agree Terry Crews is so hot. Took us a long time that night but he finally got most of it in his pussy. We’re going to keep working him until I can go balls deep with big black cock in my sissy’s pussy.

Gary sent me his STD test results (negative woo hoo!) and I sent him mine and hubby’s just in case.

I texted Vendor, no response. Not sure if he’s ghosting me or why but it sucks.

I won’t have a chance to be with anyone except my Wed night with Heidi until maybe next week. If you’d asked me if I would be this sexually active a year ago… never would have believed it.
 
Busy weekend! Hubby had a birthday. We went and saw Deadpool & Wolverine (loved it).

Took him to the adult toy store. Told the girl that my sissy needed a bigger cock for my strapon harness and asked her to help us. Sissy was obviously very hard in his shorts which she saw. We had fun teasing him about each option. My favorite moment was when then salesgirl asked him if a particular one would look better in his mouth or pussy. (I love adult store employees… they see this every day and can have fun with it).

We bought a bigger one (african skin color, veiny, thick and 11” insertable) than Goliath. He can only fit the head in his mouth. We call it Terry because we agree Terry Crews is so hot. Took us a long time that night but he finally got most of it in his pussy. We’re going to keep working him until I can go balls deep with big black cock in my sissy’s pussy.

Gary sent me his STD test results (negative woo hoo!) and I sent him mine and hubby’s just in case.

I texted Vendor, no response. Not sure if he’s ghosting me or why but it sucks.

I won’t have a chance to be with anyone except my Wed night with Heidi until maybe next week. If you’d asked me if I would be this sexually active a year ago… never would have believed it.
You are doing great, we love it, and so is your sissy hubs. What did his clit do when you fucked him?
 
Had dinner with Heidi and talked so long we had to give the waitress a big tip for not letting them turn the table. (We learn stuff watching the Bear). Petted and kissed for a bit before I came home. Early doctor appt tomorrow (routine for a condition I have).
Getting along swell with her!
 
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