I just melted. [MM] [Crossdressing] [First time]

Note: this my first attempt at a story. feedback and pm’s welcome

When I think back to that fateful day this past June, it all makes sense. At the time, I didn’t see it coming. My name is Dave and my wife is Connie – I’m 42 and she is 39. We lived a great life and early in our marriage folks would have said we were a great couple and that we were both very successful. I was an executive at a national insurance company and Connie was a VP at a fast growing biomedical company. I was rising fast thru the company back in my 20s and Connie was the receptionist at a two person shop fifteen years ago. Truthfully my career was stalled and Connie was rising.

I’m 5’8″ and about 160 and in my 20s I had been in great shape. I’m still slender and in fact I’ve been getting softer for years. I let my hair grow out and I make sure to have nearly no body hair. I’ve always had a thing for dressing up in womens clothing – it has always been my secret thing. I always considered it a fetish, something that I got off on, not that I was going to act on it.
With Connie gone on business trips more often, I was able to do my absolute favorite thing – shop for panties and womens clothing. The thrill of entering the womens section of the store and the first touch on that panty rack is something that nearly brings me to the edge each time.
I had a nice stash of clothing and since Connie had me do the laundry, I could wear pretty things nearly every day if I wanted to.
Oh, Connie and I still had sex (sometimes) on her schedule and really basic stuff. I always got the sense that my average penis (5 inches or so) just didn’t get her off.
So this fateful June day Connie called on her way back from the airport and said, “Get dressed – we are going to Ryan’s for a party.” So, Ryan is Connie’s boss. He is a complete alpha male, he’s 35 and 6’2″ and about 210. He is a crossfit nut and is just fit and ripped. He and I get along although there is this little fiction about my high flying career which is decidedly no longer high flying.
I’ve been staying dressed more, and before I got her call, I had just put on a new panty and bra set. I had given up that early thong fetish and just loved my new bikini from aerie wildflower-lace and matching bralette. I was feeling good after a nothing week at work and I looked great in these new pretty things.
When Connie called and said to be ready in 30 minutes to go to a summer party at Ryan’s, I just couldn’t imagine taking these off. Could I leave them on?
Yes.
I put on my shorts and a short sleeve button down shirt and turned around in the mirror. The panties were fine, the bralette was so thin that it didn’t show thru. I was going forward with this!
We got to the party at Ryan’s house, well really a mansion. It was a huge house with a huge number of guests. They were sitting by the pool, lounging in the first floor rooms which seemed to be just for parties.
Ryan saw us as we came in and I’m pretty sure his eyes lit up when he saw Connie. I glanced over at her and her “tell” was there, her nipples got instanly hard. Her form fitting dress had two clear pokies. She *was* fucking him. Now I am sure of it.
He greeted us warmly and we joined the party and grabbed some drinks off of a server’s tray and the party over took us.
About an hour in to the party, Ryan and I found ourselves in hallway. He grabbed my shoulder and said “Davie – let me show you my new space downstairs, it is going to be incredible.” He opened a door I didn’t know was there, and we went down a winding staircase. He was in full tourguide mode. “Here is the new home theater, here is my new wine cellar, and this is my favorite new room, the billiards room.” We entered a big room that clearly was not quite done, it smelled of wood finish and a ladder and tool box were in the corner.
The pool table was incredible, clearly an antique full size table. Ryan explained that he purchased it from a famous Boston private club and had it restored, that it was one solid piece of slate, etc. I asked if we could play a game. His blue eyes lit up.
We played a few games actually, I won the first, he the second. I had a tough shot across the huge table to win the third game. I had to lean on the table and in fact had one leg up on it, I could barely reach by stretching out – but I made it! I won two out of three.

I turned to look at Ryan, thinking he’d be mad that he lost in his new billards room, but he just had a smile on his face. In fact it was the same look I saw that got Connie so hot about an hour earlier.

I walked up to Ryan to shake his hand and say good game. This is hard to explain, but somehow when I reached my right hand out to shake his, he took it with his left hand. At that instant, I felt different. He led me, just like a man should do with his date, he led me into a kitchenette off the billiards room. He let me into the corner of the cabinets, this beautiful new room, in this beautiful cellar.
At that moment I was just his, I was waiting for him to speak, my small hand was in his firm mitt of a hand. I had never been led like that before. My knees, no my whole body was weak. He looked in my eyes for a moment. I needed him to say something.
I still didn’t know what made this transformation, briefly thru my cluttered brain a thought crossed my mind, that this was somehow to do with the pool match, that he was going to show me something in here.
That wasn’t it.
He said, “I saw your panties when you made that last incredible shot.”
I blushed, my face turning redder that I can ever remember. I looked down at my feet, they looked so little next to his.
Those were his last words. He didn’t walk away. No not even close. He unbuttoned my shorts and let them drop to the marble floor. He reached down and carefully had my nearly smooth legs step out of them. I remember watching him turn around and carefully fold them and place the shorts on the kitchen island. He then unbuttoned my shirt. When he saw my bralette he let out a little gasp, it was then that I noticed the bulge growing in his shorts. He took off my shirt in the most gentle way, again carefully folding it and placing it on top of my shorts. I let out a little shiver. It wasn’t cold down there, my body was just shaking slightly. He moved towards me, right in my space. I looked up at him, I could smell him, a mixture of expensive but subtle cologne and what can only be experienced, his musky scent.
Now what. Should I run? Cry? Tell him the underwear was a dare?
He seemed to sense my panic, and at that moment I was lifted, I still don’t really know how he did this, but he lifted me up and placed my pantied ass gently on the counter. My legs naturally opened for him. He looked in my eyes and actually pushed my hair back behind my ears. He then leaned down and kissed me.
I just melted.
I’ve never been kissed like that, it was sensual, and strong, he tasted of single malt whisky and power.
He leaned down, and pushed my bralette aside and sucked on my left nipple. I know it was my left because my right one will never get over missing out on that feeling. He had one hand moving down my smooth belly and toward my pretty panties.
No word for me are the same after this.
Before this party, I would have said he reached in my panties and stroked my cock. Now those words ring hollow. What I now say is that he reached in my pretty panties and stroked my boy clitty. His massive hands were able to rub that clitty. He stopped for a moment to lick his middle finger, he went back in my panties, I moved forward to give him access to my boy pussy. But he didn’t take me. He just touched the rim, and I guess felt how tight it was. If he said anything, I didn’t hear it. My little boy clitty was cumming right as he touched my boy pussy. It mostly stayed in my pretty panties.
I hopped down and moved him back into a barstool. I could smell his manhood and could see the bulge, but i needed to see it to feel it, and yes, to taste it.
I made a move to unzip, he stopped me. He was in control. He unzipped. He pulled down his tight boxer briefs.
Oh my god.
It was massive and beautiful. It is hard to explain, it had a life to itelf and was still growing. This uncut cock was the most beautiful I had ever seen. I leaned down and the smell hit me. It was incredible and made me want it even more.
I grabbed the massive cock with two hands and gave it a kiss, like a girl giving a blowjob for the first time *which of course was exactly what was happening*
I took it in my mouth. It filled me up – I took as much as I could and found that I do not have a gag reflex. I took a third or so and did my best to get him off. I wanted to get him off. I needed to get him off.
I did.
He gave me signal and his balls tensed up and I had the huge head of his cock just inside my pretty mouth. He errupted in me. I was determined to swallow it all. I’ve tasted my own cum on occasion, but his was so different. It was thick and full and tasted salty and complex. I felt so proud to be able to take all of Ryan’s load.
Now what.
Was this going to be the guilt of an illicit sex act. The turning off of the porn after cumming as if you weren’t just jerking it to two guys? I looked up at Ryan slowly. Half expecting him to be leaving the room already.
No. Not Ryan.
He leaned down, kissed me on the cheek. And said, “That was wonderful. I look forward to a real date in the future. There is a guest room down the hall. You’ll find a tooth brush and swimming trunks that will fit you. Leave the panties and the bra in the hamper, I’ll be finding a special place for these.” And then he left. I was frozen there, and noticed for the first time a mirror across the billards room that framed the kitchenette. I saw a beautiful girl there, glowing in a pretty bra and panty set.

Source: reddit.com/r/sexystories/comments/9crfx9/i_just_melted_mm_crossdressing_first_time