I had recently rediscovered my kink for dressing up in women’s clothing but I didn’t see it going this far.. and I’m glad it did!
I had started dressing up in my wife’s clothes while she was away for a funeral and I couldn’t believe how much I enjoyed it. I did it all the time as a kid. Mostly in my mom’s underwear and lingerie.
Another thing I discovered was how much I enjoy a dick in my ass. I used my wife’s dildo more in 3 days than she did in the last year I’m guessing.
My wife and I barely speak to each other let alone have a normal sex life. I’ve never met anyone that has a lesser libido. We probably have sex 3 or 4 times a year. She just doesn’t want sex.
I however have an enormous libido and am up for just about anything. Using my wife’s dildo on my ass was something I hadn’t expected to enjoy but I did! It wasn’t something I had never done, just something I hadn’t done in many years. Rediscovering how much I enjoy it sent me searching for something more.
About 6 months had passed by since I started dressing up in women’s clothing. I had assembled a small wardrobe of lingerie. I was now wearing women’s panties under my boxers everyday to work. On colder days I’d even wear a bra under my hoodie. To the best of my knowledge no one knew about it. I had even acquired two toys that I played with. One was a prostate massager that had some intense vibration. When I use that I spray cum everywhere! The other was a realistic dildo that was 7”. I love sticking the suction cup on a chair and just riding it until I cum!
I soon found that the dildo and massager was great but sometimes it just wasn’t enough. There was something telling me to find a man to have a secret relationship with.
I have a gay friend that I grew up with named Carlos. Him and I have known each other since 3rd grade and yes, Carlos and I have had sex many times, all of them when we were teenagers though. Once I met my wife we put a stop to us. He taught me a great deal about sex though. We used to give each other blowjobs as far back as 8th grade. By 10th grade he was letting me fuck his ass every time we hung out. Carlos is a total bottom though. In all our endeavors, he has never once asked to penetrate me.
As more and more weeks went by my desire for a man grew stronger and stronger. To the point where I knew I had to tell Carlos. He’d never judge me for anything, especially something like this. When I finally told him what I had been doing for the past 6 months he was a bit shocked, just because we haven’t spoken about this kind of stuff since our early 20’s. We’re now in our early 40’s!
He took me to a couple of gay bars that he frequently visited and after a few times I wasn’t having any luck. Carlos suggested that I come to the bar dressed like a woman, and maybe it’d attract more attention. I was extremely opposed to that idea. No way was I going to go out in public like that. The chance I ran into someone I knew was too great.
A few weeks more went by with not much luck. I had plenty of guys come sniff around at the bars but they just weren’t what I was looking for. Then out of no where my luck turned!
I am a bit of a handyman and I answered a request online to install someone’s TV wall mount. I had done stuff like this round the neighborhood for years so it was nothing new or special. Just a way to make a couple extra bucks.
I knocked on the door and as it opened I immediately was lost for words and stumbling thru sentences trying to say something coherent. The truth is, when the door opened, the man standing there in front of me was exactly the picture I had in my head of what I wanted.
His name was Dave. He was a few inches taller than I was and had black hair with a few gray hairs mixed in. He was athleticly built and had a thick black mustache and a bit of a 5 o’clock shadow as well. He was a man’s man looking fellow. I had no idea why I thought he was so gorgeous but I did! He certainly didn’t look like he needed help putting up a TV mount.
While I was placing his wall mount up, Dave confessed his lack of handyman skills. He was a civil rights lawyer and had no time for learning how to do things like that he said.
“Great job. Thank you for putting that up for me.” Dave said as I put away the last of my tools. “Wanna a beer?”
“Sounds good, thanks.” I answered
As we began to talk, I started to notice no pictures on the wall of a family. No signs that anyone else lived with him. I began asking him questions about himself and to my surprise he came right out and said he was gay and didn’t have time for a family either.
The mood changed quickly after that. Perhaps it was me that began flirting a bit. I didn’t want to flat out tell him how much I wanted him but I didn’t want to leave without something to happen.
“Thanks again for the beer.” I said trying to keep the conversation going.
“No problem. Thanks again for the TV mount.” He said with a grin and a look like he wanted to say something else but was too shy.
I’m the most shy person on earth so I know what it looks like when another shy person has something to say but is too scared.
“What?” I asked
“Huh? Oh nothing.” He responded looking down at his feet.
“You sure? My wife says my only good quality is I’m a good listener.” I said which was total bullshit but he doesn’t know that.
“Oh it’s nothing, don’t worry about it.” He said as we made our way to the door.
I put my shoes on, and left. I made it halfway down his driveway before I heard his voice yelling at me.
“Hey, you left a tool behind!” Dave yelled
I turned and headed back to the door and Dave ushered me inside and quickly closed the door behind him. As I turned around to face him to ask for my lost tool, Dave leaned in and kissed me.
“What the?!” I yelled as I pulled away.
“Oh my god! I’m so sorry! It’s just the vibes you were giving off and I happened to see you have women’s underwear on when you were putting up the TV. I’m so sorry! I feel like an idiot!” Dave frantically explained
“Yeah.. you saw the panties huh?” I asked in a shy quiet voice.
I went on to explain everything to him. It was like he was a psychiatrist and I was just dumping all of it on him. Honestly I felt bad for doing that but he didn’t seem to mind.
“I’m sorry I reacted like that. I just wasn’t prepared for it. The truth is as soon as you opened the door I was so nervous. You looked exactly like what I have been searching for.” I confessed
Dave leaned in and gave me another kiss. This time I was plenty ready for it. I quickly wrapped my arms around his waist and he put one hand on my hip and another on my cheek. Our tongues began to swirl around each other like two dancers perfectly synchronized. His thick mustache tickled my nose. As I pulled away to get a breath of air his hand slid down the back of my jeans and felt the panties I was wearing.
“Lace huh?” He asked
“Mmhmm” I muttered heading in for another kiss.
We stood in the entryway making out for almost 5 minutes.
“I really should get going.” I said
“Can we get together soon?” Dave asked
“Of course!” I replied
I gave him my number and I drove home. I couldn’t believe what had just happened! As I drove home I was even more shocked that we didn’t do anything!
When I got home I immediately texted Carlos and told him what happened. Then, as soon as my wife went to bed, I grabbed my dildo and fucked myself in the ass with it. I was so turned on that I didn’t bother dressing up and I came immediately! After I shot my load I just kept riding that dildo. All I could think about was Dave’s cock! I didn’t care about my cum, I wanted to make him cum so badly!
The next day Dave texted me and asked if I wanted to come over that Friday night. I agreed as emphatically as I could! I was extremely nervous about the whole thing though so I called Carlos and had him come over after work Thursday. Carlos was a regular at my house so my wife certainly didn’t think anything odd about him being there which was good.
We retreated to the basement and I grabbed Carlos and just told him..
“Let me suck your dick!” I butter out
“What?!” He said laughing
“I need to practice for tomorrow night. I know we haven’t played around in years but I need your help.” I begged
Carlos agreed. I mean who would turn down a blow job? So Carlos sat down on the couch and I got on my knees and started sucking on his knob. I hadn’t done this to him in 20 years. It was extremely odd but I got a handle on it quicker than I expected to. Carlos gave me some tips as well just before he shot a hot load of cum in my mouth.
“You did well man. Not bad at all.” He said with a giggle as he pulled up his pants. “ I think you’ll do just fine tomorrow. Just don’t be nervous. Go with it. Whatever happens, happens. Let him be the man.” Carlos explained
I took everything he said very seriously because I was extremely nervous.
I sent Dave a text saying I was on my way but needed some time to get ready at his place. I couldn’t leave the house wearing what I had planned. Told my wife I was going to have a few beers with some friends and then I left. When I got to Dave’s house I sat in my car for a minute two just trying to slow down my heart. He saw me sitting there and opened his front door and gestured towards me to come inside long before my heart slowed.
As I entered his house he once again closed the door behind me and kissed me. Not as intense as the other day but just a welcome kind of peck. I saw a bottle of wine and a couple glasses sitting on the table. He then showed me to the bathroom where I could ready myself.
I sat in the bathroom for a few minutes doing nothing still trying to slow my heart. It began to work as I started running through the advice Carlos gave me about just going with it. Whatever happens happens right?
I removed all my clothes and opened the bag I brought. I first put on the same black lace panties I had on the other day. It came with a matching bra but I didn’t bring it. I pulled up my pair of black silk stockings. Slipped a black dress that I stole from my wife on. I had spent the last 7 months growing my hair out so it had gotten long enough to make it look something like something a woman would do. I put on a bit of makeup and lipstick and stared at myself in the mirror for a solid 3 minutes. Finally took a deep breath and exited the bathroom.
Dave was sitting on the couch with his legs crossed as I entered the room. He had moved the wine and glasses to the coffee table in front of him and offered one glass to me.
“You look incredible!” He said handing me a glass of wine.
“Thanks.” I said blushing
Dave ushered me to the couch and sat beside me. We drank our wine and began to make small talk. I kept the small talk going as long as I could because I wanted more wine to relax me. After my 4th glass of wine I felt much more calm. Calm enough to place my hand on Dave’s thigh. His leg was solid. I could tell he was a gym guy or at least a runner.
That’s seemed to be all Dave needed as a sign, because as soon as I gave his leg a soft squeeze, Dave set his glass down, took mine from my hand and did the same and then leaned in and kissed me. Just a few soft pecks at first but then he plunged his tongue as deep into my mouth as he could. I moaned softly as he began to take control of the moment. He held me in place with his hand on my cheek once more but my hands were exploring his body. I started squeezing his arms and they were just as toned as his legs felt. Then I ran my hands up the back of his shirt and rubbed his back. It was soft skin and toned as well.
Just then Dave backed away and unbuttoned his shirt and threw it on the floor. He had a beautiful patch of chest hair that just sent me to the moon. I immediately started running my fingers through it and kissing his chest. I looked down and saw an incredible bulge in the tight jeans he was wearing. My cock had never been so hard before and I had never been more nervous in my life. It certainly looked like he had one hell of a bird in his pants.
Dave quickly stood up and grabbed my hand and pulled me to my feet as well. He ran his strong hands up my dress and lifted it over my head and threw it next to his shirt on the floor. He pulled me close and we started kissing again. His chest hair pressed against my bare chest felt soft and his hard cock pressed against my equally hard cock.
I couldn’t take it anymore. The suspense was making me more and more nervous so I just reached down and unbuttoned his jeans. Dave took a step back and pulled them down and kicked them to the small pile of clothes we were making. Sure enough, Dave had a huge cock! At first glance it looked big! As I took it in my hand I realized that it was definitely bigger than mine and bigger than my dildo.
“Wow!” I said as I looked down at his giant dick sitting in my hand
“You’re not so bad yourself.” Dave said as he grabbed ahold of my cock that had slipped out the side of my panties.
Dave then sat down on the couch and opened his legs apart. I didn’t need to ask what to do, I knew exactly what he wanted. I nervously got on my knees in front of him, placed my hands on both his legs and opened my mouth. Dave thrusted just a bit to get his cock inside my mouth and then I grabbed a firm hold on his shaft. Once inside my mouth I realized that he had at least 9” of thick meat.
As I continued to suck on Dave’s member, I became more and more worried about him entering me. Could I handle this?
Dave stood up and told me to lay down on the couch. I got more nervous! Then he positioned himself in a 69 above me and started sucking my cock as well! Wow! He was really good at this!!! He was so good that I momentarily forgot that his big dick was dangling in my face. As I snapped out of it, I opened my mouth and put his cock inside. Dave began to gently grind. He was fucking my mouth now. Since I had free hands I reached up and squeezed both of his ass cheeks. We 69nd for a few more minutes before Dave sprung up!
“I can’t take it anymore!” He grunted
Dave pulled me to my feet and lead me to his bedroom. I laid down on his bed and he grabbed something from his dresser. It was lube. The moment was here!
“I’ve never done this before!” I blurted out
“It’s ok. I’ll be safe and gentle.” He reassured me
He did exactly as he said. He placed a glob of lube on his cock and gently wiped some on my asshole. Then he pressed his cock against me and gently pushed. I wasn’t new to anything in my ass, just not an actual man’s cock.
As his tip popped inside me I let out a gasp. Dave once again reassured me and calmed me as he pushed a little further in. It helped we were in a missionary position and he leaned down and we started making out once again. After a minute or so of our tongues swirling around each other, I didn’t even notice he was fucking me. I had relaxed so much that it didn’t hurt a bit. When I did finally realize his cock was sliding in and out of my ass I moaned really loudly. It felt fucking insane!!! Nothing like a dildo!
“Still ok?” He asked
“God yes!” I yelled out
He then lifted my legs up in the air and began thrusting a bit more aggressively. I could see my stomach moving from his cock being inside me. Something I did not expect but absolutely loved!
“Oh god! This is amazing!” Dad exclaimed
Something came over me at that exact moment. Knowing that I was pleasuring him that much just made all my nerves go away. I was fully committed to making this man cum harder than he ever had! I pushed him off of me and sat up. I then plunged my tongue into his mouth for just a few seconds before turning over and posturing up on all fours.
“No more safe and gentlemanly shit! Fuck me! Fuck me hard and fast!” I demanded
Dave grabbed ahold of my hips and positioned himself behind me. I had dreamed of being fucked doggy style and it was about to happen.
Dave’s cock slid right back inside of my eager hole. I let out a loud groan and pushed my head face down into his pillow and screamed.
“Fuck me!!” I screamed
Dave’s grip on my hips tightened and his thrusts were fast and deep! His cock slid in and it of my ass so fast I thought I was going to pass out. I could feel the veins in his dick as the went in and out. With my face buried in Dave’s pillow I feel one more aggressive thrust. Dave’s cock was as deep as it could get inside my ass. I could feel every spurt of cum he had hitting my inner walls of my ass. I felt his cock throbbing as each pump of cum passed thru his cock and into my ass. I continued to moan into his pillow.
Dave finally pulled his cock out of my ass and instantly I felt his cum dripping down my legs and balls. I could see thru my own legs drop after drop of his cum pouring out of my ass and down my leg finally making a small puddle on his bed. Dave collapsed next to me covered in sweat. I was still on all fours trying to settle myself. My asshole hurt after his monster cock fucked it for 10 minutes.
When I finally laid down next to Dave, the sweat in his chest hair glistened as the light hit it. It reminded me of exactly what I wanted that night and I didn’t care that my ass was a bit sore. We kissed some more and eventually fell asleep.
I woke up around 2am and it was pitch black in his room. Dave was asleep next to me and didn’t wake as I climbed out of bed. I didn’t want to wake him up but I had to get home. I left a message in his bathroom mirror in lipstick that said.
“Thanks for the best night of my life! Can’t wait for the next time!” Then I kissed it 💋
I quietly crept out of the house after cleaning myself up and drove home. When I got home I went to the basement, put my stuff away and stroked my cock for an hour. I came 3 times but I didn’t care. All I could think about was letting Dave fuck my ass again and again!
👄This will be the best oral sex you have ever experienced.👅