I had been crossdressing for about 7 months now and had finally had sex with a man and I loved it and desperately craved more!
Following our wonderful night together, I woke up to a text message from Dave saying how much fun he had and he wanted to see me again. I was so excited to read that I pleased him enough that he wanted to see me again.
The next day Dave texted me and asked if I’d like to go out to dinner some night. I wasn’t sure I wanted to go out in public dressed in women’s clothes but something about Dave made me just agree without thinking of the consequences. Needless to say I was completely taken by this man I had only spent one night with.
I arrived a few minutes early to Dave’s house so I could get dressed. I certainly couldn’t let my wife or kids see me dressed as a woman. Dave opened the door before I could even knock. It made me feel all tingly inside to know he was as eager to see me as I was to see him. He was clearly getting ready himself as he was only wearing a white tank top and a pair of boxer shorts. As I entered his house he quickly wrapped his arms around me and kissed me quite passionately. Our tongues swirled around each other for a minute or so and he held me so tightly for a minute or so before he released me.
I quickly went to his 2nd bathroom he had downstairs in his basement to get dressed. I threw my jeans and t shirt in a bag and put on a pair of red silk thong panties. I had a pair of black stocking and a garter belt I put on as well. I wore the same black dress I had worn a few days earlier with Dave because it fit so well and it really was the only thing I had for a nice restaurant. While I waited for my hair iron to heat up I rummaged thru Dave’s drawer’s and found some interesting things. There was a box of condoms, and two dildos. The first was an 8” vibrator and the second was one of those double dildos. I had no idea why he would need one of those but I didn’t have time to ponder it. I needed to get my hair and makeup done.
Once I was ready I made my way back upstairs and saw Dave standing there waiting for me. He had a nice black suit and tie on and looked gorgeous. He took my hand, kissed me once again and we left the house. I was so nervous about being in public dressed the way I was but I couldn’t stop myself from doing whatever Dave wanted me to do.
Dave is a very successful man and knew all the nice fancy restaurants in town. Normally I would’ve been scared shitless someone I knew would see me but again, something about Dave mesmerized me and I couldn’t believe what I was willing to do.
We actually had a fantastic meal and we got out to his car and sat there in the restaurant parking lot for a while.
“Did you like the restaurant?” Dave asked me
“I did. I have never been to such a fancy restaurant before.” I answered truthfully
“What would you like to do now?” Dave asked
“I wanna suck that cock you got.” I said bluntly. I had had a few drinks and my filter was down for sure.
Dave didn’t even respond, he just climbed out of the car and got in the back seat. I joined him as quickly as I could and before I could even shut the door, Dave had pulled his 9” cock out and was rubbing it. I didn’t waste time on account of what I said was true, I really did wanna suck his dick! I reached out and grabbed a hold of his member. It was already rock hard!
“Sit back and relax, baby.” I said as I placed my hand on his chest pushing him back.
I leaned down and opened my mouth and put Dave’s cock inside. It was a chilly night and his cock was incredibly warm in my mouth. I began to bob my head up and down as my lips and tongue tickled every bit of his giant cock. Dave moaned in enjoyment and each moan made me hornier and hornier.
“Oh Christ this feels amazing! I’m gonna cum so hard!” He moaned!
Dave ran his fingers through my hair and grabbed a handful and held my head on his cock. I began to gag a bit as a rush of cum splashed against the back of my throat. I coughed a bit and then Dave released my hair from his grip and as I pulled away to catch my breath another spurt of cum hit my upper lip and nose. I opened my mouth, licked it off my lip and a third and fourth spurt him my tongue. I lapped up every drop of cum he produced and immediately sat up and kissed him.
When I began this whole fantasy I never imagined I would actually go through with having sex with a man but I always imagined what he would look like. I always pictured some fem boy because I wasn’t thinking like a woman. I was thinking like the man in me. As we drove back to Dave’s house, all I could do was look at him in awe. He was nothing like the man I envisioned when I first thought about being with a man. Dave was tall, handsome, in shape, and had a mustache and chest hair that drove me wild! The 9” bird in his pants was also a major plus!!!
“Is there any way I can convince you to stay the night with me?” Dave asked as he shut his car off as we entered his driveway.
“Honestly, there’s nothing I’d love more, I just don’t know how I’d tell my wife.” I answered
“Tell her you’ve had too much to drink and are gonna stay at a friends until you’re ok to drive.” He offered as a suggestion
It was a fantastic idea and it worked perfectly!
As Dave and I entered his house and closed the door behind us, he kissed me as he was prone to do.
“I have something for you.” He said as he walked into his kitchen. “It’s something I picked up, and I hope you like it.” He added
Dave handed me a nicely wrapped gift with a tag on it that said “To Samantha.” Samantha was the name I had decided to call myself when I dressed as a woman and he took the time to make a label with that name on it. Yes, I saved the label because it was the first time I had been called Samantha by someone and truth be told, I was totally falling for this man.
I opened the package and pulled out what was inside. It was a soft silk blue nightgown with black lace trim. It was incredibly sexy and incredibly expensive as it still had the tag on it.
“This is gorgeous! You didn’t have to do this!” I exclaimed
“Well, you needed something to sleep in if you’re gonna stay here. Plus I wanted to see you wearing this!” Dave said as he leaned in and hugged me and kissed my cheek.
“Thank you! I’ll go try it on!” I said as I headed toward his bathroom.
I removed all of my clothes and put on the nightgown. It was unbelievably soft and comfortable. It went just south of my cock and tickled my tip with every step I took. As I opened the bathroom door and boldly exited, Dave was lying on his bed in just his boxers. I just stared at his chest hair for a second not hearing what he said.
“..I said, you look amazing!” Dave said with a smile.
“Oh, thank you. I love this! It’s so soft and comfortable.” I responded with a smile as I slowly climbed into bed with him.
Dave shut off the lamp beside his bed and cuddled up next to me. His hands began to explore my body and our tongues quickly found each other. My cock had been rock hard ever since we left the restaurant!
After a few minutes of foreplay and kissing Dave surprised me by sitting up and positioning himself between my legs. Before I knew it his lips were wrapped around my cock! I instantly went light headed! It had been ages since anyone had sucked my cock! Dave was a master at it as well! I could’ve shot my load in a matter of seconds but I didn’t want to! I wanted to cum with his cock in my ass! That’s what made me hot!
“Oh my god this feels fucking incredible!” I moaned “Fuck. E Dave! I need you to fuck me right now!” I cried out
Dave sat up and pulled his boxer shorts off and reached for the line on the side table next to the bed. So eager to be fucked I started stroking his cock as he fumbled in the dark to find the tube and lube up his cock.
Before I knew it Dave’s cock was inside my ass! He was so big and I was losing my mind at how thick his cock was! Dave and I were in a missionary position and he leaned down and began kissing me as he was balls deep in my ass. You always think a 9” cock will hurt your ass but when it’s the right man and he’s kissing you and his unexplainably sexy mustache is tickling your upper lip you just don’t notice how big he is.
“You’re gonna make me cum so hard, baby!” I cried out
“Do it! Cum for me!” He grunted back at me as he increased his thrusts
Just then I splashed an entire load of hot cum all over my stomach, chest and even a bit on my chin. Dave didn’t slow down as I emptied my balls all over myself.
“I want you to cum inside me! Fill me up, daddy!” I yelled
Dave pulled his manhood out of my ass and flipped me over. He grabbed a hold of my hips and pulled my ass up. Without any hesitation, he plunged all 9 inches of his cock back inside my ass. I screamed into the pillow as it did hurt a bit but in an unbelievably good way!
My cock was still dripping cum all over Dave’s sheets! He continued to pound my ass for what felt like forever.
“Cum inside me Dave! Cum inside me!” I cried out
Finally after about 10 minutes of stretching my asshole out, Dave yelled out and pushed his cock deep inside my hole. I bit the pillow and screamed as he pumped another hot load of cum inside my ass!
When Dave pulled his cock out, for some reason I just instinctively turned around and put his cock in my mouth. Not considering where it had just been I just sucked him off until all the cum how had was in my mouth. Truth be told, it was fucking incredible! His cock shot a hot load in my ass and I immediately finished him off in my mouth!
Dave and I laid in the dark covered in sweat and me covered in my own cum. We laid silently as we tried to catch our breath and then we started to kiss and full on make out. I could’ve fallen asleep right then and there fully satisfied but apparently that wasn’t all Dave had planned!
“Wanna go hop in the shower and clean up real quick before we go to bed?” Dave finally asked
“Sounds like a good idea.” I answered
Both Dave and I hopped in the shower together. I started off by gently and seductively washing his entire body.
“Do you wanna wash me now?” I asked giving Dave a soft kiss.
“Mmhmm” Dave responded
Dave turned me around and began scrubbing my back with one hand and reaching around and stroking my cock with his other hand. I could feel his cock was rock hard again as it pressed against my ass cheeks.
Just then I felt something on my lower back. As I turned to see what it was, I saw Dave was pissing on me. When I caught him, he stopped peeing. Ironically enough, the one thing my wife and I do enjoy together is pissing on each other. It’s just we so rarely do it because we only have sex 3 or 4 time a year.
Dave looked a bit shocked and frightened when he saw me turn around.
“I’m sorry. I just wanted to try something. I should’ve asked first!” He confessed
“It’s ok.” I responded as I turned around and got on my knees. “Go for it!”
Dave had a look of shock on his face for a second or two before he relaxed a bit and started blasting my face and mouth with his warm piss. Christ, even his piss tasted amazing!
I quickly popped up and grabbed a hold of his cock and placed it against my asshole again.
“Piss in my ass!” I demanded
Dave looked shocked and honestly I was shocked as well. I had no control of what I was doing apparently.
Dave pushed the tip of his cock inside my ass once again and before I knew it I could feel him pissing inside me! Why was I so unbelievably turned on by this?! My wife had passed on me and in my mouth a few times but this was just insane!
As Dave pulled his cock out of my ass, I immediately sprayed his piss all over both our legs. I turned around and kissed him and stroked his cock before I went down on him and sucked him off one more time. All in all we were in the shower for almost an hour filling around.
We finally exited the shower and dried off. We climbed into bed naked together and I cuddled up next to him. His arms were so strong and he held me as we both drifted off to sleep.
The next morning we woke up around 7am. We wasted no time in making out and I gave him another blow job which he came in about 90 seconds!
As I drove home that morning, I knew I was already in love with him and couldn’t wait to see him again! I can’t get enough of his cock and the fluids that come out of it!!!!
👄This will be the best oral sex you have ever experienced.👅