I confessed my big secret to my cousin and got one hell of a surprise.
I’m a married man in my early 40’s with kids. My wife and I have been more or less going through the motions for the past 10 years or so. Keeping it together for the kids.
About a year ago, I rediscovered one of my kinks from my teens. Cross dressing! I absolutely love dressing in women’s clothes, whether it’s lingerie, dresses, jeans and a shirt or even just some girly pajamas to lounge around in. I have been wearing a bra and panties every day to work for almost a year now with no one knowing.. at least I think no one knows.
Cross dressing lead me down a path where I met Dave. Dave is my boyfriend that I know no one knows about. Dave is a handsome man with black hair and a little gray, a toned body with a perfect patch of chest hair and the sexiest man’s man mustache you’ve ever seen. He’s been so good to me and I can’t believe how much I love him already.
That being said..
When I was in my early teen years and discovering all these kinks I have, my cousin, who is a year older than I am lived right down the street from me and him and I hung out a lot. It was with him that all this started to be honest. We would look at porn magazines that we’d find or steal from our dads and then masturbate together. When I was 14 I showed him my small collection of women’s lingerie that I had stolen from my mom and older sister and modeled it for him. Even going as far as getting out one of my mothers dildos and sucking it while he watched and jerked off. We never did anything physical with each other just did solo stuff in front of each other.
About a month ago, my cousin came over to watch the Super Bowl. We had been drinking but weren’t drunk, and after the game we went downstairs to drink and bullshit some more. I don’t know if the beer got to me or it was just that it was him, but I asked him if I could tell him a secret and he said yes. I told him everything! My cross dressing, my boyfriend on the side.. everything. I even admitted to losing 30 pounds this year to have a more girlish figure. I wasn’t that big to begin with but now I’m down to 140 pounds.
His curiosity lead him to ask question after question and I answered every one of them honestly. Eventually he brought up the night when we were kids that I mentioned, where I modeled for him.
“Do you want me to show you what I have?” I asked worried he’d freak and leave and spill my secrets
“Sure. I’d love to see it.” He replied trying not to sound to eager
I went into this closet I have downstairs that has a toolbox and inside has some clothes, some makeup, and my toys. First I ran a brush through my hair, which is now past my shoulders. I spread some lipstick on, and took my clothes off. I only have one pair of white thigh high stockings that I pulled up. I grabbed a pair of white cotton panties and silky red and white lingerie top that Dave had gotten me for Valentine’s Day. I took a deep breath, exhaled and opened the door. My cousin was sitting on the couch and his jaw dropped and he said nothing.
“Well?” I asked
“Jesus, you actually look good! Like a real woman!” He replied
His response was welcoming enough that any shyness or scared feelings I had started to go away and I began to catch my breath now.
I went into my toolbox and grabbed one of my dildos, and I thought I’d give him a quick little show like I did when we were kids. I stood in front of him and began dancing a bit. He seemed receptive to it so I took it a step further and started giving him a lap dance. As I grinded my ass against him I could feel his cock and how hard it had gotten so again I decided to take it a step further. I got on my knees between his legs, placed the dildo where his cock would be and began sucking it. I felt his hand on the back of my head as I bobbed up and down.
“Wow! What are we doing?” He asked a bit flustered
“Whatever you want.” I replied
He pushed the dildo aside and unbuttoned his jeans. I grabbed ahold of them and tugged them down to his ankles. When I looked up, my eyes nearly jumped out of my head. He had one of the biggest dicks I had ever seen! I remember him having a big dick when we were young teens but now it had matured. He was at least 10” and thick! I honestly couldn’t believe what I was looking at!
“Good god, grown a bit since we were kids have you?!” I asked staring at his manhood
“Do you like that?” He asked
I didn’t verbally respond, I just grabbed his shaft and put his cock in my mouth. He let out a breath like he hadn’t had his dick sucked in years. His body sank into my couch and his head rolled back looking up at the ceiling. I slowly bobbed my head up and down his cock trying to get it as far into my throat as I could. I’m not the best at deep throating. Then I danced my tongue around the top of his cock and began to taste a little pre cum. I didn’t want him to cum 30 seconds in so I slide my mouth down to his balls and sucked on them for a minute or so gently stroking his shaft.
“You like this?” I asked looking up at him still holding his cock
“God yes! It feels incredible!” He exclaimed
In the 3 minutes since he took his cock out I noticed a change in his behavior. He went from, kind of stressed and quiet all night to a very relaxed, calm guy. I found out afterwards that he hadn’t had sex with his wife in almost 2 years and was very frustrated with her and their sex life. His change in demeanor is what made me continue. The further I went, the more normal and relaxed he got.
“So… are you gonna fuck me with this big monster or what?” I asked sitting back on my heels and putting my hands on my hips.
His eyes were locked on the tip of my cock sticking out of the top of my panties and it seemed like he didn’t hear what I just said. I stood up and pulled my panties down and kicked them aside. My cock pointed straight at him.
“Well?”
“What if you wife hears us?” He asked snapping out of his mini trance.
“She’s sound asleep upstairs, we’ll be just fine as long as we’re not screaming.” I answered with a smile and a little laugh
I quickly ran into my closet and grabbed some lubricant and darted back into the room where he had removed all of his clothes already. I took off my lingerie top and left my stockings on.
“How do you want me?” I asked
“Lay on your back!” He said biting his lip a bit
I laid down on the couch and put my head on the arm rest. I squirted some line in my hand and put it on my ass, then his cock. He positioned himself between my legs and pressed his cock against my ass hole.
“Are you sure about this?” He asked
“Stop worrying. I want this!” I answered running my hand down his chest and stomach.
He pulled my legs in the air and put them on his shoulders. Pressed his cock firmly against my hole and began sliding his meat inside me. When his head popped inside I bit my lip so I wouldn’t be too loud. Not gonna lie, it hurt for just a second or two.
Once he was a little deeper inside I began to relax and take him. He began thrusting a little harder and a little faster each time. I was basically curled up in a ball as my head was pressed to my chest by the arm rest and my knees were up to my face, my cock was almost to my chest. Then for a second I got some room to breathe as he pushed one of my legs aside and I quickly wrapped it around his lower back. Then he started to choke me. Not hard but it was aggressive enough to limit my breathing a bit. It was the first time anyone had done that to me and I was shocked at how much I was liking it.
His thrusting increased rather quickly and all of the sudden he let out a muffled grunt, plunged his dick as deep as he could and began pumping load after load deep inside my ass! I could feel the intensity of each spurt of cum hitting the inner walls of my anus. He had shoved his 10” cock all the way inside my hole and just held it there for 30-40 seconds.
“I can’t stop cumming.” He mumbled quietly to me
“That’s ok. I love it! Keep it going!” I encouraged him
When he finally did pull out, a quick whiff of sweat and ass filled the room, I wasn’t expecting to get fucked so I didn’t really do any kind of prep work on my ass. I look down and there was still small spurts of cum dripping out of his cock and what felt like a river draining from my hole.
Not wanting to cover my couch in cum, I quickly popped up and ran to the closet where I had a couple towels to clean up with. By the time I got there, which is only about 15 feet from the couch, there was a trail of cum going down both of my legs and had reached my ankles. I couldn’t believe how much cum he produced!
“Is this gonna be weird between us now?” He asked as I entered the room still wearing my stockings and nothing else.
“It doesn’t have to be. It is what we make of it. It’s important to know that I have a boyfriend and I do love him so I don’t think we should do this again. At least not while I’m still with Dave.” I explained
“I understand. It was fun though.” He said as he pulled up his pants.
“Yes it was!” I said as I walked over to him and gave him a kiss on the cheek.
It’s been a month or so and I haven’t done anything else with him. Dave and I continue to see each other a few nights a week behind my wife’s back. Sex with my cousin that night was pretty good, but with Dave there’s emotions behind it and I have grown to love that.
When Dave and I have sex it’s very passionate and sensual but having my cousin choke me kind of got me off. Think I’ll see if Dave is interested in doing that. I do enjoy being used and treated like a fuck doll!