Crossdressing Cougar

Friday night is my favorite night of the week. Everyone is looking to blow off steam and try to get laid. After a long week of work at the mall. I work in the clothing department and it's next to Victoria's Secret, so I can get some lingerie cheap.

I collected a vast amount of lingerie and sexy outfits. Tonight, I'm going out to a local club to find my favorite type. That type would be young and hung. Of course, I can live without a big dick pounding me. I just like them young around the early 20s.

Usually, older guys like crossdressers like me, but once in a while, a young guy decides to try some mature ass. I have the perfect outfit for tonight laid out. A snug fitting black mini dress that has long mesh sleeves, black thigh-high stockings, a garter belt attached to my corset, and a nice pair of black pairs of he

I'll be wearing a long blonde wig to finish my outfit. In my purse, I have lube and several condoms just in case. My legs are the eye catchers. They're long and muscular like a natural woman. I wear a padded brasserie to give the illusion of big breasts.

My ass is plump and actually firm. It's not bad for a 54 year old in my opinion, as I stare myself down in the mirror. I head out the door to my car. Along the way, I text my friends to see if they're coming or not. Only one was going to be there for a bit, Sarah was my go-to when stud hunting. Sarah was a few years younger than me and is also a fellow cougar.

I reach the club and pay the bouncer for entrance. The club was loud and crowded as usual, with the crowd consisting of college students. Drunk horny college students were the main patrons here. Just give a college guy some time and a few drinks, then he's up for anything. Usually, that is where I come in and give them a hot, rememberable night.

When I arrive, the first thing I typically do is go to the bar and order a daiquiri. Then I scout around looking for a cute young guy who's looking for a fun time with anyone. Well also there's times guys usually come to me and start flirting with me. Those guys are usually the best lays because they're not afraid to get laid and take charge.

I sit at the bar, sipping my drink and texting Sarah about the guys here. Her type is similar to mine, except she prefers guys who are a little older than my guys. I look up from my phone and continue to search for my stud of the night. Then I look at the booths near the back and see a group of guys who wore matching jackets of a sports team.

They were from out of town and very athletic looking. I see they were splitting off little by little, and I was searching for one who was by himself. Finally, this gorgeous and tall black man was heading to the bar not far from me. He stood easily 6'3 "or 6'4" with strong shoulders and medium length braids. He was muscular and walks like his muscles are on showcase.

Strangely I never been with a black man before, but now I'm feeling like tonight might be a night to try something, or I mean someone new. I lean back against the bar and let my legs shine out to him. At first, he didn't notice and just walked to the bar literally 10 feet away. He was ordering a drink, and as soon as the bartender heard him, I cut in and said to the bartender, "Put it on my tab, Joe."

Joe hears me and pours the drink. The cute guy hears me and stares my way. I turn my body towards him and continue to let my legs do the talking by slowly crossing over each other. He gives me a quick look around my body before taking his drink and heading towards me. He sat next to me and introduced himself to me. "Hello beautiful, the name's Benjamin, but my team calls me Big Ben."

I feel myself blush, and my body is tingling with excitement before answering, "Hey Big Ben! Good to meet you. My name is Darlene. My friends call me Darla, and hopefully, after tonight, you call me Darla as well."

He smiles and moves a little closer to me. "Darlene, huh? I thought it would be Tina Turner with those sexy ass legs." I subtly push him in an affectionate way. I let out a small giggle to go with that push.

"I wish her legs are legendary! By the way, why are you checking out my legs when my eyes are here!" I point towards my face. He definitely likes what he sees, and I'm glad he does.

"Well, it's hard not to look at those legs. If those legs look that good, it has me wondering if the rest of you look good, too?" He leans back wondering what will I do next. I stand up and do a little turn to show off my body and outfit.

"ok, ok. The rest of you looks great, too. You want to sit with me at that booth in the back?" I nodded yes and we both get up. We headed to the back of the club and sit together in a booth.

After a hour or two of talking and flirting, we're both starting to get closer to that point. Occasionally he'll touch my legs or caresses my face affectionately. He figures out that I'm a crossdresser and it didn't seemed to bother him.

"You know I'm leaving tomorrow night and I like to keep in touch with you. How about you give me your number and we can keep in touch."

"Oh honey, I don't give out my number. Nothing against you, but you young guys only want numbers to get us old women in bed and never call." I say to him while massaging his hand on the table.

"Well we can be in touch and maybe we can date or something. Don't worry, I'll call you after we hit bed tonight."

After he said that, my body was instantly going crazy and I really wanted him now. Still I had to be cool and keep him trying to seduce me. From what I learn in my life is that once you let a young guy get too confident, he'll stop trying to do anything.

Even after sex, you never let him know that he was great. Just say something like "not bad, still not great but you're getting there" or "you did good, hopefully better next time." Its not to hurt them, but encourage them to try to do better. Being young and wanting to fuck all the time doesn't make them better. So a little encouragement and a challenge will make them try harder.

"Sorry honey, I'm not trying to date. As for thinking you were getting me in bed, what makes you so confident that you're ending up in bed with me?"

"You're saying that you're not thinking about it? Because if you say you're not thinking about it, then you're definitely lying. I understand if you don't want date, but we both definitely want to fuck!".

He pulls my face to his and our lips join together. Tongues take turns in each other's mouths and our hands start groping. His right hand was under my dress, squeezing my ass gently. My left hand started feeling his crotch with curiosity of the stereotype of black men.

I learn that the stereotype fits Ben well. Maybe that's why they call him Big Ben? From what I can feel, he was long and thick like a python. He slowly pulls back from my lips and asks "so do you want me to... well you know?"

"Are you asking if I want you to bottom too?"

"Yeah, I mean I'm down for hitting this ass and shit, but I don't know about the other thing?"

"Honey, I do all the bottoming. Your job is to use your big dick on me or technically in me."

He lets out a sigh of relief and chuckles. We go back to kissing and feeling each other up for a little longer. We decided to go back to my place and go all the way. In the car on our way back to my place, he would suck on my neck and fondle my legs like a eager child wanting to rip open a present on Christmas.

He almost made me pull over and fuck him in the car. Like young guys before him, they were very eager to fuck and would show it like the way he was doing now. I love this attention young guys give when they're horny and ready. Older guys are so cool and confident in their ways, so they rarely try to be affection or show interest even.

Soon as we arrived, he quickly runs out and even opens my door to let me out. I open my house door and he quickly pulls me back to him to kiss again. We barely closed the door and he lifts me up by my ass. He holds me up against the wall and kisses me like a wild animal.

"Slow down honey, save your energy. My bed is in the room, let's try to make it there first before you hump me to death."

He causally carries me into the bedroom without breaking a sweat, showing his prowess as a athlete. He lays me on my back on the bed and steps back to start stripping off his clothes. I join him by slipping off my dress and panties to leave on my other lingerie.

For the first time I see his erected cock, it was close to 10 inches and thick like a wiffle ball bat. It pulsated with excitement and eagerness to be pleased. I lay a pillow on the floor in front of him and get on my knees on the pillow. I massage his muscular body from his chest down to his hips and around his cock.

"I hope you don't blow your load fast, I like to see what you can do with this beast."

"Oh yeah? Tell me you think you can handle Big Ben? Most girls tap out in a few minutes and I hate to see you tap out." He boast confidently.

"You hear what you said? Girls not women, and honey I'm a woman!"

I start massaging his cock slowly while I suck the head. I release tons of spit out of my mouth and rub it down his shaft. He lets out low groans and gasps of pleasure between each of my strokes. I slowly let a few inches of his cock in my mouth and keep sucking. He starts slowly pumping his hips as I continue sucking.

I let more of his cock in my mouth until it hits the back of my throat and I adjust my body downwards to let his cock go down my throat. I grab his hips for support and he picks up the pace of his pumps. He holds my head with both hands as he pumps away. He was definitely the biggest cock I ever sucked and it was challenging at first to deep throat him, but I finally figured how to accept his full erection.

He eventually stopped and pull out of my throat and say "let me hit that ass now!" I obeyed him and crawl on all fours with my ass in front of him. I pointed at my purse and say "lube and condoms are in there." He quickly digs in my purse and pull out the lube and a condom. He tries to put the condom on in a hurry and was stumbling to open it.

"Honey slow down and breath. I'm not going anywhere, so take your time."

"Damn I hate these things. Hard to open and hard to put on. I hate how they feel even." He grunts out between breaths.

I lay on my side and using my leg to rub his thigh in a comforting manner. He starts rubbing my leg from the ankle up to my thigh and back down.

"Shit I love this lingerie you're wearing. How about you let me hit it raw and I promise to pull out before busting."

I smile and say "or you can put that condom on and get over here to hit this ass." I rub my ass in a circular motion and point at the condom. He instead threw the condom to the side and head towards me with a passion.

"Fine, but you better pull out though. Now get that young cock over here and show this cougar a good time!"

He rushed over quickly and I got back on my hands and knees with my ass ready for him. He holds my hips with one hand and the other hand was guiding his pulsating cock into me. He stops and grab the lube to soak his cock. Now he was ready and continue to guide his cock towards my asshole.

It took a few minutes of pushing and pressing against my asshole before he enters me. The pain was immense as anal sex is usually is, but this was on another level and I actually like it. It took a few minutes of extreme pain, before it starts slowly fading with pleasure increasing. I grip the covers of the bed like I was falling and needed to hold on for life.

My own cock was erected and was close to bust from him fucking me. His thrusting was getting harder and faster, forcing my body to bounce off his body with each thrust. My eyes were rolling backwards in my head and my mouth was wide open, releasing moans and shrieks of excitement.

"OH FUCK! FUCK! DON'T STOP! FUCK ME HARD! PLEASE BABY! FUCK ME!" I was screaming out to him. He grabs my shoulders and pulls me back as he continues thrusting away. The bed was shaking with the movements of our bodies and squeaking loudly along with our own noises.

My hands eventually gave out and I fell on my stomach. I embrace the position and spread my legs flat. He followed what I was doing and lay his chest on my back. He rearranged himself and continues fucking me again. His thrusting was still hard, but slower from before.

I reach back with my hand and feel his muscular ass as he pounds me. He goes on for a minute or so, before he stops. He gets up and pulls out of me. He turns me on my back easily and throws my legs over his shoulders. I grab his cock to guide it back in me again and he helps by thrusting his hips.

Back in me again and without resistance this time. He leans forward over me with my legs still on his shoulders. His hands just above my head and his face hovered aboved mine. I feel his hips go back to thrusting, making those loud wet clapping noises.

I feel his heavy breathing and sweat on my face, his moans were scattered between breaths. He tries to use his tongue to touch mine and I do the same, barely touching and it was hot.

"You ready for me to go hard?" He whispers to me and I nodded yes. He let my legs fall off his shoulders and lays his entire body on mine. My face was in his chest as his body engulfed mine. My legs wrap around his waist and he starts going faster, my hands dig into his back. My eyes goes backwards again.

"I'm close to busting!" He lets out. I ignored him and just enjoy his cock destroying my insides.

"DON'T STOP! KEEP FUCKING ME! CUM IN ME! KEEP FUCKING!" I scream out from under him. He continues thrusting away for another or so, before he slows down and thrusts a couple times. He lets out a loud moan and one final thrust before he stops. He lays on me exhausted and winded, until he gets up to use the bathroom.

I lay there and feel his load of hot cum pour out of me on the bed. I was also exhausted and needed to rest for bit before getting up. After a few minutes of awkward silence, I spoke out to him to say "not bad, maybe a few times and you'll be great one day."

"Oh really? I think you're lying. You seem to be enjoying it a minute ago." He says in a confident tone.

"Yeah it was good, but I noticed you need some more experience. Don't worry you'll get there."

"Mmm hmm, sure. How about you stop talking and get over here to show your experience, unless you're all talk!" He says to me in a sarcastic tone. I laugh and crawl over to him to see he was pulsating slightly. This is why I love young guys, ready for round 2 in a few minutes. Let's see how many times I can get him to cum!

Part 2 is coming soon. I think I'll focus on the crossdresser cougar stories. Let me know if I should make this a series or write other type of stories?