HeartBreak Fuck

"Nick stop being so lame and just take your shot like a man" Jack yelled at me. Jack is that guy. The guy who is a little too overconfident and is for sure masking some deep insecurities. At 6-4 220 he's the guy who gets his fair share of ladies. Not like me at 5-9 I have always just existed.

"Alright but this is the last shot for a while" I reply. Jack is on a mission to get me fucked up tonight and like always he is winning.

"Dude you need to get over her. She was a whore. Like you literally cought her cheating on you with another guy in your bed... Tonight is a drinking night and theres nothing you can do about it" Jake said a little too loudly. Pretty sure the whole bar just heard him say that. Not that he's wrong. I did catch my now Ex in bed with another guy. Like that five years down the drain.

Alex was a smoke show, a 5-2 blond beauty. She had a body to die for. Smooth legs and some boobs you couldn't even hold in your hands. I always knew she was out of my league. That I somehow tricked her into liking me and that she would eventually wake up and leave. I just didn't think I would find out by walking in on her with Jamaal. A coworker that she constantly reassured me that I had nothing to worry about. I still can't get the image of him fucking her doggy style on our bed. The noises she was making... They didn't even notice me for at least a minute.. maybe longer. The little bit of self esteem I had vanished when I saw his dick. Jesus it must have been 9 inches at least.

"Nick I am going to go to the bathroom, finish your drink and order us a another round for when I get back" jake abruptly says and snaps me out of my little day dream.

"Sure" I mumble back as he is already halfway gone. As I was finishing my drink I feel a little push from behind and it causes me to stumble and spill my beer all down my front. I turn around ready to yell at someone for causing this to happen.

"HeY" I start saying but I get lost in the most beautiful blue eyes with blond hair. One of my biggest weaknesses She must have been 6-2 at least. She was wearing a low-cut top that showed off some huge breasts and was cut off and showed her tight stomach. The skirt she was wearing was extremely low cut and showed off her amazing legs.

"Oh, I am so sorry I didn't mean to bump into you." This mysterious beauty told me. I was like a deer in headlights. Just staring at her trying to think of something to respond with.

"Mmm its okay its pretty crowded" I mumbled back, not sure she could even make out anything I said.

"Let me buy you another to make up for it" she told me in the sexiest voice I have ever heard. She's sexy and offering to buy me a drink? What girl does that? We sat down at the bar together

"Thanks, I guess that makes up for the mess" can she me blushing I think awkwardly. The bartender brings me another drink and we start talking. More like she starts talking and I nod and smile and try to ask some insightful questions. Thank god jake saw that we were talking and went and started catching up with another buddy we new at this place. He can be a good wingman... sometimes.

"Hey, can we get two tequila shots" she ordered from the bartender before I could decline. They were there. I guess I am doing a tequila shot with this girl...

"Wait I don't even know your name yet?"

"Finish your shot and I will tell you my name" She whispered in my ear. I take zero time to think about it and kill the shot immediately. "Good boy, life will be much better if you just do as I say." The goosebumps that gave me were indescribable, in that moment I knew I just wanted to keep hearing her say that. "Becky, you can call me Becky"

"Thanks, Becky, you have most beautiful eyes, do you know that?" I surprised myself with the compliment. Where did that come from? She instantly gave me this look, like she wanted me. She puts her hand on my thigh.

"So I know this is forward, but I live right next door. Want to have a quick drink at my place?"

"Yes" I answer way to quickly. She just continues to stare at me.

"Good boy" we pay our respective tabs and walk out. I make quick eye contact with Jake and he gives me a nod and tries to hide some surprise. Not often that I ditch him for a girl I just met. Or ever... But a first time for anything I guess.

She wasn't lying her apartment was a block and a half away so we make it back quick. She immediately pours us two shots of tequila which we immediately kill. "Man I love tequila it makes me sooo turned on" She whispers in my ear. I get lost in those blue eyes again. She leans forward and starts kissing me. Its amazing. Those soft lips just know what to do. One hand is on the back of my head controlling my movements while the other is feeling up my ass. She gives me a hard squeeze and I cant help but moan into her kiss. She breaks it off and says "Good boy moan for mommy. I love that, strip for me."

I cant take my clothes off fast enough. I am naked in about 5 seconds flat. "Good boy, you have such a cute penis." She smirks As she grabs a hold of it with one hand. She starts slowly stroking it. I don't have the biggest dick, maybe 4 inches. She pushes me down into the couch and shes slowly stroking me. Giving me barely any pressure. It doesn't matter I let out another moan. Probably way to girly of one. "Do you like this"

"yes becky its so fricken hot" I moan out.

"Good boy, now flip over and get on your knees I want to see that ass of yours" before I know it I am face down ass up on the couch facing away from her. She still is slowly stroking my dick but I noticed with only 2 fingers... With her other hand she is massaging my ass. One thing about me is I have a very sensitive ass and its way to big for a boy.. I start moaning on the couch.

"Oh, does my boy like his ass being played with"

"Yes Becky" She spanks me hard. And stops stroking my dick

"Call me Mistress Becky from now"

"Yes Mistress" she starts slowly rubbing my ass again. Getting a finger really close to my hole. She can tell I want it. So, she gets some lube and starts squeezing some out all over my ass. Really making it oily. My dick is as hard as it's ever been. I feel like I am just leaking. She slowly inserts a finger. It hits a spot in me, and I just start moaning like a girl. Then she inserts another. And then another... I start losing it she is just slowly moving them in and out like she is on a mission. I have never had this turned on before.

She takes out her fingers, and I can hear her shirt come off. Then her skirt...

"Close your eyes and get on your knees in front of the couch around" I start slowly turning around and getting on the floor I can feel her guiding hands to help me. "Open them" She commanded. I slowly opened them to see her towering over me with one of the biggest dicks I had ever seen.

It must have been 8 inches long and as thick as my wrist. "Does baby boy like my dick" She whispered in her sexy voice.

"Oh shit you are huge, you are going to wreck my ass" I replied in shock. While I am a virgin back there I have always had a huge fantasy of being with a trans female. Something about a sexy woman with a huge dick had always peaked my fantasy. Especially with how sensitive my ass is...

"good boy start with giving mommy a nice blowie. Get me all lubed up for you." I waste no time in getting her head in my mouth. I try and get as much saliva on her dick as possible. I get my hands involved going up and down while sucking that head. I want to get her as turned on as possible before that hammer gets near me. After a minute or two she starts taking over and with her hand guides my head farther and farther down her shaft. I am at her mercy. When I feel a twitch and her taking her dick out of my mouth pretty fast. I knew she was close...

"alright face down ass up on the couch little boy". I immediately get in position for her. As if there was no debate on who was going to be topping here. She gives my ass another round of lube. "alright I will be slow at first, but then no mercy."

"yes mommy" I start feeling a massive object at my ass. It slowly starts going in, it passes my special spot and I see stars. My dick immediately is back to being rock hard.

"oh my baby boy likes this." She grabs onto my dick with her thumb and pointer finger and slowly strokes me as she is inserting her dick. I am moaning like a bitch in heat. She finally gets her full member in me. "You like this don't you beta boy" I am just moaning in response. She starts pulling out pressing against that special spot in me. When she's almost all the way out she drops my dick and grabs ahold of my hips and shoves her dick right back in as fast as possible causing me to moan out loud for her. "I knew you were such a bottom when I saw you in the bar" she then starts fucking me like no tomorrow. In and out, in and out. "God you are my bitch, my little bottom bitch" I can't help it and I start Cumming everywhere. She wasn't even holding my dick anymore. I came from just her dick rubbing my spot. "That's my sissy bitch, Cumming hands free the first time I fuck him, Get used to this its going to be a frequent occurrence from now on bitch boy" She then picks up speed and starts moaning a little bit. When her dick is fully in me I feel it expand start twitching Then drops the biggest load in my ass. It was such a hot experience It made me cum again. "Such a good ass to fuck" she says as she pulls out.

"Baby do me a favor and start cleaning me up with that mouth" I am out of breath just twitching. I have never had an experience like that. At that moment I knew I would do anything to experience that again.

So I turn around and slowly start licking her clean. As I am cleaning her I look up into those beautiful blue eyes and I know I made the right choice.