therapydidnthelp
06-05-2015, 06:49 PM
This is my first attempt on writing a story. It's my own fantasies, which I hope you guys will enjoy!
PS - English is not my native language, so sorry if I have a few slips now and there
No way back!
Chapter 1: My first she-male mistress - Annie
What would you do if someone would tell you that two months from now you’ll be nothing but a sex toy for a bunch of she-males? What would you do if they say that your ass and mouth will be used and abused in the kinkiest way possible by one, two or more girls with cocks? And finally: what would you do if someone tells you, you will enjoy it so much, you’d be begging for more?
What I’m about to tell you is my story. It all started two months ago, with an innocent chat with a not so innocent girl.
My name is Simon. I’m a 23 year old college graduate from Belgium. I’ve been living in New York for two years now, having been reassigned here by my employer who needed someone with my computer skills to handle the US side of the business.
Getting back to the point, after more than a year and a half of no female action what-so-ever, a guy gets pretty tired of jerking off all the time. Well so did I.
But since my social skills weren’t exactly top notch, I basically had to resort in finding someone to fuck, where else but, online. One of my colleagues mentioned this awesome site where he met his current girlfriend, where you can create a profile and find people based on specific criteria.
Well my profile sounded something like this: 23 year old male, 5’9 tall, 140 pounds, good looking, submissive, open minded, looking for top woman to fuck me.
As you can see, I like to keep things simple. And yes! I am submissive and would rather be the bottom bitch.
Needless to say, I got a few answers back, and started chatting with a few of the interested ladies. But only a few wanted to allow me to chat and cam at the same time, which of course, led me to eliminate those who didn’t want to show their faces.
Long story short, there was this one chick, Annie, who was really cute and fun to talk to at the same time. She was 25, brunette, 5’7, 34D boobs, New Yorker also, but currently working in LA for the next month.
We chatted every evening, sometimes 2 or 3 times a day, and I really felt she and I clicked. She was a very sweet girl, smart and her body was one to die for. She only had a few pictures on her account, all in swimming suits, and the only nude was a pic taken from behind showing her beautiful round, toned ass.
She told me she doesn’t want to reveal her body on web cam, and was only chatting so we can get to know each other and she if we have any connection.
Sex wise she was my goddess. She said she loved dominating boys and girls, but especially boy, loved using toys on her ‘victims’, spanking, slapping, spitting, you name it! I guess she really enjoyed watching me squirm when she talked about how she wanted to use me, how she wanted me serving for her every sexual fantasy.
There was a week left before she would be back in NY and we could finally meet. I was sitting at my computer one evening, when her Skype image popped up.
“Hi Simon! How is my favorite little boy doing?”
“Hi Annie! Nothing much. Counting the days till I get to see you face to face.”
“That’s so sweet. Actually, that’s the reason I wanted to talk to you. I don’t have much time, I have to leave in like 15 minutes. My work mates and I will be doing some Nevada desert exploring for the next 3 or 4 days, so I won’t get to talk to you until I get back.”
I was getting paranoid that she has changed her mind somehow and she doesn’t want to meet a computer geek like me anymore.
“Listen Annie; if you’ve changed your mind and you don’t want us to get together anymore, that’s ok. But please tell me now and get this over with!”
“Where did you get that from silly?” Annie laughed. “Just because a girl wants to have some fun, doesn’t mean I don’t want to tap that sweet little ass of yours when I get to NY!”
“Really? We’re still on?” I was so excited I almost hugged the monitor.
“Yes dumb ass! Of course we are.” She added still laughing at me. “But listen, I only have 5 more minutes and I really need to get a few things out in the open now, while I still have the chance.” Annie’s tone turned serious.
“I’m all ears.” I said anxious to learn what she wanted.
“First things first. I didn’t mention something about me by now, something I should’ve, but I was too afraid you would reject me if I did. Now I really wanted to tell you this before we met. I think this is the best way.” Annie’s look was serious and she had a please-be-cool-with-it face.
“What is it Annie? I’m sure it’s nothing!” I couldn’t possibly see anything she could’ve said that would make me not want to meet her.
“Well Simon, how..how open minded are you?” Annie asked.
“I think I told you everything I’m up for. I mean, if you want to explore something with me, I’m cool with that. I really like you Annie, and as far as sex goes, you can do whatever you want with me!” I said confident.
“Ok Simon! I don’t want you to freak out ok? Is just that...Well I... I am a she-male! I am a girl all the way, born like this, but I have a penis!” Annie’s eyes were as big as I ever saw them. She was waiting for me to say something, anything, but I was lost for words.
I mean a dick? How? She looks so gorgeous; I could never have guessed that.
“Simon?! Are you ok sweetie?” Annie asked after a few dozen seconds of dead silence on my behalf.
“I’m ok. But how? I mean I never saw that coming! Are you like a tranny or something” I was so confused I didn’t know what to think. I watched she-male or tranny porn before, and loved it by the way, but I never thought of meeting one of them ever. And this hot! Man was she hot. I mean Annie was smoking hot. Centerfold material hot!
“No dude! I am not a guy. I never was a guy and never had any surgery, thank God! I was born like this. I know it’s a lot to take, but I really need to know you’re cool with this before we move on.”
“I am. Really I am, but it’s unexpected, you know?” I said that without even thinking it before. My heart wanted it, my cock was rock hard at this point, and I definitely fantasized about being fucked by a dickgirl, so why the fuck not?! “I’m cool with it Annie. I mean it’s still you. Only you come with a bonus.”
“Oh I’m so glad you feel this way Simon! We’re gonna have so much fun together. You’re going to love it. I’ll fuck you so hard; you’ll want to have it in you all the time.”
“I’m sure we’ll both get a kick out of it Annie!” I said excited.
“Now listen. I need you to be a good boy and do me a favor” Annie said. “I need you to get your body hairless by the time I get back. I have a place I got to get my waxing, so I’ll text you the number, ok?”
“I guess I’ll do it. Never had my body shaven before, but if that’s what you need I’ll do it.” I wasn’t that excited, but I could see where she was coming from.
“Glad we’re on the same page. Now listen, I really have to go, so guess I’ll give you a call once I’m back to NY, ok?”
“Sure thing Annie! Have fun with your friends!”
“Thanks honey! See you later!”
……………….
I was counting the minutes until I get to finally meet Annie! She called me yesterday saying she was in town and asked me if I wanted to drop by her place today. I said yes of course, and am now on my way to her place.
She said she wanted to see me as soon as she landed, but her roommate Mindy was home waiting for her.
“I want the whole house for us when I first get my hands on you” she told me over the phone.
After she texted the address and said her roommate will be gone by 8 PM, I jumped in the shower and started to get ready for possibly the best moment of my life so far.
I was trying desperate not to jerk off, but my cock was mostly erect since she called yesterday. Even now, in the cab I was practically sweating from the tension in my jeans.
When I finally reached her place, I was so hard, I couldn’t even walk straight! She buzzed me in the
building, and told me the floor she lived at.
As soon as the elevator doors opened I was in for a sight! Annie was standing in the doorway, wearing nothing but a bathrobe which had its cord so loose, you could practically see everything! Her left breast was only showing a bit, but her right was out there for my eyes to feast on.
The bottom part of her robe was basically a tent, with her erect cock only holding so much of the material that it covered just a small part of it.
“Come here Simon! I’ve been thinking for this moment for so long, my cock is ready to explode” Annie said and pulled me inside the apartment.
She shut the door and jumped on me, kissing passionately, grabbing and squeezing my ass through my jeans. Her robe was useless at this point and I could feel her big boobs and huge cock pressing against me!
Annie then suddenly broke the kiss and grabbed my hand leading me to the bed room. She let the robe slide down her shoulders and thighs and I could finally see her round, perfect ass in front of me.
Once we got to her bed room, she stopped me in the middle on the room and moved in behind me. She took my shirt of and then proceeded unbuttoning my jeans.
“Time for me to see that beautiful ass of yours Simon” Annie said.
As soon as my jeans and boxers were around my ankles, she gave my ass a good slap on each cheek.
“Do you like that Simon? Do you want me to play with your ass” she said with lust in her tone.
“Yes please” I couldn’t take it at this point. I felt my cock was about to explode any second now.
Annie then pushed me on the bed, face first, with my ass sticking out.
“I’m going to fuck this ass so hard, you’ll never want to leave this apartment!”
Annie then slapped my ass so hard I actually jumped! She then pulled my hair and got me off the bed in a kneeling position.
Her cock was now just inches from my face and I could see just how big it is. It must’ve been a good 8 inches long and also very thick!
Annie had both hands in my hair at this point and started moving her hips and rubbed her cock all over my face.
“I want you to suck my big girl-cock now Simon! I think I’ve waited long enough!” Annie whispered and then guided the head of her huge penis toward my open mouth.
I started licking and sucking her tip, while trying to massage her balls at the same time. Annie’s moans were a good indication that I was doing a good job, but I knew she was just not the type of girl to settle with that.
Her cock soon found its way to the opening of my throat and her hands started pushing my head deeper and deeper, until my eyes watered and the gag reflex kicked in. I looked up and saw Annie’s eyes filled with lust, while her cock started moving in and out of my mouth, but every time going deeper and deeper!
I tried to control myself and let her cock slide down my throat, but the size of it was too much. My hands pushed her hips away and I gasped for air as hard as I could. My face was covered in tears and drool at this point, so I tried to wipe it clean with my t-shirt.
“I’m going to let this one go Simon, but you are never to push me away from that sweet mouth of yours, understand?” Annie was pretty pissed and intense, so I just now realized that she was all about dominating and breaking me at this point. I don’t think me trying to slow things down was going to work with her.
“I’m sorry Annie, it’s just that I could not breathe and my body just tensed up all of the sudden!”
“I know sweetie, but you need to relax and let me work my way down your sweet, tight throat! You need to work with the gag reflex and let the spit help my cock slide down. Trust me! Mothing is going to happen! You will love this” Annie said, and then bent over to give me a big kiss.
After a few seconds of passionately kissing, I was loose enough for her to fill my mouth with her bid girl-cock. But not before tying my hands behind my back using her bathrobe cord, “Just so you won’t push me away again”, Annie smiled.
I was determined to listen to her and let her guide me, and possibly enjoy the whole thing. Besides, I was a bit scared, but this was still turning me on like hell!
Annie’s swollen member soon found its way back in my mouth, and to my surprise, it went straight down my throat for about 5 inches, before hitting the back of my neck.
“Ready baby?” Annie asked with a grin on her face.
Her hips started to move faster and faster, her hands gripping tight on my hair to keep my head in place. I could feel every inch of her cock sliding inside my mouth deeper and deeper, until her balls rested on my chin.
To my surprise, I was able to fight off the gag reflex, although my spit was now covering my chin and the floor beneath us.
After a few seconds she released the grip on my head and her cock was out of my mouth with an audible pop.
“Oh baby there’s much more to come, so you need to stop sucking my dick like that!” I could see her chest turning a light shade of red and her eyes told me she must’ve struggled hard not to cum after that intense face fucking she gave me.
Annie grabbed my hair and threw me on the bed face first, with my ass sticking out, ready for her to play with it at will.
Her soft hands started to part my ass cheeks and I soon felt her warm tongue slowly massaging my ass hole. At first I had an impulse to laugh, as it tickled this sensitive region, but the more she pressed her tongue inside of me and the more her nails started to gig in my ass cheeks, the feeling was so intense I felt I was ready to shoot my load all over her sheets.
I could feel my ass muscles loosen up around her tongue and felt my tight little hole gaping around her probing mouth.
She must’ve heard my heavy breathing, and felt I was getting closer and closer to climax, so she slowly pulled her tongue out and used her hands to stretch my ass cheeks apart.
“Look at that tight little asshole” she said smiling, “it’s so tight it closed as soon as I got my tongue out”
“Put it back in Annie! I beg you” I moaned, “I was so close to cum”
“Oh no sweetie! You only cum when I say you can!” Annie said with an authoritarian voice. “I love it that you beg me to play with your asshole, but my tongue can do so much, I am afraid”. With that, Annie stepped away from the bed, not before instructing me not to move, and came back wearing a pair of nylon gloves, holding a black, rather thick, butt plug and a bottle of anal lube.
She was so beautiful standing in front of me, holding the butt plug and the lube, her nipples so hard and her black hair was covering most of the left side of her face. I wanted her to make me her bitch, to fuck and abuse me at her own will!
“Lay down on your back” she ordered, again using a demanding tone.
“I need to stretch that tender little asshole, before I can fuck you with my cock! We don’t want anything to break and you out of action for weeks, do we now?!” Annie knew exactly what she was doing, but I was so hot, I just wanted her to plant her seed deep inside my bowels and her to say those magic words and let me cum!
“Please Annie..please fuck me! I need you inside of me!” I cried out, as soon as I positioned myself as she ordered.
“Oh you will be fucked, rest assured, you little cock hungry whore!” she said grabbing a couple of pillows and placing them under my lower back.
She then moved her ass right on top of my face, positioning herself so that our bodies were now in a 69 position.
“I want you to eat my ass, you little bitch! That should keep my cock all nice and big, while I play with this virgin butt of yours!”
I was powerless, with my hands tied behind my back, between the pillows and my back, and her ass keeping my head from moving a single inch without her approval.
I started licking and probing her ass, just the way she did with mine not a couple of minutes ago.
Annie grabbed my calves and pulled my legs back so she could have a perfect view of my fresh butthole.
I felt lube being squirted all over my cock and balls, but mostly on my asshole. There was no warning when the first finger broke in my un-expecting butt ring, but the lube and the prior tongue play made it slide in all the way to the nucke.
“Isn’t that an eager little slut?! You want me to keep adding fingers to your little virgin ass, don’t you?”
She didn’t wait for any reply from me and the middle finger from the other hand entered my asshole, with barely and resistance what-so-ever, much like the first one did. She was finger fucking me with both hands to allow her to stretch my hole as much as she could.
It felt sore, but good at the same time, and to repay her for the pleasure she was giving me, my tongue was now frantically fucking her sweet asshole.
Soon another finger from each hand was added, and there were now 4 of her long, but slender, fingers fucking me!
“I can’t believe you’re taking this so well!” she said pulling my asshole wide opened. “look at this gap! I bet we can try that butt plug now!”
Annie kept stretching my ass and then bent over and used her tongue to fuck me some more. But moments later she withdrew her fingers and left me with a sensation that I have never experienced before. I felt empty without her fucking me with her fingers and tongue. My ass closed up instantly, but it kept pulsating like it wanted to suck her fingers back in.
She gave my buttcheeks a few rather hard slaps, about 5 on each side, before lifting her ass from my face and positioning herself at the edge of the bed. Annie lifted my ass, and now my knees were spread on either side of my head. My hard penis was right in my face, and Annie was now standing up behind me, my back resting on her knees.
I could see her in all her beauty, with her big boobs, with small hard nipples just waiting to be sucked, her blue eyes looking lustfully at her prize and, of course, her huge cock fully erect and ready to rip my asshole apart.
She was holding the butt plug against my asshole and started pushing it inside of me. The first few inches went in easily, and the pain was barely there, but as soon as it reached its widest part, which must’ve been around 2 inches in diameter, I felt it and started to squeeze my ass muscles.
Annie didn’t force it inside of me, instead she pulled I out then in again, and started fucking me with the butt plug.
“Oh my God that feels so good” I moaned, as I felt my ass started to loosen up and eat more and more of the toy. “Oh fuck me Annie, please fuck me deeper! Push it in!”
After a few in and out movements, where Annie admired my now gaping asshole, she finally started working the plug past its widest mark.
As soon as it went in and my little hole ate it all, it sent my body into uncontrolled shivers!
“It’s touching your prostate now you dirty little slut! You like that don’t you, you whore?” Annie asked and bent to lick my swollen balls.
“I love it Annie!” I moaned loudly. “Please make me cum for you! I can’t take the pressure anymore!”
“Let me help you release that pressure for you slut!” Annie said and with one hand grabbed the base of the butt plug and started pushing and twisting it inside of me, and with her other hand slowly caressed my cock, to the point it instantly started leaking pre-cum on my chest and face.
The plug was pressing against my prostate, and my man G spot made me shiver in anticipation of the orgasm I was about to receive.
Annie’s hand moved forward and grabbed my cock and with slow paced motions started stroking it. At the same time, she moved it toward my face.
Instinctively I opened my mouth and moved my tongue as if to catch all the liquid I was about to squirt.
The cum explosion was nothing I ever experienced before. Jet after jet of thick cum left my balls and landed all over my face, tongue, but most of it, guided by Annie, landed straight in my mouth. As soon as it was finished, Annie squeezed the last drops out of my cock and then proceeded to push the cum that rested all over my face in my mouth.
“Be a good little slut and swallow it all!”
I didn’t waste any time in obeying my mistress and swallowed my thick cum. I must admit it is not the first time I taste my own spunk, but I have never had to swallow a mouthful before. It went down with ease and I opened my mouth, smiled and wiggled my tongue out to show this perfect woman that I did just as she commended me.
“That’s a good little slut” Annie said satisfied and fed me her fingers to suck and clean the cum off of. “I think it’s time for me to see just how tight that ass of yours really is!”
She turned me around and I was now standing on all fours with the butt plug still stuck deep inside my bowls and Annie’s big penis dangling in front of my face, bigger than ever, just waiting to be sucked.
Annie grabbed the base of her cock with one hand and the back of my head with the other and proceeded fucking my mouth with her cock going all the way in and then all the way out, making her fuck stick shinny from all my spit!
She then moved both hands on my ass and squeezed and slapped it while her hips were moving rhythmically plugging her cock in and out of my throat.
My eyes were wet at this point, but I got used to the gag reflex and honestly enjoyed me being her fuck toy that my own cock was back fully erect!
Her hands soon grabbed the base of the butt plug and she slowly pulled it out of my ass.
“Look at this tight little hole!” Annie said while spreading my ass cheeks. “It just got a big plug in it, but it still refuses to keep an open gape! It’s so tight I can’t wait to give it a go!”
With that being said, Annie pulled her slippery cock from my throat and moved in behind me.
“Are you ready for my cock Simon?” “Are you ready for this lady cock to split you open?”
At this point I was so aroused I would’ve said yes to her sticking her whole foot up my ass!
“Oh yes Annie, please fuck me!” I moaned out.
“You’ll have to beg better than that bitch!” Annie ordered, and started playing with her cock at the entrance of my wet, lubed asshole.
“Please mistress, please make my ass yours! Please take this tight butt hole and fuck it all night long!” I begged loudly.
Annie pushed my head in the matrices and prepped me for the fuck of a life time I was about to receive.
Her mushroomy head was slowly pushing in and stretching my little entrance wide open! She was surprisingly gentle so the pain was little compared to the pleasure I felt by serving my mistress.
Inch after inch slowly conquered my insides, and my moans got louder and louder as her full girth was rubbing my prostate.
As soon as half her cock was inside, she stopped and started slowly fucking my ass. In and out, the rhythm increased and sure enough her cock was now pushing its way in until all 8 inches of hard cock was lying comfortably in my asshole!
“Oh God you’re so tight!” Annie moaned once her pelvis hit my ass cheeks. “I will have to take this slow, because your tight ass will make me cum too fast!”
Her hips started moving back and then forward again till her pelvis and my ass were making that slapping noise we all love. She increased her pace and by now my hole was, by my surprise, fully accommodated with Annie’s size, and I reached between my legs and started rubbing my erect dick.
“I love fucking your ass so much you little cum slut!” Annie moaned “Turn around now!” she ordered.
I was lying on my back and Annie grabbed my legs and pushed them to my chest having full access to my opened hole. My cheeks were red from her slapping me, and for a moment there it seemed she was admiring my tight little butt hole.
But that ended soon, as I felt her meaty penis powering its way deep inside of me once again. This time her fucking was anything but gentile. Her hips were slapping my ass with such force that every single thrust made my whole body shiver with pain and pleasure.
Annie’s eyes were emanating lust, her sweat was dripping from her big breasts on my body and her mouth was moaning and breathing deeply.
Her hands lost their leverage on my ankles and both grabbed my face, with her left hand grabbing and choking my neck and her right hand grabbing my jaw and making me suck on 4 of her fingers!
I have never been so roughly fucked ever before, but it felt so good I soon felt another orgasm building in my balls.
Her cock was drilling my tight asshole and with her leaning over me and trying to push even deeper in my insides, made my cock explode as soon as I grabbed it and started stroking.
Annie laughed as load after load of cum was shooting out of my cock and reached as far as my forehead! She started scattering the cum all over my face and seemed to enjoy me being covered from my belly to my face in my own cum.
But this made her fuck me even more furiously than before and by now I was gasping for air as her grip on my neck made me choke!
“Oh baby..oh fuuuuuck!” Annie yelled “I’m cuming!”
With a swift move Annie pulled her cock out of my ass and pulled me down on the floor holding a firm grip on my hair.
Instinctively I opened my mouth and watched her as she was stroking her beautiful penis! I used my tongue to play with the tip of her cock and my hands to gently squeeze her massive balls.
“Open your mouth baby!” Annie said as she tugged my head back and placed the tip of her cock on my tongue.
I looked up at her and saw the goose bumps on her body right before her climax.
The first stream of salty cum hit the back of my throat, but I managed to stop the gag and keep my mouth open for the rest. Her aim was impeccable as not a drop of her precious nectar was spilled. Her cum quickly filled my mouth and as soon as her orgasm was over she let go of my hair and I was able to grab her cock and squeeze the last drops of semen in my mouth.
I knew what she wanted me to do, so I smiled as I looked into her beautiful blue eyes, showed her the gooey prize I just received, gargled with it for a few seconds than happily swallowed it all.
“That’s a good little slut” Annie said catching her breath “I’m so glad you like to be roughed around!”
“I’d do anything for you Annie” I replied.
I found myself still licking her wonderful cock like I wanted to go for another round. “Don’t worry baby, there will be plenty of me fucking your brains out! Now it’s time to rest and enjoy the rest of the evening!”
End of chapter 1
---------------------
Hope you enjoyed reading this at least as much as I enjoyed writing it. I've been into shemale porn and stories especially for a few years now, but again this is my first try on writing one and I'm sure you guys might have a few wise words of advice! So please let me know what you think!
I want this to be a 4 or 5 parts series, so if you have any ideas you want to pitch in, it's more than welcomed!
PS - English is not my native language, so sorry if I have a few slips now and there
No way back!
Chapter 1: My first she-male mistress - Annie
What would you do if someone would tell you that two months from now you’ll be nothing but a sex toy for a bunch of she-males? What would you do if they say that your ass and mouth will be used and abused in the kinkiest way possible by one, two or more girls with cocks? And finally: what would you do if someone tells you, you will enjoy it so much, you’d be begging for more?
What I’m about to tell you is my story. It all started two months ago, with an innocent chat with a not so innocent girl.
My name is Simon. I’m a 23 year old college graduate from Belgium. I’ve been living in New York for two years now, having been reassigned here by my employer who needed someone with my computer skills to handle the US side of the business.
Getting back to the point, after more than a year and a half of no female action what-so-ever, a guy gets pretty tired of jerking off all the time. Well so did I.
But since my social skills weren’t exactly top notch, I basically had to resort in finding someone to fuck, where else but, online. One of my colleagues mentioned this awesome site where he met his current girlfriend, where you can create a profile and find people based on specific criteria.
Well my profile sounded something like this: 23 year old male, 5’9 tall, 140 pounds, good looking, submissive, open minded, looking for top woman to fuck me.
As you can see, I like to keep things simple. And yes! I am submissive and would rather be the bottom bitch.
Needless to say, I got a few answers back, and started chatting with a few of the interested ladies. But only a few wanted to allow me to chat and cam at the same time, which of course, led me to eliminate those who didn’t want to show their faces.
Long story short, there was this one chick, Annie, who was really cute and fun to talk to at the same time. She was 25, brunette, 5’7, 34D boobs, New Yorker also, but currently working in LA for the next month.
We chatted every evening, sometimes 2 or 3 times a day, and I really felt she and I clicked. She was a very sweet girl, smart and her body was one to die for. She only had a few pictures on her account, all in swimming suits, and the only nude was a pic taken from behind showing her beautiful round, toned ass.
She told me she doesn’t want to reveal her body on web cam, and was only chatting so we can get to know each other and she if we have any connection.
Sex wise she was my goddess. She said she loved dominating boys and girls, but especially boy, loved using toys on her ‘victims’, spanking, slapping, spitting, you name it! I guess she really enjoyed watching me squirm when she talked about how she wanted to use me, how she wanted me serving for her every sexual fantasy.
There was a week left before she would be back in NY and we could finally meet. I was sitting at my computer one evening, when her Skype image popped up.
“Hi Simon! How is my favorite little boy doing?”
“Hi Annie! Nothing much. Counting the days till I get to see you face to face.”
“That’s so sweet. Actually, that’s the reason I wanted to talk to you. I don’t have much time, I have to leave in like 15 minutes. My work mates and I will be doing some Nevada desert exploring for the next 3 or 4 days, so I won’t get to talk to you until I get back.”
I was getting paranoid that she has changed her mind somehow and she doesn’t want to meet a computer geek like me anymore.
“Listen Annie; if you’ve changed your mind and you don’t want us to get together anymore, that’s ok. But please tell me now and get this over with!”
“Where did you get that from silly?” Annie laughed. “Just because a girl wants to have some fun, doesn’t mean I don’t want to tap that sweet little ass of yours when I get to NY!”
“Really? We’re still on?” I was so excited I almost hugged the monitor.
“Yes dumb ass! Of course we are.” She added still laughing at me. “But listen, I only have 5 more minutes and I really need to get a few things out in the open now, while I still have the chance.” Annie’s tone turned serious.
“I’m all ears.” I said anxious to learn what she wanted.
“First things first. I didn’t mention something about me by now, something I should’ve, but I was too afraid you would reject me if I did. Now I really wanted to tell you this before we met. I think this is the best way.” Annie’s look was serious and she had a please-be-cool-with-it face.
“What is it Annie? I’m sure it’s nothing!” I couldn’t possibly see anything she could’ve said that would make me not want to meet her.
“Well Simon, how..how open minded are you?” Annie asked.
“I think I told you everything I’m up for. I mean, if you want to explore something with me, I’m cool with that. I really like you Annie, and as far as sex goes, you can do whatever you want with me!” I said confident.
“Ok Simon! I don’t want you to freak out ok? Is just that...Well I... I am a she-male! I am a girl all the way, born like this, but I have a penis!” Annie’s eyes were as big as I ever saw them. She was waiting for me to say something, anything, but I was lost for words.
I mean a dick? How? She looks so gorgeous; I could never have guessed that.
“Simon?! Are you ok sweetie?” Annie asked after a few dozen seconds of dead silence on my behalf.
“I’m ok. But how? I mean I never saw that coming! Are you like a tranny or something” I was so confused I didn’t know what to think. I watched she-male or tranny porn before, and loved it by the way, but I never thought of meeting one of them ever. And this hot! Man was she hot. I mean Annie was smoking hot. Centerfold material hot!
“No dude! I am not a guy. I never was a guy and never had any surgery, thank God! I was born like this. I know it’s a lot to take, but I really need to know you’re cool with this before we move on.”
“I am. Really I am, but it’s unexpected, you know?” I said that without even thinking it before. My heart wanted it, my cock was rock hard at this point, and I definitely fantasized about being fucked by a dickgirl, so why the fuck not?! “I’m cool with it Annie. I mean it’s still you. Only you come with a bonus.”
“Oh I’m so glad you feel this way Simon! We’re gonna have so much fun together. You’re going to love it. I’ll fuck you so hard; you’ll want to have it in you all the time.”
“I’m sure we’ll both get a kick out of it Annie!” I said excited.
“Now listen. I need you to be a good boy and do me a favor” Annie said. “I need you to get your body hairless by the time I get back. I have a place I got to get my waxing, so I’ll text you the number, ok?”
“I guess I’ll do it. Never had my body shaven before, but if that’s what you need I’ll do it.” I wasn’t that excited, but I could see where she was coming from.
“Glad we’re on the same page. Now listen, I really have to go, so guess I’ll give you a call once I’m back to NY, ok?”
“Sure thing Annie! Have fun with your friends!”
“Thanks honey! See you later!”
……………….
I was counting the minutes until I get to finally meet Annie! She called me yesterday saying she was in town and asked me if I wanted to drop by her place today. I said yes of course, and am now on my way to her place.
She said she wanted to see me as soon as she landed, but her roommate Mindy was home waiting for her.
“I want the whole house for us when I first get my hands on you” she told me over the phone.
After she texted the address and said her roommate will be gone by 8 PM, I jumped in the shower and started to get ready for possibly the best moment of my life so far.
I was trying desperate not to jerk off, but my cock was mostly erect since she called yesterday. Even now, in the cab I was practically sweating from the tension in my jeans.
When I finally reached her place, I was so hard, I couldn’t even walk straight! She buzzed me in the
building, and told me the floor she lived at.
As soon as the elevator doors opened I was in for a sight! Annie was standing in the doorway, wearing nothing but a bathrobe which had its cord so loose, you could practically see everything! Her left breast was only showing a bit, but her right was out there for my eyes to feast on.
The bottom part of her robe was basically a tent, with her erect cock only holding so much of the material that it covered just a small part of it.
“Come here Simon! I’ve been thinking for this moment for so long, my cock is ready to explode” Annie said and pulled me inside the apartment.
She shut the door and jumped on me, kissing passionately, grabbing and squeezing my ass through my jeans. Her robe was useless at this point and I could feel her big boobs and huge cock pressing against me!
Annie then suddenly broke the kiss and grabbed my hand leading me to the bed room. She let the robe slide down her shoulders and thighs and I could finally see her round, perfect ass in front of me.
Once we got to her bed room, she stopped me in the middle on the room and moved in behind me. She took my shirt of and then proceeded unbuttoning my jeans.
“Time for me to see that beautiful ass of yours Simon” Annie said.
As soon as my jeans and boxers were around my ankles, she gave my ass a good slap on each cheek.
“Do you like that Simon? Do you want me to play with your ass” she said with lust in her tone.
“Yes please” I couldn’t take it at this point. I felt my cock was about to explode any second now.
Annie then pushed me on the bed, face first, with my ass sticking out.
“I’m going to fuck this ass so hard, you’ll never want to leave this apartment!”
Annie then slapped my ass so hard I actually jumped! She then pulled my hair and got me off the bed in a kneeling position.
Her cock was now just inches from my face and I could see just how big it is. It must’ve been a good 8 inches long and also very thick!
Annie had both hands in my hair at this point and started moving her hips and rubbed her cock all over my face.
“I want you to suck my big girl-cock now Simon! I think I’ve waited long enough!” Annie whispered and then guided the head of her huge penis toward my open mouth.
I started licking and sucking her tip, while trying to massage her balls at the same time. Annie’s moans were a good indication that I was doing a good job, but I knew she was just not the type of girl to settle with that.
Her cock soon found its way to the opening of my throat and her hands started pushing my head deeper and deeper, until my eyes watered and the gag reflex kicked in. I looked up and saw Annie’s eyes filled with lust, while her cock started moving in and out of my mouth, but every time going deeper and deeper!
I tried to control myself and let her cock slide down my throat, but the size of it was too much. My hands pushed her hips away and I gasped for air as hard as I could. My face was covered in tears and drool at this point, so I tried to wipe it clean with my t-shirt.
“I’m going to let this one go Simon, but you are never to push me away from that sweet mouth of yours, understand?” Annie was pretty pissed and intense, so I just now realized that she was all about dominating and breaking me at this point. I don’t think me trying to slow things down was going to work with her.
“I’m sorry Annie, it’s just that I could not breathe and my body just tensed up all of the sudden!”
“I know sweetie, but you need to relax and let me work my way down your sweet, tight throat! You need to work with the gag reflex and let the spit help my cock slide down. Trust me! Mothing is going to happen! You will love this” Annie said, and then bent over to give me a big kiss.
After a few seconds of passionately kissing, I was loose enough for her to fill my mouth with her bid girl-cock. But not before tying my hands behind my back using her bathrobe cord, “Just so you won’t push me away again”, Annie smiled.
I was determined to listen to her and let her guide me, and possibly enjoy the whole thing. Besides, I was a bit scared, but this was still turning me on like hell!
Annie’s swollen member soon found its way back in my mouth, and to my surprise, it went straight down my throat for about 5 inches, before hitting the back of my neck.
“Ready baby?” Annie asked with a grin on her face.
Her hips started to move faster and faster, her hands gripping tight on my hair to keep my head in place. I could feel every inch of her cock sliding inside my mouth deeper and deeper, until her balls rested on my chin.
To my surprise, I was able to fight off the gag reflex, although my spit was now covering my chin and the floor beneath us.
After a few seconds she released the grip on my head and her cock was out of my mouth with an audible pop.
“Oh baby there’s much more to come, so you need to stop sucking my dick like that!” I could see her chest turning a light shade of red and her eyes told me she must’ve struggled hard not to cum after that intense face fucking she gave me.
Annie grabbed my hair and threw me on the bed face first, with my ass sticking out, ready for her to play with it at will.
Her soft hands started to part my ass cheeks and I soon felt her warm tongue slowly massaging my ass hole. At first I had an impulse to laugh, as it tickled this sensitive region, but the more she pressed her tongue inside of me and the more her nails started to gig in my ass cheeks, the feeling was so intense I felt I was ready to shoot my load all over her sheets.
I could feel my ass muscles loosen up around her tongue and felt my tight little hole gaping around her probing mouth.
She must’ve heard my heavy breathing, and felt I was getting closer and closer to climax, so she slowly pulled her tongue out and used her hands to stretch my ass cheeks apart.
“Look at that tight little asshole” she said smiling, “it’s so tight it closed as soon as I got my tongue out”
“Put it back in Annie! I beg you” I moaned, “I was so close to cum”
“Oh no sweetie! You only cum when I say you can!” Annie said with an authoritarian voice. “I love it that you beg me to play with your asshole, but my tongue can do so much, I am afraid”. With that, Annie stepped away from the bed, not before instructing me not to move, and came back wearing a pair of nylon gloves, holding a black, rather thick, butt plug and a bottle of anal lube.
She was so beautiful standing in front of me, holding the butt plug and the lube, her nipples so hard and her black hair was covering most of the left side of her face. I wanted her to make me her bitch, to fuck and abuse me at her own will!
“Lay down on your back” she ordered, again using a demanding tone.
“I need to stretch that tender little asshole, before I can fuck you with my cock! We don’t want anything to break and you out of action for weeks, do we now?!” Annie knew exactly what she was doing, but I was so hot, I just wanted her to plant her seed deep inside my bowels and her to say those magic words and let me cum!
“Please Annie..please fuck me! I need you inside of me!” I cried out, as soon as I positioned myself as she ordered.
“Oh you will be fucked, rest assured, you little cock hungry whore!” she said grabbing a couple of pillows and placing them under my lower back.
She then moved her ass right on top of my face, positioning herself so that our bodies were now in a 69 position.
“I want you to eat my ass, you little bitch! That should keep my cock all nice and big, while I play with this virgin butt of yours!”
I was powerless, with my hands tied behind my back, between the pillows and my back, and her ass keeping my head from moving a single inch without her approval.
I started licking and probing her ass, just the way she did with mine not a couple of minutes ago.
Annie grabbed my calves and pulled my legs back so she could have a perfect view of my fresh butthole.
I felt lube being squirted all over my cock and balls, but mostly on my asshole. There was no warning when the first finger broke in my un-expecting butt ring, but the lube and the prior tongue play made it slide in all the way to the nucke.
“Isn’t that an eager little slut?! You want me to keep adding fingers to your little virgin ass, don’t you?”
She didn’t wait for any reply from me and the middle finger from the other hand entered my asshole, with barely and resistance what-so-ever, much like the first one did. She was finger fucking me with both hands to allow her to stretch my hole as much as she could.
It felt sore, but good at the same time, and to repay her for the pleasure she was giving me, my tongue was now frantically fucking her sweet asshole.
Soon another finger from each hand was added, and there were now 4 of her long, but slender, fingers fucking me!
“I can’t believe you’re taking this so well!” she said pulling my asshole wide opened. “look at this gap! I bet we can try that butt plug now!”
Annie kept stretching my ass and then bent over and used her tongue to fuck me some more. But moments later she withdrew her fingers and left me with a sensation that I have never experienced before. I felt empty without her fucking me with her fingers and tongue. My ass closed up instantly, but it kept pulsating like it wanted to suck her fingers back in.
She gave my buttcheeks a few rather hard slaps, about 5 on each side, before lifting her ass from my face and positioning herself at the edge of the bed. Annie lifted my ass, and now my knees were spread on either side of my head. My hard penis was right in my face, and Annie was now standing up behind me, my back resting on her knees.
I could see her in all her beauty, with her big boobs, with small hard nipples just waiting to be sucked, her blue eyes looking lustfully at her prize and, of course, her huge cock fully erect and ready to rip my asshole apart.
She was holding the butt plug against my asshole and started pushing it inside of me. The first few inches went in easily, and the pain was barely there, but as soon as it reached its widest part, which must’ve been around 2 inches in diameter, I felt it and started to squeeze my ass muscles.
Annie didn’t force it inside of me, instead she pulled I out then in again, and started fucking me with the butt plug.
“Oh my God that feels so good” I moaned, as I felt my ass started to loosen up and eat more and more of the toy. “Oh fuck me Annie, please fuck me deeper! Push it in!”
After a few in and out movements, where Annie admired my now gaping asshole, she finally started working the plug past its widest mark.
As soon as it went in and my little hole ate it all, it sent my body into uncontrolled shivers!
“It’s touching your prostate now you dirty little slut! You like that don’t you, you whore?” Annie asked and bent to lick my swollen balls.
“I love it Annie!” I moaned loudly. “Please make me cum for you! I can’t take the pressure anymore!”
“Let me help you release that pressure for you slut!” Annie said and with one hand grabbed the base of the butt plug and started pushing and twisting it inside of me, and with her other hand slowly caressed my cock, to the point it instantly started leaking pre-cum on my chest and face.
The plug was pressing against my prostate, and my man G spot made me shiver in anticipation of the orgasm I was about to receive.
Annie’s hand moved forward and grabbed my cock and with slow paced motions started stroking it. At the same time, she moved it toward my face.
Instinctively I opened my mouth and moved my tongue as if to catch all the liquid I was about to squirt.
The cum explosion was nothing I ever experienced before. Jet after jet of thick cum left my balls and landed all over my face, tongue, but most of it, guided by Annie, landed straight in my mouth. As soon as it was finished, Annie squeezed the last drops out of my cock and then proceeded to push the cum that rested all over my face in my mouth.
“Be a good little slut and swallow it all!”
I didn’t waste any time in obeying my mistress and swallowed my thick cum. I must admit it is not the first time I taste my own spunk, but I have never had to swallow a mouthful before. It went down with ease and I opened my mouth, smiled and wiggled my tongue out to show this perfect woman that I did just as she commended me.
“That’s a good little slut” Annie said satisfied and fed me her fingers to suck and clean the cum off of. “I think it’s time for me to see just how tight that ass of yours really is!”
She turned me around and I was now standing on all fours with the butt plug still stuck deep inside my bowls and Annie’s big penis dangling in front of my face, bigger than ever, just waiting to be sucked.
Annie grabbed the base of her cock with one hand and the back of my head with the other and proceeded fucking my mouth with her cock going all the way in and then all the way out, making her fuck stick shinny from all my spit!
She then moved both hands on my ass and squeezed and slapped it while her hips were moving rhythmically plugging her cock in and out of my throat.
My eyes were wet at this point, but I got used to the gag reflex and honestly enjoyed me being her fuck toy that my own cock was back fully erect!
Her hands soon grabbed the base of the butt plug and she slowly pulled it out of my ass.
“Look at this tight little hole!” Annie said while spreading my ass cheeks. “It just got a big plug in it, but it still refuses to keep an open gape! It’s so tight I can’t wait to give it a go!”
With that being said, Annie pulled her slippery cock from my throat and moved in behind me.
“Are you ready for my cock Simon?” “Are you ready for this lady cock to split you open?”
At this point I was so aroused I would’ve said yes to her sticking her whole foot up my ass!
“Oh yes Annie, please fuck me!” I moaned out.
“You’ll have to beg better than that bitch!” Annie ordered, and started playing with her cock at the entrance of my wet, lubed asshole.
“Please mistress, please make my ass yours! Please take this tight butt hole and fuck it all night long!” I begged loudly.
Annie pushed my head in the matrices and prepped me for the fuck of a life time I was about to receive.
Her mushroomy head was slowly pushing in and stretching my little entrance wide open! She was surprisingly gentle so the pain was little compared to the pleasure I felt by serving my mistress.
Inch after inch slowly conquered my insides, and my moans got louder and louder as her full girth was rubbing my prostate.
As soon as half her cock was inside, she stopped and started slowly fucking my ass. In and out, the rhythm increased and sure enough her cock was now pushing its way in until all 8 inches of hard cock was lying comfortably in my asshole!
“Oh God you’re so tight!” Annie moaned once her pelvis hit my ass cheeks. “I will have to take this slow, because your tight ass will make me cum too fast!”
Her hips started moving back and then forward again till her pelvis and my ass were making that slapping noise we all love. She increased her pace and by now my hole was, by my surprise, fully accommodated with Annie’s size, and I reached between my legs and started rubbing my erect dick.
“I love fucking your ass so much you little cum slut!” Annie moaned “Turn around now!” she ordered.
I was lying on my back and Annie grabbed my legs and pushed them to my chest having full access to my opened hole. My cheeks were red from her slapping me, and for a moment there it seemed she was admiring my tight little butt hole.
But that ended soon, as I felt her meaty penis powering its way deep inside of me once again. This time her fucking was anything but gentile. Her hips were slapping my ass with such force that every single thrust made my whole body shiver with pain and pleasure.
Annie’s eyes were emanating lust, her sweat was dripping from her big breasts on my body and her mouth was moaning and breathing deeply.
Her hands lost their leverage on my ankles and both grabbed my face, with her left hand grabbing and choking my neck and her right hand grabbing my jaw and making me suck on 4 of her fingers!
I have never been so roughly fucked ever before, but it felt so good I soon felt another orgasm building in my balls.
Her cock was drilling my tight asshole and with her leaning over me and trying to push even deeper in my insides, made my cock explode as soon as I grabbed it and started stroking.
Annie laughed as load after load of cum was shooting out of my cock and reached as far as my forehead! She started scattering the cum all over my face and seemed to enjoy me being covered from my belly to my face in my own cum.
But this made her fuck me even more furiously than before and by now I was gasping for air as her grip on my neck made me choke!
“Oh baby..oh fuuuuuck!” Annie yelled “I’m cuming!”
With a swift move Annie pulled her cock out of my ass and pulled me down on the floor holding a firm grip on my hair.
Instinctively I opened my mouth and watched her as she was stroking her beautiful penis! I used my tongue to play with the tip of her cock and my hands to gently squeeze her massive balls.
“Open your mouth baby!” Annie said as she tugged my head back and placed the tip of her cock on my tongue.
I looked up at her and saw the goose bumps on her body right before her climax.
The first stream of salty cum hit the back of my throat, but I managed to stop the gag and keep my mouth open for the rest. Her aim was impeccable as not a drop of her precious nectar was spilled. Her cum quickly filled my mouth and as soon as her orgasm was over she let go of my hair and I was able to grab her cock and squeeze the last drops of semen in my mouth.
I knew what she wanted me to do, so I smiled as I looked into her beautiful blue eyes, showed her the gooey prize I just received, gargled with it for a few seconds than happily swallowed it all.
“That’s a good little slut” Annie said catching her breath “I’m so glad you like to be roughed around!”
“I’d do anything for you Annie” I replied.
I found myself still licking her wonderful cock like I wanted to go for another round. “Don’t worry baby, there will be plenty of me fucking your brains out! Now it’s time to rest and enjoy the rest of the evening!”
End of chapter 1
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Hope you enjoyed reading this at least as much as I enjoyed writing it. I've been into shemale porn and stories especially for a few years now, but again this is my first try on writing one and I'm sure you guys might have a few wise words of advice! So please let me know what you think!
I want this to be a 4 or 5 parts series, so if you have any ideas you want to pitch in, it's more than welcomed!