Just A Little Kinky Sex
Over the years I had fantasized more and more about kinky sex. At first it was just a little kinky but after surfing the Internet I have wanted to try almost anything and everything. The problem was I had been dating Jen. She wonderful and beautiful but she was not kinky at all. I would have loved to experiment but I loved her and was not willing to cheat. The fact I couldn't try any of the things I saw it made me want it even more. At first I spent a lot of time on bondage websites and I would even tie myself up while I masturbated. I started to pretended I was a slave to a mistress I named Valerie. I pretended Mistress Valerie was forcing me to do things to myself I didn't want to do.
As time went on I became more and more kinky. I went from looking just at girls and bondage websites to adding in she-male and gay websites. I never thought I would get a turned on thinking about cock but as you can tell, it happened. It got to a point where I would wear women's clothes and make-up while I masturbated and looked at the Internet. I even pretended Mistress Valerie gave me the name Amber. When I pretended to be Amber I would call my cock my clit, and my asshole was my pussy. I would dress up completely like a girl and fuck myself with a dildo. I would also do my best to walk and talk like a girl. As time went on I became more and more convincing as a woman. I think the fact that I'm thin, (I am five feet, five inches tall) and my face had feminine features helped me pull-off pretending to be a girl.
After about six months of this, I took it to a new level. Sometimes I would wear women's underwear under my clothes while I went out in public. I always wore them when I went to sex shops. At those shops I would buy assorted toys and videos so I could play with myself when Jen was busy or out of town. When I was alone in my fantasy world, I would watch she-male and bondage porn. I loved teasing my clit and keeping it hard without allowing myself to cum. Once the movie was over I would finally cum and I would make myself lick up every drop. It was almost like I had a second life but I justified it because I never actually cheated. Sometimes I would stuff a pair of pants and shirt with towels and have a dildo sticking out the zipper. Then I would set up a video camera, hit record and when I sucked on and rode the dildo it looked like I was making my own she-male porn. I loved watching myself on film giving head and riding a cock. I only wished it was a real cock and not just a dildo. I got real good at controlling my gag reflex to the point where I could handle an eight in dildo in my mouth. My pussy had also become use to it have the eight inches sliding in and out of it.
This went on for about a year when one day I came home to find a letter that had been place though my mail slot. The only thing on the envelope were the words, "I'm sorry". I opened the letter to find Jen had left me. She didn't say much except she was leaving the area and she was sorry for hurting me. I was crushed because I loved her and loved being with her. This is when things really changed for me.
To distract myself from the depression of her leaving, I spent more time being Amber. I went on the Internet and I bought a lot of new slutty women's clothes and tons of make-up. I even ordered a very real looking set of fake breast. I already had long hair so I didn't need to buy a wig. Kinky sex chat rooms became my best friend and I would use Amber as my log on name. I would always wear the breast and dressed up pretending I was a she-male when I did this. I spent most of my spare time either doing this or I would make my porn films and analyzed every aspect on how I acted and looked on film.
Finally my curiosity got the best of me and I decided to take Amber from fantasy to reality. I have been good at business ever since I was a little kid and my whole life I have been an entrepreneur. This is why I figured if I was going to try having sex with a man, I might as well get paid while I found out if I liked it. One thing that helped me decided to do this, is the practicing I have done made it easy to pass as a woman. Now the way I saw it, it was too dangerous to be a street whore and I could make better money as a tranny escort. I had made enough money from my previous entrepreneurial endeavors I did not need to work. Therefore, I decided to spend my time building my own She-male/Tranny website. The main purpose for the site was to have a kinky sex chat room that I could control. I also figured I would used this medium to set up my first sexual experience as Amber. However, to get people to the site I made deals with a bunch of pay websites, which had sex pictures and videos. I would get daily thumbnail pictures to show for advertising their websites. I used these pictures to draw people into the website. My website took off in no time and I branched out having chat rooms for many different fetishes.
I met a guy in one of my chat rooms that used the name Tranny-Lover. He and I spent a lot of time in private chats discussing many aspects of our lives. We also had cyber sex and did a lot of role-playing. He didn't know who I was but he knew I spent most of my time as Amber. He thought I would go out in public as Amber but that was not the case. Even though I became real comfortable being Amber I was still afraid to let anyone see me that way. Tranny-Lover decided he wanted to meet me and was willing to pay me to do it. He appeared to be very rich and he was willing to pay me $1500 to spend one evening with me. From all of the chats we had, I felt comfortable with him. To be safe, I told him the money was strictly for my time and not for sex. If any sex occurred, it would be because we mutually wanted to have sex with each other. He agreed to this and I had it recorded on my website just in case it was some kind of set up. He didn't live in my town but lived only a few hours from me.
For our encounter, I made reservations at an expensive hotel in a city between where we both lived. I had already acquired a fake ID with my picture in make-up and the name Amber Sue Williams on it. I also had gotten a couple of credit cards in Amber's name. The morning of our meeting I got up and packed multiple sets of outfits, sex toys and enough make-up to last for days. I had only planned for this to last one night, but since I was getting paid such a high price for one evening, I wanted to be prepared for anything. I drove most of the way there when I pulled into a rest stop so I could change into Amber. I have a conversion van with plenty of room in the back. I got into the back of my van for the transformation. This way no one from my town would see me as Amber, but I could arrive at the hotel as Amber.
When I got to my hotel suite, I was very pleased. The suite consisted of a living room with a comfortable couch, love seat and chair set. It was charcoal gray which looked nice on top of the cream color rug. There also was a desk, an entertainment center and a mini bar. The walls were a pale yellow with nature paintings on them. Down the hall from the living room were a bathroom and a bedroom, which also had a bathroom. The bedroom was painted a dark red and had a king size brass bed. The brass headboard was perfect for bondage. In the master bathroom there was a Jacuzzi bathtub and the shower had two showerheads.
I sat down and made myself a screwdriver from the mini-bar. Once I finished my drink I gave myself an enema and called the number Tranny-Lover had given me. I told him I had arrived and gave him the name and suite number of where I was staying. He told me he would be over shortly. I was so nervous and scared my heart started pounding just from his voice. To stay busy I spent the time practicing my walking and talking like a girl. I almost jumped out of my skin when I heard the knock on the door. I took a look in the mirror to see how I looked. I have to admit I looked beautiful and my make-up looked great. I had on a long black evening dress with a pair of high heels, which complimented the dress.
I opened the door and my jaw dropped when I saw he was such a large handsome man. He towered over me and he must have been six feet, five inches tall. He had a chiseled face, which match his large muscular body. He had short brown hair and his deep brown eyes were mesmerizing. I wondered why I guy this good looking and rich wanted to pay for a she-male. "Hi, I'm Frank and you must be Amber. May I come in?"
"Oh, I am sorry about that." I stepped back and let him in. He brushed past me as he entered my room.
"Nice suite you have here. I have to say I think you are even more beautiful than you described your self."
"Thank you, you are quite a looker your self."
"If you don't mind I want to get all of the formalities out of the way so we can spend the rest of the night having fun."
"Okay, in that case you agreed to pay me $1500 for my time. You understand that you are not paying to have sex with me, just to spend time with me."
"I absolutely agree to those terms and here is your money."
I took the money and placed it in the safe in the bedroom. When I returned to the living room I could see by the bulge in his pants he had a large hard cock. Now my heart is really pounding because I am finally going to know how it feels to suck and be fucked by a real cock. It made it even better because he is so good looking and I getting paid for it like a slutty whore. As I sway my hips back an forth as I slowly walk toward him looking at his big cock and I ask, "Do you have a name you want to be called or should I just call you Tranny-Lover."
"Well Amber, how about calling me Frank."
"Okay Frank, if you could do anything at all right now, what would it be?"
"I would watch you undo your dress and step out of it." He was so forward I stopped in my tracks.
As I did as he requested I asked, "What else would you like to happen?"
"First thing, you have a great body and your panty, bra and shoes look fantastic on you. Second, I want you to crawl over here on you hands and knees." I smiled at him as I got on all fours and started to crawl. I was so scared my clit was not in the least bit hard any more. "You look a bit scared Amber. Is it me that makes you scared? Or is this your first time?" Once his socks and shoes were removed I was ordered to kiss his feet, suck on his toes and beg to suck his dick. As my mouth and tongue worked on h "Actually it is my first time. Is that a problem?"
"Actually I like it that way. I love to see how slutty whores react to their first real cock. I hope you like it because if I have my way you will be getting it all night, he stated."
I continued to slowly crawl to him with mixed emotions. I one way I couldn't wait to finally experience what I have only dreamt about but when he said he wanted to have me all night I wondered if I could handle it. When I reached him I got up on my knees and reached for his belt buckle. He stepped back and told me I have to beg to be allowed to remove his socks and shoes before I could do anything else. I did as he requested and was allowed to untie his shoes and remove them. The problem I had was to do it with just my mouth and tongue. My hands could never leave the carpet while I did this. Getting his shoes untied was easy but removing both shoes and socks without the use if my hands took awhile.
As I kissed his feet and toes I said, "Please allow me to taste my first cock. I have waited and practiced for years just waiting for this moment. If you like what I am doing to your toes you will love how I will make your cock feel."
Frank reached down, gently raised my head by grabbing my hair and told me my next test was to remove his belt and pants with just my mouth and tongue. He told me since I would have to get up on my knees I would have to have my hands secured behind by back to prevent me from using them. He walked behind me and he tied my wrist together with his tie. Removing his belt and pants was easier than I thought it would be.
Now I started to get hard. I was actually drooling when I saw his hard cock standing straight up pressing against his underwear. It actually took a little time to remove his underpants. As I pulled them down I was inches away from his cock and I couldn't believe I have finally gotten this close. Once they were off he stepped back again and looked at me as he took off his shirt. I stared at him and all of his muscles. He was even bigger than I thought he was. He could see I was excited and walked up about a foot away from me.
With his right hand he grabbed my hair so I could get close to his cock but not touch it. I wanted to taste it so bad I stuck out my tongue but he made sure I wouldn't reach it. Frank then started to gently rub my clit up and down with his left foot. "By the way your clit is swollen I can tell you like this." He then told me to stand up which was hard to do with my hands tied and still wearing the high heels. I got up and he turned me around. My hands were untied and as he slapped me on the ass he told me to make him a drink.
I poured him a scotch on the rocks from the mini bar. When I turned back around I saw he was in the bedroom, lying in bed up against the headboard with the covers over his lower half. I brought him his drink and started to get in bed. He told me I had to stand there while he sipped his drink. I couldn't believe just a minute ago, I was only inches away and now I can't even see nor even get near his cock.
"Frank, you obviously can see how much I want your cock in my mouth. If you let me, I will let you do anything you want to me for the rest of the night. No matter how kinky your request, I will be your slave."
He just stared at me drinking his drink. "I'm not begging because you wanted me to beg before. I'm doing it because I never thought this day would come and now that I am so close, I can't stand the teasing. I need to see how your cock feels and tastes."
Frank smiled and lifted back the covers. "You said if I let you suck my dick, you would be my slave for the rest of the night?"
"Yes, I will do anything you want."
"Okay whore, make me another drink and then you can suck my dick. But you will do it at my pace so can cum when I want."
I quickly grabbed his glass and made him another drink. I gave it back to him and crawled into bed from the front. I crawled up between his legs to his cock as I had done in many in my fantasies. I started by lightly kissing his balls and slowly kissing my way up his shaft to the head. Finally my lips and tongue are on a real cock and I felt like I was in another world. I kissed the head of his cock and I was surprised how soft and smooth it felt on my lips. I sat and teased his head for a while just enjoying it and taking it all in.
While I swirled my tongue around the head of his cock I massaged his balls and shaft with my hands. I eased my mouth as far down I could go and back up his long shaft. From all of my practice I was able to take the whole thing with in a few minutes. I started picking up speed sliding up and down when he grabbed my hair.
"Slow down, I want this to last for awhile. Plus we have all night. I can tell you have practiced because I have never seen someone take my whole dick on their first blowjob, not to mention how good you are at it."
That made me feel like Amber has truly come to life and even though I was dying to taste his cum, I was willing to slow down.
I went back to working just the upper half of his shaft with my mouth and his balls and lower shaft with my hands. I would alternate my techniques and I could tell he liked it. This was much better than I ever thought it would be. I was completely focused on his cock and nothing else. Suddenly I could tell he was tensing up. He grabbed my hair and said," This is what you've been waiting for so get ready." At that moment he started shooting his load into my mouth. I was able to swallow the first two shots but the next few I couldn't. I was however able to hold it in my mouth with out any of it running out.
"Look at me while you swallow the rest of my cum." I looked him straight in the eyes and swallowed.
I told him, "Thank you so much. It was better than I could have imagined."
"Make me another drink and when you get back it will be time to fully make you a women." I once again made him a drink and when I returned to the bed he took a sip and placed the glass on the end table.
"Get in bed, kneel in front of the headboard facing it and grab the top bar. I'll be back in a minute." When Frank returned, he tied my wrist to the headboard. Once I was secured Frank grabbed my hips, pulled me back and pulled my panties off. He got his legs between my legs and spread me wide.
"Now that you took my dick in your mouth it is time for your pussy to take it." He teased my pussy with the head of his cock. I didn't feel any lube and became worried. He applied pressure but eased off. He started to ease one of his fingers into me and I was glad to feel it had been lubed. He worked another finger in and out for a few minutes. After he could tell I was getting use to his fingers he pulled his fingers out and started applying slow but firm pressure with his cock.
He slowly pushed in until he had passed my sphincter. It made me exhale and breathe hard. Frank stopped at that point so I could get use to having him inside me. It has always driven me wild when someone has kissed my ears and the back of my neck. He started doing this to me and with out thinking it made me press my hips closer to him, which caused he to completely fill me up. He whispered in my ear that he wanted to go slow.
I was losing control and told him that I need him to speed up and fuck me like I'm a little whore. He slowly worked his cock in and out of me picking up the pace as he went. I started rocking back and forth opposite his movements trying to make him go faster. This made my tits bounce up and down as I rocked back and forth. I thought it was okay to fuck myself with a dildo but having an actual cock inside me really made me feel like a woman. Frank still took his time but after awhile he was pounding in and out of me. I would also get a hard smack on the ass with every thrust. I wanted to cum so bad while he fucked me but to matter how much I begged he would never touch my clit. Frank fucked me for so long he had to pull out and apply more lube.
Finally he untied my hands and had me lay on my back. Frank grabbed my ankles and placed them on his shoulders and wasted no time getting back inside of me. I couldn't believe he had so much stamina. He must have fucked me for what seemed like an hour before he finally came. When he did he shot his load on my chest and face.
Frank then looked at me and said," With your finger, wipe up my cum and eat it. When your finish licking it all up I want you to go get a soapy cloth and wash off my dick. Then take a shower and your not allowed to play with your self in there. Get fully cleaned up and reapply your make-up like you're about to have another customer."
"What do you have in mind?"
"I am going to take a short nap and I want you to wake me up by sucking my dick. Then I plan to fuck you all over again." I went to get up and couldn't believe how sore I was. Frank laughed and commented how slowly I moved. He told me since I promised to be his sex slave he was going to get as much out of me he could. I gingerly went to the bathroom and got the cloth. After I had come back I cleaned him up, he rolled over and quickly fell asleep.
I got in the shower and sat on the floor with the water running off my face and down the cleavage from my fake breast. I thought about how sore I was but how lucky I was to experience this in this fashion. Most things you fantasize about are not as good in real life because you have built it up so much. Not only was better than the fantasy, but even after paying for the room I made a lot of money doing it.
After my shower I completely made myself up again and dressed up differently. This time I wore a lacy red body stocking that covered every thing from my neck to my ankles and wrist. The only thing exposed was my head, my hands and my ass. I knew he would love this because it gave complete access for me to be fucked. I eased into bed and placed his soft cock in my mouth. The warmth of my mouth made him start to grow and I love how it felt. Once it was hard I slowly started sucking him off again. I lubed up my finger and started teasing his asshole while I worked my lips up and down his shaft. I could tell he liked this by the moans he gave out.
Frank woke up and told me to lay down on the bed with my head propped up on a pillow against the headboard. He then placed both legs around my chest and started fucking my face. My head was pinned so I couldn't move at all. I just sat there while he fucked my mouth and had his balls smacked my chin. He started cumming and in the position I was in I started to choke. He pulled out and the last shot landed on my face. I started to wipe up his cum but Frank told me to leave it on my face and to go make him another drink.
When I handed Frank his drink I was ordered to turn around and bend over. Frank must have seen my bag of sex toys I had left in the bathroom. When he returned he inserted a large vibrating but plug I had brought. I had to stand at attention while he played with the speed of the vibrator and he drank his drink. I had no control of the speed and no matter how good it felt I had to stand still and at attention. This kept my clit rock hard. He then got out of bed and walked behind me smacking me in the ass as he passed.
"I love how exposed you are in that outfit." I was ordered to turn around a saw Frank was sitting on the couch in the living room. "Come over here, turn around right in front of me and bend over again, he ordered." When I did that I felt his hands reach between my legs and start to spread them apart. I stepped my legs apart for him and I felt the plug get pulled from inside of me. It had been vibrating inside for so long I still felt the numbing from the vibration. Looking at me he said, "Straighten up and sit on my dick."
Frank guided my hips down so I eased onto him. In that position he felt even bigger than before. He made me bounce up and down while he guided my hips making me do all of the work. In no time I was starting to break into a sweat. I was glad I had bought a good adhesive for my fake breast. With all of the bouncing and sweat they still held like a champ. My legs were getting tired but he made sure I kept on going. I was glad my pussy was still numb from the vibrating butt plug otherwise this would probably hurt like hell.
When he could tell I was slowing down he pulled me off and had me turn around facing him and sit on him again. This position gave me a rest because now I'm kneeling on the couch. Frank grabbed my ribs with his thumbs just under my breast helping me ride up and down on his cock. At this point the sweat is pouring off of me. I didn't know how much longer I could keep this up. Frank was a very strong man. He bent forward grabbing my ass and stood up holding me on his cock. I wrapped my arms around him and kissed him. He carried me to a dresser across the room and sat me on the edge of it.
Frank once again started to fuck me as he stood there. I was getting knocked against the wall he was pounding me so hard. Even with all of the sweat, getting fucked started to burn and hurt. After about ten more minutes I started to slide off the dresser since I was sweating so much. Frank stopped and had me walk to the bathroom sink facing the mirror. He removed my body stocking and had me place my hands on the counter. Once again he started fucking me. I was glad he placed more lube on his cock before he re-entered me. This took away some of the friction which was starting to burn my pussy a few minutes ago.
I looked in the mirror and watch how much he was enjoying this. We were both fucking so hard we had sweat dripping off of us. I wanted to come so bad I reached down and started to beat off. Frank grabbed my hand and placed it back on the sink counter. He held both of my hands on the counter so I couldn't pleasure myself.
"There will be time for that later and that will not be how I will make you cum." He slid in and out of me for at least twenty more minutes when he had me lean back against him. Once again he picked me up. This time he reached under my legs and carried me facing away from him. It felt weird to be carried since his grip was spreading me and his cock was still inside me. Every step he took was a new adventure.
When we got back to the bed I was placed on my back and had my wrist tied to the headboard. My ankles were placed on his shoulders again and he didn't waste any time. He went straight back to fucking me as hard as he could. My heart was pounding out of my chest when he said, "I have something for your clit." Without slowing down, he grabbed vibrating cock ring and slid it down my shaft all the ways to my balls. This made my clit become so hard it drove me crazy.
I started shouting, "MAKE ME CUM! I HAVE TO CUM! PLEASE ALLOW ME TO CUM!" Then he slid a second one and stopped half of the way down.
Now we are both bucking back and forth as I keep pleading for him to allow me to cum. Then a third was slid just past the head of my clit. This caused me to start cumming. Once I shot my first load Frank pulled out and this made me cum even harder. My cum shot so hard it hit my breasts. Frank beat off while I was cumming and he also shot his load on me. He then fell to my side and we both lay there trying to catch our breath. I told him that I have never cum that hard before and I meant it. I never dreamed I could cum that hard. We were so tired it didn't take very long before we both fell asleep.
I woke up in the morning as Frank was releasing my wrist from the headboard. He had gotten showered and dressed. He threw down a small wade of cash and told me, "This is to cover the room and a tip for being a good sport. I have a lot of friends that would pay just as much as I did to spent time with you. Actually you could make twice as much if you got implants and got rid off those fake breasts. If you want to continue this life style let me know on the chat room".
I watched him leave the room and saw he left another $500. I was very sore and my legs were wired. I slowly made my way to the bathroom. I took a quick shower to get all of the make-up off then relaxed in the Jacuzzi. I sat there and had a drink thinking about how my first experience went. The way I saw it Amber might have just found a new career.
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