A black mailed whore

Posted in: Sexual Blackmail

I sat in the restaurant with a glass of wine and my friend Jackie. I met Jackie in a support group for guys who feel they are women. Jack wore a nice black silk pants and a blue blouse with her long ear rings that topped off the entire out fit nicely. I wore a long skirt that had a slit down my right side it was navy blue with some flower design in it. I also wore my favorite blouse, white and faintly sheer you could see a dark color bra if I were wearing one but I was not.
We were celebrating my new hair; I had just had implants put in and now donned dark brown shoulder length hair. We were waiting for Jack who was Jackie�s boy friend who knew who we were.
When Jack arrived he sat down and had both of us on either side of him, he was on my right and Jackie�s left. We all sat and ate and had wine without meal. I did not realize that my skirt had slipped and now I was exposing my leg from my foot to my waist. Wearing no stocking I looked nude at this side as you could not see my matching black thong. Jackie excused herself to the bathroom and I sat cross legged with Jack.
Jack reached over and ran his hand down my exposed leg. �That�s nice� he said and I pulled my skirt over to cover my leg. �How did you get it so soft?� he asked. Not embarrassed at all I told him that after a shave I put on a moisturizer on. Jackie and I were to go out after dinner but when she returned she told me she did not feel well and was going home. Since she had a car and I didn�t I had no way home, but Jack told her he would take me home. After Jackie left Jack and I started to talk some more, I had planned to be out all night I told him so he offered to go for a walk with me since he knew the neighborhood we were in.
Jack and I left the restaurant and Jack put his arm around me and rested his hand on my ass. I was horny and had not been with a man in a long time, so if Jack wanted to feel my ass there would be no argument from me. We walked for a long time talking about this and that when we came to a park. �This is where I got my first fuck� he told me. Surprised at candor I told him I gave my first blow job in a park. It was dark and only a few lights spotted throughout the park were on when I felt something I was not expecting. Jacks finger moved between my ass cheeks and sat on my �button�. The hole to my ass, I called my button because once you push it I get very turned on, almost uncontrollably and Jack had his finger on it ready to push it at any time. I turned my head surprised to find Jacks hand had slid in threw the opening of my skirt and not on the outside of my skirt like I had thought. I couldn�t believe but he had it there since we left the restaurant that meant every one could have seen us. Unfortunately this too was a turn on for me, public sex was the best sex.
Jack gave my ass a squeeze then pushed his finger turning the button on. I was now at his mercy, if told I would have given everyone a blow job or better yet let them fuck me without mercy. Somehow Jack knew this and he stopped us in the middle of the path, dark as it was there were still people about now and then. He undid his pants and took out his cock, put his hand on the top of my head and pushed me down where there was no argument about what I was to do next. I started sucking his cock, wanting his seed in both ends. I wanted someone to come along and fill my ass at the same time. Jack placed both of his hands on my head, took a fist full of my hair in both hands and pulled hard making me deep throat his shaft. My last vice a little rough play and I go all the way! Soon Jack was pumping my mouth both hard and deep, then just before he was about to empty his seed into my mouth he pulls away. His cock twitches madly as he undoes my top and pulls it down over my shoulders, pulls my bra out and empties his load on my breast making my bra hold his load. He then has me lick his cock and any seed left before his puts his cock away. I look up at him from my knees much like a little girl asking daddy if she can have a pony, innocently but not likely.
Jack had me stand and we walked a bit more his hand now around my bare shoulders and every now and then he would push a finger or two into my bra wet his fingers and make me suck on them. We went back to my apartment. I was about to get out of the car and thank him for tonight when he got out and opened my door for me. I thought he was about to say good night when he walked me up to the door.
�What�s Jackie going to think of me?� I asked him.
�If you�re a good girl she won�t find out� he retorted. I opened my door and he followed then in to my apartment. I was still in the �on position� and felt for Jackie my best friend as I did not want to lose her. I excused myself and went to change out of my wet bra. Just as I was topless Jack walked into my room, he grabbed my arm and pulled me to him and kissed me and at the same time undid my skirt letting it fall to the ground. Now he placed both hands on my ass and pulled them apart forcing two fingers on to my button. I was putty, melting in his arms, even my own cock grew hard and my mouth watered for service. We broke our kiss �you will do what I want or I will tell Jackie what you did� I looked up into his eyes not really absorbing his words I nod in agreement. �Show me all you lingerie� he said. I pulled out everything I had then he wanted to see what clothing I had. He picked out a long halter style black dress. �You will wear this tomorrow night� I had forgotten that Jackie had her birthday party the next day. �No bra but this red thong� he said holding it up. The dress was very light to wear and you would be able to see threw it, that�s why I wear a slip with it. �Also you will lube that hot little ass of yours and be ready for a hard long fuck too� he said and with that he got up and left.
The next day I was a wreck, I had given my best friend man a blow job and now he wanted me to dress up for easy access to my button, but what could I do with my button still �on� I was stuck. I dressed as requested and went to the party. I was grateful to see so many people when I arrived. Jackie introduced me to her father. He was a tall well built man and looked to be in great shape. My small frame of 5�5� tall and 125lbs I looked up to the 6�3� man. If he was not my friend father I would have asked him out!
After a couple of hours Jack showed up beside, he leaned over and said �I have a gift for you� he pulled out of his pocket a long butt plug. �Go to the bathroom and put it in right now� He handed it to me and nudges me to go and do as I was told. I did but knew that once I had it in I would not be able to control my own actions. It would be like pushing the �on button� down and not letting go. As I came out of the bathroom plug in place Jackie asks me to keep her father company as he does not know any of her friends. I walked over and stood beside him and started some small talk, when a shock went through my whole body. I almost fell to my knees as Jack turned the butt plug he gave me to vibrate. My hips were trying to thrust forward as I fought hard to stand still. Brad (Jackie�s father) said he would get us another drink. I stood there alone when Jack came over. �I love how you want to fuck him, I saw you hip rocking back and forth� he said then showed me the remote it had everything vibrate from one to ten shock one to ten even rotate. I could have a field day and not even leave my apartment! Jack put his hand threw one of my long slits in the dress and pushed the plug in deeper and did it without anyone knowing what he was doing. �I want to have some fun, see if you can get closer to Brad a nice blow would be good� he said then left before I could say anything.
Brad returned with our drinks as we stood and talked by the cabinet where we could lean against if we wanted to. A sudden shock went threw me as Jack turned the knob to 5 or 6. I bounced slightly then caught Jack standing behind Brad some distance away. I moved closer to Brad and ask if he were single. �Yes, I am but I just can�t find a woman who I like� he said to me as I smiled at him.
As the night went on Brad stayed close to me even putting his hand on my naked back when we moved from one location to another. Almost everyone had left and Jack, Brad and I were cleaning up as Jackie past out. Brad offered to drive me home and I accepted, then Jack said he would come too so that Brad wouldn�t get lost on the way back. Brad thought that was a good idea, I on the other hand I knew it wasn�t.
We all arrived at my apartment and the three of us went in, Brad had to use the bathroom and that left me and Jack alone. Jack told me to lean over the kitchen table then reached in and took out the plug. I was glad it was out so he would have less control over me but sad cause it felt so good. �I put a small gift in your dresser where you keep your lingerie. I want you to put it on for Brad. I want you to fuck Brad tonight, I think he needs it� Brad returned from the bathroom. �Brad do you think you can find your way back? Jack asked him.
�Sure no problem, do you have to go somewhere?�
�I have to swing by and take some pictures for someone� he said then he went out the door.
�Would you like a glass of wine?� I ask brad. He said yes and we sat down on the couch. I felt much more relieved now that Jack had left and even let my bare leg show through one of the dresses slits. Brad said he wanted to ask me a few questions but did not know if it was appropriate. �You can ask me anything you want� I replied to him.
�What do you like?� he started.
�What do you mean?� I asked not sure what he really meant.
�Sexually� he said simply taking me completely off guard.]
�Oh� I started. �Well, I like the man to take control, I love a man who can get his way and let me have mine as well� I said hesitating to see what was next.
�Do you like bondage, group sex? Do you like to be photographed or video while making love?� He took a sip of his wine and had a slight slime across his lips.
�Yes, yes and yes, if it will make the man get hard again and again I would do almost anything� I said because my �on button� was pushed. I could not have imagined that I would be having this conversation with my best friend�s father. Brad said �hmmmm� and put his wine glass down and sat back. It was at this point my button took over I leaned over and put my hand on his thigh, brushed back my hair and said �do you like me?� Brad looked at me his eyes looking deep into mine then his large hand wrapped around the back of my neck and he leaned in and kissed me. He knocked me off balance and I had to move my hand to stop me from falling forward unfortunately my hand landed on his hard cock. He let out a slight moan.
�Why don�t you go and get into something more comfortable� he said breaking the kiss. I got up and went into my bedroom, I opened my linger drawer to find a collar that had �You�re willing whore� written in small letter on it. I took it out and a purple baby doll and stood there looking at the collar when Brad came in, I think I would like the whole nine yards garter stocking, I will wait out here� he said then walked out of the room. I changed quickly into a bustier with a separate garter belt. I put on my sexy lace panties with a matching push up bra. Everything matched, black lace with my nipples peeking over the top of the bra like they were supposed to. I took out an old white gown that was open in the front and slipped on the heist stilettos I had also in black and walked out into the living room. Brad sat on the couch with a large cock want out of his pants. He stood up and met me half way across the floor. �Now that�s better� he said kissing and sliding both hand through the opening of the gown.
Brad moved me over to the kitchen table that was beside us. He backed me up to it then lifted me up and sat me on it while he removed his pants. His cock was a fair size and would not normally fit easily into me if it weren�t for the butt plug I had been wearing. He gently pushed me back and pulled my panties to a side then still being gentle pushed the entire length of his cock deep inside my hole. I moaned as he lifted my legs up in the air over his should and began slowly fucking me. His mouth licked my nipples as his fingers grasped my breast into a point. Brad then pulled me up and had me almost standing with his hard cock still buried deep inside me I could hardly touch the floor. The next thing I knew I was sucking his cock when he came ordering me not to swallow until he said so. My mouth quickly filled with his seed. I loved the taste and smell and feel of the entire load, soon my mouth was overflowing and his seed ran down my cheeks, just then he pulled out his hard cock making me show him his load then swallowing it.
Brad had me on the table once again but this time he was working me. As we kissed he was jerking my hard cock when I started to shoot my load he held on and had me cum in his hand then he wiped it all over his own cock and made me lick it and suck it clean. Just when I thought we were done he scooped me up and carried me into the bedroom.
�I want you to scream with ecstasy� he said to me putting me down on the bed. We laid in bed kissing until he got hard again. He removed my panties tied my hands above my head, put both of my legs under his arms and mounted me. He started fucking my ass. �Tell me what you want� he said loudly �Tell me� he insisted. I couldn�t help myself.
�I want you to fuck me� said loudly
�Fuck you how? Tell me� he yelled louder
�Fuck me, fuck me hard, fuck me, fuck me like the whore I am� I yelled out his rhythm increasing.
�Tell me your a whore and what you will do for me slut! He said
�Im your whore I will do anything you want, I will fuck you anywhere you want, I am your whore� I yelled out as the bed was rocking violently. Once again he slows his pace and pulls his hard cock out of my hole. �Please I�m your whoring fuck me please� I begged him. He turned me over making my arms cross in front of my face. He lifts up my hips and mounts my ass again now holding my hips as he pushes ever deep inside of my hole.
�I want to hear you whore� he said
With every thrust I let out a loud yelp and said yes fuck your whore, fuck me I want your cum, I want your cum running out of me, fuck me please� I was begging for something I was getting, then he came hard and for a long time. �Oh yes, yes fuck this whore� After he was done he pulled out and untied me. He had me undress in front of him making it as sexy as I could, then we spooned in the bed until we fell asleep.
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Rating: 9.5/10 (6 votes cast)
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A black mailed whore, 9.5 out of 10 based on 6 ratings

2 Responses to “A black mailed whore”

  1. MasterHank

    Good story,, gve me a great boner as i imagined you suucking me and swallowing my cum before i drive my cock up your tight ass

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  2. triphammer73

    Your story was well told. Had me wanting to join you too, the two of us pleasuring each other until we passed out from exhaustion.

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