After being coerced into make a porn movie for a few rich internet porn surfers my life has taken a turn for the kinkier. I am a middle aged unfit unemployed male who has always enjoyed sex and recently got involved in movies. It all began over a few drinks with Helen an acquaintance. Helen was in the same situation as me unemployed, slightly overweight and very open about her needs and desires. This should paint the picture of two bored broke horny people. We were sitting in Helens unit drinking cheap cask wine. I have to say I never found Helen attractive but she had a way about her that excited me sometimes. She was no stunner but she always dressed feminine. She always wore high heels, she even wore slip on 4-1/2" heels around home, We were getting slightly drunk on the cheap wine and she started sloughing down on her lounge letting her short cotton skirt ride up showing her red panties. Being a red blooded male it is one of the things we can?t avoid looking at and my dick began to harden making a bulge in my shorts. Helen spotted my bulge and smiled ?what?s got you excited? she asked then looking down at her revealed underwear she said ?Oh sorry? then after a pause and without covering herself ?does it turn you on to look up a lady?s dress?? Slightly embarrassed about her frankness I said ?yes it does actually? I think the drink was loosening up our tongues. She then parted her legs further lifting her high heeled feet and placing them on a low coffee table giving me a full view up her chubby legs to her sexy red panties. She let her hand slip down between her legs and began stroking herself watching for my reaction the whole time. I was getting hugely turned on but also extremely embarrassed, Helen was only ever a friend and I knew it was the booze that had got us into this situation. She continued touching herself letting her shinny red painted fingernails slip under her panties and slip into her pussy. Her face was getting flushed and I could tell by her breathing that she was getting herself off and close to an orgasm. My dick was throbbing and I threw caution to the wind and stood up and pulled my shorts down. Nothing was said so I continued undressing and walked over and stood next to the still seated Helen placing my dick near her mouth. She was panting like a dog now and working her fingers in and out of her cunt at a furious rate, her panties having been discarded. I looked at her face as her mouth bobbed up and down on my cock, She certainly new how to make herself look pretty, the dark blue eye shadow blending out to a lighter shade made her eyes look gorgeous and her red lips now firmly wrapped around by about to come dick were a huge turn on. I felt my orgasm building and new I should pull my dick out before spurting as girls hate that but I couldn?t, it was too late and I spurted my load into her mouth. She gagged and pulled away reached for a tissue and spat my cum out. I didn?t know what to say, here I was naked standing next to an attractive female friend who had just given me a show then blown me so I just sat next to her and said ?thank you for everything?. ?What do you mean everything? she said? ?Well the show is what turned me on so much, you are very attractive and watching you touch your self like that well guys would pay a lot of money to see that?. There was silence for a while then she said ?would they now, let me think about that and get back to you? I was puzzled by this but gave it no thought until a phone call from her a few weeks latter. ?Joe I took your advice but I need your help, can you come over?? What advice had she taken? We arranged to meet at her place that evening, I felt uncomfortable thinking about our brief episode the previous time we had been alone. Helen is attractive and sexy and as I can?t afford to be fussy I agreed to go along. She is probably the best thing that will ever come along for me. I made my way to her apartment and knocked on the door. I could hear her high heals on the wooden floor boards as she made her way to the door. She was made up as ever, she must take a lot of time to get ready each day; it?s just a pity she did not have the body to match. After a few drinks and some small talk I asked what she needed help with.
?Well after my little tease the other night when you said guys would pay to see that it gave me an idea. I could never do it in public but over the internet well ??.? ?You have stripped on the net? I asked? ?It?s worth good money, I?ve found a web site come and look. I owe you for giving me the idea and the courage to do it.? She said The web site allowed for private shows where she would tease in front of a web cam. I made a mental note to check it out one night. ?What do you need me for? I asked. ?Well I am taking requests and I have been asked for my partner to join me, Joe you are the closet I have ever been to having a partner. It will be worth your while in more ways than one? she said looking up at me with her beautiful eyes. I was taken aback, Partner? Join her? Worth my while, what did she mean? ?How does $10000 sound to have sex with me in front of the camera? she asked? ?I?dlove to make love to you, I have fantasised about nothing else since the last time we met but I can?t do it in front of the camera? I said She smiled at that and said ?Of course you can. It will be a one on one session, this guy will pay $20000 for you to fuck me, no one else will see us. I promise it?s safe. But he does not want you to make love to me he wants to see me fucked almost raped even. What we have to do is act a role for him. I have to dress up and sit applying my make up and you have to force me to have sex?. This was a lot to take in, Partner, act out a sex scene in front of the camera I did not know if I could do it. Firstly I was starting to feel some thing for Helen so I did not want anyone else ogling her but on the other side we could both do with the money. ?I?mnot sure, the money would be good but what if our faces are plastered all over the net, and I like you I don?t want other people seeing you get fucked? I said ?You know I love the attention, I?ve always liked revealing myself, I?ll bend over in the supermarket to give some old guy a thrill or let my skirt ride up to let some truck driver have a view, you enjoyed it the other night didn?t you. I promise no one can record this the only one that will see is some rich old pervert.? She said. I agreed and went on-line to see his request. It read: You must wear black stockings and suspender belt. Silver 6?shoes with an ankle strap Red G string Short black skirt Gold revealing top Gold coloured bracelets and rings Red lipstick, blue eye makeup Hair short or tied back Sit applying make up when partner comes up and forces you into oralsex You must then willingly have anal sex and after ejaculation lick up all of his cum. If you agree to these conditions then fill out the form below and the money will be deposited in your account. You must be on-line 24 hours from receipt of payment. ?Well, what do you think? It?s an easy $20k and who knows what it could lead to. Do we do it Joe?? she said We agreed and filled in the details along with our bank account information. Helen and I had glorious sex that night and when I left next morning I was on a natural high, the thought of performing in front of an audience made me nervous but I could certainly use the money so what the fuck we were going to go through with it. The payment was in the bank the next day and I rang Helen to reminder her that tonight was the night. I arrived as horny as hell, it would not take much for me to force myself upon her, I could imagine her in her makeup and shoes and forcing her into anal sex. Helen looked gorgeous, she was dressed exactly as asked complete with rings and bracelets. ?Nervous? she asked? ?Yes a bit but I?m up for anything? I said (fateful words). We logged on to the site and waited for instructions to start when on the chat window appeared: Want to double your money? We looked at each other and clicked yes. To double your money you must perform exactly as asked but the rolls must be reversed. If you click yes you have one hour to get ready. ?What he wants me to dress up and be you? I asked? ?Iguess, hey $40k I?ll do it? said Helen ?lets click yes? ?Fuck off ? I said ?This is ridiculous I?ve never done anything like this and I don?t want to? ?$40k, Joe, You would expect me to do it for $20 what?s the big deal, we can do a lot with that sort of money? she pleaded with me. I reluctantly agreed and the process began. First I stood in the shower and shaved all over, it felt strange sort of extra naked, Helen had stripped and changed into my clothes and I picked up her stockings and started getting dressed in her clothes. Luckily she was a large girl and her skirt and gold top fitted me. The jewellery was next before she applied false finger nails to me. I squeezed into her shoes, the arch in my feet felt uncomfortable as hell and I wondered how girls put up with it every day having pressure on your toes as you stand or walk. I sat there silently feeling ridiculous as she applied my make up, the lipstick making me feel feminine. It?s time she said just sit in front of the camera and re apply your make up and I will do the rest. I sat watching the led light of the webcam and pretended to apply mascara, butterflies were doing cartwheels in my stomach when the word cam across the screen GO! Helen had fitted a huge black strapon dildo the thing was massive and game up behind me and grabbed me by the hair. I tried turning away only to have her big rubber cock thrust into the back of my throat. I gagged and spluttered as she thrust away violating my mouth. On the screen came the words SLAP HER, HARD! Helen with open hand belted me across my face nocking me back of my seat. I struggled to get up, the high heels making it awkward when Helen came around behind me forcing me into the doggie position. She raised my skirt by wiggling it over my ass and pulled my panties down around my knees. She positioned the dildo against my ass and thrust forward. The pain was unbelievable; I felt like I was getting split in two, I thought I was going to be sick. She pushed it all the way in began thrusting in and out, I felt paralysed and just lay there. I had been on the giving side of anal sex many times but had never been a receiver. No wonder girls don?t like it it is excruciatingly painful. After several minutes of this the command came on the screen: MAKE HIM CUM Thank goodness I just wanted this over. I kneeled upright facing the camera Helen was still behind me with her dildo fully inside me. She reached around and grabbed my dick and began wanking me. It did not take long until I sprayed my cum, a big load running down my stockinged leg. An other command said: RUB THE DILDO IN HIS CUM AND MAKE HIM SUCK IT CLEAN! Helen withdrew from my ass and stood up. My anus felt numb, it felt like I had no control of it and imagined it as a gapping hole that I could not willingly close. She knelt in front of me and rubbed her toy in my cum soaked stockings then stood with her dripping dildo next to my mouth. Yuk! I just wanted this over so I took it willingly in my mouth and sucked and swallowed my own juice. Finally a new message on the screen: THANK YOU and the led light blinked of. Contact me if you want another instalment; perhaps suggest the next story line for Joe & Helen kinkyxdresser@writeme.co