I Masturbate For My Bossbyfantasyboy©
I am 20 years old, slightly overweight, large breasts (very sensitive nipples) and very sexy. I was very shocked when my boss came up with his proposal. I mean, I liked him, and certainly didn't fancy him, after all he was old enough to be my father.
But I needed the money and it wasn't really prostitution. I wasn't going to have sex with him. Anyway I often played with myself in front of my boyfriends. There was something exciting and dirty about making yourself cum while someone watched you. No it definitely wasn't prostitution, was it.
I kept trying to convince myself.
I desperately needed the money. I was up to my overdraft limit. My credit card was full up and I owed lots of money to lots of people. Here was a solution to my problems and I might even enjoy it.
I slept badly that night trying to convince myself that what I was seriously thinking about doing was the right thing to do.
Of course, it wasn't prostitution. The thought kept going around in my head.
I woke up and knew that when I got into work I had to give my boss an answer.
As I walked in I knew what I was going to do. I needed the money.
He was sitting at his desk. We smiled at each other and said, 'Good morning'.
I was waiting for him to ask me whether I had reached a decision and he was waiting for me to tell him.
After a while he said, 'Well, have you decided.'
I said, 'Yes, I'll do it, but no sex, I'm not going to have sex with you.'
He said, 'Oh that's great I'll book a hotel room'.
Nothing much happened until after lunch when he came back and said he had booked a room in a local hotel for the following afternoon. He told me to phone in sick the next day and told me that I wouldn't lose any pay.
I slept rather excitedly that night. I didn't like to admit but the thought of it was turning me on. I phoned into work in the morning and said I was suffering from women's problems. It was sort of true.
The hotel was only a short walk away. We had arranged to meet at 2.30 and as I walked into the reception of the hotel I began to feel nervous, very nervous. I thought, 'What the fuck am I doing here'.
I was dressed rather ordinary, with just jeans and top. Although the top was rather low that exposed quite a lot of the cleavage that I am very proud of. But I was almost shitting myself. I nearly turned round and went back home. But I needed the money.
As I walked into the reception I saw him sitting there. I walked up to him and sat down on the sofa beside him.
He said, 'I'm not forcing you into anything, if you want to turn round and walk away its up to you, but in this bag is £100 for you if you go through with it.'
I stood up and said, 'What's the room number'.
We walked together to room 30. He put the key in the lock and opened the door and held it open for me. It was a very large room with a large double bed and a couple of armchairs and a door that led into a bathroom.
He put the bag on the bed and said, 'Everything you need is in here. I want you to use everything and enjoy it as much as I'm going to. I promise you I won't jump on you, but obviously I'm going to play with myself while I watch you.'
He turned the bag upside down and everything fell on the bed.
I walked over and looked to see what he had bought. I saw the 5 crisp £20 notes. Then there was a huge black dildo and 2 vibrators, some lipstick, a lip pencil and lip gloss. A pair of black fishnet stockings and a pair of black 5 inch high heel shoes and 20 B & H cigarettes. I realised that he wanted me to act and perform like a tart.
I rather reluctantly started to undress. Although I teased him constantly at work I was now very embarrassed as I slipped my trousers and top off. I stood in front of him in my bra and knickers and seriously thought about calling it off.
But I caught the site of the money on the bed and knew I had no choice.
Before I took my underwear off he said, 'I want you to put some lipstick on'.
He handed it to me. It was not what I usually wore. This was a bright red tarty colour. He handed me the lip pencil first and I stood in front of the full length mirror and outlined my lips. I saw him watching me closely. Then he handed me the lipstick. I coated my lips with the bright red lipstick and then followed up with the lip gloss. I have to admit I quite liked the look. I actually began to feel very tarty.
But then he shocked me and said, 'I want you to put the lipstick on your nipples now'.
I had never done that before although several boyfriends had mentioned it before. I knew I had no choice. I unhooked my bra and threw it on the bed. Amazingly my nipples were quite hard. Although I was very nervous I think I was getting a little excited. I circled my aureola with the bright red pencil then coated my erect nipples with the bright red lipstick, finally I applied the lip gloss.
I thought, 'Oh God, this is turning me on'. I loved the look of my erect lipstick coated nipples.
I turned to face him and said, 'What do you think'.
He smiled and said, 'Gorgeous, almost good enough to suck, but I know I mustn't'.
I was now only wearing my knickers and he said, 'Time for the stockings and shoes'.
I lowered my knickers and stepped out of them. I could feel my pussy getting damp. I was getting turned on. I sat on the bed and pulled the fishnet stockings up my legs and then bent down and put the shoes on and fastened the ankle straps.
He said, 'Look in the mirror and see how sexy you look'.
I stood up and admired myself. I know I'm a little overweight but I have to admit I did look sexy.
He reached onto the bed a handed me a cigarette. I put it in between my bright red lips. He offered me a light and I inhaled and blew the smoke out through my red lips.
He said, 'I want to watch you smoke. I want to watch as you suck on the cigarette and watch as you blow the plume of smoke out through your sexy red lips.'
I had never thought of smoking being sexy but when he described it like that I began to imagine it was. It was almost as if I was sucking a cock and blowing the cum out through my lips. Each time I inhaled I blew the smoke directly at him. I realised this was what he wanted.
He then said, 'When you go outside for a cigarette at work I watch you whenever I can. It turns me on watching you inhale and exhale.'
He held the ashtray for me until I had finished my cigarette. I looked in the mirror and my lipstick was still intact. My nipples were also still fully erect.
Then he said, 'I think its time to start what we are really here for.'
Then he went over to an armchair and pushed it in front of the mirrror and said, 'I want you to watch you play with yourself. I want you to watch yourself cum'.
I sat in the armchair and he said, 'Drape your legs over each side. I want you to be able to see inside your pussy.'
I did as he said. I was very wet. The anticipation was terrible. I really wanted to do this. I really wanted to cum. Although I often played with myself in bed, this was different. This was someone else as well as me.
I sat down and opened my legs and draped them over the arms.
He handed me 2 vibrators and a large black dildo. I took the smaller of the vibrators and switched it on and let it buzz over my open pussy lips and then let it wander up to my clit. I looked at myself in the mirror and saw one very sexily turned on female. I thought, Oh God, I'm going to cum very soon.
As my pussy lips opened I eased the vibrator inside but I needed something bigger. I said, 'Let me have the dildo.'
It was huge, but it was what I needed. I eased it inside me. I was amazed at how easily it went in. I have had a few black well endowed boyfriends so I was used to large cocks. In fact I love big cocks.
I was getting so turned on that I didn't notice that my boss had undressed. I saw him in the mirrror as he stroked his cock to full erection. Although I didn't want his cock I was fascinated watching him play with himself. In fact it turned me on even more.
I slowed down and eased the large black dildo deep inside me until it would go no further and then slowly withdrew it and then plunged it deep inside again. I looked at my pussy lips and was amazed at how wet they were. I was ready to cum.
I said, 'Can I cum yet'.
He replied, 'If you can cum again, yes'.
I knew I wouldn't have any trouble cumming again.
I started fucking my pussy with the dildo. I plunged it in as far as it would go then slowly withdrew it and plunged it deep inside again. I used one hand to play with my clit. I could see my fingers getting wetter as my pussy juices flowed out over them.
He was rubbing his cock faster and I sensed he was going to cum soon as he kept slowing down. His cock was only inches from my face as he stood beside me. Normally I would have taken it into my mouth and sucked him off, but not this time.
My nipples were huge. I wanted to play with them but didn't have a spare hand.
I said to him, 'Play with my nipples, pinch them, squeeze them as hard as you can.,
He let go of his cock and stood behind me. I saw his hands reach down and play with my bright red nipples. He squeezed them hard. I adored it. I plunged the dildo deeper and deeper until I knew I was there. I screamed out with pleasure as wave after wave of orgasm throbbed through my body.
As my orgasm subsided I left the dildo embedded deep inside my cunt. It felt wonderful.
He carried on playing with my nipples, but now it was gentle caressing. Suddenly he stopped and went and got me a cigarette.
I parted my lips and he put the cigarette betweeen them and then offered me a light. I inhaled deeply and as I raised my hand to remove it from my lips he did it for me and said, 'Carry on playing with yourself'.
I watched him in the mirror as he stared at me smoking and playing with my pussy. He held the cigarette between his fingers and then put it between my lips and then withdrew it after I had inhaled. All the while I was playing with my pussy while he held the cigarette for me.
I looked in the mirror and watched as one hand held the cigarette and the other stroked his cock. I blew the cigarette smoke direct at the mirror
When I had finished smoking he handed me the vibrator. The dildo was still embedded deep inside my pussy. I turned the vibrator on and put it against my clit. I was going to give myself double the pleasure.
He stood behind me again and started squeezing my nipples. My pussy was getting wetter again and I knew I could cum whenever I wanted to.
I said to him, 'Let me watch you wank yourself off.'
He released one hand from my nipples and started rubbing his cock. I watched in awe as he pleasured himself. I was fucking myself with the dildo while the vibrator got to work on my clit.
I said, 'I'm going to cum again soon and this is going to be the big one'.
He squeezed my nipple harder and rubbed his cock faster. I was fucking myself as hard as I could as I felt my orgasm start. Suddenly it happened as wave after wave of throbbing orgasm shot through my body.
He stood close to the mirror and made himself cum. I watched as streams of white hot cum landed on the mirror. He had aimed it directly at my face. I watched as his cum trickled down the mirror. We had both enjoyed watching each other cum.
We washed and cleaned up. I picked up the £100 and put it into my purse.
I handed him the vibrators and lipstick and said, 'We'll need these next time'.
If you'd like me to write a story about your wife, girlfriend, sister, neighbour etc, give me some details like storyline and what they look like. The more information you give me the more realistic I can make it.