My latest sugar daddy and I had just finished lunch. We decided that we would like to have a nice holiday and so I logged on to the computer to search for such a holiday. As I was searching the web I heard a beep which signified that an e-mail had arrived. I logged on to my mail server and this is what I found. "Hi there Yorkie! How are you donig? Fancy some excitement?"
I replied quite guardedly "Maybeeee." as it was someone I had only met last week I was not sure what I would be letting myself in for. He seemed very interesting and possibly quite kinky so I was not prepared to give him an immediate yes reply.
The next message was very surprising and I was quite shocked but very turned on by it.
"Here is a dare for you, my gorgeous sweet slutty whore. This is what I would like you to do. Wait until your period is at its heaviest then call me over !!!!! You should be dressed in a cut-out bra with a tight white sweater, crotchless panties, suspender belt and black stockings, a short swirling skirt and high heel shoes. When I arrive the mere sight of you will give me a hard on. You will slowly remove the sweater and skirt. After I have admired you dressed like this you will remove the bra and the panties. You will take me to your bedroom and lie on the bed. What will happen next I will leave to your imagination."
As I said - I was shocked but very turned on at the thought of what would happen. After some short thought I replied back. "I would like some time to think it over before I could possibly agree to such a proposition."
Back came the reply, "O.K. Whore, I will give you two days maximum for your reply. If I have not heard from you within two days it is goodbye for ever!"
I knew my sugar daddy was reluctantly willing for me to have other lovers - I had made it a condition before accepting his invitation to move in with him.
As he is much older than me the sex is not up to my preferred frequency and so I very frequently go out on the town and have one night stands.
I wondered if I should tell Charlie, my sugar daddy, about the mail and also what I should do about it myself. I must admit I felt very much inclined to accept - it sounded very sexy and thrilling. The next 36 hours had me going about my business with the thought of meeting Derek very much in the forefront of my thoughts. I finally decided. Yes I would accept the dare. I kept Derek in suspense almost up to the deadline before I replied - just the one word. "YES."
He replied almost immediately. "I await your call with great anticipation." he mailed back.
It was almost two weeks before I expected my next period so I went through this time eagerly awaiting our meeting.
In the meantime I decided to do a little shopping to buy myself a new pair of crotchless panties and a good expensive cut out nipple bra.I also needed a suitable skirt for my evening so decided to add one to my list of purchases. I already had a nice tight white sweater and a suspender belt and I made sure that my purchases matched the belt.
My period finally arrived so I sent the e-mail to Derek. "I will expect you at 6:30 pm in two days time. Everything will be as you requested."
Two days later after an early dinner with Charlie I went upstairs to get myself ready for the evening. I told Charlie to let Derek in when he arrived.
I went upstairs and changed into my outfit. I stripped naked and went into the shower. When I emerged I dried myself with a nice warm fluffy towel.
Moving into the bedroom I inserted a fresh tampon into my bleeding cunt. I put on the bra and admired myself in the mirror. My nipples stuck out of the bra quite beautifully. I decided to put a bit of bright red lipstick on each nipple to make them even more outstanding. I next put on the suspender belt and attached the sheer black stockings to the clips. I gave my clit a quick flick and caress before donning my panties. I completed my ensemble by slipping on my new skirt and finally slipped the tight white sweater over my head and eased it into position over my bra covered tits. I put on some eye shadow and mascara and finished my preparations with a nice bright red slutty looking lipstick on my lips. I was ready and waiting!
At 6:35 the doorbell rang and I heard Charlie go to the door to see who it was. Sure enough it was Derek.
Charlie invited him in and shortly after I heard them both climbing the stairs. When they entered the room Derek moved over to me and planted a long sloppy kiss on my lips. When we moved apart he gestured to Charlie to sit down on the bedside chair. he opened his holdall and proceeded to tie Charlie onto the chair - making sure his hands and feet were totally immobilised. Charlie was now in no position to interfere with anything that was now to occur.
Derek now asked me to raise my hands above my head and when I complied he fished out some silken rope and tied them together. Things were not progressing as he had stated in the e-mail. He next moved over to me, gave my nipples a quick flick and then moved his hands much lower, to my cunt that was exposed due to my wearing the crotchless panties. He now gave my clit a quick pat before he moved to the string peeking out of my cunt. He took hold of the string and slowly pulled on it, causing the newly inserted tampon to slide out of me very slowly. When it was fully out he took it in his hand and stuffed it into my mouth as a gag. I was extremely shocked but all I could do was let out a muffled scream as he had gagged me before I realised what was happening.
He now went back into his holdall and produced a pair of nipple clamps - a very vicious looking pair they were - and pulling on my nipples one at a time he elongated them and fastened each clamp in turn.
He now moved me over to the bed and pushed me down onto it. He spread my legs and fastened each to a separate corner of the bed.
He now proceeded to flick my clamped nipples with his fingers, making me even more aroused than I ever was - more than whilst I anticipated his arrival.
I wanted him inside me - NOW! as soon as possible. But, he continued to torment me - raising me to an even higher pitch of anticipation. He continued flicking my nipples with one hand whilst slowly moving his other hand down to my slavering, bleeding crotch. My own juices were flowing together with my menstrual flow and he was raising me even higher. Suddenly I was there - I came with an unexpected orgasm. I never expected to cum so soon. he pulled away and watched me in the throes of my climax. Just as I was recovering from my orgasm I felt his massive prick at the entrance to my bloody cunt. He wasted no time in thrusting it within my waiting cunt. Here I was, lying there now with him fully inside me. He remained still for quite a while before he started to move. He started moving in and out of me slowly before eventually picking up the pace. He gradually speeded up, thrusting with increasing pace. Before I realised it my second orgasm was upon me. I yelled out in ecstacy -louder than I can ever remember doing before. It seemed to affect Derek tremendously and before I had fully appreciated my climax I felt him sort of freeze and I was aware of his prick shooting his semen into my cunt. Several spasms later he finally finished cumming inside me. What next I wondered? ........ to be continued....