Bound, Gagged & Played for a Foolbyanalplayplease©
I found Teddy's ad in the newspaper. He wanted to meet a woman in his age bracket with a strong mind and a strong will. I sensed vulnerability and so I called.
He told me very quickly that he was 5'11, an investment banker and in good health from going to the gym each day after work. But he was not confident in himself and was just looking for a strong woman to hold onto. (Pull down, I thought.)
I decided to meet him for coffee during our lunch break. He was sweet and smiling. What most women would kill for. He had that easy laugh that puts people at ease. He asked about my career, my life, and myself. I was everything he wanted me to be. I play very well into the roles that men expect. It allows me to gain the upper hand later when it counts most.
We met for dinner later in the weekend and I once again played to Teddy's desire for women. I was charming, slightly quirky, well dressed, beautiful, and even vulnerable. After dinner we went back to his apartment and had sweet sex. The kind I don't like. Teddy was so passionate for one minute I felt bad about my plans for him. He came, I came, he kissed me, and I kissed back and told him I would call in the morning. He asked me to stay. I declined with excuses.
The next morning I sent him lunch through a courier service. Lunch included a hotel key. I called five minutes after the courier was to arrive. He answered with a thank you. I said, "You're welcome. 5:30, room 217." And put the phone down effectively ending his call.
I left work early at 4:00. I arrived at the semi-swanky hotel and tipped the bellhop for carrying my bag of tricks. I stripped my clothes off and left them in a heap on the floor. I headed to the large tub in the bathroom. I turned on the hot water, added pre-ordered bubbles and turned the radio on. I shimmied my naked ass all over the bathroom. Opened wide the curtains to look at the view and stood in my naked splendor for the city to see.
I danced over to the tub and shut of the water. I climbed in and let the worries of the day wash away with soft scented bubbles. I stood to rinse twenty minutes later. I parted my lower lips and rinsed the suds. I ran my fingertips over my wet clit and slid a finger into my moist pussy. I pumped my hand in and out for a few minutes. I played with my clit. I pinched my nipples and shuddered to an orgasm all over my hand. I let the water rinse away my juices and grabbed the towel. I dried myself off and slipped on a pair of thigh highs and a garter. I decided to avoid underwear. I grabbed a shirt and on second thought laid it back down and decided to remain topless. I wore nothing but stockings and a garter. A bit shocking but hot. Very hot.
I checked the clock. Only 5:00 p.m. plenty of time to organize my bag of tricks. I set a pair of handcuffs under the right side of the mattress. I put the gag and blindfold below the pillows. Rope under the throw blanket lying tauntingly on the bottom of the bed. Mini bar opened and organized. Just then the knock on the door. 5:10 p.m. Not him, but the chilled wine and fruit. I opened the door to my bellhop. He gawked at my nakedness and said, "I have your wine." I asked him to put the cart by the bed. He did as asked and stood staring at me.
"Would you like to lick my pussy before my friend arrives?" I asked. He nodded and leapt between my thighs. He pushed his nose into my clit and inhaled. He put his hands on my ass and rubbed slowly as he licked my moistening pussy. He sucked hard on my clit and alternated between stroking, licking and sucking. I stood over him with my pussy dripping onto his face. He was working furiously over my clit for a few minutes. I came with shuddering gasps and a howl. I made him lick me clean quickly. 5:25 p.m. the bellhop had to go. "Give me your number, I may call." He did as asked and walked out.
I arranged myself on the chair by the bed. Long legs crossed, breasts high and un harnessed. High heels shining and moving slightly as I waited for Teddy to arrive. 5:30 p.m. sharp. Typical businessman. The door beeps and Teddy enters. He finally turns his head to the left and sees me sitting there, he gasped.
"I don't understand. Why are we here." "Shhh, just experience." I stood up and Teddy just stood shocked at my outfit or lack thereof. "Don't I look beautiful?" I asked. Teddy had no way to say no. He mumbled a yes. I walked to him and nuzzled his neck and bit him lightly.
I began unbuttoning his shirt. "Teddy, why are you dressed when I am not?" Ted had no way to respond. I could tell he was uncomfortable but he was obeying. He was just as I suspected. He was curious and unwilling to say no to a women.
His shirt was now off and I was working on his pants. Shoes were next and then socks. He did not utter a peep until I got to his boxer-briefs. "What's going on?" I had to laugh. He was so clueless. "You are going to be pleasured and so am I." His boxer briefs were down and his cock was semi hard.
I sucked his cock into my mouth. Soon he was growing and pre cum was on my lips. I stood up and kissed him with cum tainted lips. He tasted himself a bit and I backed away. He still looked scared.
I pulled him toward the bed and pushed him down. I reached for the blindfold and placed it over his eyes. He protested. I told him to trust me. I got between his legs and licked his now hard cock until I knew it would be fruitless for him to protest.
He was unable to move much without his sight and so I walked around to the bed and reached under for the handcuffs. I pulled his arms behind his back and clicked them shut. Teddy was not too happy but I began stroking his cock and making him feel good.
I asked him to stand and with assistance he did. I helped him to sit on the dresser. I lowered myself onto his cock and felt my warm pussy fill. I groaned in delight and contracted my muscles around his hardness. I began moving up and down slightly. I heard Teddy gasping and I knew he was close to cumming. It was time for step two. I climbed off of his lap and helped him to the bed. I knew he wanted to cum. I told him he would not be cumming until I wanted him to. I told him to open his mouth.
I slid my body on top of his and placed my pussy on his lips and told him to please me. He licked and sucked obediently. He was taking to this much faster than I expected. I began grinding my pussy into his mouth. I soon came with my third orgasm of the night. The first one from Ted.
After I came I told him to open up again and reached under the pillow for the gag. I placed it in his mouth and made sure his nose was clear so he could breathe. Then I lowered my head to his cock and licked my pussy juice off of him. I told him to lie still.
He looked so sweet handcuffed, blindfolded and gagged. Now for the rope… But first, my ass needed attention. I sat back down on his now throbbing cock. I spoke to him softly, sweetly. I took some lube from the nightstand and began rubbing my asshole. I rode up and down on Teddy slowly, teasing him as I penetrated my ass with my fingers. I pushed more lube into my ass. Stretching it just as slowly as I was riding Teddy's cock.
I got off of Teddy and blew on his cock. The cold air rushed around it making it sting and tingle. Teddy muffled a groan. I took the rope out and tied his feet together. He squirmed and muffled cries came out. He was lying on his own arms but he looked all right to me. Out of pure kindness I turned him on his side and got in a spooning position with him.
I pushed my well-lubed ass against his very hard cock. "Now Teddy, You are going to fuck my ass. I will let you cum. I want hot cum dripping out of my ass soon. Very soon. I pushed the head of his cock into my ass. It was warm and throbbing. Teddy was making noises. I could not tell if they were good or bad. But he was unable to protest anyway. I pushed back further to receive the rest of his cock.
"Now Teddy, I know you did not know this was going to happen, and we don't have any safety words. But you need to cum, and my ass needs to be fucked. I know you don't like this in your head but your cock is enjoying this very much. Now cum in my ass.
He obeyed, immediately. I had only had a few seconds of my beloved anal. But he had obeyed me, just as I knew he would. I pulled my ass off of his cock. To make the rest of this work I knew he needed to be hard again.
I put my mouth on his cock straight out of my ass. I sucked him back to hardness. It was soon but in his position he had no choice but to be turned on. I made sure he was fully hard and then I got up.
I went to the wine and fruit. I drank and ate. I talked to Teddy and told him what I was ding. His erection did not go down. After I finished the fruit I called room service. I told them I had dirty dishes. I asked for them to send the bellhop. They tried refusing since he was supposed to be outside not in the kitchen. But they did as asked. Teddy heard the call and knew someone was coming to collect the plates. He was on the bed, bound and gagged and naked. He began squirming, making noises and writhing around. I walked to him and kissed his cheeks and told him that it was only the bellhop. He should appreciate what I was doing for him.
My bellhop rang, "I told you I may be calling you." He looked to the bed and saw Teddy. He laughed and said, "He cannot be servicing you too well in that position." I told my bellhop that he was doing all right but in his situation I could not be as stimulated as I would like.
I went back to the bed and pushed myself back down on Teddy's cock, my ass to his blindfolded and gagged face. My ass opened to accept him and Teddy groaned under me. I placed my arms behind myself and leaned back. I looked at the bellhop and told him to fuck my pussy.
Quick as a flash he was naked and climbing on the bed. My stocking clad legs were pushed wider and my heels were pushed into the bed. I told him he was not allowed to touch Ted but he was allowed to pound my pussy, just this once.
He climbed between my things and placed his legs over Teddy's. He entered my pussy and I was filled with two cocks. My ass was speared by the bound, gagged and helpless Ted. My pussy was full of my bellhop. We found a rhythm. I came very soon and Ted exploded for the second time inside of my ass. The bellhop was pounding me and Ted was still lying on his arms.
I told him to get up. I climbed off of Ted and got on my hand and knees. I began cleaning up Teddy's cock and the bellhop climbed behind me and fucked my pussy doggy style. He came inside of my hot pussy. The cum was dripping out of me. I told the bellhop to dress and leave. He did as told.
I took the gag out of Teddy's mouth and kissed him. He did not object as I thought he would. I untied his feet, took the handcuffs off of him. And then I took off his blindfold. Teddy was no free to move. He kissed me. He got on his knees and licked the cum from my pussy and ass. He came back to my mouth and kissed me.
He asked when we would be meeting again. I laughed and told him never. Once a man is broken in, it is time for me to move on.