Sheila

Working for an escort service puts you into a lot of strange situations. Like the time I got a call to go to a swank downtown hotel. A working girl entering one of these places stands an excellent chance of getting challenged. A guy hardly brings a glance. In fact, today the doorman called me Sir. I got a kick out of that! Anyway, I got this call to meet a gal in her room. I wasn't sure what was up and the service said she just wanted someone to keep her company. It was a weekday afternoon and I was off work at the PR firm so I took the call. I got off the elevator at the 10th floor and found room 1019. This hotel was so posh the rooms had doorbells that chimed! I pushed the button and waited a moment. I knew someone was looking out the peephole as I saw a shadow fall over it. The chain was taken off the door and the lock turned and the door opened. "Yes?" said the woman. I couldn't make her out very well because the light from the window directly behind her made her stand in darkness. Her outfit was diaphanous and the light from behind created an erotic picture of ripe womanhood.

"I'm Mike Cargo from Escorts," I said.

"Come in, Mike. I've been expecting you."

I entered the room expecting it to be a regular hotel type room. It wasn't. This was the living room of a suite. And it was beautiful. The picture window opened out onto a large balcony with a breath-taking view of Lake Michigan. The balcony was larger than my living room. The room had a large couch that looked like it could hold six, a couple of easy chairs, a huge inlaid coffee table covered with glass, a bar in the corner, a huge TV sat in the other corner. I kept looking around the room, spell-bound. "Are you looking for something in particular, Mike?" the woman said.

"No. I've just never been in a place like this. It is fantastic."

"Thank you. My husband and I like to stay here when we are in town. Come and sit down," she said reaching out for my hand. She led me to the couch and sat down. I joined her. "My name is Sheila and I want us to be good friends."

"OK, Sheila. The service didn't tell me much, just that you wanted someone to talk to."

"That's not entirely true," she said. "Although a little conversation would be nice. I had another four letter word in mind and that too ends in 'k'."

I smiled at her. In the room with the light on her face I could see she was in her late forties or early fifties. Her shape wasn't too bad. I little hefty maybe but not bad. I thought it would be an interesting afternoon. It was.

"Sheila, the service is not in the business of hooking."

"I know that silly! I was serious about the conversation and if something else happens that's not the services fault is it?"

"No, it's not. I just want you to know ahead of time that anything that happens is between you and I and not the service." We sat and talked for about half an hour about Chicago and then moved to the balcony and took in the sights. Her room was the highest thing on this side of the hotel and we were able to look over everything around us. Quite a heady feeling. I pointed out a few of the points of interest. Sheila pretended not to see one of them so I had to stand behind her and point over her shoulder at the spot. She leaned back against me gently as though it was perfectly natural to do so. I didn't say anything. When I finished pointing it out she stayed where she was. I could feel the warmth of her body through our clothes. I began to feel the stirrings in my loins. I put my arm casually over her shoulder and Sheila snuggled right in. I got a little bolder and dropped my hand to her tit. She was bra-less. She didn't say a word. I squeezed her nipple and it stood out immediately. Sheila moaned a little but didn't make a move. I massaged her tit and nipple through her gown. After a few minutes I felt Sheila's hand on my crotch. I turned her around and her mouth eagerly found mine. I caressed her back and moved my hands down to her ass and pulled her closer. She didn't resist. After a couple of minutes of dueling tongues we broke for air. Sheila took my hand and led me into the living room. I thought she was going to take me into the bedroom but I was wrong. She stopped and turned to me. She reached up and untied the bow at her throat. The gown fell to her feet. "Here. Right here," she whispered.

I stripped in record time. I took her in my arms and maneuvered her toward the couch. She resisted. "The chair," she said throatily.

I moved to the chair practically carrying her. She turned and pushed me down. I knew what she wanted and just let her go to work. She got down on her knees and pulled my head down to hers. She deep-throated me while her hand found my swelling manhood. She kept the kiss going while she stroked me to fullness. Sheila broke the kiss and slid down to my chest. She licked my nipples and gently chewed them with her teeth. She moved down licking all the way. I slid down in the chair to give her a better target and she took advantage of it. She gasped when she saw my cock. But she didn't hesitate and took it in her mouth and tried to swallow the whole thing. It was too much for her but she sure did try! Sheila was pretty good in the cock-sucking department so I just laid back and let her go.

Finally, she got up and straddled the arms of the chair. That put her several inches above my belly. She reached under and put my cockhead at the entrance to her pussy and settled slowly on it. It was obvious she had done it this way before. She knew exactly what she could do with the arms of the chair. She raised herself up to the tip of my cock and then lowered herself back down. With her legs on the arms she got maximum penetration. I swear I felt her womb with the tip of my cock. She kept that up for quite a while and suddenly began moving faster. I knew she was close but so was I. I let her go. She pumped furiously. I could feel her coming at the same time I did. She didn't stop. She came three more times in the next couple of minutes and then collapsed on my chest. She lay on my chest for a while with her legs still over the arms of the chair. Then she rose up and off my cock and got off the chair. She looked down at me. "Feel like a shower?"

"You bet!" We adjourned to the bathroom where we enjoyed a leisurely shower soaping each other and getting excited all over again. We stepped out of the shower and dried each other off. The physical contact only excited us more and we knew we were going to go at it again. The question was where? I think Sheila read my mind. "The balcony?" she asked.

We moved out to the balcony to the chaise lounge. Sheila lay on it and I began my ministrations starting with her lips and moving on to her tits and finally to her pussy. By the time I hit her honey-pot it was wet and juicy. I dove in and lapped it up. It was delicious. I found her clitoris and chewed on it a bit. Sheila writhed violently. She put her legs over my shoulders and crossed her ankles. I was captive! But what a place to be captive. I kept licking and chewing and Sheila kept opening and closing her legs around my head. I couldn't wait much longer and reached up and moved her legs. I slid up and put my staff against her opening and slid in to the hilt. We began the sweet motions of love and timed each other’s movements for maximum effect. This was one dynamite piece of ass! We pumped for several minutes. Sheila stopped me and pushed me off. I couldn't understand why. She got up and moved to the railing. She leaned over and put her ass out inviting me to enter her from behind without saying a word. I moved behind her and entered her without a hitch. We moved together. I reached up and grabbed her tits. I massaged her nipples and tits while I pumped her from behind. Sheila began moaning and moving faster and faster. I felt her pussy opening and closing as she climaxed. I knew she would come some more and kept pumping. She did. I counted four more before I filled her with my jism. We stayed that way for a few minutes catching our breath.

I had just pulled out and Sheila was standing upright when I heard hand clapping. I spun around. A man was standing in the doorway wearing only an undershirt and socks. I looked at Sheila. She smiled and said, "Don't be alarmed, darling. This is my husband, Dwayne. He gets his kicks watching me fuck other men. He's been watching us all afternoon, haven't you dear?"

"Yes, my dearest. And it was a marvelous demonstration. I came at least four times."

Sheila explained that he liked to hide in closets, etc., and watch her while he jacked off. She said he especially liked it when she had women or black men.

"Yes, yes! That's true! But you, my fine cocksmen, are fantastic. I've never seen such staying power. Oh, for a cock like yours!"