A Date With Cindy

I am posting a series of true stories about my encounters with "providers" around the country. I totally respect these women and in these stories have no intention of demeaning them. The names of the women have been changed for their protection. Everything else is as it happened.

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After an amazing and truly unique time with Carla in Cincinnati, I headed to Seattle for my next business consulting trip. I figured to be in Seattle for three or four days, but I booked an extra day in the hotel in case I got extra lucky with an escort.

Before I left Cincinnati, I searched the various sites and boards looking for companionship. Seattle seems to be fertile ground for escorts and I was having a difficult time making a decision. I finally settled on Cindy. She's nearing 50 years old, is a rather petite redhead, and had glowing reviews. It was also pretty clear that she had a kinky side. Sounded good to me!

I emailed Cindy and informed her of my upcoming trip to Seattle. I told her that I loved all her reviews and that I wanted to see what all the talk was about. I told her that I would be staying at a hotel near downtown and that I would like her to come visit me there.

In a couple of hours, Cindy responded. She was all for meeting me. I replied that I would be arriving in Seattle Thursday afternoon assuming the plane was on time. I suggested an incall at my hotel for 7:00 pm for three hours. Normally, I like longer dates, but this was the first time I had been in Seattle for a few years and I wanted to see how it went with her before, hopefully, having a second date that would last longer, perhaps overnight in my room.

It wasn't long before Cindy agreed to our date. She directed me to her website where I could learn more about her and view pictures of her. She gave me the password for the private area of the site. I easily found her website, entered the password, and spent the next hour combing thru her sexy pictures. In her public site, her face is obscured, but the private site shows all of her. Literally. She's a little over five feet tall with flowing red hair. Perhaps of touch of grey, but it looked wonderful to me. Her nude pictures show magnificent breasts. Not huge, but perfectly shaped and with erect nipples. Also, she's a total smoothie. A couple close up shots of her pussy make it clear that she's waxed. The cool thing, however, is her large pussy lips. In a couple of the pictures, she's fingering her pussy and it's obvious that she has a prominent clit. There's one memorable picture that is a close up of her clit. She has the hood pulled back and is fondling her magnificent, distended clit. I was getting hard just thinking about licking her beautiful bud.

I headed for the Cincinnati airport for the nonstop flight to Seattle. I could think of nothing but Cindy. I was going to be in Seattle for two days before I had to report to my client's office. I knew that Cindy was going to be the focus of those two days.

An on time arrival in Seattle, a short limo ride to the hotel, lunch, and I was ready for Cindy. I tried to take a nap, but it was fruitless. At about 5:00 p.m. I went back down to the lobby restaurant and had a salad with a glass of C-nay. I also ordered a bottle of a very nice Chardonnay to be sent up to my room. After eating, I went back upstairs to prepare for the evening. I took a shower, paying special attention to rid my cock and balls of any stubble. I thought about what it would be like to get waxed, but put it out of my mind. The combination of the shaving and the anticipation for what lay ahead made it nearly impossible to keep from rubbing one off, but I fought off the urge

In the days since my first contact with Cindy, we had had several teasing emails. She asked me if I traveled with gym shorts and tee shirts. I assured her that I did since I liked to workout at hotels that provided such facilities, which most of the top line hotels do these days. She said, "Put on your gym shorts and a tee shirt. That way, it won't take much time to get naked and get down to party time." Who was I to quibble?

After my shower, I shaved my face, brushed my teeth, gargled with mouthwash, and put on clean gym shorts and a new tee shirt. I was ready.

The worst part of these dates is the waiting. From her reviews, I knew that I was in for something special. I had told Cindy that I wanted her to take charge and that the only limit I had was no pain. I think that might have disappointed her a bit, but we'd have to see.

Finally, it was arrival time. As agreed, Cindy knocked on my door at 7:00 p.m. I opened the door and there stood a vision of loveliness. She's about 5-3 and maybe 130 pounds. A very nice, womanly shape. The first thing I noticed was her magnificent mane of dense red hair. I'm sure is was her natural hair color, but I couldn't check to see if the carpet matched the drapes since I knew that she was a smoothie down below. Cindy was wearing a peasant dress with a neckline that showed just a hint of cleavage. Sexy, but not too blatant.

Cindy is a beautiful woman, but in a very natural way. I'm sure she doesn't wear any makeup. Everything about her was natural, except her sex drive. From the reviews I had read, I was in for a hell of an evening.

I invited her in and gave her a perfunctory hug. My hand touched the middle of her back and it was clear that she was braless. My cock twitched and began to stiffen a bit.

Cindy had a large handbag/purse over her shoulder. She put it on the table in the corner. My gym shorts were already tenting. I offered her a glass of the Chardonnay. We clinked glasses and toasted a fun evening.

We gave each other the condensed version of our lives. Her real job is working as a nurse in a retirement home. She's divorced with no kids. She was intrigued by my job. She struggled to understand how a guy can be on the road 100% of the time. No home, no family. I said that, for me, it's normal since I have been doing it for over 30 years. (I think I'm still at the top of Delta's Sky Miles list. I never use the miles for my own travel. I donate them to a charity for kids.)

Then, with no warning, she put down her glass, stood up, and shrugged her dress off. It fell to the floor into a puddle. I was right...no bra. Also, no panties. For a 50ish year old, she had a magnificent body. A little paunch, but I love that. Perfect tits, maybe 34C. Of course, as a red head, she had lots of freckles. She did a little pirouette. I absolutely loved her rear end. There were no tan lines, but it was obvious that she had spent a little time in the sun.

I was absolutely gobsmacked by her natural beauty. No makeup, but she didn't need any. Damn! She was hot, but not in a supergalamorous way. Completely natural and totally beautiful in the MILF next door way. Except in her case it was MIWF, if you get my drift.

By now, my cock was almost at full mast. She said, "Stand up." When I did, my cock was straight out, but I still had my gym shorts on. She moved over towards me, grabbed by bottom of the tee shirt and skinned if off of me. Now, here I was naked except for my gym shorts. She moved in for a hug and my cock stabbed her right in the belly. She pulled my head down and began kissing me. She also adjusted my cock to that it was straight up between us. A nice long kiss, but no tongue yet.

She broke off the kiss and stepped back. "You're overdressed." With that, she squatted down and pulled my gym shorts off. My cock was at her eye level and she seemed excited that it was shaved bare. "I love shaved cocks. No hair in my teeth!"

With that, the two of us were totally naked standing in the living room of my hotel suite. We hugged and kissed, with the kisses getting longer and more urgent. Who turned up the thermostat?

We moved back to the couch and I sat down. She stood in front of me in all her naked, freckled glory. She retrieved our wine glasses and handed me mine. She said, "I don't know for sure it that is your glass. Wouldn't want to get any germs." That produced a nice round of laughs.

After we each took a swig of wine, she put the glasses down. I wondered what she had in mind next. I was sitting there with a rock-hard boner sticking straight up. She was staring right at me. Without breaking her stare, she moved onto the couch, straddled my lap, and impaled herself on my cock!

With her arms around my neck and my dick buried in her, she lowered her head and we began kissing. Major league kissing! All the while that we were kissing, she hand not moved her hips. My cock was deep inside her and, for the time being, remained fully inserted.

Then, all of sudden, she did something that I had never experienced. She got off me, moved back a bit, lowered her head, and started sucking my cock. She said, "I like licking my juices off of your cock." It was an unusual, but enjoyable feeling. Then she jumped up and said, "Let's take this to the bedroom."

She led me to the bed and laid down on her back. She said, "Eat me!" Sweeter words were never spoken. By this time, it was clear that she wanted to be in charge. Fine with me.

I started at the foot of the bed and slowly began crawling between her widely spread legs. It was then that I noticed her prominent pussy lips. As I got closer, she reached down and spread her lips. "I said, eat me." I was on my stomach preparing to do as I was ordered. I moved my right hand up to finger her. "No fingers. Tongue only!" Ok, my dear, you win.

I began softly. Kissing her magnificent pussy lips and gently grasped one of them between my lips. I pulled it towards me. She moaned. I switched to the other lip. More moaning. Now, I released her pussy lip, flattened my tongue, and went to work on her clit. After a minute or so of gentle teasing of her clit, she said, "Harder". I inserted my tongue as far as I could inside her and began curling it upwards. I assumed I would not be far enough inside her to hit her G spot, so I sneaked my right index finger under may tongue. I moved the finger forward a little and then curled it upwards. Bingo! I found her G spot. She was no longer giving orders as I tried to drive her over the edge. My back and neck were getting tired in this position, but I didn't want to lose the moment. She was writhing around while I tried my best to keep contact with her G spot.

All of a sudden, her body froze up. Her hips came off the bed, and she had a massive orgasm. It was the most erotic and beautiful thing I've ever witnessed. For a split second, I thought she had stopped breathing. Then, just as quickly, she collapsed back onto the bed and let out a whoosh of air from her lungs.

She started to try to talk and I held my finger to my lips. "Shh, my dear. Don't say anything." I withdrew my fingers from her pussy and move up to embrace her, side by side. She squeezed me, backed off a bit, and looked me square in the eyes. She tried to talk, but couldn't. I swear she saw her soul.

We laid there cuddled up for several minutes and her pulse and respiration returned to normal. Finally, she turned to me and said, "That was fucking unbelievable." Being the smart ass that I am, I said, "Well, technically, there was no fucking involved." She laughed and said, " Not yet. But that will happen when I get back to Earth."

We rested for a few minutes and she may have dozed off for a bit. Finally, we both stirred. We got off the bed and each took a swallow of the wine."

Cindy said, "Let's freshen up in the shower."

She headed to the bathroom and turned on the shower. It was a shower stall big enough for two people. Don't forget, I haven't cum yet. At this point, I didn't really care. Her orgasm was such a beautiful sight that I didn't care about mine. Yet.

We had fun in the shower washing, teasing, poking, and prodding. At one point, she was behind me washing my back and she slid her hand down to my butt. She put a dollop of soap on her middle finger and, without ceremony, stuck the finger in my ass. I turned my head and she said, "Don't forget. I'm a nurse and I wanted to give you a prostate exam." I asked her if I passed the exam and she said, "Well, let me check a second time to be sure." And she did. And I passed.

I was a bit surprised that the hotel had not run out of hot water. Since we had plenty of hot water, we decided to wash each other's hair. That was first for me and it was kind of fun.

Eventually, we got out of the shower. For sure, we were both very clean. In my case, even my rectum was clean and my prostate was in good shape.

I went back to the bed while Cindy fired up the hair dryer. I think I dozed for a few minutes as I lay in bed in total bliss.

She came out of the bathroom looking like an angel. She looked at me on the bed and said, "I just realized that we haven't gotten you off yet." I assured her that I was not complaining. However, my cock seemed to have other ideas. As I watched this angelic creature standing at the foot of the bed, my cock rather quickly demanded attention.

She looked at it and said, "Now we're talking."

She crawled, slowly, onto the bed with her eyes locked onto her target. I spread my legs and she knelt between them. She slowly grabbed my cock and stroked it a bit. It was rock hard and looking for love. She was on her knees and lowered her head. She proceeded to give me the best blow job I've ever had. Not quite a full deep throat, but this wonderful lady knew what she was doing.

I was reaching the point of no return and I alerted her. With my cock still in her mouth, she looked me in the eye and winked. I took that to mean that she wanted it in her mouth. A few more seconds and she got her wish. In spades. Up to that point in my time with Cindy, I had had several hard-ons, but had not cum. That was about to change. I held my breath and shot a huge load of cum into her waiting mouth. This was followed by a couple of smaller spurts. She took it all. Then she let my dick out of he mouth. She looked up at me, opened her mouth stuck out her tongue. On it was my cum load. Just as quickly, she withdrew her tongue and swallowed. I thought I'd shoot again just watching that beautiful scene.

Cindy sat up, smacked her lips, and said, "You taste good!"

She then laid down beside me and we cuddled for a few minutes while I stroked her hair and her back.

I had lost all track of time. Hell, I didn't even know what day it was!

We got off the bed and moved to the couch. We finished the wine bottle and just grinned at each other. I said, "God, you're beautiful." She played the prim and proper roll and said, "Thank you, fine sir."

Finally, I looked at the clock. Four hours had flown by. I said, "You realize that you're on overtime." She smiled and said, "I don't care. I'm having too much fun."

I said, "Well, what's the plan?" She asked me if I could produce another hard-on. I told her that it's 50-50. She said, "Let's give it a try. If I can get it hard for us, will you fuck me in the ass?"

My eyes opened wide and, no kidding, my dick stirred a bit. I said, "Cindy, my little nympho, I'd be willing to give it the old college try."

She said, "I'm no hurry. How about if I stay the night and you fuck my ass in the morning?

She definitely drove a hard bargain, but I caved in and let her stay overnight.

We went back to the bedroom, pulled back the covers, and laid down. She turned her back to me and we assumed the classic spooning position. My cock made a bit of an attempt to get hard, but it wasn't to be. I rose up and turned her head towards me. I gave her a nice goodnight kiss and we were soon asleep.

Around 7:00 a.m., I awoke in a bit of a fog. I rolled over and was momentarily surprised to see somebody in my bed. It all came rushing back. Here was a beautiful redhead asleep in my bed.

I got up, took a pee, and brushed my teeth. By the time I got back to bed, Cindy was waking. "Hey stud," she said. And there was a twitch in my dick.

She got up in all her naked glory and headed to the bathroom to duplicate my ablutions. When she came back to bed, she had her kit of bathroom goodies. She reached in and pulled out a bottle of Astroglide. She held it up and said, "Remember our deal? I have the Ass-troglide right here, emphasizing the "ass".

She rolled over to me and we broke into a great round of deep kissing. Of course, my dick responded quickly. More kissing, breast play, pussy play, and ass play. She was teasing my backdoor as we continued to make out. By then, my cock was solid.

She sat up, looked at it and said, "Ready?" Of course, I agreed. She got the lube bottle and squirted a handful on my cock. She also took a dab and rubbed in on her anus. It had been a long time since I had anal sex and I knew this was going to be special.

She got on top of me, slid forward, reached around, and grabbed my cock. She rose up a little and aimed my dick at her asshole. She slowly slid down over my cock. Damn...it was tight!

She was grinning as she slowly rose up and down, forcing my cock deeper into her with each up/down cycle. I was trying to hold out longer, but it was a losing battle. I jerked one more time and shot my load deep inside her. She let out a little yelp and shuddered. I'm not sure how an anal orgasm worked, but I swear that Cindy just had one.

Again, we collapsed on the bed and snuggled. She said, "I'm sure the maids will wonder what happened here. On the other hand, they probably have lots of stories to tell."

We had recovered sufficiently to hit the shower again. Suffice it to say that both of our bodies were never so clean by the time we left the shower.

We dried each other with the hotel's big, fluffy towels. I was still in awe of her sexy body, but there would be no more sex, at least on this visit.

We got dressed and headed down to the lobby for breakfast. Lots of heads turned as Cindy walked by on my arm. I doubt that anybody noticed me, but I didn't care.

We had a nice breakfast and just talked like old friends for about an hour. It was time for me to return to the real world and go meet my clients. I walked Cindy to her car and held the door open for her. She got behind the wheel and, while swinging her legs into the car, shot me the last view of the magnificent pussy. She looked up at me and I said, "Don't tempt me".

Cindy drove off and thus ended an unforgettable "date" in Seattle. I'm already plotting things we can do next time.