Bit of a Risk

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Answering an ad - sometimes that works out.
4.1k words
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Part 1 of the 3 part series

Updated 09/22/2022
Created 05/15/2009
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imsally
imsally
100 Followers

I am a Doctor, part time anyway. I don't know why I even became one, in that early stage of my life I knew I would need a profession and government money was available so I took it.

It didn't take very long working in a trauma center for me to realize I didn't like that part, so I went to work for an HMO in a wellness clinic. That was better, I fit right in there.

As a young woman I wasn't blessed with beauty and if any of you have read my other stories, I guess I couldn't be accused of being blessed with brains, either.

Until I got into my 40's I was on the mousy and dumpy side. Then I came into an inheritance, suddenly I could afford about anything and I do mean anything. Why my friend Lee left everything to me I just don't know. I even tried to turn it all over to her brother, he wanted no part of it. I don't understand that to this day.

One thing about sudden money, it changes a person's life. I learned quickly it also changes almost everyone a person knows, too.

I spent money on having my hair changed completely, I learned how to do makeup by going so far as to take a class in that.

I can't say I became beautiful, but I did learn to take advantage of what I had. Then I met Tom and got married. Finally I thought I was happy, completely happy.

Several years of our off and on relationship taught me a lot about myself, also. Then Tom was lost in an accident, my life took another sudden change.

My late husband Tom had brought home a bike one day and I started using it. My body instantly started to change, the 10 to 15 pounds I had fought for decades just went away and stayed away.

There were lots of changes in my life after that. I met my friend Brad's brother, Jim. One thing led to another and pretty darn quickly, and we made incredible love.

I have to say I really did like that, and I liked Jim. But he was younger than me by quite a bit, it became obvious quickly that he was just having fun, there was no long term relationship going to be.

Then Brad and my good friend Patty were forced to move to get work. Brad ran the contracting business and that could best be described as non-existent. Even the work for the government dried up.

The opportunities were coming from the Federal level, Brad changed to doing different types of excavation work for roads, bridges, things like that. That meant they had to go to where the work was. More sudden changes in my life.

There were tearful hugs all around the day they left. Brad's brother Jim had long since moved on, he found a young and pretty cocktail waitress and she wasn't the type to stand very long for Jim slipping out to spend a night in bed with a mid forties lady doctor.

Once again, I was all alone. It didn't help one bit that Winter seemed to just go on and on, the days were cold and it was always wet so I couldn't even go out and ride my bike much.

I began to do a little bar hopping but drinking never was my thing. I did find one tiny little bar that actually had some pure fruit juices so I sat and chatted with the lady bartender many times.

Once in awhile men came up to me and made their attempts but I wasn't in the mood and their clever well practiced comments and lines just got nowhere with me.

My life was dull, empty.

I did go down to a local car lot and traded off my Van, ending up with a Black Impala that they sold so cheaply I couldn't turn it down. It had one of those V-8 engines and in our world of high priced gasoline I guess no one would even give it a second look. I liked it, it was easy to drive and got pretty good mileage, better than the Van in fact. Besides, it didn't rattle like the Van did.

For a few days I felt pretty good again, the new car was fun to learn about, it had lots of toys.

You can see from the last paragraph how my life was heading, the best description would be boring.

I was sitting at the tiny little bar sipping on a glass of Pomegranate juice and chatting with Pam, the bartender when for some reason I blurted out that I thought I needed a man.

She laughed and told me that maybe if I quit rejecting every man that even came close to me I might find one.

"The last thing I need is one that I will have to figure out how to get rid of." I told her, mostly just joking.

"Besides, every single one of them seems to have a few extra drinks down themselves before they get up any courage."

"Hell, honey, hire one then." She grinned at me and then went to serve a couple that had come in.

"Hire one?" I thought.

Lord. Just what I needed, a male prostitute. There really was no way in hell I would ever dream of doing anything like that.

Pam came back down the bar to me and we chatted some more.

"If anything ever walks in that I know is maybe worth a hoot I will let you know." She grinned.

"I doubt I will ever find anyone in a bar."

"You are probably right there. Say, why not just hire one of those Massage therapists, maybe one of them could give you a nice time." She let out a giggle at that.

"Fat chance of that." I answered. I had had a few massages, they used sheets and tied little diapers and acted terrified at the idea of touching anything beyond their "boundaries".

Besides, I suspected that most male massuers were probably gay, anyway.

"Well, check out this website." Pam jotted down an address and handed it to me. Then she winked and went back down the bar.

I stuck the slip of paper in my purse and forgot about it. It was several days later when it popped back into my head, I went and got the link and typed it into my browser.

Up popped an ads website. It had everything a person could think of. I began to scan through them. Most were blatant sexual requests, and most were from men, too. Why men would post photos of themselves with an erection is beyond me, no woman would really go for that. Well, most probably wouldn't anyway. I did notice that some of them were sure big though.

I did a lot of giggling, looking at the ads and reading them.

I finally ended up on a section that advertised massages. These seemed to be less sexually oriented, at least there weren't so many photos of men's penises.

I just had the thought in my mind that anyone that would post a picture like that in public was probably not someone I was looking for.

Then I spotted a polite ad that asked for a practice partner. I was unsure of what that meant but I figured since it was the cleanest ad of the bunch I would answer.

What the hell, my email address was anonymous so it couldn't hurt.

"Hello." I wrote. "I confess to being curious about your ad and I am willing to at least chat with you about it."

I almost deleted my email, I stared at it for a solid minute or two, then clicked "send."

Lord. What in the world was wrong with me? Answering an email for a "practice partner" on a message board? I closed the screen and went in to make myself some food. Then I sat and watched a soap opera on TV.

It was later that day when I thought about it again, I opened my email and there was a response.

"Hello, back!" It read. "Thank you for responding, I really am serious about offering massage work. I am finished with my schooling but don't yet have my license so I can't charge anything. I am well mannered and want you to feel comfortable if you choose to let me serve you."

It closed with, "Would you like a pic?" and was signed, "Terry."

I thought about that for a long time. He still sounded nice, and I was thinking I could use a good massage at the least.

One from some nice looking man might be fun, and meeting this way was almost...possibly naughty?

"OK." I responded. "Your ad said full body massage, I could use a nice pleasurable experience and I am not bashful."

I put the last in there just to tease and see how he would answer.

God. What in the hell was wrong with me? I instantly wanted that email back but it was too late.

The reply came back in seconds, there was a photo of a young man about 25 or so and he was dressed in a T-shirt and blue jeans. He looked to be...normal?

"I am well mannered and we can drape to your level of comfort. Do you have any health issues I need to be concerned about?" He wrote.

"No, I am a Doctor, but I am in my 40's so I might be way too old for you. I just want a nice uninhibited rubdown and like I said I am not bashful." I answered.

OK. I was having fun now, teasing and dropping little hints. For some reason being totally anonymous helped.

"OK. You sound nice and I think we understand each other. Here is my phone number, call anytime up until 10 PM." His email came back almost before I could get my fingers off the keyboard.

I read that and hit print. I folded the sheet of paper and set it on my desk, wondering what the hell was I doing?

That evening I drove down to the bar, and I told Pam what I had done.

"You go, girl!" She grinned at me.

"What do I do if he turns out to be a serial killer or something?" I said.

"Not likely but if he gets too far out of line just mace him!"

"I don't have any mace." I told her.

"I do. Here, take this one." She pressed a little canister into my hand.

I looked at it, then at her and laughed.

"I can't believe I am even considering this." I told her.

"Oh, hell, you will probably get a free massage and maybe your stuff rubbed and that's about it." Pam giggled.

I broke up laughing, that was funny. Still, it was fun to think about but really there was no way I was going to strip down and lay there naked on a table with someone I had never met, unless they were a professional.

But Terry did say he was in school, and wanting a practice partner? I thought about that all the way home, maybe..just maybe he was sincere.

Plus the photo. He was cute. But what if the photo was a fake, what if he really was some nut case? I realized as I unlocked my door that I was arguing with myself.

I looked at the clock, it was just before 10 PM. My hand reached out and picked up the phone, punched in the number. It was almost like I did it without thinking. If I did think about it, I knew I would chicken out.

"Hello?" A male voice answered, picking up on the 2nd ring.

"Hello. My name is Sally, I was calling about your email? For massage work?" I knew my voice had a nervous edge to it.

"Oh, sure! Hi! Would you like an appointment?"

"Maybe. You said you wanted a practice partner?"

"Yes, I do. We don't get enough of that in school and I just want to work on real people in a real world situation. I can't charge anything though, not until I pass my exams and those aren't for another month."

"OK." I made my decision. "How do we do this?"

"I can come there if it's not too far, or you are welcome to come here." He gave me the address, I was surprised, it was less than 5 miles away in an apartment complex down by the community college.

"OK. I will come there, when is a good time?"

"Any time from right now to whenever you are free." He answered.

"OK. I will be there in 20 minutes." I hung up, my hands shaking. Now what the hell had I just done? I decided to just not go, then I checked my purse. The little mace canister gave me some comfort but not much.

I jumped in the shower and quickly rinsed off. Then I put on some plain white panties, slacks and a blouse. I started to put on a bra, then I realized I would probably just be taking it off so I didn't bother. I also didn't bother with makeup, simply brushing out my hair.

I figured I would just leave the panties on.

I arrived at the apartment complex a few minutes later than the half hour I had told him. I found the unit quickly, it was on the second floor. I had my hand up to knock when the door opened.

"Hi! You must be Sally." The young man standing there was tall, good looking. He had on a white T-shirt and blue jeans.

"You are Terry?" I managed lamely.

"Yep. Come on in!" He stood aside, I walked in and looked around. The apartment was neat as a pin, there were stacks of books on a table. I glanced at them, they all seemed to be about massage.

"I am sorry it is so late." I told him, still nervous.

"No problem, I work whenever I get a chance to. I want to say thank you for letting me work on you." Then he handed me a clipboard, it has all the usual medical questions. I had handed it back to him when I realized I had written down my real name and telephone number.

Terry showed me into a spare room, he had a table set up with sheets. I was relieved to see that. He told me to undress to my level of comfort and we would start out face down. Then he left.

I slid off my blouse, dropped my slacks. I was going to leave my panties on but then I thought to hell with it so I took those off, too. I slid onto the table, noticing it was nice and warm and very soft. I could feel heat coming from underneath, it was cozy. I snuggled the sheet up tightly around me.

Terry knocked and asked if I was ready, I called out that I was.

He came in, still wearing the same T-shirt and jeans.

"Let me know as we go along if you wish more or less pressure, please." He told me, then he rolled the sheet back off my shoulders and started in. In just a couple of minutes I felt my muscles begin to relax, it did feel great. He slid the center of the sheet up off my ribcage, then did some side pulls that felt wonderful. I could tell he was being overly careful with the drape. When he got to my hips he tugged the drape back over my shoulders.

"I can work your glutes through the drape if you prefer, or we can skip that part?" It was a question.

"I am not bashful, you may go ahead, please." I told him. I had gotten past being nervous, he was just doing a careful massage.

Terry slid the drape partway over my fanny and began some long deep strokes. His fingers were deliberately avoiding getting near the cleft so I told him to relax, I was just another body.

"You don't mind if I work...closer?" It was cute the way he put it.

"I don't mind at all, my poor body really needs this." I told him.

"OK." He seemed to relax, then he started long delicious strokes over my fanny. He let his hands run down the length of my legs, I felt the drape being shoved over leaving half my body bare from my hips to my feet. Then his fingers wrapped around my calves and came up, sliding sideways just before he reached my groin.

"Are you comfortable with this?" He asked again.

"Yes, fine." I managed to mumble. It did feel fantastic. Next he stepped over to my other side and began again, starting at my ribs, finally dropping to my legs and back up. I knew the sheet was now just a strip between my legs.

I was feeling comfortable with him by now, so I rolled my hips and opened my legs some more so he could reach higher up my thighs. Terry let his fingers wander tantalizingly close, I felt myself dampen slightly. Just as I was beginning to struggle to keep from turning my hips to meet his hands he stopped and pulled the drape back over me.

After working out my feet for a gloriously long time, He asked me if I wanted to turn over.

"OK." I reached down and pinched the sheet against the table and rolled over. I was completely conscious of my bare breasts hanging sideways as I turned. I noticed he reached out and held the upper portion high while I settled on my back. Tugging it up to my chin and tucking it in the sides, he began again at my shoulders. I actually dozed off for a minute or two, I woke back up when he asked me if I was bashful about my breasts.

"No, it's fine, go ahead and do whatever you like." I told him.

I was wondering why I said it like that as he slipped the sheet down to my waist. I knew my nipples were firm, hard as rocks, I was feeling very good and getting turned on.

"Well, it looks like you are enjoying this." Terry commented with a smile.

"Yes, I am." I managed.

His hands swept down and under my breasts and lifted, his palms rose up to avoid my nipples. After a half dozen strokes like that I was aching for him to touch them, pinch them, do something. That brushing by so very close was driving me nuts.

Then he placed both hands on my upper chest, and with splayed fingers he slid them down and over them. My hips came up with a mind of their own, then he reversed direction and slid them back over me, cupping both of them and lifting slightly. He repeated that motion a dozen times, I looked up at him with slitted eyes and he was grinning. Each downward stroke with his splayed fingers caused little streaks of pleasure to waft over me, my nipples got even firmer.

Then Terry reached down and gripped each tip between his thumb and forefinger, rolling them gently. A small orgasm flowed through me, my mouth came open.

He left me naked to the waist, exposed, then pulled the sheet lower to just above my pubic hair. His hands began clockwise circles on my stomach, I tried to keep my stomach muscles from rippling but I couldn't. I jumped slightly when his fingers brushed across my tuft of pubic hair.

"Are you still comfortable with this?" Terry asked.

"Yes, fine." I managed to mutter..

"I do have some techniques that most women like, but they are a bit on the...intimate side? We can skip that part if you...."

"Oh, it's fine. You are very good, go ahead if you want to. I am not...bashful." Just saying that caused my breath to catch, I was going to let this man..touch me, look at me!

I was now at the point where I knew I would let him do anything he wanted to. My legs opened wider with a mind of their own.

He poured some oil on his hands and rubbed them briskly, then started at my knee. His hands went upwards slowly, palms flat, fingers splayed out. I felt them reach the top of my thigh, then swing over into the crease between my upper thigh and my pussy. Then his fingers began tiny little circles, very gently, as he worked his way up the crease.

The touch was maddening, so close, he repeated it several times.

"Reach down and take hold of the sheet, that way you can control the draping to your level of comfort." He said, smiling.

I did as he asked, not quite sure what he meant. His fingers began again, as he got halfway up I realized what he meant, he was tracing the edge of the drape. I tugged slightly, his fingers moved right over with it. As he dropped his hands down and began the little circles again, I tugged the sheet up further. I could feel the slightly cooler air on me, those fingers stimulating me. Right there, just on the edge of my labia.

I pulled the sheet higher, knowing I was almost completely exposed.

"OK." Was all he said, as his hand slid over and rubbed across my lips. He pressed the palm of his hand flat against me and all pretense was gone, I spread my legs as wide as they would go. Terry stepped to the foot of the table, leaned forward and began to alternately flick his thumbs up and over my lips, spreading them open. Somehow he inserted one finger inside me, curling his finger upwards and stroking me as his thumbs continued that alternating flicking motion. The motion of his thumbs now slid sideways, right beside my clitoris, his touch was perfect.

Somewhere in there my knees came upwards, laying over to each side. I glanced at Terry through slitted eyes, he had his hips pressed against the end of the table, leaning forward. His eyes were staring between my legs, his fingers busy. The expression was one of lust, he was enjoying this.

I wanted desperately for him to lean forward, press his lips to me. I fantisized of him sliding upwards, on top of me, his rigid penis invading me, as tiny flashes of light sparked before my eyes.

His fingers just kept on and on, speeding and slowing, I had no control, feeling myself building more and more.

The room became hazey, then my first huge orgasm flooded over me in waves, I felt my hips press up against his hands. He kept it up, I felt myself explode again, then a series of smaller ones until finally I could no longer stand it and my hips dropped back.

imsally
imsally
100 Followers
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