My entire life, I had been an asshole.

I don’t think that is true, but that is what my ex-wives all said.

And in fact, almost every woman I had ever known or been with said the same thing.

But the truth is that they just did not want to accept that as women, they were the “inferior sex”. And therefore were only put on this planet to make babies, and take care of us men.

And even lying here in a hospital bed where I was supposed to be getting quality care the bimbos seemed to be ugly, stupid, or stupid and ugly. I was scheduled for a bypass the next day, and when I told my nurse I wanted a pizza with all the meat they could put on it, she just smiled and put some turkey and mashed potatoes in front of me. Not even any gravy on the potatoes!

“Mr. Cliff, you know you can’t have anything like that! You are going in for surgery tomorrow, and that is why you are in such trouble in the first place.”

“Yea, clogged arteries. It’s not like that stuff will hurt me now though. Just go and get it for me, will you toots?” I made my voice a bit harder, in experience I know that women really love being ordered around, even when they tried to pretend they did not.

“It’s not ‘toots’ Mr. Cliff, it’s Nurse Kelly. Now excuse me, I need to finish my rounds.” And with a sniff she walked out of the room.

Well, ya win some you lose some. Not that I was complaining a lot, my breath was so tight that I was not sure if I could even handle a handjob, let alone if she had actually blown me. In fact, it was when my secretary was blowing me that I first realized a few months ago that something was wrong.

I work as a loss prevention troubleshoter for a security company. 3-5 days on the road to different towns, checking out the security in stores, then writing a list of suggestions on what to improve. Sometimes I even returned for another 3-4 days, teaching their employees on the fine art of detecting and catching shoplifters.

And that had been a great career also. Although today with all the security cameras, it is becoming a kind of lost art form. Now a team of 2 either watches everything on a camera, or they have one on the camera and one on the floor. Not how it used to be, where we would prowl in the dark attics and watch them first hand through binoculars through one way mirrors on the ceiling.

One great thing about this job, it got me more than my share of pussy over the years. I kinda fell into it after I graduated, thinking a guard card would be a good start to my career. I got a job at a clothing store, and it happened my third week. This really hot looking MILF came in, and her knockers were huge. So I started to follow her around, trying to seem I was doing my rounds when really I was trying to get a better look at her boobs.

I was 18, she must have been around 35. Her knockers were big and soft, and I was at the end of the isle and saw her. She took one of the silk blouses off the hangar, then after holding it against her impressive chest she stuffed it in her purse! Well, I was not supposed to stop anybody, my job was to watch and report. But I just had to stop her.

I followed her as I had been told in my “Apprehension and Arrest” class, and she took 2 more blouses and a bra and they were all in her purse. As she walked to the front door I followed, waving over the manager when we got to the front. And exactly as I was taught, she walked out the front door and I reached out and grabbed her arm.

She jumped when I did that, but I held her firmly. “Excuse me Ma’am, you need to come back inside the store for a few minutes. Please, there is no reason to cause a scene. We will just do a bit of paperwork and you can be on your way.”

The manager smiled and took us into his office, and I had the gal lay the 3 silk blouses and bra on the table. The gal was crying by now, and I was torn between being firm and doing my job, and wanting to take her in my arms and show her the penalty for breaking the law with my own law stick.

About 5 minutes later the manager came back with a receipt for the clothing, and after we did some paperwork we took her back out and told her to not return or she would be prosecuted for trespassing.

After work the manager asked me to meet him in the parking lot. Turns out he was impressed by my action. “I know you are not supposed to stop them, it’s not your job. But please, if you see something like that let me know and we will do it again. But remember, you need to have all the steps before a stop, not just because you think they stole something.”

“Yes sir. Approach, Selection, Concealment, Passing all Registers, Exiting the store. I remember the class, which is why I followed her until the end there. And why I called you over, I thought you would stop her.”

“Nope, can’t do that. I did not see any of it, but your eyes told me that you had so I supported your stop. Good job, next time after you get my attention move your head from shoulder to shoulder like you are stretching your neck, then look at the perp. I will be there and we can get them again. Or I can take over watching them. So long as one of us has eyes on them at all time after concealment and we do not see them dropping the items, it is good.”

Well, in the next month I made 4 more stops. The best was when we stopped Penny Lax. I still remembered her from school, she was one of the stuck-up bitches that actually laughed at me when I asked her to a movie once. She was hot, and thought her shit did not stink. But it really stank when she was sitting in that office, the 2 bikinis that had been in her purse on the table.

The manager had just left the room to ring up the recovered items when she turned to me and said “Come on Paul, you gotta let me go! My daddy will kill me! I’m going to college in the fall, he will stop paying if he finds out I got caught stealing!” She was really crying now, and reached out and rested her hand on my arm.

Now by this time I knew we did not call the cops unless we suspected they were professional shoplifters, or people we had caught before. We only filed the paperwork in the event we caught them again. But I realized that Penny did not know that. I smiled and reached over, resting my hand on the back of her hand. “Gee, I would like to help you out Penny. But I really don’t know you all that well, and the one time I asked you out you laughed at me. So I’m not sure why I would try to help you out now, since that is how you treated me before.”

I watched her chew on her lip and wipe away her tears. I was enjoying this, seeing the cunt humiliated and scared, and did something I had always wanted to do. I reached up and wiped one of her tears off of her cheek, then let my fingers caress down, along her neck then along the cleavage I saw at the top of her open neck top. I then let my fingers caress the top of her breast for a moment before I cupped it.

“But maybe I can do something, if you were nicer to me Penny.” She looked up into my eyes, then nodded. “OK, I know Mr. Robbins holds the paperwork in here for 3 days before sending it to the police on Monday. Go out with me tonight and tomorrow night, and I will sneak out the report and nobody else will know.”

She looked into my eyes, and nodded. Bingo! He came back in, and we continued going through the warnings. He looked at me when I said I would walk her out to her car, we usually just let them go at the door. I walked her to her car, and said I would come by at 7 and pick her up. She looked at me as I chuckled, and said I already had her address, I got it when I copied her drivers license.

When I got back in, I told Mr. Robbins she had been a friend from school, and I was assuring her that things would be OK. He smiled and nodded. “That’s the way it should be Paul. Even if it is a friend, we have to do our job. But that does not prevent us from being nice.” And as I expected, he put the folder in the top filing cabinet. I already knew that was for internal use only, and was not even forwarded to Corporate.

At the end of the day I went home and took a quick shower. I picked her up wearing slacks and a nice shirt, and she had this really hot green dress on. No need to go over details, but she did make the weekend great. We went to the hills outside of town, and I finally got to feel those perfect breasts after lusting after them for over 3 years as she sucked my cock. I made her do it 2 times, and I thought I was the king of the world at the time. But looking back now, she was only decent. I took her out again the next night, and finally lost my virginity with Penny Lax. Her dress that night was laying over the seat in front of it along with my own clothes as I sank myself into her tight cunt.

Her legs and arms were around me, and she was making the most delightful moaning sounds as I shoved my cock in and out of her for maybe 5 minutes before I shot my cum into her. We did it 2 more times that night, and I know for a fact she came the second time as I was sitting and she was bouncing over and over in my lap.

We actually kissed a bit afterwards, and she apologized for being so mean to me when I asked her out. “But you were like a nobody then, Paul. You still kinda are, but you do have a great cock.” We did do it a few more times that summer, the last I had her bent over a picnic table in the park at midnight. I still remember looking down at her perfect ass as I shoved my cock in and out of her and thinking that next time I will have to fuck that ass. But we never did again, she left for college and I never saw her again.

Two weeks after my last fuck with Penny, the district manager of the store came for her monthly visit and I was called into the office. Spread out on the table were 15 reports. “Robbins here tells me you have done an outstanding job of catching shoplifters Paul. I read through the reports, and you indeed have done a superb job. Paperwork perfect, all the details needed, and clean stops every single time. How would you like to come and work for us?”

Well, after talking with them for a while I said it sounded great. No longer being a contracted guard but an actual employee of the company. A raise, occasional travel, and it even had benefits. I would be a fool to say no.

“OK, I will contact your company tomorrow and buy out your contract. Yes, we have to pay them a finder’s fee because you are their employee. Week after next be here on Monday at 8, dressed in casual clothes. I will have one of my AP supervisors start your training.”

I was stoked! The new pay was almost 50% more than I was getting then (barely above minimum wage), and I could wear normal clothes! I stopped by the guard office on Friday the next week and turned in my uniforms, and went on down to the arcade on Saturday. I tried hard to hook up with a girl there, but she only let me rub her butt a bit so I had to go home and take care of my erection myself. The bitch.

Well, on Monday I wore slacks and a button down shirt when I went into the store. Mr. Robbins pointed to his office, and for the first time I met Claudia.

Claudia was a fox. Claudia was a babe. Claudia that had legs that went from her ass to her ankles, and a chest that must have made it hard to see her feet. She smiled and told me to have a seat. She then told me about my new job. What was expected of me, and what it actually was. “You have done a pretty good job before this, and considering you were in uniform and not undercover that is even more impressive. 15 clean stops, merchandise recovered, no law enforcement involvement. That is a record I like.”

For the rest of that day it was like I was in school again. She taught me even more about what to look for, how to follow somebody, and how to react when stops go sideways. The second day was a repeat, this time going over reports and forms. How to write up the arrest report. How to inventory and process the items recovered. How to write up a formal trespass notice and contact the police.

Then I went to a world I never knew existed. We went into the back warehouse and through a door was a narrow stairway leading up. And once we got up there I was stunned. There was still another 7 feet to the ceiling, and all around the store below that I had long noticed there were mirrors. Now I had thought that was for the employees to watch the customers, I never really understood they were one-way mirrors!

“Get used to this Paul, you will be spending a lot of time up here, and in places like this. We normally work in teams, one up here and one on the floor. The one up here is in charge of spotting all they can, then sending instructions to the agent on the floor. Go ahead and take a walk around.”

It was like I was a bird, looking down on the people on the ground. No, more like a god! Looking down on mortals. She handed me a pair of binoculars, and I watched the customers through them. It was amazing!

She handed me a small transistor radio, and told me to put the white earpiece in my ear. “OK, this is only one way, but I can talk to you through this. If I see somebody that needs to be followed or stopped, I will direct you through this.” She then started to teach me the lingo of my new trade. Perps, Boosters, Caper Kiddies, Mommie Lifters, and Passers. That week was amazing, and we caught 5 gals and a guy. The guy we did call the cops on, he had over $150 in merchandise in a secret lining in his coat.

That night she asked me to join her for dinner. She took me to a Sizzler, and then she took me to a small club on the edge of town. “Paul, you are doing really good. Even better than many of those I have worked with for years. That one chick with the tan miniskirt was a good catch, how did you spot her?”

“Well, something about her eyes. She came in, and went right for the lingerie. And not the cheaper Playtex stuff, she started selecting Bali and other higher end stuff. I suspected she had already cased things out, and when I saw her select that bra that looked like it would be a fit for you I figured she was not looking for herself. I admit I lied when I said I saw her stuff it in her purse, but when it was no longer in her hand and not dropped I knew she had taken it. But I did see her put in the other 3 bras from Olga in her purse.”

“Yea, she was what we call a ‘Baby Booster’. She would not say, but I suspect she gave or sold them to friends. But what do you mean it would fit me and not her?”

I coughed. “Well, that area of the shelf was for D and DD cups, and she was maybe a B at most. Therefore I knew it was not for her but somebody else. If she was not boosting, she should never have been looking at those sizes.”

Claudia then leaned forward and whispered “Good eye, they are 38DD.”

Well, we finished our beers, and she told me she had to leave the next day and had to give me my paperwork and schedule for the next week. I followed her to her motel, then I followed her lovely ass as she went into her room. And 30 minutes later I was in heaven as she had me straddle her hips and wrapped those 38DD breasts around my cock and had me fuck them until I sprayed her upper chest, neck and chin with my cum.

Claudia was single, in her late 30s, and an amazing fuck. Several times over the next 5 years we would get together when we were working first at a high theft store, then on a stakeout for a booster team. On the job she was all business. But when work was done and those panties went down, she was all for hard play.

And it was not long until she realized I was moving fast. And as much as I liked our occasional fucks I think she suspected I might have her job soon if she did not do something. It was over 4 years later and after finally catching a two person team we had been after for 5 months, we were enjoying the last hour until it was time to clock out and head back to our home towns. After one lovely session with her bent over the railing in the mirrored attic after I had pumped my cum into her, she told me that a major department store chain was looking for an LP manager. She went to her knees licking my cock clean, and she said I might be a perfect fit for them.

“Trying to get rid of me Claudia?” I asked, reaching down to squeeze her breast.

“No, but you need to move on to something else Paul. You have learned all we can teach you, it’s time for you move up. And in this company the only place up for you is into my position. I am not getting promoted any time soon, so either you stagnate where you are, or you move up elsewhere.”

I pulled her up, then turned her to again bend over the railing, looking down at the customers. I lifted her skirt over her hips once again and slid back inside. She was still hot and wet, but almost so wet it was hard to feel since my earlier load was leaking out of her. “You just don’t want me to take your job,” I said, and pushed myself deeply into her.

That was our last fuck, and it was hot, wet, and passionate. I fucked her like crazy, both of us trying to keep quiet so the sounds would not be heard from below. Claudia frigged her clit as I pumped her, and came right after I pumped another load into her.

As we were wrapping up for the day, Claudia handed me a business card for a more upscale clothing store chain and told me I should give them a call. I did, and even though it was a 30 minute drive each way I took the job. At higher pay, and in a nice downtown shopping mall.

Man, the tits and ass were everywhere! I was soon doing a booming business, but for the most part I was prevented from doing things like before. I was never alone with a detainee, and all paperwork was sent to the company legal department. But towards the end of my 3 years there something did happen.

By this time I had already gone through wife number one. She worked in the same mall at the place that sold movies, and Carol was really hot. I even stopped fooling around with other gals, and thought I was in love. She was super in the sack, but I realized after about a year of marriage that she was not as bright as I had originally thought. So when she started talking about it being time to ditch her pills and have a kid, I moved out and on with my life.

Yea, that was not going to happen. I had known for the last 6 months it was over, but the sex was too good to give up. But I was afraid if I tried to put off her breeding desire for too long, she would just up and have an “accident”, and I would be stuck with her and a kid.

Judy however was a cute girl that worked in the “Junior Miss” section. She was 17, and I always popped a woodie when she was around. I would frequently watch her for 20 minutes at a time, either through the one-way mirrors around the ceiling, or on the cameras. Sometimes we would talk as I was following somebody, and she seemed to flirt with me whenever I did. One time I was even trailing a known booster, and Judy stood in the perfect place so I could watch the booster. We were pretending I was getting something for a girlfriend, and she took special delight in asking if she was bigger than my girlfriend was, or smaller. She grinned when I said she was the same size as my girlfriend, but looked even better.

But I knew Judy was a summer employee, and was 17 and therefore “hands off”. I was 27, which meant getting it on with her would be bad, no matter how hot she was and how hard she flirted with me. Then I saw her one day stick a package of pantyhose in her purse. I knew it was only $2, and we had a policy to not stop people unless it was $5 or more. But I was just getting off myself, so I smiled and followed her outside.

She smiled when I walked out right after she did, and flirted with me as I walked her to her car. I had opened her door for her, and right after she sat down I smiled. “Judy, I think you have something that belongs to us.” Her eyes opened in fright, but as I expected she tried to deny it. “In your purse, is a pair of pantyhose. Leggs brand, gold egg so that means Sheer Energy. I saw you take them right before you got off and slip them in your purse.”

She started to cry, and begged me not to say anything. She swore she was going to pay for them, she just did not have any and she needed them for a date that night. I was picturing the leggy girl in the pantyhose, and felt the resistance to my desires crumble. Imagining her long dark legs covered in nylon was almost more than I could stand.

I finally gave her an ultimatum. “OK Judy, you can either go back inside with me, or you can cancel your date tonight and I will see you this evening. Your choice.” She tried to beg off, saying she could not cancel her date but when I started to walk to the store with the merchandise in hand she relented. She gave me her address, and told me to pick her up at 7.

At 7:10 I had barely stopped in front of her house when she came out and immediately got into the car. She was wearing a lovely blue dress, which showed off her pert titties, and her fine looking ass. And no pantyhose, I noticed. I tried to talk to her, but she barely answered. I took her to a nice Chinese place in town, and once she realized that at a minimum I was not going to ravish her on an empty stomach she loosened up a bit. Towards the end of the night I assured her I was satisfied, and would tell nobody else about what happened. Then after we ate, I did not even ask and drove to my apartment.

Once there I pulled out some wine and poured her a glass. She sat next to me on the couch, and we finished 2 glasses before I pulled her in for a kiss. She resisted just barely for a few seconds, then surrendered herself to me. But I took things slow, not wanting to have her feel remorse at some later date and try claiming I had raped her.

I spent 15 minutes just kissing her, feeling her tremble in my arms a few times. But I knew what I wanted, I wanted to pluck this fine teen. I just knew I had to take my time in doing it. Finally we took a break to catch their breaths, and Judy admitted that I was much better at kissing than her boyfriend was.

“Well Judy, that’s probably because he is so concerned with what he wants, he is not thinking at all about what you want. Right after we started kissing I realized you really like doing it, so my only concern was in making you feel good with me.” Yes, total bullshit. But I had a feeling if I took my time I would get what I really wanted. And that was inside her panties, to hell with the risk.

Soon we were kissing again, and this time I pulled her onto my lap. Feeling her bottom pressed against my cock felt amazing, and as one hand played with the back of her neck my other was running up and down her arm, from the backs of her fingers to her shoulder and back. And finally the cue I had been looking for. Judy turned her body to face me a bit better and pressed her chest against mine.

Bingo! She was getting hot, and wanted more stimulation to her breasts, if she wanted to admit this to herself or not. I turned my body and laid on the couch, still kissing as I laid on my back with sweet Judy on top of me. And my hand left her arm and moved to her waist, slowly slipping from her hip up to under her arm then down again. I could feel the slightest of swelling on her chest upwards, and pressed in slightly each time I reached it. I knew she had to feel that through her breasts, which were now crushed against my chest. Both of her hands were running through my hair, and I lowered my other hand to the small of her back.

A few minutes later I had lowered my hand so it was caressing her bottom, and she did nothing to stop me. The thin cotton of her dress and panties now the only thing between my hand and her delectable little ass. My other hand was now caressing just up and down her side, spending more time rubbing the sides of her breasts. Then inching forward, and caressing the underside of her breast.

She was both soft and firm, and when I moved to kiss her neck and ears she moaned softly, still lightly pulling my hair as I moved forward, now caressing her entire breast. Her nipple felt hard and firm through her top and bra, and my other hand was pressing into the cleft of her ass, still pausing to caress her cheeks before caressing between them.

Her hips were now moving slowly over me as we kissed, and I knew her heat was quickly ramping up. Finally I slid my tongue particularly deep into her mouth as I slid my hand forward and grasped her breast. Her nipple was hard, and she stiffened and moaned into my mouth, but did not pull away. I had been slowly pulling up her dress as we had been making out, and after she relaxed a bit and I was really giving her firm breast a lovely squeezing I pulled up the back of her dress the rest of the way and reached to caress her ass through her panties.

Once again Judy tightened her body, but a minute or so later relaxed against me. It was like she was expecting me to go further, but as I only went a single step she was accommodating me. And she had to have known I wanted more than just making out as my price for silence, but she was not sure how far I really wanted to go.

And when I let my lips move to her neck and ears and heard lovely Judy panting in my ear, I knew it was affecting her as I wished. So after chewing on her lobe and letting my fingers squeeze and play with her nipple and feeling her press back, I let my fingers undo the buttons and reached into the top of her dress. My hand slid in and under her bra, feeling her nipple unrestrained. I felt my cock lurch in my pants as I felt her fat hard nipple. I moved my other hand up and through her top unfastened her bra, then pushed it aside and held her naked breast.

By now I had slowly eased her onto her back, and I pulled her top open. I glimpsed down and saw her breasts. Still smooth and perky with youth, with nipples that were so hard and surrounded by areola just a little darker than her skin. Poking out almost a half inch, I could not hold back and moved my head down, taking Judy’s right nipple into my mouth and sucking on it. Judy gave a whine, but instead of resisting actually pulled my mouth in tighter. I moved against the back of the couch, wedging myself between it and her, keeping her nipple between my lips and massaging with them as I licked and sucked. And then I rolled her onto her back, her ass was now under her so I started to caress her hip and legs. Each time moving a little closer to heaven.

I finally was caressing lightly along the seam of her panties over her hip, and reached forward and cupped her mound. As I had hoped, the thin cotton was damp. And she started to whisper “No, not tonight Paul, not so fast.” I did not remove my hand, but instead simply slid it up so my fingers were no longer between her thighs but instead resting over her pubic mound.

And I also noticed before I moved my lips back up to kiss her again she did not say “Do not do that”, but “Not tonight”. Which means at a future time she would welcome it, I just had to play my cards right. I let my fingers move up and down her belly, never moving much above her panty line, but not moving far below either. I would feel her tense each time I massaged her mound with my fingertips, and relax a bit before moving them up again. And each time I would massage just a smidge lower, but never coming close to her clit. Which I knew must be rigid with desire, based on how wet her panties were now. I could even smell her little cunt, I had gotten her so wet.

Finally on one of my circuits after about 10 minutes I was sucking on her nipple again and “accidentally” let my fingers move down a bit more. I let my fingertip barely graze over her hooded clit before moving it back up. I then spent almost 5 minutes continuing the massage but not moving back down to it. And I could feel her hips start to move a bit from side to side.

Finally I knew we both needed a break, so I eased off the passion, finally kissing her over and over softly as my hand rested just below her navel. I told her I needed to use the bathroom. It took almost a minute to coax my cock to go soft enough to let me piss, and after I left she slipped in for her turn. I poured us each another glass of wine.

Judy came and sat in my lap, and kissed me softly. I handed her a glass then picked up my own, resting my hand on her back. And I could tell she had not only not fastened her bra, she had removed it. She said she was enjoying being with me, and was glad I had asked her to go out with me instead. I told her I was also, and she was an amazing girl. “Judy, I hope you will go out with me again. I hope your boyfriend is not mad at you.”

“Well, he’s not really a boyfriend. Just a guy I met at a movie last week, we were going to the arcade tonight. He’s probably with some other girl now.”

“Well, if he is he is a fool. You are worth waiting for.” I then kissed her again, putting down my empty glass and taking hers and putting it next to mine. Soon our tongues were in each other’s mouths again, and sure enough when I caressed her breast through her top there was no bra underneath. I was again playing with her nipples when she broke the kiss and said she was not very comfortable.

“Well, how about we lay down on the floor then? Get the pillows from the couch, I have a blanket I can put on the floor to make it softer for us.” She smiled, and I got the large blue blanket with wolves on it I had won at a carnival and laid it on the floor. I went back into my bedroom and pulled one of my larger pillows off of the bed and pulled off my shirt. She smiled when I came back in, and she laid on her back with her head on the pillow as I laid next to her.