My life was in freefall for a while. It started with the divorce, losing my parents and most recently, the loss of my job. Not having any luck finding a good job in my field, I had to take a job as a security guard to pay the bills. Not what I expected to be using a master’s degree for, but hard times call for desperate measures.
I was going to be a night watchman at a department store. There would be two of us working the overnight shift, Pam and myself, and since she had been there longer, she was in charge. One of the store policies was there always needed to be one male and one female guard on duty, so if someone needed to be searched, it could be done by a guard of the same sex, for legal reasons. I had to walk around the store and check in at various stations, to make sure everything was alright; she would be sitting in the security office watching the monitors.
My first night, Pam walked me around the store showing me where I had to check in, and what to look out for. As we were walking, I was checking her out. I would say she was in her early forties, with light brown hair and stunning blue eyes. She was attractive, but average in the looks and body departments; the dorky security uniform didn’t help. She was taller than average, probably around 5’ 8” or so. I remember thinking if circumstances were different, I might ask her out.
After a few rounds, Pam gave me a clipboard, flashlight and radio, she told me to make rounds until 2:00 am or so, then head back to the office for a meal break. With that being said, she gave me a smile, told me to get moving and to call her on the radio if I had any questions.
The first few hours were hectic trying to remember where I needed to check in. I was trying to figure out where all the doors went to, and which ones were supposed to be locked. I was so nervous; I didn’t want to mess up and lose the only job I could find, even if it was lousy. Around 2:00, I went back to the office for my meal break, and Pam gave me the run down on the store.
This was a small family-owned chain, three stores, the one we were in was the original, the other two were both about an hour away in opposite directions. She pointed to a door on the other side of the room and told me that was Mr. Johnson’s office, and that he was the head of security. She told me he was only in this store a few days a week, and it was rare for him to be here during the overnight shift.
When my break was over, I went back to roaming around the store. After talking with Pam, and figuring out what I needed to do, it was much less stressful. My first shift ended without incident.
By the middle of my second night, I was downright bored. I could make the hour-long round in half that time, even less if I rushed. I started browsing through the store while making my rounds, checking out the new TVs, all the tools, and of course the women’s clothing department.
Did I mention that I have enjoyed dressing in women’s clothes for as long as I can remember?
I would make sure the clothing department was very secure, lingering in the lingerie section way longer than I should. The sights, the smells, the feel of all the clothes was sending my brain into overload. I started to get a familiar stirring down below. I had to keep moving; with my luck, Pam would be watching my every move on the security cameras. Over the next few weeks, I tried to find where all the cameras were. As far as I could tell, the store was pretty well covered, except the bathrooms and the fitting rooms.
One night, while walking through the lingerie department, laying on the floor was a beautiful pink silk thong with white lace ruffles around it. Now, the policy was if there was something on the floor, each department had a bin, or area where the merchandise was to be placed, that way one of the people who worked in the department could put it back where it belongs.
When I picked it up, it was the softest silkiest pair of panties I had ever touched. I was instantly hard.
As I walked towards the fitting room, where the bin was for this department, I kept feeling it and rubbing it against my cheek, I even sniffed it. This was the moment that it all turned. I don’t know what I was thinking, or what came over me. I slipped into one of the changing rooms and took off my pants and underwear, then pulled the silky thong up my legs.
I had a little trouble getting everything tucked back with the state I was in. I couldn’t believe how good they felt, I had never felt anything like it before, and my legs were starting to go weak. I pulled up my underwear and pants and continued my rounds.
I must be crazy! If anyone ever found out about this, I could be in a lot of trouble. I figured there were no cameras in the fitting room, I could wear the thong for the rest of the night. Near the end of my shift, I could go back into the fitting room to take it off and put it in the bin, no one would know.
It all went off without a hitch, and then it snowballed from there; I would grab a pair of panties a few nights a week and change into them, it got to the point I would go commando, so I didn’t have to deal with my rough boy underwear. I kept getting bolder and bolder; I started wearing garter belts, then adding stockings. I was spending more and more time in the women’s section; I knew where everything was, I knew which shoes they had in my size, which dresses they had that would fit, I knew it better than the manager.
Things kept progressing, until it got to the point that I added bras under my shirt. I wore a blazer as part of the uniform, and I always picked white bras, so no one would notice.
One night shortly after my meal break, Pam called me over the radio and asked me to come to the office when I had a minute. During our break, she had mentioned with the holidays coming up we had to go over some things, so I called her back and let her know I would be there in a minute. When I got to the office, she motioned towards one of the consoles and told me to go sit down over there.
As I passed her, she stood up. When I was reaching for the chair there was a shooting pain in the back of my legs. I had to grab the console to keep from falling on the floor. Once I had steadied myself, I reach for the back of my legs to try to figure out what happened, that’s when Pam put me in a wrist lock and slapped hand cuffs on me. I found out later she had hit me in the back of the legs with her nightstick. She pushed me over the console and started frisking me. She gave me a quick once over, then she started pushing buttons on the console. I thought since she had patted me down so quickly, she might have missed the bra.
The monitors started coming to life. Bent over the console, they were right in front of my nose. It took a minute to figure out what I was looking at, there were eight screens with different date stamps from different angles. As this was happening, Pam came back to frisk me again. She started with my shoulders, then arms, when she got to my chest, I knew I was a goner, but she kept moving down. Did she miss it?
On the video screens, there I was, walking through the lingerie section, picking up items that had fallen on the floor, and bringing them to the fitting room to be placed in the bin. Pam was now frisking my legs; maybe she won’t notice the stockings. She went down one leg and up the other. On the monitors, you could see me walking into the fitting room. I figured the next thing you would see would be me walking out. You can imagine the shock when the camera switch to a view inside the fitting room. I couldn’t imagine the shock when Pam grabbed me by the crotch, squeezing my balls and my rock-hard dick.
Why am I hard? What is wrong with me? I had to ask myself.
When I came to my senses and tried to come up with some sort of excuse, I couldn’t.
I started to plead with her not to turn me in. “I’ll do anything, please, I need this job.”
Pam chuckled a little, “Anything?” she asked.
“Anything,” I whispered, tears starting to well up in my eyes.
She walked around in front of me and looked me in the eyes, and started unbuttoning my shirt, then undid my belt and the button on my pants. Walking around behind me, she gently traced a finger on the bra. Standing behind me, she started to rub my shoulders. All of a sudden, she pulled my shirt and jacket down my arms, but because I was cuffed, they stopped at my wrists. My arms were on fire from being bent back and the jacket further restricted my movements.
“Get those shoes and pants off now, sissy boy,” she yelled at me.
I kicked my shoes off, and worked with my feet to get my pants off. Without the use of my arms it wasn’t easy. I ended up falling flat on my face, Pam roughly grabbed my pants that were stuck around my ankles, spun me so I was on my back and pulled them off. She walked around over my head so she was staring straight down at me.
In a soft, almost caring voice she said, “I will give you one chance to leave the store now, dressed as you are, and you can tell everyone you were too much of a wimp and couldn’t hack it. If you stay, you will obey my every word and do exactly what I tell you. The choice is yours."
I lay there in pain, looking up into Pam’s eyes, thinking I should run, but something inside me wouldn’t let me.
“I will obey, Mistress.” It was a faint, soft voice, almost feminine.
“Are you sure!” Pam barked. She lowered herself to her knees. Her uniform skirt enveloped my head and blocked out all the light. As she got lower, I could feel the heat coming off her pussy, and when she made contact with my face, she was soaking wet.
“Yes Ma’am,” was all I could say, although it was muffled from being buried between her thighs.
Pam roughly grabbed me by the balls and said, “I can’t hear you!”
“Yes Mistress,” I replied, much louder this time. It was at that moment I surrendered to her. I started licking her, kissing her, doing whatever I could to please her, it was the sweetest tasting pussy I ever had. Judging by the moans, I was doing a good job.
She started to tease my dick through the panties, and then started to play with my nipples through the bra. As weird as it may sound, I was in ecstasy. I ate Pam to a powerful orgasm, when she finally came down, she slapped my balls and stood up, and helped me to my feet.
Pam once again looked me in the eye and said, “You do what I say, when I say it, and the tapes will remain our little secret, correct?”
Looking at my feet, I again said, “Yes, Ma’am.”
“Good,” she said as she released the handcuffs, took my shirt, jacket and the rest of my clothes, and put them in a locker, then put a lock on it.
“Here’s the deal, Mary, with all your fooling around you are late for your rounds. You better hurry, or you’ll set off the alarm and the police will show up. I’m guessing you don’t want that. Then I want you to find some suitable clothing and then get back here, do you understand?”
“Yes Mistress.” I had to hurry to get to all the check points to keep from setting off the alarm, but I was able to do it. As I was racing through the store, I was trying to think of an outfit that she would approve of. I almost sprinted to the women’s section. Not sure how much time I had, I decided to keep the bra, panty and stockings I had on. I found a mini skirt and blouse that fit pretty well, I decided to stuff a couple pairs of nylons in my bra, to make it look better.
I found a nice pair of three-inch heels to match, then off to the cosmetics counter. Pam hadn’t said anything about that, but I so wanted to please her. I found a long auburn wig - I only wished I could have hair like that - and started doing my makeup. In all my years of dressing I never really did makeup; between not having time, not wanting to get caught with not getting it all off, and not having everything I needed, I was inexperienced to say the least.
As I was doing my makeup, trying to remember the how to videos I had seen online. Pam called over the radio, “Mary, where the hell are you? Get that pretty little ass of yours back here now.” I could have used a couple more hours to get a more convincing look, but I quickly finished and headed back to the office.
When I arrived, Pam was standing there like a drill Sargent. “Where have you been?”
“I wanted to look pretty for you, Ma’am.”
“Just like a girl, always taking forever to get ready; present yourself for inspection. Not like that, on your knees, bitch.” Pam hiked up her skirt, revealing that gorgeous pussy, it was neatly trimmed and glistening with nectar. Although I had tasted it earlier, I wasn’t able to see it buried under her skirt; it was magnificent.
“You know what to do,” was all she said.
“Yes Ma’am.” I commenced to lapping at her folds for the second time that night. As I was licking her, she took out her nightstick, put it behind my head and used it to draw my head into her. After another orgasm, she roughly pulled me off her by the hair and told me to get to my feet. She stood in front of me, inspecting me, slapping her nightstick into the palm of her hand. I hadn’t notice before, her night stick was shorter and fatter with a ball on the end, unlike any others I had seen before.
She noticed me looking at it, “Oh this, it is a special night stick, and I bet you will like it. It feels so good.” With that, she took the short end and stuck it in her pussy, grabbed the other end and was moving it back and forth. Her eyes started rolling back and her knees got weak; it must have been hitting her g-spot.
She looked at me and said, “What are you looking at, bitch? Assume the position.” I stood there not knowing what she wanted. She spun me around and pushed me, unsteady on the heels, I stumbled and ended up face down across a desk. Pam came up behind me and pinned me to the desk with one hand, with the other, she lifted my skirt and pulled my panties down. I could feel the end of the night stick on my ass, it felt cold and slippery, and she started pushing it in.
My ass was on fire as she kept trying to push it into me, and the pain was so intense. I have played with my ass before, but nothing this large or violent. I felt the ball enter me, the pain was so intense, I blacked out.
When I came to, Pam was pumping away. I tried to relax. After a while the pain decreased and it started to feel pleasurable; from the sounds, Pam was enjoying herself too. When she reached her third orgasm of the night, it sent vibrations through the nightstick, right to my p-spot and before I knew what was happening, I had an orgasm without cumming.
I had heard about them, but had never experienced one; oh my god, my whole body was shaking and convulsing. I collapsed on the desk, I thought I had died and gone to heaven. Pam was spent and fell back into a chair, with the nightstick still sticking out of her pussy, she was stroking it like it was a dick.
“You better get your rounds done, before that alarm goes off. I’m guessing you don’t want to meet the cops dressed like that, and I want you back here in twenty minutes.” I got to my feet, and with shaky legs, I set off on my rounds. Trying to run on wobbly legs in high heels is not an easy task. I just barely made it before the alarm went off.
I walked back to the office, when I arrived Pam was sitting at her console. She told me to stand in the corner. She came over and took my chin in her hand, gently turned me so I was looking right into her eyes; they were beautiful. As crazy as it sounds, I think I was falling for her.
“You look like a cheap street walker. Where did you learn to apply make up?” She took a step back and looked me up and down, “What have you done to your skirt? It's all bumpy.”
It took me a minute to figure out what she meant, but when I looked down there was a distinct bulge in the front of my skirt. I guess I should have tried to tuck away better. She told me to turn around and lift my skirt. I did as I was told, and she pulled down my panties, then I heard the tape. She tore off a piece, stuck one end just below my belly button, she tucked my balls up inside and pulled my shaft back, then wrapped the tape under and stuck the other end to my back. She pulled my panties back up and told me to straighten my skirt, I did, and the bulge was gone.
Pam open the locker with my clothes, told me to get squared away. I was to leave the panties on, and the tape in place. I had to get everything back before people started arriving for work. When I had it all done, Pam called me back into the office, she put a hand on my shoulder, leaned in close and gave me a soft kiss on the cheek.
“You have a lot of work to do, little one, but I think you will work out just fine. I want you to come better prepared tomorrow.”
To be continued...
