CAUGHT, Part 1

When I was in high school and college I used to baby-sit for some of the families in the neighborhood. It was one of the best things to ever happen to me. This was because it put me in the position of being paid to raid some lady’s lingerie drawer and have the time of my life. I had virtually limitless panties and bras and slips to choose from to dress up in and, from time to time, the opportunity to add to my collection. It was just heavenly!

For some five years I did this and never once even got close to being caught out at it. So, when I took on a new "client" my second year of college I was looking forward to what her lingerie drawer would offer me. Our initial contact was by phone, she had recently moved into the neighborhood and had heard of my services. She asked if I was interested in a weekly sitting job. I said I sure was and asked her what she needed. She told me she was divorced, had two young boys and every Thursday night she had to work. The boys went to their father’s for dinner after school and he would drop them off at her home around 7:15 PM. I was to arrive for the first evening at 6:30 when she would give me my instructions and then take off for her meeting. After that, I was to arrive at 7 PM to be there before the boys arrived.

On that first Thursday, I headed on over at the appointed hour and rang her bell. She answered and introduced herself. It turned out she was a fairly attractive woman (in a severe sort of way) in her early 30’s. She was certainly desirable and I was hoping for some nice underwear to play in…as soon as she left! Which was pretty quickly since there was not much to it.

As soon as she was heading up the street, I made a beeline for her bedroom and almost intuitively I found her lingerie drawer. As I had hoped, it was full of some lovely lingerie. In fact, there was almost too much to choose from. But since I have a weakness for black, lacy lingerie, I found a nice pair of black panties with lace trim, matching bra and garter. Knowing my time was limited, I went straightaway into her bathroom and stripped down then slipped into her panties. My cock was throbbing by then and aching to let loose. But I continued to dress up pulling on her bra and then her garter. I found a pair of hose hanging off the shower rod and slipped into those and felt complete at that point. In the large mirror before me I enjoyed the view of myself in her lovely, lacey lingerie. I especially enjoyed the swell of my cock encased in those silky panties. I began to slowly rub myself and savor the incredible excitement coursing through my entire body. Finally I could stand it no longer and let my cock explode. Over the years I’d become very adept at pulling the panties away from my cock as it shot it’s load to keep from getting it all over the panties. When I’d stopped and my heart had slowed down, I quickly cleaned up and dressed again in my street clothes, put the lingerie away as carefully as I could to be sure it did not look like it had been disturbed. Then went downstairs and turned the TV on. The kids arrived around 7:20, went to their rooms and that was it for the evening and pretty much how things went for the next 4-6 weeks.

Then everything changed. That evening I went over as usual and I’d made my way to her bedroom to make a selection. I was quietly standing at the dresser, lingerie drawer open and looking through the panties there when all of a sudden I heard a rustle behind me and her angry voice. "So! I was right you little perverted sissy. You have been in my lingerie drawer."

I was absolutely shocked. I dropped the pair of panties in my hand and turned to face her, stammering in my terror at being caught. For a moment I could say nothing and she started in again with, "Well, what about it? How could you do this? What are you doing in my underwear? Wearing it you disgusting little sissy? I’m going to call your parents and tell them exactly what I found you doing!"

With that I found my voice. "No-o-o, please don’t do that! Oh God, no. I-I’m sorry, I know I shouldn’t be doing this. Oh God please don’t tell anyone. Please….." I pleaded with her. I was scared out of my mind. I couldn’t believe after all these years someone had caught me. I’d been so careful. I realized I just gotten lazy and hadn’t made a careful check of the house. Now, I was dead.

She suddenly came into the room, fixing me with her eyes as she walked to the bed, sat down and took out a cigarette. "Light me." She ordered. Shaking, I took out my lighter and lit her cigarette for her. She leaned back on the bed, took a drag and exhaled at me. There was an evil smile playing on her face that made me feel very insecure…I also felt mildly excited and the hard-on that had instantaneously vanished at her entry began to return. I was thinking "Oh God, how can THAT be?" Meanwhile, she was looking at me appraisingly. She seemed to make up her mind suddenly and said, "Well, little sissy, if you don’t want me to tell anyone then you will have to pay. Are you prepared to pay the price?" she smiled somewhat evilly. "Go to the center of the room and face me. Then take off all of your clothes." She ordered.

Very startled, I moved to the spot indicated and then stood there, unsure of what to do. I mean it was such a unexpected demand. And I was horribly embarrassed at the thought of standing naked before this woman. But the look in her eyes left no doubt as to the serious nature of what she wanted. So, I slowly began to strip down for her. I began with my shirt, proceeded to my shoes and socks only to arrive at my pants and underpants. It was with a lot of fear I let my pants fall to my ankles and step out of them. I paused at that point. She sat forward on the bed, stubbed out the cigarette and said archly, "Well…?" So, in defeat and humiliation I slipped my underpants off and stood naked before her…an erection slowly beginning to take shape.

She smiled at that and sat back again just looking at me. Again that smile and, "Now slowly turn around for me. Not too fast either. I want to see all of you." I did as she directed and finally came all the around again. "Nice butt, cute little cock." Was all she said. More silence as she continued to simply stare at me. Finally she moved forward again. "Go over to the dresser and open the lingerie drawer." She ordered, "I think you know where that is don’t you?" I nodded.

"I think you need to understand how to address me you little sissy. When I talk to you I expect you to show the respect I deserve. So, you will say ‘Yes Mistress’ or ‘No Mistress’ or whatever makes sense at the time. Do you understand?"

"Y-y-yes, Mistress. I understand."

"Good. Now get your perverted ass over to that drawer and open it up!"

Like in a dream, I moved to her dresser and opened the lingerie drawer. Before me I could see all her lovely panties and bras that I had come to know so well. I could feel my cock getting hard again and had a feeling that would only anger her. But not matter what I tried to do; it would not stop growing.

"Alright, little sissy, let’s get you started on your way to becoming my personal servant." She said. "First, you need proper dressing which starts with underwear. Look in that drawer and find that pair of black lace panties I know you keep putting on when I’m away. And find the matching bra and garter belt while you’re at it. After that, in the drawer below you’ll find some black hose. Take a pair out too."

"Yes, Mistress." I acknowledged. My hands shaking like crazy, my heart beating so fast I thought it’d burst, I found the panties, bra and garter she asked for. I closed that drawer and opened the one below. I found a pair of black hose and pulled them out, closed the drawer and turned back around to her.

"Is this good, Mistress?" I asked. She nodded and waved me back to the center of the room where I quietly stood before her once again. She got up and walked towards me, then began a slow walk around me. As she passed behind me, she gave my ass a quick, stinging slap that immediately brought me to attention and eliminated my hard on. I began to shake again as she came back around to face me. She reached down and batted my balls just enough to hurt a bit.

"Okay my little sissy, let’s see what you look like properly dressed. And remember I am in charge here. Don’t think you can get away with anything or I will spank you properly. That swat was to make you understand who’s in charge. Understand?"

"Y-y-yes, Mistress. I will do whatever you want me to."

"That’s right. Now get that garter on and then into the hose."

It didn’t take me too long to pull the garterbelt up around my waist, carefully roll the hose and pull them up my legs. Then, from a lot of practice, I easily got the top clipped into the garters.

"Very good." She commented. "Now slip into those panties and the bra. After that, I want you to go to the closet. In the center of the floor you will find a pair of black, high heel shoes. Bring them out and put them on. Then walk back over here to the bed and stand beside me facing the wall."

I did as she asked dressing up in the panties and bra. My cock was getting hard once again and I realized there was nothing I could do about it. I was just too excited to not get hard. I went over to the closet and got the shoes. They were a bit small and hurt slightly to put on and walk in. Consequently I found myself walking in a kind of mincing step as I returned to her side. This seemed to please her too. I turned and faced the bed as she had instructed.

She was quiet for a while as I stood there. "This is training, you understand?" she said more as a statement than question.

"Yes, Mistress." I replied.

"Because of that and your invasion of my privacy on when you ransacked my lingerie drawer, you need some remedial discipline, I think. Something to demonstrate just who is in charge and what is acceptable behavior." She paused and ran the palm of her hand down the curve of my panty-clad butt. It felt really good and I responded by pushing toward her hand. She responded by a quick slap on my butt, then stepped back slightly.

"Now, you will learn about ‘assuming the position.’ This is something you will do promptly without question. Move back from the bed a step, then lean down and with your arms, brace yourself against the mattress." She instructed. "Then wait."

My heart was pounding now and I was pretty sure what was coming next. The incredible thing was I was getting even harder in anticipation of the spanking I knew I was about to get. So, I did as she asked and there I was my ass in the air completely at her mercy. She walked over to the dresser and opened a drawer. Out came a wooden paddle with some fabric wrapped around the business end. She smacked it against the palm of her hand, smiled and walked back over to me. She reached into the waistband of my panties and delicately pulled them down to expose my trembling ass. As if mocking me, she gently stroked it. "Now my little sissy, five whacks of the paddle ought to communicate to you, don’t you think?"

"Yes, Mistress, it should."

"Good, then let’s begin." And she delivered a solid whack to my butt. Despite the fabric around the paddle, it still stung a lot. I must have made some sound because she told me I had to be quiet during these "sessions," and any whining or crying on my part would just bring more of the same. I bit my lip and took the next whack. It was a bit harder and hurt even more. I could feel my butt getting hot and painful. I wondered if I could take the next three. But I had no choice. And inexorably the last three whacks came to my butt causing so much exquisite pain. I was quivering all over, still as hard as before but I had kept my silence, as she’s demanded. I began to get up and as I did so she hit me once more, really hard. "Don’t you ever get up from a ‘session’ without my permission!" She commanded. "Since you are learning I will let if go this time. But watch out…."

So, I remained in position, my sore and red ass still sticking up in the air. I felt so humiliated, like a guilty kid caught at some naughty thing. She was laughing now. "You look so silly sissy with your cute little butt up in the air. Oh we are going to get you in line. Now remember this…that is called "assuming the position." If we are upstairs and you require punishment, I will order you to assume the position. You will immediately come to the bedroom, lift your skirts and drop your panties and bend over like you are now. Then you will wait for me to administer your punishment. If we are downstairs, you will go to the couch in the living room and follow these same instructions. Am I clear enough for you, my little sissy?"

"Yes Mistress, I am very clear on this."

"Good, and don’t ever forget. Stand up, turn and face me and pull those panties up. We have some more discipline issues to deal with."

I did as she asked and then quietly waited again for my Mistress’s instructions. She tossed the paddle towards the dresser and turned to me. "I want you to lay down on the bed spread-eagled on your back."

As I lay down on the bed and stretched my arms and legs to the four corners, she went back to the dresser and pulled out some lengths of cord. With these, she carefully tied first my wrists to the posts at the head of the bed. Then she fastened my ankles to the shorter posts at the foot of the bed. I was totally helpless and in her mercy, my surreptitious tugs on the cords made that clear. She smiled down at me, pausing to admire her handiwork.

"What is important is for you to serve me absolutely and without question. And to further this, you should be as docile as possible. I can see from that bulge in your panties you need to be drained of the poison that is in you. Therefore, we are going to take care of both situations. Just lay there quietly and wait."

She left the room and went in to bathroom. I could hear her moving around in there. Then I heard her drawing a bath. As the water ran, she came back out and went down stairs, smiling at me as she went. Shortly she reappeared with a glass of wine in hand and returned to the bathroom. I struggled slightly but was completely bound. My cock remained as hard as ever and I kept feeling both excitement and dread. I was completely conflicted. I was scared as hell that this would get out. I was excited at the prospect at the same time. And I wanted to masturbate and cum more than anything in the world. It was just incredible.

In the bathroom, I could hear her as she took off her clothes and stepped into the bath. I could tell she was laying back and enjoying it along with her wine. It was obvious she was in no hurry to finish. The perfume she’d put into the bath wafted out to me, which seemed to excite me even more. Finally I heard her flick the drain and get out of the tub. She toweled off and then it was quite again. At last she flicked off the light switch and I could hear her bare feet on the carpet behind me. I tensed in anticipation of what was to come next. But she just stood there apparently enjoying my frustration and trepidation at the next phase of this evening.

After what seemed like forever, she slowly moved into view. She was wearing only a white lace garter belt and hose. I was taken aback at how lovely her body was. Her tits were nearly perfect, firm and upturned. She had a flat tummy and a dark "vee" of pubic hair at her crotch. Her skin was white and smooth. I longed to caress that skin but was helpless to do anything but look in frank admiration. She smiled seeming to appreciate my obvious admiration and excitement at seeing her as she was. I hoped this would please my mistress and prevent any more spankings this evening.

"The next step in your training will be to take care of me. It’s my thought your tongue needs to be exercised to its limit between my legs and I expect you to do an expert job of eating me thoroughly and exquisitely. You had better make me scream in pleasure. Otherwise the paddle will be your reward instead of the draining of your poisons."

She stretched and smiled sensuously, then got into bed swinging her right leg over me to straddle my chest. As I looked up it seemed all I could see were her lucious breasts and creamy white skin. She leaned forward and placed her right breast on my lips. "Lick it." She commanded. "Caress it with your tongue and make my nipples hard and erect. Make it gentle and sensual for me."

I immediately began to run my tongue over the nipple, which became erect almost at the touch of my tongue. She sighed and pushed a little harder against me. I could just sense her pubic hair brushing against my belly. I was just aching between my legs I wanted to cum so badly. I felt my pelvis thrusting gently upward. She paused and pushed it down indicating I was to be still except for my tongue on her breast. I concentrated on that and she became more and more aroused pulling back and placing her other breast in my mouth. "Now suck it!" she commanded, "gently while you are still licking."

This I did to her obvious pleasure. Low moans began to come from her and she lowered her pelvis so she could rub her vagina against my chest. As she did so, she got more and more moist as her excitement increased. I could smell her perfume mixed in with her musk and it got me even more excited too. I strained against my bonds to no avail constrained to lay there at her command. Finally she raised herself up on her knees and moved forward toward my face. Shortly her vagina was squarely over my mouth. "Eat me!" She demanded. "Use your tongue on my cunt and make me moan in pleasure."

Immediately she lowed on to my face and barely able to breathe, I began licking her vagina and pushing my tongue into her. She moaned even more and began rocking slowly in time to the thrusts of my tongue. She tasted wonderful, her smell as exciting as seeing her before me. I realized I was enjoying this almost as much as she was. Time passed and with a suddenness that surprised me she exploded in an orgasm that seemed to shake her to her core. She was wildly swinging her hips and panting her pleasure. Then as suddenly as it came on she was done. Her movement stopped and she slid down on my chest laying partly on me, partly on the bed.

We lay like that for several minutes. Then she slowly raised herself up and looked me in the eye. "That, my little sissy, was excellent. I think you have promise after all. And because of that I am going to reward you."

She swung off of me and sat alongside. She reached down and slid the waistband of my panties down and hooked it below my balls. My cock was pointing straight up and throbbing noticeably. She grabbed the shaft and began to stroke it up and down slowly. "You may not cum until I say you can, understand?"

"Yes Mistress, no cum until you say so."

She nodded and continued to stroke me. Soon she leaned over and put her mouth around my cock. Expertly she drew it in and out of the "oh" of her lips. All the time her tongue was working the shaft bringing my excitement to level I never thought possible. It was all I could do to bear down and not cum in her mouth. I think she must have realized this and relented. She went back to using her hand only this time it was more serious and shortly she said, "Okay sissy, spill that poison." And I immediately came like never before, the cum flowing all over her hand and me nearly screaming in pleasure. It went on for minutes before I eventually settled down and was left laying there bound and panting.

She nodded her approval then looked with some disgust at her hand still covered in my cum. "One of your jobs, sissy, will be to clean for me. To make a point of this, why don’t you start with my hand." She moved it towards my mouth. "Your tongue did such a nice job on my cunt, why not on my hand? Lick it up!" She ordered.

I felt like I’d been slapped. The though of eating my own cum was horrible. Yet there it was and the alternative was that paddle. Hesitantly I stuck out my tongue and tasted the slightly salty, warm cum on her hand. I felt a sudden tingle in my groin and then went at cleaning off the cum from her hand licking it eagerly. It took very little time!

After that, she got up and went back into the bathroom leaving me still tied to the bed. I again heard the water in the bathtub and shortly she was splashing around in the tub. It was a quick one and she was out again toweling off. She came back in to the bedroom and smiled. "Well, sissy, so far so good. If you keep behaving as well as you have this evening, your secret safe. But just remember that can change any time. We have just one more thing to do." With that she went to the dresser one last time an pulled out a camera…a Polaroid I could see. As I lay there on the bed bound with the panties hooked on my balls, a bra, garter and hose on she snapped a picture; then a second and third. These she let develop and then she disappeared with the pictures. I could hear her still on the second floor but that was it. In a few minutes she returned without the pictures. It was clear I was now in her complete service. She untied me, had me put my lingerie in a laundry hamper. Then I dressed and she sent me home with the admonition to be back the following Thursday at 7 PM.

On to Part 2

Back to Home