I feel like such a cute little crossdressing slut in this lingerie

I feel like such a cute little crossdressing slut in this lingerie
503 Likes 4918 Viewed

Finishing school is great. time to hit the job market. I could hardly wait to put my new degree to use. I had been sending out resumes, and answering ads all week when I had a very interesting piece of email. "We are looking for a highly qualified individual who is not afraid of hard work. An open mind, sense of adventure, and flexible schedule are mandatory.

Top notch office skills, professional appearance, and a desire to please also required. Extraordinary pay for the right individual." Hmmm. I called and set up an appointment for that afternoon. I showered and dressed carefully, wearing my new lacy lingerie, my best knock-em-dead suit, and an air of confidence. I wanted this job.

Big toy deep in my ass

it sounded like different. I also needed the work.

Her asshole used to be so tight that it was actually hard to fuck it

I drove up to a beautifully appointed large house just outside of town. It was in a park-like setting, with no neighbors visible. As I got out of my car, a valet appeared, hand outstretched for my keys. Such service - and I was just a job applicant. I was met at the door by a tuxedod butler, and shown into a plush waiting room.

Within moments, a rather prim, well dressed lady appeared. She asked for my resume, and a little bit about my qualifications. I knew I had more skills than they were asking for, so I was relaxed and poised when I answered her.

Still though, I felt my tensions rise a bit. "Hmm. I like your qualifications. This job will entail a fair amount of travel. We do ask that you pass a physical exam before we even consider the next round of interviews.

Not to worry, we have a doctor right here on the premises as we have special. requirements. Now, walk this way." She led me down a hall and into another waiting room. "He will be with you in a few moments. While you are waiting, please remove all your outer clothes.

You may keep your bra and panties on. Here is a gown for you to wear. Then, just have a seat and relax." I did as I was told, and had just sat down to read a magazine. The door opened a few moments later and a nurse in a starched white uniform entered.

"The doctor is almost ready for you. We need to record some information first. Follow me, please." I followed her into the exam room. I stood quietly as she measured my height and weight.

As I turned to get off the scale, she picked up the hem of the gown and lifted it up high. "Nice. I think the boss will be pleased.

The doctor will be right in. Have a seat on the edge of the table." The doctor breezed in, and sat down next to me, clipboard in hand. "Well, Anni. You look perfectly healthy to me. we just need to make sure you are in great shape all around." He reached behind me and untied my gown, easing it down in front.

His stethoscope was cold on my skin as he listened to my heart and lungs. I was embarrassed as I felt my nipples harden, and saw his smile. His hand grazed my nipples as he reached around to listen to the sounds from my back. "Wonderful. Now, just lie back." As I turned to lie down, he took the gown from me. "You will not be needing that anymore. I will be testing your reactions to certain stimuli as well as completely checking you out today." The air was cool as I relaxed into the exam table.

He poked and prodded and listened. I closed my eyes, wishing this to be over. The room was in soft peach tones, and the music was very soft and relaxing.

He had such soft skilled hands. I felt him reach up, and undo the front hook of my bra, peeling back the cups.

He caressed each one, moving his hands in circles, pinching my nipples between his fingers, sometimes hard, sometimes soft, always watching my reaction. Against my will, I arched my back and moaned softly.


I gasped as he reached down and took one stiff nipple into his mouth, gently biting it. He next took both hands and tucked his thumbs under the band of my panties, sliding them down my hips. I offered no resistance to him, especially when he cupped my mound in his hand, and slipped a finger between my pussy lips. "Very nice. nice reactions. Now, slide all the way down to the bottom of the table, and put your legs in the stirrups." He adjusted a light between my legs.

the warmth striking my sensitive pussy. The speculum was cold as it slid in. The nurse bustled by me, and discretly placed soft restraints on my wrists and ankles, securing me to the exam table.

"Sandy here is going to take some pictures for our records." he announced. She took several pictures of me, tied to the table, with the speculum inserted.

You look like you need some relief JOI

He then inserted a lubricated, gloved finger slowly into my virgin rosebud, caressing the outer edges, and stroking gently until I relaxed. A warm syringe followed the probing finger, and I felt a fair amount of warm fluid slide into my ass. Finally, that cold, hard speculum was removed, and I sighed deeply. "She is going to prep you now for the next part." he said as he got up to make some notes. Sandy took out a pair of scissors and began clipping my long, lush pussy hairs away. I felt powerless to resist her, even if I could have.

Free gay young men blowjob porn and xxx emo movies Aaron Needs Some

When she was satisfied, she covered my shorn cunt with a hot, wet towel. They let me lay there for several minutes this way. the heat soaking into my already hot box.

I had never been shaved before, but I had heard all about it from other girls at school. Just the thought of it made me hotter. She came back over to me, and untied my hands, retying them over my head. "Mr. James does not like any body hair." I had shaved that morning anyway, but went along with the program. She worked hot lather into my waiting pussy, all the way back to my ass. As she let the lather soften my remaining hairs, Sandy worked quietly and efficiently, shaving all the hair off close to the skin, then wiping the excess lather off.

As a final step, she rubbed this wonderful lotion in, all over my naked pussy, all the way back to my ass, then up to my breasts. The lotion was warm and soothing. My pussy was open and inviting Sandy to work more lotion in, and she obliged me by sliding her fingers between the lips, and deep within, then coming back out and massaging it deep all around. I ground my hips into her hands as best I could. I felt wonderful. relaxed.

The doctor picked up Sandy's camera and took several pictures of her at work on me. Several fingers were inserted into my pussy, soon followed by a slender vibrator, which was turned on while it was being inserted and pulled back out.

As I became aroused by this instrument, it was turned off and replaced by a larger, stronger vibrator. This was worked in and out, slowly. As I started to enjoy, it was replaced by still a larger one. "Okay. now. this may feel uncomfortable, but we need to measure your capacity." I felt a huge dong at the entrance to my pussy.

As well lubricated as I was, it slid right in, nice and deep. It was left there for a moment for a picture and a measurement, then this was also stroked in and out slowly until I relaxed and it slid in and out easily. This process was repeated several times, each time with a larger dong.

Finally, they found one that barely fit me. I groaned as they tried to work it into me, wincing at its forced entrance, feeling so completely full. I was gently lifted by the hips, and had a cushion placed under my ass. Sandy urged me down further on the table, until my ass was several inches over the edge. She worked one slender lubricated finger in, caressing the delicate tissues until they cooperated with her.

This wonderful finger was soon replaced by a thin vibrator. As soon as I relaxed to these new sensations, the doctor began moving it in and out, stopping several times to work more and more lubricant in.

The size on this was increased several times as well until they were satisfied. "Wonderful. we have our measurements, and you are in splendid shape. I am sure Mr. James will be delighted with you," he pronounced as Sandy wiped me clean. I was told to put my bra and panties back on, and given a very short silk robe to wear. Sandy then took me to an alcove to wait for the next phase. After my exam, I could hardly imagine what was next. I did not have long to wonder.

A slender, handsome young man pranced into the room, and ushered me into a plush sitting room. He had me sit next to a huge desk. A handsome gentlman with slightly greying hair and a crisp suit cme in a few moments later.

He hardly looked at me, but picked up a folder that the prancer had left on his desk with all the doctor's notes and my resume.


"What we require, Anni, is complete devotion, loyalty, and obedience. We need a combination of a secretary/personal assistant, as we are only borrowing Max. You will be responsible for carrying out all orders, completely, and fulfilling all needs.

You certainly have the skills for it, both on your resume, and in the doctor's findings. Now, if $2,000 a week is satisfactory, I say we proceed with your orientation." I looked at him with surprize in my eyes. I had the job?? And the salary was tremendous. Now, what did I have to do for this?? "How well can you follow orders?" he asked, looking me straight in the eyes. As if he read my mind, he stood up, walked over to my chair, and helped me stand up. "Untie that robe," he commanded.

"Drop it on the floor. turn around. now, bend over from the waist. Hmmmm. yes. Very very nice." he said as he led me into an inner office. This one had a huge oak desk, completely cleared off, looking out over the grounds. He led me to the open French doors in full view of a group of employees on the patio, and moved behind me.

Young babe fucked by grandpas big black cock

I could feel his breath on my neck as he reached around, and cupped my breasts, pinching the nipples through the lace. Still outdoors in front of anybody who cared to look our way, he unhooked my bra, sliding it from my shoulders, dropping it on the balcony, taking his time caressing my breasts, nuzzling my neck. I found myself melting into his arms. Next, he led me over to the desk, and positioned me so that my ass was barely on the edge, my legs were far apart, and I was leaning back on my arms.

Taking a huge pair of scissors out of the drawer, he cut the sides of my panties, slowly peeling them off. He gently pushed me down flat onto the desk, supporting my legs with his shoulders. I have had oral sex performed on me before, but nothing like this.

he took his time, nibbling, sucking, and playing with my clit until I almost screamed with delight. Next, he probed and explored my cunt with the same care. stroking slowly. He did all this quietly, not trying to arouse me. He was exploring, teasing me just the same. I was so wet and hot, and he could sense this. He would not permit me to cum, he was just testing me, checking my reactions.

He slid his hot mouth and tongue all the way down to my ass, and rimmed me, licking me all the way back up. Now, gently inserting a finger into this hole or that, he watched me intently the entire time. "I am sorry to sound rushed, but we have a staff meeting in 5 minutes, and there are introductions to be made," he pronouced as he handed me back my thin, silk robe.

I noticed with some horror that my dark nipples showed right through the thin fabric. I may as well have not worn a thing! He had Max escort me to the meeting room after handing me a notebook and several pens.

Webcam couple fuck with a toy

I was shown to a beautifully paneled meeting room with a huge, 24' table down the center, and big, overstuffed couches on two walls.

Max indicated I was to sit in a chair just to the left of the head of the table, right next to the window, and far from the doors. The staff of secretaries, public relations officers, and business managers began to filter in, scarcely paying any attention to me.

Conversation was quiet while we all waited for the boss to enter. I sat back and watched the meeting as it formed up. The attitudes became very formal as soon as my most recent interviewer entered. I was briefly introduced, and then the meeting got underway. He had two secretaries taking profuse notes. I could not understand why I was needed. I was startled to feel his hand under my robe, parting the flimsy garment right there in the meeting, only inches from his vice-president of marketing.

As I leaned back in my chair, he quietly untied my robe, and slipped a hand in to caress a tit, pinching its nipple. Just as quietly, he pulled the robe back into place, and let the meeting draw to its conclusion. Nobody even looked our way, or paid his public display any attention.

I was stunned to see how wet I was. and wondered what was next?? Who was this man that I worked for?? "Max. Take Anni to meet her new boss," my interviewer ordered. "Let's see how he likes our find." My jaw must have hit the floor at that point.

all that and I did not even know who I worked for. I was escorted down several quiet hallways and a flight of stairs into a huge room, with several pool tables and strange pieces of furniture.

Along the walls were several plush couches. This room was a large recreation area, with two gentlemen playing a game of eight ball on the table furthest from the door, quietly watching us enter the room.

Max pointed one of the men out, and whispered in my ear "That is your new boss" as he left my side. Mr. James was only slightly older than the dapper man who did my last interview, with a bit more grey at the temples.

He was about 6' tall, quite handsome, with electric blue eyes that followed every move. Those eyes were trained on me now, caressing every curve of my body as I stood there nervously and waited for him to speak.

I shivered as I saw the power in those eyes, and read the message of lust. "Well, well.


It seems the staff has picked a delightful assistant for me. They all tell me you have done very well with your auditions, even enjoying them. I like that, very much," he said with a quiet smile. At his unspoken command, I untied my robe, and walked over to him. He reached down, and opened the thin garment, peeling it from my shoulders. As I stood before everyone totally naked, I started blushing.

He gazed at me admiringly. "You have pleased them. Now, are you ready to please me?" I nodded my head slowly, unable to speak. "Good. I think we will get along just fine. I have a lot to teach you." He reached out and placed a cool hand under my right tit, lifting it slightly. His little finger extended up to graze the nipple. Guiding me by the tit, he eased me to the adjacent pool table and lifted me onto it.

Placing my ass at the edge of the raised bumper, he gently pushed me back until I was laying flat with my ass elevated, and my legs were spread far apart and supported by two staffers. Cool dry fingers caressed my sensitive, newly shaved mons, and teased from my slit all the way back to my exposed asshole. Gently parting my pussy lips, the exploring fingers dipped just slightly inside, then went back to their caresses. My clit was stroked lightly, then was grabbed by a cool, hard object that squeezed it firmly.

At about the same time, a staffer came around near my head, and with a cool quiet manner, my nipples were teased erect, pulled up, and captured by firm nipple clamps. I moaned with delight as these clamps were twisted slightly. Fingers, then a warm hard tongue were now exploring my pussy and ass.

A huge, cool, ribbed vibrator was inserted and turned on, teasing me from the inside as the mouth at my clipped clit sucked away. I bucked my hips as the warmth of a first orgasm began to wash over me. The flood of juices was eagerly lapped up as the vibrator was withdrawn and the clips removed. My boss' hungry mouth replaced the left nipple clamp, gently biting the sensitive tip. I felt the head of a huge cock at my pussy, teasing the engorged lips, then begin to enter me. This man was huge, almost uncomfortably thick!!

When he was deeply insterted, his balls slapped my ass, and I felt the head of that monster cock hit the top of my uterus. Now I understood all the tests to see if I could handle this size! As he began deep stroking, my second orgasm began to build. He noticed this, and stopped, pulling out of me. Slapping my ass firmly, he commanded, "Not yet! I am not ready to come." He lifted me from the pool table, and took me to one of the plush couches, urging me onto my knees.

Ass high in the air, my face buried in the cushions, he spread my legs far apart, and caressed my clit with his fingers gently. "This is the position I want you in when I tell you to take dictation. I want your ass in the air, legs far apart, and you on your hands and knees. You take this position on whatever furniture happens to be in the room." I nodded my agreement. As I did so, his monster cock was again at my pussy, begging for entrance. He stroked several times very deep, then grabbed my hips and began stroking harder and faster.

His hands slid down, pulling my pussy lips apart, caressing my clit. As his huge wads of come started to fill my pussy, my own orgasm began to take over. I moaned quietly as it built while he stroked and pumped his seed into me.

Street fighter porno

As he finished and slowed his stokes, it erupted with screams, cries and whimpers as wave after wave of pleasure swept over me. Staying still inside me, holding me until it subsided, he commanded, "That is the last one you may have without my permission.

I can tell you will have a lot to learn, Anni. This was just lesson one. I think you will do just fine, just fine indeed." I nodded my head slowly in agreement.