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Evening In The Office

"Caught crossdressing in the office, but with a happy ending"

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3.5k words 3.5k words

Author's Notes

"I have been crossdressing for a long time, and until this true episode, I had always been a private or "closet" crossdresser. <p> [ADVERT] </p>More episodes followed this one, and more stories will follow."

The normal workday had finished and I gladly filed away the tedious paperwork that I had been toiling with over the past few hours. Knowing that I wasn’t going to depart for a number of hours, I went to the common tea room and made myself a cup of coffee.

Back in my office, I sat back, sipped my coffee and contemplated my plan for the next hour and a half before the evening students started to arrive. By now, the building had emptied of the usual complement of tutors and students, and so I knew that I was alone in the building. The nervous tension and excitement were already building, and by the time that I had finished my coffee, my heart was positively thumping.

I took the coffee cup back to the tea room, and then returned to my office. After shutting and locking the door, I unlocked the bottom drawer of my filing cabinet and drew out my treasured cartons of goodies.

Opening the first carton, I looked inside and smiled. This is what I had been looking forward to all day. Putting the lid of the carton to one side, I quickly stripped, removing my clothes item by item until I was standing stark naked in the privacy of my own space.

Placing my hand in the carton, I removed a pair of white lace panties, cut in the G-string style. After stepping into these exotic panties, I slowly pulled them up until the crotch was comfortably nestled against my genital area, and well ensconced between my buttocks.

Returning to the opened carton, I removed my next item, holding it up so that I could inspect it with the required amount of appreciation. It was an expensive, exquisitely made white suspender belt made of elasticized cotton and finished with beautifully brocaded lace and silk.

I clipped the suspender belt around my waist, savoring the sensation of the suspender straps caressing my upper thighs. Again returning to the carton, I took out the next items, which consisted of a pair of white, fully fashioned nylon stockings. They too had been very well made, having been finished with a beautiful lace stocking top. They were also seamed and had the mandatory reinforced heels and toes. Sitting on my desk seat, I luxuriously drew the stockings over my legs and clipped them to the suspender belt straps.

Standing now, I reached into the carton and withdrew the final item, which was a white D-cup brassiere. With my hands shaking ever so slightly, I paced the straps of the brassiere over my shoulders, reached behind my back, and clipped it securely in place.

It was now time for the next carton.

Out came the pair of high heeled, white stiletto shoes that I had acquired a few weeks previously. The effect of the shoes was to push my pelvis out and so give me a more postured, feminine look and feel.

The final item that I removed was the pink, candy-striped nurses dress that I had discovered in one of the building storerooms. I had been quite excited by this find, since I estimated that the dress was just about the right size for me. The other aspect of this was that the dress buttoned at the front, a feature that was to be quite important for my impending activity.

Being a nurse tutor had certain advantages, since most of my students were female, and a number of spare student nurse uniforms were kept at the school so that they were available for students to wear during various clinical exercises. There were different uniform dresses available – a pale blue dress for trainee enrolled nurses and the pink candy-striped dress which denoted a student registered nurse. The white dress, which identified the wearer as a fully qualified registered nurse, was also available. I had always preferred the pink candy-striped – it seemed so much more feminine.

I slipped on the dress, pleased to find that it was a perfect, comfortable fit. After buttoning up the dress, I then placed the accompanying pink belt around my waist.

Satisfied that all the clothing items were in place, I moved to the door of my office, unlocked it, and peered outside, looking down the corridor that led to the elevator. All was quiet, the corridor was empty and I was perfectly happy that the building was devoid of other people. I knew that no-one was due to arrive until at least 7.00pm when the evening classes were due to start.

My office was located on the first floor of the building, and the elevator that allowed access to the floor was only four doors or office spaces away from my own office. Opposite the entrance of this people-mover was a full-length mirror, which faced the sliding doors of the elevator. This was my intended destination.

With a degree of trepidation, but also excitement, I stepped from my office and headed down the corridor toward the elevator. All was still quiet.

Arriving at the full-length mirror, I first examined the elevator indicator lights – they showed that the car was on the ground floor, one story below my present location.

I turned, facing the mirror and examined my reflection. Yes! The dress fit perfectly and followed the contour of my hips. The hem of the dress came to just above my knees – it seemed that the dress had been made especially for me.

Again I turned so that I was facing away from the mirror. Turning my head, I had an ideal view of myself from behind. Moving my hands to my hips, I started to gently pull at the dress so that the hem lifted and started to expose my thighs. Higher I lifted the dress until I could see my stocking tops and the suspender belt clips. Still slightly higher, and I could see my buttocks. A little higher, and the back of my G-string panties came into view.

By now, I was becoming quite excited and moved my hands so that they caressed my buttocks. After lingering for a few moments, I moved my hands away and lowered the dress. Yet again, I turned so that I was facing the mirror.

I started to lift the hem of my dress, slowly this time so that the excitement could continue to build. The lace stocking tops came into view together with the front suspender clips. Higher again, and the front part of my cute panties came into view. I continued to lift the dress until I could clearly see all of the G-string with the suspender belt framing my pelvis.

It was almost too much! The temptation to reach down and touch my genital area was almost overwhelming. However, I wanted to prolong this sexual tension as long as possible – to cum too soon would almost be an anticlimax. Nevertheless, I was so excited and saw that my cock was fully engorged and straining to escape the confines of my white lace panties.

I knew that my penis would release itself from the confines of the G-string in the very near future – the panties were of a relatively small size, and yet my cock was of an impressive size, especially when fully tumescent.

It was as I was admiring my vision in the mirror when I was suddenly jolted by the sound of the elevator being activated. Spinning around, I looked in horror at the elevator indicator lights. In an instant, they told me that the elevator car was ascending from the ground floor! If the car bypassed the first floor and continued to the second floor, I would be safe. However, if the car stopped at the first floor, then whoever was in the car would most certainly see me in my glory!

I had only seconds to get back to the safety of my office, so I turned and started to walk quickly to my office – running was not possible since the high-heeled stilettos would surely have caused me to trip and fall…

I had not quite reached the office door when the elevator door opened, and somebody stepped out. The person called out my name just as I reached my office, and I entered the room and shut the door as soon as I could, praying that I had not been observed.

Of course, I recognized the voice of the person who had called out my name. It was Barry, my colleague who worked with me during the evening teaching sessions.

Damn! He wasn’t supposed to be here for another hour!

My previous feeling of sexual excitement had now turned to abject nervousness, even fear… This was exacerbated as I listened to Barry approaching my office. The fear turned to despair as he knocked on the door and then turned the door handle. To my horror, the door opened – I had forgotten to lock the door!

Barry stood in the doorway and looked at me.

“Hmmm, I thought I saw someone in a pink dress,” he said, “interesting attire for the sessions this evening.” It was more of a question than a statement.

Isn’t it funny that in times of extreme stress, the human mind can come up with the most amazing excuses?

“I, um, my wife I and are going to a fancy dress party on the weekend, and this is what I’ve decided to wear… It’s, er, a cross-dressing party. She has to go in a man’s clothing… I was just trying the dress on to make sure that it was the right size.” I knew that sounded lame, but it was the best that I could do at the time.

I really didn’t think that I sounded convincing, but it was better than nothing.

“Oh, okay,” replied Barry, “interesting choice of clothing for a party, but it seems to look all right.”

“Do you think so?” I asked, “Do you think it fits me okay?” Trying to be as nonchalant as possible.

“Yes, it seems to,” Barry responded, “but I think we had better make sure. By the way, I see that you’re wearing pantyhose as well?”

“Well, yes” I replied, “I thought it would add to the general appearance. And they are not pantyhose.”

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“Oh, then what are they?” he asked.

“They, umm, are stockings. They’re easier to put on and more comfortable,” I responded.

He entered my office and sat himself down on my desk seat.

“All right, let’s have a look. Make sure everything fits.” He seemed at ease, although his face seemed to have acquired a rather ruddy glow.

“Now, just turn around so that I can have a better look,” he ordered.

So, dutifully, I did a slow rotation, feeling Barry’s eyes on me.

My nervousness was abating by this stage, but I still felt rather embarrassed at being caught in such a way. Certainly, I had lost my erection, although I didn’t feel as though I was going to burst a blood vessel.

After observing me for a number of seconds, Barry asked a surprising question.

“So what stops the stockings from falling down?” He was smiling as he asked the question.

“Well.” I responded, “I thought that suspenders would be the best to stop that from happening, so that’s what I’ve tried. Seem to work okay.” I was trying to be as a matter of fact as possible.

“That’s interesting,” he commented, “never seen those before. Do you mind if I have a look?”

“Do you really want to?” I asked, “Ummm, we’d better start getting ready for the teaching sessions soon?”

“Oh, just a quick look,” said Barry, “I’m just curious, that’s all”

“Okay,” I said, “but I’ll just show you from the back, okay?”

“Yep,” he responded, “sounds good to me”

So I turned, facing away from him, and lifted the dress so that only the stocking tops and suspender belt clips were visible.

“Very nice,” he said, “but it’s a good thing I looked, because the right stocking and suspender straps need adjusting.”

“How so?” I asked. “They feel okay to me.”

“The right suspender clip is fastened too far toward the back of your leg,” he said, “it needs to be fastened more to the side of your thigh. Here, let me adjust it for you…”

“Oh, um, okay, if you want to,” I muttered and stepped back a little closer to him.

I felt Barry start to fiddle with the suspender clip and felt it release. He continued to play with the clip and then made his suggestion.

“I can’t quite see what I’m doing,” he reported, “you’ll have to lift the dress a bit higher.”

“How much higher?” I asked. “On second thought, you lift the dress up, then you’ll know how much you need to see.”

I felt his hand go to my hips, and then he slowly drew the dress up. Higher it went, until I knew that my bottom was fully exposed. It was at this point that I started to feel a small amount of the old excitement.

“Wow,” he exclaimed, “seems you’ve got more than just stockings and a suspender belt. A G-string as well! Very nice!”

“Yes,” I responded, “there’s nothing like completing the outfit – adds to the realism…”

“It certainly does,.” he agreed whilst he finished fastening the suspender clip to the top of the stocking.

He contemplated his handiwork and then said “I think that the stockings are not quite level with each other. Why don’t you bend over just a little, and I’ll try to adjust them for you.”

Wanting to be obliging and thinking that now was not the time to terminate the proceedings, I bent slightly at the waist and wondered what was going to happen next.

His hands touched the top of the sides of my left thigh, and I felt his fingers grasping the top edge of the stocking top. He seemed to be adjusting it by pulling it up my leg slightly. He moved his right hand to obtain a better grip on the stocking top my moving his hand between my legs, and in doing so, I felt his hand brush my scrotum.

With a shock, I realized that my cock had once again become tumescent, and hoped that he had not noticed.

I felt a certain amount of relief when he finally allowed the hem of my dress to fall to my knees. Turning around to face him, I asked him if he was happy with the position of the stockings.

“I think so,” he said, “but I think that we had better check from the front – just to make sure.”

“Okay,” I replied, “but just let me lean against the desk, and then you can have a look.”

He swiveled the chair and pushed back from my desk, allowing me to move and rest my bottom against the edge of the desk.

“How would you like to do this?” I asked.

He responded, “Why don’t we undo the buttons of the dress – that will make things a bit easier. Actually, I’d like to undo the buttons if that’s okay with you?”

Agreeing, I allowed him to remove the pink belt from around my waist. He then proceeded to undo the top button near my neck, then the next, and the next until the dress was gaping open to the level of my waist so that the suspender belt was clearly visible. He was staring at my chest and smiled.

“Ah, a bra as well. Well, that certainly completes the outfit. I like what I see.”

He continued to unfasten the dress buttons until the last one was free, and then he slowly opened the dress and sat transfixed as he gazed at me, taking in my body adorned with the exotic items of women’s underwear.

His eyes travelled from my bra, slowly down to my suspender belt, and at last, came to rest on my panties.

He was gazing at the front of my G-string, obviously noticing the very large bulge of my penis as it strained against the delicate, sensual fabric.

“Well,” he said, “it would seem that there is something that needs some adjusting. If we don’t do something, then I think that something fairly important will escape.”

He was right. My cock was throbbing by this stage, and I knew that it would come free from the G-string within the next minute or so.

I smiled and nodded, indicating that he should go ahead and do any adjustment he felt was necessary.

He moved his right hand to the front of the panties, then gently manipulated his index and middle finger under the edge of the knickers. Slowly, he pulled the garment aside, allowing my now very hard cock to spring free.

Staring at this tumescent organ, he lifted his left hand and used his fingers to gently free my balls and scrotum. He cupped my balls in his hand and, still staring at my cock, he said, “Now, that is what I call a clitoris…"

I replied (in a somewhat husky voice), “And what would you usually do with a clitoris, Barry?”

His response was to smile and gently clasp by throbbing cock in his right hand.

“The first thing I would do is feel it, and start to stroke it,” he murmured.

And that he did. Still caressing my balls and scrotum, he started to stroke my clitoris along its entire length but just avoided touching the head.

It was exquisite! I looked down and saw this man playing with my clitoris, my body decorated in beautiful feminine underwear. This was something I had dreamed of doing for a long time, and now, it was happening.

My voice shaking, I asked, “And what else do you do with a clitoris like that?”

“I’ve never seen an eight-inch clitoris before,” he replied, “But there is something that I would like to do with it.”

“What would that be?” I asked.

In response, he bent his head, lifted my cock so that it was pointing up toward my face, and then ran the tip of his tongue from the tip of my penis down to my scrotum. His mouth stayed in that position and I could feel his tongue and lips exploring my balls.

With his right hand, he started to stroke my cock again, and I gasped.

“If you keep fingering my clit like that, I’m going to cum, and soon.”

“Yes, I would like to see that. So let’s see if we can make that happen.”

He suddenly pushed back the chair and started to undo the belt of his pants. Standing up, he unfastened his zipper and lowered his pants, and then his jockey shorts. Sitting back on the chair, he leaned back so that his erect cock made its presence visible.

“Okay,” he said, “I want you to turn around and sit on my lap. But take the dress off first. Slowly – I want to watch you strip.”

I pushed myself from the edge of the desk and slowly removed the dress, allowing it to drop to the floor from my shoulders. Now, I was clad only in bra, suspender belt, stockings, a slightly awry G-string and high-heeled shoes. I turned around and started to lower myself to his lap. He grasped me by the hips, and gently pulled me back so that as I sat, his cock made its way between my upper thighs. By the time that I was fully seated, his cock was jutting from between my stocking tops.

He reached around, and took his own cock in his hand and started to masturbate himself with his left hand. His right hand also appeared, and he grasped my throbbing clitoris and began to stroke and stroke and stroke.

It did not take long for him to cum. I watched in fascination as he pumped himself faster and faster, until suddenly his cock erupted, sending jets of cum over my stocking tops, and up onto the front of my suspender belt.

He gently pushed me into a standing position, turned me around and guided me backwards so that I was, once again, leaning against the edge of my desk.

He took my clitoris firmly in his right hand and started to masturbate me, this time making sure that the head of my cock was included in this fantastic massage.

Then he said the words that made me cum and cum and cum:

“I would love to dress you in a see-through negligee, with silk panties and stockings, and watch you masturbate your beautiful clitty until you cum.”

Published 
Written by Timolena1957
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