tagTranssexuals & CrossdressersRachel's New Assignment

Rachel's New Assignment

byred_fruit©

This story is a follow on from my previous story "A Hard Day at the Office" where Jack was caught by his boss Helen, after he had changed into 'Rachel' in the office toilets. When Helen finally realized Rachel was in fact Jack, she took advantage of her seniority and forced Rachel to do exactly what she was wanted, threatening to expose her to the rest of the office. Jack returned the following week nervous about what would happen next...

After I left work last Friday, somewhat bewildered at what had occurred at the hands of Helen I spent the entire weekend agonizing over what was going to happen. Surely she'd tell someone? Let slip a whisper in confidence? It was bound to get out somehow, it always did in an office like ours. All about my secret night life persona and how she found me in the ladies toilets at work! I didn't feel up to the girls night out I'd had planned last Friday night, and anyway my after hours meeting with Helen had made me too late to catch the bus down to London. Instead I'd gone home, run myself a hot bath and tried to relax with a glass of wine. But I couldn't manage it! Every time I closed my eyes, my mind replayed images of Helen's mischievous smirk and delicious curves. She now knew my secret and as a result I was totally at her mercy. I didn't want other people to find out about me and it made me nervous thinking about what would happen at work. I even spent a few fruitless hours surfing jobs on line to see if I could quit to save myself embarrassment. Deep down I knew that I wouldn't quit though. Helen had shocked me with the intensity of her lust, and I knew that I couldn't quit without seeing her again. I had to admit that I loved being dominated by sexy red haired boss.

Back at work on the Monday and I was bordering on a nervous wreck. I was paranoid that everyone knew already and that each person walking past or every glance in my direction had hidden meaning. I was sure I could hear my name slipping into other people's conversations and blushed whenever someone turned to look at me. The day slowly dragged on and after a morning barely being able to concentrate I came to the conclusion that Helen must have kept her word. More than that when Helen did walk past on her way into her office after lunch, she barely glanced at me. I knew she couldn't give me a sly wink or acknowledge me, but it hurt a little to feel used and tossed aside like that. If I didn't still have the dirty washing at home I would even question that it all happened at all! As I relaxed more into the day, I returned to my normal work patterns. After lunch Lucy, the head of administration, came over to my desk and informed me of my next assignment.

"Well, lucky you," said Lucy sarcastically, "Helen has demanded that you're going with her to a client meeting tomorrow! Sorry, you're going to have to put up with the little madam, but I think the other girls will appreciate them getting a break from her wrath! Apparently they're all way too lazy, so she wants to try out that boy instead!"

"Oh," I replied secretly thrilled at the news, "Well, what do I have to do?"

"The usual, take notes, phone calls, organize, and she normally treats the admins like some sort of slave, but at least you'll get a free meal from it," replied Lucy, "She wants to brief you in her office at 5 o'clock."

I tried not to look too excited and gave a little shrug and grimace towards Sue sat on the next desk.

"God, I hate that bitch Helen," Sue whispered to me, "She's always ordering me about when I take minutes at her meetings. 'Fetch this', ' I'll have a coffee'. If I didn't need this job so bad I swear I wouldn't take the crap. Typical that she makes you stay late too! She knows we don't get overtime like she does!"

"I know," I replied, "I've been lucky enough not to get assigned to her before. I always thought she liked girls more!"

"Yeah, well we all know what happened with Amy." she said raising an eyebrow, "She was her favorite secretary before she suddenly got sent up to the Manchester branch with a bonus and a promotion!"

"Is that actually true?" I asked.

"Well, no one could get Amy's side of the story after she got the bonus, but I bet that bitch had something to do with it."

One of the executives came through the office and we both got back to our work. There were always office rumors, and now that I'd experienced what Helen could get up to I wasn't so sure that the rumors weren't necessarily true! I couldn't concentrate much that afternoon, and when five o clock finally came around I picked up my notepad and pen and walked to Helen's office. Taking a deep breath I stood outside and knocked on the door.

"Come in," said Helen, "Ahhh, good it's you."

I smiled and Helen gestured towards a chair on the other side of the table. I closed the door and took a seat while Helen's eyes didn't leave me. She continued to study me intently as I sat waiting for her to speak.

"I honestly never would have believed it if I hadn't seen it myself Jack," she said shaking her head, "or do you prefer Rachel?"

I laughed nervously in response and waited for something to happen. Helen paused for a moment as if considering me before continuing.

"Well,it looks like we'll be seeing more of each other for the next day or so," she said with a mischievous glint in her eye.

"Yes, I heard. Where are we going?"

"Just to some boring conference center out of town I'm afraid," Helen said, "but on the up side I've got you all to myself rather than one of those moody cows from the typing pool! Honestly, you have one innocent fling with a temp and they all get uppity around me!"

"So it is true!?" I gasped.

"Sure is Hun," she said, "In fact I've still got a pair of that silly tart's knickers in one of my drawers somewhere."

She pulled out a drawer from behind the desk and fished out a skimpy white lacy thong, followed by a matching bra and a pair of hold up stockings. The thong looked worn and crumpled, and one of the stockings was heavily laddered. The other stocking was tied in a loose knot, which she absentmindedly untied while continuing to talk to me.

"Oooh, I forgot about these though," she remarked, "Mmmm, these brings back some nice memories. Right here on my desk..."

She seemed to gaze dreamily towards the wall for a few moments, before she turned her attention back to me and started to break into a crooked smile that made me feel rather uncomfortable.

"Yes, there's a thought... OK, put these on please," she demanded.

Shocked at the sudden change of direction, I thought I hadn't heard her right. I nervously looked over my shoulder and could still hear the bustle of workers leaving the office.

"W..what?" I stammered.

"I don't need to remind you that your secret is only as safe as long as my patience can last?"

"But, there's still people in the office," I begged, "Someone might see."

"Well, that didn't stop you last week did it honey?" she chided, "You were quite happy to get all dressed up in the ladies loo. Listen, the quicker you get dressed the less chance you'll get caught."

I could tell that she wasn't joking, and again I didn't seem to have much choice. Secretly I was getting excited at the thrill of knowing some of my workmates were in the next room still as I nervously got up and started to undress. Helen leaned back in her chair with a satisfied smirk on her face watching me strip off. I stood up and slipped off my shoes and socks before letting my trousers drop to the floor. Helen was clearly enjoying my nervous excitement and was starting to squirm a little in her seat. Feeling curiously shy I turned around to remove my underpants before replacing them with the lacy thong.

"Mmm, that looks good honey," said Helen, "Take off your shirt and bend over for me sweetie."

I was now feeling quite turned on with Helen directing me as her personal toy. I still could hear the gentle buzz of an office closing down on the other side of the office wall that I was now facing dressed in Helen's last office conquest's used panties! I now obediently removed my shirt and bent over the chair I had been sat in, grabbing hold of the armrests and pushing my pantie clad butt up into the air.

"You have such great legs and a cute little arse babe," said Helen, "I just want to eat you all up! Now be a good girl and put on the rest for me."

Eagerly I slipped on the matching bra and then with one foot up on the chair, slipped on the silky stockings, enjoying the familiar smooth feeling as the glided over my skin. All this excitement had got my heart pounding and my cock swelling in these panties. I reached out again for my trousers, assuming that she wanted me to wear them home and tomorrow on our trip.

"No," commanded Helen, "just sit down and let me take a look at you."

I sat back down and tried to conceal my bulge by crossing my legs.

"Aww, poor slut has got a naughty secret in her panties!" teased Helen.

I blushed crimson, and tried to avoid her gaze.

"Please Helen, can I get dressed now?" I begged.

"Not just yet honey. Let's see your hard clit", she said, "you can get dressed as soon as you come for me."

"Please..?" I begged.

"You're really only wasting time bitch!" she snapped, "Imagine what Lucy and the other girls would say if she walked through that door right now. They'd think you're such a dirty little boy! And I'd tell them all how shocked I was when you stripped off in front of me and my disgust at finding you wearing ladies underwear! Who would they believe, an office tea boy, or a managing executive? So the sooner you behave the sooner you can get dressed. OK?"

"Yes Helen," I murmured in response.

"Good girl," she said, "Now let's see you properly."

I toyed with the idea of disobeying her, but realized that I was still in her debt and had little choice. Casting another nervous glance towards the door I slipped out my cock along the edge of the tiny panties and let it hang there semi erect.

"Aww, how cute." said Helen, "maybe this will help you a little?"

She pulled open one of her drawers again and this time pulled out a dildo. It was pale blue, rubbery in texture, and was obviously curved and ridged to access sensitive parts. She briefly showed it to me before opening her red lips and licking around the tip of it. She then slipped into her mouth and sucked deeply and hungrily on it leaving a trace of red lipstick along the length of it. My cock twitched in response and instinctively I reached for it and started to stroke myself. Helen took the dildo out of her mouth and smiled, pleased at the effect she'd had. She reached below the desk out of my view and clearly was contorting herself to allow access for the toy. Still playing with myself I watched as her eyes rolled back slightly as she pushed the it firmly home.

"Mmmmmmm, that feels so good," she moaned, "This is my favorite vibrator you know. The curve means I can hold it in even if I'm standing. No one would ever realize I had it in. I've even taken it to meetings before!" she smirked, "And this is the best bit.."

She placed a small silver key fob on the desk. It had a four buttons on it, and when she pressed one and started to writhe and gyrate her hips I realized it must be a remote control vibrator. I watched as she got more and more turned on before my eyes, all the time jerking my cock in front of her desk.

"Mmmm, yeah baby, your clit looks so good."

She had leaned forward and was obviously enjoying grinding the end of the toy into her chair seat. She pressed the buttons again, which caused her to arch her back and rear up in the chair before falling forward over her desk and appear to be riding her chair by rocking her hips. Her free left hand had reached across for her full right boob and was squeezing it through the white cotton blouse. Her nipples were already clearly erect through the cotton, and she was starting to flush with color at her open collar. She looked up at me with animal desire.

"C'mon slut, spray that cum for me. Stand up so I can see you better."

I obediently stood up with my hard 8 inches now jutting out aggressively out of these panties, still pounding away while I watched my boss pleasuring herself in front of me.

"That looks delicious honey, bring it over here for me."

Taking a step forward I leaned over the front of the desk towards the leaning Helen

"No, you'll have to get on the desk," she panted.

Now too carried away with the activity to worry about my colleagues in the office next door, I eagerly got up onto my boss's desk and knelt in front of her. She propped herself up on elbows with her hands flat on the desk in front of her. She was still leaning over her side of the desk, rhythmically rocking and thrusting on her toy in her seat. By spreading my knees wide around her hands and pushing my hips up towards her I was able to position my throbbing cock perfectly for her. She eagerly devoured it, taking as much as she could in one go and sucking hard. It was as great as I remembered from last Friday, and clearly the whole scene was pleasing Helen as she seemed to be getting more frantic. I was getting pretty close myself and by the way Helen was gasping around my cock I could tell she was on the edge. She snatched at the remote once more and repeatedly punched at the buttons as she shuddered to a climax in front of me, ended up in a contorted tense position with her mouth still clamped around my cock. After a brief pause as I watched her eye lids flutter, she resumed her oral attentions to my hard cock.

I was now so very close to coming, and was bucking my hips to meet Helen's mouth on each dip along the length of my cock. I had to put one arm out behind me to relieve the pain in my tiring thighs, but couldn't stop - not yet. Helen had moved her right arm and reached down under the table to pull out her vibrator. I watched with fascination as the toy appeared again over the table edge slick with her fresh juices. My fascination turned to panic as Helen moved the toy between my thighs and started to position it between my spread ass cheeks. My eyes grew wide and instinctively I made to move away and pull out of Helen's mouth. She looked up at me with a determined glint in her eyes and bit gently into my cock. The threat was clear - you're mine, do as you're told or else. She bit harder to make her point and continued probing my butt with the toy. The toy was not huge, but I was not used to regular anal action so had to concentrate on relaxing to allow the ridged tip to pop inside me. The pain of the stretch was quickly replaced by the feeling of pleasure of getting filled by this toy. Helen resumed her oral attentions, keeping me in her warm mouth while swirling her tongue around the tip of my cock. At the same time she pushed a little harder on the toy and more slipped inside. I could feel the curve of the toy pushing inside me and the ridges were something different that I hadn't felt before.

"Mmmmmmmm, that feels so good," I moaned.

Helen looked up at me clearly satisfied with abusing me like this and continued to give glorious head. I started bucking my hips again, which caused the toy Helen was holding in my ass to move and rub at different points. It felt delicious and I quickly was working up to a frantic orgasm. Suddenly I felt the toy start to buzz powerfully inside me - Helen must have pressed the remote, and I felt as if I would pass out. The intensity of the vibrations was incredible and the sudden shock of feeling the toy moving within me made me instantly come, releasing spurt after spurt deep into Helen's waiting throat. As I continued twitching unable to move Helen sucked my deflating cock clean and pulled out the toy. I collapsed back onto my heels and then slumped forward onto the desk in a heap. Helen sniggered at the effect she'd had on me.

"You liked that then, my little slut?" she cooed, "Come here then."

She leaned in towards me and kissed me deeply. I could clearly taste my own sticky cum on her tongue. She pulled out some tissues from her desk, wrapped up the toy and put it back in her drawer. She closed her eyes for a moment and when she opened them again seemed like a different person.

"OK then Rachel," she said, once again more business like, "you may keep these underwear, but I want yours in exchange. Keep them on now and get dressed."

I groggily slid off the table and got dressed back into my trousers, shirt and jumper as if in a daze. Finally I handed over my socks and underpants to Helen.

"Spoils of war," she smirked, taking them and placing them in her desk drawer.

"see you tomorrow 9am sharp."

I left with the same feeling of guilty pleasure at being used by Helen, but I knew I wouldn't tell anyone about it. I was already looking forward to tomorrow and our few days on the road meeting clients.

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