My Life as a Secretary

We returned to my room and Charlie helped me dress for my debut at the club. I showered then sat at the vanity as she did my hair, she suggested a high ponytail, I liked what I saw as she held my hair in her hands and nodded, then she applied some product which she assured me would keep me looking great in the heat and humidity of the dance floor.

Makeup, foundation, concealer, blush, a little waterproof mascara, eyeliner, lipstick, lip liner. She stood back and I turned to see myself in the mirror, "Wow Charlie, I look hot."

She kissed my cheek, "You always did Ger."

She went through my closet, she picked out a beige knee high low hem skirt and paired it with a white round neck sleeveless top. She picked a Calvin Klein three-quarter sleeve bolero cardigan rather than a jacket and handed me a pair of high-heeled strappy sandals to round the outfit off.

I picked out my Pandora ring, necklace, and bracelet then turned to look at myself once again in the mirror.

"Thanks, Charlie, thank you so much."

She kissed me on the cheek again, "Don't cry and ruin your makeup." We took a few selfies, then hand and in hand made our way downstairs to get the shuttle to the club.

At first, I only danced with Charlie and the other girls, mostly in a group, Charlie danced with a few guys, it looked like she was having fun with them but I was too nervous to put myself out there just yet.

I had been dancing with a couple of the other girls, when I felt a very light touch on the back of my shoulder, Charlie gave me a subtle thumbs up as I turned around, his was name was Tom and he was to become the first guy I ever danced with.

Tom was tall, red hair and a well-trimmed beard, he looked like an archetypal Celtic Warrior, ruggedly handsome, out on a raid to slay his enemies, loot their possessions and take their woman.

"You're nervous," he said, "it's not me, is it? I don't bite, well at least, not until I'm asked to."

We weren't touching but dancing closely enough that we could hear each other if we spoke up a little. I laughed along with him, damn it, I did sound nervous.

"New job," I said, "first night with the girls, can't make a fool of myself."

When the dance ended he excused himself politely, and went to get a drink, I watched as his made his way up the stairs, he had a really nice ass.

"So?" Charlie asked when I sat down.

"Nice guy," I said.

"Is he coming back?"

I didn't say anything, she just cuddled me and laughed happily in my ear.

I danced with a couple more guys, and if not totally comfortable with things yet, I wasn't as self-conscious as I had been at the start of the night either.

I saw Tom making his way back to our table, a handful of bottles of water in his hands, he put one on the table before each of us, pausing only to crack the seal on each, then when his hands were clear he looked at me and reached over, "Dance?"

He led me out to the dance floor, a beat came on, damn I knew this song, salsa rhythm, I didn't know what to do. He turned me around, and pressed himself into my back, he held each of my hands and his body poured a gentle rhythm into me as we began to sway together.

"I don't know how to do this," I mouthed to him.

"Relax, just follow me."

I closed my eyes, all I could feel was his body close to mine, and the beat of the song, we started to move a little faster, I decided to trust him, and let him move me around our small space on the dance floor.

The beat was picking up, "Despacito, quiero respirar tu cuello despacito," I moved with him, his hands covered my body, I pushed my ass back into his groin, our movements were close to full-on simulation, the song continued for a few minutes, but I was lost in new feelings and emotions, it could have lasted for half an hour for all I knew.

The song finished and I was facing him now, he pulled into his arms and kissed me on the lips, very softly, then led me back to our table.

"So?" Charlie said again.

I laughed, "Nice guy."

The girls at the table held their water bottles up to toast me, it was another new and warm feeling for me to experience, I'd never really been part of a group before.

Another of the girls, Josie, leaned over, "You were hot out there girl, you've got some moves."

I pretended thirst and held my water bottle to my lips as I blushed.

Tom danced with me another couple of times that night, although nothing was quite as sexy as our Salsa routine, he left with my number, the genuine one, not the fake we all memorized, typed into his cell phone.

We got on the bus back to the hostel, I couldn't help myself I was softly singing the few word I knew to Despacito, Charlie heard me and joined in, soon the whole bus had joined us, everyone smiling at me, this time I didn't blush.

Office life.

The girls in the office told me I was being noticed, my name was being asked for, I was very flattered, but I wasn't really ready for too much attention yet.

I could hit the eighty words per minute in shorthand and typing speeds, but I was still frequently at one hundred and ten to one fifteen word P/M on the steno machine, just below the exacting requirements which would free me from confines of the pool.

We had tested all our toys to varying degrees of satisfaction, Charlie's favorite was the bullet, mine was the lifelike cock. I had been trying to persuade Charlie to wear the butterfly vibrator for weeks with no success, "Pass your steno test," she told me, "then we can think about it."

With that incentive, I knew it wouldn't be too long until I was ready, and I was still worried about one thing. I approached Charlie at lunch one day, "How will guys know what I really am Charlie?

"I don't want one thinking he's going to get one thing, and then this all falls apart because he's angry when he finds out I'm something else."

Dave was sitting beside her, he knew about me, and he knew about me and Charlie and he had told us he had no problem with our relationship, as far as he was concerned I was one hundred percent female.

"Don't worry Ger, if the wrong type of fellow is showing an interest in you, one of the senior executive will explain things to him, that type of situation has been handled before."

He squeezed Charlie legs below the table "Got to rush," he said, "tonight?"

"Not tonight hon, I think Ger and I need a little alone time if that's OK?"

He didn't sound too disappointed as he told her "Sure," then rushed off.

It was on the way back from lunch that I received my first genuine piece of sexual harassment, the elevator was crowded as it rose from the ground floor, our bodies all squeezed tightly together in the confined space. I felt a hand move softly over the rounded mounds of my ass, in the Mirror I could see one of the very senior executives standing behind me.

The elevator stopped at the fifth floor, 'Excuse me miss," he said from behind, I squeezed to the side, and his right hand helped itself to a final soft grope as he squeezed passed me.

"Who's that?" I whispered to Charlie.

"Mr. Stevens, he's in charge of acquisitions, very powerful, sits on the board."

"He just groped me."

"Welcome to the jungle Ger, he's groped every one of us, wait until it's your turn to take his dictation."

I must have looked worried.

"Don't worry?" she said, "a little touching, but mostly he just likes to look."

My education was advancing on all fronts.

Charlie on top.

We were standing in Charlie's bedroom, wearing matching pale blue silk teddies, and thong underwear, Charlie tuned her radio onto the Spanish Channel, and I smiled as she pulled me close to dance around her room.

We made love with the music playing, after we had come, Charlie went into the bathroom to clean up, she called to me through the open door.

"I signed for a package today."

"Oh," I said, "for me."

"I think we could say it was for you, yes," she came out wearing the strap-on I had purchased a few weeks ago, a latex replica of my own cock, erect and proud, "I think it's time I fucked you, honey."

I nodded and she went to lube the latex cock.

"What no foreplay?" I continued to tease her, "Wham, bam, thank you, ma'am, really?"

I was kidding her but the look she gave me was a little worried and confused, I got up kissed her then pulled her down onto the bed with me.

I instructed her in fingering my hole, getting me ready to take her cock, this had been done to me plenty of time before and I had always enjoyed it, but Charlies' fingers were special, and I came before she had me close to ready.

I told her not to stop and her fingers vigorously continued their work, I knew by the feel of them inside me that I was properly prepped now and my cock was fully hard again, so I positioned myself in front of her, head on her pillow, back angled up at 45 degrees, with my ass presented to her ready for sex.

She knelt behind me, this was her first time in the guy's role and she rushed things, she went to push into me too quickly and missed the target, the head of the cock struck forcefully between my balls and my hole and I winced with the pain.

I put my hand underneath, found the cock and guided it in for her, she grasped my hips as she pushed deeper, then drew back, pushing further in until her hips covered mine, squeezing the globes of my ass as her thrusts became more confident.

She leaned forward to whisper in my ear.

"I can see the end of my cock at the edge of your asshole, I can see you asshole pulse around it, welcoming it inside, I think it's the prettiest sight I ever saw."

It took her a little while to get used to the strap-on, and I had to guide her back in a few times, but after she got the hang of it we were a pair of well fucked exhausted girls.

"Is it good?" She asked me, "Anal?"

"It is," I told her, "I like to be fucked just as much as I like to fuck, they are entirely different sensations, and my mood during them, who I am during them, is entirely different, but my orgasms are equally intense either way."

"Girls like me, are given the choice of one thing we don't want to do when we sign up with Ms. Graham."

She was cuddling me, she hadn't taken the strap-on off, and as she breathed, it lightly brushed against my thighs.

"The thought of anal scared me, so that's what I chose."

"I don't remember being given that choice," I complained.

"It's a little different Ger.

"Anyway, I'm still a virgin in that way, but I'm considering it, and if I decide to go for it, I want you to be my first."

"What about Dave?" I asked.

"He's not here tonight," she growled, "even if he was, I love him, but I love you more, it's my choice and I choose you."

I kissed her, "Thanks, Charlie, but not tonight, it would hurt you too much and you wouldn't enjoy the experience.

"You need to be stretched, made ready, and it takes a bit of time, we'll speak to Ms. Graham tomorrow."

She was anxious, "I don't want to be trained, you get to fuck me in the ass, I might even let Dave do it, but no one else, not Ms. Graham, not James, I want it to be available only to you."

We made an appointment to see Ms. Graham the next morning, she understood perfectly and chided Charlie for being so nervous, she knew she could never be forced to do something that she didn't want to.

I stood holding her panties as she bent over the table, Ms. Graham told her to take a deep breath then slipped the small butt plug inside her. She looked at Charlie, "Four to Six weeks, I'll let you know when."

I handed Charlie's panties back to her, she got dressed and we left.

"It's a little strange," she told me.

"It gets better, honestly," I took her hand and we went back to her room to make love.

My new instructor.

I entered Ms. Graham's study to find Mr. Philips from HR sitting on the couch, he was buck naked, and Ms. Graham, dressed in just her panties was kneeling before him, sucking on his cock. I began to undress but a motion of his hand stopped me, he was looking into my eyes and I knew the exact moment his first shot of spunk flew out of the eye of his cock to fill Ms. Graham's mouth.

She rose and cleaned her lips with a tissue, then sat beside him on the couch, "Mr. Philips has kindly agreed to be your further education instructor, there's only so much I can do with the strap-on dear, you need to work with a real cock inside you too."

I nodded, "Thank you, sir."

I looked at him, he was older, certainly into his late forties, maybe even his early fifties, but he was well muscled and showed very little fat. His skin was an even tone across his entire body, he obviously sunbathed nude. On his chest were two tattoos, I didn't recognize the script, not Asian, maybe Indian and then there was his cock. It had remained erect after he had cum, he was uncircumcised, but the foreskin had rolled back under the edge of the hood leaving the purple head fully exposed. It wasn't particularly long, six maybe seven inches, but it was thick.

I had a revelation, I didn't like his cock, there was something off-putting about it, James' cock, on the other hand, was the prettiest I had ever seen, my own included. I'd thought cocks were just cocks, sure shape and size would differ from guy to guy, but I never thought I'd be judging a cock as good or bad to look at. No that wasn't fair, it wasn't ugly, it just wasn't pretty.

He didn't verbally respond, he rose from the seat and walked around me, inspecting me, his hand removed the loop of my dress from my left shoulder then my right, I shimmied and it fell to the floor, he was behind me, his hands lightly feeling my ass under my panties, I spread my legs and his finger played casually with the inside of my thighs, he kissed my neck, his hands played with my nipples for just a moment before they slid into my panties and released my erect cock.

"Nice," he said, as he worked my cock he slid my panties down to my thighs, I unhooked my bra and let it fall to the floor, he pulled me towards the bed my panties still around my things, lifted me up onto my back, with my legs dangling over the end, he pulled my panties all the way down to my ankles, then stepped over and inside the gap that was formed, "Keep your panties at your ankles, don't let them fall off, but don't stretch the elastic of the waistband, do you understand?"

"Yes sir," I said, my legs were spread but his request had forced them into a diamond shape rather than wide, he leaned over and kissed me, his hand still working my cock, then I felt the head of his cock slip inside me.

I thought I knew what fucking was, but two hours with Mr. Philips changed my mind, he left me spent, panting at his feet, as I slid off his cock for the final time that night. He insisted that I didn't hold any orgasm back during our first session, and I lost count of how many I had, he didn't hold back either, and my ass and mouth had both received full loads, I was covered in both our spunk mixed with our sweat, I was like a filly after a one mile race, I needed a good rub down and some sleep. He might not have the prettiest cock in the world, but he knew how to use it and he had easily battered me into submission to with it.

He turned to Ms. Graham, "You've done a good job, Emily, he's fairly advanced." It was like drawing fingernails down a blackboard, I hadn't been addressed using the male pronoun for nearly a year now.

"I think maybe only a half dozen session or so will be needed to round him off, and I'd say he's already ready to start dating if you give him permission."

I lay on the bed as he got dressed, kissed Ms. Graham on the cheek, "Let him have a rest for three days then schedule our next session." He reached into his coat pocket and removed a DVD, "have him watch this all the way through at least once a day beforehand" Then without so much as a look my way, he left.

Ms. Graham joined me on the bed, "did you enjoy that Geraldine?"

"Oh yes miss." She handed me the DVD, "I will have a player and TV put in your room tonight, watch this before bed each night."

She had another present for me, falsies which adhered to my body rather than filled a bra, they were a very close match to my tanned skin tone and would stay in place for a least a month, I stood and bounced up and down, they jiggled and I giggled.

My DVD was an instructional video on Gay Sex, labeled positions one through ten, Mr. Philips fucked a different man in each position, it wasn't exactly porn, it wasn't exactly sexy either, it was educational, he addressed the camera as much as he addressed his fuckee as he gave details on what to do, what to say, how to react, to give your paratner maximum pleasure. I watched and listened and learned.

Continuation.

I spent my days honing my secretarial skills, I had been allowed to scribe a few meetings with one of the senior girls sitting beside me monitoring my progress. We would transcribe our shorthand notes into typed minutes and then compare the results. I didn't make too many errors, and my weekly reviews were all positive.

I mirrored senior girls taking individual dictation for managers and executives, this wasn't so much to show me the skills and deportment necessary, I was already well enough acquainted with them, but to show me off to various people in the company hierarchy, some of whom might be interested in dating me later.

I spent my nights honing my other skills, Mr. Philips had taken me through the minimum positions he considered a good lover needed to know, all of our sessions were as rigorous as the first, and I ended up exhausted every time. While I still lay panting on the bed at the end of each time, now I was mostly just covered in sweat, he was teaching me to hold back my orgasm and come on command, each of us came only once at the end of the session, but we did so simultaneously.

I put his last DVD into the player, "Essentials of dominance and submission." I wasn't sure about that, I was also a little worried about Charlie, we didn't get to spend much time together now, and we had even less time for sex. I didn't want to worry her, so I approached Ms. Graham.

"Do you remember our discussion when we set you down this path Geraldine," I nodded, "well this is an inevitable part of it. Caroline and David are courting, this is a very important moment for both of them, they will soon decide to marry."

"So quickly," I asked.

"I know my girls, and I know their gentleman, David will ask her soon, she will say yes. It's a happy time, for all three of you, if you think about it."

I did, and she was right, Charlie, Dave and I still had to decide the exact parameters of our long-term relationship in detail, but at the moment, I'd need to sacrifice a little immediate pleasure for many more night in the future.

Ms. Grahams said I was ready to date, she sat me down and explained that once it was known I was on the market, I was probably going to be more in demand than the other girls because of my special circumstance. Sometimes this made the 'real' girls jealous, I should let her know if it got to the stage where I couldn't handle it, but she didn't expect any problems in our current group.

She told me to enjoy the process, don't fall head over heels with the first guy, but don't let every guy into my bed, I was looking to broaden my experience, but I still wanted to have only a few lovers when I walked down the aisle.

My first date.

I told Charlie, Charlie told Dave and we set our first double date. Of course I knew it would be with Jack, at Charlie's insistence I wore my highest heels, a classical thigh high little black dress which exposed just enough cleavage, and even though I knew he wouldn't get the opportunity to see it, I had a very sexy black lace corset which shaped my body nicely underneath it with matching panties and sheer lace stockings.