tagTranssexuals & CrossdressersImportant Business Comes Up Ch. 02

Important Business Comes Up Ch. 02

byEmmcee20©

In the opening chapter of this story Jason Meadows has arisen to the level of Vice President in an advertising agency and immediately become the target of office predator Dana Jones. She quickly discovers his interest in wearing lingerie under his business suit and, after an initial meeting, invites Jason to her house for further discussions about his new account amongst other things.

It was difficult to focus on work for the remainder of the afternoon. Alison, my secretary, came into the office several times to bring in coffee, notes, etc. Each time she was on the verge of saying something but didn't. Finally I asked her what was bothering her and she said she did not entirely trust Ms Jones.

"She seems to be a very aggressive woman and she has caused some people's jobs to be lost. I think she takes advantage of people. I'd hate to see something bad happen to you Mr Meadows."

It was the first personal conversation we'd had and suddenly I saw her in a new light; not just the ever-efficient secretary who seemed to know where everything is or should be, but also a caring co-worker. I considered for the first time that beneath the subdued business attire there was a rather attractive woman in her early thirties. She had only been my secretary for a matter of days but it seemed that we would be able to work well together. I assured her that I was intending to be here a while and that I appreciated her concern. It was interesting how she smiled so broadly at the thought of me being her boss for a while. She didn't seem to need the reassurance; she was so well organised and capable. I was already sure that I could trust her with any business matters.

The afternoon dragged by while I tried to imagine what the evening held in store for me once I got to Dana's place, her domain. I guess I was taking a pretty big risk but having already caught me in stockings and panties and performing oral sex on each other earlier in the day, I didn't really see that I had much choice. She had me over a barrel and I would just have to see how it all worked out. Having thought that, I was very excited to find someone who was accepting of the foibles of my sex life -- it had been some while since anyone else had known and been of any help in that area.

Finally the day was done and, with her address lodged firmly in my mind, I went home to prepare for the evening and arrival at her place by 7 p.m. After a shower and all over shave, I dressed for the evening in some of my favourite items. There was no point in being shy now! And then I found a pair of trousers and one of my favourite satin shirts to wear. I was ready and the evening was about to begin.

I drove my small sports car out to the suburbs and into one of the more luxurious areas. Finding the address was not difficult and I was soon turning in to Dana's driveway. A dozen butterflies were dancing in my stomach as I wondered exactly what this evening held firmly in its grasp and what this meant for my future both in my personal life and at work. I stopped the car and looked at the two-storey modern mansion with a wide set of steps leading to stained glass double entry doors. It oozed luxury from every feature and the soft, warm lights behind the closed drapes at several windows gently shone over the manicured gardens. I was fairly sure that Dana had someone come in to do the gardens; she didn't seem the hands on dirt type ... at least not that sort of dirt. It was just what I had imagined Dana's house would be like.

I walked up the steps, butterflies doing the rumba now, and rang the bell. Silence. Then the faint but increasing sound of clicking of heels on a hard floor and then the door swung open. There was Dana, tall and elegant in a silky red dress and matching pumps, her beautifully full breasts pushed hard against the soft material to reveal that they were unfettered by any underwear.

She smiled, "Good evening Jason. Right on time -- that's what I like to see. Someone who cares about the little things. Do come in."

"Thank you Dana," I muttered as I stepped over the threshold in more ways than one. I was now in her home and about to see how my future would be with her and at work.

The entry was spacious and open with several rooms leading from it and a staircase to the upper floor. All of it said style and comfort. Dana certainly knew how to look after herself. I walked in and she closed the door behind me. She turned and gestured to one of the rooms and, placing her hand on my backside she caressed me while making small talk as she ushered me into a large and comfortable softly-lit lounge room. Dana steered me toward a high-backed soft velour covered sofa. On the coffee table beside it was an ice bucket with a bottle of wine and a couple of stemmed crystal glasses together with a platter of finger food.

"Take a seat and relax," she commented, I guess noticing the butterflies in my manner.

We were soon chatting about all sorts of things. We had wine with a little of the food and there was soft music playing from the wall-mounted speakers though there didn't appear to be a sound system. We finally actually had a conversation. As a junior member of staff she had barely noticed me. Now that I was promoted, and on the board, Dana was prepared to chat ... amongst other things. At the moment, however, she seemed genuinely interested in just talking to me -- as a person. It was as if our 'little meeting' this afternoon hadn't happened.

We covered all sorts of topics and she had a very happy knack of making the conversation flow so that I suddenly realised she had learned a great deal about me with me only managing to find out only a few things about her. She was the eldest of two sisters who had grown up as competitors for everything. Only 18 months apart in age, they had fought for best grades, awards and of course boyfriends. Her university years got her into business and advertising and her open desire for fun. She laughed as she told me of a guy in her boarding college who was caught stealing the girls' underwear and how the idea of crossdressing had intrigued her rather than shocked. He, of course, was run out of college by the rumour mill rather than any formal punishment.

Dana leaned forward to refill my glass as she finally asked, "How long I have you been wearing women's underwear Jason?"

Despite all the relaxing chat preceding this, the question came with rather blunt overtones and stirred up the butterflies again. It was obvious that I had to tell her so I began. I explained how I was the youngest of four kids and the only boy. My step-sisters appeared on the scene when I was about 6 when their father had married my mother. She had divorced my father who had disappeared years earlier; I never really knew him and had grown up with just mum. Their mother had passed away after a long illness and our parents just hit it off. The girls were great fun to be with and they spoilt me and always looked after me. We used to play dress ups as kids and I was always the 'doll' or model for my three sisters who put me in their clothes and make-up and did my hair. Occasionally they used the 'dress-up' box which had all sorts of discarded clothes and underwear and wigs. This had all gone on until I was about 12 or 13; I guess puberty started me realising what was happening but also, by then, my two older sisters, Joanne and Glenda, had moved out to university and work. That left me at home with just my step-sister Sarah who is a few years older than me.

Later, as I got into cross-dressing and using the old dress-up box myself, I wondered whether or not there had been any sexual element in their play. The more I thought of it, the more certain I was that they had been having their own fun with me when I was too young to know about it. It was around about when I reached 15 or 16 that I started to explore the 'being their doll' idea when they weren't around -- I used to get home from school and, while I was alone in the house, I would sneak into their rooms and borrow some clothes -- mum had kept the girls' rooms ready in case they wanted to stay so they had left some clothes behind. Very convenient for me but also not their best 'dress up' things. I simply had to find a source of new things to wear. My other sister was of some help there but I was scared of being caught. After all, who else could it be if her stuff went missing or turned up stained?

I explained to Dana how my suspicions about being their toy had been confirmed when I had just turned 19 and my sister Sarah was about 22. Sarah was cute by any guy's standards and had often been ogled by my school friends when they came over. She was tall, 5' 9" maybe 9½" just like my other sisters, though I was taller, and she had long dark hair that fell to halfway down her back and model looks. All three sisters had the most beautiful sparkling blue eyes. Her long legs were stunning and her body shapely with her B cup boobs. It was no wonder that her underwear had fitted me quite well.

She introduced me to a friend of hers. Her friend Jody was gorgeous and we seemed to hit it off pretty well. She was about 5' 6" with what you would probably call an athletic build except for her very nice, very round D cup breasts that sat very prominently above her trim waist with even more prominent pointy nipples that showed through the stretched material of anything she wore. She seemed to like the more figure hugging style of clothes and, in fairness, she had a lot to show off to a guy. Any time she was around it was hard not to notice her wonderful assets and, of course, my mind bent to thinking about the type of bra she must have on to hold those beautiful boobs so firmly in place.

She was in the same art classes as Sarah at university and so she'd been to our house plenty of times, though I knew she had a place of her own. I'd known her a few months when Sarah invited me to a party at Jody's place one weekend saying I should go, it would be fun and Jody wanted me to come. When we got there it seemed pretty quiet. We went in and there was Jody in a silky blouse and jeans. Her bra showed clearly through the material and again I thought how much she must love showing off to guys or, perhaps, just me. She came over and kissed us both hello. I thought the kiss on the lips she gave Sarah was a bit odd but then the kiss she gave me was clearly more than a friendly peck as she sucked gently on my lips and held the kiss for a few seconds, sexily flicking her tongue across my lips. I'd had my share of girlfriends by then and we'd kissed and fondled but this kiss was sexy as hell. She looked very directly into my eyes as she pulled away but kept her hand on my arm, keeping that initial physical contact burning.

She steered me into the house and we sat down and Sarah organised a drink. We three were the only ones present so, unless the party was starting later, there was something going on. It was now time to be told why I was really here. It seems my sister is gay -- well bi really. Jody is her girlfriend and I was so dumb as to have never worked it out despite all the years of her friends coming over and she'd never dated a guy that I could remember for more than a couple of outings. And here I was thinking Jody was showing off to me when in fact it was for Sarah's benefit.

Sarah then explained how she had told Jody about our kids' games and Jody was interested in trying it out if I didn't mind. Well here was this stunning woman who wanted me to get into her panties literally!

Sarah quite openly explained, "I really miss the fun we used to have with Joanne and Glenda. It was always fun seeing your thick cock get hard when we put our silky undies on you and stroked and patted you. Sometimes you'd have an accident and spurt into our panties."

They had always been so understanding and said that it was something that happened to all boys. Of course that was true -- any guy having three gorgeous girls play with them would agree. I couldn't believe what I heard my sister saying. That didn't stop this sudden series of revelations just about blowing my mind and embarrassing but exciting me.

Sarah continued, "Jody wants to try it and, if you don't mind, then we should just have some fun and see what comes up." My sister wasn't subtle but the lump in my jeans told them that I was up for it! It was Sarah now who reached across and kissed me and then said, "Thanks Jace."

God this was my sister but boy could her tongue do things to your tonsils. The early days of our games were still in my memory and I had jerked off to those images many, many times! She started by explaining, "We will pamper and dress you just like we used to. All you have to do is enjoy! If anything feels too weird just say so and we'll stop."

Somewhere in my head there was a fleeting thought that 'weird' had passed years ago when she had me wearing her make-up, bra and panties -- now she was sharing me with her girlfriend. Quite quickly after this I felt their hands on my clothes. Boy, were they in for a surprise? When my jeans went down I was already wearing some lace and satin panties. I pretty well always did, having acquired a few of their old pairs and more recently bought some through mail order on line, and I hadn't gone out to this party expecting any chance of getting lucky so there was little danger of getting caught, or so I thought.

They squealed like little girls when they saw the lace-trimmed blue satin and both immediately started fondling. Soon my shoes, socks jeans and shirt were gone and they took me by the hand and led me upstairs to the bathroom. It was all decked out with soft candles and perfumes. Sarah ran a bath while Jody took my panties off and started to massage my body. My erection was aching hard at its full slightly curved 6 inches and rock hard but they avoided touching it any more. Then I got into the oiled warm water and it was wonderful. They both knelt by the bath and commenced washing me all over with soft cloths. Sarah paid close attention to my face and chest, stroking the cloth across my hard nipples and brushing them with her hand. She whispered, "Jody, look at his lovely nipples!"

They have always been super sensitive and this action had them rigid and looking for attention and her comment made the water ripple as my cock twitched. Jody washed my legs in long strokes up to my groin and then she asked me to stand in the bath. I did and she continued washing being very thorough around my puckered hole and balls but still avoiding my cock.

"We want to do this properly Jason. We want to shave your legs. Is that okay?" Like I could have said much at this time. I meekly nodded.

I stepped out of the bath and stood in the warm, sensual atmosphere. They used fluffy soft towels to pat me dry and then lathered up some soap and spread it up my legs and commenced to shave from my toes to my upper thighs; their long sensual strokes of the razor vitalised my skin as the downy hairs disappeared. I was soon hairless. They stroked my legs and it felt fantastic and I briefly went off into a world of silky stockings and suspenders, wondering how they would feel on my bare legs. I'd never shaved my legs before but had always loved the feel of stockings and, in fact, I had several pairs in my secret stash at home.

Next it was under my arms and my chest. I was apprehensive but it felt great. In not too long I was body-hair free except my crotch. Then Jody said that it was time that I was relieved of my unsightly thatch and she took a small pair of scissors and started to trim my crotch to a nice neat patch. Sarah helped by holding my cock out of the way of the scissors. Her hand gently stroking me as she moved my pulsing member to another position. She then took the safety razor and some soap and lathered my cock and took off the hairs that grew along its broad shaft and also gave me a nice neat panty line. Cock juice had been flowing for a long while and made things sticky but aromatic. Finally, my reward. Sarah took a warm towel and, from where she was squatting in front of me, washed my cock and balls clean and then leaned forward, opened her mouth and took my cock into her hot mouth, wrapped her lips around my shaft and slowly sucked me deeper. Her hot breath tantalised my shaft as she withdrew and then sucked me back into her throat. Sarah ran her long fingernails along the underside of my cock to massage, scratch and tickle my balls that occasionally bumped her chin as she took me deeply. She switched her gaze from her mouthful of my penis to a deep stare into my eyes as she let out a soft moan of pleasure.

Jody stood up and played with my nipples which jumped to attention as she caressed them. My sensitive areolae dimpled and hardened under the stroking pressure and gentle pulling; Jody commented to Sarah, "Hey Sare, his nips are just like yours ... they get so hard!" and then she leaned in and deep kissed me before leaning down to suck on my left nipple while playing with the other one.

Her comment caused Sarah to suck harder on my six-inches of cock that had again mostly disappeared into her mouth and, as her tongue swirled around and under my foreskin I could feel myself losing any hope of control. Her increasing pace had her dark mane of hair covering my nether regions and caressing my sensitive, newly-shaved legs while the heat of her mouth became a molten furnace that melted my core. I lasted for what felt like about ten seconds of this and then erupted deep in her mouth. Jody broke her lock on my titty as I grunted my release and we watched as Sarah drank down my essence. The intensity of my orgasm after all this attention and build up was gut-wrenching and I started to feel weak at the knees and had to lean forward as Jody held me close to her monumental breasts. Soon Sarah allowed my wilting cock to pop from her mouth as she looked up into my eyes again and smiled, "Thanks little brother!"

"Not so little," chuckled Jody. "Come on Jason, I think you need to sit down."

I was then led, still in a post orgasmic dream, into the bedroom and what I saw there made all of the preparations make sense. Displayed on the bed was an elegance of lingerie: a soft satin midnight-blue bra and panties set with a black suspender belt and matching sheer stockings, a dress and black patent leather shoes. I was led over to a dressing table with a large mirror and told to sit down and remain perfectly still. This was something my sisters had done to me years before so I knew the routine. In a fairly short while I was made up beautifully as a woman and my longish hair was groomed into a reasonably passable pageboy style. It was a treat to remember how my step-sisters had made me feel all those years ago and to refresh my feelings. My cock reacted, after a brief recovery period, the way it always had in the old days - it was at full attention again and every now and then received a stroke or caress. Now it was time for the clothing. Sarah explained how she had been very thorough in finding out all of my sizes from my clothes and shoes in my room at home and that she knew where I kept my feminine clothes.

"I knew you were still dressing up Jace when you left your eBay account open on your computer and I noticed the payments you'd made. Those things might come in plain packages but the account name for Jessie Meadows was the give away. Mum might believe they were things for school but I know what they really were. I just wished I'd known earlier. Think of all the fun you and I could have had since the girls left home. Joanne was always the one to get it started and I wasn't sure how you would react so I just left it ... until now," she said with a grin.

That explained why she thought I'd go for this. I continued to be the girls' mannequin as, in a matter of seconds, I was dressed in the black suspenders and I was instructed to sit on the edge of the bed so that they could draw the stockings up my legs. The silken material caressed my toes then heels and calves while they trailed their nails across my sensitive skin, one on each leg. My cock was straining under the sensations but was ignored, or so I thought. They were both concentrating so intently on their activities that it seemed that I could have been a shop-front dummy. Next the suspender clips were attached and then the bra was brought to my attention. It was almost see-through with its fine lace and, when Sarah stepped in front of me and offered it to me so that I could slip my arms through the straps, again an old habit was coming back. She arranged it across my breasts and it tingled on my nipples. She reached around me and attached the hooks, ours faces close together. The flecks of excitement in her eyes yelled her arousal at me and I knew my earlier thoughts of my sisters having their own fun with me were absolutely confirmed. She smiled as she put the bra in place and adjusted the straps so that they were taut on my shoulders and holding my small titties in place. She gently caressed the cups and my nipples reacted even more and then she stood up again.

Report Story

byEmmcee20© 2 comments/ 34122 views/ 1 favorites

Share the love

Report a Bug

Next
3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel