Important Business Comes Up Ch. 03


Having gone to Dana’s home on the evening he’d been caught out as a crossdresser, Jason explained how his sister had introduced him to going out dressed as a woman resulting in Jason’s first sexual encounter with a man. For some years he had gone back to keeping his crossdressing a secret.


Well the challenge had been set; Dana, the office man-eater, had dared me to be more adventurous in wearing my feminine attire at work. The more daring I got, the more amorous would be her response. This sounded great and would probably lead to some great sex with Dana but I also really like my job and the people I work with. The stockings she caught me in the other day was one thing, as no-one else was likely to play footsy with me under the table in a board meeting. But now she was encouraging me to be more open about my lingerie love. She obviously liked the ensemble I’d worn to her house last night but what was I prepared to risk today at work?

It was difficult to resist as I really wanted to impress Dana so that I could actually get to have sex with her but at what cost. She has this amazing power that makes me want to do as she says even though, in my head, I know it is risky. Well a business cost benefit analysis showed the risk was worth it if I could get between those beautiful long legs of hers with more than oral sex as an outcome. But what was my business strategy? I decided that something simple but creative would work. I got ready for work that morning with nervous anticipation. Dana had already seen the hold up stockings and panties I’d worn to work yesterday when she had caught me out. She’d also seen the matching bra and panties set with suspenders and stockings last night while at her house. I decided to wear a white satin camisole top under my shirt that would pass any likely scrutiny as an undershirt but would certainly have my nipples brushing that fine, sensuous material all day and probably keep them at attention. I dressed for work in my dark hold-up stockings and some matching panties and the white top under my cream business shirt and blue suit. I checked the look in the mirror. All was ready for another day at the office.

As I arrived in the office I asked my secretary, Alison, to clear an hour in the afternoon for a planning meeting with Ms Jones. She asked if I wanted her there to take notes or anything. I told her that wasn’t necessary at this early planning stage but she seemed a little put out. I wondered what was bothering her and asked if everything was okay.

“Yes, of course Mr Meadows. Everything’s fine. I will be here if you need anything,” she replied.

The day progressed steadily and I met a few other people on other accounts and true to my thoughts, my cammy top had kept grazing sensuously every time I moved. I was certainly at a heightened state of awareness when, finally, 2 p.m. arrived and Dana was at my door. I stood up but remained riveted to the spot behind my desk, admiring her every nuance of movement. She sauntered in and again paraded herself, her mere presence was enough to change the atmosphere of the room. She casually entered and perused her target up and down before settling on the lounge in my office, her blouse tightly outlining her beautiful breasts that I had been introduced to last night and her long legs showing through the split navy blue skirt to reveal the seamed stockings and navy high heels. As always, elegant and sensuous. Her eyes locked to mine as she patted the seat next to her, inviting me to sit.

“Did you enjoy last night?”

What, a test straight away? “Absolutely. It was a wonderful evening and you have a beautiful home,” I nervously responded.

“It was nice getting to know more about you Jason. You have a very interesting story for an even more interesting past-time. Tell me, what ever happened to your sister and her girlfriend?”

I explained how, after that night, we had got together as a three for many nights and weekends of similar fun over several years but quite some years ago the girls moved overseas for a job opportunity with their design business. We keep in touch but not in touch if you know what I mean. We chatted about all sorts of things related to this mutual interest that we seemed to have.

She asked me, “So where do you get your clothes?”

In the early days I didn’t have the courage to buy them so I used my sisters’ until all except Sarah had gone from home; occasionally I would swipe some when the chance arose, although that was rare and risky, or go to second hand shops on the pretence of buying costumes for a local theatre group. Since moving out of home, I had the opportunity to browse stores but still had no significant other to share my interest with. I’d kept it in the closet since Sarah and Jody left. I’d made a couple of forays out at night but my make-up skills still weren’t up to the standard and I guess I was just nervous and going solo only made that worse. As for buying my finery, I had a list of excuses to use. The old ‘I’m buying a gift for my girlfriend’ urfa escort worked but always seemed unconvincing and got some funny looks. The internet in recent times had been a blessing but I had my share of disappointments with sizes being wrong or the ‘fine lace’ cups of some bras I bought turning out to be coarse cotton. It was then that I told Dana about how I landed the new account we were to work on together and where the things she’d seen recently had all come from.

I had gone out of town to sort out some company business with a client and had finished the work early – too late to go back to the office but too early not to celebrate a free afternoon, so I went to look around the medium sized metropolis. I quickly found the more up-market shopping precinct and this quite decent sized store that sold lingerie. It had an attractive yet stylish look and clearly was popular with quite well dressed women coming and going regularly.

Having just clinched the other deal I guess I was feeling a bit brave and so I decided to do something that previously I had only wished I could do. After loitering around for a while to build up the courage, I went into the store and browsed around for a while. They make beautiful clothes and import a lot of overseas labels, but they also offered a service of making lingerie to order. The business seemed to be doing well. Finally an assistant came to help me. She was about 23 or 24 and really very attractive and shapely. I had no doubt that she used her employer’s products! Prominent on her left breast was a stylishly designed name badge that announced her as Andrea.

She asked, “Is there something I can do for you sir?” in a delightfully soft voice.

I summoned up some more courage and said, in what came out as barely a loud whisper, “I’d like to buy some lingerie.”

The assistant was patient and helpful and responded to my nervous question with, “Certainly Sir. Was there something particular that you had in mind?”

I stammered out the answer as, “Yes, … a bra and panties set.”

“Do you know the size required?”

Here it was – the moment of truth. I’d gone in there feeling reasonably confident but now the actual statement had to be said.

“No … I’m not sure. I’d like to be measured.”

There, I’d said it.

More to my shock was her reaction. I was fully expecting the ‘get out of here you pervert’ type response but instead she gave a faint smile and said, “Certainly Sir. Please come this way.”

And then she led me towards the back of the store. She left me standing there a moment while she went out the back and then came back with another woman, an older version of herself. Her buxom figure displayed a badge that said Sue. The mother was 40ish and must have had her daughter early. She was a very attractive with a great body and a very honest manner. I later found that I was right; she was 41 and had a baby at 18.

She smiled at me and quite openly announced conversationally, “I believe you’d like to make yourself feel good in some of our products.”

There was no judgment in her tone. I nodded. Looking me up and down, sizing me up I guess, she continued, “We have a confidential fitting service that can be done at your home, hotel or in store after hours. Which would you prefer?”

I explained my trip to town and that the ‘in store’ option would be great if it could be arranged that day. She told me to be back at a little after 4:30 as they close at 5 p.m. That way I could have a good look through their stock to decide what it was I wanted to have made or to buy. This was an exciting prospect. I had trouble killing time with the afternoon’s activity in my mind. Time seemed to drag.

Eventually it was 4:30 and I went back. There were a couple of women browsing and they both gave me looks that seemed to say, ‘I know what you are up to’ and it made me nervous. At last Andrea, the daughter, came to me and told me that Sue was waiting in the back room if I’d care to follow her. First she locked up after the two other customers had left and then put the closed sign up. Next we went to the back of the store.

We met and went through some pleasantries that were meant to make me feel a little more at ease. “Hi I’m Sue and this is Andrea. Welcome to our store, ‘Close To You’.”

“Hi. I’m Jason.”

“How can we help you Jason?”

“Well I’m interested in some of your products for my own use,” I stammered.

“Would you like a drink to relax while we do the fitting?”

Very soon I had a very nice glass of wine and we were chatting quite pleasantly. They found out that I was in advertising and straight away made the comment that they perhaps needed some help in that area with their business. Next we did a stroll through the store to identify the sort of things I wanted. I was in heaven as we browsed; so much beautiful lingerie.

I started out very conservatively with simple bra & panty sets but they moved me through to other sections including stockings balıkesir escort & suspenders and even a very interesting girdle and corset section. They had me feeling the materials and commenting on the colours as our banter turned rather sensual. A couple of times they took samples from the racks to press into my hands to feel the material while also feeling the warmth of their hands and occasional shoulder to shoulder pressure as we moved around the relatively confined aisles.

After a good look around, we returned to the small back room where they asked me to sit down and relax and take off my clothes. It sounds dumb I know but here I was on a sexual high and actually very relaxed with these two lovely ladies assisting me. It had not occurred to me that I would have to make myself naked in front of them. The look on my face must have said it all.

Andrea came over and said, “It’s okay. No rush. Have another wine.”

She then took my glass to refill it. When she came back there was a very noticeable difference to her clothes. She had undone several buttons and removed her bra and the blouse was rather sheer. She bent down in front of me to give me my wine and her cleavage was delightful.

“Now about your clothes …” she said.

She took my hand and made me stand. She then proceeded to slowly undress me. Sue sat quietly and watched.

In a fairly short while I was naked from the waist up. I’m not in prime condition anymore and there’s a bit of weight there. My ‘problem’ if you see it that way is that I generally put weight on in the chest before almost anywhere else. Consequently I have a nice pair of ‘man boobs’ that are nearly a B cup I think and are a great advantage to someone with my particular interest.

Sue was very polite in commenting, “A very nice chest to work with Jason.” Or perhaps she meant it.

Next was my lower half. The tent in my pants indicated that the wine had relaxed me enough and now I was enjoying the attention. Andrea took off my shoes, undid my belt and opened my pants and allowed them to drop. As she opened them she looked up at me and smiled and then turned to Sue and said, “Mum, look.”

My silk lace-edged French knickers had a big bulge and a wet spot in them. Sue said, “Leave them on for now while we sort out the bra.”

She brought a tape measure and note pad and said to me with a lovely smile, “Well ma’am, let’s get to work.”

She warmed her hands and then caressed my chest feeling the size of my titties and how hard my nipples were.

“Nice nipples,” she said as she tweaked one and circled the areola with her index finger while cupping my breast in her right hand. My sensitive nipple hardened as my cock throbbed.

Sue then explained, “I hope you don’t mind but I am training my apprentice here, so I will get her to follow up on each step of the fitting process. Is that all right?”

How could I possibly disagree as Andrea’s tits swung towards me in her blouse and she stood alongside me on the opposite side to her mother. Stood between these two lovely women, each had a soft warm hand in the small of my back.

Sue explained, “Now feel the curve of the breast and the firmness it has. Check the nipple area is firm. Lift the breast to feel how heavy it is so that you can work out how much support to give it.”

All through this they were acting on each step of the instructions. I was in ecstasy. They proceeded to caress and fondle, tweak and tickle and eventually measure. I am certain that most of this was entirely for my benefit only, but I decided not to complain.

Based on the notes taken Sue said, “I will see if we have something in stock that will be a close fit while you wait for yours to be made. Andrea can commence the measurement for the knickers you want.” With that Sue was gone into the store.

Andrea was in no rush to start the measurements. She continued to fondle me and then she slowly lowered her head and started to suck on my nipple. I gasped at the sensation as my areola puckered to the attention. The sucking became more aggressive and she started to nip and bite and as she did this she reached down to stroke my cock. I eventually got up the nerve to become an active participant and I started to fondle her full breast and tweak her nipple in the same way she was biting mine. My cock was throbbing in her hand and after some more of her torture on my aching breast, she gradually slid down my torso and onto her knees.

The front of my French knickers was saturated with pre-cum and she started to suck on that while she hooked her fingers in the waist to remove them. As she pulled them down my cock sprang up and hit her on the cheek, smearing juice. She wiped it with a finger and looked up at me and sucked it into her mouth.

She moved to take my cock also and just as she did Sue came back in with several bras in hand and said, “Wait Andrea. Let’s try this — it’s a 36B.”

I was stranded with my knickers at my ankles and a throbbing trabzon escort erection while the delightful Andrea stood up in front of me. Sue handed Andrea a beautiful ice blue soft satin bra to put on me. While she was getting it organised Sue stroked my penis and said in a very business-like manner, “It’s lovely but it has to go if you want to wear good lingerie. Andrea will take care of it for you in a minute. She gives great head — I taught her how.”

All through this she absent-mindedly continued stroking me, and my cock was twitching all over the place leaking juice all over her hand which she equally casually licked clean while looking me straight in the eyes. These were the women that the word wanton was created for. There was lust in Sue’s eyes as she held my gaze. It was while I had this distraction that Andrea pulled hard on my nipples and then said, “Bend forward. This is how to put on your bra Jason.”

She slipped the straps over my dangling arms while I was bent at the waist. “You need to lower your breasts into it and then connect the hooks and eyes — that way the bra cup is filled properly and will support you well.”

The satin feel of the material on my nipples was glorious and that, added to the secure hold on my chest, actually made my boobs stand out more than usual. With a little adjustment to the length of the straps, I was in heaven.

“Now for those panties.”

Andrea was on her knees in a flash and my cock was down her throat. She sucked and chewed and bit the head and raked her teeth along it and across the head. It was too much and I went weak at the knees and had to sit. Sue steered me back into my chair and I flopped back down.

Andrea just kept going and Sue moved behind me to reach around and caress my filled bra while my head nestled between her warm and ample breasts. It was a great come and it overflowed Andrea’s mouth. She smeared some up and down my cock, which kept it hard, and then she stroked the rest over her full tits that had fallen from her opened blouse. She crawled forward up my body, dragging her nipples up my torso and grazed my bra covered nipples with hers. She then kissed me, filling my mouth with what she had not swallowed.

Sue was on my cock immediately and she had indeed taught her daughter a lot but not everything! I came again. I actually had a second orgasm within minutes that was centred around my cock but there was nothing left to ejaculate. The trembling tingling feeling was amazing. I hadn’t come twice in that short a time since I was about 18.

I felt like I was totally spent. Weak-kneed and dizzy with pleasure. Next the tape was out to measure me up and a range of undies was decided upon. The range was a delight, a veritable rainbow of colours, styles and materials. Without doubt I preferred the satins and silks that caressed my loins. Sue explained that making these for men was a specialty they provided so that, if I wished, my manhood could be tucked away to give the more feminine crotch-line or they could be made to provide maximum sensuality.

I liked both ideas and then we browsed over the stockings and suspenders range. Gorgeous styles and patterns in an amazing vista of colours were brought before me and I selected I don’t know how many that piqued my interest. The list of my choices was growing rapidly and I eventually had to think about how I would pay for it all. Sue and Andrea finally brought proceedings to a close, helping me dress in some new lingerie. We looked down the list of the many items I’d chosen. Some were in “Close to You” bags on the counter while, as Sue had explained, others would be made to fit.

I was dressed and preparing to leave as we went back through the store. Sue then insisted on me letting her prepare a bustier for me. When she explained that it was a push up bra, corset and suspender all in one I just had to agree to try it. The whole order ended up huge with a range of styles and colours to be prepared. When I asked how much all of this was going to cost, Sue’s answer was a rather enigmatic, “Oh we’ll worry about that later when you decide what you definitely want to keep. We’ll call you in about a week — you can come to our home and try them on.”

She gave me a business card with the address on the back and then they both kissed me and let me out of the store. I drove home in a dream and my new bra and matching panties.

Work was hectic with the deal I’d closed that day but the experience with Close to You kept re-living itself in my mind all through the week as anticipation of their call grew. Sue finally phoned. She said I was to come to their house on Saturday night. I agreed and arranged to be there at about 5 p.m.

“Make sure that you are not late, we have lots for you to try on!”

On the evening I was due to go I made a point of bathing and shaving and making myself well presented. I arrived at the magnificent house on time, as requested. There was a long curving driveway that led to the marble steps to the front door of this two-storey mansion. The ivy-covered walls were in stark contrast to the white paint of the building, giving it a classical look. There was a light on the front verandah at the door where I was standing as I rang the doorbell. Sue met me at the door and ushered me in rather hurriedly with a cheerful, “Oh hello! You’re here at last. Come in, come in.”

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