Part 1.

Where to start, I suppose it was work that first stirred my interest.

I work in an office environment where I am the only guy. There are another 20 girls of various shapes sizes and ages. Quite often the subject between the younger girls is current boyfriends or one night date. 

I think my first trigger was at morning coffee time one heavily made up girl was discussing her underwear her boyfriend had bought her. One of the other girls didn’t believe her. So the first girl stood up reached under her skirt flashing a stocking top and suspender clip, and removed her tiny thong. She held it up for us all to see. The girl who didn’t believe gasped and grabbed them, gave them a feeling and passed them on. When they got to me I just took them and passed them to the next girl. Eventually the owner got them back put them on, once again flashing her stocking tops and suspender clips. 

“Oh don’t mind me, I expect you have seen your wife’s smalls.” She uttered to the laughter of the others.

“Smalls yes, but not minuscule.” I replied somewhat embarrassed.

On return to my work station I had an itch on my nose. I rubbed it and could smell the scent of her pussy from holding her thong momentarily. 

Mmmm I thought, I wonder if my wife (Karen), pussy smells as nice. I forgot all about it until after my shower, in the laundry basket there was a pair of my wife’s panties she had worn that day. I picked them up and held the still damp gusset up to my nose. The aroma was different but arousing.

It wasn’t just the aroma it was the feel, the softness. I was becoming very erect. I had to try them on. I struggled to get into them as they were smaller than my briefs and with a very rampant. It finished with me wrapping them round my cock and stroking myself with them. I managed not to cum, but leaving them in the basket, my own worn underwear on top, I clambered naked into bed with my wife. I snuggled up close my man hood pressing urgently in between her legs. Cupping her breast through her silky nightie. I aroused her nipple making it hard and erect. I slid my hand down to the hem and teased her panty covered pussy. 

“Mmmm someone is anxious, and I love it. Let me get my panties off darling.” She whispered.

She quickly removed them and threw them on the floor. 

“Please climb on top of me.” I asked.

She climbed on top and slowly lowered herself onto my iron hard cock. Now I could cup both her breasts through her sensuous nightie. The seed for my journey into silky nylon had been sewn.

Move on 6 months. I now owned secretly several items of feminine underwear also a Little black dress. Some shoes, a blonde Wig and some items of makeup. I did use some of my wife’s makeup, I guess on hindsight using hers aroused her suspicions. 

I arranged a day off work, what I didn’t know was my wife accidentally met my supervisor I work with. She asked where we were going on our day off.

My day off arrived, my wife left for her work. Giving her what I thought was enough time for safety. I showered shaved everywhere I could reach, then I started to dress in the undies I had stashed away. 1st a black corset with suspenders, I followed this with tan stockings then some panties. I tucked everything back for a smooth line. The next item was a white bra, I had watched my wife fit hers backwards then twist it round. I put my arms through the straps and padded the cups with some of my socks. Lastly I pulled the black dress over my head and settled it in place. Next was my makeup, I tried to look natural but I guess I need practice or instruction on how to. Nearly there. Taking my wig next I fitted it and finally my heels. Not too high, I didn’t want to break or twist my ankles. I hadn’t planned anything to do just sit dressed, surf the net. Making my way to the study to log on, I passed the lounge. My wife was sat on the sofa.

‘Oh heck, I’m finished, before I’ve even started’.

“I think you had better come in here and explain yourself.” She ordered.

Shaking and now taking unsure steps I joined her in the lounge. 

“Sit in the armchair.” She ordered again.

I did as instructed. 

“Now what is this all about, are you gay and want to go with guys?” She asked. 

“No definitely not, I love the feel of the soft underwear you girls have, my cotton briefs and t-shirts are rough sand paper by comparison.” I started. I continued with the events from the thong being passed round in the staff room to her knickers in the bathroom and the acquisition of the various items I was wearing and the others in the bedroom. 

When eventually finished she announced.

“Well first you need to learn how to sit properly, I can see your stocking tops and panties from here, next you need lessons in applying your makeup, not mine. Then you will need some well fitting clothes. Now back to the bedroom young lady.” She instructed me not quite so severe but quite stern still.

She followed me to the bedroom and sat me down my back to the dressing table. I watched as she went through the little case of undies open on our bed. Nice choices some of these but first things first. She removed my wig saying it was ok but an Auburn colour would suit my skin tone. The she used her makeup cleaning pads and removed all my makeup. Then starting she applied various lotions and colours of her own makeup selection, then she used a hair brush on my blonde tresses to make it look more presentable. 

“You will either need a waist of full length slip under your dress, it’s a little see through.” She told me.

This is going better than I thought it would. 

“Now we need to sort through your undies, I think tights would be better under that dress until you have a petticoat. I can’t see any in your case. So I’ll loan you a pair of tights, as my slips won’t fit you. Now take your stockings off and I’ll get some tights. 

I unclipped my stockings and removed them with my heels. Now be careful they ladder easily. She instructed me on how to put them on and set them in place. I replaced my heels.

“Now we need to get you some more clothes. Better get your wallet and cards.” She informed me.

I was thinking of online shopping, but she had other ideas. She picked a black shoulder handbag and we went back downstairs. I headed towards the study.

“Where are you going young lady?” She asked. 

“I thought we were online shopping.” I replied.

“No we are going into the shopping outlet. They will have everything you need for your new wardrobe.” She stated. The firmness back in her voice.

“What, no I can’t.” I replied extremely nervously.

“Yes you can, and will. Now put your wallet into this shoulder bag and get in the car. I’m driving, until you get more used to your heels.” She instructed.

Meekly I got in the passenger seat. 

“You need to watch me for the next time or you will expose your panties and your secret.” She told me.

Moving to the drivers side she sat on the seat and keeping her knees together swivelled in. We closed the doors and put seat belts on. It was different the belt dividing my boobs. 

After about 20 or so miles I began to feel less nervous, we were nearing the outlet. Karen parked not close but not far either. She got out and came round to me. I opened the door. 

“Knees together now.” She instructed.

I did as I was told and exited the car quite demurely. She locked the car and taking my arm she marched me as quick as I could manage into the first outlet shop. There were hundreds of dresses, skirts, blouses, heels and most exciting, lingerie all styles and colour.

“Can I help you ladies?” Enquired a senior assistant. Her badge told us she was sarah H a senior assistant. 

“Yes please, my husband requires several lingerie items also dresses, skirts and tops. But first he needs a slip to go under his dress.” Karen informed her.

I was extremely embarrassed and blushed from my toes to my hair. 

“He also requires a couple of auburn wigs and some heels.” She added.

“Of course madam, what are you sizes sir, or perhaps I should say miss?” Sarah H asked.

I felt humiliated at being, to coin a phrase, outed. 

“Follow me and we check what we have to your liking.” Sarah offered.

Before we looked at the lingerie and dresses etc.

“Perhaps madam would like to go upstairs to the fourth floor it has a selection of wigs with real or artificial hair. Also our shoe department is on the fifth floor.” Sarah H offered.

“Thank you can she pay at any cash desk?” Karen asked. 

“Yes madam, just return to the desk over there.” Sarah responded.

Sarah hurried me to the changing rooms. We went in and she quickly removed my dress. Then taking her tape measure from her pocket in her dress she took my measurements and wrote them down. While measuring my hips she noticed the corset I was wearing and the suspender clips hanging loose. 

“Do you normally wear stockings miss?” Sarah enquired.

“I did when I dressed this morning, but Karen told me to wear tights as my dress was semi transparent.” I replied.

“I love wearing stockings and suspenders, I think they are so sensual.” She replied. The next thing she did was to lift the hem of her dress to show me her lace top stockings, held taught by white suspender straps. 

She lifted it a bit higher and I could glimpse her bright pink lacy panties. The bulge of her pussy was quite pronounced. She dropped her hem to cover herself again. Her next move took me by complete surprise. She put her arms round my waist and pulled me to her. She kissed me full on the lips. Gently easing her tongue between my lips into my mouth, her hand went to my panties and caressed my growing bulge. Breaking the kiss she whispered.

“We must be quick.” 

She knelt down and in one swift movement my tights and panties were round my thighs and my now hard cock was in her warm wet mouth. One of Sarah’s hands was caressing my love eggs whilst the other was finding its way to my rosebud. Her bobbing, sucking and caressing soon had my juices rising and firing both cylinders into the back of her mouth. Now she was swallowing as she coaxed every ounce of my baby maker seed out of me. 

As my erection subsided. She ran her tongue along the underside of my cock. Sarah stood and with her open mouth I could see my cream resting on her tongue.

“Mmmm very tasty, similar to mine.” She whispered huskily.

“What do you mean?” I asked somewhat nervously.

With that Sarah stood and reached behind her back. I heard her zip and her skirt was on the floor. I could now see her white suspender trimmed with black lace and her bright pink panties. The bulge I had noticed before, thinking it was her pubic mound, was even more pronounced. She hooked her fingers into her panties and slid them down to mid thigh as were my panties and tights. As she straightened her hardening cock popped into view. 

“Your turn.” She told me indicating to her cock.

Nervously I knelt and carefully took hold of her. It twitched to my touch. 

I leant forward and my tongue licked the tip. Mmmm her sticky juice was quite sweet. So being a little bold I slipped more into my mouth. Remembering how Sarah has treated me it returned the favour. Very soon Sarah was pushing in and out. She grasped my head, holding my head still she swelled and I felt her cream pump into my mouth. 

Oh my I had scored a hat trick. My first time out dressed feminine. My first ever oral with another dresser. Finally my first ever swallow of cum. 

“Are you two finished in there?” Came from outside the changing room. 

It was Karen, she had returned from buying wigs and heels. 

“Yes thanks, just coming out.” Sarah answered replacing her skirt.

“Pull your panties and tights up.” Sarah whispered at me.

I did, but before I could put my dress on Sarah had opened the door. She went straight to Karen and hugged her.

“Thank you honey, she is wonderful and very tasty.” Sarah told her.

I just stood there semi dressed open mouthed.

“Don’t worry darling, I knew Sarah at school, she even then was a very feminine boy, and now she is and equally feminine woman, I knew you needed to meet someone for your first oral experience that was going to treat you gently. Now let’s pay for the clothes I have chosen for you. You need to thank Sarah for giving us her staff discount.” Karen explained.

“She already has and it was very tasty.” Sarah giggled. 

After we paid, on the drive home Karen informed me there would be a few more changes in my life. 

To be continued.