My Initiation

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cdandy
cdandy
196 Followers

Chapter 4

Monday morning, Mike dropped by for morning coffee.

"So how was your weekend" he said with a grin.

"Terrific" I said "and yours?"

"The best. Never had a better time. How was Michelle?"

I could tell he wanted my 'morning after' impressions

"Mind your own business" I laughed "seriously though, she was amazing." I looked at his eyes. The only giveaway. Yes they were the same. No eye shadow or other makeup of course but definitely Michelle's. They could have been brother and sister.

"That about sums up how she felt" he said "And wanted to thank you."

"Thank me?" I said "I'm the one who should be thanking her for a lovely evening."

The following Friday was just as exciting. Her taste in clothes was remarkable. This time she wore a simple, pale green skirt coming to just above the knee with a short split up the side which revealed an enticing, white lacy slip. Her white v-neck blouse showed just enough of the top of the slip to stop the heart. I stayed later than ever that night at her house. Our conversations were becoming more intimate and the time just disappeared.

Then one Friday night, our conversations took on a new turn. She asked me what I liked to see in a woman and what did I like to look at on the internet. I told her that internet porn was boring. When you've seen one or two frenzied sessions, you've seen hem all. The girls were always big chested, shaven tarts and had all the allure of a store mannequin. I told her I liked to see women with at least some clothes on. Usually underwear, I'd said blushing, but there's nothing nicer than seeing good legs beneath a miniskirt or pretty panties. A camisole top covering small neat breasts was much more of a turn-on than bare breasts. The outline of a thong under tight clothing would leave me panting. She seemed very interested in this and kept up the questions of my feminine preferences.

"Have you ever tried any female underwear on?" she asked.

"It's something that never occurred to me" I answered with surprise. "I've never really had any contact with lingerie. My wife had a white cotton panty fetish and never owned a suspender belt or stockings. She wore jersey pyjamas to bed and tights the rest of the time."

Michelle laughed. "You poor thing. You seem to like looking at it though."

I did too. I had browsed a lot of the online catalogues thinking I was looking at the models but was I really?

"Yes I do." I said. "It always seems something taboo for men. I used to go shopping with my wife and if she went anywhere near a lingerie section, I would feel slightly embarrassed. You could see all the other husbands looking around at anything but the underclothes, as if to say 'I'm not really looking at these panties and bras'. Silly really"

I felt this was leading somewhere but I had no idea where. I found out later.

As I was leaving, she handed me a small parcel saying "A present for you. For all the lovely nights out I've had."

I started to open it but she covered my hand saying "Not till you get home. Now go. It's late." She emphasised this with a squeeze and a lovely smile that set my heart eating. I wanted to kiss her and, even more, to stay the night. It was becoming more difficult to remember who I was with.

Reaching home, I stripped off and headed for the shower. It was almost three and I was tired. A long day at work followed by a long, but enjoyable, evening. On returning I climbed into bed and reached for the light. The parcel was lying where I'd left it on the chair.

Curious, I climbed back out and picked it up. It was very light and tied with gold ribbon. I opened it up and looked inside. The contents made me gasp and I felt I had to sit down. Inside were some exquisite, lacy items of women's underwear. On top lay a silky pair of French knickers. Cream, with a fine lacework around the legs and a delicate bow. I lifted them out and held them up. They were beautiful. I ran them through my fingers. The sensation was fantastic. They had a life of their own – seeming to want to slip through my hands.

I put them on the bed beside me and looked at the next item. It was a matching camisole top. The same lacework and bow. For some reason my hands were shaking. Putting this beside the panties, I looked at the last items.

They were a pair of sheer dark stockings. They were stay-ups with beautiful lace tops. As they fell across my knees There was no weight to them just a gossamer touch. I felt an electric charge in the pit of my stomach. I was breathing faster and starting to get an erection. Should I try them on? No-one could see or would know that I had tried women's underwear. I slipped one of the stockings over my foot marvelling at the sudden smoothing out of my skin. I drew it further up and over my knee. Being fair haired, there was no sign of hairy legs. Just a smooth, slightly shiny leg. I pulled it all the way up and adjusted the lace band round my thigh. It was as though all my nerve endings had come to the surface at once. I could feel air sitting on my thigh. I moved my toes and the material rippled across them. I pointed my foot and the slight stretch travelled all the way up. It was fantastic. I moaned and hurriedly put the other one on. I now had so many stimulating nerves needing attention, I didn't know where to touch or stroke.

I looked at the panties. Then making up my mind I lay them across my lap. They were so cool. I put them over my feet and slowly drew them up my legs. I had an erection now and containing it in these fine panties was difficult but moving it about only caused more friction than I could stand. I finally got them settled and reached for the camisole. I slipped it over my head and drew it down. It just came to my hips – cool, soft and incredibly sexy. My hands were just wandering over my silken body now, testing every feeling, enjoying the beautiful clothes as I looked down. My body looked pretty apart from the tent in front.

I opened the wardrobe door to have a look in the mirror and was instantly disappointed. My man's head on top of women's underwear. I looked just like all those cross dressers I'd seen on the internet. Men dressed up in girlie clothes with a hard on. I looked stupid. It was such a same to put these beautiful clothes on a man's body. My erection slowly subsided. I went back to the bed and sat down. Now that I had seen myself, looking down at the flimsy lace and nylon didn't seem so erotic. I undressed carefully and folded them back in the box. I would return these to her and ask her to wear them for me.

I woke early Saturday morning after a restless night. Dreams of being in the office dressed in just ladies underwear haunted me. No-one had seemed to notice but I kept trying to hide behind the desk in case they saw what I was wearing.

At ten o'clock the phone rang. It was Michelle.

"Good morning Steve" she said gaily

"Michele" I said warmly "I was just getting up." The lie escaped all on its own.

"I hope I didn't wake you" she said "only I been worried I might have offended you with my present."

"Of course you didn't offend me" I said quickly "They were beautiful."

"Oh good it's just that ... well making a pasta tonight and I wondered if you'd like to help me eat it"

I felt a thrill. "Hey sure" I replied "I'll bring the wine."

"Great "she said "About five then?"

"Five? " I queried "Isn't that a little early for dinner?"

"Of course not. It'll make a nice long evening." She laughed.

We said our goodbyes and I hung up the phone.

Chapter 5

I arrived at her door promptly at five clutching a bag with two bottles of wine and the parcel.

"Steve" she smiled widely "I'm so glad you came." She reached out and pulled my arm in through the door.

"I wouldn't have missed it for the world." I grinned. "Not every day I get asked to dinner by a beautiful lady.

She closed the door behind me and I passed her the bag.

"I err... brought your gift. " I said lamely "They would look much prettier on you. Please don't be offended.

"Of course not " she said taking the bag "come on."

I followed her into the lounge and sat down on the sofa.

She opened a bottle of the wine and brought me a glass. I'd made a good choice – It was excellent.

She sat down beside me with her legs tucked up and looked at me very sexily over her glass.

"What did you really think of the lingerie?" she said quietly

I looked back uncomfortably. There was to be no lie here.

"I thought they were exquisite. "I answered "I've never seen such beautiful clothes. So soft and silky. "My mind thought back to my first impression. "How the stockings just seem to have a life of their own. And the fineness of the panties, So smooth and silky. Nothing like my own underwear." My voice had fallen to a near whisper as I described how I felt as I touched them.

"Did you try them on? " She said in the same sexy voice.

Ah. The question I had been dreading. If I lied now she would know and we could be finished.

"Yes" I said and looked into her eyes. There was a slight smile on her face, but not a mocking expression - more triumphal I thought later.

"And how did they feel?"

"Amazing" I said "They were heaven." I described the feelings I'd experienced. There was no embarrassment now. We both knew what had happened. She must feel it every time she got dressed.

"Then I looked in a mirror. "I sighed "And saw a man dressed in women's underwear. I looked like those pictures you see on the internet. Usually in red or black panties with a cock pointing out, a grubby slip stretched over a fat stomach. You know the men with their heads missing." I smiled sheepishly. "I decided I couldn't let anyone see me like that and I looked awful. Not err.. pretty as I expected."

Michelle was nodding slowly. "I know Steve" she said quietly. "I've been there."

"No but you're stunning. "I exclaimed "You're a knockout. Take it from a man who has splendid taste in girls."

"At first I was just one of your 'Internet headless wonders' she said "but I knew I could do something about that. It took a while though" she admitted with a smile.

I nodded blushing. I had forgotten for a while there. "I'm sorry Michelle. I didn't mean.."

"I know that " she interrupted. "Will you do something for me though"

"I'll try "I said anxious to make up for my blunder.

"Let me dress you" she said quietly "Complete. All bells and whistles. Let me show you how you can look if it's done properly." She was speaking fast now. Not letting me interrupt.

"I. err.. " I stammered

"If you don't like the result or what I'm doing we can forget it forever"

I thought for a moment. She took my empty glass, got up and went over to the bottle of wine. As she was filling the glasses my mind was doing some fast thinking. I had enjoyed wearing the clothes. I did want to experience the feelings again and as long as only Michelle saw me, what was the harm?

"Ok" I replied "I am yours for the night to do as you will, My Lady "I stood up and bowed dramatically. She gave me my glass and I took a large gulp.

She giggled, nearly spilling her own wine. Come on then she said and walked towards the bedroom.

"What right now?" I asked

She looked back. "Mine for the evening. Remember?" she laughed.

I sighed and followed her.

I'd never been into her bedroom before and was surprised how tidy and feminine it looked. A massive king size bed covered with an ivory bedspread, decorated with pale, pink roses and green vines stood in the middle of one wall flanked by two neat bedside cabinets. Wardrobes covered one side of the room and a large vanity unit sat against the other. The curtains matched the bedspread and were, thankfully heavy and, more importantly, closed.

"Ok, clothes off" she said without turning and started fishing about in the dresser drawers.

I hadn't banked on that but it made sense so I took my shirt off and stepped out of my trousers and stood in my boxers waiting. She turned round holding out a suspender belt on one finger.

I don't think his will go with them" she said and smiled.

"Oh... no... of course. "I said. And slipped them down. This was a first for me, not being accustomed to standing naked in front of anyone.

I took the belt and she turned around to the drawers for more clothes. Eventually I figured it out and fastened it around my waist. It was pure white and made of some fine, wide, shiny lace with pale blue embroidery running through. The straps ticked my thighs enticingly. She handed me a pair of honey coloured stockings and I sat on the edge of the bed to put them on. The feeling was again, exquisite and I felt the beginnings of an erection. I clipped them to the suspenders and a pair of the most beautiful panties floated into view. They were high cut lace and matched the belt perfectly. I stood up and felt the stockings pull slightly. She handed me a matching bra and showed me how to put it on backwards round my waist and slide it up to my non existent breasts. I looked down at myself, disappointed, as if I should have magically grown something to fill the bra.

"Head up." Michelle demanded and she slipped two breast shapes into the cups. She handed me a white satin camisole top which I slid over my head and new breasts followed by a soft, silky waist slip. The hem was all lace and my erection finally made it to the vertical. The combination of soft, silky and totally erotic materials caressing my body were nearly too much. I managed to control myself with sheer willpower.

"It should really have been a full slip but I've only got one and I'm wearing it." She said and lifted the hem of her skirt to reveal a similar lacy frill. "Sit down here please "she said and indicated a chair beside to vanity unit I carefully moved over to it and sat down facing the bed where she sat with a variety of cosmetics laid out beside her. I followed her instructions, closing or opening my eyes as requested – studying her beautiful eyes when I could. After what seemed an age, she smiled approvingly and went to the wardrobe coming back with a long blonde wig. She fitted it and teased a few hairs into place with a brush.

While I fiddled with the fine material of my clothing and looked at my heavenly new shape she went to the wardrobe and returned with a pale green chiffon dress. It was multi layered and looked stunning. I stepped into it and ran my hands down my breasts as she zipped it up. Handing me some low, white sandals she stepped back and covered her mouth, her eyes wide.

"Oh God...You are beautiful." She gasped "Much more than I expected."

I twirled on my heels and the dress billowed out, creating a delicious draught on my thighs.

"Go into the bathroom and look "she said "there some full length mirrors. Walk slowly in those shoes." She seemed breathless.

They weren't very high heels but they were narrow and tricky to walk in. Every step pulled or caressed some part of my body. The straps across my shoulders, the suspenders pulling at my thighs, the hem of the skirt flicking against my calves... It was a long delicious journey.

I reached the bathroom and went in closing the door behind me. The full length mirror was covered with a towel and I realised, that all the mirrors had been covered. I smiled. This had all been planned long before I arrived.

I reached up and took the towel down. There stood a beautiful blonde girl staring back at me. She was stunning. I couldn't believe it. Instead of the pancake makeup I had expected, this was light and barely noticeable. A hint of eye shadow, faint eyeliner and she'd done something wonderful with blusher. I looked young and the shape of my face was changed. My eyebrows had been subtly moved and my lips were just the palest rose colour. I stepped back and looked at my body. I was a different shape. Curvy, sensual. Nice small breasts. I twisted round to look at the back and noticed another mirror covered behind me. I took down the towel and looked at the reflection from the mirror behind. Shapely and very sexy. I lifted the hem of my skirt and gazed at the sticking tops framed with the lacy slip. I lifted it higher and my panties came into view. Dropping the dress, I touched my hair. It felt soft and luxurious.

I must have been ages stroking the materials and admiring myself - there was a soft knock on the door and Michelle said, "are you OK in there?"

I woke as from a dream and called "uh... sure. Come in."

"You like?" She asked

"It's incredible... What you've done" I said. "

"Come and have a drink and we'll eat." She walked out and I followed slowly, savouring each step. There was no question of taking it all off before dinner. Wild dogs couldn't have torn it off me. My appetite didn't do the lovely meal justice. I felt strange and had trouble stopping myself looking down at my body and touching my legs and body.

After dinner we went into the lounge and with a glass of wine, sat on the deep sofa.

"You should keep your legs together when you sit down" she said, her eyes sparkling "It's more ladylike."

I snapped my knees closed and sat looking at my hands.

Finally I asked "Well, have you achieved your goal?"

"My goal?" she said with eyebrows raised.

"You asked my if I'd do you're a favour and dress up for you" I smiled.

"In that case, yes."

"Why did you want me like his" I asked.

"Well... you've been asking me what it felt like, why do I want to be feminine and all sorts of questions about cross dressing for weeks now. So I wanted you to find out for yourself. "She replied.

"I don't feel like a woman" I said

"But do you feel good?" she gave me a sexy smile.

I blushed. "I feel ... terrific" I said grinning.

"But, how do you feel?" She persisted.

"Sexy, beautiful, erotic. I feel like I don't ever want to take it all off." I said quietly

"Then you understand some of what I feel" she said. "The erotic feeling of dressing in underwear wears off after a while but the feeling of being beautiful doesn't. When I am living as a woman, I am alive and feel sexy. When you dated me for the first time, I felt wanted and admired. It was the highest compliment anyone could have paid me."

I nodded and took a sip of my drink. I knew Mike wasn't gay. We'd looked at women they way men have been 'checking out the talent' for generations. He'd never made any advances toward me, in fact the opposite. While I had wanted to sleep with her after 'late night coffee', We had always said goodnight the way friends do.

"Is that the only reason you asked me to dress? Because I showed an interest?" I asked.

"No." she looked guilty. "I saw I could make you beautiful. You have very sensual eyes, a lovely shaped face. You have a good figure and ..." She got up and poured another drink. We were on the malt whiskies now and both of us were in a confessional mood.

"And?" I smiled at her, accepting the glass.

"And I can't answer that at the moment." She said.

"OK. Interrogation over. I'm sorry Michelle. This is a bit of a culture shock for me. I have never worn women's clothing before and I'm finding out I may have missed something in life. Cross dressing has always seemed to be a fetish – like bondage or whipping. It's just something that's never crossed my path before. And here I am enjoying it."

"I think you need to sleep on it." she said jumping up "It's late and you have drunk too much to drive home. I've made up the spare room for you. "

Yes, I was tired the combination of excitement and drink had drained me.

She led me to the spare room and hugged me as I entered. "I'll unzip you" she sad smiling into my face "And I'll do you" I said. Not sure if she would catch the double entendre. "Judging by her expression she did!

She turned and I unzipped her dress and, sliding her hair to one side, kissed the nape of her neck.

cdandy
cdandy
196 Followers