My Initiation

We arrived in the multi-story car park and set off into the mall. For the first half hour I was looking in every shop window, not at the merchandise but at my reflection, checking my looks and making sure no-one was staring at me. Finally, I settled down and started to enjoy myself. At first it felt strange to be examining panties, bras, slips and other women's clothing. Several times a shop assistant would come over to help and Michelle never seemed to flap at all. Then in one department store, while we were looking at blouses and tops, Michelle said "Wont be a moment." and left. So here I was. In the ladies section of John Lewis, All on my own, dressed as a girl. At first I started to panic and then tried to hide amongst the clothes. She was only gone about ten minutes but it seemed the longest ten minutes of my life."

"Where have you been? "I asked in a near hysterical voice.

"I wasn't long" she said "Just had to err... you know...go."

I smiled "Sorry. I'm just having an insecurity attack"

She put a hand on mine and looked kindly at me "Sorry. I keep forgetting it's your first time out. You look so natural."

"How many times have you been out?" I said. "I bet it's not many."

"Well... "she said with an impish grin. "this makes twice. And it and it was you that gave me confidence. I feel quite comfortable."

"Wish I did "I said

"Come on. We'll go and have a drink"

We went into a small wine bar and had a salad with a glass of wine.

"You know, you really do look like a girl. " she said "I wouldn't have brought you out if I wasn't sure. If you just relax, you'll look and feel even better."

I took her at her word and really did feel better. We carried on shopping and to our delight found an exclusive lingerie shop. The assistant left us alone to browse and we had the time of our lives. Underwear to die for. All matching sets made from the most luxurious materials. Silk, satin, chiffon – there was everything. We left with two large carrier bags and two very thin credit cards. I had bought us both a gown and nightdress set. Champagne for her and white for me. Although we always shared all the clothing, I wanted these to be special. We set off back to the car feeling happy but tired.

"I've never had such a wonderful day "Michelle said as we drove home. I had to agree though I was secretly glad we were finished. Next time, I knew I would enjoy it more but at the moment, all I wanted to do was get this bloody gaff off and have a shower. I thought the gaff had been a waste of time. There was no way I would have got an erection and I'm not really that well endowed enough to have shown anything through this skirt. However, better safe than sorry, I thought.

We each headed for the shower as soon as we got to Michelle's and I dressed in a simple pale yellow cotton blouse and a gypsy style skirt. I walked into the kitchen where Michelle was just ordering a couple of pizzas, poured her a drink and took it over to the sofa. I felt wonderful. The adrenaline was still buzzing in me and I suddenly knew what I wanted. I wanted Michelle but I was still on unsure ground. I didn't want to spoil everything by forcing some sort of gay sex on her but when she looked so damned attractive, her body parts didn't bother me. To me, she was a beautiful girl. The fact that I knew she had no breasts and boasted a respectable cock wasn't an issue. I knew she had a good firm body and to be honest, I wanted to kiss and hug her... and to sleep with her. Whatever followed from that was Ka, Fate.

I answered he door when the pizzas arrived and made the guy's night by giving him a sexy smile as I gave him the money. We ate them quietly, not saying much. I thought there might be a slight tension in the room. Afterwards, we sat and drank a couple of malt whiskies, both reflection on the day's activities. "Shall we slip into something more comfortable? "Michelle said after a while.

"That's a good idea. "I said" This bra's killing me. We both cracked up laughing and went get changed.

I undressed quickly and got the new wig out of my case. I put it on and gently rearranged any loose hairs with my brush. A dab of perfume in the important places and I was ready to dress in the new negligee set I had bought that day. The nightdress was white satin with embroidery round the bust and hem. The side split came almost to my waist, revealing most of my left leg. The straps, thin and fragile looking, crossed at the back, forming a deep 'v'. It felt delicious to my body. Cool and sleek. I put the matching gown on and checked the mirror. "Wow" I said softly . I was naked underneath, not wanting to feel anything but the nightgown and, even without the breast shape... I looked good!

I walked slowly back into the lounge and saw Michelle standing by the bar, pouring us a drink. My heart stopped. She was stunning in the new gown I'd bought for her. I was similar to mine but the champagne colour suited her perfectly. I walked over and, when she saw me. Her eyes opened wide.

"Oh "she said in a strangled voice "Oh wow! you look stunning... your hair..."

"So do you" I said softly. I walked over to her.

I stood in front of her and put my hands on her hips "You are the most beautiful girl I've ever seen. " I said and thank you for letting me share in this."

We looked each other in the eyes and it happened. We kissed. We clung to each other and kissed long and hard. Our tongues intertwined and our hands explored. Our bodies pressed close together, I felt the hardness between us, both with an erection. I could feel her cock pressing against my stomach, rock hard and hot. My own pressed against the smooth material of the nightgowns and the feeling was dramatic. My erection grew even stronger.

"Can I be your girl?" I asked softly

"Oh yes" she murmured "Please... sleep with me tonight... please"

In reply, I took her hand and led her to her bedroom. We stood face to face and I undid my gown and let it drop. My erection stood out in front of my nightdress but I didn't care. I moved up close to her and said "I'm yours tonight." And undid the bow of her gown. We were both naked under the sensuous nightdresses and this only heightened the erotic feelings we both felt.

Kissing we made our way to the bed and lay down, caressing each other. We lay on the bed our fingers searching and probing . I moved my hand down her back and caressed her bottom. She arched her back, pressing her hard cock into my chest. I was slowly sliding down her body, burying my face in her breasts, her stomach.

"Let me be your girl" I repeated and knelt astride her. I lowered my head and took her hard erection between my lips through the satin nightdress and stroked her balls with my fingers.

"Yes – yes" she repeated breathlessly and lifted her hips. My hand raised the hem and stroked her inner thigh. A groan escaped her lips and I lifted the nightdress clear of her swollen cock. I licked the shaft and caressed the full balls beneath and, licking my lips, took her into my mouth. She moaned and thrust forward, pushing it deeper into me. I raised up and sucked as hard as I could. Sliding my lips back down, I could taste the saltiness in my mouth. Up and down I went, my fingers caressing her balls until with a jerk she tried to pulled away.

"Stop...wait.... I'm going to cum...stop"

I thrust back down and took her in my mouth again, ignoring her cries. Swiftly, I held her cock and masturbated her while sucking hard.

The climax was huge. She bucked and twisted as jets of salty semen filled my mouth. I swallowed as fast as I could and kept her in my mouth. Slowly the jerking stopped and an occasional shudder ran through her body. I kissed her balls, and cock as she reached down and pulled my head towards her.

"I tried to stop you" she said. "Couldn't help it."

I kissed her deeply and said "I wanted you to cum. I wanted you in me. I wanted to be your girlfriend."

She held me tight and said "I've wanted you for so long. Ever since I first talked you into dressing."

"I've wanted you since I saw you in the street," I said "I've been slowly going mad, wanting you." We were kissing and stroking between sentences and my erection was near to bursting. Every movement of the silk around my hips ad thighs was now a pleasant torture.

"You didn't get anything out of that. " she said as she moved her hand down my back, round my bum and over my hip to the top of my thigh. I couldn't answer. I raised my leg and let myself roll onto my back. She kissed me all the way down to my pubic hairs while slowly raising the gown up to my waist. I felt her licking my cock from the tip down to my balls then gently sucking them while holding onto the base of my cock. I moaned and thrust my fingers into her hair. She licked back up my shaft and then took me into he mouth. The heat was terrific and thrust upwards with my hips gasping. It was over in just a few moments. She sucked hard up and down a few times but it was too much for me. I came into her mouth but she didn't stop. Sucking and caressing till I went completely limp. I sat up and she knelt in front of me. I threw my arms round her and we kissed deeply. I could taste my cum on her tongue as they entwined.

Finally we lay down facing each other, my arm under her neck, cuddling and her knee resting between my thighs.

I stroked her face and neck "I've never done any of that or had it done to me before "I told her

"Never? "she said amazed. "I thought everyone but me had done that."

"Never. " I said. "My wife didn't go along with oral sex. You've never had it either?"

She looked down "I've never had sexual contact with anyone before. A true virgin." I lifted her chin "Well you aren't alone you know. Sex is always boasted about. Take me... I'm thirty three. I can count the amount of times I've had intercourse on both hands, "I wiggled my fingers, One hand of which was on her bottom and the other down her back. "And I can count the times I've had oral sex on two fingers."

She shivered at my touch an buried her head in my neck. I cradled her closer.

"It was fantastic." she said. "But just lying here with you is lovely. You're right, I wanted a girlfriend"

" We both have a girl now" I said gently. "Don't we?"

"Yes "she answered. "It was what I wanted. It was very quick wasn't it? "she said impishly and smiled into my face.

"Very" I replied "I was so ready for you, I just couldn't hold it back."

"Me neither." She said laughing.

"It'll be slower next time "I said.

"You mean there's going to be a next time?" she said with amusement.

"I certainly hope so. " I said and reached between her legs. I stroked her cock and felt it twitch as she gasped. My fingers tickled and lightly scratched her balls. I took her in my hand and massaged her rapidly growing erection. She lay back, spreading her legs. I knelt beside her shoulders and kissed my way down her stomach, pubic hairs and finally onto her cock. I lifted my leg over her head so I was astride her with my own erection over her face. She took my into her mouth and I gently thrust my hips up and down pushing my cock deep into her throat. I sucked as deep as I could on hers and massaged her balls with my hand. It was slow and erotic. I felt her finger trail across my anus and a shock went through my body. She lightly rubbed in a circular motion then lightly scratched. I did the same to her, rubbing gently and slowly pushing inwards. It was too much and we climaxed almost together, both swallowing and jerking with the after cum spasms.

Again we lay in each other's arms, quietly kissing and fondling. Slowly we drifted off into a exhausted sleep, still cuddling.

I woke early, before Michelle and crept out to shower and get dressed. I felt absolutely marvellous. The sex had released a lot of pent up frustrations and now the Michelle and I were lovers, the days ahead looked sunny indeed. I was standing at the sink looking out of the window when Michelle came in. She walked over and threw her arms round me and kissed me. I held her close and kissed her.

"Mm that was nice." she said seductively. "As was last night."

"Last night was wonderful" I said. "I've never had anything like, or as good, as that.

She looked and smelled gorgeous. We were both in short skirts and casual tops. I had put my original wig back on, wanting to save the curly one for special occasions.

"Well I haven't anything to compare it with but you certainly drove me wild. " she laughed. "Lets have coffee in the garden."

We went outside and sat drinking quietly.

She looked at me seriously. "Does this make us gay or what?"

I thought for a few seconds. "I'm not sure I know. I know that I wouldn't look at another man with a view to sex and I still prefer women. Last night we were women. Different body parts but that's only lust taking over. To me, you were a girl I was making love to. A very beautiful girl who I have desired for a long time now. And if I'm gay, I don't really care."

I think that's how I feel too. Please don't be offended, but I've never lusted after you at the office. Dressed as a man, you don't turn me on." She ended lamely.

I laughed. "Of course I'm not offended Michelle. It's the same with me but looking at you now, I could eat you."

"Let me finish my coffee then. "she said through lowered eyelashes.

I did. We went back into the kitchen with our cups and I cornered her at the sink. I put my arms round her and we kissed deeply. I let my hand wander up her skirt, sliding up her stockings to the lace panties I found and rubbed the bulge underneath. Dropping to my knees, I lifted her skirt and mouthed her cock through the panties. I slid them down and took her in my mouth. All the time, I caressed her lovely bum, sliding a finger up and down the crease. She was moaning and making small gasps each time I touched her anus so I licked my finger and slowly pushed it in.

"Yes Oh yes" she cried as I pushed m finger around inside her. I sucked hard on her cock and she climaxed, bending low as the spasm took her.

"Oh God, "she said as she kissed me "That was wonderful." I kissed her tenderly "Lets go out for some lunch. I think we might need the rest." I suggested. And a drive somewhere.

"Great "she said and we went off to get ready. "I'm going as I am. "said." It feels like a mini skirt day"

"Me too. "she laughed.

We set off looking for a country pub and found one in a small village in the middle of nowhere. It was one of those places where everything goes quiet as you walk in. We ordered drinks and a sandwich and took them outside. It was a beautiful day and I suggested a walk to the top .of a nearby hill. It wasn't a very long way and we were soon cresting the rise to admire a gorgeous view over the surrounding valleys. We sat in the shade of a huge oak tree and just quietly enjoyed each other's company.

"I've really had a wonderful weekend. " I said looking into her eyes. "It's been like a new life for me."

"I'm so glad "she said. "I have too. It's such a shame you have to go home this evening."

""I wish I didn't but it's work tomorrow and I need some clothes. I cant really turn up looking like this."

She laughed. "I'd love to see their faces. Give them something to gossip about."

We headed back to her house and had a quiet dinner. Afterwards we made slow, passionate love, our hands and lips bringing each to a satisfying climax.

Chapter 8

The weeks and months passed blissfully. Each weekend spent enjoying ourselves, shopping, eating out, making love. We booked a weeks holiday to Scotland in a small hotel, taking only women's clothing for the week. It was glorious not to have to change back at the end of the first weekend. It was only a small village and we soon became favourites at the local pub. Randy Scottish farmers would compete for our company and by the end of the week we'd had several offers of dates. We even kissed a few goodbye on our last night at an impromptu party held on our behalf. I saw Michelle kissing one fine 'laddy' and realised I should do the same if we wanted to come back next year and remain friendly. Several young men had been chasing me all week so I did my duty and did the rounds, putting on a fine act. It felt very strange kissing a man with a stubbly face, but somehow rather exciting. Their hands were everywhere and I was hard pressed to keep them a safe distance.

Finally we went up to our room giggling and whispering about our 'conquests'. Lying in bed after making love, I turned to Michelle.

"Tonight, I really felt like a woman for the first time. They all treated me like I was special." I mused.

"And the kissing?" she said with a smirk

"A was excited by it " I confessed. Not the sexual side, the fact that I was looked on as a member of the fair sex." I cuddled closer to Michelle.

"And?" she enquired. I looked at her.

"I want to live like this and live with you. Because I've fallen in with love with you." I said softly. She hugged me hard with a huge smile on her face and watery eyes.

"I've loved you for ages now but.." she started

"You didn't know what to do about it" I finished for her. She nodded.

"Nor did I." I said "I wasn't sure what your reaction would be. But I do love you. And I want to live with you." She looked down saying,

"What about when I'm in my work clothes, in the shower or undressed though?" She asked.

"I'll still love you" I said, tilting her head up. "You'll see me the same you know?"

"I love you all ways and looks "she said. "I even want to kiss you at work sometimes." She said smiling.

"Resist the temptation. "I said laughing. Well unless we meet in a dark cupboard.

"That can be arranged" she said in the sexiest voice I'd ever heard from her. She took hold of my limp cock and made it grow.

That started us off again. She worked her way down my body straddling my face with her legs. I still marvelled how large her cock was. It filled my mouth with plenty more to spare. She always managed to suck my six inches fully, her nose pressed to my balls. She fingered my ass and slipped a finger inside. I did the same to her knowing it would bring us both to a dramatic climax.

We had never discussed anal sex. Like most things between us, we were probably afraid to bring the subject up.

So I moved in with Michelle and put my house up for sale. It was strange leaving her house, together for work but Michelle had been right. Even dressed in a suit and tie, I still loved him. It was those beautiful eyes I think. I could look into them and lose my heart entirely.

One evening, we were just lounging about in underwear after a busy Friday at work, kissing and having a cuddle on the sofa when she said quietly, "Have you ever had anal sex?"

I looked at her "No. Have you?"

"You know I haven't " she said with a smile. "I just wondered what it would be like.

"From what I've read, It is erotic, wonderful and can be damn painful. " I said smiling

"Hmm " she said "Just what I've read."

She was looking extremely beautiful dressed in a pale pink lacy chemise and panties. The lights were low and we'd had a few drinks.

"I'd like you to fuck me" I said quietly.

"Same here" she said breathlessly. We stood up and went into the bedroom. It was like a first date all over again. we undressed each other completely, kissing each other's body as each garment was removed. I made her lay on her back on the bed and straddled her legs. I bent over and sucked her cock till it was huge and erect. Reaching over to the dressing table, I took an bottle of hand cream and massaged her cock. I looked at her face. Her eyes were closed and she was breathing deeply. I spread some of the cream across my ass and pushed a finger inside and opened myself then two fingers. I moved up and straddled her cock. Taking hold, I guided it to my anus, and started to sit back, gently pushing it into me. She was huge. 'This is going to hurt' I said to myself but pushed the tip of her cock deeper into the entrance. It wasn't as bad as I thought. The tip slid in me after a few minutes of lifting myself up and down on her cock but with some pain. I stopped and waited, eyes closed. Michelle had gone perfectly still waiting for me. The pain subsided and I sat back a bit further. Each time it hurt I would stop till it eased, then sit further down. At last I was sitting on him with no pain and I lifted up and down. I felt full but excited. I lifted up and down a few times. In fact I felt good. After a few minutes I lifted off and lay on my back with my legs raised .