• =?UTF-8?Q?My_Initiation=2c_bycdandy=c2=a9_long?= (3/3)

    From a425couple@21:1/5 to All on Fri Oct 4 15:53:38 2019
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    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 .
    Report Story

    bycdandy© 109 comments/ 636343 views/ 163 favorites

    My Initiation
    bycdandy©
    "Fuck me now" I said sexily and she got up and lay between my legs. I
    guided her in to me then put my arms round her as she pushed her cock in
    and out of my ass. She fucked me. I felt no sexual gratification other
    than I knew I was pleasing her but it did feel nice. She pumped harder
    and harder, her large cock sliding in and out while I stroked her hair,
    neck and body. Finally with a cry she climaxed into my ass. Jerking and
    lowing down, she lay across me panting and opened her eyes. I took her
    head in my hands and kissed her deeply. I could feel her softening
    inside me and pushed her bum towards me trying to stop the inevitable.
    She slipped out and I lowered my legs into a more comfortable position.

    "Oh that was terrific. "she gasped. "Did I hurt you?"

    "Only at first " I said, kissing her and grasping her round the neck.
    "It felt amazing. You can do that again any time you want."

    "She laughed. "Oh I'd like to. But you're going to do me as well you know."

    "Shower first" I said with a grin. We dashed off for the shower and both
    stood under the jets kissing. She took the gel and began to soap me all
    over. And she didn't miss a thing. Starting with my back, massaging my shoulders and working down to my buttocks. Her fingers caressed my anus,
    even slipping a finger inside as she kissed my neck. I was starting to
    get hard again. Her hands reached between my legs and gently rubbed my
    balls between her fingers.

    "Turn round" she murmured. " and began to wash my chest, working down to
    my stomach and finally my erect cock.

    "My turn to wash you. " I said after a few moments of her masturbating
    me. I didn't want to cum just yet. I took the gel and started on her
    chest then, turning off the water, began to soap her all over. I paid
    special attention to her cock and balls, keeping up the strokes till I
    felt it harden. Then I turned her round and started on her back. Working
    my way down I slid a soaped finger into her ass and started to widen her
    hole pushing her forward. She gasped as I inserted two fingers but not
    in pain but in pleasure. As soon as I thought she was wide enough for me
    to start, I soaped my cock and placed it at the entrance. Very slowly, I
    pushed backward and forward as she was able to take me inside her. My
    cock is a smaller than hers and after a few pushes slid inside. I kept
    very still for a minute until I felt her push back towards me. I new she
    was ready now and began to push slowly in and out. She was moaning with pleasure. I reached a hand round and started to masturbate her in time
    with my motions. It felt wonderful. Her ass was so tight and hot, her
    muscles tightening and contracting adding to the feeling. I lost myself
    in my ecstasy and went faster and faster. I exploded inside her with a gasp.

    My passion spent, I put both my arms round her and held her, kissing her
    neck until I slipped out of her.

    "That was wonderful" I said. She turned round and hugged me.

    "That was a fantastic feeling. It didn't hurt at all".

    "Probably cos I've not much to boast about" I said laughing.

    "Well I think it's the best cock in the world she said taking it in her
    hand."

    We showered off and dressed in our baby doll nightdresses and went to
    bed. I hadn't realised we'd been at it for three hours. It was late and
    there was work tomorrow I thought with dismay. Back to the suit and tie.

    Chapter 9

    Michelle came home from the office next morning looking worried. "I
    think the cat's out of the bag" he said "I've just overheard someone
    saying we were living together and were gay."

    "Cant be much of a rumour" I said "For once they got it right"

    "I'm not sure I can stand being the subject of their gossip." She said.
    "It's only a matter of time before they find out everything. They wont
    leave it alone you know."

    I nodded. "Come on into the lounge Michelle, I've had a bit of a plan
    going round in my head these past few weeks. I haven't mentioned it to
    you because I wanted to get the details sorted in my head." She sat down
    beside me and I put an arm around her. Her head tilted to one side
    looking at me closely.

    "I've sold my house now and there's a lot of money waiting to be put to
    good use." I took a deep breath. "I'm sick of changing into a man each
    Monday morning, then coming back to living the life I really want. It's
    time for a change. My plan is, if you're agreeable, to start our own accountancy business with the money. We're both fully qualified. We
    split everything down the middle, both of us equal partners. I live with
    you, so we really share that side of things. We can probably steal a few clients to get us started and when we get busy, hire a few others to
    work for us. The thing is, we become women accountants. No more male
    clothing. We start off as women and work as women. Now here's the catch.
    Will you marry me?"

    She took a deep breath and flung herself on top of me in joyful tears.
    "Of course I will. Yes. Yes." She cried. "And your plan. It's
    wonderful." She sat back after a few moments looking at me with an awed expression. "You'd do all that for me?"

    "For both of us Michelle. I want to be a woman just as much as you. We
    share a house and now we can share a business. Unfortunately the
    marriage wont be legal but In our eyes it will be."

    "In my eyes, you'll always be my partner." She said quietly. "I suppose
    we become lesbians."

    "Lesbians are more accepted that transvestites," I said. "Yes, we'll
    promote ourselves as lesbians."

    So we followed the plan. We became quite successful and threw away all
    our male clothing.

    The plan for next year is to complete the transformation medically. But
    that's for next year.

    The End

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    bycdandy© 109 comments/ 636343 views/ 163 favorites
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    Recent
    Comments
    by pantyhigh
    08/06/19
    Sexual Adaptation for Connection
    Great story about 2 "people" who just connect. Nice they worked through
    the sexuality without losing the relationship. Shows how sexuality can
    adapt to the situation.

    If the above comment contains any ads, links, or breaks Literotica
    rules, please report it.
    by 13thChildofLeeds
    06/20/19
    Excellent!
    So sweet and tender. Thank you for taking the time to describe the
    formation of a full relationship. Very well done.

    If the above comment contains any ads, links, or breaks Literotica
    rules, please report it.
    by Anonymous
    06/06/19
    Thank you!
    Love every word of the story, wish I was in it. Put lots of my thoughts
    and ideas where it should be, I do undertsand more of myself now. Gender
    or style is not important, what makes me comfortable is...somore...

    If the above comment contains any ads, links, or breaks Literotica
    rules, please report it.
    by Anonymous
    01/13/19
    Loved it
    I loved this... I found myself routing for both girls. Well done.

    If the above comment contains any ads, links, or breaks Literotica
    rules, please report it.
    by sweetfairie
    11/04/18
    Such a beautiful story!
    I'm not sure how many times I've read this story. I think it is the most beautiful story here--and every time that I read it, I wish that I could
    have lived such a life. Thank you for such amazing writing.more...

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