Natalie Finally Begins to Learn

Background

I am a long-haired man in my forties. I have been married, divorced and married again. I have children from both relationships. I do plenty of manly things. Yet, behind all of this is the overwhelming desire to be a sissy. I cannot explain it to myself never mind to anyone else. I fight against it mostly as it does not fit in to my everyday life but Natalie stays lurking in my head. She has been there for many years.

What I have not ever done is admit to anyone else about Natalie. She is me and I crave to be her. I crave to be treated as a woman, especially by a man. However, I do not fancy men. I do not find men attractive but if I am dressed up as Natalie then by God, I need a man to treat me right and I would submit to him and please him. And yet i would be fighting it in my head. It is that constant duality going on between the male and female me. As soon as I orgasm though, my male self re-asserts himself and I am again not interested in mens' cocks. Having read around the topic of sissies, this is a pretty classic mechanism. I know I am not alone in what I want or think.

I look at women and I assess them, as any man does. But a man would be thinking "fuck her" but the sissy is looking at her body shape and hair and clothes and make-up and shoes and how she moves. The sissy is envious, wanting what she has.

I look at women's clothing and would love to wear it myself. I am so bored by male clothing - the dullness of the colours, the designs. The lack of creativity. It is all so predictable. Female clothing though takes my breathe away. I want it. I want to feel it against me and I want to feel sexy in it. Then I want a man to want me in it.

I go through stages of shaving parts of my body smooth. I am married so i cannot just shave myself smooth as much as i crave it. Currently, my arse and bollocks are shaved smooth. My wife doesn't mention the smooth arse but likes the smooth bollocks - less hairs in her mouth. So double happy days there.

I can now wear knickers on my smooth arse, under my male trousers, sometimes to work, sometimes just around the house and i worry about being found out.

I have a CB6000 cock cage in the house and i like wearing that but of course i am my own keeper which is not the control i need with it but the feelings of restriction and loss of control are somewhat there. Again, to be someone else's caged sissy. Well...

I am too scared of being found out to initiate anything. Plus i am not feminine looking so i just plod along in a cycle of fantasy and craving and wanking and orgasm and denial.

The following is my story:

Imagine meeting Lewis one day.

He is a normal bloke, mid 30's. I am not into men so i don't see anything sexual in him, as normal with any bloke. He chats with me on the street outside his house as i walk past. He is doing some work there and i pass a comment and we end up chatting. He is on his side of the 3 foot wall and I am on the public side. He has tools strewn about and is working slowly as we chat. I am about to move on when he asks me to pass him the hammer, lying on the floor on my side of the wall. Where it is, I have to position myself side-on to him to bend down to get it. I lean over, pick it up and turn to him, handing it to him. He takes it strangely, has gone a bit quiet and looks at me in an odd way. I don't think too much of it and say my good-bye.

He waivers then says "Look, can you help me for a couple of minutes please? I need to get a concrete post from the back and it is going to be easier with two lifting it. Would you mind?"

I am happy to help out and we walk into his back garden that has higher fences and is much more secluded.

He walks in to his garage, talking mundane stuff and as i enter he turns and just looks at me.

"I am going to do something now that i normally don't do and if it is wrong then i apologise and you can just walk straight out." he says, almost falling over himself to get the sentence out in one breathe.

I look at him bewildered. I have no idea what he is talking about. I then watch in total shock as he drops his trousers and shorts to the floor and stands there with his cock stiffening quickly as i obviously just stare at it, then at him, then back at it as it flicks higher.

"i want you to get on your knees and suck me" he says and again i stare at him as though "what the Hell?" but i don't flee. I am just so shocked.

"What makes you think..." i start but he cuts me off with "I saw your knickers. As you bent down. I have always wanted a sissy to suck me off and it looks like you are it. Please leave if it isn't you. However..." and this is where he won me, "I shall spread it around that you wear female underwear. I know that bit is true because i have seen them just now on you. Whether or not you are into men, i have no idea but i am willing to bet that you don't want it becoming known. So again, come here and kneel down" And he looked at me in a sort of apologetic way but then with an essence of steel in his voice. He had the dynamic perfectly. He was the man. I was the sissy. I could feel the change in my head. I had to obey him. I did not want to obey him. I did want to obey him. I had craved this moment for nearly 30 years and here it was. Yet...

I opened my mouth to say something, realised i didn't know what to say and so closed it. I still stayed where i was.

"Look, take your trousers off. Show me your knickers. You can see i am hard and want it. Show me you are a sissy."

In a dream state now, becoming Natalie more, i nodded slightly and unbuttoned and unzipped my trousers and let them fall. I was wearing a pair of black knickers, fairly lacey (so i could feel it against my cock) and a thong, so the material cut up my arse, which i liked.

"I knew it" he gloated. His voice had gotten stronger now, more firm and he had me hooked a second time. "Come here sissy. You have a cock to service". This time i waddled over and stood before him with a sort of stunned mental state. He smiled at me, knowing he had won. "On your knees, sissy" and i got to my knees. My mind was racing. My heart was pounding. My cock was still flaccid in my knickers but I had his cock right before me, flicking gently up and down. In a trance, I moved my right hand up to hold his cock and i then leaned in to kiss the tip of his cock.

"Mmmmmm yes baby" he moaned and I was fully Natalie then.

I kissed the head of his cock many times with soft kisses, not really trying anything. I was still in a state of shock that i was actually doing this but the world had not caved in and i did actually like having his cock in my hand.

As i kissed it, so my right hand reflexively began to wank him, slowly up and down and he moaned some more so I carried on rubbing and kissing his cock. I was enjoying it. It wasn't the worst thing in the world. I liked being on my knees and i liked the feel of his cock. It was rather large, larger than mine with a now-enlarged head. I tentatively stuck my tongue out and licked under the head to the eye. I did that several times then allowed my tongue to swirl around the head. I even licked the full length of his cock from his balls to the head. I closed my eyes and thought "I was actually licking a cock"!

"Put it in your mouth and suck it now" he whispered. As he said it, he put a hand against my head and his fingers gripped through my hair. I opened my mouth then and slipped his cock into my mouth and closed my lips around the head, holding it possessively. My tongue was working busily in my mouth on the head and my hand was still rubbing the shaft. I could smell his scent and sweat and i liked it.

I moved my hand to the base of his cock and rested it on his belly and i began to bob up and down his cock, back and forth, making squelching noises and generating so much saliva that i swallowed it noisily at times, having forgotten to do it naturally. I was sure that i swallowed his pre-cum at the same time but that fueled my efforts on and i was now, inelegantly, sucking eagerly on his cock.

I moved both my hands onto his belly to brace against as i sucked him, getting more turned on by the situation.

I was lost completely in the moment of being Natalie, on her knees for a man who was hard for me. I could look after him and treat him properly. I had found my position.

He was moaning loudly now and thrusting into my mouth with little spasm movements. I liked the feel of his cock moving in and out of my mouth and i wanted to be so good to him..

I looked up at him then, to see what he was doing and he was already watching me. My eyes smiled up at him as i serviced his cock for him. He groaned deeply then and i felt his cock change. It swelled and then he was shooting his load into my mouth with no further warning. I was shocked by that. I had never managed to eat my own cum - the fun of doing so left me the instant i orgasmed, every time but here now, i was loving the moment of this man cumming in my mouth. I did not like the taste at all but i loved the fact that i had made him cum and i began to swallow the liquid: both to remove the taste and feeling of it in my mouth but also because it was the correct thing to do.

I sucked eagerly on his cock until he had stopped shuddering and to be honest, that was my greatest moment - having him squirm on his toes and making his groan loudly, flicking his head with my tongue as it became super-sensitive.

I eventually pulled away from him and let his cock go, watching it shrink and soften before my eyes. I remained on my knees though.

I was still Natalie. The male me had not regained control. I was still horny. I looked up to him. "How was that?" I asked slyly. He laughed, moving a hand over his face. "It was a good start. I guess you are going to tell me that is the first cock you have had?" I nodded up at him and kissed his cock for him in response.

He laughed some more. "Well, it won't be the last time you suck my cock, sissy, will it?" he said.

I continued to look up at him and i shook my head. I was who i was meant to be in that moment and i loved it all.

Come back tomorrow at 7pm and wear some nice lingerie. I will enjoy you sucking me again. Now, fuck off and he laughed.

I got up unsteadily, in a daze. I wiped my mouth on my hand, still tasting him in my mouth. Still feeling his lovely cock in my mouth. I pulled my trousers up and walked out and walked home.

That night i did not wank. I wanted him to make me cum tomorrow.