The long and winding night

By Lucy G.

Published on Jun 2, 2024

Transgender

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I attended to a massage course.

It seemed appropriate at the time, I guess I imagined, that muscular men or other men of my taste would like to indulge in massage therapy after their workouts, and I could touch their sexy bodies and maybe, who knows.

The course was held quite far from my home, so I've decided to stay in the adjacent hostel,. The lessons went smoothly and after a year, the course was slowly coming

to an end. There was only a month left. It was January, the weather was very unpleasant, it was quite cold and windy outside, and surprisingly snowy. I was staying in a one bed room, And therefore I could be a Lucy, safe and alone as I liked to be.

I was lying in bed in my pink Victoria Secret night dress, dreaming. My hand was on my clitty, lightly caressing it through the pink satin. The night dress consisted of very light, cute pink shorts and the tan top with spaghetti straps of the same material and colour as the shorts. I dreamily imagened a man lying next to me. The man was just a man

with no identifiable face.. Then I started to feel a desire for someone more real and decided to turn my laptop on and looked at an erotic chat site.. There was no TG room on the site, but I regularly visited Gay chat room. Surprisingly, I started talking to a guy pretty quickly. He introduced himself as Paul. And something happened that does not often happen in a chat room. only When the right partner is onth the other side and when both are in the right mood.

I should have found out, that under the special condition, a lot of

things can happen. Even the most important thing in a sissy's life.

I told Paul the usual stuff about my age, status, etc I didn't told him that I'm a sissy, even didn't told I'm bottom. Then all of a sudden he asked me for my telephone number. I froze.

I must ignore him, I told myself. I was not in the habit of giving my number to men I've met in gay chat rooms, and in fact I didn't give my number to anyone.

I was a sissy in the closet, scared that someone would find it out and

I wouldn't be the old good fellow anymore. The one, who drinked beers with friends, who pretended to love women with big tits.

But that night, there in the bed, it was dark and cold out there, me alone, my clitty alone too and we both wanted someone. I thought, so what, just the number, he won't call anyway, I knew these faggots from the Internet. Lots of guys, lots of bull-shits, and no action. So I send him my number. The phone rang immediately.

Almost mindlessly I took the call.

Paul and I talked for a long time. It was just nice and pleasant, I was stroking my clitty whole time we where on the phone, but not too much,because I didn't want to cum. I just wanted to be with a man, in my pink robe imagening that I was a woman talking to a lover. Paul asked me if I wanted to meet up. His suggestion surprised me again..

But maybe it was something in his voice or in his attitude, that made me answer all his suggestions with a yes as if I had not thought about the consequences, that I usually worried about.

And something came to my mind which probably could make the situation more acceptable, for me, for

the rational part of me, for my male part, which was without any feelings, emotionless, with little interest in sex.

Wouldn't you like a massage from me, I asked Paul? Like I told you, I'm here to learn how to give massages. We already give massages to people who want to be massaged by inexperienced therapists at a very low price.

He agreed to come the very next day.

I was on dates with a few men before, but it always brought me a lot of stress. It was obvious that the men were always planning something or let's be plain planning sex. I wanted it too, and I wanted be with a man, I wanted it all. But at the same time, there were the circumstances, me uncertain, unable to say no to anyone, afraid of the possibility it coming out

And well, it's two completely different things, shoveing a dildo up your ass or your mouth , in the safety of your home, or giving

yourself to a man, horny, rough, with no needs be kind to you, because he wants to cum, regardless, whether the sissy his penis is buried in is screaming in pain.

The next day Paul really came. He stripped down to his briefs, which hugged his private parts nicely

and the lines of his cock was clearly visible and it made me shiver a little but I was too nervous to be arouse.

From the very first moment he was very insistent and I began understand what men are really like. I've never been like that, never been so rough, driven by my own desires to get some chick. That was Probably why I was a sissy. Paul attacked me again and again,

See how hard I am? Strroke me down there, he whispered.

The problem was, that one of my colleague was standing behind me with a client and I was scared. I was scared of the man, scared of the possibility being caught stroking another man's penis.

Paul didn't care, he wanted to get off, he wanted to have sex.

He wanted it with me. One of my ultimate dream came through, a man wanted me. Why I didnn't want be his?

Paul was an average looking guy, about 45, maybe a little overweight. He

wasn't the guy I fantasized about as I was lying in bed in my sexy underwear, daydreaming. I could smelled the cigarettes on him and it didn't plese me, because I couldn't smell his true scent.

I liked his cock, I probably liked his lust and the eagerness and being

the centre of his attention but I wasn't ready to continue this adventure.

I was really like a virgin young girl , who heard a lot about what

men are like but never imagined such hunger, such lust. I really was inexperienced and unaware of how men really behaved. And my sissy soul was looking for some more romantic treat.

And here was a man in need, maybe he had not sex in a long time and I was sure he was only desperate for me because.

But I found that if a man wants it, the woman have nowhere to run. Or women probably know how to escape, but a sissy like me, very submisive and without a shred of assertiveness will just surrender. My fate was already sealed.

Paul may have known my needs better than i did.

And even a little romantic was in store for me. My colleague finished her massage sooner than I did so there wer just Paul and me in the room After I finished.. He put on his clothes, even a warm jacket, and it looked like we just going to say good bye to each other and never see each other again. But suddenly he kissed me deeply, with his tongue, I am not sure if I let his tongue slip into my mouth because I was surprised oor if I really wanted to, or I just gave in to a strong person like always did.

After kissing me he said:

i was thinking about a gift for you, because you wer so nice to me on a phone yesterday. I've thought about flowers, but it might seem weird , that I'm heading with flowers. to a massage therapy room. It's chocolate for you, just for you.

I was mesmerized, unable to speak. All I knew was , This man is treating me like a woman on a date. I am a mwoman now, at this very moment. I am a real woman with my man, with a man who wants me, even if he would only wants me for a quickie

My romantic self, or at least the romantic part of my soul was in a state of bliss and it filled me with a kind of ecstasy.

he doesn't look so bad, i thought, , on the contrary, I suddenly thought

he looks pretty good and sexy. i could probably spent a few more moments with him. Maybe he'll say

some more sweet words to me. It was so thrilling to hear those words.

Would you like to have coffee with me, he asked.

Feelings flooded my mind , I knew he was kissing me passionately, I knew I've had got the gift from this man and I was unable to thing about anything else.

I've just told him to wait because I have to change and then I would have coffee with himm.

Of course I put on my male clothes, only the panties, red thong I was wearing , no one could consider as male's'. They xcreamed Fuck me!. The back strip created a permanent sexual tension in me and I guess

that it made me more flirtatious and pleasurable. I went back to Paul and told him I was ready.

It took us a lot of time to reach the Café, even though it was

only few minutes away. We were kissing every few steps. Under the kind dark winter sky. The wind and the cold faded away. And yes, that scene was so romantic.

I tasted his tongue roughly invading my mouth, hinting at what was to come even though I wasn't thinking about it right now.

The streets were empty, just a confused sissy and a man who wanted her kiss again and again And I gave in because I liked it mmore and more an I liked this man more and more and wanted to be with him, Strange and new feelings rosed up in my poor head.

He even put my hand on his crotch while we kissed.

I was in heaven, I aroused him, , no doubt about it, his cock was hard. How great, that a woman can find out it so easily.

Did I realize in that moment that it was all going come down to me

lying under this man with my legs spread wide and my ass filled with his cock? Well, subconsciously I knew it, but surges of sexual and sensual arousement was coursing my body and soul and in this situation I began to mentally accept that inevitable must come. We walked into the café and sat in a dimly lit corner. I was aware that the scene was carefully chosen . But I already

had lost. interest in such details.

All that mattered were his kisses, his hard cock in his pants, his whispers about how sexy I was, how attracted to him I was. I didn't care about anything else.

We talked about sexy things, but my mind was too blurrry to remember anything.

I listened to him, his words whispered to my ear to hypnotize me.

Of course it worked.

Do you like my cock, dear, he asked. And he put my hand under the table on his bulge.

I blushed, but I let my hand there and started stroking it.

When the waitress came to our table to ask about our orders, I tried to pull my hand away. But he was stronger than me. I didn't look at the waitress and didn't know, if she saw my hand there. On the other hand, being here, exposed, with my soon to be lover brought me a kind of satisfaction.

At least the waitress could see who I really was. She was a little flirtatious with Paul so I assumed, she liked us and she liked our relationship.

Paul was more and more intrusive, stroking my body, kissing me, interrupting my every attempt to resist him and ignoring my whispers: No, not here, someone will notice, I whispered.

Then he said he needed go to the bathroom and He wanted me to go with him. I'll show you my cock, you want to look at it and touch it, dont you. he asked. I said nothing, I just got up and followed him like a puppy his Master.

I didn't want to be without him even for a short time and yes, , I wanted to stroke his cock and I wanted much more. We went to the bathroom and locked ourselves in a stall. He started to kissed me, I completely surrendered to his tongue, to his maleness, I let him put my hand on his crotch again. Take it out, he said. And while we kissed I unzipped his fly and there it was, beautiful hard cock of this charming man, that i was beginning to feel something for. I stroke him, he was breathing faster and faster. Then stopped me.

Show me yours, dear, he whispered.

I blushed. I can't do that ,, replied i, because I realized I had the ssexy panties under my trousers and he would found out I was a sissy.

But I was no longer the one running things. he simply unzipped my fly and pull down my trousers. I stayed there, with my clitty peeking out from under the red thong.

so we actually have a cute girl here pretending to be a boy, said he.

I'm sorry, Paul but I should have told you, that I'm, yes, like this..

Don't apologise, my dear. I found you quite feminine from the first moment.

And do you like it? I asked.

I wouldn't have met you, if I didn't like your feminine manner and attitude. And those pretty panties make it even better, showing offf that tiny thing.

I blushed again and snuggled against him, hiding my face. against his chest.

We went back to our table and sat down.

We talked some more. I told him that I've never been with a man and that I've been seduced by a few women. although I had no strong temptation to be with them. And in truth i afraid of that because I knew they would want my cock hard and I was not sure if that was gonna happen. And of course, in most cases it stayed flaccid, so I only got laid once.

Paul had his hand inside my trousers to feel the material of the panties. It seemed to me, that he liked them

You come with me, we can have a few drinks at my place and have a nice evening together and make out. And you don't have to worry about anything. Everything will be if you want it to b.

I didn't know how to answer, I wanted it and I afraid of it. It was clear to me, that if I went with him, we would make love, or he would make love to me or he would fuck me, whatever you want,. He knew it too, he knew from the first moment how to treat me and I just did what he wanted.

I would like to be with a beutiful girl tonight, in sexy panties, that I would like to take off, if the girl would like it, he whispered to my ear.

Do you have other female clothes in your hostel.

I noded.

And wouldn't you like to take them with you so you can change and be my

dressed up girl.

I nodded.

We paid and went to my hostel. I quickly packed almost everything I've had brought for Lucy.

Paul called a cab and we drove to his appartement.

to his appartement.

In the cab I was scared, excited, mixed feelings were coursing my body and brain.

I shouldn't have. I don't know him. I don't know if I can handle sex if he wants it. And he does, he's a man. And I know myself, I won't

refuse any of his suggestions.

Because I'm a sissy and he is a man, because I'm naturally submissive and he found that out. And because I want to, and I want it with Paul, whom I didn't know yesterday and now feel so strongly about.

We came to his appartement. He mixed some drinks, and lit a cigarette. I never liked the ' smell of cigarettes but I snuggled to him anyway.

and started kissing him lightly all over his body, touching the bulge in his pants now and then.

I drank two stiff whiskeys and became a little bit tipsy but I already was because of him.

Show me your wardrobe, he said.

I showed him my bag.

He took everything out of it.. He handed me the pink fishnet hold ups and the pink top of my night dress. In fishnets, I asked with a smile. I thought I was going to be your virgin bride tonight not a slut.

You're going to be the sweetest and the most innocent slut I've ever met, cutie. All pretty in pink and red. I hope my hungry cock can stand it, I'll be fucking you all night long.

I started laughing and hid my face on his chest.

I went to the bathroom, took a quick shower , cleaned my insides and put on some make up. I had a pink lipstick, and black eyeliner, mascara. My eyes were expressive and my lips perhaps kissable.

Paul got up and turned on music player. The sweet, romantic music started playing.

he pulled me over to him and started kissing me passionately , his tongue exploring my mouth. I let him in. Now I was ready let him whatever he wanted. He was the one who wanted to be plesed and I was the one who wanted to please him, because I felt his pleasure will fullfill me.

He seduced me, he got me, now I was his and he had the right to take everything.

We were dancing a kind of a sexual dance, glued together. He pulled me to him, starting making out with me. I felt his hands running over my body from top, down to my ass, lightly caressing it, only the thin strip of my panties between my entrance

and his rough wanton hand. He played with the pink strip , moving it back and forth, his fingers touching my hole now and then.

I was all his, melting in his arms, moaning, letting him do everything. I accepted his finger, probing my hole.

And then I put my hand on his manhood, so big, so dangerous and so irresistible. My hand stayed glued to that spot throughout our dance. I began kissing his neck, his chest murmuring words, he could not understand, because I didn't want him to. The words of a little sissy virgin who was full of desire for this man.

he Undid his pants and pull them down , holding his hard cock in his hand and stroking it slowly.

I gasped and stared at it, not understanding how aroused I'm at the sight of the thing which I have seen thousands times before. But well, the thing I'seen was much shorter and thinner as this of Paul, which was about to enter my mouth or pussy in a few moments. He put his hand on my sholder and I knew waht my man wanted. I wrapped

my arms around him and got down on my knees. Slowly, I felt the tip of his manhood draw a slippery trail, down my pink top.

And then there I was , in front of him, in the position that women know well. But I've only been dreaming until now. His cock was in front of me, so close that when I stuck my tongue out I could lick the tip. The flavour was a little like salty, a little like tasting of the cigarettes but I knew I want to taste it.

I started licking the head, while I pulled the foreskin back. I swallowed the head and really suck on it, like when I sucked on a candy as a child. But oh my, I've never sucked candy so sweet, no candy has ever brought me such pleasure. I tried to stick my tongue into the piss slit.

Paul groaned.

Great, you're doing great, he whispered. I also tried sticking my tongue under his foreskin running my tongue over the head, to find that spot down there, hoping he would like it when I pressed my tongue against it.

I was drunk on sucking, alcohol, the smell of the man. and the fact

I have become a woman and his lover. My hips moved involuntarily,

because I desperately needed to relieve myself Bitch in heat. Come on girl, I want to squirt my first load up your pretty ass.

he helped me up. And we headed for the bedroom. There was a king size bed. I climbed on it and lye on my back,

spread my legs and waited there, in my fishnets, top and panties

He undressed, pulled lube ot of drawer and looked at me. I lyed there in the inviting pose, opened , watching my man do his things.

It was so beautiful to be in that pose on this side of love. Waiting to see what was going to happen, what my experienced, strong and exquisite lover was goint to do to me. All I had to do was open up and give him my body to use. No one asked me to be funny, strong, hard, I was a little girl, who had a great Daddy who knew what was good for his little pink doll. She didn't have to bother.

I was just pretty in pink in his bed.

Finally, everything was as it should be. I was in the right role for me, with the right person.

He lay down next to me and started kissing me again. I felt his finger looking for my virgin hole, and when he found it, he

tried to enter it.

I have fucked a lot of times with a pretty big dildo so that was not a problem He went on to prepare my hole. Our mouts were glued together and I was making sure his cock stayed hard. I was eager. It was almost unbearable.

Why am I not a woman, almost always ready for my man.

I felt the three fingers that were actually fingering and preparing me

being pulled out

Paul quickly lay down between my spread legs, so sexy in my fishnets. All he had to do was pull my panties off and toss them aside and then

I could feel the pressure against my opening. The moment I have probably dreamed of since childhood, had arrived.

He kept the pressure steady and I felt a pop as my hole opened and the head pushed in. I moaned. He held still for a moment and then with one thrust he was all the way in.

My walls felt his cock slide in until I swallowed him whole.

His shaft and head were buried deep inside me and his balls were touching my ass.

Then he started moving his pelvis. I could feel the shaft moving inside me, as I lay under him, in the classic position. I liked the position. I could wrap my slender stockinhed legs around my lover's back as he was in me, and this made me feel -so fem.

My man's cock made his rhythmic motion inside me . I could hear his breathing next to my right ear, stroking the fantastic man with my hands and legs moaning each time he was fully inside.

Sexual fever began to consume me and then I lost the control I've been trying to maintain all my life. I started screaming and crying

Fuck me, fuck me, make me yours, i want you, i love you. More, do it to me.

He was fucking me, he wanted to get off and I was being used for that purpose. I'd never experienced such a feeling until I was used by a man.

My friends were right, sex is so fantastic, but I didn't realize it until he was sticking his dick in me. I just had to had sex differently than they did. I was in a state of ecstasy, sexual bliss, and I was whispering to him:

Please, fuck me, please, I am your slut, I'll be your slut forever, I will do anything you want.

Then he stopped, burried deeply in my ass. I realized, I was getting my reward, I was getting what was mine. I press my cunt against his crotch, trying to pull him to me with my arms and legs to get every drop of what belonged to me..

I started to cry, feeling his cock leve my pussy. Paul lay on top of me for a while, I kept hugging him, not wanting to let go. Then he rolled off and lay on his back next to me. He lit a cigarette, kissed me and said:

I seem to have a new girlfriend even though I was looking for a boyfriend. But your even better than a boy, and you're such a good fuck.

I sighed and happily snuggled up to him, kissed him deeply, then I moved down to his beautiful cock, to clean it. And get it ready for another round?

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