tagTransgender & CrossdressersRaymond My First Man Pt. 01

Raymond My First Man Pt. 01


I work from home and I am a transvestite, it is wonderful to be able to dress as I want and just enjoy life and my work as Joanne. The other day I did something I had never done before and it was so astonishing.

I would often rent hotel rooms to dress and spend the night as Joanne and enjoy myself. One such night, a Monday, I was at a hotel and I felt lonely, I decided to call a friend, a long-time friend that did not know about me but who I knew had often offered me such things as skinny dipping with him but I had never taken him up on it. I told him where I was and if he wanted to come he had better be prepared for a surprise as I had never divulged that to him. He told me he would come right over; I had about thirty minutes before he arrived.

That night I had dressed carefully and while waiting for him I made sure I was as perfect as I could to impress him. As I looked at myself in the mirror I felt quite feminine by my reflection. I had on my white dress with the black accent on the collar, sleeves and pockets. This dress was really sheer and my black satin lingerie could be seen through it. I wore my black satin bra and panties set, with my black satin garter-belt, with my black seamed stockings and my six inch black patent high heels. My make-up was perfect as were my nails also. I also had put on my jewelry, necklace, earrings, bracelets, watch and rings and also my ankle bracelet. All the jewelry was gold. My hair was also perfect and my perfume just added that special sense of femininity that I loved so much.

Although I would divulge to him a part of me that he had never seen I was aroused at what was about to happen and also a bit anxious at how he would react. Just before he arrived I looked again and through my dress all my lingerie was visible and so were my stockings. I unbuttoned one more button on my dress and took a deep breath. I said "Joanne the night you have dreamed has arrived!" I said it with the hope that it would be as wonderful as I had dreamed for a long time.

When he arrived I opened the door and stayed behind it so he would not see me until I closed it, his face registered his surprise at seeing me dressed like that. He did not know what to say. He placed his small bag on the floor and looked at me.

I walked to the centre of the room and slowly turned so he could look at me properly. I looked at him and said, "Well Raymond, do you like what you see?"

He smiled and came to me and took me in his arms he looked intently at me and kissed me on the lips. I felt so feminine at that point. He held me in his arms and asked what he should call me.

I told him, "My name is Joanne Raymond Dear!"

"Nice to meet you Joanne," he said and brought me closer to him as his lips were on mine. This time his tongue teased my lips and I parted them to allow him entry into my mouth. Soon our tongues were dancing languorously together.

Raymond put his arms around me tighter and held me close to him as I placed my arms around his neck as we continued kissing passionately. I realized that my left leg was bending at the knee as he kissed me and caressed my back. Then I felt his hands on my buttocks holding me tightly against him as his tongue seduced me.

He held me so tight that I felt his cock hardening and I felt so feminine and held him even tighter against me.

He broke the kiss and whispered in my ear, "Joanne do you know what you are doing to me?"

I whispered back, "Yes Raymond Darling and do you know what you are doing to me with your passionate kiss?"

"Let me order something to drink Darling Joanne and then we can talk."

He picked up the phone and ordered champagne from room service. I went into the adjoining bathroom to refresh my make-up and perfume as we waited, and made sure the bedroom was also ready as I hoped we would come here together.

I walked back into the living room and Raymond looked at me seductively. Just then there was a knock on the door. Raymond told me to go and open it; I was a bit apprehensive as it was my first exposure to a stranger.

I opened the door and the waiter came in with a roll tray, he looked at me and smiled as he handed the invoice to Raymond. He signed it and then the waiter left. Raymond got up and led me to the sofa; I looked at his crotch and saw his cock was still very erect. He then lowered the lights and poured the champagne.

He then sat close to me and we toasted to each other and our evening as we drank the champagne while looking at each other.

As I drank I felt his gaze upon me and was even more excited.

He put his arm around my shoulder and brought me close to him, I let my head on his shoulder as I looked at him and he looked at me.

"Joanne Darling, are you gay?"

"No Raymond Darling!"

"Are you bisexual then Darling?"

"I think so Raymond Darling."

"Darling Joanne I am gay and love being with someone of my own sex even if he dresses!"

"That is wonderful Raymond Darling."

"Remember when I invited you to my place when my parents were out for skinny dipping?"

"Yes Darling I do."

"Do you know why I was inviting you Joanne Darling?"

"I think so Raymond."

"Tell me Joanne Darling!"

"You wanted us to be naked and you would seduce me into being with you intimately."

"Yes Darling I always fancied you as a man and now even more as a woman. Why did you not come when I invited you Darling?"

"I guess I was not ready Raymond, and maybe a bit scared of what might happen."

"Thank you for being truthful Darling!"

"Raymond Darling I must confess something though."

"What is it Joanne?"

"Remember when your parents went away for a month and you invited me to stay with you. You told me I could sleep in your Mother's bedroom as you would sleep in your Father's?"

"Yes I do Darling."

"Well one night I was rummaging through your Mother's drawers and could not resist trying on some of her lingerie, I put on one of her bra, panties garter-belt and stockings. Even a pair of her highest heels."

"That is quite a confession Joanne Darling."

"I even put on some of her make-up and perfume, I felt so feminine."

"You must have as she did have some exquisite lingerie."

"I did and after I did all that, I went out of her bedroom and walked over the house as you were sleeping."

"Oh Darling, you should have come into the room I was sleeping in."

"I did Raymond Darling and you were sleeping tightly and I admired you and slowly sat on the bed before going back to my room. I still remember seeing the shape of your cock under the sheet and your head was peeking, it was beautiful. Your cock appeared so beautiful and manly. But I did not know if you would accept me as I was."

"You know that if I had awakened I would have taken you with me in the bed."

"Yes and I was hoping that you would wake up a bit, or even woke up as I was walking around the house and caught me, but it did not happened."

"Oh Joanne that is the past we are together now and that is what is important, and I must admit I fancied you as a man but even more as a woman, especially knowing your secret Darling!"

"Yes My Darling we are!"

"Wonderful Joanne, tell me have you ever sucked a cock?"

"Just when I was young experimenting but never went all the way Darling."

"Have you ever been with someone when dressed as Joanne?"

"Yes just once another TV but it was not that good Darling!"

"Joanne you told me you are not gay but you think you are bisexual, have you ever been fucked?"

"No My Darling I have not."

"So you are a virgin Joanne Darling?"

"Yes My Darling I am!"

"That is wonderful, I am curious as to why you called me tonight Darling."

I blushed and he held me tighter against him. "I was dressed and enjoying a glass of wine when I thought about you and those invitations in the past."

"Oh I am surprised, what did you think about for those invitations?"

"I was just thinking what would have happened if I had accepted one of them Darling."

"Darling every time I invited you I had only one thought in my mind, to teach you about gay love, as I said I fancied you and I thought you would be a romantic and sensual partner."

"Oh Darling Raymond, seriously you really thought that?"

"Yes Darling I did!" And he held me closer as he kissed me passionately.

He brought one of his hands to my breasts and caressed them as I also caressed his torso, my hand working on his nipples and all over even his lower torso. I was feeling so feminine at that point.

His hand caressed my back and went to my buttocks holding me tight against him, then his other hand went lower towards my legs, soon I felt him caressing my stockinged legs slowly and sensuously.

He was kissing me as I had never been kissed his tongue dancing with mine and his saliva invading my mouth, he tasted so good as his hand on my legs was making me feel so much more feminine, then he went under my dress and soon I felt his hand on the skin above my stockings. He moaned and kissed me more passionately.

We broke the kiss and looked at each other as we took our champagne flutes. I could see that he had a special look in his eyes.

"Darling Raymond let me go and get more comfortable!" I said.

"Please do Darling but I would like to use the bathroom also."

"Of course Darling just give me a few minutes and when I step into the bedroom you can use it."

I stood up and smiled at him as I made my way to the bathroom feeling very feminine. I refreshed my make-up and made sure all was perfect, before taking the door to the bedroom and he came behind me holding me tightly as he helped my unbutton my dress as he kissed my neck passionately, sending shivers through my body.

I stepped into the bedroom as I turned my head and looked at him seductively, a bit nervous as to what I was about to do but nevertheless eager. I removed my dress and hung it in the closet, then I adjusted my lingerie and verified my stockings were taut and the seams straight. I took my perfume and sprayed it at the proper areas. As I did that the scent made me feel even more feminine but I knew it was not over. Once that was done I went to the closet and removed my black negligee from its hanger. It was the first time I would wear it for someone and I was eager to slip it on. It was long and totally sheer so my lingerie was entirely exhibited through it. I slipped it on and felt even more feminine and seductive.

As I looked into the mirror to refresh my make-up, I was aroused at the sight that looked back at me. As I redid my lipstick I felt so feminine and the thought that I was about to give myself to a man made me shiver and I felt my clit and rosebud tingle.

Raymond knocked on the door, "Yes Darling."

"Are you ready Darling?"

"Almost my Darling Raymond."

"Wonderful My Darling, give me a minute or so, I will knock on the bedroom door when all is ready."

I wondered what he was doing but since I had called him I decided that I would accept what he wanted, after all after being kissed by him I was already decided.

"It is all perfect Darlings you can come out."

I took the door handle in my hand looking at my feminine hands with my red nails, knowing that soon they might soon be on his cock and it made feel even more feminine. I opened the door and there he was, he smiled and so did I. He had put candles in the room to make it more romantic.

He was standing there almost all naked only a small G-string held by strings on the sides, hiding his cock but it was so tight I could see its outline through the shiny black material. He had that look in his eyes that told me he found me beautiful.

He came to me and took me to the large sofa; he sat down and sat me beside him. We sat facing each other and he took my champagne flute and gave it to me as he took his.

He said, "Here is to us Joanne, you are beautiful and so desirable!"

"So are you my Darling Raymond!" I answered. And we clinked our glasses before drinking.

He looked at me intensely. "Joanne My Darling, you told me that you had never lost your virginity and that you had never had a cock in your mouth properly My Darling!"

"Yes My Darling it is all true!"

"My Darling does that mean that you invited me here tonight so that you could indulge what you have missed?"

"Raymond as I told you I was dressed and was also lonely, I wanted to be with someone and you were the one I thought of."

"You did not answer my question My Darling!"

I lowered my head and blushed, then brought my mouth to his ear as my hand went to rest on his thigh close to his cock.

I licked his ear and then whispered, "Yes Darling I did!"

He brought his mouth to my ear and whispered, "Joanne were you hoping that something intimate would happen?"

I moved my hand closer to his cock and whispered, "Yes My Darling Raymond!"

"I hope you are sure of this My Darling," he answered.

"My Darling Raymond I was never more sure!" And I let my hand cup his cock through his underwear. Immediately I felt it harden and loved to see my long nailed fingers holding it that way.

"Oh Joanne Darling, you are quite special and I love the way you touch my cock."

I kept caressing it and it kept getting harder. "Raymond Darling I love how you react to my caresses on your cock."

His cock appeared to be huge compared to my little clitty. I was eager to see it.

He brought his lips to mine and we kissed passionately as we caressed, I could feel his cock still hardening in my hand and he started caressing my nylon clad legs until he got to the skin above and it made me moan as he did.

It was so wonderful for me to be in his arms that way.

As I caressed the length of his cock he kept moaning and then I felt his head come out of his G-String. When my fingers touched it he moaned louder and I felt he was quite aroused as some pre-cum was leaking. I was quite aroused myself and I used my fingers to spread his pre-cum on his cockhead. He moaned and took a deep breath intake that took my breath away into his lungs as he held me tighter.

I was so aroused I could not resist anymore, my hand when to his side and pulled on the tie that held his G-String together, he moaned as I did so and then let my hand remove the small patch of cloth that hid his cock.

As soon as my hand touched his cock, again he took a deep breath as he moaned louder.

I caressed its length and then held it in my hand, I was enthralled as I held it by the size of his cock and the softness of the skin as he was hairless. I caressed it from the base to his cockhead feeling his pre-cum leaking.

He broke the kiss and looked at me. "Joanne Darling do you like it?"

I smiled and looked at it seeing my red nailed fingers around it and was simply hypnotized by his cock.

"My Darling Raymond I do not like your cock I Love it, it is so beautiful!"

I felt his cock quivering in my hand and it made my clit harder and I felt it leaking also.

He told me to stand up and he opened my negligee and caressed my panties, slowly he slipped them off along my stockinged legs and then took my clit in his hand while the other caressed my balls. He lightly kissed the head of my clit. Then bade me to sit close to him. I did so and cuddled as my hand went back to his beautiful cock.

He kissed me passionately as we both caressed each other. His cock was leaking generously now and my hand was wet with his pre-cum which I lovingly spread on his cockhead as he moaned and took deep breaths. His cock was quivering under my caresses I loved it.

"Joanne Darling do you really love my cock?"

"Raymond Darling, yes I do and I find it so splendid and marvellous!"

"Oh Joanne Darling that is lovely, but what makes you find it so?"

"Raymond My Darling maybe it is that after all this time I really see it, and also because as my female side it is quite exquisite to see my hand caressing it, with my red nails and rings!"

He looked at my hand caressing his cock, "Yes Darling I must admit that it is quite arousing to see your hand on my cock. I also love to see your clit framed by your garter-belt and stockings!"

"Thank you My Darling, you are so hairless it is so sensual!"

"I know I love it so I can feel the caresses better My Darling!"

"My Darling I shave because I want to be as feminine as possible but I agree I love shaved genitals! And your cock is so magnificent without any hair My Darling I love it!"

"You really think so Darling?"

"Yes My Darling Raymond I do!"

My clit was leaking now and I felt one of his fingers spreading it on the head, then his hand left my clit and he brought a very wet finger to my lips, "Taste yourself Joanne Darling"!

I opened my mouth and took his finger in licking it clean my tongue tasting myself and I moaned.

"Do you like Darling?"

"Oh Darling I love the taste of me!"

He took my hand off his cock and brought it to my mouth, "Now Darling taste me!" My fingers were very wet and I licked every one clean as I moaned my pleasure.

"So Darling did you like my pre-cum?"

"Raymond My Darling I loved it, your taste is luscious and appetizing!"

"I am elated that you like it My Darling as I hope you will taste more of me"!

I put my hand back on his cock with a sigh of pleasure, "Yes My Darling I want to taste more of you!"

He kissed me again passionately as his hand moved back to my clit, and he had his other hand on my breast caressing it, I felt so feminine.

As he caressed my breast, even though it was a falsie, it turned me on more and he slipped his hand under my falsie and caressed my nipple, I quivered and moaned. He caressed my nipple and pinched it, I moaned even louder.

He whispered in my ear, "My Darling your nipple is so sensitive, I love that, so much more to give you pleasure with!"

"Darling Joanne, did you really love the taste of my pre-cum?"

"Raymond Darling, I really did!"

"Was it your first time tasting pre-cum Darling?"

"Yes Darling as before when I experimented and with the other TV it did not leak enough for me to taste, so yours is the first and it is marvelous!"

"Do you want to taste more Darling?"

"You read my mind My Darling!"

I lowered my head to his crotch seeing his huge cock grow as I got nearer. I let my tongue out and put it on his cockhead, it felt so soft and spongy and the pre-cum flooded my taste buds. I loved it. I licked his cockhead clean as he caressed my clit and teased my nipple.

Once his cockhead was cleaned I took his cock between my lips and let myself swallow it, it was not that thick but so long and it filled my mouth nicely. I sucked on it as Raymond moaned and took big breaths; I knew I was pleasing him even though I could not take all of him in my mouth.

I sucked him and held his balls in my feminine hands and I felt so womanly and sensual with his cock in my mouth and he tasted so heavenly.

I was so happy that I ate his cock with desire and wantonness.

"Darling Joanne if you keep going you will make me cum!"

As he said that I knew I wanted him to cum in my mouth. I kept going until I felt his cock start quivering and suddenly it pulsed and the first jet of cum filled my mouth. It made me so proud and excited as he kept filling my mouth and moaning his pleasure. To feel his cock pulse each time was marvelous.

I held his cock in my mouth as I cleaned it and then looked at his face. His eyes were closed and he looked so peaceful and satisfied. I let his cock slip from my lips and he opened his eyes. He looked at me so lovingly and passionately. I looked at him seductively and ecstatically.

I sat beside him and opened my mouth to show him his cum before swallowing it.

"Darling Joanne I cannot believe it is your first time sucking a cock, it was so good for me and so sensual also. I loved when you showed me your mouth before swallowing it, I felt so special knowing that now you have me inside you Darling!"

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