A First Time for Both

I am in my late twenties, successful entrepreneur/investor, and I must add well endowed. Financial success came early to me thanks to incredible beginners luck in the tech industry and the advice of very wise financial planners. With money came fancy cars, fancy home and fancy women. Then I thought I found the right woman, and were devastated when I found she was going to leave me for another man who had even more money, fancier car. This was a terrible experience and I quit dating women for a while. Then I met Tracy and everything changed. This is the story.

In the tennis club I had just joined in the courts I saw this very beautiful woman. She was truly beautiful, with a petite, very slim body. She must have been around 5'3" and could not have weighed more than 100 pounds. She was blonde, with long hair and looked like a young Margot Robbie with lips like Scarlet Johansen. She had a body with very small waist, well rounded hips and very long tanned legs that would make any supermodel jealous. Her fingers were very slender, with delicate hands and feet. She was wearing women's tennis shorts, women's tennis shoes with a very loose tennis shirt. I was very attracted to her and introduced my self. She said her name was Tracy and she was new to the club also. After a round of tennis, I invited Tracy for a lunch at the club. Tracy had a great personality with a sense of humor and this sexy girlish giggle. We immediately hit it off and I got her phone number to go out. You can imagine my shock when I later saw Tracy in men's locker room and realized Tracy was a male. You can imagine the conflicts and thoughts raced through my mind. My conflicts increased when I realized how much I was still attracted to Tracy even after finding out she was a male. Tracy had no body hair, her face soft and smooth without a trace of beard. In fact there was not a trace of maleness in Tracy. I was not sure what to make of her but I was getting over my breakup with my girlfriend so Tracy and I became fast very good friends as well as tennis partners. We went outings and began to develop a close friendship. Tracy's stunning beauty also helped I must admit.

One day we were sunning on lounge chairs in the club swimming pool. I noticed Tracy was wearing a woman's bikini bottom and very loose t-shirt, which she never took off. I could not fight my curiosity any longer and asked Tracy about whether the t-shirt was for some kind of sun sensitivity. Tracy got real emotional; her eyes watered and asked me if we could go to someplace private. My home was around the corner so I offered Tracy we could go to my home to be private.

At my place I offered a drink to Tracy, sit right next to her and put my arm around her and told her she could trust me. Tracy said:

'I never discussed what I am going to tell you with anyone other than doctors and my parents. Do you promise to keep everything confidential?'

My curiosity increased even more.

'Sure Tracy. I always will be your friend no matter what you are about to share with me.'

'From birth my body did not respond to testosterone so my body developed as a female and there was nothing doctors could do. Doctors hoped when I reached puberty things will balance out. When I reached puberty instead of growing a beard my breasts started to grow like a girl's. My hips widened, skin softened and except menstruating I looked as you can see just like a woman.'

'I must admit like a gorgeous woman'

'I guess that would be a compliment and I thank you. But life was different for me. When I would try even a boy's jeans it would never fit me right. If the waist fitted my wider hips would not fit. If it fit my hips it would be too loose in the waist. It was true for underwear, shorts and even shoes. So I had to wear woman's jeans, woman's underwear, woman's shoes even woman's sport bra.'

'I have to admit I did notice that'

'I want you to understand I am not a cross dresser, transgender just different than most people.'

Tracy started to cry. I gave Tracy a huge hug.

'I want you to understand I will never share what you told me with anyone else. I want to be your friend and want to know you better. You can trust me.'

'I really appreciate it. You are the first person other than my parents I discussed this part of me. I could not date girls, some boys would try to pick me up but I was not interested. So I had to live an asexual life'

'I feel bad for you.'

Tracy's trust and opening for me brought us very close. We constantly went out and became best friends. I was taking Tracy to romantic restaurants, romantic getaways. We would have movie nights at home; Tracy would sit very close to me, stretch her legs on my lap; however she would always leave at a respectable hour with a peck on my cheek. To me Tracy was more than a friend; to me she was a very pretty, sexy girlfriend. I felt if I attempted any physical contact with Tracy it would scare her off and I would never see her again. As time progressed I noticed Tracy began to wear tight women's jeans with boots, sexy shorts with sandals showing off her pretty feet and form enhancing blouses. Tracy started to look a lot sexier. When I would take Tracy on a date to a romantic spot, I would sit very close, our legs touching, I would put my arms around her, and she would put her head on my chest. I often wondered if Tracy would notice the bulge in my pants and the affect she was having on me. Tracy enjoyed being physically close to me as she told me I comforted her. Tracy had no clue I was lusting after her. I often imagined those full lips on my cock and slender fingers wrapping around my cock.

I have a private one-bedroom beach bungalow in one of the Hawaiian Islands with a private pool and hot tub. I was planning a vacation there and invited Tracy. After a few days Tracy accepted it. When we got to my place in the island I asked Tracy about sleeping arrangements. I told Tracy I had one bedroom with a king size bed and sofa bed in the living room. Since Tracy was my guest, I could sleep on the sofa bed or since the bed was big enough we could share the king-size bed. I made sure Tracy understood it was her decision alone. It took a very long time for Tracy to come up with an answer, and she said the sofa bed would not be very comfortable for me and it would be all right if we shared the bed since it was large. After a lunch on a local restaurant we decided to sun by my private pool. I was pleasantly surprised Tracy was wearing a very skimpy string bikini in which she looked incredibly sexy.

She was lying on her stomach and I offered to apply suntan cream. Tracy after some hesitation agreed. I sat by Tracy and applied the lotion on her back while massaging her neck and shoulder area. I skipped Tracy's behind and applied the sun cream to her luscious legs taking my time. Then I went beck to my lounge laying on my back. After a while Tracy offered to return the favor to apply sun cream on my chest and legs. Tracy sat by me on the lounge and with those slender, cute hands started to apply sun cream on my chest. Tracy also took time massaging my chest area. Tracy continued to apply the sun cream on my thighs and legs. Tracy's touch was very sexy and I had a huge hard on. While she was massaging my thighs, Tracy's hands accidentally touched my hard on. Tracy pulled her hand immediately, turned beet red and without saying a word got up and moved to her lounge, putting a swim towel around her waist covering her behind and thighs.

Tract did not talk much after that; we had a very quiet dinner, watched some TV and decided to go to sleep. Tracy came to bed wearing a short teddy and provocative panties. I tried to go to sleep but just couldn't fall asleep. Imagine a beautiful woman laying a few feet from you with her panties and a short teddy. I lovingly looked over Tracy in the dark, she was sleeping on her stomach and her long tanned legs and round ass was in full view. When Tracy fell asleep I could not help it and moved slowly, closer to her. Almost involuntarily I started to caress Tracy's gorgeous legs. I had a huge hard on and became more daring and began to caress Tracy's ass first through her panties then I put my hand underneath and began to caress her beautiful, round ass. Tracy's ass was so round and firm more beautiful than most girls I dated. When Tracy did not stop me, I spooned her and placed my hard cock in her ass crack. We had both of our underwear but it was a sensational feeling. All of a sudden Tracy woke up and quickly turned towards me. To my surprise Tracy placed her leg on my hard cock and her hand on my chest. I was surprised she did not look angry but had this puzzling look. Even in the dark I could tell Tracy's face had turned beet color red. Tracy's lips were few inches from mine.

Tracy asked

'What is going on?

'I just woke up too, it was an accident. I'm truly sorry'

'I do not believe it was accident'

Tracy continued:

'For some time I felt changes in your feelings towards me. I caught you many times checking me out, especially my butt and legs.'

I was frozen silent. What could I say; I just did not want to lie.

'At first I was very confused, then I felt flattered and as time progressed I felt like I was your girlfriend rather than your buddy. I even started to buy cloths to make me look more sexy to you.'

'That I noticed, I thought you looked spectacular'

'When you hugged me I felt it was more than a friendly hug but you were hugging me like I was your girlfriend.'

'I have to add a very pretty girlfriend.'

'When you invited me to this vacation, I especially bought sexy women's underwear and skimpiest bikini bottoms for you.'

Tracy was now playing with the hair in my chest with those delicate fingers.

'Well it worked and I developed intense desire for you that I could barely control.'

'When I was applying suntan lotion and accidentally touched your hardness I was sure where you wanted to take our relation, but at the same time I got very scared.'

'Why were you scared?'

'I have not had any sexual relation whatsoever. I would not know what to do. I did not know how I would really feel if it went in that direction and if would regret it during or afterwards.'

'I was scared to make any passes at you not knowing how you would react. I guess being in the same bed with you I just could not control myself any longer.'

Tracy was moving her leg on my hard cock, which made me grow even bigger, and she felt it. Tracy blushed even more and her eyes grew big.

'Just promise me this, if we progress to the next level and I agreed to be your woman all the way would you stop if I felt shame or uncomfortable?'

'Of course, we will not do anything not comfortable for you. I respect your every wish even if you decide not to go through it.'

'You know you have to be very patient with me. You have to go very slow and gentle. You have to guide me as I really do not know what to do.'

'You do not have to do anything you are not comfortable with. All I am asking you is to let your self go, and let your woman side take over as nature intended.'

Tracy's lips were inches from mine and she looked so sexy. Tracy took the first step and gave me a quick kiss on the lips. I took the next step and started to kiss Tracy's neck, and caress arms and back underneath her teddy. I could feel Tracy was relaxing and gave me another kiss this time it lingered. I kept caressing Tracy all over and she started to move like a woman now. Tracy gave me a very wet kiss on the lips as our tongues danced. Tracy's hand almost accidentally touched my cock but she withdrew it immediately. I did not push her. I removed Tracy's teddy to my delight she had fantastic tits, very round with erect nipples. When I cupped them I could feel they were at least size B. I started twirl my tongue around her nipples and gently sucked Tracy's tits. Tracy was flushed with excitement and was wiggling all over. I cupped Tracy's ass and caressed her legs. Tracy this time deliberately touched my cock and started to stroke it. I felt like Tracy was becoming more comfortable with her transition to being my woman. Tracy became bolder and started to caress my balls while stroking my shaft. I was sucking her tits and caressing her ass. From the way Tracy wiggled her butt I knew she was enjoying the attention.

Everything was moving so naturally and passionately that I asked Tracy if she would go down on me. Tracy had this puzzling look on her face and in her most girlish voice said

'What do you mean?'

Not wanting to go into details and possibly to shock her I said wait a minute. I ran into fridge came back with a can of whipping cream and sprayed the cream on my cock and asked Tracy to lick it. Tracy got the hint and with her luscious lips and tongue started to lick my cock. Next I sprayed my balls with whipping cream, and Tracy began to lick my balls. I did not have to give any more hints and Tracy took over. Tracy rubbed those pout lips on my cock, while fondling my balls. I was in ecstasy. I had replaced whipping cream with my precum and my precum was all over Tracy's lips, chin and cheeks. Tracy was flushed and proud of her newly developed skills. Without any further guidance from me Tracy instinctively started to dance her tongue on the head of my cock. Even though it was first time Tracy was sucking a cock it felt sensational. Just like I imagined it, those full lips were around my cock while her slender, feminine fingers were gently playing with my balls. Her mouth relaxed and it was sensational. Tracy looking at me with those beautiful blue eyes shyly asked me how she was doing. I complimented her that she was better than any woman I had. She told me it was her very first cock sucking and at first was awed by my size but started to really enjoy it and felt very sexy in girlish way. I told her he was fantastic at sucking my cock. I could see passion on Tracy's eyes and as she rubbed her full lips on my shaft. I was shaking all over.

Tracy with my precum all over her face in a sexy, girlish way asked:

'Am I 100% your woman now'

'Not 100% yet.'

Tracy was puzzled:

'What do you mean not 100% yet, what else?'

I caressed her ass cheeks and teased her ass hole with my index finger. Tracy's eyes grew real big:

'You mean there? No way this big thing is going to fit there'

'I will be very gentle and slow. I have oils to make the entry easier. It might hurt a little at first, but trust me you are going to love it. You will then feel like you are a complete woman. You will have to trust me in this I guarantee you will experience pleasure like you never had before. You will totally feel what it means to be woman'

'I so far loved everything that happened, I believe I will love that also. Please excuse me as I get myself ready for you.'

Tracy went to the bathroom, and from sound of things I could tell she was getting ready for me. Meanwhile I heated oils to do my part.

When Tracy returned from bathroom, without saying a word lay on her stomach and wiggled her butt seductively.

'I am ready to be your woman 100% '

I massaged Tracy's butt and legs with hot oil. I started to kiss and lick butt cheeks. When I started to lick her hole I could tell Tracy was getting really turned on. Tracy began to lift her butt towards me. Then With plenty of oil I inserted my little finger on her hole. Tracy kind of froze at first, and then relaxed again. I progressed to index finger than to my middle finger. Tracy was sticking her butt towards me indicating ready to be fucked. I took my hard cock began to slide it inside Tracy's but crack. At this time Tracy started to moan and started to massage my cock by moving her ass up and down on my cock. I applied more oil to my cock and inserted the tip into Tracy's hole. Tracy began to breath heavily and continued to moan.

'It hurts but feels good, it tickles a little'

I inserted my cock an inch more and very slowly began in out motion. Tracy was moving her but in a circular way, which was very sexy.

'It feels so good. I feel like your woman now.'

Tracy lifted her feet pushing on my thighs encouraging me to progress. I pushed my cock all the way in and began to pound Tracy's ass. Tracy was screaming with ecstasy. Tracy's butt was meeting my every trust; there was no trace of any shyness anymore.

Then I had Tracy sit on my cock so I can watch that sexy ass go up and down sliding on my cock. I turned Tracy on her back, put those long, tanned legs on my shoulders and continued to fuck her. I lifted her from the bed; her legs still on my shoulders and started to fuck her standing up. I placed Tracy's back against the wall, still standing and started to fuck her furiously. Tracy was screaming with pleasure, her face flushed. I laid Tracy back on the bed on her stomach and continued to fuck her furiously. Tracy was moaning, screaming. I came like a hurricane inside Tracy's butt; it felt sensational.

Tracy with a very girlish voice said:

'That was the most amazing experience I had in my life. I had multiple orgasms like you wouldn't believe. Thank you being patient with me and for making me a complete woman.'

'You were sensational, and were better than any woman I had before.'

Next day we went shopping for a complete remake of Tracy. I bought Tracy dresses, female shorts, sexy female underwear, lingerie, nylon stockings, and stilettos. I took Tracy to a beauty salon to give her a sexy, feminine haircut and they added hairpiece. They applied make up and light lipstick to enhance those pout lips. Tracy had manicure and pedicure with pink nail polish. When we left the beauty salon, Tracy was wearing a short dress, wedge sandals and he looked like a bombshell. All the men were checking her out and women looking at her with jealous looks. I told to myself he is my woman, they can look but no touch.

When we went back to the beach house Tracy offered me fashion show. Tracy put some sensuous music on and began to show off her dresses with stilettos and boots all the while dancing seductively. Occasionally she would place her high heels on the arm of my chair and let me caress her legs and feet. Then Tracy in a sexy, girlish voice almost shyly said:

'I have a surprise for you'

When Tracy came out with her surprise I was stunned.

'I got this especially for you. I hope you like it.'

Tracy had bought this very sexy outfit while I was not looking. It was lacy, short short lingerie, sexy underwear with a seductive opening on the backside. Tracy had black nylons with garter belt and black platform stilettos.

'Tracy, I am speechless. You are the sexiest woman on this planet.'

Tracy began a very seductive dance, frequently putting her stiletto on the arm of my chair and giving me a look at that sweet ass while I caressed her legs. She gave a sexy giggle and placed her hand on my very visible hard on. She massaged my cock through my shorts and then without saying a word sat on my hard on, facing me with her luscious legs stretching on both sides of the chair. She gave me the most sensual lap dance imaginable. Then she got up with a very sexy look, and gently removed my shirt and shorts. She kneeled in front of me and began rub my cock through my underwear with those pout lips. She removed my underwear and began to massage my cock and balls with lubricant. Still not saying a word she sat on my cock, facing me. This time my cock just slid through her hole like butter. She kissed me very wet and passionately. I fondled her breasts through her lingerie. Tracy turned back without pulling my cock out to provide me with a gorgeous view of her ass through crotchless sheer lacy underwear. Tracy sensed I was not going to last much longer and gave me a long sexy kiss and whispered in my ear:

'I want to finish you off in my mouth and feel your seed all over my face. I want you to know I am your woman now.'