Friends With Benefits
- 1 year ago
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Tits Have Benefits free porn video
transgender – crossdressing – shemale – transformation – feminization
So there I was walking up to the most gorgeous creature in the room, a beautiful woman with incredible tits and ass and beautiful long black hair. This was the woman of my dreams who despite being the person who I could most open up to, nevertheless had been unobtainable in my mind. I had been a shy retiring nerd who could never hope to win the affections of a beautiful woman, but now things had changed and now I felt confident, because now I was a beautiful woman myself.
The story began six months ago.
My name is Andy and growing up I guess I had the same type of issues that many cross dressers had growing up. I was always a bit of a nerd at school I guess. I was intelligent in a nerdy way and on top of that I was small for a guy and physically weak. In sports I was the guy who always got picked last when picking teams and on top of that I was a bit of a daydreamer spending larger than normal quantities of time on my own immersed in my own fantasies.
Given all the above it was not surprising I was bullied and teased a lot at school, often the guys and sometimes even girls would call me a sissy (little did they know the whole truth). Given my treatment at school it is not surprising that I effectively decided that I could not compete in a male world where it appeared to me that success was defined by stature (height), physical strength and athletic ability.
The only area where I believed I could compete in a male world was my potential to get a good job in the future so naturally I worked hard at school to try to at least be successful in the world of work. When I was not working on school work I spent my time fantasizing about being a girl, apart from the fact that I liked the clothes and was always ‘borrowing’ my s****r’s clothes (I don’t think she ever realized), I also tended to find the girls more friendly towards me and I thought my temperament was more suited to being a girl given my tendency to become emotional and cry.
Apart from wanting to be a girl, I also lusted after girls as I found them to be beautiful creatures. I loved to around girls and talk girl talk and I guess I thought of myself as a lesbian in a man’s body.
Several years on I was completing a software related PhD when I met a woman who I was to become obsessed with, her name was Jane and she was the most beautiful creature I had ever seen, my height (when she wore heels she looked taller than me), beautiful black hair, perfect sized 34D breasts, and with shapely legs and ass. Her eyes were two serene pools of blue and you could get lost looking into them. Jane was an undergraduate at the time working on a degree in media studies.
Jane liked to talk to me because she found me easy to get along with, she thought me intelligent and she valued my opinion. I in turn was very much attracted to her both physically and mentally but it was clear to me that she was out of my league and would never return the feelings that I felt for her.
My opinion was borne out when it became clear to me that she was more interested in women than men and it was clear that she was getting it on with a group of close girlfriends. You could see evidence of the shared physical intimacy in the way they touched each other. She had three girlfriends who I also found hot called Jenny, Chris and Ann.
One day Jane confided in me that she was actually bisexual but that she had not had good luck with men because she was attracted to muscle bound hunks with a ‘bad attitude’ who tended to treat her like shit. As a result she tended to stick with women, although when she got d***k she would occasionally hook up with this type of guy for the night only to regret it the following morning. Whilst hearing that Jane was bisexual initially gave me hope, my hopes were dashed when she told me the type of man she liked. It felt like a cruel double blow. What chance did a guy like me have with somebody like her?
So there I was 26, and a virgin, I had never been with a girl and browsing the internet for porn to jack off with, when I stumbled on some clips showing shemales with women, my attention was drawn to one clip in particular made by a shemale called Trish. Her body was perfect, the whole of her body form was all girl, her beautiful tits, shapely ass, trim waist, long dirty blonde hair, exuding femininity out of every pore, except that she had a dick. However hard I tried I could not think of Trish as male in any way, I could only think of her as female.
Below the youtube clip there were a load of comments from people responding to the video and I was amazed by the comments from bisexual women. It was almost like a frenzy of these women saying how beautiful they thought Trish was, what they would like Trish to do to them, what they would like to do to Trish. There were also straight women, straight men, lesbians, gay men and bisexual men, falling over themselves to say how beautiful they thought Trish was it seemed like there was no limit to her appeal, but the majority of the comments were from bisexual women. It seemed like everybody wanted to be with Trish, but I wanted to be her.
Suddenly an idea entered my head and would not leave, if I had a body like Trish, if I had tits like hers, Jane could not help but be attracted to me. If the comments from all those bisexual women were anything to go by it seemed like Trish represented the ultimate in sexuality to them. I became obsessed with really becoming feminine and having tits, from that moment I had to make the fantasy a reality.
But of course I realized that achieving my goal would entail a lot of practical details, questions I had to answer like:
1.How could I grow large tits without it shrinking my penis (currently an acceptable 6.5 inches)?
2.How much weight loss would it take to get my waist down as small as I wanted?
3.How could I change my voice so it sounded feminine?
4.What about my Adam’s apple?
5.Where could I get lessons to become more feminine?
6.What about my body hair, I was fortunate to not have massive amounts but I still had it?
7.How could I afford the procedure?
The first question was the most troubling for me, I wanted my penis to be fully functional and not to suffer any loss of size yet I had heard that it would be affected by hormone treatment. Trish had given her contact information so I decided to contact her.
When I talked to Trish she was very understanding and explained to me how she had managed to acquire the body she had without losing penis size. She told me that the trick was in hormones at low doses combined with surgery for the breasts and Adams apple, botox for the lips, and a rigorous diet and procedure using a tight corset to achieve the desired waist. When I asked about training in being more feminine in terms of behavior, Trish told me that she offered training, in fact she offered the whole package including the surgeries for a very competitive price.
When I asked her what the price would be for all this I was heartbroken at hearing what it cost, there was just no way that I could afford it. Trish heard the disappointment in my voice and for some reason she suddenly warmed to me. She said, ‘look I don’t know why but I like you a lot, just for you I will do the whole thing for you at cost, that means you only pay for surgeries and hormone treatment and even those at a special price that only I can access. You can even stay at my house during the procedures, now that has got to be an offer you can’t turn down.’
When she told me the price it was still a lot of money, but with all my savings and not having to pay for accommodation during the treatment I could afford it. For some reason I did not have to think about it I just said ‘Yes’, to which Trish replied, ‘so when can you get out here, I can’t wait to get started.’
In six months time it was to be Jane’s 21st birthday party and she was already planning the venue. I told Jane that I would have to leave town for a few months I told her it was work related. I had just completed my PhD and had got a job writing software, the truth was I could write the software anywhere as long as I had my laptop with me, but Jane didn’t need to know that. Jane said ‘look I will miss you like hell, you know that, as you are the person I confide in most, actually I think of you more like a girlfriend.’ Then she gave me a long hug and having a few inches height advantage in her heels she kissed me on the forehead, just before we parted she said ‘Just don’t forget to come back for my birthday party.’ ‘Don’t worry I will be there’, I promised.
So I flew to California to meet Trish and over the next 6 months I was transformed first I was put on a basic low level female hormone treatment, and then immediately my lessons in femininity began. I was taught how to walk (with and without heals), how to sit, how to eat, how to bathe, how to go to the john, how to make my face and paint my nails. I was given coaching in how to speak softly, and in a womanly way, leading up to an operation to shorten my vocal chords and eliminate my Adam’s apple.
Every day I was required to dress in dresses or skirts, my diet was strict and the corset constraining my tummy and waist often felt unbearable. Gradually I began to grow breasts to the point where they were an A cup, every day it seemed that my nipples became more sensitive and I started to play with them at night. When I was deemed ready to pass in public I was taken out clothes shopping and exposed to trying on dresses in department stores.
I was given laser treatment to remove hairs from my skin and became accustomed to facials, body massages and hair dressers. I had been told to grow out my hair and my hair now came down to just above my shoulders and I was given blonde highlights. I became used to the beautiful female face staring back at me. I was Andy no more, now I was Andrea.
I became acquainted with Trish’s girlfriend Sandy while I was living at their house and developed a good deal of affection for both Trish and Sandy. Sandy, knowing that I was completely inexperienced sexually made it her business to teach me what women liked sexually and how to get to know my own female sexuality. And after getting my breast implants, they were now D cup, she encouraged me to run my hands over my new tits and ass and take my nipples in my fingers and squeeze.
It started to become obvious to me that seeming me run my hands over my beautiful female form made Sandy horny. She encouraged me to feel her tits also, all in the interest of learning to relate sexually to women of course. Then she would slowly run her fingers over my tits and ass, suddenly she kissed me f***efully on the lips and then moved down and took my left nipple in her mouth, taking the right nipple in her hand and massaging my breast. Suddenly I became hard as a rock, I had never felt anything approaching this when pleasuring myself in the past, my new tits were super sensitive and Sandy knew how to take advantage of this. Suddenly Sandy sucked my nipple into her mouth very hard and sustained the suction for a long time and to my amazement I came.
I spoke to Trish about what Sandy and I had done expecting him to be upset, but was surprised when she said ‘Sandy is a free spirit and she is completely open about what she does, that is what I love about her, her sexual adventures and my own help bring spice to our relationship. Besides, you are like the s****r I never had and I would share anything I had with you, I am happy for Sandy and I am happy for you that you can share this.’ At this I threw my arms around Trish’s beautiful female form and hugged her, saying ‘I love you Trish’, to which Trish replied, ‘I know Andrea, and the feeling is mutual.’ Then Trish said, ‘Sandy wants you to fuck her you know, she has wanted that ever since she first laid eyes on you, but she respects you, she respects the fact that you want your friend Jane to be your first.’ Suddenly I felt acute self doubt, ‘that all depends on whether Jane will want me.’ ‘Oh you are so naïve,’ Trish replied, ‘the way you are now I don’t think there is anyone who wouldn’t want you.’
My sex lessons with Sandy continued, she instructed me on how to do a proper job of licking her pussy and when I started to get it right I learned that the most beautiful sound in the world is a woman having a multiple orgasm, ‘oh fuck, oh fuck’ she would cry as she came with wave after wave of glorious release. After this Sandy would take my beautiful 7 inch cock in her beautiful mouth and suck me off till I came hard in her mouth, for some reason my dick had grown by half an inch, I have no idea why. ‘Now,’ proclaimed Sandy, ‘now you are ready for your friend Jane, she won’t know what’s hit her.’ Then she said, ‘she must be really beautiful for you to do what you have done for her, and I don’t mean just on the outside.’ ‘Oh she is,’ I said, ‘she is, but now I know that if I start the relationship I wish with her, it is just a bonus, now I understand that I did this really because I also wanted it for myself.’
So there I was, I had just flown back to Texas, checked into a hotel and after spending 4 long hours making myself up I had left for Jane’s party. I had had a long soak in the tub, my nails looked perfect, my long light brown hair with blonde highlights was shiny and now came just down to my shoulders. My skin was smooth as silk and my size D breasts were accentuated by the strapless sweetheart neckline of my minidress. My blue minidress looked fantastic with several layers of tulle on the flirty skirt which started just below my bust and came down to mid thigh, showing off my perfectly formed legs which ended in strappy blue sandals with 3 inch heels. Entering the venue for Jane’s 21st birthday celebration, I confidently walked in feeling secure in the knowledge of the almost magnetic attraction of my new body and personality.
Looking across the room I saw Jane and my heart leapt. I really had missed her a lot. She looked like a dream her beautiful long black hair was contrasted by the cute white babydoll minidress she was wearing which really accentuated her tits and ass and her beautiful long legs. She was wearing white bootees with 3 inch heels like mine.
I confidently walked over to Jane coming face to face with her. With the 3 inch heels we were exactly the same height and it was the first time I had felt as though I was on an even standing with Jane. I looked confidently into her beautiful blue eyes and then, suddenly, I became apprehensive. This was a private party and Andrea was not on the guest list, I couldn’t go into a long explanation of my transformation in front of a load of people. What the hell was I going to say? I had no choice but to improvise.
Quickly I introduced myself as Andrea, Andy’s b*****r. Fortunately I had mentioned that I had a s****r to Jane in the past but had not mentioned her name, or said much about her. I explained that Andy’s flight from Los Angeles was canceled and he was waiting to get reassigned to a new flight, he would not be able to make the party but would arrive tomorrow which was Jane’s actual birthday. As I was meeting him in Texas anyway, he had sent me to be his representative so to speak.
Jane told me that she was sad to hear this as she was really hoping that Andy was going to make it to her party. Then she said, ‘Andy told me he had a s****r but he never mentioned how beautiful you were, you turn me on just looking at you.’ I couldn’t help blushing a little because I was not expecting Jane to be so forward with me. However I quickly regained my composure replying, ‘he told me you looked good, but he didn’t mention how good you looked, I think you are hot, really hot.’ The recognition of mutual desire was strongly communicated in each other’s eyes.
‘So anyway,’ let me introduce you to my friends, quickly Jane introduced me to Jenny, Chris and Ann. Jenny, a hard core lesbian with a strident personality said, ‘well Andy certainly kept you a secret Andrea, he never mentioned that his s****r was a super hot chic,’ with this she let her hand briefly rub across my ass causing my constrained cock to suddenly start to harden.
I had a really good night, spending most of the time with Jane. We talked quite a lot about Andy (myself of course) and as I progressively had more to drink, I let it slip that Andy had a crush on her. Surprised Jane replied, ‘He does? I never knew. Of course I love him as a friend but I guess I never thought of him that way. I tend to go for men who are muscle bound hunks but they tend to be insensitive in my experience which is why I stick to women in my permanent relationships.’ Then she continued, ‘but Andy, well I have never thought of him that way, of all the people I know however he is the one person I can be most open with.’
Deep in thought, Jane observed, ‘talking to Andy is like talking to a woman, he has an intuitive way of looking at the things that normally I only find in women. To be honest with his stature and delicate bone structure I have often thought he would make a better woman than a man, I often wish he was a girl, I think I could have a lot of fun with him, or should I say her, if he was.’ At that moment I was struggling with conflicting emotions, on the one hand jubilation that the direction in which I had gone was the right one to make me attractive to Andrea, on the other, sadness at her measure of me as a man while at the same time thinking of myself as more female than male.
So I asked, ‘It seems to me like you are saying that Andy does not make a good male?’ Jane replied, ‘Don’t get me wrong, Andy is a better programmer than anybody I know, he is good at planning ahead, and more than capable of taking responsibility for his life. The strong muscle bound men that I am attracted to, well I find their qualities can be interesting in the short term but not the long term. The qualities I admire in women on the other hand are compassion, sensitivity, physical softness and beauty, openness and the willingness to share their emotional life. Simply said those are the qualities Andy possesses, it is just a pity that they are packaged in a male form.’
Jane was also very interested in me (as Andrea that is) and it was necessary to make up some stuff although where possible I tried to relate things to my true experience. One problem that Jane did have though, was in trying to understand why Andy had not said more about me, she said, ‘you are so open, such a caring person, you have such an intimate way of relating. I can’t believe that you would not be extremely significant in Andy’s life I can’t believe that he wouldn’t have said more about you.’
Suddenly Jane turned towards me and kissed me hard on the lips, my dick jumped immediately in response and my nipples seemed to become as hard as rocks. Just at that moment one of her hands reached for my breast, easily feeling my hard nipple through the thin material of my dress. ‘Fuck,’ Jane exclaimed ‘you are turned on by this as much as I am.’ Encouraged she deepened the kiss even further and her other hand moved to my ass cupping a buttock. ‘Your ass tits and ass are incredible’, exclaimed Jane, ‘you are fucking beautiful.’ Internally I was thinking to myself ‘YES’ here was the girl of my dreams and she thought I was beautiful, but then I started to worry about her finding out about my little secret.
Suddenly Jane said, ‘I have to have you now’, at that point the party was coming to a close anyway and Jane quickly made excuses and left, taking me back to her shared apartment. ‘What about your friends’, I exclaimed. ‘Oh don’t worry they will be hitting the bars they won’t be back till late.’ We arrived at her apartment and she slammed the door pulling me into her bedroom. Jane pulled me onto her bed and we started to frantically feel each other up. Her tits felt fantastic her ass was perfect and I could feel the wetness of her pussy through her panties.
Then suddenly came the moment I had been so anxious about, she grabbed hold of my now rock hard dick. Suddenly she pulled down my panties to see my erection in all its glory. Jane froze, staring at what she saw in amazement. Suddenly thinking that she must be horrified at what she saw I said, ‘I’m so sorry, I’m so sorry.’ ‘You’re sorry’ Jane exclaimed incredulous, then suddenly seeing the frightened look on my face she smiled broadly and said, ‘doing it with a shemale is my number one fantasy, this is incredible, you are incredible, a perfect female form and yet a shemale.’ ‘Fuck, now I want you more than ever.’
With that she quickly removed her clothes and mine and said ‘now my pussy is to damn wet, lick my pussy.’ Taking her pussy I licked around it building up the tension, then started to lick the surface of her pussy, by now she was starting to thrash around on the bed. Then I started licking her clit to which she responded saying, ‘oh my god, oh fuck’, I then sucked her clit into my mouth and noted the signs of her orgasm rippling through her body, she was yelling ‘AHH, AHH, AHH’, then I started to push my long tongue deep into her pussy, tasting her sweet juices. ‘Oh YES, YESSSSS,’ she cried out.
Then she cried, ‘I want your cock in me,’ and pushed me onto my back. Taking my 7 inch cock in her mouth she somehow managed to take me up to my balls, the feeling was incredible. But now she couldn’t wait any longer. She put her beautiful pussy over me and then engulfed my cock inside her in one swift stroke. Then with me fully inside me she was suddenly still, I looked at her and in answer to my unspoken question she said, ‘I just want to feel you inside me and look at you. It is amazing seeing your perfect feminine face, long beautiful hair, your incredible tits and yet at the same time have your dick inside me, it makes me so horny you have no idea.’ As if to confirm what you said I felt her juices streaming out of her pussy.
Then still not moving her body Jane reached down and slowly caressed my tits, gently brushing over my rock hard nipples. ‘I feel like I want you inside me forever Andrea,’ Jane said, ‘I don’t want to lose your hardness.’ With that she moved her position so that she was lying on top of me, with me still hard inside her. She kissed me tenderly moving very slowly back and forth as she did the feeling was exquisite. I could feel myself gradually building to an orgasm when Jane came, emitting beautiful noises from her mouth. At that moment I started moving inside her to bring myself to orgasm when Jane stopped me, ‘No,’ she said, ‘I want you to stay hard.’ Once she had stopped me moving she started to stroke my hair and speak to me softly saying, ‘Go to sl**p my beautiful baby girl, you are safe inside me, this is where you belong.’
Somehow I managed to sl**p, it must have been because of what I had d***k and the tiring effect of all the new experiences whatever the reason I slept, with a continuous stream of erotic dreams, every so often I would half wake up to find Jane kissing me or sucking my nipples and moving very slowly up and down on my engorged member. Finally I was awoken by daylight only to find Jane moving rapidly up and down and screaming out, ‘fuck, this is incredible, fuck me, fuck me Andrea, cum in me.’ When I did finally cum the intensity was incredible and it just seemed to go on and on, Jane’s pussy greedily sucking up my cum. In the end it was just too much and I must have passed out.
I was awoken by Jane bringing breakfast, home cooked pancakes which I ate with relish, Jane was saying to me, ‘It was amazing, you were hard all night and I used you to cum 10 times, fuck that was incredible.’ Suddenly I remembered, ‘well happy birthday Jane,’ ‘Thanks Andrea, and thanks to you I am having my best birthday ever. I am only missing one thing for it to be perfect.’ ‘What,’ I asked. ‘If only Andy was here,’ she replied. Now suddenly I felt guilty, how was I going to explain it to her, I just didn’t know how.
I had to go to the bathroom and when I did I looked in the mirror as I sat on the bowl. My face was a mess. I was in the process of slowly removing my makeup when Jane walked in, seeing my face with no makeup on it she suddenly exclaimed, ‘Andy!’ ‘Well I prefer Andrea now,’ I replied, ‘but yes.’ For a moment I saw a flash of anger in her eyes. She burst out, ‘Why didn’t you tell me? Exactly when were you going to tell me?’ My eyes were full of tears as I said, ‘I wanted to tell you when we were alone but it never seemed to be the right time, and when we got back here we were too busy making love.’
‘So are you pissed at me?’ I asked. ‘For not telling me, yes, damn right I am. That my beautiful shemale girl is you, No way! I love it, I love you, I always have, and it made me sad that there seemed to be no sexual attraction with you, but now I think you are the sexiest creature on earth, and with that she kissed me pushing her tongue down my throat. ‘Wait,’ I said, ‘I have a present for you.’ I went to fetch my hand bag and pulled out a DVD, please play it I told her.
Full of curiosity Jane put the DVD in her player and started watching, the video started with me saying in my male voice, ‘well here I am Jane, documenting my transformation to a T-girl, in the next few months I will be transformed into a female form, I am doing it because I know that I will have to become a girl to please you in the way I want to.’ There followed a documentation of the whole process I had gone through. In the process it made Jane, joyful, she laughed, she was intrigued. In the closing remarks in my new female voice I said, ‘Well in the end I have come to the conclusion that this is what I wanted for myself all along. So what can I say ‘enjoy the new bod.’
At this point Jane started to cry, concerned I asked her why she was upset, but Jane said, ‘I am not upset I am crying for joy, the fact that you could have done this for me, changed your body, grown tits, it is just amazing, I don’t think that a better birthday present is possible. I love you so much.’ She continued, ‘And by the way you didn’t have to grow tits for me, if I had known you had all this in you, this feminine side I would have accepted you as my lover as you were. But I am so fucking glad that you did grow the tits. So let me have a play with the tits you went to so much trouble to get for me.’
At this Jane started licking and sucking on my tits, with me seriously thinking that the way she was going she was going to make me cum without touching my dick. As you can imagine I have many more adventures of my new life to tell you…
*
So guys, do you want to see further chapters in this story? If you do please leave a COMMENT or THUMB UP below.
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