Tits Have Benefits Ch. 09

Following her honeymoon life starts to assume more of a normal routine for Andrea, well as normal as you can get when you are a shemale t-girl in a family with 4 lesbians.

Kate finds a shy new boyfriend and asks Andrea for help with him.

But can Andrea's idyllic lifestyle continue indefinitely, in this story things events take a nasty turn...

*

After transforming myself into a shemale and returning to claim the love of my life Jane, I was adjusting well to a life living with Jane's lesbian lovers, now also my lovers. On a combined business trip and visit to my friends, Jane and I went to California where we ended up having fun with my employer Liz as well as Trish and Sandy, ending up with me sucking Trish's dick. And later, despite my initial reservations, I took her dick inside me.

Later my sister Jill, who I had not seen for almost 2 years, came over in advance of the wedding along with her lesbian lover Ashley, and I ended up fucking and getting fucked by both of them. Just before the wedding I met Jane's brother John and his girlfriend Ally and had my first experience with a man, as I did not consider Trish to be a man.

The wedding was the best day of my life, where I was finally married to the four beautiful women I had come to love so much Jane, Jenny, Chris and Ann, and they all loved me, we all loved each other. On the wedding night as we lay together I really felt that this was where I belonged, the bride of four beautiful brides.

The honeymoon was wonderful, but when it was over all of us were looking forward to establishing some sort of normal routine as a legally joined family.

In my work on the new application for the Psynphone that I was doing for Liz, I had reached the point where we were ready to do a beta test on the product, and Liz had decided that a good place to conduct the beta test would be at our university campus so that I could supervise the application performance on a day to day basis.

All campus based students would be given the opportunity to participate in the test and if they agreed they would be given a free Psynphone along with an allocation of talk time and a monthly data allocation.

Liz had asked me to suggest a non-technical person to help me administer the test, who had to be a security minded person, given what would be some of the selling points of the new application, and I had suggested Jenny, who Liz had readily agreed to. Jenny was happy to take on this work as she would be handsomely rewarded for spending a few hours a week administering the tests.

So we had gathered the family together and Jenny was handing out the phones to each one of us. Then we were told to all strip off our tops, Jenny stripped off her own top as well. We could keep our bras on, much to Jane's disappointment.

Then Jenny went round applying a small adhesive patch to each one of us, as close to the heart as possible, explaining what they were. "This is a tiny piece of miniaturized technology is a heart monitor and is designed to monitor stress and health levels as well as general heart condition. There is a blue tooth connection to the Psynphone."

Jenny continued, "Andrea will explain how this monitor is used in the application."

I continued, "The heart monitor serves two purposes, firstly for people who are at risk of heart attack or even those that are not known to be at risk, the Psynphone will automatically call an ambulance and notify designated contacts when certain characteristic heart rhythms are detected. The application will also allow hospitals to remotely monitor the heart monitor while an ambulance is on route so that paramedics will have up to date information on the person's condition.

Secondly the monitor is also capable of detecting when the user is under high stress because they are being attacked or otherwise in severe distress, this will cause the Psynphone to automatically call the an ambulance and police as well as notifying designated contacts."

At this point Jenny commented saying, "I think right now the last function is particularly important for us given recent news that 5 women have been violently raped in this area. And to this end I also want all of you to sign up for self defense classes just in case."

After this I went on to explain the other features of the personal organizer features and social networking front end, explaining that each of us would complete a 15 minute survey at the end of each week documenting their experience in using the application.

Later that week Kate came to visit us and brought her new boyfriend with her, Allen, he like Kate was 18 years old. Allen appeared to be a very shy guy, which was surprising in a way given how outgoing Kate was. Jane and I could see that Kate really needed to talk so we excused ourselves saying we wanted Kate's advice on fashion and retiring to the bedroom.

Immediately Jane asked Kate, "Did you fuck him yet."

"No," Kate replied, "I really want to, but he is shy and I really don't want to screw it up with him as he is such a lovely person."

"So," asked Jane, "What is it you like so much about him?"

"He is so kind and considerate," replied Kate, "I feel so safe with him, I feel that I can talk to him about anything and never be judged, I just wish he wasn't so shy around me. It is like he is holding back, like he has some insecurity even with me, and that bugs me. I just want him to feel able to completely be himself with me whatever that might be."

"Do you want me to talk to him?" I enquired, "Back when I was a guy I was quite shy, I didn't feel secure, perhaps I can help him."

"Would you," replied Kate, "I would really appreciate that." And with that she gave me a big hug throwing her hands about my neck."

We, the family, invited Kate and Allen to spend the evening with us and after consuming food and quite a lot of alcohol, the girls were watching a program about makeovers for women that seemed to make Allen embarrassed for some reason. Noticing Allen's discomfort I asked Allen if he would help me with the washing up, and he jumped at the opportunity.

Once we were in the kitchen I started chatting with Allen about Kate, saying what a wonderful person I thought she was. Allen was heartily agreeing with me saying how she was so easy to speak to and so friendly.

As we talked I noticed that many of Allen's movements had a feminine appearance being very attuned to such things myself. And as we made small talk I observed that Allen was not very interested in 'manly' things, knowing what I knew about Kate I began to understand why she might be attracted to Allen.

So I said very casually, "So have you fucked Kate yet?"

In response to my question Allen's face became as red as a beetroot, he floundered a little, obviously taken back by the directness of my question. I could see that he was struggling to hide his anger at me for asking such a direct question but he simply whispered his answer, "No."

Explaining myself somewhat I continued, "Because Kate is a very spontaneous person, I am sure she wants you to fuck her, she must have dropped you many subtle hints and some not so subtle at all."

"Well yes," Allen replied, "she often invites me in for coffee after we go out, but I am always making excuses saying I have to leave. One time she really got mad at me so I agreed to stay for a few minutes, but when she started touching me a lot I made an excuse again saying I had to leave."

"Don't you like Kate?" I asked, "Don't you find her attractive? Don't you want to fuck her?" Knowing as I said these things that there was nothing that Allen wanted more than to make love to Kate.

Allen replied, "Kate is the greatest person I ever met, she is incredibly attractive, and I would love to fuck her, as you put it."

Some of his anger was beginning to show as he said these last words. This was exactly the reaction I wanted, it was only by him really getting in touch with his suppressed feelings that he would do what he desired to do as far as Kate was concerned.

Allen continued, "It's just that I am afraid that I will fuck things up between us, Kate and I that is? I have no experience sexually, I'm afraid she will not want to see me again."

Suddenly my tone became a bit harder as I said to Allen, "You expect me to believe that?" Then after leaving a dramatic pause I continued, "Sure you probably tell yourself that you are worried about your performance so you don't have to think about what might follow, but there is more to it isn't there. I doubt at your age you have problems getting an erection and you probably whack yourself off at least twice a day, probably five or more times." Allen's skin reddened as I said this.

"You know what a kind and accepting person Kate is." I continued relentlessly, "You know that she would be patient with you because you know how much she wants you."

"There is something else isn't there?" I said sternly, for the first time worrying if I was pushing the poor boy too far.

Suddenly, unexpectedly, Allen broke down and started to cry, and all I wanted to do was comfort him, so I put my arms around him allowing him to cry onto my warm breast. He felt reassured by my warmth and after letting him cry for a while I took his head in my hands wiping his long hair away from his eyes."

Then suddenly I gave Allen a quick kiss on the lips and said, "Allen, whatever it is you can trust me." And as Allen looked back at me he could see the sincerity in my eyes, so suddenly he confessed what he had been hiding.

"When I am alone I like to wear women's clothes." Allen said.

"Knew it," I said to myself, all the feminine gestures, not being preoccupied with things that interested most men, his sensitive emotional characteristics all made sense now.

As he finally said it, he looked frightened, almost as if he expected me to react with disgust or worse laugh at him, this, only moments after he had been sure he could trust me.

I said, "And you feel ashamed of yourself for this?"

"Yes," Allen replied, "I mean it isn't normal is it?"

"What is normal," I came back, "normal is a very relative term. So do you want to stop it?" I continued.

"Yes," Allen replied earnestly, "particularly now I am seeing Kate, but it is hopeless. I have tried to stop it in the past, but I always start doing it again, sometimes I feel most at home when I am dressed as female, it's hopeless, I'm hopeless."

Again he started crying and I pulled him back against my warm breast finding the feeling of his warm tears on my breast was producing nurturing feelings, and surprisingly erotic feelings, I guess it was just the effect of him being vulnerable with me.

"You know what I think?" I asked.

"What?" Allen replied.

"I think that Kate would be really pissed at you if you tried to suppress this side of you. It is part of you and helps make you the caring, sensitive, emotional person that you are, the person that Kate loves." I continued.

"You think so? Allen asked.

"I know so," I replied, "I think there is something you should know," I continued, "I am a T-girl myself, a shemale."

I could see the idea was not sinking in, so I made it as clear as possible, "I've got a dick."

"B-b-but, that's impossible," Allen replied, "You must be winding me up, nobody could look more womanly than you."

With that I pulled my panties down and lifted my skirt, saying, "Satisfied," as Allen looked at my semi-hard cock.

"You know," Allen said, "even when I see your dick clearly displayed I cannot think of you as anything other than female, but I guess you have heard that before."

"Oh all the time," I said.

"Look," I said, "I happen to know for a fact that Kate doesn't have any problems with a guy who has a feminine side, quite the opposite in fact. When I come to think about it, it was probably subconsciously picking up on the fact that you had a feminine side that drew her to you in the first place.

But right now you first need to concentrate on accepting yourself and becoming comfortable with who you are in your feminine form and I can help you there, but you have to trust me completely, what do you say about us meeting up together in a few days so I can help you explore your feminine side."

"Thanks," said Allen, "I would really appreciate that."

I noticed that Allen was already looking much more self confident, and after we returned to the girls to playful banter about what we may have been up to together, Allen sat next to Kate and I could see that his whole attitude with her was much more confident. He was more outgoing and even rested his hand on her leg when they spoke.

Kate had a big grin on her face, she looked like the cat that had swallowed the canary.

That night as Kate and Allen left us, Kate whispered in my ear, "I don't know what you said, but thank you." She squeezed my hand as she said it.

I whispered back, "The best is yet to come, believe me."

So it was that Allen arranged to meet up with me later that week in our apartment.

When I answered the door, the other girls were out at university except for Jane who did not have classes that day. Jane was at a local café, nearby waiting for my call.

As I led Allen to the bedroom he looked a bit pensive, so I started with some general chat to put him at his ease.

"So how has it been with Kate?" I asked.

"Great," replied Allen, "since I opened up to you about my cross dressing, I feel I can be much more myself with her. We even kissed one time, and I touch her we hug and stuff all the time now."

"Did you guys made love yet?" I inquired.

"No not yet," replied Allen, "I think she wants it, but I keep putting her off before things go too far. I want, I want..."

"You want to feel more comfortable with yourself before you take the next step with her." I supplied.

"Yes," Allen said. "I want to explore who I am more."

"Well you have come to just the right place," I said, "that is exactly what we are going to do."

"So," Allen inquired, "How are we going to go about this? How do we proceed?"

"Well," I replied, "You are going to meet your alter ego, the side of yourself that you have been suppressing for so long, and first that means taking a long bath, so you can smell sweet and remove all that body hair, not that you have much to speak of."

So it was that I got Allen to strip naked and get in the bath, to put him more at his ease, I just put on a short bathrobe myself, I chuckled to myself when I noticed Allen's dick hardening as he saw me in just my short robe.

As Allen bathed and applied the hair removal cream, I sprung my surprise on him.

"Look Allen," I said, "transforming you will take quite some work, and it would go much more quickly if somebody could help me with you."

Suddenly Allen looked frightened, "I-I'm not sure about that, I feel safe with you, but somebody else, I'm not sure I could do it."

At this point I replied sternly, "You said you would trust me completely, and besides you are going to have to tell other people about this sometime, Kate will have to know for example, being open about who you are with people you can trust is very important in the process of self acceptance, the sooner you start the better."

"OK," Allen replied, "If you vouch for this person."

"Don't worry, I trust her implicitly." I said. "So it's ok if I have her come along?" I reiterated. It was important that he felt happy about me bringing somebody else in to help with his transformation.

"Yes." Allen replied.

On Allen's confirmation, I called Jane, "It's ok to come now."

Jane arrived more quickly than I would have thought possible, eager to help in the transformation, quickly enough to catch Allen while he was naked, just getting out of the bath.

"OOOh," said Jane always direct, "You do have a nice bod Allen, and you look sooo good with that smooth hairless skin, your skin is so supple and soft, just like a woman, but oh my you have a lovely cock, I'm sure that would feel lovely inside me."

At Jane's words Allen reddened and he quickly grabbed for a towel to cover his private parts.

After rubbing himself down with a towel I passed Allen a short bath robe like the one I was wearing, and so as not to look out of place Jane also put on a similar bath robe.

We sat Allen down on a chair and I got to work styling Allen's long blond hair into a very feminine style while Jane gave him a manicure and a pedicure, painting his nails a bright red color.

I then went on to work on Allen's face, working on his makeup while Jane went to select some clothes for him.

When I had finished with his face even he would have had trouble recognizing himself in the mirror.

Jane, knowing what we would be doing had thoughtfully gone out and bought some breast forms and a gaff for the transformation.

And as Jane was putting the breast forms in place with a mild adhesive, Allen became a little alarmed, "How permanent is this stuff?" He asked.

"Don't worry," replied Jane, "this glue is only temporary and there is a solvent to break it down when you want to remove the breasts.

As Allen put on a red panty and bra set that Jane had laid out for him I noticed that he was getting an erection even with the gaff he was wearing. Finally he slid into a pair of strappy shoes with 4 inch heels and Jane helped zip Allen into the tight fitting red minidress. It was only at this point that we let Allen see himself in the mirror.

As Allen looked at himself his Jaw dropped, he reached and touched himself on the breast, at first he even seemed unsure that he was looking at himself.

"Oh fuck, I'm beautiful," said Allen, "thank you so much guys, I would never have believed I could look this good."

Then he turned to Jane, "What do you think?"

Jane replied, "You look totally passable, no one would ever guess you were a guy looking at you. But then as you begin to get used to being like this you will start to realize that when you are like this you are not a guy, but rather a beautiful girl."

At this I could see the pride in Allen's face.

Jane continued, "You also look totally fuckable, I would fuck you right now if I didn't know that you want Kate to be your first."

This again caused Allen's to turn red, but less so than before, he was beginning to become more confident and less embarrassed as time went by.

Jane continued, "But we can't call you Allen anymore when you are like this, have you ever thought of a feminine name for yourself."

"No," replied Allen, "up till the day I confessed to Andrea, I was just completely ashamed of this aspect of me."

"Well how about Alice," Jane supplied, "it sounds similar to Allen so it would be easy for you to remember."

"Alice," Allen repeated, "I like that name, and I think it fits me, after today I certainly can identify with 'Alice in Wonderland'."

Now it was time for our next surprise for Allen/Alice.

"Well Alice," Jane continued, "how would you like to come out to a lesbian bar with us?"

"L-Like this," Allen replied very anxiously.

"Well at the bar I am thinking of, I don't think they would take too kindly to you if you went as a guy," said Jane, "and besides you will pass as a girl no problem, and if anybody did spot that you are a t-girl it wouldn't be a problem as there are quite a few trannies who go to this bar and they are always welcome."

Jane and I had discussed taking Allen, now Alice, out before hand, but I played along pretending the suggestion was new to me.

"Now wait a minute Jane," I said, "Alice is still new to all this, it is her first day dressed and fully made up as a girl, and her first time ever dressed when she has not been alone, and you want to take her out like that. Aren't you rushing things a bit."

I could see that Allen/Alice was looking at me with relief, glad that I had stepped in on his/her behalf.