Caught by Julie

This story involves Cross Dressing and sexually explicit material, if you are under the age to legally read this in your area please go no further. If you are old enough please enjoy. This story is totally fiction, any names or actions are totally coincidental.

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Caught by Julie (TG) by andrea_tas@hotmail.com

Like many others I started cross-dressing when I was quite young, starting with clothes of my mother's, especially lingerie, whenever I had the opportunity. I also had the opportunity a couple of times to raid the next door neighbour's clothes line for some even more exciting lingerie.

Since those days I have had more opportunities to dress but it was something I always kept secret and had never been seen dressed by anyone else. I am now 28 and have a 25 year old girlfriend who, like everyone else, doesn't know my secret. Even though I love having a regular girlfriend it has meant that I have not been able to dress much at all, I have even had to stash my clothes away well out of the way of Julie finding them and have not been able to shave my legs or underarms. I have never needed to get rid of hair on my chest as it is naturally free of hair. I am about 5'9", quite thin and not very muscly. The sex we have is very good (at least for me) though as I have quite a small dick I think Julie would prefer if I was better endowed although she has never complained about it or made fun of it.

One Saturday morning I was in Julie's flat. She had gone out to the gym followed by shopping so I wasn't expecting her back for at least a couple of hours. Since we had got together I had always wanted to try on her clothes but had never had the chance till now. I selected some lovely purple bra and g-string that I loved on her and put them on. As I didn't have my breast forms with me I filled the bra cups with some stockings. Then I put on a crop top and skirt and went and admired myself in the mirror. I started thinking about putting some makeup on, thinking of how long it would take to get it on and off and whether it would be worth it. I decided to put some simple make-up on and sat down in front of her dresser and looked through her make-up. I was just putting some lipstick on when suddenly I heard Julie's voice.

"Oh my God! What are you doing?"

I froze and was speechless.

"I think you need to get out of my things and go home." Julie said. "I need to think about what you've done before I can even consider talking to you about it."

I got out of her clothes while she just stood and watched me, then put my clothes back on. All I was able to say to her was that I was sorry and then I left the house.

Later that day I got an email from her. She asked all sorts of questions like whether I had cross-dressed before, whether I had used her clothes before, whether I had my own clothes, was I bisexual, how often did I do it, why hadn't I told her and didn't I trust her. I answered as honestly as I could, telling her it was my first time in her clothes but I had dressed frequently before but only in private and gave her a quick run down of the clothes I had. I told her that I did have thoughts about doing things with guys when I was dressed but that I had never done anything with guys, and that it wasn't that I didn't trust her, it was just that I was too afraid of people's reactions to let anyone know.

A little later she emailed me back:

Hi Andrew,

I have been thinking about what you did. I am most hurt by the fact that you couldn't trust me enough to share this with me and that you went through my stuff and wore my clothes without my permission. I do think you looked quite cute in that outfit. I probably would have been happy to support you with your cross-dressing if you had talked to me about it. Now I am not sure that I can trust you and I I am not convinced that you really love and trust me.

If you love me and want our relationship to continue you are going to need to regain my trust. If this is the case you need to tell me that you will do anything I ask of you without question or complaint. I may ask things of you that you are uncomfortable with but you will have to trust me that they will be things that you will be able to handle, though it may require some adjustments to how you think about things.

Julie

I thought about it for a short time and realised that I did want the relationship to work and so I would have to trust her, not matter what she wanted. I figured there would be something that she would want that would be a punishment or to teach me a lesson. I decided I would have to trust her not to ask anything of me that I couldn't agree to but also realised I may have to agree to things that I did not want to do. I emailed her back and told her that I would do anything she requested. I then waited with slight apprehension for her to contact me again.

Hi Andrea,

The name I used should give an inkling of what I am going to ask of you. I expect to see you here at 11am tomorrow morning. I want you to look pretty, slightly sexy (but not slutty) and dressed for a nice lunch. So not every day wear but not evening wear either. You are to have shaved your legs, underarms and either trimmed or removed your pubic hair. Obviously I expect you fully made up. Let me remind you that you are to arrive dressed like this, you are not to come dressed as a guy and then get changed here. This may be a little scary for you but it should give extra incentive to look as passable as possible. I shouldn't need to remind you that if you don't agree to this without complaint that the relationship is over. You do not need to worry about lunch - I will organise that.

See you tomorrow Love Julie

Maybe I was being a bit dense but I did not expect this. In retrospect I suppose I should have thought that she might ask something along these lines, but I still wouldn't have expected it to involve me being dressed in public. It wasn't really possible for me to not do it without risking my relationship. Julie normally means what she says so I had no doubt that she would dump me if I didn't go through with it. I decided that it wasn't as if I had to interact anyone while dressed, except Julie, and that all I needed to worry about was being seen and recognised getting into or out of my car or while driving.

I went through my clothes and selected what I thought would be nice. Then I trimmed my hair including my pubes. I left the shaving till the morning so that it would all be nice and smooth and freshly shaved. I then pulled out my favourite teddy to wear for the evening and night.

I got up quite early the next morning to get myself ready in time. When I was ready I had a last look in the mirror and decided I had done the best job I had ever done of looking good. I then checked the time and it was time to go. I was scared but I forced myself to just do it and went out the house and got into the car and drove to Julie's. As far as I know no one that I knew saw me which made me a bit less nervous.

I got to Julie's and when she let me in she complimented me on how good I looked, even saying that she didn't think I would look anywhere near as lovely as I did and that if she didn't know me she wouldn't think twice about me being a girl. She looked very lovely and had picked a really nice outfit and wore a lot more makeup than she normally wears in the day. She poured us each a glass of wine and we talked about nothing much while she did a few more lunch preparations. Then she poured another wine for us each and we went out to the patio at the back. I got a sudden surprise and shock when I saw that the table had been set with three places. I was about to ask and Julie told me to just wait and see and had a look on her face that told me I was not to question her. It was hardly any time before the front doorbell rang. Julie asked me to go and answer it. I was petrified but couldn't see that I had much choice in the matter except to do as she said and trust her. I opened the door and a close friend of both of ours, Greg, was at the door.

Greg said "Wow! You must be Andrea. Julie never told me that her girlfriend was so beautiful. I'm Greg. It's so nice of the two of you lovely ladies to have me over for lunch."

I mumbled "Thank you". And let him in. He gave me a kiss on the cheek and a quick hug as he came in which threw me into a state of confusion. Surely he knows it is me so what is he playing at - what are the two of them up to. When he saw Julie he complimented her onhow lovely and how sexy she was looking and gave her a much longer cuddle and kissed her passionately on the lips to which she seemed to respond just as passionately.

I was wondering how long this had been going on but Julie said "I never knew you were such a great kisser or that you even found me attractive".

Greg replied by saying "I have always tried not to think of you as attractive in that way because you were in a relationship but that was hard because you are one of the sexiest women I know." Then he looked at me and said "And Andrea is extremely sexy too and I am sure I will find out how good a kisser she is before too long."

I realised that they had not been doing anything together but was wondering about what they had been saying to each other since yesterday. I was also so flattered by Greg's compliments that I figured I may as well just go along with things for a while.

I got Greg a glass of wine and to thank me he pulled me to him and gave me a long soft kiss on my mouth. I responded almost automatically by kissing him back quite passionately.

We had lunch and Greg continued to flirt quite openly with both of us. After lunch Julie put on some music and greg asked us to dance. He danced with both of us for a while and then a slow song came on. He took me in his arms and we danced. I could feel a very sizeable erection pressing into me as he held me close and let his hands wander over my ass and back. When the song finished he let me go.

Julie said "My that looks like a very impressive package you have there Greg. It looks like Andrea here has got you all horny.."

Greg replied "Yes she has gone and turned me on quite a bit. I hope she isn't just a cock teaser."

Julie said to me "Andrea you had better help Greg out with his problem. I know you are sweet and innocent and have never given a blowjob before but I am sure that you will know instinctively what feels good to a guy."

Even though I had had fantasies about doing this for years I was still very nervous now the opportunity had come. Again I realised that I had no choice if I wanted our relationship to continue and I did want to see what it was like to suck a guy's dick. I went over to Greg and stroked his dick through his jeans and then unzipped him. Reaching inside I freed his dick from his underwear and pulled it out through his fly. It certainly was an impressive erection. Much larger than mine. Julie gave some sounds of obvious appreciation and lust for it. I knelt down in front of him and first licked the end of his dick and then took his head into my mouth. I though about what felt good to me when I got a blowjob and tried to do that to Greg using my hands and mouth to make him feel good. Julie meanwhile started stripping Greg's clothes off until he was naked with me still in front of him sucking his dick. I could tell he was getting very close and changed my technique a little. Suddenly I felt the first spurt of come into my mouth followed by several more as I swallowed his come. It tasted different to0 mine but tasted absolutely wonderful to me. Even though I hadn't got fully hard and my dick was still tucked down in my tight panties I felt a tightness in my panties just as Greg started to come and then had come in my panties as the second spurt of his went into my mouth. It was both the first time I can remember coming without having my dick touched or in someone and also the first time I had come without having a full erection.

I released Greg's dick and stood up. I went over to Julie and whispered to her that I had made a mess in my panties and did she have a pair that I could borrow.

At this Julie said "Well Greg it looks like both of you enjoyed that. Andrea here has got so wet in her panties that she wants to borrow some of mine to change into. I guess we were right in thinking she would enjoy your attentions. Andrea, lift up your dress and show us how much of a wet spot you have in your panties."

I did as she said and they both commented that yes I had got very wet and probably needed to change my panties. They suggested I put a G-String on and that I should fix up my makeup while I was there. Then Julie leant into me and said that perhaps I should get the KY and a vibrator and make sure I am nicely lubed and loosened before I come back out. She told me that she would keep Greg amused and that it had been too long since she'd had the chance with a real man's dick rather than an overgrown clit trying to satisfy her.

I did as she said. I had had dildos and butt plugs in before so it was easy for me to do as she had requested. I was a little put out that my best friend was about to fuck my girlfriend but that was balanced by the fact that I had thoroughly enjoyed the blowjob and was very likely to have a real dick rather than a dildo in my ass sometime soon.

When I returned they were no longer in the lounge room but I heard noises coming from the bedroom. When I walked in the door I was greeted by the sight of my girlfriend being fucked fast and hard by Greg's big dick. She was making noises of enjoyment I had never heard before. I realised then that my dick was never going to satisfy her in the way that a big one could. Almost straight after I walked in Julie had what looked like a really powerful orgasm. Straight after that Greg pulled out and with two or three pulls on his dick he sprayed his come all over Julie's breasts and face.

He then told me to come and clean then both up. I went over and took his dick in my mouth, tasting the mixture of his come and Julie's juices. I then licked all of Greg's come off of Julie's breasts and face. Greg said that he would need a few minutes to recover but that he wanted some visual stimulation. He told me to take my dress off but leave my underwear on and then to eat Julie's pussy. I have always loved going down on Julie so I took to this task with great pleasure. It wasn't too long before Julie had another orgasm flooding my face with her juices.

Greg then asked which of us wanted to suck him to a new erection. Julie firmly told me that it was her turn to suck on a real man's dick and went to work with great pleasure. When she had got him fully hard again he said that my time as a virgin was about to finish. He lay me down and without removing my g-string, just moved it to the side, lined his dick up to my ass and pushed all the way in in one go. It was just as well I had lubricated otherwise this would have been quite painful. As it was it was a little uncomfortable as I didn't have as much time to adjust as I normally give myself with dildos. When he was fully in me he left it there for a short time so that I could adjust and then started to slowly fuck me. He got quicker and harder as we continued to fuck. After a few minutes he was obviously ready to come again and as I felt him start to come I again came in my panties.

Greg then pulled out and we all went to take a shower to clean up. I had thoroughly enjoyed my first time dressed with other people, my first time having sex when dressed and my first time with a man. As we had the shower Greg saw me for the first time in the nude and told me that it was no wonder Julie wanted a nice big dick with that pathetic thing you have and that I certainly made a much better girl than guy in the bedroom. After seeing Greg's performance I could only agree.

After the shower Julie and I went into her bedroom to get dressed telling Greg to just make himself comfortable and have another drink. As we got in she said that she was really proud of how I had been, was glad that I had shaved my pubes as well as everything else and indicated that this was not to be the last time I became Andrea. I told her how I was initially uncomfortable with her having sex with someone else but how much I enjoyed it after accepting it and how I realised she needed a proper man once in a while. She got out some fresh clothes for both of us and we redid our makeup before rejoining Greg.

After having another drink with Greg he said "Okay ladies we are going out to listen some music and have a dance."

I was about to say no I can't go out in public but I saw the look that Julie gave me and said nothing. She accepted the offer and we left. The pub that we were going to is one I went to fairly frequently, particularly on Sunday afternoons as it generally has some great music. There was bound to be someone there who knew me so I was petrified. We got there and sure enough I saw a few people I knew. At first I thought none of them had recognised us but then one of them come over and say hi to Greg and Julie. He then asked where Andrew was and who our lovely friend was. They introduced me as Andrea and Peter asked me to dance. Julie nodded so I said yes. Just my luck a slow song started when we got to the dance floor and Pete pulled me into his arms and danced.

After a little dancing with another very healthy bulge pressing into me Pete said into my ear "You do make a very lovely girl. Do you think Julie will let me take you to bed?"

I said that he would have to ask Julie as she made those decisions. He asked me how often I did this and I said it was my first time in public today. Meanwhile I could see Julie with Greg and two other guys in one of the booths. Greg was opposite her and the two others were very close and it looked almost certain that there was some action happening with hands under the table. After a little more dancing Pete took me over to join them. He asked Greg and Julie whether they would mind him spending some time with me to which they both said that it wasn't a problem. Julie added that she had plenty of real men to keep her amused. I could see by the smirks on the two guys faces that they knew I was a guy. Pete took me out of the pub introducing me to some of my friends along the way. Most of them didn't seem to notice anything strange but one or two gave me odd looks and emphasised Andrea when they said hi, making me pretty sure that they knew as well.

I went back to Pete's house and he wasted no time when we were in the door, taking me in his arms and kissing me passionately. I could feel his erection growing and pressing against me. He led me into the bedroom and kissed and touched me as he took my shoes and dress off leaving me in my underwear. I then started to undress him loving the feel of his body as I got down to his well-toned chest and body. He was soon just left in his jocks which were struggling to keep his erection in. I took his jocks off and was confronted by the second dick I had seen that day. He was uncircumcised and slightly longer but not as thick as Greg. I took him in my mouth and enjoyed the different taste and feel of him. In almost no time he shot a load into my mouth. I had what felt to me like an orgasm when he spurted in my mouth but I realised it was a dry orgasm which was quite strange to me.

He then kissed and massaged me for a while. He left my bra on but removed my panties revealing my small shaved dick. "Oh that is such a sweet little thing" he said. "No wonder you make such a lovely girl."

With that he took my dick in his mouth and slipped a finger in my ass. Within a minute I exploded into his mouth. He didn't swallow but kissed me and pushed all of my come back into my mouth. I could feel his dick start to grow again and decided to be a bit more active. I stroked him with my hands till he was fully erect and then climbed on top of him and eased my ass down onto his dick. I rode him fast and hard until I felt him shoot his load into my eager ass. Again I had a dry orgasm as I felt him come. It was seeming like making a man come automatically triggered an orgasm for me, whether with or without ejaculating, and that I didn't need to be hard for this to happen.

After cleaning up I left him and got a taxi back to my house. When I arrived I sent an email to Julie explaining what I had done and thanking her for the wonderful day. I didn't want to go round in case she was busy with her new men.

Late that evening I got an email in reply from Julie.

Dear Andrea,

I am so happy with how well you acted today. The fact that you obviously enjoyed it so much and that I enjoyed having a real dick (or three) does indicate that some changes are in order for our relationship. I have always loved everything we have had except for sex where I have never really been satisfied. As word will be out quite soon (and we can make it sooner if you object in any way) about you being such a sissy boy the following changes are to occur.

1. Unless given special permission for some reason you are to wear women's clothes all the time. I would suggest at first you stay with skirts and dresses until you perfect your female mannerisms at which point jeans and other things will be fine. As you know this will not cause any problems with your work and it obviously won't cause problems with your partner. You are to attempt to always look feminine and not try and get away with an androgynous look.

2. I will be moving in to your house from tomorrow. Greg and others will stay in the house as often as I see fit. I will let you know when I wish to share a man with you or give my lover permission to use you. If I choose to let a man use you for sex you will give him pleasure in whatever way he desires.

3. I will move into your bedroom. You can move your things into the spare bedroom. You will only use the main bedroom when I want you to sleep with me. This may include sleeping with me and a man.

4. I have no objection to you bringing home sexual partners, in fact I encourage you to do so to gain more experience. You are never to deceive them into thinking you are a male. You are a sissy-boy who is on her way to becoming a girl. Obviously this will normally either be at his (or her) house or in your bedroom unless it seems appropriate to me that I join in. I do say her as you may find women who are attracted to the idea of having a sissy-boy.

5. I am the one in charge of our relationship unless I give leave to a real man to take charge. Although we will share the household duties you will be responsible for most of the traditionally female chores with us sharing the other duties.

6. From as soon as I can get them you will start taking a course of hormones. This will probably further reduce the size of your pathetic equipment, but it will also start to give you more feminine appearance and real breasts. At a point in the future we will see whether implants will be required. As far as the reduction in your ability to ejaculate and the lessening of size it does not matter as I will have real men to provide penetration and you are very good with your hands and mouth. I have no doubt that you will be able to receive any satisfaction you need through other means than fucking me.

I love you and think we will have a better fuller all round relationship with you as Andrea. We will be even closer friends and partners out of bed and I will be able to receive true satisfaction in bed and will be able to share that with you when it is appropriate.

Julie

I had to read and reread the email a few times and think very hard about it. I realised she was right. I work for myself from home and don't have any face-to-face contact with my clients, it is all done through email. I can easily make gradual changes to calling myself Andrea with my new clients and perhaps even with existing ones. I enjoyed the sex as Andrea more than I have ever enjoyed sex before. The best satisfaction was the feel of a dick in my mouth or ass and feeling someone come, whether they are a guy or girl and whether with my hands mouth or ass. After seeing how a real man with a proper dick made Julie react I realised how useless my own equipment was and so it wouldn't matter if it became smaller or less likely to become erect. It would just make it even easier to hide any bulge.

I emailed her back with my full agreement. Then I cleared out my old male clothes and put my female clothes into the spare bedroom which was now to be mine. I knew I would have to do more clothes shopping and the thought of that was wonderful. I would also be able to put some more feminine touches to my bedroom and to the rest of our house. I had come to realise that I looked pretty good as a girl and that I did not care if people recognised me as being aguy in girl's clothes. I went to bed in my nightie feeling a very happy girl, looking forward to my new life, to the possibility of having real breasts and to the thoughts of living my life as a girl.