The (mis)adventures of Jenny

[Jenny Elwood]

Saturday my wife kicked me out. She wanted me out Friday but relented when I asked where I could go at 23:00 on a Friday. She said she was "gatvol" (direct translational: arse full or in better English fed up). She said she was tired of seeing my body around but my mind somewhere else. You can only feed the monster scraps by underdressing for so long since I'm not allowed any of my stuff at home. "Go and be Jenny , get it out of your system and come back in two weeks time." My arguments that two weeks was way too much fell on deaf ears. So on Saturday morning I told the kids I was going away for work and amidst all the crying I drove out.

I went to the shops first because I needed a couple of things. I buy most of my stuff from the cheap Chinese stores since my dressing is on a shoestring budget (I have a stay at home mom wife and five little mouths to feed). Besides, the chances of running into anyone I know is smaller, and they even let me try on stuff in male mode (I've never tried to pass). The clothes are mostly garish but if you sift a bit you can find some gems.

As I was about to get into my car an evidently homeless woman comes up to me and asked for some cash. She showed me her arm, which wasn't looking to good (it looked broken)and told me she had no money for the shelter the previous evening , so she got mugged and hurt her arm. Now it may come as a shock to you but in my country I've been the victim of this scam before. People are so desperate they break their own arm to garner sympathy so you'll give them more than just a couple of bucks in order for them to "pay for the hospital fees". Insane but true.
She seemed so desperate though and on face value she was sober. I was feeling guilty for buying stuff I don't really need whilst this person did not know where her next meal would come from, so I gave her some cash and some food. She tried to extract more by telling me she needed a change of underwear from the cheap shop. I was tempted to tell her I'd just bought some and I could give her some of mine, but thought better of it. My XXL's would just slip off her finger like frame anyway.

She enquired where I lived and I told her I was also homeless now, since my wife chased me away. I drove off but as I was busy paying for the parking she walked past and told me she begged at the nearby McDonald's and KFC. If ever I wanted to just talk a bit I could look her up. I suppose a seed was planted...

I slept in my office that night and booked into a cheap motel the next day. I was going to do it: The McD's drive through thing! I got dressed, put on my wig and a pair of oversize sunglasses (at night). No make-up though, I still have no clue and have been trying unsuccessfully to find someone to help me. I made the couple of steps to the car, after making sure there was no-one in the parking area, and drove out. The security at the gate looked a bit befuddled but let me pass without incident. The ladies at the drive-through seemed intrigued but said nothing and I avoided contact like the plague. Funny, in my country crossdressing is an unbeknownst concept amongst black people, yet they seem a lot more tolerant. I've grown to enjoy black people in the new South Africa, a far cry from the distrust in the old, racially segregated SA.

My homeless crony was at the exit and she didn't recognize me until I pulled off the froggy glasses. She nearly fell on her back but we had a nice chat and she even gave me a hug! I told her now she can see for herself why I'm homeless. She asked for a cigarette and I told her unfortunately this is my only vice and drove off after I gave her some money. I suppose she's only my friend due to an expectation but at least it's nice to meet a woman that does not go like a clamshell when she finds out.

Took the plunge yesterday after work of buying my first piece of make-up (bar the complementary green lipstick that goes pink at contact I got from the Chinese shop). Read up in the advice columns and memorized it: "Shave, Concealer, Foundation, Powder." What could be more simple than that? I ran into the large chain store pharmacy and thousands of little boxes, clasps?, tubes, tins and I do not know what else stared back at me. The staff started to check me out, I panicked and ran for the door. Went to the grocery store since they only had a small shelf of stuff and slipped some foundation in with my food. I was stunned at the price woman was willing to pay for such a small container though! I still managed to keep my wits about me and knew I had to get the stuff off again I could not get anything that said "facial cleanser" or whatever the packaging said I needed, so I grabbed some baby oil as I remembered someone mentioning. I figured concealor would be hard to find since most "real woman" don't need it. At least I had something to experiment with.

Last night I was emboldened and went to the KFC since I saw my friend standing there earlier. I actually engaged with the staff this time amidst the giggles and smiles. What the heck, go big or go home! My friend ran over excited to see me and I parked off for a chat. She inspected my size 17 US heels with the pantyhose in to keep them from slipping off. Shipping to SA is double the price of the shoes and for some reason I was scared the 16's would be too small. She said she was floored the other night but liked my longer wig I wore then more. I mentioned something about my make-up issues and she said she used to be a stunner before she fell into drugs and that she could help me!

We talked about other stuff and I told her I wasn't gay. I'm not too sure but I think she hinted at getting me a prostitute. I hid my disgust and told her I'd only be interested in the make-up thing, gave her my number and some cash (she has no phone obviously) and drove back to the motel.

Twelve o'clock the phone rings, it's her and I need to phone back. She sounds as if she's in trouble and needs help. For the life of me I cannot figure out how to get the phone log on my cell phone. I'm useless when it comes to phones and I don't even have a fancy one! So I drove out to go and play the rescuer (in drab). I'm not much of a fighter, but people do find my 2.00 m (6'6" for you there in the US) frame intimidating, not so much if I was wearing a dress though.

I found her at a local petrol station, she seemed okay and promptly jumped in my car. I let the trouble thing slip as she says she will go buy some make-up stuff the next day but she needs money. Now this is a watershed moment since this could go one of three ways: She could be good for her word and get the stuff, which would be good. She could go back on drugs which would be bad. Or she could use the money to get her arm sorted out, the obvious choice for me. So I decided I would give her the benefit of the doubt and give her the money, if she wasted it on drugs that would be the end of it. As we drove to an ATM she told me things about her life. The drugs, the beatings and the panga one man stuck in her leg. She showed me the battle scars of her eardrum bursting as one man hit her in the face. She says that she's going to put her life back together this year, so I said maybe she should consider helping people like me out with make-up! I was a little shocked as I handed her the money and dropped her off.

That is the story so far. Today is my wife's birthday, she is in the GG section under the name Lidea. I doubt whether she will read this since she's taking (and by the sound of it enjoying) a break from Jenny. I miss her, I love her and I'm sad that I cannot be with her on this, what should have been, a joyous day. I miss my five rug rats as well, but I have to admit I am enjoying being Jenny. What will happen in a week and a half's time I do not know. I know that I cannot put my selfish interests above that of my wife and kids, so I'll probably have to say goodbye to Jenny for a while.

[Katey888]

Crikey Jenny! That has to be one of the most extraordinary outings anecdotes ever... And in fact you're in the midst of this right now, so it's more like a real time journal... completely compelling - and I hope a wonderful experience for you.

But do be careful! I've made only a couple trips to SA some years ago - to Jo'burg and one chaperoned trip to Soweto... I don't think I've been to a scarier place although it was safe for me.. So take care! I'm sure you know what you're about...

And look for makeup tips on YouTube... it has to be easier than finding a homeless woman :) and perhaps better...?

You sound like a good and generous person to me, Jenny - hope it works out well for you back at home too... :hugs:

Katey x

[Marcelle]

Hi Jenny,

Goodness that is quite the situation you have found yourself in and still more time to go. I agree with Katey, please do be careful when you are out and about . . . remember you have your family waiting and counting on you. I can understand your angst when you are not allowed to dress as Jenny at home and hopefully sweetie, this two weeks will help. However, I don't think it will get it out of your system and in fact it may harden your resolve to present more in the future. When you go back home, you should sit with your lovely wife and perhaps discuss what can and cannot be lived with . . . perhaps a DADT relationship or a Jenny Day here and there. I truly believe you will have a hard time just quitting "cold turkey" after two weeks.

Good luck sweetie and keep us informed as things progress.

Hugs

Isha

[Beverley Sims]

Be ever mindful of what you say and do when you are in this state of mind.
You still have the family to go back to after this is over.

[MsVal]

Dear Jenny, I am so very sorry to read of your plight. There may be a bright spot here and there, but overall this reads like a tragedy. Please be aware of your surroundings and take no risks that a GG would not take. Make attempts to stay in contact with your family. Your wife may not want to talk with Jenny, but your kids would love to hear from dad.

The bright spot is that you will have two weeks to explore life as Jenny, and your wife will have two weeks to experience life as a single mom. As your adventure draws to an end you will have quiet time to ponder Jenny's future. I DO hope that you can find a way to integrate your family and your legitimate needs.

Best wishes
MsVal

[Jenny Elwood]

Hi and thank you for the responses Katey, Isha, Beverley and Val

As per usual you dealt out some sound advice, and really are the stars among this forum. (I don't think I qualify).

I suppose I'm naïve in that way but for some reason I always believe that there's hope for people who've had a hard time of it (whether it was due to their own mistakes or caused by others) to put their lives back together. That's why I put in the effort (and a substantial amount of cash in our useless currency) with my homeless friend in the hope of getting some return (that she would get her life back on track). Sadly I have to report that, like with my other hobby (share trading) I've paid my school fees yet again. I can only hope that one day it will, like with my hobby, pay huge dividends if and when I decide to do the investment again.

[sherri]

Interesting story, but you sorta lost me at "my wife kicked me out". I'd be like, uh, no, YOU go if that's what you want. OR, maybe we could take another approach to hashing this thing out. Just sayin'.

[Shelly Preston]

Jenny this is not an easy situation for you in lots of ways. I can feel your pain over what has happened. I would be surprised if two weeks as Jenny helped get her out of your system. I do think you need to sit down with your wife and discuss what arrangements you can have to please you both. DADT is one option
As she is a member here I am sure she has been told that dressing very rarely goes away.

I wish you both the best of luck going forward


I am sure the kids will be missing you already.

[Jenny Elwood]

Hi

Sherry there's a lot more involved here than my (selfish) needs to dress, for one there is the innocence of my five kids which I need to protect at all cost. I don't want them to ever see their father dressed (especially the boys). My wife is a firm Christian believer (I used to be firm too) so there's not a lot of willingness to compromise there.

Shelly thank you very much for your thoughts, you've hit the nail on the button: I can vouch for the fact that it doesn't go away. We will sit down shortly and discuss the future and see what we both can live with. I know that (and she's not going to like hearing this) Jenny is a bit more ingrained after this last week or so.

On a lighter note, I managed to put the homeless lady incident behind me quickly (she had the audacity to phone again!). Day before yesterday I spoke to my neighbour in the motel (he's been living there for a year with his wife) and told him outright the reason I had to stay there. Even showed him and his wife my dress! They are a mixed race couple so I figured they'd have had to put up with a lot of prejudice as well and might be more tolerant. He took it well.

I washed my first attempt at make-up off my face (scary stuff) and just put some lipstick with my oversize sunglasses. So as I was about to do the McD's drive through thing again, my neighbour was outside smoking so I figured what the heck and exited. He was so impressed he insisted on showing his wife. She was extremely complimentary of my look and we have a tentative date for her to help me with make-up tonight!

The McD's drive through just wasn't cutting it any more so I went out again later for a drive and decided to stop at a service station convenience shop. But for the personnel there was no-one else around. I gathered myself, managed somehow to walk in on my oversize heels, and paid for my bottled water. They all looked me up and down but nobody said a word.

It was so much fun I just had to do it again. This place had an awful ramp at the door which I knew I was going to battle with on the way out, but it didn't stop me.

"You look nice" the lady behind the counter said.

"It's my first compliment for the night" I lied.

"Oh they're just jealous" she said.

"Thanks for being so kind" I said on the way out.

Jumped in the car but had to wait for the attendant to finish washing my windscreen, so I gave him 10 bucks ($1) to buy a cool drink.

As I was backing out and contemplating a third, my water balloon (well government issue condom actually) left breast could not handle the excitement any more and promptly burst leaving me soaked down to my panties. So that was the end of that and I drove straight back to the motel.

Need to consider some proper forms, if they just weren't so expensive to get out here...

[Rhonda Darling]

Forms are expensive. It took me years to get around to buying my first pair. Suggest using the cut off feet of a pair of pantyhose. Fill them with rice (uncooked!!), dried beans, or birdseed until you get the volume you want, tie them off and trim the excess down. The knot can be positioned as a nipple, and the heft will give you a nice bounce in your bra. Voila, cheap boobs.

You'll feel great, and there is no surprise water event that can ruin a day.

Regards,
Rhonda

[Jenny Elwood]

Thanks for the tip Rhonda. I only thought afterwards how embarrassing that would have been if it happened in the shop.

[sherri]

Hi

Sherry there's a lot more involved here than my (selfish) needs to dress, for one there is the innocence of my five kids which I need to protect at all cost. I don't want them to ever see their father dressed (especially the boys). I totally understand. Ditto for me. And I'm single (divorced) so I can't preach, but this "solution" is a tad extreme, dontcha think? And besides, there is no "get it out of your system", honey, so whatcha gonna do after two weeks? You can't keep up the motel life forever. Just sayin'.

[Jenny Elwood]

You are right Sherri, definitely cannot afford to keep up the motel life.

I had hoped to sit down with my wife after the two weeks and come up with a solution. Yesterday she came up with this whole analogy about Jenny being the Goliath in my life that needs to be slain. It brought me back to earth and made me realize once again there's not a lot of room for compromise (from her side) there.

Honestly I don't know. I do know that I am "gatvol" of being bullied. So maybe, for once I will stand up for myself.

Bye

[MissTee]

Wow, Jenny. You're having a real soul searching adventure. In my experience the need to dress is always going to be there. The more you let "it" out the more "it" wants to be out. I'm fortunate to have a supportive spouse, and I can routinely dress in small doses. I've learned that helps me keep my wits about me when it comes to dressing. After a long spell of not dressing I become moody and restless, and when the chance to dress finally comes it's like a flood of emotion that can be overwhelming.

Anyway, now that you've let the Jenny out of the bottle she will be far less likely to want to go back in and stay. Hopefully you can negotiate some boundaries around dressing, and be ale to be there for your family as well. Good luck, sweetie.

[Jenny Elwood]

Hi all

Thanks for your kind thoughts MissTee. You are absolutely right in saying that Jenny has become more ingrained. I still hold out hope that we can come to some kind of agreement. I think maybe I'll stand my ground a bit firmer this time.

An Update to the Jenny situation for those interested:

Yesterday I headed out to the Chinese mall on the other side of town (in drab). I needed some make-up to experiment with and was not about to discard some very expensive little bottles, because they did not pan out. I saw, and tried on, a very nice little dress but had to decline (length issues as per usual. So I walked into a nice little dress shop and the assistants asked whether I was shopping for the wife as I looked at some skirts. "No I'm a crossdresser" I said. For the life of me I could not convince those two ladies, they just laughed at me. They had to attend to other customers before I could prove it to them by trying something on, so I shoved off. Found a nice shop and stocked up on some cheap cosmetics, got a cheap bra and some trinkets on the way out. The make-up experiment didn't go down so well but at least I'm learning, and Katey888, eat your heart out, my nails were redder than yours last night!

Last night I went out to go and fetch my compliment from the service station cashier in my white skirt (skirts have less length issues, I've found some nice below the knee skirts work well as above the knee skirts for me). Three teen aged boys nearly put me off but I figured I had the measure of those generation Playstationer's with my handbag.

Woke up very early this morning and had one of those "WoW" moments. "No, I couldn't" I thought. Bring in here one of my all time favourite movies: "Ferris Bueller's day off". I had a Ferris moment of pure unadulterated clarity: I had to go show them!

Normally I'm Ferris's dorky friend (see can't even remember the name) but this, this would be my Ferris day. I always wanted to have a friend like Ferris, I never knew that friend would be Jenny.

Now, first off there's very little chance of me ever passing in public. I can get the make-up sorted, work on the deportment and even dress inconspicuously, But I can never hide my 2.00 m frame (without heels) So I knew from the start passing was not really feasible. Add onto that the issues I have with my 4" size 17 US heels (too big) which is my only shoes that would do. I wanted to make it to the mall early before it got too busy so I just shoved a pair of pantyhose in each in the hope that they would not slip off. Boy was I wrong!

I did the bottom of my face up to the best of my abilities, slapped some lipstick on with sunglasses at the top and "passed" ordinarily well in traffic on the way there. I took a deep breath sitting in the car in front of the mall, opened the door and slid out. If I took longer to gather myself I knew I would chicken out.

I was in trouble with the heels from the start. I tried readjusting on a couple of occasions but the things kept slipping off. By now I had caused quite a bit of a scene and some people even started following me, some laughter, pointing but no-one said a word to me.

Now I have to put this into perspective: All the emotion, thoughts and dreams of both a lifetime, and a past week of living as Jenny, culminated in this moment and no-one, no-one was going to take this away from me. Tomorrow is the start of the working week (the mall would be empty though!) and by next weekend my time will be up. Jenny was out in public and everyone knew about her. Besides, bar the shoes, I...looked...good!

So my entourage kept a safe distance outside as I walked into the store. At first they (thankfully) didn't recognize me but when I told them about yesterday the lights went up. We had a nice chat and some other people also came over and had their pictures taken with me. They were all very polite and friendly. As long as I could keep my glasses on I was fine with it. The store owner started raising some concerns and I shoved off to the make-up store.

I complimented a beautiful young woman on her shoes ( the type you'll never get in my size) as I paid for my purchase. The normally expressionless Chinese shop attendants smiled and also had their pictures taken with this lamp post like lady.

I decided to make a break for the door whilst the going was good. By this time my shoes were in my hands as I could no longer do the egg walk. Nobody confronted me. Nobody harassed me. Nobody wanted to "slap the pervert". Maybe they just thought I had been dared. Maybe they thought it was some bachelors stunt. Maybe they were just stunned. I don't know, but maybe people had become a lot more tolerant in the new South Africa.


I headed back to the motel and promptly removed all traces of Jenny. If I could do this more often, maybe in a bit less extreme (and safer)of an atmosphere, maybe in a bit more of a passable manner, then it would make life not being Jenny, so much easier.

Thanks for those who have shown interest in my story.

[Katey888]

.. For those interested...

Jenny - I challenge anyone to not be interested in what you are getting up to... I am hanging on every word and sincerely hoping that you are first of all safe, and secondly having a good time - and my goodness you seem to be doing both with bells on!! :cheer:
You certainly are going at this opportunity with full head of steam - I am so in awe of your confidence and commitment to do this - I think that must be coming across to the people you're meeting in a very positive way and they're responding to your incredibly positive and generous attitude.

This is rapidly becoming a keeper thread for me - and should be for you too; The Adventures of Jenny... a best seller!!

All I can say is keep safe - keep doing it - we're with you there in spirit on this awesome journey of yours - and yes, if you can do this in more safety and less drama, I'm sure it will be a much more comfortable feeling for you... and for us, for that matter! :D
And I hope things do work out some way for you at the end of all this - I'm sure you just want to enjoy this time while it's yours... :hugs:

Take care - Katey x

[MsVal]

Jenny, I cried with you when you left home, sighed with you when you were frustrated, worried with you when you were taking chances ... now I am celebrating with you (vicariously, of course) when you take Jenny out on a shopping/ telling/ photographing/ thrilling adventure.

Just one week into the journey and you sound like you're doing well ... very well indeed.

What will the next week bring, and what will happen thereafter? I do not know, but suspect that you will come through it in grand style.

Best wishes
MsVal

[Shy_Confusion]

Jenny,

I come from a conservative Christian family. I know what that struggle is all about, and know how difficult it is. I'm pulling for you. Stay strong.
-J

[Jenny Elwood]

Hi All

Since some of you seem to be enjoying my story, I've decided to colour things in a little. I mentioned before that I had a tentative arrangement with my neighbour in the motel to have my make-up done by his wife on Friday evening. As I got there he told me that I could get dressed and come over later on. I will never pass up an opportunity to dress and now I could socialize as well!

I donned my best panty girdle underneath just to make sure there were no unexpected and embarrassing surprises and walked over quickly before anyone noticed. Turns out they were very intrigued by me the night before, and I had to field lots of the usual questions that come a crossdressers' way. I think I turned out to be a lot more boring than they had speculated!

They, on the other hand, turned out to be quite an eye-opener for this normally conservative guy, but I managed to keep my pose. He hails from Germany initially and she is from Cuba, they met in Brazil but how they ended up in the RSA I don't know. Either they have a normal business and ran a swingers club, or that IS their business. Earlier in the week he warned me about the homeless lady and said something along the lines of "organizing you something for Friday night". I had declined respectfully, but now it made more sense where he was coming from.

We delved some more into the realms of the sexual and I tried to be as open minded as I could, coming from my decidedly conservative background. He offered to show me a video of his wife with another lady... Thankfully his wife weighed in against it as well as I declined. I've never been one for porn and definitely didn't want to have to look her in the eye after that! After this the conversation kind of dried up, she'd finished the make-up, they'd indicated earlier on that they wanted to go out, so I had an excuse to leave. The people and places and experiences I've had since leaving my very narrow little world a week ago is just mind boggling. The make-up looked ok but, as I suppose you all know, not so good with your stubbles uncovered.

Just a side note to people living in the US/UK or other countries where there is organized SOCIAL clubs/societies for crossdressers. If you've been undecided about going do consider how lucky you are to have these available. In my country it is either people trying to pick each other up (mostly on facebook) or going to a gay bar if you want to go out dressed. The only organization that used to cater for it (called the Phoenix Society) faded away ten or more years ago.

I'm seriously starting to miss my family now, but I think maybe I will make a bit more of a statement if I don't ask to come home just yet. On the positive side, I'm going for a corset fitment tomorrow with a lady that actually caters to our needs, so I'll have to wear two pairs of girdles this time!

Bye all

[Jenny Elwood]

Hi Everyone!

Just had to tell you all about the blast I had last night. I hardly made a splash at the drive-through the night before, either they are just getting used to me or I am actually managing to pass! The convenience shop thing is also getting a but old so I had to try something new. I've been invited to a T-girl party at a gay bar Saturday evening but for obvious reasons (I'm going home tomorrow after work) I had to decline. So I checked them out and noticed that they are also open on Wednesdays. I felt I'd be much safer trying that out rather than probably getting beaten up in a "straight" place. Put on my purple dress (preparing took the better part of two hours, what is a girl to do!) Made up the bottom part of my face to the best of my (limited) abilities and donned my darkies. I forgot to put powder over the foundation (note to self) and put on some pink lipstick. So off I went to the other side of town.

I had no hassles on the freeway and got there in good speed. Luckily the place was quiet with no lurkers so I just walked in and up to the bar. I had stuck some money in my bra when I left, (still haven't managed to buy a purse, wasn't expecting to go out!) maybe they should consider putting pockets on dresses... The owner comes up to me and gives me a warm welcome. I felt at home immediately and nobody stared, pointed or laughed, within minutes I had made friends (as a man I take a while to make friends) and was invited by the owner to join him in taking on the local beer pong champions. I told my story in short and nobody seemed to have a problem with me being straight. Funny I told them that they have been accepted into mainstream society but people like me still had to lurk in hotel rooms.

After beating the local champions I sat down at a table with six or seven guys and we just had a good chat. Come 12 I knew I had to get back before my coach turned into a pumpkin so I greeted everyone and off I went. They were all perfect gentlemen and no-one tried to grab my bum. Got back safely (after the compulsory stop at the convenience shop) and went to bed like a good girl.

Tonight will be my last night but I think I will just have a quiet one. Spoke to the wife this morning and she sounds a bit concerned about what I've been getting up to. Looking forward to seeing her again and holding her in my arms again. I love her, that will never change.

P.S. Pics are posted in the "picture and video gallery" under "Jenny in "Trouble"".

Signing off.

Jenny

[Katey888]

Dear Jenny - I'm sure returning home will be something of a bitter-sweet experience - I sincerely hope it goes well for you and your family and that you can find some way to accommodation and harmony in yours and your family's life.

You really have taken an 'In at the deep end' approach with this experience... perhaps this will have given you a new perspective on the things you love in life and what they mean to you.

Stay safe - be happy! :)

Katey x

[BLUE ORCHID]

Hi Jenny, I sure hope that everything works out for you.

[Jenny Elwood]

Hi All

Today my time as Jenny draws to a close. I know that, just as I cannot deny the part of me that is Jenny, I also cannot deny the part of me which is husband and father. I just wish there was a way to reconcile the two. I know that being fed the scraps of underdressing will not do, I would rather dress a whole lot less often but go at it full tilt when I do. Thanks to everyone who have supported me throughout this journey of self discovery, I hope that I can return the favour in your hour of need.

Regards

[Persephone]

It has certainly been some adventure, Jenny! Thank you for allowing us to come along.

Hopefully your wife will have grown in understanding.

Hugs,
Persephone.

[MsVal]

You both have had quite the opportunity to ponder alternatives. Hopefully an intersecting path lies within them.

Best wishes
MsVal