I mean who would have predicted my mother knew I was playing with her clothes, that she would encourage me to walk about the house in heels and a skirt, that she would take me out dressed as a girl and buy me alcohol, that she would set me up with my best friend so that we end up in bed together, finishing off the adventure with my first sexual encounter.

The summer holiday was alot different to what I had expected it to be. First of all the end of term party had been something of a revelation, I mean who would have predicted my mother knew I was playing with her clothes, that she would encourage me to walk about the house in heels and a skirt, that she would take me out dressed as a girl and buy me alcohol, that she would set me up with my best friend so that we end up in bed together, finishing off the adventure with my first sexual encounter. Though I was doubtful about my mother's motives at first, about my own feelings and about Mark's reaction, I have to say what my mother has encouraged me to do has opened up new doors and I am loving every one of them.

I had set up a summer job before term ended so spent alot of time selling ice creams from a kiosk in a local park, but when I was not selling i was home trying out new feminine touches to my appearance. No one had made much of my ear peircings, some friends who saw me after the party told me the streaks were unusual but looked good in an off the wall way, but what I wanted was for my hair to grow a bit longer and get a really nice cut, but I dare not say that to friends who think I am only into games. The summer did allow me go out with my mother on occasion as Jenny, when she would buy me clothes and make up further encouraging me to be her girl, which could be unnerving at times, other times were really good as we grew closer and better able to talk. Mark was still the gaming friend he had always been, but something had changed in the relationship. There was a day mid week when we were both at home and having bored of our game sat back drinking a lager each in the sunshine. Mark was working up to asking something, and ended up blurting out that he wanted to take Jenny out. I was not ready for such a direct request, but once I had made sure he was genuine I offered to go and change, he should call round in a while.

I was always half ready to dress as I was clear skined and hair well groomed, so i only needed to apply make up, change my clothes and style my hair to be pretty much reasonable. I choose the denim mini and a loose silk top which exposed the bra straps. Mark came round and let me know he approved by giving me a kiss. Not sure what to do next I let him take the lead, soon we were cuddling on the settee like a proper couple, but before my mother came home i made sure my face was repaired and the preparations for tea were well underway. When she came home and found me dressed and Mark watching the tv, she invited him to stay and invited his mother round as well.

Mrs Jones was a little off gaurd when she saw me dressed, but recovered quickly to give me a greeting hug and kiss then let me get on with the meal. Our mothers just chatted as though it was normal to have a son dressed as a daughter making their meal for them. In the end I served the meal before sitting down to join them, rather like my mother would have done in the past. We all drank too much wine and I relaxed enough to let Mark kiss me when he left. I knew my mother would see but the expected questions never came, just a compliment on how good I was looking.

Mark and I once tried kissing when I was not in full Jenny mode, we were alone and sat next to each other when we moved to get up and lost balance so we were on top of each other, I went to kiss Mark but he pulled away as soon as I touched. I apologised and said it was spur of the moment thing, then he tried to explain how he finds girls and not boys attractive, and how he has not really come to understand why Jenny is attractive, even though he knows I am a boy. I confessed to being confused as well, that I like being Jenny and to have Mark treat me as a girl and react to me as he does is a mystery, but a very nice mystery.

And so our eight week holiday slipped by, a lot of work and money saved, but also a growing wardrobe and the odd liaison with Mark, mostly at home on the settee, but a couple of times out in the big wide world when we thought no one would catch us.

The return to college caused my life to change, weekdays were spent studying as it was going to be a hard last year, then working either Saturday or Sunday at the park, which only left one day free which was spent doing a variety of things like college activities, going out with mother or just being busy doing nothing, well everyone needs a rest sometime. Then when I was off, Mark was often working or having to catch up on the studies, so Jenny did not get out much at this time, I could sleep in female sleepwear but getting myself fully dressed was too much effort just to sit around at home for a couple of hours while I studied. I was persuaded once by mother to join her on a shopping trip as Jenny followed by an evening with Mark going to the pictures and having a pizza after, clearly we had our girl/boy friend moments but nothing too heavy. At the end of the evening Mark asked if I would be Jenny for him at least once a week because he enjoyed my company in a differnet way to when I was Jens which was still happening at college and at home when we found time to play our games. It did not take much persuasion for me to agree to being Jenny at least one evening at the weekend, this decision was followed by a poster going up at college the following day advertising a halowen dance.

Mark did comment on it and picked up a flyer, but I was more cautious we had done it once and had fun but what were the chances of doing it again and not attracting cruel comments. I told him to forget it. That was until about a week later, it takes that time for Mark to put his clothes in the wash, his mother to find the flyer, and for my mother to receive the flyer from Emma, finally catching me and asking if I was thinking of going and what was I going to dress up as. I tried very hard to explain how I thought it was not a good idea to do a fancy dress with Mark again knowing both she and Mark would want me to go as a female partner to Mark's male. In the end I was beaten into submission when later that day Mark came round to play a game and his mum came round for a gossip with my mum. It did not take long for the subject to come up and even though it was me who would be doing the main dressing up it was decided that on a democratic vote ot 3 to 1 I lost, they had even discussed the outfits and Addams family had won. It did not need great intellegence to know that Mark would get to be Gomez while I would be Morticia. My mum had not really seen any of the films and everyone else had been younger when it was last out but Mark had a CD and nipped home to get it so we could all sat down that evening to watch what we would be imitating. The story clearly was not what we were watching and as the characters appeared we, well more they, spoke of what we might be able to achieve. Mark fancied a velvet smoking jacket look, while Morticia always seemed to be in long, tight black dresses that gave her great trouble moving around. I dreaded to think how this would turn out, but I knew I was getting steam rollered into it so might as well go with it and enjoy what I can.

Within days mum was round to the costume shop and had booked a dress she knew would be ideal, and with a week before the dance she was making plans on my behalf, black stiletoes, dark burgundy nail polish and lipstick she had wanted black but I wanted some colour and not just the blushing of my cheeks, I had black underwear so thought that would be it. On the Friday she came home with the dress and asked me to try it on, it was close fitting but stretched enough to allow movement, but the bit mum liked was the way the skirt flared out below the knees, the way my knees were kept together causing we to swivel as I walked made the hem spin out and exagerate the swivelling that my hips and knees were doing, added to that the heels affected my walk, I was just going to mince everywhere. The sleeves were another thing as well, huge frilly cuffs which started at the elbow and finished below my fingers. This costume was going to take some getting used too.

The hours at the park were getting less as the evenings got darker so I was home early which pleased mum, she had been shopping for bits she said. I recognised the false nails but there were others I was not familiar with but did not have time to look at carefully before mum suggested she helps me get ready, with a hair session first. While she washed, conditioned and rinsed my hair I did the nails when not leaning over the shower, then as she styled my hair I painted them. sometimes I am thick and dont see things coming, this was one of those times, I got up to go and dress when I caught sight of myself in a mirror, my hair was jet black. Mum must have noticed my shock and reassured me it was not a permanent colour and will wash out after a few goes. In my underwear she then applies my face, quite pale skin, burgundy lips and dark eyes with the added extra of false eye lashes making the eye look even bigger. Followed by black stockings and the dress which between us we manage to wriggle me into with her pulling the zipper up, securing me into my most limiting outfit ever. She had even got me a black cape to keep me warm, then with a squirt of perfume I was ready. It was about this time I noticed that mum was wearing a rather nice new fashionable dress that I had not seen before, I complimented her on it and asked if she was going somewhere special, just out with Emma and some friends she replied, that will be nice I told her, she then felt the need to justify her getting dolled up and going out which she had not really done since dad died. Seeing me wearing nice clothes and enjoying myself being pretty had encouraged her to do the same, and the invite they had to go out that evening seemed ideal, ending with if we I can go out looking great and have some fun why can't she, why not indeed, was the ony response I could think of.

Mark had borrowed his mother's car and parked close to the door, but it was seeing him in the velvet jacket, black trousers, white shirt, red cummerbund and slicked back hair that got my attention, that and the Gomez style greeting of arm for me to link and formal greetings, once in the car he let out a whistle 'Did not like to say in front of your mum, but you are hot tonight' I squeezed his thigh and told him he was pretty hot himself.

We parked and the first person we saw was Samantha who let out a delighted squeal and came over to hug me, she and her new boyfriend were vampires, only she had the long black spike heel boots, tight black top and a riding crop which said something different, Paul just looked compliant as he wore an ill fitting black suit and fangs, I later discussed with Mark his chances of being long term and we agreed he stood no chance unless he liked the riding crop and doing as he is told. I walked in with Samantha linking arms like girlfriends and giggling as we tottered in on our heels. That was a great start to a fun evening, lots of people did not recognise us, even Mark's costume changed his appearance enough so that only close friends made him out, a few like Samantha knew me and for some reason none of them spread it about that I was really Jens, but spent the evening calling me Morticia or Jenny, so when I was with Mark I could use him as support and link his arm as I minced along by his side, when alone he was even brave enough to show some of the affection we had kept to our private times, gradually getting used to each other and the other party goers so that we even had a few dances, though I had to make them slow ones. But the close contact was not missed by Samantha and Clare who were treating me more like a girl than I was used too.

Though the dance had opened us up to new experiences of being a couple in public and for me being Jenny in a more convincing role, it was later on that our relationship moved on. I invited Mark in when we got home asking him that I would need help getting out of the dress. Once again my mother had set us up, a note to Mr and Ms Jones-Addams, Hope you had a good night, stopping at Emma's, see you in the morning. It was leaning against a bottle of vodka mix. So we opened the bottle and settled back for a drink and nice cuddle. Things moved along very nicely, mum was round at her friends again so we had the house to ourselves, and with a note similiar to the wedding dress night I knew she had set this up. After a good session on the settee I mentioned that I would need help unzipping the dress, so picked up my glass and the bottle and minced upstairs followed by an eager Mark. If boys are ever considered to be on heat like dogs, then that night I must have been, he was keen and obvious what he was hoping for. Again my mother had left her door open with a nightie draped across her double bed, he undid the fastener and helped me to wriggle out of my second skin, then we undressed Mark and fell into bed for more passionate cuddling. I was about to blow him off again when he tells me he wants to give this time not just recieve, puzzled I ask what he means, now it was his turn to look puzzled, he had seen a tube of KY jelly on the bedside and guessed I had put it there, not me must be my mother setting us up some more, so I asked what he had in mind, and soon we had worked out the basics of how Mark could make love to me and I feel him inside me making me feel the way I looked, feminine. He erupted inside me, then sadly he shrank away leaving me wanting to feel him inside me still. I knew then I would be wanting his attentions again and soon. But not that night, neither of us knew how a man can get erect again, so we cuddled until sleep took us.

The morning found me looking a mess, as well as the pillow, I had not cleaned up so make up was everywhere, it took a while to get clean and presentable, but when I finally made it to the kitchen found Mum and Mark eating toast and chatting about the evening. Mark left after breakfast and a good kiss form me to say thank you. Then it was just me and mum, I thanked her for the card and drink, and the use of her bed, fine she said just wanting to open up new experiences for me, which made me think of the KY jelly, so I thanked her for leaving it out. This rather caught her out, the jelly was for her she had not meant to leave it out, now it was my turn to be embarrassed as she rightly guessed what we had used it for and asked how it was, maybe I was feeling a closeness but whatever the reason I told her how nice it had felt, and she hugged me telling me how lucky I am to enjoy such things, then I told her I was getting really confused over my identity and did not know if I was a boy or a girl, she just told me to be myself.

Then it was time for her confession, the night out she had had with Emma was more than just the two of them, it was actually four of them, Jack and Sean being the other two, and yes they had had an enjoyable evening, it was the first time she had been out on a 'date' since dad had gone so it was never going to be much, I was fine with that as long as I did not have to call her man 'dad' and he was good for her then I would be fine with it. Then came the bigger confession, the topic of where we, Mark and I, were the night before came up, they said a fancy dress dance as Morticia and Gomez, and somehow they assumed I was a daughter and not Jens dressed up as Morticia. She reassured me that if she saw them again she would correct them but it had been fun letting them think I was a daughter.

The Sunday was going to be a quiet day, but as I was still glued to my breasts and nails I dressed in my mini kilt and pink angora top before settling down to do some course work. Just before lunch mum came in and told me she was going out with Emma, and she was looking good again so it was not just for a gossipping chat. This was followed by Mark texting asking if I would like to go round to his. As soon as mum and Emma were gone, I was round at Mark's and kissing for all I was worth, I had the jelly in my bag and had already squeezed some inside my hole in anticipation. It took us no time at all to be on a bed with my knickers down and my legs up with Mark filling me, this time I was sober and tighter, but Mark lasted better but still came without me, though he did touch what I guessed to be a g spot several times and wished I could have done more to get him to stay in there till I enjoyed these new sensations.

The second event in what I expected to be a quiet day was to find myself meeting Jack and Sean, I was watching tv with Mark after our sex adventure when I had a text off mum asking me to be scarse or be Jenny. I was already Jenny so stuck around to see what was happening. The four of them came back mid afternoon having spent their lunch in a pub, seemingly mother had not managed to tell the truth, and I could see why, both men were good looking and seemed to be good fun, Jack being well over six foot and toned why would she risk losing him when they were just being friends by admiting to a lie. I immediately realised that if I was to ever meet these men again it have to be as Jenny, mum was not going to spoil her fun by admiting the lie, it also meant she could ask me to dress, and it also meant I had another little excuse to make myself pretty.

Later at home I questioned whether she had explained to Jack that her daughter was really a son, with a hug she asked if I was sure about that. Going on to tell me how she liked Jenny, Mark clearly liked having Jenny around, and now Jack and Sean would be expecting see Jenny if they meet me again. My life as Jens was being restricted but also encouraged by those close to me, and deep inside I could not find the fight to say no, I knew that I was enjoying the whole experience far to much to stop it right then.