This is really a story of what I did during the spring half-term holiday but, in order to put it into context; I am going to start at the very beginning.
My name is Gillian. It is not the name I was given at birth but it is how I am known at home, at school and by my friends. I am sixteen years old and go to a private, mixed school for 4 to 18 year olds near to my home in Somerset. I live with my Mum and Dad and I have a sister, Jacqueline, who is 18 and is at University in Scotland.
Two events have shaped my life: my first day at school and Christmas Day 1997. I can remember my first day at school as if it was yesterday. Jackie and I were dressed in our uniforms and waiting for Mum to get the car out of the garage. It was a cold day and it was raining. I was wearing grey wool short trousers, long grey socks and a grey duffel coat. I was thoroughly miserable as the wind and rain were getting in through the gaps in my coat, my knees were bare and turning blue and my trousers had got stiff with the rain and were chafing the backs of my legs. Jackie was wearing red woollen tights under her skirt to keep her legs warm and had a knee-length pink coat on with a fur trim round the hood and cuffs. She looked as warm as toast and I thought "Why can't I wear tights and a fur-trimmed coat?" Being 4 years old, I asked Mum why I couldn't and was told not to be silly as they were only for girls. This was so unfair in my mind and it stayed in my head.
Over the next few years, my sense of the unfairness of "girls' clothes" grew and grew. Jackie could wear different coloured tights -- I had to wear thick grey socks. Jackie wore short white socks and a light summer dress in the summer -- I was still in thick grey socks, wool trousers and a long-sleeved shirt. Jackie wore pretty black patent-leather shoes with a strap -- I had heavy lace-up shoes which I had to polish. Basically, all Jackie's clothes were bright and pretty and she got a say in what Mum bought her while my clothes were all grey and ugly and my only contribution was to stand in the shop while Mum made the choices. And, to top it all, Jackie could dress like a boy any time she wanted! She was free to wear jeans, sweatshirts and trainers unless she was going to school or we were going out.
Matters came to a head on Christmas Day just before my 7th birthday. My present from Mum and Dad was an Arsenal football kit -- boring! Jackie got a new party dress in black silk with lace-trimmed puff sleeves and masses of white lace petticoats underneath. She was already wearing a red party dress with pink net petticoats that I secretly envied. It was so unfair and, before I knew what was happening, I was in flood of tears and was sitting on Mum's lap crying that I wanted a party dress and why couldn't I wear skirts and blouses and soft tights and shiny shoes. When I had quietened down and Mum and Dad were trying to think of something to say, Jackie asked "Why can't Jon wear a dress if he wants to?"
After a moment of thought, Mum said that there was no reason except that I didn't have any dresses to wear. Jackie replied that she had loads of clothes that she didn't wear any more and, in an imperious manner, grabbed me by the hand and took me upstairs to her bedroom. I passed the next hour or two in a complete daze as she basically treated me like a doll -- she took my outer clothes off me; decided that my underwear was wholly unsuitable and took that off as well; got matching vest and knickers out of a drawer and put them on me and then went through her drawers and cupboards, pulling out clothes, holding them up to me and then either putting them back or putting them on a pile on the floor. Then she tried everything on me. Skirts, dresses, tops and jumpers that didn't fit were rejected and different combinations of everything else were tried. She finally settled on a pink party-dress with white felt bunny-rabbits on it, sewn-in petticoats in white lace and a huge pink bow at the back. She added a pink fluffy cardigan and a pair of white lacy tights. She couldn't find any shoes or slippers small enough for me so she took me back down stairs to be presented to Mum and Dad.
Jackie seemed very proud when she led me into the drawing room. "Isn't Jon pretty?" she said. "I think the dress really shows off his complexion. He's got a lot more stuff that we will have to put in his room but you'll have to take us shopping to buy him some shoes. He can keep the vest and knickers and tights he's wearing but you'll have to buy him some of his own because I don't want to share with him. If you buy him some other stuff, get it so I can wear it as well." And that was that. We had Christmas dinner with me in the frock. Then, while Mum and Dad washed up, Jackie and I went upstairs. We threw out all the clothes we thought I could get away with and put Jackie's old clothes in their place. Then we went into her room and read books until we were called down for supper. After that we watched television until bedtime. Mum seemed surprised to see that I had one of Jackie's nightdresses rather than pyjamas but she didn't say anything.
On Boxing Day we visited our cousins, Laura and Tom. I can remember wearing a denim skirt and a red jumper. Mum solved the shoes problem by stuffing tissue paper in the toes of a pair of Jackie's shoes. Nobody seemed to notice. They told me later that it seemed rude to point it out and as my Mum and Dad weren't concerned, why should they be?
We went shopping the next day. Jackie was concerned that she had given me three sets of underwear and tights but soon shut up when we got to the local department store. We both went mad trying on dresses, tops, skirts and, in Jackie's case, trousers. I also got a coat and a cape and two pairs of gloves as well as a lot of underwear and tights. Mum must have spent a fortune! Then we went to the shoe shop where Mum bought me a pair of black patent-leather shoes with a strap (I hadn't forgotten) and a pair of bright pink trainers.
Mum and Dad seemed totally cool about the whole thing. Jackie and I talked about it and Jackie said that they thought I would soon get bored of the game and, anyway, I would have to change back into boys' clothes when we went back to school. I thought about this and decided that I really liked wearing girls' clothes, I didn't like wearing boys' clothes and there was no way I was ever going to wear grey shorts and socks again in my life. So we went to talk to Mum and asked her when she was going to take me to the outfitters to get me some school skirts and blouses. The conversation went along the lines of "Everybody will laugh at you"; "I don't care" and "What if you change your mind"; "I won't" and "What will you do about PE"; "I don't like PE". Finally Mum saw it my way and I got three school skirts, half a dozen blouses and a new blazer with the buttons on the left.
So along came the first day back at school. I was dressed in school uniform with black tights, covered by my new cape with pink furry earmuffs and pink fluffy gloves. It wasn't until I got out of the car that the enormity of the whole thing hit me. I stood there absolutely petrified and I was going to wet myself at any moment. Fortunately, Jackie spotted what was going on and, taking me by the hand, she marched me over to a gang of her friends. "Hello everybody. I got a new sister for Christmas. This is Gillian and we've all got to be especially nice to her and play with her and make sure nobody is nasty to her because she is my special Christmas sister." When we went into classes, she went with me to my classroom and said the same thing. And, do you know what? I never did have a problem. I didn't do PE; I stopped playing football with the boys and played skipping and generally hanging out with the girls instead. I can't remember anybody being rude or unpleasant to me.
Phew! I've just re-read what I've written and realised that it only covers 2 weeks. I better get on a bit. The next 6 years passed by quickly and without anything of note. I was, to all intents and purposes, a girl. I spent all my time as a girl and with other girls and everybody, including me, forgot that I had ever been anything else. Then came puberty! There were the obvious physical issues -- all my friends were turning into women and I was in daily dread of suddenly growing to 6 feet tall, sprouting hair everywhere and my voice breaking.
The other problem was sexuality. When we were younger, boys were held in contempt but suddenly, all the sexy clothes and makeup and hair styling was to attract boys. I didn't want to attract a boy. I wanted to kiss my girlfriends and just being with them and talking about what we were wearing and how it looked was causing problems that were hard to hide in thin knickers and a tight skirt. I was wanking off 3 times a day to keep my willy under control (calling it a knob or dick doesn't seem right when its less than 2 inches long and only 5 inches when hard).
Sooner or later I was going to get caught and one morning, just as I was getting into my stroke, Jackie wandered into my bedroom to borrow something. She was now 15 and developing a reputation as a slut. She had been going out with boys for over a year, discovered that she liked sex and her virginity was now a distant memory. She was smart, pretty and the best sister anybody could have. Her first instinct was to ask if she could watch but when she saw me burst into tears, this gave way to genuine interest and concern for my problems.
She went into solution mode as soon as I finished explaining the problem. "Don't worry about being tall. You're not 5 feet tall now so you'll never grow as big as 6 feet. You never take any exercise so you won't grow any muscles. If you take hormones you won't go hairy or get a deep voice; you'll get a woman's body and you won't have to worry about getting a stiffy. You won't need to get one anyway because only lezzies might be interested in you and they prefer girls with fannies rather that dicks."
As an aside, Jackie treated us to a 2 hour performance with the Head Girl at a beach party that summer. They were all over each other like a rash with fingers and tongues exploring everywhere and absolutely heaps of groaning and panting. Her excuse was she had had too much to drink and Morag Campbell was the butchest person at the party anyway. She had already been knobbed by every boy at the party and none of them was worth a second fuck.
"OK clevercloggs" I said. "It may well work but where do I get the hormones from? I don't think I can just go into Boots, not even in Bristol, and buy some."
"Easy" she replied. "You just go to the doctor. You tell her that you have always wanted to be a girl and you will commit suicide if you can't be and she will give you them. If you make an appointment for after school, I'll come with you. If she sees you in your school uniform she'll have to believe you."
Seeing the doctor was the easy bit. The doctor was very sympathetic but explained that there was much more to it than handing over a prescription for hormones. To cut a long story short, I had to go back with Mum and then see physiatrists and endocrinologists and have loads of blood, urine and other tests before I was given hormones. Then I had to keep going back for more tests and adjustments to the dosage.
To cut a long story short, I am now a happy, well adjusted girl. I passed 10 GCSEs at A+. I am studying 5 AS levels in the sixth form and I hope to go the Oxford to read PPE when I leave school. I'm 5'5" tall and measure 34B-22-36. I also have a girlfriend -- Carol. We were both in Monsoon trying on clothes one Saturday. It has a communal changing room and she brushed against me while taking her trousers off and noticed the bump in my knickers. My reaction was to burst into tears (I'm good at crying) as I thought she would tell everybody. Her reaction was more surprising. She started to kiss my tears and cuddle me and told me that now she knew why she fancied me but no other girl and did I fancy her and could we go out? I had always fancied her but not in a really physical way as the hormones seemed to reduce the interest along with the ability. Anyway, I said that I wanted to go out with her but I wouldn't be able to do anything with her because of the hormones.
I was wrong about the hormones. If you stop taking them until you can get a stiffy and then start again as soon as you can there isn't a problem. Once you start being unable to get one again you stop until you can. I reckon that I don't take them for about 4 weeks every 3 months. My willy might be smaller and a bit softer that it could have been but Carol hasn't complained and we've been fucking for almost nine months. The really brilliant bit is that Carol's Mum and Dad think I'm a normal girl so they let me sleep over at Carol's every couple of weeks and she's got a double bed that we share. Carol's Dad is a bit of a pervert. He's always hanging around when I'm going to and from the bathroom and he comes into the bedroom really early in the morning hoping to catch a look at me. I know because if I wake up before he comes in then I arrange for one of my boobs to poke out of my nightie then I pretend to be asleep when he comes in. He will stand and watch until I pretend to stir then he makes a big show of knocking on the door and coming in.
In fact, I think I get more sex than if I was a boy. When Jackie found out I was going out with Carol (we try to keep it a secret), she started to take the piss asking if I had to use a dildo to satisfy her. I told her that I could satisfy her with my willy because I could get a stiffy and she asked me to prove it. We were sitting in her bedroom so I slipped down my tights and knickers and pulled my willy from under my skirt and started to wank it. The next thing I knew, Jackie's hand was over mine and she was whispering in my ear to let her do it while diddled her. One thing led to another and I ended up on my back with my skirt around my waist with Jackie bouncing up and down on me like mad. When we finished she said that she understood how I kept Carol happy. I might not have the biggest willy in the world but it took forever for me to cum and she had cum three times. We fuck about once a month now. I know incest is wrong but Jackie has lots of other partners and I think that its just a way of being close together as sisters.
The other girl is Tracy who works in the beauty salon and waxes my legs. I have been having my legs waxed for a couple of years and Tracy has known my secret ever since she first did my bikini line (It might not be big but it's hard to hide in semi-transparent nylon knickers). A lot of my friends were having Brazilians done and I eventually asked Tracy if she could do mine in a Brazilian. She explained that it would look silly without having a pussy but she would be happy to wax me smooth. Tracy is about 25 or 26 with curly blonde hair and really big boobs that are always rubbing against you while she is working. She always wears Miss Dior perfume which is one of my favourites. Anyway, having this sexy-smelling woman rubbing her tits against me while fiddling with my willy and balls (I'm sure they didn't need as much re-arranging as they were getting) soon had me standing to attention. I asked her to give me a minute to calm down but her response was to wrap her mouth around my willy and start to slide it in and out. Pretty soon I was in a position I am starting to get used to -- laying on my back with a woman bouncing up and down on my willy. We do it every time I go and get waxed. Tracy says it's my reward for being a brave girl and not making any noise when she waxes the tender bits.
Oh my God! I have just realised that I've written 5 pages and still not got round to the pint of this. Right, here goes. Last Spring we had a 4 week break between the end of lessons at school and the start of our GCSE exams. After 2 weeks I was bored out of my mind. I had revised everything twice and new it all backwards. Mum and I were starting to fall out and then Jackie came to my rescue. Why didn't I come up to St Andrews and stay with her for a week. Brilliant! Even Mum thought it was a good idea and the next day she dropped me at the Railway Station with £250 in my purse - £150 for the train and £100 to spend. However, I wanted to hit the shops in Edinburgh so I had no intention of wasting my money on train fare -- I would hitch hike. I was wearing a tennis skirt with a halter top, high-heeled strappy shoes and no bra. I reckoned anybody would love to stop for a sweet little sugarbabe like me. Soon I was standing at the M5 junction with my thumb out and my cutest possible expression.
After about 5 minutes a huge green lorry pulled up. It took ages to climb up into it. The driver was smartly dressed in a green uniform. He was oldish -- at least 30 with beautiful wavy golden hair and the strongest northern accent I'd ever heard. He spoke to me about five times before I realised that he was asking me where I was going. When I told him that I was going to Scotland he told me that he was in luck as he was going back to his depot in Carlisle and you could spit into Scotland from there. So that was me sorted.
I pulled up my bag, shut the door and settled into the seat by the door -- furthest from the driver. "Ye'll after sitoop bimee t'ear mee" he said. What was that? Oh! "You'll have to sit up by me to hear me." I shuffled over next to him and settled down for the ride. He started to ask me questions as we went along - Why wasn't I at school? How old was I? Did I like school? What music did I like? What was my favourite film? I found that by leaning up close to his mouth and really concentrating I could understand him. My answers were pretty monosyllabic to start with but he was really friendly and I like to talk about my favourite subject -- me so soon I was chattering away like a good one.
Then, after a couple of hours he made me stop in my tracks. "Have you ever given a bloke a blow-job?" he asked. I flushed deep red and sat there opening and closing my mouth like a goldfish. "I'm sorry" he said. "It was in my mind and just sort of slipped out. You're a pretty young lass and your mouth is just about perfect for sucking. Please, just take it as a compliment and forget I said anything. I'll drop you at the next service area if you're worried."
"No, it's OK" I found myself saying. "And in answer to your question, no, I've never given a bloke a blow job. Why, would you like one?"
"I would love one" he said. "I've been sitting here with you blowing in my ear and every time I turn to look at you I can see right down your top. Resting your hand on my thigh and the way your skirt's ridden up to show me your pink knickers doesn't help either. I've got a raging hard-on and I'd rather you sucked it than I wanked it."
"Well I'm not sure that you would want a blow job off me. I'm not quite what I appear on the outside." Then I told him that I was transgendered (not that I think I am really) and that he should drop me off at the next junction. He told me that he didn't care if I was a man, woman or monkey. I looked as sexy as fuck and he'd love to have me hanging off the end of his knob. Put like that it seemed rude to refuse so, with more than a little trepidation, I reached down, unzipped his trousers and reached inside. Oh my God! His knob was about 10 inches long and so thick I needed both hands to hold it. It had thick veins all over it and a huge purple end. I slowly lowered my head to it and, parting my lips, let the end pop into my mouth. Then I just stayed there for a moment, tasting it. I expected it to taste of stale piss but it didn't taste of anything. It was just big, hot and very, very smooth. I started to run my tongue over it, enjoying the smooth slipperiness of it. It was exactly like rubbing your boobs through a silk top, indescribably sensual and I was starting to think I could happily keep my head in his lap and his knob-end in my mouth until we got to Carlisle. What I didn't realise was that it was driving him mad. I found out when my head was suddenly shoved under the steering wheel and I had about 6 inches of very thick knob down my throat which was trying to increase to the full 10 inches.
After a couple of seconds, which felt like minutes as my whole life started to pass in front of my eyes, he pulled me up again and pulled his knob out of my mouth. "You can't do that to a bloke" he said. "It's far too intense. It's Ok to lick it on every stroke but not all the time. Just slide it in and out of your mouth. Imagine that it's a dick going in and out of a pussy. Go nice and slow and don't worry about getting it all in -- even my missus can't manage that". So I settled back down and started to let it go in and out about 3 inches. I pushed my tongue against it as it was on the way in and sucked my cheeks together on the way out. Whatever I was doing seemed to work OK because pretty soon I was rewarded by a madly swelling, twitching knob, promptly followed by a mouth completely filled with cum. Swallowing desperately so that I didn't get any on my clothes, I managed to catch it all. God! How much was he going to produce? It seemed like a pint. Finally, he came to an end and I had a moment to savour what was in my mouth. I didn't think that it was something I was likely to do again so I wanted to get all I could from the experience. I still had a mouthful so I swished it around inside my mouth and around my tongue -- just like my Dad when he's drinking posh wine or whisky. It was weird. It tasted a bit like caviar but not as fishy. It was sticky and slippery at the same time and, ugh a bit gross, it had little lumps in it like Tartar sauce. Hmm. Different; not something I would want every day for breakfast but not bad for a change.
I carefully tidied his knob away and zipped up his trousers. Then I looked up at him and smiled. "Thank you" I said. "I really enjoyed that."
"Not as much as I did" he replied. "You were bloody marvellous. You can suck me off any time you want". To be honest, I wasn't in too much of a rush to do it again. Maybe when we got near Carlisle. The main problem was that while he had cum, I hadn't and I was feeling bloody hot! I suspected that he wouldn't be keen on returning the compliment on me and I was sure that I wasn't about to wank off in front of him.
After I had removed my head from his lap and repaired my makeup (it plays the very devil with your lippy), I settled back down next to him and we began to chat again. I found out that his name was Dave (yes, I know it would have been polite to have been introduced before I tried swallowing his knob); he was 32 years old; he had been married for 12 years to a woman called Charmaine who was 38; they had a 16 year old daughter called Elspeth and enjoyed an open marriage because they were both sex-mad and Dave was away from home for at least half of every week.
Some time later we stopped at a service area for petrol (do lorries use petrol?) and to get something to eat. Dave was really sweet and insisted on paying for my lunch. He was surprised to find out that I was a vegetarian. Honestly, the way he went on about it. It was as if he regarded a boy dressing as a girl as perfectly normal in comparison. When we went back to the lorry he gave me a hand up into the cab. As he was pushing me up he slipped his hand under my skirt and gave my bum a squeeze. It felt pretty good having a big strong hand squeezing there so, instead of pulling away and jumping up into the cab, I pushed back against his hand and enjoyed the feeling of having my cheeks squeezed and then a strong finger running against my crack. Finally he gave me an extra push and I reluctantly got up into my seat.
When he got into the cab, instead of starting the engine, he turned to look at me. "Do you fancy a fuck?" he asked.
"Duh! In case you'd forgotten, I don't have a pussy. So even if I wanted, and I'm not saying I do, there's nowhere to put your knob" I replied. At the same time I was thinking that it was a pity because I was really enjoying the naughtiness of the situation and I was remembering a conversation I had had with Carol a couple of weeks ago. She was in the middle of her period and was feeling sorry for herself and a bit catty. He had complained that I was a cheat girl and was only getting the good side of being a girl -- no periods; no fear of having to give birth which, according to her Mum was like shitting a breeze block; and never having to put up with having a big sweaty man lying on top of you shoving his meat in you for all he was worth.
"Maybe you don't have a pussy but you do have a hole. My Charmaine loves it up the arse. I reckon I shag her bum at least twice a week" Dave said. I thought about it for a bit. I didn't have to worry about periods or getting pregnant but I could experience the big sweaty man bit -- not that I would dare let Carol know.
"Won't it hurt?" I asked, worrying about the size of his knob.
"Charmaine said it hurt when I first shoved it in but, once she relaxed around it, it was fantastic. We'll need some lubrication though. Go on, what do you think?"
"OK then but promise you'll stop if it hurts me too much. What will we do for lubricant?"
"That's easy. If you give yourself a wank then you can spread the cum up the crack and into your hole" Dave replied. So knickers down to my knees, skirt up and away I went. It took no time to get a stiffy, the conversation we were having and the earlier blow-job had left me desperately randy and I could have fucked the Crack of Doom. He immediately noticed my waxed crotch. "My missus shaves down there as well" he said. "She says she has to because she often wears rubber knickers. Do you know what she did the other week? She told be to be in the sex-shop near us by 11 O'clock and to say nothing. So, there I was with all the perverts in their thick glasses and raincoats when in she walks. She walked straight up to the counter and asked, very loudly, for a pair of rubber knickers, size medium, with two dildos in them; one for her cunt and one for her arse. Of course, all the perverts were paying attention now. The bloke behind the counter found her a pair and handed them over. She made a big performance of inspecting them and holding the dildos to make sure they were big enough. When she had paid for them she asked if there was anywhere she could put them on because she was desperate. Everybody in the shop was staring at her now and I had a huge hard-on. She was shown to the store-room.
She re-appeared about 5 minutes later with the knickers in her hand but no skirt or knickers on; just her stocking, suspenders and her heels. "I'm too dry to get the one up my arse" she said. "Can one of you blokes help me out?" She walked up to this old bloke of about 50 and pulled him forward. "Please?" she said. "Just fuck my cunt for a bit to get your knob wet and then finish off up my arse." She then bent over a display cabinet full of dildos and vibrators and shoved her arse in the air.
The old bloke walked up behind her, got his knob out, and shoved it in her twat. After about 5 or 6 strokes he pulled it out and slid it up her arse. Then he pounded away for all he was worth until he came. When he pulled out, Charmaine's hole was still open. She calmly reached over for the rubber knickers, slid them up her legs, lined the dildos up with her pussy and arsehole, and pulled them up tight. She smiled sweetly at the bloke who had fucked her, thanked him and told him he could fuck her any time, put on her skirt and walked out of the shop. She told me that she then went shopping for clothes but there was nobody in any of the changing rooms to see her knickers so she went to the swimming pool where she freaked out a couple of birds when she took her knickers off and they could see two dildos slide out of her."
As Dave was talking and I was wanking, my mind was working overtime. I could imagine myself as Charmaine, bent over the display cabinet with loads of strangers watching me being buggered and I could imagine myself as the bloke doing it and I could imagine myself in the changing rooms -- stripping off to reveal rubber rather than cotton or nylon knickers then pulling them down to show that I had had a dildo up me. My mind returned just as I was about to come and I remembered to catch my cum in my hand. Then I spread it up the crack of my bum and worked it into my bum-hole.
Then I knelt down on the seat and shoved my bum as far in the air as I could. Dave leant over me and started to squeeze my boobs and stroke my bum. Then I could feel his knob sliding up and down in the cum in my crack until it came to a stop resting against my bum-hole. His hands returned to my boobs and then he pushed.
"Oh my God! Oh my God! Oh my God!" I cried. Let me offer you a piece of advice: if you get fucked up the bum for the first time, choose a bloke whose knob is smaller than 10 inches. It hurt like hell. "Dave, take it out, its agony."
"That's what Charmaine said when I first went up her" replied Dave. "I'll keep still and if you just relax, the pain will stop. Let me know when you're ready for the fucking of your life?" Fucking of my life! The way I felt I thought it would be the end of my life. I stayed very still and, pretty soon, the pain had subsided. It hadn't gone completely but I could now feel this huge hot lump in me and, know what, it felt pretty good. Very slowly, I pulled my bum back about an inch and then pushed back to re-impale myself completely. Ummm that was nice. I did it again. Nice again. Then I pulled back about 3 inches and pushed back hard. I swear I saw stars but it didn't hurt any more than before. I did it a second time. Wow, this was unbelievable. There are no words to describe the feeling; it's too fantastic.
"OK Dave, shag my brains out." Oh boy did he? 10 minutes of a 10 inch knob being shoved all the way up and then all the way back. Just as you are about to catch your breath its being rammed back in again. I couldn't believe the feelings coursing through me. Finally, his knob got even bigger and he thrust it in so hard I thought it would come out of my mouth and then he was coming. I've been told that your insides don't have the right nerves to feel hot cum being splashed into them. Don't believe it -- you can and it's brilliant.
When he pulled out of me I felt like all my bones had been removed. I fell over onto my side and curled up into a ball. Dave carefully slid my knickers off my legs and used them to wipe the cum off my bum and his knob. Then he put himself away, pulled my skirt down over my bum and sat me up in the seat. Then he started the lorry and we set off again.
We talked as we drove along. "Would you like to do it again?" Dave asked.
"Not right now. I still very sore and I can feel your cum trickling out" I replied.
"Of course not right now Silly. But in a while when I'm ready again."
"I'd like to Dave, it felt bloody brilliant but I don't think my bum's big enough for you." Dave thought about this for a while.
"I reckon I've shagged Charmaine up the arse at least a thousand times" he said. "God know how many other blokes have been up her. Now I can slide in as easy as going into her quim. I reckon you need a bit of stretching then you'll really enjoy it." I liked the idea of really enjoying it and told him so. Then we talked about my plans and if I really needed to see Jackie. I could spend the week with him and get fucked senseless 4 or 5 times a day. He would drop me off near where I lived on Friday and he would take me shopping in Edinburgh. So, while he went shopping for "something to help me stretch", I phoned Jackie from Stoke on Trent and got her to cover for me. I didn't tell her I was with a bloke. I let her think I'd been picked up by an older woman and was giving the benefit of what I hid in my knickers. Jackie was as good as gold about it.
When we got back to the lorry, Dave handed me a brown paper bag. Inside was a huge pink dildo. It was bigger than Dave's knob and had thick veins sculpted all the way up it and a big, perfectly shaped bell end. It also had a sucker on the other end. Dave told me that it was the exact copy of some porn star's knob. He told me to lick the sucker and use it to stick the dildo on the seat. Then he told me to lick the bell-end to get it really wet and then sit on it. It took me about 5 minutes to get all the way down so that my bum was taking my weight and it really hurt while it was going up me but, once I was down, it didn't feel any more painful than when Dave was shagging me. Dave started the lorry and off we went again. I could feel the engine's vibrations coming up through the dildo which felt pleasant rather than horny and it seemed to help my insides to rearrange themselves around it and for my sphincter to relax and get used to this whopping thing in it.
After about an hour, we pulled into a truck stop and Dave said we were going for a cup of tea. I gently lifted myself off the dildo and turned to jump out of the lorry. Dave told me to bring it with me. The thing wouldn't fit in my handbag so I had to walk along past all the other lorries with 3 inches of bright pink dildo sticking out of the top of it.
When we got to the building, Dave told me to go into the Ladies and wash the dildo. He would go into the canteen and get us both some tea. When I got into the canteen, Dave was sitting at a table. He seemed to know everybody in there and was happily chatting away. I started to sit down. Dave asked me why I thought I had to bring my "stretcher" with me. As I was turning bright red he told me to stick it to the chair and use it. So, red with embarrassment, I took the dildo out of my handbag, licked the base, stuck it onto the chair, gave the bell-end a quick lick and eased myself onto it. Once I had got all the way down I opened my eyes and looked around. Everybody was staring at me. Suddenly, I didn't care. I felt a complete slut. Nobody knew me and they wouldn't see me again and I bet that they all felt really jealous of Dave having such a sexy little chick with him. Dave certainly was beaming with what looked like pride. He reached over and patted the top of my head. "I thought you'd be up for it when I first picked you up. We're going to have a great week love."
I repeated the performance when we got back to the lorry and, unless I had Dave's knob up me, I was sitting on the dildo whenever I was awake for the next 4 days. By Wednesday, Dave could slide up me really easily and I didn't hurt at all. We had bought some KY jelly so I didn't have to wank before I got fucked. Dave wouldn't touch my willy (something about not being gay) but I could wank myself while he was fucking me. We did it at least 4 times every day but I can't manage more than once a day because of the hormones. I won't bore you with the details because it all gets a bit repetitive.
Dave took me to Edinburgh and I got a Chanel "little black dress"; a pair of Jimmy Choo shoes -- plain black courts with a 4 and a half inch stiletto heel -- very sexy and hell to walk in; and the most gorgeous Scottish formal dress -- in red tartan with a full long skirt, long bell sleeves, a deep plunge neckline on a fitted bodice and a white cotton and lace petticoat to wear under it. It will be perfect for Christmas with a shawl and brooch.
We stayed for one night at Dave's house. They are severely weird. Charmaine was exactly as I pictured her -- a pretty brunette with short, well styled hair slightly running to fat. Skirts a bit short for her age but she carries it well. Elspeth is a typical Chav but nice enough. She's quite pretty under all the makeup and could be a real stunner if you could get her into some decent clothes, just a little makeup to enhance rather than obliterate her features and get all the gel washed out of her hair. They were incredibly friendly; especially when you think I had just been shagged by the man of the house (we did it in the back of his car on his drive just before we went into the house. I was saying "Hello Charmaine, it's really good to meet you" while Dave's cum was running out of my bum and down my legs).
Charmaine and Elspeth took me upstairs for a bath while Dave went down to the pub for a drink. I was about to suggest a little privacy when Charmaine's hand shot up my skirt and encountered no knickers. "Oh, who's a lucky girl to have a bit extra? Elspeth love, come and look at this. I bet you've never seen such a pretty one before?"
"Ooh Mum, it looks lovely. Can I touch it Jilly?" Both of them had a play and Elspeth had a suck but, although I got a bit of a stiffy, they couldn't make me cum. Bloody hormones! Then they put me into the bath and gave me a good wash all over, paying particular attention to my willy and balls, bum and boobs. I hadn't been bathed since I was about seven and certainly not in such a lascivious way and there was something really comforting about it. Once they had got me out of the bath and dried me down I got dressed in bra, knickers and tights for the first time since I had left home. Then I put on my one decent dress (I didn't think the Chanel was appropriate and I thought that they would feel I was taking the piss) and went down stairs to chat to them in their living room.
Charmaine asked me if I had had a nice trip with Dave. I was just mumbling some anodyne reply when Elspeth said "Hasn't he got a big cock? It's easily the biggest I've ever had. It's even bigger than Sean McEvoy's and he thinks his is a whopper." I didn't know what to say. Ok, I fuck with Jackie but we're sort of sisters so it doesn't count. I couldn't imagine going to bed with Mum or Dad but, thinking about it, I bet Jackie could. Anyway, the conversation turned rapidly downhill for a while as we discussed Dave's attributes and how good he was at using them. Eventually, I managed to drag the conversation onto less torrid ground by mentioning that I had been shopping in Edinburgh. I showed them the clothes and shoes and gave them a little fashion show. I was very aware of their eyes on me when I was changing from dress to dress but they were very complimentary about the clothes.
Charmaine gave us all supper when Dave came back from the pub. It was Lancashire hot-pot. This has lamb in it so, ordinarily, I wouldn't eat it but I really didn't want to upset Charmaine by telling her that I was a vegetarian. I could feel Dave's eyes on me as Charmaine passed me a full plate of the stuff. I put my finger to my lips to tell him not to say anything and his face spit into a massive grin of unalloyed delight.
After supper and once the washing up was done, Dave said that it was time for bed. Suddenly, for the first time since we had met, he seemed a little unsure of himself. After shuffling his feet for about a minute he finally asked if I wanted to sleep on my own. Elspeth's bed would be free (how?) but I was welcome and he would regard it an honour if I slept with them. How could I possibly say no? So up to bed we went. The first surprise was the bed. Dave had bolted 2 double beds together so there was one bed that could accommodate about 5 people. The second surprise was that Elspeth came into the bedroom with us. OK, I knew that Dave had knobbed her but I had assumed that it was in private. We all took it in turns to have a wash and brush our teeth and then it was clothes off and into the bed. I just couldn't take my eyes off Charmaine's nipples. They were huge, the aureoles were the size of saucers and the nipples themselves were about 3 inches long and thicker than my thumb. "Do you fancy a suck on them love?" Charmaine asked. I didn't need a second invitation and I was clamped onto one of her boobs in less time than it takes to say it.
It was like firing a starting pistol. Everybody grabbed a bit of me and in seconds I was being transported into a world of unremitting pleasure. I could feel somebody rubbing my nipples while another hand was exploring my bum and a mouth was wrapping itself round my willy. My neck, waist and legs were being stroked. It was heaven. Slowly, we all parted and reformed and reformed and reformed. At one point, Charmaine was fucking my bum with one of her nipples while I was shagging Elspeth in the bum and she was sucking Dave off. I couldn't see where Dave's head was but, judging by the noise Charmaine was making, either he or Elspeth was attending to her pussy.
When we were all spent, Charmaine got out of bed and got 3 pairs of rubber knickers out of a drawer and gave one pair to Elspeth and the other to me. I watched, on the verge of sleep as they pulled them on, realising drowsily that they were the same as the ones Dave had described to me with 2 dildos in them -- one for each hole. Slowly, they both slid them up their legs, slipped the front dildos into their pussies then the rear ones into their bum holes then, finally pulled them up tight.
I looked at the pair that I had. Yes, 2 dildos. I pulled them on and up my legs. Then I pushed the front dildo to the front and tried to get the back one up to my bum. I couldn't manage as the front dildo kept getting in the way. Dave reached over and pulled them back down. Then he took a penknife from a bedside cabinet and sliced the front dildo off. Charmaine and Elspeth rolled me onto my back and lifted my legs up. They pulled the rubber knickers down my legs and one of them guided the remaining dildo up to my bum hole. Then they both gave a tug. Ooh that full up feeling. That done, somebody switched the light out and we all snuggled up together like a litter of puppies and went to sleep.
When I woke up, the 2 women were sitting in chairs by the bed, still in the rubber knickers that they had gone to sleep in. I was still wearing mine but, as the dildo in them was comparatively small, and it had been in all night, I could hardly feel it up my bum. Dave was stoking my boobs. Without saying a word he slowly pulled the knickers down and off my legs. I started to roll over onto my tummy but he gently pushed me back onto my back. He lifted my legs up and apart and then, for the first time, he entered me from the front. It was brilliant. It felt really good being knobbed by this guy while his wife and daughter watched. I could kiss him and lick his chest. Best of all, I could grab hold of his buttocks and encourage him to go harder into me. After last night there was no was I could get a stiffy but I did have a sort of orgasm. I started off feeling hot and twitchy inside. Then I could feel all my insides melting and then it was as if I had been given an injection of pleasure drug right in the middle of my abdomen. It was utterly fantastic.
Once we were all up, dressed and washed and had breakfast (just cornflakes and a cup of tea- no sugar), it was time for Dave and I to set off. I went to give Charmaine her rubber knickers back but, as she pointed out, they weren't a lot of use to her with a dildo missing so I could keep them as a souvenir. Her advice was to remember to wash the dildo thoroughly every time I pulled it out of my bum so that I didn't get an infection. Then it was kisses all round and off we went.
That pretty much covers my half-term holiday. Dave dropped me about a mile from home. We had a quick fuck in the grass by the side of the road before he left. I promised that I would come and visit him and his family and that I would try to bring Jackie with me as I guessed she would enjoy it.
There is a bit of a footnote. I sometimes wear the rubber knickers to school but only if I know that Carol won't be in. Could you imagine the embarrassment if she found out? I keep them in the back of my makeup drawer with the big pink dildo as I know that Mum and Dad never look in that drawer. I still use the dildo regularly. After all, you never know when your going to meet a guy who isn't bothered by the extra bits and who wants their sex ruined by pain? Whenever I'm up in my room studying, out it comes and up it goes. It can be a bit of a challenge if Mum or Dad comes in to talk and, when I first started, I used to just pull my knickers down and hop on but, one evening, Mum came in to ask about my plans for the weekend and noticed them around my knees. I had to tell her that I was just very hot. She obviously didn't believe me but she didn't push it. Now I take my knickers and tights off and hide them under my pillow first.
It took Jackie 2 days to find it when she came home for the summer. I came in from school and went up to my bedroom and there she was with it in her hand. She asked me if I was turning gay or was it something I used on Carol. I told her that I'd bought it for a dare (where around here could you buy one?) but, yes, I had tried it and it was cool. She wanted to see how I used it so I showed her. Then she stuck it on the edge of my dressing table and rubbed herself off with it. She wanted to know what it was like having something up your bum so I offered to show her and ended up shagging her bum hole.
Anyway, I'm supposed to be writing an essay on "Elastic and In-elastic Demand Curves" for Economics and I've come to the end of my story. I'm glad that I found your website to send it to as I've wanted to tell somebody for ages. Please e-mail me to let me know if you have enjoyed it. If you have I might write again about the gaps I've left and about my (few) and Jackie's (many) adventures including the end of the summer when we had a weekend in Carlisle. (Dave was very discreet and didn't let on that it was him that had been shagging me for a week. Jackie thinks he picked me up on the way home and we just got talking.)
Lots of love,
Byeeeeee
Jilly XXXXXXXX jilly_dupree@fsmail.net