Sporty Spice's First Outing by Shauna H.
I wasn't sure how far I could push things with Terri. I always thought that he would look really cute, if only I could find a way to get him 'dressed up'. Little did I think that my plan would backfire, and end up with both of us getting our first taste of cum!
Terry was my young brother-in-law, nearly 14 years old. He was very close to Sandra, (my wife), particularly since his older brother had moved abroad for work. He didn't seem to quite fit in with his friends of his own age. He was a bit of a loner, and spent more time playing on his computer then playing with his mates. He did get on quite well with the local girls, and his many female cousins. He spent an inordinate amount of time looking after his baby cousins, and took great pride in his babysitting skills. Terry tended to avoid traditional boyish activities, and his series of excuses to avoid rugby training at school became something of a running gag.
There was a big generation gap between Terry and his parents, John and Carol. Terry had come along as a 'late surprise', nearly ten years after their next youngest child. He was now the only one still living with his parents in the family home. He was of slight build, very slim and quite tall for his age. I had seen a few hints and signs of femininity in recent months. He let his fair hair grow quite long, in the style of that cute American teenage boy band, Hanson. (Wouldn't those guys look sweet in a nice, short mini-dress?) He had got me quite excited one time when Sandra asked him to fetch her new dress from upstairs. He minced along the hall, holding the dress up to his body and wiggling his little bum in a very sexy manner. I think it was this small incident that got me thinking about certain possibilities.
Terry spent a lot of time with Sandra, and since our recent marriage, he was spending even more time at our house. Sandra had known about my occasional cross-dressing activities before our marriage. I was really grateful that she accepted my special activities, especially as they weren't very frequent - only once every couple of months or so. Her natural enthusiasm for shopping overtook any concerns about my dressing, and we shared many outings browsing through the lingerie departments of local stores. She also seemed to particularly enjoy applying my make-up, and sometimes called me the 'sister she never had'. She also tolerated my time spent on the Web browsing on various interesting sites about sissies and maid training etc. Occasionally, she would pass some disapproving comments if she looked over my shoulder to see some of the more outrageous pictures that can be found, but she never got too upset about this. I really loved the stories that involved taking things much further (i.e. outings while dressed, enforced servicing of males etc.), but I never really thought these would come to life. Little did I know?
On this particular weekend, Sandra had arranged to pick up Terry from his all-boy boarding school on Friday evening. He was due to say over with us on Friday night, and to spend most of Saturday at our house, as John and Carol were away at a conference. On Saturday morning, we all rose for breakfast at around 9.00 a.m. I had intentionally left the heating off, so that the house was quite chilly. As I had expected, Terry came down for breakfast wearing a long over-sized T-shirt and his little white cotton underpants. Sandra and myself were quite snug in our towelling dressing gowns, but I could see that Terry was visibly chilled. After waiting about 10 minutes for the cold to settle in, I took the first step of my plan.
'Well, young man, you look like you are absolutely freezing, do you want something warmer to slip into?' I asked him. 'Yes, please' he replied politely, and looked up at me with his warm, innocent eyes. 'OK, we'll let's see what we can find for you', as I ran upstairs enthusiastically. I went to Sandra's wardrobe, and pulled out her satin purple dressing gown. I had bought it for her with a matching nightdress as a St Valentine's Day present some years ago. I gently stroked its silky material as I reached into the bottom of her wardrobe and pulled out Sandra's pair of fluffy pink slippers. I hurried downstairs with my goodies under my arm.
'There you go, young man'. I smiled as I dropped the slippers at his feet and held out the dressing gown for him. He looked at me with tension in his eyes. 'I'm not wearing that!'. 'Come on, come on, I don't have all day' I replied, shaking the dressing gown impatiently to hurry him on. He slid his arm into the sleeve, and I wrapped it around his little body and slipped the other sleeve on to his right arm. He pulled it over at the front, and tied the satin ribbon drawstring in a shoelace bow at the front. He smoothed down the front panels over his abdomen and thighs, and I detected a slight grin on his face as he stroked the silky material. He stepped into the slippers and sat back down to the kitchen table. 'So now I have two Sandra's' I blurted out, and tossed his hair in a friendly, safe gesture to reassure him.
We continued with breakfast, and I noticed that he seemed to be keeping one hand resting on the dressing gown on his thigh, with an almost imperceptible stroking movement. We finished our light breakfast, and Terry (as usual) sat on his ass watching TV while we cleaned up. When we all trooped upstairs to get dressed, he offered to give back the dressing gown, but I suggested that he kept it in his room, 'just in case'. I made sure that his bathroom was stocked with perfumed shower gel and shampoo, before he showered. In recent months, we had noticed that some early traces of puberty-related vanity had appeared, and he was spending more time on his 'grooming' than previously. We all got dressed, and prepared to go about a normal Saturday's business.
The next stage of my plan was taking place in the garden. Terry appeared wearing a pair of scruffy jeans and a sweatshirt. I took the lawnmower out of the shed, after suggesting that I should give the grass one last cut before the winter. In reality, the grass needed cutting like a fish needs a bicycle, but it was all part of the master plan. Terry grudgingly offered to help me out, but only after several heavy hints on my part. I asked him to hold the lawnmower while I refilled the petrol tank, after letting him have several warnings about the dangers of getting too close to the cutting blades, just to keep him on edge. As I was pouring the petrol into the tank, I gave a gentle tug onto the starting line, to get the motor to jump slightly. Terry reacted exactly according to plan, and pulled back letting the lawnmower drop down. I jerked the petrol can towards him, and gave him a liberal sprinkling of petrol, mainly on his crotch and stomach. 'You stupid little prick' I shouted, combining simulated rage with just a touch of humiliation to break down his defences. While immediately denying responsibility. I could see that he was quite shocked, and looked to be close to tears. 'Well, you'll just have to shower again and change' I instructed, in a tone that made it quite clear I wasn't in a mood for discussion or argument. 'But, I've no other clothes with me' he responded in a timid, shaky voice. 'I'll find something for you, don't worry. Now hurry, before that petrol irritates your skin'. He limped back inside, feigning a major injury. 'You'd better drop your jeans there in the kitchen' I suggested helpfully. 'Otherwise, they'll stink out the whole house'. He looked back at me, with frustration and confusion written all across his face. I just focussed on the lawnmower, so he had no opportunity for further negotiation. Out of the corner of my eye, I could see him pulling off his jeans and sweatshirt, and dropping these in the kitchen. He skipped off upstairs in just his white cotton pants, with those long elegant legs looking cuter than ever. I followed him upstairs, at a distance.
I handed him fresh pale yellow towels as he went into the bathroom. 'Here, you'll need this' I said, as I handed him a small bottle of purple liquid. 'What the hell is that?' he asked, with distaste on his face. 'Have you ever seen what petrol can do to your pubic hair?'. 'What?' he responded with a sulky voice. 'It will just all shrivel up and fall out, if you don't wash it out quick with this stuff. Go on now, before your follicles get infected'. He jumped into the bathroom and slammed the door, not quite realising what he was about to rub into his pubes. I waited patiently in our bedroom for him to finish. Sandra appeared, and asked my why I was hanging around. I told her that Terry had seemed a bit upset, and I just wanted to make sure that he was OK. She seemed reassured at my big brotherly concerns! A few minutes later, Terry edged his way out of the bathroom, looking embarrassed and sheepish. 'Are you OK' I asked. 'I think so, but most of my hair seemed to fall out in the shower' he replied, while looking down towards his crotch. I struggled to avoid smirking while I told him 'You mustn't have got that cream on quick enough'. 'What can I wear now? Your clothes are all too big for me' he asked in a kind of helpless pleading voice. 'Don't worry' I answered in a reassuring voice. 'I'll get you one of Sandra's track suits, and no-one will know the difference - OK?'. 'Suppose so' he said, while drying off his body. I went back into our room, and picked up two of the items I had laid out earlier. I lifted the pale yellow satin hipster-style briefs and her Adidas shiny pale blue tracksuit pants with bright yellow stripes down the sides into my arms and went back into Terry's room. 'Now don't laugh' I warned him. 'But all of my jocks would be too big, so these will have to do you - OK?' He laughed and was about to respond in the negative, when I interrupted 'Come on, no-one will know'. I wouldn't be the first time or the last time I would use that line on that day. 'I'll be back in a minute' I said, while leaving him discretely to come to terms with his new humiliation. I would have given anything to be able to witness his next steps, but I didn't think he would be ready for that yet, and I didn't want to jeopardise the whole deal. After a few minutes, I knocked and went back him to find him walking around the bedroom in the bright blue tracksuit pants. 'How do they fit?' I inquired. 'Well, the track suit is a little short, and the pants are'. 'Panties', I corrected, taking the opportunity to get him used to the new role. 'the panties are a bit tight, but I guess they will do'. His tight stomach muscles were looking very firm, just peeping out above the waistband of the tracksuit, the legs of which finished just at ankle length. 'OK - I'll get you something nice for on top' I said, and looked him directly in the eye. I could see he was trying to 'read' my face, to see if I was joking or not, but I kept a clear 'poker' face as I exited the room. I went back to our room, and got my second set of 'props' for the little play that was showing in the room next door.
I picked up the satin bra that matched the briefs he was wearing, along with a yellow 'belly top' of Sandra's. This nylon/lycra top was cut off just below the chest area. I reckoned that this was the moment of truth. If I could get him into the bra and top, there would be no going back. I had to handle this really carefully, with just the right balance of fun and aggression. I walked back into his room with the bra and top clearly visible on my arm. 'No way - just no way' he shouted, while backing away across the room. 'Come on', I pleaded 'Just for a laugh - You're already wearing her panties and tracksuit anyway, so what difference will it make. It will give Sandra a real laugh'. He looked really confused, so I decided that swift action was necessary. I walked towards him and said 'Come on, just turn around' while firmly holding both shoulders and turning him away from me. I put the belly top on the chair in front of him, so he would keep his eyes on it. I held the bra out in front of him. 'Now, just slip your arms through' I said in a very 'matter-of- fact' tone of voice, and I nearly exploded with pleasure and anticipation as he lifted his hands and slipped them into the loops. I pulled the straps across his back, and fastened them at the tightest setting. It seemed to be a very snug fit. I adjusted the shoulder straps to lift the bra up slightly, and turned him back around to face me. He was giggling furiously, and seemed to have got over his confusion and fear. 'OK - I guess we need just a little padding' I suggested, and reached for some cotton wool from the dresser. I handed it to him, as I reckoned it was now time to involve him actively in the process. 'Here - just fill them up a little bit, but not too much. Remember you're only thirteen'. I stood back and watched him tearing bits of cotton wool off the roll, and filling the little yellow cups with padding. As he finished, I held up the yellow belly top above his head and said 'hands up'. He obediently lifted his hands up, and slipped the belly top down his arms and over his head. I lifted it over his slightly bulging cups and smoothed it down. The yellow of the top matched his bra and panties, as well as the yellow stripes along the side of his tracksuit. What a lovely matching outfit, I thought as I stepped back to admire my creation.
'Let's show Sandra now' he giggled. 'Not just yet - we have a few more steps to go' I replied as I returned to our room. I got a pair of Sandra's 'slouch socks' that she had bought for her aerobics classes. Fortunately, these were also in matching yellow, and were designed to flop around the ankles, creating a somewhat layered and frilly effect. I also picked up a pair of Sandra's trainers (sports shoes). These were mainly white, but had nice pastel blue stripes along the sides, giving them an unmistakable feminine appearance. 'Here you go' I said, while dropping the shoes and socks beside his bed, and left him to get on with it. When I returned with one of Sandra's make-up sets, he was just tying the lace on the second trainer. The layers of the slouch socks were clearly visible at his ankles. To look at his body from the neck down, he had all the appearance of a young teenage girl, just in the early stages of puberty. Now all that was left was his face.
I sat him down on the chair, and I sat down opposite him. I turned him away from the mirror on the dressing table, as I didn't want him interrupting these next crucial steps. I decided not to use any foundation, partly because I wasn't very good at applying this, and partly because I thought he was still a little young for this. I knew my make-up skills were not brilliant, but neither are most teenage girls, so I didn't think it would matter. I got him to close his eyes and I applied some touches of yellow and green eye shadow to his eyelids. The yellow brought out the yellow of his outfit nicely. For lipstick, my first instinct was to go for a bright, very bold, pink colour, but this wouldn't have been really appropriate for his age. Instead, I took a subdued dusky wine/plum colour, and I applied a generous layer to his lips. Now for that beautiful hair of his which was crying out for some attention. I brushed it out, and brought the sides forward to frame his face. He seemed to be quite enjoying this sensation, as he sat with his eyes closed and a very relaxed smile on his dark, sultry lips. It was taking shape nicely, but it still had a somewhat boyish look. My finishing touch was to apply one of Sandra's sparkling brooches to the side of his hair, following a fashion trend that was becoming increasingly popular with young girls on TV. This really tipped him over the edge from tomboy to teenage girl. 'OK - Now you can look' I said, while turning him towards the mirror. His eyes opened wide, and I could see the sheer pleasure in his eyes. He turned his head and upper body from side to side, admiring his new profile. 'Wow' he gasped. 'Wow - she looks, oops, I look really cool'. 'You look really sexy' I confirmed. 'My own little Sporty Spice (A reference to Melanie Chisholm, singer with the UK girl group, the Spice Girls, who regularly appears on stage in sportswear).
'Are you ready to show Sandra now?' I dared him. 'Yea - let's do it' he giggled, and hopped up and ran out the door. I patted his bum gently as he skipped past me and down the stairs. I had to run to catch up with him and watch him walking along the hall into the kitchen, where Sandra was waiting. 'Oh My God, what have you two been up to' she blurted. 'I knew you must have been up to some mischief, it was just too quiet' she laughed. Then I heard a second voice coming from behind the door 'Well, well, well, who is this sexy little tart?'. It took me a few seconds to recognise the voice, then I realised who owned it. It was Carol, Terry and Sandra's mother. 'Oh shit' I thought 'that wasn't part of my plan. How is she going to react to this?' I followed him into the kitchen, to find Terri and Sandra both laughing, with Sandra primping his hair and twirling him to get the best view. Carol was sitting at the kitchen table looking on, with an unusual look on her face. It was a mixture of curiosity, interest and determination. Her eyes were wide open, and she was leaning forward in her seat, taking in this amazing sight.
'What have you done to my son?' she said in a slow, controlled but quite intimidating tone of voice. 'Come here and let me see' she summoned him, in a manner that made clear that there were no other options. Terri skipped over to her, and stood in front her with one hand on his hip, obviously revelling in his new role. She lifted his belly top to check his bra. She used her tissue to wipe off some excess lipstick at the side of his mouth, and pronounced her verdict 'Mmm - interesting. I didn't think I'd have another daughter again after all these years. Not bad, but it's missing just a little something. Who's idea was this then?'. I tried mumbling something that it had just kind of happened, when Terry blurted out 'Sean made me do it!', and silence fell on the room. 'Oh did he now' exclaimed Carol with a growing smile on her face. 'You know, I always wondered about you when Sandra told me those little stories about your 'special' nights'. I blushed and looked at Sandra, who couldn't look me in the eye. She knew she had breached my trust.
'Well, if it's good enough for Terry then it's good enough for Sean' said Carol, and grabbed my arm and led me along the hall. 'No way' I said 'No way in hell', when she surprised me by grabbing my balls quite firmly. 'Listen, you little prick' she whispered in my ear. 'You gave up your rights to control what happened when you started abusing my son. If I hear one more whimper or complaint from you today, you will find yourself at the centre of an abuse investigation. Now, try explaining that to your work-mates and the football team'. I was stunned. She had never spoken to me in that tone in the ten years that I had known her, and the fact that her grip on balls was increasing all the time convinced me that she meant business. 'But, but' I stuttered while attempting to think of something to dissuade her as she grabbed my arm and led me up the stairs.
She sat me down on the bed, and turned to our wardrobe. She went directly to my special stash of lingerie, and starting picking through my outfits. 'How did you know about them?' I stuttered. 'Oh, this isn't the first time that I've been through these' she retorted. 'Sandra always asks my advice on colour matching before she picks your outfits for those special nights'. For the second time that day, I was stunned. What I had considered to be our greatest secret had been a topic of conversation for several years it seemed. Before I had a chance to contemplate these concerns any further, Carol turned around with a cream-coloured bra and panties in her hand. 'Now, why don't you start on these while I pick the rest of your outfit for today' she commanded in an overly pleasant tone of voice. I hesitated for a moment, then she picked up the phone and asked 'Or will I just call in the police now?' I started undressing, and stepped into our bathroom with the bra and panties. 'Don't be silly, child' she scolded, and pulled me back into main bedroom. 'I brought up two sons, you know. It won't be the first little prick, I've seen. Though from what Sandra tells me, it won't be too difficult for you to keep it hidden'. I was just thankful that she hadn't discovered my little trick with the purple hair-removal cream.
I stripped off my remaining clothes and quickly lifted up one foot to pull on the cream panties. Just at that moment, Carol gave a gentle push and I ended up rolling on the bed, legs in the air, stark naked apart from a pair of cream silk panties dangling from one ankle. I was so humiliated I felt like crying. Carol tossed the matching bra onto my chest and said 'Come on, hurry up you silly child' just as Sandra came into the room. 'Now you should just wait downstairs and trust me' said Carol, as she firmly steered Sandra out of the room. 'Just leave things to me and your life will be much easier from here on out' Carol instructed, showing decisiveness that I had never seen before. She shut the door leaving Sandra outside, and she went back to the wardrobes, leaving me to struggle with my underwear. I got the panties on, but I had an unsightly bulge at the front. I was straining behind my back to get the bra fastened, when I remembered how Sandra did it each morning. I pulled the straps off my shoulders and rotated the bra to leave the fastenings at my front. I clipped it closed and wound it back to the normal position, slipping my arms through the loops. 'That's better' said Carol approvingly, 'now try these'.
I couldn't believe my eyes, but perhaps I shouldn't have been too surprised. She had in her arms an outfit that almost exactly matched how I had dressed Terri just half an hour previously. My own track suit pants were an exact match for Sandra's. She had found belly top that looked larger than Terri's, in a pale pastel blue colour. She also found an Adidas tracksuit jacket, in the reverse colours of the pants, i.e. yellow body with blue stripes along the sleeves. I was relieved to think that I should at least be able to cover up my bare abdomen. She had a pair of yellow slouch socks, and a pair of trainers that looked familiar, but somehow different. I then recognised them as my own trainers, but looking much cleaner than they had ever been since I first purchased them. I pulled on the pants, socks and shoes, and then struggled to get the belly top into position. I stood up to the mirror, and decided that the best strategy would be to try to keep Carol happy. Anyway, it didn't look too unusual, so I reckoned I would simply be able to pass off as a bit of a sports freak. 'What do you think, Carol' I asked, while waggling my hips left and right to show off my new profile. 'Not bad' she said 'but we need a few final touches to make it a bit more realistic. Now, take a seat' and she steered me towards the dressing table. 'Oh please No Carol' I begged, and she stepped towards the phone, picked it up and placed one finger on the 'nine' digit. I had no choice but to sit back down, and await her actions. 'Mmm, good job you shaved nice and close this morning' she mumbled, while smoothing on some foundation. It was quite relaxing just sitting there, letting her do all the work. She whispered gently 'Now close your eyes dear', and I felt her brushing gently against my eyelids and eyebrows. She moved onto my lashes, giving them a generous coating of mascara. I felt her apply the eyeliner pencil along my bottom lid, then she asked me to pout my lips. I felt her repeatedly wiping the lipstick onto my lips. I was wondering what colours she was using, scarlet pink or possibly dusky plum like I had used on Terri. I got a cool tingling feeling on my neck as I felt something metallic and cold gently tickling my neck and the top of my chest. She placed some kind of hat on my head, and adjusted it's position a couple of times. She pressed something onto my earlobes, and my mind was racing, wondering how I was going to look. 'Now, my dear, open up and have a peep' said Carol in a very gentle voice. I opened my eyes, and I saw what appeared to be sporty young lady in her mid-twenties, looking back at me. Carol had given me a pale blue baseball cap, with some blond hair extensions hanging out of the back in a ponytail. The cap was pushed back high on my forehead, giving a clear view of my pale blue eyelids, highlighted by the eyeliner and mascara. The foundation had given me a clear unblemished smooth skin, with what appeared to be a healthy tan. A delicate neck chain held a tiny gold heart at the top of my chest, and small gold studs were pressed onto my ears. 'Wow' I exhaled 'Wow wow wow wow wow - I don't believe it'. 'OK - Now let's show the others' she said, with a pleased tone in her voice. She brought Terri and Sandra back in, and they were both pretty amazed. Sandra did her usual trick of primping and checking my appearance and make-up, and Terri just giggled. I could also see through his pants that he was still pretty excited at what was happening. When the fuss had died down, Carol said 'OK Come on girls, less talk and more work - we've got some shopping to do'. My heart sank. 'No way' I retorted and she moved towards the phone, reminding me of the unpleasant other option. 'But what if we meet anyone we know?' I pleaded. 'Well then, you'll just have to make sure that you look your best and make sure that no-one suspects anything' she countered, and I knew I had really no choice. I picked up the tracksuit jacket to give me some 'coverage', even though it was a very feminine colour. But, when I attempted to fasten the zip, I found that it would only close up by a couple of inches, leaving my bare abdomen dangerously exposed. I looked up to see that Terri was having the same problem with his matching jacket. 'Oh dear' said Carol 'aren't those zips very unreliable. I wonder what could have possibly caused that?' with a look on her face that told me that she had direct knowledge of what caused the zips to jam. 'Let's go girls' she piped, as she directed us downstairs and out towards the car. I was heading for my usual spot in the driver's seat when Carol snatched the keys out of my hand and said 'No - I think you girls will sit in the back and enjoy the ride'. As I bent down to climb into the back seat, I felt a firm finger probing the crack of my ass. I nearly lost my footing and fell into the seat'. 'What a clumsy girl' mumbled Carol 'I hope she has better balance in her new shoes'. Terri and myself sat side by side in the back seat. My worst nightmare was quickly coming to life as we headed for one of the largest local shopping centres, the one where we had met other family members and several work colleagues in recent months. Still, the dividing lines between my worst nightmare and my favourite fantasies were a little blurred, and my sexual excitement combined with good old-fashioned curiosity was most encouraging.
As we stopped at the traffic lights, I could see Terri was getting admiring glances from some young guys in the car beside us. Terri blushed, and looked at me with a guilty grin on his face. One of the guys looked over to me, and smiled in an inviting manner. Fortunately, the lights changed and they tore away before I had a chance to decide on an appropriate reaction. We arrived at the centre, and Carol expertly parked the car into a very tight space. 'Let's go, ladies' chirped Sandra 'We're going to have a real girly day out' as herself and Carol jumped out of the car. Terri and myself looked at each other, though I had to pinch myself to remember exactly who he was. I took a deep breath as we climbed out of the car, and felt the cool November breeze chilling my bare abdomen. Terri ran ahead, deciding that his best chance of anonymity lay in staying close to Sandra and Carol. As he moved ahead of me, I could see that he made a quite convincing teenage girl. A little more awkward than most girls of that age, perhaps, and a little less confidence, but still exuding that growing awareness of sexuality that seems to flow from early teenage girls. I reckoned that he was right, and that by sticking close to Sandra and Carol, it would minimise the chances of Carol deciding to make a 'scene', so I quickly caught up with them. I could see that a couple of passers-by were giving Terri and myself a second glance. I guessed that our matching outfits in almost fluorescent colours were attracting some attention, but perhaps they would simply conclude that we were members of the same hockey team, or something like that. Anyway, no one seemed to be staring unduly, so we moved on.
I wasn't surprised to find Carol and Sandra diving into the first ladies boutique that we encountered, with myself and Terri following close by. 'Now, remember guys,' whispered Sandra 'If you just stand around staring vacantly into the distance, you just might blow your cover, so you had better look interested and get involved'. Well, there was no arguing with her logic, so I looked at Terri, he looked at me, and then we swung into action. He took down a pink mini-dress off the hanger and held it up in front of his body, asking me what I thought of it. After making some comments, I did the same, and saw Carol and Sandra smiling at their new creations. We continued browsing around the next few shops, joining in with the shopping activity like we had been doing it for years. Then, Carol steered us into the next phase of our humiliation.
She brought us into the large chain store, with a wide selection of ladies fashion and everyday wear. 'Now' announced Carol in a businesslike tone 'myself and Sandra have to get the grocery shopping done, so we're going to leave you two girls to some more pleasant tasks. You have thirty minutes to select an outfit suitable for a semi-formal evening out. Nothing too formal, and nothing too tarty. Let's keep this cutesy 'matching' theme going, so you'll make sure that you find something that suits you both. You'll need some underwear as well, so find another bra and pants set. Oh, don't forget some tights or stockings. We don't want to let those legs let you down, do we? Sean, just put the lot on your visa card please. We'll see you in thirty minutes, so don't keep us waiting'. With that, she disappeared across out of the chain store, with Sandra trailing behind her.
Terri and myself looked at each other, slightly stunned. I don't know if it was the thought of purchasing our own underwear, or the fear of when we would be wearing these clothes, but we were both pretty confused. Still, it hadn't been too bad so far, and I had always fantasised about going 'public'. I leaned over to Terri, and whispered 'I guess we'd better get on with it'. He grinned in agreement, and off we went browsing. We seemed to be initially in the section for older ladies (lots of cardigans and flowery dresses), so we moved off towards the more fashionable outfits. We passed through the 'Christmas party frock' section, and I lightly fingered some of the velvet dresses, in both long and short styles. Terri held up a classic LBD (little black dress) in front of his little body, and tilted his head to one side, looking for my approval. 'A bit too formal' I responded, and we moved onto the fashion section. We eventually found ourselves in the middle of a section of matching 'separates', i.e. long and short skirts, jackets and tops. We browsed around, holding up various combinations for each other, and giving and receiving feedback. At one point, I got a bit panicky and I started looking around to make sure that we weren't being spotted. But, no one seemed to be taking any notice of what probably looked like two sisters on a shopping trip. So, we continued browsing. Eventually, we agreed on a jacket, short sleeved top and short skirt for each of us. Terri had his eye on a bright cerise pink colour, and I was going for a more conservative pastel blue outfit. We had more or less made up our minds, when my sense of adventure outvoted my fears and piped up 'Are you going to try it on?' Terri giggled again and we looked around for changing rooms. Fortunately, they had individual rooms rather than communal rooms. We popped into a pair of rooms side by side, and struggled with our new outfits. I found the feeling of a short skirt really strange. My legs felt really bare, and my increasingly excited manhood felt really exposed. I pulled on the top, and jumped out to a little fanfare from Terri. 'Aren't you forgetting something?' he queried, with a sly grin on his face. I looked down to check my outfit, but I couldn't see anything missing. I then checked the mirror, to find a pretty good-looking young lady, from the neck down. However, I had forgotten my baseball cap and integrated ponytail, so it was pretty obvious that all was not what it seemed. I dived back into the changing room to retrieve it, and came back out to study Terri.
He had done better than me, and had the whole outfit on, including the jacket. He looked really sexy and cute, just like one of those teenage girls sometimes known as 'jailbait'! He minced around the shop floor, and I started panicking again as I was worried about attracting too much attention. 'OK OK, let's keep going, we still have to pick our underwear, remember' I reprimanded him. We ducked back into the changing rooms, and donned our original outfits again. Terri decided to leave his tracksuit jacket off, as he was a little hot from all the changing. He looked really cute with that 3-inch strip of exposed abdomen, front and back. 'Now the fun starts' I giggled 'Bra's and Knickers'. Terri's eyes lit up and we moved off to the lingerie section.
They had a wide selection of lingerie in all shapes and sizes. It was mostly in satin, as the 'everyday' cotton stuff was in a separate section. This stuff was for special occasions, and it doesn't get much more special than a guy's first night out in a skirt! We browsed around, touching almost one of each item on display, cami-tops, french knickers, basques, suspender belts etc. We had to remind ourselves that we had some serious work to do. We came back to the sections with bra/pants sets, and started looking through them. I advised Terri that we should get some of the 'brief' style panties, just to 'keep things under control' and he agreed. Eventually, we agreed on a 'matching' style, yet again. They had a nice soft bra (no nasty wiring to chafe against our tender chests) and hipster style briefs. I chose a soft pastel blue colour, and Terri picked a nice baby-pink set. 'Well, I think that's everything' I said, gathering our new purchases under our arm and heading for the cash desk. 'Here's Sandra' announced Terri. I looked up to see Sandra and Carol heading back into the store, carrying their grocery shopping. But, wait a minute, I thought, who is Sandra talking to? I could see two other ladies following closely behind, all of them grinning widely. Oh Lord no, I thought with a sinking heart. It was Pauline (our next door neighbour) and her teenage daughter Fiona, and she was looking right into my eyes. 'Well, who have we got here then?' giggled Fiona, as herself and Pauline gathered around us. Terri had a bit of a crush on Fiona for several years, but as she was just a year older than him, she was 'out of reach'. But now she came closer to him than she had ever done before, closely examining his make-up and jewellery. 'Doesn't little Terri look so cute?' she asked. 'Yeh - but her friend could do with losing a little weight' answered Pauline, and all four females burst out laughing at my bulging abdomen. Perhaps they might even have noticed my bulging crotch as well. I was so embarrassed as I blushed under my make-up. 'They have just done their first shopping trip' announced Carol proudly 'and didn't they do well'. All the girls went through our outfits and underwear, and insisted on holding up each of the purchases in front of our bodies to check for size. My heart was racing, as I scanned the shop to see if we were attracting any attention. Fortunately, the shop was not busy, so at least it was only these four strong confident females that we had to worry about.
'So, what are the outfits for? Is there an outing planned?' asked Pauline. 'Well, I just thought we might all go out for a meal tonight' said Carol, in a thoughtful voice. 'I know' said Pauline 'Why don't you and Sandra and this big girl join me at the cinema tonight, and Terri and Fiona can go to a different film if they wish. It has been pretty obvious that he has wanted to go on a date with Fiona for a long time'. My heart sank as Sandra and Carol's eyes lit up. 'Great idea' said Carol 'Now we had better go home as these two girls might need time to get changed', and all four collapsed into fits of laughter again. Terri and myself just looked at each other. I'm sure he shared my horrible feeling that this was getting totally out of my control. Carol gripped my arm and led me firmly towards the exits, and back out to the car park. My relief at getting out of public view and returning home was tempered with curious anticipation as to what was ahead for us tonight.
We returned home and I disappeared upstairs to change back into my own clothes, while Sandra and Carol busied themselves with the groceries. However, when I got into our room and opened my wardrobe, I was horrified to find that all of my clothes were missing. Carol followed me into the room and said 'Now - lots of room there for your new outfits. Why don't you hang these up while you start getting ready for tonight?' I was stunned, and I stared at her open-mouthed. She reached into her handbag and handed me the bottle of purple hair-removing lotion that I had given to Terri that morning. 'I'll be inspecting before we go out, and I don't want to see a single hair on your body anywhere from the neck down. Pubes, armpits, chest, asshole - I want the lot to be trim and bare - Understand?' I didn't feel I had any option to argue or discuss the point, as she steered me into the shower. The last thing I saw as I entered the bathroom was Terri being led down the hall by Fiona, laden down with shopping bags. 'Don't forget your make-up' she piped in a cheery matter-of-fact voice. 'But I don't have any' stammered Terri. 'Oh well, we'll just have to share mine then' she giggled as she led him next door to get changed.
I found the purple lotion to be amazingly effective. My pubes and chest hair just fell away, and clogged up in clumps around the plughole. I couldn't help getting rather excited while soaping my smooth, bare manhood, but unfortunately Carol interrupted, before things could develop. She handed me a pale pink towel, and insisted that I wrap it around my chest, not around my waist, as I would normally do. 'Now- shave twice with a fresh blade' she instructed. 'I don't want to see a five-o-clock shadow peering through your foundation later on. And use this body lotion all over. It will help ease the stinging from the hair-removal. I'll be back in fifteen minutes to help you to dress'. 'It won't take me that long to shave' I replied with enthusiasm. 'Oh take your time dear - you can't rush these things. You really have a lot to learn' she replied in a reassuring manner.
I took particular care to shave closely, and I really enjoyed applying the body lotion all over. Once again, I was just getting nicely excited with the lotion when Carol burst in. 'Oh put that little thing away please. It's just an irrelevancy now'. She dragged me back into the bedroom, and I saw my outfit for the evening laid out on the bed. 'It's always advisable to lay out your outfit beforehand. It's important to ensure that all the colours match nicely' she advised me. I noticed that she was beginning to sound like a schoolteacher guiding a slow pupil through a difficult lesson. The pale blue jacket and skirt were laid out with a bright white polo-necked top. The matching bra and knickers were to one side, but the big surprise was sitting on the floor - knee high black suede zip-up boots with heels of around 3-4 inches in height. 'Where did you get the boots?' I stuttered. 'Oh Sandra picked them up for you as a birthday present, but there's no point in waiting any longer, so we thought we might as well let you try them for size.' she replied. My eyes nearly burst out of my head. 'Now - I'll be back in about 15 minutes to do your make-up. Put the white top on beforehand because we don't want to smear your foundation. Don't put on the jacket and skirt or the boots until we finish with the make-up. See you soon' and she disappeared before I had a chance to argue or have a discussion.
I slipped quickly and gracefully into the knickers and bra. I was really surprised that despite how excited my heart was feeling, my little manhood was really quite relaxed, and wasn't causing any unsightly bulges. The bra seemed much simpler this time around and I fastened it first time. Carol had also left out a suspender belt and a pair of very sheer flesh-tone stockings. The belt was difficult to fit, but it wasn't my first time, so after a couple of attempts it was in the right position. I rolled the stockings in the way Sandra had shown me months ago, and slipped then onto my smooth legs. No nasty hairs to catch on this time! I was struggling with the rear fasteners on the belt when Carol returned. 'Oh come here child' she chided as she quickly clipped the stockings into place and let me over to the dressing table. 'Now, you'll have to start getting used to doing this yourself soon, but for tonight, you just sit back and relax and leave it all to me.'
I took her advice and closed my eyes and sat back. I felt her sponges and brushes working on my face and eyes, and I could sense the sweet smell of the cosmetics. I got very excited as she applied the lipstick right across both lips. I could then feel here putting what seemed to be a loose hat on the top of my head. She moved her hand around my earlobes and neck, and I could feel a cold metallic sensation on my neck. I was just dying to see what the end result was going to be like. She led me quickly away from the mirror before I had a chance to witness my transformation. She handed me the skirt and I stepped into it carefully. I fastened the zip, but it still felt surprisingly incomplete, like there was something missing. Carol held out the jacket and I put it on. Now the final feminine step - the boots! I sat down on the bed, unzipped the right boot and slipped my stockinged foot into the suede. I had never experienced anything like the feeling of enclosure and support that came over me in waves as I fastened the zip. I pulled on the other boot as fast as I could, and jumped to my feet to see how I looked in the mirror. However, I had forgotten about the heels on the boots, and I overbalanced straight back onto the bed. I struggled back up ungracefully and moved towards the mirror.
I couldn't believe what looked back at me. There was a tall and rather sexy looking lady with long cascading blond curls piling down onto her neck and shoulders. There were curves in all the right places and the high heels seemed to be forcing my hips forward in a pretty provocative manner. I felt a huge stirring in my panties, and I thought I was going to just explode there and then. Carol's firm hand in the small of my back steered me out of the room and down the stairs. As I teetered down in my heels, the front door burst open and Fiona appeared dragging Terri behind her. She had worked miracles with his hair, giving it body and depth and framing his face beautifully. She had added loads of jewellery and accessories, and another couple of sparkling brooches in his hair to set off the entire outfit. He was much steadier on his heels than me, and was mincing up and down the hall wiggling his bum delightfully. 'How did you get him to do that wiggle?' I whispered to Fiona. 'Oh it's amazing the effect of a little smear of toothpaste up his bum. We girls do it all the time' and she looked me directly in the eye daring me to question her. I thought it best to back off, just in case Carol heard about this toothpaste idea.
Both of us were brought into the lounge and paraded up and down for comment and suggestion from the four real girls. Just as I was getting used to my new role, Fiona looked out the window and giggled 'Great - here's the boys'. Terri's chin dropped to the floor as he stammered 'Boys - but I thought you and I were going on a date'. 'It's a double-date, silly' she countered 'I'm no dyke, so I can't go out with you'. Barry has brought along his little brother, Jamie. He's really quite cute you know. I was tempted once but ' she faded off into the distance leaving us all wondering about what had happened between her and the younger boy.
The doorbell rang, and Terri looked out the window. 'You'd think they would have dressed up. There only wearing tracksuits' he commented disdainfully as he drifted into his feminine role. Fiona dragged Terri out, giggling 'See you later' in that superficial way that only teenage girls can do. Terri's eyes caught mine as he was being led towards the door, and he gave me a pleading look. I just shrugged my shoulders, indicating that I didn't have much choice in the matter. 'They are getting the bus, so we'll see them up there later' Pauline informed me. 'You wouldn't want to cramp their style, would you' she asked me. I had no answer to that one, as I contemplated the sheer horror of climbing a bus staircase in high heels and a mini-skirt. 'Let's have a drink to help us all to relax' suggested Carol. This was from the lady who gave me grief over my two beers at Christmas dinner. Glasses of white wine appeared from nowhere, and we drank gracefully while waiting for the inevitable. 'Don't slouch girl' taunted Pauline as I took up my usual sprawling position on the couch. I had to sit up gracefully, and keep my legs together, to avoid giving a shock to anyone looking in the window. I allowed myself a little smile to notice that all the glasses were stained with lipstick, as I collected them up and returned them to the kitchen.
Pauline led us out to her car and the trip to the restaurant beside the cinema was uneventful. 'Now ladies, table for four' offered the young waiter as we approached the desk. We settled into our booth, and ordered light meals. For some reason, I just wasn't in the mood for my usual big steak, so I settled for a light salad instead. Just as we were finishing the meal, I spotted Sandra whispering into Carol's ear and pointing out behind me to the cinema lobby. I turned to see the double-daters arriving, with Terri hand-in-hand with Jamie. As they settled into the queue, Jamie carefully slid his hand around Terri's back and pulled the new girl closer to his body. Terri looked deeply into his eyes, before letting his head drop on Jamie's shoulder. Terri looked amazingly relaxed and comfortable in her new role.
We paid the bill in the restaurant with my Visa card, which had got a bit of a hammering that day. I thought I noticed the cashier doing a 'double-take' on the 'Mr' title on the card, but she didn't seem inclined to ask questions. We drifted out and joined the rest of the crowd pouring into the cinema. I wasn't even consulted on the choice of film, and was disappointed to see that we were heading in for a 'chick flick'. Obviously, Fiona and Pauline had planned the event thoroughly beforehand, as I could see the double-daters settling into their seats up at the front, as we waited at the back of the cinema to be shown to our seats.
The film was as light as my salad, but was reasonably enjoyable. However, I think I spent more time watching Terri and Jamie than watching the screen. Terri and Fiona were sitting together in the centre, with their respective dates on either side. They were giggling and whispering to each other, like any pair of old friends. Terri let his head drop onto Jamie's shoulder from the time that the curtain opened. However, as the film got going, I noticed that, in common with many teenage dates around them, Terri and Jamie were snogging furiously. Jamie was looking down on Terri's painted face as his tongue pushed into Terri's mouth. After a few minutes of this, I was surprised to see that they seemed to settle back down and relax. However, on closer examination, I noticed that Jamie's hips were bucking gently but rhythmically. Terri's right arm seemed to have disappeared, but on closer examination I thought I could see movement in Jamie's crotch area, under his track suit pants. Then I realised what was going on - 'The horny little tramp' I whispered to Pauline 'Look where Terri's hand has gone'. He must have opened the side poppers on Jamie's track suit pants and slipped his hand in, keeping Jamie thoroughly entertained. 'You can see where he learned that trick from' replied Pauline. I checked out Fiona, to find that she too had one missing arm and one enchanted boyfriend. During one of the more romantic moments of the film, Jamie seemed to throw his head back and his hips forward, and I had no doubt that Terri was feeling Jamie's warm sticky cum around his fingers.
Pauline was very intimate with me during the film, whispering in my ear and resting her fingers on my stockinged thighs quite a lot. I guessed that it was the sense of control and domination that was turning her on, but I was really enjoying it. I was hoping that perhaps things might go further later on. The only problem was that my constant erection was squashed down between the cheeks of my ass in a most uncomfortable position. The film completed with a boring Hollywood happy ending, but I quite enjoyed it anyway. We drifted out into the lobby and waited for the teenagers to join us. 'What were you up to during the film?' I whispered to Terri. 'What do you mean?' he replied with a guilty look on his face. 'Well, you did seem to have your hands full for a lot of the film' I asked. He giggled guiltily and whispered 'I think we might both be glad that the guys emptied their load, if Fiona gets her way'. 'What do you mean?' I asked 'What is she planning for later?' His face looked very serious for a moment, and he put his lips up to my ear. 'Well, she did say that we will have to ' he started to whisper before Fiona dragged him away with the two guys into the local McDonalds. As the guys took their place in the queue, Fiona dragged a bewildered Terri into the 'ladies' room.
We headed for Pauline's car as the teenagers giggled and flirted their way through their burgers and fries. Pauline got us home pretty quickly, and I was wondering how Terri was enjoying the trip home on the bus. The doorbell rang, and Fiona and Terri dragged their two dates into the lounge and put on some smoochy music. I kept asking Pauline and Carol what was going on, but they just ignored me, and told me to leave the younger ones alone. After a few minutes, Fiona exited the lounge with Terri trailing her. She pointed a finger at me and beckoned me 'OK now, upstairs and get ready for bed, quick as you can' she piped, clearly enjoying her position of authority. 'But it's too early for bed' I complained. 'Oh, don't worry' she said 'You've got a lot ahead of you before your pretty little head hits the pillow tonight'. She took my hand and led Terri and myself upstairs. I was surprised to see a pair of short satin night-dresses, laid out on Pauline's bed, with matching slippers and satin wraps. The larger size was in a pale-blue colour that matched my bra and pants set, and the other one was a cute baby- pink colour, matching Terri's lingerie. 'OK' instructed Fiona 'Drop the suits and change into the night-dresses. But keep your undies and the stockings and suspenders on. The boys really love them. Don't forget to hang up you suits, you never know when you'll need them again'. 'I'm not letting the boys see us like this' I stammered. 'Oh but you will' said Fiona in a tone that didn't leave any room for argument 'This is the high point of the night for those horny little boys. You see I always give Barry a nice blowjob to finish off the night, but I'm a bit worried about this cold sore on my lip. I don't want to give the poor young guy Herpes at 16, so I have to leave that in your capable hands - or lips' she giggled. 'Terri's already given Jamie a little release, but I think it's time for Jamie to get his first blow job'. We were led back down the stairs before we had time to respond, and I looked at Terri as he looked into my eyes. 'It won't be so bad' he reassured me 'Fiona gave me some tips, so I think I know what I'm doing'. He seemed to actually be looking forward to it. I made a snap decision there on the stairs that if Terri could do it, I could do it and perhaps I could even contribute the story to that Fictionmania web-site. It would be nice to give something back to the site that has given me such pleasure in recent years.
We entered the lounge, and the two guys were sprawled at opposite ends of the couch. The bulges in their pants and the open shirt buttons told me that there had been quite a lot of action already this evening. The boys eyes bulged open as they saw two satin clad beauties being led towards them by the 'master of ceremonies' Fiona. I think that they knew what was coming next. Fiona positioned herself between the two guys on the couch and motioned to Terri and myself to take up positions on the floor, in front of our respective targets. Fiona reached over Barry's waist and opened the poppers on both sides of the top of his track suit pants. She gently peeled down the top eighteen inches of his pants, leaving his bulging manhood pressing against his white cotton briefs. She then switched her attention to his little brother whose eyes were nearly popping out of his head at what was taking place before him. She exposed Jamie's crotch, and both Terri and myself were surprised to see that Jamie's bulge was clearly and noticeably bigger than Barry's one. 'Oh, I knew it' giggled Pauline 'I went for the wrong one'. Barry was just starting to look a little upset, when Fiona switched her attention back to him and planted wild kisses on his lips. Her hand dropped down to his crotch, and she gently ran her fingers over his bulging briefs. He had obviously forgotten completely about her little insult as he lifted his hips to try to get closer to her pleasure-giving hands. She pulled out the top of his briefs and lifted the elastic waistband down under his sac. His dick unrolled itself and popped out 'at attention', brushing off the edges of my blond tresses. Fiona walked her fingers along the length of his dick, and it twitched furiously as Barry groaned with pleasure. Fiona took my hand and brought it right up to the base of Barry's dick. 'Now, only the base for the moment, or he'll explode too early' she whispered as I wrapped my fingers around the base of his dick. 'The heat' I whispered 'as I felt his pulse rushing through his hot tool. I thought it might be a good time to explore a little, so I let my other hand explore his hairy balls, cupping them and weighing them. He groaned with each touch, and I found that I could cause a nice groan just by touching in certain places.
Fiona had turned her attention to Jamie and exposed his dick and balls in the same way. Terri wrapped his little hands with painted nails around Jamie's dick for the second time that night, though this time he had a much better view of proceedings. 'Gently, gently' chided Fiona 'you don't want him to cum too soon. Both of the guys were grunting and groaning with pleasure as we explored their hot, sweaty balls. Fiona slipped of the couch to join us two satin-clad pleasure givers on the floor. 'Now, it's time' she whispered firmly 'Just lick it like an ice-pop first, from the base all the way up to the top'. I looked at Terri and he looked at me. There was no going back now. We smiled at each other and turned our attention back to the twitching hot dicks in our hands. I got some saliva on my tongue and pushed my tongue against the base of Barry's dick. Again, he groaned in anticipation of what was to come. I licked all the way up to the top of his dick and finished with a little flourish around his sensitive glans area. His hips lifted again as he tried to get his little joystick closer to my mouth. I looked beside me to see Terri taking the bottom half of Jamie's dick into his mouth, with his little tongue darting all over it. Jamie slid his hand around Terri's neck and started stroking his neck and ears. 'Now girls' said Fiona 'Take it all in, as deep as you can go'. 'Oh yeah, please, please' laughed Barry and he rested his hand at the back of my neck and steered me towards his knob. I opened my mouth and licked my lips for lubrication. His hot meat slipped passed my lips into my mouth, and I gently ran my tongue around the top. Barry was panting widely and was clearly ready to come. I thought I could taste some salty liquid oozing from the tip, but I really couldn't concentrate to be sure. Jamie had his two hands on Terri's next and was simply just fucking his mouth. Terri was beginning to look uncomfortable, so I thought it was time to bring proceedings to an end. I slipped one hand under Barry's balls and cupped them lightly. Barry let out a fantastic grunt and forced his dick to the back of my throat. From the sound of the grunts coming from the other end of the couch, I was guessing that Jamie had released his load also. As Barry's dick slipped back down my tongue, the first gob of sperm hit the back of my tongue and started slipping down my throat. I couldn't taste anything, but could feel the thick slimy consistency of his seed. This was quickly followed by further releases of cum, each one a little less than it's predecessor, quickly filling my mouth. I slipped most of the length of his dick back out, just keeping a light grip on his knob. This gave me a bit of working space to start swallowing his load. However, I was surprised to find Fiona's lips on mine, so I let her have most of his seed. She was obviously disappointed in not getting her usual weekly load, so presumably a second-hand load was the next best thing.
My eyes caught Terri's as he licked Jamie's knob clean of his sperm. Both guys were breathing quickly as they slipped into post-ejaculation relaxation. Fiona kissed me again whispering 'Thanks, I owe you one'. She kissed Terri lightly on the forehead and said 'Well done, you did a great job' in the same tone of voice that a parent would congratulate a child on winning a medal in the school sports day! 'Why don't you two slip back up to bed while I pack these horny little things off home' she whispered. We exited the room and were heading upstairs when Pauline called us into the kitchen. 'Thanks guys' she smiled 'you just won me a 50 pound bet. Carol reckoned that you wouldn't go through with it'. I spotted that the TV in the corner was showing Fiona packing up the two guys and steering them out the door. They had been watching the whole lot via a camcorder! Sandra was looking confused and Carol was disappointed. Only Pauline was smiling 'Now, up to bed' she chipped 'and I'll send Fiona up to read you a story'.
We slipped quickly up the stairs in a mixture of exhilaration, guilt and pleasure. Fiona led us into a double bedroom, and helped Terri out of his stockings and suspenders. I did likewise with mine and struggled to keep my night-dress around my legs as I climbed into bed. Fiona helped Terri into bed, and then started stroking us both through our satin night-dresses. We lay back and looked at each other as she worked her magic on our dicks. It didn't take long for both of us to explode across the bed, Fiona, our night- dresses and each other. I think we had both drifted off into a deep sleep with some strange dreams before she had even left the room.
(the end)