I was trembling with nervous anticipation as I knocked on the door to Anita’s house just after 7 that Sunday morning.
“Your late,” she admonished me as I entered, but not in an angry tone, more one of a person who was in a bit of a hurry. She was still in her pyjamas and was clearly not wearing a bra.
“We’ve no time to mess about: lot’s to do. Follow me, but,” she stopped and looked me straight in the eye.
“If you follow me now you are accepting that you must do absolutely what I tell you; there’s no going back. You’ll be accepting that I control your submissive side – and that you want me to stretch that submissiveness. I’m serious Robert, follow me and be my Roberta come what may or turn around and we’ll call it a day. Got that?”
I followed her up the stairs, excited by the sight of her trim buttocks nestling in the smooth cotton of her pyjama bottoms, the faint scent of an aroused, musty vagina just discernible. I admit I was a little unsure as to whether I could handle whatever she made me do but deep down, I knew giving her total control of my feminine side was what I wanted.
She asked me if I’d showered before I’d left home and, after confirming I had, she ushered me into the main bedroom.
“Great. That’ll save us time. You’ll love my little treat; I’ve given a lot of thought to this and spent a bit of money too. Now, off with your clothes and go and sit at the dressing table – you can keep your panties on for the time being.”
I was wearing a light-blue pair of cotton briefs with a darker blue lace trim and bow. Anita glanced at them and smirked.
“You’ll love the ones you’ll be wearing today – much nicer than those cheap ones.”
Seated at the dressing-table, she began to paint my finger-nails with a scarlet nail polish and then my toe-nails too.
“Why are you doing all this?” I asked. “Why spend money on me – what do you get out of it?”
“Be quiet Roberta, I’m going to put your make-up on now.”
She started applying moisturiser and then various other stuff, foundation, blusher, eye-make-up. She told me she’d apply my lipstick just before we left the house. My dick was now beginning to nudge its way above the waist of my panties but Anita ignored it, concentrating on getting my make-up as perfect as she could.
Only when she started to brush and trim my hair, (informing me that shorter hair would make the wig I was going to wear sit more convincingly) did she address my earlier question.
“It’s fun and besides, after mixing at University with so many men who try and chat you up thinking they’re irresistible sex-gods, it’s nice to meet a man who isn’t like that. I can see you’re in conflict; trying to keep your inner “Roberta” suppressed but struggling to. So, I’m happy to help you bring her out. You just need someone to force you to go that bit further – you know you want to. I’m going to make you go that bit further. Besides, you came to help me out getting that woman to buy all that stuff in my name.”
My painted nails had dried, my hair was now somewhat shorter and Anita was satisfied with my make-up and assured me that once the lipstick and wig were added, few would doubt I was a woman.
“Now, stand up and take a look at yourself, tell me what you think.”
She’d opened a door on a wardrobe which had a full-length mirror on the inside. My face certainly did look pretty – she’d done a good job, but I was quite embarrassed by the way my stiff tool was pushing well over the waistband of my panties.
“Take them off now Roberta and I’ll give you what I want you to wear today: the underwear is all brand-new, just for you.”
She pulled out a large bag which I instantly recognised as being from “The Lingerie Emporium” and handed it to me.
“Go on, don’t be shy, I know you’re dying to get into them. I’m pretty sure they’ll fit and they’re yours to keep too.”
I said my thanks and took my first look inside the bag of delights: I almost swooned in excitement.
“Panties on first,” I was instructed.
I sought out the little silky briefs, black with a smoky-grey lace trim around the waist and a little bow above a sheer see-through lacy front panel also in grey. My dick was still in full-boner mode as I let the new, firm elastic clasp around my waist. But for my having a stiffy, they fitted quite snugly – something Anita spotted too.
“You might have to go and have a wank before we go out, otherwise that…” she pointed to the front of my panties, “might rather give the game away.”
Next on was a matching roll-on girdle with 4 suspender straps on each leg. My little briefs were just visible below the girdle. Anita helped me on next with a pair of black fully-fashioned seamed stockings and told me to stand still as she fastened them to the suspenders. Once satisfied that my seams were straight, she got the matching bra out and fastened that too.
“We’ll fill the cups with some old tights before we leave. Now, I’m going to wash and change and then I’ll do the finishing touches. While I’m in the shower, maybe you better go and get some hand relief. That knicker-elastic clearly won’t keep your little todger at bay. Go on, wank off in here and don’t make a mess and keep your seams straight: got that?”
I did as I was told (naturally) whilst Anita washed and changed. She came back into the bedroom in just her underwear (a white bra and small pink cotton-briefs) and asked to see how my panties looked now that I’d relieved myself; she was happy with the way my penis was now nestling snugly under the elastic and behind the gauzy frontage.
I’d checked that my seams were still straight and tried not to look too lustily at her in her underwear as she walked back to the wardrobe and extracted a one-piece dress – a little black number -which she informed me was what I was to don next together with a plastic bag, which, I realised contained lots of old pairs of tights with which I was to fill the cups of my bra.
With my bra now well-padded, Anita helped me on with the dress, which she informed me was an old one of her mother’s (my dick begin to stir just a little at this point). It fitted nicely (the recent weight I’d lost through my running and exercise regime helped make it a comfortable fit rather than a bit of a squeeze) but didn’t come that far down below my stocking-tops which did concern me slightly. (Anita re-assured me that I’d be wearing another of Edna’s clothes – a coat when we went out, but this turned out to be the same length as the dress and still left a little too much of my legs exposed for my liking: or maybe not!)
Anita then applied my lipstick, a dark red, before adding a necklace of large wooden beads of a similar shade to the lipstick.
“These will help distract from your neck and Adam’s apple, which isn’t too big anyway,” She informed me.
She then carefully applied a long blonde wig, assuring me that it was well-fastened and looked like a natural woman’s head of hair. She then helped fasten my high-heeled shoes for the day – black suede ones that fastened above the ankle and through which my painted toe-nails could be seen through the fine denier of my black stockings.
“Now, you go downstairs and practice walking in those heels whilst I get dressed. I’ll give you your coat and handbag when we come to leave. How does that feel? Excited?”
I gave her a nervous smile. Sure, I was worried about going out in public but knew there was no backing out now – especially as Anita had gone to all this trouble, but yes, in spite of the butterflies in my stomach, I was excited. I could feel my knob beginning to thicken within its lacy confines: soon it would be nuzzling up against the bow and the elastic.
I nodded and smiled back. “Yes, I’m really excited thanks, thanks a lot. But I’m very nervous too.”
“That’s understandable, but don’t worry, you look fine and besides, it’s wrong to think everyone will be staring at you – well, maybe the men will ogle at your legs, they’re really rather shapely; well suited to stockings for sure.”
Downstairs, I practised my walking in the high-heels. I also thought it prudent to practice sitting down and standing back up, just to see if I could do it without exposing my stocking-tops and suspenders.
When Anita re-appeared, she was dressed in flat-black shoes, black well-cut trousers, and a white blouse. She looked her usual pretty self but had clearly dressed in an under-stated way to contrast with my more glamorous, sexy (even slutty perhaps), appearance.
She handed me a black handbag and, from her own handbag, retrieved a perfume spray from which she sprayed the both of us.
She put on a black coat and handed me her mother’s short grey lambs-wool coat which, as I’ve said, barely came down to the hem of my dress.
“Ready now. Come on let’s get going or we’ll be late. I’m driving okay.”
“Where are we going?”
“You’ll see. The only thing I’d advise you to do is speak as little as possible, your voice is still a bit too…” she knew the word she wanted to say but hesitated as though it were somehow inappropriate.
The thrill of my going out in public in such lovely lingerie and wearing Edna’s dress was arousing and I was scared that when we reached our destination, I’d be embarrassingly aroused. Fortunately my nerves plus the fact that Anita’s driving was not yet something that inspired confidence (she’d only recently passed her driving test), helped keep my excited member within the constraints of the dainty panties.
We drove for maybe 15 minutes across town before Anita parked by the pavement of a road that adjoined the town park.
“Guessed where we’re going yet?” she asked.
I shook my head: I’d no idea.
“We’re going to the 11 O’clock mass at St. Benedict’s.”
“But that’s the other side of the park,” I pointed out.
“Yes, that’s right. It’s not raining, just a bit cool and you’ll enjoy walking there letting people – well men – ogle at you won’t you, admit it?”
There was no point arguing – especially as, deep down, she was right. I did wonder if it wasn’t actually psychology she was studying at University, so well could she read my innermost thoughts.
Before we left the car, she reached into the glove compartment and took out a small, neat black hat that had a flimsy black lace veil.
“I’ll put this on you just before we go into the church, just to help you feel more at ease.”
“You’ve thought of everything,” I conceded.
I managed to get out of the car in not-too ungainly a fashion and Anita laughed as she watched me do so.
The walk through the park to the church was tremendously arousing. I loved the gentle yank of my suspenders pulling the soft material of my stocking-tops ever so slightly further up the bare skin that separated them from my panties and roll-on girdle. We both nodded and acknowledged the various greetings from other park strollers and, although I didn’t dare look anyone square in the eye, I felt sure one or two of the men took an extra long look at my seamed-stocking clad legs.
On reaching the church, Anita fastened the hat to my wig and let the veil fall down over my face. It gave me a sense of reassurance that no one close by in the congregation would get to inspect my features too closely. I was all for taking a seat in a rear pew but Anita took my arm and walked us both down towards the front where I had to concentrate on ensuring my sitting and standing throughout the service would not result in my flashing my thighs and underwear to fellow churchgoers.
Once the service was over I assumed we’d be heading back to the car but no, Anita informed me that we were going to walk a little further away from the church and where the car was parked and go and have something to eat and drink in a nearby cafeteria.
“I’m hungry and you must be too. I’ve not had any breakfast yet and I guess you haven’t either.”
That was true and so I followed her to the cafe of her choice, once again luxuriating in the feel and pull of my lingerie and the glorious sensation of the breeze chilling the tops of my thighs and little flimsy briefs.
The cafe was quite busy but there was a corner table vacant where I thought we should sit so that I could remain as inconspicuous as possible. I made a bee-line for it, just about managing not to trip in my high-heels and sat down there before Anita had a chance to sit anywhere else.
“Take your coat off Roberta,” she insisted as I was about to sit down: she’d already taken hers off. I did as I was told and became aware that, perhaps, I looked rather “busty” but Anita assured me they looked fine and totally realistic.
Anita had a cooked breakfast and tea whereas I just had a bacon sandwich and tea. It felt re-assuring in a way to notice that I’d left a lipstick smear on the teacup, like this confirmed I was, in such a little thing, passable as a woman.
After paying for our meals, Anita told me to go to the toilet before we left. It didn’t do any good my telling her that I didn’t need to go, so, nervously I made my way past the other tables to the ladies. Anita had warned me not to just stand in the cubicle to wee, but to take my panties down and sit on the seat to do the necessary. There were three cubicles in the ladies, two were vacant but the middle one was occupied. I hastily made my way to the one furthest from the entrance and duly sat down on the seat and pulled my panties down and tried to urinate. Unfortunately, my dick was too stiff to pass water, so aroused was I by my outfit and my morning’s outing. It would have been quicker to have had a wank than to pass water and I must have been in there quite a while before finally managing to succeed in emptying my bladder.
After leaving the cafe, Anita then informed me I had yet another place to go to maximise my sensation and exhilaration at being out dressed as a woman.
“I want you to go in to that chemist and buy some tampax and panty-liners. Don’t worry about which brand or size; just come out with the goods. There’s enough money in the purse in your handbag to pay for them. I’ll wait out here for you; don’t be all day.”
There were a number of other customers in the chemist as I entered. All the cashiers were young females and I felt rather faint with embarrassment as one of them approached me to ask if I needed any help. I smiled and shook my head and muttered “no thanks”, before eventually finding the shelves that stocked the goods I was after. As I stood in the queue to pay, I noticed Anita looking in through the window, clearly amused at my discomfort.
The assistant on the till didn’t look directly at me as she rang the items through and put them in a paper-bag as I anxiously sought out the money from my purse. The chap in the queue behind me probably wasn’t paying me much attention either, but at the time, I sure felt he was.
“Well you passed that test – eventually!” Anita grinned. “Come on, back to the car now. Don’t tell me though that you didn’t enjoy our little outing this morning.”
Back at the house Anita made me sit down and tell her exactly how I’d felt; what I’d really enjoyed; what was pleasurable and what might have been going a bit too far.
There was no point in being anything but truthful with her. She seemed to really enjoy hearing me tell her about how erotic the whole experience was, and for my part, talking about these events to her was arousing too (although I never mentioned that being made to wear a dress of Edna’s had erotic overtones).
I guess the only time I didn’t, deep-down, enjoy my outing was when sat in the ladies’ toilet, panties by my ankles, trying to make my semi-stiff penis pass water.
The rest of the day though didn’t go quite as I’d hoped. Surely Anita too had got some arousal from our outing? And surely she’d now want sex with me which, in my new, luxurious underwear, would be the perfect end to the day. She’d finished her essay for University yesterday, so all I could imagine us doing now was, well, having sex.
Of course, I didn’t dare ask straight out if we were going to make love, I was after all the subordinate in this duo, I was well aware of that.
But Anita told me to change down to my shoes and underwear – which I could keep on – put back on the blouse and gymslip I’d been made to wear the day before and do the ironing that awaited me in the lounge: she was going to watch the TV as I did it.
I huffed a bit but didn’t think it right to complain – not after all she’d done for me so far, besides, complaining might stop her from letting me make love to her later in the day. Better to just get the ironing done and see what followed.
There were quite a lot of blouses, trousers, dresses and of course quite a few panties. I left the smalls ’til last and, when that was all that was left and I had the first pair on the ironing board (coffee-coloured silk French Knickers)suggested to Anita that there was no point in my ironing these as, no one would ever know if they’d been ironed or had creases, but Anita was horrified.
She became, for her, quite animated, as she explained that they must be ironed: the heat from the iron would help, she explained, kill off any bacteria that might have survived the wash. Was this true? I pondered it a little while before deciding that there may be something in it and returned to the task. Unfortunately, whilst discussing this with her and thinking about it, I’d forgotten to remove the iron from the French Knickers and they were now being scalded and smoke had started to billow around them.
I looked at the scalded silk and then at Anita who now had a look of thunder about her.
“Turn that iron off and come over here this instant,” she demanded. I did as I was told.
“They are mum’s best knickers and now you’ve ruined them and I’ll have to take the blame.”
Wimpishly I said I was sorry and that I’d pay for some new ones but that was not enough to placate her.
“Over my knee, come on. Bend over my knee; you’re going to get a good spanking for that. In fact Roberta, I wouldn’t be surprised if you did that on purpose. Maybe a spanking is something you’ve wanted all along.”
It wasn’t but I never got the chance to deny it. She pulled me towards her and, in my high-heels, I was easily pulled down on to her, my face near to the carpet, my bum above her knees. I felt her lift the hem of my gymslip up and yank my little panties down below my stocking-tops and then had to just stay there and accept my punishment. It was about 12 hard slaps to each buttock, well, more towards the top of my thighs as my girdle covered most of my cheeks. They weren’t that painful and although my butt was a little sore, not sore enough to stop me getting a full-boner erection at the sensation.
The ridiculousness of the situation wasn’t lost on me. I knew I could have overpowered her and stopped the spanking if I wanted, but I had pledged on entering the house that morning to give Anita total control and this was all part of her plan to ensure I realised I’d transferred all power to her. As I lay over her knees, I guessed she’d planned to spank me at some time or other and my scorching her mum’s knickers was the perfect excuse to.
On standing up and being told to pull my panties back up, Anita pointed at my erection and ordered me to go to the bathroom and jack-off. “Otherwise, you’ll never be able to concentrate on doing your chores properly.”
I sheepishly trotted off to the bathroom and soon emptied my stiffy in a glorious ejaculation.
After then finishing the ironing, I had to vacuum the downstairs rooms and do the washing up. Anita inspected the ironing and cleaning to see that it was acceptable and then, on agreeing that it was, told me to go upstairs and await her. Maybe, at last, the reward I craved was coming, but no such luck. The next hour was spent with her helping me remove the nail varnish and then my make-up. I was told to take off my new underwear and put back on the panties I’d arrived in this morning.
“Now Roberta,” she started,”I’m going to give you a choice; two options that I know will really turn you on – I mean “really” turn you on. You can either jerk-off into a cup in front of me and then drink your own semen, every last drop or…”
I was shaking my head in horror as she said this, hoping that the second option might be more to my liking.
She continued. “Or, I can go for a wee in to a glass and you must drink it, all of it. Which is it to be?”
“You can’t be serious!” I pleaded. “I thought that perhaps, maybe we could…”
But she didn’t let me finish.
“Roberta, what did I tell you first thing? So put any notions of our having sex out of your mind – for the time being at least. You love being the submissive beta-male and I love dominating you, in as many subtle ways as possible, just accept it. This is all part of the mind-games; the giving yourself up to my absolute control. Now, make your mind up.”
It was true what she was saying and I tried hastily to consider which of the two I’d prefer: which would be the more humiliating and thus the more satisfying.
“The second; to drink your wee,” I eventually managed to admit.
“Good. That’s more like it. You’re coming to terms with who you really are. Wait there and I’ll just get a glass and we’ll get down to business.”
I waited nervously as I heard her go down the stairs, presumably to get the glass, and then come back up and go into the bathroom. Some minutes later she emerged with a pint glass about a quarter to a half full of her urine. I gulped, that was quite a lot of liquid and I knew she’d make me drink it all.
I held out my hand to take the glass from her but she pulled it away from me just as I was about to grasp it.
“I’ve just had a great idea, you’ll love this. Come with me to the bathroom and put a towel on the floor to catch any drips.”
I followed her and did as I’d been told whereupon she handed me the glass, still warm from the recently expelled liquid.
“Wait there; don’t touch a drop until I say.”
She then took off her pink panties and dipped the gusset into the glass of urine before pulling them out and handing them to me.
“Suck them as dry as you can, go on; let me see you suck my panties dry.”
She made me do this twice before allowing me to finish off the liquid by drinking it straight down. I tried swallowing it as quickly as I could and must have pulled quite a face when I finally finished. Anita looked as happy as anything when I’d done.
“That’s my girl Roberta. Wasn’t that so much more exciting than just sex? Absolute subjugation to a woman, that’s what you yearn for isn’t it.”
Dressed as Robert again, I got a taxi home from Anita’s; carrying my bag of lingerie that Anita had bought for me. I was blown away by all that had happened and if I was ever in doubt about my beta, submissive nature before, I wasn’t now. Deep down I knew I’d loved almost every minute of it.
I was never a great beer drinker but decided to ask the taxi-driver to stop just before my place and drop me off at “The Three Crowns” pub, not far from where I lived. I hadn’t been in there for over a year but reckoned I deserved a pint of bitter as reward for my humiliation that day and to help get that taste of Anita’s golden-liquid out of my mouth.
I walked up to the bar, all set to order a pint of bitter when I noticed they only had Watney’s “Red Barrel” keg bitter. I put my money back in my pocket and walked straight out. Even for me there was some piss I wouldn’t drink.