Thomasina Ch. 03

Story Info
3. Saturday girls.
3.2k words
4.24
23k
6

Part 3 of the 3 part series

Updated 09/22/2022
Created 09/29/2010
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Thomasina: a Story of Transformation, Chapter 3 by frillypanty

3. Saturday girls

As indicated in the earlier chapters, this is a fictionalised autobiographical story. As a teen-ager, my older sister and a female cousin (not a second older sister) discovered my addiction to cross dressing and compelled ... encouraged ... assisted me (I didn't need much compulsion or encouragement) in developing my feminine persona to an extent that enabled me to comport myself, in public, as a girl, without arousing any suspicions. I've compacted their training and our early adventures into a single, long weekend -- and it all took place much longer ago than my setting.

Chapters 1 and 2 describe how Thomas's two older sisters confronted him with the knowledge that they were aware that he'd been wearing their clothes, and informed him that he was to be a girl for the rest of the Easter weekend.

I apologise to any one who's been waiting for this latest episode (of Thomasina), I've had some health problems recently which have somewhat delayed things.

I awoke to the unaccustomed feeling of sharing a bed with my two sisters; further, two naked sisters. Teresa the younger of the two, still two-and-a-half years older than me, lay in front of me, my body wrapped into hers, my arm around her with her breast clasped in my right hand. Tamsin, five years my senior, lay tucked in behind me, her breasts pressed against my back, her arm circulating my waist with her hand thrust down inside the waist-band of my panties grasping my cock -- and its consequent stalking morning erection.

Early on, during our shared night together, my chiffon nightie had been abandoned; not so my matching panties. I'd retained them throughout my tuition into the secret arts of lesbian love making, rewarded eventually by my eldest sister taking my cock in her hands, chiffon panties and all, and taking my virginity -- riding me to explosive climax. In consequence, of course, my panties were now encrusted, inside and out, with the dried residue of both my own pulsating eruption and my sister's flooding climax.

Tamsin is bi-sexual, Teresa not so. From the first, and in all my subsequent intimacy with my younger sister, our relationship has been one of a loving, sharing, caring but strictly lesbian affinity -- happy to repay my reverential lesbian homage to her femininity by fondling, caressing and even fellating my masculinity, she has never allowed me or any other man to possess her; in that respect she remains virgin. Tamsin on the other hand is happy to accede to, and is usually the instigator of, either homosexual or heterosexual intimacy ... or both at the same time. She delights most in the three of us sharing our bodies in every conceivable manner, subject to Teresa's refusal to allow the final act of heterosexual copulation.

Tamsin's first act on awaking, was to give my cock a tweak and then to withdraw her hand from inside my panties.

'Hmm,' she commented, twanging the elasticised waist band, 'these could certainly do with washing!'

So saying, she yanked the offending pantries down over my thighs, down over my legs and off my ankles. By now Teresa was also awake and watching the operation with interest and Tamsin sent us all scampering bollock naked ... well, me bollock naked at any rate, my sisters were displaying some rather more feminine attributes ... around the house picking up any discarded clothes and other items, for laundering. After the previous two days experience feminine underwear seemed to account for a pretty large proportion of the eventual load.

The washing machine loaded and started we scampered back upstairs for our now accustomed mutual shower where, in the rather restricted cubicle, our naked bodies brushed up against one-an-other and I found myself increasingly stimulated and aroused by the constant contact of my sisters wet streaming breasts, nipples, thighs and buttocks. It's a strange thing but women, when they shower, are inclined to turn inwards towards the shower head as though to protect their vulnerability. Men, on the other hand turn outward -- displaying their potency? In my new role as a member of the opposite gender, I found I was copying my sisters and turning inwards.

Anyway, shower completed, suitably dried and dusted with feminine smelling talc and wrapped in light, virtually transparent, lace be-decked negligees, we repaired to the kitchen for breakfast: after which Teresa and I were sent out into the back garden, still in our dishabille, to 'peg out' the now completed laundry. Again, the preponderance of feminine underwear was readily apparent.

*********

Now I was led upstairs again to dress. On my sister's bed were laid out three tennis outfits: two sets with short pleated skirts and white tee-shirts; one short skirted, sleeveless, collarless tennis dress; three pairs of frilly, nylon panties with matching bras'; three pairs of ankle socks and white tennis shoes. The outfits were basically white, the separate skirts and tee-shirts had pale, apple green inserts the dress had vivid orange side panels and inner darts in the pleated skirt. The underwear and ankle socks matched the colour of the inserts -- two sets in apple green, one in vivid orange. My sisters picked up a pair of green panties each; the inference was obvious, the dress was for me. Once we'd assumed our underwear, and my breast forms had been properly adjusted in my bra', the girls picked up a tee-shirt each and pilled them over their heads and quickly added the two skirts. They then helped me into the dress. I was immediately conscious of the shortness of the skirt; there was no way I was going to move around a tennis court without showing off my knickers ... and quite possibly something else beside, if my cock didn't behave itself!

So it proved. Due to our Mother work as a bursar at the University we had passes to all the sports facilities where, in the Easter vacation, we had no difficulty securing a tennis court. The girls, singly or both together, as we swapped around 'two-on-one', soon had me hopping around the court like a mad thing -- my skirt flapping up around my thighs, my only to discernable orange knickers on display. Their own skirts were equally disrupted by the movement and their knickers, too, were on show. But, in their case fleeting glimpses of silky apple green encased flanks and buttocks wasn't significant. In my case the drag of the light lacy nylon over my already sensitised cock was causing a real problem. Added to that, I was suddenly aware of a further source of arousal. The front panel of my panties was in slightly abrasive lace; this was now creating a friction, a catching and tugging sensation, across the emergent stubble on my shaven pubis where my pubic hair was beginning to re-establish; and creating its own feelings of arousal! I was acutely aware that a significant bulge was forming in the front of my briefs!

[In reality it was several days before I became aware of this last sensation but, as I've indicated above, this is a kaleidoscoped version of my emergence as a female ... fp]

Try as I might I was fast losing control of the situation. In the end, much to the delight of my sisters, after I'd seen a couple of passing girls looking at me with expressions of puzzled astonishment, I had to flee to the toilet ... remembering at the last moment to make it the Ladies toilet ... and resort to the time honoured method of relieving such emergencies. The remainder of the game passed without the added difficulty of me having to control a raging arousal ... even if I did lose every set.

That afternoon, after another shared shower and another set of clothes, my sisters announced that we were headed out for a shopping trip.

'You can't keep wearing our clothes,' Teresa told me, 'especially our underwear. It's time to buy you some pretty lingerie of your own. And some more practical everyday stuff.'

Like most males I'm not a great fan of shopping but, suddenly, I became aware of a vague sense of satisfaction at the prospect of owning some feminine underwear of my own ... underwear that no-one else had worn before me. The prospect of a trip to affect that deficiency was rather exciting. What I didn't know was that my sisters had another purpose in mind, as well ...

*********

Tamsin parked her car at the accountancy company she worked for a little way off the city centre, as she'd done many times before oh a Saturday afternoon. Obviously, from the few cars scattered around car park, she wasn't the only staff member to do so.

The trip started off much as I expected. We went first to the more conventional chain stores; Marks and Spencer, Debenham's and British Home Stores, where the girls picked out a few sets of fairly practical cotton or satin underwear. Nothing too fancy but delicate and feminine enough to feel totally different from my usual masculine fabrics and cut -- panties, bra's, suspender-belts, half and full slips -- most in pretty printed designs or motifs, edged with lace or broderie anglaise, and set with little bows. In the first shop, Marks and Spencer, having made their first selection, they ushered me into the ladies fitting rooms to try on and confirm their assessment of suitable sizes. I'm pretty slender, but slenderness in males and females is after all rather different. It transpired that for panties, suspender-belts and slips, I was a pretty standard size twelve; my bra size, to contain my breast forms and give me a trim bust-line, was 36B.

[UK size, which with a reasonable diet and regular exercise has only increased to size sixteen over the years ... fp]

Used as I had become in a very short while, to being naked and dressing in femininity before my sisters, to do so in a cubicle in a ladies fitting room in a city centre store was a whole new experience again! To the delight of both my sisters, inevitably, my arousal soon became apparent and extreme! They had directed me to retain my knickers -- a pair of fairly plain and relatively skimpy satin briefs -- which just about contained my cock in its dormant condition; at full erection, not a chance! And there was no where to go to 'offload' so to speak! For the second time within forty-eight hours my eldest sister, a huge grin on her face and with evident enjoyment, settled down on her heels before me to silently suck me off to completion, displaying her own nylon covered crotch to me as she did so. Only then could I try on the panties they'd selected; over my briefs.

The first phase of the operation over we retired, briefly, to Tamsin's car to secure the bounty in the boot [trunk] before we returned to the city centre for a cup of coffee and the next assault.

During this phase we visited some of the more fashionable outlets and boutiques and, the appropriate sizes now confirmed, my sisters picked a selection of much more feminine and fragile nature -- sets of lingerie in lacy nylon and silk -- and, having taken note of my inside leg measurement, topping things off with a few pairs of stockings and, the now not so dreaded, tights.

Finally, or so I thought at the time, we visited a few shoe shops and secured me a few pairs of shoes of my own.

Again, we retired to Tamsin's car and secured goods. I assumed that would be it for the moment, but the girls again led me back into the centre, this time to a small studio just off the main street in a cobbled alley. 'Body Piercing' the sign in the front window proclaimed; Tamsin, who seemed to know the female proprietor, struck up a conversation -- one that rather took the wind out my sails.

'My brother here has decided to explore his feminine side to the extent of dressing as a girl, at least part time, and consequently wants his ears pierced; and, as a "special female", in order to control the somewhat unusual appendage he keeps in his panties he need to undergo a certain amount of intimate body piercing.'

Talk about letting the car out of the bag! Heretofore, the atmosphere between my sisters and I had been one of 'all girls together' so to speak, and they had done their best to shield me from identification -- as a male in female attire! Now, here Tamsin was telling the shop girl all about me, in a few short sentences!

I didn't realise till the nature of the intimate body piercing became apparent, that there was no way she could keep it quiet. And, maybe, there was just an element of revenge there in this final exercise for my having 'appropriated' the more intimate items of their wardrobes over the past five years or so, without any 'by your leave'.

What ever I thought, it was now obvious I'd have to endure whatever was about to happen. And endure it I had to!

Having my ear lobes pierced, washed in surgical spirit and having gold sleeper rings fitted, was bad enough; what was to follow was altogether a different experience. After the operation on my ears, I was led through the shop into what looked like a minor gynaecological unit and instructed to 'take off your skirt and panties' and climb up onto the chair. With three obviously impatient females awaiting my compliance I didn't have a lot of choice. The chair was rather the shape of a more upright dentists chair with separated stirrups for your feet that left you totally exposed below the waist. Without preamble, the young woman grasped the underside of my foreskin with the gloved thumb and forefinger of her right hand and, with her left hand, using a larger version of the instrument she'd used on my ears she pieced the sensitive flesh and inserted a slightly larger gold sleeper ring. The pain and shock were massive -- or seemed so for a moment or two. Worse was to come. Now she grasped the loose flesh at the front of my scrotum and carried out the same exercise. I nearly passed out! When I'd recovered somewhat, my sister spoke in conversational voice.

'Some of the girls at Uni had this done to their boyfriends, you know, to keep them from screwing around. What they did was to insert a little padlock into the two rings, and keep the key. You can't screw to well with the tip of your cock fastened to the front of your balls. You'll find it a bit difficult to get an erection to. It'll solve the problem of getting unsightly and give-a-way bulges in the front of your panties and skirts.'

Having the piercings washed with surgical spirit was nearly as painful as the operation.

My sisters didn't padlock my cock to balls; instead they chose a kind of double ended necklace fastener that assuredly kept my masculinity securely doubled up. That in place, I was at last allowed to put my panties and skirt back on.

Tucked up doubled into my panties, once the initial pain and shock had subsided, I found the sensation of the fragile satin rubbing across my newly sensitised genitalia was not an unpleasing sensation. And the restraint now placed on my cock against stiffening was, in itself. a source of arousal. But, it was a subdued and still sore Thomasina that, having been adjured by the practitioner to 'make sure you clean the piercings properly', followed her sisters back to the car park.

[Again, in reality it was some months before any such restraint was fitted ... fp]

*********

On our return home the first thing I was ordered to do, by Tamsin, was to go out and gather in all the washing we'd left on the line. Then, under Teresa's instruction, whilst Tamsin prepared our evening meal I was required to iron as many of the laundered garments as required it. Used as I was to ironing my own clothes -- or some of them at least; it was a whole new experience ironing the delicate fabrics that comprised the lacy, silky underwear that made up the majority of the items.

I'd kind of wondered whether the girls had another outing planned for that Saturday evening, but my sisters had determined that it should be spent in a further bout of training: teaching me to fasten my bra' behind my back in approved feminine fashion, instead of fastening it in front of me a wriggling it round to the back; and, learning the basics of applying my own make-up. And those make-up lessons were, of course, only a beginning. It was some time before I was really confident in my own judgement and ability, to apply just the right amount of facial make-up to give me a truly feminine appearance without overdoing it. And the lessons also included the correct choice and usage of talc, body sprays and perfumes.

I was exhausted by the end of the evening.

After a final shared shower we retired to bed -- together. Again, I was clad in a short nightie and matching frilly panties whilst my sisters were naked. At least, they were until Teresa suddenly leapt out of the bed and fled into the bathroom. After the sound of a flush she returned to rummage in her dressing table draws, taking out a pair of plain satin briefs and a box of 'Tampax'.

'I've come on,' she commented, laconically.

And for the first time in my life I witnessed a girl opening and fitting a tampon, from the dispenser, into her vagina.

'Hmm,' my elder sister commented, 'that probably means I'll start any moment!'

And she too assumed a pair of satin panties.

'How do you know,' I asked, in a genuine spirit of inquiry.

'Apart from the pains I'm getting,' Tamsin told me, 'I'm due any time; and, when menstruating females live in close proximity they usually find their cycle's more-or-less coincide. I wouldn't be to surprised if the rest of Dad's weekend suddenly to a turn for the worse.'

This last thought seemed to amuse the girls immediately although it took a moment or two for the 'penny to drop' with me.

So it proved -- with Tamsin at least. Within an hour I was to witness her to using the dispenser to deposit a tampon in the appropriate chamber of her anatomy.

Of course their condition somewhat restricted our mutual activity although I at least was relieved to unclip my restraint and allow my cock to rapidly stiffen and swell to disrupt the front of my panties. Good naturedly my sisters, although access to their bodies was reduced, were quite happy to masturbate me, through the delicately frilled chiffon of my panties, and grant me the release that my cock had been craving, once it had recovered from the assault by the piercing practitioner.

One thing I'd found, with my cock doubled up between my legs, when sat down to I peed the stream was forced backwards -- like a girl.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
DianeRedfernDianeRedfernalmost 7 years ago
Wonderful Saga

Thomasina is so lucky to have such loving sisters as guides to her inner and outer selves. Very hot and wet. How about a Chapter 04?

xoxo,

Di

AnonymousAnonymousabout 11 years ago
Ditto last 2 anons

Glad there was no gay sex.

AnonymousAnonymousabout 11 years ago
A delightful departure

from the gay stories disguised with a bit of lingerie we so often find in TX-CD section.

I've been cross-dressing since I was young but I only summoned up courage to venture out many years later in my mid-teens. I remembered that on my first trip out as a girl, I went a BHS and tried on a skirt. However, for unknown reasons I didn't get it at the end. From your stories, I gathered that we physically very similar. I only wish that I had my sisters to help me out, although body piercing is really not my cup of tea.

A very nice series that brings back nervy yet titillating memories. Thank You!

AnonymousAnonymousabout 11 years ago
gaff to be used?

Instead of piercings to his cock and back near his balls there was other ways to hide or control his erection. The use of a good gaff or a false pussy works for many instead of the metal hardware. Healthier and safer with a gaff. But at least you did not have a padlock put on them. The sisters are a little too dominant and should let Tom know what is planned for him in advance. It sounds like he thinks it is only for the weekend, but they seem to want him to do this full time or the very least part time after their parents get back from their trip. I hope that they do not set him up with dating men, since he seems attracted to women only.

Share this Story

READ MORE OF THIS SERIES

Thomasina Series Info

Similar Stories

Alex to Alexis Ch. 01 Alex is feminized by his mother and sisters.in Transgender & Crossdressers
Feminized by My Girlfriend The start of how she changed my life.in Transgender & Crossdressers
Her New Girlfriend Ch. 01 Discovery: he's caught playing dress up.in Transgender & Crossdressers
From a Husband to a Dutiful Sissy Ch. 01 How I went from a loving husband and to a sissy for my wife.in Transgender & Crossdressers
Mum & Sister Dress Him Up Dumped sissy returns to mum and sister who enslave him.in Transgender & Crossdressers
More Stories