*****
Leonard was lucky in the Residential Living Lottery and got a single room in Q Dorm in his
freshman year. The odds were long and he was the first freshman in seven years to his the
mark, but he did get a room all to himself for his first year in college.
He was lucky in another way as well. Q Dorm had four wings radiating out from the
corners of a central block which held each floor's bath/shower rooms. Len's single
happened to be at the end of one of the wings on the second floor. This gave him a very nice
view in two ways. One, out his windows, and the other, down his hall: there were three
other rooms in the wing and each of those doubles were occupied by women. The whole
dorm was co-ed but not in any pattern. Just more of Leonard's luck that both upper-class
choice and the lottery had filled his wing with women.
Len was rather glad to get a single, even if it was half the size of the normal room, because
he was rather shy. He was happy to be at college but he had been worried about living with
someone he didn't know. Now, he would have time to make friends and find someone to
room with next year.
Actually, he got to know the six girls in his wing fairly quickly, which surprised him. In
231 were Anne (a short, cute blond) and Debbie (a very tall and willowy beautiful blond).
In 232 were Georgette (an average (in most ways) brunette) and Harmony (a compact,
energetic bombshell with raven-black hair). And, in 233 were Susie (another black haired
woman with the biggest breasts Len had ever seen) and Donna (another blond and the best
looking of them all). Len's room was 234.
The girls were all very easy-going and friendly, which helped Len get to know them. They
- all seven of them in the wing - became almost like a family, and the four doors were
seldom closed (though Len's was shut more often than then others').
One day about a month after the first midterms of his college career, Len was in the
basement doing his laundry. The student handbook advised that one shouldn't leave one's
clothes unattended when doing wash. Len always followed the rules, at least until he was
sure enough to break them. So, there he was in the laundry room, alone, studying Calculus
and waiting for the wash to be done.
Mid-way through his wash cycle, Len was joined by Getty and Harm who came down and
loaded up three machines with their combined loads. When they had the machines
chugging away, Getty sat down by Len and asked, "Len, honey, could you do us a favor?
Harm and I are watching this really rad movie and we don't want to miss much more of it.
Here's the quarters - could you put our clothes in the dryers when they're done...?"
Len said, "Sure, no problem." He was happy to be a help and he would be there anyway.
Getty told him how to separate the loads for the dryers and what settings to use. Then,
after giving him a peck on the cheek, she and Harm hurried back upstairs leaving Len
blushing over his calc books.
Len loaded his own wash into a dryer then, 15 minutes later the girls' loads were ready. He
followed Getty's instructions and put the quarters in, pushing the right buttons. He found
himself lingering over one of the loads, however - the one that contained the girls' frilly
underwear. He took his time moving that particular load, going piece by piece. His mind
was intrigued by the softness and sheerness of the fabric and, of course, the fact that each of
the garments had been in intimate contact with one of the girls from room 232.
Finally, the dryers were going and Len tried to go back to his calc. But, his attention kept
returning to the front-loading dryer where the lingerie tumbled colorfully in the soft heat.
Strange thoughts had been sown and were beginning to grow.
Over the next five or six weeks, Len became the official 'wash-person' of the wing. He got
very good at making sure all manner of girls clothes got clean and dry safely. The girls
repaid the time he spent downstairs with quarters for his wash and one meal a week at a
nearby diner (the cafeteria food being just as bad as college food is supposed to be). Len
really wouldn't have minded ding the girls' wash without the payment for two reasons:
first, he was very considerate and he could usually rationalize that he would be spending all
that time in the basement anyway either at his own laundry or studying in the interruption
free and quiet (enough) room; also, he was really getting into the girls' under-things and
now he was able to touch, fondle, and (at times, very secretly) even smell the pre-washed
items, which was payment enough for him to have hand laundered each item on a rock by a
stream as far as he was concerned.
Even though his fetish, so newly discovered, was growing steadily, Len didn't think of
"borrowing" any of the apparel that so fascinated him until very close to finals. Then, the
end-of-term pressures that drove the whole dorm into slightly weird behavior finally got to
him. He had noticed, after the early excitement of his fetish had passed, that he actually
studied better when in the company of the girls' underwear. So, during reading week he
thought to borrow a pair of red and black lacy panties from Donna's load of wash.
That first pair of panties did indeed help him through finals. That success led him to
'borrow' a pair every week, each time from a different girl. He kept his booty in the bottom
of the back of his shirt drawer and made sure that none of the girls ever had reason to go
near the hiding place.
Most of the next term went by the same as before, but things changed drastically around
spring semester finals. Len had been eyeing and exquisite set of shiny-blue lingerie - the
whole works in a matched set, from bra to waist-cincher, garterbelt, stockings, and panties
- that belonged to Susie. Up to that point he had taken only panties, nothing else. But he
now felt like he needed something more and that blue set seemed perfect: they even seemed
to be in his size!
Unfortunately, something like that lingerie was more easily noticed when it went missing.
Susie had already noticed the few panties that were missing from her and Donna's laundry,
and she had a really good idea who was responsible. All she had to do now was prove it.
So, when the other girls took Len out for his weekly dinner, Susie stayed behind, citing
having to study extra hard for her final the next day. She had managed to slip a bit of gum
into the lock of Len's door so that she was able to slip into his room and thoroughly search
it. She turned up the lingerie set as well as all of the missing panties - hers and Donna's,
and what had to be the other girls' as well. Thus armed with proof, she returned the room
to its pre-search state and waited for the girls to return.
The moment they got back, she called a conference in her room. Len had work to do and so
didn't feel excluded when they shut themselves in Susie's room leaving him in his. Susie
explained what she had found and asked, "What are we going to do about it, huh girls?"
There was a lot of excited and outraged chatter, then Debbie said, "You know, I've always
fancied Len, but he looks so - so pretty. I think he'd make a gorgeous girl, and he seems to
like our underwear already. Why don't we give him the chance to go all the way?
"Georgette, is your cousin going to be able to swing us that six-bedroom house? Good.
We'll get good ole Len to move in with us for the summer - he hasn't found a place yet.
Once he's there, I think we can persuade him to dress how we want him to. Oh, I almost
forgot. Anne, can your brother get a large supply of female hormones for us? I think Len
should really look the part - he'll thank us when it's done."
And so it went. Next day, Debbie told Len that if he wanted to he could move in with them
when finals were over. Anne and Georgette would share a room, leaving Len and the other
girls a room apiece. Len agreed without the slightest hesitation, overjoyed at being able to
stay close to these beauties. The day after their last final all seven of them moved into a
very nice three storey house. Len's room was larger than his dorm room, and it was the
smallest in the house. The kitchen was huge and the living room huger. Len loved it and
even more because the girls were there too.
The household got settled down within a week, and Len found his own niche quickly. The
six women all had summer jobs but he didn't. He had no trouble paying the rent - he had a
monthly stipend from his trust fund that covered it and more - but he also had lots of free
time. So, he fell into taking care of the house. He was a passable cook, he knew (quite well)
how to do laundry, and he learned how to clean the house. His remaining time was spent in
front of the TV - or in his room dressed in 'borrowed' lingerie.
Even though he now had full access to the wardrobes of all six girls, he still normally only
tried on what the girls put in the wash (not limiting himself to underwear, though) -
cleaning the garment, trying it on, then cleaning it again before putting it away. But there
were a few times when he just couldn't wait for the item to be put in the wash. He had
returned all of the things he had 'borrowed' over the school year, and now he often went
into Donna's drawer for that first pair of red and black panties, or into Susie's for that blue
lingerie set. The girls didn't wear these things often enough and they gave him a special
thrill to wear them. In fact, so far those two were the only two 'outfits' he ever dared to
jerk off in. Masturbation was new to him and those two items really helped him get off.
They were also his downfall.
Three weeks into the summer, Len was in Susie's room putting on the blue outfit. He had
put on the bra (stuffed with panties) and the corselet, and was pulling up the tiny panties
when he heard the front door slam. He was paralyzed with fear - he had never dreamed of
getting caught and now he had no idea of what to do. Quick reactions might have kept his
secret. Instead, he just stood there, blue panties halfway up his thighs, as footsteps sounded
climbing the stairs and came down the hall. It could have been any one of the girls, of
course, but he had also left the door open so when Anne stopped in the doorway and looked
in, Len almost fainted.
In his mortal embarrassment, Len didn't notice that Anne was rather startled by the size of
his equipment. She got a grip on herself and said, "What have we here, huh? You look
almost girlish enough to be wearing that lingerie - but not quite. Want to explain yourself,
Len?"
Released by her words, Len collapsed on the bed and began to cry. It took Anne a while to
get him to tell his story and he didn't stop crying until very near the end. Anne, who was
more than a little aroused by Len's kinky, half dressed state, was comforting and
understanding rather than stern or angry. She said when he was through, "Well, I
understand about this sort of thing, but stealing is wrong. You should have asked Susie to
borrow her lingerie instead of taking it, not to mention all of the other stuff. I'll have to
bring this up tonight and see what the others think."
This caused Len to start crying again and Anne finally said she'd be as gentle with the news
as she could and be on his side that night. She left him, suggesting he get dressed. She
wend back to work and Len finished his housework in worry and fear.
After dinner, Anne kept the others at the table when everyone was done eating. She gently
explained what she had found when she had come home earlier to pick up something for
work, and what Len had explained to her about it. The silence of the others at the
revelation should have warned Len that this wasn't a total surprise to the girls but he was
too worried about the outcome to notice subtleties.
As usual, Debbie spoke for the group. She said, "Well, Len, this is very serious. But we are
friends - I don't think any of us will insist that your punishment need be severe. In fact, I
think you might even enjoy what I have in mind.
"As is most fitting, the punishment will fit the crime. A cure or kill solution. Len, from
now until school starts, you will be dressed as a female from the skin out at all times. There
will be surprise inspections conducted by any one of us - if you are caught in any sort of
man's clothing you will be spanked severely. On the other hand, you can count on our help
in keeping you properly feminine. Anne, if you would do the first honors?"
A full ensemble was quickly assembled in Len's room and Anne closed the two of them in.
She said, "Strip, kid. We'll start from scratch."
Len was very shy about removing his fruit-of-the-looms but Anne finally got them off of
him. She again surveyed him in the buff and was still impressed. She thought she could
detect a hint of feminization about him already - the hormones had been only working for
three weeks - but she had no real idea of his condition before the hormone treatment began
so she couldn't really tell.
She helped him into the blue set of lingerie he had been caught in, making sure to fondle his
hefty cock as she tucked it away between his legs to present a correctly flat aspect in his
panties. When he was fully dressed in the sexy underwear, Anne was further impressed -
even without makeup Len looked remarkably feminine.
She said, "You know, Len, you look really good dressed like that. Pretty, even. Sexy, too."
She walked over to him and pressed herself up against his front, then reached up, drew his
head down, and kissed him.
Len was overwhelmed. He felt very good just wearing the lingerie and even better when
Anne complimented him in it. Then, when she kissed him, he...he was blown away! He'd
never been kissed before. Anne was hot, beautiful, and kissing him: he didn't know what to
do.
So, Anne took charge. She continued kissing him and began to caress his body, especially
his tucked away cock. Naturally, Len's organ began to respond by trying to erect, which
caused a bit of pain due to its positioning. When he began to squirm, Anne said, "Oh, poor
boy. Let's free that rod of yours so it can be happy." She pulled his panties off, releasing
Len's cock which took advantage of its freedom by erecting fully. It stood over 9 inches out
of the nest of light brown pubic hair at his crotch. His balls, naturally hairless, hung large
beneath it, all framed by the garter-straps depending from the corselet he wore.
Anne dove onto Len's cock, inhaling it half way down her throat on the first bob. She
proceeded to give Len the first blow-job of his life, and it was an event to remember. Len
had nothing to compare it with but he was still sure that Anne knew what she was doing.
She lavished her attention all over his groin, licking and sucking cock and balls and skin as
well. Midway through, Len's knees gave out and he sat down hard on the bed. Anne
followed him and continued her work, finally being rewarded by Len's orgasm and what
seemed like a quart of cum.
She kept licking and sucking even after Len stopped cumming, cleaning every last drop of
jism she could find away. When she was done, Len was hard again, sitting there staring in
a stunned fashion at Anne. She stood, looked at the beautiful figure of Len half lying there
in lingerie and hard cock, and began to disrobe.
Len just continued staring as Anne removed her blouse and skirt, revealing a familiar set of
bra and panties in lacy green. Then, she removed first the bra, revealing her beautiful
breasts, and then her panties, showing Len his first live cunt which also happened to be
shaved. Naked, Anne advanced on Len, taking hold of his throbbing rod and caressing it.
She said, "Scoot back a bit and make yourself comfortable."
Len slid his ass back on the bed and Anne followed him, retaining her hold on his cock.
When he was centered better on the bed, Anne pushed his torso down so he was lying flat
and straddled his thighs, still holding onto his cock. Len could just barely see the inner
pinkness of her cunt as the position of her legs spread her outer lips slightly. He hoped that
Anne wasn't just teasing him with promises of further pleasure.
She said, "Len, honey, are you a virgin?" After a pause, Len nodded shyly. "Fine. I'll be
gentle. You're in for a real treat, kid, a real treat." With that, she rose up on her knees far
enough to position her cunt over his cock and then began to lower herself slowly down onto
it.
Len nearly went out of his mind as Anne sank slowly onto his cock. The warm, tight
wetness felt so incredibly wonderful that he berated himself for hot seeking out sex long
before. He lay back, closed his eyes, and just let himself feel.
Anne was going wild herself. Len's cock was huge and filled her wonderfully. At first, he
just lay there making her do all the work. But eventually the pleasure of his first fuck
forced his body to respond and he began pumping his hips in perfect rhythm. His eyes
remained closed but his hands rose and blindly found her breasts, beginning to fondle them
almost absently. Anne smiled - Len seemed to be a natural lover and he would swiftly
improve with practice and a little guidance.
Time seemed to slow down for the two lovers as their pleasure built higher and higher.
Anne's orgasms fired off one after another, but her pleasure didn't diminish at all. And, the
fire in Len's loins just kept building higher and higher, seeking release. After an eternity,
Len clasped Anne's breasts tightly and thrust his hips upward as a scream escaped his lips
with his orgasm. Anne's cries of ecstasy were more subdued but as heartfelt as her cunt
spasmed around Len's pulsing rod. That final orgasm seemed to last as long as the rest of
the fuck, but at last they relaxed into sleep in each others' arms.
Very swiftly, any slight resentment Len might have felt about his 'punishment' vanished completely. For one thing, he found that he really loved women's clothes - all of them, not just underwear. And he really did look good as a woman. He quickly learned how to apply the
proper makeup for any occasion and how to make either his own hair or a wig look
properly feminine. He really got into his female role - the girls took to calling him Jane, a
name he liked. They taught him how to act feminine - voice, walk, mannerisms, etc. Within
a month Jane nee Len was almost perfectly female.
The other major reason Len-Jane went freely - eagerly, even - along with the girls'
punishment was sex. Anne spread the word about how good Len was in bed and the other
girls were quick to confirm her estimation. Len-Jane was soon hard put to be able to sleep
alone. He was 'on call' at all hours - the girls had been forced to work out a schedule to
sleep with him. One would come home at lunch time for a quick but loving roll in the hay,
another would get to play before dinner and a third after. On weekends he had the
pleasure of orgies with from two to all six of the girls, depending on their own other
commitments.
Time soon came round to the return to school. About the same time, Jane (no longer Len)
began to notice the finally visible effects of the hormones she had been taking every day,
thinking they were vitamins. One morning while showering, he suddenly realized that he
was able to cup a small handful of flesh about each nipple. A critical examination in a
full-length mirror revealed subtle changes only detectable upon close scrutiny (with an old
photograph to hand). He noticed, finally, how much his waist had narrowed (helped both
by the hormones and the corsets he normally wore) and how much his hips had flared. His
ass was now fuller and teardrop shaped, very feminine. There were further even subtler
changes - a softness of skin, a loss of muscle tome, an alteration of bodily contours so that
even his face, arms and legs looked more feminine. His hair had grown amazingly rapidly
and was now shoulder-blade length. He was actually pleased that he looked so much like a
girl even naked - three months of enforced femininity had altered Len into Jane very
thoroughly. The only male think left in Jane was his 9+ inch cock and his enjoyment in
using it.
He confronted the girls with his discovery and his glad acceptance of it. The girls were
thrilled that he wasn't angry. They celebrated his new fully female status with a wild and
exciting orgy. And when it was over, they began planning for the future.
They made arrangements to keep the house for as long as they wanted it. Donna managed,
by seducing one of the University's programmers, to get all of Len's records altered to fit
Jane allowing her to 'return' to school. And, eventually the girls introduced their new
sister to the joys of a man in bed - and they all lived happily ever after.
FIN