Oh, those lost days of our youth, how good it is we don't have to live
them over again. But they do have a charm in memory that makes us
forget the abject terror we felt when dealing with the opposite sex.
As a sophomore in College I was one of those strong but skinny kids,
no amount of working out seemed to put any bulk on my bones. I was
desperate to raise a beard, but despite ample hair on my arms, legs
and head the face simply would not cooperate. I drooled over the
girls and threw my two cents into the bull sessions with lurid tales
of my sexual adventures (cribbed directly from the fuck films I had
seen) but in truth the few dates I had been on were rather placid
affairs where attraction and fear contended in my adolescent mind to
leave me frustrated and confused at the end of the evening.
All this changed when I had a chance to share a house with two other
students, both of them female. I was desperate to get out of the
human zoo they call college dormitories, and they were desperate
enough for the extra money that they took me in. They were theater
majors, while I was an engineering nerd, but we got along well. Jan
was an cheerleader type, curly blonde hair, big boobs, an hourglass
figure and a sparkling personality that made her the life of any
party. Beth was stocky and quiet, with an athletic body and dark
hair, small breasts and given to flowing hippie clothing offstage. I
began to get used to the sight of these women in various states of
undress, but good manors always prevailed and I refrained from making
a complete fool of myself. In a short time I was "one of the girls"
and conversations didn't stop just because I walked in the room. Of
course I had some very interesting dreams.
One long holiday weekend I found myself alone in the place, my
roommates having gone home to be with family. I went out for a run,
then tried to study, but just couldn't concentrate. I was bored
enough to even do some housework and finally took the long neglected
pile of my clothes to the laundry room. Filling the machine I
realized my sweats were rather ripe so I stripped and added them to
the load. As I stood naked in the laundry room I became aware it was
festooned with bras and nylons hanging there to dry. I had removed
these garments from my roommates many times in my dreams. Hesitantly
I reached out and felt the fabric of the nearest one, and was thrilled
by the silky feel of the cups in my fingers. I lifted it up gently
and examined it, felt the firm stretch of the elastic and imagined it
filled with the owner's supple boobs. This one had to be Beth's as
the cups were rather small. Feeling faintly foolish I held it to my
chest and settling it over my pecs. The softness of the fabric felt
good against my chest so I slipped my arms into the straps and
fastened it on.
I went in search of a mirror, not a hard object to find in a house
full of women, and laughed at the sight of my prick hanging out below
the lacy bra on my chest. Well, why not, I thought. No one was home
so I returned to the laundry room and borrowed some panties and
pantyhose and put them on, stuffing the bra with a few pairs of
panties. Damn it if it didn't feel good, if I couldn't take the
clothes off a girl the next best thing was putting them on myself. I
spent the rest of the day parading around the house in my roommate's
underwear, getting an illicit thrill each time the unaccustomed feel
of the bra or the hose reminded me what I was wearing. By late
evening I was feeling quite comfortable, lounging on the couch
watching TV, just enjoying being alone. This serenity was shattered
when I heard a key in the door and before I could react Beth came in
and stopped dead as she saw me.
"Oh my!" was her only utterance as she dropped her suitcase to the
floor with a thud. Then she began to stutter "I... I... I..." but
nothing more came out. I was utterly embarrassed and tried to run
from the room but somehow my body would not respond to my commands. I
lay there unable to move as she slowly approached me.
"Oh my!", she said again. Then she started to giggle. "You know, you
look kind of cute wearing my bra. That is my bra, isn't it?" Then
she started to giggle again. I couldn't help it, her laugh was
infectious and I started laughing with her.
"I think I'm overdressed for the occasion, aren't I? You look very
comfortable there." With that she pulled her T-shirt over her head
and dropped her shorts, standing there in only her bra and panties, a
duplicate of what I was now wearing. She kicked off her sneakers and
sat on the other end of the couch. She reached out to stroke the
nylons covering my legs, her touch sent a thrill through my body,
"Oh Kieth, I'm sorry, I couldn't stand another day with my family and
had to come back early. I had no idea I would interrupt your weekend
alone." Again her hand caressed my leg, and I knew my cock would soon
fill the red lace that covered it. I reached out and took her hand
before another touch would embarrass me further. Haltingly I tried to
explain why I was wearing her clothes, but it just elicited more
giggles. She ran her fingers along the edge of my bra, again sending
a shock wave through my body. "It's a little kinky, but really, I
don't mind at all."
I reached out and matched her gesture, running a finger along the
lower line of her bra. She closed her eyes and made a small sound of
pleasure. Gathering my courage I traced the outline of the cup
covering her breast with my finger. She snuggled closer to me until
her back was nestled between the cups of my own bra. Hesitantly I
cupped her breasts in my hands through the smooth fabric of her bra.
As I gently squeezed I could feel her nipples grow and press against
my palms. She was practically purring like a cat, and emboldened, I
took her nipples between thumb and forefinger, squeezing them gently,
feeling them harden under her bra. She began to wiggle in my lap,
pressing her sweet bottom against my growing dick. I was entranced by
the silky fabric under my fingers, and the soft, warm flesh below it
bounced and caressed my fingers. I had the crazy thought that I was
glad I was wearing pantyhose so my hardening rod would not be quite so
obvious. I slipped one strap of her bra slowly down her shoulder and
peeled the cup away to expose her left breast, then repeated the
action on the right. I placed my hands over the warm flesh of her
breasts, again playing with her nipples and kissing her neck and
shoulders. With each move of her body against mine I felt the tug of
my own bra straps, which sent a cascade of thrills through me.
I couldn't believe what was happening, after all these years of dreams
and frustration I was actually touching a girl and she was enjoying
Not only that but I was wearing her clothes while I did it! Again I
gathered my courage and slipped a finger under her panties. Her bush
was as soft as anything I had ever felt. In my inexperience I really
didn't have much idea what to do, so I gently rubbed her crotch for a
bit. She seemed to like it, because she began to squirm and say
things like "Oh yes, I like that!" I parted her bush and felt the
wetness of her cunt. I was amazed at the complexity of her slit, the
many folds of flesh hidden beneath her dark hair. As I nibbled on her
ear she guided me to the places that pleasured her most. My fingers
slid up and down her slit, then probed deeply into her, my hand
practically diving into her love tunnel and filling her. Eventually
she guided my fingers to her clit. I was amazed at her reaction, the
tiniest movement elicited a huge response from her. Each time I moved
my finger she cried out and pressed into my aching prick.
"That's it! Oh Kieth, keep rubbing, I'm going to come. You're going
to make me come! Oh God. Yes!" and she exploded in orgasm beneath my
hand. I kept rubbing, trying to keep my hand over her clit as she
writhed and moaned. I could feel the waves of pleasure roll through
her body as she came, her muscles flexing and pressing her into me.
Abruptly she sprang from my lap and pulled off her panties.
"I want you in me, now!. Please Kieth, I need to be fucked!" I
fumbled with my pantyhose and my trapped cock sprang out. She spread
her legs wide as she sat on the couch, and I knelt before her. With
her hands she spread her cunt wide open, revealing her pink lips
dripping with her juices. I had never done this before, but there was
little doubt as to what to do next. I pressed my prick against the
dripping snatch, then slowly entered her. The feeling was incredible,
my cock was surrounded with a warmth that was beyond description. I
eagerly pumped into her, but it took only a few strokes before I
exploded and filled her with my cum. Well, after all this was the
first time. Beth didn't seem disappointed at all, she simply smiled
and pulled me closer, holding my shrinking prick inside her for as
long as it would stay.
She once again traced the outline of her bra on my chest with her
fingers. "Mmmm... You can wear my clothes all you want as long as
you do things like that to me. You want to borrow a nightgown
tonight?" I held myself against her, savoring the furnace heat of her
sex pressed against mine, feeling the juices of our lovemaking drip
slowly down my balls. Well, why not. If wearing a bra and panties
was what it took to get laid the first time maybe a nightgown would
lead to the second.
We spent the night together, but I didn't sleep much, I was much too
aware of the sexy body lying next to me. My normal morning erection
was much harder than usual and attracted her attention immediately.
She began to gently stroke my prick through the nylon of the
nightgown. The fabric slid sensuously over my boner, her fingers
teasing me, playing with the head and sliding down to caress my balls.
The feelings were exquisite, I lay completely spellbound as she
stroked my dick. She circled my cock with thumb and forefinger, the
nightgown covering it and allowing her to stroke my boner
effortlessly. As her hand rose up my shaft the fabric of the
nightgown slid over my balls, stimulating them with the feather touch
of the silky material. Then I discovered that nightgowns are much
better than pajamas, because you don't have to wriggle around to take
them off, just flip up the hem and before I knew it she had impaled
herself on my boner. Her powerful legs shifted effortlessly as she
rode up and down on my cock. Her weight drove me into the mattress
and then I sprang upward as she rose on my pole, only to slide down
and again pin me to the bed. I lasted longer this time, long enough
to know the joy of a good fucking. Each stroke seemed to harden my
already rigid rod, and I felt the cum gathering in my balls, aching to
spring forth. Her cunt slid up and down over my shaft, coaxing my
nectar from me until at last I shot my load into her. It felt like I
was being sucked dry, because she mercilessly kept slamming her
delectable body down on me as I pumped spurt after spurt into her. At
last I was empty and she gave me a moment to relax.
When I was quiet she grinned at me and said "Now it's my turn." With
that she slid up my body, placing her dripping snatch over my face.
Hesitantly I stuck out my tongue and licked her. Sweet and salty and
like nothing I had experienced before. I raised my head for a better
angle and she placed a pillow under it. I began to explore her with
my tongue. If I had thought there were thousands of folds in her
snatch when I explored her with my fingers, there were millions there
to find with my tongue. It didn't take long to find my way, and again
Beth guided me with comments as to what felt best. Each time I ran my
tongue over her clit she loved it, but when I probed her slit I was
rewarded with a drop of my own cum. I caressed her ass with my hands
as I explored her dripping slit, marinating my mouth in her juices.
As my tongue drove her to peaks of pleasure I had to grasp her firmly
to keep her from pulling away from my face until at last she screamed
and came on my face. It was an amazing experience, her whole body
seemed to explode as she ground herself into me. What a wonderful way
to start the day.
Eventually we got out of bed and headed for the shower, where we had a
lot of fun soaping and rinsing each other. I was surprised when she
plugged the tub when we got out and began filling it. She casually
informed me if I was going to wear her pantyhose I really had to shave
my legs first. Whoah!, Where was this leading? I had donned her bra
on a whim, but it seemed it was going a whole lot farther than I had
planned. On the other hand, screwing Beth was even better than I had
imagined and I didn't want to get her upset with me, so I climbed back
in the tub.
I have to tell all you macho guys reading this that having your legs
shaved by a willing woman is one of life's unsung pleasures. The
slippery soap, her soft, warm hands and caresses drove me wild. All
too soon I was shorn and rinsed and we returned to her bedroom.
Suddenly she stopped and turned to me.
"Maybe I'm assuming too much here, but if you really want to wear my
clothes today it's OK with me. I think I might even have a skirt or
two somewhere for you to try on if you want to." Well, to tell you
the truth I wasn't all that sure. I mean, it had been fun, but did I
want to go where this was leading? I took her in my arms and kissed
her deeply, caressing her ass and running my hands over her naked
"I'm not so sure either, but it did feel good yesterday. If you
really don't mind I guess I would like to try it for one more day."
Without a word she held a powder blue bra before me, so I slipped my
arms into the straps and she fastened it around me. Her supple
breasts pressed close to me as she did so, and her hands wandered down
my body when she had finished the job. She handed me another bra and
held her own arms out, so I returned the favor, including the
caresses. We proceeded to put panties and pantyhose on each other,
then she went to her closet.
"If you're going to be a woman today I guess you really need something
more feminine than a T-shirt and shorts. Besides, you haven't got any
hips. Here, this should work, and the long sleeves will hide your arm
hair." It was a peasant blouse in many bright colors with voluminous
sleeves and high neckline. A long print skirt (a tight fit!), my own
sandals and I was a well dressed female hippie, the height of fashion
for those times. Well, at least until I looked in the mirror. My
illusions were shattered. Despite my long hair, padded bra and skirt
I wasn't going to fool anyone, I was a very ugly girl! Beth came up
behind me and placed her hands on my bogus breasts and began to
giggle, confirming my opinion. She quickly put on a skirt and blouse
much the same as mine and we were ready to face the day.
So I spent that Sunday morning helping Beth clean the apartment and do
the routine tasks of living wearing her clothes. It was kind of fun,
but every time I looked at Beth she seemed to be having a hard time
keeping a strait face. I liked the feel of the skirt on my legs, but
after a while the bra began to itch on my back where I couldn't reach.
Not only that the stuffing against my chest made me sweat, a most
unladylike problem. Using the bathroom was a logistical nightmare,
trying to keep my skirts out of the way and climbing stairs was
required one hand to hold up the long skirt and one to carry what I
was moving. The tight skirt was getting annoying and I kept bouncing
my bosom off door frames.
When I spilled soup on my breasts at lunch Beth fell off her chair
laughing as I tried to wipe it off. Worst of all I kept having to
shift my cock around under the tight pantyhose because it felt trapped
in there. By two o'clock I was ready to call it quits, besides, I was
afraid Jan would come home and catch me like this.
We were sitting on the couch watching TV when I got up the nerve to
tell her I wanted to change into my regular clothes. She just laughed
and told me it was OK, but there was one thing she wanted to do first.
She slid off the couch and raised my skirt, then pulled down my
pantyhose, pinning my legs together with the elastic of the waistband.
She caressed my flaccid cock and gently kissed the tip. Pulling the
skirt over her head she began to suck on my cockhead. I lay back on
the couch and savored the new experience. I could feel her warm mouth
over my prick, and her hands were tracing gentle lines over my balls
and thighs. I felt myself harden inside her mouth and watched as my
skirt began to rise and fall as her head slid over the length of my
pole. Damn that felt good, I wished I could watch but the skirt was
in the way. Now it felt like her fingers were squeezing the base of
my rod as she flicked her tongue over the tip, then her fingers were
rising as her lips were falling to meet in the middle of my engorged
member. I could hear soft slurps from beneath the fabric as she
licked and sucked. Suddenly my cock was uncovered and moments later I
felt a spot of incredible warmth on my balls. She ran her tongue over
them, starting from the back and
slowly working to the front, spreading liquid fire as she went.
Suddenly my nuts were in her mouth, surrounded with softness as she
ran her tongue in circles around them. With a pop she pulled back and
I felt my sack bounce as she once again devoured my prick. she was a
madwoman, her lips racing up and down my rigid rod and sucking like a
creature possessed. Within seconds I responded by pumping my cream
into her throat, my body shuddering as orgasm ripped through me. She
kept sucking until I was completely spent, then removed herself from
under my skirt to smile at me. I could see just a little of my white
cream dripping from the corner of her lips as she grinned.
"You liked that, huh?" I told her I did. She stood and stripped off
pantyhose and panties then sat on the couch with her skirt up and legs
spread. this may have been only the second day I had had sex, but I
know an invitation when I see one. I followed her example and pulled
her skirt over my head and began to explore her cunt. Her scent was
very powerful, confined as it was under the skirt. There was a
surreal rosy half light filtered through the fabric and I hesitantly
took one finger and began to part the hair covering her slit. Her
cunt lips were especially rosy in the light, and I traced toe lips in
ever tightening circles until I slid my finger into her dripping
slash. I moved my face closer and found her clit, holding my tongue
still over her love button for a few moments, then gradually starting
to move it just a bit as I wiggled my finger in her vagina. I began
to work up a wavelike motion, sliding tongue and finger in time over
her cunt, listening to her cries of approval and deepening breathing.
I was very involved in her when I heard the door open, followed by a
surprised "Oh, my!" much as had greeted me last night. I was frozen
in place, head under her skirt as Jan stuttered and retreated to her
bedroom in haste. I made to pull back but Beth grabbed my head and
ground it into her crotch, so I returned to what I had been doing.
Once again I tasted the savory tang of her juices, lapping it up from
her clit. It didn't take long to get back in the mood and soon I felt
her tense . She lifted off the couch as she came, grunting and
pounding her fists against the cushions. I tried to hold on, but her
movements were too much and I lost contact so I simply rubbed her cunt
with my hand as she shook and gasped. Eventually she calmed down and
I withdrew from under her skirt.
When she was again capable of speech she started to giggle. "I wonder
what this is going to do to my reputation, having been caught with
another woman eating me out on the couch?" I suddenly realized Jan
would not have known it was me under Beth's skirts and would have
thought it was another woman. Suddenly I couldn't wait to remove my
bra and skirt and dress in my own clothes. I quickly changed,
thanking Beth for a wonderful experience.
I'm afraid we really confused Jan when Beth and I started to share a
room the day she caught her being eaten out by another woman, but we
just smile at each other and haven't told her what really happened. I
haven't worn her clothes since, either, but it was a great experience
and a fun thing to do one time.