Letters to Penthouse XXXVI (8 page)

Greg immediately began moving in and out of my pussy like a jackhammer. I heard him grunting behind me and felt his cock swelling
inside my canal, and if he’d been any louder or seemed any closer to orgasm, I would have stopped and warned him to watch
himself. But he seemed to be taking care to behave, so I let him be. Besides, I was having way too much fun to stop for anything.

My clit began pulsing as Greg’s cockhead scraped along my insides. I tightened my muscles in order to heighten the sensation.
His pounding cock repeatedly shoved my body forward and caused my breasts to rub against the arm of the couch. My nipples,
already tingling, grazed the nubby fabric, so I didn’t need to use my hands this time. Instead, I rubbed my clit with one
hand while I gave Greg a firm swat on the ass with the other.

I hadn’t done it for any particular reason; I’d thought it would be fun. But apparently Greg had been trained that a spank
meant “more.” He began fucking me harder and faster, and noting this response, I reached around and landed another smack on
his ass. Now he began jamming his cock into my cunt with lightning speed.

I was panting and gasping and my pussy started twitching as I felt an orgasm approach. When I squeezed my eyes shut tight,
fireworks of red, green, and blue were bursting behind my closed lids. Hot waves flowed from my cunt throughout my body and
right back to my cunt. Holding the couch tightly, I squeezed my pussy muscles around Greg’s thrusting shaft as I came. And
though I don’t know how he did it, he managed to stave off his own imminent eruption.

My body was seized with one last shock before my climax finally ended. Slumped over the couch, I looked up at the clock and
saw that it was a quarter to twelve. I had fifteen minutes to show Greg my gratitude, and though I knew it wasn’t necessary,
I wanted to give him back at least a little of the pleasure that he’d just given me.

I told the sex slave to pull out of my cunt and then I turned and got on my knees. Taking his stiff cock into my mouth, I
began to suck him hungrily, tasting the subtle perfume of my pussy juice on his skin. Although I’d expected him to grasp my
head or shoulders for balance, he had his hands clasped behind his back and stood still, waiting to receive his reward. I
don’t know who had trained him, but they’d done a terrific job!

It didn’t take Greg long to come, which wasn’t surprising considering all the time he’d spent in pursuit of my pleasure. All
I had to do was take his cock down my throat a few more times and he was blasting come into my mouth. It gushed out over my
tongue and I swallowed it all down. Then, a split second later, the clock struck midnight. Greg pulled his cock from between
my lips, gave me a little bow, walked to the door, and disappeared down the street, as naked as he’d arrived.

—Ms. G.G., Michigan

Since the alarm went off at five o’clock this morning, I have showered and shaved, gotten dressed, thoroughly scrubbed the
bathroom, and done the kitchen floor on my hands and knees. I have also cooked, served, and cleaned up breakfast. Then I dusted
and vacuumed both upstairs and downstairs. After changing the beds, I started the washing machine with the sheets and towels,
and I have just finished ironing five blouses for Cathy. Writing this letter to you is my last assignment before lunch, but
so far it has been a fairly typical Saturday.

As I sit here typing, I am wearing nylon panties and sheer pantyhose, a snug, high-waisted girdle, a long bra, a matching
nylon camisole and half-slip, a skirt, blouse, and black pumps with three-inch heels. This is my usual attire for the weekend,
unless Cathy decides that we are going out. Then I can swap the skirt and blouse for my own pants and shirt—more “normal”
men’s clothes—but I still have to wear my feminine undergarments. I am allowed to put on regular socks over the pantyhose,
as well as wear my own shoes. Oh, Cathy reminded me to tell you that shaving on Saturday involves not just my face, but the
rest of my body, from the neck down. Even the area surrounding my cock!

For the last six months, I have worn panties, hose, and a panty girdle every day, with the additions on the weekend as noted
previously. I have also had to wear very frilly baby-doll pajamas at night. How did I get into this fix? Cathy caught me wearing
her panties and pantyhose one night when her business meeting was canceled and she came home about three hours earlier than
expected. Given no other choice, I admitted that I had often tried on her things and got really aroused by the feel of nylon
against my skin. Truth of the matter is, this is something that I had been doing for many, many years, even before we were
married!

Cathy seemed to understand and even approve of my cross-dressing tendencies, and she began to buy me women’s clothes on occasion.
She got me several things for my birthday, including the skirt, blouse, and high heels that I am wearing right now. That night,
I did a real sexy fashion show for her and was too excited to even think of the possible uses she might make of the video
she took of me strutting around in my brand-new feminine garments.

A few months later, I found out that she had really set me up. One Friday night, she announced that my wearing panties and
all other things feminine was no longer going to be fun and games—it was going to be a way of life for me. I told her that
was not what I had in mind, but then she reminded me that she still had the video and could easily copy it and send it to
my clients if I didn’t do exactly as she said. But, to be honest, even though I put up an argument, secretly I was thrilled.
I loved the thought of being “made” to wear women’s clothes all of the time!

That was also the weekend I lost all of my body hair. And now my wife only calls me by my given name when we are out with
our friends. The rest of the time I am “Heather,” not only at home, but also when we are out in public alone. Just the other
day we were out shopping in a large drugstore and Cathy had a basket full of various things. When we got to the checkout,
she took out a couple of items and then turned to the cashier and said, “Since the rest is for Heather, I will let her pay
for it.” I turned bright red as the woman, with a big smile on her face, rang up lipstick, nail polish, polish remover, and
a large bottle of Nair. But Cathy was right; it was all for me.

Now I do my nails every Friday night, but if we go out, I can remove the polish. My toenails are bright red all the time,
however. Because of my painted toes and my hairless legs, I no longer go to the beach. But that’s okay—I’m just as happy staying
inside and doing things for Cathy.

It was right after the trip to the drugstore that she began requiring that I do all the chores. While I am busy around the
house, she’ll relax in a hot bubble bath or do the Sunday crossword puzzle. Then, when I am done, it’s time to take care of
her. She’s usually in bed at that time, flushed from her bath or frustrated from a particularly grueling puzzle. Still dressed
in my feminine attire, I kneel at her feet and give them a thorough massage. I make sure to pay sufficient attention to her
toes, rubbing and then kissing each one.

Cathy’s signal that she is ready for more attention is to rub the foot that isn’t in my hands over my crotch, which is throbbing
by that point. Taking care of her like this, especially while wearing women’s clothes, really turns me on. Luckily, there
is no unsightly bulge in my skirt because of the tightness of my panties and hose. I place her feet gently on the bed and
then slowly kiss my way up her legs, leaving red lipstick traces as I go.

When I get close to Cathy’s pussy, she wraps her legs around my torso and holds me tightly for what she knows is going to
be a very thorough session of cunnilingus. I lick and suck at her pink petals as she moans and groans, and when my tongue
finds her sensitive little button she really starts to writhe. She mashes her cunt against my mouth, urging me to eat her
harder, which I do. Then she comes, sending a torrent of juices into my mouth. I swallow them all and then lick her clean.

Before I became Cathy’s sissy maid, she would usually go down on me or we’d have sex after I’d brought her to orgasm with
my mouth. But no longer. Most days I’m lucky if she’ll give my cock a second glance. And after an entire day of being encased
in silky panties and tight pantyhose, and especially after licking my wife to orgasm, my dick is aching with need. I know
better than to touch it, though, because if I come without Cathy’s permission, she punishes me by ignoring my erection even
longer or taking away my pretty panties for a couple of days.

Last weekend, however, she decided to reward me for being her obedient little sissy. After she came down from her climax,
she pulled me up onto the bed so that I was lying on my back. Then she eased down my panties and hose so that they banded
around my thighs, the elastic that bit into my flesh a constant reminder that even though she was bringing me pleasure, I
was still in my wife’s thrall.

I lay there, prone, as Cathy straddled my body so that my rigid cock was an inch from the opening of her dripping-wet cunt.
Then she eased down over my aching pole until I was buried deep inside her. It felt so good that I had to hold back from coming
right away, because I knew it wouldn’t do to enjoy my orgasm before she had reached hers.

Cathy let out a long sigh when she hit bottom, and then she raised herself up so that only my cockhead was still enveloped
by her cunt. Then she slid back down until her ass cheeks once again rested on my thighs. Then it was once again back up,
and she repeated this series of movements over and over, picking up speed as she went.

Grabbing my hand, she brought it to her pussy and moved it in a circular motion, indicating that she wanted me to rub her
clitoris. I lay my hand flat against her mound and drew small circles over her tiny bud with my thumb as she continued to
ride my cock. I could feel her clit pulsing beneath my thumb as she came again with a small cry, her pussy contracting around
my shaft. It was becoming more difficult to hold back my orgasm, and Cathy must have seen the look of frustration on my face
because between gasping breaths she barked out the word, “Now!”

My balls tensed and then exploded at her command, sending at least a week’s worth of pent-up come deep inside my wife’s cunt.
She continued to fuck me throughout my eruption, and the warm cream dripped back down my spurting cock to coat my hairless
balls. Cathy didn’t let up until I was done and her pussy had milked me completely dry. Then she got up off me and headed
into the bathroom to straighten herself up.

Returning with a wet washcloth, she tossed it to me so that I could clean myself off. I wiped off my now-limp dick and pulled
my panties and stockings back up. Then I went to the kitchen to prepare a little snack for Cathy as my weekend of being her
very own panty slave resumed.

—Mr. J.K., via email

Twenty years ago, my wife, Janet, and her friend Elizabeth were college roommates, and today they’re still close. I have always
been faithful to my wife, but I fantasize about Elizabeth. With blonde hair, blue eyes, and big tits, she would be any man’s
wet dream.

Janet knows about my playful crush on her best friend, so I wasn’t too surprised when she asked me to shoot some cheesecake
photos of her. Elizabeth’s husband is a Marine stationed in Germany, and she wanted to send them to him for his birthday.
Since I’m a photography nut and have more camera and darkroom equipment than most professional photographers, the request
wasn’t that unusual. The shoot was scheduled for the following Saturday afternoon.

I set up my camera in the master bedroom, expecting Janet to be there with us, and Elizabeth wearing nothing more daring than
a nightie. I was wrong on both counts. My wife informed us that she was going to run some errands while we took the pictures,
and she gave me a little wink. I wasn’t sure what that meant at the time, but I had a vague idea. Elizabeth had shown up in
a pair of skin-tight shorts and a T-shirt, and when she turned around, I got a good view of the way the shorts exposed her
beautiful ass. I couldn’t tear my eyes away, and I hoped she wouldn’t spot the bulge forming in the front of my slacks. Swallowing
deeply and trying to think of something other than fucking her, I aimed the camera at her, wanting to start the session before
I lost control. But before I could take a picture, Elizabeth lifted up her T-shirt.