Letters to Penthouse XXXII (18 page)

That task completed, it was on to the last present, which was a strap-on dildo. Samantha announced that
each of the female guests was to strap it on and have a turn at my ass.

Nicole was first. She was somewhat miffed that I thought she was a man and wanted to make me pay for it. The women gave me
plenty of lubrication and fingered my ass good before starting, which was a good thing because Nicole rammed all the way in
on the first stroke. She stayed motionless for a minute to allow me to adapt to the dildo stretching my tight back hole. Surprisingly,
it didn’t hurt; it felt rather good. She slowly withdrew it and slammed it in again, then she started fucking my ass with
authority for a good ten or fifteen minutes. When she was done, my cock was standing at attention again. Samantha pointed
that out to everyone, telling them I must really like getting ass-fucked, and that maybe at the next get-together she would
let the men ride me, too. The very thought filled me with excitement, and I hoped that she would follow through on her sexy
threat.

After Nicole, each female guest fucked me, and I soon became a horny ass-slut, wanting more and more. When the last woman
finished drilling me, I was permitted to squirt on the coffee table again and lick it up. It was a long, exciting day—definitely
one I will never forget.

That evening when the party was over, Samantha did deliver her forty-five whacks and took her turn with the strap-on. She
then told me how much she liked watching me suck cock, and that she hoped I
liked it because from now on I would have to suck at least four cocks a month. That was five months ago, and I have sucked
many a handsome man’s cock with the audience of her choice. Her birthday is coming up, and she told me not to plan anything
because she has handled the party arrangements. I can’t wait!

—Mr. Patrick H., Jackson, Mississippi
     

I’ve always been considered a nice guy. I hold the door for people, don’t go over the speed limit, remember all my friends’
birthdays, and like to do favors for people. I’m the kind of guy people call when they need help moving or painting, rides
to the airport, and the like. Up until last night, my girlfriends had all been sweet, simple, wholesome girls; the kind who
play tennis and wear minimal makeup, who wear sensible shoes and go to bed at the same time every night.

My sex life was good, and I had no complaints, but all those relationships eventually ended. That’s when I met Colleen at
a local coffee shop. She was nothing like any of the girls I’d previously dated, with her powdered face, severely styled black
hair, and red lipstick. While the rest of the crowd sported a more hippie vibe, with long hair and long, flowing skirts, she
seemed like a serious businesswoman, sipping her iced coffee
while typing away furiously on her laptop. Her cell phone rang, and I watched as she checked who was calling, then snapped
it up and whispered furiously to the person on the other end.

I was intrigued by her because she was so different from most of the women I knew or saw around town. She seemed like the
kind of woman who knows what she wants and goes after it. I felt this urge to approach her, something I rarely do with strangers.
When she was done with her phone call, I walked over to introduce myself and asked if the seat across from her was taken.
She looked up at me as if I had interrupted her.

“You can sit there,” she said, neither friendly nor unfriendly. “I’m Colleen,” was her only other statement before she went
back to typing, her mouth tight as her eyes skimmed the words on her screen. She wasn’t angry, exactly, just focused, and
all of a sudden I wondered what she’d be like naked, in bed—whether she brought that same level of intensity when she had
sex. I blushed, even though she couldn’t have known what I was thinking. I took a sip of my almost-gone coffee as my cock
began to harden. “Matt, get me another coffee. An iced mocha,” Colleen said more than asked, thrusting her empty cup at me.
From anyone else, I might have found this behavior bordering on rudeness, but given my newfound infatuation with her demanding
nature, I let it go.

I had to walk slowly, willing my erection to go down as I approached the counter. The barista winked
at me. “Are you with that chick over there? She’s a knockout,” he said as he refreshed our beverages.

“She sure is. I’m not with her yet,” I replied, “but I sure hope to be soon.”

He handed back the coffees and said, “It’s on the house—as long as you promise to tell me what you two get up to after you
leave.” I assured him I would, then walked steadily back to our table, not spilling a drop.

Colleen gave me a quick smile before returning to her work, so I reluctantly pulled a book out of my bag and pretended to
read, all the while letting fantasies about her fill my mind. Then she abruptly snapped her laptop shut and said, “So, Matt,
what do you like to do for fun?” The question sounded innocent enough, except for the way she said “fun”—she might as well
have been saying “sex” from the way her voice dipped low on those three little letters.

“Well…” I paused, not sure how to respond to her question. I wanted to convey my complete attraction to her, but did not
want to come on too strong in case I was reading too much into her innocent words.

“I like sports, going for drives around town, and… well, I’m a little embarrassed,” I said, not sure why I was confessing
this to her. “I like to go online and chat with women. Sometimes it gets pretty racy.” I had done it once or twice, and had
never told anyone about it, but somehow this bewitching stranger seemed like a woman who’d understand.

She moved closer and said right in my ear, “And what exactly do you do with these computer babes?” Her hot breath tickled
my skin and made my cock as hard as it had been before.

I gulped, figuring there was nothing to lose at this point. “Sometimes they punish me for being a bad boy. They tease me and
beat me. But I’ve never done that in real life,” I said breathlessly, amazed that my deepest fantasies, ones I’d almost forgotten
about because no woman I’d been with had seemed at all interested, had just come out of my mouth.

“How would you feel about living out some of those naughty games—with me?” Colleen asked. “I bet I could show you a good time,
Matthew,” she purred.

“Yes,” was all I could manage to say, worried by this point that I might come in my pants right there in the café. I followed
her out, my face burning, catching a quick glimpse of the barista, who gave me a thumbs-up sign.

My whole body was tingling with anticipation, wondering how far things would go with Colleen. She was not only beautiful,
but she had a way of speaking and moving that made me want to follow her anywhere. I walked to her car and didn’t object when
she told me to sit in the backseat. We drove in silence, with my cock pressing against the zipper of my pants, until we reached
a small apartment building. As I stepped out of the car, she looked down, clearly noticing my erection. “Are you sure you’re
ready?” she
asked me. “Because once we start, I want you to be ready to take all that I give you,” she said, making sure of my decision.

“Yes, ma’am,” I replied, wanting to emphasize that I was hers for the taking.

We walked inside her apartment, and she proceeded to set down her things. When she’d hung up her coat and taken off her shoes,
she turned to me with a grin and motioned me toward her. I went to her, and we kissed. The meeting of our lips sent shock
waves of pleasure through my body, all the more so when she put her arms around me and trailed her long fingernails along
the back of my neck. I moaned against her mouth, and she broke our kiss, smiling slightly. “Yes, I think you’re very ready,”
she said to herself. “Follow me,” Colleen commanded, and I did, right into her bedroom.

She had a large four-poster bed, and I noticed that her open closet held all manner of kinky paraphernalia—a few whips, floggers,
handcuffs, and paddles. I wasn’t surprised and felt my backside tingle with eagerness. She saw where my gaze had landed and
pushed me onto the bed. “Strip,” she said, and I did, so quickly that on my first attempt I fumbled my zipper, but then I
got it, releasing my hard cock. She seemed to approve, but didn’t say a word as she selected several items from her arsenal.

I lay down on my stomach to wait for her. She returned, but I kept my eyes closed out of deference to
her. When she straddled my back, I felt that she’d changed, and her thighs were warm against my sides. I thought I felt something
silky rub against my back as she leaned over me to lift my hands above my head and shackle them together. The cuffs weren’t
the metal kind you see on cop shows; they were fuzzy on the inside and actually felt very nice. I moaned as I realized that
I wasn’t going anywhere for a while.

I was expecting her to start spanking or flogging me, but what I didn’t plan on was a feather tickling me under my arms. At
first, I laughed, my normal response when tickled, but the more she did it, the more my cock twitched. Colleen blew against
my skin, further taunting me as the feather trailed down my back, tracing my asscrack and then brushing against my inner thighs.
“Open up,” she said, and I did, spreading my legs to allow her to run the feather against my balls. Then she dropped it and
used her fingers to tickle my armpits, making me moan.

Then it was time for my spanking. “You have a fabulous ass, Matt. I was checking it out when you went to get our coffee, and
I had a feeling it’d be the perfect butt to lay my hands on,” Colleen said as she raised one hand and brought it down on my
right cheek with a resounding smack. The sound competed with the sting as my body processed this new sensation, and then she
did it again. She kept up a series of steady smacks while I simply lay there, occasionally rocking my hips, feeling the furry
lining of the cuffs against
my wrists as my hard cock rubbed against the sheets. Then she took a paddle and began whacking my butt with it, the sensations
growing stronger as the heat permeated my lower half.

“I think you should get ten more whacks, then it’s time to play with that yummy cock of yours,” she said. “Count for me,”
she demanded, and I did, saying each number out loud as her whacks got even stronger. Finally, we were up to ten, and the
sweet pain she’d inflicted upon my ass was tempered by the soothing strokes of her soft hands.

Colleen turned me over, and I saw that she was wearing a black and red lace outfit that made her look even more attractive.
Without saying anything, she slipped off her panties, leaving on the camisole that framed her breasts beautifully, and climbed
on top of me. I still couldn’t move my arms and, utterly at her mercy, I let her fuck me. She took charge of my cock, sliding
it between her pussy lips and then rocking forward and back, making sure her clit had the right stimulation to make her come.
I longed to taste her, but that would be her decision, so I lay there as she pinched my nipples, her squeezing getting stronger
as she got closer to orgasm. Finally, I felt that delicious tightening as her cunt wrapped itself snugly around my cock before
a stream of her sweet juices jetted down onto me.

Then she shocked me by climbing off and taking my pussy-soaked dick between her lips, bringing me to orgasm within seconds.

“Well, Matt, for a beginner, you certainly take to being under a woman’s control quite well,” Colleen said as she unbound
my wrists. “We should do this again very soon.” That was yesterday, and I can’t wait until the next time we see each other.

—Mr. Matt J., Eugene, Oregon
     

On the outside, I look like your average, everyday woman. I wear suits to work and sweats on the weekend. I’m married, live
in the suburbs, have a house and a wonderful husband. But things are not as ordinary as they appear on the surface. Once my
husband, Brad, and I are alone, the façade of simple domestic bliss falls away and I can settle into who I truly am: his devoted
slave. Right after we got married five years ago, we also had another, more special, private ceremony in which I pledged myself
to him, signing a contract saying he was in charge of my entire being. We’ve renewed it every year and I couldn’t be more
pleased.