Here’s a smutty new take on “employee evaluations”

Holiday 2011

In this Issue:

• Their business trip romance became a journey to pleasure
• She gives him a booty call every week, and he comes running
• A daring dress leads to a sexy one-time tryst with a total stranger
• It was a late delivery and the messenger used the back door
• He was a hound, but one woman knew how to keep him in line
• Waitressing didn’t cut it, so she found a more lucrative profession
• With her husband away she turns to other consolations
• It took him nearly fifty years to get her, but it was worth the wait
• Her neighbor thought he was too big for her. It was a challenge
• Five young guys at his daughter’s wedding were hot for his wife
• Hidden Desires
• Biker Dude
• She hadn’t wanted to even go to the party, but it worked out great
• She earned her grade the hard way—making her professor hard
• This year’s annual sex pilgrimage was truly a trip to remember
• His taste for full-figured girls was tickled right in his own back yard
• With both their spouses away, it was too good an opportunity to miss
• He offers up his body for her to play with—she takes it from there
• This sultry summer idyll features a hot stranger and a steamy climax
• Giving head came naturally to her—and was she ever hooked!
• For some of the prom-goers it was hell night, for others pure magic
• That first encounter with her boyfriend’s manhood was a hit
• They had talked about swinging with another person, but they hadn’t figured on two . . . and then four . . .
• MIDNIGHT at the TUNNEL of LOVE
• They expected it to be a threesome, but the party grew some
• Here’s a smutty new take on “employee evaluations”
• Her old flame turned up suddenly, and it was better than old times
• Her Daughter’s wingman
• A PROMISCUOUS WIFE, A RANDY FRIEND AND AN UNRELIABLE DOG
• HIS WIFE LIKES TO PLAY WAITRESS IN JUST A SEE-THROUGH NIGHTIE
• THE STRANGER WANTED TO FUCK HER, AND HER HUSBAND HELPED
• ONCE HER TUBES WERE TIED SHE COULD REALLY LET HERSELF GO

As I type this letter, I am advising my wife Rosie on how to dress. You see, this is the time of year when the company I work for does employee evaluations on all middle and upper management personnel. This evening after hours my boss will conduct my evaluation.

rosie: Yes, Charlie (my husband) is helping me get dressed. He tells me what to put on and what not to put on. The latter part seems to predominate. I am not permitted to wear panties or bra. And my pussy must be freshly shaved. For the last four years I have always participated in Charlie’s eval­uations. His boss likes me and I like him, even though he is pretty old. He is very masculine and powerful, which excites me sexually. He is also very handsome and in my opinion dresses, look and acts like a CEO should. He is classy.

You would be impressed by my helpfulness, I’m sure.

What Rosie means by my boss being “powerful” is that he takes her and uses her in any way he wants. And I thoroughly enjoy watching her thoroughly enjoy being used. At the beginning of last year’s eval­uation, for example, he told her to come stand in front of him with her feet spread wide apart. He started walking around her while running his hands over her lithe young body and asking her intimate questions.

For instance, as his hands explored the insides of her thighs, he asked, “When was the last time you were lying on your back with these beautiful legs spread wide while you watched your husband’s cock fuck in and out of your pussy?” She always wears a very short skirt so he can simply run his hand up between her legs and squeeze her soft smooth cunt. She always pulls up her skirt as fast as his hand goes up it because she wants me to see his hand and fingers manipulate her already-wet sex.

She looked me right in the eye and gasped at me, “Watch, honey, watch!”

He said, “Rosie, do you want me to give your husband a big raise?”

Of course she said, “Oh yes, please give him a big raise,” but the words came out covered with sexual wheedling and lust, sounding as though she was more interested in what his fingers were doing than promoting my raise.

rosie: Yes, yes, yes, I totally agree, but mostly what I remember is looking Charlie in the eye while I lay on my back with my legs pulled back to my shoulders and feeling his boss’s big shaft opening the walls of my dripping pussy. Charlie watched really closely as I pushed myself toward that hard cock being pushed in and out of my slit. I smiled through my lustful feelings and gasped, “Honey I hope this will help you get a good score on your evaluation.”

We got married when I was just 19 and Charlie was 33. I was/am totally enamored with him. I love to do almost anything he asks me to do. We like to please each other. It’s really fun and satisfying. He really enjoys watching me be satisfied by a nice hard cock.

One of the many ways I please him is by talking to him while I watch his boss finger my cunt. Watching those fingers slide up inside me and seeing them move over my clit makes me so full and complete that I can’t help but say, “Oh, Mr. Smith [not his real name], I like that so much! It feels so good!

I get so excited, I will say to Charlie, “Charlie, can you see his hand squeezing my pussy? Can you see his fingers going in and out of my cunt? Oh, it feels good! I want this bad! Please come close and watch. Honey, I think he’s going to make me come even before he shoves his big cock in me.”

I smile up at Mr. Smith and say, “Mr. Smith, may I lean forward and watch your big cock go in my warm snatch?” Then I say, “Charlie says I can spread myself for you anytime. All you have to do is call me and I will come satisfy you. Isn’t that right, honey? He can fuck me anytime, even if you aren’t watch­ing. I know what I’m for.”

That was last year. I pray this year is just as exciting.

I started reading Pent­house Letters long before I met Rosie, and after we were married I introduced it to her. We would read it in bed. She noticed that I got a big woody when we read stories about husbands letting other men fuck their wives. She would quiz me on the smallest detail of what I would want her to do if she was the woman in your story. I noticed that she was getting aroused just like I was.

Finally Rosie said something like, “Charlie, I want to watch you watching me as a big fat cock slips between the lips of my pussy. Will you please arrange it for me? Please.”

That “please” couldn’t be construed as anything but a heartfelt appeal. Rosie was quick to say that it was totally up to me. Then she said, “I would really like to look in your eyes while you watch another man fuck me.” Then she guided my hand to her pussy, which was wet with her warm juice.

rosie: That’s all very true. I knew what he wanted to hear from reading your stories, and I was as excited as he was. I said, “Honey, I want him to hold me and touch me all over. I want to see the expression on your face while he handles my pussy and his fingers fuck in and out of me and when I cry out in pleasure. When I start to come I will look you in the eye and say, “Watch his big cock make me come. Oh honey, watch it going in and out of my sweet honeypot! I’ll tell you when I feel his hot semen shooting up inside me. I’ll watch your expression as I tell you, ‘He’s making me come. He’s mak­ing me come.’ I want to be a wild woman for you.”

We talked about it for a long time and finally got our nerve up and applied to join a swingers’ club. At our first meeting, after we were inter­viewed by a club committee, all the members made a point to talk to us. The host and hostess acted as chaperones until our nervousness wore off. Then they introduced us to a very nice-looking couple, Darren and Roberta, who pretty much matched our ages.

Darren showed an immediate interest in my wife. Roberta said, “Darren, now don’t get too pushy!”

Rosie said with a big smile, “Oh Roberta, please don’t make him stop.”

Roberta said with just as big a smile, “Rosie, I’m so glad you feel that way, be­­cause I like to watch Darren in action, and with your permission I would like to guide his big cock into you. I want to see it spreading your cunt lips as it slips in. The best part is watching your face, because I know you’ll soon start to come, and your moans and cries will almost make me come.”

Rosie turned toward Darren, smiled and opened her arms.

rosie: God that experience was wonderful. I came so good, I thought I was go­ing to faint. I felt so drained, I thought I would never be able to stand up again. Then Roberta crawled up to Char­lie, literally crawled up to him on her knees, and with sparkling eyes and a big smile said, “I would like to welcome you to the club by sucking out and swallowing a load of your come. May I?” I may have been wiped out, but I couldn’t help but get excited again. He grabbed the back of her head and—foreplay be damned—drove his cock down her throat. As I think back, perhaps the word “drove” isn’t totally appropriate, because in my mind’s eye I see Roberta doing at least half of the “driving” downward. Charlie came almost at once, and Roberta swallowed his load, then said, “Thank you, Charlie. Welcome to our club.”

Then, as we’re putting our­selves together, who walks in and says hi but Charlie’s boss, Mr. Smith? He said, “Quite a show, Charlie. I’d be very pleased if you would introduce me to your lovely wife.” And that’s how I came to assist in my husband’s employee evaluation.

Now back to the present.

We arrive at my boss’s office at the appointed hour. He greets us with a glass of cool white wine and gets right to the point, asking me if I assisted my wife in getting dressed for his pleasure. I know he’s been antic­ipat­ing this evening, and say, “Oh yes, I made sure she followed your instructions exactly.” And I thank him for the opportunity to work for his company and for letting me watch him fuck my wife. But Rosie, you tell our readers what happened next.

rosie: Okay, honey, I like to talk about it. Mr. Smith ordered me to come before him, which I quickly did. He took me in his arms and kissed me. He has an extra­ordinarily long tongue, and it felt really good running all over the edge of my mouth.

He said, “First, my little hellcat, you’re going to take the edge off my desire by sucking my cock until I come. Would you like to go to your knees, Rosie?” Most of the time he doesn’t order me to do something, and I know why. He likes to know I want to give myself willing­ly. I would like it more if he would order me. Oh well, you can’t have everything.

I dropped down and opened my mouth wide. He looked down at me, looking cool and masculine, and took out his cock. I started sucking it. It’s way bigger than Charlie’s, so I really enjoy getting a treat like this. From our previous evaluation sessions I knew just what he likes. I concentrated on the head of his cock, turning my head back and forth. When he took over, I knew he was getting ready to come. Charlie was right there looking in my eyes, watching and smiling.

I love the feeling of a man’s cock going in and out of my mouth and down my throat even if sometimes it gets uncomfortable. He started to roar and grunt, and then I felt his powerful tool swelling and out came his jism, right down my throat. It makes me feel powerful to taste his warm come and swallow it. The expression on his face is pure satisfaction.

Then we had a glass of wine and some snacks. Mr. Smith had on a silk robe, which made him look like someone in a movie. I was sitting on the couch when, after about an hour of chatting and snacks, he got up from the bar stool and start­ed towards me with that “I want you” look. Weak as I was, I couldn’t help but feel excited. I was quivering. He was looking at me like he needed me and was coming to take me. I knew I was go­ing to be taken and I wanted that really badly. I felt so much like a woman.

As he walked towards me his hard shaft protruded from the folds of his robe. I couldn’t keep my eyes off it. I just stared at that big hard cock. By this time my pussy was so sensitive that my sex juices started running down my legs. I couldn’t help it, my legs started to spread. I wanted to open myself for him. He pushed me onto my back. My legs kept opening till he took over and pressed them to my shoulders. He said to Charlie, ‘Charlie, come and watch me fuck your wife,’ and Charlie was right there ready to watch.

My husband sat down behind me, reached over my head, hooked his hands under my knees and pulled and spread my legs wide open and tight up against my shoulders. I looked up at him and said, “He’s going to fuck me, honey, and he’s going to shove his big cock in your little hellcat’s wet, willing cunt. Watch, honey, watch while I take that big slab of meat and guide it in my little snatch.”

I watched my hand wrap around Mr. Smith’s cock and guide it in my pussy. Just imagine lying on your back propped up on your elbows, watching and feeling a big cock slide inside you with your husband right there watching closely.

I liked it a whole lot, dear reader. And I want you to know that as I think of you reading my story I’m getting excited, hoping you will be turned on by it. I promise to tell you what happens at our next evaluation.

—C.J., Los Angeles, California