Letters to Penthouse XII (34 page)

My missed-opportunity babe was Jill. She worked with me at a company where the owner had adopted a strict “no co-worker dating” policy after losing an expensive sexual harassment lawsuit. Jill and I got along great at work and I knew I had a real shot at getting into her pants. Then a fellow sales exec was caught “fraternizing” with a secretary. As punishment he was immediately transferred across the country.

That spooked Jill enough to insist we stick to being “just friends.” Because we really were friends, I just gritted my teeth and went along with her wishes.

That didn’t keep me from fantasizing about fucking her. Jill was tall and slender with dark blonde hair and perky tits that rode high on her chest. Her thighs were so slim that they didn’t touch when she stood with her legs together. That accented her crotch whenever she wore short skirts or pants. I always felt if I could only get up the nerve to slip my hand in there and palm her pussy in that open space between her thighs, she would drop all resistance and give me the ride of my life. I never tried it. I was an idiot.

She eventually took another job in a neighboring city. She wanted to move in with a guy she had been dating who lived there. That’s when I really felt like pounding my head against a wall. I couldn’t help feeling that if I wanted to keep her as a friend—even a long-distance one—I shouldn’t try busting up her new arrangement by making a play for her.

Instead, I moved in with Janet, a girl I had been seeing. She was cute and good in bed but she wasn’t Jill. For the life of me, I just couldn’t get Jill out of my head.

I kept wondering what kind of nipples Jill had—the little dime-sized ones, the big spread-out variety or something in between. I wondered if she had a thick bush of pubic hair, if she trimmed it or if she shaved her pussy bare. I pondered if she had a neat cunt with a simple straight-line split or if her inner lips were the really vulgar type that extend from the slit like slices of pink deli meat.

We kept in touch through e-mail. I guess we both thought that was more “casual” than letters or phone calls. It’s funny the kinds of rules people make up to pretend they aren’t flirting.

Every time one of Jill’s messages popped up on my computer screen at work, I fantasized about what she would be like in bed. I kept old pictures of her in my desk drawer. Sometimes I looked at them when I read her e-mails. One of the shots was taken at a company picnic. Jill was grinning and eating a chicken drumstick, which had left the bottom half of her face looking glazed. A big dollop of barbecue sauce had dripped onto her thin white T-shirt. She had tied it in a knot under her tits to leave her belly bare.

I imagined my cock pumping between her shiny, greasy, succulent lips. I fantasized about shooting so much come onto the front of her T-shirt it would go transparent, revealing the halos of her erect nipples. Then I’d whip off her shorts, slide my saliva-slippery dick up her cunt and give her a fucking on the picnic table she’d never forget.

It could have been so sweet, I told myself, if only I had bucked the rules and made a play for her back before things got complicated. So goddamned sweet.

Jill’s e-mails were usually about trivial things like TV shows, music or the latest book she had read. That’s why her latest message surprised me. “Bob’s being a real asshole lately,” it began. “Sometimes I really wonder what I ever saw in that guy.” She didn’t go into any details. It was the first time she ever said anything bad about her live-in boyfriend. I had never met the guy but that didn’t stop me from resenting the hell out of him for getting to screw her every night.

I decided it was finally time to try rolling the dice. I typed back, “If you need a break from him, Janet is at a conference out of town this weekend. That means there’s room at my place if you want to stay over.” It was the kind of comment that could be taken as a joke… or not. Just flirting, right?

I didn’t hear back from her that day, a Friday, but that night in bed I jerked off twice thinking about her. I wanted to suck her tits, eat her pussy, even run my tongue around back and lick her asshole. I was in a decent relationship but I wanted to cheat with Jill so bad it hurt. If her own situation was breaking up now, how could I resist making a run at her? It was as if fate was giving me a second chance.

I resolved before I drifted off to sleep that I would call her the next day and tell her how I felt. One way or another, I would finally get an answer about whether she ever could see me as anything more than a “pal.”

When I opened my apartment door the next morning to get my newspaper, Jill was sitting in the hallway with her back against the opposite wall. She looked better than ever, wearing a red Polo shirt, while tennis shorts and white sneakers with fold-over ankle socks. She glanced at me and cocked an eyebrow. “Well, now I guess I can’t change my mind and run away,” she said.

She came inside, sat on the sofa and obviously wanted to talk. I tried not to look too pleased with myself. She said she had been debating whether or not she should see me. I knew where this had to be leading. My dick was getting harder the whole time she spoke. Fortunately, I was wearing baggy sweatpants and an untucked T-shirt that helped disguise my condition.

Then she came out with the line I’ll remember to my dying day: “I think maybe it was you I should have ended up with all along.”

The next thing I know, I’m lying on top of her on the sofa, kissing her beautiful face and clutching her slender body close to mine. All the sexual tension that had built up between us was finally being released. Jill’s tongue was in my mouth, her fingers were in my hair and she was pressing her crotch up against mine. I knew she could feel how hard my dick was. I made thrusting motions against the front of her shorts to emphasize my erection. She let out a little moan that sounded like a purr.

She slipped her hands inside the stretchy waistband of my sweatpants and squeezed my ass. I didn’t have on underwear. I also hadn’t shaved or showered that morning. She didn’t seem to mind.

I lifted myself off her body a little so she could slip her hands around from my ass to my crotch. She grinned like a slut when her fingers found my stiff cock. I had dreamed about seeing that look on her face—the look that said, “Fuck me.”

“Mmmm, it’s nice and big,” she said, tugging on my rod. “Really big.” While she stroked my cock with one hand, her other moved down to rub my balls. I rose up to my knees on the couch cushion and pulled off my T-shirt. I pushed my sweatpants down around my thighs, showing her my throbbing dick. She responded by sitting up and taking its swollen head between her lips.

Jill was as good at sucking cock in real life as she had been in my fantasies. She used her tongue a lot while she bobbed up and down. I tugged up her shirt while she sucked me. She wasn’t wearing a bra. Her nipples were like oversized pink gumdrops when they get hard—the halos stiffening and jutting out along with the tip. She whimpered with pleasure when I rolled those plump nips between my fingertips.

“Let me eat you,” I said. “After all this time, I’ve got to taste your pussy.”

She gave me that grin again. She lay back on the sofa and undid her shorts. I saw the smooth cotton front of her panties when she tugged down her zipper. I took hold of both the shorts and the waistband of her panties at the same time. I tugged them down her smooth legs and over her sneakers in one quick motion. With her shoes and socks still on, she let her legs splay wide open to show me the pussy of my dreams.

My mouth filled with saliva. Judging by the look of her cunt, there was no doubt in my mind that Jill had known all along she was going to let me fuck her that morning. Her pussy was as perfectly groomed as a centerfold model’s. Aside from a small tuft of golden hair at the top of her slit, her crotch was shaved completely smooth. Her cunt’s outer lips bulged out like a ripe peach. Her inner lips were glistening pink ribbons with a clit like a wet nipple at the top of her groove. She was impeccably, irresistibly well-groomed.

I pushed her legs up so the tops of her knees rested against her firm tits. That brought her little anus into view. It was a dainty, puckered notch between her creamy butt cheeks. As much as I wanted to taste her cunt, I knew that her asshole should be my starting point. Jill was my goddess and a goddess deserves to have her ass eaten.

I leaned forward and circled her butthole with the tip of my tongue. Jill gasped in surprise. Her sphincter tightened at first, then relaxed as she let herself enjoy what I was doing. Nothing impresses a woman more than knowing her lover is willing to give her the most intimate attention there is—pleasuring her asshole with his tongue. Her drawstring muscle relaxed and eased open a little, showing me its shiny inner pinkness. It was plain what Jill wanted. I wasn’t about to disappoint her.

I stiffened my tongue and pushed it inside the rim of her wonderfully hot asshole. She tasted musky and exotic. Jill groaned deep in her throat, loving the overwhelming feeling of having my warm tongue up her ass. I played my tongue in and out of her tight hole, probing her. She sensuously wiggled her bare butt against my face and used the fingertips of one hand to rub her clit while I reamed her anus.

I lapped my way from her twat to her cunt. She was lubricating so much by then that her pussy was covered with her natural honey. She kept diddling her clit while I ate her box. I ran my tongue up and down her pink folds, occasionally sliding from her sex to her anus and back.

I could tell by her breathing and the way she moved her hips that she was about to come. I decided to help her out a little. I slipped my middle finger knuckle-deep in her pussy, completely coating it with her cream. Then I pushed that same finger all the way up her asshole.

Jill cried out and bucked against my mouth as she orgasmed. Her pussy flooded my mouth with juice. In all my dirtiest daydreams I had never imagined she would turn out to be one of those rare girls who has squirting climaxes. She really was too good to be true.

“Fuck me now, quick, while I’m still coming,” she wailed. Her body was covered with sweat. I quickly positioned myself between her legs and shoved my cock home. Jill arched her back and bit down hard on her bottom lip. Her stiff nipples were so deep pink now they were almost red. She panted and shook her head. Tears welled in the corners of her eyes. It was as if she were riding out a whole series of long, rolling, continuous orgasms.

I pounded my cock in and out of her slippery, clutching cunt. When it was time for my own moment of truth, I pushed as far into her body as I could before exploding.

When I finally pulled out, a lot of come dribbled from her tight snatch onto the couch cushion. I didn’t care. The sooner my girlfriend found out about me and Jill the better.

Jill asked me to eat her some more. As I licked and sucked her reddened pussy lips, I wondered if she felt the same way I did about making this a long-term arrangement. What if she only expected this to be a one-time fling? All I knew was, she sure as hell seemed to like what I was doing.

That’s when the truth hit me. All this time, Jill may have been secretly hoping that I would wise up, drop the “just friends” bullshit and pursue her. She probably had the same “grass is always greener” regrets that I did, but she knew I was too much of a goddamned “gentleman” to press her for sex. That’s why she had taken matters into her own hands by showing up on my doorstep.

When I thought of all the time I had wasted being platonic—well, it just made me enjoy eating her shaved, wide stretched cunt all the more. In this game of pursuit and capture, I had turned out to be the prey.

I didn’t mind a bit. From now on, though, I think we’ll both be happy that I can finally say, “No more Mr. Nice Guy.”—
J.T., Evansville, Indiana

HERE’S A NEW DEFINITION OF “TIME OFF FOR GOOD BEHAVIOR”

During a recent “sweeps” week, a local TV newscast ran an investigative piece about department store Peeping Tom security guards. The reporter revealed that several surveillance cameras at one mall turned out to have been installed in inappropriate places, such as in the ceilings of women’s bathrooms and changing rooms.

I can confirm that those kinds of tales are true because I’m lucky enough to work at a store that hasn’t gotten around to pulling the plug on its own “peekaboo” cameras. So long as my fellow guards and I keep those cameras’ video feeds off the monitors whenever anyone from management drops by our office, nobody will be the wiser.

Monitor duty is the best part of my shift. I love sitting alone in the dark office and watching a college girl go into a changing room, especially when she wants to try on a swimsuit. Thinking that nobody can see her, she will unbutton her blouse, unsnap and remove her bra and let her sweet tits hang free. Then they check themselves out in the mirror. I like watching the really busty ones try to wedge their swollen boobs into a bikini top that is too small. The way their creamy jugs spill over the cups is enough to make me want to spill some cream of my own.

Even though girls know they are supposed to keep their panties on when trying on bikini bottoms, you would be surprised how many of them don’t Often they are not wearing any underwear to begin with. Take it from me— seeing a fresh-faced young beauty push down her tight jeans to reveal only bare skin underneath never gets old.

Once I was lucky enough to be on monitor duty when a guy and a girl went into the ladies’ room together. The girl checked to make sure it was empty. The two of them hurried into a stall and latched the door, not knowing that a hidden camera was directly above them and I was watching their every move. Those two must have been super horny for each other, or maybe just kinky. Either way, they obviously were in a rush to fuck.

The guy shucked his pants and sat on the toilet with his hard dick pointing straight up. The girl got on her knees to blow him a little, then hiked her skirt around her waist. She straddled his crotch, took his rigid pole in her hand and lowered herself onto it I could tell from the look on her face that she was having a hell of a time as she rode up and down on his rod. He tugged down the stretchy neckline of her leotard top and sucked her tits while he fucked her.