Letters to Penthouse XXXIII

by Penthouse International

  This made me happy, as I was wearing a favorite outfit of mine, a black skirt with a pale blue blouse, but it confused me, too. Unless I was mistaken, he was flirting with me, or trying to.

  I smiled and thought, he is so cute, I should have some fun and flirt back. So I leaned back slightly in my chair, tilting my head, partially opened my mouth, and placed the end of my pencil on my bottom lip. I raised an eyebrow and said, as seductively as I could, “So, what would you like me to do for you, Mr. Gray?”

  The room got quiet. He started to speak but paused and cleared his throat, then said, “I, ah, just wanted you to take some notes for me. Surely an ambitious angel like yourself could find it in her sweet little heart to help me out of a bind?”

  I smiled and thanked him for the opportunity to help. Then I crossed my legs, giving him a quick view of my white silk panties. His eyes quickly opened wide. He cleared his throat and looked away shyly, regained his composure, and looked at me again. I smiled gently, acting as if nothing had happened, took the pencil from my mouth, and dug a little pad out of my purse.

  I waited for him to continue. He leaned back in his chair, and as he spoke, I took notes. His eyes periodically strayed down to my skirt. It was adorable! His wandering glances encouraged me to up the ante. As I casually brushed my hair back, my pencil “accidentally” fell. Bending over to pick it up made my breasts lunge gently forward and become more visible over the top of my blouse.

  I heard his chair squeak as he leaned forward for a better view. Knowing that I had his attention sent a feeling of arousal through me, making my nipples erect. Clasping the elusive pencil, I sat back in my chair and tossed my hair to one side, tilting my head to expose my elegantly shaped neck and ear. I scribbled his last words from memory and then finished by parting and crossing my legs again, giving his hungry eyes another helping of my panties.

  This time his chair let out a loud squeak! “Oh, my,” he mumbled, then readjusted himself, trying not to be too obvious. I couldn’t help giggling to myself.

  He was so flustered, I realized I might have gone too far. I backed off and continued just taking notes. After all, I only wanted to have a little fun, not lose my job!

  I wasn’t sure if it was me or what I was doing, but it started to feel warm. Droplets of sweat slid between my breasts, making my blouse clingy, so I said, “Mr. Gray, would you mind if we stopped for a minute? I’d like to get some water.”

  He sprang out of his chair. “First, call me Chip,” he said, “and second, I’ll get it!”

  A few minutes later he returned with cups for both of us. Carefully shutting the door behind him, he gave me a cup, then stood next to me drinking from his. He looked down at me, trying not to stare, or get caught staring, at the sweat sprinkled on my chest. I sipped some of my water, let out a sigh, and licked the moisture from my lips while I set my cup down. He watched me a little more, then continued pacing the room, speaking.

  After a while he sat on his couch and with new confidence said, “If you’d like, you might feel more comfortable here on the couch next to me.” He patted the cushion next to him and sat looking at me with those beautiful eyes. I melted. His bold invitation made him just too adorable. I hopped up and sat on the couch, a modest distance from him.

  He continued speaking, and I continued writing. His voice became gentler and more soothing. When he paused between sentences, I caught this incredibly gorgeous and successful man glancing at me like a teenage boy would look at the most popular girl in school. His facial expressions told me clearly what he was thinking, and damn, I was beyond just thinking!

  While he talked, he slid over to me. At some point I stopped writing and just listened. His voice got softer, his pauses longer. I felt him edging even closer, but I just sat and stared at my pad.

  As the reality of what was about to happen set in, I thought about how wrong it was. Then I thought about the money I needed ever so badly to pay my bills. Then I thought about my boyfriend, who was nice but who didn’t seem to care most of the time. How would he react if he knew? While thinking all of these thoughts, I noticed wetness on my palms. I got nervous, and was all set to put an end to it—when Chip leaned in and kissed me!

  I kissed him back.

  He put his strong arms around me, drawing me closer and deepening the kiss. I wanted to pull back but couldn’t move a muscle. My nervousness soon faded, abandoning me to this incredibly handsome man’s passionate kisses. I realized that all I wanted to do was give myself to him, to please him any way I could.

  A little voice in me wanted to shout at him, “Screw taking notes! Take me instead!”

  I don’t know how long we kissed, but my pad and pencil were on the floor now and his hands found their way to my chest and unbuttoned my blouse. He stared at my breasts. My hard nipples strained against my bra, but instead of taking it off, he slipped a warm hand inside, cupping a breast. He kissed my lips, cheek, and neck, working his way down.

  My heart racing, I shut my eyes, signaling—I hoped!—surrender to his carnal desires. He ran his tongue over the tops of my breasts, randomly kissing and teasing me until he reached the nipples. With his hot mouth he suckled them through the material, saturating them.

  When he made his way back up to my neck, the dampness of my bra gave me a cold sensation in the warm air, arousing my nipples to their peak. It was electrifying. I loved it so, I let out a quivering moan followed by a quick breath.

  Feeling a desire to be the instigator, I leaned down, found his lips, and kissed him hard. I pushed him back and climbed atop him, all the while giving him hot nibbles and wet kisses, working my way downward until I slid between his thighs and knelt on the floor.

  I kissed Chip’s chest and stomach through his shirt, stopping only to unbutton his shirt—almost tearing it in my haste. As I bared his slightly hairy chest and abdomen, I kissed the velvety skin obsessively, leaving no inch of his virile physique untouched by my mouth.

  I was totally caught up. I worked my way over his firm chest, pausing at the nipples and using my tongue to make them nice and hard before moving lower. My hands rubbed his thighs up and down, moving closer and closer to the bulge at his crotch. Every now and then, my fingers grazed it. He moaned and gulped in anticipation. I loved being the woman filling him with lust and pleasing him.

  He quickly opened his pants, dropping them down to his ankles, and his cock stood fully erect. I had been fantasizing about it all week, and now it was literally staring me in the face, all red and warm to the touch! My mouth watered as I thought about the possibilities.

  In a coy little voice I said, “Oh, my, is this all for me?” I looked up into his eyes, then back down to it. I moaned my approval as I began to touch and caress it. He let out a breath as he watched me work. Leaning down, I prolonged his agony by taking just the tip in my mouth, then pulled back a little and slid my tongue to the top.

  His moans made me bolder. I took more of him in my mouth, then worked that part up and down—slowly at first, then more vigorously. (I couldn’t contain myself!) Then I took as much of him in as I could and held it for a few seconds, only to retreat to just the tip. His luscious shaft throbbed and glistened from my saliva.

  Taking him in again, I worked him furiously, acting out what I desperately wanted him to do to me. Gradually, I tightened my grip, not just with my mouth, but with my hands. He growled, then hissed as he sucked in a breath. I thought he’d buck himself off the couch.

  Suddenly he pushed me back, stood up, and picked me up. I wrapped my legs around him, threw my arms around his neck, and kissed him. Kissing me passionately, he carried me to the desk. It was like we’d have died if we couldn’t have each other then and there.

  With a sweep of his arm he cleared everything off the desk and plopped me down on it. Standing in front of me, he grabbed my skirt and panties, sliding them off quickly. I ripped off my blouse and braced myself, thinking, “This is it! He’s going to take me now!”

  I was ready for him. But h
e stood seemingly forever (a few seconds, maybe?), looking down at me. Then he leaned down as if to kiss me, but changed direction and lifted me up. The next thing I knew, I was upside down—my thighs on his shoulders and his mouth buried deep in my crotch.

  “Oh, shit!” I screamed.

  His erection swayed in response to our wild movements. I took him back in my mouth and worked him with more vigor than before. He was licking and sucking me, driving me to the brink of ecstasy, exploring me with a skill that suggested years of experience. For sure, I thought, nothing can ever feel this good!

  I backed off but begged him not to stop. Then, just when I thought I couldn’t take any more, he stopped! He flipped me over and set me back on the desk. With his hard-on leading the way, he stepped up to me and stuffed it in me, bit by bit. He grabbed my hips and started pulling out and pushing back in, relentlessly, until his cock sank all the way in me. Then he continued driving in, over and over, with my ass sliding on the desk on every thrust, my fingers straining to get a grip on the cool surface.

  Moaning and panting, I kept calling out his name: “Chip! Chip! Oh, fucking Chip!” I was reeling from the pussy pounding I was taking, but just when I was set to come, he pulled out! He guided me off the desk, turned me around, and bent over me. I parted my legs to accommodate him as he plowed into my pussy from behind while grabbing my breasts. His moans almost drowned out the slapping of our bodies.

  My rapid panting turned to moans and then to near screams as I arrived at my destination, shaking and trembling. I came so hard, I felt dizzy. It was like the room was spinning.

  Chip’s cock jerked as he came inside me. “Oh, fucking yeah, Chip!” I screamed at the top of my lungs.

  We held our position and tried to catch our breath. He rested his head on my shoulder and gently kissed my bare back. I felt sweat from his forehead sliding against me. He pulled out of me slowly. I wasn’t surprised but still felt a little bereft.

  As we got dressed, his phone rang. While he answered it, I tried to quietly straighten up the mess we had made in his office. I heard him apologizing for having to work late. He finished by saying, “I’ll be home soon. I love you.” I took that as my cue to gather my things and leave.

  We didn’t say another word to each other, and I don’t know what will happen when I go back to work Monday morning. I know one thing, though: I’d have loved to see the look on the faces of the cleaning crew when they did Chip’s office and found my panties!

  —H.G., Madison, Wisconsin

  The Hot Young Football Hero Couldn’t Give Her the Heat She Was After

  Last year I returned to the Midwest for the first time in years for my family’s Fourth of July shindig. Now, I’m a petite 40-year-old with a fine figure and a high sex drive, and good sex has been sparse since my divorce—though not much worse than before it. I had visions of the hot farmboys I grew up with.

  When my cousin Sarah said she could get Richie to meet my flight, then take me to my hotel and shuttle me to the farm, I groaned. I remembered him as the biggest dork in the county. But Sarah, who was married to his cousin Glen, said he’d become really wealthy and was looking really good.

  I called Richie to make arrangements. He said he remembered me well and asked if I was as beautiful as he recalled. I thought, uh-oh! He took my flight info, and when I got to the airport, there he was.

  At least he claimed to be Richie. I knew he’d recently turned 50, but he didn’t look a day over 35 by the standards of all the big-city studs I knew back home. Truth to tell, he looked like he’d walked out of the pages of GQ, beyond handsome to red-hot.

  Since I hadn’t eaten, we stopped at a coffee shop, which gave us a chance to catch up. He was divorced, too, and after selling his company (“for a fucking fortune,” Sarah had said), he spent his time traveling and doing volunteer work. He said I looked great. I said “great” didn’t begin to describe how he looked. I confessed I remembered him as a dork. He chuckled.

  When I mentioned my marriage, he asked what the problem was. I said my ex “couldn’t satisfy my several large appetites.” The way he smiled, I think he got it.

  I asked if we could stop by the mall on the way to the hotel, as I was traveling light and had a few items to pick up. At a lingerie shop I had him watch me buy a half-cup bra I planned to wear to dinner that night. It would give me good shape and allow my large nipples to show through my blouse. I picked up a pair of crotchless panties, and we had a giggle. I said they’d go well with my leather miniskirt!

  Richie asked if I’d show him how I looked in my new underwear, and I said I would, if he was a good boy and took care of me before the party.

  I said I still had to stop at the drugstore for batteries. I also picked up some K-Y, and skin lotion. Richie, looking at my purchases, asked what type of digital camera takes C cells. I told him I had brought along a toy but didn’t want to have to carry batteries. Then, catching him staring at the K-Y, I explained I didn’t think I could get liquids through security.

  I called Sarah on my cell phone, and she reminded me that dinner was at 7:30. I told her I expected Richie to take good care of me. We headed for the hotel where the few out-of-towners were staying. Richie was already settled in a few doors down from me. I said I had to unpack and shower, and told him to come back in half an hour. I gave him the extra key in case I couldn’t get to the door.

  I’d showered and shaved my legs and put on a short robe when there was a knock, and there was Richie. He cracked a big smile when he saw me in my robe.

  I asked if he could give me a rub and put some of the skin lotion on my back and arms. We sat on the sofa, and he used his powerful hands to soothe my back and shoulders, then slid down the top of my robe to reach my lower back.

  I let the robe fall to my waist, and Richie reached around to cup my breasts in his gentle hands. He kissed my neck and said how beautiful I was. I said he looked wonderful, too. I said it was a long time since I’d had a good fucking, and I was ready for it this afternoon.

  Richie rubbed more lotion on my back, then lifted me as if I didn’t weigh anything and carried me to the king-size bed. He propped up my head with an extra pillow, then stepped back. I unbuttoned his shirt to reveal a beautifully toned body. I opened his belt and slid down his pants and underwear. I’d have sworn I was looking at a gorgeous, well-built 30-year-old.

  He sat on the bed facing me, took some of the lotion in his hands to warm it, and started to massage my legs. With him sitting between them, I stretched them out so he could cover them with skin lotion and make them feel all warm and tingly. His strong fingers sent chills up my spine. My legs parted and I lifted my knees, allowing my pussy lips to open.

  Richie positioned his face between my legs while he massaged my inner thighs, at times brushing the hair around my cunt. I responded sensually to his touch. He kissed my belly and moved down to my cunt. His tongue probed around my clit and in my pussy.

  I raised a leg over his shoulder, and he lifted my butt to take my pussy fully in his mouth. I was in a state of arousal like nothing I had ever experienced. Richie did things with his mouth I would have thought impossible. My ex ate me only if I insisted, and was no good at it anyway. Here was Richie, able to stimulate my clit and the inside walls of my vagina at the same time!

  As my breathing eased, I had Richie come around so I could give him some of the same treatment. We got into a 69 with me on top of him. I pushed my cunt in his face as hard as I could and took his cock in my mouth. He warned me that with age he was now able to come only once, and he wanted this to last all afternoon.

  He was so cute that I was torn: I wanted to swallow everything he could give me, but I also wanted this to last forever. I licked his balls and the underside of his penis until he was ready to explode, and then I relaxed. We both cooled down a bit.

  But I just had to find out if Richie had as much skill with his big cock as he had shown me with his mouth. I stayed on top of him and turned around to let him insert it in my c
unt. I was well rewarded. He used it more skillfully than I’d ever experienced! We fucked in every possible position before we both exploded.

  We lay then in each other’s arms, giggling about our reunion until we drifted off to sleep, waking around five, when it was time to get ready for the party. Richie asked me to show him my toy. So I put the new batteries in my rabbit and showed him how the shaft rotated to massage the vaginal walls while at the same time the little ears were positioned on the clit for a wild ride.

  Richie grabbed the K-Y, made the vibrator nice and shiny, and helped me ease it into my cunt with the ears over my clit. It’s a tight fit, but he was ever so gentle. First he turned on the ears, and as I got aroused, he put a pillow under my ass and turned on the shaft.

  The touch of the vibrator couldn’t compare with Richie’s tongue, but through skillful adjustment of the toy’s speeds he was soon driving me wild again. When he figured I’d had my fill, he withdrew the vibrator from my cunt with a squish and then licked my juices off while holding it up in the soft light.

  We giggled and went to shower together. The hotel had one of those double-glass-enclosed tile showers with a bench. We washed each other off, and as I bent over to get shampoo, Richie worked his rehardened cock into my asshole. He sat on the bench, and I worked my way down on his shaft. He slid a finger into my cunt, and I was off to the races.

  As he had warned, Richie was unable to come again. I assured him he had done a glorious job pleasing me. I’d never had a man who could come close. (Later he told me he’d perfected his oral skills while living in Paris for work—taught by his assistant, an older woman.)

  Richie dried off, and before he left for his room to dress, I said it was no reflection on our amazing afternoon, but I still meant to try to “bag” at least one more stud at the party and hoped he wouldn’t be upset.

  After he left, I unpacked my blouse and skirt, then watched in the mirror as I put on my new underwear. I adjusted the bra so my nipples were exposed and formed a nice crease in the silk blouse as it moved with me. I slid the short leather skirt on and zipped it up with the slit to the side, then put on my high heels. I was going to turn heads!