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Recently, I moved out of Seattle to a much smaller town in the Midwest. I had just gotten out of a relationship and was looking forward to being single for a while, until I realized that almost every girl in town was coupled up. There weren’t as many places to meet people as there were in Seattle, and I was starting to question the wisdom of moving so far from home when I met a woman who changed my life. Lily was a good ten years older than me, and not someone I would have usually checked out. It’s not that she’s not hot, but she’s not drop-dead model gorgeous and doesn’t go out of her way to dress flamboyantly. Her sexiness is expressed in the breathy way she talks and by her talent in the sack.
We met at a movie theater, both of us opting for the arty, indie flick versus the blockbuster seemingly everyone else had chosen. When I walked in and noticed how many empty seats there were, I was dismayed. I know some moviegoers love to have the theater to themselves, but I feed off other people’s reactions. That’s part of the thrill, so when I spotted this woman with short brown hair eating popcorn all by herself, I asked if I could sit down next to her. “I’ll share,” I said, shaking my box of Rai-sinets at her.
“Sure, sit down. I’m Lily,” she said, giving me a friendly but not flirtatious smile. We sat and enjoyed the film, munching on our combined salty and sweet treats. I actually didn’t think of her as a potential romantic match at first because I wasn’t getting that vibe from her—she later told me she’s really into movies and doesn’t like to be distracted. But we exchanged numbers afterward and began hanging out, and I found Lily to be very easy to talk to. So easy that we wound up closing out a local bar one night; I had thought two hours had passed when apparently it had been five.
She took me by surprise by making the first move of sorts by inviting me to her place, planting the idea that she might be interested in more than talking. “It’s not too far, and I have a bottle of wine we could share.” I was still fairly clueless, but as we walked, I started to notice how her ass twitched beneath her clingy skirt and wondered whether she was wearing any panties. Usually, I know right away if I want to fuck a girl, but this attraction was more of a slow build. Yet once it started, I couldn’t get rid of it, and my cock was soon rock-hard.
“Lily,” I said while in the parking lot. She turned toward me, and all of a sudden, she looked prettier than she ever had. Most of her makeup had come off during the course of the night, with just a hint of shadow remaining on her eyes. Her lips were a natural, luscious pink, and I desperately wanted to feel them pressed to mine. “I need to kiss you,” I said truthfully, and pulled her close. I mashed my lips against hers, and she immediately moved closer to me and parted her lips so I could slip my tongue inside her mouth.
I was surprised when her hands moved down to squeeze my ass. She had seemed almost asexual the other times we’d hung out, not mentioning a boyfriend or even any exes, and dressing cutely but not in anything extremely sexy. Maybe she was just waiting for the right man to unleash that side of her, because she was practically ready to undo my pants right there in the street!
“God, Lily, I had no idea what a tiger you are!” In truth, she was a real cougar, a hot older woman, and I was more than happy to let her have her way with me.
We raced to her place and didn’t even bother with the wine. She led me to her bedroom, then pushed me down, pinning my wrists to the sheets. Lily actually growled as I squirmed beneath her, my cock almost unbearably hard. “You’re all mine,” she said, grinning.
“I am. Do whatever you want to me,” I said, feeling completely comfortable letting her take control. Her nails were short but painted a dark red, and she dug them into my skin. They didn’t hurt, but sent shivers throughout my body. Lily was surprisingly strong, and even though I outweighed her, I liked the idea of choosing to submit to her, and from the way she was acting, I had the impression she’d played the domme role before.
She quickly took off all her clothes, then climbed on top of me and shoved both her breasts in my face. They were larger than I’d expected them to be, once again showing that looks can be deceiving. “Suck my tits,” she demanded. I hadn’t expected Lily to use such language, but it turned me on. I opened my mouth, letting her breasts enter and trying to keep both nipples in my mouth at once. It was a challenge, but I rose to it, literally, my cock stiffening as she straddled my chest. I savored the heat and wetness of her pussy grinding against me as my tongue lashed at her nipples. “Harder,” she hissed, and I clamped my lips down around them. I could only breathe through my nose, but I liked it, and I kept lapping at her nipples until she cried out, her screams ringing in my ears.
Had I made Lily come just from licking and biting her nipples? And if they were that sensitive, how would her pussy react to my oral caresses? I was about to find out, because Lily eased her nipples away, dragging them against my chest as she moved down my body. She took hold of my cock, wrapping her soft fingers around it. By then, our age difference no longer mattered; she clearly knew things about sex that I didn’t, and I was eager to learn everything.
She rubbed my cockhead against her sex, teasing me by letting only the very tip enter her, then sliding it out. Just when I was sure we were going to start fucking, she moved away and climbed over me so she was straddling my face. Her cunt was wet and juicy, and I eagerly welcomed her, grabbing hold of her hips and pulling her tight. At that moment, pleasing Lily was my only concern, and I trusted that she’d take care of me later. I’d gone down on plenty of women, and I’m pretty sure they enjoyed it, but none behaved as lustily as Lily did.
She grabbed my hair, slammed her pussy onto my face, and rubbed her cunt against me as if I were a toy. Her fingers were all over my head, gripping my hair, digging into the back of my neck and fondling my ears as she sought out the best position. “Right there!” she ordered when my tongue tapped against a certain spot inside her. I did my best to replicate it, and she must have liked it because she moaned and her pussy got juicier.
Soon her liquid was streaming down my throat, some coating my chin, and she was shaking. Lily climbed off me, and then proceeded to lick her cream off my face. “You take orders well,” she said, turning to stare at my cock. She held it in her hand, as if displaying it for me. “What should we do about this?” she asked, squeezing it so the head bulged between her fingers.
“Aaahh,” I said, loving the way her touch felt. I had no idea what to expect, but then she crawled forward, straddling me the reverse way from before, so her wet, pink cunt was visible, and gave me the slowest, hottest blowjob I’d ever gotten. She took her time, easing off when I seemed on the verge of climax and using her free hand to fondle my balls and stroke my inner thighs. “Oh, God,” I called out, overwhelmed by the heat from her mouth and the sight of her pussy. She swallowed me all the way, moving swiftly, as if it weren’t a problem in the least to take eight hard inches deep into her throat. Lily stayed there for a few seconds, with her lips wrapped around the base of my cock while the head reached toward the bend in her throat.
I didn’t want to come because I was trying to prolong my pleasure. But when I reached forward to stroke her wetness, I couldn’t help it. I exploded right down her throat, and Lily didn’t even gag. She just shifted so only half my cock was in her throat, and then she proceeded to milk me of all my come, swallowing every last drop. I was exhausted when we were done—and impressed.
“I didn’t even know you liked me!” I said to her later that night as we finally indulged in the bottle of wine.
“I like to surprise people,” she said. We clinked glasses, and she gave me a wink. I was hard again already, only an hour later, and couldn’t wait to fuck her for real. Lily certainly surprised me and has made me feel more than welcome in my new hometown. I look forward to many more lessons in her bedroom—and beyond.
—Mr. S.L., via email
Excerpted from Letters to Penthouse xxxvii by Penthouse International Copyright © 2010 by Penthouse International. Excerpted by permission.
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