I've been attracted to older women since my early twenties. I'm not sure why. It might be their maturity or something about my childhood or I don't know what. There are websites out there that cater to this sort of stuff. I had placed an ad on one a few months previously. Thinking myself clever, I answered the question, "What have you always wanted to do but never tried?" with, "I feel as though I've ridden all the rides in the playground of life until they aren't worth standing in line for anymore. That said, I wasn't spanked enough as a child." I wrote a few women before my trial membership expired and didn't hear back. Still, odd as it sounds, strange women began swatting my butt in public ever so often. I had almost become used to it.
One afternoon, it happened in a department store, a woman in her late 40s. I was in my early 30s at the time. Walking by me as I flipped through shirts, she breathed something in my ear and slapped my ass. I turned, a bit taken aback, then smiled at her. She trotted off and I followed. She glanced over her shoulder a few times, smiling a bit, a powerful, knowing look in her eye. Then she stopped to examine a chemise. Turning to me, she said, "You're a bit chubby."
"I'm trying to lose weight."
"Don't worry, dear. I'm only thinking out loud."
"Would you like me in white or black?" I blurted, shaking from the effort of wrenching it out of my mouth.
"Are you a virgin?"
I shook my head.
"Black then. My name's Linda."
"We'll make you lovely, dear, if that's what you really want."
"Good." I followed her about the store as she picked up a matching black dress witch a short, pleated skirt. Then shoes with low heels. When we neared the stockings, I made an uncomfortable noise and Linda smiled. "A girl can always hope," she said. I let Linda pay and, in the parking lot, she handed me the bag and took my phone number.
I didn't hear from her until the next weekend. "I'd like to come over," she said. "How long do you need to get ready."
"Give me an hour?"
I shaved again for good measure, and jumped in the shower. Once done, I gathered the clothes from atop the chair in my bedroom. I had already tried them on, but only for a few minutes. I hadn't even looked at myself. I don't understand men who crossdress as a lifestyle. Dressing up for sex is one thing, but lounging around the house in women's clothing seems to me rather like watching television with a ball gag strapped to your face. Perhaps for this reason, I didn't feel comfortable wearing the panties she had bought for me. But everything else, I put on, including the bra, which I stuffed with tissue paper.
Linda was at the door ten minutes early, dressed in women's clothing, but not femininely. I turned my cheek and she pecked me on it. "Honey, look at you," she said. I felt torn between wanting her to seduce me and wanting to fuck. Linda didn't let me think long. She reached forward grabbed my head, and we kissed, her left hand pawing at my breasts. "I am going to do you so good, so right," she said. I took her hand and led her into the bedroom. We kissed again, her hand caressing my ass, moving over my dick, squeezing it.
"You're making me so hot," I said. "My clit's so swollen."
"Oh, God, Michael." She stripped off her blouse and slid down my body. Running her hand up my leg, she looked into my eyes. "No panties? You fucking slut." I rocked my hips back and forth to encourage her to touch me there. Linda cupped my balls but would not go further.
"Please," I begged.
Still looking straight into my eyes, her finger touched the entrance to my asshole. "Would you like me to put my cock up there?"
I nodded eagerly, wobbling on my heels.
"Get on the bed then, darling." Without taking my shoes off, I climbed onto the bed, on all fours, in a position that let me look into the bathroom and watch the mirror. Linda smiled when she noticed this, then returned to preparing the dildo. Finally, behind me, she pushed my skirt up onto my back and pressed the dildo against my anus. "Michael, I'm not going to stop."
The next thing I felt was her rubber cock pushing into me. I gasped, as it filled me, opening my ass around her. I squeezed the shaft of it with my clutching anus and lowered my head as she began to fuck me. The early part of being fucked in the ass is unremarkable, one of the reasons I don't sleep with men, the other being that I'm not nearly as attracted to them. But then the warmness began to creep up my body and the shallow moans I made for Linda became louder and genuine. My asshole began to twitch and spasm around her cock, and I smiled, knowing it was getting good. It was then that I saw Linda watching my face in the mirror. When she noticed me watching, she began to slam into me harder, and my mouth dropped.
There was something about the fabric moving on my skin, and her hands on the fabric, and knowing I was wearing heels and getting fucked like a whore that suddenly came together. I groaned loudly and began to wine, "Rub my clit. Please? Rub my clit?"
Linda reached around through my legs and began toying with the head of my dick. My whines became louder and I began to buck some as she fucked me hard and deep, leaving no question but that I was being taken. We were not making love, we were not screwing. I was getting fucked. I tossed my head, not entirely aware, as she watched my face and fucked into me.
"Do you like that, Michael?"
"Do you want to cum for me, Michael?"
"Please, no. Not yet, not yet," I whined.
She withdrew her hand and I let her pound me for a few long minutes. I grew hard under her thrusts, then soft again. When I began to touch my cock, it wouldn't grow. I played with it until I began to cry out from pleasure as Linda's cock massaged the inner muscles of my spasming asshole. Rubbing up against then as they squeezed and twitched along its surface. And I talked like a slut too: "You fuck me so good. God, I love the way your cock feels in my ass. Is my asshole tight enough for you? Pound my ass. I love it. God, I'm such a fucking whore. I'm your whore tonight, Linda." All interspersed with cried of pleasure that rose in pitch until I bucked and screamed under her, begging to cum, begging for permission. Needing her in me, never wanting it to stop, but needing to cum so fucking incredibly bad.
"Cum, Michael. Cum," She grunted and began slapping my ass as I worked furiously at my limp cock. My whines and cries escalated to screams, four or five, each louder than the last, and the last a high pitched shriek of pleasure as my cock began twitching and firing again and again into the inside of my skirt and sheet. She pulled out of me and I collapsed onto it, my own cum, unsure of what had just happened.
"Whatever turns you on, I guess," I groaned.