Many thanks to LaurieLou for her help in editing this text! If it's readable, thanks to her, all grammatical blunders are mine, of course.
*****
This insane ride began when my friend and squash partner Christian invited me to a friend's dinner. I wasn't really in the mood for being the third wheel in an all-cooey company, still adjusting to being single again after the divorce after more than 25 years of marriage, but Christian waved away my hesitations. His wife Annette, he explained, had put together an amazing guest list. He would not tell anymore. So the day arrived, and I went, of course.
We were 12 people all in all, and I knew about half of them. It was then that I met Claudia. She was in her thirties, petite - maybe 1.60 meters tall, had shoulder-length red hair, and she was cute-iful - you know, beautiful, but more cute than classically beautiful? And her beauty was of that wholesome, pure kind, not the sexual kind, if you know what I mean. The sort of woman you would meet at church, the kind of beauty that Hollywood would use to light up the hopeless lives of hopeless shelters.
She had a radiant smile, too, and the cutest dimples that appeared when the smiled - the kind that make you do anything to see her smile. She wore a brownish-red shade of lipstick, and skillfully applied make-up. Glasses covered her brown eyes, and when I was close enough, I could make out the small wrinkles in her face, the laugh lines. It was then I began to really take notice of her, because I love women - not girls. I love the signs of having lived a life, and have laughed, and for the life of me I could never understand how a woman could possibly want to erase the visible signs of having lived. Maybe that was one of the differences that led to my divorce, but I did not want to linger over that thought.
Claudia was dressed in a long, red dress that just was tight enough to make sure she had curves all right, but not drawing attention to her body. With that, she wore some straightforward, moderate-height heels. I noticed with a hint of disappointment that the heels were closed, having discovered lately how much nicely painted toes turned me on. Still, that was for the best, I felt way out of my league already. After all, I was 50, balding, and while I did not sport a beer belly, I sported more of an 18-pack than a sixpack to my 1.85 meters. On top of that, I was not holding a fancy, high-income job, I was merely a college professor teaching English and German literature.
To my surprise, I found myself in a long and lively discussion with her, and amazingly, she was so easy to talk to. She was the first to understand my dislike of Philipp Roth, and was tolerant enough to weather my inevitable Salman Rushdie-rave. I hadn't felt that alive in ages! Every now and then, she put her hair behind her ear in a short, determined motion with her hands, and that small gesture, that mere flicker of her hand, was something that mesmerized me. She had carefully manicured hands, with long, slender fingers, and something about that began to... well, as I said, she was way out of my league.
And I felt guilty to see her in a sexual light already, and anxious. It had been a long while. Sex had happened twice a year in the later days of my marriage, and then often came with performance problems on my side, so even if my mind kicked into the mindset of an 18-year-old, the body was still that of the 50-year-old.
I willed myself to think about GΓΌnther Grass, and found out that I could make Claudia smile with recounting the most horrible puns by Shakespeare, so I did. I wasn't fooling myself, though; I was falling for this nice, intelligent, beautiful, and wholesome lady. Boy, rarely have I ever been so wrong.
Dinner was wonderful, and Annette was wearing a smug grin when she noticed me talking to Claudia. "She's wonderful,"
I admitted when I helped Annette carry out the dishes.
"How did you meet her?"
"She's in my book club, has just moved here, and is single. That's all I know." Annette laughed though all my pretenses of indifference.
After that, the crowd began to thin out - we had some drinks, and then it was time to leave.
"Share a ride?" Claudia offered.
I may have been out of the dating loop forever, but I wasn't stupid, so I agreed.
In the cab, she snuggled up to me. In the quietness of the car, I noticed a faint humming I had not noticed before.
"Do you hear that humming?" I asked her, not sure if that was real.
"Of course, silly," she replied, and squirmed in a most peculiar manner.
"What's wrong?" I asked, alarmed. She giggled, bent to me and licked my earlobe before whispering into my ear,
"I just came from the vibrating egg I had in my cunt all evening."
I choked, stunned beyond speech and reaction. Surely my imagination must have played a trick on me. But I felt her tongue in my ear now, and her hand on my crotch, and no imagination could have faked that.
"I could use your help in removing it, you know..."
I swear I almost lost it there and then. But we managed to reach her place, and as her door closed, she had me half-naked already. I kissed her, and she wasted no time in feeding me her tongue, but after what seemed like only seconds she turned away.
"I'm not that kind of girl..."
I looked at her, utterly dumbfounded, and I guess it showed.
"Silly, I meant I'm not the kind of girl for long moonlight kisses," she giggled. "I want something else," she said, opening my pants to prove her point, and how did she get out of her dress so fast?
I didn't have time to admire her full, natural breasts, because suddenly I found myself on my knees, with my face barely inches away from her pussy. I couldn't believe it. This was the sweetest girl possible (she stills reminded me of the character of Emma Pillsbury in Glee), but here she was, pressing my face into her pussy. I smelled her before I could taste how wet she was.
I found her clit, letting my tongue trail though her wet slit, and I could hear the humming again, and then saw the string hanging out of her. I pulled, and the vibrating egg slid out, carrying a gush of pussy juice with it. She laughed with delight as I lapped away at her cunt.
And then I saw the jewel in her ass. It was the first time I saw that in real life, and I swear it is the most exciting thing to see a plugged sweet ass for the first time as your face is grinded into a sopping wet pussy. I felt her juices drench my beard and I laughed with delight, and then ate her as she leaned against the wall.
I asked her to turn around, and buried my tongue in her butt cheeks - pulling up that plug just in time to reach the gape with my tongue. I could not believe how beautiful it looked. I zoned out and just followed instinct and had my tongue fucking her ass. As her hole slowly closed it caught my tongue in it, and she squealed in delight as her muscles tried to capture my tongue.
Two orgasms later her legs shivered, and she turned to me. I had been so utterly lost in her pussy and ass that I had not wasted any thought about my ability to perform, and just then realized I had a really aching hard-on. Claudia giggled, yelled about how she was going to use my cock to make herself cum again. I still could not process how that wholesome, pretty face could produce such dirty talk; it was like hearing your mother talk about sex, if you know what I mean. She pushed me on my back and lowered herself on my aching cock.
Now, I'm regular-sized, to be honest, and I was expecting myself to slide into that hot, wet box, but she lowered her ass - the one I could still taste on my lips - onto my cock. I had tongue-fucked her ass enough to enter her, slowly, and almost a bit too roughly for me. I was afraid to hurt her, because it did hurt me, deliciously, exquisitely - but it did not seem to bother her, it did not even slow her down.
"God yes, I love getting my ass fucked," she moaned, as if I hadn't noticed.
My cock went into an ass for the first time ever. Anal had not been a thing when I was young, and while my ex and I had talked about it, it had never happened. And I learned that anal porn is to actually having your cock up her ass like licking a picture of a candy cane is to actually biting into one. It's hot and tight and not like anything else, and if you think about what you are doing, it's almost impossible to remain in control. Her ass had my cock in a firm grip, and it felt good. She took the plug that had filled her ass and fucked her pussy with it as she began to ride me. It was out of this world - here I was, gone from barely dreaming of sneaking a kiss from this innocent maiden to having my throbbing cock up her ass.
She must have felt me throbbing, because she urged me to shoot my load - or, as she phrased it, 'my nasty hot fuck-juice' - up her ass. And so I did. Sometime later, when we had recovered a bit and were exploring each other in a 69, she confessed that she craved hard sex, dreamt of being used by multiple cocks, exposed and out of the blue, and I had reason to believe her, because she came on my face as she described her fantasy.
From that day on, we spend most of our time together - much of it with at least one of us half-naked, to tell the truth. She was under my desk at college, leaving my office with a load dripping from her nose and mouth on her blouse; I ate her ass and pussy hidden under the table in the restaurant she had lunch with her co-workers in; we rode the subway with her sitting not only on my lap; I had an app on my phone to remote-control some toys she often wore; and almost always she wanted my cum in her ass - sometimes letting it seep out of her butt over time, sometimes plugging it to keep my cum inside and use it as lube sometime later; and much more - but she never felt to tell me how she wished there were more cocks to fill her, and how she wanted to be surprised.
Weeks and then months passed, and we were still at each other like teenagers in heat - in ways that I would never have thought possible outside the realm of erotic fiction or lamest excuses of porn movie plots. But we did couple things, too, since this was real life and not a porn story: we went to movies and the theatre, we cooked and did laundry and we met each other's families, we enjoyed our circle of friends, we went on a vacation or two, and no one ever, not even her closest girlfriends, alluded to the difference between Claudia's appearance and her true nature. I was happy beyond my wildest imaginations.
I remember one morning during a weekend getaway in Florida when, after an hour of eating her pussy and her ass, I finally fucked her with her favorite 'natural' dildo, and then slid her vibe into her butt. When I activated the vibe, she started to cum, not to complain, and told me to feed her my cock, and as I did, I jokingly mentioned that both of her hands and her feet were free, so she could service six guys at once. Without batting an eye - and I can vouch for that, because I was staring at her deep brown eyes as she tried to swallow my cock (she never took off her glasses, by the way, no matter how often she made me cover them, claiming she loved licking them clean, and not wanting to get cum in her eyes, understandably) she replied,