An Email From The Past. He Hoped I'd Remember.
"Hey Dolly, I hope you remember me but I know you have a lot of friends and I have a new email address from when we last saw each other. I hope you remember me from a memorable trip to Shanghai -- bet you haven't had a lot of friends take you to China -- when we stayed at the Waldorf and had outdoor cocktails at the rooftop bar on the 58th floor of the Ritz Carlton on the other side of the river. And then we giggled about the curiosity that the transgender flight attendant had better legs than the older natural born woman flight attendant and that wonderful favor you did for me when the lights were shut as most passengers slept. Or that bowl game weekend we spent, but then I had schedule conflicts because of clients and you and I never, well, lets just say I hope you remember those times and our other fun as well. Anyway, that's who I am, now with this new email, and I saw you'll be in my city. Can we meet for an overnight visit till morning, Wednesday through Thursday? I hope you'll respond."
That's how the email read.
I read it twice. Not because I had any doubt about who it was from.
Tom was always polite. That's mostly why I re-read the email. Nope, he never mentioned a sex act anywhere in the email. Never mentioned what city he was in. Okay, he mentioned Shanghai and two hotels we'd been in, only one of which we stayed in. But he never said when, and I concluded that if his email was intercepted, we were both safe.
I always felt safe with Tom.
I hadn't had Tom as a lover in three years. No, four. Time flies when you're having fun with other friends.
We'd become pen pals, then one day, the email bounced back as undeliverable. It happens, men leave the hobby. So do the ladies. Sometimes they come back. Tom, it seemed, was back.
He was average to above average in looks, which is plenty fine I want to add. He was somewhere in the middle of the income range of the men who reserve my time for Dolly dates. He was married, one child, two dogs, and was stuck in the sandwich generation syndrome with elderly, ailing parents who were driving him slowly insane.
Tom had a thing for fitness chicks. I've got some bikini pics that he thought were from a competition. "You never entered a competition? But look at you, you look so ripped in that one?"
I explained triathlons. He thought that was even hotter, and then after our first date, when he was sweet enough to pick me up from the airport during a tour to his city, I clued him in on my previous track & field career, Olympic trials, just missing the team, and he was visibly excited.
"I'm going to get to fuck a hard bodied international track and field chick? Wow, holy shit, that's been a fetish of mine since I went to Atlanta in '96 and got some passes inside security through a client and saw those chicks up close. Sexy and fit and all kinds of fetish, and now I'm with you!"
Yeah, Tom could make a girl feel pretty good about herself. Suddenly, fourth place in the trials my year didn't seem so bad.
He started off surprisingly timid, which I thought was sweet. I had on a simple dress, well above my knees, no hose, four inch heels, a scoop neck that showed enough to be sexy but not enough to draw undo attention other than "hey, she's hot" type comments. It had sleeves, was snug to my body, and my lips were doing all the work until slowly his hands got comfortable on my body, and my hand stroked his package which reminded him that the door was closed. He'd left the envelope in the bathroom and the DO NOT DISTURB sign had been hung. He grabbed my firm ass, while kissing me passionately, his tongue pushing in deeper, like seeking a deep tunnel. I broke the kiss to say, "lunges" to answer the un-asked question.
Tom's cock was getting hard and he pressed it forward into me, and with my heels his cock lined up with my pussy. I was wearing boy shorts--much better to fly in than a thong up my ass on a plane ride, and when his lips touched my neck I purred that it felt wonderful and I wanted to feel the rest of his flesh just like his lips--directly on my skin. I started to undress him.
Sweet man, he could figure out how to get my dress off me, it really was simple once I smiled and took his hands in mine and said, "here, play with these while I show you how to unwrap me" and put his mitts on my tits. I think we were both stark naked on the bed in thirty seconds.
I gagged a few times while Tom was so excited and moving around trying for the perfect position both to get sucked off and watch me suck him off--a moving dick is harder to deep throat. And then as my lips felt his cock reach terminal hardness, I rolled a condom on him and told him to lie back. I hovered, lined up his cock, and licked my fingers just to fine-tune my body's readiness to be invaded by Tom's cock.
I sank enough to take the head and another inch of dick into my pussy, and I was well-lubed, naturally (ah, isn't being a horny slut the best! Damn near always receptive, sexually!). And then Tom started bouncing and thrusting up into me. My nails dug into the front of his shoulders. It was brief, the actually fucking often is, but the look on his face was so erotic. Trying to keep his cool, it was like screwing a secret agent. Intentionally trying not to show how good it felt. Until he climaxed. His whole body crumpled. "Oh God, Dolly, fuck....ahhhh, oh, mmm, uuuhnn, Shit, oh fuck so good, so so good." Babbling. Love when I get them babbling. Makes up for when I don't get to come. But the night was young.
I wanted him to take me standing, up against the wall, from behind the next time. Which meant like twenty five minutes later. His stamina started to betray him. Having just cum, he wasn't nearly ready again yet. But still he tried, and for that, I thank him.
We met in a variety of circumstances. Miami for a business trip. Miami on a family trip while wife was visiting her Uncle Sidney at a retirement community. Virginia Beach on a family trip with me in the next hotel over from where he was staying. Indianapolis for a college basketball tournament weekend complete with sex with Dolly (no, you can't buy such a VIP package from the NCAA, I market independently of the NCAA). New York during a trade show at the Javits Center. Well, we didn't fuck at the Javits Center, we fucked at the Grand Hyatt, but the reason Tom was in town, and brought me, was a trade show. Import Export with Vandelay industries, I joked. He didn't get the joke. "Seinfeld" I told him. Sigh.
So Tom was a decent fuck. A generous lover, and good-paying client.
And I was horny.
"Hey There!" I wrote back, "of course I remember you. Sorry you had difficulty with the old email, glad to catch up with you. You still remain my only friend who ever took me to China. Amazing country. What a great brunch buffet -- bacon, eggs, pancakes, gourmet baked goods, healthier choices, and pot stickers, lo mein, wonton soup, and that nasty congee (Chinese porridge). And how we laughed as we strolled past the Lamborghini dealership and the Harry Winston Diamonds store in a communist country. So now that I know who you are and what city you are in, yes, I happen to still have that night you asked about available. Our previous start and finish times for an overnight date still okay? Any special requests?"
I knew I didn't have to worry about special requests. He knew better than to start naming sex acts in an email. Not that I didn't want to suck his nice, circumcised cock, which he didn't manscape, explaining that his wife, the lovely woman with the sex drive of a filing cabinet, would never understand. I loved how a man with such a way with words went silent when I took him into my mouth, only some whimpers and soft gasps and grunts. He didn't so much shoot his load as it seemed to spill out of his dick. No ropes, no spurts. One complete flood of whatever he was dispensing all came out at once, without much velocity, though again, he wasn't in his twenties.
And damn but he wouldn't fuck my ass! I love anal. So taboo, to use my entire body for sex and pleasure. Giving my ass to a lover who has already had my pussy and my mouth, ah, what more is there? Okay, sure, a titty-fuck, but that's not internal, you knew what I mean. Not for Tom. "Dolly, mine is exit only, I've had hemorrhoids, the ass is something to admire and touch and tease, but not to enter, at least not for me. Why go there when there's a perfectly natural habitat waiting for my dick just an inch or so away?"
And yes, I had to gently but firmly take him in hand on that second date when it seemed like he thought because we'd clicked so well that he could bareback me. "Where you going without your raincoat, Thomas darling? Glad I caught you before any problems developed. You know I've always got condoms in case you had planned to use your own but then forgot to bring one." The look on his face told me all I needed to know. Which was (if he'd had a thought bubble over his head like in a cartoon), "Uh, gee Dolly, you know me, you know you can trust me, do I look like I've got ....."
Save it Tom. Or anyone else with the same idea. But Tom never tried again, and I suppose I've come to not be surprised by the occasional attempt.
Damned STD's. There is some seriously hot impregnation porn to be found out there, and I love the female empowerment themes of the cuckold porn where there's a thick, potent creampie from a young stud (or maybe even a big interracial buck!) in the hot wifey at the end of the video.
Yes, I've had guys who wanted to watch porn with me. It’s their time. Some of it is hot. If that what gets a gent's motor running, so be it.
Not that Tom watched porn with me. We discussed vineyards, wine industry trends, and how he'd rather just charter a yacht occasionally instead of buy one from my family's shipyard. Damn, can't blame a girl for trying. Yes, of course I've sold to clients before. Hell, I get complimented on my body (thank you boys!) but I wish I was built as great as our yachts. Hmm, could that be our new marketing campaign?
So welcome back to my bed, soon enough, Tom. Can't wait to feel your tongue inside me, smell your body's scent, taste your cum, and cling to your body as we each tense up and then release.
Purely fictional fantasy for your reading pleasure!