Long Live the Sex Letter: Gallery #233 2020
As a loyal subscriber to Hustler magazine, I was bummed when they did away with their long-running “Hot Letters” section. Those first person (written as “true”) accounts of sexual adventure were the closest thing they had to a proper short story, and I really hated to see them go. Based solely on this, I opted to let my subscription expire.
I had always considered Gallery the second-best stroke mag on the market (after all, we’re talking about a publication that published Stephen King’s “The Raft,” one of his most memorable short stories, and the inspiration for a vignette in Creepshow 2), so I switched over in typical traitorous fashion; I had no idea if they still published sex letters, but felt it was worth the gamble.
I paid for a one-year subscription, and proceeded to wait not so patiently for my first issue. She finally arrived some three months later. The first thing I noticed was the magazine’s relative thinness; in terms of page-count the current incarnation of Gallery is a rather anorexic version of its former self. Trying to keep an open mind, I took a deep breath and started flipping the glossy pages.
Imagine my surprise when I found not one, but two unattributed fuck letters for my reading enjoyment: “Sweet Cherry” and “Riding Tiffany.”
Tanya, the 18-year-old narrator of “Sweet Cherry,” is having dinner at a “nice restaurant” with 32-year-old Jimmy. All of her girlfriends have had sex, but poor Tanya is still a virgin. Of course, Jimmy’s Jimmy is “like huge and really, really thick” and he’s more than willing to use it.
But let’s not get ahead of ourselves . . .
Back to the restaurant where Tanya gets fingerfucked under the table: “He pulled his finger out almost all the way, then pushed it back between my puffy lips. Then he proceeded to pump it in and out of me.” Another diner notices the couple’s shenanigans, smiling at Tanya before they exit the restaurant to resume the action in Jimmy’s car. After informing him that she is a virgin, Tanya spreads her legs for Jimmy’s expert oral skills: “. . . his tongue slithered inside my hot pussy, and he fucked me with that hard tongue of his as he slurped and swallowed my juices.”
Primed for her first reaming, Tanya takes it like a champ, marveling at how good it feels to finally have a proper cock buried in her cooze: “Oh, this wasn’t like a finger at all! He was huge, and I felt like I was splitting in half.” While banging Tanya, Jimmy sucks her tits and fingers her clit, heightening her pleasure until the inevitable explosion: “. . . his hot jism flooded my pussy. He cried out, his cock delving deeper and deeper, and he had so much jizz that it just poured out of my drenched pussy.”
Well, so much for Tanya’s cherry . . .
But there’s more, a nice little twist ending to wrap things up. The nosy diner, along with two of his friends, begins to applaud; they watched the whole thing through the “steamed-up car window.” Stoking her exhibitionist fire, Tanya fucks Jimmy one more time, treating the appreciative voyeurs to a XXX double bill.
“Riding Tiffany” continues the barely legal theme as our titular hottie is “the 18-year-old daughter of a wealthy dentist” vacationing with her family at a dude ranch. The unnamed male narrator works at the ranch, an easy enough gig, yet far from ideal as the rural locale provides little in the way of a social life.
Saddling Tiffany’s horse, our stud can’t help but notice her ample charms: “Tiffany was any guy’s wet dream: five-foot four, with long, honey blonde hair that fell halfway down her back. She was a petite 114 pounds of tan, firm girl.” Tiffany embarks on her ride, leaving the ranch hand all to his lonesome; unable to get her out of his head, he rides to a secluded spot in the woods where he often goes to rub one out.
And that’s just what he does. Cock in hand, he hears somebody moaning. Guess who? You would be correct, my filth-loving friend: “I peeked through the brush, and what I saw almost made me cream in my pants. There was little Tiffany, naked except for her cowboy boots and hat, ramming two fingers in and out of her hot slit.” Great minds think alike . . .
The narrative veers into slapstick when he trips, falls through the foliage, and lands right in front of Tiffany. Pleasantly surprised at the intrusion, she says, “No sense in playing alone when we can play together.” I couldn’t agree more. Tiffany proceeds to suck his cock and swallow the load. Our narrator returns the favor, eating Tiffany’s pussy, a first for her as she explains: “All of the boys I’ve fooled around with thought it was gross.” I fear for the future of this country . . .
The inevitable fucking includes missionary and cowgirl, the latter providing one of the more memorable passages: “What a sight: this lovely blonde nympho, wearing nothing but cowboy boots, riding me in the middle of the woods!” With her voracious appetite for ball sauce, Tiffany dismounts and sucks our cocksman dry, ingesting her second load of the day.
As a new subscriber, I was most pleased with my first issue of Gallery. Let’s hope the next one delivers equally glorious goodies.