This is a story of casual, unprotected sex, and is a work of fiction. In real life, use a condom, damnit! Unwanted babies, HIV and all sorts of lesser sexual diseases await the idiot who “dips his wick” or “rides the rod” with impunity and without protection.

—

Fag Hag (MF, con, impreg)

by Krosis of the Collective

—

Sylvester threw his leather jacket across the living room. “Damn it!”

Jackie looked up from her book. “What’s wrong, bunkie?”

Sly sat down heavily on the couch next to his roommate and sighed. “Some of the ass in this town is so fucking far back in the closet that they’d taste like mothballs, even if I could get them out of there.”

Jackie put her book down. Her gay friend blew up like this pretty much every weekend, after attempting to trawl for some man-love and coming up empty.

“This area is so ultra-fundie that I’m more likely to get lynched than laid, Jacks! Why the hell did we move out here?” Sylvester fumed.

Well, Jackie had moved to this small town because she had been accepted for a teaching position at the local elementary school. Sly had been rooming with her when she got the assignment, and tagged along. “Sure, let’s blow this shithole city,” he had said. Sly was a bit of a potty-mouth sometimes, but Jackie loved him. He was her best friend. Some people would call her a “fag hag” for it, but she didn’t care. It was like having a girlfriend, except one with a masculine body that she could ogle whenever she wanted.

Jackie got up, gave a “stay there” hand signal, and headed to the kitchen. She returned with bottles of rye and cola, and tumblers. “Just what the doctor ordered,” she said.

Sly accepted the libation with a dour look. “What doctor?”

“Why, Doctor Love, of course,” replied Jackie. “If you’re blitzed out of your mind, you can’t feel bad.” She thought about it a moment. “Well, until the next morning.”

Soon the bottle was empty. Jackie was giving Sly a foot rub as he laid back, yammering on about the blonde piece he had chatted up at the bar.

“He had a Jude Law thing going on. Slight of build, but lips you could use as a trampoline. God, I’m so fucking horny…”

Jackie was pretty much blotto too. HE was horny? She had been so busy with work that she hadn’t met anyone even remotely interesting. All the men at work were married, and older than her, besides. She remembered her dildo, waiting for her back in her room, then her eyes fell on Sylvester’s crotch.

He had a massive bulge in his pants! His eyes were closed, and he was still describing the hottie he had almost hooked up with. Jackie gulped, unable to take her eyes off her gay friend’s swelling prominence.

“Sly…have you ever…been with a woman?” Jackie asked, continuing the foot rub but not taking her eyes off his crotch.

“Oh, fuck no, sweetie. Too…round, and certainly not enough muscles for my liking. Mmm…” He was enjoying the foot rub, eyes still closed, and his bulge got bigger. So did Jackie’s eyes.

“Wait here…” Jackie took off to her room, leaving Sylvester lying there, too drunk to do much else.

A couple minutes later she raced back across the living room into Sly’s bedroom, something tucked under her arm. There were sounds of drawers and closets opening and closing. When she returned, Sly was almost asleep.

“Hey, man, do I know you?”

Sly started awake at hearing the deliberately deep voice. He blinked a couple times, then managed to focus on the figure in front of him. He started to laugh:

“Ha ha heeeeh!! What the fuck ya doin’, Jacks?”

Jackie was dressed in a pair of Sylvester’s jeans, t-shirt and boots, her long dirty-blonde hair tucked under a baseball cap. She had used the dimmer on the lights, and that, combined with her athletic form, obtained from daily morning runs and afternoon weight training, allowed her to almost pass for a man. Almost. She had purposely worn one of Sly’s baggier t-shirts in order to hide her breasts, which, while not large, would certainly shatter the illusion.

“Feel this, cowboy…” Jackie drawled deeply, grabbed Sly’s hand and moved it to her crotch. He started, unbelieving, as he felt cock under his fingers.

“What the fuck–?”

Jackie pushed him back and undid his zipper, still keeping her voice low. “Keep telling me about the guy at the bar.” She had his cock out now, and marveled at its size: 8 inches long, and thick; bigger than anything she’d had in a while.

“Jacks, I don’t think…”

“Sshh…the guy…” She engulfed his dick with her mouth. Sylvester lay back and closed his eyes.

“Uh…his name was Bill, I think, or was it Bob? Um…he works at the steel mill. He was small, but wiry. Nice definition in his arms.” He reached over and felt the muscles in Jackie’s arms. She really did have some nice muscle tone. Kind of like a guy…

“Ohh…I’m giving you just a half-hour to stop that, shweetie.” He slurred and smiled, laying back and continuing to describe his recent would-be-beau, superimposing his form onto his best friend in the dim light and his drunken mind.

Jackie’s mouth started to get tired. She stood up, and unzipped her borrowed pants. “You want some of this in your ass, cowboy?”

Sylvester finally understood: she was wearing a strap-on rubber dildo! He snickered. “Sorry, hon, but I’m the bull, not the bitch. I like giving it, but I do give a ‘reacharound’ for my pincushion.”

She pulled down her pants a bit and got on her hands and knees in front of him on the couch. Because she had only pulled the pants down a little, he could only see her shapely ass and not her cunt. The illusion held up. His erection didn’t flag at all.

“An ass is an ass, right?” She growled. “C’mere, stud…” She wiggled her tush and tossed him a foil-wrapped condom.

“Just a sec…” He said, getting up and going over to the light switch, dimming them even more. Now she (he!) really did look like Bob (or was it Barry?) from the bar.

He shucked his trousers, put on the lubricated condom and got behind her (him!). He poked his finger at her anus a little. Too tight.

“This a virgin hole, hon? I’ll be gentle.” He stuck his thumb in his mouth, lubing it up as best he could, then pressed the thick digit at her puckered orifice. He could hear her gasp from discomfort as his insistent pushing finally made some headway. Soon his thumb was able to go in and out without too much difficulty.

There was not much more he could do. There would have to be some stretching. Luckily there was lubrication on the condom or this would really hurt, he thought. He put the tip of his penis at her asshole, pulled his thumb out and pushed his dick in before it closed up. She gasped in pain at the sudden, larger intrusion. He held himself still, then pushed a little more. Jackie’s was still facing away from him, her features pressed into the arm of the couch, but in his mind’s eye he could see her face, all scrunched up in pain. He started to lose his erection.

The shrinking of his penis actually helped to get more of his cock inside her ass, and she was no longer in so much pain. She looked back at him. “C’mon, man, give it to me,” she drawled in that low voice. “And don’t forget the reacharound.”

Heh. He pushed back into her (him!), eventually bottoming out, and he bent over to reach around for the dildo (dick!). It actually felt pretty flesh-like, and the familiar feel brought life back to his stiffy.

Jackie’s ass felt like it was on fire! She had wanted to help her friend, and maybe find some sort of release for herself, but she was NOT enjoying her first anal penetration — not at all! She just hoped he would finish soon and she could get some dildo time back in her room.

Sylvester continued playing with Jackie’s fake strap-on, and as he became more excited his drunken hand movements became more energetic. Due to the angle she had to keep her ass at in order to hide her pussy, the vibrations he was causing went up the shaft of the fake penis and right into her clitoris. It started to feel good!

Sly was getting a really good rhythm going when Jackie (Barry! Brad?) started to thrust her pelvis forward to get better stimulation from the shaft of the dildo. He started having trouble keeping the rhythm, and then slipped out.

“I got it…I got it…” Jackie reached back underneath her and grabbed his cock. She pushed back, but by reaching down she had adjusted the angle of her pelvis and this time his cock entered her wet cunt.

Immediately all the pain in her ass was forgotten. She had a cock in her pussy, finally, and it felt so good! Sly, not realizing the change in venue due to how dark it was, and never having had sex with a woman before, grabbed her hips and started to pound her hard.

All Sly knew was that it felt good. He closed his eyes and fantasized about the guy he had almost won over tonight, grunting underneath him.

Jackie was grunting hard. Her orgasm was building as she pushed back against her gay lover. Oh fuck, oh yes, fuck me!

All of a sudden both of them felt something…change. Their connection felt warmer, with greater friction. It felt ten times better than it had a moment ago, and the sudden difference sent them both over the edge.

“Ouhhh! Fuck!!” Sly yelled, as his orgasm exploded behind his eyeballs, then rocketed down his spine to his crotch as his testicles pulled up as tight as they could to his body, giving up their jam-packed contents. He rammed into her hard, again and again, as the sperm-filled semen shot up his dick and out the tip with incredible force.

Jackie screamed: “YES! OH FUCK YES! OH GOD! UHHH! AHHHH!” She thrust herself back at him as she felt his dick swell within her. She felt an expanding warmth deep within, and it intensified her orgasm as her insides churned, pulling and sucking on his spurting cock.

Finally they were spent. He pulled out of her with a wet sound. Warm liquid started to roll down her leg.

“Uh? Sly, what–?” Jackie rolled into a sitting position and felt at her thighs. Semen!

Sylvester looked at the remains of the devastated condom barely hanging on to his cock. “Oh, shit. What kind of condom was that, Jacks?”

“Ultra-thin. Only kind I use. What the fuck?”

“You can’t use those for anal sex, girl! You need the extra-thick ones. Well, good thing it was just your ass, huh?” He looked down at the thick white liquid as it dripped out of her vaginal hole. “Uhhhh……HOLY FUCK!”

Nine months later she and her new “husband” gave birth to a baby boy, although the two of them had waffled between Billy, Bobby, Barry, and Brad before finally deciding to name the boy Brett. It felt right, Sylvester said.

It sure did.

---