Several weeks have gone by, as Jim and Heather were finding a renewed passion in both life and the hope that this maybe something real. Jim had already secretly fallen for her a few years back. Heather on the other hand had been more focused on work, but something was definitely tugging her towards Jim.
Tonight, Heather had another one of her mischievous streaks and this time she was the one upping the ante!
Jim came over a little later with a bounce in his step.
“You seem chipper tonight,” Heather said with a mischievous grin.
“I just love Fridays, I know I will see you” Jim said.
Continuing, Jim said, “I brought the DVDeeeeeeeeee………..Holy Shit” stopping mid sentence Jim grew pale and wobbly kneed.
Just then, Heather put the dreaded strap-on onto the table again, grinning, "I have wanted to re-visit this," she told him, "I win, I get your cherry."
Jim thought long, took a breath, and gulped, then in vain countered, "Um, Fine... but if I win, I get yours."
The obvious challenge didn't make her hesitate in the least; she'd known what she was getting herself into the moment that she'd ever brought anal into the picture. It was something she'd always been rather curious about anyway, even though it was something that she thought was kinda dirty, the naughtiness of it had always turned her on. And fair was fair if she was making him bet his ass, she might as well have hers on the table too.
We all know too well know the scenario by now, Jim and Heather make some sports bet, the winner gets their way with the other! Well guess who lost the bet tonight………………..Me, I mean Jim!
Trudging upstairs heavily, and ever so slowly, following Heather's swaying ass. Cold comfort that he might have had that if he'd won... he was very, very unsure about how he felt about this. (And came close to begging out, very close). On one hand, yeah it was with a girl; on the other hand, he'd never wanted anything near his ass. Social stigma maybe, but it was also supposed to hurt like hell, and he didn't really see how anything painful could be sexually exciting. If she hadn't made him bet his, he probably would've never suggested that she put hers up for grabs either.
They kissed as they stripped down, and even though he was extremely nervous about the whole ordeal, he couldn't help but get hard as they touched. Setting up some pillows in the center of the bed, she had him lay face down on them, his hard cock rubbing up against the pile. Some of his hardness dissipated as he watched her put on the strap-on, a smaller vibrating cock fitting into her pussy. She flicked the switch on and paused a moment to enjoy the excitement. Now, for the “Business” end. It wasn't very big as these things go, 6” he appraised, and he knew that they made much, much bigger ones, but right now it seemed awfully threatening. To the point that he started to hyperventilate and get dizzy, he just lay over the pillows and looked back at her.
Smiling at him, her breasts swayed gently above the protruding dick as she lathered it with lubricant, making it slick and shiny. He watched with trepidation as she got behind him... his body tensed in anticipation and then shivered with reaction as she ran her hands down his back. Suddenly something wet touched his anus, but it wasn't big hard and rubber, it was soft and very wet, laving over his sensitive skin and awakening pleasure nerves that he hadn't known existed. Groaning he realized that she was licking his anus, something he'd heard about but had never thought anyone actually did. It felt fantastic.
Moving his hips with her tongue, he could feel his dick getting rock hard as it brushed against the pile of pillows, and his ass swayed with her movements. His legs spread apart a little more as he relaxed, he hadn't realized that his ass was such a bundle of nerves and pleasure points! Once he had really started to get into the licking, Heather had another surprise in store for him. Still licking and sucking the anus, she slowly inserted her lubricated finger. Gently exploring the rim of the anus and gently squeezing the area between the shaft and just inside the anus, Jim felt the most erotic sense he had ever felt. Now, ever so gently she continued to insert her finger even deeper, all the while Jim really liked it and the stigma had left him. All of a sudden!
“WOW, what was that”? Jim Screamed!
The most intense pleasure he had ever felt just came over him.
“Sweetie” Heather said, “Just relax “That is your prostate gland, you know your sex gland, that’s what gives you your orgasm sweetie. I am going to give you a prostrate massage”, is that ok?
Quivering, on the verge or orgasm already, Jim barely got out the words, “Shhhhhhiiiiiiiit Yeah”.
Gently Heather proceeded to massage his prostrate ball while slowly digging through the pillows to massage his throbbing dick.
“Could you please turn on your side”? She softly asked.
Jim rolled over, all the while she just kept her finger massaging his prostrate and stroking his glorious dick. She had grown quite fond of him, and truth be told she was really trying to give Jim a time to remember, not regret. Now on his side Heather, slowly at first then more rapidly she started to devour Jim’s dick. It couldn’t have been more than three of four minutes, before she could feel Jim getting ready to cum. Pressing and massaging his prostrate with her finger even more rapidly and in an ever so aggressive manner, Jim began to convulse! What was the largest load he had ever released, shot right down her throat, Jim screaming quite loudly was rendered helpless. He just squirmed, convulsed, and tried to shake loose from her grasp. But she had three points of contact that would just not let go. Pressing her finger into his ass ever deeply, while the grasp on his dick was vise like, and her mouth filled with a wild spurting cock, wild horses could not have pried those two apart. Now, with an actual scream, Jim unleashed a final load of cum down her throat, and just collapsed on the pile of pillows. Savoring the last of his mildly sweet tasting cum, Heather let him just lay there, face down on the pillows.
Five or ten minutes of later Heather, got him to reposition Jim on the pillows, started to gently lick his anus and play with it.
Jim was thinking to himself, “here we go again, ummmmm”. And he just smiled.
Well, Heather had other ideas! She shimmied up to his ass, oiled it up like a newborn baby, and then without hesitation began to press the cold, slick head of the dildo into him. As she started to press in he groaned, his ass stretching over the thick rubber, and his wide open just staring at the headboard, clenching for the sheets! It didn't hurt as bad as he'd thought it would, but it did make him cramp a little. She paused as it reached two inches into his body, massaging his shoulders and just moving it back and forth slightly. Inside of her the smaller dick moved, vibrated, and the clit stimulator tickled her pleasantly.
With little but firm strokes she slowly worked her way into his ass, and she wondered what it must feel like in there... what it would feel like if she had a real dick. Jim was breathing heavily, his firm ass opening up slowly and every stroke digging deeper... to his surprise he was getting completely hard again. She was again massaging his prostrate, though this time with a ribbed Dildo! As she kept pressing against the prostrate it sent jolts of pleasure straight to his balls and dick. To his surprise, he realized that he was humping back against the invasion, even though it made his ass clench in slight pain it still felt so good!
It was slow progress into Jim's tight ass; Heather was just enjoying the sensations of the dildo inside her as well as watching the progress of the dildo slide into Jim's tight hole. She'd sometimes enjoyed using a mirror to watch herself fuck herself with a dildo, but this was the first time she'd ever seen anything going into someone's ass. Running her hands over his hips and butt, she felt incredibly powerful and in control as she began pumping in and out of his body, feeling the way he trembled underneath her.
Reaching around him she grasped his dick in her hand and he jerked back against her, impaling himself further onto the rubber dong. Sliding her hand up and down his dick, she jerked him off again as she now aggressively fucked his ass, and Jim was feeling wonderful... whatever discomfort was still lingering in his ass was rapidly disappearing with the pleasure of her hand moving up and down on his dick. Even the slick movement inside his body was erotic, pressing in on him, invading him... he wondered if this was what girl's felt like. If this was how she had felt when he made love to her?... vulnerable and yet turned on, anticipatory and anxious, and incredibly erotic. Both found themselves moaning and screaming, in pleasure, pain, delight, and aggression! It was borderline out of control, or maybe it was out of control, neither knew, neither cared!
Her other hand reached around and cupped his balls, tugging on them as she humped him from behind. Now he was moving in rhythm with her, pushing back against the probing dick. The strap-on was rubbing her deliciously as she and Jim moved together, he was getting much more into it than she'd ever dream he would... she wondered exactly what it would feel like to have something inside her asshole. The enjoyment he was getting from it made her think that it might be good for her too... feeling incredibly lusty she began pummeling his ass harder, thrusting deep into his ass with powerful strokes. With each plunge into his ass she would let out a large grunt like scream. It was a lot of work, more work than she'd ever guessed a guy had to do from behind, but it felt good too... her clit was rubbing non-stop against the nubby surface of the stimulator.
As she got closer to her orgasm her strokes inside his ass got rougher, and her hands gripped his dick and balls, squeezing like she meant to milk him. The way the dildo invaded his ass made him gasp and jerk forwards, pressing her hand against his groin and pulling his balls away from his body. When she came, she fell forward and completely buried the dong in his ass, rubbing her body up in down with little movements and making the rubber bounce inside him. The steady friction and the tight squeeze on his dick had him cumming all over the pillows that he was laying on with his ass clenching around his new rubber friend.
When they finally sat down to watch a movie later, Heather's eyes glinted with laughter as he gingerly lowered himself onto the sofa.
"You just wait," he told her, having caught the expression; "I'll get you."
Smiling serenely, she surprised and delighted him by scooting closer and snuggling her head onto his shoulder, completely unafraid of the 'threat'.
“Sweetie,” she said, “Sleep over tonight will you?”
“I thought you’d never ask”, he said softly.
To be continued!