A Sissy's Walk in the Park

Dusk . . .

John arrived at the park just before 7 o'clock and parked on an angle so he could see both the driveway and the entrance to the walking trails. The man in the passenger's seat, Todd, was a friend and co-worker, and the man in the backseat, Mark, had been selected from a short list of candidates who'd responded to his ad on a fetish site based mainly on the size of his cock.

"Okay, this is it," John said to them. "She should be along any minute now so you boys might as well get moving. Remember where you're going?"

"I think so," Todd said. "Straight down the main path till we reach the fork in the road, go left, I wait on the small path on the left about a hundred yards down, and Mark waits about another hundred after that and waits in the middle of the path until he sees you."

"Right," John said. "I'll get her going down the left hand path and drive her towards Mark, when she sees him coming down the path she'll probably shoot up the little path on her left and run straight into you."

'You seem pretty sure about all this," Mark said with a hint of skepticism. "Are you sure this is cool?"

John turned in his seat so that he could look him in the eye, "It's going to be fine, trust me. You guys are going to love her."

"But, how do you know for sure she'll come?"

John smiled patiently, "Because it's Wednesday, and she always comes on Wednesdays . . . it's the only day she ever comes and it's always around this time because there's never usually anyone else here. She likes to walk alone."

With that said, the two men exited the car. John checked to make sure Mark had remembered to take the backpack with their gear along with him but said nothing when he saw him shrugging it over his shoulders as he and Todd made their way towards the entrance to the paths. The stage was set, now all he could do is wait for his star to arrive.

Tammi

John had only just met him/her that summer, but he quickly became obsessed. The day he met Tammi he'd quite literally walked into her out on the trails. He'd been out there as a last resort hoping to find some quick relief with a horny little twink and had encountered only a pair of senior citizens who were busy blowing each other in the bushes. Men had been using this particular park as a place to cruise for anonymous blowjobs from other closeted men for generations, and there were parks just like it all over the place. Parks . . . rest stops . . . public washrooms . . . everywhere. But John liked this one because it was set back from the highway a little and sheltered from view. He only came to places like this as a last resort, and at that time he'd been too busy working to make dates in the usual way. It wasn't his personal preference, but sometimes it was too convenient and too easy to resist. The place was hit or miss, they all were, but more often than not he could get his knob polished in under an hour.

The day he met Tammi, he'd struck out and was making his way back towards the entrance when he'd spotted what he thought was a female walking towards him on a merging path. She had a hoodie pulled up over her head and she had earbuds in her ears, so she didn't even know John was there until their paths connected and they were suddenly eye to eye. He was immediately struck by how tall he/she was, and how pretty. She had broad shoulders and tombstones for feet but she had a great physique and a perfect little ass.

She'd jumped back startled and looked as though she might bolt and run off. John had taken a few steps back, holding his hands up non-offensively and leaving her ample room to pass. "Sorry," he said. "Didn't mean to scare you."

She looked at the path ahead rather than him as she answered, "Don't worry about it."

"Nice day for a walk, isn't it?" John asked.

That seemed to make up her mind and she walked past him, saying nothing more, and he'd walked along behind her at a distance back to the parking lot, enjoying the view of her tight little ass and long legs.

On a whim, he returned there the following Wednesday at exactly the same time, and there was the same little blue sedan with the dark tinted windows that he'd seen her drive out in the week before. She wasn't in the car, so all John had to do was hang around the main path until she came off of the trails. This time, they talked for a few minutes before she departed.

Over the proceeding few weeks, they talked more and more, eventually even coordinating so they could meet there at a specific time, and it became apparent to him that she wasn't out there looking for an anonymous hookup; she just wanted to go outdoors . . . to walk as a female in a place where she was unlikely to be seen, mocked, or physically assaulted. And what better place than a cruisy park where closeted married guys went to polish knobs on the down low? It made sense, she/he had probably only ever been able to dress up at home, or at the homes of her lovers and in the privacy of hotel rooms. Out on the trails she had little worry of being accosted by hooligans or gay-bashers; aside from an occasional unwary dog-walkers and joggers, everyone was there for the same thing, and nobody wanted to attract attention to themselves. As long as she kept her head down and kept moving, nobody would ever mistake her for a girl looking for sex.

Tammi intrigued him, there was something dangerous and dark about her. The way she dressed in tight spandex that left little to the imagination, and the way she rimmed her eyes with dark makeup the way girls do when they're looking to get back at their fathers for something. She definitely liked sex with men and John couldn't imagine a single man out on the trails refusing her if she'd offered . . . but she wasn't offering. She liked cock and could probably have all she wanted (and more), walking into the woods with a man she'd just met and blowing him or letting him fuck her didn't interest her. So . . . John wondered, what did she want?

He'd been careful to keep their conversations rated PG, opting to wait until she was ready to turn the discussion in that direction. And, on their fifth (or maybe it was the sixth) Wednesday afternoon out on the trails, she finally did.

"Why do you come here?" she'd asked on that sunny summer afternoon.

He could only shrug, "Out of boredom, mostly. Sometimes I just want a blowjob without any feelings or legwork attached to it. Lately I've only been coming to see you."

She ignored the compliment and continued with her line, "But what do you get out of it?"

"Blowjobs, mostly," he answered simply and honestly. "Now it's your turn . . . why do you come out here, if not to hook up?"

"Well," she said hesitantly, a blush rising to her cheeks. "it's not that I don't want to . . . I don't know, maybe it's too much."

John sat on one of the log-cut fence posts lining the final stretch leading to the parking lot and encouraged her to go on, (he also happened to be sporting a huge hard on and didn't want to scare her off.) "I'm all ears . . . let's hear it."

"In all of my fantasies," she explained reluctantly, keeping her eyes on the path for anyone coming as she confessed to him, "I know people aren't supposed to fantasize about this kind of stuff . . .."

"Nonsense," he smiled, "whatever it is, I promise you I've heard worse."

So, with his cock throbbing angrily in his jeans, he patiently listened as she broke it down for him. She called it: The Five F's.

Feminized . . .

Pretty self-explanatory, but coming out to parks like these dressed as a man like everyone else and having sex with a stranger in the woods did absolutely nothing for Tammi. But dressed as a female . . . more specifically, dressed in clothing that had the effect of giving men a hard-on the way what she was wearing was giving him one, was both intoxicating and addictive. Just being out there having that conversation with him, she said, was making her heart pound.

Followed . . .

As a male, Tammi said, she could (and had) go out for walks in isolated areas like this one and never really have to worry about anything. Once in a while the cops liked to park out in the lot and write down everyone's license plate number as a deterrent, but it was pretty safe otherwise. As a girl however, she felt intensely vulnerable. Tammi could recognize the way men looked at her body when she dressed like that, and he knew exactly what they were thinking; putting their cocks inside of her. That was something that most men could go their entire lives without ever having to worry about that, but that sense of fear was a huge turn on for Tammi. And so, the idea of men following her around on the walking trails with their cocks hard as they thought about the things they'd like to do to her was an essential part of the experience.

Forced . . .

Here's where Tammi got a little bashful and John had to coax her a little in order to get the specifics, but eventually he got the picture. While being feminized removed most of her confidence in her ability to defend herself against aggressive sexual advances, it didn't erase the reality that he had the strength of a male and could probably fight someone off it push came to shove . . . after some prying, John got her to admit that being tied up, held down, handcuffed, caged or otherwise restrained was intensely erotic to her. She frequently fantasized about being in such a position while a man (or a group of men) forced their cocks inside of her. Tammi was very vague in her description here, but it seemed that a certain degree of pain would be welcome. Though she was no masochist, she wanted it to hurt a little.

Fucked . . .

At the end of the day, after the dressing up and being stalked, captured, and restrained . . . the ultimate act of emasculation; the most significant thing a man could do in regards to dominating another man's body and soul . . . was to fuck him. Fuck his mouth . . . fuck his ass . . . cum on his face . . . make him swallow semen . . . all the more powerful and devastating to his masculinity if the boy being fucked enjoys it, inadvertently or otherwise. "Rough but not violent" was how Tammi described it, which made sense considering that she'd be tied up or otherwise restrained. A hand on her throat or a few good licks with a leather belt was all the violence needed to remind her who was in charge, assuming she needed to be reminded at all.

Filmed . . .

This aspect spoke to the kinkiest side of Tammi's nature. While it was one thing to have an intense sexual encounter with a man (or several men), the memory quickly faded, blending in together with all the other experiences she'd had. Having video meant that she could relive the experience anytime she wanted to, every moan and cry, every tear shed and every man's orgasm shot into or onto her body . . . but that was just a bonus. The thing she really liked about being filmed was the exchange of power that was taking place; with video evidence of a male dressed in women's clothes sucking cock or taking it in the ass, you could just about own that person. The holder of that video could choose to send it to whoever they chose, post it just about wherever they chose, even monetize it and profit from it if they were so inclined (and providing the quality was good). Tammi admitted to him that she'd once found herself trapped in a loop where she'd been filmed during a gang-bang and found herself in another one when she went back to retrieve the footage from the first one resulting in TWO gang-bang videos, neither of which she ultimately ended up receiving a copy of let alone the original. Ever since then she insisted on maintaining control of the original, which she would then post online under her own volition, sharing it with those whom she wanted to see it. By doing so, the people who received it were given the power to ruin her life, and use it to blackmail her into further sexual encounters with her consent intact.

By the time she finished laying out her five F's, John's cock was throbbing in his pants and his underwear felt wet. He was half tempted to jump up, hard or not, grab her by the neck and bend her over the fence he was sitting on and fuck her right then and there. However, at that point Tammi was like a sexy little doe he'd stumbled upon in the woods (quite literally), and that any sudden might spook her back into the brush, never to be seen again. He'd only gone out there to have meaningless empty sex with a stranger, but he'd had the good fortune of stumbling upon something that could be more . . . much, much more.

She wasn't asking for sex and she wasn't offering it either, yet she seemed to be giving him the kind of details girls only ever give when they're interested. John had been around enough to know that Tammi would probably never offer him sexual favors, not because she didn't want to but because she simply wasn't wired that way, and never would be. If he wanted her, and he did . . . he was going to have to take her.

He began his search for like-minded men to help him.

7:20pm . . . time to hunt.

John watched Tammi's little blue sedan with the blacked-out windows drive past him and park in the space closest to the trail-entrance. The sun was still hovering over the tops of the tall forest pines and shining directly on her while John was watching her from his car, unseen in the shadows. The driver's side door swung open and she stepped out . . . the mere sight of her made him hard, despite the distance. From a hundred yards away, he could have been looking at one of those tight-bodied hot-wives who came out to his Thursday night Yoga class. Tammi had even dressed like one of them in a sports bra showing off her belly and a pair of shiny red tights that could have been body paint for all that it revealed. She was wearing her auburn hair in a pony-tail poking out the back of a baseball cap, a black windbreaker, and a pair of dark sunglasses.

She looked in his direction and held her hand up as a shield from the sun, but even with shades on she didn't and couldn't see him parked there. Apparently satisfied she was alone as usual, she locked her car and headed out onto the trails.

His eyes locked on her ass as she walked away from him . . . even at that distance he could make out the seam riding up her ass accentuating both cheeks beautifully, and leaving him to wonder what sort of panties she was wearing, or if she were wearing any at all. He waited until she'd crossed the barrier separating the parking lot from the cedar-chip path leading out to the beaten trails before exiting his vehicle and setting off after her at a slow walk.

He reached the entrance to the trails within a minute or so and stepped under the cool darkness of the forest canopy. It took a minute or two for his eyes to adjust before he saw her form, now easily a quarter of a mile up ahead of him, barely a black speck inching along the highway of brown laid out before him.

He quickened his pace to a fast walk as he tried to gauge the distance he'd need to catch up with her at just the right time; at the fork in the road where they'd first met. There was no need to panic or run . . . because while Tammi would be staying on the main path to the fork, John would be taking a short cut which would and should land him where he wanted to be at just after she'd passed. When he saw it on his right, he ducked off of the path and broke into a light jog. At the last moment, he could swear he saw her turn around to see if anyone was behind her, but he couldn't say for sure.

His route was a narrow-beaten path through the heavy brush that ran along the top of the gully as opposed to following her all the way down and all the way back up again on the other side. That said, while Tammi was walking on a nicely groomed path of wood chips, John had to move twice as fast along a hard dirt path laden with hundreds and thousands of rocks jutting out from every conceivable angle. It was hard going and by the time he reached the other side of the gully he was panting for breath and sweating hard. He rejoined the main path and carefully peered down the path to see Tammi as she began making her way up from near the bottom.

He had a few minutes . . . no more than that.

John walked a dozen paces up the right side of the fork, turned back and stood there waiting . . . any minute she'd be cresting the top of the gully, winded and physically tired if not exhausted, and that would be that.

The top of her hat appeared on the crest of the hill followed by her sunglasses, then her mouth . . . her lips painted bright red and her pony-tail swinging back and forth behind her like the pendulum of a clock. Her shoulders . . . then the curves of her tits (fake as they may be) stretching out the fabric in that sports bra. Her stomach, and finally, her hips and her crotch, which was well-tucked and barely more than a mound that could have just as easily been vulva as cock. Then her well shaped thighs, followed by her big clomping feet in sneakers.

John loved every inch of her.

She reached the top and stopped to catch her breath and turned to look back down the incline she'd just traversed and giving John a much closer look at her ass. Now he could make out the faintest line of a thong beneath the shiny red fabric wedged perfectly up her ass. He had but one thought . . . fucking that ass as hard (and for as long) as he possibly could, and filling it with hot angry cum . . . her punishment for his arousal.

She turned around and began heading up the right fork in the path, directly towards him.

Their eyes met and she stopped dead, like a deer caught in the headlights of an oncoming truck. Whatever she saw in his expression frightened her enough to take a couple of steps back at which point her gaze dropped down to the massive hard on pitching a tent in his pants, and that cause her to bolt at a quick pace up the left hand of the fork in the path, and toward her inevitable capture.

John set off after her at a leisurely pace, in no particular hurry; the other two men were waiting for them a couple of hundred yards further down the path . . . she wasn't going anywhere. Instead he relaxed and enjoyed seeing the muscles in her legs and ass twitch through the tight spandex as she attempted to flee.

Tammi looked over her shoulder nervously, and quickened her pace nearly to a jog despite the fact he wasn't even trying to catch up to her. When she looked away he smiled, anticipating the fun that was about to follow. Her pony-tail was swinging madly as she scurried down the path, totally unaware of what was waiting for her. Further down the path, about a hundred yards or so past Tammi, John could see Mark's rather large form in the middle of the path. His head appeared to be down like he was looking at something in his hands and John realized that the big goof was looking at his phone. He raised his thumb and his forefinger to his lips and let out a long whistle.

Mark's head snapped up and he spotted Tammi who saw him at the exact same moment. She turned back and stopped once again at the sight of John closing in on her. Panicked, she looked around for an escape. Lo and behold, just up ahead was the small beaten path to her left. She burst into a run and vanished up the path and into the brush. Mark began running after her until John called out to him, "Relax! She's not going anywhere!" after which he nodded in understanding and slowed his pace.

John and Mark reached the small beaten path at almost the exact same time and walked up together. The path narrowed as it cut through a dense patch of brush which then opened up into a small clearing where a massive oak had once stood. It had long since fallen and was slowly decaying on the forest floor allowing sunlight to penetrate the small area and giving birth to smaller growth that would one day take its place, feeding on its corpse. Standing beside the fallen tree, they found Todd struggling to maintain his grip on Tammi. He had one hand clamped on her elbow and the other on the back of her neck, and she was putting up a pretty good fight, but not that good, and not very hard.