Adventures of Shemale Sandra Ch. 02

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Sleeping on the (Foot)Job.
4.4k words
4.3
40.5k
12

Part 2 of the 2 part series

Updated 10/24/2022
Created 06/01/2004
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Elyquent
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12 Followers

Sandra thought about Jeff all through the next day. He had been her first, and she could still recall their experience as if it had happened only moments ago. She could feel his rough hands on her tender flesh; his sweat falling in beady drops on her soft belly; his stiffled grunts echoing in her ear. And his force! Oh how he had bent her to his will! Used her for his pleasure! She had absolutely loved it!

Recalling this, it was no surprise to her that her routine masturbation session that morning ended rather abrubtly. Normally, she would wake up and instantly become fixated on the bulge trapped inside her silky nightie; minutes upon minutes of frenzied self-gratification following. But this particular morning had been different.

At first she awoke gazing upon the usual sights. The cool morning air had riddled her deeply-tanned skin with goosebumps, her perky brown nipples were in a state of silk-induced arousal, and of course the nightie she wore to bed was embarassingly bunched-up about her waist, the fleshy rod just past it in full salute. But when she instinctively reached for her first order of business, Deja Vu struck. She recalled at that point being perched on a helplessly swollen tool, bounding up and down with all the effort she could muster, and moaning for the first time in her life not because of self-induced pleasure but because of the mutual kind.

Then she remembered the climax. Having trembled violently under its force, she could hardly forget it. It had only taken minutes to occur, but it was of the quality and quantity that even hours of her own efforts couldn't match. Not even the one that morning, which, by the time she reached another thought, had already occurred. And in well under a minute's time. It was still a splendid one though, of the variety that lasted right up until the member became limp, its shrinking mass continuing to drip that which seconds earlier it had forcefully projected. It didn't come with the usual bout of post-depression, either, thanked Sandra.

Nope, she was in high spirits that day. So much so that even the dread of the upcoming clean-up didn't hold her down. In mere moments, she had thrown off her nightie and walked to the nearby bathroom. There, some tissue was used to clean off the shiny matter from her belly and crotch, and, not longer after, the shower started up. Sandra stepped in.

It felt good to be clean, she decided with a sigh. But she knew that it wouldn't last for long. After some tidying up and and a few errands, the buxom shemale had plans for another night of fun and adventure. And getting dirty was but a requirement as far as she was concerned. Although perhaps she didn't quite expect what she got.

Her adventure started in the library of all places, where she was picking up some books for a report due Monday. It was the public library, of course, as she loathed the one tied in with her school(encounters with people there almost always met with unpleasant results, as rumors about her had spread, and she was even looked down upon by most teachers who, at one point, she had awkwardly told the details of her changes to) Her intent was to be expedient but, by an odd twist of fate, she stumbled into just the type of person she was here to avoid -- a fellow student.

He didn't seem the boisterous type, nor even the socially conscious type, but a nagging suspicion told her that he might be the nerdy conformer type; a type that wouldn't hesitate to single her out for what she is, assuming they knew. But Sandra resigned that he WAS in her way, and that she DID have to get the books for her report, so she went ahead and braved it by approaching the aisle he was on.

Timothy Landry was what he was known by, to the people who could be bothered to care. His collection of non-fiction books was rivaled only by the amount of girls he'd secretly admired, but had never made a move on in high school. He'd cursed himself for this social anxienty, in private, and in private, he'd vowed self-rehabilitation for it. Yet, in private, he still lived. And he desperately wanted that to change.

His eyes met hers for an instant and quickly darted away. Under his breath, if anyone wanted to get that close, he could be heard uttering a thousand curses. What to do, what to do, he hurriedly wondered, and silently wished at this point that he could, just for a moment, open up his bloated notepad of pick-up lines and various seduction tips. There's a hot girl just steps away from you, Timothy, he reasoned. You need to do something, his inner conscience demanded. What's wrong with you, it again questioned.

"Hello."

Sandra looked his way and noticed more a look of nervousness than of incredulousness. Her mind was at ease. "Hi," was all she said. She never in her wildest dreams thought that this scrawny, messy-haired guy would try to make a move on her. "How are you?" Timothy shot back with practiced foresight. "Uh, I'm okay..." said Sandra, trying to do a bit of her own redifining now that she wasn't so desperate for attention.

"That's good to hear," responded the guy with matching brown hair and eyes at her feet. He paused and added, "Do you go to school?" Sandra had to admit she was a little flattered by this point. "Yep, just a few miles away at the university," was her answer. Timothy seemed to be in deep thought. "Oh," he said a bit too seriously for friendly conversation, "Why aren't you at the library there?"

Like Timothy, Sandra had some pre-planned responses of her own: "I like the peace and quiet here," she stated. "Me too," he said and then backpedaled, "Not that I go to school." Sandra considered this and then spoke, "Oh? Do you work?" Deep in thought, he debated whether or not he should lie, but he couldn't think of a good enough one in time. "No, I stay with my grandmother," he muttered.

"Oh, cool."

"So can I get your phone number?" he asked both sincerely and abrubtly. Sandra laughed softly at his remark and explained that she doesn't have one. His response was, "Oh," and then his brain seemed to shut down. He was looking back through the books on the shelf nervously. Sandra felt kind of sorry of him, much like she did with Jeff, and said, "I have a house though." She was trying to keep what she said short to preserve the feminineness of her voice, but it didn't seem to matter because, as anyone at the time could have told, Timothy was quite shaken by this.

"Uh, we-well, maybe I'll stop by sometime, " he stammered. Sandra giggled; she loved being in control.

"How about now, sweety?"

"Su-sure!"

Timothy Landry's dreams had just come true. As for Sandra, well, she had just saved herself some time as well as the risk of possibly being singled out at a club or bar.

And so they walked out together, Timothy forgetting all about his book, and Sandra all about her's.

They arrived at her house after a long, quiet car drive, during which about the only thing they learned from each other was their names. Even Sandra became nervous due to how little Timothy had spoken, but somehow his apparent nervousness had made her feel more than a little kinky. She loved what she could do to guys, and it made her want to relieve all of her built-up sexual tension every time she saw a guy visibly attracted to her.

So they sat on that familiar couch where Sandra had first lost her virginity; oddly, Timothy sitting on the opposite side from her. Could he really be that naive, she wondered.

"So, what now, Timothy?" Sandra said with a mischievous smile.

He looked at her and grinned, "Sex?"

Sandra laughed.

Timothy seemed to really lighten up at this point. "God, you're the coolest woman I've ever met," he spoke next. Sandra could do nothing but blush at this remark. She stood and decided to give him a little titty show for his compliment. Sandra never wore a bra, so just walking around she was naturally teasing guys. Her breasts were hardly easy to ignore at a full 36C, and considering that she always wore tank-tops or V-necks, a lot more guys had become excited at her passing by than she could even imagine. Her shirt this particular day just happened to be a Nike V-neck, and it was having a similar reaction on the slightly flustered Timothy.

She hadn't even popped her shirt off yet, but he had certainly popped something of his own sitting on the couch. He wasn't trying to hide it either, she noticed. Still, she continued with her efforts and thrust out her chest, giving a little shake. Her tanned breats bounced around and rubbed together, creating a warm friction under her stretched shirt. She jiggled her chest some more and one of them slapped lightly against her skin. She looked at Timothy to see what his reaction was, but instead she caught him looking at something on the floor. Weird, she thought.

Sandra looked down, but had no idea what it could be. When she glanced up, he was already staring at her boobs again, so she simply shrugged it off. At this point she decided that maybe it would be a good idea to let the twins out, and then make her way back to the couch. Even though she had taped her girly parts up with stronger tape this time, she was worried that they still might pop out unwantedly soon. Her jiggling titties weren't the only thing exciting in this room, after all.

She strutted over to Timothy, swaying her hips seductively in her mini-skirt. Smiling, she bent over and pulled down the neck of her stretched, skimpy shirt. His face was only inches from where her dangling breasts were, the large, dark brown nipples crowning the tips clearly visible through the wide open neck of her shirt. He anxiously reached in and cupped one of the huge twins as best he could, tweaking the inviting nipple with his palm. Sandra stayed leaning over in front of him and then went in for a kiss. She stuck out her tongue, and Timothy took it between his lips and sucked.

Teasingly, she kept pulling her tongue away from his lips and then darting it near them again. He seemed to like it. Her next move was to place a hand on the unsightly little bulge in his pants. As soon as she did though, she heard and felt a little peeling sound and knew instantly what it was. The tape hadn't held up like she wanted. She became a little worried, but then decided that he was the type of guy who wouldn't care about her special girly parts. Standing tall, she lifted the Nike shirt over her head, while a huge bulge of her own presented itself at the front of her mini-skirt.

Her tits popped out seductively, but that didn't seem to be what he was looking at. It wasn't the floor either. No, he was staring straight at the newly-formed lump poking at the front of her skirt. "Is that a dick?" he said with startling assertiveness. Sandra blushed and nodded. His eyes lit up. "Holy shit, I love shemales!!" he said it his most confident tone yet, "I see you girls all over the Internet!!" Sandra giggled; it was a little flattering, but she didn't particularly like being compared to other girls.

"Oh yeah, do you like what you see now?" she said, not trying as hard to conceal her natural voice as she was before.

"Hell yeah!" Timothy announced.

Sandra was elated. She was about to commence her fuck of the day and it wasn't even night-time yet! She did think it odd though, that Timothy seemed to be taking the initiative now that he knew her true secret. He had already laid her back on the couch and was proceeding to peel off her mini-skirt just since he had found out the news. She might have even considered him to be rushing things; that is, if he hadn't stopped for just a moment to stare at the flimsy white panties holding in her engorged girl-cock

In all of Timothy's life he had only seen one thing that excited him more than what was now before his eyes, and he knew that he could find that other thing on her slightly thick, tanned, beautiful body, too. He was in heaven.

He reached down and grabbed a fistful of slightly damp panty and rock-hard she-cock. Indiscriminately, he then jerked them both up and down and his hand. Sandra seemed to like it. She was loving the feeling of both his hand and the cotton carressing her girly-cock. It was coaxing more precum out little by little and making her extremely horny. But that wasn't enough for her, she decided. Reaching over, Sandra roughly tugged at Timothy's shirt until he resigned to lift his arms up and allow her to take it off. He wasn't particularly built at all, but that didn't stop her from flicking her tongue across one of his red nipples. Her hands meanwhile were busy undoing the buttons and zipper on his pants.

She wanted his cock badly. So badly that she almost ripped his jeans pulling them down. But her target was in sight, only separated from her by some stretched white briefs. "Mmmm," moaned sandra. She hooked her index finger in the waistband and tugged the tight briefs just bellow his entrapped hard-on. "Oh Timothy," she said softly, biting her lip. His swollen cock was curved just a little to the right, which she thought was extremely sexy. But before she could touch it, he stood and finished taking off his remaining clothes: underwear, jeans, shoes and socks. Then he examined her.

She felt very self-conscious as he looked over her naked body, the only articles of clothes on it being a pair of skimpy, wet panties and flip-flops on her feet. But he soon got rid of those, too, taking a big whiff of her panties before throwing them aside savagely. Her flip-flops came next, and they were tossed aside as well in a similarly brutish fashion. But then something unexpected happened. He had begun to massage a part of her body no one had ever laid hands on before. He was rubbing her feet, and it felt simply amazing considering how tired they were from breaking in the new flip-flops. His fingers-tips were firmly but smoothly manipulating her soles and occasionally moving over to squeeze or pinch her toes. "That feels good Timothy, " she said, still a little surprised that a guy was doing this to her.

Sandra had begun to relax by this point. One of her hands was softly tweaking her large brown aureolas and nipples to excitedness, and the other, of course, was kneading her leaking little girly-dick. But Timothy had stopped massaging her feet before she even got to her third stroke; he was doing something even more strange now. His lips were wrapped around her painted big toe and they were sucking it rhythmically. He was tending generously to her sore feet with all the care his mouth could provide. Then he began dividing his attention between all of the toes.

"Ooohh," Sandra squeaked as Timothy reached her other big toe. This felt good, she thought. Her fist was wrapped a little more firmly around her swollen girly-rod now, and she was making sharp thrusts upwards with her pelvis as she stroked. Timothy seemed somewhat fueled by this because he suddenly stopped sucking and stood up, stroking his own meat while watching Sandra. Sandra looked at him sweetly. Finally, she thought excitedly, he's going to fuck me. She couldn't wait for him to hit her sweet spot.

"Do you have any lotion?" Timothy asked anxiously. Sandra giggled. "You won't need that sweety, " she said, "It'll fit fine." She stuck her tongue out at this, and shifted her shapely ass' position on the couch to face him. But Timothy didn't seem convinced. "Just trust me, " he said. Sandra sighed. She got up and strutted to the bathroom, her erection swinging from side-to-side as she did. Walking back, she smiled and laughed again, tossing the bottle of lotion his way. "Okay big boy," Sandra added, "If you think you need it." But his attention wasn't at all to lube up the meat between his legs.

Instead, he began to apply it to Sandra's bare feet. The lotion was of a thick consistency, and it felt both cool and gooey as it was lathered onto her slightly dirty soles. Sandra jumped and quivered a little as the coldness hit her, and then lay still wondering just what he was up to. He was really coating her feet in the stuff, even in between her toes where it felt especially squishy as she wiggled her curious toes about. But before she could ask any questions, Timothy spoke up.

"Sandra," he spoke and then paused, "have you ever given a footjob?" She laughed at his request. "Uh.. no," she answered, more than a little surprised. She began to wonder a little spitefully if he'd be making requests this bold if he hadn't found out she was a tranny. Some of this resentment stemmed from really wanting a good fucking, but a lot of it surrounded how both this guy and Jeff seemed to suddenly lose all their inhibitions once they found out about her little secret. She had begun to grow more and more jealous of real girls, but then realized that this wasn't the time or place for that.

"It's like a handjob, except with your feet," Timothy said matter-of-factly. Sandra sighed softly.

"Okay, I'll try."

Timothy had laid down in front of her by this point, and so she lifted up her oily feet and placed one on either side of his strained cock. A big smile grew on his face as she began to work on the coordination in her feet by practicing the raising and lowering of them, all on his lucky dick. It was thoroughly lubed up now from all of the lotion, and he had to admit that Sandra's soles felt absolutely lovely on it. He could feel every tiny little wrinkle on the bottom of her feet as it passed over his swollen member. It was beyond a turn-on to him; it was an obsession.

Sandra, however, felt hesitant.

"Am I doing it right?" she wondered aloud, in an almost apathetic voice.

"Oh baby, it's perfect!" he replied through labored breaths.

Her fears seemed to shrink, as did her now-partially-soft cock; she just wasn't that turned on by this. But she continued to perform the footjob on Timothy, her back and head slightly off the couch and her legs in sort of indian-style position as they guided their respective feet up and down Timothy's reddened member. There was now a squishy, almost-slapping sound recurring, and she knew that although part of it was her softening cock flapping around helplessly, hitting her stomach, that it was mostly a strong suction gained from solid lubrication and the practiced rhythm of her feet.

Sandra glanced at Timothy and noticed that he was ogling her lotioned-up feet, apparently on Cloud Nine. Slowly, she began to realize that this was actually having a massive effect on him, and at that point her desire to control began to manifest itself as gradually increasing arousal. She was starting to ger horny again.

To speed up the process, she stopped her soft little cock from its swinging and starting to yank the skin on it up and down feverishly. This, too, took more coordination. It didn't stop her though. The footjob continued.

Her feet were beginning to get relatively dry at this point, and Timothy reached over to grab the lotion. He popped the top on it and squirted some out. Being as horny as he was though, it was naturally hard to focus and so he did miss his target by a fair amount. The stuff came out in an enormous squirt, most landing on Sandra's busily jerking feet but a lot pouring onto Timothy's thighs and the couch, too. He was a bit sheepish.

But Sandra didn't seem to notice. She was speaking to him by this point

"You like that baby?" she gasped, "Are my feet turning you on?" She continued, "Your big cock feels so hard in between them that I just don't know what to do. My little toes are doing the best they can to make you cum."

Timothy was speachless, but he had started grinding in time with Sandra's greased-up feet. Meanwhile, Sandra was still tugging on her girly-cock as it switched between fully erect and partially so. It couldn't make up its mind, so she had decided to slide just one little innocent finger into the asshole under it and probe around. It seemed to be working for the most part, but she was still far away from where she wanted to be. And it appeared that she was the only one feeling this way.

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12 Followers
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