Jack Hawkland
If he’d had the money and lacked the shame, Gary would have made another appointment for the next day. More sensibly, he booked a session for the following month.
He couldn’t wait. How serious was she about her inferences? Was the lack of cash from her lazy boyfriend forcing her to consider ways of boosting her salary? Was she going to do something to “earn” a generous tip this time?
Gary didn’t want to get his hopes up too much. She was such a nice, shy, sweet girl. She was just teasing, surely?
On the long-awaited day of Gary’s fourth appointment, Teddy greeted him pleasantly, although he noticed that she was not wearing her usual “uniform.”
Her crew-neck black T-shirt had been replaced by a white top with a boat neckline. Nothing fancy, nothing provocative, but it was nice to see a little more of her skin showing—even if it was just her clavicles.
Otherwise, her fairly subdued greeting and a lack of her usual playfulness suggested that perhaps her parting comments last time were indeed just a joke that got lost in translation.
Gary showered as normal and took up his position face down on the table inside the over-scented confines of the massage room.
Teddy was quiet today, and the first half of the massage took place in almost complete silence, save for the occasional pleasantry. But it was another beautifully attuned exploration of his musculature.
It was gentler than normal—still delightful, but there seemed to be more tenderness in her strokes today. Perhaps he was overanalyzing again? But this felt more like the caring, gentle touch of a partner rather than the manipulations of a physiotherapist.
He allowed himself to embrace its delights, relaxing fully as her fingertips and palms traveled over his back, his arms, his buttocks, and then finally, his legs.
“Okay, it’s time to turn over,” she told him.
There seemed trepidation in her voice, though he couldn’t understand why. He was turning over without much in the way of an erection, and there had been no banter between them—cheeky or otherwise.
She let the towel settle over him, covering his modesty as usual, and moved to the foot of the table to start massaging his feet. It was then—finally—that he noticed.
As Teddy leaned over to begin coating his feet in oil, her loose boat-neck top gaped open, and Gary realized she wasn’t wearing a bra! He suppressed a gasp and quickly brought his arms up from his side, folding them behind his head to give him the leverage to peer down the table.
She wasn’t quite exposing herself—the business ends of her perky breasts were still hidden from view—but the window she had created allowed Gary to see them hanging delightfully within the confines of her top.
They looked smooth and tanned and were so firm and pert that even the vigorous movements of her hands barely elicited a sway.
Inevitably, Gary’s cock responded. The small towel covering him was almost thrown off as his appreciation of the view became evident. The movement must have been obvious, but Teddy ignored it, continuing to focus on her foot massage.
She was doing what Gary had been doing during previous sessions: testing the waters, maintaining plausible deniability, so that if things escalated in a way that either party wasn’t happy with, it could be explained away and laughed off.
Gary worried that if he said the wrong thing now, making Teddy feel uncomfortable or that she had made a mistake, she would immediately cover up and deny everything. He played it at her speed and let her continue without comment.
She moved up his legs. Normally, she’d go to the side of the table to do this, but now she reached up from the foot of the table, bending over in an even more exaggerated manner and affording Gary the best possible view down her top.
Those tits looked amazing! He craved a better look. A glimpse of a nipple, even a hint of areola, would suffice, but the tips of her gorgeous, supple assets remained obscured.
He had to satisfy himself by marveling at their shape, their firmness, and the fact that even without the encouragement of a bra, they almost touched in the middle, creating a stunning cleavage.
His observations were causing his rock-hard cock to twitch under the towel, and yet Teddy still didn’t acknowledge it.
She did, however, finally look up toward Gary’s face. Her expression was neutral and hard to read.
With both hands on his ankles, she smoothed her palms up his shins, her body leaning further and further over, her eyes never leaving Gary’s.
He had the best view yet down her top. He could even see her toned stomach through the gap between her hanging breasts. His cock twitched again, and Gary flashed his eyebrows at her emotionless face.
Finally, she beamed her megawatt smile back. “You relaxed?” she asked innocently.
“Well, I’m not sure that’s the word I’d use. But it’s very, very nice.”
She smiled a satisfied smile and focused again on her leg massage. With each stretch of her arms up Gary’s calves, he got an ever more generous peek at her chest.
She then used both hands to concentrate on one calf at a time, deliberately bringing her arms together as she did so, squashing her boobs together and creating an obscene amount of cleavage.
That deepened the gape of her top, and Gary got the first, briefest flashes of nipple. This was maddening. Until now, he had been grateful for the view, but now this simple white garment was vexing him.
He no longer wanted to see most of Teddy’s breasts; he wanted to see all of them.
He contracted his rock-hard cock in frustration, flexing the muscles in his groin to disturb the towel draped over him.
He flexed again and again to draw the attention of his masseuse and, in doing so, forced tiny volumes of precum to seep from his glans.
Teddy finally acknowledged the vigorous twitching of the towel and ceased her leg-fondling lunges, moving to the lower side of the massage table. Had Gary’s erectile gymnastics prematurely ended this voyeuristic display?
“Is it uncomfortable? Shall I remove the towel?”
Teddy’s inquiry was delivered without a hint of playfulness or suggestion. Despite the view she had been affording him, Gary felt she was attempting to maintain a tenuous innocence regarding how this massage was panning out. But this was the first time she had ever encouraged him to expose himself to her—and there was no disguising his level of arousal.
“Er…okay?” he tentatively responded. “I mean, as long as you’re not uncomfortable or anything…”
Teddy answered with a subtle smile and slid the towel ever so slowly, inch by agonizing inch, off Gary’s prone body. His turgid dick resisted the leisurely reveal, but when the edge of the white cotton finally lost its purchase, it eagerly sprung into view.
Initially ignoring the proud display, Teddy began massaging his thigh just above the knee.
No longer able to see her wares, Gary instead focused on her face, trying to read her expression and glean frissons of sexual excitement from her occasional glances at his exposed erection.
Alas, she was stoic, and Gary was worried that she was doing this unwillingly. But then he reminded himself that he had made no requests, no demands, no bribes, just genial innuendo. And she was responding.
He waited for her to glance at his cock and twitched it as hard as he could.
This time, the movement elicited a smile from Teddy and another unplanned reaction as more precum forced its way out of his veiny shaft. The clear, silky liquid oozed from the tip of his reddening helmet and formed a small pool just below his navel.
Teddy noticed but didn’t respond. She increased the intimacy of the massage by running her warm, lubricated fingers up the inside of Gary’s thigh, letting her fingertips graze his balls as they spread the oil.
Gary decided to chance a move. Her deliciously pert ass was within easy reach, and he tentatively pulled an arm from behind his head to reach a hand toward it.
Teddy decisively grabbed his hand and placed it firmly back by his side.
“No. No touching,” she said firmly.
Gary felt suitably admonished and more than a little guilty.
“Sorry. I’m sorry. I didn’t mean to… I’m sorry.”
Thankfully, Teddy immediately smiled to reassure him.
“Just looking today. Okay?”
“More than okay,” said Gary, trying to sound as grateful as he genuinely was. “Only… I don’t have anything to look at right now.”
Teddy smirked at the remark, shaking her head at his cheekiness. Gary left it at that, not wanting to push things any further but hoping that his words might encourage her to lean over a little more.
After a few minutes of using up the oil on her hands with Gary’s thigh, she went one better: in one swift and nonchalant movement, she pulled off her top and exposed her picture-perfect breasts.
They were spectacular. By no means small—c-cups maybe—but remarkably pert. They looked natural yet had a roundness that would have made Gary suspect otherwise, were it not for the way gravity subtly pulled on them. Puffy pink areolae surrounded firm bullet-like nipples that pointed proudly forward.
If Gary were to imagine the ideal pair of tits, they would look very much like these. She threw her discarded top onto a chair, and they wobbled joyously, confirming their all-natural quality.
This “no touching” rule was going to destroy him, but it was a small price to pay for an audience with such erotic beauty.
Teddy squirted more oil onto her hands and rubbed her palms together. Whether deliberate or not, it caused her boobs to dance around her chest, jiggling delightfully. She moved around the table and started rubbing her scented lubricant into Gary’s other thigh.
Gary was spellbound. Every manipulation of his thigh and every slide of her hands caused her breasts to bounce or wobble or jiggle in infinitely hypnotic ways. As cheesy and pervy as it sounded, he had to comment.
“Teddy, you are absolutely stunning.”
She shyly acknowledged the compliment with a suppressed grin and continued her massage.
Gary tingled every time she brushed his ball sack. He wasn’t allowed to touch her, but would she touch him? Would this massage include that most welcome of sordid clichés, the happy finish?
As her hands moved north, across his hips, she expertly avoided contacting his erect penis.
He cheekily flexed it a few times as her fingers danced around his pelvis, but instead of making contact with her hands, he only succeeded in depositing more precum onto his stomach.
If she was intending to wrap her warm fingers around his agonizing erection, it was seemingly going to be at the end of their allotted time. But it didn’t matter too much—not when her journey up the table was bringing those majestic tits closer and closer toward him.
Now her hands were on his chest, and Gary was examining every pore on her breasts, every ridge surrounding her nipples, every little freckle adding character to those glorious, majestic mammaries.
How he would love to reach up and cup them, squeeze them, bury his face in them. But he obeyed the rules and just longingly stared.
His pulse quickened as she lifted an arm from his side. As her thumbs kneaded up from his bicep and toward his forearm, his hands were brought achingly close to her chest and the fleshy mounds that he longed to brush his fingers against.
She manipulated his wrist, and his desires were met for the briefest of moments when the back of his hand grazed an unyieldingly hard nipple. Whether the contact was intentional or not, he sighed his approval.
Teddy moved to the other side of the table and repeated her actions on his other arm. This time, she held his forearm closer to her chest as she spread oil between his fingers and pulled on them as she did every session, eliciting those little cracks of air.
Each tug forced his fingertips into the warm flesh of her breasts. The side of his hand brushed over her left nipple several times before she was done with his arm, and the pool of precum collecting on his stomach grew ever wider as he flexed his manhood with each delightful contact.
Teddy gently lowered his arm and stood over him at the head of the massage table. He could no longer see her face, just the toned lines of her lower torso and the undersides of her breasts, the view accentuating the protrusion of her nipples.
She massaged his scalp for a minute or so, and Gary stared open-mouthed as each of her slow and deliberate breaths caused her chest to subtly rise and fall.
Eventually, she did exactly what Gary had hoped: she leaned over and spread her hands over his pecs, her tits hanging just centimeters above him as she smoothed his chest hair with her palms.
He was torn. Raising his head a few inches would allow him to press his face against her hanging bosom to suck those beauties, if only for a second. But this was the closest he could get to her spectacular boobs, and he didn’t want to cut the display short with a massage-ending imposition.
Besides, her strokes were going lower and lower, past his nipples and onto the top of his stomach. If she carried on like this, he wouldn’t need to extend his neck; she’d be pushing her tits into his face of her own volition. Gary opted instead to simply enjoy the view and wait.
Teddy was extending her fingers so far down his body that at full stretch, her nipples as good as touched his cheeks.
He couldn’t bear it any longer—he needed to do something. He waited until she extended her body across him again and moved his head to the side and back, flicking the tip of his nose across one of her pliant knockers.
Encouraged by her lack of response, he waited for her next stretch and moved his head to the other side, this time succeeding in burying his nose into the soft flesh of her right breast.
Hoping to get more, he anticipated her next approach by leaning his head as far back as he could and opening his mouth, hoping to feel a rivet-like nipple on his parted lips, but her tits weren’t close enough, and this final lunge was to be her last.
Her extending fingers reached the huge pool of precum that had collected on his tummy and was filling his belly button. Had he not been so aroused, her digits might have met the tip of his penis, but his steadfast erection ensured it hovered inches above its dripped deposit.
Judging by her almost perplexed examination of his clear, silky secretions between her fingers, Teddy had not intended to sink her fingers into the manifestation of his excitement, but it seemed to signal to her that it was time for the session’s climax—and Gary was so fit to burst he couldn’t wait.
She moved to the side of the table and put an ungodly amount of oil into her hands, all the while staring at Gary’s twitching cock. But she looked nervous and full of trepidation.
After a pause, she finally reached out and took Gary’s manhood into a warm and welcoming hand and squeezed it ever so gently. Oh fuck, this was heaven! He wasn’t going to last long—seconds, maybe.
He didn’t even have that long, though. Teddy pulled her hand away as if the cock in her hand was molten.
“I… I’m sorry, I can’t do that. I’m sorry… I thought I could but… But you are still married, and I have a boyfriend, and I… I’m sorry.”
She looked genuinely embarrassed and ashamed, so much so that any frustration Gary was feeling was quickly replaced by guilty empathy.
He sat bolt upright from the table to reassure the woman who had transformed from exotic temptress to naïve and vulnerable girl in a matter of milliseconds, reaching for a towel to cover himself.
“Oh God, Teddy, don’t be silly. You don’t have to do that. Really. This has been the most amazing massage I’ve ever had. You don’t have to do that if you’re not comfortable. I’d never want you to do that if you didn’t want to.”
She looked relieved and pulled a cute “my bad” expression before mouthing “thank you” to him.
As disappointed as Gary was, he wasn’t that much of a creep and certainly didn’t want to force Teddy into anything. But his welling sexual energy was going to need an outlet—something Teddy seemed all too aware of as she motioned toward the bulge under the hastily gathered towel on his lap.
“I leave you for a while,” she said. “Let you finish.”
In the time it took for Teddy to grab her top off the chair and reach the door, Gary weighed his options, considering what Teddy had obviously been comfortable with over the past hour, and decided to take a chance.
“Teddy?” he whispered as she reached for the handle. She turned to look at him with a smile, her scrunched-up top pressed against her chest for modesty.
“Would you mind staying while I finished?” he continued.
It was a bit of a gamble, but Gary didn’t want to end this majestically erotic afternoon wanking alone with just his memories.
Teddy paused to consider the request, and as she wasn’t dismissing it out of hand, Gary tried to persuade her.
“I just want to look at you a little longer,” he said. “You’re so beautiful. It will help me finish if I can look at you.”
The flattery seemed to outweigh the sleaze, and Teddy took her hand away from the door handle and threw her top back on the chair.
She sauntered back over to the foot of the massage table, purposefully swaying her chest, seemingly grateful for a chance to atone for her last-minute change of heart by doing something her client would enjoy but that she was still comfortable with.
Gary beamed a grateful smile and reclined on the massage table, finally able to do what he had been aching to do since that first glimpse down her top.
He grabbed his engorged penis. It was still slippery from Teddy’s aborted attempt to pleasure him, and the delightful sensation as he glided his hand up its length and over the swollen helmet was as close to heaven as he had been all afternoon.
With more than a hint of curiosity, Teddy approached the side of the table with her arms loosely folded, obscuring what was to be Gary’s main visual stimulus as he jerked himself into a stupor.
He allowed Teddy a closer look at his deliberate strokes—the way he used the oil to squeeze and milk his solid erection—before asking for a better view.
“You’ve got such beautiful breasts. Can I see them again?”
She complied by unfolding her arms and letting them hang at her sides. The reveal triggered a rapid increase in Gary’s pulls and yanks as he drank in the beauty of her perfect, youthful titties.
His eager manipulations drew fascination from the object of his desires, and she studied his masturbatory technique intently.
“My boyfriend is not…cut, you know?” she offered, trying to explain her obvious inquisitiveness.
“Circumcised,” panted Gary over his exertions.
Teddy just nodded as she stared intently, close enough to see exactly what he was doing but far enough away to avoid being in the firing line, so to speak.
Her study of Gary’s wanking was matched in intensity by Gary’s thorough appraisal of her tits. Such a shame he wasn’t going to touch them, to suck them, but by God, they were going to be there when he came. Which was going to be very soon indeed.
“Such amazing tits,” he gasped to encourage himself toward orgasm. This had the unintentional but wonderful result of having Teddy consider them too.
She broke off her analysis of Gary’s jerkoff technique to look down at her assets, and, much to Gary’s elation, she brought her hands up to cup them in a performative gesture.
Any chance of Gary prolonging this divine masturbatory session ended right there. As he felt his cock contract and his balls prepare to empty their contents, Teddy ran a thumb over a rock-hard nipple and looked at Gary with a cheeky smile.
His orgasm was immense. He groaned as a high-pressure jet of white pearlescence erupted from the tip of his strangled member.
Teddy gasped as it hit Gary on the underside of his chin before an equally hefty dollop landed on his chest, then another on his stomach, then several dissipating pumps onto his pelvis.
With each ejaculation, Gary grunted, and Teddy adorably gasped.
When he had finally finished emptying himself, he stared down at his body, cock still in hand, to assess the vast quantities of cum with which he had adorned himself. Gary laughed with incredulity, and Teddy joined him.
“Wow,” she finally said through the giggles. “That was a lot.”
“Well, I had something wonderful to look at.”
“I think you should have shower.”
“I think you are absolutely right.”
Gary was so charged with sexual energy and so turned on by this experience that he managed to knock another one out in the shower.
Despite not being able to get his hands on her, and despite Teddy not getting her hands on the part of him he would have liked, this had been the best massage of his life.
He wanted his tip to reflect that, but once he’d showered, dried, and dressed to leave, Teddy refused to accept all of it.
“It is so generous, please. I didn’t even do what I was supposed to do, so please. This is fine. This is super.”
My God, Gary thought. ~Massaged me topless…hung her tits over my face…let me wank myself silly while I perved over her…~and~ I got a professional massage. And she thinks ~I’m~ being generous? This girl is some kind of angel from a wet dream.~