Jack Hawkland
Gary had been so looking forward to his third session with Teddy that it bordered on unhealthy. His thoughts seemed to turn to her on an almost daily basis—the thought of her hands on his body, the way she complimented him, the way she dealt with his arousal with such good humor and amusement.
But he also remembered that for every time he felt she was flirting with him, there was a tale of a ‘pig’ that had tried to get more from her than just a massage. He didn’t want to spoil his relationship with her.
He so wanted to test how far he could take things, though.
It was a dilemma. He imagined a dozen scenarios playing out and concocted a hundred things that he might say to test the waters, but he knew he’d never be brave enough to push it too far.
She greeted him for his third appointment with a kiss on both cheeks—very continental. She seemed pleased to see him but a little more subdued today. She spoke hardly at all while tending to his back, only making the occasional inquiry about whether she was applying enough pressure.
When Gary commented that she seemed a little low today, she seemed surprised to learn she was so transparent and berated herself for taking her problems to work with her. She mumbled something about her lazy boyfriend losing his job—of course she had a boyfriend—and how expensive London was, but then quickly changed the subject.
“I would much rather talk about you,” she said. “The lovely man with the nice bottom. How have you been? I see you have taken off your ring. That is good!”
Despite the flattering comments, the massage progressed without much incident. Gary didn’t want to push his banter with Teddy when she was so obviously down in the dumps.
While regaling him with tales of the current weather in Bulgaria during an exploration of his left thigh, Teddy slid the towel over from one leg to the other to expose and work on his right thigh. But she yanked a little too hard and pulled the towel too far, revealing Gary’s rubbery, but thankfully still flaccid penis.
When she pulled the towel back the other way to cover him again, she failed to anticipate the sudden engorgement that this unexpected exposure triggered. Gary’s semi-turgid cock lurched upward to rest on his pelvis, and the top of Teddy’s hand caressed the sensitive underside of his rapidly growing phallus. She gasped with horror as she made contact.
“Sorry. Sorry, I…so sorry…”
As she struggled to contain the now almost full erection with the towel, it became a bit of a comedy of errors, as each attempt to rest the towel on Gary’s crotch simply resulted in a pitched tent.
Gary, still high from the briefest of intimate contact, did little to help. He flexed the base of his cock as hard as he could, watching with disguised glee as Teddy tried to rest the towel in a way that hid his arousal. After all, this wasn’t his fault—she was the one who had touched his cock!
Finally, after some frantic folding, a semblance of modesty was restored, albeit with a noticeable bulge beneath the white cotton.
“I’m so sorry, that’s not…that shouldn’t… I’m sorry, that was accident.”
Bless her, she seemed genuinely aghast.
“Teddy, it’s fine, really, it was an accident. I should be apologizing. It really shouldn’t react that way with just a tiny touch like that. I’m sorry…”
“No, no. I’m sorry.”
“Shall we stop apologizing to each other? It’s fine.”
“Good. Okay, is fine.” Teddy took a deep breath, then looked at Gary with a smile and a wag of her finger. “Not that kind of massage,” she reminded him.
“Hey, I didn’t do anything,” Gary teased and elicited a blush from the beautiful brunette. “Honestly, it’s fine,” he continued before muttering under his breath, “Actually, it was the highlight of my year.”
Teddy gave a loud tut.
“You have not been separated for that long!”
“Yeah, but we were in separate beds years before we split up.”
Teddy looked shocked; Gary couldn’t tell whether it was because he was oversharing or if it was the nature of the admission. Either way, she massaged in silence for a few minutes, although her frequent glances toward the ever so slowly receding bulge under the towel gave the impression she was mulling something over. Sure enough, as she moved from Gary’s thighs to his stomach and sides, she continued the conversation.
“Have you ever been to one of those places that do the other type of massage? You know, the sexy ones?”
This wasn’t helping Gary’s erection disappear, but he gladly engaged.
“I’m ashamed to say that I have. Once. I didn’t really like it.”
“No? Why not?”
“Well the woman wasn’t in a good mood, and she just took her clothes off and rubbed up and down me. It wasn’t a proper massage; she didn’t know what she was doing, and it wasn’t relaxing or anything. Then she just kind of tugged me for a while and that was that.”
“How much did you pay?”
“Fifty bucks or so.”
Teddy raised her eyebrows.
“You pay more for normal massage like this,” she said, almost apologetically.
“Well sure, but this is better. It’s a professional massage. Given the choice between receiving a bad massage from a naked woman or a great massage from a fully clothed one, I’d always choose this.”
Gary was worried he was being too obvious or too leading, but Teddy didn’t react negatively—she just carried on massaging.
“What do you think you would pay for both?” she finally inquired.
“Oh, I don’t know. A hundred? Hundred and twenty?”
“Just to take clothes off? It’s a lot.”
“Well, it depends how good the massage is. But if it was an expert massage, a proper therapeutic massage, and the girl did it naked, I think I might pay that much. I’d certainly give a big tip, anyway. She’d have to be pretty, though.”
“How pretty?”
He had already pushed this very far. Should he go further? Oh, what the hell…
“Well, if she were half as pretty as you, it would be worth it.”
She flashed a coy smile but remained silent. The session was drawing to a close anyway, but Gary felt he had possibly been a little too blatant with his suggestiveness this time. Was she now mentally filing him away as another of her ‘pig’ clients? Or was she flattered? Was she actually considering his veiled proposal?
By the end of the massage, Gary still had his erection. As he sat up from the massage table, the pitch over his crotch was even more exaggerated than when he was lying down.
“Will you have a shower?” asked Teddy, her eyes drawn to the protrusion under the towel. “Will help you… you know…cool off.”
Her gaze left no doubt about what she meant. He sighed. “Yeah, I suppose so.”
He hopped off the edge of the massage table, making no effort to gather the white cotton on his lap. As he had hoped, the small and thankfully rather lightweight towel remained draped over his covered erection as he nonchalantly strode toward the bathroom, otherwise naked.
The hysterics he heard behind him as Teddy collapsed with laughter let him know that his silly, if risqué, act was a hit with his one-woman audience. How wonderful that he was in such a place with this girl that he could make a joke of his sexual arousal and she would join him in his mirth.
After he finished showering and drying—a difficult feat, considering his erection refused to subside—he met Teddy at the door to pay her. He was slightly embarrassed to realize that while he could still afford to give her a tip, it was not as generous as his previous contributions.
“No, no…it’s fine,” she insisted. “Some people don’t tip at all. This is normal tip. It’s fine. I didn’t do anything to deserve bigger.”
She looked at him squarely. “But maybe bring more next time. Just in case.”
Gary must have seemed shocked, because his expression elicited a giggle from Teddy. But then she appeared worried that she had crossed a line.
“Joking,” she added. “I’m joking. Not that kind of massage.”
She leaned in to kiss both cheeks and promptly closed the door.
Gary stood there stunned for a few seconds and then headed down the stairs to the main entrance.
This erection really wasn’t going to go any time soon.