He had to be dreaming. There’s no way that a woman would be doing that to him otherwise. Was it a dream or was it reality?
Let’s start at the beginning…
He had a few days off work, but unfortunately, he was alone. His girlfriend was already on vacation at her beach house with a few other recently retired women she used to work with. He knew it was a “girls only” trip for them to cut loose and celebrate early retirement, and he didn’t mind staying home and taking care of the pets. He was only semi-retired, and he still needed a little cash coming into his bank account.
On his first day off, he went outside to clean the pool. The day was going to be perfect for tanning and day drinking, and he was ready to get started early. The sun was shining and there were no clouds, as he stretched out on the lounger and dialed up some music. It didn’t take him long to feel sweaty and thirsty, so before getting into the pool to cool off, he made a strong drink in a very large insulated cup.
“Ahhhh…” he said to himself after taking a big gulp.
The house with the pool was on several acres and belonged to his girlfriend, but he had moved in with her a few months ago. She had done well for herself, and he was lucky to find her by accident after searching the internet and dating many women that never seemed right for him. There was something special about this woman though, and he couldn’t place his finger on it. They both seemed to be on the same frequency on almost everything.
The strong drink on an empty stomach hit the spot, as he jumped into the water and started floating on the inflatable pool lounger. As he drifted around the pool, he realized that nobody could see him through the trees and bushes, so he took off his baggy swim shorts. He still had a bikini speedo on, but he was too shy to wear it in public. He just wore the speedo as underwear to keep his package contained under the swim shorts.
There was a newfound freedom in tossing the baggy shorts to the side of the pool, and the alcohol began to kick in after a few more swallows from the insulated cup. He was thinking naughty thoughts about his girlfriend as he snapped a picture of his speedo-clad body and sent it to her.
“Where’s the chubby?” was her text reply.
He laughed and texted back, “Do you want to see a chubby?”
The chubby was already straining under the speedo suit now. They had never had a text conversation like this before. He liked it. After a few more sips of his drink, he began snapping and sending her a few pictures of his chubby buried under the speedo. It was all fun and games until she sent a text reply.
“No cock pictures?”
He chuckled and texted back, “Men aren’t supposed to send those without being asked or told.”
She texted a meek reply back, “If you want to.”
He was disappointed. He wanted her to ask for one. Better yet, he wanted her to tell him to send her one.
“You have to say it.” He let her know how this works.
Her reply seemed to take forever. Was she already tired of this game? He was quite chubby now, and the speedo was really straining. He didn’t want the game to stop as he began typing again.
“Say it… You have to tell me.” He hit the send key and waited.
His chubby was retreating under the speedo now. Maybe he had assumed too much. She was very proper, and maybe he had ticked her off or she had taken the teasing as far as she wanted. Then the message arrived.
“Send me a cock picture.” He couldn’t believe that she had really sent that message.
His cock realized that it was time for the “curtain call” and responded accordingly. He lifted the edge of his speedo just enough to show a partial bone sprouting and snapped a picture. His hands shook a little as he sent the message to the cellular satellite Gods. They laughed and sent the picture to his girlfriend a millisecond later.
“I can do better.” He typed and texted in an attempt to save his ego and his man card. Her reply took a long time to get to him.
“Take off the speedo.”
His hands were really shaking now. He almost dropped the phone into the pool as he read the message. He smiled widely and placed the phone on the edge of the pool. There was no chance he was going to end this game by drowning his phone. The speedo was now ‘off-duty,” and he peeled it down his legs and deposited it in a twisted blob on the side of the pool.
This was no time to be shy, but he was outside, naked and floating in the pool, with a partial erection at noon. His new sundial told him what time it was. It was time to spring into action. Suddenly the thought of getting caught with a full-masted cock interfered with his performance.
“Knowing my luck, somebody shows up right about now.” He mumbled to himself as he looked around the property.
He was 3/4 cocked when he snapped the picture and sent it to his girlfriend. The Gods were really laughing now, but the message made its way to her. He continued to float around the pool, and the worrying thought of being naked outside began to fade as the alcohol increased.
“How’s this?” he texted. It was a half-hearted attempt at ending the game, but it also let her decide the next move.
What was the next move? He hadn’t really thought about that part of the game. He swam around the pool and thought about the freedom of skinny dipping. He hadn’t skinny-dipped since he was a teenager in high school. His family had a pool and since he got home after midnight from his part-time after-school job, he often stripped down and floated around naked instead of showering the sweat off of him. His heart skipped a beat when his phone chirped the message notification.
“I thought you said you could do better?”
“Oh great, now she’s making fun of me?” he thought as he contemplated the best reply to send to her. Sometimes silence is the best reply, and he waited for her to push him farther into the game.
“Go get your tripod and set it up.” Her message made him grab a towel and head for the house.
I’m sure the cats wondered what the hell he was doing as he dripped water through the house in search of his tripod. There was a new excitement in the air now. Skinny dipping with a tripod set up, he was half-drunk and well on his way to unexplored territory. Maybe she wasn’t serious. Maybe he was going to look like a fool when she says she was kidding.
Even with those doubts in his head, he texted her back, “Tripod ready.”
Now the ball was in her court. What would she do? What would HE do? Let’s find out.
