Things had now changed a bit between Tiffany and I. The next several times she visited, things proceeded much like they had for months. Drinks, foot rubs, and talking about my dating life were followed by me using my masturbation tube. The change was that she didn’t give me the option of a handjob or kissing her feet. But she always expected me to ask to kiss her feet. She never told me to ask her. She would Just sit so that her feet were out of reach while I was using my tube. She would only move them within reach if I asked… “may I kiss your feet?”
Then there was the fourth visit. Things proceeded as usual and I was using the tube and asked to kiss her feet. She moved them within reach and after a few seconds of kissing, she tilted her feet up so that only her heels were touching the cushions and her toes were in the air. Though I was in my ecstatic haze, I didn’t miss a beat and started licking and sucking her toes. I had never done this before, but I had fantasized aboutIt since I began kissing Tiffany’s feet. My orgasm was incredibly strong.
Afterwards, I looked up at Tiffany and she was smiling down at me. There was something different about her expression. I really couldn’t place what it was.
“That was great!” she said. “I’ve never had my toes sucked and I’ve always wondered what that was like. I loved it! It turned me on so much.”
“I also loved it. I’ve never done that before.” I responded with a huge grin on my face.
“Then, we may just have to do that again.” She responded.
I chuckled and we finished up as usual.
The next two times that Tiffany visited, she put her feet in front of me without me asking. But she did not lift her toes, so I just kissed them. It was the third time that I asked, “may I suck on your toes.”
“Yes, you may.” She responded with a smile and lifted her toes for me to suck and lick.
We only met like this three more times before she called me and told me she had bad news.
That evening after work we met at my place as usual. While I was on the floor rubbing her feet, I asked her what the bad news was.
“Well, Christmas is coming and Edwin and I are going to travel to visit his family for the holiday. Since they live so far away and we go out there so infrequently, we will stay there for a few weeks.”
I paused my rubbing and looked up at her a little stunned as her words sunk in.
“It’s not ideal, but it will work out. I’ve been looking into this and I have made some preparations for you while I’m gone.” She said.
“What do you mean preparations? You’re not going to let me out while you’re gone?” I asked.
“Oh, no. I’m not going to leave you unlocked while I’m gone.” She responded. “Go get your laptop.”
I stood up and walked nude, but for my device, to get my laptop and handed it to her.
She pulled up the browser and typed in a web address bookmarked it and handed it back to me. I looked at the web page she had brough up. It was an article about prostate milking. I very quickly skimmed it. Then looked up at her.
“So, while I’m gone, I want you to try and release your seamen in that way. From what I’ve read, 3 weeks without release shouldn’t hurt you, but I want to make sure you stay healthy so give that a try.” She said.
“I really don’t think I could do this to myself. Please can’t you just let me out while you’re gone. I promise you can put it back on me when you get back.” I pleaded.
“Nope. I have already made my decision. But I realize that you may not be able to do that to yourself which is where the rest of my preparations come in. Here, take this.” She said as she handed me a small wrapped package. “It is your early Christmass present.”
I looked at her with skepticism and began unwrapping it. I was now looking at this oddly shaped plastic thing. Close to the same size as my thumb. The package said it was a prostate massager. I was beginning to understand what sheintended me to do.
“You expect me to use this on myself?” I asked
“Sure, I suspect lots of guys have used things like that. I have read some reviews, and while they don’t work for every guy, they do work for some. And it’s hands-free!” She said with more excitement than I would expect.
I just told.
“And I have one more thing for you in case that doesn’t work.” She said as she handed me a piece of paper.
The paper had a phone number on it. I looked at her questioningly.
She answered my unvoiced question. “That is my friend Caitlin’s phone number. She is a nurse and a very open person, if you need any help while I’m gone, she can help you.”
“Tiffany, I couldn’t possibly call her and ask her…” I started.
She cut me off. “Caitlin already knows about our arrangement and I have already explained to her why you would be calling.”
Now I just began to blush.
“Don’t be so shy. She was very excited by what you’re doing and sounded excited by the prospect of giving you a hand.” And there Tiffany just burst out laughing.
I just grimaced at the pun. “Please Tiffany, can’t I change…” I started.
“Dan, I’m doing this all for your own good and I won’t let you change my mind. Which is why I didn’t bring the key with me today. I didn’t want you to sway me from this course.” She interjected.
I just frowned and asked “Okay, so when are you leaving for your trip?”
“Next Friday, but I won’t be coming back here between now and then because I will have to work late every night and of course pack for the trip.” She answered.
“But, but… that is a week away. That means I won’t see you for four weeks in total!” I blurted.
“Yeah, I’m sorry about that, but it can’t be helped.” She said with a feigned frown. “But the good news is that I can hang here for another drink and you can tell me about what’s going on with your lady friends.”
I told again, grabbed two more beers and resumed my position at her feet and continued to rub them while we chatted.
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