Part 17
Around 2pm the next day I got a text from Tiffany.
"Hey there, had a great lunch with Caitlin. Bad news, our long lunch today means I won't be able to stop by tonight. But I will be able to come by tomorrow. I can't wait to go shopping with you!"
I couldn't help but sigh. The first trip to the sex shop was embarrassing enough with Caitlin, but I was dreading the notion of being there looking for a dildo with Tiffany. At this point, I couldn't think of a way to get out of it that wouldn't mess up my relationship with Tiffany. And, to be honest, when I thought about Tiffany pegging me, I would get turned on.
For months I had been living with an intense internal conflict. I wanted the device off but I also craved the time I had been spending with Tiffany. Since she would not be coming over, I decided I really needed to sit down with no distraction and work out how to handle my internal turmoil. I had to acknowledge that I had feelings for Tiffany, and they were getting stronger. I also decided that I could not intentionally try to ruin her marriage. Although our interactions were definitely over the line, I absolved myself of guilt by affirming that almost everything that had happened was at her direction. I know that this was a bit of a copout, but it was one that made sense to me at the time. It had also become clear that she really enjoyed holding the key to my sex, my attention to her feet, my frustration and embarrassment; and my heart would feel like it would burst whenever she seemed happy or excited by something I could do for her.
It hit me like a ton of bricks - I love her and would do anything for her. I had known her for a long time and trusted her implicitly. I resolved that I would turn myself over to her direction. And although I decided to subordinate myself to her there was a part of me that felt oddly selfish about this decision.
Although I still had some trepidation about the plans for the next day, I felt more at peace that evening than I had in a long time. I fell asleep with a smile on my face.
The following day after work I awaited Tiffany's arrival at my apartment. She called me and said that she didn't want to waste any time and asked me to come down so we could walk to the store.
We greeted each other and began our walk. She was carrying a gym bag and her purse. I offered to carry her gym bag and she handed it to me. It was mostly small talk until we were about two blocks from the sex shop. Then Tiffany turned the conversation to what we were doing.
"You know, I'm so excited you and I are doing this! Pegging is something I've wanted to try for a long time."
"Really? I had no idea. You never mentioned it to me before." I responded.
"Well, I would have told you if I had done it. But, I have only told Edwin that I wanted to... let's just say he wasn't interested."
This last comment made me feel weird. But part of me was excited by the prospect of offering her something that he wouldn't give her.
"What other things haven't you told me about that you're interested in?" I asked
"Oh, a lot of things. But we can talk about that later. One thing at a time!" She said with a wry smile. "We are here!" She said with a bounce in her step.
We entered the store and I immediately noticed that the cashier was the same woman that was here when I came with Caitlin. She was in her early or mid twenties with short dark hair. She had a few extra ear piercings and a couple of tattoos on her arms; nothing crazy, but noticeable from a distance of about 20 or 25 feet. It was embarrassing to be back here so soon, but I had to just assure myself that she doesn't remember every customer that comes in.
About 5 feet into the store, the cashier looked over to the two of us and said with some enthusiasm "Welcome back! Let me know if you need any help."
Shit. I could not tell if she was looking at me or Tiffany, but I could immediately feel my face flush. Not knowing what to do, I just nodded in her direction and continued following Tiffany.
After a few more steps, Tiffany turned to me and asked if I had been there before. I told her that I had been with Caitlin less than two weeks earlier. "Oh, since you're a regular here, why don't you lead me to the strapon section." She said with a little too much volume for my comfort. So, I took the lead and brought her to the back corner of the store.
"Oh! So many choices! This is very exciting!" She exclaimed.
I unconsciously took a deep breath and let out a little sigh. She either didn't notice or ignored me.
She asked me to point out the one that I had gotten with Caitlin. Speaking to herself she mumbled, "I can't get one smaller than that." And then as if remembering that I was there, she turned to me and said "It's not a competition, but still, I don't want to be outdone." And then she just busted out laughing. I got red but couldn't help but let out a laugh also, and I followed up with "I can't blame you. If I could choose mine off a rack, I would choose a big one too."
"I imagine you would!" She said, returning her focus to the wall of cocks. "Hmm, I feel like this is more personal than I would have anticipated. I really want it to match my energy. Hmm..." She continued.
After very methodically scanning each of the many options, she zeroed in on one. It was actually about the same size as the one chosen by Caitlin. It was a darker beige bordering on brown. What really set it apart was its hyper realism - its head was really well defined and was veiny - even its texture looked like real skin. Another differentiating feature was the base. Caitlin's choice was just a flat round base, this one had a curved base that looked like it would rest snugly against a woman's vagina. It also had hole in the bottom for a little vibrator that was included in the package.
"I feel like this one is really speaking my language." She said with a smile. "Ok, now I want to get my own harness." At which she floated off to the section with the harnesses. She chose one with a very utilitarian look. Then we began our journey to the register.
"Did you find everything that you were looking for?" asked the cashier with a lingering eye contact that made me start to flush again.
"Yup." I said meekly.
"We will also need some lube. Do you have any recommendations for this toy?" asked Tiffany.
"Of course" said the cashier as she turned around to the shelves behind the counter. She pulled down two bottles and placed them in front of us. Putting her hand over one bottle she said, "they are both water based and appropriate for the strapon you selected. This one is thicker and what I would recommend for anal play." Moving her hand over the second bottle she continued "and this one is thinner and is what I would recommend for vaginal play or..." and she paused ever so briefly "reacharounds."
Tiffany chuckled a little at that last bit and reached into her shirt drawing out the chain that had the key to my chastity device and let it drop outside of her shirt as she said "We'll take the first one."
The cashier did not miss the key, raised her eyes to meet Tiffany's and the two of them laughed. After a few moments they regained their composure and the cashier looked at me and winked saying, "You're very lucky to have such a beautiful girlfriend as your keyholder."
"Aw, thanks." responded Tiffany "But we aren't a couple, just friends."
The cashier looked a little confused and then said "Oh, was the other g..." and then she caught herself and began to blush.
Tiffany then jumped in "Don't worry, I know about the blond. She is also my friend, Caitlin. And no, they aren't a couple either."
At this point I was starting to feel light headed and could only assume that every ounce of my blood was in my face. This could not have been more embarrassing for me. I almost felt like I wasn't there. It was like I was having the most embarrassing dream ever.
