24

Part 23

When I woke up Sunday morning I had no recollection of going to sleep. Lily was in my bed, still nude, curled up in a ball. I was famished, so I decided to start breakfast. I made two plates of fried eggs and toast and two cups of coffee and brought them to my bedroom. She was just starting to stir when I walked in and presented her with breakfast.

Bringing her cup of coffee to her face, she smiled and said "What, no pop tarts?!"

I laughed.

We ate breakfast and chatted for a while. We were already making plans for the next weekend. Although I was sexually frustrated, I felt really at ease with Lily; it just felt natural.

We did fool around more that morning. Eventually, she said she needed to go and got ready. After getting dressed, she sat on the couch and told me to put on her shoes. I knelt before her and slid on and laced each of her shoes just as I had done at the movie theater.

After Lily left, I cleaned my place and got ready for the work week.

I woke Monday morning to a text from Tiffany that said, "I hope you had a good weekend. I'd like to come by today after work. I think we should talk."

I immediately felt a sense of foreboding. Lily had informed me that Tiffany was annoyed and no one ever likes to hear the phrase 'we should talk.'

I responded that I would be around and she could come by anytime after work.

The work day definitely did not fly by. But, after what felt like an eternity, I was back home waiting for Tiffany. After buzzing her in and greeting her at the door with an awkward hug, she made her way over to the couch. I asked her if she wanted a beer and she declined. She also told me to skip the foot rub and just sit beside her on the couch.

She started with a very serious expression, "I want to start by apologizing to you. I lied to you a few times recently. I did not receive a call last week from work. I did not go to work after leaving here and my workload last week was pretty run of the mill. I'm sorry for lying."

"Okay. Why did you lie?" I asked.

"Well, truthfully, I was annoyed and disappointed that you asked to be released so you could cum. And I've been thinking about it, and I was wrong to be annoyed. I continued the lie all week because I needed some space to reflect on why I was annoyed. This weekend I came to some conclusions about what we are doing." She answered.

"Okay. Tell me what you think." I prompted her.

"To fully explain myself, I think I should share with you openly what I have been thinking from the start and how things have changed over time. Initially, I suggested locking you up to help you. And when I suggested it, I honestly only thought about helping you. It is true that I had preexisting interest in kink and chastity in particular, but I wasn't trying to make this about me and my kinks." she said.

"mmhmm" I affirmed.

"Well, that started to shift after I got you locked up. I started to get really turned on by thinking about you in that cage. I started thinking about other kinky things that I wanted to try. I placed my feet in front of you as you used the tube hoping that you would eventually take the hint and kiss them. And when you did, I relished getting you to the next step of sucking on my toes."

She continued, "I knew that I wanted to push you even further, and the opportunity arose when I knew I had to leave town for that vacation. Leaving you with the prostate massager and giving you access to Caitlin was intended to push you in the direction I wanted you to go. I didn't specifically ask Caitlin to peg you, but I thought she might. I told you that I met her online, but never specified where. I contacted her on a fetish social media site where I have a profile. We struck up a friendship there and eventually started having regular lunches and coffees. I would listen to her tales and live vicariously through her escapades."

"Okay..." I said.

"I knew that one of her biggest kinks is pegging and that she might introduce you to it. When she did, I was exuberant because it gave me an opening to pursue it with you. Up until that point, keeping you locked, the foot worship, the teasing and so on would get me worked up. Sometimes, I would masturbate at work thinking about those things. Often, I would get home after playing with you and would be so worked up that I would just pull Edwin to the bedroom to fuck me." she paused for just a moment here and let that linger.

She continued, "Often, as Edwin was fucking me, I would think of you here with your dick locked up. I would think about how I had the key and that would send me over the edge. And then, last Saturday, when I pegged you I hit a peak that I have never before experienced. Having you beg me for the pegging and then the complete control I felt as I ordered you around. Put you in a vulnerable positions and fucked you... well, it was almost too much. I thought about that non-stop until Monday when you asked to be let out to cum."

Again, she paused briefly before continuing, "When I was on my way here, I wanted to peg you again. I wanted you to beg for it. I wanted that feeling of power. But instead you asked to be released. It had been weeks and you had every right under our original understanding to ask, but it still annoyed and disappointed me."

She took a deep breath and said, "And this past weekend, after much reflection, I have decided that I have been wrong and I've gone too far." At this point, she reached into her bag and pulled out a plastic baggie that contained two small keys and set it on the couch between us. "That is why I need to give these back to you. I shouldn't hold them any longer and..." she took another deep breath. "... I think maybe we should not hang out for a while."

"Wait! What are you saying? You want to end our friendship?!" I asked in a panic.

"No, no, not at all. I just need some time to reset. I care about you and we will always be friends. But, I need some distance to break out of this. It might be a while, but eventually we will talk again." she answered.

I sat there dumbstruck for a few moments.

"Okay." she said and began to rise from the couch.

I grabbed her wrist and tugged at her to remain seated.

"No." I said flatly. "I don't accept this."

"First, I refuse to put our friendship on hold for even a second. You have been my closest friend for years and I care about you deeply. Second, you have told your side of things, but you haven't given me a chance to tell you my side of things." I started.

"I am definitely upset that you lied to me. After all of this time, I would expect that you would just be honest with me. But, I guess I do understand that it might have taken some time to sort through your feelings. Regardless, moving forward, I would hope that you would just tell me that you need that time." I said.

I continued, "You haven't taken into account that this arrangement of ours does actually seem to be bearing fruit. When you first locked me up, I went on a number of dates and was able to more clearly see when they weren't a good match for me. And, very much because of you, I am now spending time with Lily who I like a lot. And I know that you two have been talking and even have some expectations for me. I don't know what those are, but I trust you, and believe that the two of you have my best interests at heart."

She continued to listen to me, never breaking eye contact, but with little expression on her face.

"Finally, there is something I find very gratifying about doing some of those kinky things with you. So, even though you were a little manipulative in getting me to do them, I find myself enjoying some aspects of all of them. Specifically, I love how much you seem to love this stuff. And, I'm glad that I get to help you explore this side of you."

I took a deep breath and continued, "I don't want to stop seeing you. I don't want to lose your help with Lily. And, I don't want to stop helping you explore. Please keep the keys."

After a moment, she spoke. "Dan, I don't know. I don't think you understand what might be going through my head. Remember those two blogs?"

I nodded.

She continued, "I told you that I felt my interests were somewhere between the two. Well, the more I reflected last week, I realized that I really do gravitate toward the harsher of the two. I think I have a sadistic side that I've been suppressing."

"If a little pain and discomfort is the price of us continuing to see each other, I am willing to pay that price." I responded.

"Dan, I don't know..." She started.

I don't know what came over me, but I dropped from the couch to my knees on the floor in front of her and took her hands in mine and rested them on her knees.

"Please Tiffany! Please keep the keys! Please, I want you to help me by keeping me locked! I will do whatever you say! Please!" I pleaded.

She looked down at me with an expressionless face but an intensity in her eyes. She paused for a while and then finally said, "Okay. I will keep the keys and think over what my new expectations will be. I will tell you what I decide and you will have one more chance to take the keys back before we move forward. I really didn't anticipate this so I don't know what to do next. It might take me some time to work out a plan. I will probably not come back here until I know exactly what I am going to say. It might be a week or more. Understand?"

"Yes. Take what time you need. I trust you Tiffany." I said

We hugged.

She slipped the keys back into her bag and stood up. I also stood up and walked her to the door. We hugged and she said, "I'm so glad you aren't mad at me and still trust me enough to give me this responsibility."

"I love and trust you, Tiffany!" I said.

She hugged me again and squeezed me tight. She then turned and left.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Part 24

The rest of the week had gone by without any word from Tiffany. She did say she would need some time to think things through, but I was still a little unsettled. I intentionally didn't reach out to her, but I was tempted many times.

Friday rolled around and I met up with Lily for dinner. Afterwards we went to a bar and met up with some of her friends. Completely by happenstance, a couple of my friends were at the same bar. It felt a little like worlds were colliding, but everything went smoothly and people got along. I don't know for certain, but I think my friend Russell got the number of her friend Carol.

After the bar, we went back to my place. We were all over each other the moment we entered the lobby of my building. I don't remember getting into or out of the elevator; nothing existed but her lips and tongue. Inside, I stripped her down and with my clothes still on, I pushed her down to the couch and dove between her legs. With a contented sigh, she spread them wide and welcomed me in. I had enough experience with Lily's pussy that I brought her to climax quickly. It was late and we were pretty tipsy, so we worked our way to my bedroom and passed out.

Saturday morning we ate breakfast at my place and then got out to enjoy the weather. But after only a few blocks Lily said, "It is so beautiful outside, everyone is out enjoying the weather! We should go watch a movie." As she said this, she pulled me close to her and beckoned for me to kiss her. After the kiss ended, I said I would be down for whatever she wanted.

"Okay! Back to my place so I can change." She announced and started pulling me toward her building.

She had me wait outside while she went up to change. When she came back down she was dressed girlier than I had ever seen her before. She was wearing white and blue striped top, black skirt and sandals.

"You look so pretty!" I said.

"Thanks!" she beamed back.

And with that we made our way to the theater. When she suggested a movie I thought she might want to follow through on the public play she had suggested last time. When I saw her in the skirt I became pretty sure. But when she selected the oldest available movie that I was certain she didn't care about, that's when I knew what she had in store for me.

We purchased popcorn and soda and started toward our theater. I leaned toward her as we made it past the teenager that took our tickets and asked, "You aren't wearing panties, are you?"

"I am. Having you take them off is part of the fun." she said with a smile.

We got into the theater and chose seats that were as far from the entrances as possible. There were no other moviegoers at this point. Before I reclined my chair, I asked if she wanted her sandals off. She said she did, so I removed them. I kissed the top of each of her feet once after I removed each sandal.

I sat in my chair next to hers and set it to recline. She raised the armrest that separated our two chairs and leaned in to kiss me. We started making out as the commercials and trailers ran. Since the lights were still on we kept the groping to a minimum. As far as I knew, the theater was still empty, but I honestly wasn't paying attention any more.

Shortly after the lights dimmed, Lily grabbed my right hand and pulled it down to her skirt. I rubbed her pussy through her panties. I could feel that they were quite damp at this point. My slow movements were met with moans of approval that were muffled by our continued kissing.

Her breathing was getting heavier as we continued until she broke the kiss and told me to pull her panties down and put my fingers in. It was awkward in the position we were in and her help was required, but after getting them down just a few inches, I could slip my fingers inside. I alternated fingering her and rubbing her clit.

She was definitely enjoying it and she was getting close, but I think the frustration was getting to her. She broke the kissing and said almost breathlessly, "I need your tongue. Now."

We both moved our chairs into a seated position, and I slid out of mine onto the floor. I was in such a state that the disgusting movie theater floor didn't even register. I got between her knees on the floor and slid her panties all the way off. Without thinking I put them in my pocket. She opened her legs wider and lifted her skirt inviting my head inside. My world went from dark to pitch black as I moved my head into her skirt. The smell of popcorn disappeared and was replaced by the smell of her arousal.

I started licking and she had her hands on my head pulling me toward her. I knew that it would not be long as she was close before I started. Within seconds she was crushing my head with her thighs. I could hear her try to mute her sounds. When her grip finally eased, she bid me to sit back in my chair.

I started to recline my chair, but she told me to leave it. "I'm going to want more." She said and leaned in for a kiss.

For the rest of the movie, as long as I remained in my chair we held hands and would kiss and fondle. Periodically, we would take a break and look at the screen, but neither of us was really watching. Two more times she bid me to go down on her, each time prompted by a tug on my arm and her saying "again."

By the time we left, I had a stiff neck and was rubbing it. Lily noticed and said, "Poor baby! I definitely owe you another back rub! I hope you thought it was worth it."

"Oh definitely. That was a little scary, but very hot." I responded. And it was true. My constant state of arousal and inability to cum seemed to make my desire for her insatiable. I wanted to cum badly, but I was also just so turned on all of the time that I felt like I could go down on her indefinitely.

She smiled, grabbed my hand and we walked back toward my place. We grabbed some takeout on the way. We sat on the floor of my place, ate and talked. After we were done cleaning up, she pushed me to the bedroom for my back rub.

I stripped down and lay on my stomach. She also stripped down and straddled my butt. She began with my neck and immediately I felt better and was relaxed. She then moved down to my shoulders and upper back. I felt a heavy drowsiness descend on me. I also felt, once again, Lily rubbing her now wet sex against my lower back.

Sleepily, I asked "Are you humping my back?"

She let out a chuckle and said, "I guess I am."

"What are you thinking about?" I asked.

"You have a sexy back and butt and this is a great view. It turns me on." she responded.

"And you've never pegged a guy before, right?" I asked.

"Nope. I've only ever used strapons with women." she answered.

"Do you want to try with me?" I asked.

"Yes! But, I can tell you are really sleepy. Just relax. You've been through a lot today. There is always tomorrow." She responded.

I think I mumbled something back, but I wasn't awake for much longer.

I slept like a log that night.

When I woke, I was on my side but I could feel Lily gently caressing my back and butt. She was just tracing her fingers up and down, barely making contact. As I woke up more, I stretched and rolled to face her.

"Good morning, sleepy head! I am amazed, you finally slept past me." She said with a smile.

We kissed and she moved her body closer to mine. That's when I felt it; something was poking my stomach. I already knew what it was, but I broke the kiss and looked down. She was wearing the harness and dildo that Tiffany had selected.

"Morning sex?" she asked with raised eyebrows and a smile.

I leaned back in and continued kissing her. We kissed for a while before she pushed me onto my back and broke the kiss. She got down between my legs and lifted them up. She told me to lift my butt up and she crammed a pillow under my lower back.

"This is different." I let out.

"Oh, you haven't done it this way? Always face down?" she asked.

"Yeah." I responded.

"Variety is the spice of life..." she mumbled to the ether as she reached to the nightstand for the bottle of lube.

After lubing up, she pressed the tip of the dildo against my anus and leaned forward for a kiss. I bent up as much as I could so we could kiss. She slowly pushed forward and went deeper, her arms on either side of me kept my legs up. When she was all the way in, she paused and kissed me deeply. After a bit, she began gently rocking her hips. She was slow and gentle. Her focus was on kissing and eye contact. Looking into her eyes, I was lost. I could feel a welling up in my chest.

After some time, her pace did quicken; she seemed to be getting close. She pulled back suddenly and dropped my legs; with a sense of urgency she bid me to turn over. Now, laying on my stomach, she reentered me. After some quick thrusts, she buried the dildo deep and just ground herself against it until she started shaking. She let out a deep breath and collapsed on me.

After some time, she pulled out and got off me. Laying at my side she said, "I really felt a connection with you. I can't wait until you fuck me like that. How big is your dick?"

"Probably average, but I've never had any complaints." I responded, realizing how strange it is to have been intimate with Lily for weeks and yet she had no idea what my penis looks like.

"That's good! I'm a bit of a 'Goldilocks' when it comes to cock; some are too small, others too big, and then some are just right." she said, sliding her hand up and down my chest.

"Ha! Well, I think Goldilocks would approve of mine. But, given that I haven't heard from Tiffany for almost a week, I have no idea how long it will be before we can have sex the regular way." I responded.

"Well, there is no such thing as the 'regular way.' But I know what you are referring to. Don't worry too much about Tiffany. She talked to me after your conversation on Monday. She will resurface soon. She did tell me that when she offered the key back to you, you declined and gave as one of the reasons how well our dating has been going and that you trust Tiffany and me. I was touched by that." She said, leaning in for a kiss.