20

Part 19

I walked in a daze back to my apartment. The idea of Lily masturbating to the idea of me in chastity had me so unbelievably turned on. I was stuck in a logical circle. If it turns me on to turn her on, and she is turned on by me being locked up, then I must get turned on by being locked. I was starting to feel a little weird how I was almost happy to be locked; the positive feedback from both Tiffany and Lily had me feeling very confused.

I got back to my place and tried to quiet my mind. I took a cold shower and put on a movie that I hadn't seen before just to try to move my mind away from the events of the night. Eventually I went to bed, but my sleep was restless. I don't remember any details, but I think I dreamt I was with both Lily and Tiffany and I was locked. Were they making out? I can't remember.

I woke on Saturday morning and was groggy, but oddly upbeat at the prospect of going to the concert with Lily. Putting aside all of the kink stuff, she was really nice and I enjoyed talking to her.

I decided to try to make the most of the day; I took a shower and had plans to head out and spend time in the park. I needed to get out and do something to get away from the crazy soup that I had been floating in.

Then I got a text from Tiffany.

"Hey, are you home? I wanted to stop by and grab my running shoes." she wrote.

With a sigh, I responded that I was home and would wait for her. After not too long, my buzzer rang and she was on her way up. We greeted each other with a hug and she came in. She was wearing yoga pants and sports bra that were identical to the ones that I had washed and returned to the gym bag. I directed her to the bag and she removed the running shoes and sat on the couch while she changed into them.

"So, how was your date last night?" she asked, sitting back on the couch.

I told her about my experience with Lily and that I had a good time. She definitely seemed intently focused on my story as spoke. I left off the last thing that Lily had said about masturbating to the idea of me chastity.

"And I'll see her again tonight to see a small band play that she knows." I finished with.

"Oh, that's good to hear. It is also nice that she is kink-friendly so you don't have to hide your chastity from her." She responded.

"Speaking of kink; I looked over those two blogs you sent me. On the surface they share quite a bit in common, but it seems that the motivations of the two couples are somewhat different. What are your thoughts about their kinks and motivations?" I asked.

"You've always been observant of details. Yeah, they are only superficially similar. Like most things, female led relationships are on a spectrum in terms of the motivations and I think I fall in between those two perspectives. Which is probably why I follow them both. As far as the kinks go, I find a lot of what is discussed by those ladies to be appealing." She paused and smiled, "I don't think I'm going to share too much with you right now, but maybe in time."

"Aw come on, I have never held back from you. We tell each other everything!" I prodded.

"Hmm... okay, I'll say this much. I do like the idea of being begged. Of having the power in the dynamic and my partner begging me for something." she offered.

"Oh, I see. So, if I were to beg to be unlocked and to use the masturbation tube or for a hand job, that would be something you might like?"

She laughed, "Well, first, I don't have the key with me. But no, actually, a guy begging to cum is not really what I mean. After all, even when a guy's dick isn't locked in a cage like you, they are basically all begging to cum all the time. It's not really special. I think I'm more interested in begging for things that are more focused on my pleasure or amusement... hmmm... or maybe his discomfort or humiliation. It is begging to show devotion and surrender, not for direct pleasure."

I was a little disappointed to hear this answer. I was a little confused what kinds of things she might mean. The first and most obvious thought I had was begging to go down on her. But, I couldn't bring myself to voice that - it just seemed too far over the line. Then it struck me!

"Tiffany" I started as I dropped to my knees in front of her, "May I please kiss your feet. Please? Please?!"

She looked intently into my eyes and her face became very serious, but she said nothing for a moment. She was not silent for long, but it felt like it dragged on. My heart began to beat harder and I started to be nervous that I had gone too far.

"Yes, like that." she said breaking the silence but still maintaining her eye contact and serious facial expression.

Now my heart was pounding. I put my hands together in supplication and adjusted the tone of my voice but repeated my entreaty.

"I would allow you to, but I have to get my cardio in today. If I spend too much time here, I will have to skip my run. You wouldn't want me to miss my cardio, would you?" She asked.

"I guess not." I despondently replied.

"You give up too easily. Maybe you could offer me some kind of cardio activity here?" she offered.

I had to pause, I wasn't sure what she could mean. I mean, I guess cardio could be a euphemism for sex, but that wasn't on the table... Oh.

"Tiffany, would you like to do a workout with me and... Calvin?" I asked.

She burst out laughing. I began blushing and chuckled nervously along with her.

Once her laughter died down, she said, "Nice use of my pet name for the new strapon cock. But, that seemed like a polite invitation rather than begging."

I took a deep breath, "Tiffany, would you please let me kiss your feet and do a workout with me and Calvin. Please, Please Please!"

Her serious face returned and she took a deep breath, "Go get ready and call me from the bedroom when you are done."

I jumped up and double timed it to the bathroom, used the toilet and jumped in the shower to clean up. I dried off and went with a towel to the bedroom. Not being sure what to do, I decided to get to my knees and I called her.

She came to the room carrying the gym bag which is where I had put the harness and dildo. She came to stand before me and dropped the bag to her left. She was still wearing her running shoes and just extended her right foot before me. I didn't miss a beat this time, I started to untie her shoe. To pull it off, she lifted her foot off the ground and steadied herself with her hands on my head. I also removed her ankle sock. I then removed her left shoe and sock and she pulled her hands off my head.

"May I please.." I started

She interrupted, "Take Calvin out of his packaging and attach him to the harness."

I took the dildo out of the gym bag and after fumbling with the packaging, removed it and attached it to the harness.

"Now, put it on me." She said.

My heart was pounding and my hands were shaking. I had been shaky all along but it was hitting a crescendo at this point. I almost felt light headed.

I held out one loop for her to step into. Once again she steadied herself by putting her hands on my head. She slipped one foot in and then the other. I gingerly raised the harness up her calves and her thighs until it was just about in place. I hadn't really been focused on her yoga pants up until this point. But I couldn't help but notice that no panty lines were visible under her skin-tight pants. This realization made me turn my focus to her crotch. I could see the outline of her pussy. I placed the curved base of the dildo right over her beautiful mound. I then took the waistband of the harness and cinched it tight using the velcro fasteners.

She was intently watching as the harness was slid into place and fastened.

When I was done, she exclaimed, "I have a cock!"

I dropped back to rest my but on my heels.

She wiggled her hips back and forth to get the dildo to swing side to side and then up and down. She had a beaming grin as she reached down to straighten the curved base against her pussy. She also took a moment to lewdly stroke it.

"Put the towel there and get on all fours facing the mirror." She said pointing to a spot on the floor right in front of a full length mirror hanging from my closet door.

I did as I was told and waited. She was behind me, so I watched her through the mirror. She pulled the lube out of the gym bag and applied some to her new cock and stroked it until it was covered. She then came toward me and told me to lower my head to the floor. I did as I was told and now could only see my caged cock dangling between my legs and her feet and calves as she approached. I then felt the cold of lube dripping onto my anus - a feeling that was no longer foreign to me. She rubbed it in and slid in one finger.

I really couldn't believe what was happening. This did not feel real. Was that really Tiffany, one of my best friends behind me? The girl that I had quietly been longing for? My disbelief was broken when I felt the dildo press against my anus. She had moved her feet so that she was almost straddling my hips and was preparing to do squats. She steadied herself with her hands on my hips.

We hadn't exchanged any words; we were both lost in our own heads it seemed. The first thrust was deeper than I expected and I let out a little bit of a gasp. She paused for a second but then continued. My head was still down and I could see my caged penis begin to rock forward and backward as she began her rhythmic movement.

I started to lift my head so I could look at her in the mirror and she smacked my hip with her hand and said, "Head down."

I lowered my head and with my hands gripped the towel below me and braced for her pounding. I would occasionally let out a groan when she would slide in all the way. After some time, she pulled out and told me to stand up. I did and she led me over to the bed and directed me to face it and then lay on it so that my torso was on it and my legs were off the side. She then, without any warning or ceremony, slid the dildo back in and continued to rearrange my insides. After a relatively short time, I sensed her movements were becoming more rapid and frantic. Her breathing was getting heavier when she finally thrust in all the way and began roughly grinding herself against the base of the dildo. She screamed "Oh my god!" and her body shuddered and shook for a few seconds and then she collapsed on my back. She remained motionless for a while, but I could feel her heavily breathing.

When she did move, she raised herself off of my back and pulled out of me. I turned and could see that she was standing there somewhat shaky.

"That might have been the most intense orgasm I've ever had! I can't believe how fucking hot that was! And you fucking rocked it!" She exclaimed.

I couldn't help but smile at her excitement. "I'm glad that you enjoyed that."

"Oh I did! And now for the thing that you originally begged me for." she said with a smile.

With that I got to the floor and kissed each of her toes and the top of each foot. I then looked up at her and locked eyes and said "Thank you Tiffany."

"You're welcome! Now help get this harness off. I need to change and get out of here. If I don't leave now, I'll be late getting back." She said.

I took the harness off her and she grabbed the clean yoga pants from the gym bag and went to my bathroom.

After a few minutes she reemerged wearing the clean pair of yoga pants and worked her way to my couch. She asked me to grab her socks and sneakers and bring them from the bedroom. When I got to the living room, she told me to put her sock and shoes on. I kneeled before and did as she asked.

I walked her to the door and after hugging me harder than usual, she left, saying "Have fun with Lily tonight!"

Not sure what to do with myself, I started to clean up from her visit. I put the towel in the hamper and the lube back in the gym bag. I took the strapon and harness into the bathroom to clean them when I noticed Tiffany's yoga pants unceremoniously piled in the corner. I picked them up and noticed immediately the dampness. Without even a thought I brought them to my nose and inhaled. I could smell her arousal on the fabric. I took them away from my face and opened them to see a little bit of a glistening on the inside. I instinctively started to bring them to my face when I broke out of my mental fog. I dropped my hands to my sides, sank to the floor, and started to cry in frustration.

After a few minutes, I regained my composure and jumped into a cold shower. I took the worn yoga pants and put them in the washing machine.

I left my place with a book that I had wanted to start. I stopped by a coffee shop and set up on a bench in a nearby park. I was determined not to allow my sexual frustration define my day. I made a valiant effort to focus on the book and the beautiful weather in the park, but I found it difficult to put the events of the morning out of my mind.

After a few hours, I left the park so I could grab some food and get ready to meet up with Lily later.

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Part 20

I was looking forward to seeing Lily. I had eaten, taken a cold shower and tried to put the events of the morning out of my mind. As hard I tried, I could not totally forget about Tiffany pegging me. And I definitely could not forget about her ogasming while laying on my back or the damp yoga pants she left behind.

I got dressed and headed over to the music venue where I was going to meet Lily. I arrived a few minutes early and didn't see her, so I posted up outside and waited. After not too long, I saw her coming up the block. She was wearing red converse sneakers, cutoff jean shorts, black tights and a black t-shirt emblazoned with the logo and name of the band we were seeing. Normally, I was drawn to the fem type, but I have to admit that I found Lily very attractive. I think a big part of it was how well we clicked last night.

When she noticed me, she beamed a smile at me and quickened her pace to something I would describe as a bouncy jog. Her smile and exuberance drew an involuntary smile to my face and my pulse quickened. I moved toward her and we embraced.

"I'm glad to see you! Are you excited for the performance?" She started

"Yes! And I'm also excited to see you!" I responded

"Awww... Thanks! But don't get too excited, I don't want you to hurt yourself." She said with a wink.

I chuckled and she grabbed my hand and pulled me toward the doors of the venue. As we entered I stated that I wanted to get the tickets for the show.

"I appreciate that, but I am already on the list with a plus one." she said.

"Oh, you're such a VIP! How'd you manage that?" I asked.

"I used to date the drummer in the band. No need to worry though, we broke up quite a while ago and stopped fooling around a while back too." she answered.

By this point we were approaching the wall of sound that emanated from the double doors leading into the performance area. I decided to not let those revelations ruin my mood and focus on enjoying the evening.

We entered the large, dimly lit room. The stage was at the far end and there were bars on either side. The space wasn't packed yet, but there were already plenty of other concert goers. I insisted on buying drinks for the evening and we started with two scotches on the rocks.

The first band was good. She and I moved to the music and were physically flirtatious - touching and smiling often. We spoke little.

After some time and a number of additional scotches, the headlining band got up on stage. As much as I was enjoying their music, I couldn't help but focus on the drummer. Eventually I leaned in and asked her how long they dated for. She just looked at me, grabbed my face and pulled me in for a kiss. The kissing turned frantic. Those kind of passionate kisses where everything around you fades away and the whole world just becomes lip and tongues. She ended by biting my bottom lip with intense eye contact.

Then without a word, she turned around and pulled my hands to her hips and backed her ass to my crotch. I couldn't pull her close because of the device, but I did hold her tightly with my hands. The softness of her hips and the lingering buzz of our kissing gave me the feeling of floating; I'm sure the music and scotch were playing their role too.

We stayed more or less in that position until the end of their set. While the rest of the crowd was shuffling out, she told me that we were going to go hang with the band briefly to say hi and thank them for putting us on the list.

She led me to the back of the performance area and knocked on a door that said employees only. The door opened and it seemed that she was recognized and we entered. After a couple of turns we ended up in a green room where the band was hanging out. She hugged each of the band members in turn and introduced me to each one. There were other friends of the band and groupies in the mix.

We settled into a spot on a couch talking with the drummer, her ex Jason. Even sitting I could tell he was taller than me and his arms were ripped and covered with tattoos. He did seem a little dismissive of me, but I didn't really care to talk to him so I was happy to remain quiet; all the more so since she never broke physical contact with me. If her legs weren't pressed against mine, then she had her hand on my knee. I kept my arm around her shoulders on the back of the couch.

Lily eventually produced a joint and handed it to me to light up. I hadn't smoked in years, but I was no stranger. After taking a deep drag, I coughed and handed it off to Lily. After some good-natured laughing at my coughs, she took a drag and passed it on to Jason. The joint never made it back our way. Although we were invited to join the after party at some house, Lily declined saying with a coy smile that we had other plans. We said our goodbyes and left.

Holding my hand, she led me away from the venue.

"So, what are our plans?" I asked.

She spun toward me and pulled me down for a kiss. After she broke the kiss, she spun back and kept walking, pulling me along. Occasionally, she would look over at me, squeeze my hand and smile. After not too long, I realized we were heading to her building. My heart was pounding with excitement.

She led me into her building and up to her apartment. Her place was a pretty small studio. In the far right corner she had a full sized bed. In the near right corner she had a small futon. On the left wall was a small kitchen and a small table with two chairs. The back left corner had a small door that I assumed was the bathroom. The place was a total mess; clothes, shoes and other crap all over.

She pulled me over to the futon and we sank down kissing and fondling. She was below me and I had my right thigh between her legs rubbing against her pussy as we kissed. She reached down and grabbed my caged dick.

She broke the kiss, looked me in the eyes and said "I want to see."

I started to unbuckle my pants while still on the futon but she directed me to stand up.

Now standing, I decided to take my shirt off first. She sat up and ohed at my strip tease. I then removed my shoes and socks. Unbuckling my pants, I let them drop to the floor and stepped out of them. Moving forward just in my underwear, I got close to her. She reached up to the bulge and gently ran her fingers across it. She then reached up the waistband and slowly lowered my underwear.

Her eyes and smile widened as my cage came into full view.

"Amazing!" she exclaimed.

With urgency she pulled off her t-shirt; I reached out to help. She quickly undid and removed her shoes, opened and removed her shorts. I helped her slide off her stockings. She undid her black lacy bra next. Her tits were perfect; neither large nor small with perfectly sized pink niples that looked like they could cut glass. When she was down to just her matching black lacy panties, she leaned back and pointed to the floor in front of her.