22

Part 21

I couldn't go to sleep right away. Not surprisingly, I was sexually frustrated, but that wasn't the only reason sleep didn't come. Holding Lily in my arms as she slept was also keeping me awake. I really liked this girl. She was funny, smart, sexy, and we had a number of interests in common. I had a great evening with her. But, just hours earlier I had been pegged by Tiffany, who I loved. I was conflicted and my mind would not let me ease into sleep. Eventually my mind relaxed and sleep overtook me.

Some hours later I woke up with Lily wrapped around me still sleeping. With my free arm, I propped my head up and scanned her place. In the fog of last night's buzz, I only registered some basics but now I could take in more.

Her place was strewn with clothes - panties, bras, shorts, skirts, stockings, and enough shoes to open a store. Most of the clothing was boyish or gender neutral, which I was starting to find endearing. There was also a pile of books on the floor in the corner near the futon. I could not make out any of the titles, but they appeared to be mostly paperback novels. There also seemed to be small stacks of comic books scattered about. Although the place was definitely cluttered, it did seem clean.

I think my movements, despite being subtle, were enough to rouse Lily from her slumber. She stretched her legs and arched her back in a way that I could only think of as feline. She then looked up at me, smiled, and then scooted up to kiss me.

"Good morning, sexy." she said warmly.

I smiled back and asked "How did you sleep?"

"Oh, those two orgasms last night were so good, I feel like they put me in a coma. What time is it?" She said reaching for her phone.

"It's still early." she said.

"Oh, damn! Ha ha ha..." she exclaimed, still looking at her phone.

"What is it?" I inquired.

She turned her phone toward me and I could see a picture of a very large flaccid dick.

"I think that Jason might be jealous of you. He sent a dick pic saying how much he missed me." she explained.

The expression on my face turned sour. She dropped her phone and jumped on me straddling my hips, and lowered her face to mine.

"Don't be that way! I would much rather be with you than him. His dick is pretty big and as much as I enjoyed it, he is a little bit of an asshole. I never really liked him. I already like you better than him and he never made me cum the way you did last night." she encouraged, leaning in for a kiss.

I put one hand on her lower back and the other on her upper back and pulled her down to me. We embraced that like that for a while kissing. She then broke the kiss and said, "I think I promised you pop-tarts, are you ready?"

I shook my head yes and she bounced off the bed, still nude, and made her way over to the kitchen. I watched her from the bed as she prepared coffee and put some pop-tarts in the toaster. After not too long, she returned to the bed with two mugs of coffee and a small plastic plate with four pop-tarts.

"Sorry, I have no cream or sugar here since I drink it black." she apologized.

"No problem, I can handle a little black coffee. Thanks for this gourmet breakfast!" I said with a smile.

She chuckled and we ate, drank, and chatted. When we were done she cleaned everything up and she bounced back to the bed and hopped in beside me. She cuddled up beside me and began kissing my chest.

In between little kisses she uttered fragments:

"So..."

- kiss -

"...I'm wondering..."

- kiss -

"...did you..."

- kiss -

"...and Tiffany..."

- kiss -

"...use your..."

- kiss -

"...recent purchase..."

- kiss -

"...yet?"

"Uuuh, yeah, she used it yesterday morning." I answered.

She stopped kissing my chest and looked at me excitedly.

"Tell me about it, I want details!" She insisted

I was a little reluctant, but what's the big deal I guess. So, I started to tell her. I left off the bit about begging, I wasn't sure what she might think of that, but otherwise I tried to be detailed.

At the point I was telling her about kneeling in my room helping Tiffany put on the harness, Lily took my right hand and pulled it to her pussy. She was very wet. Instinctively, I started to rub her clit, but I also had stopped talking.

"Keep talking and rubbing." she said.

So, I continued with my tale and rubbing. I slid my fingers down to moisten them, and then back up to focus on her clit. She stared at me with lustful eyes as I spoke. I could tell she was getting close. Almost as if it were timed, she began to tense up and shake as I was describing Tiffany's orgasm from pegging. I stopped talking and we kissed for a while.

"That is so fucking hot! I think Tiffany is beautiful and the idea of her fucking your ass is so sexy!" She exclaimed.

"Have you ever pegged a guy?" I asked.

"No, I've never pegged a guy, but I am no stranger to wearing and using a strapon. Jessica, a friend with benefits, and I take turns using strapons on each other." she answered.

"Oh, how many friends with benefits do you have? Are they all women?" I asked.

"I have a few, and only Jessica is a woman. The other two are guys. One older guy that is kind of a dominant mentor with me, I call him when I want it rough. The other guy is a dumb college student with a nice dick and tons of stamina." she answered.

I think my face must have involuntarily given away my concern, because she continued talking "Dan! I don't want you to worry about any of that. First off, I don't really like any of them as much as you. Also, I'm not getting all jealous about your two hot keyholders. We've only just started to get to know each other. Hell, we haven't even had sex yet!" she reminded me with a grin "I want to keep seeing you and get to know you better. When the time comes to talk about exclusivity, we can worry about friends with benefits and who holds what keys."

She paused and looked me in the eyes. "Are we okay?" She made a pouty face.

I forced a laugh and said, "Sure. You're right, I'm sorry. I like you too and I think being locked makes me feel a little insecure."

"I'm super excited that we are seeing each other, and, I hope you can tell that I'm down to find out what becomes of this." She paused, "Okay, enough of this serious talk, I'm hungry again. I think you should treat me to lunch."

I was also hungry, so we got up. We took a shower together in her tiny bathroom. She washed me down and I washed her. Periodically, we stopped to kiss and make out. We went to a local diner for lunch and had a good time chatting and joking around.

We parted ways after lunch. I asked if she was free next Saturday. She said she was and would leave it free for something with me.

I walked home elated. I had a great weekend and was looking forward to seeing Tiffany on Monday. My balls ached, but I was happy.

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

Part 22

I was still in a good mood Monday morning. The first half of the work day flew by. In the early afternoon I texted Tiffany and asked if I would see her. She said she would come by and I was over the moon. It had been quite a while since I came and the last time was from a pegging with Caitlin. I really wanted to cum from stimulating my penis. I definitely hoped for a handjob from Tiffany, but would settle for the masturbation tube.

That evening, when I met Tiffany at the door she was wearing a form fitting dark blue dress and matching pumps. Her hair was pulled back in a ponytail and she was grinning from ear to ear. We embraced and she then made her way over to the couch.

I grabbed a couple of beers, gave her one and set the other on the floor. I stripped down to nothing but my chastity cage and sat at her feet. I removed each of her pumps in turn and began rubbing her feet.

"Tell me about your date with Lily." she started.

I told her about every bit of my time with Lily. Tiffany listened intently with not much of an expression on her face. When I concluded she said that she was happy that the weekend was so good.

"I have plans to meet up with Lily on Thursday for coffee. She and I have decided to meet up weekly to compare notes on your relationship." she continued.

"Ok... why is that necessary?" I asked.

"Well, I feel responsible for you. And she seems to like the current arrangement. Plus, I like her too." Tiffany answered.

With a frown, I accepted her answer. I was not convinced, but I knew arguing about it would be counterproductive.

Tiffany then asked me if I wanted to ask anything of her.

"It has been a while since I have cum and I'm in quite a bit of discomfort. I was hoping that maybe you might... let me cum today?" I asked.

She pursed her lips ever so slightly and said, "Sure. Go get the tube, lube, cuffs, and towel."

I excitedly got up and got everything needed. I returned to the couch and Tiffany took the cuffs and bound my hands behind my back. She set the tube in the couch cushion after lubing it and then unlocked my chastity device.

But rather than taking her regular place on the couch above the tube, she stood beside me.

"I got a text while you were getting everything and I have to return a call. I will make the call from your bedroom while you take care of your needs. Don't wait, I might have to go right after the call." she said.

With that, she walked off to my bedroom and shut the door. I didn't move for a few moments as I was taken aback. Before long, I realized that I needed to take advantage of this opportunity for relief, so I started to use the tube. After a few minutes, I came in the tube and pulled out. I had to continue kneeling for quite some time before I could hear Tiffany come out.

"Did you finish? I am going to have to run." She said as she approached me.

"Yeah, I'm done." I responded.

She came over and wiped me down with the towel and reattached the chastity device. After she unlocked the handcuffs, she sat down and put on her shoes.

"Is everything okay? Was it the call?" I asked

"Yeah, everything is fine. Just an issue at work. I'm actually going to have to head back there now." She answered.

With almost no ceremony she started toward the door. I followed her, but she opened the door without a hug and just turned slightly and waved as she left.

Something didn't seem right and I didn't think it was the call. No, I'm just being paranoid, I told myself.

Regardless, I was crestfallen. The day had started so positively and ended on a hollow note. Although my balls no longer ached, I had a nagging feeling that something was wrong and it was my fault.

I waited until the next day around 11am to text Tiffany. I asked her if work was okay. She didn't respond until around 5pm. She said that the shit had hit the fan and that her week was shaping up to be hell. She added that she didn't expect to be able to stop by for a while. I sent back a sad face and asked her to tell me if there was anything I could do to help.

For the rest of the week, I texted her to check in and she would just respond that things were still the same. By Thursday morning I had resolved myself that I wouldn't see her again this week.

Although I was very disappointed by my lack of interaction with Tiffany, I had been texting with Lily about Saturday. We were planning to get dinner at one of my favorite places and then off to a movie that we were both excited to see.

I stopped texting Tiffany and tried to console myself that I was probably not the reason she was upset. I figured it would be better to give her a little space and for me to focus on Lily.

I walked over to Lily's place on Saturday and met her on the sidewalk. We took a ride share to an Indian place that I really enjoy. We had a great time chatting and joking around. After dinner we walked to the theater. We got popcorn, chocolate covered raisins, licorice, and a large soda to share. We settled into our seats that were the reclining type. We were pretty early and the previews hadn't even started, so we sat and chatted.

After a little pause in our normally fluid conversation, Lily asked me "So, I gather that before being locked you weren't really into kink or BDSM. Now that you have been exposed to some of it, do you find it satisfying?"

"Hmm, yes and no. I'm not so sure about the things themselves. I guess what I mean is that having my dick locked is not what I would call fun. It is actually quite frustrating. But, I find myself really turned on by how much you and Tiffany seem to enjoy it. Same goes for pegging. I think I may be a little more into the foot stuff." I answered.

"And what about being bossed around?" She asked with a smile.

"I don't know." I said smiling "I guess it depends."

"I think I would feel more comfortable with my shoes off. Take them off for me." She directed.

"As you wish, Lily." I said with a nod of my head.

I put my chair back into a seated position and stood and moved to the front of her chair. I untied and removed each of her black converse in turn and placed them on the floor between our chairs. She watched me intently eating popcorn as I worked. There were a few other people in the theater at this point and the lights were still bright, so some of them looked. It was a little embarrassing, but I didn't care too much. I sat back down in my chair and reclined it and turned my head to her.

"Good boy." she said with a grin and leaned in for a kiss.

After kissing for a bit, we pulled apart and I said, "I might not like being bossed around all of the time, but I did like that."

"Good, because I felt a jolt when you started untying my shoe and I saw the outline of your cage through your pants. I want to sit on your face so fucking bad." She finished with almost a growl.

"We can leave if you want." I offered.

She took a deep breath and told me that she can wait. She grabbed my hand with hers and squeezed tight, and leaned back in for another kiss. Around this time, the lights began to dim and the trailers started.

We directed our focus at the screen. Occasionally, I could feel her gaze on me and I would look at her. Her stare was lustful and drew out an animalistic desire in me. Then she would turn back to the screen, and after lingering for a bit, I would look at the screen too. We did this three times before she leaned in close, kissed me and said "next time we watch a movie, remind me to wear a skirt and no panties."

"Fuck." I whispered, "I'll remind you."

She kissed me again and said, "I'm going to focus on this movie and not my soaking wet pussy, I suggest you do the same."

And then she turned back to the screen. The movie started and I tried to focus on the plot, but I just kept looking at her. She did remain focused on the movie; well, her eyes remained on the screen anyway. By the time the movie was over, I felt frantic. I wanted to strip her out of her clothes and bury my face in pussy.

I had ordered a rideshare back to my place before the credits even ended. When the lights came back on, I got out of my chair, took her shoes one by one and put them on her feet and laced them up. I grabbed her hand and started pulling her out of the theater.

"Woah, what's happening?! Where are we going?" She asked playfully.

"I want you on my face right now. We're going back to my place." I said.

"Stop!" she exclaimed, "Don't forget, I'm the boss!"

After a brief pause, she said with a grin "Now, let's go back to your place so I can sit on your face!"

After a relatively short trip that was punctuated by aggressive kissing and fondling that must have disgusted the rideshare driver, we were at my place.

We stumbled into my apartment, undressing each other as we kissed our way to my bedroom. I tried to push her down to the bed but she resisted and instead pushed me down. By this point I was already nude and she only had her panties on. She stood on my bed above me and took them off. She told me to put my arms above my head and she lowered her pussy to my mouth, never breaking eye contact. She leaned forward and pinned my arms with her hands, shifting most of her body weight in that direction. I was already licking her pussy and then she started to hump my face. She started gently but got more aggressive very quickly. Before long, she was grunting and shuddering on top of me.

She shifted downward and collapsed on my chest and we kissed lazily.

"I want to fuck you so badly." I said to her.

She smiled, "I think you will, eventually. Tiffany and I met for coffee on Thursday and discussed a timeline. When we get to a certain point, I will ask for the keys. Tiffany will give them to me for use as long as I want them. And when I am done, I will return them to her. And, eventually, if we become serious, she'll give them to me to hold."

I wasn't really sure how to react to this information. All I could manage at this point was to ask what would be the point where she would ask for the keys.

"Well, it is a certain amount of time and other factors. Sorry to be vague, but I think part of this is that you trust the two of us. And although she is annoyed with you, I think Tiffany has your best interests at heart." She answered.

"She's annoyed with me? What did she say?" I inquired.

"She didn't get into details, so I don't know." Lily answered.

She continued, "But if you do want to fuck me, there is something I'd like to try."

"What?" I asked.

"You have at least two strapons here, right? Well, I want you to wear one and fuck me." she answered.

I was a little disappointed at first, but figured it might be nice to be on the other side of a strapon, so I agreed.

I got the strapon and harness that Caitlin had used and made sure they were clean. I put the harness on and had difficulty positioning the base of the dildo so it was comfortable. Eventually, I had it in a position that wasn't terribly uncomfortable. Lily watched as I made the adjustments; her face seemed stuck somewhere between amusement and excitement. I asked if she was ready; in response she got onto all fours and arched her back. The look of her narrow waist tapering out to her perfect ass and her pussy peeking out from between her thighs had me straining against my plastic penis prison.

I got behind her and lined the fake dick up to her pussy and slowly pushed forward. I saw it slowly disappear. She let out a gasp and a moan as I thrust all the way in. Her reactions were turning me on even more, but I could feel nothing but pressure against my lower stomach. It was a real mind fuck to have sex with someone in a way that was familiar and natural, but with no sensation.

She seemed to enjoy my thrusts so I tried to make sure I moved in a way that maximized her pleasure. Even though the basic movement was natural, it took some time to get used to the lack of sensation.

We changed positions a few times, and eventually she ended up on top. She was kissing me as she moved back and forth on the dildo. Eventually she came and rested on top of me kissing.

"That was nice! I understand it is probably awkward for you, but we will have some time to practice. I'll probably be using your face most of the time." she said.

She continued, "Let me do something for you. I'd like to rub your back. Turn over."

I did as she asked and laid on my stomach after removing the strapon harness. She sat on my ass; I could feel her still damp pussy rest against my cheeks. As she rubbed my back and shoulders I could feel her pussy grind into my ass. It definitely felt like she was humping my ass and I couldn't help but think about her pegging me. Although it was a turn on to think of her pegging me, the back rub was amazing! After a relatively short amount of time, I passed out.