Tag Archives: chastity stories

After Tiffany left, I went and dropped down on my couch. I don’t know exactly how long I sat there because I was in a bit of a stupor. When the shock finally wore off, my mind began to race. I was upset at Tiffany. I needed to get out of this thing. Can I get it off myself?

That’s it! I’ll cut the damn thing off! I live in an apartment and so I don’t have a full set of tools, but I took out my little collection and stripped off my pants. I sat there at the kitchen table eyeing various tools. I even brought a pair of wire cutters closer to my junk than I ever thought I would. But, it didn’t look like there was any place to get a hold of the lock. None of my tools were meant for that kind of use.

I ran out to the local hardware store and browsed the aisles. I even asked a salesperson what he would use to cut a small lock. But all of the tools that would have worked to open the lock would also have a pretty good chance of maiming me in the process. So, I had to abandon that idea. Shit!

I was going to have to rely on Tiffany. How was I going to get the keys from her? Maybe if I played along, I could get her to take it off for a little bit, and then I would not allow it back on. Ah man, I should have done that to start with, she would probably not buy my faked cooperation now. All I could do now was give it another try and then, if that failed, take more drastic action.

My frustration at my predicament made sleep difficult that night, but eventually I went to sleep. I went to work and awaited the afternoon and another visit from Tiffany. I had no plan except to be agreeable and hope that my chance would arise for escape.

I left work a little early and hurried back to my place. I didn’t want to miss her. I sat waiting with anticipation. Eventually I was buzzed from downstairs. She was on her way up. I greeted her at the door and tried to act nonchalant.

As usual she was impeccably dressed and seemed to be in good spirits. Oddly our interaction seemed pretty unaffected by our conversation the prior day. She sat on the couch and began talking about her day at work. I grabbed a couple of beers and sat beside her. We made small talk for a while. She seemed completely unshaken and acted as if there was nothing else on her mind other than the small talk. I tried my best to act the same way, but on the inside I was feeling a bit anxious about how I could create the opportunity to get out of my cage. I was sure that if I brought it up, she would see right through it. So, I decided that I would have to wait for her to broach the subject.

Eventually, there was a pause in the small talk and she asked me for another beer. This wasn’t usual as she didn’t normally have more than one on the weeknights that she stopped by my place. I complied with her request and grabbed us both another beer. When I sat back down on the couch she began…

“So, I have thought about our conversation yesterday and have come up with a solution.” She said and reached for her purse.

“What is your solution?” I asked

Without saying anything, she pulled a pair of handcuffs out of her purse and, with them dangling from her index finger and thumb, she extended her hand toward me. She gave the cuffs a slight shake and widened her eyes and arched her eyebrows. I reached out and took a hold of the cuffs.

“What’s up with the cuffs?” I asked.

“Well, if you want to cum, you’re going to have to put them on. Lock them on one of your writs and put your arms behind your back and I’ll fasten the other.” She said.

At this point I am still unsure about her plan, but I didn’t expect cuffs to be involved. I’m angry because if I cooperate I probably won’t be able to stop her from putting the device back on. What other option do I have at this point? Besides, an opportunity for escape may still arise.

“Okay.” I said snapping one side of the cuffs to my wrist. Still seated on the couch, I turned my back to her. All the while my heart was pounding and I was hoping that this was going to work out to my advantage. I could feel her grab the unused side of the cuffs and my free wrist and pull them together. Snap. I now had my hands cuffed behind my back.

“Be gentle” I said, trying to keep the mood light.

She laughed and said “Don’t worry, I’ll take good care of you.”

She got up from the couch and helped me to stand. She told me to stay put while she went into the hallway and opened the closet. When she returned she had a large bath towel. She spread the towel out on the floor and grabbed my upper arm and led me so I was standing with the towel in front of me.

“Um… so, what exactly are we doing?” I asked.

Tiffany looked at me and smiled. “Don’t you worry, I’m sure you’ll have no complaints.”

With that she knelt down and untied my shoes and told me to step out of them. Still on her knees, she unbuckled my belt and undid the button and zipper on my pants.

OH MY GOD! IS TIFFANY GOING TO GIVE ME A BLOWJOB! I could feel my head spin and my heart race. Was this really happening? I could feel myself start to strain against the device. But before these thoughts had gone too far, Tiffany stood up and pushed my pants and underwear down. She was now standing right before me and I was naked from the waste down with my pants pooled around my ankles. She steadied me by grabbing my shoulders and told me to step out of the pants. After she kicked them aside, she fished a long necklace out from her blouse and at the end was the key. She pulled the necklace off and, bending slightly, used the key to remove the small lock. She then returned the necklace to its place inside her blouse.

She then made eye contact with me and told me to relax. She then removed the pieces of the chastity device one by one. The moment my penis was free it was swelling. It felt amazing to get hard. I never really appreciated my erection as much as I did at that moment.

“Well, it looks like someone is happy to see me!” Tiffany said with a slight chuckle while she stared at my erection.

I could feel myself begin to blush and laughed nervously. She moved over to her purse and pulled out a small bottle. She squirt some clear liquid from the bottle into her right palm, put the bottle down, and moved behind me. I immediately tensed up a little bit.

“Relax” she said. “Close your eyes.”

I could feel her body behind me and in an instant her hand was wrapped around my cock. The sensation of the lube was cold but her hand was soft and she started to stroke me. She wrapped her left arm around my waist and pressed her body up against me. I could feel her breasts pushed up against my arms.

“mmm… you are certainly working with something here. No wonder all of those girls keep giving it to you. Very nice” Tiffany cooed.

I let out a gasp. I was in ecstasy. I had been pent up for days. Tiffany was stroking and complimenting my cock. Needless to say, I didn’t last long. Before I knew it, I was shooting all over the towel and shuddering in her arms. She held me stable until I regained my balance.

“Wow, I must be really good or you haven’t come in days.” She said laughing.

“Oh, it was both. That was amazing. I feel dizzy.” I responded.

“Stand still, I’ll be right back.” She said.

After a few moments, Tiffany returned with a wet facecloth and wiped down my penis. The facecloth was pretty cold and a little rough and I stayed soft temporarily. She quickly began putting the device back on and slipped the last piece on before I became aroused again. CLICK. I was locked in once again.

I should have been angry, but I was still reeling from my first sexual release with Tiffany. She then uncuffed me and went to wash her hands. I put my pants back on and removed the towel from the floor. When I returned to the room, Tiffany was plopped down on the couch. I sat down on the couch and had a sip of my beer.

“Well, you must have liked that. You’re still smiling.” She said with a big grin.

Not until she said it, did I realize that I must have had a huge grin since I came.

“Well, that was amazing!” I said.

“I know a way you could repay me.” She started “my feet are killing me.”

And with that she slipped off her heels and swung her legs up onto my lap.

“Would you mind?” She asked.

“Of course not, it is the least that I could do.” I said with a laugh.

And with that I began to massage her perfect little feet. She let out a couple of very soft moans and told me how good it felt. I could feel my recently relieved penis start to swell up again.

We talked for a little bit and finished our beers. Before I knew it, I was hugging her goodbye at the door.

That evening I relived the experience in my mind again and again. My situation was far from ideal, but having such an intimate moment with Tiffany made my heart flutter. I was having trouble keeping my emotions at bay.

I spent he entire next day distracted and couldn’t wait to get home. Tiffany again made her appearance and the whole episode from the day before was repeated. This time no words were exchanged about what was happening. When she pulled out the cuffs, I put them on. When we were done, she just swung her feet onto my lap.

Although, I did think I noticed her pressing herself against my back a little harder – was she grinding a little? – did I imagine that?

That Thursday she sent me a text saying: “I’m not going to be able to make it tonight, sorry :(“

Although I was disappointed, I wasn’t nearly as upset as I had been just a few days before. I could deal with not being let out. Maybe it was because I still euphoric from the shift in my relationship with Tiffany.

Friday rolled around and Tiffany was again on my doorstep. Our pattern from the first two times continued. While I rubbed her feet, she shifted the conversation to my dating life.

“So, are you seeing Diane again this weekend?” She asked.

“Actually, I haven’t called her this week.” I responded.

“Oh, is there a new girl then?”

“Actually, I don’t have a date set up for this weekend. I guess I’ve been distracted.”

“Dan! Don’t forget why we’re doing this. You better set up a date with Diane or someone else for this weekend or I won’t be coming by next week.”

“But… but…” I stammered.

“No excuses. Get a date for this weekend.” And with that she smiled, put her shoes back on and left.