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After Tiffany left I went into panic mode. I needed to find a date for the weekend. I didn’t want to go a whole week without getting some relief.
I started with Diane. She seemed happy to hear from me, but was heading out of town for the weekend. I made a few more calls but had little luck. I was not going to get a date out of my phone book this late in the week. I was going to need to hit the bars and try to find some action (well, as much action as I could manage in my captive state).
I called my guy friends and we hit the town Friday night. We hit the town again on Saturday night. I did not fair well. I managed to not even get a number. Honestly, I don’t have a lot of game, but I usually don’t bat a zero either. I think my situation was making me desperate and that desperation was showing. By Sunday night, it was looking pretty grim.
I could just lie to Tiffany and tell her that I did go on a date. How would she ever know? I could make-up a new girl and say that we hung out for one night but I didn’t like her much and wouldn’t be calling her again. That might be enough to get me another week of handjobs.
The more I considered that plan, the more I leaned away from it. I have known Tiffany for a long time. And in all of that time I have never been outright dishonest with her. I don’t even know why, but I just couldn’t stomach the idea of lying to her face. I was going to tell her the truth. Maybe she would be nice and let this weekend slide.
I sent Tiffany a text at lunch on Monday and asked if she would be stopping by. She responded, asking if I went on a date over the weekend. I took a while to respond but I finally sent her the answer… “no.” She said she would be stopping by on Wednesday.
My heart sank. I knew there was a possibility that she would keep to her word, but a small part of me just wouldn’t accept that it was going to happen. I spent the rest of the afternoon at work coming up with a list of activities for Monday and Tuesday night. I needed to keep my mind busy and off of my penis.
By Wednesday afternoon I was on edge. I had called Diane Tuesday night and set up another date for the coming weekend. I hoped that I would be able to convince Tiffany to be kind and let me out of my cage.
Tiffany stopped by my place after work. I met her at the door and saw that she was wearing a light pink blouse and dress pants with black pumps. Those pants made her legs look longer than they were and the material really made her butt stand out. God! What I would do to just see that ass of hers!
As usual, she sat down on the couch and I grabbed a couple of beers. We chatted for a little while until she turned to my dating life.
“So, I’m disappointed that you didn’t have a date this past weekend.” She started.
“I’m sorry about that, but I did set up a date with Diane for this coming Saturday. I was hoping that…” I spit out as a defense until she interrupted.
“Dan, that is all well and good, but it doesn’t make up for this past weekend and what has been weighing on my mind. I am trying really hard to help you find some happiness. Honestly, I was feeling a little used.” She said.
I couldn’t help but wonder how I was taking advantage of her given that she had MY sexuality under lock and key. Regardless, I have known Tiffany long enough to know that I shouldn’t argue with her feelings.
“I’m sorry that I made you feel that way, it was not my intent. I appreciate your help and I know that you mean only the best for me.” I answered.
“ I know that you didn’t mean to make me feel that way. It is partly my fault for not taking better control of the situation and clearly explaining to you how this is going to work.” She admitted. “So, I have been thinking of ways to continue this arrangement without any problems.”
“Since you’re the one locked up, you need to start by admitting to me that I’m in control of this arrangement and that you trust my judgment.” She said with her eyes locked on mine.
“umm..” I stumbled. “Yes, you’re in control of this situation and I trust you implicitly.”
“Excellent, that is a good start. Now I’ll tell you the way this is going to work from now on. I will let you cum as many times a week as I think is appropriate based on your effort to comply with my instructions. I will be letting you cum today since I did not make it clear to you that I wanted you to be doing something significant every weekend to meet a nice girl. But today will be your only release this week.” She said.
“Ok, I….” I interrupted.
“I’m not done yet.” She smiled.
“If you ever fail to show effort on a weekend again, I will not allow you any release the following week. Also, part of the reason I have felt used is that I am trying to help you and I have been giving you handjobs. I have been enjoying the foot rubs you give me, but I need to feel more in control of this arrangement. I’d like a foot rub every time I come over, and I’d like you on the ground on your knees when you give it to me. Will you do that for me?” She asked with a flirtatious smile.
“… ok, I can do that.” I responded with a little hesitation. I started to blush. As I consented to her terms it dawned on me that I would probably consent to just about anything that she asked of me. I’ve always loved her. And although the ship sailed on that opportunity a long time ago, I can’t stop myself from hoping.
“Aww… you’re blushing.” She smiled. “… and I haven’t even gotten to the things that should make you blush.”
“Really…?” I inquired.
“So, when you’re giving me the foot rubs I want you on your knees as I said. I also want you in nothing but the chastity device. In fact, lets get to my foot rub.” As she said this our eyes were locked on each other’s. I was motionless, still processing what she had said. That is when she very subtly started to nod. That broke my trance.
I started to unbutton my shirt and she gave me a smile. Before I knew it I was standing with only my pants on and unzipping them. When I was out of my pants, I slowly knelt down before her. She slipped her pumps off. She extended her right foot to me and I began to rub while I looked up at her.
“Now for the last change.” She continued. “I will not give you any more handjobs except when I feel like you have done a great job… or at my whim.”
With that she reached for her purse and pulled out a large object. At first I didn’t recognize the object, but I soon realized that it was one of those male masturbation tubes that looks like a flashlight.
“I’ll cuff your hands as usual and you’ll cum in this.” She announced.
“That is enough foot rubbing for now. I’ve been curious to see you use this thing. Turn around so I can cuff you.”
I did as she said and she cuffed my hands behind my back.
“Tiffany, how am I supposed to use that thing if my hands are behind my back?” I asked.
“Face me again and I’ll explain.” She directed.
I turned around again on my knees and I saw her dripping lube into the end of the device. When she was done, she lifted the end of the couch cushion she was sitting on and placed the device under it so the opening was sticking out a little from the couch. She then reached into her shirt and pulled out the key to my chastity device and unlocked and removed it.
“Ok, it’s all yours. Go for it.” She said nearly breaking into laughter.
I just knelt there. I wasn’t getting hard. I was really uneasy with this situation.
“What’s wrong? I figured you’d be ready to go at the drop of a hat by now.” With that, she scooted back on the cushion and brought her foot up to my crotch and slowly and gently started to rub my penis with her toes. It wasn’t long before I was hard. Then she stopped and said “Say hello to your new friend.”
I waddled forward on my knees until my cock was just before the device and tried to push into it. It took a few attempts, but I finally aimed correctly and started to enter it. Tiffany moved up on the couch. Her legs were spread wide and the crotch of her pants was only half a foot from the opening of the device. She was staring down at my cock pumping into the fake pussy. She was fixated as I thrust back and forth. I was looking up at her – her face – her cleavage – the tight crotch of her pants. I was trying to imagine that it was her that I was fucking and not the couch. I noticed that as my rhythm increased her fingers were clenching her knees tightly. After a while I shuddered as I came into the device.
“That was hot. Wait here while I get a towel” She said as she stood up, swinging her leg over my head.
She was gone for a while – longer than it should have taken to get a towel. All the while I stayed imbedded in the device. She finally returned and wiped me clean and put the chastity device back on. She then removed the cuffs and told me to get dressed.
“So, I hope this new arrangement will have you motivated to listen to me. I’m glad that you have that date with Diane this weekend. You should try to meet more women. Maybe a speed dating event. The quicker you find a nice girl, the quicker you can go back to “regular” sex.” She smiled.
And with that she got up and made her way to the door.
“I look forward to hearing about your date next week.”
She gave me a hug. While she was hugging me she gave me a brief tight squeeze and said softly “I love you.” She then broke the hug, and without any eye contact, turned toward the door and left.
Sigh.
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.
