Pick Your Poison

I heard the door open then close and wondered if she was finally ready to deal with me. I had been cuffed spread eagle to the bed for who knows how long now. It was dark outside and I couldn't see a clock in my limited field of vision. My muscles aches and my jaw was sore, holding my Goddess' dirty panties in my mouth for so long. I had been instructed to keep them in and did not want to know what would happen if she found me without them.

It was Sunday night and my friends with benefits turned Goddess had texted me that she required my service. Being the obedient sub I am, I immediately drove across town to her apartment. When she let me in the house, I couldn't help but stare and stiffen in my boxers. She was incredible. She answered the door in a form fitting blue dress, showing off her ample chest and shapely hips. Without a word, she turned and began walking through the apartment towards the stairs. I nodded sheepishly, turning bright red as I followed her past her two friends (both attractive in their own right, but nothing like my Goddess) in the living room. I couldn't help but wonder how much they knew of the nature of our relationship. It started as something I would've been proud of, even flaunted. But as time went on, she began to assert more and more dominance, eventually taking over full control of our sexual encounters.

My heart skipped a beat as I followed her up the stairs and she did nothing to hide the view up her dress to the tight, red thong, wedged perfectly between the globes of her ass. She had been working hard in the gym and it was clearly showing. There was no hiding the growth in the front of my shorts now. As we entered her room, she snapped her fingers, signaling to me to disrobe. I quickly removed my clothes and knelt before her, my cock growing swiftly and waving lewdly in front of me.

"What a good little bitch," she had cooed, running her hands through my hair. "You've earned a little treat." With that, she bent over the bed, bunching her dress up and thrusting her ass towards my face. "You know what to do, bitch," she growled at me.

I wasted no time, diving forward and pressing my tongue past the string of her thong, licking all around her tight rose bud. My hands found her ass cheeks as my face buried forward, worshiping her hole. "My my, little bitch must really want to cum tonight if you're worshipping me that well," she moaned, pressing her ass back at my face.

Unable to speak with my mouth occupied, I increased the fervor that I was tonguing her with, hoping she would know I meant yes. I was desperate to cum. She had spent the entire Friday at the school where we work teasing me. Flashing me, rubbing me, whispering dirty things. As we left work for the day, she texted me making it very clear I was not allowed to masturbate until she said so. Saturday had not been any easier, as she bombarded me with snapchat after snapchat of her vibrator on her glorious pussy and reminding me to keep my hands off "her" cock.

I felt her shudder a little as her first mini orgasm hit her. "That'll do for now," she said, standing up. "If you want any chance at cumming, you will do exactly as I say. Now get up on all fours and spread that boypussy for me."

I immediately obliged, taking her place on the bed, my face pressed into the covers, my ass and cock thrust back towards her. Reaching back, I used my hands to spread my ass and await her next move. The furthest we had gotten with anal play was her teasing the outside of my asshole, but I trusted her and submitted fully to whatever she decided. I heard the cap of the lube and shuddered as I felt the cool touch of her finger circling my tight hole. Gradually she began to push deeper, curling her finger as each knuckle passed. My cock throbbed wildly as she pressed on my prostate, eliciting a deep loan from me. "What a slut!" She exclaimed. After several minutes, her finger slid from me, leaving me feeling truly empty. The feeing was not to last as her finger was quickly replaced with what I could only guess was a butt plug or dildo. My suspicions were confirmed as the plug slid past its widest point and settled inside me.

"In your cuffs! Now!" She ordered, slapping my ass. I quickly flipped over, securing one of my hands in a cuff and waiting for her to do the other. She did so and then proceeded to pull a silky pink thong from the dresser by the bed. "I think you'll be my pretty little pantyboy tonight," she giggled as she slid the thong up my legs, setting the string against the plug in my ass and tucking my throbbing cock into the silk.

"Now then... the girls and I are going to have some fun at the club. Try not to make too much of a mess in your little panties," she said, reaching for her purse. "Oh and just so you don't forget about me, let me leave you with a taste." My cock twitched in its silky prison as she slid her red thong down her legs, balled it up and placed it in my mouth. "You'll be sorry if that's not there when I return!"

"I almost forgot!" She exclaimed, halfway out the door. "You can have some fun while I'm gone!"

My eyes burst wide as the plug within my whirred to life, vibrating strongly against my prostate. "I'll just leave this here," she said depositing a small black remote just out of reach on the bedside table. "Don't wait up!" And with that she was gone.

So there I was... panties soaked from my dripping cock, ass sore and filled even if the vibration had run out of battery, and eagerly awaiting the tipsy Goddess stumbling back into her room. My heart skipped a beat as the door opened again and more giggling voices entered. Oh my god! She had brought her friends in to see me in this state. Despite my humiliation and embarrassment, my cock quickly responded, making a very visible tent in my little wet thong.

"Oh my god! He really is your little pantyboy bitch! I need to get one of these!" I heard one of the friends say. My goddess moved into my field of vision, now sporting only a red bra, barely containing her enormous chest. Her tits were absolutely perfect and I begged to see the nipple piercings I knew were underneath.

"You've been such a good little pantyboy! I think you've earned a chance to cum. However, my friends and I were talking, and we don't believe that you should be allowed to take up so much of our time with your need to cum and sexual pleasure. Luckily for us... well maybe not for you... my friends had some good ideas."

Her friends moved closer, both in various states of undress. My cock lurched, leaking more into my panties. Each friend held up a brown paper bag.

"We're going to give you a chance to cum tonight, pantyboy, but you're going to have to work for it! I'm going to stroke that pathetic excuse for a cock, more of a clit really, in your little pink panties for 3 minutes. I'm going to stroke at the same rate the whole time. All you have to do if you want your sweet release is cum In those three minutes."

I groaned. I knew I was close to a chance at release.

"Of course, if you do cum in time, there is a punishment that goes with it. Because obviously you can't call yourself a man if you can't last 3 minutes with a handpussy instead of even fucking or getting a blow job. Therefore, if you cum, you'll be wearing pretty little thongs for the remainder of the week. I'll be confiscating all boy underwear from now until next Sunday. Of course, you'll be free to cum all week, but never stroking or fucking like a man. No, If you cum in time tonight, you'll only be allowed to cream your panties all week using either a vibrator or rubbing your little clitty through the silky fabric."

The friend on my left tilted down her bag to show me the multitude of different colored thongs contained within.

"Now. For your sake, I hope this is not the case, but we need to talk about what happens if you take up too much time and do not cum before the timer goes off. If that's the case, then clearly you really didn't 'need' to cum yet. My friend over here has something in her bag that might help you get ready."

The other friend reached into her bag and with a huge grin, pulled forth exactly what o had begun to fear it was. It was small and pink, but there was no denying that it was a chastity cage.

"That's right, Bitch. If you can't cum in time, you'll be locked tight for the entire week. Reporting nightly to this apartment to give each of us an orgasm with your tongue, but no relief for you. If you follow all those guidelines for the week, we will play this same game next Sunday and see if your cock wants to be a little more cooperative. Shall we begin?!"

I moaned loudly into my panty gag as I felt her slippery, lubed up hand slide into my thong and encircle my hard cock.

What had I gotten myself into?!