When my best friend Stephanie asked for my help with something special, I agreed immediately, “What are friends for?” What I wasn’t expecting was what exactly I would be helping with; although I’m glad I decided to go! Stephanie had text me, asking me to come by her apartment that night, simply saying that she needed my help with something. I have known Stephanie since elementary school, and have watched her grow into the beautiful 5’6 blonde woman that she is today.
That night when I walked in, everything seemed normal. We sat down, and had a beer, making small talk. After a little while, I finally asked, “So what’s so important that I had to rush over here tonight? You didn’t break up with that new girl already, did you?” The wicked smile that crosses her lips should have tipped me off honestly, but who would ever expect what was coming next?
“No, she and I are still together, although we have hit a slight issue recently. I won’t go into details, but I wonder, could you help me handle it? I have something special in mind, and I think you’re the perfect man for the job, and you’re someone I trust completely, so I can’t imagine anyone else I would ask.”
The way she said “man for the job” struck me as kind of odd and in the back of my mind, a rather dirty thought popped up. Was Stephanie about to propose a threesome? Rationally I knew that didn’t make sense, but like any guy, I was immediately turned on by the idea. With a laugh I said “Sure Steph, I’ll have a threesome with you, I thought you’d never ask!”
All of the sudden, my best friend was gone; the sweet innocent girl I had always known was replaced with a strong woman, with a wicked look in her eyes. As she stood up, she announced over her shoulder “I like your spirit Andy, and you’re almost right. But we won’t be having a threesome!”
As she walked to the back of her apartment, I was confused. Should I get up and follow her? What did she mean by ‘almost right’? As I sat there confused, Stephanie came walking back in the room, with her hand behind her back. It took me a second to realize that she wasn’t alone either. As I watched, Stephanie walked in with a gorgeous redheaded woman crawling on the floor behind her, with a ball gag in her mouth, and a collar around her neck, which Stephanie had attached a leash too and was using to guide her pet along. The thing that shocked me was that I recognized the girl crawling on the ground. Her name was Claire, and she was a member of the cheer squad from back in highschool. What the hell was going on here?
“This is Andy, he will be assisting me with your punishment tonight Claire. This is what happens to bad little lesbians who don’t obey!” she explained to Claire as I watched. As confused as I was, my cock was growing harder by the second as the twisted part of my mind evaluated what was going on. Claire was completely naked, wearing only a ball gag in her mouth and a collar around her neck. From my angle I could see that there was a fluffy fox tail hanging from a butt plug which was wedged firmly in the former cheerleaders incredibly shaped ass, and I watched as her tits swayed back and forth as she crawled.
As turned on as I was, watching this teenage fantasy play out in front of me, I still needed answers. “Steph, what the fuck? Isn’t that Claire from highschool? Why is she crawling around your floor naked? Why am I here?”
With the crack of a belt, Stephanie ordered Claire to sit. I watched as the naked girl sat down like a dog, which pushed the butt plug in her ass deeper. Sitting down next to me, Stephanie leaned in close and whispered in my ear “Andy, I’m a dominatrix. I have been for years, but I never told you. Now though I need your help. Claire has never been with a man, but has confessed to me that she wants too. I recently caught her flirting around with people online, and decided that I would kill two birds with one stone. I get to punish her, and she gets to finally fulfill her fantasy of being fucked by a man. I know this is all very sudden, but I didn’t know how else to ask you or explain the situation. If you’re uncomfortable, I completely understand. But according to the tent in your pants, I think you might be interested in helping me… What do you say?”
I couldn’t deny how turned on I was, both by realizing that I was about to fulfill one of my own fantasies, but also by watching how uncomfortable and scared Claire’s face was as she watched Stephanie and I discuss her. There was no way I was going to miss this opportunity! With a voice loud enough for both women to hear, I asked “What would you like me to do with this slut Stephanie?”
She knew she had me then, and raised her voice as well. “Whatever you want, if Claire wants attention then she can have it! You can fuck her mouth or her pussy, but leave her ass alone. That’s for me to play with!” Standing up, she walked over to Claire and grabbed her by the chin. “This is what happens to little sluts who like to flirt and tease on the internet! Now get over there and serve your new Master. She swung the belt she was still holding in her hand, catching Claire across her ass just as she started crawling towards me, causing her to yelp around the gag that was still in her mouth. With that she walked out of the room, leaving Claire and I alone.
As the hot little redhead crawled towards me, I could see the shame in her eyes as tears started to crawl down her face. I’ve never considered myself a very sadistic man, but seeing her embarrassment and fear turned me on even more. Without thinking, I reached forward and grabbed her by the obviously dyed red hair, quickly dragging her the rest of the way. She stumbled while trying to keep up, and her head fell in my lap where she could feel how hard I was already. Still holding onto her hair, I pulled her head up to look me in the eyes. “I don’t think you remember me, do you Claire? We were in science together, and if I’m honest, I’ve wanted to do this for a long time…” As I spoke, my other hand was busy undoing my belt and pants, freeing my 8 inch cock to pop out and point directly at Claire’s face. I slid the gag out of her mouth, and jerked her head back down into my lap. “Time to get to work slut!”
Much to my surprise, Claire didn’t hesitate, bringing her hands up to brace herself against my thigh, while wrapping her free hand around the base of my shaft. It was obvious she had never sucked a cock before, as she gently bobbed her head up and down, engulfing the head and going down about an inch before coming back up. I let her do this for a minute before pushing her hands away, and seizing the back of her head to push her all the way down. She had taken most of my meat before she started gagging and trying to pull back up. “Oh no Claire, you have to get over that gag reflex! And use your tongue, as well. If you don’t make me happy then I’ll make sure Stephanie knows about it!”
This threat was clearly enough to keep her in line, as Claire stopped trying to pull away and I could feel her tongue begin to slide up and down my cock, doing her best to keep her gags under control. Eventually I released her head, allowing her to continue to suck at her own pace. Each time she went down, she pushed herself as far as she could, licking and sucking every inch of flesh she could reach. For a first timer, I was quite impressed! It was then that I got my first glimpse of what my best friends tits looked like.
Stephanie walked back in the room, completely changed. She was now wearing a pair of black lace hip huggers, and a mesh top that went from her neck to her navel, but didn’t do anything to actually cover the 34D’s that I had often imagined. If anything, the black mesh made them look even sexier. I couldn’t take my eyes off of her as she walked over and kneeled down behind Claire, who was still sucking for all she was worth. In her hand she was holding a large purple dildo, which she began caressing against Claire’s bare pussy.
“Having fun you two? I know Claire is, I don’t think I’ve ever seen my little pets cunt so wet without being touched before!” At her words Claire’s face flushed a bright red, but continued to suck me. I watched her eyes grow large as Stephanie began sliding the purple dick into her pussy, a little at a time. She was clearly in pain, but began sucking even harder as she moaned around my cock. We spent a few minutes like that, impaling the poor cheerleader between us, meanwhile both making comments about how hot she looked being double teamed and discussing other ways to use her.
Finally, Stephanie got up and sat down next to me, rubbing her pussy through the lace panties as she watched Claire work most of my meat into her throat. Again she leaned over to me, and whispered in my ear. “Do you want to fuck her?”
Her words combined with watching her rub her pussy right next to me almost pushed me over the edge. “Fuck yeah! Would that be ok, do you think?”
“She’s my toy, and I’m letting you play with it. Put on a condom and you can fuck her as hard as you’d like. Her pleasure doesn’t matter.”
I didn’t need telling twice! I quickly stood up, letting my cock pop out of Claire’s mouth, and dug into my bag, pulling out a condom. As I opened it and rolled it on, Stephanie had guided Claire’s face between her legs and pulled the panties to the side, allowing Claire full access. Kneeling down, I watched as my best friend got her pussy eaten by one of my highschool crushes, who I was going to fuck at the same time! I gently rubbed my cock up and down Claire’s lips, enjoying the sight of her glistening flesh. Pulling back slightly, I wrapped my hands around her hips and thrust forward roughly, burying myself inside of her. As I stayed there, enjoying the feeling of her pussy gripping my meat, Stephanie’s eyes met mine, and I could see the lust there as she came close to her own orgasm.
Keeping a tight hold on her hips, I began to thrust roughly into Claire. I wasn’t slow or gentle, I wanted her to feel it, and remember the pain I had brought her forever. With each thrust, her body rocked forward, pushing her lips and nose tightly against Stephanie’s pussy. The two of us used our toy roughly, with me fucking her as hard as I could while Stephanie ruthlessly grinded against her face. I could feel my balls starting to clench up, as I looked my best friend in the eyes. “I’m about to cum in your toy Steph, hope you don’t mind!” My words pushed her over the edge, grabbing Claire’s hair tightly and holding her head while she screamed out her orgasm against her face. Watching my best friend orgasm got me, as I rammed my hips forward, pushing as far in as I could, and wishing in the back of my mind that I wasn’t wearing the condom.
That was two months ago, but apparently Claire and Stephanie had an incredible time. I have been invited over several times since, and each time Claire meets me at the door wearing her butt plug and collar. Sometimes Stephanie and I share her, and sometimes it’s just me using the tight body of my highschool crush. I’m always happy to help in any way though, after all, what are friends for?