Drink or Dare

Lucy then pulled off Jay's blindfold and climbed onto his chest. He was glaring at her, nostrils flaring. Clearly he was pissed off, but a little scared now too as he was completely at her mercy. Lucy lowered her face next to Jays and said in a low voice so Dale wouldn't hear "I don't appreciate being manhandled like you did earlier. Do you treat all your girls like that Jay? I believe you do. I've heard the stories from the girls at school. You think your gods gift to women, don't you? Well I think its high time someone taught you a lesson. I think you should see what it feels like to be a woman for a while." She got up and went to her duffel bag and rummaged around inside it pulling out a pleated miniskirt, a strapless bra and makeup bag. She pulled the miniskirt over his legs and up over his waist with a little effort and some struggling on his part and hers. She then sat him up and strapped bra around him and fastened it in back. Pushing him back down she straddled his chest again and began to put the most garish makeup job on him that she could as he struggled to get his face away from her.

She lowered herself to his ear once more and hissed. "Quit it Jay! Now we want you to look nice and pretty for your big moment and if you struggle you'll wind up looking even more whorish than you do already." Jay continued to struggle till Lucy reached behind her with one hand grabbed his balls in a firm grip. Jay immediately stopped moving. "That's better. You wouldn't want me to start squeezing now would you, so be a good boy. We're almost finished anyway." Lucy put the finishing touches on Jay's makeup job and leaned back to admire her work. "Hmmm... not my best work, but It'll do." she said. She got off his chest and pulled out a long curly red wig and placed it on his head. "Oh yea. That's one ugly girl! I bet she still gets some though. What do you think Jenn?"

"Yea she not exactly a looker, but even ugly girls need lovin too." replied Jenn "And look, it seems Tiffany has fluffed your man for you. Thank you, Tiffany!" Dale didn't seem to be paying any attention to the conversation, if he could even hear it. He was too absorbed in me sucking on his shaft. "Lets get Dale up so we can prep the new lovers for their first time with each other"

I was enjoying going down on Dale as I usually do and wasn't really interested in stopping, but Jenn pulled me off the bed and stood Dale up at the foot of the bed. Then Lucy rolled Jay over onto his stomach and took another piece of rope and tied it from his wrists to the head board. She then pushed him back onto his knees which made his arms stick up behind his back. Lucy then got up and walked over to Dale. "Ok, Dale, you ready to fuck Jenn's sweet pussy? She wants it from you bad. I'm gonna guide you onto the bed and into her. If you're good I'll cut your wrists free so you can have at her, but don't take the pillowcase off Ok?"

"Uh... Ok." replied Dale

Lucy pulled out some lube and smeared it all over Jays ass which was now sticking up in the air, and rubbed some on Dale's erect cock. Jay's eyes were wide with fear and tried wiggling out of the way, but with his arms and legs tied and Jenn holding him in place he really was stuck. Lucy guided Dale on to the bed and placed the tip of his cock at Jay's quivering bunghole and rubbed it up and down then started working it in a little at a time. It took a monumental amount of effort on Lucy's part just to get Dale's enormous cock head inside Jay's virgin sphincter, but she managed it after five minutes of steady work. Jenn was groaning at Dale and egging him on so he couldn't hear Jay's muffled screams through his ball gag. Once the tip was in Dale seemed to sense it and immediately started thrusting away at Jay's ass. At first he couldn't get it in very far because Jay would rock forward every time Dale would thrust, but Jenn placed herself at Jay's head and pushed back onto his shoulders forcing him back onto Dale's immense cock. It took about another five minutes till Dale was able to fit his most of his cock inside Jay's ass with each thrust he gave.

"Ok, Dale. I'm going to cut your wrists free, but remember, keep the pillowcase on. Feel free to bang Jenn as hard as you like though." said Lucy

"Oh god yes! Fuck my pussy hard Dale! I want you to really give it to me!" screamed Jenn. Lucy then cut Dale's wrists free and he reached forward grabbing a hold of Jay's hips. With the miniskirt on Jay's waist, Dale didn't seem to realize who he was fucking and proceeded to really lay into Jay's ass all the while Jenn was cheering him on. Lucy pulled out her camera phone and started snapping off pictures, making sure she got facial shots of Jay with another man behind him. Dale was now managing to get all nine and a half inches of his enormous member into Jay's ass and even though Jay had his eyes closed, I just thought he was just bearing down through the pain. After about five minutes of steady pounding though, muffled groans started coming through his ball gag. Lucy knew exactly what was happening. He was actually enjoying the reaming his ass was getting. Lucy proceeded to cut the bonds on his wrists, but Jay made no effort to get away. Instead he propped himself up and started rocking back as Dale thrust forward. "Oh, Jay! You're such a quick learner! Aren't you my little slut? You love that cock don't you? Its Ok. You can tell me. Nod your pretty little head for me, my slut." whispered Lucy in Jay's ear. Jay obediently nodded his head and grunted through his gag. Jay was now lost in his own world. He continued to rock back in counter point to Dale's thrusting in his ass and it didn't take too long before Jay began cumming all over the bed and the miniskirt he was wearing. Dale had no idea what was happening so he continued to bang Jay's ass without pausing.

Lucy leaned down and whispered in Jay's ear again. "Now you've been such a good girl, I'm going to give you a nice treat. Tiffany is going to take your place, because she's been wanting to have Dale fuck her for the longest time. Dale wont even know that he was fucking you, and we won't tell him as long as you're a good little boy. Got it?" she asked Jay, and again he nodded obediently. "I'll clean the makeup off your face and you can take the clothes off, but you're going to let Tiffany suck your cock while Dale fucks her, Ok? This is our little treat to all three of you. You get to have your dick sucked by a hot blond, while Dale bangs her and Tiffany gets the fantasy of a lifetime realized. Guys aren't the only ones that dream of having a threesome. So are you game for that? Of course you are, what am I thinking!" she laughed.

"Ok, Dale. Hold up a second. I think its my turn now, back up just a little will you?" Lucy said out loud. Dale stopped and pulled his cock out of Jay's now stretched ass. Lucy cut Jays leg bonds and helped him off the bed while Jenn cleaned up his spunk off the sheets and laid a clean towel down for me. I took off my panties and crawled onto the bed on all fours in front Dale. I was so excited that I was finally going to feel his beautiful cock up my ass I was practically vibrating.

"I'm ready for you now Dale." said Lucy once I was in place. Dale reached out blindly and felt for my ass, grabbing my cheek with one hand and guiding his cock with the other. It took him a few seconds for him to feel around and finally line up his cock with my bunghole, but when he did he slipped it right in and buried straight to the hilt, filling me up completely. Oh my god, his huge cock felt so utterly overwhelming and filled my entire being. I never wanted anyone to screw me so bad than I wanted him to right then and there. He pulled it almost all the way out and then all the way back in again. Now his other hand was on my hip as well and began to pick up speed. Harder and harder, faster and faster he fucked my ass. I could feel his balls slapping against my taint with every thrust and it was driving me crazy. At this point Jay was all cleaned up and he got on the bed and knelt in front of me. I immediately took his cock into my mouth and sucked for all I was worth. Having just came, it took him a minute to get completely hard again, but when he did I gobbled as much of his cock down my throat as I could possibly handle. Lucy walked behind Dale now and grabbed the top of the pillowcase. "Enough of the charades Dale. See who you're really fucking!" she yelled as she yanked the pillowcase off his head. Dale looked down and saw himself fucking my ass as Jay stuffed my mouth with his cock. Apparently this really turned him on as he immediately began spilling his load deep into my ass. I could feel wave after wave of his hot seed flooding my bowels. It seemed like it lasted for two minutes and filled me with a gallon of cum, and when he was done he pulled out and flopped onto the bed exhausted.

Jay never stopped hammering my tonsils, and after Dale pulled out I was able to concentrate on deep throating him even more and playing with his balls as they slapped my chin. After a few minutes though my jaw began to get sore having been sucking cock for the last half hour straight. I pulled off of Jay's cock and stood up to look him in the eye. "I don't know if my mouth can take anymore Jay. I'm sorry."

"Thats Ok." he said. "Umm, how's your ass feel?"

That caught me totally off guard. I'd of never thought in a million years that Jay would be asking if he could fuck my ass. "I think I could handle some more if you're willing." I replied.

"Ready, willing and able!" he gushed. "Do you think we could do it missionary style so I can play with your dick while I fuck you?"

"Its her clit Jay. Not a dick. Tiffany has a clit." Lucy corrected Jay. "And try romancing her a little. Its not all about fucking. Sometimes a girl likes to be made love to."

"Oh, right. I'm sorry Tiff. Can we... uhh... make love missionary style so I can... um play with your clit?" he asked again.

"I'd like that." I said.

"Look at you, Jay! Well done! We'll make a gentleman out of you yet." said Lucy

I rolled over onto my back and spread my legs for Jay. He crawled up between them and gently guided his cock into my awaiting ass until his pelvis was grinding against mine. He reached down and softly started playing with my erect cock. Rolling it around in his hands and gently kneading my balls as he humped his cock in and out my ass. My god, this was another completely new feeling and I was loving it. He cupped his hand around my cock and started jacking me off as he continued stuffing his schlong into my love canal. After a while he began to pick up the pace on both my ass and my cock. I pulled my legs up and propped my elbows under the knees to hold them in place to give him a better angle while he pounded my sissy pussy. I began cheering him on saying "C'mon! Fuck me hard Jay! Oh yea! Fuck that pussy! Goddam your cock feels so good inside me! Fuck me good Jay! Cum in my sweet ass!" Jay let go of my cock and placed his hands under my knees propping my legs even higher. I was completely at his mercy as he relentlessly pumped me with all his might. I reached down now and continued stroking my aching cock as he slammed his mighty member inside of me till I erupted all over my stomach. Seeing this Jay could take no more and with one final thrust he went in deep and dumped a hot, huge load into my already flooded bowel. After what seemed like a minute of him streaming jiz inside of me he collapsed on top of me panting in my ear and breathing hard while his cock softened inside my now oozing ass.

While Jay had been fucking me I had lost all track of what was going on around us. Now that we were done I looked over to see Dale laying on the bed next to us with Jenn on top of him grinding away on his cock while Lucy was opposite her riding his face. Both girls were facing each other and locked in a deep kiss as their hands roamed each others and bodies and breasts. They must have been going at it since Jay and I had started because they didn't last very long and all three seemed to cum at once then the five of us just lay on the bed, exausted and covered in sweat and jiz.

After a bit of rest we all got up and washed off in the shower one at a time. I was a little disappointed that the best night of my life so far was over, but thrilled that I'd fulfilled a lifetimes worth of fantasies in a matter of hours. I was the last one to come out of the bathroom after cleaning up and found that all the party supplies had been cleaned up and put away. Jenn and Dale where talking to each other on the bed while Lucy and Dale where in the corner of the room talking as well although quietly. Lucy had a stern face on and looked as though she was lecturing Jay, but he was nodding in agreement and in the end they shook hands and walked to the bed where the rest of us were. Jenn got up and handed me a piece of paper with her and Lucy's phone numbers on it then gave me a great big hug and a peck on the cheek. "It was so nice meeting you Jim, and Tiffany too. Here's my cell number so why don't you give me a call in a few months so we can hang out and you can show me around." she said.

"You bet. I'd like that very much. I can't wait till you move to town." I replied. After Jenn pulled away Lucy stepped in and gave me a hug as well.

"It's been a real pleasure Tiffany. I hope to see more of you, soon." she told me. Then she turned to Jay and Dale. "And as for you two, you will be much more considerate to your cousin. Understand?" They both nodded in agreement. "Tiff has my phone number too and If I find out you've been treating her badly, things will go badly for you as well. Remember the fun we all had tonight. There's no reason that can't continue. You just need to drop all you preconceived notions of sexual right and wrong and just have fun."

Jay wound up getting a ride home with the girls. I found out later that he had loved being dominated by Lucy and begged her to be his dominatrix to which she happily agreed. He wound up being the first guy to join her newly formed stable of men and spent many a night trussed up and getting fucked by not only her but several of her other clients as well. Dale and Jenn hooked up several times before they graduated and she left for college, but both agreed that an exclusive relationship between the two was probably never going to work under the circumstances. I called Jenn when she moved to town and we became fast friends hanging out, dressing up and going out together. Dale and I enjoyed the rest of the spring break together as he shagged Tiffany several times before I left and all five of us got together for one last game of Drink or Dare before we all went our separate ways. True to their word, Jay and Dale never harassed me again about small frame or girly stature, in fact Tiffany wound up sleeping with each of them whenever one or the other was in town and both of them together on several occasions. But those are all stories for another time.