Elaine undid the little padlock with her delicate spikily nailed fingers, as the ladies enjoyed my apparent look of discomfort at the idea.“You’ll...be milked nicely this evening and tonight; you will beg me to fit this before midnight, so you enjoy tonight’s pleasure as you’ll not be allowed further relief until I am sure you have earned it.” Anita teased my throbbing cock with her cane.“If I had my way, there would be no use for that contraption!” The women roared with laughter and my cock. He laid me on his bed before stripping down & I told him I needed to use the ladies room. I kissed him as I passed & he spanked my bottom watching me go. In the restroom I removed my outfit leaving only my lingerie set on & fixed my makeup a bit. When I opened the door he let out a whistle & padded the bed next to him. I walked over & climbed next to him kissing him as he began rubbing me down. He quickly removed my top & bottom while saying in between long passionate kisses how sexy I looked. I felt something probing, pushing against my asshole, but of course i couldn't SEE anything. When i felt something pushing inside me i thought she was using her dildo on me until I heard a VOICE. Daymean, one of the blockers from our HS football team. Apparently the whispered rumors about him being gay were right. Sis climbed off my face now that my ankles were firmly in his grip in order to hear my protests, and begging as he pushed his mushroom head into my ass. "SIS.. PLEASEE don't.... Moving down her splendid hips my hands reached the end of her skirt and caressing her thighs lifted the skirt up.Not trying to help that much but rather willing to feel my aroused penis she slightly moved her ass. A thin string of her panties was showing thru the panty hose, running up with a small triangle. I confidently ran my hand thru her thighs from the inside and stopped feeling the heat of Iris’s pussy. Her breath became faster and louder. Thru a thin silk of her panties and panty hose,.