Mary Moves in with Tony

This story is a follow-up to "Tony's Visit to the Resort". It should stand on its own, but you might be interested in the Resort story.

Mary moved in with me after we returned from our visit to the resort. After a few months, Annie joined us for an extended visit. Usually, Mary would sleep with me, but with Annie visiting, Mary and Annie slept together in the guest room. Not sure how much sleeping was done. Every few days they would start the evening in my bedroom. Once they had taken care of me they moved to the guest bedroom.

Mary had to attend a conference for three days, so she was going to leave the two of us to our own devices. However, she left me with clear instructions, "Tony, you do everything Annie tells you to do. I do not want to come back here and learn that you haven't kept her happy. Do you understand?"

"Yes, I understand."

Mary smiled and said, "Good. Next time I'm away you can be in charge." With that, she knelt down, unzipped my pants, and gave me a blowjob swallowing every drop. "You know I love you. Have a good time. I'll be home soon."

I did understand Mary's directions. I also understood that my ass would be red for much of the time Mary was gone. Annie loved to beat me. However, she would make sure I enjoyed the overall experience. On the first night Mary was away, Annie told me to go upstairs, take off my shoes and socks and wait for her.

Annie entered my bedroom, walked up behind me, and started unbuttoning my shirt. She was wearing the standard male's fantasy costume: sheer shelf bra displaying her nipples, garter belt, sheer panties over the garter belt, seamed hose, high heels, all in black. She took off my shirt and let it drop to the floor. She ran her fingers across my nipples like she was strumming a guitar. "I know how you love it when I play with your nipples." She pinched my nipples with her nails. She changed her approach and grabbed a nipple in each hand and pinched with her thumb and forefinger, twisting and pinching until it hurt. She kept it up with my left nipple but reached into my pants with her right hand to grab my cock and stroke it. "Your cock likes it when I play with your nipples, too." She bit my shoulder while pinching and stroking. She dropped her left hand to undo my belt buckle, unbutton and unzip my pants, and pull down my pants and underpants to let them drop to the floor. She bent over to pull them out of the way.

"I need to show you who is boss tonight. Bend over the bed so I can spank your white ass. I won't hurt you...much. I'm only going to spank you with my hand as long as you are quiet and don't move. If you yell out or move your hands to your ass, I'll get my belt, and I'll stop worrying about hurting you. Do you understand?"

"Yes, I understand."

Annie started to slowly spank my ass. At first, she slowly alternated spanks on my cheeks. Then she picked up the pace. She began to repeatedly spank one cheek, then move to the other for more repeated spanks. Annie kept this up until she was satisfied with how red my ass was. She then moved to my thighs and repeated her process of spanking. It didn't take long to redden my thighs. I was tempted to move my hands to protect my thighs, but I didn't want her to get her belt. I thought she would stop when her hand started to get sore. But she didn't. She pulled on a pair of spanking gloves and restarted the whole process. When she got to the back of my thighs, I couldn't take any more. "Please. I can't take any more. Please stop."

"I told you what would happen if you weren't quiet. Now, shut up." She pulled off her panties and shoved them in my mouth. Annie reached into her nightstand drawer and pulled out her belt. She backed away from me, doubled the belt, and started to whale away on my ass with her belt. I kept quiet but tears rolled down my cheeks. She didn't do this for very long, since I was starting to bruise, and she really didn't like that. She wanted me to recover in a week so she could again spank a plain white ass.

Once Annie had completed reddening my ass she said, "I'm sorry, Tony. I didn't mean to beat you so bad, but you looked so sexy squirming around. I just love to see emotions on your face. Your crying turned me on almost as much as watching you cum. I won't beat you that hard again." She then rubbed cooling lotion on my ass and thighs. "I'm going to take my panties out since you'll need your mouth for the next part of our evening."

She sat at the head of the bed propped up against the pillows. "Come here Tony, I want you to lick my pussy until I cum." I knew what she wanted. I should lick, suck, and nibble her pussy lips and clit. Then use my fingers to make her cum and squirt all over my face. I would do this multiple times until she was too sensitive to continue and would push me away.

"Tony, that was lovely. Let me wipe some of my juices off your face." Annie used tissues to gently wipe my face and kiss me.

"Get up Tony and lay on the bed on your back. Spread your legs and lift your knees." Annie opened her nightstand drawer and pulled out a pair of nipple clamps held together by a chain. She sucked on my right nipple and pulled it until it stuck out. She placed the clamp on my nipple. She did the same with my left nipple. "You knew I wasn't done with your nipples, didn't you?" She pulled on the chain. When I grimaced, she said, "oh, that's nice."

Annie strapped on her cock, but at least it was one of the smaller ones. She squirted lube on her left hand and spread it on my ass crack. She squirted more and pushed it into my ass. She squirted more lube and covered her cock with it. "I'm going to use plenty of lube, so you can enjoy it." She placed the tip of her cock against my asshole and gently pushed. She waited until I was comfortable with it. She then pushed her cock all the way in and began her slow pull out and push in rhythm. She squirted lube onto my cock and began to massage my limp dick. She rubbed her thumb under the head of my cock. I'm especially sensitive there, and Annie knew it. I think I could cum from just that massage, but with her fucking my ass, I knew I couldn't last long.

"Relax, baby. Just enjoy it." I was soon squirting on my stomach. Annie milked all she could from my cock. She bent over and licked the cum off my stomach. "Oh, Tony, you taste so nice." She placed her mouth over mine and dribbled cum into my mouth. "Swallow, Tony. Then I'll suck your dick dry."

I loved Annie but really hoped sessions such as this would only happen every few months or so.