Educating Molly Ch. 01

I go to the gym to work out, not to meet women, but I got into discussion with an older woman, my age, who I had seen working out at my gym on several occasions. Her name is Molly. We talked about our workout goals and gave a little bit of background about ourselves. She asked if I was dating anyone and I told her I wasn't but was open to the possibility. She got more pointed and hinted at whether I was still interested in sex. "Of course I would like a friend with benefits," I said. "Who wouldn't? Everyone should have one."

She agreed and I told her that we might not be on the same page sexually. How so? "I'm not into vanilla sex anymore. I like a little kink in my sex life," I said.

"Like what?" she asked.

I told her I was into light bondage and spanking and sex toys. She agreed that she had wondered about that and was interested in trying it. I suggested we meet for coffee and discuss it further.

We met later that week at a Starbucks. I went ahead of time and took a room at a hotel and moved my gym bag full of implements to the room in the unlikely event that she showed enough interest to proceed immediately to participation. We had coffee and the more we talked, the spicier she got and I could tell she was very turned on as I explained the basics of the dom/sub dynamic. When I suggested we go to the hotel room, she readily accepted.

We got to the room and Molly was all bright and excited with anticipation. It was a plain hotel room and I had secured a room at the far end of the hotel where all the other rooms were vacant at this time of year. I sat on the edge of the bed and told her to come sit on my lap, that I was going to interview her. Molly was wearing a skirt, not too conservative, not too revealing. I told her to call me Daddy and asked if she understood.

"Yes," she replied.

I slapped her face lightly and said, "Yes Daddy."

She looked surprised at first, then smiled and repeated, "Yes, Daddy."

I asked if she was wearing underwear and told her to remove her panties. She stood up and reached under her dress and took out a pair of sexy panties which indicated she had been thinking of the possibility of sex on this first date as well.

I took her panties and set them aside on the bed and then told her she should have asked my permission to stand up and she would have to be punished for her mistake. I told her to separate her knees a little to allow me to put my hand up her dress. I then asked her when the last time she had sex with another man was and she said it had been several months.

"Did he play with your pussy," I asked and began to massage her between the legs.

"Yes Daddy," she replied, anxious to show me she was catching on.

"Did he lick your pussy?" I asked.

"No Daddy. That's why I didn't want to see him anymore."

"Did you suck his cock?"

"Yes Daddy."

"Did he come in your mouth?"

"No Daddy."

"Would you have liked that?"

"If it had been you, Daddy, I would have liked it," she answered.

I followed up with some questions about when she had first had sex, whether she had ever had sex with a woman, how often she masturbated, and whether she had ever been tied up or spanked before. By now I had inserted a finger into her cunt and she was responding with gushing wetness. I told her she was a perverted slut and would have to be punished. I told her to go into the bathroom and close the door and sit on the toilet and reflect on her punishment.

While Molly was anticipating what awaited her, I went to my gym bag and began extracting the implements which would make our session a success. There was a flogger, a leather strap and a short cane. I took out a rabbit, a flexible string of anal beads and a small, beginner size butt plug. I went to the bathroom door and opened it. She was sitting on the toilet and looked up at me expectantly. I told her to come out. She came up to me and I asked her if she had touched herself in the bathroom. "No Daddy."

"Good girl," I said.

I told her to lie across my lap with her legs and arms hanging down. She obeyed and I lifted her dress, revealing her bum. For an older woman, she had a well-formed ass, not too flabby, but not pert like a young woman's. I rubbed my hand across it. I squeezed it. I gave it a sharp slap, first one cheek, then the other, but not too hard. There was a sharp intake of breath, but otherwise she made no noise and said nothing.

"You are a very bad girl, a nasty girl, and you need to be punished. Do you understand?"

"Yes Daddy."

"What do you want me to do?"

"Please punish me Daddy."

I slapped each cheek again, making a satisfying crack. "Like that?"

"Yes Daddy."

I continued slapping her bottom, first one cheek, then the other. Crack, crack. At last, she started moaning. Some color came to her cheeks, turning them from white to a nice pink. Crack, crack. Now she began to really feel it.

"Ow," she said with a sharp intake of breath.

"Stand up," I ordered her. "Take your clothes off."

I could see she was anxious to find out what was now in store for her. Molly pulled her dress over her head and then unhooked her bra from behind. She let it fall, revealing her tits. Her body was that of an older woman. Her tits sagged down, but were a nice size and still attractive. She had wide hips and a small pot belly and spare tire, but she looked fine to me.

"I want you to go over to the table and choose the implement I will punish you with, either the flogger, the strap or the cane," I instructed her.

She walked over to the table and I admired her rosy butt. Yes, the color was just starting to look nice. She touched the implements and chose the strap. I was a good choice for her first session, since it would cause the least lasting damage. She came back and presented it to me.

"On your knees when you present me with the punishment implement," I ordered.

She got on her knees and held it out with both hands.

"Kiss it first," I told her. She kissed it lovingly and offered it up again. "Now stand and lean over the bed with you elbows on the bed and your butt as far out as you can make it." She did as order and presented her bottom to me. "Move your legs apart, shoulder width."

What a lovely site, to see my slave in training, bent over the bed with her ass in the air, awaiting punishment. I took the strap and delivered a medium to light slap across her ass. I heard her gasp, but she said nothing. I ran my hand across her ass, feeling its warmth. I slid a finger along her slit, testing its wetness. It came away coated in her cunt juices. I toyed with her ass, touching it with the strap. Tap, tap, tap. Whack. Whack. I heard a sharp intake of breath as the strap found its mark and a little moan. A nice red mark graced her ass.

"This is how a nasty girl is treated. You will learn what it feels like to be punished by your daddy. Do you understand?"

"Yes Daddy."

"Do you deserve to be punished?"

"Yes Daddy."

"What do you want Daddy to do?"

"Punish me Daddy."

I continued to spank her with the strap, not too hard, but enough to mark her butt with satisfying lines. Her ass turned a beautiful cherry red. I admired her butt and ran my hand across it, slowing her punishment, making it last. After a good ten minutes of steady strapping, I stopped and put the strap back on the table. I ordered her to stand straight and put her hands on her head. I admired my handywork from behind her. I wrapped my arms around her and fondled her breasts. I weighed them in my hand and bounced them up and down. I pinched each nipple and twisted. She cried out softly in surprise more than pain, since I wasn't pinching too hard. I slapped her ass and asked her if she liked that.

"Yes Daddy, Please pinch my nipples."

I ran my hand down her waist to her pussy and checked to see how wet it was. It was soaked. I inserted a finger and it slid in easily.

I ordered her to lay face down on the bed. I had previously put some lotion on the bedside table and I now took it and squirted some on her ass. She flinched as the cold cream fell on her hot bottom. I slowly began to massage her ass and rub the soothing cream onto her sore cheeks. She groaned in pleasure as I slowly massaged her bottom. I parted her cheeks and admired her brown wrinkled eye.

"Wink your brown eye at me," I ordered.

She contracted and released her sphincter and her asshole winked at me. I parted her cheeks further and bent down and applied my tongue. I ran my tongue across her tight hole and up and down. She groaned in pleasure. Now I reached over to the bedside table and grabbed a bottle of lube. I squirted a generous dollop onto her asshole and massaged the hole. I inserted my index finger in her ass.

"Have you been fucked in the ass before?" I asked.

"No Daddy."

"Have you been fingered in the ass before?"

"Not by anyone Daddy, but I did it myself a few times."

"You are a dirty slut and must be punished," I said. "From now on, you can only touch yourself if I give you permission, and you can only cum if I give you permission first. Do you understand?"

"Yes Daddy."

I continued to finger her brown hole and I felt it ease and relax. I inserted my middle finger along with my index finger and began plunging my fingers in and out, going as deep as possible. I pulled my fingers out and opened her cheeks as wide as possible. Her hole was now slightly open, nothing like the gape she would develop later in her training, but just big enough that my tongue was able to penetrate her a tiny bit. I applied myself to the task and she lifted her butt to accommodate me and she moaned her pleasure. I continued to ream her for several minutes. I then ordered her to turn over and spread her legs wide.

I looked at her. I took her right tit in my left hand and slapped it sharply with my right hand. I slapped it again, twice, three, four times. She cried out softly but made no effort to move away. I moved on to her left tit and struck it five times, as well. I grabbed her nipples and pulled them up and twisted them. I let them go and she lay back on the bed, looking up at me expectantly. I now contemplated her pussy. It was unshaven. I grabbed some hair between my thumb and index finger and pulled up sharply on it.

"Ow," she said. I pulled another part roughly. "Daddy please, that hurts!!" she complained.

I slapped her face. "We'll have to get rid of it then, won't we?"

"Yes Daddy, I'll shave it," she said.

"No you won't. I will do it next time we meet," I told her.

I licked my index finger and middle finger that had been in her asshole, tasting her juices and removing any bacteria that could cause a vaginal infection. I then inserted first the index finger and then both fingers in her pussy. There was no need to use the lube; her cunt was sopping wet. I played going in and out for several minutes. I added my ring finger so three fingers were now stretching her cunt. I bent down to inhale the wonderful aroma. I slowly began licking her pussy, running my tongue along her slit. I removed my fingers and inserted my tongue as far as it would go inside her main hole. With my index finger and thumb, I pulled back the hood on her clitoris and squeezed and pulled up on it. Her engorged clit was now totally exposed and I began flicking my tongue across it, slowly building up, faster and faster until it was flicking back and forth at a quick pace.

Molly began to buck, pushing her cunt up into my face, her hands squeezing the bed sheet. She was now moaning loudly, crying out little yelps. I could tell she was close. She tensed and thrust her hips up. She shuddered and cried out as she began a long and deep orgasm. It went on and on as wave after wave completely overtook her body. Finally, she settled back on the bed and relaxed. She looked up at me in awe with a slight smile on her face.

"That was amazing," she said. "I've never felt anything like it."

I slapped her. "I didn't ask for your opinion," I said. "Turn over. On your stomach."

She rolled over on her stomach and I retrieved the anal beads. They were a beginner set. I rubbed some lube on them and checked her asshole to make sure it was still lubricated. I inserted the first bead and watched as her asshole stretched to take it. I slowly continued to insert the beads, each one larger than the last. Watching her hold stretch to slowly accommodate each bead was exciting. There were eight beads and as the last one went in, her hole had expanded to twice as much as when my two fingers were in her. I ordered her to turn over on her back and raise her legs. I told her to grab behind each knee and keep her legs elevated. That gave me the best view of her cunt and asshole, with the ring at the end of the anal beads protruding from her ass. I grabbed the ring and slowly pulled the beads out, one at a time. Her ass would expand as each bead emerged and then contract again around the part linking the beads. I pulled out seven of the beads, then slowly inserted them again. I repeated the process once more. After I had inserted them again, I got the rabbit. It was medium sized, not too large, nothing like the dildos I would eventually use on her once she was well trained. It was like an average sized dick in length and girth. I worked it into her pussy and fitted the rabbit over her clit. I turned it on to the lowest setting and the rabbit began to vibrate against her clit while the cock made circular motions inside her cunt. Molly began to moan and move her hips to achieve maximum penetration and coverage. I slapped her ass and she groaned in pleasure. I upped the speed of both the rabbit and the cock as her breathing and movement increased. Molly was now openly groaning her approval, no longer caring how loud she was. I continued slapping her butt, harder and harder. I thoroughly enjoyed seeing her cunt stretched to accommodate the dick and her ass to accommodate the beads.

Molly began bucking on the bed and crying out. I knew she was close. She gave out a cry and thrust her hips as high as she could to accommodate the cock and she spasmed as she orgasmed. This one lasted several minutes and the waves cascaded over her. Finally she came to rest and lowered her bottom on the bed and let her legs fall. I pulled the rabbit out of her cunt as she sighed contentedly. "Lick it clean," I instructed her. Molly lovingly licked and sucked the rabbit dick.

"Turn over," I instructed. She did and I slowly extracted the beads from her ass. I wrapped them in a wash cloth since they had shit stains on them.

"Next time," I told her, "you will need to use an enema before you come. You can buy little single-use ones at the pharmacy."

I took her panties and wiped her cunt clean. I took the beginner's butt plug and handed it to her along with the lube.

"Put this in. You will wear it until you go to bed tonight. Then you will put it back in tomorrow morning and call me. I'll tell you when you can take it out again. Now get dressed."

She reached for her panties, but I held them back. "No, these are mine now," I said. "From now on, you wear dresses and skirts, without panties. I'm also giving you an assignment. Before we meet next time, you are to flash a stranger in public. It can be on the street, in a café or library, wherever, but it must be a stranger and it must be in public. If he comes on to you then and wants you to fuck him, you will explain to him that you are meeting your husband and can't fuck him but you'll masturbate later thinking of him and he can do the same. If he wants your phone number, give him a phony one and if he gives you his number, take it down, but erase it afterwards. Then you are to call me and describe in detail what happened, but you are not to masturbate unless you ask my permission first. Do you understand?"

"Yes Daddy."

"Alright, off with you and I'll see you next time. I'll call you when I'm ready for you."

"Goodbye Daddy."

"Goodbye."

She walked out the door, giving me a look back over her shoulder as she walked through the door, a big smile on her face. I knew she was hooked and her training would proceed just as I'd hoped. She had come twice but had forgotten to ask my permission first. She was in for a strict punishment next time. I took out my cock and put her panties up to my face, inhaling the intoxicating smell of her cunt while I masturbated.

TO BE CONTINUED