Let's see... where did I leave off.
Sorry I have't written lately. The semester got really busy and, frankly, I wanted to see how the site was going to handle the re-launch. I feel like it's more stable now.
Last time I checked in I just had my first spanking from Mrs. Montgomery. It was great. She helped me cum during the spanking, and then made me masturbate afterwards while she watched.
That became a weekly event for us. The following Friday I got home from school about lunch time and she arrived a few minutes later. My stomach was fluttering in anticipation. We had lunch and she then asked if I remembered our arrangement.
"Yes," I replied, meekly.
"Have you been a naughty girl this week?" I could feel my panties getting moist.
"And do you think it would be better if I spanked you here and now, or do you want to wait until Jack and Sally get home to watch?"
OMG, I wanted to be watched, but I wanted to be spanked again - now - just like last time. "Now, please."
Alright, Jennifer. If you want your spanking in private then you need to ask for it properly. Tell me you've been a naughty girl and ask me to spank you... go ahead.
"Mrs. Montgomery, I've been a naughty little girl. Would you please spank my bottom?"
"Alright Jennifer. From now on, I expect you to be ready for your weekly spanking when I get home on Friday. Take your pants and socks off and bring the chair into the living room - make sure it's arm-less."
I did as she said, leaving my panties in place and carrying a chair from the dining room to where she had placed it last time.
"Now, Jennifer. Go stand with your nose in the corner with your hands on your head." I did as she said.
After I was there a few minutes, she came up behind me and whispered in my ear. "This is where naughty girls wait for their spankings. I expect you to be here every Friday when I get home. Chair in place, panties ready to come off. When I ask you why you are here, you'll tell me because you've been naughty and need a spanking. Understood?"
She whispered again, "if you're not ready when I get home, I'll presume you prefer to be spanked with the kids. Got it?
"Why are you here, Jennifer?"
"Because I was naughty, and need a spanking."
She rubbed my bottom through my panties and asked, "where do naughty little girls get spanked?"
"On the bare bottom, ma'am."
"All right, then. Come over here." Mrs Montgomery took my hand and led me to the chair. She sat in front of me and hooked her fingers in my panties, sliding them down over my bottom. I think she was surprised that I had shaved completely bald. I stepped out of the panties and went over her lap.
I haven't figured out how she does it, but I'm straddling one leg and laying across the other, with her foot hooked in my ankles. I can't move my feet and she is holding my arm behind her back - I'm immobile and I can feel her knee against my puss again.
The spanking was what I needed. Rhythmic, like daddy used to do. 3 swats at a time to one cheek, then 3 to the other. My clitty bounced on her knee as she swatted me with her hand. She rested after each set, hand stroking my burning bottom. She asked me questions as she rubbed me and probed me. Sometimes rubbing my butt hole, sometimes stroking my wet pussy lips. I needed to cum so bad. And she asked... are you going to cum for me like a naughty girl?
That put me over the edge. I grunted, flexed, spasmed, clenched my butt, and came so good. I humped her knee for several spasms, then rested, then several more spasms as she rubbed my puss again.
I moaned out loud as she fingered me to another cum. And then I was really surprised when her wet slippery finger moved up to my bottom and pressed against my hole. I squealed. She held me in place.
"Shhh... I know baby. You're not used to this yet. It's okay. Just relax. I'm not going to take your bottom just yet. I want you to get used to the feeling though. Relax and enjoy the pressure."
OMG, she just kept her finger there against my bottom hole. Rubbing it in circles. My clit still rubbed her knee. I could feel myself opening slightly for her finger, but she kept her promise and didn't go inside. Just kept rubbing her finger around the hole with just the right pressure.
"It's okay sweetie. I know what naughty little girls like you need."
Something about how she called me a naughty little girl worked for me. It took me back to my childhood spankings and how naughty I felt being spanked on the bare bottom by mom and dad. And how masturbating afterwards made me feel even naughtier. And now having my bottom explored after a spanking just seemed like the next logical step in my journey to the ultimate naughtiness.
I came again. The attention she gave my bottom was exquisite. It was so over the top naughty to have this woman spank me and then probe my bottom while I came.
After I came I just went limp. She rubbed my sore bottom some more and tried to comfort me. "All better, Jennifer? You had a nice big cum for me, didn't you?"
"Oh, God" was all I could say.
"I know, baby. I'm proud of you for opening yourself to me like that. You have a sensitive little bottom hole, don't you? Have you ever let someone play with your bottom before like that?"
"No," I replied. "I just had no idea. I've never cum so much."
"Like I said, I know what naughty girls like you need. Obviously, I can't help you cum if I ever have to spank you in front of the kids, but as long as you properly prepare and ask for your spanking while we have some privacy, we can explore your bottom a little more thoroughly every week. Okay?"
She punctuated the question with another swat to my bottom. I squealed again and agreed. I would be ready every week.
She asked if I wanted to masturbate again like naughty girls do after their spankings - like she knew I did as a child. I had to decline this time, though, as I didn't think I could cum again so soon. She accepted that, but told me I was forbidden to masturbate for the rest of the day unless I called her at work for permission.
As I got up, she commented on my bald puss. "Interesting that you decided to shave your puss just as Sally is starting to get hair."
I reached for my panties, but she did not allow me to put them on. She took them and put them in her pocket, saying I could have them back when she got home. I asked about Sally and Jack, who would be home in a couple of hours. She said I could simply stay in my room or put on a pair of shorts, but no panties.
I started to put the chair back in the dining room, but she stopped me. "No need to put that away. We'll be using it again tonight." My stomach turned and my eyes went wide. I was afraid she would spank me again tonight in front of the kids. I guess she read my mind because she went on to explain, "no, not for you. Jack will be getting a spanking tonight. He failed to do several of his chores this week."
She went back to work then. For the rest of the day all I could think about was how I would finally get to see Jack get a spanking. I though of my brother and how I loved watching his spankings.
With my panties off and my bald pussy, I eventually got wet and decided I needed to masturbate. I called Mrs. Montgomery and asked if it was okay. She agreed, but made me leave the phone on so she could hear me. She didn't say much - just a few okays here and there - I guess she was surrounded by co-workers. After I came, she finished the call by asking if that solved the problem. She thanked me for calling, and hung up.
I won't bore you with a weekly recount of how she spanked me after school on Fridays. Suffice it to say that she did so every week like clockwork. I would be standing in the corner, in my panties, chair ready. She kept her word of helping me explore anal eroticism. She eventually inserted her finger just as I started to cum - the most intense cum ever. She even got me my own butt plug, which she now inserts before my spankings. And after this Friday's spanking she told me she wanted me to research something called "figging." I called her after I looked it up and asked for permission to masturbate again. She made me re-insert the plug before she would let me. I'm really looking forward to that.
I guess I'll stop for now. I do have more to tell you, though. I guess I'll tell you about Jack's spanking next, and then about some other interesting things that happened.
I've enjoyed the comments some of you have made about my stories, and the stories that others have been inspired to write. I hope more people will tell us about their spanking experiences and how they led to masturbation.