Sweet Caroline is slowly groomed to crave spankings and anal sex in addition to wearing very adult sexy clothing and lingerie
I went out to Macy’s and bought size 0 petite women’s clothes for Caroline. A nice very tight black dress, short pleated skirt, tight sweater blouse. Also bought the smallest size thong panties, shelf bra (size A) and garter belt. Als the extra small size black seamed nylons. I had to guess on the shoe size and got her size 4 heels with 3” heels. Didn’t want to go too big.
Caroline rushed over the next day, bubbling with energy only a teen girl could have. I let her in and she immediately threw her arms around me, wrapped her leg around me and kissed me passionately, her tongue going deep in my mouth.
Took a lot of effort to push her off. “now, now Caroline” I said, “first things first.”
“if you want to be my girl, you have to dress like a woman” I said. Caroline nodded yes quickly. “Anything you want Ed, I’ll do it.”
“Caroline, apparently you forgot what I told you as you called me Ed again.” “So I need to punish you with a spanking” I said.
Caroline nodded yes, in shame. “I’m sorry sir, I’m just so excited to be with you” Caroline apologized.
I lead Caroline to the living room, and told her to get over my knee.
Caroline was very obedient and laid across my lap. I made sure her pussy/clit was against my knee. I rubbed Caroline’s buns in a circular motion causing her pussy to grind against my knee. I wanted Caroline to orgasm from the spanking so that she would look forward to the pain. I enjoy spanking Caroline, seeing her buns wiggle with each smack, and I wanted her to crave me spanking her.
When I could feel Caroline’s wetness on my knee I started with light spanks (SMACK, SMACK, SMACK,SMACK). Caroline let out a little squeal and her legs went out a little.
Then I rubbed her buns in a circular motion, getting Caroline to start moaning.
Then harder spanks (SMACK, SMACK,SMACK,SMACK). Caroline was squirming and moaning. Then even harder spanks (SMACK, SMACK,SMACK,SMACK). This sent Caroline over the edge as her legs went straight out and she orgasmed, with her moaning (OHHHHHHHH).
I told Caroline to get off my knee and kneel in front of me. Caroline was very obedient, rubbed her buns, and apologized “sir, I promise not to use your first name again, sir” Caroline said apologetically. I nodded my approval.
I told Caroline if she’s going to be my girl, she needs to dress like an adult women. She nodded yes, and I told Caroline “your adult clothes are in the guest bedroom. Go up there and get dressed for me.”
Caroline nodded yes energetically and ran upstairs. Within a few minutes, Caroline came down naked holding the garter belt and said “Sir, I don’t know what to do with this, please help.” I patiently said “yes” and went up to help.
Standing behind Caroline I said “OK Caroline, this goes around your waist” putting the garter belt on her. “Now we put on your nylons.” I pulled out one nylon, bunched it up and told Caroline “now pull your feet toward you so I can put these on.” Caroline nodded yes, and did as was told.
I put on the nylons over her foot, and slowly slid them up her leg, my hands firmly caressing the inside of her legs. Caroline moaned a little, putting her hands behind her head and grabbing the back of my head.
I clasped the nylons using the garter belt. “you see how that’s done Caroline” I asked? Caroline just said “uh huh” obviously too horny and hot to say anything.
I then slid the other nylon on her other leg, caressing her legs all the way up. Caroline’s back arched as she moaned even louder. My plan was working. I wanted Caroline to associated dressing naughty with pleasure. After clasping the other nylon, I told Caroline to stand up. Oh what a lovely view of her lovely legs encased in black seamed nylons. I told Caroline to put her thong panty on now which she obediently did.
“OK Caroline, I think you know how to put the rest on” I said. Caroline looked a little disappointed, but I didn’t want her to orgasm just yet.
I went downstairs and wait patiently. 10 minutes later, Caroline came down. Her short dress just barely covering her lovely ass and stockings tops. The shelf bra pushing out her tiny tits so there was some cleavage. Caroline was a little wobbly with the heels, but she’ll get used to it.
“Caroline, you need some adult makeup” I said. Caroline said “yes sir, anything to please you sir.”
Having watched my wife many times, I put the eye liner, lipstick and other makeup on Caroline. Oh, she looked like the perfect little whore. I showed Caroline and she smiled “oh I look so sexy with this makeup. I wish I could wear this all the time. Does this please you sir?”
I said “yes Caroline, this pleases me very much.” “Now Caroline, you need to sweep the floors so my wife knows you did something here.”
Caroline agreed and wobbled off and starting sweeping. “Caroline do you remember the proper way for you to bend over to sweep the dirt into the dustpan” I asked. Caroline, nodded yes with a smile.
I watched as Caroline swept and each time she bent over, I could see her lovely stocking tops, buns and panty. Oh what a lovely view. Caroline even stopped pulling her dress down. She was obviously ready for another orgasm.
I told Caroline to sit with me again. We kissed, I caressed her legs, then her pussy, she started moaning and kissing deeper. It was hot. I couldn’t believe this young girl was so fucking horny.
I pulled her away and said “OK Caroline, now I need to punish you, your getting a little to handsy, so over me knee again!”
Caroline gave me that pouty look, but she stood up (her dress hiked up to her hips), and laid across my lap. I pulled her panty down to her ankles and massage her buns in a circular motion again making her pussy grind against my knee. I knew she was already close to cumming and I wanted her to enjoy receiving spanks. So I let her have it SMACK,SMACK,SMACK,SMACK… I kept spanking her hard till she started screaming in agony and ecstasy as she again orgasmed, and I kept spanking her hard SMACk,SMACK,SMACK,SMACK…. And she kept screaming and writhing around and orgasming.
I stopped and had Caroline kneel in front of me again. Tears steaming down her face, I told her it’s about time she pleasured me. I didn’t even need to tell her what she needed to do as she eagerly unzipped my pants, pulled out my cock and without hesitation started giving me a blowjob. I couldn’t believe it, she was like a pro. But I didn’t want to cum in her mouth. I had other plans. So I yanked on her hair and told her to stop.
Caroline’s eyes were almost shut, she was still making sucking motions with her mouth, obviously wanting more. But again I had other plans.
“Caroline, I want you to get on the sofa and kneel with your head on the sofa and your ass up.” Caroline was like a doggy and hopped on the sofa and did as told. I then pulled out lube I had nearby and started greasing up her butt hole. Caroline looked back at me with that WTF look.
I said “now Caroline, this is how you have sex and not get pregnant.” Caroline said “will it hurt?”
I said, well yes, this first time, but you’ll eventually be able to do this and enjoy.
After lubing up Caroline, I massaged her pussy and clit again, sticking my finger in her hole and gently caressing her G spot. Again, moaning and starting to make a fucking motion with her body, I gently inserted my cock in her butt hole. I told Caroline “now push against my cock, be relaxed, and let me enter you.”
Caroline was very obedient and pushed gently till finally my cock went in her hole. I continued stroking her clit and g spot as Caroline was moaning more and more. She started bucking against my cock, and without me even moving I was fucking her. Her speed increased, as my fingering speed increased, and as we reached a climax I squirted my load in her slutty hole just as she screamed out in bliss.
It was important to me that Caroline orgasm with the anal fucking so that she would associate anal fucking with pleasure. Just like I did with the spanking.
After we were done, I pulled Caroline into me and kissed her passionately as she kissed me back passionately.
Caroline asked “do you do this with your wife?” I said “no Caroline, you are very special to me and you are the only one I make love to that way.”
Caroline smiled and said “thank you sir, I’m glad I’m special to you because I love you, and I’ll do anything to make you love me to.”
After lots of kissing and hugging, I sent Caroline on her way.
I already had plans for Caroline next week at the mall. There I would have her dress slutty and teach her how to walk slutty. This was going to be fun!
