Jane Goes Back To School

Carla Collins was a beautiful, intelligent, loving, uninhibited, freakpig of a girlfriend. The kind of girl men would fight over to possess and fantasize about for a lifetime after they lost her. I'm honest enough to admit I loved her. I love her still. Planned a life with her once, but it didn't work out.

Her parents loved me. My parents loved her. We both liked Jimmy Buffet and Gordon Lightfoot. We were great together. All the math added up to prove the two of us should have sailed the seas of life on a grand adventure. But that didn't happen. We definitely were great together. At least we were when times were good. When times were bad it was horrible. Cups and bowls shattering against the apartment walls type of horrible. Emotionally it was worse. For both of us.

We both knew it was no way to live a life and we were both, surprisingly, mature enough to admit it to ourselves and to each other. So we took one last trip. We went to the coast and spent a glorious week on a borrowed cabin cruiser. Both of us trying to pack a lifetime of love and sex and intimate conversation into seven days of naked skin, sunshine and rum. It was magical. It was heaven. But both of us knew it was the ending to the brief love story of Carla and Sam.

Bittersweet. But friends. Always "what if" friends. I still visited her parents, Jane and Doc, on Christmas Day. She was at my parents on Christmas Eve. Each of us dragging whatever person we were dating along and insisting that they accept the situation, as it wasn't going to change. It was comfortable. She was there for my sister's sweet sixteen birthday bash. I was there for the funeral of her brother. We were friends. As deeply intimate and emotionally open as that one word could ever describe.

Then one summer BBQ at my rent house changed everything. Music was playing, several cases of Dos Equis were on ice (Original brown bottle, of course) and there were ribeyes and sirloins cold smoking on the pit. Several co-eds were getting some sun in bikini tops and cut offs. The guys were throwing a Frisbee on the freshly cut grass and peacocking to get the attention of the tanning girls.

I was flirting with a svelte redhead named Melanie. She was sticking close to me, happy to be my little step and fetch it girl. The little slut was blessed with long thick copper hair, lots of freckles, long lean thighs, a firm ass and a submissive kink.

Yep, it was a good day. It looked to be an even better night. I had ropes already tied onto the bedframe in strategic locations and the redhead wannbe slavegirl had brought her leather gimp mask and a braided black leather cat o'nine tails that looked like it would leave scars.

I was busy planning out the patterns I would leave on the skin of the barely 18 Melanie when Carla walked in with her current loser boyfriend and I watched as he went straight to MY beer without even waving in my direction. Rude little fucker.

Carla gave me a hug and kiss on the cheek as I watched him take two beers and walk away from us to join the guys in the yard.

"Real winner you got there, babe. Rude. Didn't even bring you a beer," I whispered.

"Yeah, but he has a nice boat out on the lake that I use whenever I want - so I'll string him along for the summer," she laughed.

"Bitch," I said as I pecked her cheek.

"Man whore," she replied with a smile. Watching Melanie's face as she tried to figure out this new possible obstruction to my affections "You gonna wreck this little redhead's pussy tonight?"

Yep, that's my girl. Was my girl. Life's complicated.

"Melanie, go on out there and get some sun. Show off that tiny bikini and tease the boys a little bit. It's OK if they touch you," I ordered and she hopped to obey.

"Aw....I want one," Carla said in a pout.

"I'll share with you babe, you know that. She's got a really soft mouth."

"I need you to do me a favor and its a big one Sam," she said suddenly seriously, looking into my eyes.

"Anything Carla. You know I'm way past all in with you. Who do you want dead?"

"Nothing like that.....this time," she smiled. "I need you take care of my Mom."

"What's wrong with Jane? How can I help?" I said. I was worried and willing to shut down the party immediately if necessary.

"See that's why I'll always love you, Sam. You're half way to the door and don't even know what the problem is."

Evidently, that earned me another kiss. Right on the edge of my mouth. It was sweet.

"Tease," I said. "Really, what's wrong?"

"Mom is coming back to college for her Masters of Education degree and I want YOU to watch out for her. She'll be here Sunday night to Friday afternoon every week when Fall classes start and I'm worried she'll just sit in her apartment and study."

"Well, babe. I mean...what do you want me to do? Make sure she gets to class?"

"Take her out. Take her to the bars. Make her dance. Invite her to your parties. I want her to have fun. She deserves it."

"Carla. You have given me strict instructions to never speak to your mother about the parties I throw. Are you seriously saying that you want me to ask Jane to come to the annual Pajama Party? Does she even own a lace teddy?" I smirked.

"Well, maybe save that for next year. And I mean it. I want her to have fun but you have to keep all the horny freshmen away from my mom," Carla said.

"I don't know. That's a tall order, babe. Jane's a MILF if you get past the Mary Tyler Moore haircut and those sensible shoes. The boys'll be lining up for some....personal tutoring," I laughed as I danced out of range of the well thrown fist I knew was headed my way.

"Asshole!" Carla yelled at me with a smile as her punch mostly missed me. "Listen, I personally think Mom needs to get laid. And it needs to be someone who will take care of her. I just don't want to know about it. Understand?"

I was silent as I weighed what I thought I had just heard. Calculated. Rechecked. Did the mathin my head. It felt like my life might depend on me not misunderstanding what Carla just said.

"Sooooo...make Jane feel safe and welcome. Show Jane around. Take Jane out to dinner. Take Jane dancing and to the movies, etc. Make sure Jane gets home safely. And if Jane invites me into her apartment....you are saying...what? I check to see if she actually owns a lace teddy? I carry her to bed and show her why you really love me so much?"

"I'm saying that when you tell me about the nice dinner you had, the drinks you bought her, the movie you two saw together, you stop at the point where you walked my sweet, Christian, married, middle school teacher of a mother to her door and said goodnight," Carla said steadily. "And if she invites you in, I want you to keep her up all night and then make her late for class the next day like you used to make me, Sam. I always thought you had a really soft mouth baby. Be soft with my mother."

"But, what about Doc? Don't you think he'll be against this plan?" I asked as I was pretty confused.

"He doesn't ever need to know. He's had low testosterone since they've been married. Mom told me. She's pent up, Sam. She admitted that to me too. I need you to seduce her and turn her out. Gently. Make her feel like an attractive sexy woman again."

I couldn't breathe. The world stopped as Carla looked into my eyes. My heartbeat was at least 140.

"Carla, I promise that if I am....offered the opportunity I will treat Jane exactly how I treated you," I said in all seriousness.

"Sam, remember that she's over 50. She can't take the pounding you put me through. Go slow. Be sweet. Be soft. IF she offers," Carla said quietly.

"Hell. Yes, Ma'am," I replied. My cock throbbing in my jeans.

Carla kissed me again. Soft and sweet. On the mouth. A kiss that told a ten thousand word story of her love for me. I reached out and held her hand in mine, both of us forgetting the rest of the world around us as only old lovers can do. I squeezed just a little trying to let her know that I was still hers and she could trust me with her heart and now her mother's heart as well.

"I know," Carla said as she walked away to find her rude loser boyfriend.

There were a few weeks left until Fall classes started and Carla made sure to keep me up to date on her mother's anticipated arrival. I was still spending a fortune on film, taking polaroids of a gimped up redhead in bondage and servicing one of her college classmates after I had blown a couple of loads into her cunny. Both of them were natural born freaks. Fuckpigs who had dedicated their lives to be used. Life was good.

But, even with all the rope, and whips and paddles and dripping red haired quim I was fucking.....I was always cumming to a mental image of Jane. I couldn't wait to try and seduce her.

Finally, the day came when Carla stopped by my house after moving Jane into her college apartment not too far away from my rent house. I had one redhead tied face up on my bed. I was in the middle of teaching the more dominant slut, Nikki, exactly who was the boss. The subby slave freak, Melanie, was sitting in the closet. Gagged and bagged with a black hood. The little gimp got off on being used as a sex slave. I got off on using her like a faceless sex toy. Nikki got off on - well, fucking everything, as far as I could tell.

Both of those sluts loved me just enough to lose all sexual inhibitions.

I didn't love either of them enough to spare them the least bit of pain, degradation or humiliation I could imagine.

We three were made for each other.

Of course, Carla always had a key to any house I was in and walked into the bedroom right as I was giving Nikki's throat a stretching and slapping her full tits like they'd offended me. She was blindfolded and bound at the ankles, knees and wrists. I heard the door open and looked over as Carla entered the room.

"Mmmmm. Does it suck pussy too?" Carla grinned as she crossed to me and put her arm around my waist.

"It will do whatever it's told, won't you? You dirty cumpig?" I said as I slapped Nikki's tit so hard her whole body shook.

"Look at me, Sam," Carla said. She put both hands on my face and looked into my eyes. Her mouth opened slightly and I saw her tongue peeking out. I kept thrusting into the gagging co-ed beneath me.

"Look into my eyes, baby. Hold me," Carla ordered and I complied. I wrapped my arms around her and pulled her close feeling her perfect pillowy breasts against my naked chest.

"I'm going to make you cum, Sam. Me. The woman you love," she whispered as she stared into my eyes.

And then it happened. Carla leaned in and kissed me. Like it was the first time we met. Or maybe like it was the last time she would kiss me on this earth. And I just lost myself in her eyes and the feel of her lips. I thrust my hips forward and unloaded my cum down Nikki's tight throat, ignoring her gagging, bucking body and muffled screams for oxygen.

"Put that street trash to sleep, Sam," Carla said quietly. "I'm still a jealous bitch when it comes to you."

I held my cock in Nikki's throat until her chest shuddered and she finally stilled before I pulled out. She immediately took a deep breath.

Sneaky whore was playing possum all along. "I'll have to remember that," I thought and gave her tits a few more vigorous slaps.

"You want some of this, my love?" I asked Carla.

"Sam, I'm all hot and sweaty and dirty down there. I've been working all day," Carla said with a grin. "Of course, this whore is going to suck my pussy. For hours."

I helped Carla remove her clothes as she took my place on Nikki's face.

She grabbed both nipples firmly and said, "Time for you to learn who the bottom bitch is in this house!"

I think I counted four strong orgasms, as I gently kissed and loved on Carla from behind while Nikki tongue fucked her swampy cunny. Carla had no compunction against just rubbing herself off on the dirty red head's face while I whispered how sexy she looked, how beautiful she was, and how much I loved her. As a friend of course. Fuck that. I loved her as I'd never loved any other woman. She's definitely bottom bitch.

Nikki had a long night. We left her tied there and grabbed the gimp out of the closet. All of us fucked on top of her and eventually slept on her. Me, Carla and little gimp Melanie. Of course, I made that subbie pig take her turn at eating pussy. Carla's of course after I'd filled her with cum. I decided Nikki's dirty snatch didn't deserve any cock.

I woke up the next day without the love of my life but with two extremely submissive sluts. Life was good. But it was time to go MILF hunting.

Carla had left a note with Jane's address and a photo copy of her class schedule on the bar beside my coffee maker. They were held down with a spare key to Jane's apartment. Just in case the note said. Carla left a snarky PS - "Do not use this key to break in and rape my mother - unless she specifically asks you to".

Monday morning found me casually sitting outside one of the main buildings of the campus. I was sitting on a low wall waiting for Jane to walk out of her first class and make her way to her next one.

I didn't have any class to go to for another hour having just finished World Lit. I actually snuck out early to make sure I would be in position to "casually" meet up with Jane.

She walked out of the building and down the steps not noticing me. She was slim and petite and wearing a skirt and blouse that reminded me of a teacher or professor and definitely not a student, but I could still see her legs were toned and her tummy was flat. She had only B cup tits. Not like the pillowy D cups her daughter had, but still she was a tight little package once you got past the mousy, librarian like exterior. Maybe it was the glasses or the shoulder length brown hair with bangs she sported. But no one gave her a second look except for me. She was my prey this morning.

I was looking directly into her eyes when she saw me. She gasped as she recognized me and my smirking grin. Then I was rewarded with a big wide mouthed smile. Almost identical, if older, to the smile that had swallowed my cock on so many occasions. Fuck I wanted this woman. And I had permission. I was going to make her forget that she was married and then when I was balls deep inside her, I was going to make her cum remembering she was cheating on her husband with her daughter's ex boyfriend.

"Well, hello little school girl!" I said playfully. I received a tight hug followed by a little slap on the arm for my comment.

"Stop Sam!" she giggled, "What are you doing here?"

"I was looking for a victim actually," I said.

"A victim?"

"Yes Ma'am, I'm going dancing tonight and I'm looking for a girl with sexy toes to step on," I grinned. "What color are your toes painted gorgeous?" I flirted.

"Stop! You are horrible teasing me," she said.

"Ok, ok, no dancing tonight. How about I buy you dinner instead Jane? We can catch up."

"I'd like that," she said shyly, looking for all thr world like a girl being asked on her first date. I bet her husband wouldn't approve.

"Great! I'll pick you up at seven. Jeans and a t shirt is the dress code, sexy!" I said, quickly kissing her cheek and touching just above her ass before walking off.

"Wait! You don't know where I live!" she raised her voice to say.

"I know everything Jane!" I called back without turning around. "I'll find you."

At almost 7PM, it was dark outside as I was pulling up in front of Jane's college apartment. It was upstairs in a nice big complex, no doubt filled with college kids. I knocked on the door and started counting the seconds in my head.

One, two, thr.....yeah, she was waiting by the door. She was wearing a comfortable looking but fitted soft t-shirt and a tight pair of jeans, her feet bare except for her well worn low cut white All Stars.

The jeans showed off the womanly curve of her narrow hips, the t-shirt allowing the strap of her dark blue bra to peak out. She wasn't wearing glasses and her hair was pulled back into a low pony tail.

Oh yeah, I was going to enjoy this.

"Hello, Gorgeous. Damn you're making me hungry," I said moving in closer and staring into her eyes. "I'm ready to...eat. Are you?"

Her eyes brightened even more than before as she recognized the compliment and the insinuated invitation to ride my face like a straight seat Yamaha over a bumpy mountain trail. I'd help her climb that mountain until she reached its climax.

"Sam, that's naughty," she said half heartedly, "You shouldn't tease me like that. I'm Carla's mom."

"You're the original perfection reflected in Carla's beauty. I'm just at your feet, Jane. I can't help it," I said never breaking eye contact.

"Oh," she whispered as she looked down and moved a nonexistent piece of hair behind her delicate ear. I could see the crows feet at the corner of her brown eyes tighten as she smiled. "Thank you, Sam."

"It's simply the truth Jane and we should always be honest with each other," I replied earnestly. "Are you all ready for our first date?"

"Very," she breathed. "First date?"

"Oh, yes Ma'am. I want to see you open that door again. Many times. And every time just as happy to see me as today."

She didn't reply. She simply took a deep breath and stepped forward as if she'd made a life changing decision. I didn't step back and her movement carried her so far into my personal space that her tiny titties were touching my chest. As she pulled the door shut firmly behind her, I looked down to see her looking up at me. He eyes closer to my belt buckle than my nipples.

"I'm ready Sam," she said looking uo at me with determination. "I'm all yours. Take me....anywhere."

"Yes, Ma'am," I replied turning and sliding my left arm possessively around her. She was so small that my left hand naturally landed just under her left tit. I could feel the strap of her bra under my index finger and after we navigated down the steps, I rubbed my finger slowly back and forth on the underside of her tit as we walked to my truck.

I took her to the driver's side and opened the door. I reached down and picked her up easily around the hips and set her onto the driver's side on the bench seat of my baby. A raised Ford truck with the Explorer Package. Jane had to weigh less than a hundred pounds. Fuck, my cock was hard and throbbing already.

She scooted over as I climbed in and settled into my seat pressing the clutch and the break and turning the key.

"Sam? There's no seatbelt here," she said.

"It's OK, Mrs. Collins. I would never hurt you," I said. "I'll drive you slow...and careful. Make sure you get there safe." I moved the long shift rod into Reverse and she spread her knees wide to accommodate my hand as I deliberately and slowly ran through each gear before ending my movement up and away from her tiny pussy.

I could hear her swallow before she said, "You know Sam, that you're....I...I'm old enough to be your mother. Are you sure you're OK with...taking me out? What will your friends think?"

"Guys will definitely be jealous. The girls are going to hate you for your beauty."

"Oh, stop Sam. You're lying. I'm not special," she said. " But what about you taking an old woman around town. How do you feel about that?"

I had pulled out of the parking space and was easing my truck out onto the road in 1st gear. As I started to answer, I made sure to time it with the shifts.

"You are special, Jane."

2nd gear. My hand within an inch of her sex. A sharp intake of breath as my arm brushed her tit.

"I know there's a connection between us. The hugs. The way you've looked at me all this time."

3rd gear away. Her right hand moving up her leg from her knee to past mid thigh as she scooted tighter into my right side. Her soft "Yes." barely audible over the big V8 engine rumble.

"Don't lie and say you haven't felt it."