The Education of Lisa Ch. 02

Having decided that anal intercourse wasn't, by literal definition, sex, my boyfriend Jerry (free of sin) fucked me up the butt at least twice a week. This was fun at first, but like all of the sex performed within the bounds of Jerry's arbitrary pre-marital guidelines, it finally left me unfulfilled.

It seemed that Jerry considered anything that might involve my clitoris to be dreadfully sinful. Actual vaginal intercourse, of course, spelled instant damnation. Fellatio was perfectly acceptable (the President himself had said so) but cunnilingus was the first step on the road to hell. Jerry didn't even like to stroke me off with his hand. If he so much as touched my pussy, he would go into the bathroom and wash his hands with anti-bacterial soap.

At first, I would use my own hand to bring myself off while Jerry banged my back door, but Jerry had told me very seriously that I wasn't to do that. Masturbation, you see, was the worst sin of all. So all I could do was wait for him to get off up my ass, then go home and masturbate in private. Not very satisfying.

The sex wasn't the only problem. Jerry's self-righteousness and egotistical nature extended to all areas of his life. He was fastidious and stingy. A shameless bootlicker towards people whom he perceived as socially superior, and a raging terror towards those he felt to be beneath him. He enjoyed bullying waitresses and sales clerks.

"I'm going to be a lawyer," he would tell me. "I might even run for office one day. I have to spend every moment of my life in preparation for that possibility. If you want to be my wife, that means you have to live that way, too." This was when I wore clothes he didn't approve of, or acted publicly in an "immature" fashion.

But Jerry sure did love his butt-fucking. I'm not sure how he worked this into his immaculate Young Republican self-image. After all, he didn't seem all that dignified or conservative when he begged me to "Squeeze it! Oh God, Lisa, squeeze your asshole!" Or when he wiped the shit off his dick afterwards.

It was during his umpteenth trip down my Hershey Highway when I finally reached the end of my tether. I was in a bad mood already, Jerry having humiliated me in front of my own mother that day by saying that I had some growing up to do before I would make a good lawyer's wife. ("But," he conceded as I gnashed my teeth, "I do see potential.") Then he had dragged me to a boring party at the house of the lawyer in whose office he interned, practically ignoring me for three hours while he brown-nosed. After the party, he had the nerve to say that he felt that my dress showed too much cleavage and that I had embarrassed him. Then, after all this, he took me back to his house and whined until I got down on all fours and let him lube me up and stick it in. In his enthusiastic plunging, he stuck me at a bad angle and I felt a sharp pain deep inside.

"Ow!" I cried, pulling away. "God damn it, be careful Jerry."

"Hey," he said. "Watch your language. You know I don't like it when you talk like that."

I just stared at him, jaw open in disbelief. He stared back, nonplused.

"You could at least let me finish," he said.

That was when I lost it. Three years worth of resentments came pouring out of me all at once. I screamed and raged against him for hours, tears pouring my face. If he would have apologized, or even gotten angry back at me, I might have found it in my heart to forgive him. But Jerry, instead, countered my every point with his infuriating lawyer's logic. He never raised his voice or lost control, and in Jerry's mind I knew that meant he had won the battle.

I left his place in a boil, the literal pain in my ass serving as a reminder of how little I was getting out of this relationship.

I had no intention of ever seeing him again, and every day apart cemented my decision. had been with Jerry for so long that it was at first difficult to picture life without him. But, away from his constant influence, life without Jerry seemed more and more like a glorious new world of possibilities.

Then the roses began to arrive. A dozen every day, delivered promptly at noon, until the smell made me want to gag. Every bouquet contained a tiny note, a handwritten apology of appalling insincerity. I knew he charged them to the platinum Visa card his father had given him as a graduation present, and this fact angered me almost as much as the knowledge that he fully expected me to relent. In Jerry's world, angry girlfriends were always won over by a constant onslaught of roses.

After a week of this, my anger cooled and finally froze over. In this chilly state of mind, I was able to plan and orchestrate a scheme to get that jerk out of my life forever. Revenge. It would be cold and it would be sweet.

I called Jerry on the phone one night, putting on my little girl voice, the one he could never resist. He apologized and admitted being wrong, but I could tell from the smug tone of his voice that he thought he had won again. Yet another victory for the junior lawyer. This only strengthened my resolve.

I told him that I forgave him, but that he owed me. What did he owe me? Anything I wanted. In bed.

"Now, Lisa," he said seriously. "You know we can't have intercourse until we're married."

"That's not what I want," I said coyly.

"Well, OK," Jerry said, intrigued despite himself. "I guess we can really do anything except that."

Just you wait, asshole, I thought. He invited me over that night. It was Bridge night for his parents, and we would have the place to ourselves. Perfect. I grabbed the bag of toys I had prepared and drove over to Jerry's to begin my night of fun.

He kissed me as I arrived, and I kissed him back even though he repulsed me now. I didn't want him to get suspicious.

"What's in the bag?" he asked.

"You'll see," I teased. "Let's go into your room."

Grinning, Jerry led me into his bedroom.

"Now you have to whatever I tell you to," I said. "I'm the master and you are the slave."

"Sure, babe," he winked and went to kiss me again. I pulled away.

"Did I tell you to kiss me?" I snarled. "Keep your shitty lips off me until I tell you otherwise."

Jerry's grin faltered a little, but I smiled at him to show it was all part of the game.

"Take off your clothes," I commanded. Jerry stripped down. He was already hard.

"Now lay on the bed."

Jerry did so. From my bag I pulled out a pair of handcuffs. Jerry's eyes nearly bugged out of his head.

"I don't know, Lisa," he said doubtfully.

"Shut the fuck up!" I yelled. "I didn't tell you to say anything, shithead. Now put your hands over your head."

Jerry eyed me strangely, but obeyed. I fastened his wrists to his headboard and then pulled a second item from my bag. A single red rose. Jerry seemed apprehensive, but this dissolved as I began to lightly trace the soft petals all up and down his cock and balls. Jerry shivered with pleasure as I brushed slowly from the base of his scrotum to the tip of his penis. A tiny drop of semen stained the flower petal and this sight aroused me even further.

"Oh, yeah," Jerry whispered.

"Shhh," I hissed.

My tongue followed the path already blazed by the rose. I licked his scrotum, then took his cock into my mouth and proceeded to give him the slowest, wettest blowjob he had ever received. Jerry moaned out loud, and I paid careful attention. The last thing I wanted was for him to come. When I sensed that he was getting close, I withdrew my mouth.

"Don't stop," Jerry begged.

"Did I tell you to talk?"

I stood and hitched up my skirt. I wasn't wearing panties.

Jerry was aghast. "You went out like that?" he said. "What if somebody saw you?"

To shut him up, I straddled his face and buried his mouth under my cunt, very wet by now. From Jerry, I heard a muffled protest.

"What was that?" I said. "Sorry, can't hear you. You shouldn't talk with your mouth full, anyway."

I wriggled against his tightly pursed lips, but couldn't get him to give me even a little bit of help.

"Lick it, you moron," I said, then I remembered that Jerry was an ass man. I leaned back slightly until I felt Jerry's nose in my puss and his lips against my butt-hole. "Lick my ass, Jerry, or I swear to God I'll smother you."

Jerry was in fact gasping for breath. I had all his airways very effectively blocked. Finally, I felt a meek little lick on my ass.

"You can do better than that," I said. "Come on, give me some real tongue and I'll let you breathe."

Jerry's tongue jutted out desperately, penetrating me. The feeling was oddly pleasant, but the real satisfaction came from knowing the disgust Jerry must surely be feeling. Sure enough, when I rolled, off him, Jerry was gagging, his face dripping with my juices. I had to laugh.

"I don't think it's very funny," Jerry said miserably.

"Oh trust me, it's hilarious," I giggled.

"All right, Lisa," he said firmly. "I've had enough of this. We're done."

"Not even close," I said. "Roll over."

"What?" Jerry barked. "No."

"What did you say?"

"I said no," Jerry was getting pissed now. Not even a trace of his lawyer cool.

"Really," I said. Into the bag again. Item number three, a Polaroid camera. This was when Jerry really started to freak, thrashing around and yelling. I snapped several good shots of Jerry pulling at the cuffs, with his limp cock flopping around comically. I showed him one of the better ones.

"I think I'll send this one to your boss," I said. "Or do you think your dad would like it better?"

"You cunt!" Jerry screamed.

"I know a place in town that makes real good color copies of pictures. I can send out dozens of them, to everyone you know."

"No, you fucking bitch!"

"Oh, be nice," I said mildly. "I'll let you burn them all if you just be a good boy and roll over."

"Fine! Fucking fine!"

"I'm going to undo the cuffs for a second, but don't get any ideas. If you try to get away, I'll fight you. I'm sure you could beat me up, but I don't think a domestic violence conviction would look good on your resume."

Jerry looked like he was about to cry. I undid the cuffs, let him roll over on his stomach, then re-did them. Jerry's ass, admittedly cute, was sticking up into the air.

"Now the real fun begins," I said.

Items four and five from the bad black bag. A long thin candle and a tube of KY. Jerry couldn't see these articles, but he had a fairly good idea what was happening when I squirted a great glob of jelly into his butt crack and started rubbing it in.

"No!" he begged.

"Shut up, you big baby," I said. "And relax. It'll hurt a lot less if you relax."

Jerry whimpered, and before he could really tense up, I plunged the candle several inches into his slicked-up rear. He screamed out loud, and it was like music to my ears. I got a real charge out of butt-fucking the butt-fucker for a change. Eventually, though, he started moving with the motion of the candle and I started getting the feeling that he was enjoying this. Couldn't have that, now.

I pulled the candle out of his ass with a wet plop and threw it aside. I pulled the sixth and final item from the bag. A thin leather belt. I made a few practice cracks against the mattress, which got Jerry screaming again. Then I started to sincerely wail on his ass.

"That's for making me feel like a child." CRACK! "That's for embarrassing me in front of my friends." CRACK! "That's for being such a selfless prick in bed." CRACK!

I had a list of about twenty such charges, but I stopped after ten or so when the big red welts began to form on Jerry's ass. After all, I'm not really cruel by nature.

Jerry was practically sobbing, begging me to stop.

"Almost done, Jerry," I soothed. Then I stuck two things up his ass. The second was the stem of the rose. Jerry yelped in pain as the thorn sliced his rectum.

"Pull it out, please," he cried.

"Pull it out?" I said. "That would HURT. Besides, you look really pretty with a rose sticking out of your ass. In fact . . ." I snapped another picture.

Jerry, tears pouring into his pillow, waved his butt around to try and work the rose out. He looked like a doggy wagging his tail, and this unexpected association got me laughing hard again.

"Look at me, Jerry," I said. He shook his head, crying into the bed. "Look at me, you little bitch!"

Jerry looked up at me, face red from tears.

"Watch carefully," I said. I lifted my skirt and slid my fingers down into my dripping wet vagina. I tweaked my clitoris and in my jacked-up state, that was about all it took to bring myself to a thunderous orgasm.

"I guess I'm going to hell now," I said with a shrug when the shudders had subsided. "Can't be worse than dating you."

"Lisa," he moaned. "Please . . ."

"Too late," I said. "You should have treated me better."

I gathered my things and started out the door.

"Aren't you going to let me go?" Jerry begged.

"Uh . . ." I pretended to consider. "No, I don't think so. But I did leave you the key to the cuffs. It's up your ass."

When this sank in, Jerry really started to bellow.

"When your mom and dad come home, I'm sure one of them will reach up your butt and pull out the key for you. After all, I know how close you are."

"You're going to pay for this!" Jerry screamed. "You're going to jail, bitch."

"I kind of doubt that, Jerry," I said. "I don't think this is a story you're going to tell to too many people, even the police."

With that, I was gone. I got in my car and had to stroke myself off one more time before I drove home.

On the way, I felt bad about what I'd done to Jerry. That is, for about a minute until I remembered all the butt-fucking I'd been subjected to. Then I just felt happy about life without that loser. Priority number one in my post-Jerry life: lose my virginity to the first likely candidate. I couldn't believe I had been saving it for so long, for such an amazing jerk. The embarrassment of the fact made me want to fuck somebody, anybody.

To that end I already had a plan. My very best girlfriend Carrie had won two tickets to a Tom Petty concert by calling in to a radio station, and she'd asked me to come along. Petty never failed to get me hot, and I knew there would be lots of guys there looking to get laid. The first even halfway cute guy who approached me would get more than he bargained for.

That was the plan, anyway. Little was I to know that I was the one in for a surprise.

To Be Continued...