Mom had her arms crossed and was tapping her foot on the floor. I knew I was in for it now. “I purposely left the news of this assignment until today. My word Billy you’re acting like a child. Judge Abernathy told me she wanted you as her clerk as she called it, and said you’ve had the making of an excellent lawyer for years. You even told me you wanted to be a lawyer so why throw a hissy fit now?”
I was whining and I knew it. “I’m happy to do anything for the judge, you know how much I admire her. You know I have a huge problem with Olivia and her reputation. She is not a good girl and you know what I mean.”
Mom’s cheeks flashed red. “That’s all gossip and hearsay and there’s not a shred of evidence. You will present yourself to the judge at 6:45am dressed to impress. All five of your bosses so far are begging for you to work for them next summer. I expect even better from you for the judge. Go to your room and get ready for the next week. I purchased a blue sport coat so you’ll look extra sharp for tomorrow.”
I had no choice; I followed directions. Judge Abernathy was a fantasy of every middle school boy. She was 5’10” tall, silky chestnut hair—all natural color too, smoldering blue eyes, a smoking hot cleavage that was always enhanced by lacy push up bras that always peeked out a bit, form hugging business suits, various colors of shiny silk stockings and stiletto heels. I was a study hall monitor in middle school and mom prepped me for weeks. “When you meet the judge, you are to say; “Good morning your honor, how may I assist you?’”
On the day the Judge walked in the front door carrying a large box, I jumped from my seat and ran over to her. “Good morning your honor, I’m Billy; please let me assist you.” I grabbed the box and the back of my hand grazed one of her firm breasts and I blushed scarlet. If the judge felt anything she ignored it. I had dreams about touching that breast for years.
Instead she gushed over me. “Oh Billy; you are my handsome boy. I’m going to tell your mother what a joy you are.” She kissed me on the cheek but wiped off the lipstick with a silky thumb. She whispered, “We can’t have all your girlfriends being jealous now can we? Bring that along.” I took her and her package to the principal’s office and she took my arm as I escorted her out. The fantasies I had about the judge could fill several books.
The next morning I was twenty minutes early and Olivia came along all together too cheery. “Ah, if it is not my precious little William. I am to be your tutor for the next two days. I have little hope you’ll be anything but a dolt.” Don’t get me wrong, Olivia is a knock out. Great body, same hair as her mom, a bubble butt she wiggles all the time, 38c breasts that jiggle and shake and brown eyes that make me weak. She’s just mean to most guys and extra mean to me.
Olivia kept me hopping from the time we walked in until 6:00pm. I made copies, I put returned files in the correct cabinets. I got files judges needed and delivered them to every judge but her mom. I emptied waste paper baskets and I even got Olivia lunch while I stood and watched her eat. I’d kill her before the five days was up if she kept this up. At 6:00pm, Olivia took me to a conference room in a distant part of the courthouse and made me walk behind her. Her legs shone in those stocking and her butt looked better than I remembered. I was going to flick the tip of my cock because of my raging hard on, but Olivia stopped suddenly and spun around. At that point I was luckily looking at the back of her head. She opened a door and said; “Enter this room William.” I followed her in and there was not much light. She put a chair in the corner and made me sit on it. “You sole job tonight is to please me with your tongue. Sit on your hands so you’re not tempted to touch me. Take off that splendid jacket first.”
I did as directed and Olivia quickly removed her suit and blouse. She was wearing a one-piece black lace piece of lingerie that had slits for her nipples and pussy. Olivia slipped two fingers into her pussy and made a show of stroking herself noisily and groaning. I sat on my hands and Olivia roughly grabbed my cock through my trousers. “Ooh, that feels like a nice sized dick but it stays tucked away and no beating your meat tonight. I want to see a nice pair of blue balls tomorrow. Now suck my tits.” She pulled the slips apart slightly on her lingerie and pinched her nipples and groaned some more. I would have obeyed, but Olivia held them just out of my reach and squeezed them and pulled on her nipples. “Oh William, they do taste sweet. Here is your first taste of my tits.” I licked her nipples as she presented each one in turn. Olivia even held still long enough so I could suck each one for around a minute. “Yes, that was well done. Now suck them and make them harder.” I did as directed and Olivia moaned with delight. She held my head in place and groaned as I please her. I was pleasing myself too but my cock was trapped in my pants and the pain was considerable,
Without warning she placed a leg on the arm of my chair and thrust my face into her pussy. “Suck it now and suck it good. Make me come William.” I slipped my tongue between her labia and found her clit and sucked it greedily. I was gentle but increased the suction and tempo of my licking. It did not take long before Olivia orgasmed. She never said a word until she was completely dressed. “Go wash your face and get dressed. If you ever tell a soul, I’ll make you wish you’d never been born.” As I stood, she really put a twist on my hard-on and whispered, “Remember, hands off your sperm; it is all mine.” Olivia grinned as she continued to twist my cock. She only let me go when I groaned in pain.
When I walked in the door at home, mom let me have both barrels. “The judge called and wanted to know where you were all day. I told her you sure never came home. I want to know where were you slacking off.”
I whined even more. “Olivia watched me work and she kept me pretty much locked in the basement all day. She never even let me eat lunch and she just let me go ten minutes ago. She hates me I tell you.” Mom let me eat and I rushed to bed.
Olivia was even worse on Tuesday. She actually would time me and make me run to a certain judge’s chamber in a certain amount of time. I had to get doughnuts for the bailiffs and deliver each one in person. She was laughing at me as I started to get more tired. She actually gave me water to drink and made me eat something. At 6:00pm she took me to the same room and did the same thing as yesterday. “Oh my precious little William, you need to please me again. Same rules and let’s see if you followed directions.” She really grabbed my balls even harder and twisted them. She made a big show of unzipping my pants, pulling out my cock and balled and squeezing them as hard as she could. I grunted, but made no other sound. Olivia put my cock and balls back inside my pants and zipped me up. “That is the way a good boy behaves. Now you know the drill. Make me come with your tongue and no touching. Olivia did not last five minutes and she was wetter today. She must have been playing with herself all day long. When she came, she ground her pussy all over my face and laughed. “That was very pleasurable. I have tomorrow off. We’ll see if my mother is as pleased with your behavior as I am.” After she dressed, Olivia just left and I was forced to clean myself up on my own. I was so angry with my mother I ate on the way home.
As soon as I walked in the door she just scowled. I hit her with both barrels. “Olivia will not be around to boss me around tomorrow. I will do everything I can to please the judge. You will be impressed.”
I fell asleep immediately and the next day when I prepared for work, I dressed to impress Judge Abernathy. I was there early and Judge Abernathy grinned when she saw me waiting for her outside her chambers. I rushed to help her with her briefcase. “I’m sorry I did not come to see you the last few days. Olivia kept me hopping all day long. You let me know what you need and I’ll make sure you are satisfied.”
The judge just beamed at me and walked over and put a very warm hand on my cheek. She gently stroked my cheek and her perfume kind of reminded me of roses. “Now tell me the truth; where have you been the past two days? I need every detail and I can tell if you lie.” I’m a sap or the judge put a spell on me. I told her everything and even the way Olivia made me pleasure her both nights. The judge hugged me and said softly, “Oh you poor, dear boy. I will deal with Olivia tomorrow, but you need my help today. Sit on the sofa.”
Judge Abernathy’s butt is entrancing. I watched it jiggle as she locked the door and removed her jacket. Her breasts are equally seductive. They jiggle and wiggle with every step she takes. She stood in front of me and all I could hear was the pounding of the blood in my ears. She took a pillow from the sofa and put it on the floor in front of me. She kept eye contact with me the entire time. She traced the line of my jaw with her finger and said huskily; “You wouldn’t mind if I take your cock in my mouth, would you?” I shook my head no mutely as she pulled my pants down. When she saw my cock she smiled and said, “Oh wow! That is a very nice one; I really like your cock. I’m going to suck you now.” Her mouth was so warm and her tongue knew right where to lick to arouse and stimulate. She was making the same kind of noise I make when I’m eating delicious food. “I like a big thick cock like yours; they are my favorites. I’m going to make you cum quickly now, but we’ll enjoy ourselves later.” In addition to her mouth she rubbed my cock with both hands and fondled my balls. Before I could even issue a warning, my cock exploded my cum down the judge’s throat and she made contented noises the entire time she drank my sperm. “Oh Billy, you are such a dear sweet boy. Now let’s get you set up downstairs. I have a hunch Olivia told the rest of the staff not to show up and she worked you to the bone.”
The staff explained to the judge that Olivia had told them to take the two days off with pay. Working with three other people was much easier. I told the other clerks it was all fine and Olivia was just playing a trick on me since we knew each other our entire lives. We even had time to eat lunch together and everyone pitched in and bought me lunch. I had decided right then, I’d do this job next summer and see if being a lawyer was right for me. A note came down that I was to see Judge Abernathy immediately and everyone waved good bye. The secretary let me in and she took off. The judge dismissed the bailiff and called mom on the phone. “Oh darling you have no idea how hard Billy worked the last three days. He went overboard trying to impress me. Now you know he didn’t need to do that.” Mom must have talked for a long time because the judge kept blowing me kisses and winking at me. Mom finally took a breath. “I know darling, but I’m sorry to say I’m putting him through the wringer tonight. He’ll find out what being a lawyer means. He’ll be home around 10:20pm and of course I’ll feed him. Just so you know, next summer and every summer until he’s a lawyer, he’s working for me. You take care now.” The judge grinned at me and rubbed her neck.
I ran over behind her and massaged the stiffness out of her neck. The judge made those same noises like she was enjoying a meal, so I worked my way onto her shoulders. The judge broke contact and led me by the hand to an oak chair with arms. I helped her take her coat off and I hung the jacket up. I came back and started kneading her shoulders, The judge unbuttoned the top two buttons of her blouse and I could see a silky royal blue bra. Along with her perfume and cleavage, the noises she made caused my cock to stand at attention. The judge leaned back and rubbed the back of her head on my cock. “Oh Billy, come around in front of me. I need to assess your skills.” I hurried around and Judge Abernathy unbuttoned her blouse and pulled it off. It was my turn to make some pleased noises. “I’m glad you approve. Now kiss me gently and massage my breasts like the gentleman you are.”
My knees buckled when the judge kissed me and she held me up by grabbing my butt with one hand and my head with the other. I got myself under control and ran both hands tenderly over the silk of her bra. I felt her nipples stiffen so I traced the outline of both of them with my thumbs. The judge moaned, but was too busy sucking my lower lip to speak so I gently squeezed one nipple and worked it between my thumb and forefinger. The judge forced our bodies together and my cock and her pussy were perfectly lined up. I could feel the heat from her body as we rubbed our groins together. I had no idea anything could feel so sexy. I gave her breasts a firm squeeze and Judge Abernathy said, “Make me come with your mouth Billy. I need it so badly.”
I fumbled around until I found the zipper for her skirt and helped her step out of it. I stroked her pussy through her silky panties and the judge pushed my hands out of the way and she pulled down her panties and I let them slip to her ankles. She had an innie so I spread her slit and her clit popped out dripping wet and I caught her juice on my tongue and slowly licked up and down for a few minutes. I backed off to take a look and her clit was so pink and stiff, I just sucked it between my teeth and flicked my tongue faster and faster. The judge thrust her hips forward, put a hand on the back of my head, and held me there as her orgasm exploded through her body. I thought we’d spend the rest of the time making wild, passionate sex, but the judge got dressed, fixed her face, made me wash and we had a working dinner and I did help her with a case until 10:00pm.
I made sure I was even earlier on Thursday, but Judge Abernathy beat me there. “Good morning Billy, come in and lock the door.” I did as I was told and Judge Abernathy was sitting on the sofa with a red satin top with spaghetti straps. “Come here you darling boy. You’re going to titty fuck me this morning.” She bent down, quickly pulled out my pecker and almost swallowed my cock in one gulp, but all she was doing was getting my cock lubricated with her spit. She popped off me, pulled down her top, and shoved my glistening dick between her bare breasts. “Oh yeah, Billy; I like that. Yes, shove your hips against me. Oh I like that when you push against my tits. That is the way to do it. I like that. Shove that big, thick cock between my breasts.” I was thrusting against her and she loved it. “It feels so good, yes pump that cock, can you feel how hot my tits are? Oh, yes I really like that.”
She took my dick and slapped her tits with it and rubbed it all over her nipples. She made sure to rub my cock head with her nipples until I was oozing pre-cum. “Ooh, you won’t tell a soul about this will you Billy?” I tried to answer, but she sucked my full length down her throat and rubbed her nose in my pubic hairs. I looked down and the judge winked at me while she cupped her breasts and tweaked her nipples. “You like my tits don’t you Billy? I bet you want to come all over them, but you’re a good boy and you won’t do that. You’re going to shoot all your sweet sperm down my throat. Do it now Billy.” The judge swallowed my cock and in under a minute I was splashing her tonsils with my sperm. We got our clothes straightened up, dressed and the judge decided we should go over what we worked on last night. Olivia walked in on us discussing the merits of the case.
Judge Abernathy was very terse and stern with Olivia. “From now on darling, do not forge my name on time sheets. I went back and replaced your copies, but if it happens again, I’ll have to fire you. You owe William an apology. He covered for you saying it was a practical joke, but do not ever use another staff member like that again. Now shoo, both of you! I have work to do.”
As far as Olivia was concerned, I had thrown her under the bus. “Thanks for squealing to my mom. You can really stand up to her I see.” I chose to remain silent. “At least covered for me. You must have been here late last night. I bet you just ate it up listening to her call you her darling boy.”
I yawned. “I was here until after ten, then she had me up at dawn to go over everything again. I may be her darling boy, but she’d kick me to Cleveland if I ever pulled a stunt like you pulled. She has your back Olivia. And I didn’t cover for you, I did it for your mom. I had hoped I save you from having a family scandal plastered all over the newspapers and television.” Olivia blushed but she never apologized
There was a big burly guy waiting by the clerk’s door with a bunch of flowers and he stiffened when he saw me. “Hey you little slug, what you doing with my girl?” I looked around and Olivia smacked me on the back of the head.
She smiled and cooed. “Are these for me Bruiser? You’re too good to me. This looser is Billy, he’s a new intern. He gets lost easily so I had to walk him down the stairs. Don’t worry, our date is still on. Be here right on time so we can spend our whole vacation together.” She stood on her tiptoes and kissed his cheek. Mr. no-neck just cracked his knuckles at me.
We had a great day at work and everything went well. Today, there was no fooling around—just work. The judge even forgot about dinner. Just before I left, she slipped a note in my pocket and winked. “Make sure your mom doesn’t find it and read it in the car on the way home.”
I read the note in my car; “A Gentleman is always prepared. I like ones that please the woman.” oxoxox JA I stopped off at the all night pharmacy, but they only had three types of condoms and I brought all three.
The first bit of good news I got was Olivia was off today. The second piece that made me happier was we were through at noon. I expected to have a free afternoon until Christine gave me a note from the judge. “Sorry Billy: Something has come up and I need you to work until five. We have a big case to work on. I’ll call your mom. Thanks JA”
Christine laughed her head off. “You’ll probably work until ten and she never eats at night so you’ll starve. Have fun!” I slumped down on the table. The rest of the clerks went home happy at noon and I headed to the judge’s chambers.
Her door was open and she was on the phone. She waved me in and did not do much talking. She was taking notes like crazy. At least there were sandwiches and chips on the table. We ate in silence and I took the trash to the garbage bin in the hall. The judge was hiding behind the door and when I walked in the room, she closed the door and locked me in. “Did you do as I suggested?”
I nodded. “Yes, I did Judge Abernathy, but they only had three kinds and I don’t know these styles.” I held the condoms out and she took them and put them on the table.
We kissed for a bit and she finally said, “If we are going to be lovers, you can call me Jane. Now let’s see what you have.” She looked at the condoms closely and laughed. “You have no idea what these are for do you?”
I nodded. “I sure do. Condoms stop the transmission of sexual disease and prevent pregnancies.”
Jane came over and held my hand. “These condoms are for anal sex and you’ve never done that have you?” I blushed to my toes and looked at the floor. Jane lifted my chin and she said quietly, “I love anal so let me show you how it works. I’m sure you’ll like it.” I helped Jane off with her clothes, hung them neatly and today she wore no underwear, just stockings. She pulled a bottle of lube from her purse and sat on the sofa and had me strip. “You need to put plenty of lube in my asshole but be gentle. One of the condoms is made for this. I might be a bit tight at first, but go slowly and I’ll enjoy myself.” I was as gentle as I could be. I started by lubing her asshole with one finger, then two and finally three. Jane pulled on her nipples, bit her lip and moaned. “You naughty boy; stop teasing and use the extra lubed kind of condom.”
I did as directed and Jane was furiously stroking her clit and almost crying. I slowly inserted my dick in her ass and I slipped in easily. Jane muttered, “Oh you have such a nice cock. Do it slowly until I take over. Go slow.” I think I was too slow but Jane smiled and stroked her clit harder. She started thrusting against me and I could see her clit jutting out between her labia. Jane thrust her hips forward and moaned, “Grab my hips you naughty boy and pound my ass. You know I want it.” I did not go all out at first, but the way Jane growled urged me on. I grabbed her hips and just kept pounding until Jane softly squealed and her orgasm shook her body. I went into her bathroom and started to wash. Jane snuck in and lathered my cock and balls. “I need you nice and clean now. You’re going to give me what I’ve been waiting for since Monday.” I’m pretty sure I was more than clean enough, but Jane washed me and soaped me until my poor dick was twitching.
She actually led me back to the couch by my dick and I made all kinds of noise to make sure she understood how much I liked the way she stroked and fondled me. The next condom she chose was so tight, I wasn’t sure it fit correctly. Jane cooed and said, “Oh that’s perfect. I’m going to lube you up and ride you. I doubt you’ll come, so just try and help me have as many orgasms as possible.
Jane loved riding me and I loved feeling her pussy pound my dick, but I was never coming with this condom on. I concentrated on stroking her clit, and Jane came quickly but gently. I reached up and kneaded her breasts and listened to her moans of pleasure. This took way more time. I started concentrating more on her nipples and Jane used her hands on my thighs for more leverage. He second orgasm was more intense. Jane tried to stand twice before her feet were stable. She mounted me so we were facing each other and I bent down and licked her breasts and sucked her nipples. She had a tiny orgasm and sat there gasping, until I started thrusting into her while sucking her nipples. She pulled my head off of her and put her arms around my neck. I stood and flipped her around so she was seated and I could thrust into her with all my might. Jane squirted so much juice, I thought I had broken something inside her. I ran to the bathroom and got a few towels and some cleaner and cleaned up. Jane laughed quietly as she led me back to wash me a second time. It took a long time before I was clean according to Jane.
Jane put me on the couch and put a pillow on the floor. When I tried to reach for her pussy, she slapped my hands away. “Unlike you, I can only take so much. You want me to suck your cock but you’re going to have to ask nicely.”
I took Jane’s face in my hands and kissed her gently. “Since the first time I brushed that magnificent breast of yours in eighth grade, all I have fantasized about is you.” I kissed her again and she slumped against me. “I almost cried last night when I realized this was my last day with you. You made all my dreams come true but I need something to remind me I need to come back next summer. I need the best blow job you can give me.” I kissed Jane again and she made her yummy sounds.
Jane gave me a playful slap on the knee. “I always wondered if you felt my boob you naughty boy. I just love sucking this nice big cock. I’d keep you at home from college, but you need your education to become a lawyer. I’m going to suck just the head for a long time and french kiss it. Just relax and let me enjoy your delicious cock.” Jane was better than her word. In five minutes my pubic hair was soaked from her spit. She had both hands wrapped around my dick and she would rotate her hands as she moved them up and down varying the pressure. She licked my balls and said, “I’m going to drain you of your cum and if any hussy tries to move in on you at school, you better drive them off. This cock is mine.” Jane pulled my head down for a sloppy french kiss and then she sucked my dick so far down her throat I thought she’d gag, but she didn’t. I was holding back my sperm as Jane came off me and whispered, “Give me all your sperm you naughty boy and do it now. I’m sucking you dry.” I lasted until she had taken my entire length down her throat four times before I shot my sperm into her. She sucked and swallowed and even after I stopped spurting cum, she kept on sucking until I was limp. I lay back on the couch groaning in pleasure. Jane laughed. “Come on my darling boy. We need to get dressed for dinner. Your mother is meeting us. She wants to make sure you pleased me this week.”
Mom was waiting at the restaurant and she stared me down. She turned to the judge and asked, “Go ahead Jane; how bad was it?”
Jane laughed. “You should be proud of your son. He has a quick mind and the rest of the clerks love him. Too bad it’s his last day. I could really use him since Olivia is on vacation for the next two weeks.”
Mom laughed and said, “Oh Jane you made me the happiest mom in the world. Billy has two more weeks of summer vacation before cross country practice starts. I’ll make sure he’s at your chambers at 6:30am ready to help you with your briefs on Monday morning.”
Jane winked at me without mom seeing. Jane clapped. “That’s the best news I’ve heard in months. I need help with my briefs. Billy is going to know all about the law when I get done with him in two weeks.”
I didn’t say a word. Two more weeks with Jane—that’s the way to make all my dreams come true.
THE END: UNTIL NEXT SUMMER
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