Sorority Auxiliary Bk 2, Ch 2: Great Expectations Part 1b

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micheleFFS
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Sorority Auxiliary Bk 2, Ch 2: Great Expectations Part 1b

Post by micheleFFS »

Samantha came in, still carrying her laptop bag, evidently straight from campus. She looked a lot like the first day I talked to her, blonde hair framing her face, light make-up, bright red lipstick, very tight sweater, mini, tan pantyhose, flats. She gave me a smile, not quite her TCD, and sat next to me. “Here,” she said, replacing my hand with hers, “let me help you.”

“Of course,” I said happily. Might she rescind her standard that I be fucked by four different women before she took me again? Amanda’s report...

She stroked me very slowly using a light grip, her voice at the same cadence. “You had a big Thanksgiving, didn’t you?”

“It was wonderful — and very surprising!”

“Christina and Zoe enjoyed similar surprises. Zoe’s was kinda like yours. You did more fucking than you ever did in your life, didn’t you?”

“Oh, yes.” Samantha’s hand technique made me crave more. I twitched my hips.

“Hold still.” She gave me her false smile. I was in for it. “Amanda wrote that you were a fast learner and fucked her very well to many orgasms. She actually said you were a very good fuck already. High praise.”

“I’m very grateful to her for lots of things.” Keeping my hips still was not easy.

“I know what you’re thinking.” Her unwavering eyes held mine enthralled.

OK, I’ll bite. “What?”

“You think Amanda’s very favorable report will persuade some of the girls to engulf you, right?”

“The thought crossed my mind. How could it not?”

“Inevitable hopes. I know what you’re thinking right now.”

I raised my eyebrows and looked at her.

“You’re thinking that maybe I’ll be intrigued enough to take you upstairs to my bed and find out just how much you learned about fucking, right?”

“Inevitable hopes, as you say.” Precum lubed her hand.

“I do like being fucked. By a trained submissive who won’t cum unless I allow it. Are you that kind of boy, Jenny?”

“Yes.” My voice sounded funny. More precum.

“I like being fucked by a boy who afraid of the consequences if he doesn’t fuck me to my high standard. Are you that boy, Jenny?”

“I’m always a bit afraid of you, Samantha, even when you make my heart melt.”

She favored me with a smle.“A beautiful answer, Jenny. I like being fucked by a boy who thinks only of my pleasure without a care for his own. Are you that boy, Jenny?”

“I never stop thinking of the pleasure I can give any woman who accepts me into her, and attempt to make it the best for her, but I likewise am very aware of my own pleasure.” My toes twitched from the effort to keep my hips still. She got me so frustrated, so fast!

“An honest answer and the best that can be expected from a boy who’s still new to serving women and to fucking. You’ve come a long way since I met you in the student union, Jenny. Hold still and keep your hands to yourself.” She kissed me, long and deep, holding my head with her free hand while never varying her maddening penile massage. Precum flowed.

“I do so like to be well fucked. When I fucked you, you were a virgin. I know you’ve fucked three of us since. Do you come well recommended?”

Panting, on edge, fighting for control of my body and my insistent desire to spray, I managed, “All 4s or better and 4s or better on my fucking!”

“Hmmmm.... Very, very good. I’ll take it under advisement.” She propped her chin on her hand. The Thinker Giving a Hand Job. She stirred my balls with her other hand. “Hmmmm.... On the one hand.... On the other hand... It has been a very long time.” She resumed stroking me. “.... All that delightful thrusting, deep inside me.... A boy I lured into sexual servitude.... Promises to be a superior experience... But in the end, no, you need more experience.”

She squeezed with both hands, twisting my cock, crushing my balls, then let go!

I screamed and flopped back, panting, tears filling my eyes.

Sam stood up with her back to me, spread he legs, bent over and flipped up her skirt. Lace top thigh highs, no panties, a dripping, aromatic pussy. Her action put her in reach of the frantically masturbating Talissa. Grasping his cock, she said, “Come. I need an experienced boy.” She straightened, letting the skirt cover her again, leading Talissa out by the cock. He gave me an apologetic look, as if to say “It’s not my fault.”

I lay on the couch on my side, clutching my poor cock and balls, tears flowing. Not even a half an hour back in TDK and look at me. What was that said about pussywhipping?

As I lay there, in pain, feeling sorry for myself, Elaine returned with Bethie, who fondled the tip of his newly freed prick. Voyeuristic Elaine smirked as another boy brought himself to erection.

As Bethie reached his full length and girth, Marci came in, carrying a small valise. She took in the scene with a glance, then waved her hand at the space on the couch where my head lay. “Move over. I want to sit down.”

I curled up even tighter.

Plunking herself down, Marci crossed her legs, revealing the welts at the tops of her stockings, the sexy sight leaving me unmoved in my condition.

“What are you covering up for? Nothing we haven’t seen hundreds of times. Take your hands away. Oh, no wonder you hid. Below Stairs, soft as a pre-teen. A shocking way to present yourself to me, a Sister who’s taken an interest in you. Do you have any excuse?”

“Nice to see you too, Mistress Marci. Sister Samantha cockteased the hell out of me, busted my balls, twisted my cock, then took Talissa off to fuck him.”

Marcie laughed. “That’s no excuse for a limp dick.” Her voice developed an edge. “Nor does it excuse sarcasm and resentment. Take that.” Her hand shot out and she crushed my balls.

I screamed again, curling full fetal, clutching myself anew, fresh tears flowing.

Marci and Elaine laughed. I moaned. Bethie said, “Oh, you poor boy.”

As my moans subsided, Marci made one of her turnarounds. She cradled my head in her lap and kissed me.

I lay there, unwilling to kiss back.

Marci stroked my cheek, drying some of my tears. Her hand probed under mine.

I whimpered in fear.

“Jenny, you know I like messing with your head and hurting your body. I’ve always been interested in your development and you equally bring out the nastiest and the sweetest parts of me. Let me hold your poor abused cock and comfort it. I promise you, no more testicle pain today and no pain at all while we’re downstairs. And I’ll be very nice to you when we’re upstairs.” She kissed me again.

I moved my hands aside and Marci’s cool fingers soothed my aching seeds. I put my arms around her and rested my head against her stomach.

Marci soothed me with one hand on my ballsack, the other in my hair. Bethie handed her tissues, and she gave them to me to dry my tears. Marci rubbed my cockhead, and up I went, much to my surprise. She soon told me to sit up and made me go to the edge, dripping more precum. My balls still ached.

“Agony to ecstasy,” said Bethie. Elaine had left. “I’m very glad you’re feeling better.”

I smiled my thanks.

“Ok, now that you’ve recovered, we’ll get started on what’s planned for you today. Bring your rollaway and my case.”

She led me to the dining room and had me set up a portable lighted make-up mirror from her valise on one of the tables. I displayed my feminine clothing on another table, and lined up my make-up by the mirror. As I did, several Sisters gathered, Veronica first. Angela, without Talissa. Dorothea arrived, looking pleased.

Marci handed me a cape to fasten at my neck and, with a sigh and a rueful shake of my head I could not suppress, I applied my make-up in front of all those Sisters. More arrived during this humiliating performance.

My spectators participated vocally. “What’s that? It’s too red for you.”

“It’s beard cover, only goes where I develop stubble,” I explained.

“Don’t worry, he had a real make-up artist teach him.” This from Veronica.

The comments never stopped. “I bet you a massage he puts on too much powder.”

“I won’t take the bet; I don’t want to give you a massage.”

In the face of this teasing, I grew determined to show them Henrietta had taught me well. I concentrated on doing my best.

“Careful, don’t smudge.” “Don’t be a wimp, you can build up more mascara than that.” “That’s not enough, outline those lips wider.” “Your brightest red, make yourself slutty.”

Marci put on my wig and fluffed it. Done, I faced my audience with a proud smile. “Well, not bad.” “He actually looks cute.” Applause, no less.

That’s when satiated, smiling Samantha entered, followed by grinning Talissa, limp dick still glistening from their mingled fluids. I felt a very unjustified, strong pang of jealousy and envy, quickly suppressed before the crowd.

Marci looked at me more closely than the others and nodded approvingly. “Nicely done.” She turned to the audience. “Jenny’ s got a pretty face, but is she sexy and seductive? Show us, Jenny.” She handed me my bra.

I stared at the floor as I fastened the rear clasp and spun the bra around. Marci handed me my forms and suddenly I possessed one of the larger busts in the room. Mingled laughter and applause prompted me to twist this way and that, giving them my profile.

Marci handed me my garter belt and draped the stockings over a chair back. “Sit down and give us a show with your stockings and legs.”

I blushed. Amanda and Henrietta said I wasn’t very seductive. I gulped and decided to go over the top. Bravely, I faced the crowd with an exaggerated simper.

“Cute!” “Not!” Ugh!” “Ooh, la la.”

I slowly rolled up one stocking, placed my toes inside and stretched my leg, continually checking the seam as Henrietta taught me. I did the same with the other leg to much criticism.

“Too fast.” “No toe point?” “Turn the leg, smooth the nylon.” “You’ll never get a man that way, Jenny.”

Flushed anew, I fastened the front clips, stood and twisted as I checked my seams a final time and clipped in four remaining garters. I tugged on panties to match my bra, buttoned my blouse, stepped into my skirt and heels. Marci fitted me with my silly hat and stepped back. Somehow, I faced the audience and curtsied. I turned a bit sideways, one hand on a cocked hip, the other brushing my wig, with an over shoulder simper.

“Wow!” “She really is cute.” “Hubba, hubba!” Even a wolf whistle. Loud applause. My heart sank. I was way more of a hit than I wanted to be.

“But wait! There’s more!” Marci held up my little fanny pack. “Our new maid comes ready to party with her Pleasure Pouch at h er side. Show everyone what you’ve got.”

I exaggerated my resentful pout, but dutifully showed off the nipple clamps, small vibrator, lube, cockring, anal plug and beads, and the short slapper. More applause.

Dorothea beamed. “We’ve got a real maid again, girls. It’s been over a year. Jenny, you’re a real cutie. Expect to be in uniform for Sorority formal occasions and parties.” She patted my face.

“Yes, Mistress,” I said miserably.

“In fact, you’ll serve any of us who want to eat downstairs tonight. Dinner’s in 20 minutes. For now, see if anyone wants refreshments.”

“Yes, Mistress.”

Marci said, “A moment, please. Have your fun with our new maid, Jenny, but I ask that you respect a promise I made that she won’t have any real pain, especially in her sensitive little balls, while downstairs. After dinner upstairs, that’s a different matter. Thanks, Sisters.”

A general murmur of assent followed this request. I expressed my heartfelt thanks to Marci.

Few Sisters drifted back upstairs; most moved to seats in the dining or living rooms and called loudly for juice, crackers and cheese, and the like. I stood there, perplexed. Where to start? I had to laugh. “Ladies, please wait a moment. I shall return with refreshments.”

Steffie and Nicola bustled about, fully clad, but took the time to point at me and laugh as I tottered about in my heels, putting glasses, plates, two varieties of juice, cheese, crackers, and a few cut veggies on a rolling table.

The boys were doing a service shift. Part of our initial training consisted learning to cook, clean and maintain the various appliances of the Sorority house. Work this into the appropriate place in book 1. Service shifts were short, about two hours, always included a free meal and sometimes led to sexual service to a Sister at the end. We all did about two a week. It looked like maid Jenny might get more of them. Ugh!

After poking fun at me, they gave me a hand with the snacks and watched from the door as I started my rounds.

I paraded around the two large rooms, pushing the cart, curtseying to each group of amused Sisters. My fake boobs attracted many feels, my bottom received several whacks, I raised my skirts to display my stockings. I bowed to the inevitable and got into the good-natured fun. I simpered, I wriggled, I acted outraged at the slaps to my rear. “Don’t do that,” I pouted. “Keep your hands to yourself,” I snarled.

Eighteen of the twenty Sisters were in the House at the time and they all decided to eat together in the dining room, an unprecedented event in my experience. Steffie and Nicola set the table, I ran back and forth, bringing food to the women, filling incessant beverage requests. Between trips, I managed a few bites to eat in the kitchen. The teasing, slapping and poking never stopped. Mistakes such has handing the wrong drink to a Sister met with mock severity and mild swats. Steffie and Nicola couldn’t stop laughing.

Finally, the meal ended. Marci and Veronica led me upstairs to their room, carrying the luggage. When we arrived, I said, “Mistresses, I am experiencing a genuine feminine feeling for sure.” I swayed a bit as I stood.

Veronica looked curious. Marci cocked her head, then said, “I bet I know. Yes, Jenny, you may remove your heels.”

“Thank you, Mistress, I never walked so much in heels and they kept me on the run.” I touched the wall for balance as I slipped out of my heels.

“Very cute, Jenny,” said Marci. “That action is utterly feminine.”

I shook my head.

“You really need to be more sexy and seductive, Jenny. Amanda wrote me. She complimented me on beginning your feminisation, but said she expects me to fine tune your skills or she’ll hold me responsible. You’ve seen enough of my dual nature to realize that falling into her hands will not be entirely unpleasant for me, but if my training of you falls short of her expectations of me, I will take it out on you and so will Veronica. I think, if you disappoint us in this area, we would be disinclined to see you for some time.”

“I see. I shall try my best to please you both and Mistress Amanda at the same time.” Marci and Veronica had given me the two best nights of my life. If I had any chance of repeating such delights, I’d keep them happy.

Marci told me to lay out all my new feminine goodies. She and Veronica looked them over and discussed my “needs” — pleated skirt, red dress, formal gown, waist cincher (whatever that was), heels in matching colors.

I shook my head and sighed. Hadn’t any of them noticed I was good at fucking? Under Marci’s direction, I stored my finery in a linen closet and a chest of drawers in the hall near the washroom.

Back in their room, Veronica sat in one of the chairs, ostentatiously looking bored. She wore a pair of jeans and a tailored shirt.

“Veronica’s a man and you’re going to seduce him. I’ll coach you as needed.” Marci stood to one side.

This was probably Marci’s idea of being nice to me. For the next hour, I practiced lifting my skirt to adjust a garter while glancing at Veronica from under my lashes, standing with one leg thrust forward and the other turned sideways “to maximize the allure of your stockings and legs.” I presented my enhanced profile and threw back my shoulders. I crossed my legs, dangled a shoe.

Both Sisters professed to be disappointed in me. Veronica yawned at my efforts, Marci shook her head. “That’s enough for today, Jenny. I expect you to practice on your own in your room. We’ll make you into a foxy vixen yet.”

“I’m annoyed that a girl as pretty as you couldn’t arouse me,” added Veronica with a deep voice. “Bend over my lap.”

I draped myself across her as ordered. Veronica smacked me and Marci took a hand, too.

“You have too much protection,” said Veronica. “Take your skirt off.”

“Yes, and get the slapper and paddle from the toy drawer,” added Marci.

I preferred the spanking to feminisation training. I discarded the skirt and remembered to spread my legs and exaggerate my bend at the waist as I reached for the implements.

“All kidding aside, you do have good legs, Jenny dear,” said Veronica with an admiring glance.

“Thank you, Mistress.” On the whole, I agreed my legs looked surprisingly good. I felt glad despite myself. Imagine if I had lousy legs. I’d get punished for them all the time. I held out both implements.

Veronica selected the paddle, leaving the slapper for Marci. Veronica pointed to her lap, and I bent over again. The broad smash of the wooden paddle contrasted with the sharp thwack of the leather slapper, really heating me up.

Marci resumed feminisation training, much to my surprise and dismay. “A sissy girl like you should take a spanking a lot differently than a male sex servant. Kick those pretty legs to attract attention. Protest. Complain. Put on a real show, Jenny.”

Was there no end to it? “Ohhh! Ow! Oh, please, it hurts!” I kicked my legs like I was swimming.

“Wait! Time out,” called Marci. “That frantic kicking’s not convincing at all. Wait for the blow and react to it. Control your performance. Maybe decide whether to react with the leg on the side struck or the opposite side. You always react to a spank in some way or another. Now turn your reaction into a sexy kick. Don’t be afraid to lose your shoes as part of the act.”

I had to laugh. “Lessons in how to take a spanking! What next?”

They both laughed, then Veronica took over. “Quiet, you!” Smash.

“Oooh, Mistress, that hurt!” I kicked the same side leg, flexing my knee.

“Good, Jenny, that’s a nice, sexy, girly kick. Keep it up.” Marci emphasized her speech with a strong slapper blow. Thwack.

“Oh, Mistress Marci. My poor bum.”

“Let’s see how red you are,” came her only response. She tugged my panties down below my hips. “Not red enough. Good. Let’s keep going, Ronnie.” Thwap! Smash!

I squealed and kicked, feeling utterly foolish. Turned out to be quite a spanking. I was in real pain, mostly from the paddle, before long. My cheeks stung and my kicks weren’t entirely fake.

After a while, they each felt a cheek. “Nice and warm. Does it sting, Jenny?” Veronica asked sweetly.

If she could patronize me, I could be sarca...no, unwise. “Yes, it stings. Thank you, Mistresses.

Marci squeezed my rump and raked her nails over me.

“Ohhhh!”

“I love playing with freshly spanked bum!” she said, continuing. I squirmed over Veronica’s lap.

“Well, as usual, spanking made me horny,” announced Veronica. “Get up.”

I stood up and enjoyed the sights as they skimmed out of their jeans and panties. Naked from the waist down, they lay on the bed, Marci’s thigh resting on her lover’s.

“I’m sorry you didn’t get enough at Thanksgiving. Here are a couple of dishes you’ll like,” invited Veronica.

“Don’t forget to play with your food.” Marci wriggled her fingers suggestively.

Two beautiful, shaved pussies, Veronica’s with large, protruding inner lips glistening from arousal, Marci’s with thicker outer lips. What an aroma. The stinging buns, the beautiful, differing cunts, and my irrepressible hope for a fuck had me very hard indeed. I licked Veronica first while my fingers explored Marci’s moistening sex.

I decided to get a bit of my own back and to tease them. As Veronica’s moans deepened, I switched to Marci. Marci was less verbal but a few spasms told me it was time to go back to Veronica.

Their wordless moans complemented each other, so I glanced up. They kissed each other and Marci sought to undo Veronica’s blouse buttons. Those two together was such a beautiful sight. Made me drip precum. I switched back to Marci with my mouth.

The two pussies tasted different, but I won’t attempt to convey those essences. I loved licking from one to the other. I remembered what all these women kept stressing — that the best servants forgot about their own pleasure. Well, I tried my best to give them max pleasure, but it was so darn fun doing so! How could I ignore that? Why would I want to?

I switched partners again, by now with little reaction from the Sisters. Another glance showed that Marci had won her tussle with Veronica’s blouse and bra. She avidly suckled a nipple.

I gave up all attempts to ignore my own pleasure. I hoped I’d watch them lick each other and they’d let me fuck them again. That was the absolute best!

Marci propped up her upper body and tugged her top off, then embraced Veronica again. She pushed my lips away from Veronica. “Do you still need him?” she asked her partner.

My heart sank.

“No, love, I’ve got you, and that’s all I need. Jenny, you are dismissed. Put your uniform on and leave it Below Stairs at the end of your shift.”

Big sigh. “Yes, Mistress.” I didn’t even bother to remind Marci she’d promised to be extra nice to me. She’d insist she had been. I could hear her saying, “Well, you got to eat two pussies. What more do you want?”

I gathered my shoes and skirt, snapped my panties into place and wished them a wonderful time together. I wasn’t totally hypocritical.

I plodded back Below Stairs, looking pretty bedraggled, half dressed as I was.

Talissa lay back in one of easy chairs, eyes closed, masturbating. Probably remembering fucking Samantha, I figured. He heard me and opened his eyes.

“I’m supposed to stay dressed tonight,” I explained as I zipped up the skirt at the side. “Veronica and Marci trained me to act sexy, even to take a spanking like a sexy girl. That got them both horny and they had me licking them both. It was hot! I imagined all sorts of stuff to come, but all of a sudden, they decided they didn’t need a guy and they kicked me out.”

“You have been in for it today, maid Jenny. After I came downstairs, I got into laughing at you as the maid along with everyone else, but that seemed like good-natured fun compared to the deliberate cruelty of Sam and Veronica.

“Now, by our rules, I’m supposed to tell you what I did upstairs, but I bet you don’t need to know.”

“Thanks, Talissa. Let’s leave it that I don’t begrudge you a good time.” Halloween sure had cleared the air between us.

Throughout the rest of the evening, several sisters got me out from Below Stairs to serve them hot chocolate, or cheese and crackers. I knew they’d read Amanda’s report ‘cause most of them mentioned it. Amanda put the part about my good fucking skills at the beginning of the report, but no one alluded to that at all. Feminisation, feminisation, and more feminisation. Phooey on pheminisation, I want to phuck!

Thursday, my next shift, I arrived Below Stairs thankful no one told me to get dressed up. Nicola and Bethie were there, masturbating as usual. I joined them, fondling my tip to get started, glad as ever to be released. “Hi, you two. It’s nice to see you. Good Thanksgiving breaks?”

“Mine was OK,” said Bethie. “I was with relatives the whole time, but I like my relatives.”

“Mine was kinda boring, but it was better than being trained to be a girl,” teased Nicola.

I shook my head. “I hope they forget.”

“Fat chance.”

I picked up a magazine I’d not seen before. Inside were the usual leather-clad mistresses and cringing, submissive males. I read a story about an executive in an insurance company who got caught operating a hidden camera in the washroom. A junior exec and a secretary got good proof and blackmailed him into taking spankings on a regular basis. They quickly learned he liked the spankings, so they stopped and turned to cock and ball torture instead. That he didn’t like. They got pretty extreme - carpenter’s clamps, weights, heavy beatings. Dorothea was into that big time, I knew. I was afraid of her.

So guess who came in and wordlessly summoned me with a crooked finger? She carried a tablet computer and led me to one of the sitting areas in the living room. “Place a chair where you can look on with me.”

Dorothea looked as regal as ever, despite her casual dress of jeans and a form-fitting top. She wore spike-heeled boots, emphasizing her confident strides. Her direct gaze pinned my eyes. She turned her back to one of the more comfortable chairs and slowly lowered herself to sit, then opened the tablet with a flourish.

For the next 45 minutes, out of my sex service shift, she had me “assist” her in completing my feminine wardrobe. While I sat there, Nicola walked upstairs with Doris. Later, Bethie accompanied Teresa. I could have been eating pussy or even getting my ass plastered. Instead, I toadied to Dorothea. She suggested different articles of clothing, and I agreed. She chose colors and I agreed. Who was paying for all this crap? I gathered my nerve.

“Mistress Dorothea, am I expected to pay for all this? It’s close to $300 so far.”

“Oh, I was so eager to get on with the shopping that I forgot to explain it to you. These initial purchases come from our entertainment fund. You certainly are entertaining, Jenny, dear. You do have some expenses. You and all the servants already keep an ever-growing supply of panties so we don’t get bored with you. But as the maid, you’ll have an additional expense I’m sure you’ll take for the honor it is. You are to keep up a supply of various stockings and to replace your bras before they wear out. With care, Sandy at the lingerie shop will help you with choices and give you a special discount the others don’t get.”

“Thanks, I think,” I said.

Dorothea burst into laughter. “Oh, Jenny, you look so cute like that, all confused. You’re so easy. Maybe when we’re done here I’ll take you upstairs and toy with you.”

“I’m always ready to be taken,” I said.

As she finished the order, I again got up my nerve to ask a question. “Mistress Dorothea, am I expected to be dressed as a girl all the time now? Or when these clothes get here?”

“No, the only times you’ll be required to be girly is at official functions like the ceremony part of Halloween, and when one of the Sisters wants you that way. Marci loves to feminize, as you know, and there are some of us who like a chick with a dick. I know all you boys are pathetically eager to get laid. You’ll have a better chance with those girls.” She held up a hand, seeing that I was about to ask a question. “No, I’m not going to tell you their names. Perhaps they were only interested in the last maid. She was so popular we changed her name to Yvette to go with her French maid uniform. She wasn’t force femmed like you, she loved it and came here already a crossdresser.

“The next occasion you’ll be the maid is for the holiday party, just before the end of finals. It’s not as big a deal as the initiation or Halloween ‘cause some people are studying and others have left for home, but it’s fun and ends with playtime for all. You’ll be released from duties if anyone wants to use you that way.”

She looked at me speculatively. “I’ve hardly done anything with you since the second heat of the tryouts. You were good then, and now you have some real experience. I have some time. Upstairs with you!”

I followed her up. She wore jeans very tight on her buns. Dorothea’s room was on the third floor. Actually she occupied a suite of two rooms, one a bedroom. the other an office with a large filing cabinet. One wall of the bedroom supported a St. Andrew’s cross and a pegboard covered with restraints, clamps, and various spanking implements. “Wow, this is quite the room.”

“Presidential perks,” said Dorothea. “Lie down on your back on the bed. Good boy.” She sat on the bed and grasped my limp cock, squeezing it gently. “I remember you had good endurance and kept mostly erect during a hard spanking. I selected you for myself because of Amanda’s recommendation. I hurt you and teased you to the brink, didn’t I?”

“You sure did, Mistress Dorothea. Ill never forget it. I’d never had any sort of sexual experience, let alone all that stimulation. I was so excited! And when you showed me my very first pussy and I smelled it...I would have lost in another second. I’m glad I won.” Huh. That’s what I said, and I meant it, despite the cage, the frustration, the whipsaw of emotions.

Dorothea slowly stroked me as we talked. “I’m glad you were one of the winners, too. I haven’t indulged myself with you much, but since I’m to graduate in June, I intend to give you the benefit of my tender mercies between now and then.”

I gulped.

She laughed and reached for something from her bedside table. “You quake in fear of the agony, but I am confident that you’ll soon count the ecstasy worth the price. I’m going to toy with you, Jenny, on my scale light to low medium. I have no concern how you might evaluate my play; I will amuse myself with you as I like.”

The object she retrieved from the table proved to be a piece of string, red and about 1/8 inch diameter. As she spoke in her soft, menacing voice, she bound first my scrotum, then my cock near the base. She resumed stroking me, occasionally pinching my cockhead.

“I like to present my males with dilemmas and to give them some control over how I toy with them. I am going to hurt you quite a bit. I will also give you great pleasure if you submit willingly and completely. If you resist or attempt to cover yourself or flinch away so as to spoil my intent, I will bind you. From that moment on, you will experience no pleasure, I assure you, until you experience the pleasure of relief when I am no longer amused at toying with you.”

The string made my cock incredibly hard and sensitive. It seemed to grow in size as well. So far, despite her menacing words, Dorothea had greatly enhanced my pleasure.

“I prefer my toys to yield willingly, not knowing how I will play with them. However, you may, if you wish, now, and only now, request bondage so you cannot thwart my intent. If you choose bondage now, I shall inflict extra pain, but far short of what I will do if bondage becomes necessary later. If you do not choose bondage, I shall grant you more pleasure than pain. Which do you choose? I know it’s difficult for you boys to think clearly while under sexual stimulation, so I’ll withdraw while you decide. Bondage or freedom?” She let go of my cock.

My foremost thought was that I wanted her to resume stroking my cock! I weighed my tiny experience with cock and ball torture against Dorothea’s penchant and reputation for it. She said she’d be low on her scale, but what did that mean? What was her scale? In the end, I realized there was no way I’d give up a chance for more pleasure from her. “Freedom, please, Mistress Dorothea. And thank you, Mistress, for the free, informed choice.”

She resumed stroking, very slowly but with a tighter grip than she’d used before. “It’s all the same to me, but I am pleased when a first timer like you challenges me by choosing freedom. About 60% of first timers choose freedom. Of those, 55% end up in involuntary bondage. 100% of those choose to be bound at the beginning at all subsequent sessions. Where will you fall? Time will tell.”

I gulped.

Still stroking me, she opened a drawer in her bedside table and took out a cloth bag, placing it between us.

“I want precum from you, Jenny. Then I’ll move on.”

The bonds increased sensitivity by restricting fluid (Could I never turn of my inner scientist?), so it paradoxically made it harder to precum as pleasure increased. I kept trying, a sort of anti-Kegel. Finally, if felt the spreading fluid.

“Good boy, nice and aroused. How did you react when Amanda clamped your nipples and your perineum?”

“They hurt at first, mistress, and they were always distracting. They hurt like hell when they came off.”

“I see. Stroke yourself. Edge and let me know when you’re there.” She busied herself with several thin plastic clothespins from the bag.

I concentrated my efforts on my cockhead. “Edging, Mistress.”

“Good. Now use only your thumb and forefinger on your rim and your tip. Splay your other fingers out of my way.”

Frightened, I took a deep breath and obeyed.

Dorothea placed a pin where my cock met my balls, on center, right over my tube. “Don’t stop, more precum. Keep on edge.”

I gasped, nearly hyperventilating. Nowhere near the edge. I tried to calm down, to convert the pain to pleasure, squeezing my tip rapidly. “It’s hard, Mistress. I’m trying, truly I am!”

“Perhaps this will help,” she said in a falsely sweet voice as she placed another pin directly above the first.

“Yahhh!” Tears filled my eyes and I blinked them back. I spasmodically squeezed my tip so I’d remain obedient. I couldn’t imagine converting this unrelenting stinging into pleasure.

Dorothea used one hand to keep my dick upright so I couldn’t get a good look at the tight little pinchers. With a mocking smile, she added a third, then a fourth, immediately afterwards.

Moaning wordlessly, I rolled my head back and forth, desperately trying to dissipate that intolerable sting, but with little success. I kept spasmodically squeezing my cockhead, since she hadn’t told me to stop.

“Jenny, be quiet a moment and listen.”

I stopped moaning, but my breath was ragged. I stared at her, eyes wild.

“Jenny, I know all you boys like it when we stroke your eager, stiff cocks. So, I’m going to take over for you in a moment...with this.”

She held up an object I couldn’t understand. Wooden, it had an obvious handle. At the end were two curved projections. Opposite the one closer to the handle was a wing nut, evidently for adjustment. The inside of the curved pieces was lined with some fabric. Dorothea put lube on the fabric. “These are my Dickalipers, made by Althea to my design. Do you like?”

Speech came with difficulty. “Can’t tell. Must feel them first.”

“Oh, I see. Perhaps you’re right. Would you like me to use them on you?”

Grr. She was going to anyway. “Yes, Mistress, please use the...Dickalipers on me.”

“Ok, I’ll grant your request. Remove your hand from your cockhead.”

As soon as I let go, she placed a fifth pin right on my frenulum. “Yaaannnn!” I gasped, pounding my fists on the bed. My hips rose involuntarily, and I forced them to stop. Tears filled my eyes. Why couldn’t those things vary or move, anything but that steady grip, grip, grip!

I felt a soothing coolness on my dick. Glancing down, I saw she’d lubed me as well as her infernal Dickaliper, and now adjusted the device near the base of my cock. I felt new pressure, just above the red band that kept me inflated under this onslaught. I took a deep breath, as ready as possible for her to clamp me again.

Instead, she slid the Dickaliper up my shaft, all the way to the rim of my tip. It gripped nearly all the way around, leaving an open path to avoid the pins. Dorothea moved it back down, up, down. She jerked me off with this thing. I noticed the pressure as it slid, but it felt way more good than threatening. The entire experience, pins and stroking, felt...confusing.

Always with that slow cadence and modulated tone, Dorothea worked on me, sliding the device, captivating my eyes. “I’m told that the pressure of the Dickalipers is just a bit more than optimum for a hand. Do you agree?”

“Yes, Dorothea.”

Several strokes later came the next question. “I’m also told that the sensation of the Dickalipers, though tight, is more pleasurable than not. Do you agree?”

“Yes, Dorothea.”

“I see. I reward boys who like my torments. You may cum whenever you wish, Jenny.”

My eyes widened. A rare opportunity! I closed my eyes to better concentrate on the pleasurable aspects of this novel stimulation. I didn’t feel like cumming, though.

“Thank you for permission, Mistress”

“Would you like me to vary the cadence to help you cum, Jenny dear?”

“Perhaps faster, please?” I had no idea how to make myself cum this way.

“All right, Jenny.” Her hand rose and fell, usually with a tiny twist at the top, while the calipers measured my cockrim.

“Hmmmm, not even precum, Jenny. Usually, a technique like this works, doesn’t it Jenny?”

Through gritted teeth, “Yes, Mistress.”

“These Dickalipers are very versatile. If I tighten them a little bit more.. (She deftly adjusted the width.)... they can grip your rim and roll over you sensitive tip. Here’s a bit of lube to help you.” She flipped the tool over my expanded cockhead slowly, then a bit faster. “Does that feel good? Can it help you to cum?”

The sensation was marvelous but extremely frustrating. I wanted to cum, I needed to cum, but I couldn’t even give her some precum. Instead, a new ache manifested itself. “Blue balls, Mistress. All of a sudden.”

“What a shame. Your blue balls would be released if you came. You see, Jenny, I love cocks. I love hurting them and I love pleasuring them. I want you to cum for me, Jenny, to please me. You want to cum for me, don’t you?”

“Oh, yes, Mistress, yes! I’m desperate to cum, Mistress.”

“Then why don’t you, you ungrateful wretch?” she growled at me. She wrenched the Dickalipers from me and tossed it aside.

That hurt. I whimpered in fear.

“I’m going to punish this ungrateful, useless cock. Permission to cum is revoked.” Without warning, she ran a Wartenberg wheel over me. Then, as suddenly as it appeared the wheel was gone, replaced by her fingers, gently stroking the shaft. It strained to expand under her skillful fingers. Her voice returned to that maddening slow cadence. “Jenny, it was thoughtless and inconsiderate of me not to remember that a boy in your condition, cock and balls bound, with your little cum tube pinched can’t possibly cum. You went through all that effort for nothing! Poor Jenny.” She patted my face.

I didn’t trust myself to say anything. Uh, oh, that sardonic smile again.

“Jenny, I know something you don’t know.”

“What is that, Mistress?”

“You know how clothespins are constructed, don’t you?”

“Yes, Mistress.”

“With a hole that goes through the spring?”

“Yes, Mistress.”

“Well, there’s a fishing line through the pins on your cock.” She held up her hand, from which depended two strands of clear fishing line.

My eyes widened. I started to take a deep breath....

Mistress yanked the line hard.

I screamed as all the clothespins flew off me at the same instant. My body thrashed like I’d been electrocuted. My hands flew to my cock...I forced them away. My scream became gasps as I hyperventilated. The only mercy was the short time it took for renewed circulation to mostly relieve the pain. Before long, I merely panted, still recovering from that sharp pain. The most sensitive part of my shaft still felt very tender.

Dorothea watched me intently, licking her lips, an evil grin on her face. “You did so well, Jenny, allowing me access to your cock despite how I mistreated it. You almost forgot yourself and covered up at the end, didn’t you?”

I nodded.

“I bet that even now you would like to gently hold your sore little penis and comfort it, wouldn’t you?”

I nodded again, gasped, “Yes, Mistress Dorothea.”

“I think you would like it better if I comforted your penis, don’t you?”

I blanched. “I...I don’t know, Mistress.”

Dorothea looked surprised and puzzled. “Really? I thought all you boys dream each day of a Sister playing with your penises. Are you saying you don’t want me to play with your penis?”

“We do, or at least I sure do, but, forgive me for being so bold, Mistress Dorothea, but with you, I never know if it will be to make it feel good or to hurt it. I’m frightened.”

All questions fled from her face, replaced by a satisfied smile. “Ah. How nice. Jenny, remember who is to be pleased here. Now ask me nicely to play with your penis.”

I took a deep breath. “Mistress Dorothea, my penis is your toy and I beg you to amuse yourself with it as you see fit.”

She cocked one eyebrow at me. “Well, you know how to spread it on thick when you want to. Scoot down until your hips are at the foot of the bed.” She strode across the room and swung a light chair from in front of her make-up mirror to the foot of the bed. She paused, then sat as regally as she had downstairs.

“Just as I thought. The string kept you a bit stiff throughout the ordeal. I promised you if you declined bondage and never restricted my access, I’d grant you more pleasure than pain. Tell me your orgasm permission status.”

“You granted me permission to cum, for which I thank you, Mistress, but revoked the permission when I was unable to avail myself of the opportunity.”

Mistress looked at me with distaste, stood, and made elaborate brushing motions down her body, then swung her backhand away from herself. “I feel verbally slimed. Talk normally, or I’ll consider myself released from my promise!”

“Yes, Mistress.”

She sat back down and took my cock in her hand. She inspected the urethra. “Beautiful. Tiny bite marks remain from the teeth of the clothespins. Does it feel sore?”

“Yes, Mistress, it does.” I could not keep all the anxiety out of my voice. What was she up to?

“I think your cock would benefit from some soothing liquid. What do you think?”

“Depends on the liquid, I suppose, Mistress.” I eyed her warily.

“Perhaps some cool water, not too hot, not too cold. Hmmm, I’ve got it. Human saliva.” With that, she slowly licked the front of my shaft from ballsack to cockhead.

“Oh! Thank you, Mistress.” What a surprise.

She favored me with a big smile. “You did very well, though frightened, Jenny, and you deserve a reward. Besides, I like sucking cock. Lie back and relax.” She nibbled my cockhead.

“Thank you so much, Mistress. This feels wonderful.” She sucked in most of my shaft, her lips straining forward. Then she licked the shaft again, gave me a few strokes with her hand, massaging my cockhead with her thumb. My erection throbbed, stimulated by the restricted flow from the string. It felt huge to me.

“There, Jenny, does it feel better now?” It looks longer and thicker.”

“It feels quite a bit better, Mistress, thank you. May I possibly have more of the same treatment, please?”

“How predictable that you should ask.” With that, she nibbled my cockhead again.

Moans of pleasure filled the air. I lay back, transported. Dorothea held my shaft between her thumb and forefinger, sliding them up and down again and again. She used enough pressure that it felt like a barely tight clamp constricting the sides, an altogether delightful sensation. When she got to the top of one stroke, she withdrew her lips and held my tip between the same digits. Without changing expression, she pinched my cockhead cruelly, digging her nails in.

“Aaaahhhhuhhhh,” I gasped.

“Always, a bit of pain to keep you guessing, sweet Jenny.” With that, she took my cockhead back in her mouth. A few seconds later, she slowly eased more and more of my shaft into her mouth.

I propped myself on my elbows the better to enjoy the view.

Dorothea sped up, taking in most of my shaft, bobbing her head up and down like pornstars I’d seen. I loved it! Brought me right to the edge. I sighed and moaned, muttering, “Thank you, Mistress,” from time to time.

She caught my eye and raised her eyebrows, then took my entire length inside her. She kept it down, massaging my tip with her throat. Wow, that felt good! I saw tears fill her eyes before she raised her had.

“Oh, Mistress, how wonderful. You’re so good to me!”

“Always?” She continued stroking me.

I laughed. “When you’re good to me, you’re very, very good, but when you’re bad, you’re horrid.”

She laughed. “Horrid, am I? Take that.” She slapped my cock several times, giving me sharp, brief pain with each strike while my shaft went to and fro. “Some men like to degrade their sex partners by smacking their cocks on their faces or parts of their bodies. I love to reverse this by slapping my boys dicks around. How do you like it?”

“To be honest, Mistress, I kinda do like it. It doesn’t hurt all that much and it looks kinda neat waving around like a tree in the wind.” I laughed.

Dorothea giggled, of all things for a Mistress to do. “You like it! Goody!” So of course, she started slapping it harder and faster. “Still like it?”

“Well, it doesn’t hurt that much, Mistress, but eventually I’ll lose my erection if you keep it up like this, string or no string.”

She actually stopped, totally to my surprise. “Well, I don’t want that, not yet.” She licked it up and down again, then took it back in her mouth and sucked the head, then most of the shaft, bobbing her head again.

Oh, that felt good. I hoped she’d deep throat me again and she didn’t disappoint me. She gobbled me right up and did that gulping massage thing that felt soooo good. Her gleaming eyes caught mine — she wanted to see how good she made me feel. Not the usual thing from the Sisters.

She let me go and caught her breath, grinning. “Like that, Jenny?” She stroked by cock with a light grip and a slow cadence.

“Oh, Mistress, I love it. Thank you so much.”

“You have a nice, responsive cock, Jenny. It’s fun to play with. I will mount you and engulf you one day, but not yet. You’ll earn that pleasure by accepting more pain.” She held my scrotum in one hand, moving her fingers to stir my balls. “You have blue balls, correct?”

“Yes, mistress, kinda minimally blue, a dull ache.”

“Tied and blue testicles, my favorite.” She closed her hand on them without exerting pressure. Nevertheless, I felt nervous.

Dorothea got a faraway look in her eye. “All girls are trained to kick a guy in the balls if he gets too frisky, so we learn early that they’re vulnerable. But I remember when I realized how much guys care about their balls. My first real boyfriend was late, didn’t call, and told me it wasn’t his fault and that I shouldn’t make a big deal of it. Pissed me off.

“I was a virgin in those days, and I’d never been naked with Jimmy, my boyfriend. But I’d just read about a girl who spanked her boyfriend, and that sounded very exciting. So I told Jimmy he’d either let me spank him for his rudeness or I’d break up with him. I don’t know what he was going to say, but when I added, ‘A bare-assed spanking to make sure you’re properly embarrassed,’ he got this gleam in his eye and agreed right away. Any idea what he was thinking, Jenny?”

I laughed. “He hoped the sight of him naked would get you so hot, you’d both lose your virginities. He’s just like any of the rest of us — a spanking or worse is worth it if we get laid in the end.”

“Well, you’re right, of course. I saw right through that, but he stripped and bent over my lap. I noticed he had a big stiffie. He couldn’t take that much pain (All of you guys took way more even in the application ordeal.) before he started squirming, kicking, and trying to protect himself with his hands.

“I felt his hardon bouncing against me and I realized he might cum on me. So I hooked his ballsack between my fingers, two on each side, like this.” My scrotum lay on her palm, with two fingers curled around it on either side where it met my stiff cock.

I gulped. Throughout this reminiscence, she kept on stroking my cock. Felt wonderful, had me dripping precum, going on and off the edge, yet with a simmering fear of what she’d do to my tender blue balls.

“As soon as I held his balls, Jimmy stopped moving completely. 'Please, Dot, don’t do that, you can hurt me a lot there. Please let go.’ Wow! I’d never heard a boy beg before, but I loved it. Made me wet in a way his naked body didn’t.

“I told him that it made him hold still, so I’d keep possession of the balls (He was a football quarterback.) until I he fulfilled his penalty. After that, he kept absolutely still. I spanked him until he was red and warm and I was hot and dripping, but I didn’t let on. I had him get dressed, much to his dismay, told him he was forgiven, and we went on like nothing happened. I spanked him several more times, always holding his balls. We were each other’s first fucks, couple of teenagers fumbling around and finally getting it right. Eventually, his arrogance got to be too much for me and I dumped him. I never did bust his balls, though. I should have; would’ve done us both good.”

She gazed at me with a tender smile. “You know how this delightful session will end, don’t you, Jenny?”

I gulped. “Yes, Mistress, I’m afraid I do.”

“Good, but first more pleasure for us both.”

Ah, she nibbled my cockhead again. I’d be a fool not to enjoy this, I told myself. I closed my eyes and lay back, the better to appreciate the sensations. Warm lips, an agile tongue, smooth fingers sliding up to meet descending lips, head bobbing, varying pace, capped by a long deep throating! Oh, I loved it! She still held my balls, so the pleasure came with a background of fear, but it felt so good!

She teared up and gagged, so she came up for air, smiling, blinking, breathing.

“Oh, Mistress, this is sooo nice of you! Thank you so much!”

“Are your balls more blue after that treatment?”

“Oh, yes, Mistress, yes they are. Touchy testicles, just as you like.”

She smiled and bent down to resume sucking my cock. More of that marvelous... My eyes flew open as pressure came on my balls — not pain, just pressure. Oh, I felt scared for a moment. Mistress Dorothea resumed pleasuring me, toying with me, as she put it.

She kept going like that, head bobbing, tip-licking, shaft-engulfing but every few seconds, pressure on my shrinking balls. Felt wonderful, yet with an increasing backdrop of fear. Mistress kept the pressure light, never painful, yet I knew I’d never be allowed release. I edged several times, grunting with the effort to accept the pleasure while avoiding the peak I desired so much.

Mistress again took my full length into her mouth, working her throat on my cockhead, then squeezing my balls again. What a mix of feelings!

Gasping, she released me and grinned. “Feel good, Jenny?” Ropes of my precum joined my cock and her lips.

“Good and scared, Mistress.”

“I haven’t hurt your balls since I took hold of them, have I?”

“Not yet, Mistress, but I’m very aware of my fate.”

She tousled my hair. “My sweet boy.” As before, she stroked me continually. Precum flowed copiously and my balls ached. “Jenny, when I resume sucking your cock, I promise that I won’t crush your nuts for several squeezes. I want you to concentrate on the sensation without fear and tell me how it feels. Do you trust me?”

“Of course I trust you, Mistress.”

“Good.’ With a smile, she once again took my cockhead between her lips. Soon, her head resumed that up and down motion I loved. That’s when she put on the pressure on.

I took a deep breath and tried to relax. The pressure was gentle; she’d already squeezed harder. Another breath. “Mistress, I must say that this pressure feels good if I’m not terrified.”

“Good, Jenny.” She closed the trap a bit more. “Still good?” She mumbled a bit over my cock.

More deep breathing. “Still good, Mistress. I’m very surprised.” I relaxed and enjoyed the tight sensation surrounding my aching jewels. She slowly tightened her grip while her lips went up and down my shaft. “I’m at the edge of pain, Mistress.”

She nodded without pausing her cocksucking. She went on to deep throat me once again.

Incredible sensations. Edging for pain and edging for pleasure at the same time. “Uh, uh, uh! Hard not to cum, Mistress!” Desperate, I bore down as hard as I could to avoid disobedience.

“Gluh!” gasped Mistress, once again blinking rapidly. She favored me with a very fond look and stroked my cheek. “I’m very proud of you, Jenny. You know what’s coming and I want you to hold your body as still as possible when it happens. Will you do that for me?”

High pitched, I replied, “Yes, Mistress, whatever you wish.”

“Good boy.”

I lay back, taking deep breaths to relax. It’s inevitable, I told myself. Accept it. Enjoy the blowjob. I did, too, with her varied techniques and the gentle pressure on my ballsack. The pressure increased. I took a deep breath. She relented. Again and again, head down, tight squeeze, head up, release. After a while, she again took my entire length. Deep tip massage, squeeze, release, squeeze, release, finally a tight squeeze!

“Ahhhh!!!!!” I bellowed as loud as I ever had. Legs flailed, fists pounded. My body convulsed, yet I managed to keep toward her instead of rolling away to curl up as I wished. My head thrashed. Still she kept sucking my cock! She shifted her head...

“AaaaaaHHHHHH! I screamed again, this time rolling to one side, crashing to the floor. She’d bit they length of my cock as she crushed my poor balls a second time. I curled up, clutching myself, sobbing and moaning, tears flowing freely. I don’t know how long I remained like that, curled up, sobbing and crying. It seemed like a long time. Finally, the intolerable pain eased a bit. I lay there, waiting for it to subside more, weeping. I realized Dorothea was gently stroking my head.

“Ah, Jenny, you did so well. I love getting in a second squeeze! You all scream so much more after the second one.” She kissed the nape of my neck. She actually lay down behind me, spooning. “I love giving ball pain to boys. Very few rebel. Most respond with increased docility and devotion. I hope you’ll be like that, Jenny.” She kept petting me. Her arm over my waist went nowhere near my cock and balls.

My breathing returned to normal, albeit slowly. The acute pain merged slowly with the dull ache of the blue balls, though amplified. My poor balls had been attacked both within and without, so to speak. The shaft pain from Mistress’s teeth subsided relatively fast.

“When you’re ready to sit up, I’ll get you some water.”

“Oh, Mistress, I know I’m supposed to be grateful for anything you give me and I am very grateful for so much of what you did, but it’s very hard to be honest and grateful for the very end of otherwise fantastic oral sex from you.”

She laughed gently. “Yes, and you’re also required to be honest. You said that quite well. In a few days, I’ll ask you how you feel about this time together.”

“Thank you, Mistress. I...I think I’m ready to sit up, now, Mistress.”

“OK. Don’t get up yet until I return with the water. You might need support.”

A few moments later, with Mistress’s arm around my waist, she guided me to the chair she’d used. Once seated, I eagerly drank from the bottle she offered me. Fear and pain make you thirsty. I noticed Mistress was naked from the waist down. Her slit, topped by a Mohawk of hair, glistened and some dry fluid remained on her thighs.

She saw my gaze and chose to explain. “I told you I like sucking cock, Jenny, and busting your cute little balls twice made me so horny, but it was your screams and involuntary twitches, curling up and rolling about that sent my hand into my panties. I had a big, gushing cum while you moaned. After that, there was no sense keeping my pants on. I’m not done, either. I need to cum more after such a hot session.” She sat on the bed so our positions were reversed. “Oh, wait, you like big breasts, don’t you?”

“Yes, Mistress, I do.”

She whisked off her top and the sports bra beneath. Dorothea’s breasts, full with large, dark aureola, jiggled a bit as she wriggled her shoulders. “Worthy of worship, are they not?” She stood, placing them more in my reach.

“Oh, yes, Mistress, yes; thank you for the privilege of worship.” I stood and lifted the orbs. Heavy and soft, they felt marvelous. I raised and lowered them alternately, earning a smile from Dorothea. My thumbs over her nipples produced nearly instantaneous erections. I sucked first one, then the other.

Dorothea moaned. Pussysmell wafted up.

I slipped one, then two, wriggling fingers inside her.

Dorothea moaned and pressed my head to her breast, hips thrusting. She ground her clit area against the heel of my hand. “Ahhhh, yes! Wonderful.” She tousled my hair. “A nice cum for me. That’s enough breast worship for now.” She lay back down, legs spread, pointing to her pussy.

I resumed my seat and scooted the chair forward. I didn’t waste time with foreplay. I palmed the insides of her thighs as I noticed her prominent inner pussylips. I twisted my head and sucked one between my lips, massaging it. I rolled my lips over my teeth and pulled her wet lip outward until it slipped from my grip.

I shifted my attention to her clit, licking it with my tongue tip as I slipped my two fingers into her damp warmth.

She rewarded my efforts by cumming nearly instantly. I kept on, since my technique clearly pleased my Mistress. She came nearly continuously, crying out, “Oh, yes, yes,” pausing to gather breath, then doing it again.

My fingers went as fast as they could, and I sucked the clit between my teeth so it lay fully open to my darting tongue.

That did it. Dorothea screamed wordlessly and pulled my head into her pussy. She held me there, hands laced in my hair, pushing my head toward her then away, back and forth. Then, with a final, “Ahhhh,” she flung my head away from her and lay there, panting for a few moments, eyes closed.

To my surprise, given what I’d been through, I had a throbbing boner, complete with very tender, aching balls. I slowly pumped it, as usual paying attention to the tip.

Dorothea’s eyes fluttered open. She smiled at me and took a deep breath. “A wonderful session, Jenny. I promised you pain, but more pleasure. Would you agree I accomplished that?”

“On balance, yes, Mistress, but the pain sure was extreme — and the build-up frightening.”

“Well. then, I succeeded perfectly,” she said smugly. “Stand up,” she commanded. “Beautiful,” she said, eyeing my stiffie. “You return all that pain with desire. I’ll take over.” Mistress stroked me once m ore, using a tighter grip and faster pace than I had. Right away, I leaked precum and edged.

“Edging, Mistress, thank you.”

“Good. Remain there.”

Her next speech, punctuated by my usual guttural sounds of effort not to cum, both terrified and reassured me.

“Jenny, I insist any male who finishes a private session with me leave my presence limp, whether from cumming or pain or exhaustion. This is difficult with such a nice, persistently erect penis as yours, but I will not be thwarted. I feel you have endured enough testicle pain, so I will reduce your erection by other means.” With that, she painfully twisted my cock, even bending like a grotesque shepherd's crook.

I grunted and moaned, but at least I wasn’t screaming and rolling all over the floor. Sure enough, my dick withered.

Dorothea looked on with approval. “Good. This was very enjoyable, Jenny, and I will use you like this again in the near future. But for now, replace my chair and go Below Stairs. Begin restoring your boner now. I spent longer with you than I anticipated and I need to study.”

“Thank you, Mistress, for using me as your toy. It truly was way more fun than not, despite the double ball busting. Also, you showed me that testicle pressure up to the point of pain is pleasurable. Thank you again.” I replaced her chair. Obediently playing with my tip, I went downstairs.
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