Sissy and the Dean

Prissy was in the college library preparing for a Womens Literature exam when an unexpected text message arrived.

"Ms. Prissy - Please come to my office at 2 pm today. Dean Laddimore."

The sissy had once met the Dean of Women Students. Laddimore was a statuesque lady with raven black hair who wore skirted business suits. Dean had summoned Prissy to her office when she learned that he had chosen to major in Womens Studies. She was suspicious that he was a pervert seeking easy access to co-eds. When Prissy arrived in a Lolita outfit complete with sun bonnet and frilly parasol she understood that he was no threat to the female students.

Still in the library Prissy indulged in delightful fantasies. Perhaps the Dean will spank me for breaking a college rule, he mused. I must wear my prettiest petticoats and silkiest nylon panties in case she takes me over her knee.

Prissy returned to his dorm room to get ready for the appointment. He removed the lilac sundress he had worn to the library along with the matching hair ribbon, his sheer-to-the-waist pantyhose and his lacy bra. Then he wrapped himself in a towel and headed to the womens lavatory for a shower. There Prissy shampooed his hair, shaved his legs and underarms, and scrubbed himself all over with a floral scented body wash.

Upon returning to his room Prissy found Colleen waiting for him. She was a very attractive senior woman who agreed to have a sissy roommate provided that he was caged for chastity.

"I heard that you have an appointment with the Dean, Prissy."

"How did you know that?" asked a very puzzled Prissy.

"A little birdie told me" she replied. "I just thought you might like some help with your clothes and makeup."

"Oh, I would, Colleen!" squealed the sissy. "Thank you!"

"Fine. Have you decided what to wear?"

Prissy explained to Colleen that he hoped that Dean would spank him. So he intended to wear his prettiest undies -- pink and white petticoats and his embroidered nylon panties.

"They're bridal white briefs with lace trim around the leg holes, a pretty daisy on the tummy panel and a sweet little bow on the elastic waistband" he gushed.

"That sounds fine, Prissy. Although I don't think Dean plans to spank you, at least not today."

Colleen towel dried and brushed out Prissy's blonde hair while they discussed which dress, hosiery and heels he would wear. The sissy felt deliciously girlie being groomed by Colleen and discussing feminine attire.

Prissy was unable to decide what to wear apart from his frilly undies. So, Colleen instructed him to put on the panties while she looked through his closet for a lovely dress.

Collen settled on a mid-thigh chiffon party frock in chartreuse with a white organza overlay on the bodice and sleeves. The skirt featured chantilly lace on the hemline. She held the dress in front of Prissy who was now in his embroidered panties. When Colleen told Prissy how lovely he would look for Dean Laddimore the sissy leaked cum into the nylon briefs.

"Do you need a corset for this dress, Prissy?" asked Colleen.

"Yes, I need a tight one. It's a size small."

Colleen selected an overbust foundation garment in ivory with six garter straps. Then she noticed the damp spot on Prissy's panties and pointed it out to him. He was deeply embarrassed and blushed sheepishly.

"You've been a naughty girl, Prissy. We don't have time for punishment though. So, we'll just have to put you in period panties."

Prissy was so disappointed about soiling his favorite knickers that tears welled up in his blue eyes. He sorted through his lingerie drawer and chose a pair of yellow plastic panties with elastic bands on the legs to prevent leaks. Colleen handed him a maxi-pad which he inserted in the undies before he slid them up his legs.

The sissy was now ready to be laced into his corset. So Prissy sucked in his tummy and held onto the lacing bar while Colleen tightened the garment firmly around his already small waist. When she fed the garter straps under the sissy's panties he leaked jiz onto his sanitary pad. The very aroused ninny beamed a bright smile at Colleen. She was smiling too and responded with a little kiss on his cheek.

Prissy put on his petticoats, the pink one over the white. Then he and Colleen admired his girlish figure in their full length mirror. The corset defined his bust and waist nicely and the dainty petticoats flared at his hips. Sissy's implants nicely overflowed the corset cups, too. He looked forward to giving Dean Laddimore a glimpse of his ivory white breasts.

"Let's get you into your party dress now, Prissy" said Colleen.

She slipped the frock over sissy's head and zipped it up. Prissy's boobs held up the strapless dress. Then Colleen wrapped the white lace-trimmed ribbon belt around sissy's waist and tied a large bow in the back. The pretty dress was snug over Prissy's corseted figure. Seamed nylon stockings, chartreuse high heels with white ribbon bows along with a large hair bow completed sissy's look. He felt wonderfully feminine when he twirled in front of the mirror. Colleen applauded.

Then Colleen said "We have more than enough time for your makeup. In the meanwhile, would you like to thank me for helping you get ready?"

"Yes, please Colleen! I'd love to show my appreciation."

Prissy was well versed in this drill. He untied and removed Colleen's trainers, unzipped her butt shaping blue jeans and helped her out of them. Then he removed the cute striped knit jersey over her head. Finally he took off her underwire bra and cotton panties. The gusset was already damp.

Colleen sat on the bed with her legs spread wide apart in happy anticipation. Prissy knelt before her. The sissy had become an expert at servicing Colleen's wonderful pussy. She had taught him the 'ear signals' that many women now used with their boyfriends. A clockwise twist of the right ear meant 'lick faster' while a reverse twist meant to slow down. The left ear was used to indicate harder or softer pressure.

Today Collen started Prissy with slow and gentle licking while gradually increasing the sissy's tempo and pressure. Soon she was panting loudly and forcing Prissy's face deeper into her crotch. Her body began to quiver all over before a powerful orgasm swept over her. After the climax Colleen kept sissy's head firmly between her thighs. Prissy knew that she wanted more so he continued ministering to Colleen's pussy and she came two more times.

Prissy licked all the juice from Colleen's thighs, her labia and her vagina. She relaxed while the sissy cleaned her. Then he helped her dress.

Time had flown by while Colleen and Prissy were making love and now it was nearly time for his appointment with the Dean.

"Let's hurry, Prissy" said Colleen. "We still have to do your makeup."

"Would you please do it, Colleen?" Prissy pleaded. "You're so much better than me."

Colleen agreed and began with foundation and then blush. She lined sissy's eyes with a pencil and then applied a sparkly bronze eyeshadow. She colored his lips coral and added a glossy overcoat. Prissy was delighted with his girlishly feminine face.

Colleen was pleased with her work, too. She placed her hands on Prissy's corseted waist and squeezed him gently. His sanitary pad received another squirt of juice. The sissy was glad that he had changed into plastic panties. Then Colleen patted Prissy's derriere and sent him on his way to meet with the Dean.

---

The Dean's office was across campus in the administration building. Her secretary, Fiona, informed the sissy that Dean would see him shortly and asked Prissy to sit. He smoothed his short skirt and petticoats and then sat. Fiona glanced up hoping for a beaver shot but Prissy was coyly sitting cross-legged. When Fiona's phone buzzed Prissy heard Dean Laddimore instruct her to send him in.

Dean welcomed Prissy with a warm handshake. She complimented him on his pretty dress and offered him a seat in front of her desk. After a little chit-chat she came to reason for their meeting.

"Prissy, you probably know that some of the female students give sexaul favors to the male faculty members. I don't mind that as long as the student is not taking a class from the professor."

"However, I believe that women like myself deserve equal treatment. I don't expect red-blooded young men to service a middle aged lady when they can pursue sexy co-eds their own age. So, I've asked some of the girls who are rooming with sissies, like your Colleen, for recommendations. She tells me that your cunnilingus skills are excellent."

Prissy was shocked that Colleen had revealed their intimacy to the Dean and his face grew red.

"I hope that I haven't upset you, Prissy" offered the Dean.

Prissy took a moment to compose himself before he responded.

"I'm sorry, Dean Laddimore, but I wasn't expecting that. Just to be clear, are you suggesting that I could be your sissy lover?"

"Yes, Prissy." Then she smiled and said "Let's sit together and talk about it."

Dean took the sissy's hand and led him to a love set in the corner of her office. Prissy was excited to sit next to this important woman.

She told the sissy that she loved his eye shadow and his floral scent. Then she leaned over and french kissed him while running both hands gently through his long hair. Prissy became aroused and his cum moistened the pad in his plastic panties again.

Soon Dean's hands traveled from his hair to his breasts. Prissy had never had been fondled by a woman and he began to fidget nervously. Dean sensed his discomfort and moved her hands from his titties to his slender waist. She caressed him tenderly and resumed kissing his lips.

The sissy was amazed at how this strong woman could also be such a sensitive lover. Prissy's anxiety passed and when Dean's hand returned to his breasts a second time he quietly surrendered to her. Soon he was feeling deliciously weak and vulnerable, and he began moaning softly.

Dean understood that the sissy had relaxed. So, she placed a palm gently on Prissy's knee and waited for a reaction. When he nodded his assent Dean slid her warm hand up his nylon hosiery. She found the garter clip at the top of the stocking. Then she played with the elastic strap attached to his corset which made the sissy giggle.

Now with her hand at sissy's crotch Dean encountered his plastic panties. Her middle finger explored inside a leg opening and she discovered his damp sanitary pad. Finally, she felt his chastity device and she fingered the lock.

"This stays in place today, Prissy, but someday it might come off when I'm in the mood."

Prissy's penis had only been inside silicone vaginas. So, the thought of a genuine woman riding him with her real pussy was beyond his wildest fantasies. He gasped and began to sob tears of job. Dean dried the sissy's eyes with a tissue and nestled his face into her soft bosom until he regained his composure.

Then she dismissed him. "On your way out" said the Dean "ask Fiona to set up a dinner date for us at the Hide-Away restaurant."

---

Colleen was with her boyfriend on the evening of Prissy's dinner with Dean Laddimore. However, she had laid out a red micro dress for him to wear along with padded panties and a pushup bra. Prissy donned the sexy attire and waited for Dean to escort him to dinner.

Dean had hired a limo for the evening and the chauffeur drove them to the Hide-Away. During the long drive Dean frenched him and felt him up and down. Prissy was ready for the Dean's assertiveness this time and warmed to her advances.

"I'll give whatever you want tonight, Dean" he whispered in her ear.

"That's a good girl, Prissy" she responded. "This will be a lovely evening for both of us, my dear."

The hostess at the restaurant ushered them into a dimly lit private room. When the waitress arrived Dean ordered for both of them -- a 12 ounce steak for herself and a garden salad for Prissy. They ate in silence while exchanging amorous glances. The Dean occasionally held the sissy's hand to reassure him. When they had finished and the waitress returned to collect their plates Dean asked her to lock the door.

Their private room had a small bar next to a sofa. Dean led Prissy to the bar and poured herself two fingers of single malt scotch. She offered the sissy a tonic water which he gratefully accepted. Then she took him to the sofa and sat back with her drink. Prissy knelt before her.

The Dean parted her legs and Prissy gasped at the glorious sight before his eyes. Dean Laddimore was wearing a black lace Chantelle garterbelt. The eight straps held up exclusive Chervin nylon stockings from Paris. The sissy had only dreamed of owning such glamorous lingerie himself. Now he was a witness to these sensuous feminine garments adorning the most beautiful pussy he had even beheld. The Dean's public hairs were professionally styled, her labia were flawless and they framed a succulent erect clitoris waiting to be licked.

From his kneeling position Prissy gazed upward at Dean. He batted his fake eyelashes hoping for permission to begin servicing her. She nodded her consent and added "I don't use ear signals with experienced sissies. You should know what to do."

Prissy applied his tongue lovingly to Dean's coochie and started licking. He began slowly, then adjusted his speed and intensity according to her breathing. Dean soon began panting and she pressed his face more deeply into her pussy. As he accelerated the rhythm and pressure she began scratching his neck and back with her sharp nails. Then she screamed and climaxed squirting pussy juice onto his face.

The Dean and the sissy rested for a while, she on the sofa and he still on his knees. Then she spoke momentus words.

"I said that you might someday be freed from chastity in order to satisfy me. It seems that the time has come."

Dean motioned for Prissy to join her on the sofa and she extracted a miniature key from her bra. She lifted his tiny skirt, pulled down the pretty panties and unlocked sissy's cage. Then she straddled him and stroked her pussy with the tip of his stiff rod. Dean squeezed tightly on the base of his dick so the sissy would not ejaculate too soon. Then she fucked him for over an hour climaxing multiple times. Finally, she released her grip on his cock and Prissy rocketed a huge load of cum into her hungry snatch.

After he recovered his breath sissy cleaned the Dean's thighs and pussy and swallowed the pungent juices. Dean locked his chastity and then summoned the chauffeur. He drove them back to campus with Prissy and the Dean embracing tenderly in the back seat.