Sissy and the Sex Ed Class Pt. 03

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A shy co-ed uses a nancy boy to pop her cherry.
3.1k words
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Part 2 of the 3 part series

Updated 10/28/2023
Created 10/23/2023
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I hope you find this story amusing. Comments are welcome. All the characters are of legal age.

As told in parts 1 and 2, I have been working with Miss Doreen who is a teaching assistant at Whitehurst College for Female Domination. She and her professor, Dr. Madden, tested me and decided that I was a suitable sissy to service co-eds in their sexual education courses. Miss Doreen introduced me to Miss Melanie, a shy virgin freshman. Miss Doreen showed Miss Melanie how to manipulate my hands and fingers to masturbate herself. Now the stage was set for the final act.

I dreamt about Miss Melanie the night after she used me to jill off. In the erotic vision she was dressed in thong panties and a pushup bra that showcased her wonderful figure. The dream segued to a wedding ceremony where I wore a traditional bridal gown lavished with Duchesse lace and a long veil. When I awoke in a sweat from the splendid fantasy my pink negligee was wet with cum.

Miss Doreen texted me the next day with instructions to meet her and Miss Melanie in Room 23 at the Sex Ed building. She added that Miss Melanie wanted me in a mini dress and purple undies.

I wore a leopard print bodycon dress with a Hanky Panky purple garter belt and matching tanga panties. The ladies had not yet arrived when I got there at one o'clock, but the door was ajar so I went inside. I was shocked to see restraints on the bed. While I was very fond of Miss Melanie I was not so fond on bondage.

I sat on a love seat nervously waiting for what seemed like an eternity until the lovely women arrived. They were buoyant and laughing when they entered the room. The pair had probably enjoyed cocktails with their lunches.

"Well, Timmy" said Miss Doreen chuckling "Are you ready?"

That was rather abrupt and insensitive, I thought.

"Don't I get hugs first?" I asked plaintively.

"Of course you do sweetie" said Miss Doreen with a grin. She looked elegant in a lavender mock neck maxi dress. Miss Doreen walked to where I was now standing, embraced me and pecked my cheek. Then Miss Melanie did the same but kissed me on the mouth. She wore a lovely mauve ruffle-sleeve blouse and a short black skirt.

"I love your dress, Timmy" said Miss Melanie "Thanks for wearing a mini for me, darling. I'm looking forward to playing with you." She gently held both of my hands and gazed warmly into my eyes. My heart melted.

"I'm looking forward to being played with, Miss Melanie, but am I going to be restrained?" I asked nervously.

Miss Doreen responded to the question "Yes, Timmy. Melanie thinks that she might be ready to go all the way. However, she's still a little anxious about it. So I suggested that we tie you down. You won't mind will you, honey boy?"

The question was rhetorical because Miss Doreen immediately led me to the bed, pushed me down and bound my hands and feet.

Miss Melanie disrobed without any reticence. She had obviously overcome her earlier shyness. Her Adore Me lingerie set was gorgeous. The Brazilian style panties had a vivid flower motif on each side of the pink crotch panel. A coordinating balconette bra repeated the floral design and its adjustable pink straps matched the panty.

My weenie stirred in my tanga panties when she beamed a sexy smile my way.

Miss Melanie needed no prompting from Miss Doreen. She lifted my skirt, pulled down my purple knickers and straddled me. After examining my little weenie she easily slid the narrow rod into her warm moist pussy. The long awaited deed was done.

"That was easy, Doreen" said Miss Melanie happily "and it didn't hurt a bit!"

"Now use him, Melanie" said Miss Doreen "Remember what I said about wrapping your thumb and index finger around his cock and squeezing so he can't cum."

Miss Melanie clamped my weenie and then used my dick like a warm fleshy dildo. She bobbed up and down on top of me and soon climaxed euphorically.

"Great job, Melanie!" shouted Miss Doreen.

"I did it, Doreen! I did it!" yelled Miss Melanie.

"You certainly did, Melanie! You popped your cherry and orgasmed too! How about we go back to the bar and celebrate?"

"I'm all in, girl!" replied Miss Melanie joyously.

Miss Doreen hugged me and praised me for being a good girl. Miss Melanie embraced me and kissed me after she dressed. Then she whispered "I'll phone you, sweetheart."

I was glad that Miss Melanie would call me. My immediate problem though was the raging boner under my skirt. I managed to contain myself until the ladies went out the door. Then it erupted leaving a big gooey mess on my leopard print skirt.

Miss Melanie called the following day.

"Timmy, dear" she said "would you like to get together with me right now?"

"Oh yes!" I answered "shall we meet at the Lab?"

"No, sweetheart" she said "Doreen has given me permission to see you in my dorm suite. Can you come over right away?"

"May I please have time to shower and dress prettily for you, Miss Melanie?" I asked.

"Okay, but be here in thirty minutes. Otherwise I'm going to lock you out and jill off by myself" she teased.

I hurriedly showered with a stiffy between my legs and girlish feelings overwhelming me. Then I slipped into crotchless pantyhose, G-string panties and a lacy bralette. I wore a provocative red satin mini skirt and a sheer white blouse. My black bralette showed through the thin top invitingly.

When Miss Melanie opened the door to her dorm suite she was totally naked. I almost fainted!

"Come in, my sweet sissy boy!" she said in a sultry voice.

I relished the vision of her bare body and said "Thank you for inviting me, Miss Melanie. I'm so happy to be together with you again!"

"Shut up and come with me, Timmy!" she hissed like a cat "We're going to the bedroom right now and I don't have much time."

Miss Melanie shared the suite with two other female students. Their bedroom doors were open and I saw one girl face sitting a pansy in bridal lingerie. The other co-ed was on top of a young man in a pink camisole and she was energetically screwing him. The two women were so focused on their sexual pursuits that they didn't even notice us.

Miss Melanie ran me down the hall toward her room so fast that I tripped in my high heels and landed on the floor. So, she dragged me the rest of the way and pushed me down on the sheets. Next she sprawled on top of me, lifted my red mini skirt and pulled aside my G-string panties. She looked hungrily at my little dickie for a moment and then impaled herself. She remembered Miss Doreen's advice and clamped her thumb and forefinger around my rod to prevent me from cumming and pleasured herself.

I was so glad that Miss Melanie had learned to control my penis. I was in sissy love with her and cared only for her satisfaction. Miss Melanie fucked me until she climaxed and then immediately hopped off.

"That was fun, sweetie" she said "but you must leave now. I've got an exam in my Seducing and Controlling Your Boss course.

I was sad that Miss Melanie would fuck me and make me leave right away. My sissy emotions engulfed me and I began crying into my embroidered hanky.

"Could we possibly spend some more time together, Miss Melanie" I sobbed "Maybe we could meet after your exam?"

She looked at me pityingly and said "I'm sorry Timmy but I'm going to be busy the next couple of days. I'll call you when I have more time." Then she gave me a peck on the cheek and hustled me out the door.

I was alone in my apartment moping that evening. I wondered whether Miss Melanie was just another in a long line of women who have used me as a sex toy. My misery ended abruptly when she called.

"I'm sorry I rushed you out this afternoon, honey boy" she said "I was frazzled because of the exam. Why don't you come over now and bring a tooth brush."

"Thank you, Miss Melanie! Thank you!" I gushed.

I was in sissy heaven as I dressed in my favorite peignoir set and a packed a few cosmetics in an overnight bag. Sissies in lingerie are a common sight on the Whitehurst College campus. So I felt perfectly normal sashaying to the dormitory.

Miss Melanie answered the door wearing a rather sexless linen kaftan.

"I asked you here to keep me company, Timmy" she explained with a smile "I'm not in the mood for screwing right now."

"Oh, Miss Melanie" I replied with a light heart "I am so happy that I'm more than just a sex toy for you!"

"I am using you for sex, Timmy. Let's be clear about that, but I'm beginning to like you as a person too."

Then she changed the subject. "There are some cold cuts and wine in the frig, Timmy. Make me a plate and pour me a glass of white."

"Yes, Miss Melanie!" I said enthusiastically.

I arranged slices of ham and roast beef along with some crackers and cheese on a dish. Then I poured the wine and served Miss Melanie on the sofa in the common room. I sat on the floor at her feet. She nibbled at the snack but drained the wine quickly.

Just then the roommate who had been face sitting her sissy earlier entered the suite. She smiled knowingly and chortled "Is that little twit your dip stick, Melanie?"

"Go fuck yourself, Susan" said Miss Melanie "Timmy is my friend!" I was elated that Miss Melanie would defend my honor and refer to me as a friend. Susan stuck out her tongue but went quietly to her room.

"More wine, Timmy" said Miss Melanie handing me the glass before I could thank her.

In the kitchen I fantasized about serving Miss Melanie wine and cheese in my French maid outfit. The black satin dress has a three layer tulle petticoat. I have lacy anklets and patent leather femboy shoes to go with it.

When my attention returned to the task at hand I filled the glass. Then I took the wine to Miss Melanie who was just finishing a phone call.

"Guess who that was, Timmy" she said.

"Was it Miss Doreen?" I asked.

"Yes, it was. And when I told her you were just visiting she told me to quit wasting time. She said I should practice on you even if I'm not horny. I don't know how I feel about that. What about you, sweetheart?"

"I'll do whatever you want, Miss Melanie" I responded "but what I like most is making you happy."

Miss Melanie accepted the wine glass still thinking about what Miss Doreen had said. I took my place on the carpet by her legs.

She leisurely enjoyed her second drink. Then she sent me back to the kitchen for a third glass.

When I returned she drained the glass at once.

Then in a honeyed voice she said "Come up here and sit next to me, darling."

Melanie gently pushed me backwards on the sofa, smiled mischievously and put her hand inside my peignoir robe. Her gentle fingers found my breast and tenderly massaged it as she kissed me.

"Maybe it's the wine, sweetie, but I'm horny for you now" she said with a tender smile "Let's go to bed so you can make me happy."

Miss Melanie spent a good long time screwing me. She climaxed five times while keeping a tight grip on my dick.

"If I let go, Timmy, can you control yourself?"

"Yes, Miss Melanie" I said "I'll do anything for you."

"Good girl" she said "I want to keep you inside me but my hand is getting tired."

Miss Melanie released my dick and we soon fell asleep with her still on top of me. Then, in the early morning hours she nudged me awake.

"I want to feel jizz inside me, Timmy" she whispered.

My dick had become limp and fallen out of her pussy during the night. When she frenched me and fondled my breasts my little weenie quickly hardened again.

She slid the stiff rod back inside her and pumped me until I spewed a massive load of cum into her pussy. I shouted joyously.

"Wow, Timmy, that was amazing!" she said with passion.

We fell blissfully asleep again until late in the morning. Miss Melanie was holding me in her arms when I awoke and we spooned in bed until almost noon. I fixed a big breakfast with bacon, eggs, sausage, toast and coffee for her.

"Aren't you eating?" she asked me.

"No, Miss Melanie" I answered "I'm dieting."

"Alright, Timmy. Why don't you run along then and I'll call you later."

After returning to my apartment, I showered and changed into a knee length floral skirt and off-white blouse. While applying my daytime makeup I enjoyed wonderful memories of the previous night.

My happy mood came to an abrupt end though when my phone chimed.

"I'm afraid we're in trouble, Timmy" said Miss Melanie. "Susan heard you shout when you climaxed last night and she reported us. We have to meet with professor Madden at two o'clock today. Come to the courtyard of the Sex Ed building at a quarter to two and I'll fill you in."

I did not understand why we were in trouble but I knew that I must look my best for Miss Melanie and the professor. I decide to keep the skirt and blouse that I was already wearing because it was a conservative ensemble but I wanted an innocent face.

I browsed L'Oreal and Maybelline makeup ideas online until I found a soft look that I liked. I had the foundation, concealer and blush that I needed and applied them carefully. The visage looking back from the mirror was as delicate as a flower.

Miss Melanie was wearing a chic business suit with pencil trousers and stiletto heels when we met in the courtyard. I knew she would impress Dr. Madden. She embraced me and we sat side by side on a patio bench.

"Darling" she said sorrowfully "I made a mistake when I let you climax last night. Sissies are not allowed to cum anywhere on the college grounds and there are serious consequences for both of us."

I did not want any harm to come to Miss Melanie and I started crying. She put an arm around my shoulders and blotted my tears with a tissue from her purse. We sat together with our soft hands intertwined until Miss Melanie received a text telling her to proceed to Dr. Madden's office.

The imposing woman was sitting behind a large black desk. Miss Doreen was there too, seated in an arm chair. There were also two female security guards standing by. I started sobbing again.

"Melanie, will you please stop that sissy from blubbering!" demanded Dr. Madden.

I made an extra effort to stop crying and held my lace hanky to my eyes. Then Miss Melanie and I sat in straight back chairs in front of the professor's big desk.

"Let's get straight to the point of his meeting, Melanie" said the professor "It has been reported to me that this sissy climaxed in your bed last night. As you know, there is a strict rule against sissy orgasms on campus. So, what do you have to say for yourself?"

"I'm sorry, professor Madden" she pleaded "but I got excited and wanted to feel his jizz inside me. I promise it won't happen again."

"That's a pitiful excuse, Melanie, and I do not accept it. The punishment is a year of chastity for you and expulsion of your sissy from our program. You're dismissed."

One security guard led Miss Melanie away to be put in chastity. The other wrenched my arm behind my back, marched me to the campus gates and hurled me into the street.

I was completely distraught and worried sick about Miss Melanie. She finally phoned two days later.

"Miss Doreen interceded for us, Timmy" she said with a glimmer of hope in her voice. "Professor Madden will release me from chastity but only on one condition. You have to become my sissy bride and promise to love, honor and obey me. I know it's a lot to ask but would you do that for me, sweetie pie?"

"Oh yes, Miss Melanie!" I squealed "I can't imagine anything more wonderful!"

The wedding took place on a Saturday in the college chapel with most of the faculty and student body in attendance. I wore an eyelet lace bridal gown complete with a blue garter lent to me by Miss Doreen. A lesbian minister read the vows and I fervently promised my obedience and love to Miss Melanie.

Sissy wedding receptions at Whitehurst College include a pegging of the bride ceremony. Miss Melanie would do the honors with help from Miss Doreen and two bridesmaids appointed by professor Madden.

Miss Doreen positioned me with my tush toward the guests. Then the bridesmaids lifted my skirt and petticoats while Miss Melanie removed my bridal panties. The two maids continued holding up my dress and pettis to show my bare bottom. There was plenty of giggling and laughter from the attendees.

Next, Miss Doreen parted my legs and attached a wide spreader bar between my ankles. Then she bent me forward at my waist. Finally, Miss Melanie lubed my opening and consummated our marriage with a pink strap-on. Everyone in the audience cheered.

The wedding photographer asked Miss Melanie to continue pumping me while she recorded video from every angle. Then the guests were invited to file past us at the altar and take snapshots with their smart phones. I smiled for all the picture takers.

When it was all over Miss Melanie and I had a lovely honeymoon at a cottage in the Poconos. She enjoyed my nancy boy bedroom services as much as I liked giving them. Now that we were married I was even allowed to climax when Miss Melanie gave permission.

After the honeymoon we moved to an off-campus apartment where I embarked on my wifely duties. I wear my frilly French maid uniform every morning to perform my household chores. Then I change to a playful party dress in the afternoon when Miss Melanie returns from her classes. We're in love and my sissy heart is happier than I had ever imagined!

The End

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Whippet_DarlingWhippet_Darling5 months agoAuthor

Dear SissyBoy1Warszawa,

Thanks for your appreciation of my story. Part 3 is the end of this story but I will continue writing about other sisses like Timmy.

Sincererly,

Whippet_Darling

SissyBoy1WarszawaSissyBoy1Warszawa5 months ago

@Whippet_Darling I can't find words to express my thanks and admiration for the wonderful and beautiful story of Sissy Timm, full of interesting action and sexy events. I really like the training of sissy Timm, the beautiful wedding of Melania with sissy Timm (I would like to undergo such training and experience the wedding with my mistress). It's a pity that you don't write further fate of Timmo and his Mistress Melania, introducing further sexual training of both the Sissy and his Mistress, and maybe also introducing the participation of Miss Doreen and other people. Maybe you will decide to add more stories about Sissy Timmy. 📖🧒🏻‍♀️👧🏻👰🏻♂️🤵🏻♀️❤️👨🏻‍🎓⚧️👩🏻.

ps. Sorry for any mistakes and linguistic inaccuracies, but I don't speak English.

SissyBoy from Warsaw, Poland. 📖👩🏻‍🦳♀️❤️🧒🏻⚧️👧🏻.

📖👩🏻‍🦳♀️❤️🧒🏻⚧️👧🏻📖❤️

@Whippet_Darling nie umiem znaleźć słów aby wyrazić swoje podziękowania i wyrazy podziwu za wspaniałe i piękne, pełne interesujących akcji i seksownych zdarzeń historię Maminsynka Timma. Bardzo podoba Mi się szkolenie maminsynka Timma, piękny ślub Melanii z maminsynkiem Timmem (sam/a bym chciała przejść takie szkolenie i przeżyć ślub ze swoją Panią). Szkoda że nie piszesz dalszych losów Timma i jego Pani Melanii wprowadzając dalsze szkolenie seksualne zarówno Maminsynka i jego Pani, a może jeszcze wprowadzając udziału Panny Doreen i innych osób. Może jednak zdecydujesz się na dopisanie następnych losów Maminsynka Timma. 📖🧒🏻‍♀️👧🏻👰🏻♂️🤵🏻♀️❤️👨🏻‍🎓⚧️👩🏻.

ps. Przepraszam za błędy i niedokładności językowe ale nie znam języka angielskiego.

SissyBoy z Warszawy, Polska. 📖👩🏻‍🦳♀️❤️🧒🏻⚧️👧🏻.

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