The Repressed Librarian

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A Spinster in Training...
9.5k words
4.5
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Part 1 of the 3 part series

Updated 06/07/2023
Created 06/26/2015
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It was the late afternoon on an October Sunday. Bill was naked- lying on his rumpled bed. It would be his turn to shower away the remnants of his 'afternoon delight' in a few minutes. They hadn't had full sex yet; he was making his virgin girlfriend, Sally, wait another week. Bill smiled as he lay in bed and thought about her. He could hear the water running in the shower and could visualize her naked as the water ran over her sensuous body. His cock stiffened from the image but his mind quickly flashed back to late August when he'd first met her.

He was a 24 year old grad student and she a 21 year old college senior at the same large University. As a frequent visitor to the University library all summer he knew the fall term would bring a large contingent of new part time staff. It would facilitate his research if he got friendly with one or more of the newbies so he needed to make an effort to check them out.

On the first day of the term he'd noticed Sally as one of the numerous new young assistant librarians. In fact, he'd done more than notice her. He'd done a double take and mentally chuckled to himself that she looked like a 'spinster in training.'

Her skirt had been long and loose-ending just above the ankle. Above the waist she wore a shapeless sweater over a white blouse. As she moved about Bill did his best to assess her upper body. While the sweater was baggy it would hug her body a bit as she reached for the higher shelves. Bill concluded that she was reasonably fit but had the chest of a boy. Since he was a tit man this revelation was disappointing but didn't really matter as he couldn't imagine she held any potential as a girlfriend. She wore no make-up and her face was dominated by black framed eyeglasses. Her brunette hair was worn in a bun at the back of her head. All in all she personified the image of plain. She was the classic librarian- quiet, efficient and up tight as she diligently pushed a cart full of books around and re-shelved them in their coded spaces. Looks aside, she might be helpful with his research requests since she seemed to take her job so seriously. On the other hand, any fantasy he'd had of combining work and romance wasn't going to work with her. He'd keep looking for another librarian.

In the library about a week later Bill needed some help from the research desk. He found the next available assistant to be the new young woman he'd silently dissected and discarded from a distance. He felt guilty about his mental cruelty but as he stood just a few feet away his earlier assessment still seemed essentially accurate. Her name tag identified her as "Sally M". Up close, if one could ignore her ugly glasses, it was possible to see that her face was attractive but her overall appearance remained staid and non-sexual. He asked for her assistance and over the next few minutes found that she was a senior with her major in his field of study, history. Even though her interest was ancient history and his was centuries later he found she was quite facile in discussing potential research sources. She was easy to talk to and turned out to be very helpful in his research within the first thirty minutes- saving him half a day.

A few hours later as Bill left the library Sally was leaving at the same time. He held the door for her and they descended the stairs next to each other- both turning toward the right at the foot of the stairs and walking in the same direction. Bill felt he should say something before the woman thought he was stalking her. "Thanks for your help earlier. I'm headed to the café for coffee. Would you like to join me?"

Sally accepted his invitation saying that was also her destination. He introduced himself again and they made small talk as they walked the few hundred feet to the coffee shop. Their time together as they drank their coffee went quickly as they spoke of her courses and his two research projects.

On Bill's next visit to the library Sally assisted him with his research again and they agreed to meet and go for lunch later. As they walked and sat across from each other Bill studied Sally's face, body and movements. Her glasses were so prominent that he wondered why a young girl would have selected them. Contact lenses would change her face completely. Even if she couldn't wear contacts some frameless or light colored frames would give her face a much more attractive look. He imagined signing her up for a make-over and how she might look at the 'reveal'.

Visualizing her with no glasses, flowing hair and bold make up Bill felt like a pervert but he couldn't help but visualize her naked. Her flat chest was a negative but otherwise his mind imagined a fit and potentially sexy woman. His mind even flew off in an amusing fantasy- when he was wealthy he could buy her big breast implants and they'd live happily ever after. He knew this was sexist and crude but he still found it amusing. If she could read his mind she'd undoubtedly slap him and storm off. In fact, given her sexless appearance she'd probably call the campus police and report that he assaulted her.

Bill's fantasy ended and he dealt with reality. Sally was a very intelligent, pleasant young woman. He could enjoy a woman's friendship without sex- especially if she was of great value in his library work.

Each of them enjoyed their time together and as they parted agreed they'd like to have lunch again. No specifics were set since they knew they'd be seeing each other at the library. During the following week they seemed to bump into each other on campus and at the library almostgs but their schedules never synced up for lunch. every day. They shared coffee on two morninings.

The next week was a carbon copy of the first with lots of brief meetings- all of them pleasant. After several such chance encounters Bill asked Sally out to a casual supper on the upcoming Friday. He knew she worked at the library until 6 PM and offered to pick her up there.

In accepting his invitation Sally inquired where they'd be going. Bill was surprised at the question but said he thought they'd go to a small bistro he liked in the city about twenty minutes away. Sally said that sounded great and felt she needed to add, "I'm sorry about asking; it's just that I dress a little differently on campus and nearby. I'll explain on Friday." She asked that he give her 45 minutes to go home to change after work and then gave him her address so he could pick her up there. She explained that she rented an apartment in a female-only dorm style apartment house. Men weren't allowed past the lobby so he should simply wait in his car and she'd come out to him. He described his car and they were all set.

On Friday Bill arrived at her address and idled at the curb. Within a few minutes Sally was sliding into the passenger seat. Bill's eyes immediately noticed that Sally was wearing a skirt that ended above her knee. It wasn't short but it was noticeably different from those he'd seen her wear at the library. Her calves looked nice and he noted she was wearing sexy three inch heels- not the shoes he would have expected.

As Bill raised his face to greet her he was dumbstruck by Sally's chest. She was wearing a tailored shirt which revealed a distinct bust she'd never shown before. He instantly concluded that she must be wearing a heavily padded bra. He didn't know whether to be pleased by her effort to dress up for him or saddened by her feeling that she needed to pad her chest. As their eyes met an instant later Bill realized that Sally wasn't wearing glasses and had her hair down. Her face and hair were beautiful but he stumbled at complimenting her- afraid it would sound like a criticism of her normal look.

Sally sensed Bill was uncomfortable and salvaged the moment by lightly saying, "I guess I look a quite different than usual. I can explain that."

"Wow," was Bill's stupid sounding but sincere response. "You look great."

Sally said, "Thanks. There's a simple explanation. Well, simple is probably not the right word. Psychologically, there's a complex- probably weird explanation but I like to describe it as simple."

Bill kept his eyes on her- trying to stay focused on her face and not drop his eyes to her chest. She continued, "In high school when I developed a woman's body there were several boys who harassed me- nothing physical- just crude teasing that I couldn't handle.

"It was a very tough time for me. I was on the school swim team. After having two good seasons my times went up even though I was training hard. My coach essentially told me my breasts had gotten too big and I'd never be a great swimmer. Then she told me the principal wanted me off the team because my nipples were too obvious in my suit. The coach suggested we could pad the suit but she made it clear my times weren't going to be helped and all but asked me to quit which I did. Anyway, one of the junior guys overheard all of that. He told his friends and the guys all started making snide breast and nipple comments whenever they saw me.

"I begged my parents to let me transfer to the local Catholic school. After lots of tears and family drama they agreed. When I started at the new school I wore a spandex tube over my breasts rather than a bra, wore only loose tops, got big ugly glasses and kept my hair in a pony-tail. My boy problems disappeared. When I went to college I did the same thing and I've kept my image the same for four years at the library and around the campus and town."

Bill hesitated and then haltingly replied, "I don't know what to say. I'm sorry you had a problem and I guess I should say I'm happy you solved it but hiding your beauty for so long is...a little sad. I'm at a loss to know what I should say. Telling you I'd like you to look sexy would be selfish on my part but hiding yourself needs to stop sometime."

"I know. I know. You'll be pleased to learn that tonight is the first date I've had in years for which I tried to look nice. From our numerous encounters I concluded that you were not creepy and were someone that should see the real me."

"Not creepy," questioned Bill lightly. "Wow, I guess I should be proud. Is there any particular behavior I should avoid to stay off the creepy list? I'm sorry, I shouldn't have said that. Seriously, you're a beautiful woman. I'm sorry you've felt you needed to hide."

"I'm sorry, too. Let's go to dinner. I'll try not to act neurotic." She then joked, "But please understand if some guy makes a remark about my breasts or something I might go off on them."

Bill nodded and smiled. Internally he was torn between being thrilled that Sally looked so great and fearing she was a mental basket case. He could sympathize with her past bad experience but couldn't understand her multi-year reaction. As a guy he knew that he was probably being insensitive. He'd seen his share of crime shows on TV in which the raped woman is mentally devastated and the men are clueless. Still, Sally said the guys in high school hadn't touched her; they'd merely teased her verbally. She was certainly a bit overly sensitive- or crazy. Sooner or later he was bound to say the wrong thing. He wondered if there was any hope of a normal sex life with Sally or would she cut off his balls if he tried to fondle her tits. His dilemma was funny to a point but far from it if she really was crazy.

They arrived at the bistro and ordered drinks at the bar. Standing next to Sally gave Bill his first full view of her body and overall appearance. She was even more attractive then he'd thought in the confines of the car. Even though her top was not tight Bill could see the outline of very nice breasts. He guessed she was a "C" cup and marveled at how she'd looked so flat chested in all of their previous encounters.

Without the big black eye glasses and with the addition of some make-up her face was close to beautiful. The pale lipstick she wore highlighted a very sensuous mouth that had previously been unremarkable. Her flowing hair was below shoulder length and looked incredibly soft and silky. He tried not to stare at her body but made numerous subtle tours up and down her 5' 6" frame. She had a great body and what looked like very nice legs. The skirt was still a little long for a full assessment but her legs from her feet to past her knees certainly looked good.

Bill felt he should complement Sally on how great she looked but remained nervous. He still didn't know how to handle her very fragile mind. He wondered whether he might have a future with her or would he find her too psychotic. After a slight hesitation he said, "I trust it isn't creepy to tell you how great you look. It's hard to believe you could transform yourself so much."

"Don't be afraid; I wanted to look nice for you. I know my past behavior was an over-reaction. You probably think I'm a real loon. Actually, for the past several years to some degree my lifestyle was laziness. It was easier to continue as the dull librarian than it was to fend off guys."

After a second round of drinks the couple moved to a table for dinner. Sitting across from her Bill enjoyed Sally's beauty and continued to wonder how she could have lived for several years in denial of her looks. He assumed she had contact lenses in place of her missing eye glasses and was shocked to learn the glasses were simple glass- they weren't corrective lenses. She admitted that she just wore them to discourage male attention. She volunteered that she still routinely wore a constrictive sleeve over her breasts under her loose tops. She confessed that the sleeve was uncomfortable but something she'd gotten used to.

Bill did a lot of nodding but avoided saying very much. He feared any comment about her breasts might be humorous or playfully suggestive to him but 'creepy' to her. The fact that Sally had nice breasts but had hidden them for years was definitely odd to the extreme. Every girl he'd ever dated was either proud of her tits or had whined that she wished they were bigger. He couldn't imagine a girl having a nice rack like Sally's and deliberately compressing it.

Bill wondered if he'd ever get to see Sally's tits and play with them. Would she ever wear a tight top or perhaps wear a tee with no bra? Her past behavior made her forbidden tits all the more appealing. They were now a challenge; the mountaintop that lures the climbers. Sally was about 21 or 22; he might be the first person to see her tits and if he was lucky, the first guy to enjoy them with his hands and mouth. That thought was exciting.

Sally continued to explain her admittedly unusual behavior and concluded by saying she expected to continue her bland look through graduation; after four years looking as she did she'd be too embarrassed to change all of a sudden. After graduation she'd dress as a normal woman. In fact, she boasted she'd already gone on a job interview as herself. Bill felt relieved. It seemed that maybe Sally wasn't crazy.

Bill commented that it was great that Sally seemed ready to 'come out' as the beautiful woman she was. He added that he felt very lucky to be one of the first to be with the real Sally.

"Not one of the first; the first and only." Sally added that she trusted that Bill would keep her secret since on campus she would continue to dress as the bland librarian. Bill nodded his agreement but suggested that she consider gradually loosening up. Perhaps she might give up her glasses and tell anyone that asked that she had surgery or got contacts.

Sally smiled and said that was a possibility. "You really don't like my glasses, do you?"

Bill admitted that they definitely hid her beauty. "It might be shallow of me but you really are two different people with and without the glasses."

Sally smiled saying that was the idea; she'd picked the boldest glasses she could find and thought of them as a 'man repellant'.

A friend of Bill's stopped at the table which interrupted their conversation. He sat down and had a drink while they ate their dinner- thus relieving Bill from the pressure of the couple's awkward conversation. They enjoyed the rest of the evening which included a romantic walk through a park near the bistro.

At the front door of her apartment house Bill hugged Sally and kissed her goodnight with some passion which she seemed to share. Bill walked back to his car feeling there might be a future with Sally but still intimidated by her apparent fear of men.

On Monday Bill noted that Sally's librarian look was back including her glasses. When they met for lunch that day Bill observed, "I hoped you were going to lose the glasses after having imaginary eye surgery. I guess you weren't ready."

"I am. In fact I asked my boss for Wednesday and Thursday off so I could have my eyes done. It was hugely embarrassing when she questioned having them both done at the same time and I had to ad lib that only one needs correction."

Bill smiled and questioned, "Which one?"

"My left, if you must know."

"Well, that's what happens when you lie. You have to make up more lies."

Sally continued, "I told my boss I had met a guy who hated my glasses and insisted that I have surgery even though I was scared to death. She told me I should dump him if he was so controlling."

"He sounds like a real bastard. Did you tell her that he also loves natural breasts- neither enhanced nor shrink wrapped- just natural?"

"No. I don't discuss my breasts with my boss or co-workers. No one but you has any idea that I have breasts. I did tell her that I liked dating a guy who was dominant and in control."

"Well, I for one am very glad you were honest with me- and I'm glad you have breasts. You really should loosen up sexually. I know that sounds very self-serving but I think it's also what's good for you."

Sally smiled and said that she wasn't as sexually repressed as he thought. After checking around to confirm they had privacy she said, "Since I'm being open with you I should probably mention that under my plain clothes I usually wear a sexy thong or bikini panties. I've always done that as my secret sexual gesture but now I'll do it as a tease for you. You'll be the only one in the library that knows what's under my long granny skirt. Today it's a blue silk thong."

Bill gave her a wide-eyed stare. With her librarian look he'd not suspected she might wear sexy lingerie and was certainly surprised that she felt comfortable enough with him to mention it.

"Okay. Now I'm totally at a loss to know what to say. How am I supposed to avoid being thought of as creepy when you tell me about your sexy panties?"

"You're right. I'm giving you mixed messages. In a nutshell, the real me has a strong sexual side. I'm inexperienced but think about sex quite a bit. For the past several years I've hidden that to the outside world. I like you and trust you. I'm thinking I'd like to experiment sexually with you if you don't mind my inexperience. I don't know where to start and would love to just put my sexual future in your hands."

Bill said, "Okay. As a horny guy I'd love to take you up on that but with the reaction you had to past creepy behavior I have to worry that you might change your mind and... well, either go to the cops or cut off my balls or something. You can understand that, right?"

"Yes, I've frightened you with my past over-reaction to some crude teenagers. I've matured. Would it help if I assured you that for the past couple of years I've just been lazy. I haven't been afraid." Sally leaned forward and reached across the small table placing her hand gently on Bill's. In a low voice she said, "In fact, I fantasize a lot about sex with men- over the past month with you in particular. When I've masturbated thinking about you I've never taken a knife to your balls or even threatened them."

Bill smiled at her seductive statement replying, "That's a good start. This is going to sound weird but let's just take it slow. Let's put any sex off for a while."

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