Maggie and the Headmaster

Maggie loved her work as School Secretary which gave her a first floor apartment above a wing of the private girls boarding school set in parkland in Surrey. The head was a married man who lived across the park with his wife. They had no children and he had been appointed when the previous head had been reported as a missing person. She had developed depression and appeared to have taken her own life as the police had never been able to trace her through phone record, bank account or passport use or other inquiries.

Roger the head teacher had daily contact with her of course and as the school year progressed Maggie came to like him. She had no contact with his wife who worked full time and did not join in school life.

Maggie enjoyed being single and in her twenties. The teaching staff were predominantly female or married couples who were House Heads. The system worked well, the school was popular and rated outstanding.

Maggie felt settled if a little remote from the rest of the world. She was well paid and had an annual salary increase. She lived rent free but had to pay utility bills which were modest as the school had solar panels, was well insulated and had a biomass unit which heated the main building.

Maggie had been driving an old car but the school offered her use of an electric school vehicle and charge point so she scrapped her old car and signed up for the school vehicle. She shopped as part of the teacher pool purchase scheme. Life was simple routine and comfortable.

Maggie had been in a relationship with another student at University and was no longer a virgin. She had an IUD but in the months at the school it had not seen use.

Maggie masturbated frequently and enjoyed romance and erotic stories. Her TV viewing also triggered fantasies. She loved to play for at least an hour before bedtime and enjoyed rubbing lubrication around her clit and bringing herself to clitoral orgasms before drifting off to sleep.

The school was so popular with many overseas students from wealthy families and Embassies preferring to educate at a single sex school which was safe for their daughters and had high percentage of top UK university entrants. It was partnered with a number of organisations which were centres of excellence for students pursuing careers in various professions.

One day the head had finished their session and dictated letters to Maggie when for the first time he expressed an interest in her complimenting her on her hair.

Maggie was a red head. She wore large glasses for work, was freckled but plain and dressed in a business suit. She was very efficient and she liked to appear professional. She also felt horny when he spoke to her about non school things. She asked "Do you like red hair? A lot of people don't it seems."

"I find it very attractive and like your long hair."

Maggie thought he was flirting so she she tried "I have quite long hair in winter but prefer to remove it in summer!"

It was outrageous but he enjoyed the thought and behind his desk his cock stiffened. "So its Easter soon are you long or short?"

Maggie laughed "Neatly trimmed and about to be waxed."

She was wet and warm now and a little surprised he was having this conversation. "When did you first feel attracted to redheads?"

"I was a teenager and in a swimming pool at University. I looked up and could see ginger pubic hair either side of her swimsuit crotch."

"I swim here with the female teaching group. I always trim before swimming otherwise my bush shows like that. I enjoy the women only sessions although some of the lesbian teachers have hit on me. Friendly but obviously interested. I'm 100% man focused."

"Maggie I have an Easter Conference to attend and it would be useful to have a p.a. with me to help set up the school presentation to side meetings. Would you like to come; own room staying in a country hotel wing of a village gastro pub?"

Maggie had planned a solo weekend break but nothing was fixed. She could help him and do her own tour around if he dropped her in the city. She agreed and he made the booking using the school credit card to pay for 2 rooms.

Maggie felt very horny as she returned to work in her personal office.

She asked in the staff room about his wife. No one knew her but she was a busy hospital consultant. She lived on site but no one knew any more than that and they lived very privately. This was the case with several staff on site; only Heads of School Houses with pastoral care as couples were known to all. The teaching staff were ethnically diverse as were the students. The Physical Education department teachers were all lesbians and had discreet relationships onsite and with other partners. They were sportswomen of distinction and the school had among the student body elite students who played at national level. The school had a tradition of coaches in various sports fulfilling these teaching posts and attracted students pursuing sporting careers. It was a sporting centre of excellence and partnered with a range of sports facilities.

Roger went home that evening with a hope that his flirting might develop. He and his wife had not had sex for years. The marriage was convenient to his career and she would say the same. She was always tired after work and liked to relax and sleep. They had agreed that either of them could seek sex with others before they came to the school. They rarely entertained although she supported him at one or two school events and their social media accounts reflected each other's personal achievements. Roger had been helped by being married to an eminent consultant with a strong medical research background. His previous headship had also been helped by his wife's appearance on TV and radio to discuss her research.

Roger masturbated dreaming of his young red headed secretary that evening. He was excited by her long red hair and the prospect of kissing and licking a young vagina. She might want him to have sex with her. He would set up a holiday venue for her; then he could visit her for sex.

The couple set off in his car to travel by motorway to the conference at a Midlands venue. Roger was driving with an aching hard on. Maggie had spent time on her mobile phone. She had noticed the bulge and had wondered how big he was. She was wet wearing slacks and a thong. Although she was plain and had no bust to attract him she knew her red head excited him.

"So Roger what are the plans on arrival?"

"Oh relaxing and dining I booked a table in the restaurant."

"Sounds good. I looked at the menu."

"Tomorrow is the conference registration. No need to attend the main conference but in the evening I have a presentation to give to the smaller venue; you would be an enormous help with that."

"I think you look as though you could do with a hand right now."

She reached over and slid a hand inside and felt a rigid sticky shaft. She wanted to let him know she was looking for sex with him.

He had to concentrate hard on driving whilst Maggie explored inside his clothing. He suggested a toilet stop at the next service area.

"Roger I like what I'm holding. When we get settled in the hotel will you want me to do anything with this?"

"I would love you to sleep with me tonight."

"OK no problem; perhaps you could brush my hair and undress me?" Maggie needed sex to calm her growing excitement."

They sat in the car again after the stop. He had used the rapid charge parking bay whilst they had a break and checked their phones.

"Maggie I must ask do you have a hairy bush?"

"No very smooth after waxing for summer. I do have a strip of hair above, thought you might like that."

"It won't take long to reach our hotel now"

"It felt like you might need something when we arrive!"

"Oh if you could help with that aching years long frustration in some way!" He wanted to allow the young woman to relax and feel comfortable before he did anything to her."

Maggie wondered what to call his erect shaft. She had grown up calling it willy but had always wondered with her boyfriend whether to call it dick, prick or cock. He had referred to his cock so cock it was to be. She had grown up calling it her vag and she wondered how a headteacher would call it. The staff room used cunt when the need arose and many of the students referred to their cunts. Maggie felt comfortable with the word but would Roger say that?

They arrived and Roger carried her luggage to the room. The room was comfortable and close to a hedge and field of sheep mothers and new born lambs. No one to look in during daylight so perfect spot to sleep peacefully with no traffic noise in the small village with farm vehicles forming the only traffic. The hotel wing was small and well back from the road.

Roger had given her an extra case which was full of lingerie. Open crotch and peep hole bras in a range of colours. The bras were the correct size but he didn't know the her left nipple was inverted so her 34B chest was better without a bra. She was dressing in a knee length dress and had a bra slip underneath. Roger knocked and she let him in. He was dressed smart casual for dinner and she asked him to brush her hair whilst she did her makeup. She had managed to match a pair of silk knickers he had bought for her and was wearing self support stockings. He ran his fingers through her hair and brushed down her ginger hair.

"Should I let my hair down or not?"

"I like it long Maggie." She saw his bulge in the mirror as she applied her lippy and brushed her cheeks. She wore little make up; this was as much as she wore for an evening dinner.

She asked him to help her into her dress. "Maggie may I look at your underwear before you dress." She sat on the bed and spread her legs.

"You can put these knickers on me if you like."

He could see her smooth creamy lips open and her tiny pink winking vagina. He gently kissed her lips and stretched her labia open adoring her sex scent and sweet taste.

"Yes Roger lick me." He found her hood and flicked his tongue around it as she gasped with the sudden orgasm as she flopped back on the bed. She giggled at the sudden naughtiness she felt. She surprised herself at the rapid orgasm.

He was aching for sex but Maggie offered the knickers to him.

"Do you think you could leave them off this evening?" Maggie had never been out without underwear in her life but he was paying her this evening so she blushed and he slipped her dress over her head and zipped her into it. He slipped his hand up under the rear of the dress and gently fingered her with two fingers inside her. Surprised by the touch and excited she bent over and he slid his finger in and felt her grip him with her creamy velvet then release. He could feel her rhythm as she allowed him to explore her most private part. He withdrew and licked his fingers smelling once again her young scent.

"I hope I didn't offend you. You are beautiful. We could sleep in either of the rooms later."

They left and had a drink at the bar and were shown to a quiet window table in a bow window. They had an excellent meal. Throughout Maggie concentrated on her naked wet sex throbbing and feeling sexy. This whole relationship was exciting. He was asking her for her body, occasionally parting her legs with his foot. She wanted to be open to him. She was almost begging for the meal to end and they left for their rooms. He suggested he come to her room after he had changed into his running gear. This meant he could jog next morning and also would not look unusual in the hotel corridor.

Maggie slipped off her clothes and slipped into the open crotch silky under wear, she rolled and pinched her nipples and put on the matching top and coaxed her nipples through. The silky feel against her skin persuaded her inverted nipple to respond.

Roger knocked gently and undressed. He was hard for her and soon buried his face between her legs and offering her his erection. He was rigid average length and a little thicker particularly the bulbous end. Maggie quickly responded to his licking with a rapid series of clitoral orgasms which took her breath away. She gripped him in her hands as spasm after spasm continued. She was so glad to have a male body after so long.

She tried to handle him but she was so excited, she wanted to feel him inside her.

"Roger do you want to put it in me?"

"Of course I will be gentle." He slipped on a condom and asked "How do you want to lie on your back or side?"

Maggie lay on her side and lifted her leg vertically and he slid into her panties and gently opened her lips and eased his bell end into her contracting opening. She relaxed and he sank slowly into her slippery warm velvet. He began to move very gently inside her young body stroking her hair, smelling her hair and tasting her as he gently increased his thrusting to her obvious pleasure. He was excited how readily and quickly she came and he played against her swollen clitoris.

Their sex was silent apart from Maggie's gasps and panting as she had orgasms after orgasm. Roger couldn't last long and came from the squeezing from Maggie.

He spurted many times in that long aching ejaculation.

"Wow Roger I was horny but have never had so many orgasms!"

Roger went back to work licking her and she let go and came again and again. She had been licked before but never had this excitement with her boyfriend at University.

Roger slipped another condom on and asked her to bend over on all fours at the side of the bed he tested how willing she was to have him slam inside her. She grunted at each thrust and had a noisy series of orgasms as he pulled back then slammed hard up inside her as she came squeezing him. He tried not to ejaculate as long as he could but pumped a load. They were both perspiring after his effort and her hot sex.

Roger couldn't get a third erection but asked if he could sleep with her. Maggie agreed but she felt she wanted no romance just a sexual relationship with him. She felt OK about that good sex with a married man and she would not allow their professional relationship to be affected.

The next morning he went for a run whilst she showered and dressed in her business suit. They had breakfast and a successful conference presentation. She was wet as they went for supper. Roger undressed her in his bedroom longing to smell her wetness and sniffing her thong. He licked her for as long as he could and she could take the shuddering orgasms that came and came.

He wanted to fill her again and bent her over the bed and repeated strong thrusting as she gasped at the intensity of his pounding inside her. She loved every thrust and realised he had emptied himself inside her. Their sex continued once more. She felt tender as she slept naked wet and deeply.

Next morning he woke and she was wet enough to want him inside her. After sex he donned his running gear and came back dressed for breakfast with Maggie. They left for work and then drove home. Maggie was elated all day the rush of hormones from her multiple orgasms left her warm, aroused and wet. Roger asked her for her soiled underwear to remind him of her smell and taste and asked if she would sleep with him again. She volunteered to use part of his presentation so that she could contribute to presentations about the school and they would work to fashion presentations. Maggie was very confident and committed to the school. They would develop sharing when Maggie was horny and wet and she was happy to leave her worn underwear in sealed bags for him to use. She was always amused to imagine Roger sniffing the underwear she wore in bed. He always laundered her underwear and returned them. She felt comfortable and hungry for the end of term when she could have him lick and slip inside her eager cunt again.

So Maggie began to be useful not only as Secretary but also as an occasional partner. Roger rented an isolated cottage for part of the summer break. Discreet and comfortable for their needs. So their play together began...